#------------------------------------------------------------------------------
#$Date: 2017-03-02 05:59:04 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/53/1545374.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_1545374
loop_
_publ_author_name
'Crandall, Laura A.'
'Dawadi, Mahesh B.'
'Burrell, Tailon'
'Odoom, Adwoa'
'Ziegler, Christopher J.'
_publ_section_title
;
 Structure and electronics in dimeric boron π expanded azine and salphen
 complexes.
;
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_paper_doi               10.1039/c6pp00479b
_journal_year                    2017
_chemical_formula_sum            'C32 H30 B2 F4 N2 O4 S2'
_chemical_formula_weight         668.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-21 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6836(7)
_cell_length_b                   5.6340(4)
_cell_length_c                   27.2833(19)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.32
_cell_volume                     1480.15(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17125
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.224
_diffrn_reflns_theta_max         25.224
_diffrn_reflns_theta_min         1.501
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.2476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2353
_reflns_number_total             2661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6pp00479b2.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1545374
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
B1 B 0.77147(19) 0.6148(4) 0.07887(7) 0.0189(4) Uani 1 1 d . .
C1 C 0.59890(16) 0.5226(3) 0.15496(6) 0.0176(4) Uani 1 1 d . .
C2 C 0.70427(17) 0.3655(3) 0.14532(6) 0.0178(4) Uani 1 1 d . .
C3 C 0.73361(17) 0.1631(3) 0.17492(6) 0.0198(4) Uani 1 1 d . .
H3 H 0.8014 0.0520 0.1668 0.024 Uiso 1 1 calc R U
C4 C 0.66426(16) 0.1276(3) 0.21520(6) 0.0193(4) Uani 1 1 d . .
H4 H 0.6827 -0.0120 0.2343 0.023 Uiso 1 1 calc R U
C5 C 0.56483(17) 0.2935(3) 0.22955(6) 0.0186(4) Uani 1 1 d . .
C6 C 0.50482(18) 0.2643(3) 0.27396(7) 0.0199(4) Uani 1 1 d . .
H6 H 0.5272 0.1283 0.2938 0.024 Uiso 1 1 calc R U
C7 C 0.41431(17) 0.4302(3) 0.28881(6) 0.0210(4) Uani 1 1 d . .
H7 H 0.3751 0.4107 0.3190 0.025 Uiso 1 1 calc R U
C8 C 0.38006(17) 0.6289(3) 0.25897(6) 0.0208(4) Uani 1 1 d . .
H8 H 0.3170 0.7432 0.2692 0.025 Uiso 1 1 calc R U
C9 C 0.43604(17) 0.6614(3) 0.21519(6) 0.0188(4) Uani 1 1 d . .
H9 H 0.4107 0.7968 0.1955 0.023 Uiso 1 1 calc R U
C10 C 0.53071(16) 0.4954(3) 0.19930(6) 0.0172(4) Uani 1 1 d . .
C11 C 0.55301(17) 0.6888(3) 0.11752(6) 0.0175(4) Uani 1 1 d . .
H11 H 0.4700 0.7756 0.1202 0.021 Uiso 1 1 calc R U
C12 C 0.55937(17) 0.8660(3) 0.03901(6) 0.0177(4) Uani 1 1 d . .
C13 C 0.42770(17) 0.8089(3) 0.01700(6) 0.0197(4) Uani 1 1 d . .
H13 H 0.3790 0.6774 0.0286 0.024 Uiso 1 1 calc R U
C14 C 0.63258(17) 1.0551(3) 0.02210(6) 0.0193(4) Uani 1 1 d . .
H14 H 0.7231 1.0916 0.0371 0.023 Uiso 1 1 calc R U
C15 C 0.0970(2) 0.1244(4) 0.05198(7) 0.0316(5) Uani 1 1 d . .
H15A H 0.1226 -0.0040 0.0305 0.047 Uiso 1 1 calc R U
H15B H 0.0540 0.2541 0.0318 0.047 Uiso 1 1 calc R U
H15C H 0.0309 0.0645 0.0739 0.047 Uiso 1 1 calc R U
C16 C 0.1620(2) 0.4440(4) 0.12220(8) 0.0332(5) Uani 1 1 d . .
H16A H 0.0880 0.3653 0.1380 0.050 Uiso 1 1 calc R U
H16B H 0.1216 0.5679 0.0999 0.050 Uiso 1 1 calc R U
H16C H 0.2285 0.5158 0.1475 0.050 Uiso 1 1 calc R U
F1 F 0.79722(10) 0.56579(18) 0.03123(4) 0.0252(3) Uani 1 1 d . .
F2 F 0.86779(10) 0.77471(17) 0.10063(4) 0.0248(3) Uani 1 1 d . .
N1 N 0.62163(14) 0.7256(2) 0.07948(5) 0.0168(3) Uani 1 1 d . .
O1 O 0.77587(11) 0.3936(2) 0.10667(4) 0.0200(3) Uani 1 1 d . .
O2 O 0.29592(13) 0.0362(2) 0.12323(5) 0.0308(4) Uani 1 1 d . .
S1 S 0.24897(4) 0.23149(8) 0.08808(2) 0.02316(19) 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'
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'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 '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'
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_3
F1 B1 F2 110.75(14) .
F1 B1 O1 108.75(14) .
F2 B1 O1 110.61(14) .
F1 B1 N1 110.32(14) .
F2 B1 N1 108.42(14) .
O1 B1 N1 107.96(13) .
C2 C1 C11 117.47(15) .
C2 C1 C10 119.84(15) .
C11 C1 C10 122.34(14) .
O1 C2 C1 121.71(15) .
O1 C2 C3 117.39(14) .
C1 C2 C3 120.81(15) .
C4 C3 C2 119.65(15) .
C3 C4 C5 122.01(16) .
C6 C5 C10 120.06(15) .
C6 C5 C4 120.77(15) .
C10 C5 C4 119.12(15) .
C7 C6 C5 120.62(16) .
C6 C7 C8 119.44(15) .
C9 C8 C7 121.30(16) .
C8 C9 C10 120.51(16) .
C9 C10 C5 118.06(15) .
C9 C10 C1 123.80(15) .
C5 C10 C1 118.11(15) .
N1 C11 C1 121.91(15) .
C14 C12 C13 120.87(16) .
C14 C12 N1 119.40(14) .
C13 C12 N1 119.73(15) .
C12 C13 C14 119.71(16) 3_675
C12 C14 C13 119.41(15) 3_675
C11 N1 C12 119.34(14) .
C11 N1 B1 119.34(14) .
C12 N1 B1 121.31(13) .
C2 O1 B1 121.67(13) .
O2 S1 C16 106.70(9) .
O2 S1 C15 106.34(9) .
C16 S1 C15 96.16(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.377(2) .
B1 F2 1.384(2) .
B1 O1 1.457(2) .
B1 N1 1.581(2) .
C1 C2 1.397(2) .
C1 C11 1.422(2) .
C1 C10 1.446(2) .
C2 O1 1.3315(19) .
C2 C3 1.409(2) .
C3 C4 1.362(2) .
C4 C5 1.426(2) .
C5 C6 1.408(3) .
C5 C10 1.424(2) .
C6 C7 1.372(2) .
C7 C8 1.403(2) .
C8 C9 1.375(2) .
C9 C10 1.410(2) .
C11 N1 1.307(2) .
C12 C14 1.386(2) .
C12 C13 1.388(2) .
C12 N1 1.438(2) .
C13 C14 1.391(2) 3_675
C14 C13 1.391(2) 3_675
C15 S1 1.7872(19) .
C16 S1 1.782(2) .
O2 S1 1.4981(13) .
