#------------------------------------------------------------------------------ #$Date: 2019-12-17 21:28:55 +0000 (Tue, 17 Dec 2019) $ #$Revision: 245265 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500082.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_3500082 loop_ _publ_author_name 'Thierry Maris' _journal_name_full 'Personal communication to COD' _journal_year 2019 _chemical_formula_moiety 'C20 H44 N, Br' _chemical_formula_sum 'C20 H44 Br N' _chemical_formula_weight 378.47 _space_group_crystal_system orthorhombic _space_group_IT_number 68 _space_group_name_Hall '-C 2a 2ac' _space_group_name_H-M_alt 'C c c a :2' _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 90 _cell_formula_units_Z 4 _cell_length_a 10.5034(7) _cell_length_b 22.9748(18) _cell_length_c 9.2342(6) _cell_measurement_reflns_used 7399 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 68.272 _cell_measurement_theta_min 4.629 _cell_volume 2228.3(3) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _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 0.995 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker Microstar X8' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'Helios Mirror Optics' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10906 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.553 _diffrn_reflns_theta_min 6.668 _diffrn_source 'Rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 2.477 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.5643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1021 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.7493. 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 1.128 _exptl_crystal_description block _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _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 0.306 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 53 _refine_ls_number_reflns 1025 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0330 _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^)+(0.0514P)^2^+1.8804P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0862 _refine_ls_wR_factor_ref 0.0902 _refine_special_details ; ? ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 933 _reflns_number_total 1025 _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 JW1758 in Ccca #68 CELL 1.54178 10.5034 22.9748 9.2342 90 90 90 ZERR 4 0.0007 0.0018 0.0006 0 0 0 LATT 7 SYMM -X,0.5-Y,+Z SYMM +X,0.5-Y,0.5-Z SYMM -X,+Y,0.5-Z SFAC C H N Br UNIT 80 176 4 4 L.S. 20 0 0 511 PLAN 3 TEMP -123.15 BOND $H CONF fmap 2 acta REM E:/PROJETS/2013/C5NBr/OLEX2/C5NBr.hkl WGHT 0.0514 1.8804 FVAR 0.19198 Br1 4 0.50000 0.25000 0.25000 10.25000 0.04690 0.05297 0.02866 = 0.00000 0.00000 -0.00000 N1 3 0.00000 0.25000 0.25000 10.25000 0.02835 0.02717 0.01855 = 0.00000 0.00000 -0.00000 C1 1 0.08233 0.28723 0.15101 11.00000 0.03225 0.03278 0.01863 = 0.00046 0.00249 0.00045 AFIX 23 H1a 2 0.13809 0.26116 0.09389 11.00000 -1.20000 H1b 2 0.02603 0.30786 0.08203 11.00000 -1.20000 AFIX 0 C2 1 0.16497 0.33178 0.22680 11.00000 0.03301 0.03803 0.02344 = -0.00105 0.00193 -0.00507 AFIX 23 H2a 2 0.22317 0.31187 0.29504 11.00000 -1.20000 H2b 2 0.11066 0.35879 0.28303 11.00000 -1.20000 AFIX 0 C3 1 0.24224 0.36594 0.11618 11.00000 0.03330 0.03860 0.02710 = 0.00290 0.00092 -0.00277 AFIX 23 H3a 2 0.29984 0.33894 0.06434 11.00000 -1.20000 H3b 2 0.18368 0.38326 0.04407 11.00000 -1.20000 AFIX 0 C4 1 0.32016 0.41369 0.18467 11.00000 0.04978 0.04957 0.03544 = 0.00008 0.00357 -0.01659 AFIX 23 H4a 2 0.37771 0.39632 0.25776 11.00000 -1.20000 H4b 2 0.26227 0.44083 0.23564 11.00000 -1.20000 AFIX 0 C5 1 0.39914 0.44779 0.07614 11.00000 0.04721 0.05222 0.04283 = 0.00826 0.00167 -0.01511 AFIX 137 H5a 2 0.34296 0.46486 0.00281 11.00000 -1.50000 H5b 2 0.46020 0.42165 0.02915 11.00000 -1.50000 H5c 2 0.44524 0.47889 0.12642 11.00000 -1.50000 AFIX 0 HKLF 4 END ; _cod_data_source_file c5nbr.cif _cod_data_source_block c5nbr _cod_original_sg_symbol_Hall '-C 2b 2bc' _cod_original_sg_symbol_H-M 'C c c a' _cod_database_code 3500082 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H2A,H2B} of C2, {H4A,H4B} of C4, {H3A,H3B} of C3, {H1A,H1B} of C1 At 1.5 times of: {H5A,H5B,H5C} of C5 2.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B) 2.b Idealised Me refined as rotating group: C5(H5A,H5B,H5C) ; _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' '-x, -y+1/2, z' 'x, -y+1/2, -z+1/2' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z' 'x+1/2, -y+1, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z' '-x, y-1/2, z-1/2' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z' '-x+1/2, y, z-1/2' 'x+1/2, -y+1/2, z-1/2' 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 0.5000 0.2500 0.2500 0.0428(2) Uani 1 4 d S T P . . N1 N 0.0000 0.2500 0.2500 0.0247(6) Uani 1 4 d S T P . . C1 C 0.08233(15) 0.28723(7) 0.15101(16) 0.0279(4) Uani 1 1 d . . . . . H1A H 0.1381 0.2612 0.0939 0.033 Uiso 1 1 calc R U . . . H1B H 0.0260 0.3079 0.0820 0.033 Uiso 1 1 calc R U . . . C2 C 0.16497(17) 0.33178(8) 0.22680(18) 0.0315(4) Uani 1 1 d . . . . . H2A H 0.2232 0.3119 0.2950 0.038 Uiso 1 1 calc R U . . . H2B H 0.1107 0.3588 0.2830 0.038 Uiso 1 1 calc R U . . . C3 C 0.24224(16) 0.36594(8) 0.11618(18) 0.0330(4) Uani 1 1 d . . . . . H3A H 0.2998 0.3389 0.0643 0.040 Uiso 1 1 calc R U . . . H3B H 0.1837 0.3833 0.0441 0.040 Uiso 1 1 calc R U . . . C4 C 0.32016(19) 0.41369(9) 0.1847(2) 0.0449(5) Uani 1 1 d . . . . . H4A H 0.3777 0.3963 0.2578 0.054 Uiso 1 1 calc R U . . . H4B H 0.2623 0.4408 0.2356 0.054 Uiso 1 1 calc R U . . . C5 C 0.39914(19) 0.44779(9) 0.0761(2) 0.0474(5) Uani 1 1 d . . . . . H5A H 0.3430 0.4649 0.0028 0.071 Uiso 1 1 calc R U . . . H5B H 0.4602 0.4216 0.0291 0.071 Uiso 1 1 calc R U . . . H5C H 0.4452 0.4789 0.1264 0.071 Uiso 1 1 calc R U . . . 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 0.0469(3) 0.0530(3) 0.0287(3) 0.000 0.000 0.000 N1 0.0283(14) 0.0272(14) 0.0185(14) 0.000 0.000 0.000 C1 0.0323(8) 0.0328(9) 0.0186(7) 0.0005(6) 0.0025(6) 0.0004(7) C2 0.0330(9) 0.0380(10) 0.0234(8) -0.0010(7) 0.0019(6) -0.0051(7) C3 0.0333(8) 0.0386(9) 0.0271(8) 0.0029(7) 0.0009(7) -0.0028(7) C4 0.0498(11) 0.0496(11) 0.0354(10) 0.0001(9) 0.0036(9) -0.0166(9) C5 0.0472(10) 0.0522(12) 0.0428(11) 0.0083(9) 0.0017(9) -0.0151(9) 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' N N 0.0311 0.0180 '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' 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 C1 N1 C1 106.15(12) . 2 C1 N1 C1 111.59(12) . 4 C1 N1 C1 110.73(12) 2 4 C1 N1 C1 110.73(12) . 3 C1 N1 C1 111.59(12) 2 3 C1 N1 C1 106.15(12) 4 3 N1 C1 H1A 108.4 . . N1 C1 H1B 108.4 . . H1A C1 H1B 107.5 . . C2 C1 N1 115.36(11) . . C2 C1 H1A 108.4 . . C2 C1 H1B 108.4 . . C1 C2 H2A 109.6 . . C1 C2 H2B 109.6 . . C1 C2 C3 110.13(13) . . H2A C2 H2B 108.1 . . C3 C2 H2A 109.6 . . C3 C2 H2B 109.6 . . C2 C3 H3A 109.1 . . C2 C3 H3B 109.1 . . H3A C3 H3B 107.8 . . C4 C3 C2 112.52(14) . . C4 C3 H3A 109.1 . . C4 C3 H3B 109.1 . . C3 C4 H4A 108.9 . . C3 C4 H4B 108.9 . . C3 C4 C5 113.27(16) . . H4A C4 H4B 107.7 . . C5 C4 H4A 108.9 . . C5 C4 H4B 108.9 . . C4 C5 H5A 109.5 . . C4 C5 H5B 109.5 . . C4 C5 H5C 109.5 . . H5A C5 H5B 109.5 . . H5A C5 H5C 109.5 . . H5B C5 H5C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.5215(15) 2 N1 C1 1.5214(15) . N1 C1 1.5215(15) 4 N1 C1 1.5215(15) 3 C1 H1A 0.9900 . C1 H1B 0.9900 . C1 C2 1.514(2) . C2 H2A 0.9900 . C2 H2B 0.9900 . C2 C3 1.523(2) . C3 H3A 0.9900 . C3 H3B 0.9900 . C3 C4 1.508(2) . C4 H4A 0.9900 . C4 H4B 0.9900 . C4 C5 1.519(3) . C5 H5A 0.9800 . C5 H5B 0.9800 . C5 H5C 0.9800 . 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 N1 C1 C2 C3 179.96(12) . . . . C1 N1 C1 C2 54.36(11) 4 . . . C1 N1 C1 C2 175.08(16) 2 . . . C1 N1 C1 C2 -63.65(12) 3 . . . C1 C2 C3 C4 176.27(15) . . . . C2 C3 C4 C5 179.32(17) . . . . _cod_database_fobs_code 3500082