#------------------------------------------------------------------------------
#$Date: 2022-03-19 00:55:50 +0200 (Sat, 19 Mar 2022) $
#$Revision: 273815 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/98/7129873.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_7129873
loop_
_publ_author_name
'Shao, Rui'
'Zhao, Haixia'
'Ding, Shumin'
'Li, Lianjie'
'Chen, Chen'
'Wang, Jian'
'Shang, Yongjia'
_publ_section_title
;
 Silver-promoted dearomative [3 + 4] cycloaddition of anthranils with
 α‑isocyanoacetates: access to benzodiazepines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00807F
_journal_year                    2022
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24
_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     dual
_audit_creation_date             2020-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-05 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.296(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8038(11)
_cell_length_b                   8.8160(15)
_cell_length_c                   19.236(3)
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.363
_cell_measurement_theta_min      2.545
_cell_volume                     1144.5(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.865
_diffrn_reflns_theta_min         2.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1014 before and 0.0602 after correction. The Ratio of minimum to maximum transmission is 0.8444. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0645
_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)+(0.0752P)²+0.3925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1755
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1589
_reflns_number_total             2701
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00807f2.cif
_cod_data_source_block           201120c_0m_a
_cod_database_code               7129873
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C7(H7), C2(H2A), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O3 O 0.2495(2) 0.9914(2) 0.49546(10) 0.0552(6) Uani 1 1 d . . . . .
O2 O 0.7192(2) 0.4911(2) 0.60221(9) 0.0495(5) Uani 1 1 d . . . . .
O1 O 0.7129(3) 0.6579(2) 0.51420(10) 0.0601(6) Uani 1 1 d . . . . .
N2 N 0.1028(3) 0.8534(2) 0.57245(11) 0.0417(5) Uani 1 1 d . . . . .
H2 H -0.007671 0.860566 0.545444 0.050 Uiso 1 1 calc R . . . .
N1 N 0.4450(3) 0.8344(2) 0.56619(11) 0.0447(6) Uani 1 1 d . . . . .
H1 H 0.547288 0.889589 0.562263 0.054 Uiso 1 1 calc R . . . .
C1 C 0.0882(3) 0.7984(3) 0.64059(13) 0.0370(6) Uani 1 1 d . . . . .
C9 C 0.2654(3) 0.8966(3) 0.54340(13) 0.0383(6) Uani 1 1 d . . . . .
C8 C 0.4811(3) 0.6892(3) 0.59555(13) 0.0381(6) Uani 1 1 d . . . . .
C6 C 0.2155(3) 0.6887(3) 0.67417(13) 0.0404(6) Uani 1 1 d . . . . .
C7 C 0.3818(3) 0.6248(3) 0.64285(13) 0.0405(6) Uani 1 1 d . . . . .
H7 H 0.422665 0.528118 0.657704 0.049 Uiso 1 1 calc R . . . .
C10 C 0.6486(4) 0.6123(3) 0.56543(14) 0.0412(6) Uani 1 1 d . . . . .
C2 C -0.0711(4) 0.8521(3) 0.67278(14) 0.0475(7) Uani 1 1 d . . . . .
H2A H -0.155262 0.925233 0.650493 0.057 Uiso 1 1 calc R . . . .
C11 C 0.8829(4) 0.4149(3) 0.57421(15) 0.0539(8) Uani 1 1 d . . . . .
H11A H 0.988473 0.486818 0.569745 0.065 Uiso 1 1 calc R . . . .
H11B H 0.837725 0.374033 0.528136 0.065 Uiso 1 1 calc R . . . .
C5 C 0.1754(4) 0.6349(4) 0.73926(15) 0.0584(8) Uani 1 1 d . . . . .
H5 H 0.257262 0.560921 0.761942 0.070 Uiso 1 1 calc R . . . .
C3 C -0.1044(4) 0.7967(4) 0.73805(16) 0.0606(8) Uani 1 1 d . . . . .
H3 H -0.210061 0.833480 0.759350 0.073 Uiso 1 1 calc R . . . .
C4 C 0.0179(5) 0.6884(4) 0.77094(16) 0.0665(9) Uani 1 1 d . . . . .
H4 H -0.004891 0.650892 0.814397 0.080 Uiso 1 1 calc R . . . .
C12 C 0.9568(5) 0.2916(4) 0.62208(18) 0.0749(10) Uani 1 1 d . . . . .
H12A H 1.002091 0.332862 0.667465 0.112 Uiso 1 1 calc GR . . . .
H12B H 1.064491 0.240920 0.604035 0.112 Uiso 1 1 calc GR . . . .
H12C H 0.851899 0.220400 0.625955 0.112 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
C10 O2 C11 114.3(2) . . ?
C1 N2 H2 115.3 . . ?
C9 N2 H2 115.3 . . ?
C9 N2 C1 129.5(2) . . ?
C9 N1 H1 116.6 . . ?
C9 N1 C8 126.8(2) . . ?
C8 N1 H1 116.6 . . ?
C6 C1 N2 123.6(2) . . ?
C2 C1 N2 116.4(2) . . ?
C2 C1 C6 119.9(2) . . ?
O3 C9 N2 119.8(2) . . ?
O3 C9 N1 120.1(2) . . ?
N2 C9 N1 120.1(2) . . ?
N1 C8 C10 111.0(2) . . ?
C7 C8 N1 125.8(2) . . ?
C7 C8 C10 123.2(2) . . ?
C1 C6 C7 122.8(2) . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 119.2(2) . . ?
C8 C7 C6 127.3(2) . . ?
C8 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
O2 C10 C8 113.3(2) . . ?
O1 C10 O2 124.1(2) . . ?
O1 C10 C8 122.6(2) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.8 . . ?
O2 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
O2 C11 C12 109.0(2) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
O3 C9 1.240(3) . ?
O2 C10 1.336(3) . ?
O2 C11 1.460(3) . ?
O1 C10 1.198(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.413(3) . ?
N2 C9 1.356(3) . ?
N1 H1 0.8600 . ?
N1 C9 1.360(3) . ?
N1 C8 1.408(3) . ?
C1 C6 1.400(3) . ?
C1 C2 1.398(3) . ?
C8 C7 1.328(3) . ?
C8 C10 1.504(4) . ?
C6 C7 1.461(3) . ?
C6 C5 1.398(4) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.392(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.472(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(4) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C6 C7 2.6(4) . . . . ?
N2 C1 C6 C5 -174.9(2) . . . . ?
N2 C1 C2 C3 175.9(2) . . . . ?
N1 C8 C7 C6 0.3(4) . . . . ?
N1 C8 C10 O2 165.4(2) . . . . ?
N1 C8 C10 O1 -13.4(3) . . . . ?
C1 N2 C9 O3 -152.9(3) . . . . ?
C1 N2 C9 N1 28.0(4) . . . . ?
C1 C6 C7 C8 25.9(4) . . . . ?
C1 C6 C5 C4 -1.0(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C9 N2 C1 C6 -44.7(4) . . . . ?
C9 N2 C1 C2 139.3(3) . . . . ?
C9 N1 C8 C7 -43.3(4) . . . . ?
C9 N1 C8 C10 135.9(3) . . . . ?
C8 N1 C9 O3 -151.0(3) . . . . ?
C8 N1 C9 N2 28.2(4) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C7 C8 C10 O2 -15.4(4) . . . . ?
C7 C8 C10 O1 165.8(3) . . . . ?
C7 C6 C5 C4 -178.6(3) . . . . ?
C10 O2 C11 C12 175.7(3) . . . . ?
C10 C8 C7 C6 -178.8(2) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C11 O2 C10 O1 -0.9(4) . . . . ?
C11 O2 C10 C8 -179.7(2) . . . . ?
C5 C6 C7 C8 -156.6(3) . . . . ?
