The contrasting reactivity of <i>trans</i>- <i>vs. cis</i>-azobenzenes (ArN[double bond, length as m-dash]NAr) with benzynes.
Sneddon, Dorian S.; Hoye, Thomas R.; Chemical science 14 (2023) 6730–6737; doi:10.1039/d3sc02253f

data_1569333
_publ_section_title
;
 The contrasting reactivity of <i>trans</i>- <i>vs. cis</i>-azobenzenes
 (ArN[double bond, length as m-dash]NAr) with benzynes.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6730
_journal_page_last               6737
_journal_paper_doi               10.1039/d3sc02253f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C41 H32 Cl2 N2 O6, C H2 Cl2'
_chemical_formula_sum            'C42 H34 Cl4 N2 O6'
_chemical_formula_weight         804.51
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-03-25 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                88.001(2)
_cell_angle_beta                 88.826(2)
_cell_angle_gamma                64.702(2)
_cell_formula_units_Z            2
_cell_length_a                   11.5264(8)
_cell_length_b                   12.3665(9)
_cell_length_c                   14.7242(8)
_cell_measurement_reflns_used    9331
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.26
_cell_volume                     1896.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon-III CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44925
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_min         1.954
_diffrn_source                   micro
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS, Krause, L. et al. J. Appl. Cryst. 48 (2015) 3-10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.7011
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         10652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0450
_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/[\s^2^(Fo^2^)+(0.0518P)^2^+1.3286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8797
_reflns_number_total             10652
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02253f2.cif
_cod_data_source_block           23015z_a
_cod_database_code               1569333
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.899
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              93525
_shelx_hkl_checksum              95210