#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:05:05 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291022 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/30/7063071.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_7063071
loop_
_publ_author_name
'Chen, Yanqi'
'Hao, Subin'
'Yin, Lingfeng'
'Song, Xinluo'
'Liu, Zhiyao'
'Li, Mingde'
'Dang, Li'
_publ_section_title
;
 Metal-free cascade reactions for one-pot tetrahydroquinoxaline
 construction through nitroarene reduction and imine hydrogenation with
 water
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6103
_journal_page_last               6108
_journal_paper_doi               10.1039/D3NJ05093A
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-08-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-31 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.805(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1113(5)
_cell_length_b                   6.7331(3)
_cell_length_c                   11.6092(7)
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.6540
_cell_measurement_theta_min      6.5350
_cell_volume                     610.06(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  26.00   0.50    0.50    --    0.00 -77.00-180.00   78
  2  ω    -88.00 -44.00   0.50    0.50    --    0.00 -77.00-180.00   88
  3  ω    -87.00 -39.00   0.50    0.50    --    0.00 -38.00 -60.00   96
  4  ω     27.00 118.00   0.50    0.50    --   89.30 -82.00  30.00  182
  5  ω     16.00 106.00   0.50    0.50    --   89.30 -15.00 -30.00  180
  6  ω     72.00 120.00   0.50    0.50    --   89.30 -82.00 -90.00   96
  7  ω      8.00 110.00   0.50    0.50    --   89.30 -15.00  60.00  204
  8  ω     59.00  84.00   0.50    0.50    --   89.30 -45.00  90.00   50
  9  ω     28.00 101.00   0.50    0.50    --   89.30 -61.00  30.00  146
;
_diffrn_measurement_device       'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1912826000
_diffrn_orient_matrix_UB_12      0.0038543000
_diffrn_orient_matrix_UB_13      0.0696680000
_diffrn_orient_matrix_UB_21      -0.0494012000
_diffrn_orient_matrix_UB_22      -0.0043483000
_diffrn_orient_matrix_UB_23      0.1190161000
_diffrn_orient_matrix_UB_31      0.0046852000
_diffrn_orient_matrix_UB_32      -0.2285274000
_diffrn_orient_matrix_UB_33      -0.0009140000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2450
_diffrn_reflns_theta_full        70.57
_diffrn_reflns_theta_max         70.57
_diffrn_reflns_theta_min         3.96
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic blackish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_coef       0.0040(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.4440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                1398
_reflns_number_total             1479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3nj05093a2.cif
_cod_data_source_block           20230310a
_cod_depositor_comments
'Adding full bibliography for 7063070--7063071.cif.'
_cod_database_code               7063071
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H O N'
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7C(H7C)
2.b Aromatic/amide H refined with riding coordinates:
 N2N(H2N), N1N(H1N), C13C(H13C), C14C(H14C), C15C(H15C), C4C(H4C), C6C(H6C),
 C2C(H2C), C3C(H3C), C1C(H1C)
2.c Idealised Me refined as rotating group:
 C11C(H11A,H11B,H11C)
;
_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 1.505
_oxdiff_exptl_absorpt_empirical_full_min 0.652
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1O O 0.5766(3) 0.4819(4) 1.00728(18) 0.0385(6) Uani 1 1 d . . .
N2N N 0.4264(3) 0.6552(5) 0.8466(2) 0.0332(7) Uani 1 1 d . . .
H2N H 0.4137 0.7500 0.8931 0.040 Uiso 1 1 calc R . .
N1N N 0.4457(4) 0.3494(5) 0.6948(3) 0.0456(8) Uani 1 1 d . . .
H1N H 0.4344 0.2474 0.6487 0.055 Uiso 1 1 calc R . .
C8C C 0.5165(4) 0.4934(6) 0.8978(3) 0.0343(8) Uani 1 1 d . . .
C9C C 0.3522(4) 0.6794(5) 0.7229(3) 0.0311(8) Uani 1 1 d . . .
C5C C 0.7383(4) 0.3142(5) 0.8307(3) 0.0314(7) Uani 1 1 d . . .
C10C C 0.3665(4) 0.5251(6) 0.6465(3) 0.0330(8) Uani 1 1 d . . .
C12C C 0.2916(4) 0.5445(6) 0.5223(3) 0.0333(8) Uani 1 1 d . . .
C13C C 0.2010(4) 0.7183(6) 0.4817(3) 0.0379(9) Uani 1 1 d . . .
H13C H 0.1500 0.7331 0.4001 0.045 Uiso 1 1 calc R . .
C14C C 0.1842(5) 0.8688(6) 0.5579(3) 0.0415(9) Uani 1 1 d . . .
H14C H 0.1204 0.9812 0.5278 0.050 Uiso 1 1 calc R . .
C7C C 0.5461(4) 0.3273(6) 0.8182(3) 0.0342(8) Uani 1 1 d . . .
H7C H 0.5112 0.2029 0.8485 0.041 Uiso 1 1 calc R . .
C15C C 0.2629(4) 0.8524(6) 0.6802(3) 0.0365(8) Uani 1 1 d . . .
H15C H 0.2557 0.9552 0.7321 0.044 Uiso 1 1 calc R . .
C4C C 0.8223(5) 0.4709(7) 0.7951(3) 0.0436(9) Uani 1 1 d . . .
H4C H 0.7612 0.5841 0.7629 0.052 Uiso 1 1 calc R . .
C6C C 0.8271(5) 0.1451(6) 0.8787(3) 0.0398(9) Uani 1 1 d . . .
H6C H 0.7700 0.0399 0.9029 0.048 Uiso 1 1 calc R . .
C2C C 1.0852(5) 0.2873(8) 0.8553(4) 0.0600(14) Uani 1 1 d . . .
H2C H 1.2022 0.2785 0.8631 0.072 Uiso 1 1 calc R . .
C11C C 0.3069(5) 0.3825(6) 0.4382(3) 0.0431(9) Uani 1 1 d . . .
H11A H 0.4252 0.3647 0.4406 0.065 Uiso 1 1 calc R . .
H11B H 0.2427 0.4174 0.3584 0.065 Uiso 1 1 calc R . .
H11C H 0.2626 0.2613 0.4615 0.065 Uiso 1 1 calc R . .
C3C C 0.9953(5) 0.4617(8) 0.8066(4) 0.0562(12) Uani 1 1 d . . .
H3C H 1.0521 0.5676 0.7830 0.067 Uiso 1 1 calc R . .
C1C C 1.0033(5) 0.1324(8) 0.8910(3) 0.0546(12) Uani 1 1 d . . .
H1C H 1.0639 0.0190 0.9232 0.065 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8C N2N H2N 117.6 . . ?
C8C N2N C9C 124.8(3) . . ?
C9C N2N H2N 117.6 . . ?
C10C N1N H1N 118.0 . . ?
C10C N1N C7C 124.0(3) . . ?
C7C N1N H1N 118.0 . . ?
O1O C8C N2N 121.1(3) . . ?
O1O C8C C7C 120.0(3) . . ?
N2N C8C C7C 118.9(3) . . ?
C10C C9C N2N 118.5(3) . . ?
C15C C9C N2N 119.9(3) . . ?
C15C C9C C10C 121.6(3) . . ?
C4C C5C C7C 120.1(3) . . ?
C4C C5C C6C 120.4(3) . . ?
C6C C5C C7C 119.5(3) . . ?
N1N C10C C9C 119.2(3) . . ?
N1N C10C C12C 121.0(3) . . ?
C9C C10C C12C 119.7(3) . . ?
C10C C12C C11C 120.8(3) . . ?
C13C C12C C10C 117.7(3) . . ?
C13C C12C C11C 121.5(3) . . ?
C12C C13C H13C 118.8 . . ?
C14C C13C C12C 122.4(3) . . ?
C14C C13C H13C 118.8 . . ?
C13C C14C H14C 120.0 . . ?
C13C C14C C15C 119.9(4) . . ?
C15C C14C H14C 120.0 . . ?
N1N C7C C8C 112.8(3) . . ?
N1N C7C C5C 112.6(3) . . ?
N1N C7C H7C 107.7 . . ?
C8C C7C C5C 108.2(3) . . ?
C8C C7C H7C 107.7 . . ?
C5C C7C H7C 107.7 . . ?
C9C C15C C14C 118.6(3) . . ?
C9C C15C H15C 120.7 . . ?
C14C C15C H15C 120.7 . . ?
C5C C4C H4C 119.6 . . ?
C3C C4C C5C 120.7(4) . . ?
C3C C4C H4C 119.6 . . ?
C5C C6C H6C 120.1 . . ?
C5C C6C C1C 119.8(4) . . ?
C1C C6C H6C 120.1 . . ?
C3C C2C H2C 119.5 . . ?
C1C C2C H2C 119.5 . . ?
C1C C2C C3C 121.1(3) . . ?
C12C C11C H11A 109.5 . . ?
C12C C11C H11B 109.5 . . ?
C12C C11C H11C 109.5 . . ?
H11A C11C H11B 109.5 . . ?
H11A C11C H11C 109.5 . . ?
H11B C11C H11C 109.5 . . ?
C4C C3C C2C 118.5(4) . . ?
C4C C3C H3C 120.7 . . ?
C2C C3C H3C 120.7 . . ?
C6C C1C H1C 120.3 . . ?
C2C C1C C6C 119.5(5) . . ?
C2C C1C H1C 120.3 . . ?
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
O1O C8C 1.234(4) . ?
N2N H2N 0.8600 . ?
N2N C8C 1.355(5) . ?
N2N C9C 1.406(4) . ?
N1N H1N 0.8600 . ?
N1N C10C 1.389(5) . ?
N1N C7C 1.450(4) . ?
C8C C7C 1.511(5) . ?
C9C C10C 1.392(5) . ?
C9C C15C 1.390(5) . ?
C5C C7C 1.529(4) . ?
C5C C4C 1.379(5) . ?
C5C C6C 1.381(5) . ?
C10C C12C 1.409(4) . ?
C12C C13C 1.394(5) . ?
C12C C11C 1.491(5) . ?
C13C H13C 0.9300 . ?
C13C C14C 1.375(5) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.393(5) . ?
C7C H7C 0.9800 . ?
C15C H15C 0.9300 . ?
C4C H4C 0.9300 . ?
C4C C3C 1.374(5) . ?
C6C H6C 0.9300 . ?
C6C C1C 1.400(5) . ?
C2C H2C 0.9300 . ?
C2C C3C 1.417(7) . ?
C2C C1C 1.360(7) . ?
C11C H11A 0.9600 . ?
C11C H11B 0.9600 . ?
C11C H11C 0.9600 . ?
C3C H3C 0.9300 . ?
C1C H1C 0.9300 . ?
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
O1O C8C C7C N1N 171.0(3) . . . . ?
O1O C8C C7C C5C -63.7(4) . . . . ?
N2N C8C C7C N1N -10.3(4) . . . . ?
N2N C8C C7C C5C 115.0(3) . . . . ?
N2N C9C C10C N1N 3.1(4) . . . . ?
N2N C9C C10C C12C 179.3(3) . . . . ?
N2N C9C C15C C14C -177.2(3) . . . . ?
N1N C10C C12C C13C 174.3(3) . . . . ?
N1N C10C C12C C11C -4.7(5) . . . . ?
C8C N2N C9C C10C 2.1(4) . . . . ?
C8C N2N C9C C15C -179.8(3) . . . . ?
C9C N2N C8C O1O -179.3(3) . . . . ?
C9C N2N C8C C7C 2.0(5) . . . . ?
C9C C10C C12C C13C -1.9(4) . . . . ?
C9C C10C C12C C11C 179.2(3) . . . . ?
C5C C4C C3C C2C 0.3(6) . . . . ?
C5C C6C C1C C2C 0.0(5) . . . . ?
C10C N1N C7C C8C 16.1(5) . . . . ?
C10C N1N C7C C5C -106.7(4) . . . . ?
C10C C9C C15C C14C 0.9(5) . . . . ?
C10C C12C C13C C14C 0.5(5) . . . . ?
C12C C13C C14C C15C 1.6(5) . . . . ?
C13C C14C C15C C9C -2.3(5) . . . . ?
C7C N1N C10C C9C -13.0(5) . . . . ?
C7C N1N C10C C12C 170.8(3) . . . . ?
C7C C5C C4C C3C 179.5(3) . . . . ?
C7C C5C C6C C1C -179.7(3) . . . . ?
C15C C9C C10C N1N -175.0(3) . . . . ?
C15C C9C C10C C12C 1.2(5) . . . . ?
C4C C5C C7C N1N 61.8(4) . . . . ?
C4C C5C C7C C8C -63.5(4) . . . . ?
C4C C5C C6C C1C -0.2(5) . . . . ?
C6C C5C C7C N1N -118.6(4) . . . . ?
C6C C5C C7C C8C 116.0(3) . . . . ?
C6C C5C C4C C3C 0.0(5) . . . . ?
C11C C12C C13C C14C 179.4(3) . . . . ?
C3C C2C C1C C6C 0.3(6) . . . . ?
C1C C2C C3C C4C -0.5(6) . . . . ?
