#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:42:07 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290266 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159762.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_7159762
loop_
_publ_author_name
'Le, Duc Long'
'Nguyen, Le Anh'
'Vo, Ngoc Binh'
'Nguyen, Thi Thu Tram'
'Ngo, Quoc Anh'
'Retailleau, Pascal'
'Nguyen, Thanh Binh'
_publ_section_title
;
 Sodium sulfide-promoted regiodefined redox condensation of
 o-nitroanilines with aryl ketones to benzo[a]phenazines and quinoxalines
;
_journal_issue                   6
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1167
_journal_page_last               1171
_journal_paper_doi               10.1039/D3OB02028B
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.144
_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'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-26
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.633(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6512(5)
_cell_length_b                   4.9125(2)
_cell_length_c                   12.4349(9)
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6730
_cell_measurement_theta_min      3.3840
_cell_volume                     570.43(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac5-024 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  90.00   0.50    3.00    --    6.50  37.00  69.00  228
  2  ω      4.00  62.00   0.50    3.00    --   -7.20  37.00  69.00  116
  3  ω     -1.00  25.00   0.50    3.00    --    6.50  57.00 -90.00   52
  4  ω    -22.00  83.00   0.50    3.00    --    6.50  57.00 120.00  210
  5  ω     29.00  95.00   0.50    3.00    --    6.50  57.00 -60.00  132
  6  ω    -21.00   5.00   0.50    3.00    --    6.50  57.00-180.00   52
  7  ω    -24.00  81.00   0.50    3.00    --   -7.20  57.00 -30.00  210
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221082000
_diffrn_orient_matrix_UB_12      0.0669004000
_diffrn_orient_matrix_UB_13      -0.0521083000
_diffrn_orient_matrix_UB_21      0.0706062000
_diffrn_orient_matrix_UB_22      -0.0100682000
_diffrn_orient_matrix_UB_23      -0.0067661000
_diffrn_orient_matrix_UB_31      -0.0171336000
_diffrn_orient_matrix_UB_32      -0.1275177000
_diffrn_orient_matrix_UB_33      -0.0267934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.9965
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10735
_diffrn_reflns_point_group_measured_fraction_full 0.9883
_diffrn_reflns_point_group_measured_fraction_max 0.9375
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       stick
_exptl_crystal_F_000             283.744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: deuterated chloroform'
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.6002
_refine_diff_density_min         -0.4865
_refine_diff_density_rms         0.0565
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_d_res_high            0.7301
_refine_ls_d_res_low             6.0158
_refine_ls_extinction_coef       0.0165(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.0551
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0070P)²+0.0996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0400
_refine_ls_wR_factor_ref         0.0419
_reflns_Friedel_coverage         0.864
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              17
_reflns_limit_l_min              -16
_reflns_number_gt                2440
_reflns_number_total             2878
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob02028b2.cif
_cod_data_source_block           TD55
_cod_depositor_comments
'Adding full bibliography for 7159759--7159762.cif.'
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7159762
_chemical_oxdiff_formula         'C19 H14 Br N2'
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(H2) \\sim Ueq, Uanis(H10) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.02
;
_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 2.104
_oxdiff_exptl_absorpt_empirical_full_min 0.767
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_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.901550(18) -0.29600(2) 0.392181(18) 0.05089(8) Uani 1.000000 . .
N1 N 0.44159(16) 0.5657(3) 0.30458(12) 0.0314(3) Uani 1.000000 . .
N2 N 0.57306(17) 0.4182(3) 0.13563(13) 0.0391(4) Uani 1.000000 . .
C4 C 0.7192(2) 0.0924(3) 0.25715(18) 0.0366(4) Uani 1.000000 . .
H4 H 0.769(3) 0.032(5) 0.1931(19) 0.070(8) Uani 1.000000 . .
C3 C 0.61145(19) 0.2963(3) 0.23691(15) 0.0311(4) Uani 1.000000 . .
C8 C 0.54543(18) 0.3718(3) 0.32160(14) 0.0291(4) Uani 1.000000 . .
C5 C 0.75763(19) -0.0255(3) 0.36003(18) 0.0363(4) Uani 1.000000 . .
C7 C 0.5888(2) 0.2434(5) 0.42631(16) 0.0365(5) Uani 1.000000 . .
H7 H 0.537(2) 0.303(4) 0.4882(17) 0.054(7) Uani 1.000000 . .
C6 C 0.6931(2) 0.0476(4) 0.4452(2) 0.0390(4) Uani 1.000000 . .
H6 H 0.724(2) -0.056(5) 0.522(2) 0.064(7) Uani 1.000000 . .
C1 C 0.40436(16) 0.6820(5) 0.20629(13) 0.0305(4) Uani 1.000000 . .
C2 C 0.4728(2) 0.6046(4) 0.12143(17) 0.0395(5) Uani 1.000000 . .
H2 H 0.446(2) 0.681(8) 0.0434(15) 0.069(7) Uani 1.000000 . U
C9 C 0.29066(19) 0.8917(3) 0.18650(16) 0.0330(4) Uani 1.000000 . .
C10 C 0.2487(2) 1.0330(4) 0.08609(18) 0.0433(5) Uani 1.000000 . .
H10 H 0.298(3) 0.993(5) 0.0199(17) 0.061(6) Uani 1.000000 . U
C13 C 0.1164(2) 1.1516(4) 0.2539(2) 0.0499(7) Uani 1.000000 . .
H13 H 0.067(2) 1.179(8) 0.323(2) 0.072(7) Uani 1.000000 . .
C14 C 0.2226(2) 0.9536(4) 0.2697(2) 0.0428(5) Uani 1.000000 . .
H14 H 0.254(3) 0.845(5) 0.346(2) 0.073(8) Uani 1.000000 . .
C11 C 0.1411(2) 1.2285(6) 0.0697(2) 0.0528(5) Uani 1.000000 . .
H11 H 0.108(3) 1.349(6) -0.007(2) 0.099(10) Uani 1.000000 . .
C12 C 0.0755(3) 1.2902(4) 0.1535(2) 0.0507(6) Uani 1.000000 . .
H12 H -0.010(3) 1.440(6) 0.140(2) 0.086(9) Uani 1.000000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 1 -1 0.0408
-13 -1 1 0.0408
-1 4 5 0.2425
0 -4 -5 0.2440
0 0 1 0.0606
0 0 -1 0.0553
-12 0 11 0.0525
12 -1 -11 0.0612
12 0 4 0.0476
7 0 -17 0.0584
-1 0 0 0.0368
-3 -6 6 0.2702
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
C1 N1 C8 117.83(15) . . ?
C2 N2 C3 116.86(16) . . ?
C3 C4 H4 120.6(12) . . ?
C5 C4 H4 120.8(12) . . ?
C5 C4 C3 118.57(18) . . ?
C4 C3 N2 119.44(16) . . ?
C8 C3 N2 120.46(16) . . ?
C8 C3 C4 120.10(17) . . ?
C3 C8 N1 121.46(16) . . ?
C7 C8 N1 119.46(16) . . ?
C7 C8 C3 119.08(16) . . ?
C4 C5 Br1 120.45(15) . . ?
C6 C5 Br1 117.52(15) . . ?
C6 C5 C4 122.03(18) . . ?
H7 C7 C8 117.5(11) . . ?
C6 C7 C8 120.43(19) . . ?
C6 C7 H7 122.1(11) . . ?
C7 C6 C5 119.8(2) . . ?
H6 C6 C5 118.9(13) . . ?
H6 C6 C7 121.3(13) . . ?
C2 C1 N1 120.12(19) . . ?
C9 C1 N1 118.32(15) . . ?
C9 C1 C2 121.56(16) . . ?
C1 C2 N2 123.28(19) . . ?
H2 C2 N2 112.9(17) . . ?
H2 C2 C1 123.8(17) . . ?
C10 C9 C1 122.03(17) . . ?
C14 C9 C1 119.84(16) . . ?
C14 C9 C10 118.13(18) . . ?
H10 C10 C9 120.8(13) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 118.4(13) . . ?
C14 C13 H13 115.1(17) . . ?
C12 C13 H13 124.7(16) . . ?
C12 C13 C14 120.1(2) . . ?
C13 C14 C9 121.1(2) . . ?
H14 C14 C9 118.2(13) . . ?
H14 C14 C13 120.7(13) . . ?
H11 C11 C10 122.7(15) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 116.7(15) . . ?
C11 C12 C13 119.3(2) . . ?
H12 C12 C13 120.5(16) . . ?
H12 C12 C11 120.2(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
Br1 C5 1.8907(18) . ?
N1 C8 1.360(2) . ?
N1 C1 1.314(2) . ?
N2 C3 1.359(2) . ?
N2 C2 1.311(2) . ?
C4 H4 1.07(2) . ?
C4 C3 1.420(2) . ?
C4 C5 1.367(3) . ?
C3 C8 1.411(2) . ?
C8 C7 1.412(3) . ?
C5 C6 1.404(3) . ?
C7 H7 1.062(19) . ?
C7 C6 1.369(3) . ?
C6 H6 1.05(2) . ?
C1 C2 1.430(2) . ?
C1 C9 1.480(3) . ?
C2 H2 1.01(2) . ?
C9 C10 1.396(3) . ?
C9 C14 1.392(3) . ?
C10 H10 1.07(2) . ?
C10 C11 1.391(3) . ?
C13 H13 1.09(2) . ?
C13 C14 1.391(3) . ?
C13 C12 1.389(3) . ?
C14 H14 1.06(2) . ?
C11 H11 1.10(3) . ?
C11 C12 1.383(3) . ?
C12 H12 1.09(3) . ?
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
Br1 C5 C4 C3 -179.49(13) . . . . ?
Br1 C5 C6 C7 179.68(15) . . . . ?
N1 C8 C3 N2 0.45(19) . . . . ?
N1 C8 C3 C4 -179.78(15) . . . . ?
N1 C8 C7 C6 179.97(17) . . . . ?
N1 C1 C2 N2 0.3(2) . . . . ?
N1 C1 C9 C10 177.36(17) . . . . ?
N1 C1 C9 C14 -2.4(2) . . . . ?
N2 C3 C4 C5 179.17(16) . . . . ?
N2 C3 C8 C7 -179.29(17) . . . . ?
N2 C2 C1 C9 -179.45(18) . . . . ?
C4 C3 C8 C7 0.48(19) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C3 C8 C7 C6 -0.28(19) . . . . ?
C8 C7 C6 C5 0.2(2) . . . . ?
C1 C9 C10 C11 179.8(2) . . . . ?
C1 C9 C14 C13 179.34(19) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C9 C14 C13 C12 0.6(2) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
H2 0.0200
H10 0.0200
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
13.2541 0.5675 -0.7203 -0.2175 0.9350 -0.2802
-13.2541 -0.5675 0.7203 0.2175 -0.9350 0.2802
-0.9874 4.0007 4.9901 0.0295 -0.1438 -0.6269
-0.0121 -4.0003 -4.9922 -0.0072 0.0732 0.6441
-0.0014 -0.0001 1.0002 -0.0521 -0.0069 -0.0268
0.0014 0.0001 -1.0002 0.0521 0.0069 0.0268
-12.0102 0.0048 10.9758 -0.3061 -0.9223 -0.0889
12.0054 -1.0050 -10.9736 0.2392 0.9320 0.2165
11.9893 -0.0058 4.0265 -0.4753 0.8193 -0.3126
7.0207 -0.0021 -16.9875 0.7298 0.6107 0.3351
-0.9996 0.0005 -0.0022 0.0222 -0.0706 0.0171
-3.0358 -5.9999 6.0073 -0.6473 -0.1946 0.6562
