# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zhangyif_0224_2
_database_code_depnum_ccdc_archive 'CCDC 2270021'
loop_
_audit_author_name
_audit_author_address
'Guo-Qiang Xu'
;Lanzhou University
China
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-09-29 downloaded from the CCDC.
;
_audit_creation_date             2023-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H18 N2)'
_chemical_formula_sum            'C36 H36 N4'
_chemical_formula_weight         524.69
_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                   13.9327(3)
_cell_length_b                   11.0108(3)
_cell_length_c                   19.2787(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.663(2)
_cell_angle_gamma                90
_cell_volume                     2873.84(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8888
_cell_measurement_temperature    300.89(10)
_cell_measurement_theta_max      75.7050
_cell_measurement_theta_min      2.3480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20922
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.374
_diffrn_reflns_theta_min         3.548
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.89(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_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    -73.00 -16.00   1.00    0.20    --  -45.40 114.00  11.00   57
  2  ω    -72.00 -42.00   1.00    0.80    -- -100.00  61.00   0.00   30
  3  ω    -51.00 -26.00   1.00    0.80    -- -100.00  61.00  30.00   25
  4  ω    -66.00 -28.00   1.00    0.80    -- -100.00  61.00 -30.00   38
  5  ω    -53.00 -25.00   1.00    0.80    -- -100.00  45.00-120.00   28
  6  ω    -54.00 -27.00   1.00    0.80    -- -100.00  45.00-180.00   27
  7  ω    -92.00 -67.00   1.00    0.80    -- -100.00 114.00  11.00   25
  8  ω   -109.00 -26.00   1.00    0.80    -- -100.00  77.00   0.00   83
  9  ω    -54.00 -25.00   1.00    0.80    -- -100.00  45.00 120.00   29
 10  ω   -117.00 -92.00   1.00    0.80    -- -100.00 170.00 154.00   25
 11  ω   -111.00 -77.00   1.00    0.80    -- -100.00 125.00 -90.00   34
 12  ω   -177.00-140.00   1.00    0.80    -- -100.00 -30.00 120.00   37
 13  ω   -135.00 -88.00   1.00    0.80    -- -100.00 -30.00 120.00   47
 14  ω   -118.00 -53.00   1.00    0.20    --  -45.40-170.00 138.00   65
 15  ω     58.00  83.00   1.00    0.20    --   45.40 170.00 154.00   25
 16  ω     83.00 169.00   1.00    0.80    --  109.66 114.00  11.00   86
 17  ω    137.00 163.00   1.00    0.80    --  109.66  45.00  90.00   26
 18  ω     89.00 122.00   1.00    0.80    --  109.66  45.00  90.00   33
 19  ω     93.00 175.00   1.00    0.80    --  109.66  61.00 -90.00   82
 20  ω     63.00  88.00   1.00    0.80    --  109.66-114.00 -78.00   25
 21  ω     36.00 109.00   1.00    0.80    --  109.66-125.00  30.00   73
 22  ω     90.00 115.00   1.00    0.80    --  109.66-170.00 138.00   25
 23  ω     56.00  81.00   1.00    0.20    --   45.40-170.00 138.00   25
 24  ω     43.00  68.00   1.00    0.80    --  109.66 -61.00  60.00   25
 25  ω     27.00  52.00   1.00    0.20    --   45.40-114.00 -78.00   25
 26  ω    -28.00  39.00   1.00    0.20    --   45.40 -37.00 150.00   67
 27  ω   -118.00 -18.00   1.00    0.20    --  -45.40 -77.00-150.00  100
 28  ω   -143.00-106.00   1.00    0.80    -- -100.00-114.00 -78.00   37
;
_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      -0.0336255000
_diffrn_orient_matrix_UB_12      0.1145873000
_diffrn_orient_matrix_UB_13      0.0335684000
_diffrn_orient_matrix_UB_21      -0.0744727000
_diffrn_orient_matrix_UB_22      -0.0767006000
_diffrn_orient_matrix_UB_23      0.0288890000
_diffrn_orient_matrix_UB_31      0.0792283000
_diffrn_orient_matrix_UB_32      -0.0235758000
_diffrn_orient_matrix_UB_33      0.0692864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                4190
_reflns_number_total             5716
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.0021(2)
_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   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.055
_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)+(0.0640P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C27(H27A,H27B), C36(H36A,H36B), C7(H7B,H7A), C23(H23A,H23B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C15(H15), C19(H19), C26(H26), C30(H30), C32(H32),
 C34(H34), C35(H35), C2(H2A), C11(H11), C17(H17), C20(H20), C21(H21), C24(H24),
 C28(H28), C29(H29), C31(H31), C33(H33)
;
_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 0.69983(9) 0.33549(11) 0.61247(6) 0.0662(3) Uani 1 1 d . . . . .
N2 N 0.59897(9) 0.50910(12) 0.41064(7) 0.0700(3) Uani 1 1 d . . . . .
H2 H 0.5428(14) 0.5119(15) 0.3793(9) 0.081(5) Uiso 1 1 d . . . . .
C1 C 0.76770(9) 0.39449(15) 0.57533(7) 0.0635(3) Uani 1 1 d . . . . .
H1 H 0.806520 0.456010 0.606572 0.076 Uiso 1 1 calc R U . . .
C3 C 0.56671(10) 0.39377(17) 0.75221(7) 0.0739(4) Uani 1 1 d . . . . .
H3 H 0.536238 0.349573 0.782113 0.089 Uiso 1 1 calc R U . . .
C4 C 0.83542(11) 0.28977(17) 0.56507(8) 0.0792(5) Uani 1 1 d . . . . .
H4A H 0.859694 0.301478 0.522354 0.095 Uiso 1 1 calc R U . . .
H4B H 0.891248 0.282434 0.605856 0.095 Uiso 1 1 calc R U . . .
C5 C 0.70428(13) 0.62716(15) 0.34589(8) 0.0785(4) Uani 1 1 d . . . . .
H5 H 0.654475 0.646196 0.305994 0.094 Uiso 1 1 calc R U . . .
C6 C 0.75980(9) 0.52608(13) 0.46185(7) 0.0583(3) Uani 1 1 d . . . . .
C8 C 0.68498(10) 0.55885(13) 0.40163(7) 0.0620(3) Uani 1 1 d . . . . .
C13 C 0.85576(10) 0.56836(16) 0.46659(8) 0.0730(4) Uani 1 1 d . . . . .
H13 H 0.906527 0.549663 0.505946 0.088 Uiso 1 1 calc R U . . .
C15 C 0.79928(16) 0.66536(18) 0.35191(10) 0.0931(5) Uani 1 1 d . . . . .
H15 H 0.814431 0.710429 0.315114 0.112 Uiso 1 1 calc R U . . .
C16 C 0.65604(9) 0.39672(14) 0.65891(7) 0.0592(3) Uani 1 1 d . . . . .
C19 C 0.60921(10) 0.33278(15) 0.70467(7) 0.0668(4) Uani 1 1 d . . . . .
H19 H 0.606862 0.248404 0.702876 0.080 Uiso 1 1 calc R U . . .
C22 C 0.71484(9) 0.45278(13) 0.50643(7) 0.0587(3) Uani 1 1 d . . . . .
C26 C 0.61296(10) 0.58211(16) 0.71110(8) 0.0707(4) Uani 1 1 d . . . . .
H26 H 0.614662 0.666475 0.713439 0.085 Uiso 1 1 calc R U . . .
C27 C 0.76949(13) 0.17914(18) 0.55815(9) 0.0853(5) Uani 1 1 d . . . . .
H27A H 0.808085 0.105376 0.569447 0.102 Uiso 1 1 calc R U . . .
H27B H 0.727549 0.172489 0.510376 0.102 Uiso 1 1 calc R U . . .
C30 C 0.56825(11) 0.51794(18) 0.75649(8) 0.0763(4) Uani 1 1 d . . . . .
H30 H 0.539911 0.558093 0.789132 0.092 Uiso 1 1 calc R U . . .
C32 C 0.61755(10) 0.44551(15) 0.47349(8) 0.0670(4) Uani 1 1 d . . . . .
H32 H 0.570369 0.403506 0.491007 0.080 Uiso 1 1 calc R U . . .
C34 C 0.65511(9) 0.52352(14) 0.66243(7) 0.0631(3) Uani 1 1 d . . . . .
H34 H 0.683207 0.568840 0.631618 0.076 Uiso 1 1 calc R U . . .
C35 C 0.87349(13) 0.63839(19) 0.41164(11) 0.0920(5) Uani 1 1 d . . . . .
H35 H 0.936799 0.668257 0.414733 0.110 Uiso 1 1 calc R U . . .
C36 C 0.70908(12) 0.20340(15) 0.61250(9) 0.0742(4) Uani 1 1 d . . . . .
H36A H 0.644732 0.165019 0.598473 0.089 Uiso 1 1 calc R U . . .
H36B H 0.742780 0.173811 0.659310 0.089 Uiso 1 1 calc R U . . .
N3 N 0.72566(13) 0.29860(15) 0.33761(9) 0.0863(4) Uani 1 1 d . . . . .
H3A H 0.7329(17) 0.370(2) 0.3357(12) 0.111(8) Uiso 1 1 d . . . . .
N4 N 0.47386(8) 0.07015(14) 0.32688(6) 0.0739(4) Uani 1 1 d . . . . .
C2 C 0.95879(14) 0.1359(3) 0.40905(11) 0.1126(8) Uani 1 1 d . . . . .
H2A H 1.026977 0.144705 0.423669 0.135 Uiso 1 1 calc R U . . .
C7 C 0.41829(11) 0.03072(16) 0.25725(8) 0.0723(4) Uani 1 1 d . . . . .
H7B H 0.383186 0.098260 0.230380 0.087 Uiso 1 1 calc R U . . .
H7A H 0.371066 -0.031834 0.261660 0.087 Uiso 1 1 calc R U . . .
C9 C 0.79981(12) 0.21807(16) 0.36301(8) 0.0741(4) Uani 1 1 d . . . . .
C10 C 0.42752(9) 0.11040(13) 0.37821(7) 0.0622(3) Uani 1 1 d . . . . .
C11 C 0.32481(10) 0.12283(15) 0.36263(8) 0.0698(4) Uani 1 1 d . . . . .
H11 H 0.287467 0.102135 0.317535 0.084 Uiso 1 1 calc R U . . .
C12 C 0.57567(10) 0.02348(14) 0.34323(8) 0.0682(4) Uani 1 1 d . . . . .
H12 H 0.589270 -0.018893 0.389218 0.082 Uiso 1 1 calc R U . . .
C14 C 0.65111(9) 0.12091(14) 0.34549(7) 0.0617(3) Uani 1 1 d . . . . .
C17 C 0.91757(13) 0.0233(3) 0.41244(11) 0.1069(7) Uani 1 1 d . . . . .
H17 H 0.958526 -0.042475 0.428751 0.128 Uiso 1 1 calc R U . . .
C18 C 0.75621(10) 0.10501(14) 0.36746(7) 0.0642(3) Uani 1 1 d . . . . .
C20 C 0.63667(12) 0.23992(15) 0.32871(9) 0.0758(4) Uani 1 1 d . . . . .
H20 H 0.575215 0.276687 0.313336 0.091 Uiso 1 1 calc R U . . .
C21 C 0.43211(13) 0.18642(17) 0.49591(9) 0.0822(5) Uani 1 1 d . . . . .
H21 H 0.468867 0.208522 0.540935 0.099 Uiso 1 1 calc R U . . .
C23 C 0.57327(11) -0.06847(17) 0.28361(11) 0.0859(5) Uani 1 1 d . . . . .
H23A H 0.637002 -0.073564 0.271677 0.103 Uiso 1 1 calc R U . . .
H23B H 0.554973 -0.148432 0.297235 0.103 Uiso 1 1 calc R U . . .
C24 C 0.47993(11) 0.14397(16) 0.44625(8) 0.0749(4) Uani 1 1 d . . . . .
H24 H 0.548424 0.137508 0.458211 0.090 Uiso 1 1 calc R U . . .
C25 C 0.49549(13) -0.01849(19) 0.22165(10) 0.0883(5) Uani 1 1 d . . . . .
H25A H 0.522377 0.045322 0.197135 0.106 Uiso 1 1 calc R U . . .
H25B H 0.468487 -0.081989 0.187766 0.106 Uiso 1 1 calc R U . . .
C28 C 0.81730(12) 0.00594(18) 0.39226(9) 0.0830(5) Uani 1 1 d . . . . .
H28 H 0.790420 -0.070704 0.395065 0.100 Uiso 1 1 calc R U . . .
C29 C 0.33104(14) 0.19700(16) 0.48053(10) 0.0846(5) Uani 1 1 d . . . . .
H29 H 0.299113 0.224826 0.514730 0.102 Uiso 1 1 calc R U . . .
C31 C 0.90208(15) 0.2353(2) 0.38475(10) 0.0991(7) Uani 1 1 d . . . . .
H31 H 0.930285 0.311397 0.382726 0.119 Uiso 1 1 calc R U . . .
C33 C 0.27836(12) 0.16546(17) 0.41344(10) 0.0824(5) Uani 1 1 d . . . . .
H33 H 0.209941 0.173017 0.402049 0.099 Uiso 1 1 calc R U . . .


_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 1.4657(17) . ?
N1 C16 1.3736(18) . ?
N1 C36 1.460(2) . ?
N2 H2 0.869(18) . ?
N2 C8 1.3655(19) . ?
N2 C32 1.370(2) . ?
C1 H1 0.9800 . ?
C1 C4 1.532(2) . ?
C1 C22 1.5021(19) . ?
C3 H3 0.9300 . ?
C3 C19 1.378(2) . ?
C3 C30 1.369(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C27 1.512(3) . ?
C5 H5 0.9300 . ?
C5 C8 1.389(2) . ?
C5 C15 1.367(3) . ?
C6 C8 1.4117(19) . ?
C6 C13 1.3982(19) . ?
C6 C22 1.4273(19) . ?
C13 H13 0.9300 . ?
C13 C35 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C35 1.386(3) . ?
C16 C19 1.4042(19) . ?
C16 C34 1.398(2) . ?
C19 H19 0.9300 . ?
C22 C32 1.3566(18) . ?
C26 H26 0.9300 . ?
C26 C30 1.382(2) . ?
C26 C34 1.379(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C36 1.515(2) . ?
C30 H30 0.9300 . ?
C32 H32 0.9300 . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
N3 H3A 0.80(2) . ?
N3 C9 1.362(2) . ?
N3 C20 1.372(2) . ?
N4 C7 1.4488(19) . ?
N4 C10 1.3764(18) . ?
N4 C12 1.4711(18) . ?
C2 H2A 0.9300 . ?
C2 C17 1.374(3) . ?
C2 C31 1.366(3) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 C25 1.507(2) . ?
C9 C18 1.397(2) . ?
C9 C31 1.400(2) . ?
C10 C11 1.3978(19) . ?
C10 C24 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C33 1.378(2) . ?
C12 H12 0.9800 . ?
C12 C14 1.495(2) . ?
C12 C23 1.526(2) . ?
C14 C18 1.4358(19) . ?
C14 C20 1.353(2) . ?
C17 H17 0.9300 . ?
C17 C28 1.372(3) . ?
C18 C28 1.397(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C24 1.371(2) . ?
C21 C29 1.374(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C25 1.514(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C33 1.373(3) . ?
C31 H31 0.9300 . ?
C33 H33 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
C16 N1 C1 122.55(12) . . ?
C16 N1 C36 122.78(12) . . ?
C36 N1 C1 112.01(12) . . ?
C8 N2 H2 124.8(11) . . ?
C8 N2 C32 109.23(11) . . ?
C32 N2 H2 125.7(11) . . ?
N1 C1 H1 109.4 . . ?
N1 C1 C4 102.56(13) . . ?
N1 C1 C22 112.53(10) . . ?
C4 C1 H1 109.4 . . ?
C22 C1 H1 109.4 . . ?
C22 C1 C4 113.31(12) . . ?
C19 C3 H3 119.2 . . ?
C30 C3 H3 119.2 . . ?
C30 C3 C19 121.57(14) . . ?
C1 C4 H4A 111.0 . . ?
C1 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C27 C4 C1 103.76(12) . . ?
C27 C4 H4A 111.0 . . ?
C27 C4 H4B 111.0 . . ?
C8 C5 H5 121.3 . . ?
C15 C5 H5 121.3 . . ?
C15 C5 C8 117.47(15) . . ?
C8 C6 C22 107.22(11) . . ?
C13 C6 C8 118.52(13) . . ?
C13 C6 C22 134.26(12) . . ?
N2 C8 C5 130.67(14) . . ?
N2 C8 C6 107.01(12) . . ?
C5 C8 C6 122.31(14) . . ?
C6 C13 H13 120.7 . . ?
C35 C13 C6 118.56(15) . . ?
C35 C13 H13 120.7 . . ?
C5 C15 H15 119.3 . . ?
C5 C15 C35 121.46(16) . . ?
C35 C15 H15 119.3 . . ?
N1 C16 C19 120.49(14) . . ?
N1 C16 C34 122.17(12) . . ?
C34 C16 C19 117.33(13) . . ?
C3 C19 C16 120.67(15) . . ?
C3 C19 H19 119.7 . . ?
C16 C19 H19 119.7 . . ?
C6 C22 C1 125.51(11) . . ?
C32 C22 C1 128.00(13) . . ?
C32 C22 C6 106.47(12) . . ?
C30 C26 H26 119.3 . . ?
C34 C26 H26 119.3 . . ?
C34 C26 C30 121.30(16) . . ?
C4 C27 H27A 111.2 . . ?
C4 C27 H27B 111.2 . . ?
C4 C27 C36 102.83(14) . . ?
H27A C27 H27B 109.1 . . ?
C36 C27 H27A 111.2 . . ?
C36 C27 H27B 111.2 . . ?
C3 C30 C26 118.38(15) . . ?
C3 C30 H30 120.8 . . ?
C26 C30 H30 120.8 . . ?
N2 C32 H32 125.0 . . ?
C22 C32 N2 110.06(13) . . ?
C22 C32 H32 125.0 . . ?
C16 C34 H34 119.7 . . ?
C26 C34 C16 120.70(14) . . ?
C26 C34 H34 119.7 . . ?
C13 C35 C15 121.62(16) . . ?
C13 C35 H35 119.2 . . ?
C15 C35 H35 119.2 . . ?
N1 C36 C27 103.81(13) . . ?
N1 C36 H36A 111.0 . . ?
N1 C36 H36B 111.0 . . ?
C27 C36 H36A 111.0 . . ?
C27 C36 H36B 111.0 . . ?
H36A C36 H36B 109.0 . . ?
C9 N3 H3A 124.6(17) . . ?
C9 N3 C20 108.95(15) . . ?
C20 N3 H3A 125.5(17) . . ?
C7 N4 C12 111.78(12) . . ?
C10 N4 C7 121.60(11) . . ?
C10 N4 C12 123.42(11) . . ?
C17 C2 H2A 119.2 . . ?
C31 C2 H2A 119.2 . . ?
C31 C2 C17 121.64(17) . . ?
N4 C7 H7B 110.9 . . ?
N4 C7 H7A 110.9 . . ?
N4 C7 C25 104.30(12) . . ?
H7B C7 H7A 108.9 . . ?
C25 C7 H7B 110.9 . . ?
C25 C7 H7A 110.9 . . ?
N3 C9 C18 107.36(14) . . ?
N3 C9 C31 130.65(19) . . ?
C18 C9 C31 121.95(19) . . ?
N4 C10 C11 120.49(12) . . ?
N4 C10 C24 122.16(12) . . ?
C24 C10 C11 117.32(13) . . ?
C10 C11 H11 119.7 . . ?
C33 C11 C10 120.64(14) . . ?
C33 C11 H11 119.7 . . ?
N4 C12 H12 109.3 . . ?
N4 C12 C14 113.03(13) . . ?
N4 C12 C23 102.82(12) . . ?
C14 C12 H12 109.3 . . ?
C14 C12 C23 112.84(13) . . ?
C23 C12 H12 109.3 . . ?
C18 C14 C12 125.60(13) . . ?
C20 C14 C12 128.60(13) . . ?
C20 C14 C18 105.80(13) . . ?
C2 C17 H17 119.3 . . ?
C28 C17 C2 121.4(2) . . ?
C28 C17 H17 119.3 . . ?
C9 C18 C14 107.53(14) . . ?
C9 C18 C28 118.58(14) . . ?
C28 C18 C14 133.85(15) . . ?
N3 C20 H20 124.8 . . ?
C14 C20 N3 110.30(15) . . ?
C14 C20 H20 124.8 . . ?
C24 C21 H21 119.3 . . ?
C24 C21 C29 121.37(15) . . ?
C29 C21 H21 119.3 . . ?
C12 C23 H23A 111.0 . . ?
C12 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
C25 C23 C12 103.73(13) . . ?
C25 C23 H23A 111.0 . . ?
C25 C23 H23B 111.0 . . ?
C10 C24 H24 119.5 . . ?
C21 C24 C10 121.01(14) . . ?
C21 C24 H24 119.5 . . ?
C7 C25 C23 103.08(14) . . ?
C7 C25 H25A 111.1 . . ?
C7 C25 H25B 111.1 . . ?
C23 C25 H25A 111.1 . . ?
C23 C25 H25B 111.1 . . ?
H25A C25 H25B 109.1 . . ?
C17 C28 C18 119.03(19) . . ?
C17 C28 H28 120.5 . . ?
C18 C28 H28 120.5 . . ?
C21 C29 H29 120.8 . . ?
C33 C29 C21 118.34(16) . . ?
C33 C29 H29 120.8 . . ?
C2 C31 C9 117.3(2) . . ?
C2 C31 H31 121.3 . . ?
C9 C31 H31 121.3 . . ?
C11 C33 H33 119.3 . . ?
C29 C33 C11 121.31(15) . . ?
C29 C33 H33 119.3 . . ?

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 C4 C27 30.84(14) . . . . ?
N1 C1 C22 C6 174.01(13) . . . . ?
N1 C1 C22 C32 -7.3(2) . . . . ?
N1 C16 C19 C3 178.85(12) . . . . ?
N1 C16 C34 C26 -178.12(12) . . . . ?
C1 N1 C16 C19 -166.14(12) . . . . ?
C1 N1 C16 C34 14.45(18) . . . . ?
C1 N1 C36 C27 -13.03(16) . . . . ?
C1 C4 C27 C36 -39.13(15) . . . . ?
C1 C22 C32 N2 -178.39(14) . . . . ?
C4 C1 C22 C6 -70.19(19) . . . . ?
C4 C1 C22 C32 108.47(17) . . . . ?
C4 C27 C36 N1 31.93(15) . . . . ?
C5 C15 C35 C13 2.3(3) . . . . ?
C6 C13 C35 C15 -1.2(3) . . . . ?
C6 C22 C32 N2 0.47(17) . . . . ?
C8 N2 C32 C22 0.19(18) . . . . ?
C8 C5 C15 C35 -0.8(3) . . . . ?
C8 C6 C13 C35 -1.1(2) . . . . ?
C8 C6 C22 C1 177.97(13) . . . . ?
C8 C6 C22 C32 -0.93(16) . . . . ?
C13 C6 C8 N2 -178.60(13) . . . . ?
C13 C6 C8 C5 2.7(2) . . . . ?
C13 C6 C22 C1 -2.5(3) . . . . ?
C13 C6 C22 C32 178.63(16) . . . . ?
C15 C5 C8 N2 179.90(16) . . . . ?
C15 C5 C8 C6 -1.7(2) . . . . ?
C16 N1 C1 C4 150.85(12) . . . . ?
C16 N1 C1 C22 -87.05(15) . . . . ?
C16 N1 C36 C27 -174.91(12) . . . . ?
C19 C3 C30 C26 0.7(2) . . . . ?
C19 C16 C34 C26 2.45(18) . . . . ?
C22 C1 C4 C27 -90.73(15) . . . . ?
C22 C6 C8 N2 1.05(15) . . . . ?
C22 C6 C8 C5 -177.67(14) . . . . ?
C22 C6 C13 C35 179.32(16) . . . . ?
C30 C3 C19 C16 0.2(2) . . . . ?
C30 C26 C34 C16 -1.7(2) . . . . ?
C32 N2 C8 C5 177.80(16) . . . . ?
C32 N2 C8 C6 -0.78(16) . . . . ?
C34 C16 C19 C3 -1.71(18) . . . . ?
C34 C26 C30 C3 0.1(2) . . . . ?
C36 N1 C1 C4 -11.08(14) . . . . ?
C36 N1 C1 C22 111.02(14) . . . . ?
C36 N1 C16 C19 -6.15(19) . . . . ?
C36 N1 C16 C34 174.44(12) . . . . ?
N3 C9 C18 C14 -1.70(16) . . . . ?
N3 C9 C18 C28 179.92(14) . . . . ?
N3 C9 C31 C2 179.15(17) . . . . ?
N4 C7 C25 C23 31.57(18) . . . . ?
N4 C10 C11 C33 -178.66(16) . . . . ?
N4 C10 C24 C21 178.48(16) . . . . ?
N4 C12 C14 C18 172.96(12) . . . . ?
N4 C12 C14 C20 -6.3(2) . . . . ?
N4 C12 C23 C25 29.69(17) . . . . ?
C2 C17 C28 C18 0.3(3) . . . . ?
C7 N4 C10 C11 -4.8(2) . . . . ?
C7 N4 C10 C24 177.40(15) . . . . ?
C7 N4 C12 C14 111.64(15) . . . . ?
C7 N4 C12 C23 -10.32(18) . . . . ?
C9 N3 C20 C14 -2.14(19) . . . . ?
C9 C18 C28 C17 1.0(2) . . . . ?
C10 N4 C7 C25 -173.72(15) . . . . ?
C10 N4 C12 C14 -88.40(18) . . . . ?
C10 N4 C12 C23 149.65(15) . . . . ?
C10 C11 C33 C29 0.1(3) . . . . ?
C11 C10 C24 C21 0.6(2) . . . . ?
C12 N4 C7 C25 -13.33(19) . . . . ?
C12 N4 C10 C11 -162.83(15) . . . . ?
C12 N4 C10 C24 19.3(2) . . . . ?
C12 C14 C18 C9 -178.96(13) . . . . ?
C12 C14 C18 C28 -0.9(3) . . . . ?
C12 C14 C20 N3 -179.62(14) . . . . ?
C12 C23 C25 C7 -38.13(17) . . . . ?
C14 C12 C23 C25 -92.39(15) . . . . ?
C14 C18 C28 C17 -176.80(17) . . . . ?
C17 C2 C31 C9 -0.2(3) . . . . ?
C18 C9 C31 C2 1.7(2) . . . . ?
C18 C14 C20 N3 1.01(17) . . . . ?
C20 N3 C9 C18 2.34(17) . . . . ?
C20 N3 C9 C31 -175.42(16) . . . . ?
C20 C14 C18 C9 0.43(16) . . . . ?
C20 C14 C18 C28 178.45(16) . . . . ?
C21 C29 C33 C11 0.7(3) . . . . ?
C23 C12 C14 C18 -70.90(18) . . . . ?
C23 C12 C14 C20 109.85(17) . . . . ?
C24 C10 C11 C33 -0.7(2) . . . . ?
C24 C21 C29 C33 -0.9(3) . . . . ?
C29 C21 C24 C10 0.2(3) . . . . ?
C31 C2 C17 C28 -0.7(3) . . . . ?
C31 C9 C18 C14 176.29(13) . . . . ?
C31 C9 C18 C28 -2.1(2) . . . . ?

_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 2.051
_oxdiff_exptl_absorpt_empirical_full_min 0.505
