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#$Date: 2019-03-21 01:30:50 +0200 (Thu, 21 Mar 2019) $
#$Revision: 214234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/07/1550768.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_1550768
loop_
_publ_author_name
'Colin-Molina, Abraham'
'Jellen, Marcus J.'
'García-Quezada, Eduardo'
'Cifuentes-Quintal, Miguel Eduardo'
'Murillo, Fernando'
'Barroso, Jorge'
'Pérez-Estrada, Salvador'
'Toscano, Rubén A.'
'Merino, Gabriel'
'Rodríguez-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_moiety         'C30 H18 Br2 N2'
_chemical_formula_sum            'C30 H18 Br2 N2'
_chemical_formula_weight         566.28
_chemical_melting_point          584.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-24 deposited with the CCDC.    2019-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5701(2)
_cell_length_b                   30.1408(16)
_cell_length_c                   16.5121(8)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.90
_cell_measurement_theta_min      2.47
_cell_volume                     2272.47(19)
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_collection       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22659
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.026
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    3.590
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       lamina
_exptl_crystal_F_000             1128
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: N,N-dimethylformamide'
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0430
_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/[σ²(Fo²)+(0.0370P)²+2.8221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2112
_reflns_number_total             3338
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc04398a4.cif
_cod_data_source_block           042RMB17
_cod_database_code               1550768
_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   0.263
_shelx_estimated_absorpt_t_max   0.870
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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
Br1 Br -0.67816(7) 0.43648(2) 0.49780(2) 0.05467(12) Uani 1 1 d . . .
C1 C 0.000000 0.51860(10) 0.250000 0.0364(8) Uani 1 2 d S T P
C2 C 0.0758(6) 0.54160(8) 0.32024(15) 0.0402(6) Uani 1 1 d . . .
H2 H 0.126975 0.526185 0.367525 0.048 Uiso 1 1 calc R U .
C3 C 0.0757(6) 0.58753(8) 0.32035(16) 0.0416(6) Uani 1 1 d . . .
H3 H 0.126451 0.602910 0.367703 0.050 Uiso 1 1 calc R U .
C4 C 0.000000 0.61059(11) 0.250000 0.0395(8) Uani 1 2 d S T P
N5 N 0.000000 0.47146(9) 0.250000 0.0378(7) Uani 1 2 d S T P
C6 C -0.1477(5) 0.44426(7) 0.30310(15) 0.0354(5) Uani 1 1 d . . .
C7 C -0.3264(5) 0.45627(9) 0.36516(15) 0.0394(6) Uani 1 1 d . . .
H7 H -0.365285 0.485816 0.376837 0.047 Uiso 1 1 calc R U .
C8 C -0.4436(6) 0.42202(9) 0.40866(15) 0.0412(6) Uani 1 1 d . . .
C9 C -0.3916(6) 0.37759(9) 0.39263(17) 0.0482(7) Uani 1 1 d . . .
H9 H -0.473511 0.355547 0.423915 0.058 Uiso 1 1 calc R U .
C10 C -0.2169(6) 0.36662(9) 0.32974(17) 0.0466(7) Uani 1 1 d . . .
H10 H -0.181791 0.336969 0.317958 0.056 Uiso 1 1 calc R U .
C11 C -0.0934(5) 0.39967(8) 0.28399(15) 0.0373(5) Uani 1 1 d . . .
N12 N 0.000000 0.65773(9) 0.250000 0.0437(7) Uani 1 2 d S T P
C13 C 0.1450(6) 0.68479(8) 0.19602(15) 0.0408(6) Uani 1 1 d . . .
C14 C 0.3231(6) 0.67326(9) 0.13354(17) 0.0496(7) Uani 1 1 d . . .
H14 H 0.359819 0.643695 0.121448 0.060 Uiso 1 1 calc R U .
C15 C 0.4437(7) 0.70702(10) 0.09003(18) 0.0579(8) Uani 1 1 d . . .
H15 H 0.564774 0.700051 0.047961 0.069 Uiso 1 1 calc R U .
C16 C 0.3892(7) 0.75135(10) 0.10735(19) 0.0567(8) Uani 1 1 d . . .
H16 H 0.470847 0.773454 0.076146 0.068 Uiso 1 1 calc R U .
C17 C 0.2166(6) 0.76277(9) 0.16984(18) 0.0497(7) Uani 1 1 d . . .
H17 H 0.182747 0.792472 0.181521 0.060 Uiso 1 1 calc R U .
C18 C 0.0919(6) 0.72946(8) 0.21586(16) 0.0408(6) Uani 1 1 d . . .
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
C2 C1 C2 119.8(3) 2 .
C2 C1 N5 120.10(15) 2 .
C2 C1 N5 120.10(15) . .
C1 C2 C3 120.2(2) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C2 C3 C4 120.1(2) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C3 C4 C3 119.8(3) . 2
C3 C4 N12 120.12(15) . .
C3 C4 N12 120.13(15) 2 .
C6 N5 C6 108.0(3) . 2
C6 N5 C1 125.99(13) . .
C6 N5 C1 125.99(13) 2 .
C7 C6 N5 128.9(2) . .
C7 C6 C11 122.1(2) . .
N5 C6 C11 109.0(2) . .
C8 C7 C6 116.4(2) . .
C8 C7 H7 121.8 . .
C6 C7 H7 121.8 . .
C7 C8 C9 123.4(2) . .
C7 C8 Br1 118.3(2) . .
C9 C8 Br1 118.3(2) . .
C10 C9 C8 119.0(2) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
C9 C10 C11 120.1(2) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C10 C11 C6 119.1(2) . .
C10 C11 C11 134.00(15) . 2
C6 C11 C11 106.94(14) . 2
C13 N12 C13 108.5(3) . 2
C13 N12 C4 125.76(14) . .
C13 N12 C4 125.76(14) 2 .
C14 C13 N12 129.7(2) . .
C14 C13 C18 121.7(2) . .
N12 C13 C18 108.6(2) . .
C15 C14 C13 117.7(3) . .
C15 C14 H14 121.1 . .
C13 C14 H14 121.1 . .
C14 C15 C16 121.6(3) . .
C14 C15 H15 119.2 . .
C16 C15 H15 119.2 . .
C17 C16 C15 120.7(3) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C16 C17 C18 119.4(3) . .
C16 C17 H17 120.3 . .
C18 C17 H17 120.3 . .
C17 C18 C13 118.9(2) . .
C17 C18 C18 133.96(16) . 2
C13 C18 C18 107.16(15) . 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.907(3) .
C1 C2 1.383(3) 2
C1 C2 1.383(3) .
C1 N5 1.421(4) .
C2 C3 1.384(4) .
C2 H2 0.9300 .
C3 C4 1.385(3) .
C3 H3 0.9300 .
C4 N12 1.421(4) .
N5 C6 1.395(3) .
N5 C6 1.395(3) 2
C6 C7 1.385(3) .
C6 C11 1.405(3) .
C7 C8 1.379(4) .
C7 H7 0.9300 .
C8 C9 1.387(4) .
C9 C10 1.376(4) .
C9 H9 0.9300 .
C10 C11 1.385(3) .
C10 H10 0.9300 .
C11 C11 1.438(5) 2
N12 C13 1.396(3) .
N12 C13 1.396(3) 2
C13 C14 1.385(4) .
C13 C18 1.409(3) .
C14 C15 1.374(4) .
C14 H14 0.9300 .
C15 C16 1.391(4) .
C15 H15 0.9300 .
C16 C17 1.369(4) .
C16 H16 0.9300 .
C17 C18 1.395(4) .
C17 H17 0.9300 .
C18 C18 1.434(5) 2
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 Br1 0.93 3.13 3.946(3) 147.9 5_466
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_4
C2 C1 C2 C3 0.05(18) 2 .
N5 C1 C2 C3 -179.95(17) . .
C1 C2 C3 C4 -0.1(3) . .
C2 C3 C4 C3 0.05(17) . 2
C2 C3 C4 N12 -179.95(17) . .
C2 C1 N5 C6 -126.50(17) 2 .
C2 C1 N5 C6 53.50(17) . .
C2 C1 N5 C6 53.50(17) 2 2
C2 C1 N5 C6 -126.50(17) . 2
C6 N5 C6 C7 -178.8(3) 2 .
C1 N5 C6 C7 1.2(3) . .
C6 N5 C6 C11 0.18(13) 2 .
C1 N5 C6 C11 -179.82(13) . .
N5 C6 C7 C8 -179.7(2) . .
C11 C6 C7 C8 1.4(4) . .
C6 C7 C8 C9 -0.4(4) . .
C6 C7 C8 Br1 177.40(19) . .
C7 C8 C9 C10 -0.7(4) . .
Br1 C8 C9 C10 -178.4(2) . .
C8 C9 C10 C11 0.7(4) . .
C9 C10 C11 C6 0.4(4) . .
C9 C10 C11 C11 -179.8(4) . 2
C7 C6 C11 C10 -1.5(4) . .
N5 C6 C11 C10 179.4(2) . .
C7 C6 C11 C11 178.6(3) . 2
N5 C6 C11 C11 -0.4(3) . 2
C3 C4 N12 C13 127.48(18) . .
C3 C4 N12 C13 -52.52(18) 2 .
C3 C4 N12 C13 -52.52(18) . 2
C3 C4 N12 C13 127.48(18) 2 2
C13 N12 C13 C14 178.0(3) 2 .
C4 N12 C13 C14 -2.0(3) . .
C13 N12 C13 C18 0.04(13) 2 .
C4 N12 C13 C18 -179.96(13) . .
N12 C13 C14 C15 -178.9(3) . .
C18 C13 C14 C15 -1.2(4) . .
C13 C14 C15 C16 -0.3(5) . .
C14 C15 C16 C17 1.3(5) . .
C15 C16 C17 C18 -0.7(5) . .
C16 C17 C18 C13 -0.7(4) . .
C16 C17 C18 C18 179.2(4) . 2
C14 C13 C18 C17 1.7(4) . .
N12 C13 C18 C17 179.8(2) . .
C14 C13 C18 C18 -178.3(3) . 2
N12 C13 C18 C18 -0.1(3) . 2
