Fe(acac)<sub>2</sub>/TBHP-promoted synthesis of 11-functionalized dibenzodiazepines <i>via</i> alkoxycarbonylation and carboxamidation of <i>o</i>-isocyanodiaryl amines.
Yuan, Sitian; Liu, Yi; Ni, Mengjia; Hao, Tianxin; Peng, Yiyuan; Ding, Qiuping; Chemical communications (Cambridge, England) 58 (2022) 10985–10988; doi:10.1039/d2cc04348c

data_7130670
_publ_section_title
;
 Fe(acac)<sub>2</sub>/TBHP-promoted synthesis of 11-functionalized
 dibenzodiazepines <i>via</i> alkoxycarbonylation and carboxamidation of
 <i>o</i>-isocyanodiaryl amines.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10985
_journal_page_last               10988
_journal_paper_doi               10.1039/d2cc04348c
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-24 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   43.7224(17)
_cell_length_b                   14.1940(6)
_cell_length_c                   8.7864(3)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9950
_cell_measurement_theta_min      4.2450
_cell_volume                     5452.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0706
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -87.00  12.00   0.75   45.54    --  -15.92 -19.00 -90.00  132
  2  \w    -83.00  10.00   0.75   45.54    --  -15.92 -77.00  30.00  124
  3  \w    -89.00 -35.00   0.75   45.54    --  -15.92 178.00 -60.00   72
  4  \w      0.00  41.25   0.75   45.54    --   16.70  57.00-150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146011000
_diffrn_orient_matrix_UB_12      0.0211182000
_diffrn_orient_matrix_UB_13      -0.0083385000
_diffrn_orient_matrix_UB_21      0.0070611000
_diffrn_orient_matrix_UB_22      -0.0437534000
_diffrn_orient_matrix_UB_23      0.0171063000
_diffrn_orient_matrix_UB_31      -0.0000113000
_diffrn_orient_matrix_UB_32      -0.0118466000
_diffrn_orient_matrix_UB_33      -0.0784213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8647
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.198
_diffrn_reflns_theta_min         3.423
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0361P)^2^+6.7467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2788
_reflns_number_total             2909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04348c2.cif
_cod_data_source_block           yst7102
_cod_depositor_comments
'Adding full bibliography for 7130670--7130671.cif.'
_cod_database_code               7130670
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C12(H12), C11(H11), C4(H4), C6(H6), C13(H13), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
;
_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 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.691