# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_d8v18379
_database_code_depnum_ccdc_archive 'CCDC 1457168'
loop_
_audit_author_name
_audit_author_address
bdc
;henan normal university
China
;
_audit_update_record             
;
2018-10-23 deposited with the CCDC.	2019-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H31 N O'
_chemical_formula_weight         409.55

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6917(2)
_cell_length_b                   22.9933(5)
_cell_length_c                   10.4658(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.2200(10)
_cell_angle_gamma                90
_cell_volume                     2381.82(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8338
_cell_measurement_theta_min      10.075
_cell_measurement_theta_max      140.169

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3215
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25467
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.393
_diffrn_reflns_theta_max         64.998
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.930
_reflns_number_total             4014
_reflns_number_gt                3228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1228P)²+0.7742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4014
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2129
_refine_ls_wR_factor_gt          0.1954
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11304(17) 0.56147(9) 0.0175(2) 0.0631(6) Uani 1 1 d . . . . .
N1 N 0.62286(19) 0.63648(8) 0.05677(19) 0.0422(5) Uani 1 1 d . . . . .
C1 C 0.8160(2) 0.69192(10) 0.1022(2) 0.0433(6) Uani 1 1 d . . . . .
C2 C 0.9338(3) 0.72367(12) 0.1634(3) 0.0551(7) Uani 1 1 d . . . . .
H2 H 0.9493 0.7441 0.2448 0.066 Uiso 1 1 calc R U . . .
C3 C 1.0274(3) 0.72471(13) 0.1025(3) 0.0651(8) Uani 1 1 d . . . . .
H3 H 1.1068 0.7458 0.1432 0.078 Uiso 1 1 calc R U . . .
C4 C 1.0047(3) 0.69485(14) -0.0179(3) 0.0653(8) Uani 1 1 d . . . . .
H4 H 1.0695 0.6955 -0.0572 0.078 Uiso 1 1 calc R U . . .
C5 C 0.8868(3) 0.66382(13) -0.0811(3) 0.0602(8) Uani 1 1 d . . . . .
H5 H 0.8710 0.6444 -0.1637 0.072 Uiso 1 1 calc R U . . .
C6 C 0.7917(2) 0.66202(10) -0.0198(2) 0.0459(6) Uani 1 1 d . . . . .
C7 C 0.6613(2) 0.62973(11) -0.0633(2) 0.0456(6) Uani 1 1 d . . . . .
H7 H 0.5942 0.6490 -0.1436 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6741(3) 0.56567(12) -0.0975(3) 0.0611(7) Uani 1 1 d . . . . .
H8A H 0.7472 0.5480 -0.0230 0.092 Uiso 1 1 calc R U . . .
H8B H 0.6917 0.5632 -0.1807 0.092 Uiso 1 1 calc R U . . .
H8C H 0.5915 0.5457 -0.1100 0.092 Uiso 1 1 calc R U . . .
C9 C 0.7048(2) 0.68154(9) 0.1555(2) 0.0387(5) Uani 1 1 d . . . . .
C10 C 0.7698(2) 0.66280(10) 0.3062(2) 0.0409(5) Uani 1 1 d . . . . .
H10 H 0.7889 0.6937 0.3680 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8050(2) 0.61126(10) 0.3678(2) 0.0440(6) Uani 1 1 d . . . . .
C12 C 0.8713(2) 0.61039(12) 0.5185(2) 0.0504(6) Uani 1 1 d . . . . .
H12 H 0.8898 0.6464 0.5622 0.060 Uiso 1 1 calc R U . . .
C13 C 0.9080(3) 0.56415(16) 0.5994(3) 0.0691(9) Uani 1 1 d . . . . .
C14 C 0.7789(5) 0.55346(14) 0.2955(3) 0.0948(13) Uani 1 1 d . . . . .
H14A H 0.7207 0.5587 0.2006 0.142 Uiso 1 1 calc R U . . .
H14B H 0.7364 0.5278 0.3393 0.142 Uiso 1 1 calc R U . . .
H14C H 0.8630 0.5369 0.3004 0.142 Uiso 1 1 calc R U . . .
C15 C 0.4931(2) 0.62172(10) 0.0477(2) 0.0423(6) Uani 1 1 d . . . . .
C16 C 0.3915(3) 0.60533(11) -0.0780(2) 0.0510(6) Uani 1 1 d . . . . .
H16 H 0.4085 0.6072 -0.1588 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2676(3) 0.58658(12) -0.0837(3) 0.0573(7) Uani 1 1 d . . . . .
H17 H 0.2024 0.5758 -0.1683 0.069 Uiso 1 1 calc R U . . .
C18 C 0.2375(2) 0.58335(10) 0.0330(3) 0.0495(6) Uani 1 1 d . . . . .
C19 C 0.3339(2) 0.60182(11) 0.1579(3) 0.0499(6) Uani 1 1 d . . . . .
H19 H 0.3141 0.6020 0.2372 0.060 Uiso 1 1 calc R U . . .
C20 C 0.4590(2) 0.61990(11) 0.1639(2) 0.0489(6) Uani 1 1 d . . . . .
H20 H 0.5231 0.6313 0.2486 0.059 Uiso 1 1 calc R U . . .
C21 C 0.0844(3) 0.55590(14) 0.1373(4) 0.0697(8) Uani 1 1 d . . . . .
H21A H -0.0026 0.5381 0.1143 0.105 Uiso 1 1 calc R U . . .
H21B H 0.0840 0.5937 0.1762 0.105 Uiso 1 1 calc R U . . .
H21C H 0.1522 0.5321 0.2032 0.105 Uiso 1 1 calc R U . . .
C22 C 0.6229(2) 0.73747(10) 0.1504(2) 0.0423(6) Uani 1 1 d . . . . .
H22A H 0.5559 0.7290 0.1894 0.051 Uiso 1 1 calc R U . . .
H22B H 0.6837 0.7666 0.2085 0.051 Uiso 1 1 calc R U . . .
C23 C 0.5510(3) 0.76346(12) 0.0064(3) 0.0542(7) Uani 1 1 d . . . . .
H23A H 0.6176 0.7783 -0.0275 0.065 Uiso 1 1 calc R U . . .
H23B H 0.4999 0.7332 -0.0564 0.065 Uiso 1 1 calc R U . . .
C24 C 0.4572(3) 0.81174(11) 0.0086(2) 0.0485(6) Uani 1 1 d . . . . .
C25 C 0.3250(3) 0.80026(15) -0.0116(4) 0.0748(9) Uani 1 1 d . . . . .
H25 H 0.2941 0.7622 -0.0300 0.090 Uiso 1 1 calc R U . . .
C26 C 0.2365(4) 0.84236(19) -0.0059(5) 0.0938(12) Uani 1 1 d . . . . .
H26 H 0.1474 0.8330 -0.0210 0.113 Uiso 1 1 calc R U . . .
C27 C 0.2810(4) 0.89819(19) 0.0222(4) 0.0877(12) Uani 1 1 d . . . . .
H27 H 0.2220 0.9271 0.0266 0.105 Uiso 1 1 calc R U . . .
C28 C 0.4114(4) 0.91196(14) 0.0438(3) 0.0829(11) Uani 1 1 d . . . . .
H28 H 0.4411 0.9502 0.0634 0.099 Uiso 1 1 calc R U . . .
C29 C 0.5013(3) 0.86857(13) 0.0366(3) 0.0626(8) Uani 1 1 d . . . . .
H29 H 0.5901 0.8781 0.0507 0.075 Uiso 1 1 calc R U . . .
H13A H 0.956(3) 0.5667(17) 0.703(4) 0.092(11) Uiso 1 1 d . . . . .
H13B H 0.900(4) 0.527(2) 0.559(4) 0.100(13) Uiso 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
O1 C18 1.373(3) . ?
O1 C21 1.404(4) . ?
N1 C15 1.396(3) . ?
N1 C7 1.471(3) . ?
N1 C9 1.491(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.385(3) . ?
C1 C9 1.512(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(4) . ?
C7 C8 1.534(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.526(3) . ?
C9 C22 1.545(3) . ?
C10 C11 1.333(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.465(3) . ?
C11 C14 1.502(4) . ?
C12 C13 1.323(4) . ?
C12 H12 0.9300 . ?
C13 H13A 1.01(4) . ?
C13 H13B 0.95(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.396(3) . ?
C15 C16 1.404(3) . ?
C16 C17 1.374(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.531(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.501(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.374(4) . ?
C24 C29 1.382(4) . ?
C25 C26 1.371(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.363(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.407(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C21 117.2(2) . . ?
C15 N1 C7 120.54(18) . . ?
C15 N1 C9 121.59(17) . . ?
C7 N1 C9 112.64(18) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 C9 128.1(2) . . ?
C6 C1 C9 111.3(2) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C7 110.9(2) . . ?
C5 C6 C7 129.4(2) . . ?
N1 C7 C6 102.60(18) . . ?
N1 C7 C8 112.3(2) . . ?
C6 C7 C8 113.2(2) . . ?
N1 C7 H7 109.5 . . ?
C6 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C1 101.03(17) . . ?
N1 C9 C10 116.04(18) . . ?
C1 C9 C10 108.16(18) . . ?
N1 C9 C22 112.19(17) . . ?
C1 C9 C22 111.70(18) . . ?
C10 C9 C22 107.60(17) . . ?
C11 C10 C9 133.3(2) . . ?
C11 C10 H10 113.4 . . ?
C9 C10 H10 113.4 . . ?
C10 C11 C12 117.7(2) . . ?
C10 C11 C14 125.3(2) . . ?
C12 C11 C14 116.9(2) . . ?
C13 C12 C11 127.3(3) . . ?
C13 C12 H12 116.3 . . ?
C11 C12 H12 116.3 . . ?
C12 C13 H13A 123(2) . . ?
C12 C13 H13B 119(2) . . ?
H13A C13 H13B 117(3) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C20 121.9(2) . . ?
N1 C15 C16 121.7(2) . . ?
C20 C15 C16 116.4(2) . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 121.6(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
O1 C18 C17 117.1(2) . . ?
O1 C18 C19 124.3(2) . . ?
C17 C18 C19 118.6(2) . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 122.5(2) . . ?
C19 C20 H20 118.7 . . ?
C15 C20 H20 118.7 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C9 115.27(19) . . ?
C23 C22 H22A 108.5 . . ?
C9 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C9 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C24 C23 C22 111.3(2) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C29 117.5(3) . . ?
C25 C24 C23 120.6(3) . . ?
C29 C24 C23 121.8(3) . . ?
C26 C25 C24 123.0(4) . . ?
C26 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
C27 C26 C25 119.0(4) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C24 C29 C28 119.8(3) . . ?
C24 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?

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
C6 C1 C2 C3 -0.7(4) . . . . ?
C9 C1 C2 C3 175.6(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C9 C1 C6 C5 -176.7(2) . . . . ?
C2 C1 C6 C7 178.2(2) . . . . ?
C9 C1 C6 C7 1.4(3) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 -176.8(2) . . . . ?
C15 N1 C7 C6 167.80(19) . . . . ?
C9 N1 C7 C6 13.0(2) . . . . ?
C15 N1 C7 C8 -70.4(3) . . . . ?
C9 N1 C7 C8 134.8(2) . . . . ?
C1 C6 C7 N1 -8.5(2) . . . . ?
C5 C6 C7 N1 169.3(2) . . . . ?
C1 C6 C7 C8 -129.7(2) . . . . ?
C5 C6 C7 C8 48.1(3) . . . . ?
C15 N1 C9 C1 -166.61(19) . . . . ?
C7 N1 C9 C1 -12.1(2) . . . . ?
C15 N1 C9 C10 76.7(3) . . . . ?
C7 N1 C9 C10 -128.7(2) . . . . ?
C15 N1 C9 C22 -47.5(3) . . . . ?
C7 N1 C9 C22 107.0(2) . . . . ?
C2 C1 C9 N1 -170.3(2) . . . . ?
C6 C1 C9 N1 6.3(2) . . . . ?
C2 C1 C9 C10 -48.0(3) . . . . ?
C6 C1 C9 C10 128.6(2) . . . . ?
C2 C1 C9 C22 70.3(3) . . . . ?
C6 C1 C9 C22 -113.2(2) . . . . ?
N1 C9 C10 C11 23.6(4) . . . . ?
C1 C9 C10 C11 -89.0(3) . . . . ?
C22 C9 C10 C11 150.2(3) . . . . ?
C9 C10 C11 C12 177.8(2) . . . . ?
C9 C10 C11 C14 -3.9(5) . . . . ?
C10 C11 C12 C13 176.4(3) . . . . ?
C14 C11 C12 C13 -2.1(5) . . . . ?
C7 N1 C15 C20 170.9(2) . . . . ?
C9 N1 C15 C20 -36.5(3) . . . . ?
C7 N1 C15 C16 -6.1(3) . . . . ?
C9 N1 C15 C16 146.4(2) . . . . ?
N1 C15 C16 C17 174.9(2) . . . . ?
C20 C15 C16 C17 -2.3(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C21 O1 C18 C17 177.4(2) . . . . ?
C21 O1 C18 C19 -2.1(4) . . . . ?
C16 C17 C18 O1 -177.0(2) . . . . ?
C16 C17 C18 C19 2.6(4) . . . . ?
O1 C18 C19 C20 176.1(2) . . . . ?
C17 C18 C19 C20 -3.4(4) . . . . ?
C18 C19 C20 C15 1.4(4) . . . . ?
N1 C15 C20 C19 -175.8(2) . . . . ?
C16 C15 C20 C19 1.4(4) . . . . ?
N1 C9 C22 C23 -51.8(3) . . . . ?
C1 C9 C22 C23 60.8(3) . . . . ?
C10 C9 C22 C23 179.3(2) . . . . ?
C9 C22 C23 C24 171.0(2) . . . . ?
C22 C23 C24 C25 -89.7(3) . . . . ?
C22 C23 C24 C29 87.4(3) . . . . ?
C29 C24 C25 C26 0.4(5) . . . . ?
C23 C24 C25 C26 177.7(3) . . . . ?
C24 C25 C26 C27 -0.6(6) . . . . ?
C25 C26 C27 C28 0.2(6) . . . . ?
C26 C27 C28 C29 0.3(6) . . . . ?
C25 C24 C29 C28 0.1(4) . . . . ?
C23 C24 C29 C28 -177.1(2) . . . . ?
C27 C28 C29 C24 -0.5(5) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_bdc-20180810
_database_code_depnum_ccdc_archive 'CCDC 1861504'
loop_
_audit_author_name
_audit_author_address
'dachang dachang bai'
;hennan normal university
China
;
_audit_update_record             
;
2018-08-11 deposited with the CCDC.	2019-02-22 downloaded from the CCDC.
;
_audit_creation_date             2018-08-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C20 H20 N'
_chemical_formula_sum            'C20 H20 F6 N P'
_chemical_formula_weight         419.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1 H1'
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'
P P 0.2955 0.4335 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.90880(10)
_cell_length_b                   16.7762(3)
_cell_length_c                   13.3993(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.0040(10)
_cell_angle_gamma                90
_cell_volume                     1965.78(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8404
_cell_measurement_temperature    296.6(4)
_cell_measurement_theta_max      71.9380
_cell_measurement_theta_min      5.2580
_shelx_estimated_absorpt_T_max   0.738
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15460
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.295
_diffrn_reflns_theta_min         4.271
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.6(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  32.00   1.00    1.00    --  -35.45  57.00 -30.00   84
  2  ω    -32.00  62.00   1.00    1.00    --   35.45 -77.00   0.00   94
  3  ω     23.00  89.00   1.00    1.00    --   35.45-125.00-120.00   66
  4  ω      1.00  74.00   1.00    1.00    --   35.45 -99.00-180.00   73
  5  ω     23.00  89.00   1.00    1.00    --   35.45-125.00  30.00   66
  6  ω     19.00 103.00   1.00    1.00    --   35.45  57.00 120.00   84
  7  ω      1.00  74.00   1.00    1.00    --   35.45 -99.00-120.00   73
  8  ω    -32.00  62.00   1.00    1.00    --   35.45 -77.00-120.00   94
  9  ω     23.00  89.00   1.00    1.00    --   35.45-125.00 -60.00   66
 10  ω      6.00 107.00   1.00    1.00    --   35.45  19.00 -30.00  101
 11  ω      6.00 107.00   1.00    1.00    --   35.45  19.00 -30.00  101
 12  ω     42.00 127.00   1.00    1.17    --  108.69 -61.00 -60.00   85
 13  ω     91.00 177.00   1.00    1.17    --  108.69  45.00  30.00   86
 14  ω     91.00 177.00   1.00    1.17    --  108.69  45.00  90.00   86
 15  ω    100.00 178.00   1.00    1.17    --  108.69 111.00 -30.00   78
 16  ω     39.00 109.00   1.00    1.17    --  108.69 -95.00 -60.00   70
 17  ω     39.00 130.00   1.00    1.17    --  108.69 -30.00 -90.00   91
 18  ω     91.00 176.00   1.00    1.17    --  108.69  61.00  60.00   85
 19  ω     57.00 151.00   1.00    1.17    --  108.69 178.00-120.00   94
 20  ω     19.00 103.00   1.00    1.00    --   35.45  57.00-150.00   84
 21  ω    -32.00  52.00   1.00    1.00    --   35.45 -57.00  60.00   84
 22  ω      9.00 103.00   1.00    1.00    --   35.45  77.00 -90.00   94
 23  ω      9.00 103.00   1.00    1.00    --   35.45  77.00  90.00   94
 24  ω      9.00 103.00   1.00    1.00    --   35.45  77.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146707000
_diffrn_orient_matrix_UB_12      0.0828965000
_diffrn_orient_matrix_UB_13      -0.0466939000
_diffrn_orient_matrix_UB_21      0.1704600000
_diffrn_orient_matrix_UB_22      0.0025450000
_diffrn_orient_matrix_UB_23      0.0504412000
_diffrn_orient_matrix_UB_31      0.0419163000
_diffrn_orient_matrix_UB_32      -0.0394236000
_diffrn_orient_matrix_UB_33      -0.0948496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3174
_reflns_number_total             3818
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.060
_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)+(0.1232P)²+0.8684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2163
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C12(H12), C17(H17), C20(H20), C15(H15), C13(H13),
 C14(H14), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_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
P2 P 0.80476(8) 0.30468(5) 0.45652(6) 0.0605(3) Uani 1 1 d . . . . .
C11 C 0.7158(2) 0.41434(14) 0.94961(16) 0.0423(5) Uani 1 1 d . . . . .
F1 F 0.9396(3) 0.28864(18) 0.3979(2) 0.1178(9) Uani 1 1 d . . . . .
F4 F 0.7146(3) 0.34990(17) 0.36237(18) 0.1149(9) Uani 1 1 d . . . . .
N9 N 0.8250(3) 0.45697(15) 0.81472(18) 0.0617(6) Uani 1 1 d . . . . .
F3 F 0.9013(3) 0.2592(2) 0.55077(18) 0.1236(11) Uani 1 1 d . . . . .
C10 C 0.7457(3) 0.38488(15) 0.84785(18) 0.0466(6) Uani 1 1 d . . . . .
C24 C 0.5943(3) 0.36783(15) 0.77937(18) 0.0492(6) Uani 1 1 d . . . . .
H24 H 0.542671 0.322375 0.793816 0.059 Uiso 1 1 calc R . . . .
C16 C 0.7614(3) 0.49178(17) 0.9668(2) 0.0563(7) Uani 1 1 d . . . . .
C8 C 0.8296(3) 0.51853(16) 0.8834(2) 0.0594(7) Uani 1 1 d . . . . .
C21 C 0.8568(3) 0.31550(16) 0.8637(2) 0.0522(6) Uani 1 1 d . . . . .
H21 H 0.957232 0.328115 0.904773 0.063 Uiso 1 1 calc R . . . .
C25 C 0.5276(3) 0.41105(17) 0.70070(19) 0.0546(6) Uani 1 1 d . . . . .
H25 H 0.580839 0.455206 0.683960 0.065 Uiso 1 1 calc R . . . .
F7 F 0.7270(4) 0.22495(17) 0.4128(3) 0.1490(12) Uani 1 1 d . . . . .
F6 F 0.8836(4) 0.38482(19) 0.4970(3) 0.1558(14) Uani 1 1 d . . . . .
C12 C 0.6506(3) 0.3726(2) 1.0164(2) 0.0608(7) Uani 1 1 d . . . . .
H12 H 0.618449 0.320388 1.002090 0.073 Uiso 1 1 calc R . . . .
C26 C 0.3775(3) 0.39551(19) 0.6378(2) 0.0615(7) Uani 1 1 d . . . . .
C23 C 0.8602(4) 0.2567(2) 0.7799(2) 0.0718(9) Uani 1 1 d . . . . .
H23A H 0.784454 0.262414 0.717914 0.086 Uiso 1 1 calc R . . . .
H23B H 0.959325 0.237736 0.770189 0.086 Uiso 1 1 calc R . . . .
C22 C 0.8070(4) 0.23104(18) 0.8721(2) 0.0682(8) Uani 1 1 d . . . . .
H22A H 0.873321 0.196306 0.918896 0.082 Uiso 1 1 calc R . . . .
H22B H 0.698489 0.220978 0.866633 0.082 Uiso 1 1 calc R . . . .
F5 F 0.6748(4) 0.3202(3) 0.5166(3) 0.1745(18) Uani 1 1 d . . . . .
C17 C 0.8885(4) 0.4634(2) 0.7309(2) 0.0721(9) Uani 1 1 d . . . . .
H17 H 0.886127 0.421209 0.685587 0.087 Uiso 1 1 calc R . . . .
C20 C 0.8977(4) 0.5908(2) 0.8664(3) 0.0850(12) Uani 1 1 d . . . . .
H20 H 0.899342 0.633139 0.911441 0.102 Uiso 1 1 calc R . . . .
C15 C 0.7400(4) 0.5294(2) 1.0569(3) 0.0815(11) Uani 1 1 d . . . . .
H15 H 0.768123 0.582268 1.070173 0.098 Uiso 1 1 calc R . . . .
C13 C 0.6324(4) 0.4080(3) 1.1053(3) 0.0835(11) Uani 1 1 d . . . . .
H13 H 0.590355 0.379326 1.152642 0.100 Uiso 1 1 calc R . . . .
C14 C 0.6759(4) 0.4854(3) 1.1248(3) 0.0885(12) Uani 1 1 d . . . . .
H14 H 0.662019 0.508912 1.185193 0.106 Uiso 1 1 calc R . . . .
C19 C 0.9615(5) 0.5980(3) 0.7829(4) 0.1015(16) Uani 1 1 d . . . . .
H19 H 1.008573 0.645624 0.771216 0.122 Uiso 1 1 calc R . . . .
C27 C 0.3182(5) 0.4474(3) 0.5672(3) 0.0917(13) Uani 1 1 d . . . . .
C28 C 0.2963(5) 0.3217(3) 0.6550(3) 0.1019(14) Uani 1 1 d . . . . .
H28A H 0.358252 0.276466 0.645894 0.153 Uiso 1 1 calc GR . . . .
H28B H 0.201223 0.318995 0.607263 0.153 Uiso 1 1 calc GR . . . .
H28C H 0.276522 0.321653 0.722942 0.153 Uiso 1 1 calc GR . . . .
C18 C 0.9580(4) 0.5364(3) 0.7151(3) 0.0968(14) Uani 1 1 d . . . . .
H18 H 1.002117 0.542959 0.658081 0.116 Uiso 1 1 calc R . . . .
H27A H 0.222(5) 0.443(3) 0.523(3) 0.099(13) Uiso 1 1 d . . . . .
H27B H 0.373(5) 0.491(3) 0.562(3) 0.098(15) Uiso 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
P2 F1 1.578(2) . ?
P2 F4 1.557(2) . ?
P2 F3 1.582(2) . ?
P2 F7 1.568(3) . ?
P2 F6 1.565(3) . ?
P2 F5 1.553(3) . ?
C11 C10 1.521(3) . ?
C11 C16 1.368(4) . ?
C11 C12 1.352(4) . ?
N9 C10 1.509(3) . ?
N9 C8 1.378(4) . ?
N9 C17 1.355(4) . ?
C10 C24 1.506(3) . ?
C10 C21 1.516(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.323(4) . ?
C16 C8 1.442(4) . ?
C16 C15 1.407(4) . ?
C8 C20 1.394(4) . ?
C21 H21 0.9800 . ?
C21 C23 1.500(4) . ?
C21 C22 1.495(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.461(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(5) . ?
C26 C27 1.321(5) . ?
C26 C28 1.474(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.469(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C18 1.406(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.353(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(6) . ?
C14 H14 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.373(7) . ?
C27 H27A 0.94(4) . ?
C27 H27B 0.88(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 P2 F3 88.03(14) . . ?
F4 P2 F1 90.22(15) . . ?
F4 P2 F3 178.14(16) . . ?
F4 P2 F7 89.44(17) . . ?
F4 P2 F6 89.43(18) . . ?
F7 P2 F1 89.56(19) . . ?
F7 P2 F3 91.17(19) . . ?
F6 P2 F1 89.1(2) . . ?
F6 P2 F3 89.9(2) . . ?
F6 P2 F7 178.3(2) . . ?
F5 P2 F1 178.64(17) . . ?
F5 P2 F4 91.04(18) . . ?
F5 P2 F3 90.70(16) . . ?
F5 P2 F7 91.0(2) . . ?
F5 P2 F6 90.4(2) . . ?
C16 C11 C10 111.2(2) . . ?
C12 C11 C10 126.6(2) . . ?
C12 C11 C16 122.2(2) . . ?
C8 N9 C10 111.1(2) . . ?
C17 N9 C10 126.9(3) . . ?
C17 N9 C8 122.0(3) . . ?
N9 C10 C11 100.1(2) . . ?
N9 C10 C21 109.1(2) . . ?
C24 C10 C11 108.57(19) . . ?
C24 C10 N9 112.8(2) . . ?
C24 C10 C21 115.1(2) . . ?
C21 C10 C11 110.16(19) . . ?
C10 C24 H24 116.7 . . ?
C25 C24 C10 126.5(2) . . ?
C25 C24 H24 116.7 . . ?
C11 C16 C8 108.7(2) . . ?
C11 C16 C15 119.0(3) . . ?
C15 C16 C8 132.2(3) . . ?
N9 C8 C16 108.7(2) . . ?
N9 C8 C20 120.1(3) . . ?
C20 C8 C16 131.1(3) . . ?
C10 C21 H21 114.5 . . ?
C23 C21 C10 120.4(2) . . ?
C23 C21 H21 114.5 . . ?
C22 C21 C10 122.9(2) . . ?
C22 C21 H21 114.5 . . ?
C22 C21 C23 58.7(2) . . ?
C24 C25 H25 117.1 . . ?
C24 C25 C26 125.7(3) . . ?
C26 C25 H25 117.1 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C25 C26 C28 118.8(3) . . ?
C27 C26 C25 119.5(4) . . ?
C27 C26 C28 121.6(4) . . ?
C21 C23 H23A 117.7 . . ?
C21 C23 H23B 117.7 . . ?
H23A C23 H23B 114.8 . . ?
C22 C23 C21 60.46(19) . . ?
C22 C23 H23A 117.7 . . ?
C22 C23 H23B 117.7 . . ?
C21 C22 H22A 117.7 . . ?
C21 C22 H22B 117.7 . . ?
C23 C22 C21 60.8(2) . . ?
C23 C22 H22A 117.7 . . ?
C23 C22 H22B 117.7 . . ?
H22A C22 H22B 114.8 . . ?
N9 C17 H17 121.3 . . ?
N9 C17 C18 117.4(4) . . ?
C18 C17 H17 121.3 . . ?
C8 C20 H20 120.8 . . ?
C19 C20 C8 118.4(4) . . ?
C19 C20 H20 120.8 . . ?
C16 C15 H15 121.1 . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 H15 121.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C20 C19 H19 119.3 . . ?
C20 C19 C18 121.4(4) . . ?
C18 C19 H19 119.3 . . ?
C26 C27 H27A 126(3) . . ?
C26 C27 H27B 116(3) . . ?
H27A C27 H27B 117(4) . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C10 C24 C25 106.6(3) . . . . ?
C11 C10 C21 C23 156.6(3) . . . . ?
C11 C10 C21 C22 86.3(3) . . . . ?
C11 C16 C8 N9 0.2(3) . . . . ?
C11 C16 C8 C20 -177.6(3) . . . . ?
C11 C16 C15 C14 1.2(4) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
N9 C10 C24 C25 -3.4(4) . . . . ?
N9 C10 C21 C23 -94.5(3) . . . . ?
N9 C10 C21 C22 -164.8(2) . . . . ?
N9 C8 C20 C19 -1.5(4) . . . . ?
N9 C17 C18 C19 0.4(5) . . . . ?
C10 C11 C16 C8 -2.5(3) . . . . ?
C10 C11 C16 C15 178.9(2) . . . . ?
C10 C11 C12 C13 179.7(3) . . . . ?
C10 N9 C8 C16 2.2(3) . . . . ?
C10 N9 C8 C20 -179.7(2) . . . . ?
C10 N9 C17 C18 -179.5(3) . . . . ?
C10 C24 C25 C26 -177.1(2) . . . . ?
C10 C21 C23 C22 -112.3(3) . . . . ?
C10 C21 C22 C23 108.2(3) . . . . ?
C24 C10 C21 C23 33.4(4) . . . . ?
C24 C10 C21 C22 -36.9(4) . . . . ?
C24 C25 C26 C27 173.9(3) . . . . ?
C24 C25 C26 C28 -6.3(5) . . . . ?
C16 C11 C10 N9 3.6(2) . . . . ?
C16 C11 C10 C24 -114.8(2) . . . . ?
C16 C11 C10 C21 118.4(2) . . . . ?
C16 C11 C12 C13 -1.5(4) . . . . ?
C16 C8 C20 C19 176.0(3) . . . . ?
C16 C15 C14 C13 -0.8(5) . . . . ?
C8 N9 C10 C11 -3.5(2) . . . . ?
C8 N9 C10 C24 111.7(2) . . . . ?
C8 N9 C10 C21 -119.0(2) . . . . ?
C8 N9 C17 C18 -1.0(4) . . . . ?
C8 C16 C15 C14 -177.0(3) . . . . ?
C8 C20 C19 C18 0.9(5) . . . . ?
C21 C10 C24 C25 -129.4(3) . . . . ?
C12 C11 C10 N9 -177.5(2) . . . . ?
C12 C11 C10 C24 64.1(3) . . . . ?
C12 C11 C10 C21 -62.8(3) . . . . ?
C12 C11 C16 C8 178.5(2) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C17 N9 C10 C11 175.1(3) . . . . ?
C17 N9 C10 C24 -69.7(3) . . . . ?
C17 N9 C10 C21 59.5(3) . . . . ?
C17 N9 C8 C16 -176.4(2) . . . . ?
C17 N9 C8 C20 1.6(4) . . . . ?
C20 C19 C18 C17 -0.4(6) . . . . ?
C15 C16 C8 N9 178.5(3) . . . . ?
C15 C16 C8 C20 0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.834
_oxdiff_exptl_absorpt_empirical_full_min 0.655
