#------------------------------------------------------------------------------
#$Date: 2017-05-05 18:23:27 +0200 (Fri 05 de May de 2017) $
#$Revision: 196256 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/56/7155614.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_7155614
loop_
_publ_author_name
'Miao, Fang'
'Lim, Zheng Long'
'Hu, Pan'
'Dong, Shaoqiang'
'Qi, Qingbiao'
'Zhang, Xiaojie'
'Wu, Jishan'
_publ_section_title
;
 BODIPY blocked anthroxyl radicals: the substituent effect on reactivity
 and fluorescence turn-on detection of a hydroxyl radical.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3188
_journal_page_last               3191
_journal_paper_doi               10.1039/c7ob00586e
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C13.50 H11 B0.50 F N O0.50'
_chemical_formula_sum            'C13.5 H11 B0.5 F N O0.5'
_chemical_formula_weight         219.64
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-09 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.9610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1844(5)
_cell_length_b                   20.7250(6)
_cell_length_c                   6.8775(2)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.278
_cell_measurement_theta_min      3.652
_cell_volume                     2124.84(11)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2015.5.2'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9574
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.278
_diffrn_reflns_theta_min         3.652
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0450
_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)+(0.0706P)²+1.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1838
_reflns_number_total             2077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob00586e2.cif
_cod_data_source_block           g271
_cod_original_formula_sum        'C13.50 H11 B0.50 F N O0.50'
_cod_database_code               7155614
_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   0.690
_shelx_estimated_absorpt_t_max   0.961
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
B1 B 0.5000 0.87969(11) 0.2500 0.0413(7) Uani 1 2 d S T P
F1 F 0.56308(7) 0.91836(5) 0.3683(2) 0.0703(5) Uani 1 1 d . . .
N1 N 0.45393(8) 0.83555(6) 0.3817(2) 0.0337(3) Uani 1 1 d . . .
O1 O 0.5000 0.46437(7) 0.2500 0.0409(4) Uani 1 2 d S T P
C1 C 0.40736(12) 0.85413(8) 0.5208(3) 0.0440(4) Uani 1 1 d . . .
C2 C 0.37835(12) 0.79963(8) 0.6113(3) 0.0451(4) Uani 1 1 d . . .
H2 H 0.3442 0.8000 0.7135 0.054 Uiso 1 1 calc R U .
C3 C 0.40783(10) 0.74525(7) 0.5267(2) 0.0332(4) Uani 1 1 d . . .
C4 C 0.45562(9) 0.76788(6) 0.3807(2) 0.0268(3) Uani 1 1 d . . .
C5 C 0.5000 0.73521(8) 0.2500 0.0229(4) Uani 1 2 d S T P
C6 C 0.5000 0.66343(8) 0.2500 0.0220(4) Uani 1 2 d S T P
C7 C 0.57921(8) 0.62963(6) 0.33899(19) 0.0230(3) Uani 1 1 d . . .
C8 C 0.65883(9) 0.66259(7) 0.4276(2) 0.0259(3) Uani 1 1 d . . .
H8 H 0.6596 0.7084 0.4294 0.031 Uiso 1 1 calc R U .
C9 C 0.73474(9) 0.62896(7) 0.5108(2) 0.0307(3) Uani 1 1 d . . .
H9 H 0.7875 0.6517 0.5691 0.037 Uiso 1 1 calc R U .
C10 C 0.73468(10) 0.56167(7) 0.5100(2) 0.0339(4) Uani 1 1 d . . .
H10 H 0.7874 0.5388 0.5678 0.041 Uiso 1 1 calc R U .
C11 C 0.65863(10) 0.52816(7) 0.4258(2) 0.0327(4) Uani 1 1 d . . .
H11 H 0.6593 0.4823 0.4262 0.039 Uiso 1 1 calc R U .
C12 C 0.58036(9) 0.56105(6) 0.3396(2) 0.0262(3) Uani 1 1 d . . .
C13 C 0.38962(16) 0.92314(9) 0.5612(4) 0.0653(7) Uani 1 1 d . . .
H13A H 0.4442 0.9485 0.5623 0.098 Uiso 1 1 calc R U .
H13B H 0.3716 0.9267 0.6902 0.098 Uiso 1 1 calc R U .
H13C H 0.3414 0.9395 0.4576 0.098 Uiso 1 1 calc R U .
C14 C 0.39007(12) 0.67728(8) 0.5815(2) 0.0403(4) Uani 1 1 d . . .
H14A H 0.3720 0.6768 0.7110 0.060 Uiso 1 1 calc R U .
H14B H 0.4447 0.6515 0.5880 0.060 Uiso 1 1 calc R U .
H14C H 0.3419 0.6590 0.4815 0.060 Uiso 1 1 calc R U .
C15 C 0.5000 0.52423(9) 0.2500 0.0297(4) Uani 1 2 d S T P
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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
F1 B1 F1 109.42(19) . 2_655
F1 B1 N1 110.28(6) . 2_655
F1 B1 N1 109.72(8) 2_655 2_655
F1 B1 N1 109.72(8) . .
F1 B1 N1 110.28(6) 2_655 .
N1 B1 N1 107.40(16) 2_655 .
C1 N1 C4 107.52(13) . .
C1 N1 B1 127.12(13) . .
C4 N1 B1 125.34(12) . .
N1 C1 C2 109.66(13) . .
N1 C1 C13 122.90(19) . .
C2 C1 C13 127.42(18) . .
C3 C2 C1 108.46(16) . .
C3 C2 H2 125.8 . .
C1 C2 H2 125.8 . .
C2 C3 C4 106.10(14) . .
C2 C3 C14 125.03(15) . .
C4 C3 C14 128.87(13) . .
C5 C4 N1 119.95(13) . .
C5 C4 C3 131.79(13) . .
N1 C4 C3 108.26(12) . .
C4 C5 C4 122.02(17) . 2_655
C4 C5 C6 118.99(9) . .
C4 C5 C6 118.99(9) 2_655 .
C7 C6 C7 121.13(16) . 2_655
C7 C6 C5 119.44(8) . .
C7 C6 C5 119.44(8) 2_655 .
C8 C7 C12 118.07(12) . .
C8 C7 C6 121.83(12) . .
C12 C7 C6 120.10(12) . .
C9 C8 C7 120.81(12) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 120.35(13) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C11 C10 C9 120.39(13) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 120.59(13) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C11 C12 C7 119.80(12) . .
C11 C12 C15 119.63(13) . .
C7 C12 C15 120.58(12) . .
C1 C13 H13A 109.5 . .
C1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C3 C14 H14A 109.5 . .
C3 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C3 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O1 C15 C12 121.24(8) . .
O1 C15 C12 121.24(8) . 2_655
C12 C15 C12 117.51(16) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.3875(16) .
B1 F1 1.3876(16) 2_655
B1 N1 1.5450(19) 2_655
B1 N1 1.5450(19) .
N1 C1 1.349(2) .
N1 C4 1.4028(17) .
O1 C15 1.241(2) .
C1 C2 1.400(3) .
C1 C13 1.491(2) .
C2 C3 1.381(2) .
C2 H2 0.9500 .
C3 C4 1.425(2) .
C3 C14 1.496(2) .
C4 C5 1.3968(16) .
C5 C4 1.3968(16) 2_655
C5 C6 1.488(2) .
C6 C7 1.4255(15) .
C6 C7 1.4255(15) 2_655
C7 C8 1.4212(18) .
C7 C12 1.4213(18) .
C8 C9 1.3751(19) .
C8 H8 0.9500 .
C9 C10 1.395(2) .
C9 H9 0.9500 .
C10 C11 1.377(2) .
C10 H10 0.9500 .
C11 C12 1.4003(19) .
C11 H11 0.9500 .
C12 C15 1.4714(17) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C12 1.4714(17) 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
F1 B1 N1 C1 58.90(17) . .
F1 B1 N1 C1 -61.70(18) 2_655 .
N1 B1 N1 C1 178.77(15) 2_655 .
F1 B1 N1 C4 -119.14(15) . .
F1 B1 N1 C4 120.26(16) 2_655 .
N1 B1 N1 C4 0.74(9) 2_655 .
C4 N1 C1 C2 -0.04(17) . .
B1 N1 C1 C2 -178.36(12) . .
C4 N1 C1 C13 -178.52(15) . .
B1 N1 C1 C13 3.2(2) . .
N1 C1 C2 C3 0.17(19) . .
C13 C1 C2 C3 178.56(17) . .
C1 C2 C3 C4 -0.23(18) . .
C1 C2 C3 C14 -179.50(15) . .
C1 N1 C4 C5 -179.83(11) . .
B1 N1 C4 C5 -1.47(17) . .
C1 N1 C4 C3 -0.10(16) . .
B1 N1 C4 C3 178.26(10) . .
C2 C3 C4 C5 179.89(13) . .
C14 C3 C4 C5 -0.9(3) . .
C2 C3 C4 N1 0.20(16) . .
C14 C3 C4 N1 179.44(15) . .
N1 C4 C5 C4 0.71(8) . 2_655
C3 C4 C5 C4 -178.95(17) . 2_655
N1 C4 C5 C6 -179.29(8) . .
C3 C4 C5 C6 1.05(17) . .
C4 C5 C6 C7 -104.80(8) . .
C4 C5 C6 C7 75.20(8) 2_655 .
C4 C5 C6 C7 75.20(8) . 2_655
C4 C5 C6 C7 -104.80(8) 2_655 2_655
C7 C6 C7 C8 179.75(13) 2_655 .
C5 C6 C7 C8 -0.25(13) . .
C7 C6 C7 C12 0.22(8) 2_655 .
C5 C6 C7 C12 -179.78(8) . .
C12 C7 C8 C9 0.21(19) . .
C6 C7 C8 C9 -179.32(11) . .
C7 C8 C9 C10 -0.2(2) . .
C8 C9 C10 C11 0.0(2) . .
C9 C10 C11 C12 0.1(2) . .
C10 C11 C12 C7 -0.1(2) . .
C10 C11 C12 C15 179.83(12) . .
C8 C7 C12 C11 -0.08(19) . .
C6 C7 C12 C11 179.46(11) . .
C8 C7 C12 C15 -179.98(10) . .
C6 C7 C12 C15 -0.43(16) . .
C11 C12 C15 O1 0.32(14) . .
C7 C12 C15 O1 -179.78(8) . .
C11 C12 C15 C12 -179.68(14) . 2_655
C7 C12 C15 C12 0.22(8) . 2_655
