# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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data_1401cd46_0m
_database_code_depnum_ccdc_archive 'CCDC 1058690'
_audit_update_record             
;
2015-04-09 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 2ac 2ab'
#Added by publCIF




_diffrn_radiation_monochromator  graphite
#Added by publCIF


_audit_creation_date             2015-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C20 H15 N2'
_chemical_formula_sum            'C20 H15 B F4 N2'
_chemical_formula_weight         370.15
_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'
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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.5582(7)
_cell_length_b                   12.3717(7)
_cell_length_c                   23.8099(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3404.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5271
_cell_measurement_temperature    115
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0482 before and 0.0418 after correction.
The Ratio of minimum to maximum transmission is 0.8016.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_temperature      115
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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_source                   'X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2882
_reflns_number_total             3884
_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 (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.026
_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)+(0.0574P)²+1.8783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1362
_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. Others
 Sof(F2A)=Sof(F4A)=Sof(F3A)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1), C20(H20), C19(H19), C16(H16), C17(H17), C18(H18), C7(H7),
 C12(H12), C3(H3), C2(H2), C11(H11)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
F1 F 0.91676(14) 0.56311(11) 0.29594(7) 0.0747(5) Uani 1 1 d . . . . .
C4 C 0.6442(2) 0.64630(19) 0.27468(10) 0.0538(6) Uani 1 1 d . . . . .
H4A H 0.5935 0.7089 0.2801 0.081 Uiso 1 1 calc GR . . . .
H4B H 0.6972 0.6402 0.3066 0.081 Uiso 1 1 calc GR . . . .
H4C H 0.5972 0.5806 0.2720 0.081 Uiso 1 1 calc GR . . . .
N2 N 0.71099(13) 0.66014(12) 0.22274(7) 0.0370(4) Uani 1 1 d . . . . .
C5 C 0.80517(13) 0.57915(13) 0.08700(8) 0.0291(4) Uani 1 1 d . . . . .
C15 C 0.98888(14) 0.28303(13) 0.07889(9) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.83700(13) 0.47913(12) -0.01673(8) 0.0286(4) Uani 1 1 d . . . . .
C6 C 0.76561(13) 0.62837(13) 0.03860(8) 0.0309(4) Uani 1 1 d . . . . .
H6 H 0.7274 0.6962 0.0408 0.037 Uiso 1 1 calc R . . . .
B B 0.91258(19) 0.45353(17) 0.30751(9) 0.0351(5) Uani 1 1 d . . . . .
F2 F 0.9933(3) 0.4358(2) 0.35130(15) 0.0623(12) Uani 0.464(4) 1 d . . P A 1
F3 F 0.8131(3) 0.3996(3) 0.3248(2) 0.0784(15) Uani 0.464(4) 1 d . . P A 1
C1 C 0.70801(15) 0.59476(15) 0.17877(9) 0.0377(4) Uani 1 1 d . . . . .
H1 H 0.6604 0.5325 0.1752 0.045 Uiso 1 1 calc R . . . .
N1 N 0.78269(11) 0.63050(11) 0.14029(6) 0.0308(3) Uani 1 1 d . . . . .
C10 C 0.86651(13) 0.48132(12) 0.08614(8) 0.0280(4) Uani 1 1 d . . . . .
C20 C 0.91553(14) 0.43181(14) 0.13537(8) 0.0340(4) Uani 1 1 d . . . . .
H20 H 0.9063 0.4654 0.1710 0.041 Uiso 1 1 calc R . . . .
C19 C 0.97479(15) 0.33763(14) 0.13132(9) 0.0377(4) Uani 1 1 d . . . . .
H19 H 1.0078 0.3071 0.1642 0.045 Uiso 1 1 calc R . . . .
C16 C 1.04570(15) 0.18298(14) 0.07435(10) 0.0434(5) Uani 1 1 d . . . . .
H16 H 1.0790 0.1507 0.1068 0.052 Uiso 1 1 calc R . . . .
C17 C 1.05352(16) 0.13128(15) 0.02314(10) 0.0469(6) Uani 1 1 d . . . . .
H17 H 1.0919 0.0635 0.0209 0.056 Uiso 1 1 calc R . . . .
C18 C 1.00696(15) 0.17578(15) -0.02481(9) 0.0425(5) Uani 1 1 d . . . . .
H18 H 1.0129 0.1380 -0.0594 0.051 Uiso 1 1 calc R . . . .
C13 C 0.95081(14) 0.27643(13) -0.02305(8) 0.0347(4) Uani 1 1 d . . . . .
C14 C 0.94161(13) 0.33025(13) 0.02951(8) 0.0305(4) Uani 1 1 d . . . . .
C9 C 0.88159(13) 0.43103(12) 0.03295(7) 0.0275(4) Uani 1 1 d . . . . .
C7 C 0.78140(13) 0.57946(13) -0.01298(8) 0.0305(4) Uani 1 1 d . . . . .
H7 H 0.7544 0.6141 -0.0461 0.037 Uiso 1 1 calc R . . . .
C12 C 0.90038(15) 0.32521(15) -0.07178(8) 0.0369(4) Uani 1 1 d . . . . .
H12 H 0.9040 0.2883 -0.1067 0.044 Uiso 1 1 calc R . . . .
C3 C 0.83481(15) 0.72260(14) 0.16120(8) 0.0354(4) Uani 1 1 d . . . . .
H3 H 0.8916 0.7653 0.1428 0.042 Uiso 1 1 calc R . . . .
C2 C 0.79004(15) 0.74047(15) 0.21247(8) 0.0384(4) Uani 1 1 d . . . . .
H2 H 0.8095 0.7981 0.2371 0.046 Uiso 1 1 calc R . . . .
F4 F 0.9614(5) 0.3893(3) 0.26364(14) 0.0895(16) Uani 0.464(4) 1 d . . P A 1
C11 C 0.84765(15) 0.42263(14) -0.06915(8) 0.0341(4) Uani 1 1 d . . . . .
H11 H 0.8173 0.4541 -0.1024 0.041 Uiso 1 1 calc R . . . .
F2A F 0.8694(4) 0.4491(3) 0.36057(11) 0.0894(14) Uani 0.536(4) 1 d . . P A 2
F4A F 1.0112(3) 0.4101(2) 0.3003(3) 0.103(2) Uani 0.536(4) 1 d . . P A 2
F3A F 0.8252(3) 0.4230(2) 0.27261(14) 0.0742(11) Uani 0.536(4) 1 d . . P A 2


_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
F1 B 1.384(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N2 1.468(3) . ?
N2 C1 1.323(2) . ?
N2 C2 1.372(2) . ?
C5 C6 1.381(2) . ?
C5 N1 1.443(2) . ?
C5 C10 1.403(2) . ?
C15 C19 1.429(3) . ?
C15 C16 1.405(2) . ?
C15 C14 1.422(2) . ?
C8 C9 1.421(2) . ?
C8 C7 1.401(2) . ?
C8 C11 1.436(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(2) . ?
B F2 1.416(3) . ?
B F3 1.392(4) . ?
B F4 1.429(4) . ?
B F2A 1.360(3) . ?
B F4A 1.272(3) . ?
B F3A 1.362(3) . ?
C1 H1 0.9500 . ?
C1 N1 1.334(2) . ?
N1 C3 1.382(2) . ?
C10 C20 1.439(2) . ?
C10 C9 1.422(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.355(2) . ?
C19 H19 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9500 . ?
C18 C13 1.405(2) . ?
C13 C14 1.422(3) . ?
C13 C12 1.432(3) . ?
C14 C9 1.429(2) . ?
C7 H7 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.352(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.344(3) . ?
C2 H2 0.9500 . ?
C11 H11 0.9500 . ?

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
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
C1 N2 C4 125.55(17) . . ?
C1 N2 C2 108.62(16) . . ?
C2 N2 C4 125.79(17) . . ?
C6 C5 N1 118.69(14) . . ?
C6 C5 C10 122.37(16) . . ?
C10 C5 N1 118.94(15) . . ?
C16 C15 C19 122.47(18) . . ?
C16 C15 C14 118.54(18) . . ?
C14 C15 C19 118.97(15) . . ?
C9 C8 C11 119.25(15) . . ?
C7 C8 C9 118.99(16) . . ?
C7 C8 C11 121.74(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.33(15) . . ?
C7 C6 H6 119.8 . . ?
F1 B F2 105.97(19) . . ?
F1 B F3 123.9(2) . . ?
F1 B F4 112.7(2) . . ?
F2 B F4 101.0(3) . . ?
F3 B F2 104.6(3) . . ?
F3 B F4 106.0(3) . . ?
F2A B F1 103.7(2) . . ?
F2A B F3A 106.5(3) . . ?
F4A B F1 110.8(2) . . ?
F4A B F2A 115.9(4) . . ?
F4A B F3A 117.8(3) . . ?
F3A B F1 100.1(2) . . ?
N2 C1 H1 125.6 . . ?
N2 C1 N1 108.89(16) . . ?
N1 C1 H1 125.6 . . ?
C1 N1 C5 125.06(14) . . ?
C1 N1 C3 107.94(16) . . ?
C3 N1 C5 126.98(14) . . ?
C5 C10 C20 123.68(17) . . ?
C5 C10 C9 116.90(15) . . ?
C9 C10 C20 119.41(15) . . ?
C10 C20 H20 119.8 . . ?
C19 C20 C10 120.48(18) . . ?
C19 C20 H20 119.8 . . ?
C15 C19 H19 119.1 . . ?
C20 C19 C15 121.76(17) . . ?
C20 C19 H19 119.1 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.45(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.45(17) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C13 120.7(2) . . ?
C13 C18 H18 119.7 . . ?
C18 C13 C14 118.42(18) . . ?
C18 C13 C12 122.52(18) . . ?
C14 C13 C12 119.04(15) . . ?
C15 C14 C9 119.84(17) . . ?
C13 C14 C15 120.44(15) . . ?
C13 C14 C9 119.70(16) . . ?
C8 C9 C10 120.92(14) . . ?
C8 C9 C14 119.59(16) . . ?
C10 C9 C14 119.49(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.36(16) . . ?
C6 C7 H7 119.8 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.44(18) . . ?
C11 C12 H12 119.3 . . ?
N1 C3 H3 126.4 . . ?
C2 C3 N1 107.16(16) . . ?
C2 C3 H3 126.4 . . ?
N2 C2 H2 126.3 . . ?
C3 C2 N2 107.39(17) . . ?
C3 C2 H2 126.3 . . ?
C8 C11 H11 119.6 . . ?
C12 C11 C8 120.86(17) . . ?
C12 C11 H11 119.6 . . ?

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
C4 N2 C1 N1 -177.85(17) . . . . ?
C4 N2 C2 C3 177.91(18) . . . . ?
N2 C1 N1 C5 178.83(14) . . . . ?
N2 C1 N1 C3 -0.01(19) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C5 N1 C3 C2 -178.69(15) . . . . ?
C5 C10 C20 C19 -179.34(15) . . . . ?
C5 C10 C9 C8 0.6(2) . . . . ?
C5 C10 C9 C14 -178.92(13) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C14 C9 C8 178.47(14) . . . . ?
C15 C14 C9 C10 -2.1(2) . . . . ?
C6 C5 N1 C1 108.61(19) . . . . ?
C6 C5 N1 C3 -72.8(2) . . . . ?
C6 C5 C10 C20 175.65(15) . . . . ?
C6 C5 C10 C9 -3.2(2) . . . . ?
C1 N2 C2 C3 0.2(2) . . . . ?
C1 N1 C3 C2 0.11(19) . . . . ?
N1 C5 C6 C7 -177.38(14) . . . . ?
N1 C5 C10 C20 -4.2(2) . . . . ?
N1 C5 C10 C9 176.97(13) . . . . ?
N1 C3 C2 N2 -0.17(19) . . . . ?
C10 C5 C6 C7 2.8(2) . . . . ?
C10 C5 N1 C1 -71.5(2) . . . . ?
C10 C5 N1 C3 107.08(18) . . . . ?
C10 C20 C19 C15 -1.3(2) . . . . ?
C20 C10 C9 C8 -178.32(14) . . . . ?
C20 C10 C9 C14 2.2(2) . . . . ?
C19 C15 C16 C17 177.58(17) . . . . ?
C19 C15 C14 C13 -177.98(15) . . . . ?
C19 C15 C14 C9 0.3(2) . . . . ?
C16 C15 C19 C20 -177.15(16) . . . . ?
C16 C15 C14 C13 0.7(2) . . . . ?
C16 C15 C14 C9 178.92(14) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C17 C18 C13 C14 -1.0(2) . . . . ?
C17 C18 C13 C12 -179.47(16) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?
C18 C13 C14 C9 -177.92(14) . . . . ?
C18 C13 C12 C11 -179.41(16) . . . . ?
C13 C14 C9 C8 -3.3(2) . . . . ?
C13 C14 C9 C10 176.20(14) . . . . ?
C13 C12 C11 C8 -2.1(3) . . . . ?
C14 C15 C19 C20 1.4(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C14 C13 C12 C11 2.1(2) . . . . ?
C9 C8 C7 C6 -2.9(2) . . . . ?
C9 C8 C11 C12 -0.7(2) . . . . ?
C9 C10 C20 C19 -0.5(2) . . . . ?
C7 C8 C9 C10 2.4(2) . . . . ?
C7 C8 C9 C14 -178.11(14) . . . . ?
C7 C8 C11 C12 -179.17(15) . . . . ?
C12 C13 C14 C15 178.84(14) . . . . ?
C12 C13 C14 C9 0.6(2) . . . . ?
C2 N2 C1 N1 -0.1(2) . . . . ?
C11 C8 C9 C10 -176.14(14) . . . . ?
C11 C8 C9 C14 3.3(2) . . . . ?
C11 C8 C7 C6 175.60(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop with grease'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_1411cd49_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1058691'
_audit_update_record             
;
2015-04-09 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
#Added by publCIF


_publcif_datablock.id            {f3b9cbf9-bde3-4536-90f6-5c511b720a68}


_symmetry_space_group_name_hall  '-P 1'
#Added by publCIF



_audit_creation_date             2015-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C24 H17 N2, C2 H3 N'
_chemical_formula_sum            'C26 H20 B F4 N3'
_chemical_formula_weight         461.26
_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'
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'

_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                   8.5758(6)
_cell_length_b                   10.4878(7)
_cell_length_c                   12.8368(8)
_cell_angle_alpha                75.320(2)
_cell_angle_beta                 78.092(2)
_cell_angle_gamma                74.019(2)
_cell_volume                     1062.06(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.575
_cell_measurement_theta_min      2.788
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0527 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.9706.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            52383
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         2.788
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4020
_reflns_number_total             4913
_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 (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.5707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1019
_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:
 C1(H1), C20(H20), C4(H4), C24(H24), C15(H15), C7(H7), C13(H13), C14(H14),
 C23(H23), C6(H6), C21(H21), C16(H16), C22(H22), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C26(H26A,H26B,H26C)
;
_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
F2 F 0.20158(11) 0.39503(9) 1.12139(8) 0.0357(2) Uani 1 1 d . . . . .
F4 F 0.47042(12) 0.38396(10) 1.11741(8) 0.0355(2) Uani 1 1 d . . . . .
F1 F 0.37777(11) 0.19041(9) 1.15842(8) 0.0336(2) Uani 1 1 d . . . . .
F3 F 0.39247(12) 0.31789(11) 0.98618(7) 0.0375(2) Uani 1 1 d . . . . .
N1 N 0.82688(13) 0.22575(10) 0.83263(8) 0.0147(2) Uani 1 1 d . . . . .
N2 N 0.87620(13) 0.27841(11) 0.97487(8) 0.0158(2) Uani 1 1 d . . . . .
C11 C 0.68981(14) 0.31605(12) 0.55916(10) 0.0131(2) Uani 1 1 d . . . . .
C10 C 0.75259(14) 0.32851(12) 0.64976(9) 0.0130(2) Uani 1 1 d . . . . .
C18 C 0.69183(14) 0.41815(12) 0.46161(10) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.98315(15) 0.14827(12) 0.85237(10) 0.0144(2) Uani 1 1 d . . . . .
C19 C 0.63059(15) 0.40633(13) 0.37051(10) 0.0152(2) Uani 1 1 d . . . . .
C2 C 1.01334(15) 0.18137(12) 0.94340(10) 0.0149(2) Uani 1 1 d . . . . .
C12 C 0.62630(15) 0.20245(13) 0.56488(10) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.76801(16) 0.30202(13) 0.90767(10) 0.0163(2) Uani 1 1 d . . . . .
H1 H 0.6639 0.3641 0.9122 0.020 Uiso 1 1 calc R . . . .
N3 N 1.13161(19) 0.10012(14) 0.53014(11) 0.0356(3) Uani 1 1 d . . . . .
C17 C 0.75462(15) 0.53189(13) 0.45527(10) 0.0155(2) Uani 1 1 d . . . . .
C9 C 0.75004(15) 0.22444(12) 0.74281(10) 0.0144(2) Uani 1 1 d . . . . .
C20 C 0.63518(15) 0.50785(13) 0.27562(10) 0.0176(3) Uani 1 1 d . . . . .
H20 H 0.5940 0.5011 0.2145 0.021 Uiso 1 1 calc R . . . .
C4 C 1.09723(16) 0.05595(13) 0.79743(10) 0.0169(3) Uani 1 1 d . . . . .
H4 H 1.0768 0.0349 0.7345 0.020 Uiso 1 1 calc R . . . .
C24 C 0.56506(17) 0.19341(13) 0.47144(11) 0.0194(3) Uani 1 1 d . . . . .
H24 H 0.5223 0.1178 0.4747 0.023 Uiso 1 1 calc R . . . .
C15 C 0.81365(15) 0.44554(13) 0.64180(10) 0.0160(2) Uani 1 1 d . . . . .
H15 H 0.8544 0.4553 0.7021 0.019 Uiso 1 1 calc R . . . .
C7 C 1.15955(16) 0.12179(13) 0.98614(10) 0.0177(3) Uani 1 1 d . . . . .
H7 H 1.1803 0.1441 1.0485 0.021 Uiso 1 1 calc R . . . .
C13 C 0.62385(16) 0.10337(13) 0.66149(11) 0.0183(3) Uani 1 1 d . . . . .
H13 H 0.5794 0.0281 0.6666 0.022 Uiso 1 1 calc R . . . .
C14 C 0.68575(16) 0.11427(13) 0.74962(10) 0.0173(3) Uani 1 1 d . . . . .
H14 H 0.6842 0.0464 0.8146 0.021 Uiso 1 1 calc R . . . .
C23 C 0.56704(16) 0.29028(13) 0.37898(10) 0.0187(3) Uani 1 1 d . . . . .
H23 H 0.5257 0.2814 0.3186 0.022 Uiso 1 1 calc R . . . .
C6 C 1.27265(16) 0.02853(13) 0.93286(11) 0.0200(3) Uani 1 1 d . . . . .
H6 H 1.3736 -0.0151 0.9597 0.024 Uiso 1 1 calc R . . . .
C21 C 0.69881(16) 0.61784(14) 0.26963(10) 0.0198(3) Uani 1 1 d . . . . .
H21 H 0.7024 0.6849 0.2042 0.024 Uiso 1 1 calc R . . . .
C16 C 0.81363(16) 0.54216(13) 0.54896(10) 0.0179(3) Uani 1 1 d . . . . .
H16 H 0.8539 0.6191 0.5458 0.021 Uiso 1 1 calc R . . . .
C22 C 0.75734(16) 0.63082(14) 0.35854(11) 0.0194(3) Uani 1 1 d . . . . .
H22 H 0.7995 0.7072 0.3539 0.023 Uiso 1 1 calc R . . . .
C5 C 1.24261(16) -0.00362(13) 0.84002(11) 0.0201(3) Uani 1 1 d . . . . .
H5 H 1.3241 -0.0679 0.8056 0.024 Uiso 1 1 calc R . . . .
C8 C 0.85615(18) 0.34287(14) 1.06714(11) 0.0210(3) Uani 1 1 d . . . . .
H8A H 0.8378 0.2775 1.1354 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.7619 0.4211 1.0627 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.9554 0.3731 1.0650 0.031 Uiso 1 1 calc GR . . . .
C25 C 1.08565(18) 0.14098(14) 0.44788(11) 0.0237(3) Uani 1 1 d . . . . .
C26 C 1.02800(19) 0.19433(16) 0.34304(12) 0.0268(3) Uani 1 1 d . . . . .
H26A H 1.1115 0.1580 0.2865 0.040 Uiso 1 1 calc GR . . . .
H26B H 1.0074 0.2935 0.3264 0.040 Uiso 1 1 calc GR . . . .
H26C H 0.9263 0.1675 0.3455 0.040 Uiso 1 1 calc GR . . . .
B B 0.36084(19) 0.32143(15) 1.09614(12) 0.0195(3) 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
F2 B 1.3891(18) . ?
F4 B 1.3869(17) . ?
F1 B 1.3892(17) . ?
F3 B 1.3895(17) . ?
N1 C3 1.3988(16) . ?
N1 C1 1.3379(16) . ?
N1 C9 1.4458(15) . ?
N2 C2 1.3911(16) . ?
N2 C1 1.3273(16) . ?
N2 C8 1.4654(16) . ?
C11 C10 1.4260(16) . ?
C11 C18 1.4272(16) . ?
C11 C12 1.4206(17) . ?
C10 C9 1.4001(16) . ?
C10 C15 1.4350(17) . ?
C18 C19 1.4217(17) . ?
C18 C17 1.4163(17) . ?
C3 C2 1.3902(17) . ?
C3 C4 1.3898(18) . ?
C19 C20 1.4018(17) . ?
C19 C23 1.4366(18) . ?
C2 C7 1.3937(18) . ?
C12 C24 1.4381(17) . ?
C12 C13 1.4023(17) . ?
C1 H1 0.9500 . ?
N3 C25 1.142(2) . ?
C17 C16 1.4356(17) . ?
C17 C22 1.4026(17) . ?
C9 C14 1.3879(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3867(18) . ?
C24 H24 0.9500 . ?
C24 C23 1.3533(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3546(18) . ?
C7 H7 0.9500 . ?
C7 C6 1.3814(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3862(18) . ?
C14 H14 0.9500 . ?
C23 H23 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.4066(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.3877(19) . ?
C16 H16 0.9500 . ?
C22 H22 0.9500 . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C25 C26 1.452(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C3 N1 C9 124.26(10) . . ?
C1 N1 C3 108.10(10) . . ?
C1 N1 C9 127.60(11) . . ?
C2 N2 C8 125.19(11) . . ?
C1 N2 C2 108.62(10) . . ?
C1 N2 C8 126.20(11) . . ?
C10 C11 C18 119.71(11) . . ?
C12 C11 C10 120.60(11) . . ?
C12 C11 C18 119.70(11) . . ?
C11 C10 C15 119.15(11) . . ?
C9 C10 C11 117.36(11) . . ?
C9 C10 C15 123.49(11) . . ?
C19 C18 C11 120.20(11) . . ?
C17 C18 C11 120.07(11) . . ?
C17 C18 C19 119.73(11) . . ?
C2 C3 N1 106.41(11) . . ?
C4 C3 N1 131.26(11) . . ?
C4 C3 C2 122.32(11) . . ?
C18 C19 C23 118.73(11) . . ?
C20 C19 C18 118.85(12) . . ?
C20 C19 C23 122.42(11) . . ?
N2 C2 C7 131.56(12) . . ?
C3 C2 N2 106.71(11) . . ?
C3 C2 C7 121.73(12) . . ?
C11 C12 C24 118.81(11) . . ?
C13 C12 C11 119.13(11) . . ?
C13 C12 C24 122.06(12) . . ?
N1 C1 H1 124.9 . . ?
N2 C1 N1 110.16(11) . . ?
N2 C1 H1 124.9 . . ?
C18 C17 C16 118.55(11) . . ?
C22 C17 C18 119.48(11) . . ?
C22 C17 C16 121.97(12) . . ?
C10 C9 N1 119.35(11) . . ?
C14 C9 N1 118.15(11) . . ?
C14 C9 C10 122.36(11) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.04(12) . . ?
C21 C20 H20 119.5 . . ?
C3 C4 H4 122.0 . . ?
C5 C4 C3 116.00(12) . . ?
C5 C4 H4 122.0 . . ?
C12 C24 H24 119.3 . . ?
C23 C24 C12 121.44(12) . . ?
C23 C24 H24 119.3 . . ?
C10 C15 H15 119.8 . . ?
C16 C15 C10 120.47(11) . . ?
C16 C15 H15 119.8 . . ?
C2 C7 H7 121.9 . . ?
C6 C7 C2 116.29(12) . . ?
C6 C7 H7 121.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.60(12) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.93(11) . . ?
C13 C14 H14 120.0 . . ?
C19 C23 H23 119.4 . . ?
C24 C23 C19 121.12(11) . . ?
C24 C23 H23 119.4 . . ?
C7 C6 H6 119.1 . . ?
C7 C6 C5 121.88(12) . . ?
C5 C6 H6 119.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.47(12) . . ?
C22 C21 H21 119.8 . . ?
C17 C16 H16 119.0 . . ?
C15 C16 C17 122.02(12) . . ?
C15 C16 H16 119.0 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.43(12) . . ?
C21 C22 H22 119.8 . . ?
C4 C5 C6 121.78(12) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C25 C26 179.32(16) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F2 B F1 108.88(12) . . ?
F2 B F3 109.62(12) . . ?
F4 B F2 109.48(12) . . ?
F4 B F1 110.50(12) . . ?
F4 B F3 108.49(12) . . ?
F1 B F3 109.86(12) . . ?

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
N1 C3 C2 N2 -0.72(13) . . . . ?
N1 C3 C2 C7 179.83(11) . . . . ?
N1 C3 C4 C5 179.99(12) . . . . ?
N1 C9 C14 C13 -174.43(11) . . . . ?
N2 C2 C7 C6 -179.12(12) . . . . ?
C11 C10 C9 N1 173.95(10) . . . . ?
C11 C10 C9 C14 -1.64(18) . . . . ?
C11 C10 C15 C16 -0.83(18) . . . . ?
C11 C18 C19 C20 -179.61(11) . . . . ?
C11 C18 C19 C23 0.07(17) . . . . ?
C11 C18 C17 C16 -0.69(17) . . . . ?
C11 C18 C17 C22 179.38(11) . . . . ?
C11 C12 C24 C23 0.08(19) . . . . ?
C11 C12 C13 C14 -1.40(19) . . . . ?
C10 C11 C18 C19 179.57(11) . . . . ?
C10 C11 C18 C17 -0.56(17) . . . . ?
C10 C11 C12 C24 -179.64(11) . . . . ?
C10 C11 C12 C13 0.93(18) . . . . ?
C10 C9 C14 C13 1.21(19) . . . . ?
C10 C15 C16 C17 -0.46(19) . . . . ?
C18 C11 C10 C9 -179.01(11) . . . . ?
C18 C11 C10 C15 1.33(17) . . . . ?
C18 C11 C12 C24 -0.07(18) . . . . ?
C18 C11 C12 C13 -179.51(11) . . . . ?
C18 C19 C20 C21 0.34(18) . . . . ?
C18 C19 C23 C24 -0.07(19) . . . . ?
C18 C17 C16 C15 1.23(19) . . . . ?
C18 C17 C22 C21 0.12(19) . . . . ?
C3 N1 C1 N2 -0.18(14) . . . . ?
C3 N1 C9 C10 -99.60(14) . . . . ?
C3 N1 C9 C14 76.17(16) . . . . ?
C3 C2 C7 C6 0.18(18) . . . . ?
C3 C4 C5 C6 -0.42(19) . . . . ?
C19 C18 C17 C16 179.18(11) . . . . ?
C19 C18 C17 C22 -0.75(18) . . . . ?
C19 C20 C21 C22 -0.99(19) . . . . ?
C2 N2 C1 N1 -0.28(14) . . . . ?
C2 C3 C4 C5 1.19(18) . . . . ?
C2 C7 C6 C5 0.57(18) . . . . ?
C12 C11 C10 C9 0.55(17) . . . . ?
C12 C11 C10 C15 -179.11(11) . . . . ?
C12 C11 C18 C19 0.00(17) . . . . ?
C12 C11 C18 C17 179.87(11) . . . . ?
C12 C24 C23 C19 0.0(2) . . . . ?
C12 C13 C14 C9 0.37(19) . . . . ?
C1 N1 C3 C2 0.56(13) . . . . ?
C1 N1 C3 C4 -178.38(13) . . . . ?
C1 N1 C9 C10 77.61(16) . . . . ?
C1 N1 C9 C14 -106.62(15) . . . . ?
C1 N2 C2 C3 0.62(14) . . . . ?
C1 N2 C2 C7 -179.99(13) . . . . ?
C17 C18 C19 C20 0.52(17) . . . . ?
C17 C18 C19 C23 -179.80(11) . . . . ?
C9 N1 C3 C2 178.24(11) . . . . ?
C9 N1 C3 C4 -0.7(2) . . . . ?
C9 N1 C1 N2 -177.76(11) . . . . ?
C9 C10 C15 C16 179.53(12) . . . . ?
C20 C19 C23 C24 179.60(12) . . . . ?
C20 C21 C22 C17 0.7(2) . . . . ?
C4 C3 C2 N2 178.35(11) . . . . ?
C4 C3 C2 C7 -1.11(19) . . . . ?
C24 C12 C13 C14 179.19(12) . . . . ?
C15 C10 C9 N1 -6.41(18) . . . . ?
C15 C10 C9 C14 178.00(12) . . . . ?
C7 C6 C5 C4 -0.5(2) . . . . ?
C13 C12 C24 C23 179.49(13) . . . . ?
C23 C19 C20 C21 -179.32(12) . . . . ?
C16 C17 C22 C21 -179.80(12) . . . . ?
C22 C17 C16 C15 -178.85(12) . . . . ?
C8 N2 C2 C3 -179.44(11) . . . . ?
C8 N2 C2 C7 -0.1(2) . . . . ?
C8 N2 C1 N1 179.79(11) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop with grease'
_olex2_submission_special_instructions 'No special instructions were received'
