#------------------------------------------------------------------------------ #$Date: 2019-12-17 21:28:31 +0000 (Tue, 17 Dec 2019) $ #$Revision: 245263 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500080.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_3500080 loop_ _publ_author_name 'Thierry Maris' _journal_name_full 'Personal communication to COD' _journal_year 2019 _chemical_formula_moiety 'C12 H28 N, Br' _chemical_formula_sum 'C12 H28 Br N' _chemical_formula_weight 266.26 _space_group_crystal_system tetragonal _space_group_IT_number 82 _space_group_name_Hall 'I -4' _space_group_name_H-M_alt 'I -4' _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 2 _cell_length_a 8.2048(2) _cell_length_b 8.2048(2) _cell_length_c 10.7389(2) _cell_measurement_reflns_used 4819 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 71.898 _cell_measurement_theta_min 6.791 _cell_volume 722.93(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 0.997 _diffrn_measured_fraction_theta_max 0.987 _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 0.0400 _diffrn_reflns_av_unetI/netI 0.0222 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4812 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.481 _diffrn_reflns_theta_min 6.791 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 3.616 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.5810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1467 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.7710. 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 1.223 _exptl_crystal_description block _exptl_crystal_F_000 284 _exptl_crystal_recrystallization_method 'Recrystallised from EtOAc' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _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 0.178 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 335 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.030(12) _refine_ls_extinction_coef 0.0063(10) _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 1.114 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 34 _refine_ls_number_reflns 717 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all 0.0199 _refine_ls_R_factor_gt 0.0199 _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^)+(0.0355P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.0491 _refine_special_details ; ? ; _reflns_Friedel_coverage 0.879 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.985 _reflns_number_gt 716 _reflns_number_total 717 _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 C3NBr in I-4 CELL 1.54178 8.2048 8.2048 10.7389 90 90 90 ZERR 2 0.0002 0.0002 0.0002 0 0 0 LATT -2 SYMM +Y,-X,-Z SYMM -Y,+X,-Z SYMM -X,-Y,+Z SFAC C H N Br UNIT 24 56 2 2 L.S. 30 PLAN 3 TEMP -123.15 CONF BOND $H fmap 2 acta EXTI 0.006281 REM E:/PROJETS/2013/C3NBr/OLEX2/C3NBr.hkl WGHT 0.0355 FVAR 0.37302 Br1 4 1.00000 0.00000 1.00000 10.25000 0.03148 0.03148 0.03245 = 0.00000 0.00000 0.00000 C3 1 0.74343 0.13482 0.63110 11.00000 0.04289 0.02830 0.04512 = -0.00345 -0.01001 -0.00379 AFIX 137 H3A 2 0.67954 0.19273 0.56796 11.00000 -1.50000 H3B 2 0.67502 0.05220 0.67125 11.00000 -1.50000 H3C 2 0.83703 0.08184 0.59141 11.00000 -1.50000 AFIX 0 C2 1 0.80388 0.25615 0.72901 11.00000 0.03530 0.03108 0.03186 = 0.00014 -0.00174 -0.00666 AFIX 23 H2A 2 0.71004 0.31030 0.76958 11.00000 -1.20000 H2B 2 0.86745 0.19843 0.79378 11.00000 -1.20000 AFIX 0 C1 1 0.91024 0.38195 0.66466 11.00000 0.02954 0.02572 0.02196 = -0.00169 -0.00276 -0.00051 AFIX 23 H1A 2 0.84089 0.44609 0.60730 11.00000 -1.20000 H1B 2 0.99189 0.32375 0.61338 11.00000 -1.20000 AFIX 0 N1 3 1.00000 0.50000 0.75000 10.25000 0.02449 0.02449 0.01805 = 0.00000 0.00000 0.00000 HKLF 4 END ; _cod_data_source_file c3nbr.cif _cod_data_source_block c3nbr _cod_original_cell_volume 722.93(4) _cod_database_code 3500080 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H1A,H1B} of C1, {H2A,H2B} of C2 At 1.5 times of: {H3A,H3B,H3C} of C3 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C1(H1A,H1B) 2.b Idealised Me refined as rotating group: C3(H3A,H3B,H3C) ; _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, -z' '-y, x, -z' '-x, -y, z' 'x+1/2, y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -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 1.0000 0.0000 1.0000 0.0318(2) Uani 1 4 d S T P . . C3 C 0.7434(4) 0.1348(3) 0.6311(3) 0.0388(6) Uani 1 1 d . . . . . H3A H 0.6795 0.1927 0.5680 0.058 Uiso 1 1 calc R U . . . H3B H 0.6750 0.0522 0.6712 0.058 Uiso 1 1 calc R U . . . H3C H 0.8370 0.0818 0.5914 0.058 Uiso 1 1 calc R U . . . C2 C 0.8039(3) 0.2561(3) 0.7290(3) 0.0327(5) Uani 1 1 d . . . . . H2A H 0.7100 0.3103 0.7696 0.039 Uiso 1 1 calc R U . . . H2B H 0.8674 0.1984 0.7938 0.039 Uiso 1 1 calc R U . . . C1 C 0.9102(3) 0.3820(3) 0.6647(2) 0.0257(5) Uani 1 1 d . . . . . H1A H 0.8409 0.4461 0.6073 0.031 Uiso 1 1 calc R U . . . H1B H 0.9919 0.3238 0.6134 0.031 Uiso 1 1 calc R U . . . N1 N 1.0000 0.5000 0.7500 0.0223(8) Uani 1 4 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 0.0315(2) 0.0315(2) 0.0325(3) 0.000 0.000 0.000 C3 0.0429(16) 0.0283(14) 0.0451(14) -0.0035(11) -0.0100(12) -0.0038(10) C2 0.0353(14) 0.0311(14) 0.0319(12) 0.0001(10) -0.0017(10) -0.0067(11) C1 0.0295(12) 0.0257(12) 0.0220(10) -0.0017(9) -0.0028(8) -0.0005(9) N1 0.0245(11) 0.0245(11) 0.0181(17) 0.000 0.000 0.000 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 H3A C3 H3B 109.5 . . H3A C3 H3C 109.5 . . H3B C3 H3C 109.5 . . C2 C3 H3A 109.5 . . C2 C3 H3B 109.5 . . C2 C3 H3C 109.5 . . C3 C2 H2A 110.0 . . C3 C2 H2B 110.0 . . H2A C2 H2B 108.4 . . C1 C2 C3 108.4(2) . . C1 C2 H2A 110.0 . . C1 C2 H2B 110.0 . . C2 C1 H1A 108.3 . . C2 C1 H1B 108.3 . . C2 C1 N1 115.87(17) . . H1A C1 H1B 107.4 . . N1 C1 H1A 108.3 . . N1 C1 H1B 108.3 . . C1 N1 C1 111.22(9) . 7_646 C1 N1 C1 106.02(18) . 4_765 C1 N1 C1 111.22(9) 7_646 4_765 C1 N1 C1 111.22(9) . 6_566 C1 N1 C1 106.02(18) 7_646 6_566 C1 N1 C1 111.22(9) 4_765 6_566 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C3 H3A 0.9800 . C3 H3B 0.9800 . C3 H3C 0.9800 . C3 C2 1.530(4) . C2 H2A 0.9900 . C2 H2B 0.9900 . C2 C1 1.518(3) . C1 H1A 0.9900 . C1 H1B 0.9900 . C1 N1 1.523(2) . N1 C1 1.523(2) 7_646 N1 C1 1.523(2) 4_765 N1 C1 1.523(2) 6_566 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 C3 C2 C1 N1 -172.2(2) . . . . C2 C1 N1 C1 61.9(3) . . . 7_646 C2 C1 N1 C1 -177.1(3) . . . 4_765 C2 C1 N1 C1 -56.0(3) . . . 6_566 _cod_database_fobs_code 3500080