#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:18:57 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238536 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/76/7237695.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_7237695
loop_
_publ_author_name
'Shao, Tao'
'Liu, Tianyan'
'Liu, Hui'
'Zhang, Mingzhu'
'Shen, Yu'
'Gao, Awei'
'Tian, Xiaohe'
'Zhang, Qiong'
'Wu, Jieying'
'Tian, Yupeng'
_publ_section_title
;
 Identification of fatty liver disease at diverse stages using two-photon
 absorption of triphenylamine-based BODIPY analogues
;
_journal_issue                   23
_journal_name_full               'Journal of Materials Chemistry B'
_journal_page_first              3704
_journal_paper_doi               10.1039/C9TB00421A
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C18 H21 B F2 N2 O'
_chemical_formula_weight         330.18
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-12-01 deposited with the CCDC.	2019-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.863(2)
_cell_length_b                   12.769(4)
_cell_length_c                   16.939(5)
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.8085
_cell_measurement_theta_min      2.404
_cell_volume                     1700.7(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12087
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(8)
_refine_ls_extinction_coef       0.0166(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                2470
_reflns_number_total             2985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9tb00421a2.cif
_cod_data_source_block           aai
_cod_original_cell_volume        1700.6(9)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7237695
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C6 C 0.0552(2) 0.82019(14) 0.54183(10) 0.0467(4) Uani 1 1 d .
H6 H 0.1124 0.7631 0.5205 0.056 Uiso 1 1 calc R
C8 C -0.0377(2) 0.91769(13) 0.65660(10) 0.0422(4) Uani 1 1 d .
C7 C 0.0395(2) 0.82913(13) 0.62193(10) 0.0429(4) Uani 1 1 d .
C11 C -0.0413(2) 0.92739(13) 0.73880(10) 0.0448(5) Uani 1 1 d .
H11 H -0.0806 0.9897 0.7606 0.054 Uiso 1 1 calc R
C5 C -0.0144(2) 0.89668(14) 0.49126(10) 0.0453(4) Uani 1 1 d .
C9 C -0.1052(2) 0.99380(14) 0.60581(11) 0.0513(5) Uani 1 1 d .
H9 H -0.1567 1.0529 0.6273 0.062 Uiso 1 1 calc R
C10 C -0.0975(2) 0.98343(15) 0.52609(11) 0.0539(5) Uani 1 1 d .
H10 H -0.1474 1.0339 0.4940 0.065 Uiso 1 1 calc R
C12 C 0.0153(2) 0.87050(15) 0.87051(10) 0.0466(5) Uani 1 1 d .
C17 C 0.0762(3) 0.96296(16) 0.90053(11) 0.0582(5) Uani 1 1 d .
H17 H 0.1076 1.0167 0.8665 0.070 Uiso 1 1 calc R
C4 C -0.0995(3) 0.95395(16) 0.35812(11) 0.0590(5) Uani 1 1 d .
H4A H -0.2059 0.9719 0.3837 0.071 Uiso 1 1 calc R
H4B H -0.1263 0.9136 0.3112 0.071 Uiso 1 1 calc R
C16 C 0.0911(3) 0.97654(19) 0.98094(12) 0.0656(6) Uani 1 1 d .
H16 H 0.1323 1.0398 1.0003 0.079 Uiso 1 1 calc R
C13 C -0.0341(3) 0.79275(16) 0.92207(11) 0.0658(6) Uani 1 1 d .
H13 H -0.0775 0.7301 0.9027 0.079 Uiso 1 1 calc R
C15 C 0.0463(2) 0.89842(18) 1.03351(11) 0.0592(5) Uani 1 1 d .
C14 C -0.0192(3) 0.80770(17) 1.00234(12) 0.0708(6) Uani 1 1 d .
H14 H -0.0546 0.7549 1.0364 0.085 Uiso 1 1 calc R
C18 C 0.0714(3) 0.9123(2) 1.12192(11) 0.0846(8) Uani 1 1 d .
H18A H 0.0032 0.9698 1.1401 0.127 Uiso 1 1 calc R
H18B H 0.1891 0.9264 1.1327 0.127 Uiso 1 1 calc R
H18C H 0.0377 0.8494 1.1488 0.127 Uiso 1 1 calc R
C2 C 0.1136(3) 0.81124(16) 0.37472(11) 0.0604(6) Uani 1 1 d .
H2A H 0.2122 0.8008 0.4082 0.072 Uiso 1 1 calc R
H2B H 0.1532 0.8387 0.3246 0.072 Uiso 1 1 calc R
C1 C 0.0288(3) 0.70751(19) 0.36093(14) 0.0836(7) Uani 1 1 d .
H1A H -0.0107 0.6798 0.4103 0.125 Uiso 1 1 calc R
H1B H 0.1088 0.6597 0.3378 0.125 Uiso 1 1 calc R
H1C H -0.0660 0.7167 0.3258 0.125 Uiso 1 1 calc R
C3 C -0.0104(3) 1.05387(19) 0.33347(14) 0.0854(7) Uani 1 1 d .
H3A H 0.0216 1.0928 0.3796 0.128 Uiso 1 1 calc R
H3B H -0.0859 1.0953 0.3017 0.128 Uiso 1 1 calc R
H3C H 0.0894 1.0369 0.3035 0.128 Uiso 1 1 calc R
N2 N 0.00836(18) 0.85241(11) 0.78665(8) 0.0442(4) Uani 1 1 d .
N1 N 0.00067(19) 0.88861(12) 0.41175(8) 0.0534(4) Uani 1 1 d .
O1 O 0.10188(16) 0.75318(9) 0.66857(7) 0.0569(4) Uani 1 1 d .
B1 B 0.0635(3) 0.74365(17) 0.75115(13) 0.0493(5) Uani 1 1 d .
F2 F -0.06955(15) 0.67323(8) 0.76199(7) 0.0676(4) Uani 1 1 d .
F1 F 0.20586(15) 0.70852(9) 0.79013(6) 0.0663(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 0.0033 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
C7 C6 C5 120.67(16)
C11 C8 C9 122.81(16)
C11 C8 C7 119.60(16)
C9 C8 C7 117.58(16)
O1 C7 C6 119.35(15)
O1 C7 C8 119.39(15)
C6 C7 C8 121.24(16)
N2 C11 C8 122.95(16)
N1 C5 C6 121.13(16)
N1 C5 C10 120.93(16)
C6 C5 C10 117.93(15)
C10 C9 C8 121.69(18)
C9 C10 C5 120.77(17)
C17 C12 C13 118.91(17)
C17 C12 N2 121.12(16)
C13 C12 N2 119.93(17)
C12 C17 C16 120.29(19)
N1 C4 C3 113.77(17)
C17 C16 C15 121.6(2)
C14 C13 C12 120.1(2)
C14 C15 C16 117.16(18)
C14 C15 C18 121.7(2)
C16 C15 C18 121.1(2)
C15 C14 C13 121.9(2)
N1 C2 C1 113.03(17)
C11 N2 C12 120.19(15)
C11 N2 B1 119.28(14)
C12 N2 B1 120.52(15)
C5 N1 C4 121.76(16)
C5 N1 C2 121.87(16)
C4 N1 C2 116.34(15)
C7 O1 B1 123.86(14)
F1 B1 F2 109.75(16)
F1 B1 O1 108.94(17)
F2 B1 O1 109.94(17)
F1 B1 N2 109.19(17)
F2 B1 N2 108.20(16)
O1 B1 N2 110.80(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C7 1.367(2)
C6 C5 1.410(2)
C8 C11 1.398(2)
C8 C9 1.402(2)
C8 C7 1.411(2)
C7 O1 1.3436(19)
C11 N2 1.314(2)
C5 N1 1.356(2)
C5 C10 1.415(3)
C9 C10 1.358(2)
C12 C17 1.372(3)
C12 C13 1.378(3)
C12 N2 1.440(2)
C17 C16 1.378(3)
C4 N1 1.463(2)
C4 C3 1.514(3)
C16 C15 1.383(3)
C13 C14 1.378(3)
C15 C14 1.373(3)
C15 C18 1.521(3)
C2 N1 1.469(2)
C2 C1 1.501(3)
N2 B1 1.574(3)
O1 B1 1.436(3)
B1 F1 1.375(2)
B1 F2 1.392(2)
