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_7130671
_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         'C17 H17 N3 O'
_chemical_formula_sum            'C17 H17 N3 O'
_chemical_formula_weight         279.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 95.252(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4266(7)
_cell_length_b                   13.3424(11)
_cell_length_c                   13.1891(12)
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1230
_cell_measurement_theta_min      4.0460
_cell_volume                     1476.6(2)
_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 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.876
_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    -88.00 -35.00   1.00    6.20    --  -15.92-178.00  60.00   53
  2  \w      0.00  84.00   1.00    6.20    --   16.85  57.00   0.00   84
  3  \w    -55.00  46.00   1.00    6.20    --   16.85 -19.00-150.00  101
  4  \w    -35.00  53.00   1.00    6.20    --  -15.92  37.00  60.00   88
  5  \w      0.00  78.00   1.00    6.20    --   16.85  57.00-180.00   78
;
_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      0.0049103000
_diffrn_orient_matrix_UB_12      0.0194037000
_diffrn_orient_matrix_UB_13      0.0502772000
_diffrn_orient_matrix_UB_21      0.0835878000
_diffrn_orient_matrix_UB_22      -0.0081809000
_diffrn_orient_matrix_UB_23      0.0048239000
_diffrn_orient_matrix_UB_31      0.0121921000
_diffrn_orient_matrix_UB_32      0.0487600000
_diffrn_orient_matrix_UB_33      -0.0191015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12970
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.278
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44840
_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    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0595P)^2^+0.3356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2796
_reflns_number_total             3538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04348c2.cif
_cod_data_source_block           yst9501
_cod_depositor_comments
'Adding full bibliography for 7130670--7130671.cif.'
_cod_database_code               7130671
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.62
_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:
 C6(H6), C13(H13), C4(H4), C5(H5), C10(H10), C3(H3), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_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 1.878
_oxdiff_exptl_absorpt_empirical_full_min 0.534