#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:11:19 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234592 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036353.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_4036353
loop_
_publ_author_name
'Wang, Xinyang'
'Zhang, Fan'
'Gao, Jianhua'
'Fu, Yubin'
'Zhao, Wuxue'
'Tang, Ruizhi'
'Zhang, Wanzheng'
'Zhuang, Xiaodong'
'Feng, Xinliang'
_publ_section_title
;
 Synthesis and Properties of C(2h)-Symmetric BN-Heteroacenes Tailored
 through Aromatic Central Cores.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10127
_journal_page_last               10133
_journal_paper_doi               10.1021/acs.joc.5b01718
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C42 H38 B2 N2 O2 S2'
_chemical_formula_weight         688.48
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.2880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.0682(4)
_cell_length_b                   10.3044(3)
_cell_length_c                   15.0172(5)
_cell_measurement_temperature    173(2)
_cell_volume                     1801.39(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex II 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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20472
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9564
_exptl_absorpt_correction_T_min  0.9154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0435
_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)+(0.0759P)²+1.1977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                2805
_reflns_number_total             3178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01718_si_002.cif
_cod_data_source_block           3d
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4036353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S1 S 0.81606(4) 0.64545(5) 0.07025(3) 0.02825(18) Uani 1 1 d .
N1 N 0.95092(15) 0.43974(17) 0.34154(12) 0.0309(4) Uani 1 1 d .
H1A H 0.9789 0.4020 0.3954 0.037 Uiso 1 1 calc R
B1 B 1.0174(2) 0.4328(2) 0.27680(16) 0.0282(5) Uani 1 1 d .
C1 C 0.69775(19) 0.6383(2) 0.23242(16) 0.0359(5) Uani 1 1 d .
H1B H 0.6681 0.6870 0.1776 0.043 Uiso 1 1 calc R
C2 C 0.6388(2) 0.6357(2) 0.29947(18) 0.0439(6) Uani 1 1 d .
H2A H 0.5683 0.6813 0.2904 0.053 Uiso 1 1 calc R
C3 C 0.6827(2) 0.5661(2) 0.38064(17) 0.0439(6) Uani 1 1 d .
H3A H 0.6417 0.5645 0.4266 0.053 Uiso 1 1 calc R
C4 C 0.7847(2) 0.4996(2) 0.39487(16) 0.0385(5) Uani 1 1 d .
H4A H 0.8140 0.4528 0.4506 0.046 Uiso 1 1 calc R
C5 C 0.84555(17) 0.5008(2) 0.32727(14) 0.0306(5) Uani 1 1 d .
C6 C 0.80151(17) 0.56952(19) 0.24429(14) 0.0293(4) Uani 1 1 d .
C7 C 0.86260(16) 0.56102(19) 0.17380(14) 0.0267(4) Uani 1 1 d .
C8 C 0.95830(16) 0.48385(18) 0.17933(14) 0.0263(4) Uani 1 1 d .
C9 C 0.98790(16) 0.48152(18) 0.09121(13) 0.0246(4) Uani 1 1 d .
C10 C 0.92085(16) 0.57018(18) 0.02694(13) 0.0245(4) Uani 1 1 d .
C11 C 1.06792(16) 0.40440(18) 0.06136(13) 0.0248(4) Uani 1 1 d .
C12 C 1.13431(18) 0.2935(2) 0.11519(14) 0.0325(5) Uani 1 1 d .
H12A H 1.1843 0.2553 0.0803 0.049 Uiso 1 1 calc R
H12B H 1.0807 0.2275 0.1257 0.049 Uiso 1 1 calc R
H12C H 1.1813 0.3254 0.1747 0.049 Uiso 1 1 calc R
C13 C 1.14686(18) 0.3907(2) 0.31425(14) 0.0299(5) Uani 1 1 d .
C14 C 1.1812(2) 0.2760(2) 0.36287(15) 0.0379(5) Uani 1 1 d .
H14A H 1.1247 0.2189 0.3742 0.045 Uiso 1 1 calc R
C15 C 1.2967(2) 0.2436(2) 0.39517(17) 0.0454(6) Uani 1 1 d .
H15A H 1.3182 0.1638 0.4267 0.054 Uiso 1 1 calc R
C16 C 1.3796(2) 0.3262(3) 0.38170(17) 0.0446(6) Uani 1 1 d .
H16A H 1.4585 0.3042 0.4042 0.054 Uiso 1 1 calc R
C17 C 1.3482(2) 0.4416(2) 0.33534(18) 0.0428(6) Uani 1 1 d .
H17A H 1.4056 0.4996 0.3266 0.051 Uiso 1 1 calc R
C18 C 1.23302(19) 0.4732(2) 0.30146(16) 0.0365(5) Uani 1 1 d .
H18A H 1.2125 0.5525 0.2690 0.044 Uiso 1 1 calc R
O01 O 0.97424(17) 0.2847(2) 0.51413(15) 0.0665(6) Uani 1 1 d .
C01 C 1.1204(3) 0.1356(4) 0.5761(3) 0.0908(13) Uani 1 1 d .
H01A H 1.1431 0.1525 0.5191 0.136 Uiso 1 1 calc R
H01B H 1.1038 0.0430 0.5799 0.136 Uiso 1 1 calc R
H01C H 1.1830 0.1607 0.6294 0.136 Uiso 1 1 calc R
C02 C 1.0167(2) 0.2119(2) 0.57568(17) 0.0439(6) Uani 1 1 d .
C03 C 0.9706(3) 0.1973(4) 0.6578(2) 0.0680(9) Uani 1 1 d .
H03A H 0.9030 0.2529 0.6506 0.102 Uiso 1 1 calc R
H03B H 1.0296 0.2228 0.7134 0.102 Uiso 1 1 calc R
H03C H 0.9490 0.1066 0.6633 0.102 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 0.0033 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'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C7 S1 C10 90.91(9) .
C5 N1 B1 125.48(18) .
C5 N1 H1A 117.3 .
B1 N1 H1A 117.3 .
N1 B1 C8 115.48(18) .
N1 B1 C13 117.19(18) .
C8 B1 C13 126.87(18) .
C2 C1 C6 120.7(2) .
C2 C1 H1B 119.7 .
C6 C1 H1B 119.7 .
C1 C2 C3 120.0(2) .
C1 C2 H2A 120.0 .
C3 C2 H2A 120.0 .
C4 C3 C2 120.7(2) .
C4 C3 H3A 119.7 .
C2 C3 H3A 119.7 .
C3 C4 C5 120.1(2) .
C3 C4 H4A 119.9 .
C5 C4 H4A 119.9 .
N1 C5 C4 121.28(19) .
N1 C5 C6 118.83(18) .
C4 C5 C6 119.84(19) .
C1 C6 C5 118.68(19) .
C1 C6 C7 123.13(19) .
C5 C6 C7 118.13(18) .
C8 C7 C6 124.70(18) .
C8 C7 S1 114.06(15) .
C6 C7 S1 121.20(15) .
C7 C8 C9 110.75(17) .
C7 C8 B1 114.98(18) .
C9 C8 B1 133.84(17) .
C11 C9 C10 117.52(17) .
C11 C9 C8 130.45(18) .
C10 C9 C8 112.00(16) .
C11 C10 C9 126.03(18) 3_765
C11 C10 S1 122.15(15) 3_765
C9 C10 S1 111.81(14) .
C10 C11 C9 116.28(18) 3_765
C10 C11 C12 118.89(17) 3_765
C9 C11 C12 124.70(18) .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C14 C13 C18 117.34(19) .
C14 C13 B1 123.43(19) .
C18 C13 B1 119.19(18) .
C15 C14 C13 121.3(2) .
C15 C14 H14A 119.4 .
C13 C14 H14A 119.4 .
C16 C15 C14 120.2(2) .
C16 C15 H15A 119.9 .
C14 C15 H15A 119.9 .
C15 C16 C17 119.7(2) .
C15 C16 H16A 120.1 .
C17 C16 H16A 120.1 .
C16 C17 C18 120.2(2) .
C16 C17 H17A 119.9 .
C18 C17 H17A 119.9 .
C17 C18 C13 121.1(2) .
C17 C18 H18A 119.4 .
C13 C18 H18A 119.4 .
C02 C01 H01A 109.5 .
C02 C01 H01B 109.5 .
H01A C01 H01B 109.5 .
C02 C01 H01C 109.5 .
H01A C01 H01C 109.5 .
H01B C01 H01C 109.5 .
O01 C02 C01 121.8(3) .
O01 C02 C03 121.7(3) .
C01 C02 C03 116.4(2) .
C02 C03 H03A 109.5 .
C02 C03 H03B 109.5 .
H03A C03 H03B 109.5 .
C02 C03 H03C 109.5 .
H03A C03 H03C 109.5 .
H03B C03 H03C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.741(2) .
S1 C10 1.7487(19) .
N1 C5 1.384(3) .
N1 B1 1.416(3) .
N1 H1A 0.8800 .
B1 C8 1.542(3) .
B1 C13 1.575(3) .
C1 C2 1.378(3) .
C1 C6 1.409(3) .
C1 H1B 0.9500 .
C2 C3 1.393(4) .
C2 H2A 0.9500 .
C3 C4 1.375(3) .
C3 H3A 0.9500 .
C4 C5 1.401(3) .
C4 H4A 0.9500 .
C5 C6 1.410(3) .
C6 C7 1.443(3) .
C7 C8 1.386(3) .
C8 C9 1.459(3) .
C9 C11 1.412(3) .
C9 C10 1.417(3) .
C10 C11 1.393(3) 3_765
C11 C10 1.393(3) 3_765
C11 C12 1.503(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.393(3) .
C13 C18 1.395(3) .
C14 C15 1.390(3) .
C14 H14A 0.9500 .
C15 C16 1.368(4) .
C15 H15A 0.9500 .
C16 C17 1.380(4) .
C16 H16A 0.9500 .
C17 C18 1.387(3) .
C17 H17A 0.9500 .
C18 H18A 0.9500 .
O01 C02 1.196(3) .
C01 C02 1.476(4) .
C01 H01A 0.9800 .
C01 H01B 0.9800 .
C01 H01C 0.9800 .
C02 C03 1.488(4) .
C03 H03A 0.9800 .
C03 H03B 0.9800 .
C03 H03C 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_4
C5 N1 B1 C8 -7.8(3) .
C5 N1 B1 C13 164.95(18) .
C6 C1 C2 C3 1.0(4) .
C1 C2 C3 C4 0.1(4) .
C2 C3 C4 C5 -0.3(4) .
B1 N1 C5 C4 178.3(2) .
B1 N1 C5 C6 -4.1(3) .
C3 C4 C5 N1 177.0(2) .
C3 C4 C5 C6 -0.5(3) .
C2 C1 C6 C5 -1.8(3) .
C2 C1 C6 C7 175.4(2) .
N1 C5 C6 C1 -176.10(19) .
C4 C5 C6 C1 1.5(3) .
N1 C5 C6 C7 6.6(3) .
C4 C5 C6 C7 -175.77(19) .
C1 C6 C7 C8 -173.2(2) .
C5 C6 C7 C8 4.0(3) .
C1 C6 C7 S1 4.3(3) .
C5 C6 C7 S1 -178.60(15) .
C10 S1 C7 C8 3.55(16) .
C10 S1 C7 C6 -174.13(17) .
C6 C7 C8 C9 170.86(18) .
S1 C7 C8 C9 -6.7(2) .
C6 C7 C8 B1 -15.6(3) .
S1 C7 C8 B1 166.84(14) .
N1 B1 C8 C7 16.8(3) .
C13 B1 C8 C7 -155.13(19) .
N1 B1 C8 C9 -171.55(19) .
C13 B1 C8 C9 16.5(4) .
C7 C8 C9 C11 -170.85(19) .
B1 C8 C9 C11 17.2(4) .
C7 C8 C9 C10 7.2(2) .
B1 C8 C9 C10 -164.7(2) .
C11 C9 C10 C11 -5.0(3) 3_765
C8 C9 C10 C11 176.65(18) 3_765
C11 C9 C10 S1 173.70(14) .
C8 C9 C10 S1 -4.6(2) .
C7 S1 C10 C11 179.54(17) 3_765
C7 S1 C10 C9 0.76(15) .
C10 C9 C11 C10 4.5(3) 3_765
C8 C9 C11 C10 -177.51(18) 3_765
C10 C9 C11 C12 -171.32(18) .
C8 C9 C11 C12 6.6(3) .
N1 B1 C13 C14 55.2(3) .
C8 B1 C13 C14 -133.0(2) .
N1 B1 C13 C18 -122.6(2) .
C8 B1 C13 C18 49.2(3) .
C18 C13 C14 C15 -1.7(3) .
B1 C13 C14 C15 -179.5(2) .
C13 C14 C15 C16 1.7(4) .
C14 C15 C16 C17 -0.4(4) .
C15 C16 C17 C18 -0.8(4) .
C16 C17 C18 C13 0.8(4) .
C14 C13 C18 C17 0.4(3) .
B1 C13 C18 C17 178.3(2) .
