# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_2
_database_code_depnum_ccdc_archive 'CCDC 1823667'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C32 H23 N2'
_chemical_formula_sum            'C32 H23 B F4 N2'
_chemical_formula_weight         522.33
_chemical_absolute_configuration ad
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9397(16)
_cell_length_b                   12.0611(19)
_cell_length_c                   21.140(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2534.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1886
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.38
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0491 before and 0.0443 after correction. The Ratio of minimum to maximum transmission is 0.9320. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10881
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.359
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      150.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3221
_reflns_number_total             4592
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      0.989
_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)+(0.0326P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C15(H15), C12(H12), C9(H9), C11(H11), C18(H18), C22(H22), C28(H28),
 C17(H17), C32(H32), C10(H10), C7(H7), C30(H30), C29(H29), C5(H5), C26(H26),
 C6(H6), C16(H16), C31(H31), C23(H23), C25(H25), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.7205(2) 0.37736(17) 0.61833(10) 0.0449(6) Uani 1 1 d . . . . .
F2 F 0.4996(2) 0.34538(19) 0.60225(11) 0.0519(7) Uani 1 1 d . . . . .
F4 F 0.6328(3) 0.3890(2) 0.52004(10) 0.0547(7) Uani 1 1 d . . . . .
F3 F 0.5811(3) 0.51812(17) 0.59290(11) 0.0624(8) Uani 1 1 d . . . . .
N2 N 0.4393(3) 0.3978(2) 0.37733(13) 0.0211(7) Uani 1 1 d . . . . .
N1 N 0.3929(3) 0.3394(2) 0.42211(13) 0.0247(7) Uani 1 1 d . . . . .
C2 C 0.5894(3) 0.2566(3) 0.38984(15) 0.0215(8) Uani 1 1 d . . . . .
C3 C 0.4812(4) 0.2509(3) 0.43151(16) 0.0221(8) Uani 1 1 d . . . . .
C8 C 0.6766(3) 0.4443(3) 0.34563(16) 0.0210(8) Uani 1 1 d . . . . .
C13 C 0.7039(3) 0.4719(3) 0.28270(16) 0.0200(8) Uani 1 1 d . . . . .
C14 C 0.6199(3) 0.4040(3) 0.24076(16) 0.0205(8) Uani 1 1 d . . . . .
C1 C 0.5686(3) 0.3545(3) 0.34752(15) 0.0200(8) Uani 1 1 d . . . . .
C21 C 0.3186(4) 0.5736(3) 0.40359(16) 0.0227(9) Uani 1 1 d . . . . .
C19 C 0.5423(3) 0.3323(3) 0.27715(16) 0.0209(8) Uani 1 1 d . . . . .
C27 C 0.2540(4) 0.4540(3) 0.30764(16) 0.0238(9) Uani 1 1 d . . . . .
C20 C 0.3657(4) 0.4947(3) 0.35145(15) 0.0236(8) Uani 1 1 d . . . . .
H20 H 0.4308 0.5369 0.3246 0.028 Uiso 1 1 calc R . . . .
C4 C 0.4690(4) 0.1700(3) 0.47817(17) 0.0292(9) Uani 1 1 d . . . . .
H4 H 0.3943 0.1673 0.5062 0.035 Uiso 1 1 calc R . . . .
C15 C 0.6095(4) 0.4015(3) 0.17519(16) 0.0279(9) Uani 1 1 d . . . . .
H15 H 0.6619 0.4496 0.1495 0.033 Uiso 1 1 calc R . . . .
C12 C 0.8010(4) 0.5512(3) 0.26942(17) 0.0253(9) Uani 1 1 d . . . . .
H12 H 0.8198 0.5721 0.2270 0.030 Uiso 1 1 calc R . . . .
C9 C 0.7452(4) 0.4918(3) 0.39543(16) 0.0245(9) Uani 1 1 d . . . . .
H9 H 0.7260 0.4716 0.4379 0.029 Uiso 1 1 calc R . . . .
C11 C 0.8703(4) 0.5995(3) 0.31948(17) 0.0282(9) Uani 1 1 d . . . . .
H11 H 0.9373 0.6537 0.3110 0.034 Uiso 1 1 calc R . . . .
C18 C 0.4543(4) 0.2570(3) 0.25051(17) 0.0264(9) Uani 1 1 d . . . . .
H18 H 0.4021 0.2085 0.2760 0.032 Uiso 1 1 calc R . . . .
C22 C 0.3819(4) 0.5821(3) 0.46158(17) 0.0283(9) Uani 1 1 d . . . . .
H22 H 0.4553 0.5346 0.4714 0.034 Uiso 1 1 calc R . . . .
C28 C 0.1569(4) 0.3801(3) 0.32866(17) 0.0266(9) Uani 1 1 d . . . . .
H28 H 0.1595 0.3530 0.3708 0.032 Uiso 1 1 calc R . . . .
C17 C 0.4450(4) 0.2549(3) 0.18497(17) 0.0304(9) Uani 1 1 d . . . . .
H17 H 0.3861 0.2036 0.1651 0.036 Uiso 1 1 calc R . . . .
C32 C 0.2495(4) 0.4938(3) 0.24638(17) 0.0306(9) Uani 1 1 d . . . . .
H32 H 0.3164 0.5439 0.2318 0.037 Uiso 1 1 calc R . . . .
C10 C 0.8432(3) 0.5698(3) 0.38158(18) 0.0273(9) Uani 1 1 d . . . . .
H10 H 0.8923 0.6034 0.4150 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6928(4) 0.1813(3) 0.39360(17) 0.0280(9) Uani 1 1 d . . . . .
H7 H 0.7679 0.1845 0.3659 0.034 Uiso 1 1 calc R . . . .
C30 C 0.0503(4) 0.3865(3) 0.22694(18) 0.0336(10) Uani 1 1 d . . . . .
H30 H -0.0198 0.3637 0.1994 0.040 Uiso 1 1 calc R . . . .
C29 C 0.0565(4) 0.3461(3) 0.28789(18) 0.0310(9) Uani 1 1 d . . . . .
H29 H -0.0090 0.2944 0.3020 0.037 Uiso 1 1 calc R . . . .
C5 C 0.5727(4) 0.0942(3) 0.48101(18) 0.0360(10) Uani 1 1 d . . . . .
H5 H 0.5694 0.0366 0.5116 0.043 Uiso 1 1 calc R . . . .
C26 C 0.2138(4) 0.6457(3) 0.38955(19) 0.0335(10) Uani 1 1 d . . . . .
H26 H 0.1697 0.6407 0.3498 0.040 Uiso 1 1 calc R . . . .
C6 C 0.6821(4) 0.1001(3) 0.43999(17) 0.0337(10) Uani 1 1 d . . . . .
H6 H 0.7519 0.0468 0.4439 0.040 Uiso 1 1 calc R . . . .
C16 C 0.5204(4) 0.3266(3) 0.14843(18) 0.0315(10) Uani 1 1 d . . . . .
H16 H 0.5110 0.3246 0.1037 0.038 Uiso 1 1 calc R . . . .
C31 C 0.1468(4) 0.4603(3) 0.20635(18) 0.0340(10) Uani 1 1 d . . . . .
H31 H 0.1428 0.4884 0.1644 0.041 Uiso 1 1 calc R . . . .
C23 C 0.3386(4) 0.6601(3) 0.50577(18) 0.0350(10) Uani 1 1 d . . . . .
H23 H 0.3809 0.6645 0.5460 0.042 Uiso 1 1 calc R . . . .
C25 C 0.1730(4) 0.7247(3) 0.43281(19) 0.0401(11) Uani 1 1 d . . . . .
H25 H 0.1027 0.7747 0.4224 0.048 Uiso 1 1 calc R . . . .
C24 C 0.2344(4) 0.7308(3) 0.4910(2) 0.0405(11) Uani 1 1 d . . . . .
H24 H 0.2048 0.7840 0.5211 0.049 Uiso 1 1 calc R . . . .
B1 B 0.6090(5) 0.4075(3) 0.5835(2) 0.0295(11) 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
F1 B1 1.380(5) . ?
F2 B1 1.379(5) . ?
F4 B1 1.379(5) . ?
F3 B1 1.377(5) . ?
N2 N1 1.267(3) . ?
N2 C1 1.523(4) . ?
N2 C20 1.484(4) . ?
N1 C3 1.396(4) . ?
C2 C3 1.392(5) . ?
C2 C1 1.496(4) . ?
C2 C7 1.374(4) . ?
C3 C4 1.393(4) . ?
C8 C13 1.398(5) . ?
C8 C1 1.525(4) . ?
C8 C9 1.379(5) . ?
C13 C14 1.468(4) . ?
C13 C12 1.388(4) . ?
C14 C19 1.391(4) . ?
C14 C15 1.390(4) . ?
C1 C19 1.534(4) . ?
C21 C20 1.530(4) . ?
C21 C22 1.382(5) . ?
C21 C26 1.389(5) . ?
C19 C18 1.381(4) . ?
C27 C20 1.527(5) . ?
C27 C28 1.386(5) . ?
C27 C32 1.382(4) . ?
C20 H20 1.0000 . ?
C4 H4 0.9500 . ?
C4 C5 1.380(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.390(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.387(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.389(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.394(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.381(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.381(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.387(5) . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.389(5) . ?
C30 H30 0.9500 . ?
C30 C29 1.379(5) . ?
C30 C31 1.378(5) . ?
C29 H29 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.393(5) . ?
C26 H26 0.9500 . ?
C26 C25 1.381(5) . ?
C6 H6 0.9500 . ?
C16 H16 0.9500 . ?
C31 H31 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.378(5) . ?
C25 H25 0.9500 . ?
C25 C24 1.375(5) . ?
C24 H24 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
N1 N2 C1 115.2(3) . . ?
N1 N2 C20 122.3(3) . . ?
C20 N2 C1 122.3(3) . . ?
N2 N1 C3 107.6(3) . . ?
C3 C2 C1 108.1(3) . . ?
C7 C2 C3 120.6(3) . . ?
C7 C2 C1 131.3(3) . . ?
C2 C3 N1 111.0(3) . . ?
C2 C3 C4 123.4(3) . . ?
C4 C3 N1 125.5(3) . . ?
C13 C8 C1 109.3(3) . . ?
C9 C8 C13 122.1(3) . . ?
C9 C8 C1 128.5(3) . . ?
C8 C13 C14 109.3(3) . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 C14 131.2(3) . . ?
C19 C14 C13 109.2(3) . . ?
C15 C14 C13 131.1(3) . . ?
C15 C14 C19 119.8(3) . . ?
N2 C1 C8 111.2(2) . . ?
N2 C1 C19 108.5(3) . . ?
C2 C1 N2 98.1(3) . . ?
C2 C1 C8 118.6(3) . . ?
C2 C1 C19 117.7(3) . . ?
C8 C1 C19 102.6(3) . . ?
C22 C21 C20 123.1(3) . . ?
C22 C21 C26 119.0(3) . . ?
C26 C21 C20 117.7(3) . . ?
C14 C19 C1 109.5(3) . . ?
C18 C19 C14 122.3(3) . . ?
C18 C19 C1 128.2(3) . . ?
C28 C27 C20 121.2(3) . . ?
C32 C27 C20 118.7(3) . . ?
C32 C27 C28 120.1(3) . . ?
N2 C20 C21 112.1(3) . . ?
N2 C20 C27 109.2(2) . . ?
N2 C20 H20 106.9 . . ?
C21 C20 H20 106.9 . . ?
C27 C20 C21 114.5(3) . . ?
C27 C20 H20 106.9 . . ?
C3 C4 H4 122.3 . . ?
C5 C4 C3 115.5(3) . . ?
C5 C4 H4 122.3 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H15 121.0 . . ?
C13 C12 H12 120.7 . . ?
C13 C12 C11 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 117.9(3) . . ?
C10 C9 H9 121.0 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C19 C18 H18 121.3 . . ?
C19 C18 C17 117.5(3) . . ?
C17 C18 H18 121.3 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(4) . . ?
C23 C22 H22 119.9 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(3) . . ?
C29 C28 H28 120.2 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C27 C32 H32 120.2 . . ?
C27 C32 C31 119.6(4) . . ?
C31 C32 H32 120.2 . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C2 C7 H7 121.7 . . ?
C2 C7 C6 116.7(3) . . ?
C6 C7 H7 121.7 . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C31 C30 C29 119.5(4) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.7(4) . . ?
C30 C29 H29 119.6 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.7(4) . . ?
C25 C26 H26 119.7 . . ?
C7 C6 C5 122.4(4) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.8(4) . . ?
C17 C16 H16 119.1 . . ?
C32 C31 H31 119.7 . . ?
C30 C31 C32 120.5(4) . . ?
C30 C31 H31 119.7 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.1 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 120.0(4) . . ?
C24 C25 H25 120.0 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(4) . . ?
C25 C24 H24 119.9 . . ?
F2 B1 F1 109.7(3) . . ?
F2 B1 F4 109.1(3) . . ?
F4 B1 F1 109.8(4) . . ?
F3 B1 F1 109.8(4) . . ?
F3 B1 F2 109.0(4) . . ?
F3 B1 F4 109.4(3) . . ?

_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_6
_database_code_depnum_ccdc_archive 'CCDC 1823671'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C33 H25 N2'
_chemical_formula_sum            'C34 H25 F3 N2 O3 S'
_chemical_formula_weight         598.62
_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'
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'
O O 0.0106 0.0060 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.4490(6)
_cell_length_b                   17.2112(9)
_cell_length_c                   19.6802(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.062(3)
_cell_angle_gamma                90
_cell_volume                     2861.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2322
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.86
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0485 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.9162.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17762
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.686
_diffrn_ambient_temperature      149.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3271
_reflns_number_total             5831
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.606
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.004
_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)+(0.0626P)²+1.5114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1525
_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:
 C4(H4), C12(H12), C7(H7), C22(H22), C5(H5), C10(H10), C11(H11), C6(H6),
 C9(H9), C28(H28), C17(H17), C18(H18), C15(H15), C32(H32), C26(H26), C29(H29),
 C16(H16), C30(H30), C23(H23), C25(H25), C24(H24), C31(H31)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_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
S1 S 0.11002(11) 0.36205(5) 0.81662(5) 0.0367(3) Uani 1 1 d . . . . .
F2 F 0.3108(3) 0.46132(12) 0.76711(12) 0.0568(6) Uani 1 1 d . . . . .
N2 N 0.5592(3) 0.29743(13) 0.68345(11) 0.0168(5) Uani 1 1 d . . . . .
O2 O 0.2381(3) 0.30799(13) 0.82449(13) 0.0474(7) Uani 1 1 d . . . . .
N1 N 0.6486(3) 0.35398(13) 0.71693(12) 0.0212(6) Uani 1 1 d . . . . .
F3 F 0.2909(3) 0.46465(14) 0.87613(13) 0.0792(8) Uani 1 1 d . . . . .
O3 O 0.0293(3) 0.35958(16) 0.75213(13) 0.0531(7) Uani 1 1 d . . . . .
O1 O 0.0078(3) 0.36626(18) 0.87431(14) 0.0666(9) Uani 1 1 d . . . . .
F1 F 0.1081(3) 0.51386(14) 0.81172(17) 0.0983(11) Uani 1 1 d . . . . .
C8 C 0.3605(3) 0.32667(16) 0.58331(14) 0.0182(6) Uani 1 1 d . . . . .
C13 C 0.3395(4) 0.28082(16) 0.52491(14) 0.0207(7) Uani 1 1 d . . . . .
C3 C 0.6809(3) 0.41363(16) 0.67073(15) 0.0192(7) Uani 1 1 d . . . . .
C2 C 0.6192(3) 0.39698(16) 0.60739(15) 0.0187(7) Uani 1 1 d . . . . .
C1 C 0.5309(3) 0.32034(15) 0.60836(14) 0.0173(6) Uani 1 1 d . . . . .
C20 C 0.5338(3) 0.22747(16) 0.70839(15) 0.0198(7) Uani 1 1 d . . . . .
C19 C 0.6004(4) 0.25976(15) 0.56170(14) 0.0193(7) Uani 1 1 d . . . . .
C14 C 0.4884(4) 0.23919(16) 0.51189(14) 0.0217(7) Uani 1 1 d . . . . .
C4 C 0.7650(4) 0.48219(17) 0.68346(17) 0.0276(8) Uani 1 1 d . . . . .
H4 H 0.8076 0.4942 0.7272 0.033 Uiso 1 1 calc R . . . .
C12 C 0.1943(4) 0.28026(18) 0.49083(16) 0.0287(8) Uani 1 1 d . . . . .
H12 H 0.1790 0.2500 0.4509 0.034 Uiso 1 1 calc R . . . .
C7 C 0.6386(4) 0.44660(17) 0.55345(16) 0.0256(7) Uani 1 1 d . . . . .
H7 H 0.5959 0.4346 0.5097 0.031 Uiso 1 1 calc R . . . .
C27 C 0.6234(4) 0.19421(17) 0.76590(15) 0.0238(7) Uani 1 1 d . . . . .
C22 C 0.4647(4) 0.11145(17) 0.63936(16) 0.0288(8) Uani 1 1 d . . . . .
H22 H 0.5744 0.0995 0.6380 0.035 Uiso 1 1 calc R . . . .
C5 C 0.7829(4) 0.53174(17) 0.62844(18) 0.0309(8) Uani 1 1 d . . . . .
H5 H 0.8389 0.5791 0.6351 0.037 Uiso 1 1 calc R . . . .
C21 C 0.4143(4) 0.17739(16) 0.67305(15) 0.0217(7) Uani 1 1 d . . . . .
C10 C 0.0935(4) 0.36928(18) 0.57410(17) 0.0306(8) Uani 1 1 d . . . . .
H10 H 0.0074 0.3987 0.5908 0.037 Uiso 1 1 calc R . . . .
C11 C 0.0727(4) 0.32449(19) 0.51605(17) 0.0301(8) Uani 1 1 d . . . . .
H11 H -0.0273 0.3243 0.4932 0.036 Uiso 1 1 calc R . . . .
C6 C 0.7230(4) 0.51521(18) 0.56489(18) 0.0327(8) Uani 1 1 d . . . . .
H6 H 0.7389 0.5505 0.5286 0.039 Uiso 1 1 calc R . . . .
C9 C 0.2394(4) 0.37152(17) 0.60822(16) 0.0259(7) Uani 1 1 d . . . . .
H9 H 0.2549 0.4030 0.6474 0.031 Uiso 1 1 calc R . . . .
C28 C 0.7843(4) 0.21032(18) 0.77678(17) 0.0301(8) Uani 1 1 d . . . . .
H28 H 0.8355 0.2487 0.7504 0.036 Uiso 1 1 calc R . . . .
C17 C 0.7890(4) 0.17404(18) 0.51444(16) 0.0318(8) Uani 1 1 d . . . . .
H17 H 0.8914 0.1512 0.5147 0.038 Uiso 1 1 calc R . . . .
C18 C 0.7504(4) 0.22828(17) 0.56383(16) 0.0244(7) Uani 1 1 d . . . . .
H18 H 0.8252 0.2432 0.5980 0.029 Uiso 1 1 calc R . . . .
C33 C 0.6266(4) 0.36700(19) 0.78929(15) 0.0298(8) Uani 1 1 d . . . . .
H33A H 0.5313 0.3397 0.8039 0.045 Uiso 1 1 calc GR . . . .
H33B H 0.6148 0.4228 0.7978 0.045 Uiso 1 1 calc GR . . . .
H33C H 0.7188 0.3473 0.8148 0.045 Uiso 1 1 calc GR . . . .
C15 C 0.5280(4) 0.18524(18) 0.46211(16) 0.0311(8) Uani 1 1 d . . . . .
H15 H 0.4542 0.1709 0.4273 0.037 Uiso 1 1 calc R . . . .
C32 C 0.5500(4) 0.13786(19) 0.80570(16) 0.0333(8) Uani 1 1 d . . . . .
H32 H 0.4408 0.1266 0.7987 0.040 Uiso 1 1 calc R . . . .
C26 C 0.2528(4) 0.19284(18) 0.67799(16) 0.0275(8) Uani 1 1 d . . . . .
H26 H 0.2174 0.2375 0.7017 0.033 Uiso 1 1 calc R . . . .
C29 C 0.8684(4) 0.1697(2) 0.82645(18) 0.0407(9) Uani 1 1 d . . . . .
H29 H 0.9777 0.1804 0.8339 0.049 Uiso 1 1 calc R . . . .
C16 C 0.6787(4) 0.15328(18) 0.46512(17) 0.0339(8) Uani 1 1 d . . . . .
H16 H 0.7069 0.1158 0.4321 0.041 Uiso 1 1 calc R . . . .
C30 C 0.7948(5) 0.1140(2) 0.86506(18) 0.0429(10) Uani 1 1 d . . . . .
H30 H 0.8539 0.0863 0.8987 0.052 Uiso 1 1 calc R . . . .
C23 C 0.3559(4) 0.06318(19) 0.60774(18) 0.0381(9) Uani 1 1 d . . . . .
H23 H 0.3908 0.0193 0.5829 0.046 Uiso 1 1 calc R . . . .
C25 C 0.1449(4) 0.1425(2) 0.64808(19) 0.0401(9) Uani 1 1 d . . . . .
H25 H 0.0347 0.1519 0.6522 0.048 Uiso 1 1 calc R . . . .
C24 C 0.1961(5) 0.0788(2) 0.61222(19) 0.0426(10) Uani 1 1 d . . . . .
H24 H 0.1212 0.0455 0.5905 0.051 Uiso 1 1 calc R . . . .
C31 C 0.6363(5) 0.0984(2) 0.85518(17) 0.0402(9) Uani 1 1 d . . . . .
H31 H 0.5860 0.0605 0.8824 0.048 Uiso 1 1 calc R . . . .
C34 C 0.2072(5) 0.4547(2) 0.8168(2) 0.0473(10) 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
S1 O2 1.434(3) . ?
S1 O3 1.430(3) . ?
S1 O1 1.441(3) . ?
S1 C34 1.794(4) . ?
F2 C34 1.330(4) . ?
N2 N1 1.391(3) . ?
N2 C1 1.544(3) . ?
N2 C20 1.319(3) . ?
N1 C3 1.402(4) . ?
N1 C33 1.457(4) . ?
F3 C34 1.365(5) . ?
F1 C34 1.320(4) . ?
C8 C13 1.403(4) . ?
C8 C1 1.517(4) . ?
C8 C9 1.379(4) . ?
C13 C14 1.474(4) . ?
C13 C12 1.387(4) . ?
C3 C2 1.373(4) . ?
C3 C4 1.398(4) . ?
C2 C1 1.516(4) . ?
C2 C7 1.375(4) . ?
C1 C19 1.515(4) . ?
C20 C27 1.466(4) . ?
C20 C21 1.490(4) . ?
C19 C14 1.396(4) . ?
C19 C18 1.379(4) . ?
C14 C15 1.395(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.379(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.395(4) . ?
C27 C28 1.400(4) . ?
C27 C32 1.399(4) . ?
C22 H22 0.9500 . ?
C22 C21 1.385(4) . ?
C22 C23 1.379(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.370(5) . ?
C21 C26 1.396(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(5) . ?
C10 C9 1.393(4) . ?
C11 H11 0.9500 . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(4) . ?
C17 C16 1.380(5) . ?
C18 H18 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.387(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.383(5) . ?
C26 H26 0.9500 . ?
C26 C25 1.380(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.378(5) . ?
C16 H16 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.377(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(5) . ?
C25 H25 0.9500 . ?
C25 C24 1.378(5) . ?
C24 H24 0.9500 . ?
C31 H31 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
O2 S1 O1 114.19(17) . . ?
O2 S1 C34 103.44(17) . . ?
O3 S1 O2 115.04(17) . . ?
O3 S1 O1 114.71(18) . . ?
O3 S1 C34 103.82(18) . . ?
O1 S1 C34 103.56(19) . . ?
N1 N2 C1 110.4(2) . . ?
C20 N2 N1 123.6(2) . . ?
C20 N2 C1 124.5(2) . . ?
N2 N1 C3 108.4(2) . . ?
N2 N1 C33 119.5(2) . . ?
C3 N1 C33 123.5(2) . . ?
C13 C8 C1 109.3(2) . . ?
C9 C8 C13 121.5(3) . . ?
C9 C8 C1 129.1(3) . . ?
C8 C13 C14 108.7(2) . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 C14 131.5(3) . . ?
C2 C3 N1 111.2(2) . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 N1 127.4(3) . . ?
C3 C2 C1 110.4(2) . . ?
C3 C2 C7 121.5(3) . . ?
C7 C2 C1 128.0(3) . . ?
C8 C1 N2 117.3(2) . . ?
C2 C1 N2 99.6(2) . . ?
C2 C1 C8 113.4(2) . . ?
C19 C1 N2 110.5(2) . . ?
C19 C1 C8 103.2(2) . . ?
C19 C1 C2 113.3(2) . . ?
N2 C20 C27 123.9(3) . . ?
N2 C20 C21 117.9(2) . . ?
C27 C20 C21 118.0(2) . . ?
C14 C19 C1 109.6(3) . . ?
C18 C19 C1 128.2(3) . . ?
C18 C19 C14 122.2(3) . . ?
C19 C14 C13 108.9(3) . . ?
C15 C14 C13 131.5(3) . . ?
C15 C14 C19 119.6(3) . . ?
C3 C4 H4 121.9 . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 H4 121.9 . . ?
C13 C12 H12 120.7 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.7 . . ?
C2 C7 H7 121.0 . . ?
C2 C7 C6 118.0(3) . . ?
C6 C7 H7 121.0 . . ?
C28 C27 C20 121.8(3) . . ?
C32 C27 C20 118.4(3) . . ?
C32 C27 C28 119.4(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.1(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 H5 118.6 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 C26 119.9(3) . . ?
C26 C21 C20 120.8(3) . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C8 C9 C10 118.0(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.4(3) . . ?
C29 C28 H28 120.3 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(3) . . ?
C19 C18 C17 118.0(3) . . ?
C19 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
N1 C33 H33A 109.5 . . ?
N1 C33 H33B 109.5 . . ?
N1 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.8(3) . . ?
C16 C15 H15 121.1 . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 120.1(3) . . ?
C31 C32 H32 120.0 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.3(3) . . ?
C25 C26 H26 120.4 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C17 C16 C15 122.3(3) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C32 C31 H31 119.9 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 119.9 . . ?
F2 C34 S1 112.4(3) . . ?
F2 C34 F3 106.3(3) . . ?
F3 C34 S1 110.1(3) . . ?
F1 C34 S1 113.3(3) . . ?
F1 C34 F2 107.7(3) . . ?
F1 C34 F3 106.6(3) . . ?

_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_4
_database_code_depnum_ccdc_archive 'CCDC 1823669'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 N2'
_chemical_formula_sum            'C32 H22 N2'
_chemical_formula_weight         434.51
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.2204(15)
_cell_length_b                   10.9447(12)
_cell_length_c                   17.0214(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.336(3)
_cell_angle_gamma                90
_cell_volume                     2278.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6573
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.77
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0370 before and 0.0330 after correction.
The Ratio of minimum to maximum transmission is 0.9546.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21404
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.998
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5524
_reflns_number_total             7238
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.485
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         7238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.017
_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)+(0.0708P)²+0.9486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1448
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C32(H32), C18(H18), C9(H9), C31(H31), C28(H28), C12(H12), C10(H10), C7(H7),
 C17(H17), C15(H15), C4(H4), C30(H30), C29(H29), C6(H6), C16(H16), C11(H11),
 C5(H5), C26(H26), C25(H25), C22(H22), C24(H24), C23(H23)
;
_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
N2 N 0.22926(8) 0.27125(10) 0.63852(6) 0.0192(2) Uani 1 1 d . . . . .
N1 N 0.16298(9) 0.28977(11) 0.68189(7) 0.0262(2) Uani 1 1 d . . . . .
C19 C 0.22087(9) 0.07988(11) 0.55345(7) 0.0188(2) Uani 1 1 d . . . . .
C27 C 0.33558(9) 0.32989(11) 0.55439(8) 0.0197(2) Uani 1 1 d . . . . .
C8 C 0.38737(9) 0.11367(11) 0.66991(7) 0.0190(2) Uani 1 1 d . . . . .
C14 C 0.30431(10) 0.01868(11) 0.53787(8) 0.0205(2) Uani 1 1 d . . . . .
C20 C 0.25351(9) 0.35717(11) 0.59278(7) 0.0196(2) Uani 1 1 d . . . . .
C1 C 0.26577(9) 0.13753(11) 0.64110(7) 0.0181(2) Uani 1 1 d . . . . .
C3 C 0.15510(10) 0.17848(13) 0.71737(8) 0.0233(2) Uani 1 1 d . . . . .
C13 C 0.40731(10) 0.03794(11) 0.61093(8) 0.0202(2) Uani 1 1 d . . . . .
C32 C 0.30240(10) 0.29044(12) 0.47038(8) 0.0226(2) Uani 1 1 d . . . . .
H32 H 0.2278 0.2707 0.4393 0.027 Uiso 1 1 calc R . . . .
C2 C 0.21523(9) 0.08497(12) 0.69942(7) 0.0213(2) Uani 1 1 d . . . . .
C18 C 0.11486(10) 0.08322(13) 0.49428(8) 0.0255(3) Uani 1 1 d . . . . .
H18 H 0.0588 0.1236 0.5063 0.031 Uiso 1 1 calc R . . . .
C21 C 0.20774(10) 0.48104(12) 0.57999(8) 0.0235(2) Uani 1 1 d . . . . .
C9 C 0.47086(10) 0.15145(13) 0.74351(8) 0.0239(3) Uani 1 1 d . . . . .
H9 H 0.4564 0.2024 0.7832 0.029 Uiso 1 1 calc R . . . .
C31 C 0.37763(11) 0.27978(13) 0.43194(8) 0.0275(3) Uani 1 1 d . . . . .
H31 H 0.3543 0.2529 0.3747 0.033 Uiso 1 1 calc R . . . .
C28 C 0.44526(10) 0.35992(13) 0.59872(8) 0.0244(3) Uani 1 1 d . . . . .
H28 H 0.4685 0.3887 0.6555 0.029 Uiso 1 1 calc R . . . .
C12 C 0.51294(11) -0.00224(13) 0.62652(9) 0.0273(3) Uani 1 1 d . . . . .
H12 H 0.5273 -0.0547 0.5875 0.033 Uiso 1 1 calc R . . . .
C10 C 0.57695(10) 0.11280(14) 0.75788(8) 0.0285(3) Uani 1 1 d . . . . .
H10 H 0.6359 0.1392 0.8074 0.034 Uiso 1 1 calc R . . . .
C7 C 0.22056(11) -0.03096(14) 0.73222(8) 0.0272(3) Uani 1 1 d . . . . .
H7 H 0.2627 -0.0931 0.7201 0.033 Uiso 1 1 calc R . . . .
C17 C 0.09231(12) 0.02576(15) 0.41646(9) 0.0314(3) Uani 1 1 d . . . . .
H17 H 0.0201 0.0274 0.3745 0.038 Uiso 1 1 calc R . . . .
C15 C 0.28124(12) -0.03919(13) 0.46007(9) 0.0274(3) Uani 1 1 d . . . . .
H15 H 0.3368 -0.0813 0.4484 0.033 Uiso 1 1 calc R . . . .
C4 C 0.09595(11) 0.15452(15) 0.76870(8) 0.0297(3) Uani 1 1 d . . . . .
H4 H 0.0537 0.2165 0.7808 0.036 Uiso 1 1 calc R . . . .
C30 C 0.48676(12) 0.30816(14) 0.47680(9) 0.0308(3) Uani 1 1 d . . . . .
H30 H 0.5382 0.3003 0.4504 0.037 Uiso 1 1 calc R . . . .
C29 C 0.52075(11) 0.34809(14) 0.56034(9) 0.0299(3) Uani 1 1 d . . . . .
H29 H 0.5955 0.3673 0.5912 0.036 Uiso 1 1 calc R . . . .
C6 C 0.16203(12) -0.05458(16) 0.78405(9) 0.0326(3) Uani 1 1 d . . . . .
H6 H 0.1641 -0.1338 0.8074 0.039 Uiso 1 1 calc R . . . .
C16 C 0.17482(13) -0.03394(14) 0.39981(9) 0.0324(3) Uani 1 1 d . . . . .
H16 H 0.1582 -0.0720 0.3462 0.039 Uiso 1 1 calc R . . . .
C11 C 0.59730(11) 0.03595(15) 0.70051(9) 0.0313(3) Uani 1 1 d . . . . .
H11 H 0.6699 0.0091 0.7120 0.038 Uiso 1 1 calc R . . . .
C5 C 0.10094(11) 0.03751(16) 0.80138(8) 0.0330(3) Uani 1 1 d . . . . .
H5 H 0.0616 0.0198 0.8365 0.040 Uiso 1 1 calc R . . . .
C26 C 0.23372(12) 0.55738(13) 0.52373(9) 0.0299(3) Uani 1 1 d . . . . .
H26 H 0.2757 0.5254 0.4939 0.036 Uiso 1 1 calc R . . . .
C25 C 0.19964(13) 0.67783(14) 0.51076(11) 0.0379(3) Uani 1 1 d . . . . .
H25 H 0.2166 0.7266 0.4712 0.045 Uiso 1 1 calc R . . . .
C22 C 0.14366(12) 0.53164(14) 0.62196(12) 0.0379(4) Uani 1 1 d . . . . .
H22 H 0.1216 0.4821 0.6585 0.045 Uiso 1 1 calc R . . . .
C24 C 0.14084(14) 0.72764(15) 0.55520(14) 0.0473(5) Uani 1 1 d . . . . .
H24 H 0.1201 0.8113 0.5481 0.057 Uiso 1 1 calc R . . . .
C23 C 0.11264(15) 0.65449(17) 0.60989(16) 0.0537(5) Uani 1 1 d . . . . .
H23 H 0.0715 0.6883 0.6398 0.064 Uiso 1 1 calc R . . . .


_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
N2 N1 1.3584(14) . ?
N2 C20 1.3352(16) . ?
N2 C1 1.5365(16) . ?
N1 C3 1.3810(18) . ?
C19 C14 1.3993(17) . ?
C19 C1 1.5176(16) . ?
C19 C18 1.3810(16) . ?
C27 C20 1.4941(16) . ?
C27 C32 1.3953(17) . ?
C27 C28 1.3958(17) . ?
C8 C1 1.5145(16) . ?
C8 C13 1.4020(17) . ?
C8 C9 1.3812(17) . ?
C14 C13 1.4691(17) . ?
C14 C15 1.3932(18) . ?
C20 C21 1.4669(17) . ?
C1 C2 1.5057(16) . ?
C3 C2 1.3990(18) . ?
C3 C4 1.4011(17) . ?
C13 C12 1.3901(17) . ?
C32 H32 0.9500 . ?
C32 C31 1.3877(18) . ?
C2 C7 1.3772(19) . ?
C18 H18 0.9500 . ?
C18 C17 1.3924(19) . ?
C21 C26 1.408(2) . ?
C21 C22 1.412(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.3947(18) . ?
C31 H31 0.9500 . ?
C31 C30 1.387(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.3911(18) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.4008(19) . ?
C17 H17 0.9500 . ?
C17 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C30 H30 0.9500 . ?
C30 C29 1.389(2) . ?
C29 H29 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.392(2) . ?
C16 H16 0.9500 . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.383(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.386(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.382(3) . ?
C23 H23 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
N1 N2 C1 112.78(10) . . ?
C20 N2 N1 124.00(11) . . ?
C20 N2 C1 123.02(10) . . ?
N2 N1 C3 106.10(10) . . ?
C14 C19 C1 110.08(10) . . ?
C18 C19 C14 121.94(11) . . ?
C18 C19 C1 127.98(11) . . ?
C32 C27 C20 120.82(11) . . ?
C32 C27 C28 118.96(11) . . ?
C28 C27 C20 119.63(11) . . ?
C13 C8 C1 109.60(10) . . ?
C9 C8 C1 128.77(11) . . ?
C9 C8 C13 121.57(11) . . ?
C19 C14 C13 108.35(10) . . ?
C15 C14 C19 119.62(11) . . ?
C15 C14 C13 131.87(12) . . ?
N2 C20 C27 119.31(11) . . ?
N2 C20 C21 124.09(11) . . ?
C21 C20 C27 116.55(11) . . ?
C19 C1 N2 111.52(9) . . ?
C8 C1 N2 117.18(10) . . ?
C8 C1 C19 102.54(9) . . ?
C2 C1 N2 99.75(9) . . ?
C2 C1 C19 112.55(10) . . ?
C2 C1 C8 113.76(10) . . ?
N1 C3 C2 113.97(11) . . ?
N1 C3 C4 126.19(13) . . ?
C2 C3 C4 119.83(13) . . ?
C8 C13 C14 108.96(10) . . ?
C12 C13 C8 119.94(12) . . ?
C12 C13 C14 131.07(12) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.45(12) . . ?
C31 C32 H32 119.8 . . ?
C3 C2 C1 107.20(11) . . ?
C7 C2 C1 130.71(12) . . ?
C7 C2 C3 122.09(12) . . ?
C19 C18 H18 120.9 . . ?
C19 C18 C17 118.22(12) . . ?
C17 C18 H18 120.9 . . ?
C26 C21 C20 117.12(12) . . ?
C26 C21 C22 117.36(13) . . ?
C22 C21 C20 125.47(13) . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.17(12) . . ?
C10 C9 H9 120.9 . . ?
C32 C31 H31 119.9 . . ?
C30 C31 C32 120.23(12) . . ?
C30 C31 H31 119.9 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.50(12) . . ?
C29 C28 H28 119.8 . . ?
C13 C12 H12 120.7 . . ?
C13 C12 C11 118.62(13) . . ?
C11 C12 H12 120.7 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.69(12) . . ?
C11 C10 H10 119.7 . . ?
C2 C7 H7 121.0 . . ?
C2 C7 C6 118.03(14) . . ?
C6 C7 H7 121.0 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.35(12) . . ?
C16 C17 H17 119.8 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.45(13) . . ?
C16 C15 H15 120.8 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.03(14) . . ?
C5 C4 H4 121.0 . . ?
C31 C30 H30 120.1 . . ?
C31 C30 C29 119.89(12) . . ?
C29 C30 H30 120.1 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 119.96(12) . . ?
C30 C29 H29 120.0 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.26(14) . . ?
C5 C6 H6 119.9 . . ?
C17 C16 C15 121.39(13) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 120.99(12) . . ?
C10 C11 H11 119.5 . . ?
C4 C5 C6 121.76(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C21 C26 H26 119.2 . . ?
C25 C26 C21 121.68(14) . . ?
C25 C26 H26 119.2 . . ?
C26 C25 H25 119.9 . . ?
C26 C25 C24 120.25(16) . . ?
C24 C25 H25 119.9 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.11(16) . . ?
C23 C22 H22 119.9 . . ?
C25 C24 H24 120.3 . . ?
C23 C24 C25 119.39(15) . . ?
C23 C24 H24 120.3 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.12(17) . . ?
C24 C23 H23 119.4 . . ?

_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_3
_database_code_depnum_ccdc_archive 'CCDC 1823668'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C35 H32 N2 P), C6 H4 Cl2, 0.5(B F4)'
_chemical_formula_sum            'C23.50 H20 B0.50 Cl2 F2 N P0.50'
_chemical_formula_weight         446.19
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   10.6050(13)
_cell_length_b                   10.7240(12)
_cell_length_c                   18.967(2)
_cell_angle_alpha                89.741(4)
_cell_angle_beta                 87.191(4)
_cell_angle_gamma                87.511(4)
_cell_volume                     2152.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9492
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.9477.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31682
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.199
_diffrn_reflns_theta_min         1.075
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6785
_reflns_number_total             9505
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.628
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         9505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.012
_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)+(0.0527P)²+2.0878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1326
_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 Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C26(H26), C7(H7), C25(H25), C22(H22), C4(H4), C15(H15),
 C12(H12), C10(H10), C11(H11), C17(H17), C5(H5), C6(H6), C16(H16), C32(H32),
 C24(H24), C23(H23), C31(H31), C38(H38), C28(H28), C36(H36), C41(H41), C37(H37),
  C30(H30), C29(H29), C43(H43), C46(H46), C45(H45), C44(H44)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C33(H33A,H33B,H33C)
;
_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
P1 P 0.41857(5) 0.63836(5) 0.33457(3) 0.02055(14) Uani 1 1 d . . . . .
Cl2 Cl 0.83081(6) 0.60957(6) 0.26495(4) 0.03956(17) Uani 1 1 d . . . . .
Cl1 Cl 0.82999(8) 0.33983(7) 0.20122(4) 0.0502(2) Uani 1 1 d . . . . .
Cl3 Cl 0.49069(8) 0.79657(9) 0.79750(5) 0.0618(2) Uani 1 1 d . . . . .
Cl4 Cl 0.27768(9) 0.98852(9) 0.85753(5) 0.0647(3) Uani 1 1 d . . . . .
F1 F 0.67010(19) 0.70840(19) 0.42918(9) 0.0601(5) Uani 1 1 d . . . . .
N2 N 0.29282(17) 0.69369(16) 0.21814(9) 0.0175(4) Uani 1 1 d . . . . .
N1 N 0.29675(17) 0.61810(16) 0.28248(9) 0.0188(4) Uani 1 1 d . . . . .
F3 F 0.80958(17) 0.7497(2) 0.50960(11) 0.0758(7) Uani 1 1 d . . . . .
F4 F 0.6050(2) 0.7715(3) 0.54009(14) 0.1007(9) Uani 1 1 d . . . . .
C2 C 0.2538(2) 0.4796(2) 0.19530(11) 0.0194(4) Uani 1 1 d . . . . .
C13 C 0.4025(2) 0.6515(2) 0.04935(11) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.2562(2) 0.49633(19) 0.26735(11) 0.0188(4) Uani 1 1 d . . . . .
C14 C 0.2667(2) 0.6687(2) 0.03807(11) 0.0204(4) Uani 1 1 d . . . . .
C19 C 0.1988(2) 0.6330(2) 0.09939(11) 0.0191(4) Uani 1 1 d . . . . .
C18 C 0.0692(2) 0.6223(2) 0.09976(12) 0.0256(5) Uani 1 1 d . . . . .
H18 H 0.0238 0.5933 0.1406 0.031 Uiso 1 1 calc R . . . .
C9 C 0.5354(2) 0.5629(2) 0.13866(12) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.5448 0.5246 0.1835 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4168(2) 0.6000(2) 0.11669(11) 0.0198(4) Uani 1 1 d . . . . .
C26 C 0.2379(2) 0.9487(2) 0.31281(12) 0.0256(5) Uani 1 1 d . . . . .
H26 H 0.2969 0.9817 0.2792 0.031 Uiso 1 1 calc R . . . .
C7 C 0.2161(2) 0.3675(2) 0.16878(12) 0.0262(5) Uani 1 1 d . . . . .
H7 H 0.2123 0.3557 0.1193 0.031 Uiso 1 1 calc R . . . .
C25 C 0.2225(3) 1.0015(2) 0.37959(13) 0.0306(6) Uani 1 1 d . . . . .
H25 H 0.2733 1.0682 0.3919 0.037 Uiso 1 1 calc R . . . .
F2 F 0.6909(3) 0.5848(2) 0.51987(12) 0.1081(10) Uani 1 1 d . . . . .
C21 C 0.1675(2) 0.8479(2) 0.29468(11) 0.0217(5) Uani 1 1 d . . . . .
C22 C 0.0785(2) 0.8045(2) 0.34424(12) 0.0263(5) Uani 1 1 d . . . . .
H22 H 0.0293 0.7363 0.3326 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2218(2) 0.4042(2) 0.31548(12) 0.0248(5) Uani 1 1 d . . . . .
H4 H 0.2221 0.4176 0.3649 0.030 Uiso 1 1 calc R . . . .
C34 C 0.5144(2) 0.7553(2) 0.29657(12) 0.0254(5) Uani 1 1 d . . . . .
H34A H 0.5417 0.7315 0.2482 0.038 Uiso 1 1 calc GR . . . .
H34B H 0.5888 0.7638 0.3246 0.038 Uiso 1 1 calc GR . . . .
H34C H 0.4657 0.8350 0.2960 0.038 Uiso 1 1 calc GR . . . .
C15 C 0.2037(2) 0.7021(2) -0.02214(12) 0.0272(5) Uani 1 1 d . . . . .
H15 H 0.2492 0.7288 -0.0635 0.033 Uiso 1 1 calc R . . . .
C12 C 0.5074(2) 0.6713(2) 0.00507(12) 0.0270(5) Uani 1 1 d . . . . .
H12 H 0.4983 0.7074 -0.0403 0.032 Uiso 1 1 calc R . . . .
C10 C 0.6407(2) 0.5829(2) 0.09384(12) 0.0290(5) Uani 1 1 d . . . . .
H10 H 0.7228 0.5589 0.1083 0.035 Uiso 1 1 calc R . . . .
C11 C 0.6262(2) 0.6376(2) 0.02818(13) 0.0311(6) Uani 1 1 d . . . . .
H11 H 0.6989 0.6522 -0.0015 0.037 Uiso 1 1 calc R . . . .
C17 C 0.0068(2) 0.6550(2) 0.03900(13) 0.0307(6) Uani 1 1 d . . . . .
H17 H -0.0823 0.6493 0.0386 0.037 Uiso 1 1 calc R . . . .
C5 C 0.1868(2) 0.2916(2) 0.28794(13) 0.0291(5) Uani 1 1 d . . . . .
H5 H 0.1643 0.2259 0.3192 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1840(2) 0.2731(2) 0.21561(14) 0.0311(6) Uani 1 1 d . . . . .
H6 H 0.1600 0.1952 0.1981 0.037 Uiso 1 1 calc R . . . .
C35 C 0.3586(2) 0.6848(2) 0.42008(12) 0.0284(5) Uani 1 1 d . . . . .
H35A H 0.3084 0.7633 0.4166 0.043 Uiso 1 1 calc GR . . . .
H35B H 0.4292 0.6968 0.4505 0.043 Uiso 1 1 calc GR . . . .
H35C H 0.3053 0.6200 0.4403 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.2886(2) 0.5983(2) 0.15750(11) 0.0189(4) Uani 1 1 d . . . . .
C33 C 0.5112(2) 0.4964(2) 0.34497(12) 0.0272(5) Uani 1 1 d . . . . .
H33A H 0.4596 0.4346 0.3696 0.041 Uiso 1 1 calc GR . . . .
H33B H 0.5844 0.5128 0.3726 0.041 Uiso 1 1 calc GR . . . .
H33C H 0.5403 0.4643 0.2984 0.041 Uiso 1 1 calc GR . . . .
C16 C 0.0734(2) 0.6959(2) -0.02095(13) 0.0314(6) Uani 1 1 d . . . . .
H16 H 0.0292 0.7198 -0.0616 0.038 Uiso 1 1 calc R . . . .
C32 C 0.3157(3) 0.9184(2) 0.13879(12) 0.0320(6) Uani 1 1 d . . . . .
H32 H 0.3902 0.8852 0.1591 0.038 Uiso 1 1 calc R . . . .
C24 C 0.1339(3) 0.9576(2) 0.42824(13) 0.0327(6) Uani 1 1 d . . . . .
H24 H 0.1233 0.9945 0.4737 0.039 Uiso 1 1 calc R . . . .
C23 C 0.0603(2) 0.8594(3) 0.41063(13) 0.0321(6) Uani 1 1 d . . . . .
H23 H -0.0019 0.8299 0.4436 0.039 Uiso 1 1 calc R . . . .
C27 C 0.1980(2) 0.8797(2) 0.16344(11) 0.0257(5) Uani 1 1 d . . . . .
C20 C 0.1818(2) 0.7852(2) 0.22265(11) 0.0204(5) Uani 1 1 d . . . . .
H20 H 0.1037 0.7391 0.2152 0.024 Uiso 1 1 calc R . . . .
C31 C 0.3246(4) 1.0059(3) 0.08436(14) 0.0465(8) Uani 1 1 d . . . . .
H31 H 0.4050 1.0320 0.0675 0.056 Uiso 1 1 calc R . . . .
C39 C 0.8626(2) 0.4796(2) 0.31702(13) 0.0294(5) Uani 1 1 d . . . . .
C38 C 0.8886(2) 0.4958(3) 0.38721(13) 0.0362(6) Uani 1 1 d . . . . .
H38 H 0.8907 0.5773 0.4064 0.043 Uiso 1 1 calc R . . . .
C28 C 0.0899(3) 0.9313(2) 0.13317(13) 0.0365(6) Uani 1 1 d . . . . .
H28 H 0.0088 0.9064 0.1498 0.044 Uiso 1 1 calc R . . . .
C36 C 0.9089(3) 0.2738(3) 0.40107(15) 0.0445(7) Uani 1 1 d . . . . .
H36 H 0.9250 0.2030 0.4300 0.053 Uiso 1 1 calc R . . . .
C40 C 0.8604(2) 0.3605(3) 0.28903(13) 0.0315(6) Uani 1 1 d . . . . .
C41 C 0.8832(3) 0.2580(3) 0.33114(15) 0.0396(6) Uani 1 1 d . . . . .
H41 H 0.8813 0.1764 0.3121 0.047 Uiso 1 1 calc R . . . .
C37 C 0.9113(3) 0.3916(3) 0.42902(14) 0.0444(7) Uani 1 1 d . . . . .
H37 H 0.9287 0.4018 0.4773 0.053 Uiso 1 1 calc R . . . .
C30 C 0.2156(4) 1.0549(3) 0.05482(15) 0.0559(10) Uani 1 1 d . . . . .
H30 H 0.2217 1.1141 0.0175 0.067 Uiso 1 1 calc R . . . .
C47 C 0.4037(3) 0.8900(3) 0.74159(16) 0.0383(6) Uani 1 1 d . . . . .
C29 C 0.0995(4) 1.0182(3) 0.07939(15) 0.0499(9) Uani 1 1 d . . . . .
H29 H 0.0252 1.0525 0.0594 0.060 Uiso 1 1 calc R . . . .
C42 C 0.3087(3) 0.9727(3) 0.76751(16) 0.0396(6) Uani 1 1 d . . . . .
C43 C 0.2388(3) 1.0437(3) 0.72132(19) 0.0491(8) Uani 1 1 d . . . . .
H43 H 0.1728 1.0995 0.7390 0.059 Uiso 1 1 calc R . . . .
C46 C 0.4295(3) 0.8801(3) 0.66988(17) 0.0488(8) Uani 1 1 d . . . . .
H46 H 0.4944 0.8232 0.6521 0.059 Uiso 1 1 calc R . . . .
C45 C 0.3608(4) 0.9532(3) 0.62374(18) 0.0573(9) Uani 1 1 d . . . . .
H45 H 0.3796 0.9479 0.5743 0.069 Uiso 1 1 calc R . . . .
C44 C 0.2648(3) 1.0337(3) 0.6498(2) 0.0574(9) Uani 1 1 d . . . . .
H44 H 0.2164 1.0826 0.6182 0.069 Uiso 1 1 calc R . . . .
B1 B 0.6937(3) 0.7075(3) 0.49962(15) 0.0319(6) 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
P1 N1 1.6863(18) . ?
P1 C34 1.776(2) . ?
P1 C35 1.778(2) . ?
P1 C33 1.791(2) . ?
Cl2 C39 1.736(3) . ?
Cl1 C40 1.729(2) . ?
Cl3 C47 1.727(3) . ?
Cl4 C42 1.731(3) . ?
F1 B1 1.371(3) . ?
N2 N1 1.463(2) . ?
N2 C1 1.546(3) . ?
N2 C20 1.499(3) . ?
N1 C3 1.427(3) . ?
F3 B1 1.350(3) . ?
F4 B1 1.351(4) . ?
C2 C3 1.381(3) . ?
C2 C7 1.387(3) . ?
C2 C1 1.509(3) . ?
C13 C14 1.470(3) . ?
C13 C8 1.402(3) . ?
C13 C12 1.385(3) . ?
C3 C4 1.391(3) . ?
C14 C19 1.398(3) . ?
C14 C15 1.389(3) . ?
C19 C18 1.384(3) . ?
C19 C1 1.526(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.386(3) . ?
C9 C10 1.393(3) . ?
C8 C1 1.532(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.389(3) . ?
C26 C21 1.394(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.387(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.380(4) . ?
F2 B1 1.370(4) . ?
C21 C22 1.392(3) . ?
C21 C20 1.523(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C16 H16 0.9500 . ?
C32 H32 0.9500 . ?
C32 C27 1.391(4) . ?
C32 C31 1.395(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.389(4) . ?
C23 H23 0.9500 . ?
C27 C20 1.518(3) . ?
C27 C28 1.399(3) . ?
C20 H20 1.0000 . ?
C31 H31 0.9500 . ?
C31 C30 1.391(5) . ?
C39 C38 1.386(3) . ?
C39 C40 1.386(4) . ?
C38 H38 0.9500 . ?
C38 C37 1.387(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.381(4) . ?
C36 H36 0.9500 . ?
C36 C41 1.380(4) . ?
C36 C37 1.374(4) . ?
C40 C41 1.376(4) . ?
C41 H41 0.9500 . ?
C37 H37 0.9500 . ?
C30 H30 0.9500 . ?
C30 C29 1.368(5) . ?
C47 C42 1.386(4) . ?
C47 C46 1.378(4) . ?
C29 H29 0.9500 . ?
C42 C43 1.380(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.374(5) . ?
C46 H46 0.9500 . ?
C46 C45 1.385(5) . ?
C45 H45 0.9500 . ?
C45 C44 1.380(5) . ?
C44 H44 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
N1 P1 C34 108.73(10) . . ?
N1 P1 C35 109.23(10) . . ?
N1 P1 C33 111.58(10) . . ?
C34 P1 C35 110.22(12) . . ?
C34 P1 C33 109.93(12) . . ?
C35 P1 C33 107.14(11) . . ?
N1 N2 C1 104.92(15) . . ?
N1 N2 C20 110.33(15) . . ?
C20 N2 C1 113.91(16) . . ?
N2 N1 P1 116.87(13) . . ?
C3 N1 P1 121.14(14) . . ?
C3 N1 N2 108.74(15) . . ?
C3 C2 C7 119.8(2) . . ?
C3 C2 C1 109.81(18) . . ?
C7 C2 C1 130.2(2) . . ?
C8 C13 C14 108.35(19) . . ?
C12 C13 C14 131.3(2) . . ?
C12 C13 C8 120.3(2) . . ?
C2 C3 N1 110.19(18) . . ?
C2 C3 C4 122.4(2) . . ?
C4 C3 N1 127.4(2) . . ?
C19 C14 C13 108.78(18) . . ?
C15 C14 C13 130.7(2) . . ?
C15 C14 C19 120.3(2) . . ?
C14 C19 C1 110.49(18) . . ?
C18 C19 C14 120.71(19) . . ?
C18 C19 C1 128.5(2) . . ?
C19 C18 H18 120.7 . . ?
C19 C18 C17 118.5(2) . . ?
C17 C18 H18 120.7 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C13 C8 C1 110.23(18) . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 C1 129.11(19) . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C21 120.7(2) . . ?
C21 C26 H26 119.7 . . ?
C2 C7 H7 120.5 . . ?
C6 C7 C2 118.9(2) . . ?
C6 C7 H7 120.5 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C21 C20 122.9(2) . . ?
C22 C21 C26 118.3(2) . . ?
C22 C21 C20 118.7(2) . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C3 C4 H4 121.5 . . ?
C5 C4 C3 117.0(2) . . ?
C5 C4 H4 121.5 . . ?
P1 C34 H34A 109.5 . . ?
P1 C34 H34B 109.5 . . ?
P1 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 H15 120.5 . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C11 C12 H12 120.6 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
P1 C35 H35A 109.5 . . ?
P1 C35 H35B 109.5 . . ?
P1 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C2 C1 N2 103.27(16) . . ?
C2 C1 C19 112.24(17) . . ?
C2 C1 C8 118.12(18) . . ?
C19 C1 N2 115.86(17) . . ?
C19 C1 C8 101.16(17) . . ?
C8 C1 N2 106.68(16) . . ?
P1 C33 H33A 109.5 . . ?
P1 C33 H33B 109.5 . . ?
P1 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C27 C32 H32 120.0 . . ?
C27 C32 C31 120.1(3) . . ?
C31 C32 H32 120.0 . . ?
C25 C24 H24 120.0 . . ?
C25 C24 C23 119.9(2) . . ?
C23 C24 H24 120.0 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.2 . . ?
C32 C27 C20 122.7(2) . . ?
C32 C27 C28 118.7(2) . . ?
C28 C27 C20 118.6(2) . . ?
N2 C20 C21 111.63(17) . . ?
N2 C20 C27 108.26(18) . . ?
N2 C20 H20 108.4 . . ?
C21 C20 H20 108.4 . . ?
C27 C20 C21 111.79(18) . . ?
C27 C20 H20 108.4 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 C32 120.0(3) . . ?
C30 C31 H31 120.0 . . ?
C38 C39 Cl2 119.3(2) . . ?
C38 C39 C40 120.2(2) . . ?
C40 C39 Cl2 120.41(19) . . ?
C39 C38 H38 120.4 . . ?
C39 C38 C37 119.2(3) . . ?
C37 C38 H38 120.4 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C41 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C37 C36 C41 120.3(3) . . ?
C39 C40 Cl1 120.4(2) . . ?
C41 C40 Cl1 119.6(2) . . ?
C41 C40 C39 119.9(2) . . ?
C36 C41 H41 120.0 . . ?
C40 C41 C36 120.0(3) . . ?
C40 C41 H41 120.0 . . ?
C38 C37 H37 119.8 . . ?
C36 C37 C38 120.4(3) . . ?
C36 C37 H37 119.8 . . ?
C31 C30 H30 119.9 . . ?
C29 C30 C31 120.1(3) . . ?
C29 C30 H30 119.9 . . ?
C42 C47 Cl3 121.3(2) . . ?
C46 C47 Cl3 118.7(2) . . ?
C46 C47 C42 120.0(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C47 C42 Cl4 120.5(2) . . ?
C43 C42 Cl4 119.6(2) . . ?
C43 C42 C47 119.9(3) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 C42 120.0(3) . . ?
C44 C43 H43 120.0 . . ?
C47 C46 H46 120.0 . . ?
C47 C46 C45 120.0(3) . . ?
C45 C46 H46 120.0 . . ?
C46 C45 H45 120.1 . . ?
C44 C45 C46 119.7(3) . . ?
C44 C45 H45 120.1 . . ?
C43 C44 C45 120.4(3) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
F3 B1 F1 110.4(2) . . ?
F3 B1 F4 110.6(2) . . ?
F3 B1 F2 109.2(3) . . ?
F4 B1 F1 113.7(3) . . ?
F4 B1 F2 107.3(3) . . ?
F2 B1 F1 105.4(2) . . ?

_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_5
_database_code_depnum_ccdc_archive 'CCDC 1823670'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 Cl3 Ga N2, C3 H3, 0.5(C5 H12)'
_chemical_formula_sum            'C37.50 H31 Cl3 Ga N2'
_chemical_formula_weight         685.71
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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                   10.1320(16)
_cell_length_b                   11.6757(18)
_cell_length_c                   15.355(2)
_cell_angle_alpha                85.260(4)
_cell_angle_beta                 78.703(4)
_cell_angle_gamma                68.857(5)
_cell_volume                     1661.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9458
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      3.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0707 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35986
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         3.963
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5641
_reflns_number_total             7277
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.617
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7277
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.030
_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)+(0.0492P)²+0.5557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C37 \\sim C37-C38
 with sigma of 0.002
 C37-C38 \\sim C38-C39
 with sigma of 0.002
 C39-C40 \\sim C39-C38
 with sigma of 0.002
 C36-C38 \\sim C37-C39
 with sigma of 0.002
 C36-C38 \\sim C38-C40
 with sigma of 0.002
3. Rigid bond restraints
 C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40: within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) C38(0.5) H38A(0.5) H38B(0.5) C39(0.5) H39A(0.5) H39B(0.5) C40(0.5)
 H40A(0.5) H40B(0.5) H40C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
6.b Me refined with riding coordinates:
 C36(H36A,H36B,H36C), C40(H40A,H40B,H40C)
6.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C18(H18), C7(H7), C26(H26), C9(H9), C12(H12), C23(H23), C11(H11),
 C10(H10), C15(H15), C31(H31), C4(H4), C30(H30), C32(H32), C28(H28), C5(H5),
 C17(H17), C6(H6), C16(H16), C25(H25), C24(H24), C29(H29), C35(H35), C34(H34),
 C33(H33)
;
_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
Ga1 Ga 0.58477(3) 0.50456(2) 0.68841(2) 0.02196(9) Uani 1 1 d . . . . .
Cl1 Cl 0.75542(7) 0.46996(6) 0.76475(5) 0.03904(17) Uani 1 1 d . . . . .
Cl3 Cl 0.38712(7) 0.63681(6) 0.75719(4) 0.03775(17) Uani 1 1 d . . . . .
Cl2 Cl 0.63885(10) 0.56934(6) 0.55599(5) 0.0571(2) Uani 1 1 d . . . . .
N2 N 0.64209(19) 0.24540(15) 0.72322(11) 0.0164(4) Uani 1 1 d . . . . .
N1 N 0.54994(19) 0.35112(16) 0.68785(11) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.4127(2) 0.3414(2) 0.70811(14) 0.0200(5) Uani 1 1 d . . . . .
C22 C 0.8858(2) 0.1474(2) 0.82793(14) 0.0220(5) Uani 1 1 d . . . . .
H22 H 0.8207 0.2235 0.8526 0.026 Uiso 1 1 calc R . . . .
C18 C 0.6428(3) -0.0304(2) 0.71231(16) 0.0275(5) Uani 1 1 d . . . . .
H18 H 0.6152 0.0050 0.6577 0.033 Uiso 1 1 calc R . . . .
C2 C 0.4104(2) 0.2427(2) 0.76494(14) 0.0217(5) Uani 1 1 d . . . . .
C20 C 0.7802(2) 0.20218(18) 0.69002(14) 0.0175(4) Uani 1 1 d . . . . .
C27 C 0.8358(2) 0.2387(2) 0.59967(14) 0.0210(5) Uani 1 1 d . . . . .
C7 C 0.2850(3) 0.2181(2) 0.79295(17) 0.0325(6) Uani 1 1 d . . . . .
H7 H 0.2835 0.1508 0.8319 0.039 Uiso 1 1 calc R . . . .
C21 C 0.8820(2) 0.1159(2) 0.74331(14) 0.0191(4) Uani 1 1 d . . . . .
C13 C 0.6180(2) 0.0905(2) 0.92997(14) 0.0217(5) Uani 1 1 d . . . . .
C8 C 0.5572(2) 0.2035(2) 0.88777(14) 0.0199(5) Uani 1 1 d . . . . .
C26 C 0.9798(3) 0.0046(2) 0.70664(16) 0.0293(5) Uani 1 1 d . . . . .
H26 H 0.9804 -0.0160 0.6479 0.035 Uiso 1 1 calc R . . . .
C9 C 0.5052(3) 0.3131(2) 0.93209(15) 0.0265(5) Uani 1 1 d . . . . .
H9 H 0.4621 0.3887 0.9029 0.032 Uiso 1 1 calc R . . . .
C14 C 0.6602(2) -0.0091(2) 0.86570(15) 0.0222(5) Uani 1 1 d . . . . .
C19 C 0.6226(2) 0.0420(2) 0.78438(14) 0.0206(5) Uani 1 1 d . . . . .
C12 C 0.6291(3) 0.0883(2) 1.01889(15) 0.0298(6) Uani 1 1 d . . . . .
H12 H 0.6703 0.0127 1.0485 0.036 Uiso 1 1 calc R . . . .
C23 C 0.9849(3) 0.0675(2) 0.87661(16) 0.0282(5) Uani 1 1 d . . . . .
H23 H 0.9887 0.0895 0.9340 0.034 Uiso 1 1 calc R . . . .
C11 C 0.5788(3) 0.1984(3) 1.06355(16) 0.0336(6) Uani 1 1 d . . . . .
H11 H 0.5864 0.1977 1.1243 0.040 Uiso 1 1 calc R . . . .
C10 C 0.5178(3) 0.3096(2) 1.02166(16) 0.0335(6) Uani 1 1 d . . . . .
H10 H 0.4843 0.3838 1.0538 0.040 Uiso 1 1 calc R . . . .
C1 C 0.5568(2) 0.18140(19) 0.79109(14) 0.0189(4) Uani 1 1 d . . . . .
C15 C 0.7241(3) -0.1360(2) 0.87477(17) 0.0309(6) Uani 1 1 d . . . . .
H15 H 0.7517 -0.1720 0.9292 0.037 Uiso 1 1 calc R . . . .
C31 C 0.8186(3) 0.2691(2) 0.44476(16) 0.0362(6) Uani 1 1 d . . . . .
H31 H 0.7696 0.2708 0.3976 0.043 Uiso 1 1 calc R . . . .
C4 C 0.2892(3) 0.4177(2) 0.67698(16) 0.0269(5) Uani 1 1 d . . . . .
H4 H 0.2912 0.4842 0.6374 0.032 Uiso 1 1 calc R . . . .
C30 C 0.9455(3) 0.2916(3) 0.42709(17) 0.0427(7) Uani 1 1 d . . . . .
H30 H 0.9826 0.3103 0.3681 0.051 Uiso 1 1 calc R . . . .
C32 C 0.7620(3) 0.2441(2) 0.53032(15) 0.0264(5) Uani 1 1 d . . . . .
H32 H 0.6731 0.2306 0.5422 0.032 Uiso 1 1 calc R . . . .
C28 C 0.9656(3) 0.2590(2) 0.58154(16) 0.0314(6) Uani 1 1 d . . . . .
H28 H 1.0174 0.2536 0.6280 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1632(3) 0.3930(2) 0.70583(17) 0.0345(6) Uani 1 1 d . . . . .
H5 H 0.0773 0.4445 0.6864 0.041 Uiso 1 1 calc R . . . .
C17 C 0.7051(3) -0.1573(2) 0.72286(18) 0.0342(6) Uani 1 1 d . . . . .
H17 H 0.7195 -0.2094 0.6748 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1606(3) 0.2941(3) 0.76271(19) 0.0398(7) Uani 1 1 d . . . . .
H6 H 0.0735 0.2784 0.7810 0.048 Uiso 1 1 calc R . . . .
C16 C 0.7462(3) -0.2085(2) 0.80224(19) 0.0362(6) Uani 1 1 d . . . . .
H16 H 0.7906 -0.2950 0.8072 0.043 Uiso 1 1 calc R . . . .
C25 C 1.0759(3) -0.0755(2) 0.75670(18) 0.0398(7) Uani 1 1 d . . . . .
H25 H 1.1404 -0.1523 0.7329 0.048 Uiso 1 1 calc R . . . .
C24 C 1.0777(3) -0.0438(2) 0.84111(18) 0.0374(6) Uani 1 1 d . . . . .
H24 H 1.1435 -0.0991 0.8750 0.045 Uiso 1 1 calc R . . . .
C29 C 1.0195(3) 0.2872(3) 0.49525(18) 0.0436(7) Uani 1 1 d . . . . .
H29 H 1.1068 0.3034 0.4830 0.052 Uiso 1 1 calc R . . . .
C35 C 0.5847(4) 0.8806(3) 0.4772(2) 0.0493(8) Uani 1 1 d . . . . .
H35 H 0.6431 0.7987 0.4607 0.059 Uiso 1 1 calc R . . . .
C34 C 0.4691(4) 0.9018(3) 0.5442(2) 0.0475(8) Uani 1 1 d . . . . .
H34 H 0.4480 0.8347 0.5750 0.057 Uiso 1 1 calc R . . . .
C33 C 0.3819(4) 1.0217(3) 0.5676(2) 0.0497(8) Uani 1 1 d . . . . .
H33 H 0.3003 1.0370 0.6137 0.060 Uiso 1 1 calc R . . . .
C36 C 0.8624(15) 0.3894(14) 1.0111(9) 0.125(4) Uani 0.5 1 d D U P A -1
H36A H 0.7860 0.3589 1.0400 0.187 Uiso 0.5 1 calc R . P A -1
H36B H 0.8229 0.4597 0.9725 0.187 Uiso 0.5 1 calc R . P A -1
H36C H 0.9391 0.3240 0.9755 0.187 Uiso 0.5 1 calc R . P A -1
C37 C 0.9214(10) 0.4279(11) 1.0793(6) 0.109(2) Uani 0.5 1 d D U P A -1
H37A H 0.9582 0.3566 1.1188 0.131 Uiso 0.5 1 calc R . P A -1
H37B H 0.8423 0.4921 1.1159 0.131 Uiso 0.5 1 calc R . P A -1
C38 C 1.0379(10) 0.4758(9) 1.0442(7) 0.113(2) Uani 0.5 1 d D U P A -1
H38A H 1.0726 0.4958 1.0949 0.136 Uiso 0.5 1 calc R . P A -1
H38B H 1.1191 0.4102 1.0102 0.136 Uiso 0.5 1 calc R . P A -1
C39 C 0.9974(11) 0.5856(10) 0.9867(8) 0.125(3) Uani 0.5 1 d D U P A -1
H39A H 0.9062 0.6459 1.0168 0.150 Uiso 0.5 1 calc R . P A -1
H39B H 0.9791 0.5620 0.9310 0.150 Uiso 0.5 1 calc R . P A -1
C40 C 1.1049(15) 0.6461(12) 0.9637(11) 0.130(4) Uani 0.5 1 d D U P A -1
H40A H 1.0691 0.7178 0.9255 0.194 Uiso 0.5 1 calc R . P A -1
H40B H 1.1220 0.6724 1.0181 0.194 Uiso 0.5 1 calc R . P A -1
H40C H 1.1950 0.5882 0.9322 0.194 Uiso 0.5 1 calc R . P A -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
Ga1 Cl1 2.1767(7) . ?
Ga1 Cl3 2.1726(7) . ?
Ga1 Cl2 2.1483(8) . ?
Ga1 N1 1.9479(18) . ?
N2 N1 1.395(2) . ?
N2 C20 1.314(3) . ?
N2 C1 1.541(3) . ?
N1 C3 1.408(3) . ?
C3 C2 1.391(3) . ?
C3 C4 1.395(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.391(3) . ?
C22 C23 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C18 C17 1.395(3) . ?
C2 C7 1.383(3) . ?
C2 C1 1.514(3) . ?
C20 C27 1.481(3) . ?
C20 C21 1.481(3) . ?
C27 C32 1.401(3) . ?
C27 C28 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.395(4) . ?
C21 C26 1.401(3) . ?
C13 C8 1.403(3) . ?
C13 C14 1.475(3) . ?
C13 C12 1.389(3) . ?
C8 C9 1.377(3) . ?
C8 C1 1.529(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.402(3) . ?
C14 C19 1.400(3) . ?
C14 C15 1.395(3) . ?
C19 C1 1.523(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.386(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.388(4) . ?
C31 H31 0.9500 . ?
C31 C30 1.374(4) . ?
C31 C32 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C30 H30 0.9500 . ?
C30 C29 1.390(4) . ?
C32 H32 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.392(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.384(4) . ?
C6 H6 0.9500 . ?
C16 H16 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.382(4) . ?
C24 H24 0.9500 . ?
C29 H29 0.9500 . ?
C35 H35 0.9500 . ?
C35 C34 1.361(5) . ?
C35 C33 1.394(4) 2_676 ?
C34 H34 0.9500 . ?
C34 C33 1.392(4) . ?
C33 C35 1.394(4) 2_676 ?
C33 H33 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C36 C37 1.474(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.475(6) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.473(6) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.473(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
Cl3 Ga1 Cl1 109.54(3) . . ?
Cl2 Ga1 Cl1 112.26(4) . . ?
Cl2 Ga1 Cl3 110.05(3) . . ?
N1 Ga1 Cl1 106.72(5) . . ?
N1 Ga1 Cl3 106.45(6) . . ?
N1 Ga1 Cl2 111.61(6) . . ?
N1 N2 C1 111.08(16) . . ?
C20 N2 N1 121.01(17) . . ?
C20 N2 C1 127.17(17) . . ?
N2 N1 Ga1 118.87(13) . . ?
N2 N1 C3 105.84(16) . . ?
C3 N1 Ga1 124.15(14) . . ?
C2 C3 N1 112.08(19) . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 N1 126.8(2) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C19 C18 H18 121.2 . . ?
C19 C18 C17 117.6(2) . . ?
C17 C18 H18 121.2 . . ?
C3 C2 C1 109.20(19) . . ?
C7 C2 C3 120.8(2) . . ?
C7 C2 C1 129.8(2) . . ?
N2 C20 C27 120.80(19) . . ?
N2 C20 C21 119.83(19) . . ?
C27 C20 C21 119.37(19) . . ?
C32 C27 C20 119.5(2) . . ?
C28 C27 C20 120.8(2) . . ?
C28 C27 C32 119.6(2) . . ?
C2 C7 H7 120.7 . . ?
C2 C7 C6 118.5(2) . . ?
C6 C7 H7 120.7 . . ?
C22 C21 C20 120.34(19) . . ?
C22 C21 C26 119.8(2) . . ?
C26 C21 C20 119.81(19) . . ?
C8 C13 C14 109.08(19) . . ?
C12 C13 C8 119.5(2) . . ?
C12 C13 C14 131.5(2) . . ?
C13 C8 C1 109.39(18) . . ?
C9 C8 C13 122.1(2) . . ?
C9 C8 C1 128.5(2) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 C21 119.5(2) . . ?
C25 C26 H26 120.2 . . ?
C8 C9 H9 121.1 . . ?
C8 C9 C10 117.8(2) . . ?
C10 C9 H9 121.1 . . ?
C19 C14 C13 108.87(19) . . ?
C15 C14 C13 131.3(2) . . ?
C15 C14 C19 119.8(2) . . ?
C18 C19 C14 121.8(2) . . ?
C18 C19 C1 128.4(2) . . ?
C14 C19 C1 109.78(19) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 C13 118.7(2) . . ?
C11 C12 H12 120.6 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C12 C11 H11 119.2 . . ?
C10 C11 C12 121.5(2) . . ?
C10 C11 H11 119.2 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C2 C1 N2 98.79(16) . . ?
C2 C1 C8 113.06(18) . . ?
C2 C1 C19 116.92(18) . . ?
C8 C1 N2 113.76(17) . . ?
C19 C1 N2 112.00(17) . . ?
C19 C1 C8 102.86(17) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 H15 120.8 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.6(2) . . ?
C32 C31 H31 119.7 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 H4 121.1 . . ?
C31 C30 H30 119.9 . . ?
C31 C30 C29 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C27 C32 H32 120.1 . . ?
C31 C32 C27 119.9(2) . . ?
C31 C32 H32 120.1 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.9(2) . . ?
C29 C28 H28 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C33 120.5(3) . 2_676 ?
C33 C35 H35 119.7 2_676 . ?
C35 C34 H34 120.0 . . ?
C35 C34 C33 119.9(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C33 H33 120.2 2_676 . ?
C34 C33 C35 119.5(3) . 2_676 ?
C34 C33 H33 120.2 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C37 C36 H36C 109.5 . . ?
C36 C37 H37A 108.6 . . ?
C36 C37 H37B 108.6 . . ?
C36 C37 C38 114.8(6) . . ?
H37A C37 H37B 107.5 . . ?
C38 C37 H37A 108.6 . . ?
C38 C37 H37B 108.6 . . ?
C37 C38 H38A 108.6 . . ?
C37 C38 H38B 108.6 . . ?
H38A C38 H38B 107.5 . . ?
C39 C38 C37 114.9(6) . . ?
C39 C38 H38A 108.6 . . ?
C39 C38 H38B 108.6 . . ?
C38 C39 H39A 108.5 . . ?
C38 C39 H39B 108.5 . . ?
C38 C39 C40 115.1(6) . . ?
H39A C39 H39B 107.5 . . ?
C40 C39 H39A 108.5 . . ?
C40 C39 H39B 108.5 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_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_7
_database_code_depnum_ccdc_archive 'CCDC 1823672'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H27 N3 O'
_chemical_formula_sum            'C39 H27 N3 O'
_chemical_formula_weight         553.63
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.697(4)
_cell_length_b                   9.825(2)
_cell_length_c                   16.948(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.627(8)
_cell_angle_gamma                90
_cell_volume                     2779.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3597
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0391 before and 0.0368 after correction.
The Ratio of minimum to maximum transmission is 0.9544.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16132
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.106
_diffrn_reflns_theta_min         2.396
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.927
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3948
_reflns_number_total             5688
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.212
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.012
_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)+(0.0444P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C38(H38), C4(H4), C22(H22), C9(H9), C7(H7), C18(H18), C5(H5),
 C6(H6), C23(H23), C17(H17), C34(H34), C37(H37), C11(H11), C15(H15), C12(H12),
 C10(H10), C32(H32), C24(H24), C35(H35), C36(H36), C16(H16), C25(H25), C28(H28),
  C31(H31), C29(H29), C30(H30)
;
_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
O1 O 0.72845(7) 0.61808(12) 0.27535(6) 0.0275(3) Uani 1 1 d . . . . .
N3 N 0.79999(8) 0.49388(13) 0.37021(7) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.66938(8) 0.52927(13) 0.38614(7) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.69240(8) 0.42481(12) 0.44382(6) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.59256(10) 0.49088(16) 0.35559(8) 0.0179(4) Uani 1 1 d . . . . .
C2 C 0.57571(10) 0.35914(16) 0.37839(8) 0.0187(4) Uani 1 1 d . . . . .
C21 C 0.82003(10) 0.30044(16) 0.47003(8) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.64827(10) 0.29616(15) 0.42023(8) 0.0166(3) Uani 1 1 d . . . . .
C20 C 0.78072(10) 0.43677(16) 0.45035(8) 0.0174(3) Uani 1 1 d . . . . .
C39 C 0.73282(10) 0.55282(16) 0.33633(8) 0.0194(4) Uani 1 1 d . . . . .
C19 C 0.68629(10) 0.18920(16) 0.36649(8) 0.0178(3) Uani 1 1 d . . . . .
C13 C 0.64637(10) 0.07536(16) 0.48008(8) 0.0188(4) Uani 1 1 d . . . . .
C33 C 0.80325(10) 0.54042(16) 0.51582(8) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.62845(10) 0.21210(16) 0.49231(8) 0.0185(4) Uani 1 1 d . . . . .
C14 C 0.68220(10) 0.06105(16) 0.40206(8) 0.0192(4) Uani 1 1 d . . . . .
C27 C 0.87612(10) 0.54560(17) 0.34577(8) 0.0217(4) Uani 1 1 d . . . . .
C26 C 0.86876(10) 0.22952(17) 0.41971(9) 0.0227(4) Uani 1 1 d . . . . .
H26 H 0.8802 0.2668 0.3695 0.027 Uiso 1 1 calc R . . . .
C38 C 0.74661(11) 0.62524(16) 0.54893(8) 0.0230(4) Uani 1 1 d . . . . .
H38 H 0.6919 0.6193 0.5322 0.028 Uiso 1 1 calc R . . . .
C4 C 0.53960(11) 0.56823(17) 0.31053(8) 0.0224(4) Uani 1 1 d . . . . .
H4 H 0.5523 0.6584 0.2950 0.027 Uiso 1 1 calc R . . . .
C22 C 0.80507(11) 0.24340(16) 0.54387(8) 0.0219(4) Uani 1 1 d . . . . .
H22 H 0.7735 0.2921 0.5801 0.026 Uiso 1 1 calc R . . . .
C9 C 0.59814(11) 0.25716(17) 0.56284(8) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.5848 0.3502 0.5704 0.028 Uiso 1 1 calc R . . . .
C7 C 0.50269(10) 0.30157(18) 0.35837(9) 0.0241(4) Uani 1 1 d . . . . .
H7 H 0.4901 0.2118 0.3748 0.029 Uiso 1 1 calc R . . . .
C18 C 0.71678(10) 0.20311(17) 0.29160(8) 0.0217(4) Uani 1 1 d . . . . .
H18 H 0.7171 0.2891 0.2659 0.026 Uiso 1 1 calc R . . . .
C5 C 0.46692(10) 0.50846(18) 0.28881(9) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.4296 0.5577 0.2565 0.030 Uiso 1 1 calc R . . . .
C6 C 0.44773(11) 0.37795(18) 0.31348(9) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.3968 0.3405 0.2997 0.031 Uiso 1 1 calc R . . . .
C23 C 0.83545(11) 0.11740(17) 0.56473(9) 0.0264(4) Uani 1 1 d . . . . .
H23 H 0.8231 0.0786 0.6143 0.032 Uiso 1 1 calc R . . . .
C17 C 0.74702(11) 0.08753(18) 0.25499(8) 0.0247(4) Uani 1 1 d . . . . .
H17 H 0.7694 0.0955 0.2043 0.030 Uiso 1 1 calc R . . . .
C34 C 0.88286(11) 0.55013(17) 0.54184(9) 0.0269(4) Uani 1 1 d . . . . .
H34 H 0.9218 0.4908 0.5208 0.032 Uiso 1 1 calc R . . . .
C37 C 0.77044(12) 0.71930(17) 0.60687(9) 0.0283(4) Uani 1 1 d . . . . .
H37 H 0.7315 0.7763 0.6298 0.034 Uiso 1 1 calc R . . . .
C11 C 0.60641(12) 0.02586(18) 0.61067(9) 0.0294(4) Uani 1 1 d . . . . .
H11 H 0.6000 -0.0373 0.6524 0.035 Uiso 1 1 calc R . . . .
C15 C 0.71140(11) -0.05391(17) 0.36486(9) 0.0255(4) Uani 1 1 d . . . . .
H15 H 0.7085 -0.1409 0.3891 0.031 Uiso 1 1 calc R . . . .
C12 C 0.63428(11) -0.01970(17) 0.53889(9) 0.0261(4) Uani 1 1 d . . . . .
H12 H 0.6448 -0.1135 0.5304 0.031 Uiso 1 1 calc R . . . .
C10 C 0.58788(11) 0.16132(18) 0.62250(9) 0.0276(4) Uani 1 1 d . . . . .
H10 H 0.5679 0.1895 0.6718 0.033 Uiso 1 1 calc R . . . .
C32 C 0.91458(12) 0.47978(19) 0.28580(9) 0.0314(5) Uani 1 1 d . . . . .
H32 H 0.8913 0.4013 0.2617 0.038 Uiso 1 1 calc R . . . .
C24 C 0.88386(11) 0.04736(18) 0.51378(10) 0.0303(4) Uani 1 1 d . . . . .
H24 H 0.9050 -0.0392 0.5281 0.036 Uiso 1 1 calc R . . . .
C35 C 0.90571(12) 0.64597(18) 0.59835(9) 0.0326(5) Uani 1 1 d . . . . .
H35 H 0.9605 0.6535 0.6146 0.039 Uiso 1 1 calc R . . . .
C36 C 0.84939(12) 0.73053(17) 0.63120(9) 0.0309(5) Uani 1 1 d . . . . .
H36 H 0.8651 0.7956 0.6701 0.037 Uiso 1 1 calc R . . . .
C16 C 0.74495(11) -0.03870(18) 0.29132(9) 0.0275(4) Uani 1 1 d . . . . .
H16 H 0.7667 -0.1157 0.2657 0.033 Uiso 1 1 calc R . . . .
C25 C 0.90114(11) 0.10464(18) 0.44170(10) 0.0295(4) Uani 1 1 d . . . . .
H25 H 0.9354 0.0581 0.4070 0.035 Uiso 1 1 calc R . . . .
C28 C 0.90790(12) 0.66491(19) 0.37733(10) 0.0337(5) Uani 1 1 d . . . . .
H28 H 0.8793 0.7146 0.4155 0.040 Uiso 1 1 calc R . . . .
C31 C 0.98774(14) 0.5293(2) 0.26094(12) 0.0480(6) Uani 1 1 d . . . . .
H31 H 1.0146 0.4840 0.2198 0.058 Uiso 1 1 calc R . . . .
C29 C 0.98122(14) 0.7110(2) 0.35291(12) 0.0481(6) Uani 1 1 d . . . . .
H29 H 1.0042 0.7904 0.3761 0.058 Uiso 1 1 calc R . . . .
C30 C 1.02136(14) 0.6427(2) 0.29521(14) 0.0527(6) Uani 1 1 d . . . . .
H30 H 1.0722 0.6742 0.2792 0.063 Uiso 1 1 calc R . . . .


_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
O1 C39 1.2166(17) . ?
N3 C20 1.5127(18) . ?
N3 C39 1.373(2) . ?
N3 C27 1.441(2) . ?
N1 N2 1.4613(16) . ?
N1 C3 1.420(2) . ?
N1 C39 1.392(2) . ?
N2 C1 1.511(2) . ?
N2 C20 1.480(2) . ?
C3 C2 1.382(2) . ?
C3 C4 1.380(2) . ?
C2 C1 1.518(2) . ?
C2 C7 1.378(2) . ?
C21 C20 1.524(2) . ?
C21 C26 1.384(2) . ?
C21 C22 1.400(2) . ?
C1 C19 1.539(2) . ?
C1 C8 1.519(2) . ?
C20 C33 1.545(2) . ?
C19 C14 1.398(2) . ?
C19 C18 1.388(2) . ?
C13 C8 1.393(2) . ?
C13 C14 1.474(2) . ?
C13 C12 1.385(2) . ?
C33 C38 1.391(2) . ?
C33 C34 1.392(2) . ?
C8 C9 1.384(2) . ?
C14 C15 1.389(2) . ?
C27 C32 1.379(2) . ?
C27 C28 1.388(2) . ?
C26 H26 0.9500 . ?
C26 C25 1.388(2) . ?
C38 H38 0.9500 . ?
C38 C37 1.398(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.394(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.383(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.385(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(2) . ?
C37 H37 0.9500 . ?
C37 C36 1.374(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C11 C10 1.382(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.391(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.384(3) . ?
C36 H36 0.9500 . ?
C16 H16 0.9500 . ?
C25 H25 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.380(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.370(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.375(3) . ?
C30 H30 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
C39 N3 C20 109.87(12) . . ?
C39 N3 C27 116.60(12) . . ?
C27 N3 C20 126.94(12) . . ?
C3 N1 N2 105.96(11) . . ?
C39 N1 N2 109.40(12) . . ?
C39 N1 C3 121.17(12) . . ?
N1 N2 C1 107.06(11) . . ?
N1 N2 C20 103.70(11) . . ?
C20 N2 C1 124.28(12) . . ?
C2 C3 N1 109.61(13) . . ?
C4 C3 N1 127.83(15) . . ?
C4 C3 C2 122.55(16) . . ?
C3 C2 C1 110.25(14) . . ?
C7 C2 C3 120.10(15) . . ?
C7 C2 C1 129.54(15) . . ?
C26 C21 C20 124.38(13) . . ?
C26 C21 C22 118.19(15) . . ?
C22 C21 C20 117.44(14) . . ?
N2 C1 C2 99.17(12) . . ?
N2 C1 C19 121.42(13) . . ?
N2 C1 C8 110.96(11) . . ?
C2 C1 C19 109.80(11) . . ?
C2 C1 C8 114.09(13) . . ?
C8 C1 C19 101.98(12) . . ?
N3 C20 C21 114.91(12) . . ?
N3 C20 C33 110.30(12) . . ?
N2 C20 N3 101.49(11) . . ?
N2 C20 C21 111.62(12) . . ?
N2 C20 C33 109.13(12) . . ?
C21 C20 C33 109.12(12) . . ?
O1 C39 N3 127.29(15) . . ?
O1 C39 N1 125.05(15) . . ?
N3 C39 N1 107.62(12) . . ?
C14 C19 C1 109.48(12) . . ?
C18 C19 C1 129.95(14) . . ?
C18 C19 C14 120.44(14) . . ?
C8 C13 C14 108.65(13) . . ?
C12 C13 C8 120.46(14) . . ?
C12 C13 C14 130.75(15) . . ?
C38 C33 C20 122.04(15) . . ?
C38 C33 C34 119.04(15) . . ?
C34 C33 C20 118.92(14) . . ?
C13 C8 C1 110.62(12) . . ?
C9 C8 C1 127.89(14) . . ?
C9 C8 C13 121.48(14) . . ?
C19 C14 C13 109.09(13) . . ?
C15 C14 C19 120.96(14) . . ?
C15 C14 C13 129.92(14) . . ?
C32 C27 N3 118.67(15) . . ?
C32 C27 C28 119.96(17) . . ?
C28 C27 N3 121.20(15) . . ?
C21 C26 H26 119.6 . . ?
C21 C26 C25 120.74(14) . . ?
C25 C26 H26 119.6 . . ?
C33 C38 H38 120.1 . . ?
C33 C38 C37 119.76(17) . . ?
C37 C38 H38 120.1 . . ?
C3 C4 H4 121.5 . . ?
C3 C4 C5 117.09(16) . . ?
C5 C4 H4 121.5 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.96(15) . . ?
C23 C22 H22 119.5 . . ?
C8 C9 H9 121.1 . . ?
C8 C9 C10 117.73(15) . . ?
C10 C9 H9 121.1 . . ?
C2 C7 H7 120.7 . . ?
C2 C7 C6 118.52(16) . . ?
C6 C7 H7 120.7 . . ?
C19 C18 H18 120.9 . . ?
C19 C18 C17 118.25(15) . . ?
C17 C18 H18 120.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.20(16) . . ?
C6 C5 H5 119.4 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.48(17) . . ?
C5 C6 H6 119.8 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.23(15) . . ?
C24 C23 H23 119.9 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.12(14) . . ?
C16 C17 H17 119.4 . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.40(17) . . ?
C35 C34 H34 119.8 . . ?
C38 C37 H37 119.5 . . ?
C36 C37 C38 121.02(17) . . ?
C36 C37 H37 119.5 . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.29(15) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.40(15) . . ?
C16 C15 H15 120.8 . . ?
C13 C12 C11 118.19(15) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.78(14) . . ?
C11 C10 H10 119.6 . . ?
C27 C32 H32 120.3 . . ?
C27 C32 C31 119.38(19) . . ?
C31 C32 H32 120.3 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.31(16) . . ?
C25 C24 H24 120.3 . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.54(18) . . ?
C36 C35 H35 119.7 . . ?
C37 C36 C35 119.21(16) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C17 C16 C15 120.73(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C26 C25 H25 119.7 . . ?
C24 C25 C26 120.51(16) . . ?
C24 C25 H25 119.7 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.63(18) . . ?
C29 C28 H28 120.2 . . ?
C32 C31 H31 119.7 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.5(2) . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 119.7(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
