#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118083.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_7118083
loop_
_publ_author_name
'Changjiang Yu'
'Lijuan Jiao'
'Tingting Li'
'Qinghua Wu'
'Wei Miao'
'Jun Wang'
'Yun Wei'
'Xiaolong Mu'
'Erhong Hao'
_publ_section_title
;
 Fusion and planarization of bisBODIPY: a new family of photostable near
 infrared dyes
;
_journal_name_full               Chem.Commun.
_journal_page_first              16852
_journal_paper_doi               10.1039/C5cc07304A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C29 H34 B2 F4 N4'
_chemical_formula_weight         536.22
_chemical_name_systematic        4
_chemical_properties_physical    Light-sensitive
_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_block_doi                 10.5517/cc1jq2y8
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-31 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.917(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.145(4)
_cell_length_b                   7.6970(12)
_cell_length_c                   14.341(2)
_cell_measurement_reflns_used    4314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.76
_cell_volume                     2823.8(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11814
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0828P)²+3.8667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1807
_refine_ls_wR_factor_ref         0.1978
_reflns_number_gt                2360
_reflns_number_total             3260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc07304a2.cif
_cod_data_source_block           150106a_0m
_cod_original_cell_volume        2823.7(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7118083
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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.41498(12) 1.0688(4) 0.21822(18) 0.0559(7) Uani 1 1 d . . .
C1 C 0.48193(8) 1.2854(3) 0.32618(15) 0.0449(5) Uani 1 1 d . . .
C2 C 0.49751(10) 1.3151(3) 0.42423(17) 0.0567(6) Uani 1 1 d . . .
H2 H 0.5213 1.3989 0.4529 0.068 Uiso 1 1 calc R . .
C3 C 0.47187(10) 1.1999(3) 0.47055(16) 0.0572(6) Uani 1 1 d . . .
H3 H 0.4748 1.1912 0.5361 0.069 Uiso 1 1 calc R . .
C4 C 0.44039(8) 1.0976(3) 0.40122(14) 0.0465(5) Uani 1 1 d . . .
C5 C 0.41090(9) 0.9533(3) 0.41367(15) 0.0511(5) Uani 1 1 d . . .
H5 H 0.4101 0.9177 0.4753 0.061 Uiso 1 1 calc R . .
C6 C 0.38296(9) 0.8610(3) 0.33866(15) 0.0494(5) Uani 1 1 d . . .
C7 C 0.35111(11) 0.7114(3) 0.3348(2) 0.0643(7) Uani 1 1 d . . .
C8 C 0.33079(11) 0.6791(4) 0.2408(2) 0.0699(7) Uani 1 1 d . . .
C9 C 0.35027(10) 0.8094(3) 0.18740(18) 0.0608(6) Uani 1 1 d . . .
C10 C 0.33874(14) 0.8301(5) 0.0820(2) 0.0921(11) Uani 1 1 d . . .
H10A H 0.3193 0.9352 0.0650 0.138 Uiso 1 1 calc R . .
H10B H 0.3186 0.7327 0.0530 0.138 Uiso 1 1 calc R . .
H10C H 0.3709 0.8358 0.0598 0.138 Uiso 1 1 calc R . .
C11 C 0.29511(15) 0.5329(5) 0.1973(3) 0.1016(12) Uani 1 1 d . . .
H11A H 0.3033 0.4999 0.1367 0.122 Uiso 1 1 calc R . .
H11B H 0.3009 0.4326 0.2391 0.122 Uiso 1 1 calc R . .
C12 C 0.24010(17) 0.5854(7) 0.1824(4) 0.151(2) Uani 1 1 d . . .
H12A H 0.2310 0.6058 0.2430 0.227 Uiso 1 1 calc R . .
H12B H 0.2184 0.4949 0.1494 0.227 Uiso 1 1 calc R . .
H12C H 0.2349 0.6900 0.1452 0.227 Uiso 1 1 calc R . .
C13 C 0.34306(16) 0.6093(5) 0.4200(3) 0.1028(12) Uani 1 1 d . . .
H13A H 0.3553 0.4926 0.4157 0.154 Uiso 1 1 calc R . .
H13B H 0.3065 0.6073 0.4214 0.154 Uiso 1 1 calc R . .
H13C H 0.3622 0.6628 0.4771 0.154 Uiso 1 1 calc R . .
C14 C 0.5000 1.3915(4) 0.2500 0.0519(8) Uani 1 2 d S . .
C15 C 0.45414(12) 1.5116(3) 0.2048(2) 0.0751(8) Uani 1 1 d . . .
H15A H 0.4654 1.5897 0.1609 0.113 Uiso 1 1 calc R . .
H15B H 0.4430 1.5771 0.2540 0.113 Uiso 1 1 calc R . .
H15C H 0.4256 1.4424 0.1715 0.113 Uiso 1 1 calc R . .
F1 F 0.44765(8) 1.0003(3) 0.16483(13) 0.1130(9) Uani 1 1 d . . .
F2 F 0.38262(10) 1.1856(3) 0.16512(15) 0.1307(10) Uani 1 1 d . . .
N1 N 0.44614(6) 1.1541(2) 0.31132(11) 0.0417(4) Uani 1 1 d . . .
N2 N 0.38186(7) 0.9174(2) 0.24605(12) 0.0471(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'
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'
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
F2 B1 F1 109.3(2) . .
F2 B1 N1 110.9(2) . .
F1 B1 N1 111.5(2) . .
F2 B1 N2 109.0(2) . .
F1 B1 N2 107.5(2) . .
N1 B1 N2 108.46(17) . .
N1 C1 C2 109.03(19) . .
N1 C1 C14 126.36(18) . .
C2 C1 C14 124.51(19) . .
C3 C2 C1 108.2(2) . .
C3 C2 H2 125.9 . .
C1 C2 H2 125.9 . .
C2 C3 C4 107.3(2) . .
C2 C3 H3 126.4 . .
C4 C3 H3 126.4 . .
C5 C4 N1 122.49(19) . .
C5 C4 C3 128.5(2) . .
N1 C4 C3 108.8(2) . .
C6 C5 C4 122.4(2) . .
C6 C5 H5 118.8 . .
C4 C5 H5 118.8 . .
C5 C6 N2 119.4(2) . .
C5 C6 C7 131.8(2) . .
N2 C6 C7 108.7(2) . .
C8 C7 C6 107.0(2) . .
C8 C7 C13 128.0(3) . .
C6 C7 C13 125.0(3) . .
C7 C8 C9 107.1(2) . .
C7 C8 C11 128.6(3) . .
C9 C8 C11 124.3(3) . .
N2 C9 C8 110.1(2) . .
N2 C9 C10 122.8(2) . .
C8 C9 C10 127.2(2) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 C8 111.0(4) . .
C12 C11 H11A 109.4 . .
C8 C11 H11A 109.4 . .
C12 C11 H11B 109.4 . .
C8 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C7 C13 H13A 109.5 . .
C7 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C7 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C1 C14 C1 114.8(2) 2_655 .
C1 C14 C15 107.10(13) 2_655 2_655
C1 C14 C15 110.50(14) . 2_655
C1 C14 C15 110.50(14) 2_655 .
C1 C14 C15 107.10(13) . .
C15 C14 C15 106.6(3) 2_655 .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C1 N1 C4 106.69(17) . .
C1 N1 B1 131.79(18) . .
C4 N1 B1 121.51(17) . .
C9 N2 C6 107.13(19) . .
C9 N2 B1 127.50(19) . .
C6 N2 B1 125.21(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F2 1.356(3) .
B1 F1 1.365(3) .
B1 N1 1.558(3) .
B1 N2 1.552(3) .
C1 N1 1.364(3) .
C1 C2 1.400(3) .
C1 C14 1.516(3) .
C2 C3 1.364(3) .
C2 H2 0.9300 .
C3 C4 1.396(3) .
C3 H3 0.9300 .
C4 C5 1.385(3) .
C4 N1 1.398(3) .
C5 C6 1.368(3) .
C5 H5 0.9300 .
C6 N2 1.392(3) .
C6 C7 1.416(3) .
C7 C8 1.366(4) .
C7 C13 1.502(4) .
C8 C9 1.419(4) .
C8 C11 1.512(4) .
C9 N2 1.339(3) .
C9 C10 1.488(4) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.467(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C1 1.516(3) 2_655
C14 C15 1.546(3) 2_655
C14 C15 1.546(3) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
