#------------------------------------------------------------------------------
#$Date: 2017-03-02 05:59:04 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/53/1545373.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_1545373
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            'C28 H18 B2 F4 N2 O2'
_chemical_formula_weight         512.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5217(9)
_cell_length_b                   12.6033(10)
_cell_length_c                   16.7317(15)
_cell_measurement_reflns_used    7797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.32
_cell_measurement_theta_min      5.29
_cell_volume                     2218.8(3)
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12464
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        65.666
_diffrn_reflns_theta_max         65.666
_diffrn_reflns_theta_min         5.287
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0827
_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)+(0.0607P)²+8.8386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1736
_reflns_number_total             1857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6pp00479b2.cif
_cod_data_source_block           4
_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               1545373
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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
_atom_site_refinement_flags_occupancy
B1 B 0.8407(5) 0.8592(5) 0.3657(3) 0.0403(13) Uani 1 1 d . . .
C1 C 0.6231(4) 0.8633(4) 0.4160(3) 0.0352(10) Uani 1 1 d . . .
C2 C 0.5259(4) 0.8063(4) 0.4568(3) 0.0406(11) Uani 1 1 d . . .
H2 H 0.5456 0.7416 0.4831 0.049 Uiso 1 1 calc R U .
C3 C 0.4061(5) 0.8440(4) 0.4580(3) 0.0411(11) Uani 1 1 d . . .
H3 H 0.3421 0.8039 0.4844 0.049 Uiso 1 1 calc R U .
C4 C 0.3720(4) 0.9415(4) 0.4212(3) 0.0370(11) Uani 1 1 d . . .
C5 C 0.2474(5) 0.9809(4) 0.4270(3) 0.0413(11) Uani 1 1 d . . .
H5 H 0.1838 0.9396 0.4527 0.050 Uiso 1 1 calc R U .
C6 C 0.2172(5) 1.0768(4) 0.3966(3) 0.0447(12) Uani 1 1 d . . .
H6 H 0.1327 1.1026 0.4009 0.054 Uiso 1 1 calc R U .
C7 C 0.3101(5) 1.1384(4) 0.3585(3) 0.0479(13) Uani 1 1 d . . .
H7 H 0.2886 1.2064 0.3380 0.057 Uiso 1 1 calc R U .
C8 C 0.4316(4) 1.1011(4) 0.3508(3) 0.0414(11) Uani 1 1 d . . .
H8 H 0.4932 1.1432 0.3240 0.050 Uiso 1 1 calc R U .
C9 C 0.4671(4) 1.0011(4) 0.3818(3) 0.0347(10) Uani 1 1 d . . .
C10 C 0.5946(4) 0.9590(4) 0.3778(3) 0.0338(10) Uani 1 1 d . . .
C11 C 0.6946(4) 1.0118(4) 0.3380(3) 0.0371(11) Uani 1 1 d . . .
H11 H 0.6774 1.0790 0.3147 0.045 Uiso 1 1 calc R U .
C12 C 0.9066(4) 1.0317(3) 0.2907(3) 0.0353(10) Uani 1 1 d . . .
C13 C 0.9080(4) 1.1424(4) 0.2924(3) 0.0416(11) Uani 1 1 d . . .
H13 H 0.8464 1.1803 0.3225 0.050 Uiso 1 1 calc R U .
C14 C 1.0000 1.1958(5) 0.2500 0.0449(17) Uani 1 2 d S T P
H14 H 1.0000 1.2712 0.2500 0.054 Uiso 1 2 calc R U P
C15 C 1.0000 0.9766(5) 0.2500 0.0356(14) Uani 1 2 d S T P
H15 H 1.0000 0.9012 0.2500 0.043 Uiso 1 2 calc R U P
F1 F 0.9513(3) 0.8644(3) 0.40846(19) 0.0567(9) Uani 1 1 d . . .
F2 F 0.8523(3) 0.7892(2) 0.30201(18) 0.0519(8) Uani 1 1 d . . .
N1 N 0.8090(3) 0.9737(3) 0.3314(2) 0.0329(9) Uani 1 1 d . . .
O1 O 0.7380(3) 0.8230(3) 0.41656(18) 0.0397(8) 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'
B B 0.0090 0.0039 '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'
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
_geom_angle_site_symmetry_3
F1 B1 F2 110.9(4) . .
F1 B1 O1 110.0(4) . .
F2 B1 O1 108.5(4) . .
F1 B1 N1 108.9(4) . .
F2 B1 N1 108.6(4) . .
O1 B1 N1 110.0(4) . .
O1 C1 C10 122.4(4) . .
O1 C1 C2 117.6(4) . .
C10 C1 C2 120.1(4) . .
C3 C2 C1 120.1(4) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C2 C3 C4 122.3(4) . .
C2 C3 H3 118.8 . .
C4 C3 H3 118.8 . .
C5 C4 C9 120.3(4) . .
C5 C4 C3 120.7(4) . .
C9 C4 C3 118.9(4) . .
C6 C5 C4 120.6(5) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 120.3(5) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C8 C7 C6 120.3(5) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C8 C9 121.3(5) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C8 C9 C4 117.2(4) . .
C8 C9 C10 123.8(4) . .
C4 C9 C10 118.9(4) . .
C1 C10 C11 117.5(4) . .
C1 C10 C9 119.7(4) . .
C11 C10 C9 122.7(4) . .
N1 C11 C10 123.8(4) . .
N1 C11 H11 118.1 . .
C10 C11 H11 118.1 . .
C15 C12 C13 120.3(5) . .
C15 C12 N1 119.2(4) . .
C13 C12 N1 120.5(4) . .
C14 C13 C12 119.1(5) . .
C14 C13 H13 120.4 . .
C12 C13 H13 120.4 . .
C13 C14 C13 121.4(6) . 3_755
C13 C14 H14 119.3 . .
C13 C14 H14 119.3 3_755 .
C12 C15 C12 119.7(6) 3_755 .
C12 C15 H15 120.1 3_755 .
C12 C15 H15 120.1 . .
C11 N1 C12 121.0(4) . .
C11 N1 B1 119.9(4) . .
C12 N1 B1 119.0(3) . .
C1 O1 B1 124.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.369(6) .
B1 F2 1.388(6) .
B1 O1 1.449(6) .
B1 N1 1.588(7) .
C1 O1 1.312(5) .
C1 C10 1.398(6) .
C1 C2 1.423(6) .
C2 C3 1.348(7) .
C2 H2 0.9500 .
C3 C4 1.421(7) .
C3 H3 0.9500 .
C4 C5 1.405(7) .
C4 C9 1.415(6) .
C5 C6 1.350(7) .
C5 H5 0.9500 .
C6 C7 1.401(7) .
C6 H6 0.9500 .
C7 C8 1.369(7) .
C7 H7 0.9500 .
C8 C9 1.413(7) .
C8 H8 0.9500 .
C9 C10 1.444(6) .
C10 C11 1.412(6) .
C11 N1 1.301(5) .
C11 H11 0.9500 .
C12 C15 1.383(5) .
C12 C13 1.396(6) .
C12 N1 1.433(6) .
C13 C14 1.376(6) .
C13 H13 0.9500 .
C14 C13 1.377(6) 3_755
C14 H14 0.9500 .
C15 C12 1.383(5) 3_755
C15 H15 0.9500 .
