#------------------------------------------------------------------------------
#$Date: 2018-01-13 08:05:03 +0200 (Sat, 13 Jan 2018) $
#$Revision: 205169 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242318.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242318
loop_
_publ_author_name
'Joshi, Dhruval J.'
'Jun, Meesook'
'Yang, Lijing'
'Lough, Alan J.'
'Yan, Hongbin'
_publ_section_title
;
 Further investigation on the nitration of BODIPY with cupric nitrate:
 crystal structures of
 4,4-difluoro-1,3,5,7,8-pentamethyl-2-nitro-4-bora-3a,4a-diaza-s-indacene,
 4,4-difluoro-3-nitro-8-phenyl-4-bora-3a,4a-diaza-s-indacene, and
 3-chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-diaza-s-indacene
;
_journal_coeditor_code           HB7723
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              103
_journal_page_last               108
_journal_paper_doi               10.1107/S2056989017018564
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C14 H16 B F2 N3 O2'
_chemical_formula_moiety         'C14 H16 B F2 N3 O2'
_chemical_formula_sum            'C14 H16 B F2 N3 O2'
_chemical_formula_weight         307.11
_chemical_name_systematic
4,4-Difluoro-1,3,5,7,8-pentamethyl-2-nitro-4-bora-3a,4a-diaza-s-indacene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                110.762(3)
_cell_angle_beta                 101.468(4)
_cell_angle_gamma                95.463(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2837(9)
_cell_length_b                   8.6660(9)
_cell_length_c                   10.6619(12)
_cell_measurement_reflns_used    4795
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.55
_cell_volume                     689.83(13)
_computing_cell_refinement       APEX2
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18324
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.110
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS, Bruker, 2014)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0736P)²+0.2040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                2192
_reflns_number_total             3194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7723sup1.cif
_cod_data_source_block           5a
_cod_database_code               2242318
_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   0.979
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
F F1 0.30619(16) 0.28032(15) 0.74821(12) 0.0257(3) Uani d 1
F F2 0.51390(15) 0.22107(15) 0.63858(12) 0.0242(3) Uani d 1
O O1 0.9463(2) 0.7217(2) 1.08010(18) 0.0364(5) Uani d 1
O O2 0.8553(2) 0.9556(2) 1.11463(18) 0.0393(5) Uani d 1
N N1 0.3009(2) 0.3522(2) 0.54914(17) 0.0158(4) Uani d 1
N N2 0.5130(2) 0.5113(2) 0.77068(17) 0.0161(4) Uani d 1
N N3 0.8424(2) 0.8035(2) 1.05038(19) 0.0254(4) Uani d 1
C C1 0.6403(3) 0.5461(3) 0.8834(2) 0.0179(4) Uani d 1
C C2 0.7004(3) 0.7192(3) 0.9354(2) 0.0195(5) Uani d 1
C C3 0.6077(3) 0.7943(3) 0.8555(2) 0.0192(5) Uani d 1
C C4 0.4894(3) 0.6603(2) 0.7513(2) 0.0167(4) Uani d 1
C C5 0.3633(3) 0.6568(2) 0.6372(2) 0.0169(4) Uani d 1
C C6 0.2766(3) 0.5046(2) 0.5355(2) 0.0158(4) Uani d 1
C C7 0.1555(3) 0.4640(3) 0.4053(2) 0.0179(5) Uani d 1
C C8 0.1121(3) 0.2929(3) 0.3481(2) 0.0196(5) Uani d 1
H H8A 0.0351 0.2293 0.2615 0.024 Uiso calc 1
C C9 0.2001(3) 0.2260(3) 0.4383(2) 0.0186(5) Uani d 1
C C10 0.6895(3) 0.4176(3) 0.9389(2) 0.0224(5) Uani d 1
H H10A 0.5940 0.3260 0.9097 0.034 Uiso calc 1
H H10B 0.7241 0.4690 1.0403 0.034 Uiso calc 1
H H10C 0.7828 0.3732 0.9032 0.034 Uiso calc 1
C C11 0.6437(3) 0.9751(3) 0.8742(2) 0.0277(5) Uani d 1
H H11A 0.7646 1.0172 0.9089 0.041 Uiso calc 1
H H11B 0.5858 1.0410 0.9408 0.041 Uiso calc 1
H H11C 0.6042 0.9854 0.7850 0.041 Uiso calc 1
C C12 0.3210(3) 0.8177(3) 0.6290(2) 0.0237(5) Uani d 1
H H12A 0.2066 0.7970 0.5722 0.036 Uiso calc 1
H H12B 0.3995 0.8622 0.5871 0.036 Uiso calc 1
H H12C 0.3295 0.8993 0.7224 0.036 Uiso calc 1
C C13 0.0903(3) 0.5777(3) 0.3373(2) 0.0238(5) Uani d 1
H H13A 0.0292 0.5107 0.2411 0.036 Uiso calc 1
H H13B 0.1843 0.6567 0.3390 0.036 Uiso calc 1
H H13C 0.0148 0.6400 0.3873 0.036 Uiso calc 1
C C14 0.1843(3) 0.0471(3) 0.4224(2) 0.0220(5) Uani d 1
H H14A 0.1568 0.0359 0.5043 0.033 Uiso calc 1
H H14B 0.2905 0.0092 0.4124 0.033 Uiso calc 1
H H14C 0.0952 -0.0217 0.3398 0.033 Uiso calc 1
B B1 0.4081(3) 0.3348(3) 0.6781(2) 0.0175(5) Uani d 1
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
C9 N1 C6 108.30(17)
C9 N1 B1 125.81(17)
C6 N1 B1 125.47(17)
C1 N2 C4 109.29(17)
C1 N2 B1 125.41(17)
C4 N2 B1 125.30(17)
O1 N3 O2 123.0(2)
O1 N3 C2 118.71(18)
O2 N3 C2 118.29(19)
N2 C1 C2 106.78(18)
N2 C1 C10 122.98(19)
C2 C1 C10 130.1(2)
C1 C2 C3 110.67(19)
C1 C2 N3 123.69(19)
C3 C2 N3 125.57(19)
C2 C3 C4 104.34(18)
C2 C3 C11 125.6(2)
C4 C3 C11 129.8(2)
N2 C4 C3 108.91(17)
N2 C4 C5 120.27(18)
C3 C4 C5 130.80(19)
C6 C5 C4 120.20(18)
C6 C5 C12 119.87(19)
C4 C5 C12 119.91(18)
C5 C6 N1 120.78(18)
C5 C6 C7 131.91(18)
N1 C6 C7 107.31(17)
C8 C7 C6 106.11(17)
C8 C7 C13 124.27(19)
C6 C7 C13 129.57(19)
C7 C8 C9 109.13(19)
C7 C8 H8A 125.4
C9 C8 H8A 125.4
N1 C9 C8 109.12(18)
N1 C9 C14 123.11(18)
C8 C9 C14 127.73(19)
C1 C10 H10A 109.5
C1 C10 H10B 109.5
H10A C10 H10B 109.5
C1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C3 C11 H11A 109.5
C3 C11 H11B 109.5
H11A C11 H11B 109.5
C3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C5 C12 H12A 109.5
C5 C12 H12B 109.5
H12A C12 H12B 109.5
C5 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
C9 C14 H14A 109.5
C9 C14 H14B 109.5
H14A C14 H14B 109.5
C9 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
F1 B1 F2 109.40(17)
F1 B1 N1 110.37(18)
F2 B1 N1 110.00(17)
F1 B1 N2 110.71(17)
F2 B1 N2 109.91(18)
N1 B1 N2 106.41(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.385(3)
F2 B1 1.390(3)
O1 N3 1.229(2)
O2 N3 1.233(2)
N1 C9 1.345(3)
N1 C6 1.408(3)
N1 B1 1.546(3)
N2 C1 1.351(3)
N2 C4 1.403(3)
N2 B1 1.550(3)
N3 C2 1.431(3)
C1 C2 1.401(3)
C1 C10 1.488(3)
C2 C3 1.402(3)
C3 C4 1.407(3)
C3 C11 1.500(3)
C4 C5 1.427(3)
C5 C6 1.388(3)
C5 C12 1.497(3)
C6 C7 1.446(3)
C7 C8 1.367(3)
C7 C13 1.496(3)
C8 C9 1.410(3)
C8 H8A 0.9500
C9 C14 1.489(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8A O2 1_444 0.95 2.46 3.290(3) 146
C10 H10C O1 2_767 0.98 2.46 3.371(3) 155
C12 H12B F2 2_666 0.98 2.53 3.329(3) 139
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
C4 N2 C1 C2 -0.9(2)
B1 N2 C1 C2 179.69(18)
C4 N2 C1 C10 175.32(19)
B1 N2 C1 C10 -4.1(3)
N2 C1 C2 C3 1.0(2)
C10 C1 C2 C3 -174.9(2)
N2 C1 C2 N3 -176.23(19)
C10 C1 C2 N3 7.9(4)
O1 N3 C2 C1 22.4(3)
O2 N3 C2 C1 -158.0(2)
O1 N3 C2 C3 -154.4(2)
O2 N3 C2 C3 25.1(3)
C1 C2 C3 C4 -0.7(2)
N3 C2 C3 C4 176.5(2)
C1 C2 C3 C11 -175.5(2)
N3 C2 C3 C11 1.7(3)
C1 N2 C4 C3 0.5(2)
B1 N2 C4 C3 179.93(18)
C1 N2 C4 C5 179.00(18)
B1 N2 C4 C5 -1.6(3)
C2 C3 C4 N2 0.1(2)
C11 C3 C4 N2 174.6(2)
C2 C3 C4 C5 -178.2(2)
C11 C3 C4 C5 -3.6(4)
N2 C4 C5 C6 -7.6(3)
C3 C4 C5 C6 170.4(2)
N2 C4 C5 C12 170.72(18)
C3 C4 C5 C12 -11.2(3)
C4 C5 C6 N1 5.5(3)
C12 C5 C6 N1 -172.83(19)
C4 C5 C6 C7 -174.0(2)
C12 C5 C6 C7 7.7(3)
C9 N1 C6 C5 178.89(19)
B1 N1 C6 C5 6.0(3)
C9 N1 C6 C7 -1.5(2)
B1 N1 C6 C7 -174.36(18)
C5 C6 C7 C8 -179.9(2)
N1 C6 C7 C8 0.5(2)
C5 C6 C7 C13 2.5(4)
N1 C6 C7 C13 -177.1(2)
C6 C7 C8 C9 0.6(2)
C13 C7 C8 C9 178.35(19)
C6 N1 C9 C8 1.9(2)
B1 N1 C9 C8 174.73(19)
C6 N1 C9 C14 -175.81(19)
B1 N1 C9 C14 -3.0(3)
C7 C8 C9 N1 -1.6(2)
C7 C8 C9 C14 176.0(2)
C9 N1 B1 F1 -64.5(3)
C6 N1 B1 F1 107.2(2)
C9 N1 B1 F2 56.3(3)
C6 N1 B1 F2 -132.0(2)
C9 N1 B1 N2 175.34(18)
C6 N1 B1 N2 -13.0(3)
C1 N2 B1 F1 70.1(3)
C4 N2 B1 F1 -109.2(2)
C1 N2 B1 F2 -50.9(3)
C4 N2 B1 F2 129.82(19)
C1 N2 B1 N1 -169.97(18)
C4 N2 B1 N1 10.8(3)

_cod_database_fobs_code 2242318
