#------------------------------------------------------------------------------
#$Date: 2016-11-08 21:51:30 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/07/7040711.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_7040711
loop_
_publ_author_name
'Wang, Xiaoqing'
'Liu, Qingsong'
'Qi, Fen'
'Li, Lin'
'Yu, Hai-Dong'
'Liu, Zhipeng'
'Huang, Wei'
_publ_section_title
;
 Benzothiazole-pyrimidine-based BODIPY analogues: promising luminophores
 with fluorescence sensing and imaging ability and asymmetrization-induced
 solid-state emission.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17274
_journal_page_last               17280
_journal_paper_doi               10.1039/c6dt03469a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C19 H12 B F2 N5 O0 S'
_chemical_formula_weight         391.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv70
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-23 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.1001(6)
_cell_length_b                   41.434(3)
_cell_length_c                   11.4739(7)
_cell_measurement_reflns_used    843
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9740
_cell_measurement_theta_min      4.2640
_cell_volume                     3375.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(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           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6772
_diffrn_reflns_theta_full        67.24
_diffrn_reflns_theta_max         67.24
_diffrn_reflns_theta_min         4.27
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_T_max  0.9230
_exptl_absorpt_correction_T_min  0.9051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.0975
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0665P)²+5.0420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2071
_refine_ls_wR_factor_ref         0.2418
_reflns_number_gt                1673
_reflns_number_total             3026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt03469a2.cif
_cod_data_source_block           exp_6642
_cod_depositor_comments
'Adding full bibliography for 7040707--7040713.cif.'
_cod_original_cell_volume        3375.4(5)
_cod_database_code               7040711
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 0.3427(3) 0.53559(4) 0.45699(18) 0.0606(6) Uani 1 1 d .
F1 F 0.1545(6) 0.64770(9) 0.4280(4) 0.0714(13) Uani 1 1 d .
F2 F 0.4707(7) 0.64870(9) 0.4326(4) 0.0688(13) Uani 1 1 d .
N2 N 0.3083(7) 0.63736(11) 0.6110(5) 0.0452(13) Uani 1 1 d .
N1 N 0.3173(8) 0.59748(11) 0.4422(4) 0.0447(13) Uani 1 1 d .
N5 N 0.2819(8) 0.69308(12) 0.5872(5) 0.0511(15) Uani 1 1 d .
H20 H 0.2638 0.6881 0.5153 0.061 Uiso 1 1 calc R
N3 N 0.2961(9) 0.67354(12) 0.7748(5) 0.0582(16) Uani 1 1 d .
C7 C 0.3317(9) 0.57368(14) 0.5199(6) 0.0479(16) Uani 1 1 d .
C6 C 0.3216(10) 0.58629(14) 0.3258(6) 0.0457(16) Uani 1 1 d .
C13 C 0.2953(9) 0.66769(15) 0.6598(6) 0.0467(16) Uani 1 1 d .
C14 C 0.2929(9) 0.72655(15) 0.6100(6) 0.0451(16) Uani 1 1 d .
C9 C 0.3226(9) 0.61121(15) 0.6866(6) 0.0491(17) Uani 1 1 d .
C5 C 0.3089(11) 0.60456(16) 0.2270(6) 0.0582(19) Uani 1 1 d .
H5 H 0.2957 0.6269 0.2315 0.070 Uiso 1 1 calc R
C1 C 0.3368(10) 0.55267(14) 0.3184(6) 0.0460(16) Uani 1 1 d .
C11 C 0.3261(11) 0.61681(16) 0.8064(6) 0.0560(18) Uani 1 1 d .
H11 H 0.3373 0.5998 0.8590 0.067 Uiso 1 1 calc R
C19 C 0.3732(9) 0.74020(16) 0.7094(6) 0.0512(17) Uani 1 1 d .
H19 H 0.4181 0.7270 0.7688 0.061 Uiso 1 1 calc R
C18 C 0.3859(9) 0.77358(16) 0.7191(6) 0.0531(18) Uani 1 1 d .
H18 H 0.4392 0.7826 0.7856 0.064 Uiso 1 1 calc R
C8 C 0.3346(10) 0.57960(15) 0.6394(6) 0.0528(18) Uani 1 1 d .
C17 C 0.3213(10) 0.79334(17) 0.6324(7) 0.061(2) Uani 1 1 d .
H17 H 0.3311 0.8156 0.6395 0.073 Uiso 1 1 calc R
C15 C 0.2262(9) 0.74671(15) 0.5230(7) 0.0549(19) Uani 1 1 d .
H15 H 0.1710 0.7378 0.4568 0.066 Uiso 1 1 calc R
N4 N 0.3660(11) 0.53317(14) 0.7877(6) 0.081(2) Uani 1 1 d .
C4 C 0.3162(11) 0.58917(18) 0.1202(7) 0.064(2) Uani 1 1 d .
H4 H 0.3073 0.6014 0.0524 0.077 Uiso 1 1 calc R
B1 B 0.3122(12) 0.63347(18) 0.4740(7) 0.051(2) Uani 1 1 d .
C16 C 0.2405(10) 0.77958(16) 0.5332(7) 0.059(2) Uani 1 1 d .
H16 H 0.1962 0.7928 0.4737 0.071 Uiso 1 1 calc R
C3 C 0.3366(11) 0.55593(18) 0.1119(7) 0.063(2) Uani 1 1 d .
H3 H 0.3432 0.5461 0.0392 0.076 Uiso 1 1 calc R
C12 C 0.3128(11) 0.64752(17) 0.8437(7) 0.062(2) Uani 1 1 d .
H12 H 0.3155 0.6510 0.9238 0.074 Uiso 1 1 calc R
C2A C 0.3471(10) 0.53745(17) 0.2128(7) 0.061(2) Uani 1 1 d .
H2A H 0.3609 0.5152 0.2086 0.073 Uiso 1 1 calc R
C10B C 0.3519(11) 0.55344(17) 0.7207(7) 0.064(2) 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 0.0181 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'
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'
S S 0.3331 0.5567 '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'
B B 0.0090 0.0039 '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 S1 C1 90.5(3)
C13 N2 C9 117.4(6)
C13 N2 B1 119.9(5)
C9 N2 B1 122.7(5)
C7 N1 C6 112.8(5)
C7 N1 B1 124.2(6)
C6 N1 B1 122.9(5)
C13 N5 C14 130.5(6)
C13 N3 C12 115.8(6)
N1 C7 C8 121.9(6)
N1 C7 S1 113.4(5)
C8 C7 S1 124.6(5)
C5 C6 C1 120.4(6)
C5 C6 N1 126.9(6)
C1 C6 N1 112.7(5)
N3 C13 N5 117.9(6)
N3 C13 N2 124.3(6)
N5 C13 N2 117.8(6)
C15 C14 C19 119.0(6)
C15 C14 N5 116.1(6)
C19 C14 N5 124.8(6)
N2 C9 C11 119.1(6)
N2 C9 C8 118.9(6)
C11 C9 C8 122.0(6)
C6 C5 C4 118.5(6)
C2A C1 C6 121.1(6)
C2A C1 S1 128.3(5)
C6 C1 S1 110.5(5)
C12 C11 C9 118.0(7)
C18 C19 C14 119.7(6)
C17 C18 C19 121.0(7)
C7 C8 C9 122.5(6)
C7 C8 C10B 120.5(6)
C9 C8 C10B 116.9(6)
C18 C17 C16 119.1(7)
C16 C15 C14 120.8(7)
C5 C4 C3 121.5(7)
F1 B1 F2 109.8(6)
F1 B1 N1 110.2(6)
F2 B1 N1 110.2(6)
F1 B1 N2 109.0(6)
F2 B1 N2 108.1(6)
N1 B1 N2 109.6(5)
C15 C16 C17 120.4(7)
C4 C3 C2A 119.6(7)
N3 C12 C11 125.3(7)
C1 C2A C3 118.8(6)
N4 C10B C8 178.3(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.737(6)
S1 C1 1.741(7)
F1 B1 1.372(9)
F2 B1 1.375(9)
N2 C13 1.379(8)
N2 C9 1.392(8)
N2 B1 1.580(10)
N1 C7 1.333(7)
N1 C6 1.414(8)
N1 B1 1.535(9)
N5 C13 1.345(8)
N5 C14 1.414(8)
N3 C13 1.342(8)
N3 C12 1.342(8)
C7 C8 1.393(9)
C6 C5 1.367(9)
C6 C1 1.400(8)
C14 C15 1.385(9)
C14 C19 1.394(9)
C9 C11 1.394(9)
C9 C8 1.420(9)
C5 C4 1.382(9)
C1 C2A 1.368(9)
C11 C12 1.346(9)
C19 C18 1.390(9)
C18 C17 1.367(9)
C8 C10B 1.435(10)
C17 C16 1.397(10)
C15 C16 1.371(8)
N4 C10B 1.143(9)
C4 C3 1.388(9)
C3 C2A 1.390(10)
