# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20171025SZ_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1587415'
_audit_update_record             
;
2017-11-24 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        2,7-diphenyl-1,3,6,8-tetramethylBOPHY
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 B2 F4 N4'
_chemical_formula_weight         490.11

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4590(5)
_cell_length_b                   32.400(2)
_cell_length_c                   8.9587(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.775(2)
_cell_angle_gamma                90
_cell_volume                     2295.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5004
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.67

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20473
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5275
_reflns_number_gt                3575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²+0.9206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5275
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.9465(3) 0.44153(8) 1.0628(3) 0.0203(5) Uani 1 1 d . . . . .
B2 B 0.4948(3) 0.48964(8) 0.7706(3) 0.0208(5) Uani 1 1 d . . . . .
C1 C 0.7693(3) 0.35118(8) 0.4136(3) 0.0268(5) Uani 1 1 d . . . . .
H1 H 0.738282 0.377815 0.368328 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7324(3) 0.31671(8) 0.3155(3) 0.0332(6) Uani 1 1 d . . . . .
H2 H 0.676961 0.320029 0.203644 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7750(3) 0.27766(8) 0.3782(3) 0.0353(6) Uani 1 1 d . . . . .
H3 H 0.747836 0.254188 0.310274 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8579(3) 0.27296(8) 0.5413(3) 0.0327(6) Uani 1 1 d . . . . .
H4 H 0.888038 0.246198 0.585633 0.039 Uiso 1 1 calc R U . . .
C5 C 0.8967(3) 0.30740(7) 0.6397(3) 0.0272(5) Uani 1 1 d . . . . .
H5 H 0.955134 0.303924 0.751049 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8517(3) 0.34711(7) 0.5785(3) 0.0225(5) Uani 1 1 d . . . . .
C7 C 0.8926(3) 0.38383(7) 0.6845(3) 0.0215(5) Uani 1 1 d . . . . .
C8 C 0.8748(3) 0.38651(7) 0.8361(3) 0.0198(5) Uani 1 1 d . . . . .
C9 C 0.8172(3) 0.35469(7) 0.9262(3) 0.0270(5) Uani 1 1 d . . . . .
H9A H 0.915859 0.340976 1.003141 0.041 Uiso 1 1 calc R U . . .
H9B H 0.746816 0.334216 0.851439 0.041 Uiso 1 1 calc R U . . .
H9C H 0.751210 0.367984 0.983221 0.041 Uiso 1 1 calc R U . . .
C10 C 0.9533(3) 0.42192(7) 0.6554(2) 0.0196(5) Uani 1 1 d . . . . .
C11 C 0.9922(3) 0.43547(7) 0.5118(3) 0.0239(5) Uani 1 1 d . . . . .
H11A H 1.029638 0.411656 0.465631 0.036 Uiso 1 1 calc R U . . .
H11B H 1.081881 0.456327 0.543805 0.036 Uiso 1 1 calc R U . . .
H11C H 0.890305 0.447281 0.432365 0.036 Uiso 1 1 calc R U . . .
C12 C 0.9706(3) 0.44692(7) 0.7880(2) 0.0186(5) Uani 1 1 d . . . . .
C13 C 1.0183(3) 0.48777(7) 0.8154(2) 0.0205(5) Uani 1 1 d . . . . .
H13 H 1.050503 0.501302 0.736511 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2435(3) 0.33888(7) 0.4645(3) 0.0271(5) Uani 1 1 d . . . . .
H14 H 0.205090 0.364319 0.411221 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2047(3) 0.30237(8) 0.3794(3) 0.0336(6) Uani 1 1 d . . . . .
H15 H 0.140441 0.302935 0.268292 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2586(3) 0.26516(8) 0.4547(3) 0.0343(6) Uani 1 1 d . . . . .
H16 H 0.230370 0.240109 0.396068 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3538(3) 0.26443(7) 0.6156(3) 0.0311(6) Uani 1 1 d . . . . .
H17 H 0.392046 0.238841 0.667674 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3938(3) 0.30107(7) 0.7019(3) 0.0259(5) Uani 1 1 d . . . . .
H18 H 0.459649 0.300253 0.812537 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3387(3) 0.33889(7) 0.6283(3) 0.0223(5) Uani 1 1 d . . . . .
C20 C 0.3790(3) 0.37788(7) 0.7195(3) 0.0203(5) Uani 1 1 d . . . . .
C21 C 0.4346(3) 0.41458(7) 0.6684(3) 0.0200(5) Uani 1 1 d . . . . .
C22 C 0.4672(3) 0.42273(7) 0.5177(3) 0.0257(5) Uani 1 1 d . . . . .
H22A H 0.367685 0.435896 0.439841 0.039 Uiso 1 1 calc R U . . .
H22B H 0.490068 0.396606 0.474109 0.039 Uiso 1 1 calc R U . . .
H22C H 0.565119 0.441045 0.540360 0.039 Uiso 1 1 calc R U . . .
C23 C 0.3651(3) 0.38633(7) 0.8684(3) 0.0201(5) Uani 1 1 d . . . . .
C24 C 0.3067(3) 0.35831(7) 0.9717(3) 0.0251(5) Uani 1 1 d . . . . .
H24A H 0.224259 0.338586 0.904428 0.038 Uiso 1 1 calc R U . . .
H24B H 0.253978 0.374748 1.033200 0.038 Uiso 1 1 calc R U . . .
H24C H 0.403844 0.343296 1.045100 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4145(3) 0.42773(7) 0.9044(3) 0.0188(5) Uani 1 1 d . . . . .
C26 C 0.4254(3) 0.45151(7) 1.0358(3) 0.0212(5) Uani 1 1 d . . . . .
H26 H 0.393867 0.438815 1.116638 0.025 Uiso 1 1 calc R U . . .
F1 F 0.80820(17) 0.43595(4) 1.10703(15) 0.0286(3) Uani 1 1 d . . . . .
F2 F 1.08938(18) 0.42419(4) 1.17601(15) 0.0291(3) Uani 1 1 d . . . . .
F3 F 0.35755(17) 0.50972(4) 0.65985(15) 0.0285(3) Uani 1 1 d . . . . .
F4 F 0.63898(17) 0.49717(4) 0.73736(16) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.9218(2) 0.42470(6) 0.8966(2) 0.0191(4) Uani 1 1 d . . . . .
N2 N 1.0233(2) 0.50986(5) 0.9413(2) 0.0179(4) Uani 1 1 d . . . . .
N3 N 0.4573(2) 0.44411(5) 0.7802(2) 0.0191(4) Uani 1 1 d . . . . .
N4 N 0.4760(2) 0.49046(5) 1.0587(2) 0.0186(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.373(3) . ?
B1 F2 1.392(3) . ?
B1 N1 1.529(3) . ?
B1 N2 1.598(3) 3_767 ?
B2 F4 1.376(3) . ?
B2 F3 1.392(3) . ?
B2 N3 1.518(3) . ?
B2 N4 1.596(3) 3_667 ?
C1 C2 1.386(3) . ?
C1 C6 1.398(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.485(3) . ?
C7 C10 1.397(3) . ?
C7 C8 1.421(3) . ?
C8 N1 1.353(3) . ?
C8 C9 1.494(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.402(3) . ?
C10 C11 1.501(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.380(3) . ?
C12 N1 1.386(3) . ?
C13 N2 1.324(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 C19 1.401(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.477(3) . ?
C20 C23 1.406(3) . ?
C20 C21 1.414(3) . ?
C21 N3 1.349(3) . ?
C21 C22 1.494(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C25 1.408(3) . ?
C23 C24 1.500(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.382(3) . ?
C25 N3 1.391(3) . ?
C26 N4 1.325(3) . ?
C26 H26 0.9500 . ?
N2 N2 1.402(3) 3_767 ?
N4 N4 1.399(3) 3_667 ?

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
_geom_angle_publ_flag
F1 B1 F2 110.19(18) . . ?
F1 B1 N1 113.46(19) . . ?
F2 B1 N1 110.41(19) . . ?
F1 B1 N2 107.20(18) . 3_767 ?
F2 B1 N2 108.06(19) . 3_767 ?
N1 B1 N2 107.29(17) . 3_767 ?
F4 B2 F3 109.99(19) . . ?
F4 B2 N3 113.81(19) . . ?
F3 B2 N3 110.89(19) . . ?
F4 B2 N4 106.72(18) . 3_667 ?
F3 B2 N4 107.49(18) . 3_667 ?
N3 B2 N4 107.63(18) . 3_667 ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.8(2) . . ?
C5 C6 C7 121.2(2) . . ?
C1 C6 C7 121.1(2) . . ?
C10 C7 C8 107.18(19) . . ?
C10 C7 C6 127.3(2) . . ?
C8 C7 C6 125.5(2) . . ?
N1 C8 C7 108.85(19) . . ?
N1 C8 C9 121.38(19) . . ?
C7 C8 C9 129.8(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C12 106.65(19) . . ?
C7 C10 C11 128.7(2) . . ?
C12 C10 C11 124.6(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 120.96(19) . . ?
C13 C12 C10 129.8(2) . . ?
N1 C12 C10 109.12(19) . . ?
N2 C13 C12 126.1(2) . . ?
N2 C13 H13 117.0 . . ?
C12 C13 H13 117.0 . . ?
C15 C14 C19 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C19 C14 H14 119.6 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 117.9(2) . . ?
C18 C19 C20 121.2(2) . . ?
C14 C19 C20 120.9(2) . . ?
C23 C20 C21 107.02(19) . . ?
C23 C20 C19 127.6(2) . . ?
C21 C20 C19 125.3(2) . . ?
N3 C21 C20 109.37(19) . . ?
N3 C21 C22 121.5(2) . . ?
C20 C21 C22 129.1(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 C25 106.58(19) . . ?
C20 C23 C24 128.6(2) . . ?
C25 C23 C24 124.8(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N3 120.70(19) . . ?
C26 C25 C23 130.6(2) . . ?
N3 C25 C23 108.68(18) . . ?
N4 C26 C25 125.7(2) . . ?
N4 C26 H26 117.2 . . ?
C25 C26 H26 117.2 . . ?
C8 N1 C12 108.19(17) . . ?
C8 N1 B1 129.48(18) . . ?
C12 N1 B1 121.78(18) . . ?
C13 N2 N2 117.4(2) . 3_767 ?
C13 N2 B1 118.07(17) . 3_767 ?
N2 N2 B1 123.8(2) 3_767 3_767 ?
C21 N3 C25 108.34(18) . . ?
C21 N3 B2 128.64(18) . . ?
C25 N3 B2 122.35(18) . . ?
C26 N4 N4 117.9(2) . 3_667 ?
C26 N4 B2 117.75(17) . 3_667 ?
N4 N4 B2 123.7(2) 3_667 3_667 ?

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.060

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_20170614szjl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1587416'
_audit_update_record             
;
2017-11-24 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,7-dithienyl-1,3,6,8-tetramethylBOPHY
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 B2 F4 N4 S2'
_chemical_formula_weight         502.16

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'
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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.769(5)
_cell_length_b                   5.3789(18)
_cell_length_c                   15.474(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.141(5)
_cell_angle_gamma                90
_cell_volume                     1089.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1316
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.17

_exptl_crystal_description       block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7261
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.723
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1914
_reflns_number_gt                1394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1261P)²+0.7728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2284
_refine_ls_wR_factor_gt          0.1980
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4062(3) 0.1055(8) 0.5761(3) 0.0246(10) Uani 1 1 d . . . . .
C1 C 0.2208(3) 0.4239(8) 0.5758(3) 0.0339(10) Uani 1 1 d . . . . .
H1A H 0.1637 0.3120 0.5583 0.051 Uiso 1 1 calc R U . . .
H1B H 0.1976 0.5868 0.5855 0.051 Uiso 1 1 calc R U . . .
H1C H 0.2697 0.3659 0.6310 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2694(3) 0.4346(7) 0.5026(2) 0.0272(9) Uani 1 1 d . . . . .
C3 C 0.2413(3) 0.5816(7) 0.4214(2) 0.0257(9) Uani 1 1 d . . . . .
C4 C 0.3106(3) 0.5231(7) 0.3742(2) 0.0257(9) Uani 1 1 d . . . . .
C5 C 0.3779(3) 0.3424(7) 0.4265(2) 0.0251(8) Uani 1 1 d . . . . .
C6 C 0.3111(3) 0.6182(8) 0.2834(2) 0.0321(10) Uani 1 1 d . . . . .
H6A H 0.2430 0.6136 0.2416 0.048 Uiso 1 1 calc R U . . .
H6B H 0.3549 0.5158 0.2607 0.048 Uiso 1 1 calc R U . . .
H6C H 0.3358 0.7863 0.2896 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4566(3) 0.2133(7) 0.4097(2) 0.0259(9) Uani 1 1 d . . . . .
H7 H 0.4729 0.2568 0.3578 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1570(3) 0.7589(7) 0.3945(2) 0.0286(9) Uani 1 1 d . . . . .
C9 C 0.0012(3) 0.9818(10) 0.3782(3) 0.0483(13) Uani 1 1 d . . . . .
H9 H -0.0616 1.0342 0.3823 0.058 Uiso 1 1 calc R U . A 1
C10 C 0.0518(4) 1.1107(9) 0.3318(3) 0.0473(12) Uani 1 1 d . . . . .
H10 H 0.0258 1.2579 0.3019 0.057 Uiso 1 1 calc R U . B 1
C11 C 0.05344(14) 0.7403(4) 0.42474(13) 0.0479(6) Uani 0.5 1 d . . P C 2
H11 H 0.0325 0.6220 0.4591 0.058 Uiso 0.5 1 calc R U P C 2
C11' C 0.15560(12) 1.0031(3) 0.33006(11) 0.0381(6) Uani 0.5 1 d . . P C 2
H11' H 0.2021 1.0586 0.3018 0.046 Uiso 0.5 1 calc R U P C 2
F1 F 0.45843(15) 0.2216(4) 0.65770(13) 0.0333(7) Uani 1 1 d . . . . .
F2 F 0.34212(15) -0.0742(4) 0.59182(14) 0.0313(6) Uani 1 1 d . . . . .
N1 N 0.5109(2) 0.0336(6) 0.46037(18) 0.0251(8) Uani 1 1 d . . . . .
N2 N 0.3500(2) 0.2909(6) 0.50417(19) 0.0253(8) Uani 1 1 d . . . . .
S1 S 0.15560(12) 1.0031(3) 0.33006(11) 0.0381(6) Uani 0.5 1 d . . P C 1
S1' S 0.05344(14) 0.7403(4) 0.42474(13) 0.0479(6) Uani 0.5 1 d . . P C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F2 1.381(5) . ?
B1 F1 1.392(4) . ?
B1 N2 1.515(5) . ?
B1 N1 1.607(5) 3_656 ?
C1 C2 1.486(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.347(5) . ?
C2 C3 1.432(5) . ?
C3 C4 1.406(5) . ?
C3 C8 1.459(5) . ?
C4 C5 1.411(5) . ?
C4 C6 1.498(5) . ?
C5 C7 1.378(5) . ?
C5 N2 1.398(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N1 1.320(5) . ?
C7 H7 0.9300 . ?
C8 S1' 1.637(4) . ?
C8 C11 1.637(4) . ?
C8 C11' 1.645(4) . ?
C8 S1 1.645(4) . ?
C9 C10 1.339(7) . ?
C9 S1' 1.549(5) . ?
C9 C11 1.549(5) . ?
C9 H9 0.9300 . ?
C10 S1 1.550(5) . ?
C10 C11' 1.550(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11' H11' 0.9300 . ?
N1 N1 1.398(5) 3_656 ?
N1 B1 1.607(5) 3_656 ?

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
_geom_angle_publ_flag
F2 B1 F1 109.4(3) . . ?
F2 B1 N2 112.5(3) . . ?
F1 B1 N2 111.9(3) . . ?
F2 B1 N1 107.4(3) . 3_656 ?
F1 B1 N1 107.7(3) . 3_656 ?
N2 B1 N1 107.7(3) . 3_656 ?
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 . . ?
N2 C2 C3 109.2(3) . . ?
N2 C2 C1 121.9(3) . . ?
C3 C2 C1 128.9(3) . . ?
C4 C3 C2 106.9(3) . . ?
C4 C3 C8 127.3(3) . . ?
C2 C3 C8 125.8(3) . . ?
C3 C4 C5 106.7(3) . . ?
C3 C4 C6 127.8(3) . . ?
C5 C4 C6 125.4(3) . . ?
C7 C5 N2 120.3(3) . . ?
C7 C5 C4 130.8(3) . . ?
N2 C5 C4 108.8(3) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C5 126.2(3) . . ?
N1 C7 H7 116.9 . . ?
C5 C7 H7 116.9 . . ?
C3 C8 S1' 124.4(3) . . ?
C3 C8 C11 124.4(3) . . ?
C3 C8 C11' 123.6(3) . . ?
C11 C8 C11' 112.0(2) . . ?
C3 C8 S1 123.6(3) . . ?
S1' C8 S1 112.0(2) . . ?
C10 C9 S1' 116.1(4) . . ?
C10 C9 C11 116.1(4) . . ?
C10 C9 H9 121.9 . . ?
S1' C9 H9 121.9 . . ?
C9 C10 S1 116.9(4) . . ?
C9 C10 C11' 116.9(4) . . ?
C9 C10 H10 121.6 . . ?
S1 C10 H10 121.6 . . ?
C9 C11 C8 97.8(2) . . ?
C9 C11 H11 131.1 . . ?
C8 C11 H11 131.1 . . ?
C10 C11' C8 97.2(2) . . ?
C10 C11' H11' 131.4 . . ?
C8 C11' H11' 131.4 . . ?
C7 N1 N1 118.2(4) . 3_656 ?
C7 N1 B1 117.8(3) . 3_656 ?
N1 N1 B1 123.9(4) 3_656 3_656 ?
C2 N2 C5 108.4(3) . . ?
C2 N2 B1 128.4(3) . . ?
C5 N2 B1 123.2(3) . . ?
C10 S1 C8 97.2(2) . . ?
C9 S1' C8 97.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C4 -1.1(4) . . . . ?
C1 C2 C3 C4 -179.5(4) . . . . ?
N2 C2 C3 C8 179.4(3) . . . . ?
C1 C2 C3 C8 0.9(6) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C8 C3 C4 C5 -180.0(3) . . . . ?
C2 C3 C4 C6 177.0(3) . . . . ?
C8 C3 C4 C6 -3.5(6) . . . . ?
C3 C4 C5 C7 176.5(4) . . . . ?
C6 C4 C5 C7 -0.2(6) . . . . ?
C3 C4 C5 N2 0.2(4) . . . . ?
C6 C4 C5 N2 -176.4(3) . . . . ?
N2 C5 C7 N1 1.1(6) . . . . ?
C4 C5 C7 N1 -174.8(4) . . . . ?
C4 C3 C8 S1' 153.1(3) . . . . ?
C2 C3 C8 S1' -27.5(5) . . . . ?
C4 C3 C8 C11 153.1(3) . . . . ?
C2 C3 C8 C11 -27.5(5) . . . . ?
C4 C3 C8 C11' -27.2(5) . . . . ?
C2 C3 C8 C11' 152.2(3) . . . . ?
C4 C3 C8 S1 -27.2(5) . . . . ?
C2 C3 C8 S1 152.2(3) . . . . ?
S1' C9 C10 S1 0.1(5) . . . . ?
C11 C9 C10 C11' 0.1(5) . . . . ?
C10 C9 C11 C8 1.1(4) . . . . ?
C3 C8 C11 C9 177.8(3) . . . . ?
C11' C8 C11 C9 -1.9(3) . . . . ?
C9 C10 C11' C8 -1.3(4) . . . . ?
C3 C8 C11' C10 -177.7(3) . . . . ?
C11 C8 C11' C10 2.0(3) . . . . ?
C5 C7 N1 N1 -0.9(6) . . . 3_656 ?
C5 C7 N1 B1 175.6(3) . . . 3_656 ?
C3 C2 N2 C5 1.2(4) . . . . ?
C1 C2 N2 C5 179.8(3) . . . . ?
C3 C2 N2 B1 -180.0(3) . . . . ?
C1 C2 N2 B1 -1.4(6) . . . . ?
C7 C5 N2 C2 -177.6(3) . . . . ?
C4 C5 N2 C2 -0.9(4) . . . . ?
C7 C5 N2 B1 3.5(5) . . . . ?
C4 C5 N2 B1 -179.8(3) . . . . ?
F2 B1 N2 C2 56.4(5) . . . . ?
F1 B1 N2 C2 -67.2(5) . . . . ?
N1 B1 N2 C2 174.6(3) 3_656 . . . ?
F2 B1 N2 C5 -124.9(3) . . . . ?
F1 B1 N2 C5 111.5(4) . . . . ?
N1 B1 N2 C5 -6.8(5) 3_656 . . . ?
C9 C10 S1 C8 -1.3(4) . . . . ?
C3 C8 S1 C10 -177.7(3) . . . . ?
S1' C8 S1 C10 2.0(3) . . . . ?
C10 C9 S1' C8 1.1(4) . . . . ?
C3 C8 S1' C9 177.8(3) . . . . ?
S1 C8 S1' C9 -1.9(3) . . . . ?

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.128

