#------------------------------------------------------------------------------
#$Date: 2019-11-04 13:12:03 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222839 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/42/4034296.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_4034296
loop_
_publ_author_name
'Han, Yi'
'Hu, Zhenzhu'
'Liu, Meifang'
'Li, Mengwei'
'Wang, Tingting'
'Chen, Yulan'
_publ_section_title
;
 Synthesis, Characterization, and Properties of Diazapyrenes via
 Bischler-Napieralski Reaction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3953
_journal_page_last               3959
_journal_paper_doi               10.1021/acs.joc.8b03096
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         '2(C8 H5 Br N)'
_chemical_formula_sum            'C16 H10 Br2 N2'
_chemical_formula_weight         390.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                110.57(3)
_cell_angle_beta                 103.01(3)
_cell_angle_gamma                93.22(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9089(16)
_cell_length_b                   8.3573(17)
_cell_length_c                   11.052(2)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8704
_cell_measurement_theta_min      2.0395
_cell_volume                     659.0(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6381
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         2.039
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.140
_exptl_absorpt_correction_T_max  0.5788
_exptl_absorpt_correction_T_min  0.1926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.966
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.257
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0343
_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)+(0.0283P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1727
_reflns_number_total             2323
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b03096_si_002.cif
_cod_data_source_block           r20171229a1
_cod_database_code               4034296
_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   0.579
_shelx_estimated_absorpt_t_min   0.193
_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:
 C2(H2), C6(H6), C10(H10), C14(H14)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Br1 Br 0.36396(6) 0.19173(6) 0.98030(4) 0.02037(15) Uani 1 1 d .
Br2 Br 0.87122(6) 0.35894(5) 0.12904(4) 0.02137(16) Uani 1 1 d .
N1 N 0.6291(4) 0.2746(4) 0.4812(4) 0.0145(8) Uani 1 1 d .
N2 N 0.8777(4) 0.8057(4) 0.6034(3) 0.0137(8) Uani 1 1 d .
C1 C 0.4114(5) 0.1249(5) 0.8087(4) 0.0141(10) Uani 1 1 d .
C2 C 0.3738(5) -0.0493(5) 0.7256(4) 0.0131(10) Uani 1 1 d .
H2 H 0.325093 -0.132110 0.754043 0.016 Uiso 1 1 calc R
C3 C 0.4079(5) -0.1000(5) 0.6023(4) 0.0119(10) Uani 1 1 d .
C4 C 0.4816(5) 0.0263(5) 0.5633(4) 0.0101(9) Uani 1 1 d .
C5 C 0.5198(5) 0.2018(5) 0.6473(4) 0.0104(9) Uani 1 1 d .
C6 C 0.4824(5) 0.2503(5) 0.7743(4) 0.0123(10) Uani 1 1 d .
H6 H 0.506382 0.367684 0.834146 0.015 Uiso 1 1 calc R
C7 C 0.5932(5) 0.3231(5) 0.5995(4) 0.0109(9) Uani 1 1 d .
C8 C 0.6342(5) 0.5110(5) 0.6833(4) 0.0169(10) Uani 1 1 d .
H8A H 0.689301 0.572025 0.637563 0.025 Uiso 1 1 calc GR
H8B H 0.714839 0.528454 0.769875 0.025 Uiso 1 1 calc GR
H8C H 0.525663 0.556113 0.697549 0.025 Uiso 1 1 calc GR
C9 C 0.9263(5) 0.5856(5) 0.2641(4) 0.0152(10) Uani 1 1 d .
C10 C 0.9969(5) 0.7176(5) 0.2336(4) 0.0122(10) Uani 1 1 d .
H10 H 1.023569 0.694276 0.149981 0.015 Uiso 1 1 calc R
C11 C 1.0283(5) 0.8871(5) 0.3297(4) 0.0117(9) Uani 1 1 d .
C12 C 0.9880(5) 0.9152(5) 0.4522(4) 0.0112(9) Uani 1 1 d .
C13 C 0.9192(5) 0.7767(5) 0.4808(4) 0.0113(9) Uani 1 1 d .
C14 C 0.8883(5) 0.6097(5) 0.3855(4) 0.0120(10) Uani 1 1 d .
H14 H 0.842632 0.514773 0.402772 0.014 Uiso 1 1 calc R
C15 C 0.9048(5) 0.9636(5) 0.6917(4) 0.0114(10) Uani 1 1 d .
C16 C 0.8576(5) 0.9868(5) 0.8209(4) 0.0156(10) Uani 1 1 d .
H16A H 0.814474 0.873805 0.819703 0.023 Uiso 1 1 calc GR
H16B H 0.765864 1.060884 0.830818 0.023 Uiso 1 1 calc GR
H16C H 0.961679 1.040662 0.896267 0.023 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'
Br Br -0.2901 2.4595 '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'
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
C7 N1 C3 119.1(4) . 2_656
C15 N2 C13 118.9(4) . .
C2 C1 Br1 118.4(3) . .
C6 C1 Br1 118.3(3) . .
C6 C1 C2 123.3(4) . .
C1 C2 H2 120.4 . .
C3 C2 C1 119.2(4) . .
C3 C2 H2 120.4 . .
N1 C3 C4 121.6(4) 2_656 .
C2 C3 N1 119.4(4) . 2_656
C2 C3 C4 119.0(4) . .
C3 C4 C4 119.0(5) . 2_656
C5 C4 C3 121.7(4) . .
C5 C4 C4 119.3(5) . 2_656
C4 C5 C6 118.0(4) . .
C4 C5 C7 118.3(4) . .
C6 C5 C7 123.7(4) . .
C1 C6 C5 118.8(4) . .
C1 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
N1 C7 C5 122.6(4) . .
N1 C7 C8 116.6(4) . .
C5 C7 C8 120.8(4) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 Br2 117.8(3) . .
C10 C9 C14 123.9(4) . .
C14 C9 Br2 118.2(3) . .
C9 C10 H10 120.9 . .
C9 C10 C11 118.3(4) . .
C11 C10 H10 120.9 . .
C10 C11 C15 123.7(4) . 2_776
C12 C11 C10 118.8(4) . .
C12 C11 C15 117.4(4) . 2_776
C11 C12 C12 119.7(5) . 2_776
C11 C12 C13 121.3(4) . .
C12 C12 C13 119.0(5) 2_776 .
N2 C13 C12 121.0(4) . .
C14 C13 N2 119.4(4) . .
C14 C13 C12 119.6(4) . .
C9 C14 C13 118.1(4) . .
C9 C14 H14 121.0 . .
C13 C14 H14 121.0 . .
N2 C15 C11 123.9(4) . 2_776
N2 C15 C16 116.5(4) . .
C11 C15 C16 119.6(4) 2_776 .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.910(4) .
Br2 C9 1.907(4) .
N1 C3 1.397(5) 2_656
N1 C7 1.327(5) .
N2 C13 1.407(5) .
N2 C15 1.307(5) .
C1 C2 1.393(6) .
C1 C6 1.367(6) .
C2 H2 0.9500 .
C2 C3 1.373(6) .
C3 C4 1.415(6) .
C4 C4 1.415(8) 2_656
C4 C5 1.404(6) .
C5 C6 1.422(6) .
C5 C7 1.447(6) .
C6 H6 0.9500 .
C7 C8 1.488(5) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.386(5) .
C9 C14 1.388(6) .
C10 H10 0.9500 .
C10 C11 1.407(6) .
C11 C12 1.403(6) .
C11 C15 1.444(6) 2_776
C12 C12 1.411(8) 2_776
C12 C13 1.414(6) .
C13 C14 1.389(5) .
C14 H14 0.9500 .
C15 C16 1.507(6) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
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_4
Br1 C1 C2 C3 -179.6(3) . .
Br1 C1 C6 C5 179.4(3) . .
Br2 C9 C10 C11 176.3(3) . .
Br2 C9 C14 C13 -176.3(3) . .
N1 C3 C4 C4 0.0(7) 2_656 2_656
N1 C3 C4 C5 -179.7(3) 2_656 .
N2 C13 C14 C9 178.3(3) . .
C1 C2 C3 N1 179.8(4) . 2_656
C1 C2 C3 C4 0.5(6) . .
C2 C1 C6 C5 0.2(6) . .
C2 C3 C4 C4 179.4(4) . 2_656
C2 C3 C4 C5 -0.3(6) . .
C3 N1 C7 C5 1.2(6) 2_656 .
C3 N1 C7 C8 -179.5(3) 2_656 .
C3 C4 C5 C6 0.1(6) . .
C3 C4 C5 C7 -179.3(4) . .
C4 C4 C5 C6 -179.6(4) 2_656 .
C4 C4 C5 C7 1.0(7) 2_656 .
C4 C5 C6 C1 -0.1(6) . .
C4 C5 C7 N1 -1.5(6) . .
C4 C5 C7 C8 179.2(4) . .
C6 C1 C2 C3 -0.4(6) . .
C6 C5 C7 N1 179.1(4) . .
C6 C5 C7 C8 -0.1(6) . .
C7 C5 C6 C1 179.3(4) . .
C9 C10 C11 C12 0.4(6) . .
C9 C10 C11 C15 -177.6(4) . 2_776
C10 C9 C14 C13 1.6(6) . .
C10 C11 C12 C12 -177.6(4) . 2_776
C10 C11 C12 C13 0.8(6) . .
C11 C12 C13 N2 -179.5(4) . .
C11 C12 C13 C14 -0.9(6) . .
C12 C12 C13 N2 -1.1(7) 2_776 .
C12 C12 C13 C14 177.5(4) 2_776 .
C12 C13 C14 C9 -0.3(6) . .
C13 N2 C15 C11 1.5(6) . 2_776
C13 N2 C15 C16 179.9(3) . .
C14 C9 C10 C11 -1.7(6) . .
C15 N2 C13 C12 -0.4(6) . .
C15 N2 C13 C14 -179.0(4) . .
C15 C11 C12 C12 0.6(7) 2_776 2_776
C15 C11 C12 C13 179.0(3) 2_776 .
