#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031968.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_4031968
loop_
_publ_author_name
'Xu, Cheng'
'Jia, Feng-Cheng'
'Zhou, Zhi-Wen'
'Zheng, Si-Jie'
'Li, Han'
'Wu, An-Xin'
_publ_section_title
;
 Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromoaldehydes,
 Benzylamines, and Sodium Azide for the Assembly of Quinazoline
 Derivatives.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3000
_journal_page_last               3006
_journal_paper_doi               10.1021/acs.joc.5b02843
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.14
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.323(5)
_cell_angle_beta                 89.896(5)
_cell_angle_gamma                86.032(5)
_cell_formula_units_Z            4
_cell_length_a                   6.0845(18)
_cell_length_b                   7.566(2)
_cell_length_c                   25.221(7)
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.84
_cell_volume                     1157.8(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7273
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    3.526
_exptl_absorpt_correction_T_max  0.5694
_exptl_absorpt_correction_T_min  0.5109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0924P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                3053
_reflns_number_total             4005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02843_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4031968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.52152(7) 0.81902(6) 1.193805(16) 0.06701(19) Uani 1 1 d .
Br2 Br 0.37404(7) 0.04389(6) 0.309780(16) 0.06395(18) Uani 1 1 d .
C1 C 1.2768(5) 0.6835(5) 0.89740(14) 0.0436(8) Uani 1 1 d .
C2 C 1.3908(6) 0.6583(5) 0.84941(17) 0.0577(10) Uani 1 1 d .
H2 H 1.5348 0.6084 0.8500 0.069 Uiso 1 1 calc R
C3 C 1.2940(7) 0.7057(6) 0.80252(18) 0.0685(12) Uani 1 1 d .
H3 H 1.3695 0.6859 0.7709 0.082 Uiso 1 1 calc R
C4 C 1.0782(8) 0.7852(6) 0.80179(17) 0.0715(13) Uani 1 1 d .
H4 H 1.0127 0.8193 0.7695 0.086 Uiso 1 1 calc R
C5 C 0.9640(6) 0.8131(6) 0.84716(15) 0.0576(10) Uani 1 1 d .
H5 H 0.8215 0.8660 0.8456 0.069 Uiso 1 1 calc R
C6 C 1.0590(5) 0.7628(5) 0.89676(14) 0.0433(8) Uani 1 1 d .
C7 C 1.0443(5) 0.7384(4) 0.98683(13) 0.0397(8) Uani 1 1 d .
C8 C 1.3628(6) 0.6372(5) 0.94742(15) 0.0508(9) Uani 1 1 d .
H8 H 1.5061 0.5862 0.9495 0.061 Uiso 1 1 calc R
C9 C 0.9220(5) 0.7645(4) 1.03696(13) 0.0397(8) Uani 1 1 d .
C10 C 0.7106(5) 0.8459(5) 1.03697(14) 0.0451(8) Uani 1 1 d .
H10 H 0.6480 0.8890 1.0051 0.054 Uiso 1 1 calc R
C11 C 0.5915(6) 0.8642(5) 1.08331(15) 0.0489(9) Uani 1 1 d .
H11 H 0.4484 0.9162 1.0828 0.059 Uiso 1 1 calc R
C12 C 0.6878(6) 0.8042(5) 1.13002(14) 0.0451(8) Uani 1 1 d .
C13 C 0.8999(6) 0.7274(5) 1.13181(15) 0.0540(9) Uani 1 1 d .
H13 H 0.9639 0.6899 1.1640 0.065 Uiso 1 1 calc R
C14 C 1.0151(6) 0.7071(5) 1.08527(14) 0.0478(9) Uani 1 1 d .
H14 H 1.1577 0.6542 1.0861 0.057 Uiso 1 1 calc R
C15 C 0.2384(6) 0.1086(5) 0.37490(14) 0.0417(8) Uani 1 1 d .
C16 C 0.0238(6) 0.1785(5) 0.37506(14) 0.0505(9) Uani 1 1 d .
H16 H -0.0570 0.1896 0.3437 0.061 Uiso 1 1 calc R
C17 C -0.0701(5) 0.2320(5) 0.42223(14) 0.0447(8) Uani 1 1 d .
H17 H -0.2153 0.2793 0.4226 0.054 Uiso 1 1 calc R
C18 C 0.0495(5) 0.2159(4) 0.46912(13) 0.0364(7) Uani 1 1 d .
C19 C 0.2649(5) 0.1437(5) 0.46750(13) 0.0417(8) Uani 1 1 d .
H19 H 0.3470 0.1324 0.4986 0.050 Uiso 1 1 calc R
C20 C 0.3598(6) 0.0882(5) 0.42059(14) 0.0464(9) Uani 1 1 d .
H20 H 0.5036 0.0378 0.4200 0.056 Uiso 1 1 calc R
C21 C -0.0494(5) 0.2764(4) 0.51968(13) 0.0376(7) Uani 1 1 d .
C22 C -0.3523(6) 0.4026(5) 0.56062(15) 0.0475(9) Uani 1 1 d .
H22 H -0.4970 0.4510 0.5597 0.057 Uiso 1 1 calc R
C23 C -0.2408(5) 0.3937(4) 0.60953(14) 0.0408(8) Uani 1 1 d .
C24 C -0.0248(5) 0.3174(4) 0.60858(14) 0.0405(8) Uani 1 1 d .
C25 C 0.0943(6) 0.3018(5) 0.65610(15) 0.0545(10) Uani 1 1 d .
H25 H 0.2353 0.2458 0.6566 0.065 Uiso 1 1 calc R
C26 C 0.0060(7) 0.3674(6) 0.70143(17) 0.0671(12) Uani 1 1 d .
H26 H 0.0897 0.3607 0.7323 0.081 Uiso 1 1 calc R
C27 C -0.2104(7) 0.4456(6) 0.70233(16) 0.0588(10) Uani 1 1 d .
H27 H -0.2703 0.4884 0.7338 0.071 Uiso 1 1 calc R
C28 C -0.3302(7) 0.4580(5) 0.65748(16) 0.0531(9) Uani 1 1 d .
H28 H -0.4735 0.5094 0.6581 0.064 Uiso 1 1 calc R
N1 N 1.2531(4) 0.6615(4) 0.99158(12) 0.0476(7) Uani 1 1 d .
N2 N 0.9445(4) 0.7886(4) 0.94224(11) 0.0418(7) Uani 1 1 d .
N3 N 0.0709(4) 0.2577(4) 0.56272(11) 0.0399(6) Uani 1 1 d .
N4 N -0.2640(4) 0.3466(4) 0.51653(11) 0.0429(7) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 '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
C8 C1 C2 124.7(3)
C8 C1 C6 115.6(3)
C2 C1 C6 119.7(3)
C3 C2 C1 120.9(4)
C2 C3 C4 119.5(4)
C5 C4 C3 121.3(4)
C4 C5 C6 120.6(4)
N2 C6 C5 120.8(3)
N2 C6 C1 121.2(3)
C5 C6 C1 118.0(3)
N2 C7 N1 126.0(3)
N2 C7 C9 118.2(3)
N1 C7 C9 115.9(3)
N1 C8 C1 123.6(3)
C14 C9 C10 118.3(3)
C14 C9 C7 120.9(3)
C10 C9 C7 120.8(3)
C11 C10 C9 121.3(3)
C12 C11 C10 118.7(3)
C11 C12 C13 121.7(3)
C11 C12 Br1 119.2(3)
C13 C12 Br1 119.0(3)
C12 C13 C14 119.0(3)
C9 C14 C13 121.0(3)
C20 C15 C16 121.6(3)
C20 C15 Br2 118.7(3)
C16 C15 Br2 119.6(3)
C15 C16 C17 119.2(3)
C18 C17 C16 120.7(3)
C17 C18 C19 118.5(3)
C17 C18 C21 120.9(3)
C19 C18 C21 120.6(3)
C20 C19 C18 121.2(3)
C15 C20 C19 118.8(3)
N3 C21 N4 126.1(3)
N3 C21 C18 118.3(3)
N4 C21 C18 115.6(3)
N4 C22 C23 123.6(3)
C24 C23 C22 115.6(3)
C24 C23 C28 119.6(3)
C22 C23 C28 124.8(3)
N3 C24 C25 119.8(3)
N3 C24 C23 121.7(3)
C25 C24 C23 118.5(3)
C26 C25 C24 120.6(4)
C25 C26 C27 120.8(4)
C28 C27 C26 119.6(4)
C27 C28 C23 120.7(4)
C8 N1 C7 116.4(3)
C7 N2 C6 117.2(3)
C21 N3 C24 116.7(3)
C22 N4 C21 116.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.901(3)
Br2 C15 1.899(3)
C1 C8 1.392(5)
C1 C2 1.405(5)
C1 C6 1.416(5)
C2 C3 1.350(6)
C3 C4 1.406(6)
C4 C5 1.352(6)
C5 C6 1.410(5)
C6 N2 1.353(4)
C7 N2 1.312(4)
C7 N1 1.365(4)
C7 C9 1.477(5)
C8 N1 1.308(4)
C9 C14 1.390(5)
C9 C10 1.387(4)
C10 C11 1.380(5)
C11 C12 1.368(5)
C12 C13 1.378(5)
C13 C14 1.373(5)
C15 C20 1.369(5)
C15 C16 1.374(5)
C16 C17 1.378(5)
C17 C18 1.388(5)
C18 C19 1.386(4)
C18 C21 1.480(5)
C19 C20 1.379(5)
C21 N3 1.309(4)
C21 N4 1.376(4)
C22 N4 1.303(4)
C22 C23 1.407(5)
C23 C24 1.399(5)
C23 C28 1.411(5)
C24 N3 1.368(4)
C24 C25 1.399(5)
C25 C26 1.355(5)
C26 C27 1.406(6)
C27 C28 1.344(6)
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
C8 C1 C2 C3 179.4(4)
C6 C1 C2 C3 -1.3(6)
C1 C2 C3 C4 1.6(7)
C2 C3 C4 C5 -0.9(8)
C3 C4 C5 C6 0.0(7)
C4 C5 C6 N2 -179.3(4)
C4 C5 C6 C1 0.3(6)
C8 C1 C6 N2 -0.7(5)
C2 C1 C6 N2 179.9(3)
C8 C1 C6 C5 179.7(3)
C2 C1 C6 C5 0.3(5)
C2 C1 C8 N1 -179.8(4)
C6 C1 C8 N1 0.8(6)
N2 C7 C9 C14 177.2(3)
N1 C7 C9 C14 -2.2(5)
N2 C7 C9 C10 -2.4(5)
N1 C7 C9 C10 178.2(3)
C14 C9 C10 C11 -2.4(5)
C7 C9 C10 C11 177.2(3)
C9 C10 C11 C12 1.6(6)
C10 C11 C12 C13 0.3(6)
C10 C11 C12 Br1 -177.3(3)
C11 C12 C13 C14 -1.5(6)
Br1 C12 C13 C14 176.1(3)
C10 C9 C14 C13 1.2(5)
C7 C9 C14 C13 -178.4(3)
C12 C13 C14 C9 0.7(6)
C20 C15 C16 C17 1.1(6)
Br2 C15 C16 C17 -177.3(3)
C15 C16 C17 C18 0.0(6)
C16 C17 C18 C19 -0.5(5)
C16 C17 C18 C21 178.8(3)
C17 C18 C19 C20 -0.1(5)
C21 C18 C19 C20 -179.5(3)
C16 C15 C20 C19 -1.7(6)
Br2 C15 C20 C19 176.7(3)
C18 C19 C20 C15 1.2(6)
C17 C18 C21 N3 179.9(3)
C19 C18 C21 N3 -0.8(5)
C17 C18 C21 N4 0.4(5)
C19 C18 C21 N4 179.7(3)
N4 C22 C23 C24 -0.8(5)
N4 C22 C23 C28 178.0(3)
C22 C23 C24 N3 0.7(5)
C28 C23 C24 N3 -178.2(3)
C22 C23 C24 C25 -178.9(3)
C28 C23 C24 C25 2.1(5)
N3 C24 C25 C26 177.0(4)
C23 C24 C25 C26 -3.4(6)
C24 C25 C26 C27 2.9(7)
C25 C26 C27 C28 -1.1(7)
C26 C27 C28 C23 -0.1(6)
C24 C23 C28 C27 -0.4(6)
C22 C23 C28 C27 -179.3(4)
C1 C8 N1 C7 -0.7(6)
N2 C7 N1 C8 0.4(5)
C9 C7 N1 C8 179.8(3)
N1 C7 N2 C6 -0.3(5)
C9 C7 N2 C6 -179.7(3)
C5 C6 N2 C7 -179.9(3)
C1 C6 N2 C7 0.5(5)
N4 C21 N3 C24 -1.5(5)
C18 C21 N3 C24 179.0(3)
C25 C24 N3 C21 -180.0(3)
C23 C24 N3 C21 0.4(5)
C23 C22 N4 C21 -0.2(5)
N3 C21 N4 C22 1.4(5)
C18 C21 N4 C22 -179.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094686
