#------------------------------------------------------------------------------
#$Date: 2016-10-08 00:32:20 +0200 (Sat 08 de Oct de 2016) $
#$Revision: 187158 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/53/7055356.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_7055356
loop_
_publ_author_name
'Meng, Qianli'
'Fronczek, Frank R.'
'Vicente, M Graça H'
_publ_section_title
;
 Synthesis and spectroscopic properties of
 β,β'-dibenzo-3,5,8-triaryl-BODIPYs.
;
_journal_issue                   7
_journal_name_full
'New journal of chemistry = Nouveau journal de chimie'
_journal_page_first              5740
_journal_page_last               5751
_journal_paper_doi               10.1039/C5NJ03324A
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C35 H29 B F2 N4 O4'
_chemical_formula_sum            'C35 H29 B F2 N4 O4'
_chemical_formula_weight         618.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_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
_audit_update_record
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.931(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7880(6)
_cell_length_b                   12.5007(6)
_cell_length_c                   15.9397(7)
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      33.10
_cell_measurement_theta_min      2.89
_cell_volume                     2804.7(2)
_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 0.999
_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  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31542
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.20
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1288
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         5374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0468
_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)+(0.0699P)²+1.8012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                4112
_reflns_number_total             5374
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5nj03324a2.cif
_cod_data_source_block           Compound5c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7055354--7055362.cif.

 Adding full bibliography for 7055354--7055362.cif.
;
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c  '
_cod_database_code               7055356
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
F1 F 0.43808(9) 0.47371(9) 0.17680(8) 0.0517(4) Uani 1 1 d .
O1 O 0.27986(7) 0.09319(7) 0.33551(7) 0.0233(2) Uani 1 1 d .
O2 O 0.30789(8) 0.13403(8) 0.47816(7) 0.0255(2) Uani 1 1 d .
N1 N 0.44741(6) 0.60962(7) 0.29151(6) 0.00913(16) Uani 1 1 d .
N2 N 0.30291(7) 0.15692(8) 0.40093(7) 0.01612(19) Uani 1 1 d .
C1 C 0.40939(7) 0.57976(8) 0.35009(7) 0.00905(17) Uani 1 1 d .
C2 C 0.39821(7) 0.67157(8) 0.39669(7) 0.00957(18) Uani 1 1 d .
C3 C 0.36384(8) 0.67952(8) 0.47048(8) 0.01183(19) Uani 1 1 d .
H3A H 0.4133 0.6516 0.5310 0.014 Uiso 1 1 calc R
H3B H 0.3061 0.6352 0.4516 0.014 Uiso 1 1 calc R
C4 C 0.34135(8) 0.79566(9) 0.48318(8) 0.01304(19) Uani 1 1 d .
H4A H 0.2816 0.8176 0.4286 0.016 Uiso 1 1 calc R
H4B H 0.3321 0.8016 0.5404 0.016 Uiso 1 1 calc R
C5 C 0.42158(8) 0.86997(9) 0.49194(8) 0.0135(2) Uani 1 1 d .
H5A H 0.4822 0.8452 0.5439 0.016 Uiso 1 1 calc R
H5B H 0.4089 0.9432 0.5070 0.016 Uiso 1 1 calc R
C6 C 0.43009(8) 0.87166(8) 0.40008(7) 0.01207(19) Uani 1 1 d .
H6A H 0.3770 0.9136 0.3522 0.014 Uiso 1 1 calc R
H6B H 0.4903 0.9069 0.4109 0.014 Uiso 1 1 calc R
C7 C 0.42791(7) 0.75985(8) 0.36426(7) 0.00946(18) Uani 1 1 d .
C8 C 0.45839(7) 0.72084(8) 0.29844(7) 0.00953(18) Uani 1 1 d .
C9 C 0.5000 0.77566(11) 0.2500 0.0098(2) Uani 1 2 d S
C10 C 0.38147(7) 0.47041(8) 0.36049(7) 0.00993(18) Uani 1 1 d .
C11 C 0.34277(7) 0.39788(8) 0.28486(7) 0.01133(18) Uani 1 1 d .
H11 H 0.3346 0.4191 0.2244 0.014 Uiso 1 1 calc R
C12 C 0.31652(8) 0.29568(8) 0.29785(8) 0.01232(19) Uani 1 1 d .
H12 H 0.2912 0.2465 0.2469 0.015 Uiso 1 1 calc R
C13 C 0.32784(7) 0.26627(8) 0.38645(8) 0.01237(19) Uani 1 1 d .
C14 C 0.36276(8) 0.33634(8) 0.46179(8) 0.01268(19) Uani 1 1 d .
H14 H 0.3684 0.3153 0.5214 0.015 Uiso 1 1 calc R
C15 C 0.38940(8) 0.43814(8) 0.44824(7) 0.01159(19) Uani 1 1 d .
H15 H 0.4135 0.4871 0.4994 0.014 Uiso 1 1 calc R
C16 C 0.5000 0.89459(11) 0.2500 0.0109(2) Uani 1 2 d S
C17 C 0.41429(8) 0.95056(9) 0.20771(8) 0.0139(2) Uani 1 1 d .
H17 H 0.3558 0.9128 0.1785 0.017 Uiso 1 1 calc R
C18 C 0.41482(10) 1.06177(9) 0.20855(8) 0.0187(2) Uani 1 1 d .
H18 H 0.3564 1.0998 0.1805 0.022 Uiso 1 1 calc R
C19 C 0.5000 1.11761(13) 0.2500 0.0211(3) Uani 1 2 d S
H19 H 0.5000 1.1936 0.2500 0.025 Uiso 1 2 calc SR
B1 B 0.5000 0.53652(14) 0.2500 0.0164(3) 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
C1 N1 C8 107.07(8) . .
C1 N1 B1 127.41(9) . .
C8 N1 B1 122.81(9) . .
O1 N2 O2 123.91(10) . .
O1 N2 C13 117.85(10) . .
O2 N2 C13 118.23(10) . .
N1 C1 C2 109.42(9) . .
N1 C1 C10 125.22(9) . .
C2 C1 C10 125.32(9) . .
C7 C2 C1 107.75(9) . .
C7 C2 C3 122.74(9) . .
C1 C2 C3 129.49(9) . .
C2 C3 C4 110.70(8) . .
C2 C3 H3A 109.5 . .
C4 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
C4 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C5 C4 C3 110.92(9) . .
C5 C4 H4A 109.5 . .
C3 C4 H4A 109.5 . .
C5 C4 H4B 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 108.0 . .
C4 C5 C6 110.49(9) . .
C4 C5 H5A 109.6 . .
C6 C5 H5A 109.6 . .
C4 C5 H5B 109.6 . .
C6 C5 H5B 109.6 . .
H5A C5 H5B 108.1 . .
C7 C6 C5 110.71(9) . .
C7 C6 H6A 109.5 . .
C5 C6 H6A 109.5 . .
C7 C6 H6B 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
C2 C7 C8 106.62(9) . .
C2 C7 C6 123.45(9) . .
C8 C7 C6 129.84(9) . .
C9 C8 N1 121.04(9) . .
C9 C8 C7 129.70(9) . .
N1 C8 C7 109.11(8) . .
C8 C9 C8 121.33(13) . 2_655
C8 C9 C16 119.34(6) . .
C8 C9 C16 119.34(6) 2_655 .
C15 C10 C11 118.41(9) . .
C15 C10 C1 118.91(9) . .
C11 C10 C1 122.61(9) . .
C12 C11 C10 120.57(10) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C13 119.04(10) . .
C11 C12 H12 120.5 . .
C13 C12 H12 120.5 . .
C14 C13 C12 122.12(10) . .
C14 C13 N2 118.85(10) . .
C12 C13 N2 119.03(10) . .
C13 C14 C15 118.38(10) . .
C13 C14 H14 120.8 . .
C15 C14 H14 120.8 . .
C14 C15 C10 121.42(10) . .
C14 C15 H15 119.3 . .
C10 C15 H15 119.3 . .
C17 C16 C17 119.84(14) 2_655 .
C17 C16 C9 120.08(7) 2_655 .
C17 C16 C9 120.08(7) . .
C18 C17 C16 119.76(12) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 120.50(12) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C18 C19 C18 119.63(15) 2_655 .
C18 C19 H19 120.2 2_655 .
C18 C19 H19 120.2 . .
F1 B1 F1 110.56(17) . 2_655
F1 B1 N1 112.39(6) . .
F1 B1 N1 106.43(5) 2_655 .
F1 B1 N1 106.43(5) . 2_655
F1 B1 N1 112.39(6) 2_655 2_655
N1 B1 N1 108.73(12) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.3785(13) .
O1 N2 1.2291(14) .
O2 N2 1.2312(14) .
N1 C1 1.3708(13) .
N1 C8 1.3993(13) .
N1 B1 1.5684(13) .
N2 C13 1.4694(14) .
C1 C2 1.4208(14) .
C1 C10 1.4685(14) .
C2 C7 1.3873(14) .
C2 C3 1.5054(14) .
C3 C4 1.5298(15) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.5254(15) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.5298(15) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.5043(14) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.4239(14) .
C8 C9 1.3989(12) .
C9 C8 1.3989(12) 2_655
C9 C16 1.487(2) .
C10 C15 1.4058(14) .
C10 C11 1.4076(14) .
C11 C12 1.3872(14) .
C11 H11 0.9500 .
C12 C13 1.3903(15) .
C12 H12 0.9500 .
C13 C14 1.3833(15) .
C14 C15 1.3875(14) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C17 1.3960(13) 2_655
C16 C17 1.3960(13) .
C17 C18 1.3902(16) .
C17 H17 0.9500 .
C18 C19 1.3884(16) .
C18 H18 0.9500 .
C19 C18 1.3884(16) 2_655
C19 H19 0.9500 .
B1 F1 1.3785(13) 2_655
B1 N1 1.5685(13) 2_655
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
C8 N1 C1 C2 -1.53(11) . .
B1 N1 C1 C2 160.01(8) . .
C8 N1 C1 C10 176.50(10) . .
B1 N1 C1 C10 -21.96(15) . .
N1 C1 C2 C7 1.43(12) . .
C10 C1 C2 C7 -176.60(10) . .
N1 C1 C2 C3 -176.94(10) . .
C10 C1 C2 C3 5.03(17) . .
C7 C2 C3 C4 15.26(14) . .
C1 C2 C3 C4 -166.59(10) . .
C2 C3 C4 C5 -47.27(12) . .
C3 C4 C5 C6 65.35(12) . .
C4 C5 C6 C7 -46.82(12) . .
C1 C2 C7 C8 -0.73(12) . .
C3 C2 C7 C8 177.78(9) . .
C1 C2 C7 C6 -177.66(9) . .
C3 C2 C7 C6 0.84(16) . .
C5 C6 C7 C2 15.10(14) . .
C5 C6 C7 C8 -161.07(11) . .
C1 N1 C8 C9 177.00(8) . .
B1 N1 C8 C9 14.41(13) . .
C1 N1 C8 C7 1.07(11) . .
B1 N1 C8 C7 -161.51(7) . .
C2 C7 C8 C9 -175.65(9) . .
C6 C7 C8 C9 1.01(18) . .
C2 C7 C8 N1 -0.20(12) . .
C6 C7 C8 N1 176.47(10) . .
N1 C8 C9 C8 -7.23(7) . 2_655
C7 C8 C9 C8 167.76(13) . 2_655
N1 C8 C9 C16 172.77(7) . .
C7 C8 C9 C16 -12.24(13) . .
N1 C1 C10 C15 148.22(10) . .
C2 C1 C10 C15 -34.06(15) . .
N1 C1 C10 C11 -34.86(15) . .
C2 C1 C10 C11 142.86(11) . .
C15 C10 C11 C12 -2.40(15) . .
C1 C10 C11 C12 -179.33(10) . .
C10 C11 C12 C13 0.83(16) . .
C11 C12 C13 C14 1.27(16) . .
C11 C12 C13 N2 -178.06(9) . .
O1 N2 C13 C14 -173.82(10) . .
O2 N2 C13 C14 4.95(15) . .
O1 N2 C13 C12 5.53(15) . .
O2 N2 C13 C12 -175.71(11) . .
C12 C13 C14 C15 -1.68(16) . .
N2 C13 C14 C15 177.65(9) . .
C13 C14 C15 C10 0.01(16) . .
C11 C10 C15 C14 1.99(16) . .
C1 C10 C15 C14 179.04(10) . .
C8 C9 C16 C17 115.79(7) . 2_655
C8 C9 C16 C17 -64.21(7) 2_655 2_655
C8 C9 C16 C17 -64.20(7) . .
C8 C9 C16 C17 115.80(7) 2_655 .
C17 C16 C17 C18 -0.44(7) 2_655 .
C9 C16 C17 C18 179.56(7) . .
C16 C17 C18 C19 0.89(15) . .
C17 C18 C19 C18 -0.44(7) . 2_655
C1 N1 B1 F1 76.50(13) . .
C8 N1 B1 F1 -124.61(12) . .
C1 N1 B1 F1 -44.66(13) . 2_655
C8 N1 B1 F1 114.23(12) . 2_655
C1 N1 B1 N1 -165.94(11) . 2_655
C8 N1 B1 N1 -7.05(6) . 2_655
