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_1569334
_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         'C31 H30 N2 O3 Si, 0.25(C2 H3 N)'
_chemical_formula_sum            'C31.5 H30.75 N2.25 O3 Si'
_chemical_formula_weight         516.92
_chemical_name_common            23003z
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-25 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                105.035(7)
_cell_angle_beta                 102.319(7)
_cell_angle_gamma                97.010(8)
_cell_formula_units_Z            8
_cell_length_a                   11.824(4)
_cell_length_b                   19.935(6)
_cell_length_c                   24.553(8)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20.92
_cell_measurement_theta_min      2.26
_cell_volume                     5363(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0964
_diffrn_reflns_av_unetI/netI     0.1358
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40278
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        21.994
_diffrn_reflns_theta_max         21.994
_diffrn_reflns_theta_min         1.912
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             2188
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.7447
_exptl_transmission_factor_min   0.6139
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         13075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1737
_refine_ls_R_factor_gt           0.0931
_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/[\s^2^(Fo^2^)+(0.0717P)^2^+26.4674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7246
_reflns_number_total             13075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02253f2.cif
_cod_data_source_block           23003z
_cod_depositor_comments
;

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C126 H123 N9 O12 Si4'
_cod_original_formula_weight         2067.69
_cod_original_formula_moiety         '4(C31 H30 N2 O3 Si), C2 H3 N'
_cod_original_formula_units_Z            2
_cod_database_code               1569334
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              77046
_shelx_hkl_checksum              26487