#------------------------------------------------------------------------------ #$Date: 2016-03-03 15:50:20 +0000 (Thu, 03 Mar 2016) $ #$Revision: 177184 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500033.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500033 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _journal_name_full 'Personal communication to COD' _journal_year 2016 _chemical_formula_moiety 'C8 H4 N2 O2' _chemical_formula_sum 'C8 H4 N2 O2' _chemical_formula_weight 160.13 _chemical_name_common 'Benzene, 1,4-diisocyanato-' _chemical_name_systematic 1,4-Diisocyanatobenzene _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2016-01-28 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _cell_angle_alpha 103.240(3) _cell_angle_beta 102.529(3) _cell_angle_gamma 95.290(3) _cell_formula_units_Z 1 _cell_length_a 3.6601(2) _cell_length_b 6.0299(3) _cell_length_c 8.3765(4) _cell_measurement_reflns_used 2051 _cell_measurement_temperature 100 _cell_measurement_theta_max 60.726 _cell_measurement_theta_min 6.638 _cell_volume 173.701(16) _computing_cell_refinement ; 'SAINT (2013) V8.35A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; 'SAINT (2013) V8.35A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_unetI/netI 0.0221 _diffrn_reflns_laue_measured_fraction_full 1.000 _diffrn_reflns_laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 797 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.695 _diffrn_reflns_theta_min 4.868 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 0.618 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.5630 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. For component 1: wR2(int) was 0.1530 before and 0.0785 after correction. The Ratio of minimum to maximum transmission not present. The \l/2 correction factor is Not present For component 2: wR2(int) was 0.1665 before and 0.0565 after correction. The Ratio of minimum to maximum transmission not present. The \l/2 correction factor is Not present For component 3: wR2(int) was 0.1623 before and 0.0734 after correction. The Ratio of minimum to maximum transmission is 0.68. The \l/2 correction factor is Not present Final HKLF 4 output contains 11091 reflections, Rint = 0.0863 (8593 with I > 3sig(I), Rint = 0.0840) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.531 _exptl_crystal_description platelet _exptl_crystal_F_000 82 _exptl_crystal_preparation 'comercial source used as received' _exptl_crystal_recrystallization_method 'extracted from the bottle' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.025 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.337 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.069 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 55 _refine_ls_number_reflns 797 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0426 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.0521P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.1075 _reflns_Friedel_coverage 0.000 _reflns_friedel_fraction_full . _reflns_friedel_fraction_max . _reflns_number_gt 732 _reflns_number_total 797 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file PhNCO.cif _cod_data_source_block phnco _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 4287 2015-11-16 14:04:37Z antanas ; _cod_database_code 3500033 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.985 _shelx_estimated_absorpt_t_min 0.918 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2) ; _shelx_res_file ; phnco.res created by SHELXL-2014/7 TITL PhNCO_a.res in P-1 REM Old TITL PhNCO in P-1 #2 REM SHELXT solution in P-1 REM R1 0.101, Rweak 0.005, Alpha 0.016, Orientation as input REM Formula found by SHELXT: C4 N O CELL 1.34139 3.6601 6.0299 8.3765 103.24 102.529 95.29 ZERR 1 0.0002 0.0003 0.0004 0.003 0.003 0.003 LATT 1 SFAC C H N O DISP C 0.014 0.007 57.748 DISP H -0 0 0.648 DISP N 0.025 0.014 110.512 DISP O 0.039 0.025 193.954 UNIT 8 4 2 2 L.S. 12 PLAN 5 SIZE 0.025 0.1 0.14 TEMP 0 BOND $H LIST 4 MORE -1 CONF fmap 2 acta REM REM REM WGHT 0.060100 0.052100 FVAR 1.84449 O1 4 0.208810 0.129593 0.392110 11.00000 0.04308 0.02544 = 0.01809 0.00026 0.00389 0.00970 N1 3 0.261328 0.407939 0.648389 11.00000 0.03172 0.02133 = 0.01634 0.00213 0.00163 0.00480 C1 1 0.457051 0.711894 1.098395 11.00000 0.02214 0.01645 = 0.01937 -0.00039 0.00387 0.00208 AFIX 43 H1 2 0.429399 0.852891 1.164604 11.00000 -1.20000 AFIX 0 C2 1 0.340720 0.662245 0.923312 11.00000 0.02160 0.01842 = 0.01968 0.00431 0.00275 0.00374 AFIX 43 H2 2 0.233910 0.769826 0.871405 11.00000 -1.20000 AFIX 0 C3 1 0.384456 0.451421 0.826049 11.00000 0.02083 0.02060 = 0.01456 0.00054 0.00163 0.00036 C4 1 0.244516 0.259642 0.524239 11.00000 0.02637 0.02207 = 0.01960 0.00621 0.00194 0.00536 HKLF 4 REM PhNCO_a.res in P-1 REM R1 = 0.0426 for 732 Fo > 4sig(Fo) and 0.0453 for all 797 data REM 55 parameters refined using 0 restraints END WGHT 0.0600 0.0527 REM Highest difference peak 0.337, deepest hole -0.202, 1-sigma level 0.069 Q1 1 0.3902 0.5613 0.8807 11.00000 0.05 0.34 Q2 1 0.3213 0.4253 0.7389 11.00000 0.05 0.30 Q3 1 0.4259 0.6800 1.0129 11.00000 0.05 0.27 Q4 1 0.3644 0.3275 0.6127 11.00000 0.05 0.26 Q5 1 0.0100 0.1823 0.4188 11.00000 0.05 0.22 ; _shelx_res_checksum 27058 _shelx_hkl_file ; 1 0 0 1198.18 21.90 2 0 0 632.74 8.80 3 0 0 0.80 0.20 4 0 0 10.70 0.60 -4 1 0 1.50 0.40 -3 1 0 526.55 8.00 -2 1 0 193.28 2.50 -1 1 0 2601.84 51.29 0 1 0 997.40 36.40 1 1 0 8.50 0.20 2 1 0 100.79 1.50 3 1 0 20.30 0.60 4 1 0 10.60 0.50 -4 2 0 45.40 1.00 -3 2 0 28.60 0.60 -2 2 0 23.10 0.40 -1 2 0 151.18 2.90 0 2 0 313.37 4.60 1 2 0 2.20 0.10 2 2 0 2.50 0.20 3 2 0 8.20 0.40 4 2 0 10.20 0.60 -4 3 0 6.40 0.50 -3 3 0 36.90 0.80 -2 3 0 0.70 0.10 -1 3 0 76.99 1.10 0 3 0 1.00 0.10 1 3 0 460.45 5.40 2 3 0 60.29 1.00 3 3 0 0.20 0.30 -4 4 0 0.90 0.50 -3 4 0 20.50 1.00 -2 4 0 402.16 5.20 -1 4 0 360.36 4.50 0 4 0 51.99 0.90 1 4 0 80.79 1.20 2 4 0 11.10 0.50 3 4 0 3.50 0.40 -3 5 0 14.40 0.50 -2 5 0 164.78 2.50 -1 5 0 140.09 2.30 0 5 0 45.10 0.80 1 5 0 8.40 0.40 2 5 0 17.40 0.70 3 5 0 2.80 0.60 -3 6 0 20.70 0.90 -2 6 0 13.90 0.60 -1 6 0 56.59 1.20 0 6 0 19.50 0.60 1 6 0 27.90 1.10 2 6 0 7.00 0.70 -2 7 0 5.40 0.80 -1 7 0 125.29 2.10 0 7 0 102.19 3.10 1 7 0 11.60 0.90 -1 -7 1 32.30 1.20 0 -7 1 9.70 0.60 1 -7 1 5.70 0.40 2 -7 1 39.10 1.30 -2 -6 1 7.20 0.50 -1 -6 1 39.10 0.90 0 -6 1 123.09 3.40 1 -6 1 58.39 1.60 2 -6 1 0.10 0.40 3 -6 1 36.30 1.00 -3 -5 1 10.50 0.80 -2 -5 1 10.10 0.50 -1 -5 1 1.30 0.30 0 -5 1 297.07 5.30 1 -5 1 441.96 7.00 2 -5 1 6.50 0.30 3 -5 1 4.10 0.40 -3 -4 1 28.70 0.80 -2 -4 1 132.89 2.40 -1 -4 1 0.70 0.20 0 -4 1 205.38 3.40 1 -4 1 17.00 0.40 2 -4 1 35.80 0.60 3 -4 1 20.70 0.70 4 -4 1 7.30 0.60 -4 -3 1 2.00 0.40 -3 -3 1 9.00 0.40 -2 -3 1 7.50 0.30 -1 -3 1 50.19 0.80 0 -3 1 110.49 2.60 1 -3 1 23.50 0.50 2 -3 1 0.30 0.10 3 -3 1 52.69 0.90 4 -3 1 1.20 0.40 -4 -2 1 3.50 0.40 -3 -2 1 32.40 0.80 -2 -2 1 1.00 0.20 -1 -2 1 12.10 0.30 0 -2 1 944.31 21.80 1 -2 1 299.47 5.10 2 -2 1 1175.38 15.90 3 -2 1 3.60 0.30 4 -2 1 19.60 0.70 -4 -1 1 0.30 0.30 -3 -1 1 46.90 1.00 -2 -1 1 301.07 3.70 -1 -1 1 9999.00 265.17 0 -1 1 618.54 43.80 1 -1 1 3644.44 86.29 2 -1 1 34.10 0.60 3 -1 1 65.59 1.10 4 -1 1 9.10 0.50 -4 0 1 156.78 2.70 -3 0 1 48.20 0.90 -2 0 1 1561.14 18.60 -1 0 1 2861.71 55.59 0 0 1 80.19 2.40 1 0 1 134.79 2.50 2 0 1 134.89 1.90 3 0 1 22.30 0.50 4 0 1 10.50 0.60 -4 1 1 45.40 1.00 -3 1 1 10.40 0.40 -2 1 1 13.80 0.30 -1 1 1 329.87 4.70 0 1 1 161.58 2.90 1 1 1 29.70 0.70 2 1 1 42.10 0.90 3 1 1 23.70 0.70 4 1 1 8.30 0.50 -4 2 1 14.60 0.70 -3 2 1 0.60 0.30 -2 2 1 1.50 0.10 -1 2 1 15.00 0.40 0 2 1 1011.50 14.90 1 2 1 144.49 2.00 2 2 1 4.30 0.20 3 2 1 39.50 1.40 4 2 1 35.10 0.90 -4 3 1 27.60 0.80 -3 3 1 176.68 2.60 -2 3 1 214.78 2.70 -1 3 1 269.47 3.80 0 3 1 417.46 4.10 1 3 1 0.40 0.20 2 3 1 3.60 0.30 3 3 1 6.10 0.40 -4 4 1 32.90 1.10 -3 4 1 211.98 3.90 -2 4 1 93.39 1.40 -1 4 1 8.30 0.30 0 4 1 7.60 0.20 1 4 1 47.00 0.80 2 4 1 3.00 0.60 3 4 1 12.50 0.90 -3 5 1 29.90 0.70 -2 5 1 99.69 1.80 -1 5 1 3.60 0.30 0 5 1 56.49 1.10 1 5 1 15.10 0.80 2 5 1 2.80 0.40 -3 6 1 6.10 0.50 -2 6 1 80.29 1.40 -1 6 1 130.99 2.30 0 6 1 27.70 0.80 1 6 1 2.40 0.40 2 6 1 101.69 2.40 -2 7 1 137.49 2.20 -1 7 1 1.30 0.40 0 7 1 6.50 0.90 -1 -7 2 56.59 1.30 0 -7 2 4.50 0.50 1 -7 2 15.80 0.70 2 -7 2 39.60 1.00 -2 -6 2 24.40 0.70 -1 -6 2 172.48 2.90 0 -6 2 198.58 9.50 1 -6 2 0.50 0.40 2 -6 2 29.50 0.80 3 -6 2 0.70 0.50 -3 -5 2 28.10 1.00 -2 -5 2 6.00 0.40 -1 -5 2 185.98 3.30 0 -5 2 54.89 1.20 1 -5 2 15.30 0.50 2 -5 2 22.40 0.60 3 -5 2 8.50 0.40 -3 -4 2 14.70 0.50 -2 -4 2 7.40 0.40 -1 -4 2 15.60 0.40 0 -4 2 13.70 0.40 1 -4 2 29.70 0.60 2 -4 2 32.00 0.70 3 -4 2 8.10 0.40 4 -4 2 0.60 0.40 -4 -3 2 5.50 0.50 -3 -3 2 3.50 0.90 -2 -3 2 7.60 0.30 -1 -3 2 62.29 1.00 0 -3 2 90.49 1.80 1 -3 2 1215.28 16.00 2 -3 2 9.60 0.30 3 -3 2 55.09 0.90 4 -3 2 42.30 1.10 -4 -2 2 0.40 0.40 -3 -2 2 90.79 1.60 -2 -2 2 1358.56 16.30 -1 -2 2 116.89 1.80 0 -2 2 4461.95 214.88 1 -2 2 238.28 4.00 2 -2 2 222.08 2.70 3 -2 2 19.20 0.60 4 -2 2 62.49 1.30 -4 -1 2 3.10 0.40 -3 -1 2 638.44 10.50 -2 -1 2 1056.19 13.60 -1 -1 2 221.68 2.90 0 -1 2 0.60 0.10 1 -1 2 628.54 10.60 2 -1 2 30.30 0.50 3 -1 2 42.00 0.90 4 -1 2 18.40 0.80 -4 0 2 4.10 0.40 -3 0 2 14.00 0.50 -2 0 2 39.60 0.50 -1 0 2 211.18 2.70 0 0 2 404.96 8.60 1 0 2 143.39 2.50 2 0 2 54.29 0.80 3 0 2 1.10 0.30 4 0 2 19.40 0.90 -4 1 2 1.90 0.40 -3 1 2 32.40 0.70 -2 1 2 15.00 0.30 -1 1 2 356.76 4.60 0 1 2 315.57 5.60 1 1 2 5.40 0.20 2 1 2 84.69 1.20 3 1 2 83.99 1.60 4 1 2 0.50 0.60 -4 2 2 42.20 1.20 -3 2 2 42.90 0.80 -2 2 2 252.47 2.90 -1 2 2 765.22 8.80 0 2 2 32.60 0.40 1 2 2 0.30 0.10 2 2 2 104.49 2.00 3 2 2 17.90 0.70 -4 3 2 148.19 2.50 -3 3 2 41.30 0.80 -2 3 2 9.00 0.30 -1 3 2 11.40 0.30 0 3 2 80.49 0.90 1 3 2 1.00 0.20 2 3 2 29.90 0.80 3 3 2 0.80 0.40 -4 4 2 42.60 1.10 -3 4 2 78.19 1.30 -2 4 2 0.80 0.30 -1 4 2 83.49 1.50 0 4 2 8.70 0.30 1 4 2 34.30 0.60 2 4 2 3.00 0.40 3 4 2 31.60 1.30 -3 5 2 22.90 0.60 -2 5 2 120.29 2.30 -1 5 2 31.80 0.80 0 5 2 25.60 0.90 1 5 2 198.78 4.00 2 5 2 14.80 0.90 -3 6 2 139.19 2.40 -2 6 2 1.70 0.40 -1 6 2 26.50 0.80 0 6 2 147.59 3.40 1 6 2 111.69 2.60 -1 7 2 18.50 0.80 0 7 2 2.10 0.60 -1 -7 3 47.20 1.00 0 -7 3 6.70 0.70 1 -7 3 46.80 1.30 2 -7 3 1.70 0.40 -2 -6 3 122.69 2.20 -1 -6 3 63.29 1.30 0 -6 3 2.60 0.70 1 -6 3 6.80 0.40 2 -6 3 4.70 0.30 3 -6 3 12.80 0.50 -3 -5 3 0.70 0.40 -2 -5 3 0.90 0.30 -1 -5 3 12.90 0.70 0 -5 3 53.49 1.20 1 -5 3 9.00 0.50 2 -5 3 27.60 1.30 3 -5 3 0.70 0.30 -3 -4 3 9.20 0.40 -2 -4 3 1.10 0.30 -1 -4 3 8.90 0.30 0 -4 3 409.46 7.20 1 -4 3 16.40 0.40 2 -4 3 77.89 1.20 3 -4 3 47.50 0.90 -4 -3 3 20.70 0.90 -3 -3 3 160.68 4.60 -2 -3 3 6.90 0.30 -1 -3 3 1391.76 22.40 0 -3 3 319.97 5.30 1 -3 3 378.96 5.10 2 -3 3 20.00 0.40 3 -3 3 211.18 3.10 4 -3 3 3.00 0.50 -4 -2 3 257.97 4.90 -3 -2 3 343.97 4.60 -2 -2 3 118.39 1.50 -1 -2 3 111.89 1.50 0 -2 3 644.34 13.10 1 -2 3 24.30 0.40 2 -2 3 167.18 2.00 3 -2 3 15.70 0.60 4 -2 3 37.40 1.30 -4 -1 3 54.09 1.10 -3 -1 3 0.60 0.20 -2 -1 3 37.30 0.50 -1 -1 3 331.07 4.40 0 -1 3 95.49 2.00 1 -1 3 143.49 1.70 2 -1 3 8.80 0.30 3 -1 3 75.59 1.60 4 -1 3 85.19 2.00 -4 0 3 22.70 0.70 -3 0 3 5.80 0.30 -2 0 3 6.00 0.20 -1 0 3 147.39 1.60 0 0 3 26.80 0.60 1 0 3 138.09 1.80 2 0 3 151.88 1.80 3 0 3 19.70 0.90 4 0 3 85.79 1.90 -4 1 3 0.50 0.40 -3 1 3 100.89 1.40 -2 1 3 376.06 4.10 -1 1 3 55.39 0.60 0 1 3 0.40 0.10 1 1 3 632.04 7.70 2 1 3 75.79 1.30 3 1 3 0.20 0.40 -4 2 3 10.30 0.60 -3 2 3 39.90 0.70 -2 2 3 17.40 0.30 -1 2 3 30.70 0.40 0 2 3 36.80 0.50 1 2 3 18.20 0.40 2 2 3 1.20 0.30 3 2 3 8.70 0.50 -4 3 3 37.50 1.00 -3 3 3 0.40 0.30 -2 3 3 69.29 1.00 -1 3 3 0.80 0.10 0 3 3 103.59 1.40 1 3 3 0.90 0.20 2 3 3 22.40 0.90 3 3 3 126.19 2.50 -4 4 3 1.00 0.70 -3 4 3 62.69 1.10 -2 4 3 12.40 0.40 -1 4 3 74.89 1.30 0 4 3 174.18 2.10 1 4 3 15.50 0.50 2 4 3 395.56 7.90 -3 5 3 0.70 0.40 -2 5 3 45.30 1.00 -1 5 3 190.88 6.70 0 5 3 236.78 4.00 1 5 3 22.10 0.70 2 5 3 54.19 2.60 -2 6 3 25.60 0.80 -1 6 3 32.70 0.90 0 6 3 1.40 0.40 1 6 3 1.30 0.60 -1 -7 4 0.30 0.40 0 -7 4 12.00 2.70 1 -7 4 2.10 0.40 2 -7 4 12.30 0.50 -2 -6 4 15.80 0.60 -1 -6 4 28.00 0.90 0 -6 4 2.30 0.40 1 -6 4 37.20 1.00 2 -6 4 1.30 0.30 -3 -5 4 0.70 0.40 -2 -5 4 0.50 0.30 -1 -5 4 64.79 1.50 0 -5 4 21.60 0.70 1 -5 4 33.80 1.00 2 -5 4 28.30 0.70 3 -5 4 71.89 1.50 -3 -4 4 0.70 0.40 -2 -4 4 272.27 4.40 -1 -4 4 151.98 2.40 0 -4 4 236.28 4.10 1 -4 4 6.20 0.30 2 -4 4 388.26 5.00 3 -4 4 10.30 0.50 -4 -3 4 96.09 2.80 -3 -3 4 52.39 1.30 -2 -3 4 118.29 1.70 -1 -3 4 187.38 2.90 0 -3 4 2.00 0.20 1 -3 4 377.86 5.00 2 -3 4 2.90 0.20 3 -3 4 48.40 1.00 -4 -2 4 6.40 0.50 -3 -2 4 1.70 0.30 -2 -2 4 97.89 1.30 -1 -2 4 6.20 0.20 0 -2 4 205.78 3.00 1 -2 4 27.10 0.50 2 -2 4 178.68 2.40 3 -2 4 108.39 2.10 -4 -1 4 0.40 0.40 -3 -1 4 7.90 0.40 -2 -1 4 23.70 0.50 -1 -1 4 75.29 0.80 0 -1 4 70.09 1.20 1 -1 4 86.79 1.00 2 -1 4 87.89 1.10 3 -1 4 245.88 4.20 -4 0 4 29.20 0.80 -3 0 4 89.69 1.50 -2 0 4 3.90 0.20 -1 0 4 2.40 0.10 0 0 4 1333.17 22.00 1 0 4 187.58 2.40 2 0 4 36.90 0.60 3 0 4 14.70 0.60 -4 1 4 38.00 1.00 -3 1 4 18.40 0.50 -2 1 4 0.60 0.20 -1 1 4 84.59 0.80 0 1 4 10.10 0.20 1 1 4 1.70 0.20 2 1 4 35.10 0.70 3 1 4 0.30 0.40 -4 2 4 1.20 0.50 -3 2 4 35.40 0.70 -2 2 4 7.60 0.20 -1 2 4 113.99 1.30 0 2 4 20.90 0.40 1 2 4 1.10 0.20 2 2 4 108.69 2.10 3 2 4 1.10 0.40 -4 3 4 19.10 0.80 -3 3 4 0.70 0.40 -2 3 4 67.19 1.10 -1 3 4 77.69 1.00 0 3 4 14.20 0.30 1 3 4 687.43 10.20 2 3 4 306.57 5.70 -4 4 4 0.50 0.50 -3 4 4 33.50 0.90 -2 4 4 154.58 2.20 -1 4 4 324.07 4.70 0 4 4 105.39 1.30 1 4 4 233.88 3.50 2 4 4 5.80 0.50 -3 5 4 24.60 0.80 -2 5 4 97.79 1.80 -1 5 4 0.50 0.40 0 5 4 0.30 0.40 1 5 4 20.50 1.10 -2 6 4 28.90 1.50 -1 6 4 4.90 0.50 0 6 4 0.40 0.70 -1 -7 5 0.90 0.40 0 -7 5 24.80 1.20 1 -7 5 0.40 0.60 -2 -6 5 5.90 0.40 -1 -6 5 16.10 0.70 0 -6 5 3.30 0.40 1 -6 5 6.90 0.50 2 -6 5 27.30 0.70 -3 -5 5 78.59 1.70 -2 -5 5 43.40 1.10 -1 -5 5 66.79 1.60 0 -5 5 3.70 0.30 1 -5 5 385.96 7.30 2 -5 5 13.20 0.50 3 -5 5 80.99 1.60 -3 -4 5 67.19 1.40 -2 -4 5 34.20 0.80 -1 -4 5 2.50 0.30 0 -4 5 308.87 5.30 1 -4 5 8.40 0.40 2 -4 5 55.69 1.20 3 -4 5 5.00 0.40 -4 -3 5 1.10 0.50 -3 -3 5 16.40 0.60 -2 -3 5 0.50 0.30 -1 -3 5 120.19 1.60 0 -3 5 11.60 0.40 1 -3 5 225.98 3.00 2 -3 5 67.99 1.10 3 -3 5 0.30 0.30 -4 -2 5 8.40 0.60 -3 -2 5 0.60 0.30 -2 -2 5 53.79 0.80 -1 -2 5 7.30 0.20 0 -2 5 0.20 0.20 1 -2 5 179.48 2.20 2 -2 5 407.96 5.30 3 -2 5 42.20 1.00 -4 -1 5 12.20 0.60 -3 -1 5 2.40 0.30 -2 -1 5 12.20 0.40 -1 -1 5 567.34 5.60 0 -1 5 158.58 2.80 1 -1 5 241.68 2.60 2 -1 5 95.69 1.40 3 -1 5 17.80 0.80 -4 0 5 11.60 0.60 -3 0 5 0.10 0.30 -2 0 5 69.19 1.10 -1 0 5 107.99 1.10 0 0 5 0.60 0.20 1 0 5 30.70 0.70 2 0 5 2.00 0.20 3 0 5 4.70 0.40 -4 1 5 13.80 0.70 -3 1 5 3.40 0.30 -2 1 5 49.80 0.80 -1 1 5 34.70 0.40 0 1 5 16.10 0.40 1 1 5 37.70 0.60 2 1 5 2.40 0.50 3 1 5 105.99 2.20 -4 2 5 0.80 0.50 -3 2 5 27.70 1.50 -2 2 5 4.20 0.30 -1 2 5 3.80 0.10 0 2 5 812.82 10.10 1 2 5 432.26 5.80 2 2 5 79.69 1.50 -4 3 5 10.50 0.80 -3 3 5 76.39 1.40 -2 3 5 243.28 3.70 -1 3 5 236.18 2.70 0 3 5 698.23 8.60 1 3 5 7.80 0.40 2 3 5 5.00 0.50 -3 4 5 136.49 2.60 -2 4 5 0.50 0.40 -1 4 5 19.50 0.80 0 4 5 9.10 0.30 1 4 5 1.20 0.40 -3 5 5 9.80 0.70 -2 5 5 2.00 0.50 -1 5 5 12.50 0.70 0 5 5 7.80 0.90 1 5 5 15.50 0.80 -1 -7 6 0.50 0.40 0 -7 6 1.20 2.00 1 -7 6 0.90 0.40 -2 -6 6 7.60 0.50 -1 -6 6 4.80 0.50 0 -6 6 222.58 4.60 1 -6 6 7.20 0.50 2 -6 6 144.59 3.30 -3 -5 6 4.10 0.50 -2 -5 6 3.10 0.40 -1 -5 6 157.28 3.70 0 -5 6 47.40 1.30 1 -5 6 45.40 1.00 2 -5 6 1.60 0.30 -3 -4 6 0.90 0.40 -2 -4 6 52.09 2.30 -1 -4 6 0.30 0.30 0 -4 6 184.18 3.70 1 -4 6 20.70 0.60 2 -4 6 25.00 0.70 3 -4 6 32.30 0.80 -4 -3 6 0.70 0.50 -3 -3 6 25.60 0.90 -2 -3 6 2.50 0.30 -1 -3 6 41.30 0.80 0 -3 6 198.98 2.50 1 -3 6 326.07 4.50 2 -3 6 19.70 0.60 3 -3 6 22.50 1.00 -4 -2 6 4.60 0.70 -3 -2 6 17.60 0.70 -2 -2 6 125.69 2.30 -1 -2 6 19.30 0.40 0 -2 6 391.06 6.70 1 -2 6 243.58 3.20 2 -2 6 12.70 0.60 3 -2 6 6.90 0.70 -4 -1 6 0.80 0.50 -3 -1 6 39.70 1.10 -2 -1 6 119.89 2.20 -1 -1 6 0.30 0.10 0 -1 6 0.30 0.20 1 -1 6 1.80 0.20 2 -1 6 21.40 0.60 3 -1 6 0.20 0.50 -4 0 6 0.70 0.50 -3 0 6 8.10 0.50 -2 0 6 7.80 0.40 -1 0 6 30.50 0.40 0 0 6 0.20 0.30 1 0 6 8.40 0.40 2 0 6 99.09 1.60 3 0 6 38.60 1.20 -4 1 6 10.00 0.80 -3 1 6 4.90 0.50 -2 1 6 0.30 0.30 -1 1 6 401.56 4.40 0 1 6 417.86 6.80 1 1 6 186.18 3.20 2 1 6 180.88 2.80 -4 2 6 25.50 1.50 -3 2 6 89.99 1.90 -2 2 6 247.38 4.20 -1 2 6 988.60 11.70 0 2 6 3.40 0.20 1 2 6 66.59 1.20 2 2 6 11.00 0.70 -3 3 6 1.30 0.50 -2 3 6 89.59 1.80 -1 3 6 0.20 0.20 0 3 6 0.20 0.30 1 3 6 32.40 0.80 2 3 6 0.30 0.50 -3 4 6 1.40 0.60 -2 4 6 29.30 0.90 -1 4 6 13.90 0.60 0 4 6 3.80 0.40 1 4 6 10.10 1.40 -2 5 6 23.70 1.00 -1 5 6 7.50 0.70 0 5 6 95.29 3.20 -2 -6 7 76.29 1.60 -1 -6 7 50.69 1.40 0 -6 7 30.10 1.00 1 -6 7 4.30 0.50 -2 -5 7 3.50 0.40 -1 -5 7 60.19 1.30 0 -5 7 3.40 0.40 1 -5 7 61.99 1.20 2 -5 7 34.70 1.10 -3 -4 7 1.70 0.50 -2 -4 7 59.19 1.30 -1 -4 7 135.29 2.30 0 -4 7 108.69 2.10 1 -4 7 0.50 0.30 2 -4 7 48.50 0.90 -3 -3 7 14.30 0.70 -2 -3 7 2.70 0.40 -1 -3 7 270.57 4.00 0 -3 7 251.27 4.00 1 -3 7 1.70 0.30 2 -3 7 0.20 0.30 -4 -2 7 16.20 0.80 -3 -2 7 55.29 1.50 -2 -2 7 0.60 0.40 -1 -2 7 17.10 0.50 0 -2 7 0.20 0.40 1 -2 7 35.40 0.80 2 -2 7 4.20 0.40 -4 -1 7 0.50 0.70 -3 -1 7 0.20 0.50 -2 -1 7 23.70 0.70 -1 -1 7 11.00 0.30 0 -1 7 6.10 0.30 1 -1 7 38.20 0.90 2 -1 7 50.89 1.00 -4 0 7 10.40 1.10 -3 0 7 2.00 0.50 -2 0 7 97.69 1.70 -1 0 7 156.28 1.80 0 0 7 186.38 3.90 1 0 7 325.77 7.10 2 0 7 15.00 0.50 -4 1 7 11.30 0.90 -3 1 7 165.28 3.20 -2 1 7 708.43 12.20 -1 1 7 0.30 0.20 0 1 7 222.28 4.50 1 1 7 13.50 0.60 2 1 7 15.40 0.80 -3 2 7 139.89 2.80 -2 2 7 22.10 0.80 -1 2 7 1.20 0.20 0 2 7 48.10 0.80 1 2 7 4.90 0.30 2 2 7 21.90 1.40 -3 3 7 15.20 0.90 -2 3 7 15.10 0.70 -1 3 7 1.90 0.30 0 3 7 2.50 0.30 1 3 7 13.50 0.80 -2 4 7 10.70 1.00 -1 4 7 92.69 3.10 0 4 7 24.60 4.00 -1 -6 8 0.80 0.50 0 -6 8 51.79 1.80 1 -6 8 26.00 1.20 -2 -5 8 63.39 1.60 -1 -5 8 10.10 0.50 0 -5 8 8.80 0.60 1 -5 8 48.10 0.90 -3 -4 8 17.00 0.80 -2 -4 8 144.79 2.90 -1 -4 8 127.89 2.20 0 -4 8 0.20 0.30 1 -4 8 6.80 0.40 2 -4 8 0.80 0.40 -3 -3 8 3.80 0.60 -2 -3 8 44.70 1.30 -1 -3 8 11.10 1.00 0 -3 8 25.20 0.80 1 -3 8 8.60 0.50 2 -3 8 19.50 0.70 -3 -2 8 9.50 0.80 -2 -2 8 8.10 0.70 -1 -2 8 3.80 0.30 0 -2 8 1.90 0.50 1 -2 8 49.30 1.20 2 -2 8 0.80 0.40 -3 -1 8 9.00 0.70 -2 -1 8 23.30 1.40 -1 -1 8 89.49 1.20 0 -1 8 270.47 3.50 1 -1 8 10.90 0.70 2 -1 8 9.80 0.80 -3 0 8 291.07 5.80 -2 0 8 1.10 0.40 -1 0 8 257.67 3.20 0 0 8 5.70 0.70 1 0 8 56.79 1.60 2 0 8 27.20 1.00 -3 1 8 44.30 1.30 -2 1 8 8.50 0.50 -1 1 8 21.50 0.50 0 1 8 21.90 0.70 1 1 8 37.80 1.50 -3 2 8 5.20 0.60 -2 2 8 10.90 0.60 -1 2 8 1.20 0.30 0 2 8 22.40 0.60 1 2 8 20.60 1.30 -2 3 8 45.40 1.50 -1 3 8 12.80 0.70 0 3 8 0.10 0.40 -2 -5 9 24.40 1.50 -1 -5 9 3.50 0.50 0 -5 9 16.20 0.70 -2 -4 9 16.70 0.90 -1 -4 9 6.20 0.50 0 -4 9 4.70 0.40 1 -4 9 11.90 0.60 -3 -3 9 0.80 0.70 -2 -3 9 4.90 0.60 -1 -3 9 2.00 0.40 0 -3 9 23.00 0.90 1 -3 9 6.70 0.50 -3 -2 9 0.60 0.80 -2 -2 9 32.20 1.40 -1 -2 9 125.09 2.00 0 -2 9 1.00 0.60 1 -2 9 12.20 0.50 -3 -1 9 2.50 0.70 -2 -1 9 160.88 4.00 -1 -1 9 0.30 0.40 0 -1 9 73.29 1.20 1 -1 9 47.70 1.80 -3 0 9 12.10 1.00 -2 0 9 1.40 0.50 -1 0 9 30.90 0.80 0 0 9 31.00 0.80 1 0 9 14.60 0.90 -3 1 9 7.30 0.70 -2 1 9 7.70 0.50 -1 1 9 22.60 0.70 0 1 9 22.00 0.80 1 1 9 0.40 0.60 -2 2 9 9.10 0.70 -1 2 9 1.80 0.40 0 2 9 47.60 1.30 -1 -4 10 6.60 0.60 0 -4 10 10.80 0.50 -2 -3 10 31.10 1.30 -1 -3 10 0.80 0.50 0 -3 10 4.40 0.90 -2 -2 10 0.90 1.40 -1 -2 10 45.50 1.20 0 -2 10 49.99 1.20 -2 -1 10 11.60 2.70 -1 -1 10 10.70 0.50 0 -1 10 32.60 1.00 -2 0 10 11.70 1.20 -1 0 10 20.30 0.90 0 0 10 11.20 0.60 -2 1 10 4.80 0.70 -1 1 10 23.40 0.90 _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 80197 _shelx_shelxl_version_number 2014/7 _olex2_date_sample_submission 2015-11-05 _olex2_exptl_crystal_mounting_method 'mounted on a cryoloop' _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2088(3) 0.12959(15) 0.39211(11) 0.0300(3) Uani 1 1 d . . . . . N1 N 0.2613(3) 0.40794(17) 0.64839(12) 0.0242(3) Uani 1 1 d . . . . . C1 C 0.4571(3) 0.71189(19) 1.09839(14) 0.0204(3) Uani 1 1 d . . . . . H1 H 0.4294 0.8529 1.1646 0.024 Uiso 1 1 calc R . . . . C2 C 0.3407(3) 0.66225(19) 0.92331(14) 0.0203(3) Uani 1 1 d . . . . . H2 H 0.2339 0.7698 0.8714 0.024 Uiso 1 1 calc R . . . . C3 C 0.3845(3) 0.45142(19) 0.82605(14) 0.0199(3) Uani 1 1 d . . . . . C4 C 0.2445(3) 0.2596(2) 0.52424(14) 0.0230(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0431(6) 0.0254(5) 0.0181(5) 0.0003(4) 0.0039(4) 0.0097(4) N1 0.0317(6) 0.0213(5) 0.0163(5) 0.0021(4) 0.0016(4) 0.0048(4) C1 0.0221(6) 0.0165(5) 0.0194(6) -0.0004(4) 0.0039(4) 0.0021(4) C2 0.0216(5) 0.0184(6) 0.0197(6) 0.0043(4) 0.0028(4) 0.0037(4) C3 0.0208(5) 0.0206(6) 0.0146(5) 0.0005(4) 0.0016(4) 0.0004(4) C4 0.0264(6) 0.0221(6) 0.0196(6) 0.0062(5) 0.0019(4) 0.0054(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0140 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C4 N1 C3 139.61(11) . . C2 C1 H1 120.3 . . C2 C1 C3 119.36(11) . 2_667 C3 C1 H1 120.3 2_667 . C1 C2 H2 120.1 . . C3 C2 C1 119.72(11) . . C3 C2 H2 120.1 . . C1 C3 N1 121.26(11) 2_667 . C2 C3 N1 117.82(11) . . C2 C3 C1 120.92(11) . 2_667 O1 C4 N1 172.52(13) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C4 1.1738(14) . N1 C3 1.4124(14) . N1 C4 1.1921(15) . C1 H1 0.9300 . C1 C2 1.3879(16) . C1 C3 1.3922(17) 2_667 C2 H2 0.9300 . C2 C3 1.3875(16) . C3 C1 1.3923(17) 2_667 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 C2 C3 N1 179.85(10) . . . . C1 C2 C3 C1 0.15(19) . . . 2_667 C3 C1 C2 C3 -0.15(19) 2_667 . . . C4 N1 C3 C1 -0.1(2) . . . 2_667 C4 N1 C3 C2 -179.79(14) . . . . _cod_database_fobs_code 3500033