#------------------------------------------------------------------------------
#$Date: 2015-10-09 11:13:33 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161242 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/62/7036270.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_7036270
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         'C24 H16 B2 F4 N4'
_chemical_formula_sum            'C24 H16 B2 F4 N4'
_chemical_formula_weight         458.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2014-06-02 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.260(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.06279(19)
_cell_length_b                   11.7071(4)
_cell_length_c                   14.5542(5)
_cell_measurement_reflns_used    8890
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.06
_cell_volume                     1026.86(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11689
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         4.859
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  0.771
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0438
_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)+(0.0680P)²+0.2281P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1719
_reflns_number_total             1882
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt01925g2.cif
_cod_data_source_block           20140423
_cod_depositor_comments
'Adding full bibliography for 7036270--7036272.cif.'
_cod_database_code               7036270
_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   0.775
_shelx_estimated_absorpt_t_max   0.781
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
F1 F 1.07503(15) 0.19630(7) 0.40276(6) 0.0304(3) Uani 1 1 d . .
F2 F 0.87664(15) 0.34948(8) 0.44056(6) 0.0322(3) Uani 1 1 d . .
N1 N 0.8132(2) 0.27732(11) 0.28378(8) 0.0234(3) Uani 1 1 d . .
N2 N 1.1621(2) 0.37869(10) 0.33899(8) 0.0237(3) Uani 1 1 d . .
C1 C 0.6337(3) 0.20920(13) 0.27748(11) 0.0283(4) Uani 1 1 d . .
H1 H 0.5797 0.1710 0.3281 0.034 Uiso 1 1 calc R U
C2 C 0.5375(3) 0.20245(13) 0.18552(11) 0.0282(4) Uani 1 1 d . .
H2 H 0.4104 0.1592 0.1630 0.034 Uiso 1 1 calc R U
C3 C 0.6629(2) 0.27071(12) 0.13397(10) 0.0232(3) Uani 1 1 d . .
H3 H 0.6389 0.2829 0.0691 0.028 Uiso 1 1 calc R U
C4 C 0.8333(2) 0.31907(12) 0.19551(10) 0.0207(3) Uani 1 1 d . .
C5 C 1.0022(2) 0.39547(12) 0.17959(10) 0.0204(3) Uani 1 1 d . .
C6 C 1.1660(2) 0.42472(12) 0.25093(9) 0.0212(3) Uani 1 1 d . .
C7 C 1.3529(2) 0.49731(13) 0.25269(10) 0.0241(3) Uani 1 1 d . .
H7 H 1.3957 0.5409 0.2025 0.029 Uiso 1 1 calc R U
C8 C 1.4615(3) 0.49297(14) 0.34096(11) 0.0288(4) Uani 1 1 d . .
H8 H 1.5940 0.5323 0.3629 0.035 Uiso 1 1 calc R U
C9 C 1.3393(3) 0.41961(14) 0.39205(11) 0.0294(4) Uani 1 1 d . .
H9 H 1.3767 0.4013 0.4554 0.035 Uiso 1 1 calc R U
C10 C 1.1888(2) 0.44277(12) 0.03864(9) 0.0205(3) Uani 1 1 d . .
H10 H 1.3178 0.4035 0.0648 0.025 Uiso 1 1 calc R U
C11 C 1.0017(2) 0.44768(12) 0.08668(9) 0.0194(3) Uani 1 1 d . .
C12 C 0.8127(2) 0.50521(12) 0.04685(9) 0.0205(3) Uani 1 1 d . .
H12 H 0.6842 0.5086 0.0788 0.025 Uiso 1 1 calc R U
B1 B 0.9795(3) 0.29933(15) 0.37083(11) 0.0246(4) 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C1 N1 C4 107.28(12) .
C1 N1 B1 127.09(13) .
C4 N1 B1 125.49(12) .
C9 N2 C6 107.36(12) .
C9 N2 B1 126.42(13) .
C6 N2 B1 126.16(12) .
N1 C1 C2 110.35(14) .
N1 C1 H1 124.8 .
C2 C1 H1 124.8 .
C3 C2 C1 106.84(14) .
C3 C2 H2 126.6 .
C1 C2 H2 126.6 .
C2 C3 C4 107.23(13) .
C2 C3 H3 126.4 .
C4 C3 H3 126.4 .
N1 C4 C5 121.13(13) .
N1 C4 C3 108.26(12) .
C5 C4 C3 130.61(13) .
C4 C5 C6 120.48(13) .
C4 C5 C11 119.06(13) .
C6 C5 C11 120.43(13) .
N2 C6 C5 120.41(13) .
N2 C6 C7 108.05(12) .
C5 C6 C7 131.54(14) .
C8 C7 C6 107.15(13) .
C8 C7 H7 126.4 .
C6 C7 H7 126.4 .
C7 C8 C9 106.92(14) .
C7 C8 H8 126.5 .
C9 C8 H8 126.5 .
N2 C9 C8 110.51(13) .
N2 C9 H9 124.7 .
C8 C9 H9 124.7 .
C12 C10 C11 120.35(13) 3_765
C12 C10 H10 119.8 3_765
C11 C10 H10 119.8 .
C10 C11 C12 119.05(13) .
C10 C11 C5 121.18(12) .
C12 C11 C5 119.76(12) .
C10 C12 C11 120.60(13) 3_765
C10 C12 H12 119.7 3_765
C11 C12 H12 119.7 .
F2 B1 F1 109.11(12) .
F2 B1 N1 111.46(13) .
F1 B1 N1 109.72(13) .
F2 B1 N2 111.03(13) .
F1 B1 N2 109.44(13) .
N1 B1 N2 106.03(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.3956(19) .
F2 B1 1.3789(19) .
N1 C1 1.3442(19) .
N1 C4 1.3922(18) .
N1 B1 1.552(2) .
N2 C9 1.3417(19) .
N2 C6 1.3929(18) .
N2 B1 1.554(2) .
C1 C2 1.403(2) .
C1 H1 0.9500 .
C2 C3 1.380(2) .
C2 H2 0.9500 .
C3 C4 1.410(2) .
C3 H3 0.9500 .
C4 C5 1.398(2) .
C5 C6 1.399(2) .
C5 C11 1.4837(19) .
C6 C7 1.414(2) .
C7 C8 1.379(2) .
C7 H7 0.9500 .
C8 C9 1.400(2) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C12 1.3845(19) 3_765
C10 C11 1.398(2) .
C10 H10 0.9500 .
C11 C12 1.3991(19) .
C12 C10 1.3845(19) 3_765
C12 H12 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 1.69(18) . .
B1 N1 C1 C2 -174.09(14) . .
N1 C1 C2 C3 -0.76(19) . .
C1 C2 C3 C4 -0.48(17) . .
C1 N1 C4 C5 178.28(13) . .
B1 N1 C4 C5 -5.9(2) . .
C1 N1 C4 C3 -1.96(16) . .
B1 N1 C4 C3 173.90(13) . .
C2 C3 C4 N1 1.50(16) . .
C2 C3 C4 C5 -178.77(15) . .
N1 C4 C5 C6 5.1(2) . .
C3 C4 C5 C6 -174.56(14) . .
N1 C4 C5 C11 -173.11(12) . .
C3 C4 C5 C11 7.2(2) . .
C9 N2 C6 C5 178.82(13) . .
B1 N2 C6 C5 -3.9(2) . .
C9 N2 C6 C7 -0.80(16) . .
B1 N2 C6 C7 176.50(13) . .
C4 C5 C6 N2 -0.4(2) . .
C11 C5 C6 N2 177.77(12) . .
C4 C5 C6 C7 179.06(14) . .
C11 C5 C6 C7 -2.7(2) . .
N2 C6 C7 C8 0.96(17) . .
C5 C6 C7 C8 -178.60(15) . .
C6 C7 C8 C9 -0.74(18) . .
C6 N2 C9 C8 0.34(18) . .
B1 N2 C9 C8 -176.95(14) . .
C7 C8 C9 N2 0.26(19) . .
C12 C10 C11 C12 0.4(2) 3_765 .
C12 C10 C11 C5 -178.16(12) 3_765 .
C4 C5 C11 C10 -127.45(14) . .
C6 C5 C11 C10 54.31(19) . .
C4 C5 C11 C12 54.00(19) . .
C6 C5 C11 C12 -124.25(15) . .
C10 C11 C12 C10 -0.4(2) . 3_765
C5 C11 C12 C10 178.18(12) . 3_765
C1 N1 B1 F2 -62.3(2) . .
C4 N1 B1 F2 122.69(15) . .
C1 N1 B1 F1 58.7(2) . .
C4 N1 B1 F1 -116.33(15) . .
C1 N1 B1 N2 176.80(14) . .
C4 N1 B1 N2 1.75(19) . .
C9 N2 B1 F2 58.67(19) . .
C6 N2 B1 F2 -118.13(15) . .
C9 N2 B1 F1 -61.8(2) . .
C6 N2 B1 F1 121.37(14) . .
C9 N2 B1 N1 179.89(13) . .
C6 N2 B1 N1 3.10(19) . .
