#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:31:50 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234445 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/62/4036246.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_4036246
loop_
_publ_author_name
'Zhao, Ning'
'Xuan, Sunting'
'Fronczek, Frank R.'
'Smith, Kevin M.'
'Vicente, M Graça H'
_publ_section_title
;
 Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective
 Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8377
_journal_page_last               8383
_journal_paper_doi               10.1021/acs.joc.5b01147
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C29 H17 B F2 N2 S5'
_chemical_formula_sum            'C29 H17 B F2 N2 S5'
_chemical_formula_weight         602.56
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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
_cell_angle_beta                 120.434(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.337(2)
_cell_length_b                   10.7880(10)
_cell_length_c                   13.697(2)
_cell_measurement_reflns_used    5884
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      2.546
_cell_volume                     2591.0(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Nonius KappaCCD '
_diffrn_measurement_method       'φ and ω scans'
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21886
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_correction_T_min  0.8441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0407
_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)+(0.0503P)²+2.8336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                2490
_reflns_number_total             3087
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo5b01147_si_004.cif
_cod_data_source_block           Compound8
_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_cell_volume        2591.0(5)
_cod_original_sg_symbol_H-M      'C 2/c         '
_cod_database_code               4036246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.20440(3) 0.35120(5) 0.06046(5) 0.04439(17) Uani 1 1 d . . .
F1 F 0.05190(6) 0.22855(10) 0.33833(9) 0.0341(3) Uani 1 1 d . . .
N1 N 0.04194(8) 0.38990(14) 0.20768(13) 0.0296(3) Uani 1 1 d . . .
C1 C 0.08250(10) 0.35547(16) 0.15786(15) 0.0295(4) Uani 1 1 d . A .
C2 C 0.10461(10) 0.46217(17) 0.12108(15) 0.0306(4) Uani 1 1 d . . .
C3 C 0.07595(10) 0.56359(17) 0.14978(16) 0.0323(4) Uani 1 1 d . . .
H3 H 0.0810 0.6480 0.1350 0.039 Uiso 1 1 calc R . .
C4 C 0.03812(10) 0.51926(16) 0.20450(16) 0.0314(4) Uani 1 1 d . . .
C5 C 0.0000 0.5840(2) 0.2500 0.0314(6) Uani 1 2 d S . .
C6 C 0.09999(11) 0.22626(17) 0.14636(15) 0.0307(4) Uani 1 1 d D . .
S1 S 0.04767(12) 0.15539(13) 0.01847(18) 0.0379(5) Uani 0.415(3) 1 d PD A 1
C7 C 0.1558(6) 0.1470(9) 0.2207(8) 0.049(3) Uani 0.415(3) 1 d PD A 1
H7 H 0.1862 0.1665 0.2989 0.059 Uiso 0.415(3) 1 calc PR A 1
S1A S 0.18138(11) 0.16008(16) 0.25569(15) 0.0425(4) Uani 0.585(3) 1 d PD A 2
C7A C 0.0712(3) 0.1530(5) 0.0538(4) 0.0360(14) Uiso 0.585(3) 1 d PD A 2
H7A H 0.0296 0.1787 -0.0169 0.043 Uiso 0.585(3) 1 calc PR A 2
C8 C 0.16631(15) 0.0326(2) 0.1753(2) 0.0485(6) Uani 1 1 d D . .
H8 H 0.2052 -0.0279 0.2120 0.058 Uiso 1 1 calc R A 1
C9 C 0.10716(13) 0.03320(19) 0.06791(19) 0.0417(5) Uani 1 1 d D A .
H9 H 0.0990 -0.0358 0.0199 0.050 Uiso 1 1 calc R B 1
C10 C 0.14893(11) 0.46986(18) 0.06416(16) 0.0328(4) Uani 1 1 d . . .
C11 C 0.15499(12) 0.5752(2) 0.01065(16) 0.0380(4) Uani 1 1 d . . .
H11 H 0.1290 0.6509 0.0034 0.046 Uiso 1 1 calc R . .
C12 C 0.20536(13) 0.5549(2) -0.03192(17) 0.0445(5) Uani 1 1 d . . .
H12 H 0.2163 0.6164 -0.0714 0.053 Uiso 1 1 calc R . .
C13 C 0.23580(13) 0.4405(2) -0.01075(19) 0.0453(5) Uani 1 1 d . . .
H13 H 0.2707 0.4126 -0.0328 0.054 Uiso 1 1 calc R . .
C14 C 0.0000 0.7195(2) 0.2500 0.0335(6) Uani 1 2 d SD . .
S3 S -0.0766(2) 0.8066(3) 0.2219(4) 0.0349(6) Uani 0.50 1 d PD C 1
C15 C 0.0618(8) 0.8017(12) 0.2807(17) 0.039(3) Uani 0.50 1 d PD . 2
H15 H 0.1128 0.7759 0.3074 0.047 Uiso 0.50 1 calc PR . 2
C16 C -0.03698(17) 0.9327(2) 0.2339(2) 0.0614(8) Uani 1 1 d D . .
H16 H -0.0652 1.0075 0.2189 0.074 Uiso 1 1 d R C .
B1 B 0.0000 0.3022(3) 0.2500 0.0306(6) Uani 1 2 d S . .
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'
F F 0.0171 0.0103 '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'
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
C13 S2 C10 92.14(11) . .
C1 N1 C4 107.17(15) . .
C1 N1 B1 126.99(15) . .
C4 N1 B1 125.58(16) . .
N1 C1 C2 109.77(16) . .
N1 C1 C6 123.67(17) . .
C2 C1 C6 126.56(17) . .
C3 C2 C1 106.58(17) . .
C3 C2 C10 124.56(18) . .
C1 C2 C10 128.86(17) . .
C2 C3 C4 107.80(17) . .
C2 C3 H3 126.1 . .
C4 C3 H3 126.1 . .
N1 C4 C3 108.68(16) . .
N1 C4 C5 121.22(18) . .
C3 C4 C5 130.09(17) . .
C4 C5 C4 120.2(2) . 2
C4 C5 C14 119.88(12) . .
C4 C5 C14 119.88(12) 2 .
C7A C6 C7 97.7(4) . .
C7A C6 C1 130.1(3) . .
C7 C6 C1 131.8(4) . .
C7 C6 S1 109.5(4) . .
C1 C6 S1 118.57(14) . .
C7A C6 S1A 110.0(2) . .
C1 C6 S1A 118.56(14) . .
S1 C6 S1A 122.13(13) . .
C9 S1 C6 89.45(14) . .
C6 C7 C8 117.4(6) . .
C6 C7 H7 121.3 . .
C8 C7 H7 121.3 . .
C8 S1A C6 89.63(13) . .
C6 C7A C9 116.6(4) . .
C6 C7A H7A 121.7 . .
C9 C7A H7A 121.7 . .
C9 C8 C7 102.7(4) . .
C9 C8 S1A 118.31(18) . .
C9 C8 H8 128.6 . .
C7 C8 H8 128.6 . .
S1A C8 H8 112.8 . .
C8 C9 C7A 105.1(3) . .
C8 C9 S1 120.34(19) . .
C8 C9 H9 119.8 . .
C7A C9 H9 135.0 . .
S1 C9 H9 119.8 . .
C11 C10 C2 124.76(18) . .
C11 C10 S2 110.93(15) . .
C2 C10 S2 124.24(14) . .
C10 C11 C12 111.3(2) . .
C10 C11 H11 124.4 . .
C12 C11 H11 124.4 . .
C13 C12 C11 113.5(2) . .
C13 C12 H12 123.2 . .
C11 C12 H12 123.2 . .
C12 C13 S2 112.10(18) . .
C12 C13 H13 123.9 . .
S2 C13 H13 123.9 . .
C15 C14 C15 102.5(11) . 2
C15 C14 C5 128.7(6) . .
C15 C14 C5 128.7(6) 2 .
C15 C14 S3 107.3(5) 2 2
C5 C14 S3 123.80(13) . 2
C15 C14 S3 107.3(5) . .
C5 C14 S3 123.80(13) . .
S3 C14 S3 112.4(3) 2 .
C16 S3 C14 95.4(2) . .
C14 C15 C16 111.5(9) . 2
C14 C15 H15 124.3 . .
C16 C15 H15 124.3 2 .
C16 C16 C15 107.1(5) 2 2
C16 C16 S3 118.31(16) 2 .
C16 C16 H16 121.8 2 .
C15 C16 H16 130.9 2 .
S3 C16 H16 119.9 . .
F1 B1 F1 109.9(2) . 2
F1 B1 N1 110.65(7) . .
F1 B1 N1 109.88(7) 2 .
F1 B1 N1 109.88(7) . 2
F1 B1 N1 110.65(7) 2 2
N1 B1 N1 105.8(2) . 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S2 C13 1.708(2) .
S2 C10 1.724(2) .
F1 B1 1.384(2) .
N1 C1 1.362(2) .
N1 C4 1.397(2) .
N1 B1 1.568(2) .
C1 C2 1.418(3) .
C1 C6 1.467(3) .
C2 C3 1.387(3) .
C2 C10 1.463(3) .
C3 C4 1.402(3) .
C3 H3 0.9500 .
C4 C5 1.403(2) .
C5 C4 1.403(2) 2
C5 C14 1.461(4) .
C6 C7A 1.350(5) .
C6 C7 1.373(10) .
C6 S1 1.702(3) .
C6 S1A 1.727(2) .
S1 C9 1.682(3) .
C7 C8 1.445(9) .
C7 H7 0.9500 .
S1A C8 1.690(3) .
C7A C9 1.449(5) .
C7A H7A 0.9500 .
C8 C9 1.348(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.391(3) .
C11 C12 1.429(3) .
C11 H11 0.9500 .
C12 C13 1.345(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.417(12) .
C14 C15 1.417(12) 2
C14 S3 1.689(4) 2
C14 S3 1.689(4) .
S3 C16 1.547(4) .
C15 C16 1.480(13) 2
C15 H15 0.9500 .
C16 C16 1.336(6) 2
C16 C15 1.480(13) 2
C16 H16 0.9500 .
B1 F1 1.384(2) 2
B1 N1 1.568(2) 2
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
C4 N1 C1 C2 -0.6(2) . .
B1 N1 C1 C2 173.80(13) . .
C4 N1 C1 C6 179.03(17) . .
B1 N1 C1 C6 -6.6(3) . .
N1 C1 C2 C3 -0.2(2) . .
C6 C1 C2 C3 -179.76(18) . .
N1 C1 C2 C10 179.64(17) . .
C6 C1 C2 C10 0.1(3) . .
C1 C2 C3 C4 0.9(2) . .
C10 C2 C3 C4 -178.98(17) . .
C1 N1 C4 C3 1.1(2) . .
B1 N1 C4 C3 -173.36(13) . .
C1 N1 C4 C5 -179.75(14) . .
B1 N1 C4 C5 5.8(2) . .
C2 C3 C4 N1 -1.2(2) . .
C2 C3 C4 C5 179.72(16) . .
N1 C4 C5 C4 -2.80(12) . 2
C3 C4 C5 C4 176.2(2) . 2
N1 C4 C5 C14 177.20(12) . .
C3 C4 C5 C14 -3.8(2) . .
N1 C1 C6 C7A 107.3(4) . .
C2 C1 C6 C7A -73.2(4) . .
N1 C1 C6 C7 -81.8(8) . .
C2 C1 C6 C7 97.7(8) . .
N1 C1 C6 S1 102.0(2) . .
C2 C1 C6 S1 -78.5(2) . .
N1 C1 C6 S1A -87.7(2) . .
C2 C1 C6 S1A 91.8(2) . .
C7A C6 S1 C9 11.6(12) . .
C7 C6 S1 C9 -4.8(6) . .
C1 C6 S1 C9 172.24(17) . .
S1A C6 S1 C9 2.30(19) . .
C7A C6 C7 C8 4.9(10) . .
C1 C6 C7 C8 -168.1(4) . .
S1 C6 C7 C8 8.4(10) . .
S1A C6 C7 C8 -146(3) . .
C7A C6 S1A C8 -5.6(3) . .
C7 C6 S1A C8 25(2) . .
C1 C6 S1A C8 -173.46(17) . .
S1 C6 S1A C8 -3.5(2) . .
C7 C6 C7A C9 -0.4(7) . .
C1 C6 C7A C9 172.8(2) . .
S1 C6 C7A C9 -164.9(15) . .
S1A C6 C7A C9 6.8(5) . .
C6 C7 C8 C9 -7.6(10) . .
C6 C7 C8 S1A 151(3) . .
C6 S1A C8 C9 3.6(2) . .
C6 S1A C8 C7 -19.8(18) . .
C7 C8 C9 C7A 6.2(6) . .
S1A C8 C9 C7A -0.6(3) . .
C7 C8 C9 S1 3.7(6) . .
S1A C8 C9 S1 -3.1(3) . .
C6 C7A C9 C8 -4.1(5) . .
C6 C7A C9 S1 167.8(12) . .
C6 S1 C9 C8 0.5(2) . .
C6 S1 C9 C7A -8.6(9) . .
C3 C2 C10 C11 -14.0(3) . .
C1 C2 C10 C11 166.22(19) . .
C3 C2 C10 S2 162.76(15) . .
C1 C2 C10 S2 -17.0(3) . .
C13 S2 C10 C11 0.28(16) . .
C13 S2 C10 C2 -176.85(17) . .
C2 C10 C11 C12 177.10(18) . .
S2 C10 C11 C12 0.0(2) . .
C10 C11 C12 C13 -0.4(3) . .
C11 C12 C13 S2 0.6(3) . .
C10 S2 C13 C12 -0.50(18) . .
C4 C5 C14 C15 -45.4(10) . .
C4 C5 C14 C15 134.6(10) 2 .
C4 C5 C14 C15 134.6(10) . 2
C4 C5 C14 C15 -45.4(10) 2 2
C4 C5 C14 S3 -39.9(2) . 2
C4 C5 C14 S3 140.1(2) 2 2
C4 C5 C14 S3 140.1(2) . .
C4 C5 C14 S3 -39.9(2) 2 .
C15 C14 S3 C16 5.7(11) . .
C15 C14 S3 C16 -39(8) 2 .
C5 C14 S3 C16 -178.78(13) . .
S3 C14 S3 C16 1.22(13) 2 .
C15 C14 C15 C16 -1.3(5) 2 2
C5 C14 C15 C16 178.7(5) . 2
S3 C14 C15 C16 135(9) 2 2
S3 C14 C15 C16 -6.1(16) . 2
C14 S3 C16 C16 -4.0(4) . 2
C14 S3 C16 C15 19(4) . 2
C1 N1 B1 F1 64.8(2) . .
C4 N1 B1 F1 -121.83(19) . .
C1 N1 B1 F1 -56.7(2) . 2
C4 N1 B1 F1 116.6(2) . 2
C1 N1 B1 N1 -176.22(18) . 2
C4 N1 B1 N1 -2.86(12) . 2
