# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_120612a_0m
_database_code_depnum_ccdc_archive 'CCDC 1445551'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C31 H23 B F2 N2 O2'

_chemical_formula_weight         504.32



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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   7.683(4)

_cell_length_b                   12.170(6)

_cell_length_c                   13.064(6)

_cell_angle_alpha                85.699(6)

_cell_angle_beta                 81.017(7)

_cell_angle_gamma                86.489(6)

_cell_volume                     1201.6(10)

_cell_formula_units_Z            2

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    2741

_cell_measurement_theta_min      2.23

_cell_measurement_theta_max      25.81



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.16

_exptl_crystal_size_mid          0.13

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.394

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             524

_exptl_absorpt_coefficient_mu    0.097

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9846

_exptl_absorpt_correction_T_max  0.9884

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            10133

_diffrn_reflns_av_R_equivalents  0.0462

_diffrn_reflns_av_sigmaI/netI    0.0724

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -15

_diffrn_reflns_limit_k_max       15

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         1.58

_diffrn_reflns_theta_max         27.64

_reflns_number_total             5338

_reflns_number_gt                3105

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1200P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         5338

_refine_ls_number_parameters     345

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1144

_refine_ls_R_factor_gt           0.0721

_refine_ls_wR_factor_ref         0.2199

_refine_ls_wR_factor_gt          0.1870

_refine_ls_goodness_of_fit_ref   1.033

_refine_ls_restrained_S_all      1.033

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group





























































B1 B 0.2433(4) 0.1854(3) 0.0439(2) 0.0445(7) Uani 1 1 d . . .
C1 C 0.3259(3) 0.1011(2) 0.2240(2) 0.0450(6) Uani 1 1 d . . .
C2 C 0.3578(3) -0.0066(2) 0.2716(2) 0.0460(6) Uani 1 1 d . . .
C3 C 0.3992(4) -0.0438(3) 0.3701(2) 0.0555(7) Uani 1 1 d . . .
H3 H 0.4146 0.0057 0.4184 0.067 Uiso 1 1 calc R . .
C4 C 0.4161(4) -0.1559(3) 0.3925(2) 0.0655(9) Uani 1 1 d . . .
H4 H 0.4418 -0.1821 0.4575 0.079 Uiso 1 1 calc R . .
C5 C 0.3954(4) -0.2318(3) 0.3197(2) 0.0630(8) Uani 1 1 d . . .
H5 H 0.4041 -0.3070 0.3381 0.076 Uiso 1 1 calc R . .
C6 C 0.3628(4) -0.1965(2) 0.2225(2) 0.0534(7) Uani 1 1 d . . .
H6 H 0.3535 -0.2471 0.1739 0.064 Uiso 1 1 calc R . .
C7 C 0.3437(3) -0.0832(2) 0.1972(2) 0.0455(6) Uani 1 1 d . . .
C8 C 0.3051(3) -0.0207(2) 0.1068(2) 0.0443(6) Uani 1 1 d . . .
C9 C 0.2717(3) -0.0545(2) 0.0139(2) 0.0473(6) Uani 1 1 d . . .
H9 H 0.2867 -0.1293 0.0029 0.057 Uiso 1 1 calc R . .
C10 C 0.2172(3) 0.0159(2) -0.0637(2) 0.0445(6) Uani 1 1 d . . .
C11 C 0.1858(3) -0.0033(2) -0.1645(2) 0.0440(6) Uani 1 1 d . . .
C12 C 0.1961(4) -0.1004(2) -0.2186(2) 0.0547(7) Uani 1 1 d . . .
H12 H 0.2282 -0.1686 -0.1879 0.066 Uiso 1 1 calc R . .
C13 C 0.1572(4) -0.0907(3) -0.3179(2) 0.0644(8) Uani 1 1 d . . .
H13 H 0.1683 -0.1530 -0.3559 0.077 Uiso 1 1 calc R . .
C14 C 0.1011(4) 0.0104(3) -0.3636(2) 0.0612(8) Uani 1 1 d . . .
H14 H 0.0713 0.0132 -0.4301 0.073 Uiso 1 1 calc R . .
C15 C 0.0892(4) 0.1056(2) -0.3119(2) 0.0536(7) Uani 1 1 d . . .
H15 H 0.0520 0.1727 -0.3425 0.064 Uiso 1 1 calc R . .
C16 C 0.1354(3) 0.0984(2) -0.2113(2) 0.0449(6) Uani 1 1 d . . .
C17 C 0.1382(3) 0.1797(2) -0.13837(18) 0.0418(6) Uani 1 1 d . . .
C18 C 0.3278(3) 0.2052(2) 0.27587(19) 0.0450(6) Uani 1 1 d . . .
C19 C 0.4084(3) 0.2989(2) 0.2251(2) 0.0477(6) Uani 1 1 d . . .
H19 H 0.4579 0.2984 0.1555 0.057 Uiso 1 1 calc R . .
C20 C 0.4139(4) 0.3924(2) 0.2791(2) 0.0547(7) Uani 1 1 d . . .
C21 C 0.3421(4) 0.3935(3) 0.3826(2) 0.0661(9) Uani 1 1 d . . .
H21 H 0.3477 0.4561 0.4185 0.079 Uiso 1 1 calc R . .
C22 C 0.2615(4) 0.3017(3) 0.4330(2) 0.0619(8) Uani 1 1 d . . .
H22 H 0.2125 0.3025 0.5027 0.074 Uiso 1 1 calc R . .
C23 C 0.2540(4) 0.2083(2) 0.3795(2) 0.0546(7) Uani 1 1 d . . .
H23 H 0.1987 0.1470 0.4135 0.066 Uiso 1 1 calc R . .
C24 C 0.5584(5) 0.4929(3) 0.1301(2) 0.0789(10) Uani 1 1 d . . .
H24A H 0.6541 0.4386 0.1178 0.118 Uiso 1 1 calc R . .
H24B H 0.6007 0.5650 0.1093 0.118 Uiso 1 1 calc R . .
H24C H 0.4680 0.4785 0.0905 0.118 Uiso 1 1 calc R . .
C25 C 0.0950(3) 0.2986(2) -0.15895(19) 0.0440(6) Uani 1 1 d . . .
C26 C 0.1652(4) 0.3466(2) -0.2544(2) 0.0489(7) Uani 1 1 d . . .
H26 H 0.2415 0.3047 -0.3004 0.059 Uiso 1 1 calc R . .
C27 C 0.1244(4) 0.4560(2) -0.2831(2) 0.0533(7) Uani 1 1 d . . .
C28 C 0.0095(4) 0.5186(3) -0.2154(2) 0.0618(8) Uani 1 1 d . . .
H28 H -0.0201 0.5918 -0.2340 0.074 Uiso 1 1 calc R . .
C29 C -0.0597(4) 0.4711(3) -0.1206(2) 0.0589(8) Uani 1 1 d . . .
H29 H -0.1357 0.5135 -0.0749 0.071 Uiso 1 1 calc R . .
C30 C -0.0201(4) 0.3617(2) -0.0905(2) 0.0527(7) Uani 1 1 d . . .
H30 H -0.0695 0.3311 -0.0260 0.063 Uiso 1 1 calc R . .
C31 C 0.1936(6) 0.6088(3) -0.4060(3) 0.0944(13) Uani 1 1 d . . .
H31A H 0.0750 0.6312 -0.4157 0.142 Uiso 1 1 calc R . .
H31B H 0.2725 0.6258 -0.4690 0.142 Uiso 1 1 calc R . .
H31C H 0.2257 0.6475 -0.3508 0.142 Uiso 1 1 calc R . .
F1 F 0.3876(2) 0.24656(13) 0.00501(12) 0.0636(5) Uani 1 1 d . . .
F2 F 0.1087(2) 0.25029(13) 0.09254(12) 0.0642(5) Uani 1 1 d . . .
N1 N 0.2963(3) 0.09159(17) 0.12541(15) 0.0426(5) Uani 1 1 d . . .
N2 N 0.1875(3) 0.12929(16) -0.05024(15) 0.0420(5) Uani 1 1 d . . .
O1 O 0.4889(3) 0.48761(18) 0.23631(16) 0.0733(7) Uani 1 1 d . . .
O2 O 0.2049(3) 0.49299(17) -0.38001(16) 0.0731(7) 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 F2 1.366(3) . ?
B1 F1 1.381(3) . ?
B1 N2 1.578(4) . ?
B1 N1 1.581(4) . ?
C1 N1 1.357(3) . ?
C1 C2 1.431(4) . ?
C1 C18 1.483(4) . ?
C2 C3 1.410(4) . ?
C2 C7 1.416(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.418(4) . ?
C8 C9 1.375(4) . ?
C8 N1 1.402(3) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.404(3) . ?
C10 C11 1.414(4) . ?
C11 C16 1.399(4) . ?
C11 C12 1.414(4) . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.409(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.427(3) . ?
C17 N2 1.359(3) . ?
C17 C25 1.479(4) . ?
C18 C23 1.386(4) . ?
C18 C19 1.403(4) . ?
C19 C20 1.389(4) . ?
C19 H19 0.9300 . ?
C20 O1 1.368(3) . ?
C20 C21 1.379(4) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O1 1.406(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.380(4) . ?
C25 C30 1.394(4) . ?
C26 C27 1.386(4) . ?
C26 H26 0.9300 . ?
C27 O2 1.375(3) . ?
C27 C28 1.385(4) . ?
C28 C29 1.369(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.388(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 O2 1.426(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?



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 111.1(2) . . ?
F2 B1 N2 111.9(2) . . ?
F1 B1 N2 107.2(2) . . ?
F2 B1 N1 108.3(2) . . ?
F1 B1 N1 109.9(2) . . ?
N2 B1 N1 108.4(2) . . ?
N1 C1 C2 109.2(2) . . ?
N1 C1 C18 126.5(2) . . ?
C2 C1 C18 124.3(2) . . ?
C3 C2 C7 120.2(2) . . ?
C3 C2 C1 132.9(3) . . ?
C7 C2 C1 107.0(2) . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 C8 133.0(3) . . ?
C2 C7 C8 106.6(2) . . ?
C9 C8 N1 120.8(2) . . ?
C9 C8 C7 130.4(3) . . ?
N1 C8 C7 108.7(2) . . ?
C8 C9 C10 123.9(3) . . ?
C8 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 N2 120.6(2) . . ?
C9 C10 C11 131.4(2) . . ?
N2 C10 C11 108.1(2) . . ?
C16 C11 C12 120.5(3) . . ?
C16 C11 C10 107.3(2) . . ?
C12 C11 C10 132.2(3) . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C11 C16 C15 120.8(2) . . ?
C11 C16 C17 107.3(2) . . ?
C15 C16 C17 131.9(2) . . ?
N2 C17 C16 108.7(2) . . ?
N2 C17 C25 127.2(2) . . ?
C16 C17 C25 124.1(2) . . ?
C23 C18 C19 118.9(2) . . ?
C23 C18 C1 118.7(2) . . ?
C19 C18 C1 122.3(2) . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
O1 C20 C21 115.4(2) . . ?
O1 C20 C19 124.1(2) . . ?
C21 C20 C19 120.5(3) . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.8(3) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 119.0(2) . . ?
C26 C25 C17 117.2(2) . . ?
C30 C25 C17 123.7(2) . . ?
C25 C26 C27 121.5(2) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
O2 C27 C28 125.3(3) . . ?
O2 C27 C26 115.2(2) . . ?
C28 C27 C26 119.6(3) . . ?
C29 C28 C27 119.0(3) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 122.2(3) . . ?
C28 C29 H29 118.9 . . ?
C30 C29 H29 118.9 . . ?
C29 C30 C25 118.8(3) . . ?
C29 C30 H30 120.6 . . ?
C25 C30 H30 120.6 . . ?
O2 C31 H31A 109.5 . . ?
O2 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O2 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 N1 C8 108.5(2) . . ?
C1 N1 B1 128.6(2) . . ?
C8 N1 B1 122.7(2) . . ?
C17 N2 C10 108.6(2) . . ?
C17 N2 B1 127.7(2) . . ?
C10 N2 B1 122.5(2) . . ?
C20 O1 C24 118.0(2) . . ?
C27 O2 C31 117.4(2) . . ?



_diffrn_measured_fraction_theta_max 0.955

_diffrn_reflns_theta_full        27.64

_diffrn_measured_fraction_theta_full 0.955

_refine_diff_density_max         0.327

_refine_diff_density_min         -0.328

_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_120628b
_database_code_depnum_ccdc_archive 'CCDC 1445552'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C29 H17 B F4 N2'

_chemical_formula_weight         480.26



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'
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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/n



loop_

_symmetry_equiv_pos_as_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'



_cell_length_a                   12.1936(18)

_cell_length_b                   15.062(2)

_cell_length_c                   12.2515(18)

_cell_angle_alpha                90.00

_cell_angle_beta                 97.131(2)

_cell_angle_gamma                90.00

_cell_volume                     2232.7(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    5816

_cell_measurement_theta_min      2.52

_cell_measurement_theta_max      26.71



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.15

_exptl_crystal_size_mid          0.13

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.429

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    0.107

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9842

_exptl_absorpt_correction_T_max  0.9873

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            18545

_diffrn_reflns_av_R_equivalents  0.0463

_diffrn_reflns_av_sigmaI/netI    0.0416

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -19

_diffrn_reflns_limit_k_max       19

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         2.15

_diffrn_reflns_theta_max         27.61

_reflns_number_total             5131

_reflns_number_gt                3294

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.8862P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         5131

_refine_ls_number_parameters     325

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0873

_refine_ls_R_factor_gt           0.0517

_refine_ls_wR_factor_ref         0.1418

_refine_ls_wR_factor_gt          0.1215

_refine_ls_goodness_of_fit_ref   0.999

_refine_ls_restrained_S_all      0.999

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group





















































B1 B 0.5743(2) 0.08200(18) 0.2835(2) 0.0509(6) Uani 1 1 d . . .
C1 C 0.74996(16) 0.00662(13) 0.38874(16) 0.0425(5) Uani 1 1 d . . .
C2 C 0.78871(16) -0.01379(13) 0.50039(17) 0.0453(5) Uani 1 1 d . . .
C3 C 0.88228(18) -0.06004(16) 0.54889(19) 0.0566(6) Uani 1 1 d . . .
H3 H 0.9322 -0.0846 0.5059 0.068 Uiso 1 1 calc R . .
C4 C 0.8981(2) -0.06799(17) 0.6605(2) 0.0647(7) Uani 1 1 d . . .
H4 H 0.9595 -0.0985 0.6939 0.078 Uiso 1 1 calc R . .
C5 C 0.8233(2) -0.03094(16) 0.7261(2) 0.0646(7) Uani 1 1 d . . .
H5 H 0.8362 -0.0378 0.8020 0.078 Uiso 1 1 calc R . .
C6 C 0.7316(2) 0.01508(14) 0.68088(17) 0.0526(5) Uani 1 1 d . . .
H6 H 0.6824 0.0392 0.7250 0.063 Uiso 1 1 calc R . .
C7 C 0.71434(17) 0.02465(13) 0.56626(16) 0.0441(5) Uani 1 1 d . . .
C8 C 0.63139(16) 0.06832(13) 0.49364(15) 0.0416(4) Uani 1 1 d . . .
C9 C 0.53863(17) 0.11515(12) 0.51368(16) 0.0439(5) Uani 1 1 d . . .
H9 H 0.5256 0.1231 0.5862 0.053 Uiso 1 1 calc R . .
C10 C 0.46438(16) 0.15075(12) 0.43115(15) 0.0403(4) Uani 1 1 d . . .
C11 C 0.36959(17) 0.20613(12) 0.43371(16) 0.0416(4) Uani 1 1 d . . .
C12 C 0.31602(19) 0.24041(14) 0.51952(18) 0.0516(5) Uani 1 1 d . . .
H12 H 0.3428 0.2293 0.5927 0.062 Uiso 1 1 calc R . .
C13 C 0.2230(2) 0.29074(15) 0.4923(2) 0.0596(6) Uani 1 1 d . . .
H13 H 0.1863 0.3138 0.5483 0.072 Uiso 1 1 calc R . .
C14 C 0.1816(2) 0.30843(15) 0.3832(2) 0.0587(6) Uani 1 1 d . . .
H14 H 0.1180 0.3425 0.3679 0.070 Uiso 1 1 calc R . .
C15 C 0.23318(17) 0.27648(13) 0.29782(18) 0.0497(5) Uani 1 1 d . . .
H15 H 0.2053 0.2880 0.2251 0.060 Uiso 1 1 calc R . .
C16 C 0.32943(16) 0.22579(12) 0.32397(16) 0.0408(4) Uani 1 1 d . . .
C17 C 0.39948(16) 0.18252(12) 0.25602(15) 0.0383(4) Uani 1 1 d . . .
C18 C 0.80200(15) -0.02087(14) 0.29192(17) 0.0443(5) Uani 1 1 d . . .
C19 C 0.82262(16) 0.03790(15) 0.20932(17) 0.0503(5) Uani 1 1 d . . .
H19 H 0.8027 0.0972 0.2140 0.060 Uiso 1 1 calc R . .
C20 C 0.87226(19) 0.00916(17) 0.1206(2) 0.0624(6) Uani 1 1 d . . .
H20 H 0.8854 0.0484 0.0650 0.075 Uiso 1 1 calc R . .
C21 C 0.9017(2) -0.07792(19) 0.1160(2) 0.0667(7) Uani 1 1 d . . .
C22 C 0.88590(19) -0.13784(17) 0.1959(2) 0.0642(6) Uani 1 1 d . . .
H22 H 0.9082 -0.1966 0.1910 0.077 Uiso 1 1 calc R . .
C23 C 0.83581(17) -0.10869(15) 0.28461(19) 0.0530(5) Uani 1 1 d . . .
H23 H 0.8245 -0.1484 0.3403 0.064 Uiso 1 1 calc R . .
C24 C 0.39208(15) 0.18956(13) 0.13592(15) 0.0390(4) Uani 1 1 d . . .
C25 C 0.38422(17) 0.27388(14) 0.08879(17) 0.0473(5) Uani 1 1 d . . .
H25 H 0.3821 0.3235 0.1337 0.057 Uiso 1 1 calc R . .
C26 C 0.37948(18) 0.28476(15) -0.02353(18) 0.0540(6) Uani 1 1 d . . .
H26 H 0.3742 0.3411 -0.0548 0.065 Uiso 1 1 calc R . .
C27 C 0.38281(18) 0.21095(16) -0.08751(16) 0.0526(5) Uani 1 1 d . . .
C28 C 0.38746(18) 0.12701(16) -0.04565(17) 0.0543(6) Uani 1 1 d . . .
H28 H 0.3875 0.0780 -0.0918 0.065 Uiso 1 1 calc R . .
C29 C 0.39208(17) 0.11635(14) 0.06671(16) 0.0470(5) Uani 1 1 d . . .
H29 H 0.3952 0.0595 0.0965 0.056 Uiso 1 1 calc R . .
F1 F 0.62338(13) 0.13209(15) 0.21242(13) 0.1110(8) Uani 1 1 d . . .
F2 F 0.53299(13) 0.00342(11) 0.23615(13) 0.0974(6) Uani 1 1 d . . .
F3 F 0.94813(16) -0.10699(13) 0.02708(15) 0.1065(6) Uani 1 1 d . . .
F4 F 0.38158(13) 0.22217(11) -0.19752(10) 0.0804(5) Uani 1 1 d . . .
N1 N 0.65621(13) 0.05614(10) 0.38645(12) 0.0403(4) Uani 1 1 d . . .
N2 N 0.47844(13) 0.13731(10) 0.32130(12) 0.0378(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 1.348(3) . ?
B1 F2 1.385(3) . ?
B1 N2 1.552(3) . ?
B1 N1 1.558(3) . ?
C1 N1 1.362(2) . ?
C1 C2 1.424(3) . ?
C1 C18 1.472(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.411(3) . ?
C3 C4 1.362(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.423(3) . ?
C8 C9 1.381(3) . ?
C8 N1 1.396(2) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.393(2) . ?
C10 C11 1.429(3) . ?
C11 C12 1.403(3) . ?
C11 C16 1.404(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.403(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.423(3) . ?
C17 N2 1.356(2) . ?
C17 C24 1.467(3) . ?
C18 C19 1.391(3) . ?
C18 C23 1.392(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(4) . ?
C20 H20 0.9300 . ?
C21 F3 1.361(3) . ?
C21 C22 1.363(4) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C29 1.391(3) . ?
C24 C25 1.393(3) . ?
C25 C26 1.380(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.364(3) . ?
C26 H26 0.9300 . ?
C27 F4 1.357(2) . ?
C27 C28 1.363(3) . ?
C28 C29 1.380(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?



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 112.0(2) . . ?
F1 B1 N2 107.69(19) . . ?
F2 B1 N2 109.63(19) . . ?
F1 B1 N1 111.8(2) . . ?
F2 B1 N1 106.77(19) . . ?
N2 B1 N1 108.87(16) . . ?
N1 C1 C2 108.38(17) . . ?
N1 C1 C18 125.58(17) . . ?
C2 C1 C18 126.04(18) . . ?
C3 C2 C7 120.5(2) . . ?
C3 C2 C1 132.0(2) . . ?
C7 C2 C1 107.50(18) . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 118.0(2) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 C8 132.9(2) . . ?
C2 C7 C8 106.83(17) . . ?
C9 C8 N1 120.84(17) . . ?
C9 C8 C7 131.26(18) . . ?
N1 C8 C7 107.89(17) . . ?
C10 C9 C8 123.09(18) . . ?
C10 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C9 C10 N2 120.24(18) . . ?
C9 C10 C11 132.07(18) . . ?
N2 C10 C11 107.64(16) . . ?
C12 C11 C16 120.02(19) . . ?
C12 C11 C10 133.18(19) . . ?
C16 C11 C10 106.80(16) . . ?
C13 C12 C11 118.0(2) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 117.8(2) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C11 C16 C15 121.04(18) . . ?
C11 C16 C17 107.48(17) . . ?
C15 C16 C17 131.41(19) . . ?
N2 C17 C16 108.59(16) . . ?
N2 C17 C24 125.35(16) . . ?
C16 C17 C24 125.97(17) . . ?
C19 C18 C23 118.4(2) . . ?
C19 C18 C1 122.83(19) . . ?
C23 C18 C1 118.67(19) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 118.6(2) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 F3 118.7(2) . . ?
C20 C21 C22 123.1(2) . . ?
F3 C21 C22 118.2(2) . . ?
C21 C22 C23 118.0(2) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C29 C24 C25 118.36(18) . . ?
C29 C24 C17 123.34(18) . . ?
C25 C24 C17 118.30(17) . . ?
C26 C25 C24 120.9(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 118.4(2) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
F4 C27 C28 119.0(2) . . ?
F4 C27 C26 118.2(2) . . ?
C28 C27 C26 122.9(2) . . ?
C27 C28 C29 118.6(2) . . ?
C27 C28 H28 120.7 . . ?
C29 C28 H28 120.7 . . ?
C28 C29 C24 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
C1 N1 C8 109.39(16) . . ?
C1 N1 B1 127.27(16) . . ?
C8 N1 B1 122.45(16) . . ?
C17 N2 C10 109.48(15) . . ?
C17 N2 B1 126.82(16) . . ?
C10 N2 B1 123.65(16) . . ?



_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        27.61

_diffrn_measured_fraction_theta_full 0.990

_refine_diff_density_max         0.424

_refine_diff_density_min         -0.530

_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_121109b_0m
_database_code_depnum_ccdc_archive 'CCDC 1445553'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;
_audit_creation_date             2016-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C31 H23 B F2 N2 O2'
_chemical_formula_sum            'C31 H23 B F2 N2 O2'
_chemical_formula_weight         504.32
_chemical_melting_point          ?
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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2591(10)
_cell_length_b                   10.3442(10)
_cell_length_c                   12.7331(12)
_cell_angle_alpha                96.5350(10)
_cell_angle_beta                 104.5740(10)
_cell_angle_gamma                104.6180(10)
_cell_volume                     1242.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4437
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      28.6246
_cell_measurement_theta_min      2.4902
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7999
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10880
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.704
_diffrn_reflns_theta_min         1.683
_diffrn_ambient_temperature      293.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -100.0000 - 80.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.1704
	          2theta: -10.0105
scan:
	Number of images: 360
	           Slice: -100.0000 - 80.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.1704
	          2theta: -10.0105
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_number_total             5371
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0035
_diffrn_orient_matrix_UB_12      -0.1347
_diffrn_orient_matrix_UB_13      -0.0390
_diffrn_orient_matrix_UB_21      0.0509
_diffrn_orient_matrix_UB_22      -0.0372
_diffrn_orient_matrix_UB_23      0.0812
_diffrn_orient_matrix_UB_31      -0.0389
_diffrn_orient_matrix_UB_32      -0.0175
_diffrn_orient_matrix_UB_33      0.0275
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4054
_reflns_number_total             5665
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0082(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.007
_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)+(0.0505P)²+0.4466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C29(H29),
  C30(H30)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.2291(3) 0.8698(2) 0.94247(17) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.4911(2) 0.3237(2) 1.1531(2) 0.0611(5) Uani 1 1 d . . . . .
H1A H 0.4731 0.3258 1.0757 0.092 Uiso 1 1 calc GR . . . .
H1B H 0.4948 0.2346 1.1651 0.092 Uiso 1 1 calc GR . . . .
H1C H 0.5795 0.3894 1.1933 0.092 Uiso 1 1 calc GR . . . .
F1 F 0.11145(17) 0.76018(12) 0.88898(10) 0.0852(5) Uani 1 1 d . . . . .
N1 N 0.22171(14) 0.91009(14) 1.06326(11) 0.0386(3) Uani 1 1 d . . . . .
O1 O 0.38117(15) 0.35551(13) 1.19064(12) 0.0586(4) Uani 1 1 d . . . . .
C2 C 0.34872(19) 0.47152(17) 1.16992(15) 0.0451(4) Uani 1 1 d . . . . .
F2 F 0.34879(17) 0.84016(17) 0.94136(12) 0.0921(5) Uani 1 1 d . . . . .
N2 N 0.22108(14) 0.99421(14) 0.88336(11) 0.0381(3) Uani 1 1 d . . . . .
O2 O 0.37156(17) 0.63647(16) 0.49967(13) 0.0728(5) Uani 1 1 d . . . . .
C3 C 0.42949(19) 0.57479(18) 1.13291(15) 0.0450(4) Uani 1 1 d . . . . .
H3 H 0.5107 0.5659 1.1168 0.054 Uiso 1 1 calc R . . . .
C4 C 0.38911(18) 0.69166(18) 1.11983(14) 0.0430(4) Uani 1 1 d . . . . .
H4 H 0.4442 0.7608 1.0953 0.052 Uiso 1 1 calc R . . . .
C5 C 0.26801(18) 0.70735(17) 1.14267(14) 0.0405(4) Uani 1 1 d . . . . .
C6 C 0.1866(2) 0.60035(19) 1.17752(17) 0.0510(5) Uani 1 1 d . . . . .
H6 H 0.1041 0.6077 1.1921 0.061 Uiso 1 1 calc R . . . .
C7 C 0.2261(2) 0.48462(19) 1.19064(18) 0.0550(5) Uani 1 1 d . . . . .
H7 H 0.1701 0.4145 1.2136 0.066 Uiso 1 1 calc R . . . .
C8 C 0.22882(17) 0.83440(17) 1.14351(14) 0.0394(4) Uani 1 1 d . . . . .
C9 C 0.19296(17) 0.89949(17) 1.23261(14) 0.0397(4) Uani 1 1 d . . . . .
C10 C 0.1873(2) 0.86707(19) 1.33612(15) 0.0484(4) Uani 1 1 d . . . . .
H10 H 0.2093 0.7900 1.3570 0.058 Uiso 1 1 calc R . . . .
C11 C 0.1489(2) 0.9516(2) 1.40497(16) 0.0531(5) Uani 1 1 d . . . . .
H11 H 0.1439 0.9313 1.4734 0.064 Uiso 1 1 calc R . . . .
C12 C 0.1166(2) 1.0687(2) 1.37446(15) 0.0508(5) Uani 1 1 d . . . . .
H12 H 0.0893 1.1235 1.4227 0.061 Uiso 1 1 calc R . . . .
C13 C 0.12451(19) 1.10386(18) 1.27514(15) 0.0448(4) Uani 1 1 d . . . . .
H13 H 0.1048 1.1825 1.2561 0.054 Uiso 1 1 calc R . . . .
C14 C 0.16303(17) 1.01817(17) 1.20324(14) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.18076(17) 1.02338(16) 1.09645(14) 0.0383(4) Uani 1 1 d . . . . .
C16 C 0.16300(17) 1.11660(17) 1.02925(14) 0.0397(4) Uani 1 1 d . . . . .
H16 H 0.1336 1.1895 1.0537 0.048 Uiso 1 1 calc R . . . .
C17 C 0.18693(17) 1.10660(16) 0.92724(14) 0.0380(4) Uani 1 1 d . . . . .
C18 C 0.19174(17) 1.19912(17) 0.85278(14) 0.0388(4) Uani 1 1 d . . . . .
C19 C 0.16620(18) 1.32629(18) 0.85396(16) 0.0456(4) Uani 1 1 d . . . . .
H19 H 0.1425 1.3668 0.9126 0.055 Uiso 1 1 calc R . . . .
C20 C 0.1773(2) 1.38897(19) 0.76585(17) 0.0523(5) Uani 1 1 d . . . . .
H20 H 0.1601 1.4730 0.7648 0.063 Uiso 1 1 calc R . . . .
C21 C 0.2139(2) 1.3291(2) 0.67727(17) 0.0552(5) Uani 1 1 d . . . . .
H21 H 0.2197 1.3739 0.6186 0.066 Uiso 1 1 calc R . . . .
C22 C 0.24134(19) 1.20607(19) 0.67530(16) 0.0484(4) Uani 1 1 d . . . . .
H22 H 0.2661 1.1674 0.6164 0.058 Uiso 1 1 calc R . . . .
C23 C 0.23107(17) 1.13994(17) 0.76456(14) 0.0399(4) Uani 1 1 d . . . . .
C24 C 0.24824(17) 1.01225(17) 0.78659(14) 0.0392(4) Uani 1 1 d . . . . .
C25 C 0.28319(18) 0.91298(17) 0.71441(14) 0.0413(4) Uani 1 1 d . . . . .
C26 C 0.19533(19) 0.78066(18) 0.67263(15) 0.0458(4) Uani 1 1 d . . . . .
H26 H 0.1138 0.7515 0.6936 0.055 Uiso 1 1 calc R . . . .
C27 C 0.2276(2) 0.69243(19) 0.60073(16) 0.0504(5) Uani 1 1 d . . . . .
H27 H 0.1670 0.6049 0.5725 0.060 Uiso 1 1 calc R . . . .
C28 C 0.3501(2) 0.7334(2) 0.57026(16) 0.0510(5) Uani 1 1 d . . . . .
C29 C 0.4389(2) 0.8636(2) 0.61066(17) 0.0555(5) Uani 1 1 d . . . . .
H29 H 0.5213 0.8916 0.5906 0.067 Uiso 1 1 calc R . . . .
C30 C 0.4043(2) 0.9526(2) 0.68150(16) 0.0493(4) Uani 1 1 d . . . . .
H30 H 0.4637 1.0409 0.7076 0.059 Uiso 1 1 calc R . . . .
C31 C 0.4940(3) 0.6725(3) 0.4635(3) 0.0961(9) Uani 1 1 d . . . . .
H31A H 0.4935 0.7492 0.4276 0.144 Uiso 1 1 calc GR . . . .
H31B H 0.4946 0.5970 0.4125 0.144 Uiso 1 1 calc GR . . . .
H31C H 0.5764 0.6958 0.5260 0.144 Uiso 1 1 calc GR . . . .


_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 1.388(3) . ?
B1 N1 1.573(2) . ?
B1 F2 1.341(2) . ?
B1 N2 1.572(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.425(2) . ?
N1 C8 1.355(2) . ?
N1 C15 1.398(2) . ?
O1 C2 1.360(2) . ?
C2 C3 1.384(2) . ?
C2 C7 1.384(3) . ?
N2 C17 1.394(2) . ?
N2 C24 1.353(2) . ?
O2 C28 1.367(2) . ?
O2 C31 1.422(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C5 C6 1.397(2) . ?
C5 C8 1.468(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(2) . ?
C9 C10 1.408(2) . ?
C9 C14 1.407(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.404(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(2) . ?
C14 C15 1.422(2) . ?
C15 C16 1.376(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(2) . ?
C17 C18 1.423(2) . ?
C18 C19 1.404(2) . ?
C18 C23 1.413(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.403(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.404(2) . ?
C23 C24 1.425(2) . ?
C24 C25 1.471(2) . ?
C25 C26 1.393(2) . ?
C25 C30 1.390(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.386(3) . ?
C28 C29 1.376(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(3) . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

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 N1 106.99(15) . . ?
F1 B1 N2 109.24(16) . . ?
F2 B1 F1 111.61(18) . . ?
F2 B1 N1 112.25(17) . . ?
F2 B1 N2 108.88(16) . . ?
N2 B1 N1 107.76(14) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
C8 N1 B1 127.50(14) . . ?
C8 N1 C15 109.08(14) . . ?
C15 N1 B1 122.53(14) . . ?
C2 O1 C1 118.44(15) . . ?
O1 C2 C3 125.06(17) . . ?
O1 C2 C7 115.52(16) . . ?
C3 C2 C7 119.41(16) . . ?
C17 N2 B1 123.37(14) . . ?
C24 N2 B1 127.07(14) . . ?
C24 N2 C17 109.55(14) . . ?
C28 O2 C31 117.87(19) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.88(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.27(16) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.73(16) . . ?
C4 C5 C8 123.80(15) . . ?
C6 C5 C8 118.15(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.21(17) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.47(17) . . ?
C6 C7 H7 119.8 . . ?
N1 C8 C5 127.10(15) . . ?
N1 C8 C9 108.60(14) . . ?
C9 C8 C5 124.29(15) . . ?
C10 C9 C8 132.22(16) . . ?
C14 C9 C8 107.52(14) . . ?
C14 C9 C10 120.24(16) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.27(17) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.28(17) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.43(17) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.14(17) . . ?
C14 C13 H13 120.9 . . ?
C9 C14 C15 106.59(15) . . ?
C13 C14 C9 120.62(15) . . ?
C13 C14 C15 132.79(16) . . ?
N1 C15 C14 108.20(14) . . ?
C16 C15 N1 121.25(15) . . ?
C16 C15 C14 130.55(16) . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C17 122.83(16) . . ?
C17 C16 H16 118.6 . . ?
N2 C17 C18 107.91(14) . . ?
C16 C17 N2 120.79(15) . . ?
C16 C17 C18 131.20(16) . . ?
C19 C18 C17 132.78(16) . . ?
C19 C18 C23 120.57(15) . . ?
C23 C18 C17 106.65(14) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 C18 117.98(17) . . ?
C20 C19 H19 121.0 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.44(17) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.51(17) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 120.9 . . ?
C21 C22 C23 118.19(18) . . ?
C23 C22 H22 120.9 . . ?
C18 C23 C24 107.28(14) . . ?
C22 C23 C18 120.29(16) . . ?
C22 C23 C24 132.38(17) . . ?
N2 C24 C23 108.60(15) . . ?
N2 C24 C25 125.20(15) . . ?
C23 C24 C25 126.15(15) . . ?
C26 C25 C24 122.33(15) . . ?
C30 C25 C24 119.73(16) . . ?
C30 C25 C26 117.87(16) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.84(17) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.33(18) . . ?
C28 C27 H27 119.8 . . ?
O2 C28 C27 114.94(18) . . ?
O2 C28 C29 125.11(18) . . ?
C29 C28 C27 119.95(18) . . ?
C28 C29 H29 120.3 . . ?
C28 C29 C30 119.35(18) . . ?
C30 C29 H29 120.3 . . ?
C25 C30 C29 121.64(18) . . ?
C25 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
O2 C31 H31A 109.5 . . ?
O2 C31 H31B 109.5 . . ?
O2 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

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
B1 N1 C8 C5 10.9(3) . . . . ?
B1 N1 C8 C9 -169.84(16) . . . . ?
B1 N1 C15 C14 170.57(15) . . . . ?
B1 N1 C15 C16 -9.0(2) . . . . ?
B1 N2 C17 C16 2.5(2) . . . . ?
B1 N2 C17 C18 179.18(15) . . . . ?
B1 N2 C24 C23 -178.81(16) . . . . ?
B1 N2 C24 C25 3.7(3) . . . . ?
C1 O1 C2 C3 -12.3(3) . . . . ?
C1 O1 C2 C7 169.04(18) . . . . ?
F1 B1 N1 C8 64.5(2) . . . . ?
F1 B1 N1 C15 -103.55(18) . . . . ?
F1 B1 N2 C17 105.19(18) . . . . ?
F1 B1 N2 C24 -76.5(2) . . . . ?
N1 B1 N2 C17 -10.7(2) . . . . ?
N1 B1 N2 C24 167.57(15) . . . . ?
N1 C8 C9 C10 -178.06(18) . . . . ?
N1 C8 C9 C14 0.22(19) . . . . ?
N1 C15 C16 C17 -1.4(3) . . . . ?
O1 C2 C3 C4 -176.83(17) . . . . ?
O1 C2 C7 C6 176.98(18) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
F2 B1 N1 C8 -58.3(2) . . . . ?
F2 B1 N1 C15 133.69(17) . . . . ?
F2 B1 N2 C17 -132.69(17) . . . . ?
F2 B1 N2 C24 45.6(3) . . . . ?
N2 B1 N1 C8 -178.17(15) . . . . ?
N2 B1 N1 C15 13.8(2) . . . . ?
N2 C17 C18 C19 179.40(17) . . . . ?
N2 C17 C18 C23 -0.68(18) . . . . ?
N2 C24 C25 C26 56.6(2) . . . . ?
N2 C24 C25 C30 -126.59(19) . . . . ?
O2 C28 C29 C30 179.65(19) . . . . ?
C3 C2 C7 C6 -1.7(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 C8 172.28(17) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C4 C5 C8 N1 51.1(3) . . . . ?
C4 C5 C8 C9 -128.13(19) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C5 C8 C9 C10 1.3(3) . . . . ?
C5 C8 C9 C14 179.55(15) . . . . ?
C6 C5 C8 N1 -135.58(19) . . . . ?
C6 C5 C8 C9 45.2(2) . . . . ?
C7 C2 C3 C4 1.8(3) . . . . ?
C8 N1 C15 C14 0.62(18) . . . . ?
C8 N1 C15 C16 -178.92(15) . . . . ?
C8 C5 C6 C7 -172.63(18) . . . . ?
C8 C9 C10 C11 179.74(19) . . . . ?
C8 C9 C14 C13 -179.88(16) . . . . ?
C8 C9 C14 C15 0.16(18) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C14 C15 N1 -0.47(18) . . . . ?
C9 C14 C15 C16 179.01(17) . . . . ?
C10 C9 C14 C13 -1.4(3) . . . . ?
C10 C9 C14 C15 178.69(16) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C12 C13 C14 C15 179.82(18) . . . . ?
C13 C14 C15 N1 179.58(18) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C9 C10 C11 1.6(3) . . . . ?
C14 C15 C16 C17 179.14(17) . . . . ?
C15 N1 C8 C5 -179.82(16) . . . . ?
C15 N1 C8 C9 -0.51(19) . . . . ?
C15 C16 C17 N2 4.7(3) . . . . ?
C15 C16 C17 C18 -171.10(17) . . . . ?
C16 C17 C18 C19 -4.4(3) . . . . ?
C16 C17 C18 C23 175.56(17) . . . . ?
C17 N2 C24 C23 -0.33(18) . . . . ?
C17 N2 C24 C25 -177.77(15) . . . . ?
C17 C18 C19 C20 -178.51(18) . . . . ?
C17 C18 C23 C22 178.31(16) . . . . ?
C17 C18 C23 C24 0.48(18) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C18 C23 C24 N2 -0.10(19) . . . . ?
C18 C23 C24 C25 177.31(16) . . . . ?
C19 C18 C23 C22 -1.8(3) . . . . ?
C19 C18 C23 C24 -179.59(15) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C18 0.7(3) . . . . ?
C21 C22 C23 C24 177.95(18) . . . . ?
C22 C23 C24 N2 -177.56(18) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C18 C19 C20 1.6(3) . . . . ?
C23 C24 C25 C26 -120.4(2) . . . . ?
C23 C24 C25 C30 56.4(2) . . . . ?
C24 N2 C17 C16 -176.07(15) . . . . ?
C24 N2 C17 C18 0.64(18) . . . . ?
C24 C25 C26 C27 176.63(17) . . . . ?
C24 C25 C30 C29 -177.88(17) . . . . ?
C25 C26 C27 C28 1.2(3) . . . . ?
C26 C25 C30 C29 -0.9(3) . . . . ?
C26 C27 C28 O2 179.18(17) . . . . ?
C26 C27 C28 C29 -1.0(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C25 1.1(3) . . . . ?
C30 C25 C26 C27 -0.2(3) . . . . ?
C31 O2 C28 C27 178.9(2) . . . . ?
C31 O2 C28 C29 -0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
