#------------------------------------------------------------------------------
#$Date: 2015-10-09 11:13:33 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161242 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/62/7036272.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_7036272
loop_
_publ_author_name
'Kesavan, Praseetha E.'
'Das, Sudipta'
'Lone, Mohsin Y.'
'Jha, Prakash C.'
'Mori, Shigeki'
'Gupta, Iti'
_publ_section_title
;
 Bridged bis-BODIPYs: their synthesis, structures and properties.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17209
_journal_page_last               17221
_journal_paper_doi               10.1039/c5dt01925g
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C36 H25 B2 F4 N5'
_chemical_formula_sum            'C36 H25 B2 F4 N5'
_chemical_formula_weight         625.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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_update_record
;
2014-10-09 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.599(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.107(13)
_cell_length_b                   9.399(4)
_cell_length_c                   13.496(7)
_cell_measurement_reflns_used    4521
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.06
_cell_measurement_theta_min      2.33
_cell_volume                     2981(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_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            24454
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0570P)²+2.4655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3004
_reflns_number_total             3597
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt01925g2.cif
_cod_data_source_block           ProfFuruta
_cod_depositor_comments
'Adding full bibliography for 7036270--7036272.cif.'
_cod_database_code               7036272
_audit_block_doi                 10.5517/cc13hysb
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.23547(5) 0.21933(15) 0.15294(10) 0.0343(4) Uani 1 1 d . . .
F2 F 0.30932(6) 0.16084(14) 0.10124(10) 0.0345(4) Uani 1 1 d . . .
N1 N 0.31114(7) 0.38969(18) 0.18514(13) 0.0201(4) Uani 1 1 d . . .
N2 N 0.32542(7) 0.16590(18) 0.28786(13) 0.0214(4) Uani 1 1 d . . .
N3 N 0.5000 0.6782(2) 0.7500 0.0200(5) Uani 1 2 d S T P
C1 C 0.29573(9) 0.4838(2) 0.10527(16) 0.0247(5) Uani 1 1 d . . .
H1 H 0.2713 0.4634 0.0350 0.030 Uiso 1 1 calc R U .
C2 C 0.32073(9) 0.6165(2) 0.14007(17) 0.0252(5) Uani 1 1 d . . .
H2 H 0.3162 0.7005 0.0988 0.030 Uiso 1 1 calc R U .
C3 C 0.35321(8) 0.6018(2) 0.24573(16) 0.0215(4) Uani 1 1 d . . .
H3 H 0.3756 0.6738 0.2906 0.026 Uiso 1 1 calc R U .
C4 C 0.34708(8) 0.4593(2) 0.27529(15) 0.0190(4) Uani 1 1 d . . .
C5 C 0.36978(8) 0.3870(2) 0.37234(15) 0.0173(4) Uani 1 1 d . . .
C6 C 0.35815(8) 0.2409(2) 0.37826(15) 0.0189(4) Uani 1 1 d . . .
C7 C 0.37269(9) 0.1446(2) 0.46438(17) 0.0230(5) Uani 1 1 d . . .
H7 H 0.3945 0.1657 0.5361 0.028 Uiso 1 1 calc R U .
C8 C 0.34937(9) 0.0141(2) 0.42504(17) 0.0273(5) Uani 1 1 d . . .
H8 H 0.3526 -0.0713 0.4643 0.033 Uiso 1 1 calc R U .
C9 C 0.32034(9) 0.0315(2) 0.31706(18) 0.0271(5) Uani 1 1 d . . .
H9 H 0.2998 -0.0415 0.2705 0.033 Uiso 1 1 calc R U .
C10 C 0.40464(8) 0.4632(2) 0.46885(15) 0.0172(4) Uani 1 1 d . . .
C11 C 0.38775(8) 0.5968(2) 0.49367(15) 0.0198(4) Uani 1 1 d . . .
H11 H 0.3543 0.6400 0.4461 0.024 Uiso 1 1 calc R U .
C12 C 0.41881(8) 0.6668(2) 0.58609(15) 0.0200(4) Uani 1 1 d . . .
H12 H 0.4062 0.7564 0.6020 0.024 Uiso 1 1 calc R U .
C13 C 0.46858(8) 0.6063(2) 0.65609(15) 0.0175(4) Uani 1 1 d . . .
C14 C 0.48687(8) 0.4753(2) 0.63045(14) 0.0172(4) Uani 1 1 d . . .
H14 H 0.5214 0.4348 0.6764 0.021 Uiso 1 1 calc R U .
C15 C 0.45520(8) 0.4045(2) 0.53903(15) 0.0167(4) Uani 1 1 d . . .
H15 H 0.4679 0.3149 0.5235 0.020 Uiso 1 1 calc R U .
C16 C 0.5000 0.8307(3) 0.7500 0.0182(6) Uani 1 2 d S T P
C17 C 0.47837(9) 0.9049(2) 0.81675(17) 0.0248(5) Uani 1 1 d . . .
H17 H 0.4636 0.8545 0.8624 0.030 Uiso 1 1 calc R U .
C18 C 0.47837(10) 1.0522(2) 0.81661(18) 0.0319(5) Uani 1 1 d . . .
H18 H 0.4636 1.1030 0.8621 0.038 Uiso 1 1 calc R U .
C19 C 0.5000 1.1253(3) 0.7500 0.0355(8) Uani 1 2 d S T P
H19 H 0.5000 1.2264 0.7500 0.043 Uiso 1 2 calc R U P
B1 B 0.29373(10) 0.2313(3) 0.17730(18) 0.0234(5) Uani 1 1 d . . .
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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s11243-015-9912-7 2015
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 C4 107.84(17) . .
C1 N1 B1 125.86(17) . .
C4 N1 B1 126.27(17) . .
C9 N2 C6 107.78(17) . .
C9 N2 B1 125.87(17) . .
C6 N2 B1 125.83(18) . .
C13 N3 C13 122.6(2) 2_656 .
C13 N3 C16 118.70(11) 2_656 .
C13 N3 C16 118.70(11) . .
N1 C1 C2 110.42(18) . .
N1 C1 H1 124.8 . .
C2 C1 H1 124.8 . .
C3 C2 C1 106.88(19) . .
C3 C2 H2 126.6 . .
C1 C2 H2 126.6 . .
C2 C3 C4 107.55(18) . .
C2 C3 H3 126.2 . .
C4 C3 H3 126.2 . .
N1 C4 C5 120.74(18) . .
N1 C4 C3 107.30(17) . .
C5 C4 C3 131.96(18) . .
C4 C5 C6 119.91(18) . .
C4 C5 C10 120.55(18) . .
C6 C5 C10 119.53(17) . .
N2 C6 C5 120.70(18) . .
N2 C6 C7 107.26(18) . .
C5 C6 C7 132.02(19) . .
C8 C7 C6 107.44(19) . .
C8 C7 H7 126.3 . .
C6 C7 H7 126.3 . .
C7 C8 C9 107.1(2) . .
C7 C8 H8 126.5 . .
C9 C8 H8 126.5 . .
N2 C9 C8 110.41(19) . .
N2 C9 H9 124.8 . .
C8 C9 H9 124.8 . .
C15 C10 C11 117.91(17) . .
C15 C10 C5 121.39(18) . .
C11 C10 C5 120.69(17) . .
C12 C11 C10 121.28(18) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C11 C12 C13 120.21(19) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C12 C13 C14 119.01(17) . .
C12 C13 N3 119.88(18) . .
C14 C13 N3 121.10(17) . .
C15 C14 C13 120.60(17) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C10 120.93(18) . .
C14 C15 H15 119.5 . .
C10 C15 H15 119.5 . .
C17 C16 C17 119.9(3) 2_656 .
C17 C16 N3 120.07(14) 2_656 .
C17 C16 N3 120.07(14) . .
C18 C17 C16 120.0(2) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 119.8(2) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
C18 C19 C18 120.5(3) . 2_656
C18 C19 H19 119.7 . .
C18 C19 H19 119.7 2_656 .
F1 B1 F2 109.53(17) . .
F1 B1 N1 110.12(19) . .
F2 B1 N1 111.32(18) . .
F1 B1 N2 109.74(17) . .
F2 B1 N2 109.87(19) . .
N1 B1 N2 106.21(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.386(3) .
F2 B1 1.389(3) .
N1 C1 1.342(3) .
N1 C4 1.396(2) .
N1 B1 1.545(3) .
N2 C9 1.343(3) .
N2 C6 1.398(3) .
N2 B1 1.550(3) .
N3 C13 1.408(2) 2_656
N3 C13 1.408(2) .
N3 C16 1.433(4) .
C1 C2 1.400(3) .
C1 H1 0.9500 .
C2 C3 1.378(3) .
C2 H2 0.9500 .
C3 C4 1.421(3) .
C3 H3 0.9500 .
C4 C5 1.406(3) .
C5 C6 1.412(3) .
C5 C10 1.474(3) .
C6 C7 1.416(3) .
C7 C8 1.382(3) .
C7 H7 0.9500 .
C8 C9 1.391(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C15 1.402(3) .
C10 C11 1.404(3) .
C11 C12 1.383(3) .
C11 H11 0.9500 .
C12 C13 1.395(3) .
C12 H12 0.9500 .
C13 C14 1.399(3) .
C14 C15 1.381(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C17 1.392(3) 2_656
C16 C17 1.392(3) .
C17 C18 1.385(3) .
C17 H17 0.9500 .
C18 C19 1.385(3) .
C18 H18 0.9500 .
C19 C18 1.385(3) 2_656
C19 H19 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 N1 C1 C2 0.0(2) . .
B1 N1 C1 C2 -178.12(19) . .
N1 C1 C2 C3 0.5(2) . .
C1 C2 C3 C4 -0.8(2) . .
C1 N1 C4 C5 179.49(18) . .
B1 N1 C4 C5 -2.4(3) . .
C1 N1 C4 C3 -0.5(2) . .
B1 N1 C4 C3 177.60(18) . .
C2 C3 C4 N1 0.8(2) . .
C2 C3 C4 C5 -179.2(2) . .
N1 C4 C5 C6 2.6(3) . .
C3 C4 C5 C6 -177.4(2) . .
N1 C4 C5 C10 -175.98(17) . .
C3 C4 C5 C10 4.0(3) . .
C9 N2 C6 C5 -178.72(18) . .
B1 N2 C6 C5 -6.6(3) . .
C9 N2 C6 C7 -0.1(2) . .
B1 N2 C6 C7 172.07(18) . .
C4 C5 C6 N2 1.7(3) . .
C10 C5 C6 N2 -179.72(17) . .
C4 C5 C6 C7 -176.6(2) . .
C10 C5 C6 C7 2.0(3) . .
N2 C6 C7 C8 0.7(2) . .
C5 C6 C7 C8 179.1(2) . .
C6 C7 C8 C9 -0.9(2) . .
C6 N2 C9 C8 -0.5(2) . .
B1 N2 C9 C8 -172.67(19) . .
C7 C8 C9 N2 0.9(3) . .
C4 C5 C10 C15 -135.9(2) . .
C6 C5 C10 C15 45.5(3) . .
C4 C5 C10 C11 44.6(3) . .
C6 C5 C10 C11 -134.0(2) . .
C15 C10 C11 C12 -2.1(3) . .
C5 C10 C11 C12 177.32(18) . .
C10 C11 C12 C13 1.2(3) . .
C11 C12 C13 C14 1.0(3) . .
C11 C12 C13 N3 179.96(17) . .
C13 N3 C13 C12 148.3(2) 2_656 .
C16 N3 C13 C12 -31.7(2) . .
C13 N3 C13 C14 -32.75(14) 2_656 .
C16 N3 C13 C14 147.25(14) . .
C12 C13 C14 C15 -2.2(3) . .
N3 C13 C14 C15 178.87(16) . .
C13 C14 C15 C10 1.2(3) . .
C11 C10 C15 C14 1.0(3) . .
C5 C10 C15 C14 -178.51(17) . .
C13 N3 C16 C17 118.32(14) 2_656 2_656
C13 N3 C16 C17 -61.68(14) . 2_656
C13 N3 C16 C17 -61.68(14) 2_656 .
C13 N3 C16 C17 118.32(14) . .
C17 C16 C17 C18 0.03(15) 2_656 .
N3 C16 C17 C18 -179.97(15) . .
C16 C17 C18 C19 -0.1(3) . .
C17 C18 C19 C18 0.03(15) . 2_656
C1 N1 B1 F1 -65.1(3) . .
C4 N1 B1 F1 117.2(2) . .
C1 N1 B1 F2 56.6(3) . .
C4 N1 B1 F2 -121.2(2) . .
C1 N1 B1 N2 176.16(18) . .
C4 N1 B1 N2 -1.6(3) . .
C9 N2 B1 F1 57.9(3) . .
C6 N2 B1 F1 -112.9(2) . .
C9 N2 B1 F2 -62.6(3) . .
C6 N2 B1 F2 126.6(2) . .
C9 N2 B1 N1 176.85(19) . .
C6 N2 B1 N1 6.1(3) . .
