#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:28:59 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/62/4036237.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_4036237
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         'C9 H6 B Cl F2 N2'
_chemical_formula_sum            'C9 H6 B Cl F2 N2'
_chemical_formula_weight         226.42
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 101.2270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6639(2)
_cell_length_b                   13.5236(3)
_cell_length_c                   9.0732(2)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      40.13
_cell_measurement_theta_min      2.71
_cell_volume                     922.38(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38035
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         40.25
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_correction_T_min  0.8878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         5796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                4798
_reflns_number_total             5796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo5b01147_si_013.cif
_cod_data_source_block           NZhao35
_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_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               4036237
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 0.53019(2) 0.243269(12) 0.536831(19) 0.01845(4) Uani 1 1 d .
F1 F 0.26856(6) 0.47331(3) 0.02632(5) 0.01713(8) Uani 1 1 d .
F2 F 0.18556(6) 0.56585(3) 0.20839(5) 0.01829(8) Uani 1 1 d .
N1 N 0.46615(7) 0.47854(4) 0.26903(6) 0.01237(8) Uani 1 1 d .
N2 N 0.17944(7) 0.38805(4) 0.23316(6) 0.01143(8) Uani 1 1 d .
C1 C 0.59341(9) 0.54500(5) 0.25903(8) 0.01640(10) Uani 1 1 d .
H1 H 0.5781 0.6010 0.1947 0.020 Uiso 1 1 calc R
C2 C 0.75279(9) 0.51984(5) 0.35753(8) 0.01848(11) Uani 1 1 d .
H2 H 0.8619 0.5552 0.3713 0.022 Uiso 1 1 calc R
C3 C 0.72045(8) 0.43387(5) 0.43060(8) 0.01602(10) Uani 1 1 d .
H3 H 0.8029 0.3989 0.5040 0.019 Uiso 1 1 calc R
C4 C 0.54071(8) 0.40815(4) 0.37483(7) 0.01228(9) Uani 1 1 d .
C5 C 0.43672(8) 0.32978(4) 0.40665(7) 0.01202(9) Uani 1 1 d .
C6 C 0.25950(8) 0.31804(4) 0.33706(6) 0.01133(9) Uani 1 1 d .
C7 C 0.13252(8) 0.24478(4) 0.35189(7) 0.01366(10) Uani 1 1 d .
H7 H 0.1511 0.1881 0.4149 0.016 Uiso 1 1 calc R
C8 C -0.02442(8) 0.27167(5) 0.25649(8) 0.01603(10) Uani 1 1 d .
H8 H -0.1341 0.2369 0.2419 0.019 Uiso 1 1 calc R
C9 C 0.00922(8) 0.36016(5) 0.18536(7) 0.01487(10) Uani 1 1 d .
H9 H -0.0758 0.3951 0.1140 0.018 Uiso 1 1 calc R
B1 B 0.27136(9) 0.47987(5) 0.17956(8) 0.01231(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01827(7) 0.01545(7) 0.01821(7) 0.00563(5) -0.00485(5) 0.00026(4)
F1 0.02292(19) 0.01822(17) 0.00992(15) 0.00147(13) 0.00233(13) -0.00188(14)
F2 0.02151(19) 0.00988(15) 0.0229(2) -0.00068(13) 0.00278(15) 0.00398(13)
N1 0.0146(2) 0.01121(18) 0.01151(19) 0.00020(14) 0.00314(15) -0.00136(15)
N2 0.01209(18) 0.01021(17) 0.01147(19) 0.00156(14) 0.00099(15) 0.00090(14)
C1 0.0184(3) 0.0154(2) 0.0165(2) 0.0005(2) 0.0061(2) -0.00391(19)
C2 0.0156(2) 0.0205(3) 0.0199(3) -0.0018(2) 0.0048(2) -0.0051(2)
C3 0.0135(2) 0.0184(2) 0.0156(2) -0.0019(2) 0.00141(19) -0.00190(18)
C4 0.0129(2) 0.0124(2) 0.0111(2) -0.00054(16) 0.00124(17) -0.00067(16)
C5 0.0135(2) 0.01069(19) 0.0110(2) 0.00080(16) 0.00030(17) 0.00069(16)
C6 0.0124(2) 0.00989(19) 0.0110(2) 0.00109(16) 0.00056(16) 0.00051(15)
C7 0.0138(2) 0.0114(2) 0.0154(2) 0.00207(17) 0.00194(18) -0.00037(16)
C8 0.0130(2) 0.0144(2) 0.0198(3) 0.0027(2) 0.0012(2) -0.00090(18)
C9 0.0124(2) 0.0145(2) 0.0166(2) 0.00228(19) -0.00006(18) 0.00094(17)
B1 0.0157(3) 0.0098(2) 0.0112(2) 0.00066(18) 0.00194(19) 0.00092(18)
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C1 N1 C4 107.35(5)
C1 N1 B1 126.41(5)
C4 N1 B1 126.24(5)
C9 N2 C6 107.43(5)
C9 N2 B1 126.43(5)
C6 N2 B1 126.13(5)
N1 C1 C2 110.32(6)
N1 C1 H1 124.8
C2 C1 H1 124.8
C3 C2 C1 107.03(6)
C3 C2 H2 126.5
C1 C2 H2 126.5
C2 C3 C4 106.72(6)
C2 C3 H3 126.6
C4 C3 H3 126.6
C5 C4 N1 119.30(5)
C5 C4 C3 132.12(6)
N1 C4 C3 108.57(5)
C4 C5 C6 122.79(5)
C4 C5 Cl1 118.90(4)
C6 C5 Cl1 118.31(4)
C5 C6 N2 119.52(5)
C5 C6 C7 131.78(5)
N2 C6 C7 108.69(5)
C8 C7 C6 106.64(5)
C8 C7 H7 126.7
C6 C7 H7 126.7
C7 C8 C9 107.17(5)
C7 C8 H8 126.4
C9 C8 H8 126.4
N2 C9 C8 110.07(5)
N2 C9 H9 125.0
C8 C9 H9 125.0
F2 B1 F1 109.09(5)
F2 B1 N2 110.57(5)
F1 B1 N2 110.06(5)
F2 B1 N1 110.73(5)
F1 B1 N1 110.37(5)
N2 B1 N1 105.99(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7168(6)
F1 B1 1.3892(8)
F2 B1 1.3856(8)
N1 C1 1.3423(8)
N1 C4 1.3931(8)
N1 B1 1.5544(9)
N2 C9 1.3460(8)
N2 C6 1.3915(7)
N2 B1 1.5518(8)
C1 C2 1.4077(10)
C1 H1 0.9500
C2 C3 1.3844(10)
C2 H2 0.9500
C3 C4 1.4153(9)
C3 H3 0.9500
C4 C5 1.3898(8)
C5 C6 1.3909(8)
C6 C7 1.4134(8)
C7 C8 1.3866(9)
C7 H7 0.9500
C8 C9 1.4071(9)
C8 H8 0.9500
C9 H9 0.9500
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
C4 N1 C1 C2 -0.10(7)
B1 N1 C1 C2 179.75(6)
N1 C1 C2 C3 0.07(8)
C1 C2 C3 C4 -0.01(8)
C1 N1 C4 C5 -179.69(6)
B1 N1 C4 C5 0.47(9)
C1 N1 C4 C3 0.09(7)
B1 N1 C4 C3 -179.75(6)
C2 C3 C4 C5 179.69(7)
C2 C3 C4 N1 -0.05(7)
N1 C4 C5 C6 0.02(9)
C3 C4 C5 C6 -179.70(6)
N1 C4 C5 Cl1 179.82(4)
C3 C4 C5 Cl1 0.10(10)
C4 C5 C6 N2 -1.39(9)
Cl1 C5 C6 N2 178.81(4)
C4 C5 C6 C7 179.53(6)
Cl1 C5 C6 C7 -0.27(9)
C9 N2 C6 C5 -179.00(6)
B1 N2 C6 C5 2.41(9)
C9 N2 C6 C7 0.28(7)
B1 N2 C6 C7 -178.31(6)
C5 C6 C7 C8 178.94(7)
N2 C6 C7 C8 -0.22(7)
C6 C7 C8 C9 0.08(8)
C6 N2 C9 C8 -0.23(7)
B1 N2 C9 C8 178.36(6)
C7 C8 C9 N2 0.09(8)
C9 N2 B1 F2 59.84(8)
C6 N2 B1 F2 -121.83(6)
C9 N2 B1 F1 -60.76(8)
C6 N2 B1 F1 117.57(6)
C9 N2 B1 N1 179.89(6)
C6 N2 B1 N1 -1.78(8)
C1 N1 B1 F2 -59.55(8)
C4 N1 B1 F2 120.27(6)
C1 N1 B1 F1 61.35(8)
C4 N1 B1 F1 -118.83(6)
C1 N1 B1 N2 -179.49(6)
C4 N1 B1 N2 0.32(8)
