#------------------------------------------------------------------------------ #$Date: 2019-03-21 01:30:50 +0200 (Thu, 21 Mar 2019) $ #$Revision: 214234 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/07/1550771.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_1550771 loop_ _publ_author_name 'Colin-Molina, Abraham' 'Jellen, Marcus J.' 'Garc\'ia-Quezada, Eduardo' 'Cifuentes-Quintal, Miguel Eduardo' 'Murillo, Fernando' 'Barroso, Jorge' 'P\'erez-Estrada, Salvador' 'Toscano, Rub\'en A.' 'Merino, Gabriel' 'Rodr\'iguez-Molina, Braulio' _publ_section_title ; Origin of the isotropic motion in crystalline molecular rotors with carbazole stators ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC04398A _journal_year 2019 _chemical_formula_sum 'C30 H18 Br2 N2' _chemical_formula_weight 566.28 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2019-02-11 deposited with the CCDC. 2019-03-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.262(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.2718(16) _cell_length_b 17.063(3) _cell_length_c 8.0988(14) _cell_measurement_reflns_used 9906 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 30.00 _cell_measurement_theta_min 2.39 _cell_volume 1273.6(4) _computing_cell_refinement 'APEX2 v2012.10.0(Bruker, 2012)' _computing_data_collection 'APEX2 v2012.10.0(Bruker, 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker, 2012)' _computing_molecular_graphics 'XP V 5.1 (Bruker, 1998)' _computing_publication_material 'CIFTAB V 2013/2 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-2012 (Bruker, 2013)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 52.0833 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker D8 Venture \k geometry diffractometer 208039-1' _diffrn_measurement_method '\f and \w-scans' _diffrn_radiation_monochromator 'Helios multilayer mirror' _diffrn_radiation_source 'micro-focus X-ray source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1438 _diffrn_reflns_av_unetI/netI 0.0872 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 39214 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.128 _diffrn_reflns_theta_min 2.210 _exptl_absorpt_coefficient_mu 3.203 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.5556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Sheldrick, 2012)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.477 _exptl_crystal_description platy-prism _exptl_crystal_F_000 564 _exptl_crystal_size_max 0.189 _exptl_crystal_size_mid 0.142 _exptl_crystal_size_min 0.026 _refine_diff_density_max 0.551 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 3424 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.1714 _refine_ls_R_factor_gt 0.0633 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+2.5258P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1034 _refine_ls_wR_factor_ref 0.1338 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1652 _reflns_number_total 3424 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8sc04398a4.cif _cod_data_source_block 253RMB17_a _cod_database_code 1550771 _shelx_shelxl_version_number 2016/6 _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_min 0.583 _shelx_estimated_absorpt_t_max 0.921 _shelx_res_file ; TITL 253RMB17_a.res in P2(1)/c 253RMB17_a.res created by SHELXL-2016/6 at 13:45:19 on 18-Aug-2017 REM Old TITL 253RMB17 REM SHELXT solution in P2(1)/c REM R1 0.171, Rweak 0.045, Alpha 0.039, Orientation as input REM Formula found by SHELXT: C15 N Br CELL 0.71073 9.2718 17.0628 8.0988 90.000 96.262 90.000 ZERR 2.000 0.0016 0.0030 0.0014 0.000 0.005 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N BR UNIT 60 36 4 4 ACTA TEMP 25 SIZE 0.026 0.142 0.189 L.S. 20 BOND $H LIST 6 FMAP 2 PLAN 20 HTAB WGHT 0.036700 2.525800 FVAR 0.45937 BR1 4 1.163667 0.616171 0.970226 11.00000 0.04600 0.07473 = 0.07352 0.00584 -0.00275 -0.00179 N1 3 0.602647 0.588994 0.745458 11.00000 0.04087 0.03926 = 0.03056 0.00573 0.00951 -0.00456 C1 1 0.517060 0.620575 0.608123 11.00000 0.04255 0.03340 = 0.02273 0.00220 0.00790 -0.00081 C2 1 0.370549 0.611947 0.560427 11.00000 0.04505 0.05573 = 0.03432 0.00304 0.00847 -0.00152 AFIX 43 H2 2 0.313125 0.580188 0.619881 11.00000 -1.20000 AFIX 0 C3 1 0.311187 0.653114 0.418101 11.00000 0.04778 0.06117 = 0.04267 -0.00556 0.00509 0.00436 AFIX 43 H3 2 0.212960 0.648346 0.381543 11.00000 -1.20000 AFIX 0 C5 1 0.544162 0.707969 0.380948 11.00000 0.06508 0.03978 = 0.03116 0.00417 0.01109 0.00130 AFIX 43 H5 2 0.601053 0.739839 0.321072 11.00000 -1.20000 AFIX 0 C4 1 0.397857 0.700222 0.333259 11.00000 0.07516 0.05014 = 0.03127 0.00611 -0.00115 0.01623 AFIX 43 H4 2 0.356452 0.727705 0.240833 11.00000 -1.20000 AFIX 0 C6 1 0.605219 0.667695 0.519076 11.00000 0.04950 0.03228 = 0.02719 0.00017 0.00927 0.00059 C7 1 0.749875 0.664460 0.605730 11.00000 0.04630 0.03298 = 0.03143 0.00340 0.01598 -0.00361 C8 1 0.881302 0.697972 0.578924 11.00000 0.06143 0.04685 = 0.04484 0.00852 0.01423 -0.00709 AFIX 43 H8 2 0.887182 0.730227 0.487335 11.00000 -1.20000 AFIX 0 C9 1 1.003056 0.683707 0.687262 11.00000 0.04094 0.04798 = 0.05984 -0.00068 0.01766 -0.01361 AFIX 43 H9 2 1.091023 0.706948 0.670543 11.00000 -1.20000 AFIX 0 C10 1 0.993761 0.634591 0.821152 11.00000 0.04146 0.04416 = 0.04565 -0.00416 0.01034 -0.00227 C11 1 0.865246 0.599613 0.853806 11.00000 0.04274 0.03878 = 0.03595 0.00648 0.01074 -0.00084 AFIX 43 H11 2 0.860687 0.566939 0.945002 11.00000 -1.20000 AFIX 0 C12 1 0.743604 0.615714 0.743754 11.00000 0.03952 0.03219 = 0.03697 0.00192 0.01325 -0.00222 C13 1 0.550531 0.543533 0.875008 11.00000 0.03803 0.03116 = 0.02652 0.00560 0.01328 -0.00144 C14 1 0.568769 0.570338 1.036411 11.00000 0.04775 0.03231 = 0.03174 0.00115 0.00834 -0.00730 AFIX 43 H14 2 0.615292 0.617852 1.061264 11.00000 -1.20000 AFIX 0 C15 1 0.481899 0.473249 0.839351 11.00000 0.04608 0.04081 = 0.02611 -0.00289 0.00651 -0.00471 AFIX 43 H15 2 0.469636 0.455039 0.730490 11.00000 -1.20000 AFIX 0 HKLF 4 REM 253RMB17_a.res in P2(1)/c REM R1 = 0.0633 for 1652 Fo > 4sig(Fo) and 0.1714 for all 3424 data REM 154 parameters refined using 0 restraints END WGHT 0.0367 2.5257 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.551, deepest hole -0.414, 1-sigma level 0.079 Q1 1 0.1576 0.6199 0.3363 11.00000 0.05 0.55 Q2 1 0.6951 0.6708 0.5208 11.00000 0.05 0.34 Q3 1 0.8792 0.7266 0.5577 11.00000 0.05 0.32 Q4 1 0.9258 0.6220 0.8594 11.00000 0.05 0.31 Q5 1 1.1303 0.5792 0.8907 11.00000 0.05 0.31 Q6 1 0.2753 0.6199 0.4454 11.00000 0.05 0.30 Q7 1 0.2805 0.6794 0.3231 11.00000 0.05 0.29 Q8 1 0.5450 0.5984 0.6943 11.00000 0.05 0.28 Q9 1 0.6751 0.6173 0.7671 11.00000 0.05 0.28 Q10 1 1.0965 0.6462 0.8873 11.00000 0.05 0.28 Q11 1 0.7634 0.6255 0.6534 11.00000 0.05 0.28 Q12 1 0.3585 0.6444 0.4176 11.00000 0.05 0.26 Q13 1 1.2420 0.6667 0.8627 11.00000 0.05 0.26 Q14 1 0.6399 0.5915 1.0991 11.00000 0.05 0.25 Q15 1 0.3178 0.5893 0.5831 11.00000 0.05 0.25 Q16 1 0.2977 0.4979 0.6215 11.00000 0.05 0.25 Q17 1 0.7378 0.6057 1.1856 11.00000 0.05 0.25 Q18 1 0.1218 0.4981 0.5349 11.00000 0.05 0.25 Q19 1 0.8147 0.6723 0.5574 11.00000 0.05 0.25 Q20 1 0.5378 0.4985 0.8756 11.00000 0.05 0.24 ; _shelx_res_checksum 67103 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Br1 Br 1.16367(6) 0.61617(3) 0.97023(7) 0.0654(2) Uani 1 1 d . . N1 N 0.6026(4) 0.5890(2) 0.7455(4) 0.0365(9) Uani 1 1 d . . C1 C 0.5171(4) 0.6206(2) 0.6081(5) 0.0326(9) Uani 1 1 d . . C2 C 0.3705(5) 0.6119(3) 0.5604(5) 0.0447(11) Uani 1 1 d . . H2 H 0.313125 0.580188 0.619881 0.054 Uiso 1 1 calc R U C3 C 0.3112(5) 0.6531(3) 0.4181(6) 0.0505(12) Uani 1 1 d . . H3 H 0.212960 0.648346 0.381543 0.061 Uiso 1 1 calc R U C5 C 0.5442(6) 0.7080(3) 0.3809(5) 0.0449(12) Uani 1 1 d . . H5 H 0.601053 0.739839 0.321072 0.054 Uiso 1 1 calc R U C4 C 0.3979(6) 0.7002(3) 0.3333(6) 0.0527(13) Uani 1 1 d . . H4 H 0.356452 0.727705 0.240833 0.063 Uiso 1 1 calc R U C6 C 0.6052(5) 0.6677(2) 0.5191(5) 0.0359(10) Uani 1 1 d . . C7 C 0.7499(5) 0.6645(2) 0.6057(5) 0.0360(10) Uani 1 1 d . . C8 C 0.8813(5) 0.6980(3) 0.5789(6) 0.0504(13) Uani 1 1 d . . H8 H 0.887182 0.730227 0.487335 0.061 Uiso 1 1 calc R U C9 C 1.0031(5) 0.6837(3) 0.6873(6) 0.0487(12) Uani 1 1 d . . H9 H 1.091023 0.706948 0.670543 0.058 Uiso 1 1 calc R U C10 C 0.9938(5) 0.6346(3) 0.8212(6) 0.0433(11) Uani 1 1 d . . C11 C 0.8652(5) 0.5996(2) 0.8538(5) 0.0387(11) Uani 1 1 d . . H11 H 0.860687 0.566939 0.945002 0.046 Uiso 1 1 calc R U C12 C 0.7436(4) 0.6157(2) 0.7438(5) 0.0356(9) Uani 1 1 d . . C13 C 0.5505(4) 0.5435(2) 0.8750(5) 0.0312(9) Uani 1 1 d . . C14 C 0.5688(5) 0.5703(2) 1.0364(5) 0.0370(10) Uani 1 1 d . . H14 H 0.615292 0.617852 1.061264 0.044 Uiso 1 1 calc R U C15 C 0.4819(5) 0.4732(2) 0.8394(5) 0.0375(10) Uani 1 1 d . . H15 H 0.469636 0.455039 0.730490 0.045 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 0.0460(3) 0.0747(4) 0.0735(4) 0.0058(3) -0.0028(2) -0.0018(3) N1 0.041(2) 0.039(2) 0.0306(19) 0.0057(16) 0.0095(16) -0.0046(16) C1 0.043(2) 0.033(2) 0.023(2) 0.0022(19) 0.0079(17) -0.001(2) C2 0.045(3) 0.056(3) 0.034(2) 0.003(2) 0.008(2) -0.002(2) C3 0.048(3) 0.061(3) 0.043(3) -0.006(3) 0.005(2) 0.004(3) C5 0.065(3) 0.040(3) 0.031(2) 0.004(2) 0.011(2) 0.001(2) C4 0.075(4) 0.050(3) 0.031(3) 0.006(2) -0.001(2) 0.016(3) C6 0.049(3) 0.032(2) 0.027(2) 0.0002(19) 0.009(2) 0.001(2) C7 0.046(3) 0.033(2) 0.031(2) 0.003(2) 0.016(2) -0.004(2) C8 0.061(3) 0.047(3) 0.045(3) 0.009(2) 0.014(3) -0.007(2) C9 0.041(3) 0.048(3) 0.060(3) -0.001(3) 0.018(2) -0.014(2) C10 0.041(3) 0.044(3) 0.046(3) -0.004(2) 0.010(2) -0.002(2) C11 0.043(3) 0.039(3) 0.036(2) 0.006(2) 0.011(2) -0.001(2) C12 0.040(2) 0.032(2) 0.037(2) 0.002(2) 0.0132(19) -0.002(2) C13 0.038(2) 0.031(2) 0.027(2) 0.0056(18) 0.0133(18) -0.0014(19) C14 0.048(3) 0.032(2) 0.032(2) 0.001(2) 0.008(2) -0.007(2) C15 0.046(3) 0.041(2) 0.026(2) -0.003(2) 0.0065(19) -0.005(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 C12 N1 C1 108.6(3) . . C12 N1 C13 125.5(3) . . C1 N1 C13 125.7(3) . . C2 C1 C6 122.0(4) . . C2 C1 N1 129.5(4) . . C6 C1 N1 108.5(4) . . C1 C2 C3 117.4(4) . . C1 C2 H2 121.3 . . C3 C2 H2 121.3 . . C4 C3 C2 120.2(5) . . C4 C3 H3 119.9 . . C2 C3 H3 119.9 . . C4 C5 C6 119.0(4) . . C4 C5 H5 120.5 . . C6 C5 H5 120.5 . . C3 C4 C5 121.9(4) . . C3 C4 H4 119.0 . . C5 C4 H4 119.0 . . C5 C6 C1 119.5(4) . . C5 C6 C7 133.6(4) . . C1 C6 C7 106.9(3) . . C8 C7 C12 119.0(4) . . C8 C7 C6 134.0(4) . . C12 C7 C6 107.1(4) . . C9 C8 C7 120.2(4) . . C9 C8 H8 119.9 . . C7 C8 H8 119.9 . . C8 C9 C10 119.5(4) . . C8 C9 H9 120.3 . . C10 C9 H9 120.3 . . C9 C10 C11 122.7(4) . . C9 C10 Br1 118.7(3) . . C11 C10 Br1 118.5(3) . . C10 C11 C12 116.7(4) . . C10 C11 H11 121.7 . . C12 C11 H11 121.7 . . N1 C12 C11 129.1(4) . . N1 C12 C7 109.0(4) . . C11 C12 C7 122.0(4) . . C15 C13 C14 119.7(4) . . C15 C13 N1 120.3(4) . . C14 C13 N1 120.0(4) . . C15 C14 C13 119.9(4) 3_667 . C15 C14 H14 120.0 3_667 . C13 C14 H14 120.0 . . C13 C15 C14 120.4(4) . 3_667 C13 C15 H15 119.8 . . C14 C15 H15 119.8 3_667 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C10 1.903(5) . N1 C12 1.386(5) . N1 C1 1.402(5) . N1 C13 1.431(5) . C1 C2 1.379(6) . C1 C6 1.401(6) . C2 C3 1.409(6) . C2 H2 0.9300 . C3 C4 1.373(7) . C3 H3 0.9300 . C5 C4 1.376(7) . C5 C6 1.381(6) . C5 H5 0.9300 . C4 H4 0.9300 . C6 C7 1.445(6) . C7 C8 1.384(6) . C7 C12 1.400(6) . C8 C9 1.374(7) . C8 H8 0.9300 . C9 C10 1.381(6) . C9 H9 0.9300 . C10 C11 1.384(6) . C11 C12 1.387(6) . C11 H11 0.9300 . C13 C15 1.373(6) . C13 C14 1.378(5) . C14 C15 1.375(6) 3_667 C14 H14 0.9300 . C15 H15 0.9300 .