#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/36/1513645.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_1513645
loop_
_publ_author_name
'Choi, Sohee'
'Bouffard, Jean'
'Kim, Youngmi'
_publ_section_title
;
 Aggregation-induced emission enhancement of a meso-trifluoromethyl BODIPY
 via J-aggregation
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              751
_journal_paper_doi               10.1039/c3sc52495g
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C14 H17 B F2 N2'
_chemical_formula_sum            'C14 H17 B F2 N2'
_chemical_formula_weight         262.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3274(11)
_cell_length_b                   7.1032(6)
_cell_length_c                   16.0113(15)
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.20
_cell_volume                     1288.3(2)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9171
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0526
_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)+(0.0933P)²+0.0903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                1098
_reflns_number_total             1734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc52495g.txt
_cod_data_source_block           BDPCH3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               1513645
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
B1 B 0.7511(2) 0.2500 0.59100(17) 0.0371(6) Uani 1 2 d S
F1 F 0.80030(9) 0.09094(17) 0.62746(7) 0.0572(4) Uani 1 1 d .
N1 N 0.61626(16) 0.2500 0.60291(11) 0.0323(5) Uani 1 2 d S
N2 N 0.77414(17) 0.2500 0.49644(12) 0.0327(5) Uani 1 2 d S
C1 C 0.5582(2) 0.2500 0.67681(14) 0.0370(6) Uani 1 2 d S
C2 C 0.4372(2) 0.2500 0.66164(15) 0.0395(6) Uani 1 2 d S
H2 H 0.3774 0.2500 0.7032 0.047 Uiso 1 2 calc SR
C3 C 0.4182(2) 0.2500 0.57640(15) 0.0361(6) Uani 1 2 d S
C4 C 0.5320(2) 0.2500 0.53833(13) 0.0310(5) Uani 1 2 d S
C5 C 0.6187(3) 0.2500 0.75926(16) 0.0482(7) Uani 1 2 d S
H5A H 0.6851 0.1617 0.7579 0.072 Uiso 0.50 1 calc PR
H5B H 0.5628 0.2114 0.8027 0.072 Uiso 0.50 1 calc PR
H5C H 0.6479 0.3769 0.7715 0.072 Uiso 0.50 1 calc PR
C6 C 0.2983(2) 0.2500 0.53689(18) 0.0452(6) Uani 1 2 d S
H6A H 0.2384 0.2243 0.5796 0.068 Uiso 0.50 1 calc PR
H6B H 0.2949 0.1524 0.4937 0.068 Uiso 0.50 1 calc PR
H6C H 0.2831 0.3733 0.5116 0.068 Uiso 0.50 1 calc PR
C7 C 0.5678(2) 0.2500 0.45442(14) 0.0327(5) Uani 1 2 d S
C8 C 0.4762(2) 0.2500 0.38743(14) 0.0412(6) Uani 1 2 d S
H8A H 0.4523 0.3798 0.3754 0.062 Uiso 0.50 1 calc PR
H8B H 0.4075 0.1776 0.4061 0.062 Uiso 0.50 1 calc PR
H8C H 0.5088 0.1926 0.3368 0.062 Uiso 0.50 1 calc PR
C9 C 0.6876(2) 0.2500 0.43352(14) 0.0319(5) Uani 1 2 d S
C10 C 0.7472(2) 0.2500 0.35523(14) 0.0384(6) Uani 1 2 d S
C11 C 0.8668(2) 0.2500 0.37338(16) 0.0441(6) Uani 1 2 d S
H11 H 0.9287 0.2500 0.3334 0.053 Uiso 1 2 calc SR
C12 C 0.8816(2) 0.2500 0.45974(15) 0.0377(6) Uani 1 2 d S
C13 C 0.6975(3) 0.2500 0.26829(16) 0.0500(7) Uani 1 2 d S
H13A H 0.6389 0.3508 0.2631 0.075 Uiso 0.50 1 calc PR
H13B H 0.6598 0.1284 0.2571 0.075 Uiso 0.50 1 calc PR
H13C H 0.7613 0.2707 0.2280 0.075 Uiso 0.50 1 calc PR
C14 C 0.9939(2) 0.2500 0.50754(18) 0.0490(7) Uani 1 2 d S
H14A H 1.0062 0.1258 0.5327 0.074 Uiso 0.50 1 calc PR
H14B H 0.9901 0.3455 0.5516 0.074 Uiso 0.50 1 calc PR
H14C H 1.0596 0.2788 0.4698 0.074 Uiso 0.50 1 calc PR
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
F1 B1 F1 108.9(2) 7_565
F1 B1 N2 110.26(14) 7_565
F1 B1 N2 110.26(14) .
F1 B1 N1 110.25(14) 7_565
F1 B1 N1 110.25(14) .
N2 B1 N1 106.89(19) .
C1 N1 C4 108.23(19) .
C1 N1 B1 126.16(19) .
C4 N1 B1 125.61(18) .
C12 N2 C9 108.4(2) .
C12 N2 B1 125.5(2) .
C9 N2 B1 126.01(19) .
N1 C1 C2 109.0(2) .
N1 C1 C5 123.5(2) .
C2 C1 C5 127.5(2) .
C3 C2 C1 109.0(2) .
C3 C2 H2 125.5 .
C1 C2 H2 125.5 .
C2 C3 C4 106.4(2) .
C2 C3 C6 123.9(2) .
C4 C3 C6 129.7(2) .
C7 C4 N1 120.4(2) .
C7 C4 C3 132.2(2) .
N1 C4 C3 107.40(19) .
C1 C5 H5A 109.5 .
C1 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C1 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C3 C6 H6A 109.5 .
C3 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C3 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
C9 C7 C4 120.7(2) .
C9 C7 C8 120.2(2) .
C4 C7 C8 119.1(2) .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C7 C9 N2 120.4(2) .
C7 C9 C10 132.2(2) .
N2 C9 C10 107.5(2) .
C11 C10 C9 106.2(2) .
C11 C10 C13 124.1(2) .
C9 C10 C13 129.6(2) .
C10 C11 C12 109.0(2) .
C10 C11 H11 125.5 .
C12 C11 H11 125.5 .
N2 C12 C11 108.8(2) .
N2 C12 C14 123.2(2) .
C11 C12 C14 128.0(2) .
C10 C13 H13A 109.5 .
C10 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C10 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C12 C14 H14A 109.5 .
C12 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C12 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.3885(19) 7_565
B1 F1 1.3885(19) .
B1 N2 1.536(3) .
B1 N1 1.539(3) .
N1 C1 1.354(3) .
N1 C4 1.408(3) .
N2 C12 1.352(3) .
N2 C9 1.406(3) .
C1 C2 1.392(3) .
C1 C5 1.487(3) .
C2 C3 1.382(4) .
C2 H2 0.9500 .
C3 C4 1.425(3) .
C3 C6 1.499(3) .
C4 C7 1.404(3) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C9 1.397(3) .
C7 C8 1.492(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.424(3) .
C10 C11 1.385(4) .
C10 C13 1.502(3) .
C11 C12 1.393(3) .
C11 H11 0.9500 .
C12 C14 1.485(4) .
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_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
F1 B1 N1 C1 -60.15(15) 7_565
F1 B1 N1 C1 60.15(15) .
N2 B1 N1 C1 180.0 .
F1 B1 N1 C4 119.85(15) 7_565
F1 B1 N1 C4 -119.85(15) .
N2 B1 N1 C4 0.0 .
F1 B1 N2 C12 60.16(15) 7_565
F1 B1 N2 C12 -60.16(15) .
N1 B1 N2 C12 180.0 .
F1 B1 N2 C9 -119.84(15) 7_565
F1 B1 N2 C9 119.84(15) .
N1 B1 N2 C9 0.0 .
C4 N1 C1 C2 0.0 .
B1 N1 C1 C2 180.0 .
C4 N1 C1 C5 180.0 .
B1 N1 C1 C5 0.0 .
N1 C1 C2 C3 0.0 .
C5 C1 C2 C3 180.0 .
C1 C2 C3 C4 0.0 .
C1 C2 C3 C6 180.0 .
C1 N1 C4 C7 180.0 .
B1 N1 C4 C7 0.0 .
C1 N1 C4 C3 0.0 .
B1 N1 C4 C3 180.0 .
C2 C3 C4 C7 180.0 .
C6 C3 C4 C7 0.0 .
C2 C3 C4 N1 0.0 .
C6 C3 C4 N1 180.0 .
N1 C4 C7 C9 0.0 .
C3 C4 C7 C9 180.0 .
N1 C4 C7 C8 180.0 .
C3 C4 C7 C8 0.0 .
C4 C7 C9 N2 0.0 .
C8 C7 C9 N2 180.0 .
C4 C7 C9 C10 180.0 .
C8 C7 C9 C10 0.0 .
C12 N2 C9 C7 180.0 .
B1 N2 C9 C7 0.0 .
C12 N2 C9 C10 0.0 .
B1 N2 C9 C10 180.0 .
C7 C9 C10 C11 180.0 .
N2 C9 C10 C11 0.0 .
C7 C9 C10 C13 0.0 .
N2 C9 C10 C13 180.0 .
C9 C10 C11 C12 0.0 .
C13 C10 C11 C12 180.0 .
C9 N2 C12 C11 0.0 .
B1 N2 C12 C11 180.0 .
C9 N2 C12 C14 180.0 .
B1 N2 C12 C14 0.0 .
C10 C11 C12 N2 0.0 .
C10 C11 C12 C14 180.0 .
