#------------------------------------------------------------------------------ #$Date: 2019-12-17 21:43:01 +0000 (Tue, 17 Dec 2019) $ #$Revision: 245270 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500087.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_3500087 loop_ _publ_author_name 'Thierry Maris' _journal_name_full 'Personal communication to COD' _journal_year 2019 _chemical_formula_moiety 'C8 H20 N, Br' _chemical_formula_sum 'C8 H20 Br N' _chemical_formula_weight 210.16 _space_group_crystal_system trigonal _space_group_IT_number 167 _space_group_name_Hall '-R 3 2"c' _space_group_name_H-M_alt 'R -3 c :H' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary fmap _audit_creation_date 2013-03-14 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 18 _cell_length_a 12.0127(2) _cell_length_b 12.0127(2) _cell_length_c 35.1627(8) _cell_measurement_reflns_used 8728 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 72.903 _cell_measurement_theta_min 4.939 _cell_volume 4394.34(14) _computing_cell_refinement 'SAINT v8.27A (Bruker, 2012)' _computing_data_collection 'APEX2 (Bruker, 2012)' _computing_data_reduction 'SAINT v8.27A (Bruker, 2012)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Smart 6000' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'Montel 200 Mirrors Optics' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_unetI/netI 0.0169 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 17958 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 73.089 _diffrn_reflns_theta_min 4.939 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 5.204 _exptl_absorpt_correction_T_max 0.7537 _exptl_absorpt_correction_T_min 0.5082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1468 before and 0.0613 after correction. The Ratio of minimum to maximum transmission is 0.6743. The \l/2 correction factor is 0.0015. ; _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 1.429 _exptl_crystal_description block _exptl_crystal_F_000 1980 _exptl_crystal_recrystallization_method 'Recrystallized from EtOAc' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _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 0.615 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.080 _refine_ls_extinction_coef 0.00015(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 50 _refine_ls_number_reflns 984 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0262 _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^)+(0.0444P)^2^+4.3537P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.0743 _refine_special_details ; ? ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 920 _reflns_number_total 984 _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)' _iucr_refine_instructions_details ; TITL C2NBr in R-3c #167 CELL 1.54178 12.0127 12.0127 35.1627 90 90 120 ZERR 18 0.0002 0.0002 0.0008 0 0 0 LATT 3 SYMM -Y,+X-Y,+Z SYMM +Y-X,-X,+Z SYMM -Y+X,-Y,0.5-Z SYMM -X,-X+Y,0.5-Z SYMM +Y,+X,0.5-Z SFAC C H Br N UNIT 144 360 18 18 L.S. 20 PLAN 3 SIZE 0.08 0.15 0.18 TEMP -123.15 REM reset to R-3c #167 BOND $H CONF fmap 2 acta EXTI 0.000154 REM E:\PROJETS\2013\C2NBr\OLEX2\C2NBr.hkl WGHT 0.0444 4.3537 FVAR 0.04796 Br1 3 0.00000 0.00000 0.00000 10.16667 0.02463 0.02463 0.02534 = -0.00000 -0.00000 0.01232 Br2 3 0.66667 0.33333 0.01140 10.33333 0.02764 0.02764 0.02703 = -0.00000 -0.00000 0.01382 C4 1 0.32667 0.32669 0.01066 11.00000 0.02768 0.03024 0.02199 = -0.00258 -0.00317 0.01442 AFIX 137 H4a 2 0.26113 0.29586 -0.00935 11.00000 -1.50000 H4b 2 0.36517 0.27154 0.01172 11.00000 -1.50000 H4c 2 0.39353 0.41520 0.00506 11.00000 -1.50000 AFIX 0 C3 1 0.26506 0.32276 0.04867 11.00000 0.02261 0.03303 0.02315 = -0.00163 -0.00418 0.01555 AFIX 23 H3a 2 0.18214 0.24117 0.05037 11.00000 -1.20000 H3b 2 0.24605 0.39397 0.04946 11.00000 -1.20000 AFIX 0 C1 1 0.36317 0.21702 0.08643 11.00000 0.02900 0.02186 0.02498 = 0.00055 0.00135 0.01489 AFIX 23 H1a 2 0.41867 0.22844 0.10861 11.00000 -1.20000 H1b 2 0.40817 0.21251 0.06340 11.00000 -1.20000 AFIX 0 C2 1 0.23763 0.09042 0.09074 11.00000 0.04334 0.02133 0.03127 = 0.00029 0.00279 0.00828 AFIX 137 H2a 2 0.18571 0.07373 0.06771 11.00000 -1.50000 H2b 2 0.19013 0.09547 0.11271 11.00000 -1.50000 H2c 2 0.25622 0.02054 0.09459 11.00000 -1.50000 AFIX 0 N1 4 0.34581 0.33333 0.08333 10.50000 0.01813 0.01986 0.01911 = -0.00080 -0.00040 0.00993 HKLF 4 END ; _cod_data_source_file c2nbr.cif _cod_data_source_block c2nbr _cod_original_cell_volume 4394.3(2) _cod_original_sg_symbol_H-M 'R -3 c' _cod_database_code 3500087 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H1A,H1B} of C1, {H3A,H3B} of C3 At 1.5 times of: {H2A,H2B,H2C} of C2, {H4A,H4B,H4C} of C4 2.a Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C1(H1A,H1B) 2.b Idealised Me refined as rotating group: C4(H4A,H4B,H4C), C2(H2A,H2B,H2C) ; _shelx_estimated_absorpt_t_max 0.681 _shelx_estimated_absorpt_t_min 0.454 _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. ; _shelxl_version_number 2012-9 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' 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 Br1 Br 0.0000 0.0000 0.0000 0.02487(17) Uani 1 6 d S T P . . Br2 Br 0.6667 0.3333 0.01140(2) 0.02744(17) Uani 1 3 d S T P . . C4 C 0.32668(13) 0.32669(14) 0.01066(4) 0.0267(4) Uani 1 1 d . . . . . H4A H 0.2611 0.2959 -0.0093 0.040 Uiso 1 1 calc R U . . . H4B H 0.3652 0.2715 0.0117 0.040 Uiso 1 1 calc R U . . . H4C H 0.3935 0.4152 0.0051 0.040 Uiso 1 1 calc R U . . . C3 C 0.26506(13) 0.32276(14) 0.04867(4) 0.0255(3) Uani 1 1 d . . . . . H3A H 0.1821 0.2412 0.0504 0.031 Uiso 1 1 calc R U . . . H3B H 0.2460 0.3940 0.0495 0.031 Uiso 1 1 calc R U . . . C1 C 0.36317(14) 0.21702(13) 0.08643(4) 0.0243(3) Uani 1 1 d . . . . . H1A H 0.4187 0.2284 0.1086 0.029 Uiso 1 1 calc R U . . . H1B H 0.4082 0.2125 0.0634 0.029 Uiso 1 1 calc R U . . . C2 C 0.23763(17) 0.09042(15) 0.09074(5) 0.0355(4) Uani 1 1 d . . . . . H2A H 0.1857 0.0737 0.0677 0.053 Uiso 1 1 calc R U . . . H2B H 0.1901 0.0955 0.1127 0.053 Uiso 1 1 calc R U . . . H2C H 0.2562 0.0205 0.0946 0.053 Uiso 1 1 calc R U . . . N1 N 0.34581(12) 0.3333 0.0833 0.0188(3) Uani 1 2 d S T P . . 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 Br1 0.0246(2) 0.0246(2) 0.0253(3) 0.000 0.000 0.01232(10) Br2 0.02764(18) 0.02764(18) 0.0270(2) 0.000 0.000 0.01382(9) C4 0.0277(8) 0.0302(8) 0.0220(7) -0.0026(6) -0.0032(6) 0.0144(6) C3 0.0226(7) 0.0330(8) 0.0231(7) -0.0016(6) -0.0042(5) 0.0156(6) C1 0.0290(7) 0.0219(7) 0.0250(7) 0.0005(6) 0.0014(6) 0.0149(6) C2 0.0433(10) 0.0213(7) 0.0313(8) 0.0003(6) 0.0028(7) 0.0083(7) N1 0.0181(6) 0.0199(8) 0.0191(8) -0.0008(6) -0.0004(3) 0.0099(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 H4A C4 H4B 109.5 . . H4A C4 H4C 109.5 . . H4B C4 H4C 109.5 . . C3 C4 H4A 109.5 . . C3 C4 H4B 109.5 . . C3 C4 H4C 109.5 . . C4 C3 H3A 108.5 . . C4 C3 H3B 108.5 . . C4 C3 N1 114.96(11) . . H3A C3 H3B 107.5 . . N1 C3 H3A 108.5 . . N1 C3 H3B 108.5 . . H1A C1 H1B 107.7 . . C2 C1 H1A 108.8 . . C2 C1 H1B 108.8 . . N1 C1 H1A 108.8 . . N1 C1 H1B 108.8 . . N1 C1 C2 113.82(13) . . C1 C2 H2A 109.5 . . C1 C2 H2B 109.5 . . C1 C2 H2C 109.5 . . H2A C2 H2B 109.5 . . H2A C2 H2C 109.5 . . H2B C2 H2C 109.5 . . C3 N1 C3 106.94(14) . 16_554 C1 N1 C3 110.87(8) . 16_554 C1 N1 C3 110.86(8) 16_554 16_554 C1 N1 C3 110.85(8) . . C1 N1 C3 110.86(8) 16_554 . C1 N1 C1 106.51(14) . 16_554 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C4 H4A 0.9800 . C4 H4B 0.9800 . C4 H4C 0.9800 . C4 C3 1.5170(19) . C3 H3A 0.9900 . C3 H3B 0.9900 . C3 N1 1.5231(15) . C1 H1A 0.9900 . C1 H1B 0.9900 . C1 C2 1.522(2) . C1 N1 1.5163(16) . C2 H2A 0.9800 . C2 H2B 0.9800 . C2 H2C 0.9800 . N1 C3 1.5231(15) 16_554 N1 C1 1.5163(16) 16_554 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 C4 C3 N1 C3 173.29(15) . . . 16_554 C4 C3 N1 C1 -65.75(14) . . . . C4 C3 N1 C1 52.33(15) . . . 16_554 C2 C1 N1 C3 -60.66(15) . . . . C2 C1 N1 C3 57.95(15) . . . 16_554 C2 C1 N1 C1 178.65(15) . . . 16_554 _cod_database_fobs_code 3500087