#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:38:03 +0300 (Tue, 05 May 2020) $
#$Revision: 251540 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/61/7126145.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_7126145
loop_
_publ_author_name
'Shan, Xiang-Huan'
'Yang, Bo'
'Qu, Jian-Ping'
'Kang, Yan-Biao'
_publ_section_title
;
 CuSO₄-Catalyzed dual annulation to synthesize O, S or
 N-containing tetracyclic heteroacenes.
;
_journal_issue                   29
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4063
_journal_page_last               4066
_journal_paper_doi               10.1039/d0cc01172j
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H8 Br N O'
_chemical_formula_sum            'C14 H8 Br N O'
_chemical_formula_weight         286.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-11 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.28779(11)
_cell_length_b                   5.59996(10)
_cell_length_c                   24.2843(4)
_cell_measurement_reflns_used    7946
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      73.6760
_cell_measurement_theta_min      5.4350
_cell_volume                     1127.07(3)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9432
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.781
_diffrn_reflns_theta_min         3.640
_exptl_absorpt_coefficient_mu    4.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0305
_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)+(0.0559P)²+0.2593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2201
_reflns_number_total             2233
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01172j2.cif
_cod_data_source_block           y-3-4-1
_cod_depositor_comments
'Adding full bibliography for 7126144--7126145.cif.'
_cod_database_code               7126145
_shelxl_version_number           2013-4
_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   0.495
_shelx_estimated_absorpt_t_min   0.447
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), N1(H1), C3(H3), C6(H6), C10(H10), C13(H13), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34174(6) 0.87852(10) 0.49856(2) 0.0685(2) Uani 1 1 d . . . . .
O1 O 0.6275(3) 0.9769(5) 0.30614(12) 0.0389(5) Uani 1 1 d . . . . .
C11 C 0.8488(4) 0.9245(8) 0.1241(2) 0.0461(9) Uani 1 1 d . . . . .
H11 H 0.9172 1.0231 0.1040 0.055 Uiso 1 1 calc R . . . .
C4 C 0.4757(4) 0.6345(6) 0.32107(15) 0.0348(7) Uani 1 1 d . . . . .
C2 C 0.3413(5) 0.5631(9) 0.4068(2) 0.0475(9) Uani 1 1 d . . . . .
H2 H 0.2762 0.4690 0.4292 0.057 Uiso 1 1 calc R . . . .
N1 N 0.5520(4) 0.4956(5) 0.21927(13) 0.0366(6) Uani 1 1 d . . . . .
H1 H 0.5069 0.3595 0.2136 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5321(4) 0.8516(6) 0.34289(15) 0.0367(7) Uani 1 1 d . . . . .
C14 C 0.6474(4) 0.6207(6) 0.18244(18) 0.0350(8) Uani 1 1 d . . . . .
C3 C 0.3792(5) 0.4884(7) 0.35394(17) 0.0421(8) Uani 1 1 d . . . . .
H3 H 0.3409 0.3434 0.3406 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5430(4) 0.6297(5) 0.26672(15) 0.0348(7) Uani 1 1 d . . . . .
C9 C 0.7025(4) 0.8373(6) 0.20688(15) 0.0334(7) Uani 1 1 d . . . . .
C6 C 0.4978(5) 0.9285(7) 0.39589(17) 0.0430(8) Uani 1 1 d . . . . .
H6 H 0.5376 1.0712 0.4100 0.052 Uiso 1 1 calc R . . . .
C10 C 0.8038(4) 0.9904(7) 0.17691(16) 0.0383(7) Uani 1 1 d . . . . .
H10 H 0.8399 1.1330 0.1922 0.046 Uiso 1 1 calc R . . . .
C13 C 0.6919(5) 0.5583(7) 0.12894(17) 0.0415(8) Uani 1 1 d . . . . .
H13 H 0.6551 0.4180 0.1128 0.050 Uiso 1 1 calc R . . . .
C8 C 0.6310(4) 0.8330(6) 0.26024(15) 0.0342(7) Uani 1 1 d . . . . .
C1 C 0.4007(5) 0.7781(8) 0.42609(15) 0.0460(8) Uani 1 1 d . . . . .
C12 C 0.7932(5) 0.7133(8) 0.10068(16) 0.0462(8) Uani 1 1 d . . . . .
H12 H 0.8249 0.6747 0.0650 0.055 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'
Br Br -0.6763 1.2805 '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
C8 O1 C5 103.8(3) . . ?
C10 C11 C12 121.1(4) . . ?
C5 C4 C7 103.5(3) . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 137.7(3) . . ?
C1 C2 C3 119.8(4) . . ?
C7 N1 C14 107.2(3) . . ?
O1 C5 C4 112.7(3) . . ?
O1 C5 C6 123.9(3) . . ?
C6 C5 C4 123.4(4) . . ?
N1 C14 C9 110.2(3) . . ?
N1 C14 C13 128.8(3) . . ?
C13 C14 C9 121.1(4) . . ?
C2 C3 C4 118.9(4) . . ?
N1 C7 C4 143.3(3) . . ?
C8 C7 C4 107.4(3) . . ?
C8 C7 N1 109.3(3) . . ?
C10 C9 C14 119.7(3) . . ?
C10 C9 C8 136.9(3) . . ?
C8 C9 C14 103.4(3) . . ?
C1 C6 C5 115.1(4) . . ?
C11 C10 C9 118.6(3) . . ?
C12 C13 C14 117.6(4) . . ?
O1 C8 C9 137.4(3) . . ?
C7 C8 O1 112.6(3) . . ?
C7 C8 C9 110.0(3) . . ?
C2 C1 Br1 118.5(3) . . ?
C6 C1 Br1 117.4(3) . . ?
C6 C1 C2 124.1(4) . . ?
C13 C12 C11 121.9(4) . . ?
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 C1 1.911(4) . ?
O1 C5 1.384(5) . ?
O1 C8 1.376(5) . ?
C11 C10 1.385(6) . ?
C11 C12 1.391(7) . ?
C4 C5 1.406(5) . ?
C4 C3 1.395(5) . ?
C4 C7 1.433(5) . ?
C2 C3 1.385(7) . ?
C2 C1 1.383(7) . ?
N1 C14 1.384(5) . ?
N1 C7 1.377(5) . ?
C5 C6 1.387(5) . ?
C14 C9 1.426(5) . ?
C14 C13 1.395(6) . ?
C7 C8 1.362(5) . ?
C9 C10 1.403(5) . ?
C9 C8 1.425(5) . ?
C6 C1 1.376(6) . ?
C13 C12 1.389(6) . ?
