# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_ql_1_133_1
_database_code_depnum_ccdc_archive 'CCDC 1888246'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H22 N4 O'
_chemical_formula_sum            'C28 H22 N4 O'
_chemical_formula_weight         430.49
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.2269(2)
_cell_length_b                   27.1036(8)
_cell_length_c                   11.1290(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.4517(14)
_cell_angle_gamma                90
_cell_volume                     2179.83(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.79
_cell_measurement_theta_min      4.29
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1046 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.8475.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23216
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.995
_diffrn_reflns_theta_min         3.261
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3841
_reflns_number_total             4566
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.054
_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)+(0.0371P)²+0.9515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C19(H19),
 C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
C1 C 0.0507(2) 0.55523(5) 0.76451(13) 0.0290(3) Uani 1 1 d . . . . .
H1 H -0.018359 0.568337 0.698925 0.035 Uiso 1 1 calc R . . . .
C2 C 0.0138(2) 0.57071(6) 0.88106(14) 0.0361(4) Uani 1 1 d . . . . .
H2 H -0.081466 0.594145 0.894807 0.043 Uiso 1 1 calc R . . . .
C3 C 0.1148(3) 0.55225(6) 0.97705(14) 0.0384(4) Uani 1 1 d . . . . .
H3 H 0.088315 0.562802 1.056476 0.046 Uiso 1 1 calc R . . . .
C4 C 0.2547(2) 0.51830(6) 0.95715(14) 0.0364(4) Uani 1 1 d . . . . .
H4 H 0.325531 0.505966 1.022854 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2912(2) 0.50237(6) 0.84151(13) 0.0297(3) Uani 1 1 d . . . . .
H5 H 0.386606 0.478901 0.828361 0.036 Uiso 1 1 calc R . . . .
C6 C 0.18905(19) 0.52052(5) 0.74399(12) 0.0245(3) Uani 1 1 d . . . . .
C7 C 0.22742(18) 0.50047(5) 0.62314(12) 0.0234(3) Uani 1 1 d . . . . .
C8 C 0.22680(18) 0.52057(5) 0.50522(12) 0.0234(3) Uani 1 1 d . . . . .
C12 C 0.17887(19) 0.56984(5) 0.45642(13) 0.0259(3) Uani 1 1 d . . . . .
C13 C 0.2155(2) 0.57814(6) 0.32501(13) 0.0327(3) Uani 1 1 d . . . . .
H13A H 0.168333 0.610623 0.301195 0.049 Uiso 1 1 calc GR . . . .
H13B H 0.153091 0.552514 0.277609 0.049 Uiso 1 1 calc GR . . . .
H13C H 0.349036 0.576673 0.310656 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.37696(19) 0.40009(5) 0.45330(13) 0.0245(3) Uani 1 1 d . . . . .
C16 C 0.4486(2) 0.39729(5) 0.33785(13) 0.0266(3) Uani 1 1 d . . . . .
H16 H 0.447465 0.425411 0.286879 0.032 Uiso 1 1 calc R . . . .
C17 C 0.5215(2) 0.35308(5) 0.29821(13) 0.0295(3) Uani 1 1 d . . . . .
H17 H 0.570055 0.350910 0.219300 0.035 Uiso 1 1 calc R . . . .
C18 C 0.5249(2) 0.31148(5) 0.37268(14) 0.0282(3) Uani 1 1 d . . . . .
C19 C 0.4440(2) 0.31490(5) 0.48602(14) 0.0284(3) Uani 1 1 d . . . . .
H19 H 0.439749 0.286564 0.536162 0.034 Uiso 1 1 calc R . . . .
C20 C 0.3701(2) 0.35887(5) 0.52631(13) 0.0275(3) Uani 1 1 d . . . . .
H20 H 0.315132 0.360747 0.603427 0.033 Uiso 1 1 calc R . . . .
C22 C 0.7634(2) 0.26583(6) 0.26019(13) 0.0302(3) Uani 1 1 d . . . . .
C23 C 0.7872(2) 0.22608(6) 0.18158(15) 0.0374(4) Uani 1 1 d . . . . .
H23 H 0.700301 0.199770 0.180954 0.045 Uiso 1 1 calc R . . . .
C24 C 0.9363(3) 0.22495(7) 0.10498(16) 0.0482(5) Uani 1 1 d . . . . .
H24 H 0.952326 0.197706 0.052386 0.058 Uiso 1 1 calc R . . . .
C25 C 1.0611(3) 0.26288(8) 0.10441(18) 0.0557(6) Uani 1 1 d . . . . .
H25 H 1.160284 0.262687 0.048873 0.067 Uiso 1 1 calc R . . . .
C26 C 1.0429(3) 0.30186(7) 0.18538(19) 0.0486(5) Uani 1 1 d . . . . .
H26 H 1.132198 0.327569 0.186587 0.058 Uiso 1 1 calc R . . . .
C27 C 0.8951(2) 0.30331(6) 0.26417(15) 0.0355(4) Uani 1 1 d . . . . .
H27 H 0.883847 0.329573 0.320176 0.043 Uiso 1 1 calc R . . . .
C28 C 0.5229(2) 0.22130(5) 0.36967(13) 0.0307(3) Uani 1 1 d . . . . .
C29 C 0.6217(3) 0.18610(7) 0.43377(17) 0.0470(4) Uani 1 1 d . . . . .
H29 H 0.745188 0.192443 0.459332 0.056 Uiso 1 1 calc R . . . .
C30 C 0.5369(4) 0.14122(7) 0.46007(18) 0.0641(7) Uani 1 1 d . . . . .
H30 H 0.603690 0.116845 0.503815 0.077 Uiso 1 1 calc R . . . .
C31 C 0.3586(4) 0.13169(7) 0.4238(2) 0.0665(7) Uani 1 1 d . . . . .
H31 H 0.303571 0.100668 0.440881 0.080 Uiso 1 1 calc R . . . .
C32 C 0.2608(3) 0.16685(7) 0.3632(2) 0.0568(6) Uani 1 1 d . . . . .
H32 H 0.136332 0.160585 0.339781 0.068 Uiso 1 1 calc R . . . .
C33 C 0.3420(2) 0.21178(6) 0.33550(15) 0.0376(4) Uani 1 1 d . . . . .
H33 H 0.273169 0.236080 0.292911 0.045 Uiso 1 1 calc R . . . .
N9 N 0.28361(16) 0.48527(4) 0.42882(10) 0.0244(2) Uani 1 1 d . . . . .
N10 N 0.31334(16) 0.44646(4) 0.49822(10) 0.0238(3) Uani 1 1 d . . . . .
N11 N 0.28281(16) 0.45346(4) 0.61572(10) 0.0249(3) Uani 1 1 d . . . . .
N21 N 0.60748(18) 0.26675(5) 0.33651(13) 0.0344(3) Uani 1 1 d . . . . .
O14 O 0.11113(16) 0.60175(4) 0.51921(10) 0.0334(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.391(2) . ?
C1 C6 1.393(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(2) . ?
C6 C7 1.4788(18) . ?
C7 C8 1.4209(19) . ?
C7 N11 1.3383(18) . ?
C8 C12 1.482(2) . ?
C8 N9 1.3463(17) . ?
C12 C13 1.505(2) . ?
C12 O14 1.2169(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 C16 1.3911(19) . ?
C15 C20 1.383(2) . ?
C15 N10 1.4300(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(2) . ?
C18 C19 1.398(2) . ?
C18 N21 1.4111(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9500 . ?
C22 C23 1.399(2) . ?
C22 C27 1.393(2) . ?
C22 N21 1.4165(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.368(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.396(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(2) . ?
C28 C33 1.382(2) . ?
C28 N21 1.4253(19) . ?
C29 H29 0.9500 . ?
C29 C30 1.394(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.372(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.362(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(2) . ?
C33 H33 0.9500 . ?
N9 N10 1.3215(16) . ?
N10 N11 1.3414(16) . ?

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
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.99(14) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.48(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.87(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.00(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.56(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.08(13) . . ?
C1 C6 C7 122.50(13) . . ?
C5 C6 C7 118.38(13) . . ?
C8 C7 C6 134.42(13) . . ?
N11 C7 C6 117.66(12) . . ?
N11 C7 C8 107.87(12) . . ?
C7 C8 C12 133.09(12) . . ?
N9 C8 C7 108.19(12) . . ?
N9 C8 C12 118.73(12) . . ?
C8 C12 C13 116.63(12) . . ?
O14 C12 C8 121.59(13) . . ?
O14 C12 C13 121.77(13) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C15 N10 119.59(12) . . ?
C20 C15 C16 120.94(13) . . ?
C20 C15 N10 119.46(12) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.17(13) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.95(13) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 N21 121.91(13) . . ?
C19 C18 C17 118.40(13) . . ?
C19 C18 N21 119.69(13) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.03(14) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.37(13) . . ?
C19 C20 H20 120.3 . . ?
C23 C22 N21 119.39(15) . . ?
C27 C22 C23 119.62(15) . . ?
C27 C22 N21 120.97(13) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.25(17) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.31(17) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.01(16) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.44(18) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 120.4 . . ?
C26 C27 C22 119.24(16) . . ?
C26 C27 H27 120.4 . . ?
C29 C28 N21 120.51(16) . . ?
C33 C28 C29 119.70(16) . . ?
C33 C28 N21 119.78(15) . . ?
C28 C29 H29 120.6 . . ?
C28 C29 C30 118.9(2) . . ?
C30 C29 H29 120.6 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.1(2) . . ?
C31 C30 H30 119.5 . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.77(18) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.3(2) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 120.22(19) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
N10 N9 C8 104.21(11) . . ?
N9 N10 C15 123.13(11) . . ?
N9 N10 N11 115.47(11) . . ?
N11 N10 C15 121.40(11) . . ?
C7 N11 N10 104.26(11) . . ?
C18 N21 C22 121.76(12) . . ?
C18 N21 C28 119.04(12) . . ?
C22 N21 C28 119.01(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C6 C7 C8 37.1(2) . . . . ?
C1 C6 C7 N11 -145.99(14) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
C2 C1 C6 C7 176.36(14) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C5 C6 C7 -177.03(14) . . . . ?
C5 C6 C7 C8 -145.43(16) . . . . ?
C5 C6 C7 N11 31.51(19) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C6 C7 C8 C12 -3.1(3) . . . . ?
C6 C7 C8 N9 176.62(14) . . . . ?
C6 C7 N11 N10 -177.66(11) . . . . ?
C7 C8 C12 C13 173.88(15) . . . . ?
C7 C8 C12 O14 -7.0(2) . . . . ?
C7 C8 N9 N10 0.79(14) . . . . ?
C8 C7 N11 N10 0.04(14) . . . . ?
C8 N9 N10 C15 -179.74(12) . . . . ?
C8 N9 N10 N11 -0.83(15) . . . . ?
C12 C8 N9 N10 -179.46(12) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C15 N10 N11 C7 179.43(12) . . . . ?
C16 C15 C20 C19 3.3(2) . . . . ?
C16 C15 N10 N9 14.1(2) . . . . ?
C16 C15 N10 N11 -164.76(13) . . . . ?
C16 C17 C18 C19 3.3(2) . . . . ?
C16 C17 C18 N21 -176.56(14) . . . . ?
C17 C18 C19 C20 -3.0(2) . . . . ?
C17 C18 N21 C22 32.5(2) . . . . ?
C17 C18 N21 C28 -142.35(15) . . . . ?
C18 C19 C20 C15 -0.2(2) . . . . ?
C19 C18 N21 C22 -147.37(15) . . . . ?
C19 C18 N21 C28 37.8(2) . . . . ?
C20 C15 C16 C17 -3.0(2) . . . . ?
C20 C15 N10 N9 -167.34(13) . . . . ?
C20 C15 N10 N11 13.8(2) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C22 C27 C26 3.4(2) . . . . ?
C23 C22 N21 C18 -149.11(16) . . . . ?
C23 C22 N21 C28 25.7(2) . . . . ?
C23 C24 C25 C26 3.0(3) . . . . ?
C24 C25 C26 C27 -2.1(3) . . . . ?
C25 C26 C27 C22 -1.1(3) . . . . ?
C27 C22 C23 C24 -2.6(2) . . . . ?
C27 C22 N21 C18 32.3(2) . . . . ?
C27 C22 N21 C28 -152.86(16) . . . . ?
C28 C29 C30 C31 -0.1(3) . . . . ?
C29 C28 C33 C32 -1.2(2) . . . . ?
C29 C28 N21 C18 -123.47(17) . . . . ?
C29 C28 N21 C22 61.6(2) . . . . ?
C29 C30 C31 C32 -1.4(3) . . . . ?
C30 C31 C32 C33 1.5(3) . . . . ?
C31 C32 C33 C28 -0.3(3) . . . . ?
C33 C28 C29 C30 1.4(2) . . . . ?
C33 C28 N21 C18 57.9(2) . . . . ?
C33 C28 N21 C22 -117.07(17) . . . . ?
N9 C8 C12 C13 -5.79(19) . . . . ?
N9 C8 C12 O14 173.31(13) . . . . ?
N9 N10 N11 C7 0.50(15) . . . . ?
N10 C15 C16 C17 175.56(13) . . . . ?
N10 C15 C20 C19 -175.30(13) . . . . ?
N11 C7 C8 C12 179.77(14) . . . . ?
N11 C7 C8 N9 -0.53(15) . . . . ?
N21 C18 C19 C20 176.82(14) . . . . ?
N21 C22 C23 C24 178.81(15) . . . . ?
N21 C22 C27 C26 -178.04(16) . . . . ?
N21 C28 C29 C30 -177.24(15) . . . . ?
N21 C28 C33 C32 177.43(14) . . . . ?

_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_ql_1023_d7
_database_code_depnum_ccdc_archive 'CCDC 1888252'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N4 O'
_chemical_formula_sum            'C23 H20 N4 O'
_chemical_formula_weight         368.43
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.5248(5)
_cell_length_b                   9.9507(5)
_cell_length_c                   18.3419(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.599(2)
_cell_angle_gamma                90
_cell_volume                     1894.04(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.58
_cell_measurement_theta_min      4.26
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1314 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.9439.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26941
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.803
_diffrn_reflns_theta_min         4.260
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3425
_reflns_number_total             3950
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.055
_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)+(0.0371P)²+0.6925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0917
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_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
C1 C 0.67315(12) 0.11053(14) 0.31523(7) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.687892 0.171577 0.277706 0.031 Uiso 1 1 calc R . . . .
C2 C 0.69382(13) -0.02586(14) 0.30664(8) 0.0305(3) Uani 1 1 d . . . . .
H2 H 0.722150 -0.057768 0.263243 0.037 Uiso 1 1 calc R . . . .
C3 C 0.67321(13) -0.11564(14) 0.36127(8) 0.0302(3) Uani 1 1 d . . . . .
H3 H 0.686749 -0.209086 0.355239 0.036 Uiso 1 1 calc R . . . .
C4 C 0.63271(13) -0.06841(14) 0.42484(8) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.619734 -0.129688 0.462636 0.035 Uiso 1 1 calc R . . . .
C5 C 0.61099(12) 0.06829(13) 0.43352(7) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.582596 0.099859 0.476969 0.030 Uiso 1 1 calc R . . . .
C6 C 0.63088(11) 0.15886(12) 0.37854(7) 0.0206(2) Uani 1 1 d . . . . .
C7 C 0.60058(11) 0.30263(12) 0.38383(6) 0.0193(2) Uani 1 1 d . . . . .
N8 N 0.49374(9) 0.34354(10) 0.40784(5) 0.0198(2) Uani 1 1 d . . . . .
N9 N 0.49159(9) 0.47670(10) 0.39681(5) 0.0188(2) Uani 1 1 d . . . . .
N10 N 0.58889(9) 0.52590(10) 0.36722(5) 0.0199(2) Uani 1 1 d . . . . .
C11 C 0.66028(11) 0.41678(12) 0.35889(6) 0.0197(2) Uani 1 1 d . . . . .
C12 C 0.78919(11) 0.42808(12) 0.33723(6) 0.0204(2) Uani 1 1 d . . . . .
O13 O 0.87385(8) 0.34976(10) 0.36394(5) 0.0266(2) Uani 1 1 d . . . . .
C14 C 0.81485(11) 0.53456(12) 0.28480(6) 0.0193(2) Uani 1 1 d . . . . .
C15 C 0.71822(11) 0.58441(13) 0.23004(7) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.631709 0.555040 0.227530 0.027 Uiso 1 1 calc R . . . .
C16 C 0.74926(13) 0.67710(14) 0.17928(7) 0.0267(3) Uani 1 1 d . . . . .
H16 H 0.684366 0.708649 0.140793 0.032 Uiso 1 1 calc R . . . .
C17 C 0.87450(13) 0.72389(13) 0.18447(7) 0.0267(3) Uani 1 1 d . . . . .
H17 H 0.894534 0.789354 0.150430 0.032 Uiso 1 1 calc R . . . .
C18 C 0.97095(12) 0.67541(14) 0.23929(7) 0.0260(3) Uani 1 1 d . . . . .
H18 H 1.056644 0.707888 0.242852 0.031 Uiso 1 1 calc R . . . .
C19 C 0.94164(12) 0.57966(13) 0.28866(7) 0.0229(3) Uani 1 1 d . . . . .
H19 H 1.007833 0.544481 0.325255 0.027 Uiso 1 1 calc R . . . .
C20 C 0.38599(11) 0.55811(12) 0.40981(6) 0.0184(2) Uani 1 1 d . . . . .
C21 C 0.29290(11) 0.50583(12) 0.44753(6) 0.0203(2) Uani 1 1 d . . . . .
H21 H 0.300750 0.416506 0.466008 0.024 Uiso 1 1 calc R . . . .
C22 C 0.18871(11) 0.58428(13) 0.45810(6) 0.0204(2) Uani 1 1 d . . . . .
H22 H 0.125921 0.547616 0.484101 0.025 Uiso 1 1 calc R . . . .
C23 C 0.17346(11) 0.71714(12) 0.43125(6) 0.0201(2) Uani 1 1 d . . . . .
C24 C 0.26981(12) 0.76719(13) 0.39318(7) 0.0218(2) Uani 1 1 d . . . . .
H24 H 0.262840 0.856253 0.374277 0.026 Uiso 1 1 calc R . . . .
C25 C 0.37402(12) 0.68888(12) 0.38295(6) 0.0210(2) Uani 1 1 d . . . . .
H25 H 0.437807 0.724733 0.357403 0.025 Uiso 1 1 calc R . . . .
N26 N 0.07007(10) 0.79455(11) 0.44139(6) 0.0253(2) Uani 1 1 d . . . . .
C27 C -0.03458(12) 0.73661(14) 0.47339(7) 0.0262(3) Uani 1 1 d . . . . .
H27A H -0.076129 0.665431 0.440935 0.039 Uiso 1 1 calc GR . . . .
H27B H -0.097860 0.806585 0.478821 0.039 Uiso 1 1 calc GR . . . .
H27C H -0.000441 0.698683 0.522024 0.039 Uiso 1 1 calc GR . . . .
C28 C 0.05212(14) 0.92592(14) 0.40711(8) 0.0302(3) Uani 1 1 d . . . . .
H28A H 0.126397 0.982974 0.425649 0.045 Uiso 1 1 calc GR . . . .
H28B H -0.026390 0.967105 0.419152 0.045 Uiso 1 1 calc GR . . . .
H28C H 0.044219 0.916509 0.353361 0.045 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.3876(19) . ?
C1 C6 1.3963(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3929(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3940(18) . ?
C6 C7 1.4725(17) . ?
C7 N8 1.3377(16) . ?
C7 C11 1.4107(17) . ?
N8 N9 1.3400(15) . ?
N9 N10 1.3298(14) . ?
N9 C20 1.4272(15) . ?
N10 C11 1.3435(16) . ?
C11 C12 1.4802(17) . ?
C12 O13 1.2230(15) . ?
C12 C14 1.4856(17) . ?
C14 C15 1.3960(17) . ?
C14 C19 1.3984(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3877(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3862(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3907(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.3842(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3911(17) . ?
C20 C25 1.3896(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.3857(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.4106(17) . ?
C23 C24 1.4142(17) . ?
C23 N26 1.3709(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3835(17) . ?
C25 H25 0.9500 . ?
N26 C27 1.4512(17) . ?
N26 C28 1.4491(17) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.60(13) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.12(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.73(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.38(13) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.09(12) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 119.47(11) . . ?
C5 C6 C1 119.08(12) . . ?
C5 C6 C7 121.34(11) . . ?
N8 C7 C6 121.37(11) . . ?
N8 C7 C11 107.82(11) . . ?
C11 C7 C6 130.38(11) . . ?
C7 N8 N9 104.19(10) . . ?
N8 N9 C20 122.01(10) . . ?
N10 N9 N8 115.53(10) . . ?
N10 N9 C20 122.23(10) . . ?
N9 N10 C11 103.43(10) . . ?
C7 C11 C12 128.75(11) . . ?
N10 C11 C7 109.03(10) . . ?
N10 C11 C12 121.61(11) . . ?
C11 C12 C14 120.11(10) . . ?
O13 C12 C11 118.90(11) . . ?
O13 C12 C14 120.98(11) . . ?
C15 C14 C12 122.00(11) . . ?
C15 C14 C19 119.80(11) . . ?
C19 C14 C12 118.11(11) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.61(11) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.31(12) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.28(12) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.76(12) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.18(12) . . ?
C18 C19 H19 119.9 . . ?
C21 C20 N9 120.23(11) . . ?
C25 C20 N9 119.96(10) . . ?
C25 C20 C21 119.78(11) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.89(11) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.72(11) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 116.95(11) . . ?
N26 C23 C22 121.74(11) . . ?
N26 C23 C24 121.32(11) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.23(12) . . ?
C25 C24 H24 119.4 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.43(11) . . ?
C24 C25 H25 119.8 . . ?
C23 N26 C27 120.32(11) . . ?
C23 N26 C28 119.80(11) . . ?
C28 N26 C27 118.75(11) . . ?
N26 C27 H27A 109.5 . . ?
N26 C27 H27B 109.5 . . ?
N26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N26 C28 H28A 109.5 . . ?
N26 C28 H28B 109.5 . . ?
N26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C6 C7 N8 134.87(12) . . . . ?
C1 C6 C7 C11 -36.66(19) . . . . ?
C2 C1 C6 C5 0.70(19) . . . . ?
C2 C1 C6 C7 -175.54(12) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.27(18) . . . . ?
C4 C5 C6 C7 175.90(12) . . . . ?
C5 C6 C7 N8 -41.28(17) . . . . ?
C5 C6 C7 C11 147.19(13) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C6 C7 N8 N9 -172.97(10) . . . . ?
C6 C7 C11 N10 171.83(11) . . . . ?
C6 C7 C11 C12 -17.1(2) . . . . ?
C7 N8 N9 N10 0.14(13) . . . . ?
C7 N8 N9 C20 174.76(10) . . . . ?
C7 C11 C12 O13 -26.44(19) . . . . ?
C7 C11 C12 C14 154.53(12) . . . . ?
N8 C7 C11 N10 -0.58(13) . . . . ?
N8 C7 C11 C12 170.45(11) . . . . ?
N8 N9 N10 C11 -0.49(13) . . . . ?
N8 N9 C20 C21 12.15(16) . . . . ?
N8 N9 C20 C25 -166.05(10) . . . . ?
N9 N10 C11 C7 0.62(12) . . . . ?
N9 N10 C11 C12 -171.16(10) . . . . ?
N9 C20 C21 C22 -178.17(10) . . . . ?
N9 C20 C25 C24 177.91(11) . . . . ?
N10 N9 C20 C21 -173.59(10) . . . . ?
N10 N9 C20 C25 8.21(16) . . . . ?
N10 C11 C12 O13 143.58(12) . . . . ?
N10 C11 C12 C14 -35.44(16) . . . . ?
C11 C7 N8 N9 0.26(12) . . . . ?
C11 C12 C14 C15 -29.88(17) . . . . ?
C11 C12 C14 C19 153.70(11) . . . . ?
C12 C14 C15 C16 -175.54(11) . . . . ?
C12 C14 C19 C18 177.79(11) . . . . ?
O13 C12 C14 C15 151.11(12) . . . . ?
O13 C12 C14 C19 -25.31(17) . . . . ?
C14 C15 C16 C17 -2.40(19) . . . . ?
C15 C14 C19 C18 1.29(18) . . . . ?
C15 C16 C17 C18 1.9(2) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C14 -1.82(19) . . . . ?
C19 C14 C15 C16 0.82(18) . . . . ?
C20 N9 N10 C11 -175.10(10) . . . . ?
C20 C21 C22 C23 0.24(18) . . . . ?
C21 C20 C25 C24 -0.31(17) . . . . ?
C21 C22 C23 C24 -0.25(17) . . . . ?
C21 C22 C23 N26 179.68(11) . . . . ?
C22 C23 C24 C25 -0.02(17) . . . . ?
C22 C23 N26 C27 -6.68(18) . . . . ?
C22 C23 N26 C28 -174.38(12) . . . . ?
C23 C24 C25 C20 0.29(18) . . . . ?
C24 C23 N26 C27 173.25(11) . . . . ?
C24 C23 N26 C28 5.55(18) . . . . ?
C25 C20 C21 C22 0.04(17) . . . . ?
N26 C23 C24 C25 -179.95(11) . . . . ?

_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_ql_160_1
_database_code_depnum_ccdc_archive 'CCDC 1888248'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N5'
_chemical_formula_sum            'C27 H19 N5'
_chemical_formula_weight         413.47
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.7931(3)
_cell_length_b                   10.0013(4)
_cell_length_c                   10.8744(4)
_cell_angle_alpha                95.079(2)
_cell_angle_beta                 90.2830(10)
_cell_angle_gamma                100.4010(10)
_cell_volume                     1043.23(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.17
_cell_measurement_theta_min      4.08
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0786 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.9320.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            34077
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         4.082
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3215
_reflns_number_total             3655
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.020
_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)+(0.0368P)²+0.3718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0834
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C26(H26), C27(H27), C28(H28),
  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
C1 C 0.23949(14) 0.90135(14) 0.61830(12) 0.0254(3) Uani 1 1 d . . . . .
H1 H 0.304779 0.974582 0.657829 0.030 Uiso 1 1 calc R . . . .
C2 C 0.09906(14) 0.90630(15) 0.62016(13) 0.0304(3) Uani 1 1 d . . . . .
H2 H 0.068859 0.983019 0.661744 0.036 Uiso 1 1 calc R . . . .
C3 C 0.00187(14) 0.80123(15) 0.56239(13) 0.0310(3) Uani 1 1 d . . . . .
H3 H -0.094269 0.805353 0.564070 0.037 Uiso 1 1 calc R . . . .
C4 C 0.04765(14) 0.68995(14) 0.50207(13) 0.0284(3) Uani 1 1 d . . . . .
H4 H -0.017899 0.617656 0.461509 0.034 Uiso 1 1 calc R . . . .
C5 C 0.18748(13) 0.68270(14) 0.50011(12) 0.0247(3) Uani 1 1 d . . . . .
H5 H 0.216953 0.605331 0.459017 0.030 Uiso 1 1 calc R . . . .
C6 C 0.28513(13) 0.78835(13) 0.55813(11) 0.0223(3) Uani 1 1 d . . . . .
N7 N 0.42845(11) 0.78104(11) 0.55575(9) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.51653(13) 0.83649(13) 0.65900(11) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.64985(13) 0.90734(13) 0.64126(13) 0.0251(3) Uani 1 1 d . . . . .
H9 H 0.683168 0.915809 0.559901 0.030 Uiso 1 1 calc R . . . .
C10 C 0.73406(14) 0.96548(14) 0.74152(14) 0.0322(3) Uani 1 1 d . . . . .
H10 H 0.825316 1.012704 0.728487 0.039 Uiso 1 1 calc R . . . .
C11 C 0.68683(16) 0.95558(15) 0.86035(14) 0.0360(4) Uani 1 1 d . . . . .
H11 H 0.743827 0.998239 0.928878 0.043 Uiso 1 1 calc R . . . .
C12 C 0.55537(16) 0.88269(15) 0.87839(13) 0.0337(3) Uani 1 1 d . . . . .
H12 H 0.522824 0.873985 0.959969 0.040 Uiso 1 1 calc R . . . .
C13 C 0.47063(15) 0.82221(14) 0.77865(12) 0.0276(3) Uani 1 1 d . . . . .
H13 H 0.381244 0.771050 0.792143 0.033 Uiso 1 1 calc R . . . .
C14 C 0.48675(13) 0.72899(13) 0.44657(11) 0.0215(3) Uani 1 1 d . . . . .
C15 C 0.58474(13) 0.64441(13) 0.45412(12) 0.0237(3) Uani 1 1 d . . . . .
H15 H 0.612646 0.622592 0.532586 0.028 Uiso 1 1 calc R . . . .
C16 C 0.64154(13) 0.59210(13) 0.34825(12) 0.0228(3) Uani 1 1 d . . . . .
H16 H 0.708089 0.534410 0.353701 0.027 Uiso 1 1 calc R . . . .
C17 C 0.60044(12) 0.62465(12) 0.23407(11) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.50471(13) 0.71038(13) 0.22453(11) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.478531 0.733439 0.145988 0.026 Uiso 1 1 calc R . . . .
C19 C 0.44799(13) 0.76175(13) 0.33086(12) 0.0224(3) Uani 1 1 d . . . . .
H19 H 0.381972 0.819934 0.325052 0.027 Uiso 1 1 calc R . . . .
N20 N 0.65872(10) 0.56993(10) 0.12515(9) 0.0194(2) Uani 1 1 d . . . . .
N21 N 0.73746(10) 0.47422(10) 0.12816(9) 0.0209(2) Uani 1 1 d . . . . .
C22 C 0.77810(12) 0.45455(12) 0.01185(11) 0.0199(3) Uani 1 1 d . . . . .
C23 C 0.71899(12) 0.54319(12) -0.05761(11) 0.0199(3) Uani 1 1 d . . . . .
N24 N 0.64356(10) 0.61514(11) 0.01579(9) 0.0209(2) Uani 1 1 d . . . . .
C25 C 0.87037(13) 0.35663(12) -0.02173(12) 0.0213(3) Uani 1 1 d . . . . .
C26 C 0.91578(13) 0.33616(13) -0.14211(12) 0.0243(3) Uani 1 1 d . . . . .
H26 H 0.883494 0.382861 -0.205562 0.029 Uiso 1 1 calc R . . . .
C27 C 1.00803(14) 0.24779(13) -0.16974(12) 0.0264(3) Uani 1 1 d . . . . .
H27 H 1.039379 0.235325 -0.251779 0.032 Uiso 1 1 calc R . . . .
C28 C 1.05450(13) 0.17780(13) -0.07840(13) 0.0265(3) Uani 1 1 d . . . . .
H28 H 1.117385 0.117298 -0.097634 0.032 Uiso 1 1 calc R . . . .
C29 C 1.00859(13) 0.19656(13) 0.04175(13) 0.0265(3) Uani 1 1 d . . . . .
H29 H 1.039723 0.148182 0.104509 0.032 Uiso 1 1 calc R . . . .
C30 C 0.91775(13) 0.28544(13) 0.07018(12) 0.0240(3) Uani 1 1 d . . . . .
H30 H 0.887378 0.298218 0.152516 0.029 Uiso 1 1 calc R . . . .
C31 C 0.73363(13) 0.56811(13) -0.18497(12) 0.0221(3) Uani 1 1 d . . . . .
N32 N 0.74964(12) 0.58659(12) -0.28704(10) 0.0283(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.3853(19) . ?
C1 C6 1.3997(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3845(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3930(18) . ?
C6 N7 1.4188(16) . ?
N7 C8 1.4211(16) . ?
N7 C14 1.4181(16) . ?
C8 C9 1.3916(18) . ?
C8 C13 1.3896(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3830(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3956(18) . ?
C14 C19 1.3957(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3832(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3870(18) . ?
C17 C18 1.3892(17) . ?
C17 N20 1.4258(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3833(17) . ?
C19 H19 0.9500 . ?
N20 N21 1.3356(14) . ?
N20 N24 1.3261(14) . ?
N21 C22 1.3364(16) . ?
C22 C23 1.4111(18) . ?
C22 C25 1.4726(17) . ?
C23 N24 1.3403(16) . ?
C23 C31 1.4321(17) . ?
C25 C26 1.3944(18) . ?
C25 C30 1.4008(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.3898(18) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.3919(19) . ?
C29 H29 0.9500 . ?
C29 C30 1.3844(18) . ?
C30 H30 0.9500 . ?
C31 N32 1.1482(17) . ?

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
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.95(13) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.12(13) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.73(13) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.96(13) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.29(12) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 N7 120.80(12) . . ?
C5 C6 C1 118.94(12) . . ?
C5 C6 N7 120.26(11) . . ?
C6 N7 C8 120.15(10) . . ?
C6 N7 C14 120.09(10) . . ?
C14 N7 C8 119.53(10) . . ?
C9 C8 N7 120.18(11) . . ?
C13 C8 N7 120.71(12) . . ?
C13 C8 C9 119.11(12) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.30(13) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.66(13) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.16(13) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.72(13) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 119.99(13) . . ?
C12 C13 H13 120.0 . . ?
C15 C14 N7 119.96(11) . . ?
C15 C14 C19 119.19(11) . . ?
C19 C14 N7 120.85(11) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.52(12) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.38(12) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 121.05(12) . . ?
C16 C17 N20 119.19(11) . . ?
C18 C17 N20 119.75(11) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.16(12) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.68(12) . . ?
C18 C19 H19 119.7 . . ?
N21 N20 C17 121.88(10) . . ?
N24 N20 C17 122.20(10) . . ?
N24 N20 N21 115.86(10) . . ?
N20 N21 C22 104.54(10) . . ?
N21 C22 C23 106.97(11) . . ?
N21 C22 C25 120.77(11) . . ?
C23 C22 C25 132.24(11) . . ?
C22 C23 C31 130.38(11) . . ?
N24 C23 C22 109.81(11) . . ?
N24 C23 C31 119.75(11) . . ?
N20 N24 C23 102.82(10) . . ?
C26 C25 C22 121.70(12) . . ?
C26 C25 C30 118.95(12) . . ?
C30 C25 C22 119.31(11) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.35(12) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.39(12) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C29 119.64(12) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.28(12) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 H30 119.8 . . ?
C29 C30 C25 120.39(12) . . ?
C29 C30 H30 119.8 . . ?
N32 C31 C23 177.66(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C6 N7 C8 34.92(18) . . . . ?
C1 C6 N7 C14 -139.68(13) . . . . ?
C2 C1 C6 C5 0.44(19) . . . . ?
C2 C1 C6 N7 -179.66(12) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 0.09(19) . . . . ?
C4 C5 C6 N7 -179.81(12) . . . . ?
C5 C6 N7 C8 -145.19(12) . . . . ?
C5 C6 N7 C14 40.22(17) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C6 N7 C8 C9 -139.76(12) . . . . ?
C6 N7 C8 C13 39.53(18) . . . . ?
C6 N7 C14 C15 -139.94(13) . . . . ?
C6 N7 C14 C19 40.40(17) . . . . ?
N7 C8 C9 C10 177.75(12) . . . . ?
N7 C8 C13 C12 -176.82(12) . . . . ?
N7 C14 C15 C16 179.48(11) . . . . ?
N7 C14 C19 C18 -179.77(11) . . . . ?
C8 N7 C14 C15 45.44(17) . . . . ?
C8 N7 C14 C19 -134.23(13) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C8 C13 C12 2.48(19) . . . . ?
C9 C10 C11 C12 2.1(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C13 C8 C9 C10 -1.55(19) . . . . ?
C14 N7 C8 C9 34.86(17) . . . . ?
C14 N7 C8 C13 -145.85(12) . . . . ?
C14 C15 C16 C17 0.12(19) . . . . ?
C15 C14 C19 C18 0.57(19) . . . . ?
C15 C16 C17 C18 0.91(19) . . . . ?
C15 C16 C17 N20 -179.67(11) . . . . ?
C16 C17 C18 C19 -1.19(18) . . . . ?
C16 C17 N20 N21 9.05(17) . . . . ?
C16 C17 N20 N24 -167.78(11) . . . . ?
C17 C18 C19 C14 0.44(18) . . . . ?
C17 N20 N21 C22 -176.84(10) . . . . ?
C17 N20 N24 C23 176.77(10) . . . . ?
C18 C17 N20 N21 -171.52(11) . . . . ?
C18 C17 N20 N24 11.65(17) . . . . ?
C19 C14 C15 C16 -0.85(19) . . . . ?
N20 C17 C18 C19 179.40(11) . . . . ?
N20 N21 C22 C23 -0.04(12) . . . . ?
N20 N21 C22 C25 178.76(10) . . . . ?
N21 N20 N24 C23 -0.24(13) . . . . ?
N21 C22 C23 N24 -0.10(14) . . . . ?
N21 C22 C23 C31 176.90(12) . . . . ?
N21 C22 C25 C26 -178.96(11) . . . . ?
N21 C22 C25 C30 -1.17(17) . . . . ?
C22 C23 N24 N20 0.19(13) . . . . ?
C22 C25 C26 C27 176.96(11) . . . . ?
C22 C25 C30 C29 -177.64(11) . . . . ?
C23 C22 C25 C26 -0.5(2) . . . . ?
C23 C22 C25 C30 177.28(12) . . . . ?
N24 N20 N21 C22 0.18(13) . . . . ?
C25 C22 C23 N24 -178.71(12) . . . . ?
C25 C22 C23 C31 -1.7(2) . . . . ?
C25 C26 C27 C28 0.81(19) . . . . ?
C26 C25 C30 C29 0.21(18) . . . . ?
C26 C27 C28 C29 -0.15(19) . . . . ?
C27 C28 C29 C30 -0.48(19) . . . . ?
C28 C29 C30 C25 0.44(19) . . . . ?
C30 C25 C26 C27 -0.84(18) . . . . ?
C31 C23 N24 N20 -177.18(11) . . . . ?

_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_ql_151_2
_database_code_depnum_ccdc_archive 'CCDC 1888247'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H23 Cl N4 O'
_chemical_formula_sum            'C33 H23 Cl N4 O'
_chemical_formula_weight         527.00
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.7632(3)
_cell_length_b                   9.9216(2)
_cell_length_c                   17.6080(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.7020(10)
_cell_angle_gamma                90
_cell_volume                     2570.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.54
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0962 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.9280.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.866
_diffrn_reflns_theta_min         3.003
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4987
_reflns_number_total             5515
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00201(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.031
_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)+(0.0284P)²+1.5195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0810
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18),
 C19(H19), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
;
_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
C1 C 0.57304(8) 0.27707(13) 0.36546(7) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.552766 0.354780 0.337487 0.024 Uiso 1 1 calc R . . . .
C2 C 0.63870(8) 0.19444(14) 0.33776(8) 0.0226(3) Uani 1 1 d . . . . .
H2 H 0.663277 0.215850 0.291039 0.027 Uiso 1 1 calc R . . . .
C3 C 0.66846(9) 0.08061(14) 0.37824(8) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.712824 0.023364 0.359022 0.030 Uiso 1 1 calc R . . . .
C4 C 0.63314(9) 0.05076(14) 0.44690(8) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.653798 -0.026854 0.474779 0.031 Uiso 1 1 calc R . . . .
C5 C 0.56783(9) 0.13342(13) 0.47523(8) 0.0215(3) Uani 1 1 d . . . . .
H5 H 0.544472 0.112738 0.522551 0.026 Uiso 1 1 calc R . . . .
C6 C 0.53654(8) 0.24674(12) 0.43421(7) 0.0172(2) Uani 1 1 d . . . . .
C7 C 0.46206(8) 0.33141(12) 0.45898(7) 0.0163(2) Uani 1 1 d . . . . .
C8 C 0.42845(8) 0.35692(12) 0.53074(7) 0.0170(2) Uani 1 1 d . . . . .
C12 C 0.46295(8) 0.32074(13) 0.60963(7) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.39987(8) 0.33638(13) 0.67134(7) 0.0188(3) Uani 1 1 d . . . . .
C15 C 0.43326(9) 0.39355(14) 0.74031(8) 0.0240(3) Uani 1 1 d . . . . .
H15 H 0.493931 0.426171 0.746166 0.029 Uiso 1 1 calc R . . . .
C16 C 0.37855(10) 0.40320(15) 0.80051(8) 0.0264(3) Uani 1 1 d . . . . .
H16 H 0.400568 0.444634 0.847048 0.032 Uiso 1 1 calc R . . . .
C17 C 0.29138(9) 0.35138(14) 0.79150(8) 0.0236(3) Uani 1 1 d . . . . .
C18 C 0.25627(9) 0.29478(13) 0.72362(8) 0.0222(3) Uani 1 1 d . . . . .
H18 H 0.196054 0.260280 0.718544 0.027 Uiso 1 1 calc R . . . .
C19 C 0.31075(9) 0.28931(13) 0.66289(7) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.287030 0.253246 0.615378 0.024 Uiso 1 1 calc R . . . .
C21 C 0.28237(8) 0.55238(12) 0.41110(7) 0.0151(2) Uani 1 1 d . . . . .
C22 C 0.25172(8) 0.53458(12) 0.33512(7) 0.0169(2) Uani 1 1 d . . . . .
H22 H 0.276155 0.464943 0.305897 0.020 Uiso 1 1 calc R . . . .
C23 C 0.18487(8) 0.61988(12) 0.30234(7) 0.0168(2) Uani 1 1 d . . . . .
H23 H 0.163295 0.608115 0.250437 0.020 Uiso 1 1 calc R . . . .
C24 C 0.14901(8) 0.72306(12) 0.34512(7) 0.0155(2) Uani 1 1 d . . . . .
C25 C 0.18236(8) 0.73978(12) 0.42116(7) 0.0171(2) Uani 1 1 d . . . . .
H25 H 0.159041 0.810189 0.450494 0.020 Uiso 1 1 calc R . . . .
C26 C 0.24882(8) 0.65524(12) 0.45427(7) 0.0163(2) Uani 1 1 d . . . . .
H26 H 0.271241 0.667415 0.505937 0.020 Uiso 1 1 calc R . . . .
C28 C 0.07829(8) 0.84889(12) 0.23553(7) 0.0156(2) Uani 1 1 d . . . . .
C29 C -0.00418(8) 0.85482(12) 0.19069(7) 0.0178(2) Uani 1 1 d . . . . .
H29 H -0.059391 0.834230 0.212356 0.021 Uiso 1 1 calc R . . . .
C30 C -0.00536(9) 0.89082(13) 0.11449(7) 0.0209(3) Uani 1 1 d . . . . .
H30 H -0.061569 0.895263 0.084206 0.025 Uiso 1 1 calc R . . . .
C31 C 0.07512(9) 0.92047(13) 0.08208(7) 0.0214(3) Uani 1 1 d . . . . .
H31 H 0.074247 0.941972 0.029447 0.026 Uiso 1 1 calc R . . . .
C32 C 0.15680(9) 0.91836(13) 0.12731(7) 0.0210(3) Uani 1 1 d . . . . .
H32 H 0.211761 0.941128 0.105844 0.025 Uiso 1 1 calc R . . . .
C33 C 0.15845(8) 0.88321(12) 0.20358(7) 0.0181(2) Uani 1 1 d . . . . .
H33 H 0.214486 0.882510 0.234224 0.022 Uiso 1 1 calc R . . . .
C34 C 0.01144(8) 0.85629(12) 0.35858(7) 0.0151(2) Uani 1 1 d . . . . .
C35 C -0.03331(8) 0.76572(13) 0.40282(7) 0.0191(3) Uani 1 1 d . . . . .
H35 H -0.018726 0.672507 0.401824 0.023 Uiso 1 1 calc R . . . .
C36 C -0.09925(8) 0.81148(14) 0.44841(7) 0.0211(3) Uani 1 1 d . . . . .
H36 H -0.129269 0.749474 0.478920 0.025 Uiso 1 1 calc R . . . .
C37 C -0.12154(8) 0.94704(14) 0.44969(7) 0.0203(3) Uani 1 1 d . . . . .
H37 H -0.166353 0.978163 0.481260 0.024 Uiso 1 1 calc R . . . .
C38 C -0.07808(8) 1.03698(13) 0.40465(7) 0.0200(3) Uani 1 1 d . . . . .
H38 H -0.093929 1.129773 0.404842 0.024 Uiso 1 1 calc R . . . .
C39 C -0.01148(8) 0.99244(12) 0.35919(7) 0.0178(2) Uani 1 1 d . . . . .
H39 H 0.018305 1.054648 0.328634 0.021 Uiso 1 1 calc R . . . .
Cl20 Cl 0.22324(3) 0.35848(4) 0.86784(2) 0.03539(11) Uani 1 1 d . . . . .
N9 N 0.35701(7) 0.44091(10) 0.52040(6) 0.0168(2) Uani 1 1 d . . . . .
N10 N 0.34987(7) 0.46410(10) 0.44602(6) 0.0159(2) Uani 1 1 d . . . . .
N11 N 0.41041(7) 0.40051(10) 0.40612(6) 0.0169(2) Uani 1 1 d . . . . .
N27 N 0.08016(7) 0.80929(11) 0.31292(6) 0.0181(2) Uani 1 1 d . . . . .
O13 O 0.54094(6) 0.28273(10) 0.62442(5) 0.0263(2) 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
C1 H1 0.9500 . ?
C1 C2 1.3882(18) . ?
C1 C6 1.3976(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3893(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3943(17) . ?
C6 C7 1.4777(17) . ?
C7 C8 1.4177(17) . ?
C7 N11 1.3421(15) . ?
C8 C12 1.4838(17) . ?
C8 N9 1.3447(15) . ?
C12 C14 1.4959(17) . ?
C12 O13 1.2193(15) . ?
C14 C15 1.3934(18) . ?
C14 C19 1.3926(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3876(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(2) . ?
C17 C18 1.3825(19) . ?
C17 Cl20 1.7451(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.3907(18) . ?
C19 H19 0.9500 . ?
C21 C22 1.3880(17) . ?
C21 C26 1.3879(17) . ?
C21 N10 1.4276(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3893(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.4003(17) . ?
C24 C25 1.3981(17) . ?
C24 N27 1.4115(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.3828(17) . ?
C26 H26 0.9500 . ?
C28 C29 1.3970(17) . ?
C28 C33 1.3936(17) . ?
C28 N27 1.4163(15) . ?
C29 H29 0.9500 . ?
C29 C30 1.3871(17) . ?
C30 H30 0.9500 . ?
C30 C31 1.3910(19) . ?
C31 H31 0.9500 . ?
C31 C32 1.3898(19) . ?
C32 H32 0.9500 . ?
C32 C33 1.3857(18) . ?
C33 H33 0.9500 . ?
C34 C35 1.3910(17) . ?
C34 C39 1.3928(17) . ?
C34 N27 1.4237(15) . ?
C35 H35 0.9500 . ?
C35 C36 1.3880(18) . ?
C36 H36 0.9500 . ?
C36 C37 1.3852(19) . ?
C37 H37 0.9500 . ?
C37 C38 1.3858(19) . ?
C38 H38 0.9500 . ?
C38 C39 1.3899(17) . ?
C39 H39 0.9500 . ?
N9 N10 1.3253(14) . ?
N10 N11 1.3392(14) . ?

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
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.47(12) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.06(13) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.71(12) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.55(13) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.01(13) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 118.83(11) . . ?
C5 C6 C1 119.17(11) . . ?
C5 C6 C7 121.90(11) . . ?
C8 C7 C6 133.45(11) . . ?
N11 C7 C6 118.68(11) . . ?
N11 C7 C8 107.85(10) . . ?
C7 C8 C12 132.29(11) . . ?
N9 C8 C7 108.53(10) . . ?
N9 C8 C12 118.81(11) . . ?
C8 C12 C14 117.94(10) . . ?
O13 C12 C8 121.36(12) . . ?
O13 C12 C14 120.67(11) . . ?
C15 C14 C12 118.59(11) . . ?
C19 C14 C12 121.78(12) . . ?
C19 C14 C15 119.55(12) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.49(13) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.77(13) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Cl20 119.11(11) . . ?
C18 C17 C16 121.98(13) . . ?
C18 C17 Cl20 118.91(11) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.76(12) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.38(12) . . ?
C18 C19 H19 119.8 . . ?
C22 C21 N10 119.87(11) . . ?
C26 C21 C22 121.25(11) . . ?
C26 C21 N10 118.88(11) . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.16(11) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.59(11) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 N27 121.24(11) . . ?
C25 C24 C23 118.88(11) . . ?
C25 C24 N27 119.88(11) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 120.91(11) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.19(11) . . ?
C25 C26 H26 120.4 . . ?
C29 C28 N27 120.18(11) . . ?
C33 C28 C29 119.42(11) . . ?
C33 C28 N27 120.40(11) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 119.91(12) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.53(12) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.46(12) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.31(12) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 H33 119.8 . . ?
C32 C33 C28 120.31(12) . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C39 119.70(11) . . ?
C35 C34 N27 119.85(11) . . ?
C39 C34 N27 120.45(11) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.02(12) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.38(12) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.2 . . ?
C36 C37 C38 119.62(12) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 H38 119.8 . . ?
C37 C38 C39 120.49(12) . . ?
C39 C38 H38 119.8 . . ?
C34 C39 H39 120.1 . . ?
C38 C39 C34 119.77(12) . . ?
C38 C39 H39 120.1 . . ?
N10 N9 C8 103.86(10) . . ?
N9 N10 C21 121.90(10) . . ?
N9 N10 N11 115.73(9) . . ?
N11 N10 C21 122.37(10) . . ?
N10 N11 C7 104.04(10) . . ?
C24 N27 C28 120.74(10) . . ?
C24 N27 C34 119.66(10) . . ?
C28 N27 C34 119.60(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C6 C7 C8 -158.07(13) . . . . ?
C1 C6 C7 N11 23.53(17) . . . . ?
C2 C1 C6 C5 0.90(18) . . . . ?
C2 C1 C6 C7 -175.57(11) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 -1.29(19) . . . . ?
C4 C5 C6 C7 175.06(12) . . . . ?
C5 C6 C7 C8 25.6(2) . . . . ?
C5 C6 C7 N11 -152.84(12) . . . . ?
C6 C1 C2 C3 0.15(19) . . . . ?
C6 C7 C8 C12 8.8(2) . . . . ?
C6 C7 C8 N9 -178.50(12) . . . . ?
C6 C7 N11 N10 179.22(10) . . . . ?
C7 C8 C12 C14 -166.28(13) . . . . ?
C7 C8 C12 O13 15.6(2) . . . . ?
C7 C8 N9 N10 -0.48(13) . . . . ?
C8 C7 N11 N10 0.44(13) . . . . ?
C8 C12 C14 C15 -136.53(12) . . . . ?
C8 C12 C14 C19 46.77(17) . . . . ?
C8 N9 N10 C21 -178.59(11) . . . . ?
C8 N9 N10 N11 0.83(14) . . . . ?
C12 C8 N9 N10 173.37(10) . . . . ?
C12 C14 C15 C16 -176.45(12) . . . . ?
C12 C14 C19 C18 174.39(12) . . . . ?
C14 C15 C16 C17 1.9(2) . . . . ?
C15 C14 C19 C18 -2.27(19) . . . . ?
C15 C16 C17 C18 -2.3(2) . . . . ?
C15 C16 C17 Cl20 178.10(11) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C14 1.92(19) . . . . ?
C19 C14 C15 C16 0.3(2) . . . . ?
C21 C22 C23 C24 0.31(18) . . . . ?
C21 N10 N11 C7 178.60(11) . . . . ?
C22 C21 C26 C25 1.25(18) . . . . ?
C22 C21 N10 N9 -153.78(11) . . . . ?
C22 C21 N10 N11 26.85(17) . . . . ?
C22 C23 C24 C25 0.72(18) . . . . ?
C22 C23 C24 N27 -179.08(11) . . . . ?
C23 C24 C25 C26 -0.80(18) . . . . ?
C23 C24 N27 C28 -35.06(17) . . . . ?
C23 C24 N27 C34 144.50(12) . . . . ?
C24 C25 C26 C21 -0.17(18) . . . . ?
C25 C24 N27 C28 145.13(12) . . . . ?
C25 C24 N27 C34 -35.30(17) . . . . ?
C26 C21 C22 C23 -1.32(18) . . . . ?
C26 C21 N10 N9 26.43(17) . . . . ?
C26 C21 N10 N11 -152.95(11) . . . . ?
C28 C29 C30 C31 0.35(19) . . . . ?
C29 C28 C33 C32 -2.25(18) . . . . ?
C29 C28 N27 C24 139.05(12) . . . . ?
C29 C28 N27 C34 -40.52(17) . . . . ?
C29 C30 C31 C32 -2.23(19) . . . . ?
C30 C31 C32 C33 1.87(19) . . . . ?
C31 C32 C33 C28 0.37(19) . . . . ?
C33 C28 C29 C30 1.88(18) . . . . ?
C33 C28 N27 C24 -41.42(17) . . . . ?
C33 C28 N27 C34 139.01(12) . . . . ?
C34 C35 C36 C37 0.59(19) . . . . ?
C35 C34 C39 C38 0.76(18) . . . . ?
C35 C34 N27 C24 -48.10(16) . . . . ?
C35 C34 N27 C28 131.47(12) . . . . ?
C35 C36 C37 C38 0.50(19) . . . . ?
C36 C37 C38 C39 -0.97(19) . . . . ?
C37 C38 C39 C34 0.34(18) . . . . ?
C39 C34 C35 C36 -1.22(18) . . . . ?
C39 C34 N27 C24 132.02(12) . . . . ?
C39 C34 N27 C28 -48.41(16) . . . . ?
Cl20 C17 C18 C19 179.99(10) . . . . ?
N9 C8 C12 C14 21.61(17) . . . . ?
N9 C8 C12 O13 -156.51(12) . . . . ?
N9 N10 N11 C7 -0.81(14) . . . . ?
N10 C21 C22 C23 178.89(11) . . . . ?
N10 C21 C26 C25 -178.96(11) . . . . ?
N11 C7 C8 C12 -172.68(13) . . . . ?
N11 C7 C8 N9 0.03(14) . . . . ?
N27 C24 C25 C26 179.01(11) . . . . ?
N27 C28 C29 C30 -178.59(11) . . . . ?
N27 C28 C33 C32 178.22(11) . . . . ?
N27 C34 C35 C36 178.90(11) . . . . ?
N27 C34 C39 C38 -179.36(11) . . . . ?
O13 C12 C14 C15 41.60(18) . . . . ?
O13 C12 C14 C19 -135.09(14) . . . . ?

_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_ql_1020_h
_database_code_depnum_ccdc_archive 'CCDC 1888250'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H23 Br N4 O'
_chemical_formula_sum            'C33 H23 Br N4 O'
_chemical_formula_weight         571.46
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.7956(4)
_cell_length_b                   9.9124(3)
_cell_length_c                   17.6965(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.2860(10)
_cell_angle_gamma                90
_cell_volume                     2584.33(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.20
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    2.442
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8482.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.061
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.943
_diffrn_reflns_theta_min         2.999
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5169
_reflns_number_total             5503
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.032
_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)+(0.0286P)²+1.8016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0660
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
;
_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
C1 C 0.56795(10) 0.13345(14) 0.47244(8) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.544452 0.111132 0.519035 0.021 Uiso 1 1 calc R . . . .
C2 C 0.63306(10) 0.05106(15) 0.44380(9) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.653327 -0.027850 0.470726 0.026 Uiso 1 1 calc R . . . .
C3 C 0.66849(10) 0.08363(15) 0.37614(9) 0.0215(3) Uani 1 1 d . . . . .
H3 H 0.712613 0.026905 0.356661 0.026 Uiso 1 1 calc R . . . .
C4 C 0.63914(10) 0.19958(15) 0.33699(9) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.663757 0.222792 0.291000 0.023 Uiso 1 1 calc R . . . .
C5 C 0.57393(9) 0.28131(14) 0.36511(8) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.553978 0.360318 0.338128 0.020 Uiso 1 1 calc R . . . .
C6 C 0.53730(9) 0.24851(14) 0.43280(8) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.46295(9) 0.33219(13) 0.45759(8) 0.0137(3) Uani 1 1 d . . . . .
N8 N 0.41119(8) 0.40272(12) 0.40548(7) 0.0139(2) Uani 1 1 d . . . . .
N9 N 0.35060(7) 0.46457(11) 0.44545(6) 0.0128(2) Uani 1 1 d . . . . .
N10 N 0.35787(8) 0.43909(12) 0.51915(6) 0.0141(2) Uani 1 1 d . . . . .
C11 C 0.42975(9) 0.35501(13) 0.52910(8) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.46471(9) 0.31692(14) 0.60740(8) 0.0157(3) Uani 1 1 d . . . . .
O13 O 0.54244(7) 0.27731(11) 0.62179(6) 0.0222(2) Uani 1 1 d . . . . .
C14 C 0.40297(9) 0.33295(14) 0.66900(8) 0.0152(3) Uani 1 1 d . . . . .
C15 C 0.31356(9) 0.28585(14) 0.66111(8) 0.0162(3) Uani 1 1 d . . . . .
H15 H 0.288937 0.249593 0.613944 0.019 Uiso 1 1 calc R . . . .
C16 C 0.26048(10) 0.29172(14) 0.72181(8) 0.0180(3) Uani 1 1 d . . . . .
H16 H 0.200360 0.257073 0.717257 0.022 Uiso 1 1 calc R . . . .
C17 C 0.29717(10) 0.34928(15) 0.78923(8) 0.0185(3) Uani 1 1 d . . . . .
Br18 Br 0.22467(2) 0.35784(2) 0.87252(2) 0.02631(6) Uani 1 1 d . . . . .
C19 C 0.38434(10) 0.40175(16) 0.79773(8) 0.0214(3) Uani 1 1 d . . . . .
H19 H 0.407066 0.444091 0.843771 0.026 Uiso 1 1 calc R . . . .
C20 C 0.43771(10) 0.39104(15) 0.73744(8) 0.0196(3) Uani 1 1 d . . . . .
H20 H 0.498375 0.423513 0.742823 0.024 Uiso 1 1 calc R . . . .
C21 C 0.28267(8) 0.55314(13) 0.41091(7) 0.0126(2) Uani 1 1 d . . . . .
C22 C 0.25252(9) 0.53771(14) 0.33485(7) 0.0140(3) Uani 1 1 d . . . . .
H22 H 0.277389 0.469250 0.305420 0.017 Uiso 1 1 calc R . . . .
C23 C 0.18569(9) 0.62321(14) 0.30214(8) 0.0144(3) Uani 1 1 d . . . . .
H23 H 0.164427 0.612672 0.250165 0.017 Uiso 1 1 calc R . . . .
C24 C 0.14939(9) 0.72491(13) 0.34520(7) 0.0128(2) Uani 1 1 d . . . . .
C25 C 0.18198(9) 0.73944(14) 0.42158(8) 0.0142(3) Uani 1 1 d . . . . .
H25 H 0.158134 0.808606 0.451154 0.017 Uiso 1 1 calc R . . . .
C26 C 0.24851(9) 0.65432(14) 0.45455(8) 0.0140(3) Uani 1 1 d . . . . .
H26 H 0.270523 0.664950 0.506345 0.017 Uiso 1 1 calc R . . . .
N27 N 0.08082(8) 0.81196(12) 0.31294(6) 0.0150(2) Uani 1 1 d . . . . .
C28 C 0.07848(9) 0.85164(13) 0.23582(7) 0.0127(2) Uani 1 1 d . . . . .
C29 C -0.00395(9) 0.85628(13) 0.19061(8) 0.0149(3) Uani 1 1 d . . . . .
H29 H -0.058944 0.835319 0.211827 0.018 Uiso 1 1 calc R . . . .
C30 C -0.00537(10) 0.89161(14) 0.11457(8) 0.0180(3) Uani 1 1 d . . . . .
H30 H -0.061579 0.895275 0.084013 0.022 Uiso 1 1 calc R . . . .
C31 C 0.07478(11) 0.92168(14) 0.08276(8) 0.0189(3) Uani 1 1 d . . . . .
H31 H 0.073676 0.942845 0.030328 0.023 Uiso 1 1 calc R . . . .
C32 C 0.15643(10) 0.92050(14) 0.12827(8) 0.0178(3) Uani 1 1 d . . . . .
H32 H 0.211155 0.943090 0.107078 0.021 Uiso 1 1 calc R . . . .
C33 C 0.15862(9) 0.88652(14) 0.20460(8) 0.0153(3) Uani 1 1 d . . . . .
H33 H 0.214604 0.887011 0.235546 0.018 Uiso 1 1 calc R . . . .
C34 C 0.01184(9) 0.85810(13) 0.35772(7) 0.0125(2) Uani 1 1 d . . . . .
C35 C -0.01219(9) 0.99417(14) 0.35770(8) 0.0147(3) Uani 1 1 d . . . . .
H35 H 0.016916 1.056623 0.327215 0.018 Uiso 1 1 calc R . . . .
C36 C -0.07886(9) 1.03814(14) 0.40241(8) 0.0173(3) Uani 1 1 d . . . . .
H36 H -0.095186 1.130826 0.402390 0.021 Uiso 1 1 calc R . . . .
C37 C -0.12172(9) 0.94750(15) 0.44710(8) 0.0173(3) Uani 1 1 d . . . . .
H37 H -0.166813 0.978134 0.477953 0.021 Uiso 1 1 calc R . . . .
C38 C -0.09837(9) 0.81181(15) 0.44649(8) 0.0180(3) Uani 1 1 d . . . . .
H38 H -0.127783 0.749490 0.476836 0.022 Uiso 1 1 calc R . . . .
C39 C -0.03215(9) 0.76687(14) 0.40168(8) 0.0164(3) Uani 1 1 d . . . . .
H39 H -0.016869 0.673823 0.401017 0.020 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
C1 H1 0.9500 . ?
C1 C2 1.393(2) . ?
C1 C6 1.3928(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3978(19) . ?
C6 C7 1.4763(18) . ?
C7 N8 1.3400(18) . ?
C7 C11 1.4172(19) . ?
N8 N9 1.3403(15) . ?
N9 N10 1.3231(15) . ?
N9 C21 1.4288(16) . ?
N10 C11 1.3499(17) . ?
C11 C12 1.4825(18) . ?
C12 O13 1.2196(17) . ?
C12 C14 1.4939(19) . ?
C14 C15 1.3977(19) . ?
C14 C20 1.396(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3891(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 Br18 1.9031(14) . ?
C17 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3869(18) . ?
C21 C26 1.3891(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.3876(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.4003(19) . ?
C24 C25 1.4002(18) . ?
C24 N27 1.4117(17) . ?
C25 H25 0.9500 . ?
C25 C26 1.3838(19) . ?
C26 H26 0.9500 . ?
N27 C28 1.4177(17) . ?
N27 C34 1.4240(17) . ?
C28 C29 1.3964(19) . ?
C28 C33 1.3969(19) . ?
C29 H29 0.9500 . ?
C29 C30 1.3887(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.391(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.389(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.3896(19) . ?
C33 H33 0.9500 . ?
C34 C35 1.3948(18) . ?
C34 C39 1.3928(19) . ?
C35 H35 0.9500 . ?
C35 C36 1.3903(19) . ?
C36 H36 0.9500 . ?
C36 C37 1.388(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.389(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.3893(19) . ?
C39 H39 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
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.04(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.39(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.75(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.98(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.61(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.22(12) . . ?
C1 C6 C7 121.83(12) . . ?
C5 C6 C7 118.84(12) . . ?
N8 C7 C6 118.87(12) . . ?
N8 C7 C11 107.95(11) . . ?
C11 C7 C6 133.16(12) . . ?
C7 N8 N9 104.06(11) . . ?
N8 N9 C21 122.25(11) . . ?
N10 N9 N8 115.81(11) . . ?
N10 N9 C21 121.94(11) . . ?
N9 N10 C11 103.76(11) . . ?
C7 C11 C12 132.39(12) . . ?
N10 C11 C7 108.41(12) . . ?
N10 C11 C12 118.81(12) . . ?
C11 C12 C14 118.09(12) . . ?
O13 C12 C11 121.21(13) . . ?
O13 C12 C14 120.67(12) . . ?
C15 C14 C12 121.89(13) . . ?
C20 C14 C12 118.43(13) . . ?
C20 C14 C15 119.61(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.40(13) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.55(13) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 Br18 118.72(11) . . ?
C19 C17 C16 122.30(13) . . ?
C19 C17 Br18 118.98(11) . . ?
C17 C19 H19 120.7 . . ?
C17 C19 C20 118.50(14) . . ?
C20 C19 H19 120.7 . . ?
C14 C20 H20 119.7 . . ?
C19 C20 C14 120.54(14) . . ?
C19 C20 H20 119.7 . . ?
C22 C21 N9 119.87(12) . . ?
C22 C21 C26 121.21(12) . . ?
C26 C21 N9 118.92(12) . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.38(12) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.46(12) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 118.95(12) . . ?
C23 C24 N27 121.16(12) . . ?
C25 C24 N27 119.88(12) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.84(12) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.14(12) . . ?
C25 C26 H26 120.4 . . ?
C24 N27 C28 120.78(11) . . ?
C24 N27 C34 119.77(11) . . ?
C28 N27 C34 119.43(11) . . ?
C29 C28 N27 120.22(12) . . ?
C29 C28 C33 119.58(12) . . ?
C33 C28 N27 120.20(12) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.86(13) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.58(13) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.47(13) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.46(13) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 H33 120.0 . . ?
C32 C33 C28 119.99(13) . . ?
C32 C33 H33 120.0 . . ?
C35 C34 N27 120.41(12) . . ?
C39 C34 N27 119.87(12) . . ?
C39 C34 C35 119.72(12) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 C34 119.81(13) . . ?
C36 C35 H35 120.1 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.44(13) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.2 . . ?
C36 C37 C38 119.68(12) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.26(13) . . ?
C39 C38 H38 119.9 . . ?
C34 C39 H39 120.0 . . ?
C38 C39 C34 120.07(13) . . ?
C38 C39 H39 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C6 C7 N8 -152.20(13) . . . . ?
C1 C6 C7 C11 26.2(2) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C1 C6 C7 174.70(13) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C4 C5 C6 C7 -175.22(13) . . . . ?
C5 C6 C7 N8 23.80(19) . . . . ?
C5 C6 C7 C11 -157.84(15) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C7 N8 N9 179.04(11) . . . . ?
C6 C7 C11 N10 -178.31(14) . . . . ?
C6 C7 C11 C12 9.2(3) . . . . ?
C7 N8 N9 N10 -0.73(15) . . . . ?
C7 N8 N9 C21 178.92(12) . . . . ?
C7 C11 C12 O13 14.4(2) . . . . ?
C7 C11 C12 C14 -167.74(14) . . . . ?
N8 C7 C11 N10 0.18(16) . . . . ?
N8 C7 C11 C12 -172.35(14) . . . . ?
N8 N9 N10 C11 0.83(15) . . . . ?
N8 N9 C21 C22 26.29(19) . . . . ?
N8 N9 C21 C26 -153.22(12) . . . . ?
N9 N10 C11 C7 -0.58(14) . . . . ?
N9 N10 C11 C12 173.13(12) . . . . ?
N9 C21 C22 C23 179.19(12) . . . . ?
N9 C21 C26 C25 -179.30(12) . . . . ?
N10 N9 C21 C22 -154.08(12) . . . . ?
N10 N9 C21 C26 26.41(19) . . . . ?
N10 C11 C12 O13 -157.56(14) . . . . ?
N10 C11 C12 C14 20.35(19) . . . . ?
C11 C7 N8 N9 0.29(14) . . . . ?
C11 C12 C14 C15 47.86(18) . . . . ?
C11 C12 C14 C20 -135.22(14) . . . . ?
C12 C14 C15 C16 174.34(13) . . . . ?
C12 C14 C20 C19 -176.68(13) . . . . ?
O13 C12 C14 C15 -134.23(15) . . . . ?
O13 C12 C14 C20 42.7(2) . . . . ?
C14 C15 C16 C17 2.1(2) . . . . ?
C15 C14 C20 C19 0.3(2) . . . . ?
C15 C16 C17 Br18 179.90(10) . . . . ?
C15 C16 C17 C19 0.5(2) . . . . ?
C16 C17 C19 C20 -2.7(2) . . . . ?
C17 C19 C20 C14 2.2(2) . . . . ?
Br18 C17 C19 C20 177.93(11) . . . . ?
C20 C14 C15 C16 -2.5(2) . . . . ?
C21 N9 N10 C11 -178.81(12) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C21 C26 C25 1.2(2) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C22 C23 C24 N27 -179.45(12) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C23 C24 N27 C28 -33.60(19) . . . . ?
C23 C24 N27 C34 144.89(13) . . . . ?
C24 C25 C26 C21 -0.3(2) . . . . ?
C24 N27 C28 C29 137.97(13) . . . . ?
C24 N27 C28 C33 -42.12(19) . . . . ?
C24 N27 C34 C35 133.31(14) . . . . ?
C24 N27 C34 C39 -46.86(18) . . . . ?
C25 C24 N27 C28 146.56(13) . . . . ?
C25 C24 N27 C34 -34.95(19) . . . . ?
C26 C21 C22 C23 -1.3(2) . . . . ?
N27 C24 C25 C26 179.33(12) . . . . ?
N27 C28 C29 C30 -178.20(12) . . . . ?
N27 C28 C33 C32 177.61(12) . . . . ?
N27 C34 C35 C36 -179.19(12) . . . . ?
N27 C34 C39 C38 178.85(13) . . . . ?
C28 N27 C34 C35 -48.18(18) . . . . ?
C28 N27 C34 C39 131.65(14) . . . . ?
C28 C29 C30 C31 0.4(2) . . . . ?
C29 C28 C33 C32 -2.5(2) . . . . ?
C29 C30 C31 C32 -2.1(2) . . . . ?
C30 C31 C32 C33 1.5(2) . . . . ?
C31 C32 C33 C28 0.8(2) . . . . ?
C33 C28 C29 C30 1.9(2) . . . . ?
C34 N27 C28 C29 -40.53(18) . . . . ?
C34 N27 C28 C33 139.39(13) . . . . ?
C34 C35 C36 C37 0.0(2) . . . . ?
C35 C34 C39 C38 -1.3(2) . . . . ?
C35 C36 C37 C38 -0.6(2) . . . . ?
C36 C37 C38 C39 0.3(2) . . . . ?
C37 C38 C39 C34 0.7(2) . . . . ?
C39 C34 C35 C36 1.0(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_ql_151_1
_database_code_depnum_ccdc_archive 'CCDC 1888249'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H24 N4 O'
_chemical_formula_sum            'C33 H24 N4 O'
_chemical_formula_weight         492.56
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.0532(2)
_cell_length_b                   29.8500(8)
_cell_length_c                   10.4081(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.3969(9)
_cell_angle_gamma                90
_cell_volume                     2501.92(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.62
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.9092.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34122
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.922
_diffrn_reflns_theta_min         2.961
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4808
_reflns_number_total             5299
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.019
_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)+(0.0373P)²+1.1049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0891
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
;
_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
C1 C 0.09314(14) 0.44333(4) 0.54757(11) 0.0207(2) Uani 1 1 d . . . . .
H1 H 0.043202 0.453864 0.624281 0.025 Uiso 1 1 calc R . . . .
C2 C 0.04009(15) 0.40361(4) 0.49238(12) 0.0235(2) Uani 1 1 d . . . . .
H2 H -0.046979 0.387083 0.531237 0.028 Uiso 1 1 calc R . . . .
C3 C 0.11272(15) 0.38767(4) 0.38091(12) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.075938 0.360290 0.343907 0.030 Uiso 1 1 calc R . . . .
C4 C 0.23946(15) 0.41191(4) 0.32359(12) 0.0248(3) Uani 1 1 d . . . . .
H4 H 0.290489 0.400991 0.247768 0.030 Uiso 1 1 calc R . . . .
C5 C 0.29134(14) 0.45213(4) 0.37739(11) 0.0197(2) Uani 1 1 d . . . . .
H5 H 0.376063 0.469071 0.336917 0.024 Uiso 1 1 calc R . . . .
C6 C 0.22002(13) 0.46784(4) 0.49035(10) 0.0178(2) Uani 1 1 d . . . . .
C7 C 0.27384(13) 0.51107(4) 0.54436(10) 0.0176(2) Uani 1 1 d . . . . .
C8 C 0.27613(14) 0.52758(4) 0.67155(10) 0.0184(2) Uani 1 1 d . . . . .
C12 C 0.26060(14) 0.50328(4) 0.79645(11) 0.0197(2) Uani 1 1 d . . . . .
C14 C 0.20474(14) 0.52873(4) 0.91086(11) 0.0192(2) Uani 1 1 d . . . . .
C15 C 0.10300(14) 0.56634(4) 0.89926(12) 0.0232(2) Uani 1 1 d . . . . .
H15 H 0.068955 0.576313 0.816494 0.028 Uiso 1 1 calc R . . . .
C16 C 0.05133(16) 0.58923(4) 1.00732(13) 0.0294(3) Uani 1 1 d . . . . .
H16 H -0.019423 0.614535 0.998764 0.035 Uiso 1 1 calc R . . . .
C17 C 0.10248(19) 0.57532(4) 1.12735(13) 0.0343(3) Uani 1 1 d . . . . .
H17 H 0.068586 0.591408 1.201436 0.041 Uiso 1 1 calc R . . . .
C18 C 0.2032(2) 0.53797(5) 1.14046(12) 0.0356(3) Uani 1 1 d . . . . .
H18 H 0.237926 0.528517 1.223548 0.043 Uiso 1 1 calc R . . . .
C19 C 0.25351(17) 0.51429(4) 1.03290(12) 0.0280(3) Uani 1 1 d . . . . .
H19 H 0.320898 0.488359 1.042285 0.034 Uiso 1 1 calc R . . . .
C20 C 0.42071(13) 0.61965(4) 0.50050(10) 0.0171(2) Uani 1 1 d . . . . .
C21 C 0.49432(15) 0.62112(4) 0.37999(11) 0.0205(2) Uani 1 1 d . . . . .
H21 H 0.493985 0.595421 0.326142 0.025 Uiso 1 1 calc R . . . .
C22 C 0.56790(15) 0.66047(4) 0.33973(11) 0.0217(2) Uani 1 1 d . . . . .
H22 H 0.615767 0.661902 0.256666 0.026 Uiso 1 1 calc R . . . .
C23 C 0.57308(14) 0.69821(4) 0.41923(11) 0.0189(2) Uani 1 1 d . . . . .
C24 C 0.49452(14) 0.69629(4) 0.53875(11) 0.0192(2) Uani 1 1 d . . . . .
H24 H 0.493990 0.721952 0.592733 0.023 Uiso 1 1 calc R . . . .
C25 C 0.41753(14) 0.65723(4) 0.57888(10) 0.0189(2) Uani 1 1 d . . . . .
H25 H 0.362997 0.656199 0.659468 0.023 Uiso 1 1 calc R . . . .
C27 C 0.81225(14) 0.73409(4) 0.31500(10) 0.0184(2) Uani 1 1 d . . . . .
C28 C 0.92115(15) 0.69877(4) 0.34062(11) 0.0228(2) Uani 1 1 d . . . . .
H28 H 0.892180 0.676785 0.402553 0.027 Uiso 1 1 calc R . . . .
C29 C 1.07104(16) 0.69541(4) 0.27674(13) 0.0267(3) Uani 1 1 d . . . . .
H29 H 1.143503 0.671058 0.294795 0.032 Uiso 1 1 calc R . . . .
C30 C 1.11609(15) 0.72737(4) 0.18653(12) 0.0258(3) Uani 1 1 d . . . . .
H30 H 1.218859 0.725106 0.142734 0.031 Uiso 1 1 calc R . . . .
C31 C 1.00872(15) 0.76264(4) 0.16140(11) 0.0247(3) Uani 1 1 d . . . . .
H31 H 1.039001 0.784778 0.100300 0.030 Uiso 1 1 calc R . . . .
C32 C 0.85779(15) 0.76615(4) 0.22399(11) 0.0216(2) Uani 1 1 d . . . . .
H32 H 0.785243 0.790388 0.204960 0.026 Uiso 1 1 calc R . . . .
C33 C 0.59357(14) 0.78013(4) 0.41438(11) 0.0194(2) Uani 1 1 d . . . . .
C34 C 0.42522(15) 0.78879(4) 0.39587(11) 0.0218(2) Uani 1 1 d . . . . .
H34 H 0.355098 0.766321 0.360347 0.026 Uiso 1 1 calc R . . . .
C35 C 0.35948(15) 0.83018(4) 0.42917(12) 0.0248(3) Uani 1 1 d . . . . .
H35 H 0.244223 0.835731 0.417361 0.030 Uiso 1 1 calc R . . . .
C36 C 0.46100(16) 0.86346(4) 0.47957(12) 0.0253(3) Uani 1 1 d . . . . .
H36 H 0.416138 0.891895 0.501095 0.030 Uiso 1 1 calc R . . . .
C37 C 0.62840(16) 0.85481(4) 0.49818(12) 0.0244(2) Uani 1 1 d . . . . .
H37 H 0.698294 0.877510 0.532714 0.029 Uiso 1 1 calc R . . . .
C38 C 0.69558(15) 0.81326(4) 0.46694(11) 0.0221(2) Uani 1 1 d . . . . .
H38 H 0.810230 0.807507 0.481338 0.026 Uiso 1 1 calc R . . . .
N9 N 0.32611(12) 0.57060(3) 0.66942(9) 0.01863(19) Uani 1 1 d . . . . .
N10 N 0.35339(11) 0.57842(3) 0.54573(8) 0.01669(19) Uani 1 1 d . . . . .
N11 N 0.32367(11) 0.54395(3) 0.46650(9) 0.01744(19) Uani 1 1 d . . . . .
N26 N 0.65868(12) 0.73738(3) 0.38043(10) 0.0214(2) Uani 1 1 d . . . . .
O13 O 0.29932(12) 0.46381(3) 0.80235(8) 0.0284(2) 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
C1 H1 0.9500 . ?
C1 C2 1.3838(16) . ?
C1 C6 1.3938(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3870(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3891(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3879(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3933(16) . ?
C6 C7 1.4716(15) . ?
C7 C8 1.4126(15) . ?
C7 N11 1.3362(14) . ?
C8 C12 1.4947(15) . ?
C8 N9 1.3460(14) . ?
C12 C14 1.4849(16) . ?
C12 O13 1.2201(14) . ?
C14 C15 1.3947(16) . ?
C14 C19 1.3952(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3825(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3869(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3917(16) . ?
C20 C25 1.3873(15) . ?
C20 N10 1.4262(13) . ?
C21 H21 0.9500 . ?
C21 C22 1.3821(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.3983(16) . ?
C23 C24 1.4007(15) . ?
C23 N26 1.4174(14) . ?
C24 H24 0.9500 . ?
C24 C25 1.3864(15) . ?
C25 H25 0.9500 . ?
C27 C28 1.3959(16) . ?
C27 C32 1.3973(15) . ?
C27 N26 1.4194(14) . ?
C28 H28 0.9500 . ?
C28 C29 1.3858(17) . ?
C29 H29 0.9500 . ?
C29 C30 1.3888(18) . ?
C30 H30 0.9500 . ?
C30 C31 1.3861(18) . ?
C31 H31 0.9500 . ?
C31 C32 1.3870(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.3922(17) . ?
C33 C38 1.3949(16) . ?
C33 N26 1.4252(14) . ?
C34 H34 0.9500 . ?
C34 C35 1.3890(16) . ?
C35 H35 0.9500 . ?
C35 C36 1.3872(18) . ?
C36 H36 0.9500 . ?
C36 C37 1.3849(18) . ?
C37 H37 0.9500 . ?
C37 C38 1.3925(16) . ?
C38 H38 0.9500 . ?
N9 N10 1.3282(13) . ?
N10 N11 1.3389(13) . ?

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
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.84(11) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.69(11) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.73(11) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.83(11) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.45(11) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.79(10) . . ?
C5 C6 C1 119.45(10) . . ?
C5 C6 C7 119.70(10) . . ?
C8 C7 C6 131.74(10) . . ?
N11 C7 C6 120.09(10) . . ?
N11 C7 C8 108.06(10) . . ?
C7 C8 C12 130.18(10) . . ?
N9 C8 C7 108.62(9) . . ?
N9 C8 C12 120.28(10) . . ?
C14 C12 C8 118.47(10) . . ?
O13 C12 C8 119.31(10) . . ?
O13 C12 C14 122.17(10) . . ?
C15 C14 C12 121.57(10) . . ?
C15 C14 C19 119.27(11) . . ?
C19 C14 C12 119.15(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.48(11) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.96(12) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.23(12) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.34(12) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 120.2 . . ?
C18 C19 C14 119.70(12) . . ?
C18 C19 H19 120.2 . . ?
C21 C20 N10 119.33(10) . . ?
C25 C20 C21 120.95(10) . . ?
C25 C20 N10 119.68(10) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.09(10) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.10(10) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C24 118.73(10) . . ?
C22 C23 N26 120.57(10) . . ?
C24 C23 N26 120.69(10) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.51(10) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.2 . . ?
C24 C25 C20 119.52(10) . . ?
C24 C25 H25 120.2 . . ?
C28 C27 C32 118.64(10) . . ?
C28 C27 N26 120.60(10) . . ?
C32 C27 N26 120.76(10) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.74(11) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.47(11) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.5 . . ?
C31 C30 C29 118.94(11) . . ?
C31 C30 H30 120.5 . . ?
C30 C31 H31 119.5 . . ?
C30 C31 C32 121.08(11) . . ?
C32 C31 H31 119.5 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.11(11) . . ?
C31 C32 H32 119.9 . . ?
C34 C33 C38 119.54(10) . . ?
C34 C33 N26 119.44(10) . . ?
C38 C33 N26 121.02(10) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.20(11) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.44(11) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.34(11) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.6 . . ?
C36 C37 C38 120.85(11) . . ?
C38 C37 H37 119.6 . . ?
C33 C38 H38 120.2 . . ?
C37 C38 C33 119.62(11) . . ?
C37 C38 H38 120.2 . . ?
N10 N9 C8 103.60(9) . . ?
N9 N10 C20 122.50(9) . . ?
N9 N10 N11 115.58(9) . . ?
N11 N10 C20 121.78(9) . . ?
C7 N11 N10 104.13(9) . . ?
C23 N26 C27 120.44(9) . . ?
C23 N26 C33 119.17(9) . . ?
C27 N26 C33 120.29(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.34(17) . . . . ?
C1 C6 C7 C8 30.30(18) . . . . ?
C1 C6 C7 N11 -145.45(11) . . . . ?
C2 C1 C6 C5 0.43(16) . . . . ?
C2 C1 C6 C7 177.50(10) . . . . ?
C2 C3 C4 C5 -0.70(17) . . . . ?
C3 C4 C5 C6 1.61(17) . . . . ?
C4 C5 C6 C1 -1.47(16) . . . . ?
C4 C5 C6 C7 -178.57(10) . . . . ?
C5 C6 C7 C8 -152.63(12) . . . . ?
C5 C6 C7 N11 31.61(15) . . . . ?
C6 C1 C2 C3 0.47(17) . . . . ?
C6 C7 C8 C12 15.6(2) . . . . ?
C6 C7 C8 N9 -175.61(11) . . . . ?
C6 C7 N11 N10 176.50(9) . . . . ?
C7 C8 C12 C14 -157.48(11) . . . . ?
C7 C8 C12 O13 25.00(18) . . . . ?
C7 C8 N9 N10 -0.65(12) . . . . ?
C8 C7 N11 N10 -0.17(12) . . . . ?
C8 C12 C14 C15 27.72(16) . . . . ?
C8 C12 C14 C19 -153.13(11) . . . . ?
C8 N9 N10 C20 -175.25(10) . . . . ?
C8 N9 N10 N11 0.58(12) . . . . ?
C12 C8 N9 N10 169.44(10) . . . . ?
C12 C14 C15 C16 179.38(11) . . . . ?
C12 C14 C19 C18 179.52(12) . . . . ?
C14 C15 C16 C17 1.02(19) . . . . ?
C15 C14 C19 C18 -1.30(19) . . . . ?
C15 C16 C17 C18 -1.2(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C14 1.2(2) . . . . ?
C19 C14 C15 C16 0.22(17) . . . . ?
C20 C21 C22 C23 1.64(18) . . . . ?
C20 N10 N11 C7 175.61(9) . . . . ?
C21 C20 C25 C24 -2.57(17) . . . . ?
C21 C20 N10 N9 159.85(10) . . . . ?
C21 C20 N10 N11 -15.74(16) . . . . ?
C21 C22 C23 C24 -3.24(18) . . . . ?
C21 C22 C23 N26 175.68(11) . . . . ?
C22 C23 C24 C25 1.93(17) . . . . ?
C22 C23 N26 C27 -39.24(16) . . . . ?
C22 C23 N26 C33 144.34(11) . . . . ?
C23 C24 C25 C20 0.92(17) . . . . ?
C24 C23 N26 C27 139.66(11) . . . . ?
C24 C23 N26 C33 -36.76(16) . . . . ?
C25 C20 C21 C22 1.30(17) . . . . ?
C25 C20 N10 N9 -17.76(16) . . . . ?
C25 C20 N10 N11 166.66(10) . . . . ?
C27 C28 C29 C30 0.44(19) . . . . ?
C28 C27 C32 C31 -0.21(17) . . . . ?
C28 C27 N26 C23 -32.03(16) . . . . ?
C28 C27 N26 C33 144.35(11) . . . . ?
C28 C29 C30 C31 -0.04(19) . . . . ?
C29 C30 C31 C32 -0.48(18) . . . . ?
C30 C31 C32 C27 0.62(18) . . . . ?
C32 C27 C28 C29 -0.31(17) . . . . ?
C32 C27 N26 C23 148.17(11) . . . . ?
C32 C27 N26 C33 -35.45(16) . . . . ?
C33 C34 C35 C36 0.84(17) . . . . ?
C34 C33 C38 C37 -1.09(17) . . . . ?
C34 C33 N26 C23 -46.63(15) . . . . ?
C34 C33 N26 C27 136.94(11) . . . . ?
C34 C35 C36 C37 -0.95(18) . . . . ?
C35 C36 C37 C38 0.03(18) . . . . ?
C36 C37 C38 C33 0.99(18) . . . . ?
C38 C33 C34 C35 0.19(17) . . . . ?
C38 C33 N26 C23 132.76(11) . . . . ?
C38 C33 N26 C27 -43.66(16) . . . . ?
N9 C8 C12 C14 34.85(15) . . . . ?
N9 C8 C12 O13 -142.68(12) . . . . ?
N9 N10 N11 C7 -0.26(12) . . . . ?
N10 C20 C21 C22 -176.27(10) . . . . ?
N10 C20 C25 C24 174.99(10) . . . . ?
N11 C7 C8 C12 -168.25(11) . . . . ?
N11 C7 C8 N9 0.53(13) . . . . ?
N26 C23 C24 C25 -176.99(10) . . . . ?
N26 C27 C28 C29 179.88(11) . . . . ?
N26 C27 C32 C31 179.60(11) . . . . ?
N26 C33 C34 C35 179.60(10) . . . . ?
N26 C33 C38 C37 179.51(10) . . . . ?
O13 C12 C14 C15 -154.83(12) . . . . ?
O13 C12 C14 C19 24.32(17) . . . . ?

_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_ql_1105_q
_database_code_depnum_ccdc_archive 'CCDC 1888253'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H19 F5 N4 O'
_chemical_formula_sum            'C33 H19 F5 N4 O'
_chemical_formula_weight         582.52
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.4579(2)
_cell_length_b                   8.3826(2)
_cell_length_c                   16.9770(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.2450(10)
_cell_angle_gamma                90
_cell_volume                     1298.60(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9565
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.82
_cell_measurement_theta_min      4.85
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0705 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.9087.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32608
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.947
_diffrn_reflns_theta_min         2.698
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Venture Photon II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                5450
_reflns_number_total             5496
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 2480 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(19)
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5496
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.060
_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)+(0.0306P)²+0.2794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0607
_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), C25(H25), C28(H28), C29(H29), C36(H36), C1(H1), C5(H5), C32(H32),
 C38(H38), C41(H41), C4(H4), C42(H42), C33(H33), C2(H2), C39(H39), C3(H3),
 C35(H35), C34(H34), C40(H40)
;
_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
F16 F 0.35970(10) 0.65080(12) 0.31517(6) 0.0185(2) Uani 1 1 d . . . . .
F20 F 0.68342(11) 0.26918(12) 0.47143(6) 0.0203(2) Uani 1 1 d . . . . .
F17 F 0.52727(12) 0.66268(13) 0.20834(6) 0.0237(2) Uani 1 1 d . . . . .
F18 F 0.77237(12) 0.48195(14) 0.23403(6) 0.0249(2) Uani 1 1 d . . . . .
F19 F 0.85006(11) 0.28609(13) 0.36505(7) 0.0249(2) Uani 1 1 d . . . . .
O10 O 0.28136(12) 0.43566(15) 0.41745(7) 0.0176(2) Uani 1 1 d . . . . .
N22 N 0.60327(14) 0.50482(17) 0.65481(8) 0.0142(3) Uani 1 1 d . . . . .
N23 N 0.48048(14) 0.45188(17) 0.67153(8) 0.0150(3) Uani 1 1 d . . . . .
N21 N 0.60164(15) 0.50624(17) 0.57659(8) 0.0146(3) Uani 1 1 d . . . . .
N30 N 1.07940(14) 0.65966(18) 0.92099(8) 0.0163(3) Uani 1 1 d . . . . .
C26 C 0.94956(17) 0.68970(19) 0.77673(10) 0.0160(3) Uani 1 1 d . . . . .
H26 H 1.021161 0.764484 0.770278 0.019 Uiso 1 1 calc R . . . .
C27 C 0.96320(17) 0.61848(19) 0.85312(10) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.46741(16) 0.45021(19) 0.53933(9) 0.0141(3) Uani 1 1 d . . . . .
C6 C 0.24552(17) 0.3477(2) 0.59514(10) 0.0150(3) Uani 1 1 d . . . . .
C11 C 0.47920(18) 0.5582(2) 0.32836(10) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.39132(17) 0.41547(19) 0.59873(10) 0.0142(3) Uani 1 1 d . . . . .
C9 C 0.41193(17) 0.44632(18) 0.44987(10) 0.0138(3) Uani 1 1 d . . . . .
C25 C 0.83267(18) 0.6525(2) 0.71020(10) 0.0156(3) Uani 1 1 d . . . . .
H25 H 0.824486 0.700676 0.658554 0.019 Uiso 1 1 calc R . . . .
C28 C 0.85869(17) 0.50507(19) 0.86058(9) 0.0145(3) Uani 1 1 d . . . . .
H28 H 0.868552 0.452655 0.911352 0.017 Uiso 1 1 calc R . . . .
C37 C 1.06381(17) 0.64058(19) 1.00163(9) 0.0145(3) Uani 1 1 d . . . . .
C24 C 0.72807(17) 0.54352(19) 0.72056(10) 0.0140(3) Uani 1 1 d . . . . .
C31 C 1.22176(17) 0.6907(2) 0.91080(9) 0.0154(3) Uani 1 1 d . . . . .
C29 C 0.74149(17) 0.46832(19) 0.79518(10) 0.0149(3) Uani 1 1 d . . . . .
H29 H 0.670585 0.392234 0.801152 0.018 Uiso 1 1 calc R . . . .
C12 C 0.56410(19) 0.5669(2) 0.27322(10) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.72911(19) 0.3748(2) 0.35332(11) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.68942(19) 0.4742(2) 0.28635(10) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.64299(18) 0.3692(2) 0.40800(10) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.51650(18) 0.46001(19) 0.39676(9) 0.0147(3) Uani 1 1 d . . . . .
C36 C 1.30515(19) 0.8157(2) 0.95313(11) 0.0202(3) Uani 1 1 d . . . . .
H36 H 1.266228 0.881642 0.987834 0.024 Uiso 1 1 calc R . . . .
C1 C 0.18189(18) 0.2290(2) 0.53930(10) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.228054 0.196592 0.498528 0.021 Uiso 1 1 calc R . . . .
C5 C 0.17521(18) 0.3961(2) 0.65413(11) 0.0184(3) Uani 1 1 d . . . . .
H5 H 0.217062 0.477842 0.691815 0.022 Uiso 1 1 calc R . . . .
C32 C 1.27931(19) 0.5953(2) 0.85961(10) 0.0198(3) Uani 1 1 d . . . . .
H32 H 1.223401 0.508993 0.831129 0.024 Uiso 1 1 calc R . . . .
C38 C 0.93584(18) 0.6891(2) 1.02103(10) 0.0176(3) Uani 1 1 d . . . . .
H38 H 0.859014 0.737513 0.980547 0.021 Uiso 1 1 calc R . . . .
C41 C 1.1599(2) 0.5496(2) 1.14037(11) 0.0217(4) Uani 1 1 d . . . . .
H41 H 1.236701 0.501828 1.181129 0.026 Uiso 1 1 calc R . . . .
C4 C 0.04436(19) 0.3248(2) 0.65773(11) 0.0225(4) Uani 1 1 d . . . . .
H4 H -0.002829 0.357834 0.697961 0.027 Uiso 1 1 calc R . . . .
C42 C 1.17657(18) 0.5714(2) 1.06218(10) 0.0179(3) Uani 1 1 d . . . . .
H42 H 1.264660 0.539163 1.049858 0.022 Uiso 1 1 calc R . . . .
C33 C 1.4185(2) 0.6260(2) 0.85005(11) 0.0243(4) Uani 1 1 d . . . . .
H33 H 1.456651 0.561621 0.814419 0.029 Uiso 1 1 calc R . . . .
C2 C 0.05122(19) 0.1584(2) 0.54335(11) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.008478 0.077365 0.505408 0.027 Uiso 1 1 calc R . . . .
C39 C 0.92070(19) 0.6665(2) 1.09963(11) 0.0220(3) Uani 1 1 d . . . . .
H39 H 0.833088 0.699086 1.112388 0.026 Uiso 1 1 calc R . . . .
C3 C -0.01759(18) 0.2056(2) 0.60268(12) 0.0242(4) Uani 1 1 d . . . . .
H3 H -0.106607 0.156323 0.605493 0.029 Uiso 1 1 calc R . . . .
C35 C 1.4455(2) 0.8442(3) 0.94473(12) 0.0257(4) Uani 1 1 d . . . . .
H35 H 1.503048 0.927865 0.974764 0.031 Uiso 1 1 calc R . . . .
C34 C 1.50151(19) 0.7503(3) 0.89238(11) 0.0259(4) Uani 1 1 d . . . . .
H34 H 1.596374 0.771326 0.885691 0.031 Uiso 1 1 calc R . . . .
C40 C 1.0325(2) 0.5968(2) 1.15958(10) 0.0229(4) Uani 1 1 d . . . . .
H40 H 1.021788 0.581668 1.213169 0.028 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
F16 C11 1.3404(19) . ?
F20 C15 1.3386(19) . ?
F17 C12 1.333(2) . ?
F18 C13 1.3323(18) . ?
F19 C14 1.335(2) . ?
O10 C9 1.216(2) . ?
N22 N23 1.3415(18) . ?
N22 N21 1.3241(18) . ?
N22 C24 1.432(2) . ?
N23 C7 1.336(2) . ?
N21 C8 1.345(2) . ?
N30 C27 1.410(2) . ?
N30 C37 1.4240(19) . ?
N30 C31 1.4259(19) . ?
C26 H26 0.9500 . ?
C26 C27 1.403(2) . ?
C26 C25 1.392(2) . ?
C27 C28 1.401(2) . ?
C8 C7 1.415(2) . ?
C8 C9 1.471(2) . ?
C6 C7 1.478(2) . ?
C6 C1 1.397(2) . ?
C6 C5 1.400(2) . ?
C11 C12 1.386(2) . ?
C11 C10 1.391(2) . ?
C9 C10 1.508(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.391(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(2) . ?
C37 C38 1.396(2) . ?
C37 C42 1.398(2) . ?
C24 C29 1.391(2) . ?
C31 C36 1.392(2) . ?
C31 C32 1.393(2) . ?
C29 H29 0.9500 . ?
C12 C13 1.386(2) . ?
C14 C13 1.379(2) . ?
C14 C15 1.388(2) . ?
C15 C10 1.388(2) . ?
C36 H36 0.9500 . ?
C36 C35 1.392(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.392(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.392(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.389(2) . ?
C41 C40 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.389(3) . ?
C42 H42 0.9500 . ?
C33 H33 0.9500 . ?
C33 C34 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.389(3) . ?
C3 H3 0.9500 . ?
C35 H35 0.9500 . ?
C35 C34 1.392(3) . ?
C34 H34 0.9500 . ?
C40 H40 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
N23 N22 C24 119.46(13) . . ?
N21 N22 N23 115.65(13) . . ?
N21 N22 C24 124.71(13) . . ?
C7 N23 N22 104.53(13) . . ?
N22 N21 C8 103.24(12) . . ?
C27 N30 C37 120.17(13) . . ?
C27 N30 C31 120.23(12) . . ?
C37 N30 C31 118.48(13) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 120.99(14) . . ?
C26 C27 N30 120.91(14) . . ?
C28 C27 N30 120.61(14) . . ?
C28 C27 C26 118.48(14) . . ?
N21 C8 C7 109.32(13) . . ?
N21 C8 C9 121.97(14) . . ?
C7 C8 C9 128.40(14) . . ?
C1 C6 C7 122.19(15) . . ?
C1 C6 C5 119.41(15) . . ?
C5 C6 C7 118.21(15) . . ?
F16 C11 C12 118.00(15) . . ?
F16 C11 C10 119.98(14) . . ?
C12 C11 C10 122.00(15) . . ?
N23 C7 C8 107.27(14) . . ?
N23 C7 C6 118.77(14) . . ?
C8 C7 C6 133.93(15) . . ?
O10 C9 C8 120.87(14) . . ?
O10 C9 C10 118.86(14) . . ?
C8 C9 C10 120.25(13) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 C26 118.95(14) . . ?
C24 C25 H25 120.5 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.98(14) . . ?
C29 C28 H28 119.5 . . ?
C38 C37 N30 120.63(15) . . ?
C38 C37 C42 119.25(14) . . ?
C42 C37 N30 120.12(14) . . ?
C25 C24 N22 121.19(14) . . ?
C29 C24 N22 117.80(14) . . ?
C29 C24 C25 121.01(15) . . ?
C36 C31 N30 119.98(15) . . ?
C36 C31 C32 119.53(15) . . ?
C32 C31 N30 120.48(15) . . ?
C28 C29 C24 119.52(14) . . ?
C28 C29 H29 120.2 . . ?
C24 C29 H29 120.2 . . ?
F17 C12 C11 121.17(15) . . ?
F17 C12 C13 119.83(14) . . ?
C13 C12 C11 119.00(15) . . ?
F19 C14 C13 119.75(15) . . ?
F19 C14 C15 120.79(15) . . ?
C13 C14 C15 119.45(15) . . ?
F18 C13 C12 119.60(15) . . ?
F18 C13 C14 119.92(15) . . ?
C14 C13 C12 120.48(15) . . ?
F20 C15 C14 117.76(15) . . ?
F20 C15 C10 120.51(14) . . ?
C14 C15 C10 121.71(15) . . ?
C11 C10 C9 118.82(14) . . ?
C15 C10 C11 117.36(14) . . ?
C15 C10 C9 123.58(14) . . ?
C31 C36 H36 119.9 . . ?
C31 C36 C35 120.15(16) . . ?
C35 C36 H36 119.9 . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 120.03(16) . . ?
C2 C1 H1 120.0 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.19(16) . . ?
C4 C5 H5 119.9 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.22(17) . . ?
C33 C32 H32 119.9 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.05(16) . . ?
C39 C38 H38 120.0 . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C40 C41 C42 120.76(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.19(16) . . ?
C3 C4 H4 119.9 . . ?
C37 C42 H42 120.0 . . ?
C41 C42 C37 120.06(16) . . ?
C41 C42 H42 120.0 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.18(17) . . ?
C34 C33 H33 119.9 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.40(17) . . ?
C3 C2 H2 119.8 . . ?
C38 C39 H39 119.7 . . ?
C40 C39 C38 120.61(16) . . ?
C40 C39 H39 119.7 . . ?
C4 C3 C2 119.77(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C36 C35 H35 119.9 . . ?
C36 C35 C34 120.10(17) . . ?
C34 C35 H35 119.9 . . ?
C33 C34 C35 119.79(16) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C41 C40 C39 119.27(16) . . ?
C41 C40 H40 120.4 . . ?
C39 C40 H40 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F16 C11 C12 F17 -0.9(2) . . . . ?
F16 C11 C12 C13 178.97(14) . . . . ?
F16 C11 C10 C9 6.7(2) . . . . ?
F16 C11 C10 C15 -178.79(14) . . . . ?
F20 C15 C10 C11 -178.36(14) . . . . ?
F20 C15 C10 C9 -4.1(2) . . . . ?
F17 C12 C13 F18 0.2(2) . . . . ?
F17 C12 C13 C14 179.82(15) . . . . ?
F19 C14 C13 F18 -0.5(2) . . . . ?
F19 C14 C13 C12 179.91(15) . . . . ?
F19 C14 C15 F20 -1.6(2) . . . . ?
F19 C14 C15 C10 -179.75(15) . . . . ?
O10 C9 C10 C11 41.9(2) . . . . ?
O10 C9 C10 C15 -132.28(17) . . . . ?
N22 N23 C7 C8 -0.26(17) . . . . ?
N22 N23 C7 C6 178.11(14) . . . . ?
N22 N21 C8 C7 -0.27(17) . . . . ?
N22 N21 C8 C9 173.79(14) . . . . ?
N22 C24 C29 C28 -178.61(14) . . . . ?
N23 N22 N21 C8 0.11(18) . . . . ?
N23 N22 C24 C25 -154.67(15) . . . . ?
N23 N22 C24 C29 25.5(2) . . . . ?
N21 N22 N23 C7 0.10(18) . . . . ?
N21 N22 C24 C25 30.4(2) . . . . ?
N21 N22 C24 C29 -149.48(16) . . . . ?
N21 C8 C7 N23 0.34(18) . . . . ?
N21 C8 C7 C6 -177.67(16) . . . . ?
N21 C8 C9 O10 -160.71(16) . . . . ?
N21 C8 C9 C10 17.6(2) . . . . ?
N30 C27 C28 C29 177.59(15) . . . . ?
N30 C37 C38 C39 178.57(16) . . . . ?
N30 C37 C42 C41 -178.58(16) . . . . ?
N30 C31 C36 C35 178.59(16) . . . . ?
N30 C31 C32 C33 -179.86(16) . . . . ?
C26 C27 C28 C29 -2.5(2) . . . . ?
C26 C25 C24 N22 178.02(15) . . . . ?
C26 C25 C24 C29 -2.1(2) . . . . ?
C27 N30 C37 C38 -44.6(2) . . . . ?
C27 N30 C37 C42 134.80(17) . . . . ?
C27 N30 C31 C36 139.43(17) . . . . ?
C27 N30 C31 C32 -41.5(2) . . . . ?
C27 C26 C25 C24 0.4(2) . . . . ?
C27 C28 C29 C24 0.8(2) . . . . ?
C8 C9 C10 C11 -136.52(16) . . . . ?
C8 C9 C10 C15 49.3(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C11 C12 C13 F18 -179.67(15) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C7 C8 C9 O10 12.1(3) . . . . ?
C7 C8 C9 C10 -169.52(15) . . . . ?
C7 C6 C1 C2 173.87(15) . . . . ?
C7 C6 C5 C4 -174.12(15) . . . . ?
C9 C8 C7 N23 -173.23(15) . . . . ?
C9 C8 C7 C6 8.8(3) . . . . ?
C25 C26 C27 N30 -178.21(15) . . . . ?
C25 C26 C27 C28 1.9(2) . . . . ?
C25 C24 C29 C28 1.5(2) . . . . ?
C37 N30 C27 C26 154.78(15) . . . . ?
C37 N30 C27 C28 -25.3(2) . . . . ?
C37 N30 C31 C36 -52.6(2) . . . . ?
C37 N30 C31 C32 126.42(17) . . . . ?
C37 C38 C39 C40 0.4(3) . . . . ?
C24 N22 N23 C7 -175.28(14) . . . . ?
C24 N22 N21 C8 175.22(15) . . . . ?
C31 N30 C27 C26 -37.5(2) . . . . ?
C31 N30 C27 C28 142.47(16) . . . . ?
C31 N30 C37 C38 147.45(16) . . . . ?
C31 N30 C37 C42 -33.2(2) . . . . ?
C31 C36 C35 C34 1.6(3) . . . . ?
C31 C32 C33 C34 1.0(3) . . . . ?
C12 C11 C10 C9 -174.76(15) . . . . ?
C12 C11 C10 C15 -0.3(2) . . . . ?
C14 C15 C10 C11 -0.3(2) . . . . ?
C14 C15 C10 C9 173.94(15) . . . . ?
C13 C14 C15 F20 178.77(15) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C15 C14 C13 F18 179.16(15) . . . . ?
C15 C14 C13 C12 -0.5(3) . . . . ?
C10 C11 C12 F17 -179.45(15) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C36 C31 C32 C33 -0.8(3) . . . . ?
C36 C35 C34 C33 -1.5(3) . . . . ?
C1 C6 C7 N23 -142.57(16) . . . . ?
C1 C6 C7 C8 35.3(3) . . . . ?
C1 C6 C5 C4 0.9(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C5 C6 C7 N23 32.3(2) . . . . ?
C5 C6 C7 C8 -149.84(18) . . . . ?
C5 C6 C1 C2 -1.0(2) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C32 C31 C36 C35 -0.5(3) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C38 C37 C42 C41 0.8(3) . . . . ?
C38 C39 C40 C41 0.0(3) . . . . ?
C42 C37 C38 C39 -0.8(2) . . . . ?
C42 C41 C40 C39 0.0(3) . . . . ?
C40 C41 C42 C37 -0.4(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_ql_1020i
_database_code_depnum_ccdc_archive 'CCDC 1888251'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H23 F N4 O'
_chemical_formula_sum            'C33 H23 F N4 O'
_chemical_formula_weight         510.55
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.0102(3)
_cell_length_b                   30.2706(10)
_cell_length_c                   10.4005(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3798(17)
_cell_angle_gamma                90
_cell_volume                     2519.67(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.48
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.9422.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            61906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.007
_diffrn_reflns_theta_min         2.920
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4674
_reflns_number_total             5445
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00117(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.052
_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)+(0.0254P)²+1.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0871
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
;
_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
C1 C 0.10688(16) 0.55710(4) 0.53726(13) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.054650 0.547280 0.612471 0.025 Uiso 1 1 calc R . . . .
C2 C 0.06254(17) 0.59746(4) 0.48246(14) 0.0241(3) Uani 1 1 d . . . . .
H2 H -0.021346 0.614962 0.519551 0.029 Uiso 1 1 calc R . . . .
C3 C 0.13998(17) 0.61237(4) 0.37391(14) 0.0255(3) Uani 1 1 d . . . . .
H3 H 0.110617 0.640261 0.337700 0.031 Uiso 1 1 calc R . . . .
C4 C 0.26064(17) 0.58648(4) 0.31807(13) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.314273 0.596698 0.243915 0.029 Uiso 1 1 calc R . . . .
C5 C 0.30255(16) 0.54566(4) 0.37097(12) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.382577 0.527599 0.331257 0.025 Uiso 1 1 calc R . . . .
C6 C 0.22798(15) 0.53098(4) 0.48202(12) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.27367(15) 0.48778(4) 0.53723(12) 0.0188(3) Uani 1 1 d . . . . .
N8 N 0.31823(13) 0.45463(3) 0.46075(10) 0.0183(2) Uani 1 1 d . . . . .
N9 N 0.34361(13) 0.42051(3) 0.54135(10) 0.0178(2) Uani 1 1 d . . . . .
N10 N 0.31835(13) 0.42884(4) 0.66441(10) 0.0191(2) Uani 1 1 d . . . . .
C11 C 0.27466(16) 0.47173(4) 0.66483(12) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.26338(16) 0.49587(4) 0.78965(12) 0.0207(3) Uani 1 1 d . . . . .
O13 O 0.31083(14) 0.53408(3) 0.79822(9) 0.0304(2) Uani 1 1 d . . . . .
C14 C 0.20148(16) 0.47115(4) 0.90144(12) 0.0202(3) Uani 1 1 d . . . . .
C15 C 0.09375(16) 0.43530(5) 0.88392(13) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.060326 0.426249 0.799252 0.028 Uiso 1 1 calc R . . . .
C16 C 0.03496(18) 0.41273(5) 0.98863(14) 0.0274(3) Uani 1 1 d . . . . .
H16 H -0.039939 0.388578 0.977218 0.033 Uiso 1 1 calc R . . . .
C17 C 0.08823(19) 0.42632(5) 1.10957(14) 0.0287(3) Uani 1 1 d . . . . .
F18 F 0.03528(14) 0.40334(3) 1.21209(9) 0.0426(3) Uani 1 1 d . . . . .
C19 C 0.1942(2) 0.46152(5) 1.13174(14) 0.0307(3) Uani 1 1 d . . . . .
H19 H 0.228451 0.469857 1.216847 0.037 Uiso 1 1 calc R . . . .
C20 C 0.24950(18) 0.48450(5) 1.02615(13) 0.0255(3) Uani 1 1 d . . . . .
H20 H 0.320366 0.509429 1.038747 0.031 Uiso 1 1 calc R . . . .
C21 C 0.40801(15) 0.37921(4) 0.49940(12) 0.0186(3) Uani 1 1 d . . . . .
C22 C 0.48249(17) 0.37685(4) 0.38119(13) 0.0218(3) Uani 1 1 d . . . . .
H22 H 0.483268 0.401833 0.325930 0.026 Uiso 1 1 calc R . . . .
C23 C 0.55549(17) 0.33752(4) 0.34528(13) 0.0237(3) Uani 1 1 d . . . . .
H23 H 0.603941 0.335448 0.263665 0.028 Uiso 1 1 calc R . . . .
C24 C 0.55923(16) 0.30081(4) 0.42685(13) 0.0206(3) Uani 1 1 d . . . . .
C25 C 0.47875(16) 0.30363(4) 0.54344(13) 0.0206(3) Uani 1 1 d . . . . .
H25 H 0.476093 0.278599 0.598432 0.025 Uiso 1 1 calc R . . . .
C26 C 0.40281(16) 0.34264(4) 0.57941(12) 0.0199(3) Uani 1 1 d . . . . .
H26 H 0.347586 0.344299 0.658352 0.024 Uiso 1 1 calc R . . . .
N27 N 0.64527(14) 0.26184(4) 0.39304(11) 0.0228(2) Uani 1 1 d . . . . .
C28 C 0.79677(16) 0.26433(4) 0.32679(13) 0.0200(3) Uani 1 1 d . . . . .
C29 C 0.83777(17) 0.23160(4) 0.23872(13) 0.0225(3) Uani 1 1 d . . . . .
H29 H 0.763914 0.207496 0.222508 0.027 Uiso 1 1 calc R . . . .
C30 C 0.98619(18) 0.23426(5) 0.17490(13) 0.0258(3) Uani 1 1 d . . . . .
H30 H 1.013510 0.211704 0.115834 0.031 Uiso 1 1 calc R . . . .
C31 C 1.09528(17) 0.26936(5) 0.19605(14) 0.0269(3) Uani 1 1 d . . . . .
H31 H 1.196041 0.271151 0.151274 0.032 Uiso 1 1 calc R . . . .
C32 C 1.05469(18) 0.30183(5) 0.28379(15) 0.0273(3) Uani 1 1 d . . . . .
H32 H 1.128364 0.326019 0.299308 0.033 Uiso 1 1 calc R . . . .
C33 C 0.90762(17) 0.29920(4) 0.34879(14) 0.0244(3) Uani 1 1 d . . . . .
H33 H 0.882030 0.321483 0.409202 0.029 Uiso 1 1 calc R . . . .
C34 C 0.58003(17) 0.21985(4) 0.42723(13) 0.0211(3) Uani 1 1 d . . . . .
C35 C 0.68379(17) 0.18738(4) 0.48232(13) 0.0230(3) Uani 1 1 d . . . . .
H35 H 0.798975 0.193339 0.499640 0.028 Uiso 1 1 calc R . . . .
C36 C 0.61793(18) 0.14618(4) 0.51187(13) 0.0252(3) Uani 1 1 d . . . . .
H36 H 0.688958 0.123946 0.548333 0.030 Uiso 1 1 calc R . . . .
C37 C 0.44927(19) 0.13736(5) 0.48841(14) 0.0270(3) Uani 1 1 d . . . . .
H37 H 0.404990 0.109161 0.508120 0.032 Uiso 1 1 calc R . . . .
C38 C 0.34608(18) 0.17003(5) 0.43604(14) 0.0274(3) Uani 1 1 d . . . . .
H38 H 0.230231 0.164314 0.421429 0.033 Uiso 1 1 calc R . . . .
C39 C 0.41052(17) 0.21101(4) 0.40475(13) 0.0237(3) Uani 1 1 d . . . . .
H39 H 0.339024 0.233083 0.367953 0.028 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
C1 H1 0.9500 . ?
C1 C2 1.3881(19) . ?
C1 C6 1.3937(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3881(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3949(18) . ?
C6 C7 1.4685(18) . ?
C7 N8 1.3382(16) . ?
C7 C11 1.4130(18) . ?
N8 N9 1.3404(14) . ?
N9 N10 1.3282(15) . ?
N9 C21 1.4275(16) . ?
N10 C11 1.3444(16) . ?
C11 C12 1.4958(17) . ?
C12 O13 1.2194(16) . ?
C12 C14 1.4851(18) . ?
C14 C15 1.3939(19) . ?
C14 C20 1.3972(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(2) . ?
C17 F18 1.3558(16) . ?
C17 C19 1.376(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3905(18) . ?
C21 C26 1.3866(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3845(18) . ?
C23 H23 0.9500 . ?
C23 C24 1.3977(18) . ?
C24 C25 1.3994(18) . ?
C24 N27 1.4178(16) . ?
C25 H25 0.9500 . ?
C25 C26 1.3870(18) . ?
C26 H26 0.9500 . ?
N27 C28 1.4221(17) . ?
N27 C34 1.4250(16) . ?
C28 C29 1.3977(18) . ?
C28 C33 1.3921(18) . ?
C29 H29 0.9500 . ?
C29 C30 1.3879(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.389(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.3947(19) . ?
C34 C39 1.3941(19) . ?
C35 H35 0.9500 . ?
C35 C36 1.3935(19) . ?
C36 H36 0.9500 . ?
C36 C37 1.389(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.386(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.3876(19) . ?
C39 H39 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
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.04(13) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.37(13) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.95(12) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.81(13) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.46(12) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.34(12) . . ?
C1 C6 C7 120.70(12) . . ?
C5 C6 C7 119.94(12) . . ?
N8 C7 C6 120.25(11) . . ?
N8 C7 C11 108.01(11) . . ?
C11 C7 C6 131.69(12) . . ?
C7 N8 N9 104.08(10) . . ?
N8 N9 C21 122.07(10) . . ?
N10 N9 N8 115.54(10) . . ?
N10 N9 C21 122.16(10) . . ?
N9 N10 C11 103.69(10) . . ?
C7 C11 C12 130.46(12) . . ?
N10 C11 C7 108.68(11) . . ?
N10 C11 C12 119.98(11) . . ?
O13 C12 C11 119.80(12) . . ?
O13 C12 C14 122.26(12) . . ?
C14 C12 C11 117.86(11) . . ?
C15 C14 C12 121.00(12) . . ?
C15 C14 C20 119.45(12) . . ?
C20 C14 C12 119.54(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.68(13) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 117.99(13) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C19 123.45(13) . . ?
F18 C17 C16 118.09(14) . . ?
F18 C17 C19 118.46(13) . . ?
C17 C19 H19 121.0 . . ?
C17 C19 C20 118.08(13) . . ?
C20 C19 H19 121.0 . . ?
C14 C20 H20 119.8 . . ?
C19 C20 C14 120.32(13) . . ?
C19 C20 H20 119.8 . . ?
C22 C21 N9 119.28(11) . . ?
C26 C21 N9 119.70(11) . . ?
C26 C21 C22 120.95(12) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.96(12) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.24(12) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.59(12) . . ?
C23 C24 N27 120.62(12) . . ?
C25 C24 N27 120.79(12) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.57(12) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.57(12) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C24 N27 C28 120.62(11) . . ?
C24 N27 C34 119.55(11) . . ?
C28 N27 C34 119.82(10) . . ?
C29 C28 N27 120.56(12) . . ?
C33 C28 N27 120.79(12) . . ?
C33 C28 C29 118.65(12) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.11(12) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.00(13) . . ?
C31 C30 H30 119.5 . . ?
C30 C31 H31 120.6 . . ?
C30 C31 C32 118.89(13) . . ?
C32 C31 H31 120.6 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.47(13) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 H33 119.6 . . ?
C32 C33 C28 120.87(13) . . ?
C32 C33 H33 119.6 . . ?
C35 C34 N27 120.84(12) . . ?
C39 C34 N27 119.60(12) . . ?
C39 C34 C35 119.56(12) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 C34 119.78(13) . . ?
C36 C35 H35 120.1 . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.51(13) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 120.3 . . ?
C38 C37 C36 119.47(13) . . ?
C38 C37 H37 120.3 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.57(13) . . ?
C39 C38 H38 119.7 . . ?
C34 C39 H39 120.0 . . ?
C38 C39 C34 120.09(13) . . ?
C38 C39 H39 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.1(2) . . . . ?
C1 C6 C7 N8 146.68(12) . . . . ?
C1 C6 C7 C11 -30.3(2) . . . . ?
C2 C1 C6 C5 -0.55(19) . . . . ?
C2 C1 C6 C7 -178.67(12) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -1.89(19) . . . . ?
C4 C5 C6 C1 2.01(19) . . . . ?
C4 C5 C6 C7 -179.85(12) . . . . ?
C5 C6 C7 N8 -31.43(18) . . . . ?
C5 C6 C7 C11 151.64(14) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
C6 C7 N8 N9 -177.40(11) . . . . ?
C6 C7 C11 N10 176.65(12) . . . . ?
C6 C7 C11 C12 -14.4(2) . . . . ?
C7 N8 N9 N10 0.26(14) . . . . ?
C7 N8 N9 C21 -174.29(11) . . . . ?
C7 C11 C12 O13 -26.6(2) . . . . ?
C7 C11 C12 C14 156.37(13) . . . . ?
N8 C7 C11 N10 -0.56(14) . . . . ?
N8 C7 C11 C12 168.44(12) . . . . ?
N8 N9 N10 C11 -0.60(14) . . . . ?
N8 N9 C21 C22 15.14(18) . . . . ?
N8 N9 C21 C26 -167.96(11) . . . . ?
N9 N10 C11 C7 0.67(13) . . . . ?
N9 N10 C11 C12 -169.68(11) . . . . ?
N9 C21 C22 C23 175.34(12) . . . . ?
N9 C21 C26 C25 -174.25(11) . . . . ?
N10 N9 C21 C22 -159.04(12) . . . . ?
N10 N9 C21 C26 17.85(18) . . . . ?
N10 C11 C12 O13 141.37(13) . . . . ?
N10 C11 C12 C14 -35.67(17) . . . . ?
C11 C7 N8 N9 0.19(13) . . . . ?
C11 C12 C14 C15 -26.98(18) . . . . ?
C11 C12 C14 C20 154.18(12) . . . . ?
C12 C14 C15 C16 -179.23(12) . . . . ?
C12 C14 C20 C19 -179.36(13) . . . . ?
O13 C12 C14 C15 156.06(13) . . . . ?
O13 C12 C14 C20 -22.8(2) . . . . ?
C14 C15 C16 C17 -1.1(2) . . . . ?
C15 C14 C20 C19 1.8(2) . . . . ?
C15 C16 C17 F18 -177.82(12) . . . . ?
C15 C16 C17 C19 1.2(2) . . . . ?
C16 C17 C19 C20 0.2(2) . . . . ?
C17 C19 C20 C14 -1.7(2) . . . . ?
F18 C17 C19 C20 179.17(13) . . . . ?
C20 C14 C15 C16 -0.4(2) . . . . ?
C21 N9 N10 C11 173.94(11) . . . . ?
C21 C22 C23 C24 -1.7(2) . . . . ?
C22 C21 C26 C25 2.59(19) . . . . ?
C22 C23 C24 C25 3.7(2) . . . . ?
C22 C23 C24 N27 -175.24(13) . . . . ?
C23 C24 C25 C26 -2.6(2) . . . . ?
C23 C24 N27 C28 36.09(19) . . . . ?
C23 C24 N27 C34 -144.66(13) . . . . ?
C24 C25 C26 C21 -0.5(2) . . . . ?
C24 N27 C28 C29 -147.25(13) . . . . ?
C24 N27 C28 C33 33.13(19) . . . . ?
C24 N27 C34 C35 -134.01(13) . . . . ?
C24 N27 C34 C39 46.31(18) . . . . ?
C25 C24 N27 C28 -142.81(13) . . . . ?
C25 C24 N27 C34 36.44(18) . . . . ?
C26 C21 C22 C23 -1.5(2) . . . . ?
N27 C24 C25 C26 176.35(12) . . . . ?
N27 C28 C29 C30 -179.78(12) . . . . ?
N27 C28 C33 C32 -179.59(13) . . . . ?
N27 C34 C35 C36 -178.34(12) . . . . ?
N27 C34 C39 C38 179.12(12) . . . . ?
C28 N27 C34 C35 45.25(18) . . . . ?
C28 N27 C34 C39 -134.43(13) . . . . ?
C28 C29 C30 C31 -0.6(2) . . . . ?
C29 C28 C33 C32 0.8(2) . . . . ?
C29 C30 C31 C32 0.8(2) . . . . ?
C30 C31 C32 C33 -0.1(2) . . . . ?
C31 C32 C33 C28 -0.7(2) . . . . ?
C33 C28 C29 C30 -0.2(2) . . . . ?
C34 N27 C28 C29 33.50(19) . . . . ?
C34 N27 C28 C33 -146.12(13) . . . . ?
C34 C35 C36 C37 -0.8(2) . . . . ?
C35 C34 C39 C38 -0.6(2) . . . . ?
C35 C36 C37 C38 -0.4(2) . . . . ?
C36 C37 C38 C39 1.2(2) . . . . ?
C37 C38 C39 C34 -0.7(2) . . . . ?
C39 C34 C35 C36 1.3(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_ql_1023_d5_0m
_database_code_depnum_ccdc_archive 'CCDC 1888254'
loop_
_audit_author_name
_audit_author_address
'QI LAI'
;Jilin University
China
;
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H28 N4 O Si'
_chemical_formula_sum            'C30 H28 N4 O Si'
_chemical_formula_weight         488.65
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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                   9.8270(5)
_cell_length_b                   19.5256(9)
_cell_length_c                   14.1862(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.903(2)
_cell_angle_gamma                90
_cell_volume                     2559.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9504
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.07
_cell_measurement_theta_min      4.79
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0863 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            55930
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.861
_diffrn_reflns_theta_min         4.013
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4885
_reflns_number_total             5457
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+1.2550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0906
_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:
 C27(H27), C33(H33), C36(H36), C16(H16), C22(H22), C30(H30), C35(H35),
 C17(H17), C19(H19), C14(H14), C29(H29), C32(H32), C20(H20), C28(H28), C26(H26),
  C23(H23), C34(H34), C15(H15), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_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
Si4 Si 1.22350(4) 0.39742(2) 0.82200(2) 0.01743(9) Uani 1 1 d . . . . .
C27 C 0.55259(16) 0.74411(7) 0.34891(11) 0.0259(3) Uani 1 1 d . . . . .
H27 H 0.633537 0.772602 0.355062 0.031 Uiso 1 1 calc R . . . .
O11 O 1.14686(10) 0.36426(5) 1.01142(7) 0.0240(2) Uani 1 1 d . . . . .
C33 C 0.02739(15) 0.70204(7) 0.49466(10) 0.0219(3) Uani 1 1 d . . . . .
H33 H -0.032824 0.741221 0.474279 0.026 Uiso 1 1 calc R . . . .
N6 N 0.96918(12) 0.47589(5) 0.75154(8) 0.0172(2) Uani 1 1 d . . . . .
N8 N 0.85398(12) 0.46908(5) 0.86484(8) 0.0170(2) Uani 1 1 d . . . . .
N7 N 0.85376(12) 0.49312(5) 0.77726(8) 0.0167(2) Uani 1 1 d . . . . .
N24 N 0.39710(12) 0.64674(6) 0.51372(8) 0.0207(2) Uani 1 1 d . . . . .
C1 C 1.38410(15) 0.41599(8) 0.93494(11) 0.0271(3) Uani 1 1 d . . . . .
H1A H 1.383074 0.464336 0.953233 0.041 Uiso 1 1 calc GR . . . .
H1B H 1.472669 0.406239 0.920267 0.041 Uiso 1 1 calc GR . . . .
H1C H 1.381076 0.387166 0.990742 0.041 Uiso 1 1 calc GR . . . .
C36 C 0.20249(14) 0.58715(7) 0.55246(9) 0.0187(2) Uani 1 1 d . . . . .
H36 H 0.261608 0.547525 0.571579 0.022 Uiso 1 1 calc R . . . .
C31 C 0.25542(14) 0.64556(6) 0.51989(9) 0.0181(2) Uani 1 1 d . . . . .
C16 C 0.94615(16) 0.33683(7) 1.21979(10) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.995199 0.313515 1.280688 0.028 Uiso 1 1 calc R . . . .
C22 C 0.52569(14) 0.60171(7) 0.68176(10) 0.0200(3) Uani 1 1 d . . . . .
H22 H 0.458315 0.624010 0.706076 0.024 Uiso 1 1 calc R . . . .
C2 C 1.25667(16) 0.43582(8) 0.71148(11) 0.0264(3) Uani 1 1 d . . . . .
H2A H 1.171114 0.429210 0.651503 0.040 Uiso 1 1 calc GR . . . .
H2B H 1.340342 0.413515 0.701886 0.040 Uiso 1 1 calc GR . . . .
H2C H 1.275996 0.484911 0.722944 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.97830(14) 0.43334(6) 0.89865(9) 0.0172(2) Uani 1 1 d . . . . .
C30 C 0.31616(15) 0.66032(7) 0.33098(10) 0.0218(3) Uani 1 1 d . . . . .
H30 H 0.235266 0.631733 0.324559 0.026 Uiso 1 1 calc R . . . .
C18 C 0.73676(13) 0.53186(6) 0.71172(9) 0.0169(2) Uani 1 1 d . . . . .
C10 C 1.02990(14) 0.39332(6) 0.99303(9) 0.0181(2) Uani 1 1 d . . . . .
C35 C 0.06322(15) 0.58690(7) 0.55697(9) 0.0208(3) Uani 1 1 d . . . . .
H35 H 0.028477 0.547348 0.580542 0.025 Uiso 1 1 calc R . . . .
C17 C 1.01687(14) 0.35033(6) 1.15256(9) 0.0192(3) Uani 1 1 d . . . . .
H17 H 1.114376 0.336040 1.167525 0.023 Uiso 1 1 calc R . . . .
C21 C 0.51045(14) 0.60755(6) 0.57984(9) 0.0181(2) Uani 1 1 d . . . . .
C12 C 0.94610(14) 0.38487(6) 1.06261(9) 0.0177(2) Uani 1 1 d . . . . .
C19 C 0.72384(14) 0.53680(7) 0.61132(9) 0.0186(2) Uani 1 1 d . . . . .
H19 H 0.792186 0.514786 0.587634 0.022 Uiso 1 1 calc R . . . .
C14 C 0.73282(15) 0.39206(8) 1.11020(10) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.635576 0.406497 1.096086 0.030 Uiso 1 1 calc R . . . .
C29 C 0.33585(16) 0.68754(7) 0.24597(10) 0.0250(3) Uani 1 1 d . . . . .
H29 H 0.267854 0.677683 0.181575 0.030 Uiso 1 1 calc R . . . .
C32 C 0.16717(15) 0.70346(7) 0.49150(10) 0.0208(3) Uani 1 1 d . . . . .
H32 H 0.202666 0.743680 0.470098 0.025 Uiso 1 1 calc R . . . .
C3 C 1.18899(16) 0.30367(7) 0.80434(11) 0.0257(3) Uani 1 1 d . . . . .
H3A H 1.163599 0.285399 0.860530 0.039 Uiso 1 1 calc GR . . . .
H3B H 1.276260 0.280691 0.801663 0.039 Uiso 1 1 calc GR . . . .
H3C H 1.108940 0.295597 0.741521 0.039 Uiso 1 1 calc GR . . . .
C20 C 0.61064(14) 0.57404(7) 0.54579(9) 0.0192(2) Uani 1 1 d . . . . .
H20 H 0.601128 0.576797 0.476970 0.023 Uiso 1 1 calc R . . . .
C28 C 0.45405(17) 0.72896(7) 0.25457(11) 0.0256(3) Uani 1 1 d . . . . .
H28 H 0.467691 0.746939 0.196199 0.031 Uiso 1 1 calc R . . . .
C5 C 1.05148(13) 0.43760(6) 0.82814(9) 0.0169(2) Uani 1 1 d . . . . .
C25 C 0.41509(14) 0.67500(6) 0.42555(9) 0.0185(2) Uani 1 1 d . . . . .
C26 C 0.53264(15) 0.71754(7) 0.43435(10) 0.0230(3) Uani 1 1 d . . . . .
H26 H 0.599317 0.728439 0.498796 0.028 Uiso 1 1 calc R . . . .
C23 C 0.63754(14) 0.56389(7) 0.74726(9) 0.0201(3) Uani 1 1 d . . . . .
H23 H 0.646283 0.559902 0.815817 0.024 Uiso 1 1 calc R . . . .
C34 C -0.02534(15) 0.64397(7) 0.52730(10) 0.0215(3) Uani 1 1 d . . . . .
H34 H -0.120996 0.643339 0.529282 0.026 Uiso 1 1 calc R . . . .
C15 C 0.80372(15) 0.35732(7) 1.19832(10) 0.0231(3) Uani 1 1 d . . . . .
H15 H 0.754780 0.347509 1.244102 0.028 Uiso 1 1 calc R . . . .
C13 C 0.80318(15) 0.40601(7) 1.04204(10) 0.0229(3) Uani 1 1 d . . . . .
H13 H 0.753959 0.429867 0.981662 0.028 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
Si4 C1 1.8621(14) . ?
Si4 C2 1.8640(14) . ?
Si4 C3 1.8631(14) . ?
Si4 C5 1.8924(13) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(2) . ?
C27 C26 1.3923(19) . ?
O11 C10 1.2276(16) . ?
C33 H33 0.9500 . ?
C33 C32 1.3899(19) . ?
C33 C34 1.3900(19) . ?
N6 N7 1.3470(15) . ?
N6 C5 1.3400(16) . ?
N8 N7 1.3274(14) . ?
N8 C9 1.3457(16) . ?
N7 C18 1.4251(16) . ?
N24 C31 1.4246(17) . ?
N24 C21 1.4124(16) . ?
N24 C25 1.4321(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C36 H36 0.9500 . ?
C36 C31 1.3959(18) . ?
C36 C35 1.3917(19) . ?
C31 C32 1.3981(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3833(19) . ?
C16 C15 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.4066(18) . ?
C22 C23 1.3861(18) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C9 C10 1.4825(17) . ?
C9 C5 1.4193(17) . ?
C30 H30 0.9500 . ?
C30 C29 1.3903(19) . ?
C30 C25 1.3925(18) . ?
C18 C19 1.3896(17) . ?
C18 C23 1.3895(18) . ?
C10 C12 1.4945(17) . ?
C35 H35 0.9500 . ?
C35 C34 1.3881(19) . ?
C17 H17 0.9500 . ?
C17 C12 1.4008(17) . ?
C21 C20 1.3982(18) . ?
C12 C13 1.3960(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3879(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3840(19) . ?
C14 C13 1.3938(19) . ?
C29 H29 0.9500 . ?
C29 C28 1.386(2) . ?
C32 H32 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C20 H20 0.9500 . ?
C28 H28 0.9500 . ?
C25 C26 1.3935(19) . ?
C26 H26 0.9500 . ?
C23 H23 0.9500 . ?
C34 H34 0.9500 . ?
C15 H15 0.9500 . ?
C13 H13 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
C1 Si4 C2 107.80(7) . . ?
C1 Si4 C3 111.67(7) . . ?
C1 Si4 C5 112.85(6) . . ?
C2 Si4 C5 106.66(6) . . ?
C3 Si4 C2 110.98(7) . . ?
C3 Si4 C5 106.80(6) . . ?
C28 C27 H27 120.0 . . ?
C28 C27 C26 120.01(13) . . ?
C26 C27 H27 120.0 . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.78(12) . . ?
C34 C33 H33 119.6 . . ?
C5 N6 N7 104.54(10) . . ?
N7 N8 C9 103.24(10) . . ?
N6 N7 C18 121.50(10) . . ?
N8 N7 N6 115.60(10) . . ?
N8 N7 C18 122.83(10) . . ?
C31 N24 C25 118.27(10) . . ?
C21 N24 C31 121.12(10) . . ?
C21 N24 C25 119.00(10) . . ?
Si4 C1 H1A 109.5 . . ?
Si4 C1 H1B 109.5 . . ?
Si4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C31 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C31 120.08(12) . . ?
C36 C31 N24 121.04(11) . . ?
C36 C31 C32 119.45(12) . . ?
C32 C31 N24 119.51(11) . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.02(12) . . ?
C15 C16 H16 120.0 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C23 C22 C21 120.99(12) . . ?
Si4 C2 H2A 109.5 . . ?
Si4 C2 H2B 109.5 . . ?
Si4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N8 C9 C10 125.81(11) . . ?
N8 C9 C5 109.56(11) . . ?
C5 C9 C10 124.60(11) . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C25 119.95(13) . . ?
C25 C30 H30 120.0 . . ?
C19 C18 N7 118.52(11) . . ?
C23 C18 N7 120.80(11) . . ?
C23 C18 C19 120.67(12) . . ?
O11 C10 C9 116.31(11) . . ?
O11 C10 C12 119.67(11) . . ?
C9 C10 C12 123.97(11) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 C36 120.54(12) . . ?
C34 C35 H35 119.7 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C12 120.63(12) . . ?
C12 C17 H17 119.7 . . ?
C22 C21 N24 120.70(11) . . ?
C20 C21 N24 120.86(11) . . ?
C20 C21 C22 118.43(12) . . ?
C17 C12 C10 116.14(11) . . ?
C13 C12 C10 124.79(11) . . ?
C13 C12 C17 119.01(12) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.72(12) . . ?
C20 C19 H19 120.1 . . ?
C15 C14 H14 119.8 . . ?
C15 C14 C13 120.42(13) . . ?
C13 C14 H14 119.8 . . ?
C30 C29 H29 119.8 . . ?
C28 C29 C30 120.43(13) . . ?
C28 C29 H29 119.8 . . ?
C33 C32 C31 119.83(12) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
Si4 C3 H3A 109.5 . . ?
Si4 C3 H3B 109.5 . . ?
Si4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.78(12) . . ?
C19 C20 H20 119.6 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.79(12) . . ?
C29 C28 H28 120.1 . . ?
N6 C5 Si4 119.74(9) . . ?
N6 C5 C9 107.07(11) . . ?
C9 C5 Si4 133.08(9) . . ?
C30 C25 N24 120.59(12) . . ?
C30 C25 C26 119.65(12) . . ?
C26 C25 N24 119.77(12) . . ?
C27 C26 C25 120.15(13) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C22 C23 C18 119.39(11) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.31(12) . . ?
C35 C34 H34 120.3 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.01(13) . . ?
C14 C15 H15 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.90(12) . . ?
C14 C13 H13 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C10 C12 C17 7.76(18) . . . . ?
O11 C10 C12 C13 -169.29(13) . . . . ?
N6 N7 C18 C19 16.51(17) . . . . ?
N6 N7 C18 C23 -163.64(12) . . . . ?
N8 N7 C18 C19 -160.39(11) . . . . ?
N8 N7 C18 C23 19.47(18) . . . . ?
N8 C9 C10 O11 -179.70(12) . . . . ?
N8 C9 C10 C12 2.6(2) . . . . ?
N8 C9 C5 Si4 -176.33(10) . . . . ?
N8 C9 C5 N6 -0.40(14) . . . . ?
N7 N6 C5 Si4 176.81(8) . . . . ?
N7 N6 C5 C9 0.23(13) . . . . ?
N7 N8 C9 C10 -177.58(11) . . . . ?
N7 N8 C9 C5 0.37(13) . . . . ?
N7 C18 C19 C20 179.80(11) . . . . ?
N7 C18 C23 C22 179.43(12) . . . . ?
N24 C31 C32 C33 178.21(12) . . . . ?
N24 C21 C20 C19 178.57(12) . . . . ?
N24 C25 C26 C27 178.69(12) . . . . ?
C1 Si4 C5 N6 128.42(10) . . . . ?
C1 Si4 C5 C9 -56.06(14) . . . . ?
C36 C31 C32 C33 -0.86(19) . . . . ?
C36 C35 C34 C33 -1.18(19) . . . . ?
C31 N24 C21 C22 -39.99(18) . . . . ?
C31 N24 C21 C20 140.43(13) . . . . ?
C31 N24 C25 C30 -42.21(17) . . . . ?
C31 N24 C25 C26 137.83(13) . . . . ?
C31 C36 C35 C34 1.33(19) . . . . ?
C16 C17 C12 C10 -176.75(12) . . . . ?
C16 C17 C12 C13 0.49(19) . . . . ?
C22 C21 C20 C19 -1.03(19) . . . . ?
C2 Si4 C5 N6 10.23(12) . . . . ?
C2 Si4 C5 C9 -174.25(12) . . . . ?
C9 N8 N7 N6 -0.24(13) . . . . ?
C9 N8 N7 C18 176.83(11) . . . . ?
C9 C10 C12 C17 -174.65(11) . . . . ?
C9 C10 C12 C13 8.3(2) . . . . ?
C30 C29 C28 C27 -0.8(2) . . . . ?
C30 C25 C26 C27 -1.3(2) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C10 C9 C5 Si4 1.7(2) . . . . ?
C10 C9 C5 N6 177.59(11) . . . . ?
C10 C12 C13 C14 176.39(13) . . . . ?
C35 C36 C31 N24 -179.36(11) . . . . ?
C35 C36 C31 C32 -0.30(18) . . . . ?
C17 C16 C15 C14 -0.8(2) . . . . ?
C17 C12 C13 C14 -0.6(2) . . . . ?
C21 N24 C31 C36 -30.75(18) . . . . ?
C21 N24 C31 C32 150.19(12) . . . . ?
C21 N24 C25 C30 123.52(14) . . . . ?
C21 N24 C25 C26 -56.44(17) . . . . ?
C21 C22 C23 C18 0.6(2) . . . . ?
C19 C18 C23 C22 -0.72(19) . . . . ?
C29 C30 C25 N24 -179.31(12) . . . . ?
C29 C30 C25 C26 0.6(2) . . . . ?
C32 C33 C34 C35 0.0(2) . . . . ?
C3 Si4 C5 N6 -108.50(11) . . . . ?
C3 Si4 C5 C9 67.02(13) . . . . ?
C28 C27 C26 C25 0.9(2) . . . . ?
C5 N6 N7 N8 0.00(14) . . . . ?
C5 N6 N7 C18 -177.11(11) . . . . ?
C5 C9 C10 O11 2.64(19) . . . . ?
C5 C9 C10 C12 -175.03(12) . . . . ?
C25 N24 C31 C36 134.67(12) . . . . ?
C25 N24 C31 C32 -44.40(17) . . . . ?
C25 N24 C21 C22 154.71(12) . . . . ?
C25 N24 C21 C20 -24.88(18) . . . . ?
C25 C30 C29 C28 0.4(2) . . . . ?
C26 C27 C28 C29 0.2(2) . . . . ?
C23 C22 C21 N24 -179.35(12) . . . . ?
C23 C22 C21 C20 0.2(2) . . . . ?
C23 C18 C19 C20 -0.05(19) . . . . ?
C34 C33 C32 C31 1.0(2) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C15 C14 C13 C12 0.0(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
