#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:28:13 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/62/4036235.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_4036235
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 H4 B Cl3 F2 N2'
_chemical_formula_sum            'C9 H4 B Cl3 F2 N2'
_chemical_formula_weight         295.30
_space_group_IT_number           138
_space_group_name_Hall           '-P 4ac 2ac'
_space_group_name_H-M_alt        'P 42/n c m :2'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4ac 2ac'
_symmetry_space_group_name_H-M   'P 42/n c m :2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4318(4)
_cell_length_b                   14.4318(4)
_cell_length_c                   5.3189(2)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      30.87
_cell_measurement_theta_min      2.82
_cell_volume                     1107.80(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            28453
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.8975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         934
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0285
_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)+(0.0326P)²+0.7678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                846
_reflns_number_total             934
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo5b01147_si_012.cif
_cod_data_source_block           NZhao41
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Tetragonal' was changed to
'tetragonal' 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 4ac 2ac '
_cod_original_sg_symbol_H-M      'P 42/n c m '
_cod_database_code               4036235
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x, z+1/2'
'y, -x+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'y+1/2, x+1/2, -z'
'-y, -x, -z'
'-x, -y, -z'
'y-1/2, -x, -z-1/2'
'-y, x-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'x-1/2, y-1/2, -z'
'-y-1/2, -x-1/2, z'
'y, x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.33847(2) 0.33847(2) -0.22185(9) 0.02033(14) Uani 1 2 d S
Cl2 Cl 0.35169(4) 0.64831(4) 0.5000 0.0273(2) Uani 0.50 2 d SPD
F1 F 0.33697(9) 0.57985(11) 0.6379(3) 0.0194(3) Uani 0.50 1 d PD
N1 N 0.42627(8) 0.49486(6) 0.32430(19) 0.0156(2) Uani 0.50 1 d PD
C1N C 0.42627(8) 0.49486(6) 0.32430(19) 0.0156(2) Uani 0.50 1 d P
C1 C 0.36359(9) 0.47440(9) 0.1388(2) 0.0169(2) Uani 1 1 d .
H1 H 0.3100 0.5094 0.0968 0.020 Uiso 1 1 d R
C2 C 0.39298(8) 0.39298(8) 0.0227(3) 0.0162(3) Uani 1 2 d S
B1 B 0.41820(9) 0.58180(9) 0.5000 0.0183(6) Uani 0.50 2 d SPD
C1B C 0.43543(6) 0.56457(6) 0.5000 0.0183(6) Uani 0.50 2 d SPD
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 0.02064(16) 0.02064(16) 0.0197(2) -0.00205(11) -0.00205(11) -0.00260(15)
Cl2 0.0189(3) 0.0189(3) 0.0441(6) -0.0092(3) -0.0092(3) 0.0065(3)
F1 0.0118(6) 0.0230(8) 0.0234(8) -0.0021(6) 0.0036(6) -0.0005(5)
N1 0.0144(5) 0.0136(5) 0.0188(5) 0.0017(4) 0.0011(4) -0.0021(4)
C1N 0.0144(5) 0.0136(5) 0.0188(5) 0.0017(4) 0.0011(4) -0.0021(4)
C1 0.0153(5) 0.0147(5) 0.0207(6) 0.0025(4) -0.0008(4) -0.0013(4)
C2 0.0158(5) 0.0158(5) 0.0169(8) 0.0003(4) 0.0003(4) -0.0040(6)
B1 0.0162(8) 0.0162(8) 0.0226(9) 0.0013(5) 0.0013(5) -0.0049(10)
C1B 0.0162(8) 0.0162(8) 0.0226(9) 0.0013(5) 0.0013(5) -0.0049(10)
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'
Cl Cl 0.1484 0.1585 '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'
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
Cl2 F1 B1 61.84(11) . .
Cl2 F1 C1B 72.02(7) . .
B1 F1 C1B 10.18(6) . .
C1 N1 C1B 135.07(11) . .
C1 N1 C1N 108.32(7) . 16
C1B N1 C1N 116.61(7) . 16
C1 N1 N1 108.32(7) . 16
C1B N1 N1 116.61(7) . 16
C1 N1 B1 123.51(10) . .
C1B N1 B1 11.56(7) . .
C1N N1 B1 128.17(6) 16 .
N1 N1 B1 128.17(6) 16 .
N1 C1 C2 107.44(11) . .
N1 C1 H1 126.3 . .
C2 C1 H1 126.3 . .
C1 C2 C1 108.49(16) . 16
C1 C2 Cl1 125.75(8) . .
C1 C2 Cl1 125.76(8) 16 .
F1 B1 F1 108.42(19) . 8_666
Cl2 B1 C1N 128.17(6) . 8_666
F1 B1 C1N 111.12(8) . 8_666
F1 B1 C1N 111.26(8) 8_666 8_666
Cl2 B1 N1 128.17(6) . 8_666
F1 B1 N1 111.12(8) . 8_666
F1 B1 N1 111.26(8) 8_666 8_666
Cl2 B1 N1 128.17(6) . .
F1 B1 N1 111.26(8) . .
F1 B1 N1 111.12(8) 8_666 .
C1N B1 N1 103.65(13) 8_666 .
N1 B1 N1 103.65(13) 8_666 .
C1N C1B N1 126.78(13) 8_666 .
N1 C1B N1 126.78(13) 8_666 .
C1N C1B F1 108.72(8) 8_666 .
N1 C1B F1 108.72(8) 8_666 .
N1 C1B F1 108.86(8) . .
C1N C1B F1 108.86(8) 8_666 8_666
N1 C1B F1 108.86(8) 8_666 8_666
N1 C1B F1 108.72(8) . 8_666
C1N C1B Cl2 116.61(7) 8_666 .
N1 C1B Cl2 116.61(7) 8_666 .
N1 C1B Cl2 116.61(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7116(18) .
Cl2 C1B 1.7092(10) .
F1 B1 1.3833(10) .
F1 C1B 1.6143(14) .
N1 C1 1.3710(16) .
N1 C1B 1.3794(8) .
N1 C1N 1.400(2) 16
N1 N1 1.400(2) 16
N1 B1 1.5688(10) .
C1 C2 1.3934(16) .
C1 H1 0.9500 .
C2 C1 1.3934(16) 16
B1 F1 1.3833(10) 8_666
B1 N1 1.5688(10) 8_666
C1B C1N 1.3794(8) 8_666
C1B N1 1.3794(8) 8_666
