#------------------------------------------------------------------------------
#$Date: 2016-11-08 21:51:30 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/07/7040708.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_7040708
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            'C14 H9 B F2 N4 O S'
_chemical_formula_weight         330.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv2v
_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                83.834(14)
_cell_angle_beta                 86.891(13)
_cell_angle_gamma                87.700(13)
_cell_formula_units_Z            2
_cell_length_a                   4.7639(7)
_cell_length_b                   11.7169(19)
_cell_length_c                   12.608(2)
_cell_measurement_reflns_used    595
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3220
_cell_measurement_theta_min      4.8930
_cell_volume                     698.24(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0798
_diffrn_reflns_av_sigmaI/netI    0.1401
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3742
_diffrn_reflns_theta_full        67.22
_diffrn_reflns_theta_max         67.22
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  0.8517
_exptl_absorpt_correction_T_min  0.8331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Kelly
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0850
_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)+(0.0370P)²+0.5157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2286
_reflns_number_gt                1340
_reflns_number_total             2482
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt03469a2.cif
_cod_data_source_block           exp_6221
_cod_depositor_comments
'Adding full bibliography for 7040707--7040713.cif.'
_cod_original_cell_volume        698.21(19)
_cod_database_code               7040708
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.7905(4) 0.94746(16) 0.88881(16) 0.0606(6) Uani 1 1 d .
B1 B 0.6878(16) 0.7091(6) 0.6815(7) 0.0461(19) Uani 1 1 d .
F1 F 0.8252(8) 0.7404(3) 0.5855(3) 0.0564(11) Uani 1 1 d .
F2 F 0.4196(7) 0.6775(3) 0.6700(3) 0.0555(11) Uani 1 1 d .
N1 N 0.6739(10) 0.8123(4) 0.7505(4) 0.0440(13) Uani 1 1 d .
N2 N 0.8634(11) 0.6067(4) 0.7458(4) 0.0429(13) Uani 1 1 d .
N3 N 1.0434(13) 0.4140(5) 0.7410(5) 0.0614(17) Uani 1 1 d .
N4 N 1.2981(15) 0.7508(6) 1.0355(6) 0.084(2) Uani 1 1 d .
O1 O 0.7382(10) 0.4986(4) 0.6192(4) 0.0590(14) Uani 1 1 d .
C1 C 0.5577(14) 0.9982(6) 0.7898(6) 0.0494(17) Uani 1 1 d .
C2 C 0.4292(16) 1.1065(6) 0.7761(7) 0.067(2) Uani 1 1 d .
H2 H 0.4564 1.1618 0.8219 0.080 Uiso 1 1 calc R
C3 C 0.2568(18) 1.1279(7) 0.6899(7) 0.073(2) Uani 1 1 d .
H3 H 0.1688 1.2000 0.6768 0.087 Uiso 1 1 calc R
C4 C 0.2137(17) 1.0452(6) 0.6237(7) 0.071(2) Uani 1 1 d .
H4 H 0.0932 1.0621 0.5681 0.085 Uiso 1 1 calc R
C5 C 0.3429(15) 0.9383(6) 0.6371(6) 0.0574(19) Uani 1 1 d .
H5 H 0.3159 0.8833 0.5909 0.069 Uiso 1 1 calc R
C6 C 0.5177(14) 0.9153(6) 0.7235(6) 0.0493(17) Uani 1 1 d .
C7 C 0.8260(14) 0.8182(6) 0.8355(5) 0.0487(16) Uani 1 1 d .
C8 C 0.9943(14) 0.7247(6) 0.8770(5) 0.0510(18) Uani 1 1 d .
C9 C 1.1607(16) 0.7373(6) 0.9661(6) 0.0566(19) Uani 1 1 d .
C10 C 1.0114(14) 0.6199(6) 0.8335(5) 0.0481(16) Uani 1 1 d .
C11 C 1.1793(15) 0.5245(7) 0.8750(6) 0.060(2) Uani 1 1 d .
H11 H 1.2831 0.5293 0.9347 0.072 Uiso 1 1 calc R
C12 C 1.1869(17) 0.4272(7) 0.8274(7) 0.068(2) Uani 1 1 d .
H12 H 1.2977 0.3655 0.8559 0.082 Uiso 1 1 calc R
C13 C 0.8890(14) 0.5029(6) 0.7037(6) 0.0501(17) Uani 1 1 d .
C14 C 0.7395(18) 0.3904(6) 0.5738(7) 0.074(3) Uani 1 1 d .
H14A H 0.9266 0.3715 0.5474 0.112 Uiso 1 1 calc R
H14B H 0.6145 0.3967 0.5161 0.112 Uiso 1 1 calc R
H14C H 0.6784 0.3312 0.6277 0.112 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 0.0181 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 89.7(3)
F2 B1 F1 112.2(6)
F2 B1 N1 108.1(6)
F1 B1 N1 109.4(6)
F2 B1 N2 110.6(6)
F1 B1 N2 109.5(6)
N1 B1 N2 106.8(5)
C7 N1 C6 112.0(6)
C7 N1 B1 124.5(5)
C6 N1 B1 123.2(5)
C10 N2 C13 118.1(5)
C10 N2 B1 123.9(5)
C13 N2 B1 117.7(5)
C13 N3 C12 116.1(7)
C13 O1 C14 117.2(5)
C6 C1 C2 122.6(7)
C6 C1 S1 110.8(5)
C2 C1 S1 126.5(6)
C1 C2 C3 116.2(7)
C4 C3 C2 121.6(7)
C5 C4 C3 122.0(7)
C4 C5 C6 117.1(7)
C1 C6 C5 120.5(6)
C1 C6 N1 113.1(6)
C5 C6 N1 126.4(6)
N1 C7 C8 121.6(6)
N1 C7 S1 114.3(5)
C8 C7 S1 124.1(5)
C10 C8 C7 122.5(6)
C10 C8 C9 118.2(6)
C7 C8 C9 119.2(6)
N4 C9 C8 177.6(9)
N2 C10 C8 119.6(6)
N2 C10 C11 117.2(6)
C8 C10 C11 123.2(6)
C12 C11 C10 119.4(7)
C11 C12 N3 123.7(7)
N3 C13 O1 121.0(6)
N3 C13 N2 125.4(6)
O1 C13 N2 113.6(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.720(7)
S1 C1 1.755(7)
B1 F2 1.364(8)
B1 F1 1.366(9)
B1 N1 1.561(9)
B1 N2 1.607(8)
N1 C7 1.335(8)
N1 C6 1.412(7)
N2 C10 1.368(8)
N2 C13 1.377(8)
N3 C13 1.310(8)
N3 C12 1.343(9)
N4 C9 1.149(9)
O1 C13 1.323(8)
O1 C14 1.446(8)
C1 C6 1.372(9)
C1 C2 1.385(9)
C2 C3 1.394(10)
C3 C4 1.374(10)
C4 C5 1.371(9)
C5 C6 1.403(9)
C7 C8 1.403(9)
C8 C10 1.396(9)
C8 C9 1.432(9)
C10 C11 1.418(9)
C11 C12 1.343(10)
