# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_r20200810a
_audit_block_doi                 10.5517/ccdc.csd.cc2c5h68
_database_code_depnum_ccdc_archive 'CCDC 2180019'
loop_
_audit_author_name
_audit_author_address
'Yan Kou'
;Tianjin University
China
;
_audit_update_record             
;
2022-06-18 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_audit_creation_date             2020-08-22
_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         'C44 H44 N2'
_chemical_formula_sum            'C44 H44 N2'
_chemical_formula_weight         600.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.4324(5)
_cell_length_b                   14.6018(14)
_cell_length_c                   16.6369(14)
_cell_angle_alpha                109.684(8)
_cell_angle_beta                 98.078(7)
_cell_angle_gamma                93.683(7)
_cell_volume                     1671.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4454
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.7470
_cell_measurement_theta_min      2.2950
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.609
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00   12.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00   12.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00   12.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015587000
_diffrn_orient_matrix_UB_12      -0.0387861000
_diffrn_orient_matrix_UB_13      0.0166414000
_diffrn_orient_matrix_UB_21      0.0063598000
_diffrn_orient_matrix_UB_22      0.0342744000
_diffrn_orient_matrix_UB_23      0.0425723000
_diffrn_orient_matrix_UB_31      -0.0968667000
_diffrn_orient_matrix_UB_32      -0.0046076000
_diffrn_orient_matrix_UB_33      -0.0048891000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3416
_reflns_number_total             6813
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       CrystalClear(Rigaku,2008)
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.009(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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6813
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0887
_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)+(0.1204P)²+0.2588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H42 of C42, H41 of C41, H40 of C40, H43 of C43, H24 of
  C24, H25 of C25, H26 of C26, H28 of C28, H32 of C32, H5 of C5, H4 of C4, H3
  of C3, H2 of C2, H18 of C18, H19 of C19
 At 1.5 times of:
  All C(H,H,H) groups, H10 of C10
2. Restrained distances
 C10-H10
 0.95 with sigma of 0.01
3.a Riding coordinates:
 C10(H10)
3.b Ternary CH refined with riding coordinates:
 C32(H32)
3.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C33(H33A,
 H33B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C24(H24), C25(H25),
 C26(H26), C28(H28), C40(H40), C41(H41), C42(H42), C43(H43)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C34(H34A,H34B,H34C), C38(H38A,H38B,
 H38C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.4587(4) 0.1537(2) 0.42167(19) 0.0291(7) Uani 1 1 d . . . . .
N2 N 0.9601(4) 0.6202(2) 0.16313(19) 0.0321(7) Uani 1 1 d . . . . .
C1 C 0.4616(4) 0.1854(2) 0.5101(2) 0.0260(8) Uani 1 1 d . . . . .
C2 C 0.3909(5) 0.1178(3) 0.5446(2) 0.0318(9) Uani 1 1 d . . . . .
H2 H 0.341378 0.053539 0.507153 0.038 Uiso 1 1 calc R . . . .
C3 C 0.3931(5) 0.1441(3) 0.6316(2) 0.0353(9) Uani 1 1 d . . . . .
H3 H 0.343724 0.098278 0.654216 0.042 Uiso 1 1 calc R . . . .
C4 C 0.4682(5) 0.2389(3) 0.6881(2) 0.0338(9) Uani 1 1 d . . . . .
H4 H 0.468910 0.257362 0.748689 0.041 Uiso 1 1 calc R . . . .
C5 C 0.5401(5) 0.3042(3) 0.6545(2) 0.0308(9) Uani 1 1 d . . . . .
H5 H 0.593271 0.367477 0.692887 0.037 Uiso 1 1 calc R . . . .
C6 C 0.5376(4) 0.2802(2) 0.5648(2) 0.0241(8) Uani 1 1 d . . . . .
C7 C 0.6037(4) 0.3478(2) 0.5258(2) 0.0231(8) Uani 1 1 d . . . . .
C8 C 0.5802(4) 0.3176(2) 0.4339(2) 0.0215(7) Uani 1 1 d . . . . .
C9 C 0.5153(4) 0.2147(2) 0.3851(2) 0.0253(8) Uani 1 1 d . . . . .
C10 C 0.5038(5) 0.1660(2) 0.2878(2) 0.0322(9) Uani 1 1 d D . . . .
H10 H 0.581035 0.204135 0.259604 0.048 Uiso 1 1 d DR . . . .
C11 C 0.5736(5) 0.0653(3) 0.2635(3) 0.0398(10) Uani 1 1 d . . . . .
H11A H 0.503583 0.023258 0.287160 0.048 Uiso 1 1 calc R . . . .
H11B H 0.551470 0.033862 0.199642 0.048 Uiso 1 1 calc R . . . .
C12 C 0.7743(6) 0.0718(3) 0.2975(3) 0.0538(13) Uani 1 1 d . . . . .
H12A H 0.844149 0.114449 0.275335 0.081 Uiso 1 1 calc GR . . . .
H12B H 0.813757 0.006240 0.278363 0.081 Uiso 1 1 calc GR . . . .
H12C H 0.795916 0.098961 0.360998 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.3027(5) 0.1596(3) 0.2449(2) 0.0402(10) Uani 1 1 d . . . . .
H13A H 0.230159 0.107225 0.255971 0.048 Uiso 1 1 calc R . . . .
H13B H 0.255908 0.222104 0.274153 0.048 Uiso 1 1 calc R . . . .
C14 C 0.2668(6) 0.1397(3) 0.1480(3) 0.0527(12) Uani 1 1 d . . . . .
H14A H 0.300552 0.074032 0.117121 0.063 Uiso 1 1 calc R . . . .
H14B H 0.345047 0.188652 0.135140 0.063 Uiso 1 1 calc R . . . .
C15 C 0.0629(7) 0.1441(4) 0.1142(3) 0.0765(16) Uani 1 1 d . . . . .
H15A H -0.013882 0.090939 0.122275 0.092 Uiso 1 1 calc R . . . .
H15B H 0.026247 0.207249 0.149282 0.092 Uiso 1 1 calc R . . . .
C16 C 0.0266(8) 0.1340(4) 0.0198(4) 0.0912(19) Uani 1 1 d . . . . .
H16A H 0.061560 0.071335 -0.015377 0.137 Uiso 1 1 calc GR . . . .
H16B H 0.098569 0.187834 0.011711 0.137 Uiso 1 1 calc GR . . . .
H16C H -0.103919 0.136303 0.001959 0.137 Uiso 1 1 calc GR . . . .
C17 C 0.6313(4) 0.3890(2) 0.3962(2) 0.0220(7) Uani 1 1 d . . . . .
C18 C 0.5771(4) 0.3789(2) 0.3076(2) 0.0249(8) Uani 1 1 d . . . . .
H18 H 0.487602 0.326356 0.271722 0.030 Uiso 1 1 calc R . . . .
C19 C 0.6479(4) 0.4411(2) 0.2728(2) 0.0234(8) Uani 1 1 d . . . . .
H19 H 0.609296 0.429386 0.212920 0.028 Uiso 1 1 calc R . . . .
C20 C 0.7791(4) 0.5240(2) 0.3225(2) 0.0217(7) Uani 1 1 d . . . . .
C21 C 0.8007(4) 0.5477(2) 0.4133(2) 0.0191(7) Uani 1 1 d . . . . .
C22 C 0.7301(4) 0.4810(2) 0.4498(2) 0.0207(7) Uani 1 1 d . . . . .
C23 C 0.7581(4) 0.5069(2) 0.5418(2) 0.0211(7) Uani 1 1 d . . . . .
C24 C 0.6912(4) 0.4422(2) 0.5770(2) 0.0237(8) Uani 1 1 d . . . . .
H24 H 0.704260 0.461692 0.638231 0.028 Uiso 1 1 calc R . . . .
C25 C 0.8522(4) 0.6019(2) 0.5959(2) 0.0259(8) Uani 1 1 d . . . . .
H25 H 0.870083 0.619486 0.657159 0.031 Uiso 1 1 calc R . . . .
C26 C 0.9149(4) 0.6661(2) 0.5614(2) 0.0252(8) Uani 1 1 d . . . . .
H26 H 0.974102 0.728626 0.598777 0.030 Uiso 1 1 calc R . . . .
C27 C 0.8944(4) 0.6420(2) 0.4687(2) 0.0223(8) Uani 1 1 d . . . . .
C28 C 0.9586(4) 0.7068(2) 0.4328(2) 0.0225(8) Uani 1 1 d . . . . .
H28 H 1.010252 0.770819 0.470111 0.027 Uiso 1 1 calc R . . . .
C29 C 0.9509(4) 0.6822(2) 0.3427(2) 0.0222(8) Uani 1 1 d . . . . .
C30 C 0.8714(4) 0.5869(2) 0.2861(2) 0.0229(8) Uani 1 1 d . . . . .
C31 C 0.8951(4) 0.5582(2) 0.1963(2) 0.0259(8) Uani 1 1 d . . . . .
C32 C 0.8620(5) 0.4520(2) 0.1329(2) 0.0268(8) Uani 1 1 d . . . . .
H32 H 0.843076 0.408155 0.166740 0.032 Uiso 1 1 calc R . . . .
C33 C 1.0280(5) 0.4245(3) 0.0893(2) 0.0335(9) Uani 1 1 d . . . . .
H33A H 0.997773 0.358080 0.044818 0.040 Uiso 1 1 calc R . . . .
H33B H 1.054208 0.470711 0.059224 0.040 Uiso 1 1 calc R . . . .
C34 C 1.1997(5) 0.4259(3) 0.1519(3) 0.0445(11) Uani 1 1 d . . . . .
H34A H 1.299856 0.406364 0.119679 0.067 Uiso 1 1 calc GR . . . .
H34B H 1.175374 0.380133 0.181809 0.067 Uiso 1 1 calc GR . . . .
H34C H 1.234125 0.492201 0.194615 0.067 Uiso 1 1 calc GR . . . .
C35 C 0.6901(5) 0.4349(3) 0.0646(2) 0.0334(9) Uani 1 1 d . . . . .
H35A H 0.718045 0.463567 0.021044 0.040 Uiso 1 1 calc R . . . .
H35B H 0.592911 0.469361 0.092963 0.040 Uiso 1 1 calc R . . . .
C36 C 0.6177(5) 0.3254(3) 0.0180(2) 0.0428(11) Uani 1 1 d . . . . .
H36A H 0.719912 0.289884 -0.003937 0.051 Uiso 1 1 calc R . . . .
H36B H 0.577005 0.298948 0.060860 0.051 Uiso 1 1 calc R . . . .
C37 C 0.4616(6) 0.3047(3) -0.0566(3) 0.0485(11) Uani 1 1 d . . . . .
H37A H 0.497328 0.335974 -0.097214 0.058 Uiso 1 1 calc R . . . .
H37B H 0.354190 0.334062 -0.034185 0.058 Uiso 1 1 calc R . . . .
C38 C 0.4084(6) 0.1956(3) -0.1052(3) 0.0610(14) Uani 1 1 d . . . . .
H38A H 0.304537 0.185557 -0.151869 0.091 Uiso 1 1 calc GR . . . .
H38B H 0.373729 0.164124 -0.065133 0.091 Uiso 1 1 calc GR . . . .
H38C H 0.512451 0.166685 -0.129928 0.091 Uiso 1 1 calc GR . . . .
C39 C 1.0148(5) 0.7167(2) 0.2154(2) 0.0284(8) Uani 1 1 d . . . . .
C40 C 1.0769(5) 0.7816(3) 0.1757(2) 0.0366(9) Uani 1 1 d . . . . .
H40 H 1.073274 0.758834 0.114765 0.044 Uiso 1 1 calc R . . . .
C41 C 1.1416(5) 0.8763(3) 0.2240(3) 0.0374(10) Uani 1 1 d . . . . .
H41 H 1.180035 0.919624 0.196358 0.045 Uiso 1 1 calc R . . . .
C42 C 1.1521(5) 0.9101(3) 0.3130(2) 0.0334(9) Uani 1 1 d . . . . .
H42 H 1.200604 0.975983 0.346299 0.040 Uiso 1 1 calc R . . . .
C43 C 1.0926(5) 0.8488(2) 0.3536(2) 0.0295(8) Uani 1 1 d . . . . .
H43 H 1.099627 0.872996 0.414690 0.035 Uiso 1 1 calc R . . . .
C44 C 1.0213(4) 0.7507(2) 0.3056(2) 0.0242(8) 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
N1 C1 1.382(4) . ?
N1 C9 1.314(4) . ?
N2 C31 1.308(4) . ?
N2 C39 1.382(4) . ?
C1 C2 1.407(4) . ?
C1 C6 1.403(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.410(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(5) . ?
C6 C7 1.447(4) . ?
C7 C8 1.423(4) . ?
C7 C24 1.409(5) . ?
C8 C9 1.457(4) . ?
C8 C17 1.442(4) . ?
C9 C10 1.520(5) . ?
C10 H10 1.0352 . ?
C10 C11 1.534(5) . ?
C10 C13 1.546(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.504(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.519(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.554(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.510(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.428(4) . ?
C17 C22 1.421(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.346(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.431(4) . ?
C20 C21 1.414(4) . ?
C20 C30 1.446(4) . ?
C21 C22 1.421(4) . ?
C21 C27 1.439(4) . ?
C22 C23 1.427(4) . ?
C23 C24 1.371(4) . ?
C23 C25 1.443(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.344(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.445(4) . ?
C27 C28 1.372(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.411(4) . ?
C29 C30 1.425(4) . ?
C29 C44 1.446(4) . ?
C30 C31 1.449(5) . ?
C31 C32 1.535(4) . ?
C32 H32 1.0000 . ?
C32 C33 1.526(5) . ?
C32 C35 1.532(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.524(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.543(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.508(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.520(6) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.413(5) . ?
C39 C44 1.406(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.359(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.384(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.375(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.409(5) . ?

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
C9 N1 C1 120.4(3) . . ?
C31 N2 C39 119.6(3) . . ?
N1 C1 C2 117.6(3) . . ?
N1 C1 C6 121.9(3) . . ?
C6 C1 C2 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.1(3) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 117.5(3) . . ?
C1 C6 C7 118.3(3) . . ?
C5 C6 C7 124.1(3) . . ?
C8 C7 C6 119.0(3) . . ?
C24 C7 C6 121.4(3) . . ?
C24 C7 C8 119.6(3) . . ?
C7 C8 C9 116.9(3) . . ?
C7 C8 C17 118.0(3) . . ?
C17 C8 C9 125.0(3) . . ?
N1 C9 C8 122.8(3) . . ?
N1 C9 C10 112.6(3) . . ?
C8 C9 C10 124.7(3) . . ?
C9 C10 H10 114.8 . . ?
C9 C10 C11 112.3(3) . . ?
C9 C10 C13 107.6(3) . . ?
C11 C10 H10 104.1 . . ?
C11 C10 C13 112.0(3) . . ?
C13 C10 H10 105.9 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.4(3) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 108.1 . . ?
C10 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C14 C13 C10 116.9(3) . . ?
C14 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C13 C14 C15 111.9(4) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 113.1(5) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C8 124.9(3) . . ?
C22 C17 C8 120.0(3) . . ?
C22 C17 C18 114.8(3) . . ?
C17 C18 H18 118.7 . . ?
C19 C18 C17 122.6(3) . . ?
C19 C18 H18 118.7 . . ?
C18 C19 H19 118.7 . . ?
C18 C19 C20 122.6(3) . . ?
C20 C19 H19 118.7 . . ?
C19 C20 C30 124.2(3) . . ?
C21 C20 C19 114.9(3) . . ?
C21 C20 C30 120.6(3) . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 C27 118.6(3) . . ?
C22 C21 C27 120.2(3) . . ?
C17 C22 C23 119.6(3) . . ?
C21 C22 C17 121.0(3) . . ?
C21 C22 C23 119.4(3) . . ?
C22 C23 C25 119.3(3) . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 C25 121.2(3) . . ?
C7 C24 H24 118.7 . . ?
C23 C24 C7 122.6(3) . . ?
C23 C24 H24 118.7 . . ?
C23 C25 H25 119.4 . . ?
C26 C25 C23 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 119.3 . . ?
C25 C26 C27 121.4(3) . . ?
C27 C26 H26 119.3 . . ?
C21 C27 C26 118.4(3) . . ?
C28 C27 C21 119.7(3) . . ?
C28 C27 C26 121.9(3) . . ?
C27 C28 H28 118.7 . . ?
C27 C28 C29 122.7(3) . . ?
C29 C28 H28 118.7 . . ?
C28 C29 C30 119.1(3) . . ?
C28 C29 C44 122.2(3) . . ?
C30 C29 C44 118.7(3) . . ?
C20 C30 C31 124.4(3) . . ?
C29 C30 C20 118.1(3) . . ?
C29 C30 C31 117.4(3) . . ?
N2 C31 C30 122.8(3) . . ?
N2 C31 C32 113.2(3) . . ?
C30 C31 C32 123.8(3) . . ?
C31 C32 H32 108.0 . . ?
C33 C32 C31 111.0(3) . . ?
C33 C32 H32 108.0 . . ?
C33 C32 C35 110.4(3) . . ?
C35 C32 C31 111.4(3) . . ?
C35 C32 H32 108.0 . . ?
C32 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C34 C33 C32 113.7(3) . . ?
C34 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.0 . . ?
C32 C35 H35B 109.0 . . ?
C32 C35 C36 113.0(3) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C35 C36 H36A 108.6 . . ?
C35 C36 H36B 108.6 . . ?
H36A C36 H36B 107.6 . . ?
C37 C36 C35 114.7(3) . . ?
C37 C36 H36A 108.6 . . ?
C37 C36 H36B 108.6 . . ?
C36 C37 H37A 109.1 . . ?
C36 C37 H37B 109.1 . . ?
C36 C37 C38 112.3(4) . . ?
H37A C37 H37B 107.9 . . ?
C38 C37 H37A 109.1 . . ?
C38 C37 H37B 109.1 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C39 C40 117.4(3) . . ?
N2 C39 C44 122.9(3) . . ?
C44 C39 C40 119.5(3) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.5(4) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 119.7 . . ?
C40 C41 C42 120.6(4) . . ?
C42 C41 H41 119.7 . . ?
C41 C42 H42 119.8 . . ?
C43 C42 C41 120.3(3) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.9(3) . . ?
C44 C43 H43 119.6 . . ?
C39 C44 C29 117.3(3) . . ?
C39 C44 C43 118.2(3) . . ?
C43 C44 C29 124.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.8(3) . . . . ?
N1 C1 C6 C5 -177.7(3) . . . . ?
N1 C1 C6 C7 4.0(5) . . . . ?
N1 C9 C10 C11 -43.9(4) . . . . ?
N1 C9 C10 C13 79.8(4) . . . . ?
N2 C31 C32 C33 47.9(4) . . . . ?
N2 C31 C32 C35 -75.4(4) . . . . ?
N2 C39 C40 C41 -176.6(3) . . . . ?
N2 C39 C44 C29 -5.9(5) . . . . ?
N2 C39 C44 C43 175.2(3) . . . . ?
C1 N1 C9 C8 -1.1(5) . . . . ?
C1 N1 C9 C10 179.3(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C1 C6 C7 C8 3.4(5) . . . . ?
C1 C6 C7 C24 -176.3(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
C4 C5 C6 C1 -1.3(5) . . . . ?
C4 C5 C6 C7 176.9(3) . . . . ?
C5 C6 C7 C8 -174.9(3) . . . . ?
C5 C6 C7 C24 5.5(5) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C6 C7 C8 C9 -9.0(4) . . . . ?
C6 C7 C8 C17 174.3(3) . . . . ?
C6 C7 C24 C23 178.7(3) . . . . ?
C7 C8 C9 N1 8.2(5) . . . . ?
C7 C8 C9 C10 -172.2(3) . . . . ?
C7 C8 C17 C18 -164.0(3) . . . . ?
C7 C8 C17 C22 10.4(4) . . . . ?
C8 C7 C24 C23 -0.9(5) . . . . ?
C8 C9 C10 C11 136.5(3) . . . . ?
C8 C9 C10 C13 -99.8(4) . . . . ?
C8 C17 C18 C19 -170.8(3) . . . . ?
C8 C17 C22 C21 172.5(3) . . . . ?
C8 C17 C22 C23 -7.9(4) . . . . ?
C9 N1 C1 C2 177.0(3) . . . . ?
C9 N1 C1 C6 -5.2(5) . . . . ?
C9 C8 C17 C18 19.5(5) . . . . ?
C9 C8 C17 C22 -166.0(3) . . . . ?
C9 C10 C11 C12 -64.6(4) . . . . ?
C9 C10 C13 C14 163.7(3) . . . . ?
C10 C13 C14 C15 -175.0(4) . . . . ?
C11 C10 C13 C14 -72.3(4) . . . . ?
C13 C10 C11 C12 174.2(3) . . . . ?
C13 C14 C15 C16 174.6(4) . . . . ?
C17 C8 C9 N1 -175.3(3) . . . . ?
C17 C8 C9 C10 4.3(5) . . . . ?
C17 C18 C19 C20 -2.0(5) . . . . ?
C17 C22 C23 C24 0.8(4) . . . . ?
C17 C22 C23 C25 -177.6(3) . . . . ?
C18 C17 C22 C21 -12.6(4) . . . . ?
C18 C17 C22 C23 167.1(3) . . . . ?
C18 C19 C20 C21 -12.5(4) . . . . ?
C18 C19 C20 C30 173.8(3) . . . . ?
C19 C20 C21 C22 14.1(4) . . . . ?
C19 C20 C21 C27 -165.3(3) . . . . ?
C19 C20 C30 C29 160.1(3) . . . . ?
C19 C20 C30 C31 -22.4(5) . . . . ?
C20 C21 C22 C17 -1.6(5) . . . . ?
C20 C21 C22 C23 178.7(3) . . . . ?
C20 C21 C27 C26 179.6(3) . . . . ?
C20 C21 C27 C28 0.7(4) . . . . ?
C20 C30 C31 N2 171.8(3) . . . . ?
C20 C30 C31 C32 -13.4(5) . . . . ?
C21 C20 C30 C29 -13.3(4) . . . . ?
C21 C20 C30 C31 164.2(3) . . . . ?
C21 C22 C23 C24 -179.5(3) . . . . ?
C21 C22 C23 C25 2.1(4) . . . . ?
C21 C27 C28 C29 -5.6(5) . . . . ?
C22 C17 C18 C19 14.5(5) . . . . ?
C22 C21 C27 C26 0.3(4) . . . . ?
C22 C21 C27 C28 -178.6(3) . . . . ?
C22 C23 C24 C7 3.6(5) . . . . ?
C22 C23 C25 C26 -0.4(5) . . . . ?
C23 C25 C26 C27 -1.3(5) . . . . ?
C24 C7 C8 C9 170.7(3) . . . . ?
C24 C7 C8 C17 -6.1(4) . . . . ?
C24 C23 C25 C26 -178.8(3) . . . . ?
C25 C23 C24 C7 -178.0(3) . . . . ?
C25 C26 C27 C21 1.4(5) . . . . ?
C25 C26 C27 C28 -179.7(3) . . . . ?
C26 C27 C28 C29 175.6(3) . . . . ?
C27 C21 C22 C17 177.7(3) . . . . ?
C27 C21 C22 C23 -2.0(4) . . . . ?
C27 C28 C29 C30 0.8(5) . . . . ?
C27 C28 C29 C44 -179.1(3) . . . . ?
C28 C29 C30 C20 8.4(4) . . . . ?
C28 C29 C30 C31 -169.2(3) . . . . ?
C28 C29 C44 C39 176.9(3) . . . . ?
C28 C29 C44 C43 -4.2(5) . . . . ?
C29 C30 C31 N2 -10.7(5) . . . . ?
C29 C30 C31 C32 164.1(3) . . . . ?
C30 C20 C21 C22 -172.0(3) . . . . ?
C30 C20 C21 C27 8.7(4) . . . . ?
C30 C29 C44 C39 -3.1(5) . . . . ?
C30 C29 C44 C43 175.8(3) . . . . ?
C30 C31 C32 C33 -127.3(3) . . . . ?
C30 C31 C32 C35 109.3(4) . . . . ?
C31 N2 C39 C40 -177.4(3) . . . . ?
C31 N2 C39 C44 6.5(5) . . . . ?
C31 C32 C33 C34 64.0(4) . . . . ?
C31 C32 C35 C36 -162.2(3) . . . . ?
C32 C35 C36 C37 -173.4(3) . . . . ?
C33 C32 C35 C36 74.1(4) . . . . ?
C35 C32 C33 C34 -172.0(3) . . . . ?
C35 C36 C37 C38 174.5(4) . . . . ?
C39 N2 C31 C30 2.1(5) . . . . ?
C39 N2 C31 C32 -173.2(3) . . . . ?
C39 C40 C41 C42 1.6(6) . . . . ?
C40 C39 C44 C29 178.1(3) . . . . ?
C40 C39 C44 C43 -0.8(5) . . . . ?
C40 C41 C42 C43 -1.7(6) . . . . ?
C41 C42 C43 C44 0.5(5) . . . . ?
C42 C43 C44 C29 -178.1(3) . . . . ?
C42 C43 C44 C39 0.8(5) . . . . ?
C44 C29 C30 C20 -171.6(3) . . . . ?
C44 C29 C30 C31 10.8(4) . . . . ?
C44 C39 C40 C41 -0.3(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_045377_ky_160k_a
_audit_block_doi                 10.5517/ccdc.csd.cc2c5hgj
_database_code_depnum_ccdc_archive 'CCDC 2180027'
loop_
_audit_author_name
_audit_author_address
'Yan Kou'
;Tianjin University
China
;
_audit_update_record             
;
2022-06-18 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-07
_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         'C22 H22 N'
_chemical_formula_sum            'C22 H22 N'
_chemical_formula_weight         300.40
_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      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                   5.43800(10)
_cell_length_b                   17.7484(5)
_cell_length_c                   19.3921(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.455(2)
_cell_angle_gamma                90
_cell_volume                     1871.04(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      3.3510
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11255
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.780
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  73.00   0.50    2.00    --   45.75  57.00 -30.00   84
  2  ω     76.00 104.00   0.50    2.00    --   45.75  57.00 -30.00   56
  3  ω    106.00 131.00   0.50   11.97    --  101.75  96.00 -90.00   50
  4  ω     69.00  98.00   0.50   11.97    --  101.75 -45.00 150.00   58
  5  ω     39.00 109.00   0.50   11.97    --  101.75 -96.00 161.00  140
  6  ω     -8.00  78.00   0.50    2.00    --   45.75 -96.00 161.00  172
  7  ω    -32.00  26.00   0.50    2.00    --  -45.75  96.00 -90.00  116
  8  ω    -53.00 -27.00   0.50   11.97    -- -100.00  45.00 120.00   52
  9  ω    -96.00 -70.00   0.50   11.97    -- -100.00  45.00 120.00   52
 10  ω   -116.00 -27.00   0.50   11.97    -- -100.00 125.00  60.00  178
 11  ω   -105.00 -50.00   0.50   11.97    -- -100.00  96.00 -90.00  110
 12  ω    -71.00 -34.00   0.50   11.97    -- -100.00  45.00 -90.00   74
 13  ω   -159.00 -87.00   0.50   11.97    -- -100.00 -96.00 161.00  144
 14  ω   -119.00 -94.00   0.50    2.00    --  -45.75-125.00  30.00   50
 15  ω   -117.00 -76.00   0.50    2.00    --  -45.75-125.00 -60.00   82
 16  ω   -170.00 -84.00   0.50   11.97    -- -100.00 -61.00 -90.00  172
 17  ω   -167.00-110.00   0.50   11.97    -- -100.00 -45.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1595770000
_diffrn_orient_matrix_UB_12      0.0665091000
_diffrn_orient_matrix_UB_13      0.0258540000
_diffrn_orient_matrix_UB_21      -0.0869778000
_diffrn_orient_matrix_UB_22      0.0470365000
_diffrn_orient_matrix_UB_23      -0.0628132000
_diffrn_orient_matrix_UB_31      -0.2175772000
_diffrn_orient_matrix_UB_32      0.0297706000
_diffrn_orient_matrix_UB_33      0.0413156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2867
_reflns_number_total             3630
_reflns_odcompleteness_completeness 99.97
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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 (Sheldrick, 2015)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0814
_refine_ls_restrained_S_all      1.062
_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)+(0.1275P)²+1.2041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2466
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N -0.2191(4) 0.71475(13) 0.44517(12) 0.0513(6) Uani 1 1 d . . . . .
C1 C -0.2120(5) 0.74104(16) 0.51244(15) 0.0512(7) Uani 1 1 d . . . . .
C2 C -0.3892(6) 0.79506(18) 0.53020(18) 0.0621(8) Uani 1 1 d . . . . .
H2 H -0.512277 0.809892 0.497314 0.074 Uiso 1 1 calc R . . . .
C3 C -0.3843(6) 0.82639(19) 0.59515(18) 0.0656(9) Uani 1 1 d . . . . .
H3 H -0.505424 0.862219 0.607410 0.079 Uiso 1 1 calc R . . . .
C4 C -0.2009(6) 0.80533(18) 0.64289(19) 0.0660(8) Uani 1 1 d . . . . .
H4 H -0.195772 0.827582 0.687453 0.079 Uiso 1 1 calc R . . . .
C5 C -0.0271(6) 0.75251(17) 0.62589(16) 0.0575(7) Uani 1 1 d . . . . .
H5 H 0.095950 0.738694 0.659190 0.069 Uiso 1 1 calc R . . . .
C6 C -0.0275(5) 0.71871(15) 0.56065(15) 0.0482(6) Uani 1 1 d . . . . .
C7 C 0.1378(5) 0.65928(15) 0.54064(14) 0.0450(6) Uani 1 1 d . . . . .
C8 C 0.3322(5) 0.63559(15) 0.58408(14) 0.0463(6) Uani 1 1 d . . . . .
H8 H 0.362483 0.661427 0.626356 0.056 Uiso 1 1 calc R . . . .
C9 C 0.4806(4) 0.57589(15) 0.56725(13) 0.0432(6) Uani 1 1 d . . . . .
C10 C 0.4284(4) 0.53293(14) 0.50665(12) 0.0405(6) Uani 1 1 d . . . . .
C11 C 0.2339(4) 0.55592(14) 0.46109(13) 0.0408(6) Uani 1 1 d . . . . .
C12 C 0.1007(4) 0.62393(15) 0.47553(13) 0.0413(6) Uani 1 1 d . . . . .
C13 C -0.0691(4) 0.66164(16) 0.42651(14) 0.0468(6) Uani 1 1 d . . . . .
C14 C 0.1722(5) 0.50637(15) 0.40500(13) 0.0450(6) Uani 1 1 d . . . . .
H14 H 0.030872 0.517112 0.376891 0.054 Uiso 1 1 calc R . . . .
C15 C 0.3072(5) 0.44528(15) 0.39080(13) 0.0449(6) Uani 1 1 d . . . . .
H15 H 0.261921 0.415096 0.352059 0.054 Uiso 1 1 calc R . . . .
C16 C -0.0730(5) 0.64850(17) 0.34890(14) 0.0495(7) Uani 1 1 d . . . . .
H16 H 0.077812 0.619510 0.337045 0.059 Uiso 1 1 calc R . . . .
C17 C -0.3006(5) 0.60164(17) 0.32673(16) 0.0554(7) Uani 1 1 d . . . . .
H17A H -0.321811 0.560602 0.360635 0.066 Uiso 1 1 calc R . . . .
H17B H -0.447733 0.634358 0.328447 0.066 Uiso 1 1 calc R . . . .
C18 C -0.2898(8) 0.5673(3) 0.2556(2) 0.0805(11) Uani 1 1 d . . . . .
H18A H -0.264205 0.607193 0.221594 0.121 Uiso 1 1 calc GR . . . .
H18B H -0.444726 0.541191 0.244810 0.121 Uiso 1 1 calc GR . . . .
H18C H -0.153328 0.531319 0.254351 0.121 Uiso 1 1 calc GR . . . .
C19 C -0.0694(5) 0.72376(18) 0.31024(15) 0.0560(7) Uani 1 1 d . . . . .
H19A H -0.080404 0.713503 0.260075 0.067 Uiso 1 1 calc R . . . .
H19B H -0.217185 0.752981 0.322431 0.067 Uiso 1 1 calc R . . . .
C20 C 0.1572(6) 0.7718(2) 0.32522(18) 0.0638(8) Uani 1 1 d . . . . .
H20A H 0.173477 0.780706 0.375527 0.077 Uiso 1 1 calc R . . . .
H20B H 0.305307 0.744256 0.310609 0.077 Uiso 1 1 calc R . . . .
C21 C 0.1440(8) 0.8449(2) 0.2892(2) 0.0881(12) Uani 1 1 d . . . . .
H21A H 0.003002 0.873920 0.306515 0.106 Uiso 1 1 calc R . . . .
H21B H 0.114048 0.835860 0.239306 0.106 Uiso 1 1 calc R . . . .
C22 C 0.3766(10) 0.8911(3) 0.2990(3) 0.1148(17) Uani 1 1 d . . . . .
H22A H 0.513061 0.865690 0.276578 0.172 Uiso 1 1 calc GR . . . .
H22B H 0.415148 0.896616 0.348377 0.172 Uiso 1 1 calc GR . . . .
H22C H 0.351834 0.941064 0.278354 0.172 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
N1 C1 1.385(4) . ?
N1 C13 1.304(3) . ?
C1 C2 1.408(4) . ?
C1 C6 1.411(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(4) . ?
C6 C7 1.445(4) . ?
C7 C8 1.399(4) . ?
C7 C12 1.420(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(4) . ?
C9 C10 1.424(4) . ?
C9 C15 1.445(4) 3_666 ?
C10 C10 1.431(5) 3_666 ?
C10 C11 1.421(3) . ?
C11 C12 1.439(4) . ?
C11 C14 1.432(4) . ?
C12 C13 1.470(4) . ?
C13 C16 1.522(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.342(4) . ?
C15 H15 0.9500 . ?
C16 H16 1.0000 . ?
C16 C17 1.543(4) . ?
C16 C19 1.532(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.510(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.473(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.516(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C13 N1 C1 120.2(2) . . ?
N1 C1 C2 117.2(3) . . ?
N1 C1 C6 122.1(2) . . ?
C2 C1 C6 120.6(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 117.6(3) . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 124.6(3) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 C6 119.1(2) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 C15 122.1(2) . 3_666 ?
C10 C9 C15 117.7(2) . 3_666 ?
C9 C10 C10 119.2(3) . 3_666 ?
C11 C10 C9 119.3(2) . . ?
C11 C10 C10 121.5(3) . 3_666 ?
C10 C11 C12 119.4(2) . . ?
C10 C11 C14 116.9(2) . . ?
C14 C11 C12 123.6(2) . . ?
C7 C12 C11 118.9(2) . . ?
C7 C12 C13 116.5(2) . . ?
C11 C12 C13 124.6(2) . . ?
N1 C13 C12 122.5(3) . . ?
N1 C13 C16 113.1(2) . . ?
C12 C13 C16 124.2(2) . . ?
C11 C14 H14 118.9 . . ?
C15 C14 C11 122.2(2) . . ?
C15 C14 H14 118.9 . . ?
C9 C15 H15 119.1 3_666 . ?
C14 C15 C9 121.9(2) . 3_666 ?
C14 C15 H15 119.1 . . ?
C13 C16 H16 108.4 . . ?
C13 C16 C17 110.4(2) . . ?
C13 C16 C19 110.5(2) . . ?
C17 C16 H16 108.4 . . ?
C19 C16 H16 108.4 . . ?
C19 C16 C17 110.7(2) . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 C16 115.0(3) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 108.6 . . ?
C16 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C16 114.6(2) . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 111.9(3) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C20 C21 C22 112.8(4) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
N1 C1 C2 C3 -176.6(3) . . . . ?
N1 C1 C6 C5 175.7(3) . . . . ?
N1 C1 C6 C7 -8.1(4) . . . . ?
N1 C13 C16 C17 -78.4(3) . . . . ?
N1 C13 C16 C19 44.4(3) . . . . ?
C1 N1 C13 C12 4.1(4) . . . . ?
C1 N1 C13 C16 -170.7(2) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C6 C7 C8 177.4(2) . . . . ?
C1 C6 C7 C12 -3.0(4) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 175.8(2) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -175.5(3) . . . . ?
C5 C6 C7 C8 -6.6(4) . . . . ?
C5 C6 C7 C12 173.0(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C7 C8 C9 175.8(2) . . . . ?
C6 C7 C12 C11 -168.3(2) . . . . ?
C6 C7 C12 C13 13.4(3) . . . . ?
C7 C8 C9 C10 -4.5(4) . . . . ?
C7 C8 C9 C15 175.2(2) . . . 3_666 ?
C7 C12 C13 N1 -14.6(4) . . . . ?
C7 C12 C13 C16 159.7(2) . . . . ?
C8 C7 C12 C11 11.3(3) . . . . ?
C8 C7 C12 C13 -167.0(2) . . . . ?
C8 C9 C10 C10 -174.4(3) . . . 3_666 ?
C8 C9 C10 C11 4.9(3) . . . . ?
C9 C10 C11 C12 2.7(3) . . . . ?
C9 C10 C11 C14 -173.5(2) . . . . ?
C10 C10 C11 C12 -177.9(3) 3_666 . . . ?
C10 C10 C11 C14 5.9(4) 3_666 . . . ?
C10 C11 C12 C7 -10.8(3) . . . . ?
C10 C11 C12 C13 167.4(2) . . . . ?
C10 C11 C14 C15 -7.4(3) . . . . ?
C11 C12 C13 N1 167.2(2) . . . . ?
C11 C12 C13 C16 -18.6(4) . . . . ?
C11 C14 C15 C9 2.1(4) . . . 3_666 ?
C12 C7 C8 C9 -3.8(4) . . . . ?
C12 C11 C14 C15 176.6(2) . . . . ?
C12 C13 C16 C17 106.9(3) . . . . ?
C12 C13 C16 C19 -130.3(3) . . . . ?
C13 N1 C1 C2 -176.1(3) . . . . ?
C13 N1 C1 C6 7.6(4) . . . . ?
C13 C16 C17 C18 -164.2(3) . . . . ?
C13 C16 C19 C20 61.1(3) . . . . ?
C14 C11 C12 C7 165.1(2) . . . . ?
C14 C11 C12 C13 -16.7(4) . . . . ?
C15 C9 C10 C10 5.9(4) 3_666 . . 3_666 ?
C15 C9 C10 C11 -174.7(2) 3_666 . . . ?
C16 C19 C20 C21 -177.2(3) . . . . ?
C17 C16 C19 C20 -176.2(3) . . . . ?
C19 C16 C17 C18 73.1(3) . . . . ?
C19 C20 C21 C22 -175.6(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.118 0.000 0.500 163.4 55.7 ?
2 -0.393 0.500 0.000 163.4 55.7 ?

_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 1.698
_oxdiff_exptl_absorpt_empirical_full_min 0.621
