#------------------------------------------------------------------------------
#$Date: 2020-05-08 15:46:23 +0300 (Fri, 08 May 2020) $
#$Revision: 251921 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134934.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_4134934
loop_
_publ_author_name
'Santos Hurtado, Carina'
'Bastien, Guillaume'
'Mašát, Milan'
'Stoček, Jakub Radek'
'Dracinsky, Martin'
'Rončević, Igor'
'Císařová, Ivana'
'Rogers, Charles T.'
'Kaleta, Jiří'
_publ_section_title
;
 Regular 2-D Arrays of Surface-Mounted Molecular Switches: Switching
 Monitored by UV-vis and NMR Spectroscopy.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c01753
_journal_year                    2020
_chemical_compound_source        'synthesized by Dr. Guillaume Bastien'
_chemical_formula_moiety         'C22 H30 N2 O2, 2(C H Cl3)'
_chemical_formula_sum            'C24 H32 Cl6 N2 O2'
_chemical_formula_weight         593.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                108.089(2)
_cell_angle_beta                 95.389(2)
_cell_angle_gamma                100.572(2)
_cell_formula_units_Z            1
_cell_length_a                   6.2193(3)
_cell_length_b                   9.1548(6)
_cell_length_c                   13.0735(7)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4795
_cell_measurement_theta_min      2.4018
_cell_volume                     686.43(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service vV6.2.4'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26932
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.402
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.673
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0362
_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)+(0.0493P)²+0.5251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2851
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01753_si_005.cif
_cod_data_source_block           mo_jk_ga192_kaleta
_cod_database_code               4134934
_shelx_shelxl_version_number     2018/3
_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   0.668
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.5581(2) 0.57249(14) 0.50957(10) 0.0166(2) Uani 1 1 d . . . . .
O1 O 0.7075(2) 0.64046(14) 0.59317(9) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.5130(2) 0.64967(16) 0.43014(11) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.6237(2) 0.61948(17) 0.34023(12) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.5741(3) 0.68930(18) 0.26190(12) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.4238(3) 0.78869(18) 0.27690(12) 0.0214(3) Uani 1 1 d . . . . .
C5 C 0.3234(2) 0.82134(17) 0.37093(12) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.3695(2) 0.75171(17) 0.45031(12) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.7937(3) 0.51968(19) 0.32988(13) 0.0231(3) Uani 1 1 d . . . . .
H7A H 0.835813 0.507021 0.400247 0.035 Uiso 1 1 calc R U . . .
H7B H 0.924997 0.571327 0.307848 0.035 Uiso 1 1 calc R U . . .
H7C H 0.730741 0.415865 0.274822 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6829(3) 0.6564(2) 0.16098(14) 0.0320(4) Uani 1 1 d . . . . .
H8A H 0.757070 0.569341 0.155831 0.048 Uiso 1 1 calc R U . . .
H8B H 0.792254 0.750997 0.165425 0.048 Uiso 1 1 calc R U . . .
H8C H 0.570024 0.627683 0.096266 0.048 Uiso 1 1 calc R U . . .
C9 C 0.3733(3) 0.8631(2) 0.19154(15) 0.0339(4) Uani 1 1 d . . . . .
H9A H 0.267512 0.785455 0.129909 0.051 Uiso 1 1 calc R U . . .
H9B H 0.510485 0.898043 0.166073 0.051 Uiso 1 1 calc R U . . .
H9C H 0.309290 0.953860 0.223377 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1651(3) 0.9308(2) 0.38883(15) 0.0297(4) Uani 1 1 d . . . . .
H10A H 0.242990 1.035205 0.439163 0.044 Uiso 1 1 calc R U . . .
H10B H 0.040894 0.888360 0.419946 0.044 Uiso 1 1 calc R U . . .
H10C H 0.108858 0.939865 0.318991 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2718(3) 0.79050(19) 0.55426(13) 0.0247(3) Uani 1 1 d . . . . .
H11A H 0.114988 0.736391 0.538716 0.037 Uiso 1 1 calc R U . . .
H11B H 0.285127 0.904653 0.584302 0.037 Uiso 1 1 calc R U . . .
H11C H 0.351718 0.755649 0.607287 0.037 Uiso 1 1 calc R U . . .
C1S C 0.8281(3) 0.7213(2) 0.84415(13) 0.0273(3) Uani 1 1 d . . . . .
H1S H 0.770310 0.651342 0.767154 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 1.04377(9) 0.87393(7) 0.84320(5) 0.04763(16) Uani 1 1 d . . . . .
Cl2 Cl 0.60873(8) 0.79687(6) 0.90127(4) 0.03795(14) Uani 1 1 d . . . . .
Cl3 Cl 0.92532(9) 0.60758(7) 0.91734(4) 0.04261(15) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O1 N1 N1 120.97(15) . 2_666 ?
O1 N1 C1 121.26(12) . . ?
N1 N1 C1 117.75(14) 2_666 . ?
C6 C1 C2 124.38(14) . . ?
C6 C1 N1 118.32(13) . . ?
C2 C1 N1 117.27(13) . . ?
C1 C2 C3 117.18(14) . . ?
C1 C2 C7 121.10(13) . . ?
C3 C2 C7 121.70(13) . . ?
C2 C3 C4 120.32(13) . . ?
C2 C3 C8 119.53(14) . . ?
C4 C3 C8 120.14(14) . . ?
C5 C4 C3 120.61(14) . . ?
C5 C4 C9 119.97(15) . . ?
C3 C4 C9 119.41(14) . . ?
C4 C5 C6 120.07(14) . . ?
C4 C5 C10 120.97(14) . . ?
C6 C5 C10 118.96(14) . . ?
C1 C6 C5 117.30(13) . . ?
C1 C6 C11 121.61(14) . . ?
C5 C6 C11 121.06(14) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Cl1 C1S Cl3 110.72(10) . . ?
Cl1 C1S Cl2 111.01(10) . . ?
Cl3 C1S Cl2 109.76(9) . . ?
Cl1 C1S H1S 108.4 . . ?
Cl3 C1S H1S 108.4 . . ?
Cl2 C1S H1S 108.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.2728(16) . ?
N1 N1 1.325(2) 2_666 ?
N1 C1 1.4594(18) . ?
C1 C6 1.392(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.404(2) . ?
C2 C7 1.509(2) . ?
C3 C4 1.406(2) . ?
C3 C8 1.512(2) . ?
C4 C5 1.405(2) . ?
C4 C9 1.514(2) . ?
C5 C6 1.410(2) . ?
C5 C10 1.513(2) . ?
C6 C11 1.509(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1S Cl1 1.7542(18) . ?
C1S Cl3 1.7623(17) . ?
C1S Cl2 1.7650(18) . ?
C1S H1S 1.0000 . ?
