#------------------------------------------------------------------------------
#$Date: 2019-07-08 12:15:06 +0300 (Mon, 08 Jul 2019) $
#$Revision: 216831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/20/1552022.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_1552022
loop_
_publ_author_name
'Beatrice S. L. Collins'
'Jos C. M. Kistemaker'
'Edwin Otten'
'Ben L. Feringa'
_publ_section_title
;
 A chemically powered unidirectional rotary molecular motor based on a
 palladium redox cycle
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              860
_journal_page_last               866
_journal_paper_doi               10.1038/nchem.2543
_journal_volume                  8
_journal_year                    2016
_chemical_formula_sum            'C19 H14 Br F O S'
_chemical_formula_weight         389.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0067(4)
_cell_length_b                   11.0733(4)
_cell_length_c                   13.4281(4)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      3.02
_cell_volume                     1636.62(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28088
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_min         3.018
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0159
_refine_ls_R_factor_gt           0.0152
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0177P)²+0.0440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0389
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                3868
_reflns_number_total             3960
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nchem.2543-s3.cif
_cod_data_source_block           mo_molan327_0m
_cod_database_code               1552022
_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   0.363
_shelx_estimated_absorpt_t_max   0.557
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.41187(2) 0.57624(2) 0.85443(2) 0.01270(5) Uani 1 1 d . . . . .
S2 S 0.34382(4) 0.89500(4) 0.86621(3) 0.01213(9) Uani 1 1 d . . . . .
C4 C 0.30788(17) 0.59482(17) 1.15047(14) 0.0177(4) Uani 1 1 d . . . . .
H4 H 0.3403 0.5695 1.2126 0.021 Uiso 1 1 calc R U . . .
C12 C 0.20869(17) 0.81972(17) 0.82073(13) 0.0119(3) Uani 1 1 d . . . . .
C5 C 0.19568(17) 0.65153(16) 1.14700(15) 0.0168(4) Uani 1 1 d . . . . .
H5 H 0.1500 0.6626 1.2063 0.020 Uiso 1 1 calc R U . . .
C2 C 0.32594(17) 0.61389(16) 0.97334(13) 0.0116(3) Uani 1 1 d . . . . .
C8 C 0.06383(18) 0.66269(16) 0.82883(14) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.21487(17) 0.67513(16) 0.96782(13) 0.0109(3) Uani 1 1 d . . . . .
C7 C 0.16352(16) 0.71969(16) 0.87182(13) 0.0116(3) Uani 1 1 d . . . . .
C3 C 0.37313(16) 0.57494(18) 1.06351(13) 0.0157(3) Uani 1 1 d . . . . .
H3 H 0.4495 0.5350 1.0658 0.019 Uiso 1 1 calc R U . . .
C11 C 0.15870(18) 0.85922(18) 0.73127(14) 0.0161(4) Uani 1 1 d . . . . .
H11 H 0.1907 0.9283 0.6985 0.019 Uiso 1 1 calc R U . . .
C9 C 0.01303(19) 0.69707(18) 0.73936(16) 0.0204(4) Uani 1 1 d . . . . .
H9 H -0.0535 0.6538 0.7118 0.024 Uiso 1 1 calc R U . . .
C6 C 0.15023(18) 0.69219(16) 1.05622(14) 0.0143(4) Uani 1 1 d . . . . .
H6 H 0.0739 0.7322 1.0544 0.017 Uiso 1 1 calc R U . . .
C10 C 0.06151(19) 0.79642(18) 0.69059(15) 0.0195(4) Uani 1 1 d . . . . .
H10 H 0.0279 0.8217 0.6288 0.023 Uiso 1 1 calc R U . . .
F1 F 0.01604(11) 0.56580(11) 0.87661(9) 0.0276(3) Uani 1 1 d . . . . .
O1 O 0.41378(12) 0.93439(12) 0.77658(9) 0.0181(3) Uani 1 1 d . . . . .
C15 C 0.25487(18) 1.24455(17) 0.91645(14) 0.0160(4) Uani 1 1 d . . . . .
H15 H 0.2754 1.3209 0.8889 0.019 Uiso 1 1 calc R U . . .
C16 C 0.17814(17) 1.23906(17) 0.99917(14) 0.0137(4) Uani 1 1 d . . . . .
C13 C 0.27194(16) 1.02862(16) 0.91432(13) 0.0119(3) Uani 1 1 d . . . . .
C18 C 0.19578(17) 1.02077(17) 0.99687(14) 0.0152(4) Uani 1 1 d . . . . .
H18 H 0.1766 0.9443 1.0249 0.018 Uiso 1 1 calc R U . . .
C14 C 0.30192(17) 1.13948(17) 0.87348(14) 0.0146(4) Uani 1 1 d . . . . .
H14 H 0.3538 1.1441 0.8170 0.018 Uiso 1 1 calc R U . . .
C17 C 0.14834(18) 1.12527(17) 1.03773(14) 0.0161(4) Uani 1 1 d . . . . .
H17 H 0.0946 1.1198 1.0929 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1303(2) 1.35113(18) 1.04852(15) 0.0208(4) Uani 1 1 d . . . . .
H19A H 0.1504 1.4217 1.0077 0.031 Uiso 1 1 calc R U . . .
H19B H 0.1673 1.3597 1.1145 0.031 Uiso 1 1 calc R U . . .
H19C H 0.0419 1.3450 1.0555 0.031 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O1 S2 C13 106.02(8) . .
O1 S2 C12 106.62(8) . .
C13 S2 C12 97.96(8) . .
C5 C4 C3 120.29(18) . .
C11 C12 C7 122.23(17) . .
C11 C12 S2 118.11(15) . .
C7 C12 S2 119.50(14) . .
C4 C5 C6 119.73(18) . .
C3 C2 C1 121.61(16) . .
C3 C2 Br1 118.60(14) . .
C1 C2 Br1 119.73(13) . .
F1 C8 C9 118.25(17) . .
F1 C8 C7 117.93(16) . .
C9 C8 C7 123.79(18) . .
C6 C1 C2 117.73(17) . .
C6 C1 C7 119.79(17) . .
C2 C1 C7 122.48(16) . .
C8 C7 C12 115.94(16) . .
C8 C7 C1 120.49(16) . .
C12 C7 C1 123.57(16) . .
C2 C3 C4 119.44(17) . .
C10 C11 C12 119.14(18) . .
C8 C9 C10 118.32(18) . .
C5 C6 C1 121.15(18) . .
C9 C10 C11 120.54(18) . .
C16 C15 C14 121.07(17) . .
C15 C16 C17 118.32(17) . .
C15 C16 C19 121.80(17) . .
C17 C16 C19 119.86(18) . .
C14 C13 C18 120.94(17) . .
C14 C13 S2 118.85(13) . .
C18 C13 S2 119.97(14) . .
C17 C18 C13 119.40(17) . .
C13 C14 C15 119.09(16) . .
C18 C17 C16 121.16(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.9021(17) .
S2 O1 1.4939(13) .
S2 C13 1.7980(19) .
S2 C12 1.8111(19) .
C4 C5 1.386(3) .
C4 C3 1.388(3) .
C12 C11 1.392(3) .
C12 C7 1.395(2) .
C5 C6 1.392(3) .
C2 C3 1.386(2) .
C2 C1 1.400(3) .
C8 F1 1.356(2) .
C8 C9 1.379(3) .
C8 C7 1.391(3) .
C1 C6 1.397(3) .
C1 C7 1.491(2) .
C11 C10 1.388(3) .
C9 C10 1.387(3) .
C15 C16 1.397(3) .
C15 C14 1.398(3) .
C16 C17 1.401(3) .
C16 C19 1.502(3) .
C13 C14 1.384(2) .
C13 C18 1.393(3) .
C18 C17 1.383(3) .
