#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:41:53 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130671.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_7130671
loop_
_publ_author_name
'Yuan, Sitian'
'Liu, Yi'
'Ni, Mengjia'
'Hao, Tianxin'
'Peng, Yiyuan'
'Ding, Qiuping'
_publ_section_title
;
 Fe(acac)₂/TBHP-promoted synthesis of 11-functionalized
 dibenzodiazepines via alkoxycarbonylation and carboxamidation of
 o-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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -35.00   1.00    6.20    --  -15.92-178.00  60.00   53
  2  ω      0.00  84.00   1.00    6.20    --   16.85  57.00   0.00   84
  3  ω    -55.00  46.00   1.00    6.20    --   16.85 -19.00-150.00  101
  4  ω    -35.00  53.00   1.00    6.20    --  -15.92  37.00  60.00   88
  5  ω      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       'ω 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/[σ²(Fo²)+(0.0595P)²+0.3356P] where P=(Fo²+2Fc²)/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 > 2σ(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
_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 99.62
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.04326(13) 0.41953(9) 0.65254(9) 0.0390(3) Uani 1 1 d . . . . .
O1 O -0.10953(14) 0.53199(9) 0.82300(12) 0.0709(4) Uani 1 1 d . . . . .
N1 N 0.19445(14) 0.22901(8) 0.69178(9) 0.0397(3) Uani 1 1 d . . . . .
N3 N -0.24578(14) 0.39016(10) 0.78236(10) 0.0495(3) Uani 1 1 d . . . . .
C2 C 0.22697(15) 0.26547(10) 0.79281(10) 0.0355(3) Uani 1 1 d . . . . .
C14 C 0.24852(15) 0.29420(11) 0.61668(10) 0.0366(3) Uani 1 1 d . . . . .
C9 C 0.17543(16) 0.38798(11) 0.60140(10) 0.0363(3) Uani 1 1 d . . . . .
C6 C 0.17197(18) 0.38679(11) 0.92101(11) 0.0433(3) Uani 1 1 d . . . . .
H6 H 0.118926 0.443937 0.940057 0.052 Uiso 1 1 calc R . . . .
C8 C 0.03243(15) 0.40260(10) 0.74665(10) 0.0339(3) Uani 1 1 d . . . . .
C7 C 0.14785(15) 0.35214(10) 0.82072(10) 0.0337(3) Uani 1 1 d . . . . .
C15 C -0.11536(17) 0.44723(11) 0.78779(11) 0.0426(3) Uani 1 1 d . . . . .
C13 C 0.36735(19) 0.26647(13) 0.55524(12) 0.0505(4) Uani 1 1 d . . . . .
H13 H 0.416727 0.204401 0.564686 0.061 Uiso 1 1 calc R . . . .
C4 C 0.3506(2) 0.25238(15) 0.96417(13) 0.0585(5) Uani 1 1 d . . . . .
H4 H 0.418529 0.218746 1.012272 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2735(2) 0.33717(13) 0.99188(12) 0.0553(4) Uani 1 1 d . . . . .
H5 H 0.289624 0.361085 1.058252 0.066 Uiso 1 1 calc R . . . .
C10 C 0.2202(2) 0.45002(13) 0.52439(11) 0.0496(4) Uani 1 1 d . . . . .
H10 H 0.169387 0.511331 0.512600 0.059 Uiso 1 1 calc R . . . .
C3 C 0.32868(19) 0.21614(12) 0.86544(12) 0.0484(4) Uani 1 1 d . . . . .
H3 H 0.382112 0.158671 0.847669 0.058 Uiso 1 1 calc R . . . .
C12 C 0.4124(2) 0.33003(16) 0.48069(13) 0.0623(5) Uani 1 1 d . . . . .
H12 H 0.492491 0.310815 0.440693 0.075 Uiso 1 1 calc R . . . .
C11 C 0.3397(2) 0.42160(16) 0.46504(13) 0.0619(5) Uani 1 1 d . . . . .
H11 H 0.370703 0.464328 0.414751 0.074 Uiso 1 1 calc R . . . .
C16 C -0.2545(2) 0.28919(13) 0.74187(15) 0.0609(5) Uani 1 1 d . . . . .
H16A H -0.324310 0.288073 0.680152 0.091 Uiso 1 1 calc GR . . . .
H16B H -0.294802 0.244914 0.790824 0.091 Uiso 1 1 calc GR . . . .
H16C H -0.149999 0.267659 0.727799 0.091 Uiso 1 1 calc GR . . . .
C1 C 0.2202(2) 0.12187(12) 0.67689(15) 0.0603(5) Uani 1 1 d . . . . .
H1A H 0.332364 0.107805 0.684737 0.090 Uiso 1 1 calc GR . . . .
H1B H 0.177111 0.102917 0.609726 0.090 Uiso 1 1 calc GR . . . .
H1C H 0.167969 0.084518 0.726442 0.090 Uiso 1 1 calc GR . . . .
C17 C -0.3926(2) 0.43137(18) 0.8157(2) 0.0863(7) Uani 1 1 d . . . . .
H17A H -0.411996 0.402476 0.880111 0.129 Uiso 1 1 calc GR . . . .
H17B H -0.479965 0.416004 0.766269 0.129 Uiso 1 1 calc GR . . . .
H17C H -0.382525 0.502753 0.822795 0.129 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C9 122.73(12) . . ?
C2 N1 C14 113.36(11) . . ?
C2 N1 C1 116.26(13) . . ?
C14 N1 C1 116.30(12) . . ?
C15 N3 C16 124.36(13) . . ?
C15 N3 C17 119.10(15) . . ?
C16 N3 C17 116.51(14) . . ?
C7 C2 N1 118.25(12) . . ?
C3 C2 N1 122.50(13) . . ?
C3 C2 C7 119.19(13) . . ?
C9 C14 N1 118.76(12) . . ?
C13 C14 N1 122.32(13) . . ?
C13 C14 C9 118.88(14) . . ?
C14 C9 N2 123.43(12) . . ?
C10 C9 N2 116.67(13) . . ?
C10 C9 C14 119.47(13) . . ?
C5 C6 C7 120.70(15) . . ?
N2 C8 C7 128.64(12) . . ?
N2 C8 C15 114.30(12) . . ?
C7 C8 C15 116.92(11) . . ?
C2 C7 C8 120.20(12) . . ?
C6 C7 C2 119.34(13) . . ?
C6 C7 C8 120.34(12) . . ?
O1 C15 N3 123.58(14) . . ?
O1 C15 C8 119.42(13) . . ?
N3 C15 C8 117.00(12) . . ?
C12 C13 C14 120.71(16) . . ?
C5 C4 C3 120.85(15) . . ?
C4 C5 C6 119.73(15) . . ?
C11 C10 C9 120.73(16) . . ?
C4 C3 C2 120.19(15) . . ?
C11 C12 C13 120.43(15) . . ?
C12 C11 C10 119.75(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C9 1.4178(17) . ?
N2 C8 1.2731(17) . ?
O1 C15 1.2218(18) . ?
N1 C2 1.4213(18) . ?
N1 C14 1.4240(18) . ?
N1 C1 1.4619(19) . ?
N3 C15 1.3335(19) . ?
N3 C16 1.449(2) . ?
N3 C17 1.458(2) . ?
C2 C7 1.4008(19) . ?
C2 C3 1.391(2) . ?
C14 C9 1.401(2) . ?
C14 C13 1.3946(19) . ?
C9 C10 1.389(2) . ?
C6 C7 1.3983(19) . ?
C6 C5 1.377(2) . ?
C8 C7 1.4763(18) . ?
C8 C15 1.5243(18) . ?
C13 C12 1.378(2) . ?
C4 C5 1.371(3) . ?
C4 C3 1.386(2) . ?
C10 C11 1.384(2) . ?
C12 C11 1.374(3) . ?
