#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:01:31 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/75/7227515.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_7227515
loop_
_publ_author_name
'Fang, Wenyan'
'Zhang, Yuyang'
'Zhang, Gaobin'
'Kong, Lin'
'Yang, Longmei'
'Yang, Jiaxiang'
_publ_section_title
;
 Multi-stimuli-responsive fluorescence of a highly emissive difluoroboron
 complex in both solution and solid states
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1294
_journal_paper_doi               10.1039/C6CE02376B
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C24 H23 N3 O S'
_chemical_formula_weight         401.52
_chemical_name_common            S3
_chemical_name_systematic
;
 ?
;
_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_creation_method           SHELXL-97
_audit_update_record
;
2017-01-08 deposited with the CCDC.
2017-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 119.293(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.886(3)
_cell_length_b                   10.6027(18)
_cell_length_c                   16.7359(18)
_cell_measurement_reflns_used    5199
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.28
_cell_volume                     4160.8(10)
_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      296(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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14422
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0396
_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)+(0.0604P)²+1.3973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2829
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce02376b2.cif
_cod_data_source_block           S3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7227515--7227516.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7227515
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
S1 S 0.07565(2) 0.32945(6) -0.24867(3) 0.0700(2) Uani 1 1 d .
O1 O 0.33943(7) 0.52293(13) 0.50943(9) 0.0784(5) Uani 1 1 d .
H1 H 0.3242 0.5031 0.4556 0.094 Uiso 1 1 d R
N1 N 0.43778(8) 0.33709(17) 0.80599(10) 0.0671(5) Uani 1 1 d .
N2 N 0.29005(6) 0.37459(15) 0.36705(9) 0.0515(4) Uani 1 1 d .
N3 N 0.05533(8) 0.2652(3) -0.07611(12) 0.0927(7) Uani 1 1 d .
C1 C 0.43845(11) 0.5301(3) 0.88852(17) 0.0932(8) Uani 1 1 d .
H1A H 0.4026 0.5601 0.8403 0.140 Uiso 1 1 calc R
H1B H 0.4619 0.6006 0.9218 0.140 Uiso 1 1 calc R
H1C H 0.4320 0.4776 0.9294 0.140 Uiso 1 1 calc R
C2 C 0.46790(10) 0.4552(2) 0.84815(14) 0.0782(7) Uani 1 1 d .
H2A H 0.4707 0.5058 0.8022 0.094 Uiso 1 1 calc R
H2B H 0.5063 0.4357 0.8959 0.094 Uiso 1 1 calc R
C3 C 0.50638(11) 0.1611(3) 0.87929(18) 0.0925(8) Uani 1 1 d .
H3A H 0.4989 0.1279 0.8211 0.139 Uiso 1 1 calc R
H3B H 0.5157 0.0932 0.9223 0.139 Uiso 1 1 calc R
H3C H 0.5378 0.2190 0.9014 0.139 Uiso 1 1 calc R
C4 C 0.45410(9) 0.2291(2) 0.86848(13) 0.0675(6) Uani 1 1 d .
H4A H 0.4225 0.1701 0.8457 0.081 Uiso 1 1 calc R
H4B H 0.4613 0.2583 0.9281 0.081 Uiso 1 1 calc R
C5 C 0.40164(8) 0.32602(19) 0.71360(12) 0.0525(5) Uani 1 1 d .
C6 C 0.38583(8) 0.43081(19) 0.65517(12) 0.0576(5) Uani 1 1 d .
H6 H 0.3984 0.5106 0.6800 0.069 Uiso 1 1 calc R
C7 C 0.35211(8) 0.41824(17) 0.56170(12) 0.0525(4) Uani 1 1 d .
C8 C 0.37917(8) 0.20733(19) 0.67325(12) 0.0562(5) Uani 1 1 d .
H8 H 0.3876 0.1361 0.7101 0.067 Uiso 1 1 calc R
C9 C 0.34529(8) 0.19698(18) 0.58104(13) 0.0555(5) Uani 1 1 d .
H9 H 0.3309 0.1179 0.5565 0.067 Uiso 1 1 calc R
C10 C 0.33105(7) 0.29975(17) 0.52126(11) 0.0477(4) Uani 1 1 d .
C11 C 0.29916(8) 0.28408(18) 0.42387(12) 0.0517(4) Uani 1 1 d .
H11 H 0.2843 0.2048 0.4006 0.062 Uiso 1 1 calc R
C12 C 0.25860(7) 0.35330(17) 0.27172(11) 0.0473(4) Uani 1 1 d .
C13 C 0.21207(7) 0.27260(18) 0.23073(11) 0.0504(4) Uani 1 1 d .
H13 H 0.2015 0.2255 0.2670 0.061 Uiso 1 1 calc R
C14 C 0.18129(7) 0.26172(17) 0.13644(11) 0.0484(4) Uani 1 1 d .
H14 H 0.1501 0.2077 0.1101 0.058 Uiso 1 1 calc R
C15 C 0.27357(8) 0.42178(17) 0.21571(12) 0.0521(4) Uani 1 1 d .
H15 H 0.3045 0.4766 0.2420 0.062 Uiso 1 1 calc R
C16 C 0.24317(7) 0.40942(17) 0.12158(11) 0.0501(4) Uani 1 1 d .
H16 H 0.2544 0.4548 0.0855 0.060 Uiso 1 1 calc R
C17 C 0.19600(7) 0.32994(16) 0.07995(11) 0.0444(4) Uani 1 1 d .
C18 C 0.16016(7) 0.32352(16) -0.02101(11) 0.0450(4) Uani 1 1 d .
C19 C 0.10169(8) 0.2903(2) -0.05331(12) 0.0593(5) Uani 1 1 d .
C20 C 0.17850(7) 0.35089(16) -0.08096(12) 0.0475(4) Uani 1 1 d .
H20 H 0.2174 0.3667 -0.0545 0.057 Uiso 1 1 calc R
C21 C 0.14753(7) 0.35959(16) -0.17914(12) 0.0479(4) Uani 1 1 d .
C22 C 0.17166(8) 0.39956(18) -0.23166(12) 0.0557(5) Uani 1 1 d .
H22 H 0.2100 0.4203 -0.2072 0.067 Uiso 1 1 calc R
C23 C 0.13210(9) 0.4052(2) -0.32534(13) 0.0655(5) Uani 1 1 d .
H23 H 0.1413 0.4305 -0.3697 0.079 Uiso 1 1 calc R
C24 C 0.07917(10) 0.3699(2) -0.34432(13) 0.0705(6) Uani 1 1 d .
H24 H 0.0480 0.3679 -0.4032 0.085 Uiso 1 1 calc R
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'
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'
S S 0.1246 0.1234 '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
C24 S1 C21 91.61(10)
C7 O1 H1 109.6
C5 N1 C4 122.51(17)
C5 N1 C2 122.28(17)
C4 N1 C2 114.88(16)
C11 N2 C12 120.54(16)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C1 112.3(2)
N1 C2 H2A 109.1
C1 C2 H2A 109.1
N1 C2 H2B 109.1
C1 C2 H2B 109.1
H2A C2 H2B 107.9
C4 C3 H3A 109.5
C4 C3 H3B 109.5
H3A C3 H3B 109.5
C4 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N1 C4 C3 113.25(18)
N1 C4 H4A 108.9
C3 C4 H4A 108.9
N1 C4 H4B 108.9
C3 C4 H4B 108.9
H4A C4 H4B 107.7
N1 C5 C6 121.65(17)
N1 C5 C8 121.04(17)
C6 C5 C8 117.31(16)
C7 C6 C5 121.45(18)
C7 C6 H6 119.3
C5 C6 H6 119.3
O1 C7 C6 118.26(17)
O1 C7 C10 120.51(16)
C6 C7 C10 121.23(17)
C9 C8 C5 120.37(17)
C9 C8 H8 119.8
C5 C8 H8 119.8
C8 C9 C10 123.06(18)
C8 C9 H9 118.5
C10 C9 H9 118.5
C9 C10 C7 116.48(16)
C9 C10 C11 121.67(17)
C7 C10 C11 121.78(16)
N2 C11 C10 123.07(17)
N2 C11 H11 118.5
C10 C11 H11 118.5
C13 C12 C15 118.44(15)
C13 C12 N2 123.63(16)
C15 C12 N2 117.86(16)
C14 C13 C12 120.46(17)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C17 121.43(16)
C13 C14 H14 119.3
C17 C14 H14 119.3
C16 C15 C12 120.93(16)
C16 C15 H15 119.5
C12 C15 H15 119.5
C15 C16 C17 120.93(17)
C15 C16 H16 119.5
C17 C16 H16 119.5
C16 C17 C14 117.79(15)
C16 C17 C18 121.55(16)
C14 C17 C18 120.54(15)
C20 C18 C19 120.33(15)
C20 C18 C17 124.63(15)
C19 C18 C17 114.99(15)
N3 C19 C18 177.6(2)
C18 C20 C21 130.29(16)
C18 C20 H20 114.9
C21 C20 H20 114.9
C22 C21 C20 123.66(16)
C22 C21 S1 110.16(13)
C20 C21 S1 126.12(14)
C21 C22 C23 112.77(17)
C21 C22 H22 123.6
C23 C22 H22 123.6
C24 C23 C22 112.79(18)
C24 C23 H23 123.6
C22 C23 H23 123.6
C23 C24 S1 112.67(15)
C23 C24 H24 123.7
S1 C24 H24 123.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C24 1.704(2)
S1 C21 1.7292(18)
O1 C7 1.350(2)
O1 H1 0.8147
N1 C5 1.371(2)
N1 C4 1.466(3)
N1 C2 1.471(3)
N2 C11 1.287(2)
N2 C12 1.411(2)
N3 C19 1.142(2)
C1 C2 1.496(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.510(3)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.402(3)
C5 C8 1.416(3)
C6 C7 1.378(2)
C6 H6 0.9300
C7 C10 1.408(3)
C8 C9 1.359(3)
C8 H8 0.9300
C9 C10 1.400(3)
C9 H9 0.9300
C10 C11 1.432(2)
C11 H11 0.9300
C12 C13 1.389(2)
C12 C15 1.392(3)
C13 C14 1.382(2)
C13 H13 0.9300
C14 C17 1.393(2)
C14 H14 0.9300
C15 C16 1.381(2)
C15 H15 0.9300
C16 C17 1.393(2)
C16 H16 0.9300
C17 C18 1.481(2)
C18 C20 1.348(2)
C18 C19 1.434(3)
C20 C21 1.436(2)
C20 H20 0.9300
C21 C22 1.390(3)
C22 C23 1.401(3)
C22 H22 0.9300
C23 C24 1.350(3)
C23 H23 0.9300
C24 H24 0.9300
