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#$Date: 2020-05-08 15:44:15 +0300 (Fri, 08 May 2020) $
#$Revision: 251916 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134929.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_4134929
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 Dr. Carina Santos Hurtado'
_chemical_formula_moiety         'C12 H7 Cl2 I N2'
_chemical_formula_sum            'C12 H7 Cl2 I N2'
_chemical_formula_weight         377.00
_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                95.9810(10)
_cell_angle_beta                 91.2570(10)
_cell_angle_gamma                103.049(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0496(4)
_cell_length_b                   7.3004(4)
_cell_length_c                   12.5978(6)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5379
_cell_measurement_theta_min      2.8823
_cell_volume                     627.47(6)
_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 0.989
_diffrn_measured_fraction_theta_max 0.991
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19287
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.882
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.954
_exptl_absorpt_correction_T_max  0.60
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.189
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0274(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+0.6239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2817
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01753_si_001.cif
_cod_data_source_block           04_mo_jk_carina_kaleta
_cod_database_code               4134929
_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   0.431
_shelx_estimated_absorpt_t_max   0.605
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
I1 I 0.76088(2) 0.05531(2) 0.91448(2) 0.02510(6) Uani 1 1 d . . . . .
Cl1 Cl 0.63869(6) 0.36521(6) 0.24449(4) 0.02155(10) Uani 1 1 d . . . . .
Cl2 Cl 0.67203(7) 0.65538(6) 0.07602(3) 0.02339(10) Uani 1 1 d . . . . .
N1 N 0.7400(2) 0.5332(2) 0.46657(12) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.7903(2) 0.6047(2) 0.56058(12) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.7492(2) 0.6716(2) 0.39330(13) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.7072(2) 0.6045(2) 0.28513(14) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.7189(2) 0.7339(2) 0.21004(13) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.7688(2) 0.9272(2) 0.24126(14) 0.0174(3) Uani 1 1 d . . . . .
H4 H 0.776576 1.014061 0.189495 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8074(3) 0.9929(2) 0.34904(14) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.840704 1.125067 0.371010 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7975(2) 0.8663(2) 0.42433(14) 0.0173(3) Uani 1 1 d . . . . .
H6 H 0.823725 0.912303 0.497764 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7829(2) 0.4707(2) 0.63568(14) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.8382(3) 0.5478(3) 0.74052(15) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.878397 0.681175 0.757287 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8347(3) 0.4302(3) 0.82074(14) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.872473 0.482205 0.892413 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7754(2) 0.2361(3) 0.79476(14) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.7206(3) 0.1567(3) 0.68979(15) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.681418 0.023249 0.673174 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7241(3) 0.2746(3) 0.61019(14) 0.0187(3) Uani 1 1 d . . . . .
H12 H 0.686530 0.222452 0.538531 0.022 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
N2 N1 C1 113.02(14) . . ?
N1 N2 C7 114.46(15) . . ?
C6 C1 C2 119.46(15) . . ?
C6 C1 N1 123.46(16) . . ?
C2 C1 N1 117.08(15) . . ?
C3 C2 C1 119.32(15) . . ?
C3 C2 Cl1 119.95(13) . . ?
C1 C2 Cl1 120.73(13) . . ?
C4 C3 C2 120.94(16) . . ?
C4 C3 Cl2 118.73(13) . . ?
C2 C3 Cl2 120.33(13) . . ?
C3 C4 C5 119.45(16) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.25(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.56(16) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C12 120.34(16) . . ?
C8 C7 N2 115.19(15) . . ?
C12 C7 N2 124.47(16) . . ?
C9 C8 C7 120.14(17) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.09(17) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.39(16) . . ?
C9 C10 I1 120.04(13) . . ?
C11 C10 I1 118.55(13) . . ?
C12 C11 C10 119.26(17) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C7 119.78(17) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
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
I1 C10 2.0949(17) . ?
Cl1 C2 1.7233(17) . ?
Cl2 C3 1.7253(17) . ?
N1 N2 1.253(2) . ?
N1 C1 1.429(2) . ?
N2 C7 1.424(2) . ?
C1 C6 1.396(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(3) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
