#------------------------------------------------------------------------------
#$Date: 2025-08-20 18:06:18 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301834 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/64/4126423.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_4126423
loop_
_publ_author_name
'Dong, Mingxin'
'Babalhavaeji, Amirhossein'
'Collins, Catherine V.'
'Jarrah, Kareem'
'Sadovski, Oleg'
'Dai, Qiuyun'
'Woolley, G. Andrew'
_publ_section_title
;
 Near-Infrared Photoswitching of Azobenzenes under Physiological
 Conditions.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b06471
_journal_year                    2017
_chemical_formula_moiety         'C18 H16 Br2 N2 O6, 2(C H Cl3)'
_chemical_formula_sum            'C20 H18 Br2 Cl6 N2 O6'
_chemical_formula_weight         754.88
_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_date             2016-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.652(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8792(4)
_cell_length_b                   15.5118(5)
_cell_length_c                   8.0195(3)
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.3810
_cell_measurement_theta_min      5.0200
_cell_volume                     1325.45(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -96.00 -58.00   1.00    1.00    --  -41.49 125.00  30.00   38
  2  ω   -110.00 -24.00   1.00    1.00    --  -41.49 -37.00 150.00   86
  3  ω   -110.00 -21.00   1.00    1.00    --  -41.49 -37.00-120.00   89
  4  ω     25.00 100.00   1.00    1.00    --  107.19 -94.00 -30.00   75
  5  ω     90.00 131.00   1.00    1.00    --  107.19 -45.00  60.00   41
  6  ω     79.00 130.00   1.00    1.00    --  107.19 -30.00  30.00   51
  7  ω     80.00 168.00   1.00    1.00    --  107.19  30.00-120.00   88
  8  ω    142.00 178.00   1.00    1.00    --  107.19 125.00  30.00   36
  9  ω     37.00 120.00   1.00    1.00    --  107.19 -61.00 -30.00   83
 10  ω     36.00  73.00   1.00    1.00    --  107.19 -45.00  60.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1328785000
_diffrn_orient_matrix_UB_12      0.0116483000
_diffrn_orient_matrix_UB_13      -0.1087352000
_diffrn_orient_matrix_UB_21      -0.0565366000
_diffrn_orient_matrix_UB_22      -0.0161643000
_diffrn_orient_matrix_UB_23      0.1586641000
_diffrn_orient_matrix_UB_31      0.0064176000
_diffrn_orient_matrix_UB_32      0.0972404000
_diffrn_orient_matrix_UB_33      0.0392116000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4813
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.096
_diffrn_reflns_theta_min         4.149
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.304
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0609P)²+1.0201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2130
_reflns_number_total             2590
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b06471_si_003.cif
_cod_data_source_block           20160428b
_cod_original_cell_volume        1325.44(8)
_cod_database_code               4126423
_chemical_oxdiff_formula         c1h1n1o1Br1
_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.
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.650
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
Br1 Br 0.09014(4) 0.27078(3) 0.00540(6) 0.02430(16) Uani 1 1 d .
Cl2 Cl 0.17632(11) 0.45544(8) 0.66375(15) 0.0349(3) Uani 1 1 d .
Cl1 Cl 0.35958(10) 0.54576(7) 0.91359(13) 0.0263(3) Uani 1 1 d .
Cl3 Cl 0.13848(11) 0.63582(8) 0.73625(16) 0.0370(3) Uani 1 1 d .
O1 O 0.3512(3) 0.21457(19) 0.1588(4) 0.0290(7) Uani 1 1 d .
O2 O 0.5444(2) 0.31359(18) 0.3653(3) 0.0195(6) Uani 1 1 d .
O3 O 0.2734(3) 0.55328(18) 0.3274(4) 0.0205(6) Uani 1 1 d .
N1 N 0.5121(3) 0.4737(2) 0.4449(4) 0.0178(7) Uani 1 1 d .
C9 C 0.1567(4) 0.5937(3) 0.2507(6) 0.0244(9) Uani 1 1 d .
H9A H 0.1506 0.5976 0.1299 0.037 Uiso 1 1 calc GR
H9B H 0.1534 0.6505 0.2971 0.037 Uiso 1 1 calc GR
H9C H 0.0881 0.5600 0.2741 0.037 Uiso 1 1 calc GR
C1 C 0.5687(4) 0.2314(3) 0.2938(5) 0.0221(9) Uani 1 1 d .
H1A H 0.6388 0.2034 0.3679 0.026 Uiso 1 1 calc R
H1B H 0.5907 0.2402 0.1837 0.026 Uiso 1 1 calc R
C10 C 0.2504(4) 0.5551(3) 0.7178(5) 0.0224(9) Uani 1 1 d .
H10 H 0.2953 0.5719 0.6285 0.027 Uiso 1 1 calc R
C8 C 0.4276(4) 0.3470(3) 0.3016(5) 0.0170(8) Uani 1 1 d .
C6 C 0.2871(4) 0.4688(2) 0.2864(5) 0.0160(8) Uani 1 1 d .
C2 C 0.4545(4) 0.1752(3) 0.2739(6) 0.0288(10) Uani 1 1 d .
H2A H 0.4724 0.1193 0.2302 0.035 Uiso 1 1 calc R
H2B H 0.4323 0.1666 0.3839 0.035 Uiso 1 1 calc R
C7 C 0.4049(3) 0.4310(3) 0.3493(5) 0.0156(8) Uani 1 1 d .
C3 C 0.3336(4) 0.2985(3) 0.1998(5) 0.0190(8) Uani 1 1 d .
C5 C 0.1937(4) 0.4217(3) 0.1815(5) 0.0172(8) Uani 1 1 d .
H5 H 0.1161 0.4467 0.1381 0.021 Uiso 1 1 calc R
C4 C 0.2175(4) 0.3368(3) 0.1420(5) 0.0179(8) 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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 O1 C2 112.3(3) .
C8 O2 C1 114.5(3) .
C6 O3 C9 116.4(3) .
N1 N1 C7 114.3(4) 3_666
O3 C9 H9A 109.5 .
O3 C9 H9B 109.5 .
O3 C9 H9C 109.5 .
H9A C9 H9B 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
O2 C1 H1A 109.7 .
O2 C1 H1B 109.7 .
O2 C1 C2 110.0(3) .
H1A C1 H1B 108.2 .
C2 C1 H1A 109.7 .
C2 C1 H1B 109.7 .
Cl2 C10 Cl1 109.8(2) .
Cl2 C10 Cl3 110.7(2) .
Cl2 C10 H10 109.0 .
Cl1 C10 Cl3 109.4(2) .
Cl1 C10 H10 109.0 .
Cl3 C10 H10 109.0 .
O2 C8 C7 116.9(3) .
O2 C8 C3 122.0(4) .
C3 C8 C7 121.1(4) .
O3 C6 C7 116.7(3) .
O3 C6 C5 123.2(4) .
C5 C6 C7 120.0(4) .
O1 C2 C1 110.2(4) .
O1 C2 H2A 109.6 .
O1 C2 H2B 109.6 .
C1 C2 H2A 109.6 .
C1 C2 H2B 109.6 .
H2A C2 H2B 108.1 .
C8 C7 N1 114.3(3) .
C8 C7 C6 119.4(3) .
C6 C7 N1 125.9(4) .
O1 C3 C8 122.3(4) .
O1 C3 C4 119.4(4) .
C4 C3 C8 118.4(4) .
C6 C5 H5 120.4 .
C6 C5 C4 119.2(4) .
C4 C5 H5 120.4 .
C3 C4 Br1 118.3(3) .
C3 C4 C5 121.9(4) .
C5 C4 Br1 119.8(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.886(4) .
Cl2 C10 1.757(4) .
Cl1 C10 1.773(4) .
Cl3 C10 1.774(4) .
O1 C2 1.438(5) .
O1 C3 1.365(5) .
O2 C1 1.443(5) .
O2 C8 1.372(4) .
O3 C9 1.438(5) .
O3 C6 1.367(5) .
N1 N1 1.268(7) 3_666
N1 C7 1.424(5) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C2 1.500(6) .
C10 H10 0.9800 .
C8 C7 1.394(6) .
C8 C3 1.394(5) .
C6 C7 1.407(5) .
C6 C5 1.389(5) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.388(6) .
C5 H5 0.9300 .
C5 C4 1.391(6) .
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
O1 C3 C4 Br1 -1.1(5) .
O1 C3 C4 C5 179.2(4) .
O2 C1 C2 O1 61.6(5) .
O2 C8 C7 N1 6.1(5) .
O2 C8 C7 C6 179.3(3) .
O2 C8 C3 O1 0.8(6) .
O2 C8 C3 C4 179.3(4) .
O3 C6 C7 N1 -3.0(6) .
O3 C6 C7 C8 -175.4(3) .
O3 C6 C5 C4 177.9(4) .
N1 N1 C7 C8 -146.9(4) 3_666
N1 N1 C7 C6 40.4(6) 3_666
C9 O3 C6 C7 174.8(3) .
C9 O3 C6 C5 -2.2(5) .
C1 O2 C8 C7 -171.9(3) .
C1 O2 C8 C3 10.8(5) .
C8 O2 C1 C2 -40.8(5) .
C8 C3 C4 Br1 -179.6(3) .
C8 C3 C4 C5 0.7(6) .
C6 C5 C4 Br1 178.1(3) .
C6 C5 C4 C3 -2.2(6) .
C2 O1 C3 C8 20.0(6) .
C2 O1 C3 C4 -158.5(4) .
C7 C8 C3 O1 -176.4(4) .
C7 C8 C3 C4 2.1(6) .
C7 C6 C5 C4 1.0(6) .
C3 O1 C2 C1 -50.1(5) .
C3 C8 C7 N1 -176.5(4) .
C3 C8 C7 C6 -3.3(6) .
C5 C6 C7 N1 174.1(4) .
C5 C6 C7 C8 1.7(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125564
