# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_ty0324_6
_database_code_depnum_ccdc_archive 'CCDC 2287503'
loop_
_audit_author_name
_audit_author_address
'Wang Long'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C33 H27 N3)'
_chemical_formula_sum            'C66 H54 N6'
_chemical_formula_weight         931.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3710(2)
_cell_length_b                   12.7781(8)
_cell_length_c                   37.6747(14)
_cell_angle_alpha                95.179(4)
_cell_angle_beta                 90.024(3)
_cell_angle_gamma                90.619(4)
_cell_volume                     2575.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5376
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      75.0720
_cell_measurement_theta_min      2.3570
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            28395
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.243
_diffrn_reflns_theta_min         2.355
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00   7.00   1.00    0.50    --   44.44 -19.00  60.00   25
  2  ω    -33.00  22.00   1.00    0.50    --   44.44 -19.00  90.00   55
  3  ω     25.00 109.00   1.00    0.50    --   44.44  38.00   2.00   84
  4  ω    104.00 149.00   1.00    1.50    --  109.62  38.00   2.00   45
  5  ω    -10.00  39.00   1.00    0.50    --   44.44 -38.00-152.00   49
  6  ω     52.00 103.00   1.00    1.50    --  109.62 -77.00  60.00   51
  7  ω     77.00 102.00   1.00    1.50    --  109.62 -77.00 -90.00   25
  8  ω     38.00  87.00   1.00    1.50    --  109.62 -77.00-150.00   49
  9  ω     37.00  95.00   1.00    1.50    --  109.62-125.00-180.00   58
 10  ω    -63.00 -26.00   1.00    1.50    -- -100.00  61.00 -30.00   37
 11  ω    -73.00 -26.00   1.00    1.50    -- -100.00  61.00 -60.00   47
 12  ω    -55.00 -26.00   1.00    1.50    -- -100.00  61.00-180.00   29
 13  ω    -62.00 -27.00   1.00    1.50    -- -100.00  61.00-150.00   35
 14  ω    -53.00 -27.00   1.00    1.50    -- -100.00  45.00 -90.00   26
 15  ω    -32.00  -6.00   1.00    0.50    --  -44.44  38.00   2.00   26
 16  ω    -54.00 -29.00   1.00    1.50    -- -100.00  45.00  30.00   25
 17  ω    -54.00 -25.00   1.00    1.50    -- -100.00  45.00  90.00   29
 18  ω    -52.00 -27.00   1.00    1.50    -- -100.00  45.00 120.00   25
 19  ω   -153.00 -85.00   1.00    1.50    -- -100.00 -30.00  90.00   68
 20  ω   -166.00-133.00   1.00    1.50    -- -100.00 -45.00 -30.00   33
 21  ω   -127.00 -80.00   1.00    1.50    -- -100.00 -45.00 -30.00   47
 22  ω   -119.00 -25.00   1.00    0.50    --  -44.44 -38.00-152.00   94
 23  ω   -158.00 -83.00   1.00    1.50    -- -100.00 -38.00-152.00   75
 24  ω   -129.00 -88.00   1.00    1.50    -- -100.00  82.00 169.00   41
 25  ω   -119.00 -94.00   1.00    0.50    --  -44.32-179.00 120.00   25
 26  ω   -121.00 -79.00   1.00    0.50    --  -44.32 179.00  30.00   42
 27  ω    -13.00  14.00   1.00    0.50    --   44.32 -19.00-150.00   27
 28  ω    -53.00 -27.00   1.00    1.50    -- -100.00 125.00   0.00   26
 29  ω    -58.00 -27.00   1.00    1.50    -- -100.00 125.00 120.00   31
 30  ω   -164.00-131.00   1.00    1.50    -- -100.00-125.00-150.00   33
 31  ω   -112.00 -86.00   1.00    1.50    -- -100.00 -30.00 -90.00   26
 32  ω   -112.00 -64.00   1.00    1.50    -- -100.00 125.00   0.00   48
 33  ω   -111.00 -37.00   1.00    1.50    -- -100.00 125.00-120.00   74
 34  ω   -112.00 -70.00   1.00    1.50    -- -100.00 125.00 120.00   42
 35  ω    -52.00 -26.00   1.00    1.50    -- -100.00  45.00  60.00   26
 36  ω    -73.00 -41.00   1.00    1.50    -- -100.00  61.00  60.00   32
 37  ω   -111.00 -78.00   1.00    1.50    -- -100.00 125.00 -90.00   33
 38  ω   -174.00-136.00   1.00    1.50    -- -100.00 -30.00 -90.00   38
 39  ω   -116.00 -84.00   1.00    1.50    -- -100.00-125.00-150.00   32
 40  ω   -175.00-143.00   1.00    1.50    -- -100.00 -30.00 120.00   32
 41  ω   -129.00 -88.00   1.00    1.50    -- -100.00 -30.00 120.00   41
 42  ω    147.00 173.00   1.00    1.50    --  109.62  30.00 -90.00   26
 43  ω     64.00 102.00   1.00    1.50    --  109.62 -77.00 150.00   38
 44  ω     70.00  95.00   1.00    1.50    --  109.62 -94.00-150.00   25
 45  ω     53.00  79.00   1.00    1.50    --  109.62 -94.00   0.00   26
;
_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      0.0334322000
_diffrn_orient_matrix_UB_12      -0.1179538000
_diffrn_orient_matrix_UB_13      -0.0112142000
_diffrn_orient_matrix_UB_21      -0.1363697000
_diffrn_orient_matrix_UB_22      -0.0271494000
_diffrn_orient_matrix_UB_23      0.0340050000
_diffrn_orient_matrix_UB_31      -0.2501335000
_diffrn_orient_matrix_UB_32      -0.0024680000
_diffrn_orient_matrix_UB_33      -0.0201020000
_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                5613
_reflns_number_total             10113
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00104(9)
_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   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         10113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0996
_refine_ls_restrained_S_all      1.100
_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)+3.9127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2029
_refine_ls_wR_factor_ref         0.2266
_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:
 C3(H3), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32),
 C33(H33), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44), C45(H45),
  C46(H46), C47(H47), C48(H48), C50(H50), C51(H51), C53(H53), C54(H54),
 C56(H56), C57(H57), C58(H58), C59(H59), C60(H60), C62(H62), C63(H63), C64(H64),
  C65(H65), C66(H66)
;
_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 0.5357(7) 0.1273(3) 0.62840(9) 0.0614(10) Uani 1 1 d . . . . .
N2 N 0.5405(6) 0.0810(3) 0.66007(10) 0.0530(8) Uani 1 1 d . . . . .
N3 N 0.6999(8) 0.6188(2) 0.60698(10) 0.0615(10) Uani 1 1 d . . . . .
C1 C 0.3598(7) 0.1153(4) 0.67987(12) 0.0557(11) Uani 1 1 d . . . . .
C2 C 0.1961(8) 0.1911(3) 0.66221(11) 0.0539(10) Uani 1 1 d . . . . .
H2A H 0.184215 0.257648 0.676622 0.065 Uiso 1 1 calc R U . . .
H2B H 0.030166 0.162021 0.657867 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3358(7) 0.2042(3) 0.62642(11) 0.0513(10) Uani 1 1 d . . . . .
H3 H 0.225652 0.181471 0.606388 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3176(8) 0.0832(3) 0.71539(11) 0.0514(10) Uani 1 1 d . . . . .
C5 C 0.4835(10) 0.0139(5) 0.72945(14) 0.0779(15) Uani 1 1 d . . . . .
H5 H 0.622832 -0.010949 0.716839 0.093 Uiso 1 1 calc R U . . .
C6 C 0.4282(12) -0.0164(4) 0.76401(15) 0.0792(16) Uani 1 1 d . . . . .
H6 H 0.531964 -0.063627 0.774015 0.095 Uiso 1 1 calc R U . . .
C7 C 0.2229(12) 0.0226(5) 0.78324(15) 0.0900(19) Uani 1 1 d . . . . .
H7 H 0.195413 0.003716 0.806192 0.108 Uiso 1 1 calc R U . . .
C8 C 0.0656(12) 0.0870(5) 0.76893(14) 0.0830(16) Uani 1 1 d . . . . .
H8 H -0.075214 0.110050 0.781549 0.100 Uiso 1 1 calc R U . . .
C9 C 0.1094(10) 0.1196(5) 0.73569(14) 0.0778(15) Uani 1 1 d . . . . .
H9 H 0.000582 0.166357 0.726424 0.093 Uiso 1 1 calc R U . . .
C10 C 0.6891(9) 0.0946(3) 0.60146(11) 0.0550(10) Uani 1 1 d . . . . .
C11 C 0.8641(9) 0.0124(4) 0.60586(13) 0.0659(12) Uani 1 1 d . . . . .
H11 H 0.861945 -0.022003 0.626587 0.079 Uiso 1 1 calc R U . . .
C12 C 1.0355(10) -0.0158(3) 0.57944(14) 0.0705(14) Uani 1 1 d . . . . .
H12 H 1.147929 -0.069052 0.582570 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0415(12) 0.0341(5) 0.54852(14) 0.0868(17) Uani 1 1 d . . . . .
H13 H 1.162337 0.017073 0.531350 0.104 Uiso 1 1 calc R U . . .
C14 C 0.8647(10) 0.1104(4) 0.54317(13) 0.0742(14) Uani 1 1 d . . . . .
H14 H 0.860257 0.139524 0.521426 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6937(9) 0.1444(4) 0.56974(12) 0.0636(12) Uani 1 1 d . . . . .
H15 H 0.585217 0.198903 0.566415 0.076 Uiso 1 1 calc R U . . .
C16 C 0.4324(7) 0.3134(3) 0.62203(10) 0.0460(9) Uani 1 1 d . . . . .
C17 C 0.3032(8) 0.3757(3) 0.60017(11) 0.0538(10) Uani 1 1 d . . . . .
H17 H 0.159546 0.350546 0.588378 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3933(9) 0.4773(3) 0.59618(12) 0.0600(11) Uani 1 1 d . . . . .
H18 H 0.306187 0.520439 0.582033 0.072 Uiso 1 1 calc R U . . .
C19 C 0.6076(7) 0.5140(3) 0.61280(11) 0.0499(10) Uani 1 1 d . . . . .
C20 C 0.7275(8) 0.4543(3) 0.63509(11) 0.0549(10) Uani 1 1 d . . . . .
H20 H 0.867864 0.480814 0.647420 0.066 Uiso 1 1 calc R U . . .
C21 C 0.6409(7) 0.3526(3) 0.63968(11) 0.0475(9) Uani 1 1 d . . . . .
H21 H 0.725458 0.311504 0.654791 0.057 Uiso 1 1 calc R U . . .
C22 C 0.6869(9) 0.6529(4) 0.57277(12) 0.0707(14) Uani 1 1 d . . . . .
C23 C 0.7412(12) 0.5874(4) 0.54382(15) 0.0866(17) Uani 1 1 d . . . . .
H23 H 0.788732 0.519241 0.547190 0.104 Uiso 1 1 calc R U . . .
C24 C 0.7300(15) 0.6166(7) 0.50903(18) 0.124(3) Uani 1 1 d . . . . .
H24 H 0.756460 0.568874 0.489295 0.149 Uiso 1 1 calc R U . . .
C25 C 0.6756(14) 0.7237(7) 0.50570(19) 0.118(3) Uani 1 1 d . . . . .
H25 H 0.676587 0.748577 0.483251 0.142 Uiso 1 1 calc R U . . .
C26 C 0.6219(14) 0.7910(7) 0.5349(2) 0.117(3) Uani 1 1 d . . . . .
H26 H 0.577600 0.859952 0.532201 0.140 Uiso 1 1 calc R U . . .
C27 C 0.6333(11) 0.7568(4) 0.56754(16) 0.0865(18) Uani 1 1 d . . . . .
H27 H 0.604607 0.804160 0.587303 0.104 Uiso 1 1 calc R U . . .
C28 C 0.8019(8) 0.6841(4) 0.63601(12) 0.0655(12) Uani 1 1 d . . . . .
C29 C 1.0155(10) 0.7409(4) 0.63157(16) 0.0767(15) Uani 1 1 d . . . . .
H29 H 1.096048 0.737922 0.609659 0.092 Uiso 1 1 calc R U . . .
C30 C 1.1086(11) 0.8037(5) 0.6611(2) 0.097(2) Uani 1 1 d . . . . .
H30 H 1.258720 0.839522 0.658997 0.116 Uiso 1 1 calc R U . . .
C31 C 0.9879(15) 0.8138(6) 0.6925(2) 0.105(2) Uani 1 1 d . . . . .
H31 H 1.051831 0.857864 0.711371 0.126 Uiso 1 1 calc R U . . .
C32 C 0.7730(13) 0.7599(4) 0.69647(16) 0.0880(17) Uani 1 1 d . . . . .
H32 H 0.688607 0.768387 0.718074 0.106 Uiso 1 1 calc R U . . .
C33 C 0.6761(10) 0.6919(4) 0.66885(13) 0.0716(13) Uani 1 1 d . . . . .
H33 H 0.532246 0.652686 0.672010 0.086 Uiso 1 1 calc R U . . .
N4 N -0.0398(6) 0.3699(2) 0.87064(9) 0.0507(8) Uani 1 1 d . . . . .
N5 N -0.0398(7) 0.4153(3) 0.83927(9) 0.0532(9) Uani 1 1 d . . . . .
N6 N -0.1877(8) -0.1218(3) 0.89217(10) 0.0727(12) Uani 1 1 d . . . . .
C34 C 0.1706(8) 0.2940(3) 0.87279(11) 0.0499(10) Uani 1 1 d . . . . .
H34 H 0.283606 0.318340 0.892315 0.060 Uiso 1 1 calc R U . . .
C35 C 0.2977(7) 0.3010(3) 0.83740(12) 0.0512(10) Uani 1 1 d . . . . .
H35A H 0.468538 0.325515 0.840620 0.061 Uiso 1 1 calc R U . . .
H35B H 0.296442 0.233463 0.823420 0.061 Uiso 1 1 calc R U . . .
C36 C 0.1447(7) 0.3790(3) 0.82004(10) 0.0432(8) Uani 1 1 d . . . . .
C37 C 0.1895(8) 0.4125(3) 0.78424(11) 0.0537(10) Uani 1 1 d . . . . .
C38 C 0.3889(8) 0.3782(4) 0.76517(12) 0.0620(11) Uani 1 1 d . . . . .
H38 H 0.500710 0.333761 0.774973 0.074 Uiso 1 1 calc R U . . .
C39 C 0.4309(10) 0.4078(5) 0.73135(14) 0.0837(16) Uani 1 1 d . . . . .
H39 H 0.567919 0.382138 0.718378 0.100 Uiso 1 1 calc R U . . .
C40 C 0.2674(11) 0.4763(4) 0.71660(14) 0.0771(15) Uani 1 1 d . . . . .
H40 H 0.296212 0.498432 0.694105 0.093 Uiso 1 1 calc R U . . .
C41 C 0.0656(12) 0.5097(5) 0.73587(15) 0.0927(19) Uani 1 1 d . . . . .
H41 H -0.049443 0.552981 0.726152 0.111 Uiso 1 1 calc R U . . .
C42 C 0.0310(9) 0.4808(4) 0.76895(13) 0.0633(12) Uani 1 1 d . . . . .
H42 H -0.104346 0.507489 0.782079 0.076 Uiso 1 1 calc R U . . .
C43 C -0.2060(7) 0.4050(3) 0.89807(11) 0.0496(10) Uani 1 1 d . . . . .
C44 C -0.3709(8) 0.4835(3) 0.89422(13) 0.0552(11) Uani 1 1 d . . . . .
H44 H -0.371059 0.517549 0.873419 0.066 Uiso 1 1 calc R U . . .
C45 C -0.5359(9) 0.5125(4) 0.92080(15) 0.0748(14) Uani 1 1 d . . . . .
H45 H -0.648012 0.565807 0.917639 0.090 Uiso 1 1 calc R U . . .
C46 C -0.5406(9) 0.4649(4) 0.95211(14) 0.0682(13) Uani 1 1 d . . . . .
H46 H -0.651740 0.486224 0.970190 0.082 Uiso 1 1 calc R U . . .
C47 C -0.3791(10) 0.3864(4) 0.95584(14) 0.0715(14) Uani 1 1 d . . . . .
H47 H -0.382656 0.351461 0.976452 0.086 Uiso 1 1 calc R U . . .
C48 C -0.2110(9) 0.3577(3) 0.92975(12) 0.0615(11) Uani 1 1 d . . . . .
H48 H -0.097348 0.305201 0.933294 0.074 Uiso 1 1 calc R U . . .
C49 C 0.0765(7) 0.1835(3) 0.87755(11) 0.0463(9) Uani 1 1 d . . . . .
C50 C -0.1369(8) 0.1397(3) 0.86012(11) 0.0536(10) Uani 1 1 d . . . . .
H50 H -0.222664 0.179968 0.844902 0.064 Uiso 1 1 calc R U . . .
C51 C -0.2232(7) 0.0423(3) 0.86435(11) 0.0493(9) Uani 1 1 d . . . . .
H51 H -0.368563 0.017978 0.852825 0.059 Uiso 1 1 calc R U . . .
C52 C -0.0927(8) -0.0237(3) 0.88643(10) 0.0525(10) Uani 1 1 d . . . . .
C53 C 0.1230(8) 0.0175(3) 0.90335(11) 0.0527(10) Uani 1 1 d . . . . .
H53 H 0.213743 -0.023456 0.917810 0.063 Uiso 1 1 calc R U . . .
C54 C 0.2020(7) 0.1179(3) 0.89878(11) 0.0506(10) Uani 1 1 d . . . . .
H54 H 0.346163 0.143200 0.910432 0.061 Uiso 1 1 calc R U . . .
C55 C -0.2891(8) -0.1867(3) 0.86365(12) 0.0526(11) Uani 1 1 d . . . . .
C56 C -0.1805(11) -0.1966(3) 0.83145(13) 0.0689(13) Uani 1 1 d . . . . .
H56 H -0.034283 -0.159018 0.828228 0.083 Uiso 1 1 calc R U . . .
C57 C -0.2748(13) -0.2595(4) 0.80309(15) 0.0919(19) Uani 1 1 d . . . . .
H57 H -0.196121 -0.262183 0.781043 0.110 Uiso 1 1 calc R U . . .
C58 C -0.4867(14) -0.3188(4) 0.8074(2) 0.099(2) Uani 1 1 d . . . . .
H58 H -0.550277 -0.362605 0.788419 0.119 Uiso 1 1 calc R U . . .
C59 C -0.6059(11) -0.3124(4) 0.8407(2) 0.0871(19) Uani 1 1 d . . . . .
H59 H -0.745719 -0.353646 0.844385 0.105 Uiso 1 1 calc R U . . .
C60 C -0.5120(9) -0.2441(4) 0.86783(16) 0.0731(14) Uani 1 1 d . . . . .
H60 H -0.596929 -0.235485 0.889391 0.088 Uiso 1 1 calc R U . . .
C61 C -0.1863(9) -0.1555(3) 0.92725(13) 0.0631(12) Uani 1 1 d . . . . .
C62 C -0.1202(10) -0.2574(5) 0.93151(16) 0.0795(15) Uani 1 1 d . . . . .
H62 H -0.077534 -0.303373 0.911965 0.095 Uiso 1 1 calc R U . . .
C63 C -0.1186(13) -0.2903(5) 0.9662(2) 0.108(2) Uani 1 1 d . . . . .
H63 H -0.088585 -0.360433 0.969394 0.130 Uiso 1 1 calc R U . . .
C64 C -0.1610(17) -0.2201(7) 0.9955(2) 0.136(3) Uani 1 1 d . . . . .
H64 H -0.146197 -0.240766 1.018463 0.163 Uiso 1 1 calc R U . . .
C65 C -0.2246(13) -0.1205(6) 0.99022(16) 0.108(2) Uani 1 1 d . . . . .
H65 H -0.265986 -0.075352 1.010039 0.130 Uiso 1 1 calc R U . . .
C66 C -0.2318(11) -0.0819(5) 0.95718(14) 0.0855(17) Uani 1 1 d . . . . .
H66 H -0.264488 -0.011652 0.954602 0.103 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 N2 1.379(5) . ?
N1 C3 1.469(6) . ?
N1 C10 1.347(5) . ?
N2 C1 1.281(5) . ?
N3 C19 1.457(5) . ?
N3 C22 1.400(5) . ?
N3 C28 1.421(6) . ?
C1 C2 1.512(6) . ?
C1 C4 1.452(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.564(5) . ?
C3 H3 0.9800 . ?
C3 C16 1.507(5) . ?
C4 C5 1.400(6) . ?
C4 C9 1.414(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.422(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.333(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.438(7) . ?
C10 C15 1.404(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.402(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(6) . ?
C16 C21 1.369(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.402(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(6) . ?
C19 C20 1.352(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.401(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.347(8) . ?
C22 C27 1.393(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.419(11) . ?
C25 H25 0.9300 . ?
C25 C26 1.367(11) . ?
C26 H26 0.9300 . ?
C26 C27 1.342(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(7) . ?
C28 C33 1.406(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.402(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.344(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.354(9) . ?
C32 H32 0.9300 . ?
C32 C33 1.391(7) . ?
C33 H33 0.9300 . ?
N4 N5 1.363(4) . ?
N4 C34 1.504(5) . ?
N4 C43 1.411(5) . ?
N5 C36 1.294(5) . ?
N6 C52 1.384(5) . ?
N6 C55 1.403(6) . ?
N6 C61 1.426(6) . ?
C34 H34 0.9800 . ?
C34 C35 1.508(6) . ?
C34 C49 1.520(5) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.493(5) . ?
C36 C37 1.470(5) . ?
C37 C38 1.345(6) . ?
C37 C42 1.387(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.379(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.396(8) . ?
C40 H40 0.9300 . ?
C40 C41 1.356(8) . ?
C41 H41 0.9300 . ?
C41 C42 1.344(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.363(6) . ?
C43 C48 1.386(6) . ?
C44 H44 0.9300 . ?
C44 C45 1.366(6) . ?
C45 H45 0.9300 . ?
C45 C46 1.375(7) . ?
C46 H46 0.9300 . ?
C46 C47 1.350(7) . ?
C47 H47 0.9300 . ?
C47 C48 1.363(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.406(6) . ?
C49 C54 1.389(5) . ?
C50 H50 0.9300 . ?
C50 C51 1.346(6) . ?
C51 H51 0.9300 . ?
C51 C52 1.425(5) . ?
C52 C53 1.397(6) . ?
C53 H53 0.9300 . ?
C53 C54 1.373(6) . ?
C54 H54 0.9300 . ?
C55 C56 1.342(6) . ?
C55 C60 1.414(6) . ?
C56 H56 0.9300 . ?
C56 C57 1.371(7) . ?
C57 H57 0.9300 . ?
C57 C58 1.378(9) . ?
C58 H58 0.9300 . ?
C58 C59 1.407(9) . ?
C59 H59 0.9300 . ?
C59 C60 1.373(8) . ?
C60 H60 0.9300 . ?
C61 C62 1.377(7) . ?
C61 C66 1.424(7) . ?
C62 H62 0.9300 . ?
C62 C63 1.409(8) . ?
C63 H63 0.9300 . ?
C63 C64 1.379(11) . ?
C64 H64 0.9300 . ?
C64 C65 1.353(11) . ?
C65 H65 0.9300 . ?
C65 C66 1.381(8) . ?
C66 H66 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
N2 N1 C3 113.7(3) . . ?
C10 N1 N2 120.6(4) . . ?
C10 N1 C3 125.4(3) . . ?
C1 N2 N1 109.6(3) . . ?
C22 N3 C19 119.2(4) . . ?
C22 N3 C28 121.2(4) . . ?
C28 N3 C19 119.6(4) . . ?
N2 C1 C2 113.0(4) . . ?
N2 C1 C4 122.9(4) . . ?
C4 C1 C2 124.1(4) . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C1 C2 C3 102.7(3) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
N1 C3 C2 100.7(3) . . ?
N1 C3 H3 109.2 . . ?
N1 C3 C16 112.9(3) . . ?
C2 C3 H3 109.2 . . ?
C16 C3 C2 115.3(4) . . ?
C16 C3 H3 109.2 . . ?
C5 C4 C1 119.4(4) . . ?
C5 C4 C9 119.7(4) . . ?
C9 C4 C1 120.9(4) . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(5) . . ?
C6 C5 H5 121.7 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(6) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(5) . . ?
C8 C9 H9 119.5 . . ?
N1 C10 C11 120.0(4) . . ?
N1 C10 C15 121.0(4) . . ?
C15 C10 C11 118.8(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.5(5) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.7(5) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 H15 120.6 . . ?
C14 C15 C10 118.8(5) . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C3 118.9(3) . . ?
C21 C16 C3 121.4(3) . . ?
C21 C16 C17 119.7(4) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.7(4) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 N3 119.3(4) . . ?
C20 C19 N3 120.8(4) . . ?
C20 C19 C18 119.9(4) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.3(4) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 N3 120.7(5) . . ?
C23 C22 C27 117.6(5) . . ?
C27 C22 N3 121.5(5) . . ?
C22 C23 H23 118.3 . . ?
C22 C23 C24 123.4(6) . . ?
C24 C23 H23 118.3 . . ?
C23 C24 H24 122.1 . . ?
C23 C24 C25 115.7(7) . . ?
C25 C24 H24 122.1 . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.6(7) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 H27 118.9 . . ?
C26 C27 C22 122.2(7) . . ?
C26 C27 H27 118.9 . . ?
C29 C28 N3 120.1(5) . . ?
C29 C28 C33 120.8(5) . . ?
C33 C28 N3 119.0(4) . . ?
C28 C29 H29 121.1 . . ?
C28 C29 C30 117.8(6) . . ?
C30 C29 H29 121.1 . . ?
C29 C30 H30 118.9 . . ?
C31 C30 C29 122.1(6) . . ?
C31 C30 H30 118.9 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.9(6) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.4 . . ?
C31 C32 C33 121.2(6) . . ?
C33 C32 H32 119.4 . . ?
C28 C33 H33 120.9 . . ?
C32 C33 C28 118.1(5) . . ?
C32 C33 H33 120.9 . . ?
N5 N4 C34 112.2(3) . . ?
N5 N4 C43 120.0(3) . . ?
C43 N4 C34 127.4(3) . . ?
C36 N5 N4 108.8(3) . . ?
C52 N6 C55 119.9(3) . . ?
C52 N6 C61 119.7(4) . . ?
C55 N6 C61 120.4(3) . . ?
N4 C34 H34 110.2 . . ?
N4 C34 C35 101.9(3) . . ?
N4 C34 C49 111.8(3) . . ?
C35 C34 H34 110.2 . . ?
C35 C34 C49 112.4(3) . . ?
C49 C34 H34 110.2 . . ?
C34 C35 H35A 111.1 . . ?
C34 C35 H35B 111.1 . . ?
H35A C35 H35B 109.1 . . ?
C36 C35 C34 103.3(3) . . ?
C36 C35 H35A 111.1 . . ?
C36 C35 H35B 111.1 . . ?
N5 C36 C35 113.8(3) . . ?
N5 C36 C37 121.2(4) . . ?
C37 C36 C35 125.0(4) . . ?
C38 C37 C36 120.7(4) . . ?
C38 C37 C42 117.4(4) . . ?
C42 C37 C36 121.8(4) . . ?
C37 C38 H38 119.4 . . ?
C37 C38 C39 121.3(5) . . ?
C39 C38 H38 119.4 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.0(5) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.8 . . ?
C41 C40 C39 118.4(5) . . ?
C41 C40 H40 120.8 . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.4(5) . . ?
C42 C41 H41 119.8 . . ?
C37 C42 H42 118.8 . . ?
C41 C42 C37 122.5(5) . . ?
C41 C42 H42 118.8 . . ?
C44 C43 N4 121.9(4) . . ?
C44 C43 C48 117.6(4) . . ?
C48 C43 N4 120.4(4) . . ?
C43 C44 H44 119.9 . . ?
C43 C44 C45 120.3(5) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 119.1 . . ?
C44 C45 C46 121.8(5) . . ?
C46 C45 H45 119.1 . . ?
C45 C46 H46 121.0 . . ?
C47 C46 C45 118.1(5) . . ?
C47 C46 H46 121.0 . . ?
C46 C47 H47 119.6 . . ?
C46 C47 C48 120.8(5) . . ?
C48 C47 H47 119.6 . . ?
C43 C48 H48 119.3 . . ?
C47 C48 C43 121.4(5) . . ?
C47 C48 H48 119.3 . . ?
C50 C49 C34 122.8(4) . . ?
C54 C49 C34 121.6(4) . . ?
C54 C49 C50 115.6(3) . . ?
C49 C50 H50 118.3 . . ?
C51 C50 C49 123.3(4) . . ?
C51 C50 H50 118.3 . . ?
C50 C51 H51 119.9 . . ?
C50 C51 C52 120.3(4) . . ?
C52 C51 H51 119.9 . . ?
N6 C52 C51 120.3(4) . . ?
N6 C52 C53 122.3(4) . . ?
C53 C52 C51 117.3(4) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.5(3) . . ?
C54 C53 H53 119.8 . . ?
C49 C54 H54 118.5 . . ?
C53 C54 C49 123.0(4) . . ?
C53 C54 H54 118.5 . . ?
N6 C55 C60 120.8(4) . . ?
C56 C55 N6 121.8(4) . . ?
C56 C55 C60 117.4(5) . . ?
C55 C56 H56 118.4 . . ?
C55 C56 C57 123.2(6) . . ?
C57 C56 H56 118.4 . . ?
C56 C57 H57 120.2 . . ?
C56 C57 C58 119.7(6) . . ?
C58 C57 H57 120.2 . . ?
C57 C58 H58 120.3 . . ?
C57 C58 C59 119.4(6) . . ?
C59 C58 H58 120.3 . . ?
C58 C59 H59 120.6 . . ?
C60 C59 C58 118.8(6) . . ?
C60 C59 H59 120.6 . . ?
C55 C60 H60 119.3 . . ?
C59 C60 C55 121.4(6) . . ?
C59 C60 H60 119.3 . . ?
C62 C61 N6 118.5(5) . . ?
C62 C61 C66 121.3(5) . . ?
C66 C61 N6 120.0(4) . . ?
C61 C62 H62 120.8 . . ?
C61 C62 C63 118.4(6) . . ?
C63 C62 H62 120.8 . . ?
C62 C63 H63 119.5 . . ?
C64 C63 C62 120.9(6) . . ?
C64 C63 H63 119.5 . . ?
C63 C64 H64 120.7 . . ?
C65 C64 C63 118.7(6) . . ?
C65 C64 H64 120.7 . . ?
C64 C65 H65 118.0 . . ?
C64 C65 C66 124.0(7) . . ?
C66 C65 H65 118.0 . . ?
C61 C66 H66 121.8 . . ?
C65 C66 C61 116.4(6) . . ?
C65 C66 H66 121.8 . . ?

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 N2 C1 C2 2.1(5) . . . . ?
N1 N2 C1 C4 -178.5(4) . . . . ?
N1 C3 C16 C17 142.3(4) . . . . ?
N1 C3 C16 C21 -39.1(5) . . . . ?
N1 C10 C11 C12 -174.8(4) . . . . ?
N1 C10 C15 C14 177.1(5) . . . . ?
N2 N1 C3 C2 -4.8(4) . . . . ?
N2 N1 C3 C16 118.7(4) . . . . ?
N2 N1 C10 C11 -1.5(7) . . . . ?
N2 N1 C10 C15 -177.1(4) . . . . ?
N2 C1 C2 C3 -4.9(5) . . . . ?
N2 C1 C4 C5 1.8(7) . . . . ?
N2 C1 C4 C9 -177.2(4) . . . . ?
N3 C19 C20 C21 -178.2(4) . . . . ?
N3 C22 C23 C24 179.5(6) . . . . ?
N3 C22 C27 C26 179.5(5) . . . . ?
N3 C28 C29 C30 -179.7(5) . . . . ?
N3 C28 C33 C32 -177.2(5) . . . . ?
C1 C2 C3 N1 5.3(4) . . . . ?
C1 C2 C3 C16 -116.5(4) . . . . ?
C1 C4 C5 C6 -178.5(4) . . . . ?
C1 C4 C9 C8 178.2(5) . . . . ?
C2 C1 C4 C5 -178.9(4) . . . . ?
C2 C1 C4 C9 2.1(7) . . . . ?
C2 C3 C16 C17 -102.8(4) . . . . ?
C2 C3 C16 C21 75.9(5) . . . . ?
C3 N1 N2 C1 2.0(5) . . . . ?
C3 N1 C10 C11 -174.8(4) . . . . ?
C3 N1 C10 C15 9.6(7) . . . . ?
C3 C16 C17 C18 179.9(4) . . . . ?
C3 C16 C21 C20 179.8(4) . . . . ?
C4 C1 C2 C3 175.7(4) . . . . ?
C4 C5 C6 C7 -1.5(8) . . . . ?
C5 C4 C9 C8 -0.8(8) . . . . ?
C5 C6 C7 C8 2.8(9) . . . . ?
C6 C7 C8 C9 -3.0(9) . . . . ?
C7 C8 C9 C4 2.1(9) . . . . ?
C9 C4 C5 C6 0.5(8) . . . . ?
C10 N1 N2 C1 -172.1(4) . . . . ?
C10 N1 C3 C2 169.0(4) . . . . ?
C10 N1 C3 C16 -67.6(6) . . . . ?
C10 C11 C12 C13 -0.1(8) . . . . ?
C11 C10 C15 C14 1.5(7) . . . . ?
C11 C12 C13 C14 -3.1(8) . . . . ?
C12 C13 C14 C15 5.6(9) . . . . ?
C13 C14 C15 C10 -4.7(8) . . . . ?
C15 C10 C11 C12 0.9(7) . . . . ?
C16 C17 C18 C19 1.5(7) . . . . ?
C17 C16 C21 C20 -1.5(6) . . . . ?
C17 C18 C19 N3 177.8(4) . . . . ?
C17 C18 C19 C20 -3.9(7) . . . . ?
C18 C19 C20 C21 3.6(7) . . . . ?
C19 N3 C22 C23 -41.1(7) . . . . ?
C19 N3 C22 C27 143.1(5) . . . . ?
C19 N3 C28 C29 137.0(5) . . . . ?
C19 N3 C28 C33 -45.0(6) . . . . ?
C19 C20 C21 C16 -0.9(7) . . . . ?
C21 C16 C17 C18 1.2(7) . . . . ?
C22 N3 C19 C18 -40.1(6) . . . . ?
C22 N3 C19 C20 141.7(5) . . . . ?
C22 N3 C28 C29 -42.9(7) . . . . ?
C22 N3 C28 C33 135.2(5) . . . . ?
C22 C23 C24 C25 4.8(10) . . . . ?
C23 C22 C27 C26 3.6(9) . . . . ?
C23 C24 C25 C26 -4.2(11) . . . . ?
C24 C25 C26 C27 3.6(11) . . . . ?
C25 C26 C27 C22 -3.2(10) . . . . ?
C27 C22 C23 C24 -4.5(9) . . . . ?
C28 N3 C19 C18 140.0(5) . . . . ?
C28 N3 C19 C20 -38.2(6) . . . . ?
C28 N3 C22 C23 138.7(5) . . . . ?
C28 N3 C22 C27 -37.1(7) . . . . ?
C28 C29 C30 C31 -3.8(9) . . . . ?
C29 C28 C33 C32 0.8(8) . . . . ?
C29 C30 C31 C32 2.0(10) . . . . ?
C30 C31 C32 C33 1.3(10) . . . . ?
C31 C32 C33 C28 -2.7(9) . . . . ?
C33 C28 C29 C30 2.3(8) . . . . ?
N4 N5 C36 C35 -0.2(4) . . . . ?
N4 N5 C36 C37 178.8(3) . . . . ?
N4 C34 C35 C36 0.0(4) . . . . ?
N4 C34 C49 C50 38.7(5) . . . . ?
N4 C34 C49 C54 -143.4(4) . . . . ?
N4 C43 C44 C45 177.3(4) . . . . ?
N4 C43 C48 C47 -176.4(4) . . . . ?
N5 N4 C34 C35 -0.1(4) . . . . ?
N5 N4 C34 C49 -120.3(4) . . . . ?
N5 N4 C43 C44 0.5(6) . . . . ?
N5 N4 C43 C48 178.6(4) . . . . ?
N5 C36 C37 C38 176.7(4) . . . . ?
N5 C36 C37 C42 -2.7(6) . . . . ?
N6 C52 C53 C54 -175.6(4) . . . . ?
N6 C55 C56 C57 179.9(5) . . . . ?
N6 C55 C60 C59 -176.3(4) . . . . ?
N6 C61 C62 C63 179.9(5) . . . . ?
N6 C61 C66 C65 -179.4(5) . . . . ?
C34 N4 N5 C36 0.2(4) . . . . ?
C34 N4 C43 C44 172.0(4) . . . . ?
C34 N4 C43 C48 -10.0(6) . . . . ?
C34 C35 C36 N5 0.1(4) . . . . ?
C34 C35 C36 C37 -178.9(4) . . . . ?
C34 C49 C50 C51 -179.4(4) . . . . ?
C34 C49 C54 C53 -179.4(4) . . . . ?
C35 C34 C49 C50 -75.2(5) . . . . ?
C35 C34 C49 C54 102.8(5) . . . . ?
C35 C36 C37 C38 -4.4(6) . . . . ?
C35 C36 C37 C42 176.2(4) . . . . ?
C36 C37 C38 C39 179.0(5) . . . . ?
C36 C37 C42 C41 -178.1(5) . . . . ?
C37 C38 C39 C40 1.4(8) . . . . ?
C38 C37 C42 C41 2.5(8) . . . . ?
C38 C39 C40 C41 -1.9(9) . . . . ?
C39 C40 C41 C42 2.7(9) . . . . ?
C40 C41 C42 C37 -3.1(9) . . . . ?
C42 C37 C38 C39 -1.6(7) . . . . ?
C43 N4 N5 C36 172.9(3) . . . . ?
C43 N4 C34 C35 -172.1(3) . . . . ?
C43 N4 C34 C49 67.7(5) . . . . ?
C43 C44 C45 C46 0.6(7) . . . . ?
C44 C43 C48 C47 1.8(6) . . . . ?
C44 C45 C46 C47 -1.2(8) . . . . ?
C45 C46 C47 C48 2.1(7) . . . . ?
C46 C47 C48 C43 -2.5(7) . . . . ?
C48 C43 C44 C45 -0.8(6) . . . . ?
C49 C34 C35 C36 119.8(3) . . . . ?
C49 C50 C51 C52 -2.2(7) . . . . ?
C50 C49 C54 C53 -1.3(6) . . . . ?
C50 C51 C52 N6 176.9(4) . . . . ?
C50 C51 C52 C53 0.6(6) . . . . ?
C51 C52 C53 C54 0.5(6) . . . . ?
C52 N6 C55 C56 42.0(7) . . . . ?
C52 N6 C55 C60 -137.7(4) . . . . ?
C52 N6 C61 C62 -137.8(5) . . . . ?
C52 N6 C61 C66 36.9(7) . . . . ?
C52 C53 C54 C49 -0.1(7) . . . . ?
C54 C49 C50 C51 2.5(7) . . . . ?
C55 N6 C52 C51 42.9(7) . . . . ?
C55 N6 C52 C53 -141.1(5) . . . . ?
C55 N6 C61 C62 43.4(7) . . . . ?
C55 N6 C61 C66 -141.9(5) . . . . ?
C55 C56 C57 C58 -2.1(8) . . . . ?
C56 C55 C60 C59 4.0(7) . . . . ?
C56 C57 C58 C59 1.1(9) . . . . ?
C57 C58 C59 C60 2.3(8) . . . . ?
C58 C59 C60 C55 -4.9(7) . . . . ?
C60 C55 C56 C57 -0.4(7) . . . . ?
C61 N6 C52 C51 -135.9(5) . . . . ?
C61 N6 C52 C53 40.1(7) . . . . ?
C61 N6 C55 C56 -139.3(5) . . . . ?
C61 N6 C55 C60 41.1(7) . . . . ?
C61 C62 C63 C64 -5.6(10) . . . . ?
C62 C61 C66 C65 -4.8(8) . . . . ?
C62 C63 C64 C65 5.4(12) . . . . ?
C63 C64 C65 C66 -5.1(13) . . . . ?
C64 C65 C66 C61 4.8(11) . . . . ?
C66 C61 C62 C63 5.3(8) . . . . ?

_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 2.170
_oxdiff_exptl_absorpt_empirical_full_min 0.468
####################################################################### 
# 
# 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_02-0306
_database_code_depnum_ccdc_archive 'CCDC 2287504'
loop_
_audit_author_name
_audit_author_address
'Wang Long'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N3'
_chemical_formula_sum            'C23 H23 N3'
_chemical_formula_weight         341.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.1432(4)
_cell_length_b                   18.2504(12)
_cell_length_c                   16.2875(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.118(6)
_cell_angle_gamma                90
_cell_volume                     1797.70(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4161
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      27.6560
_cell_measurement_theta_min      3.3740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark colourless'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11594
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  39.00   1.00    5.50    --   11.90 -57.00 -90.00   94
  2  ω    -14.00  77.00   1.00    5.50    --   11.90  77.00-180.00   91
  3  ω    -12.00  84.00   1.00    5.50    --   11.90  57.00  60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0315289000
_diffrn_orient_matrix_UB_12      0.0231609000
_diffrn_orient_matrix_UB_13      0.0350239000
_diffrn_orient_matrix_UB_21      0.0331501000
_diffrn_orient_matrix_UB_22      0.0273239000
_diffrn_orient_matrix_UB_23      -0.0262633000
_diffrn_orient_matrix_UB_31      -0.1079797000
_diffrn_orient_matrix_UB_32      0.0151224000
_diffrn_orient_matrix_UB_33      -0.0063023000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2582
_reflns_number_total             3167
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.064
_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)+(0.0383P)²+0.4494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0987
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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 1.0122(2) 0.00372(8) 0.63474(10) 0.0385(4) Uani 1 1 d . . . . .
N2 N 0.49405(19) 0.29172(7) 0.47180(7) 0.0235(3) Uani 1 1 d . . . . .
N3 N 0.39180(19) 0.35337(7) 0.49753(7) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.8065(2) 0.21374(8) 0.54300(9) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.6745(2) 0.17075(9) 0.58456(9) 0.0262(4) Uani 1 1 d . . . . .
H2 H 0.534644 0.188932 0.592339 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7414(2) 0.10204(9) 0.61498(10) 0.0274(4) Uani 1 1 d . . . . .
H3 H 0.646129 0.073978 0.642760 0.033 Uiso 1 1 calc R U . . .
C4 C 0.9477(2) 0.07291(9) 0.60558(9) 0.0259(4) Uani 1 1 d . . . . .
C5 C 1.0830(2) 0.11773(9) 0.56619(10) 0.0272(4) Uani 1 1 d . . . . .
H5 H 1.226023 0.100966 0.560555 0.033 Uiso 1 1 calc R U . . .
C6 C 1.0125(2) 0.18604(9) 0.53525(9) 0.0258(4) Uani 1 1 d . . . . .
H6 H 1.107585 0.214701 0.508013 0.031 Uiso 1 1 calc R U . . .
C7 C 1.2129(3) -0.02794(10) 0.61464(11) 0.0375(4) Uani 1 1 d . . . . .
H7A H 1.203199 -0.029195 0.553948 0.056 Uiso 1 1 calc R U . . .
H7B H 1.231038 -0.077903 0.636839 0.056 Uiso 1 1 calc R U . . .
H7C H 1.340190 0.001875 0.639541 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8525(3) -0.04621(10) 0.65872(13) 0.0449(5) Uani 1 1 d . . . . .
H8A H 0.793323 -0.025618 0.705846 0.067 Uiso 1 1 calc R U . . .
H8B H 0.924020 -0.093263 0.675086 0.067 Uiso 1 1 calc R U . . .
H8C H 0.731578 -0.053678 0.611533 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7330(2) 0.28859(8) 0.50971(9) 0.0234(4) Uani 1 1 d . . . . .
H9 H 0.823607 0.303644 0.467186 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7470(2) 0.34833(9) 0.57687(10) 0.0274(4) Uani 1 1 d . . . . .
H10A H 0.767819 0.326636 0.633421 0.033 Uiso 1 1 calc R U . . .
H10B H 0.869848 0.382729 0.573703 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5265(2) 0.38617(9) 0.55568(9) 0.0228(4) Uani 1 1 d . . . . .
C12 C 0.4648(2) 0.45236(8) 0.59668(9) 0.0236(4) Uani 1 1 d . . . . .
C13 C 0.2518(3) 0.48188(9) 0.57729(10) 0.0285(4) Uani 1 1 d . . . . .
H13 H 0.143874 0.458101 0.537194 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1961(3) 0.54476(9) 0.61528(10) 0.0340(4) Uani 1 1 d . . . . .
H14 H 0.050017 0.563567 0.601892 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3529(3) 0.58091(10) 0.67320(10) 0.0359(4) Uani 1 1 d . . . . .
H15 H 0.314910 0.624690 0.698908 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5631(3) 0.55282(9) 0.69299(10) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.670869 0.577364 0.732473 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6188(3) 0.48901(9) 0.65574(10) 0.0304(4) Uani 1 1 d . . . . .
H17 H 0.764168 0.469829 0.670591 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4158(2) 0.26501(8) 0.39116(9) 0.0221(3) Uani 1 1 d . . . . .
C19 C 0.2057(2) 0.28401(9) 0.34824(10) 0.0270(4) Uani 1 1 d . . . . .
H19 H 0.112516 0.314549 0.374188 0.032 Uiso 1 1 calc R U . . .
C20 C 0.1333(3) 0.25842(10) 0.26802(10) 0.0322(4) Uani 1 1 d . . . . .
H20 H -0.008769 0.272250 0.239091 0.039 Uiso 1 1 calc R U . . .
C21 C 0.2649(3) 0.21302(10) 0.22951(10) 0.0343(4) Uani 1 1 d . . . . .
H21 H 0.214854 0.195867 0.174351 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4699(3) 0.19307(10) 0.27254(10) 0.0332(4) Uani 1 1 d . . . . .
H22 H 0.560313 0.161218 0.246877 0.040 Uiso 1 1 calc R U . . .
C23 C 0.5466(3) 0.21857(9) 0.35245(10) 0.0286(4) Uani 1 1 d . . . . .
H23 H 0.688726 0.204358 0.380931 0.034 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 C4 1.382(2) . ?
N1 C7 1.450(2) . ?
N1 C8 1.442(2) . ?
N2 N3 1.3887(17) . ?
N2 C9 1.4905(18) . ?
N2 C18 1.4042(19) . ?
N3 C11 1.2902(19) . ?
C1 C2 1.387(2) . ?
C1 C6 1.389(2) . ?
C1 C9 1.509(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(2) . ?
C4 C5 1.400(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 1.0000 . ?
C9 C10 1.536(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.506(2) . ?
C11 C12 1.462(2) . ?
C12 C13 1.398(2) . ?
C12 C17 1.396(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(2) . ?
C18 C23 1.393(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C7 119.36(14) . . ?
C4 N1 C8 120.16(13) . . ?
C8 N1 C7 117.08(14) . . ?
N3 N2 C9 111.77(11) . . ?
N3 N2 C18 117.70(11) . . ?
C18 N2 C9 121.64(12) . . ?
C11 N3 N2 109.38(12) . . ?
C2 C1 C6 117.29(14) . . ?
C2 C1 C9 121.59(13) . . ?
C6 C1 C9 121.10(13) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.67(14) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.32(15) . . ?
C4 C3 H3 119.3 . . ?
N1 C4 C3 121.14(14) . . ?
N1 C4 C5 122.27(14) . . ?
C5 C4 C3 116.59(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.33(14) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.74(14) . . ?
C5 C6 H6 119.1 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C1 113.21(12) . . ?
N2 C9 H9 109.3 . . ?
N2 C9 C10 101.27(11) . . ?
C1 C9 H9 109.3 . . ?
C1 C9 C10 114.25(12) . . ?
C10 C9 H9 109.3 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 103.12(11) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
N3 C11 C10 112.98(14) . . ?
N3 C11 C12 122.30(13) . . ?
C12 C11 C10 124.70(13) . . ?
C13 C12 C11 121.49(13) . . ?
C17 C12 C11 120.78(14) . . ?
C17 C12 C13 117.72(15) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.10(15) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.26(16) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.50(16) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.37(16) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.04(16) . . ?
C16 C17 H17 119.5 . . ?
C19 C18 N2 121.03(14) . . ?
C23 C18 N2 120.32(13) . . ?
C23 C18 C19 118.65(14) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.22(15) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.87(14) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.85(15) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.25(16) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.14(14) . . ?
C22 C23 H23 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 178.09(15) . . . . ?
N2 N3 C11 C10 0.07(17) . . . . ?
N2 N3 C11 C12 -178.81(13) . . . . ?
N2 C9 C10 C11 -10.86(15) . . . . ?
N2 C18 C19 C20 178.59(14) . . . . ?
N2 C18 C23 C22 -179.22(15) . . . . ?
N3 N2 C9 C1 134.79(13) . . . . ?
N3 N2 C9 C10 12.02(15) . . . . ?
N3 N2 C18 C19 -19.3(2) . . . . ?
N3 N2 C18 C23 160.98(13) . . . . ?
N3 C11 C12 C13 2.8(2) . . . . ?
N3 C11 C12 C17 -176.02(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C9 C10 C11 -132.90(13) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C9 N2 -39.93(19) . . . . ?
C2 C1 C9 C10 75.31(17) . . . . ?
C2 C3 C4 N1 -178.83(15) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 -2.5(2) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C6 C1 C9 N2 141.95(14) . . . . ?
C6 C1 C9 C10 -102.81(16) . . . . ?
C7 N1 C4 C3 172.25(14) . . . . ?
C7 N1 C4 C5 -8.3(2) . . . . ?
C8 N1 C4 C3 13.7(2) . . . . ?
C8 N1 C4 C5 -166.93(16) . . . . ?
C9 N2 N3 C11 -8.12(16) . . . . ?
C9 N2 C18 C19 -163.96(14) . . . . ?
C9 N2 C18 C23 16.4(2) . . . . ?
C9 C1 C2 C3 179.86(14) . . . . ?
C9 C1 C6 C5 179.39(14) . . . . ?
C9 C10 C11 N3 7.41(17) . . . . ?
C9 C10 C11 C12 -173.74(14) . . . . ?
C10 C11 C12 C13 -175.91(15) . . . . ?
C10 C11 C12 C17 5.2(2) . . . . ?
C11 C12 C13 C14 -179.05(15) . . . . ?
C11 C12 C17 C16 178.14(15) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C12 C17 C16 -0.8(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C17 C12 C13 C14 -0.2(2) . . . . ?
C18 N2 N3 C11 -156.07(13) . . . . ?
C18 N2 C9 C1 -78.71(17) . . . . ?
C18 N2 C9 C10 158.52(13) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C19 C18 C23 C22 1.1(2) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C23 -1.1(3) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C23 C18 C19 C20 -1.7(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 1.743
_oxdiff_exptl_absorpt_empirical_full_min 0.654
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2287505'
loop_
_audit_author_name
_audit_author_address
'Wang Long'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H25 N3'
_chemical_formula_sum            'C33 H25 N3'
_chemical_formula_weight         463.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N '
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                   8.65070(10)
_cell_length_b                   16.2619(2)
_cell_length_c                   17.5966(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.7040(10)
_cell_angle_gamma                90
_cell_volume                     2472.68(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12157
_cell_measurement_temperature    294.52(10)
_cell_measurement_theta_max      75.5370
_cell_measurement_theta_min      2.4960
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16418
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.672
_diffrn_reflns_theta_min         3.703
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.52(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -71.00   0.50    1.00    --  -43.18-129.00-139.00   92
  2  ω   -117.00 -66.00   0.50    1.00    --  -43.18-140.00  47.00  102
  3  ω    -76.00 -51.00   0.50    1.00    --  -43.18 129.00 -65.00   50
  4  ω     68.00  93.00   0.50    1.00    --   43.18-129.00-139.00   50
  5  ω     72.00 100.00   0.50    1.00    --   43.18-140.00  47.00   56
  6  ω    -57.00 -28.00   0.50    2.80    --  -90.25 129.00 -65.00   58
  7  ω    -98.00 -66.00   0.50    2.80    --  -90.25-140.00  47.00   64
  8  ω     83.00 112.00   0.50    2.80    --  109.26-140.00  47.00   58
  9  ω     63.00 113.00   0.50    2.80    --  109.26-129.00-139.00  100
 10  ω    105.00 130.00   0.50    2.80    --  109.26 140.00 107.00   50
 11  ω     97.00 138.00   0.50    2.80    --  109.26 129.00 -65.00   82
 12  ω     -8.00  30.00   0.50    1.00    --  -43.18  57.00-180.00   76
 13  ω   -112.00 -16.00   0.50    1.00    --  -43.18 -77.00  60.00  192
 14  ω    -65.00 -15.00   0.50    1.00    --  -43.18  57.00-180.00  100
 15  ω    -51.00 -26.00   0.50    2.80    --  -90.25  45.00  60.00   50
 16  ω    -45.00 -20.00   0.50    2.80    --  -90.25  45.00  90.00   50
 17  ω    -42.00 -16.00   0.50    2.80    --  -90.25  61.00 -60.00   52
 18  ω    -63.00 -27.00   0.50    2.80    --  -90.25  61.00 -90.00   72
 19  ω    -51.00 -23.00   0.50    2.80    --  -90.25  45.00   0.00   56
 20  ω    -46.00 -20.00   0.50    2.80    --  -90.25  45.00 -60.00   52
 21  ω    -51.00 -26.00   0.50    2.80    --  -90.25  45.00 150.00   50
 22  ω    -43.00 -17.00   0.50    2.80    --  -90.25  45.00 -30.00   52
 23  ω     91.00 135.00   0.50    2.80    --  109.26  15.00  90.00   88
 24  ω     38.00  71.00   0.50    2.80    --  109.26 -61.00-150.00   66
 25  ω    148.00 177.00   0.50    2.80    --  109.26  15.00  90.00   58
 26  ω     59.00  88.00   0.50    2.80    --  109.26  15.00  90.00   58
 27  ω     42.00  67.00   0.50    2.80    --  109.26 -61.00  90.00   50
 28  ω    151.00 178.00   0.50    2.80    --  109.26 125.00-180.00   54
 29  ω     45.00  71.00   0.50    2.80    --  109.26 -61.00  30.00   52
 30  ω     81.00 107.00   0.50    2.80    --  109.26-102.00 112.97   52
 31  ω     35.00  67.00   0.50    2.80    --  109.26 -61.00-180.00   64
 32  ω     97.00 122.00   0.50    2.80    --  109.26 125.00-180.00   50
 33  ω     51.00  77.00   0.50    2.80    --  109.26-102.00 112.97   52
 34  ω     40.00  71.00   0.50    2.80    --  109.26 -61.00 120.00   62
 35  ω     70.00  96.00   0.50    2.80    --  109.26 -94.00-150.00   52
 36  ω     37.00  62.00   0.50    2.80    --  109.26 -94.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154482000
_diffrn_orient_matrix_UB_12      0.0920360000
_diffrn_orient_matrix_UB_13      -0.0188977000
_diffrn_orient_matrix_UB_21      -0.0049041000
_diffrn_orient_matrix_UB_22      -0.0206966000
_diffrn_orient_matrix_UB_23      -0.0854814000
_diffrn_orient_matrix_UB_31      -0.1776318000
_diffrn_orient_matrix_UB_32      0.0086040000
_diffrn_orient_matrix_UB_33      -0.0034437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4463
_reflns_number_total             4898
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00256(19)
_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   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.197
_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)+(0.0339P)²+0.9780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1262
_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:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64841(16) 0.69921(9) 0.11073(8) 0.0451(3) Uani 1 1 d . . . . .
N2 N 0.11543(17) 0.51288(9) 0.28838(8) 0.0481(4) Uani 1 1 d . . . . .
N3 N 0.09944(16) 0.46275(9) 0.35084(8) 0.0438(3) Uani 1 1 d . . . . .
C1 C 0.77382(19) 0.75020(10) 0.12808(10) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.8193(2) 0.78582(11) 0.19695(11) 0.0494(4) Uani 1 1 d . . . . .
H2 H 0.762482 0.778304 0.239979 0.059 Uiso 1 1 calc R U . . .
C3 C 0.9517(2) 0.83274(13) 0.19940(13) 0.0612(5) Uani 1 1 d . . . . .
H3 H 0.984320 0.857961 0.244800 0.073 Uiso 1 1 calc R U . . .
C4 C 1.0378(2) 0.84324(14) 0.13526(14) 0.0678(6) Uani 1 1 d . . . . .
H4 H 1.127027 0.875178 0.138699 0.081 Uiso 1 1 calc R U . . .
C5 C 0.9935(2) 0.80735(13) 0.06695(13) 0.0591(5) Uani 1 1 d . . . . .
H5 H 1.052134 0.814674 0.024497 0.071 Uiso 1 1 calc R U . . .
C6 C 0.85936(19) 0.75977(11) 0.06235(10) 0.0446(4) Uani 1 1 d . . . . .
C7 C 0.7819(2) 0.71164(11) 0.00301(10) 0.0454(4) Uani 1 1 d . . . . .
C8 C 0.8135(2) 0.69344(13) -0.07212(11) 0.0589(5) Uani 1 1 d . . . . .
H8 H 0.898058 0.717009 -0.094529 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7176(3) 0.64012(15) -0.11257(12) 0.0689(6) Uani 1 1 d . . . . .
H9 H 0.738486 0.627117 -0.162522 0.083 Uiso 1 1 calc R U . . .
C10 C 0.5898(3) 0.60533(14) -0.07972(12) 0.0676(6) Uani 1 1 d . . . . .
H10 H 0.526242 0.569865 -0.108512 0.081 Uiso 1 1 calc R U . . .
C11 C 0.5548(2) 0.62197(13) -0.00583(11) 0.0562(5) Uani 1 1 d . . . . .
H11 H 0.468871 0.598763 0.015691 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6531(2) 0.67486(11) 0.03531(9) 0.0439(4) Uani 1 1 d . . . . .
C13 C 0.53573(19) 0.67326(10) 0.16275(9) 0.0404(4) Uani 1 1 d . . . . .
C14 C 0.4283(2) 0.72837(11) 0.18747(10) 0.0502(4) Uani 1 1 d . . . . .
H14 H 0.430977 0.782984 0.171903 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3164(2) 0.70210(11) 0.23564(11) 0.0503(4) Uani 1 1 d . . . . .
H15 H 0.244928 0.739657 0.252909 0.060 Uiso 1 1 calc R U . . .
C16 C 0.30910(19) 0.62084(10) 0.25846(9) 0.0408(4) Uani 1 1 d . . . . .
C17 C 0.5334(2) 0.59249(11) 0.18696(10) 0.0470(4) Uani 1 1 d . . . . .
H17 H 0.608011 0.555651 0.171563 0.056 Uiso 1 1 calc R U . . .
C18 C 0.4197(2) 0.56665(10) 0.23420(10) 0.0469(4) Uani 1 1 d . . . . .
H18 H 0.417492 0.512061 0.249869 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1829(2) 0.59360(11) 0.30988(10) 0.0455(4) Uani 1 1 d . . . . .
H19 H 0.100845 0.635163 0.309090 0.055 Uiso 1 1 calc R U . . .
C20 C 0.2405(2) 0.57778(12) 0.39249(10) 0.0521(5) Uani 1 1 d . . . . .
H20A H 0.352521 0.574368 0.396872 0.063 Uiso 1 1 calc R U . . .
H20B H 0.205886 0.620510 0.426190 0.063 Uiso 1 1 calc R U . . .
C21 C 0.16724(18) 0.49647(11) 0.40954(9) 0.0415(4) Uani 1 1 d . . . . .
C22 C 0.17987(19) 0.45506(11) 0.48364(10) 0.0449(4) Uani 1 1 d . . . . .
C23 C 0.1135(2) 0.37854(12) 0.49522(11) 0.0542(5) Uani 1 1 d . . . . .
H23 H 0.056942 0.353076 0.455586 0.065 Uiso 1 1 calc R U . . .
C24 C 0.1306(3) 0.34002(14) 0.56487(13) 0.0682(6) Uani 1 1 d . . . . .
H24 H 0.087135 0.288377 0.571655 0.082 Uiso 1 1 calc R U . . .
C25 C 0.2119(3) 0.37774(17) 0.62463(13) 0.0749(7) Uani 1 1 d . . . . .
H25 H 0.223759 0.351584 0.671544 0.090 Uiso 1 1 calc R U . . .
C26 C 0.2747(3) 0.45375(17) 0.61434(13) 0.0757(7) Uani 1 1 d . . . . .
H26 H 0.327788 0.479782 0.654759 0.091 Uiso 1 1 calc R U . . .
C27 C 0.2602(2) 0.49228(15) 0.54447(11) 0.0611(5) Uani 1 1 d . . . . .
H27 H 0.304688 0.543727 0.538112 0.073 Uiso 1 1 calc R U . . .
C28 C 0.02022(19) 0.49923(11) 0.22326(10) 0.0443(4) Uani 1 1 d . . . . .
C29 C 0.0193(2) 0.55363(13) 0.16186(11) 0.0557(5) Uani 1 1 d . . . . .
H29 H 0.075340 0.602389 0.165767 0.067 Uiso 1 1 calc R U . . .
C30 C -0.0647(2) 0.53515(15) 0.09526(12) 0.0629(5) Uani 1 1 d . . . . .
H30 H -0.062407 0.571301 0.054376 0.075 Uiso 1 1 calc R U . . .
C31 C -0.1507(2) 0.46511(15) 0.08820(12) 0.0653(6) Uani 1 1 d . . . . .
H31 H -0.205441 0.452925 0.042842 0.078 Uiso 1 1 calc R U . . .
C32 C -0.1549(3) 0.41260(15) 0.14974(12) 0.0671(6) Uani 1 1 d . . . . .
H32 H -0.215206 0.365293 0.146041 0.081 Uiso 1 1 calc R U . . .
C33 C -0.0711(2) 0.42923(13) 0.21663(11) 0.0571(5) Uani 1 1 d . . . . .
H33 H -0.075840 0.393275 0.257554 0.068 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 1.388(2) . ?
N1 C12 1.387(2) . ?
N1 C13 1.4320(19) . ?
N2 N3 1.3807(19) . ?
N2 C19 1.479(2) . ?
N2 C28 1.397(2) . ?
N3 C21 1.286(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.411(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(2) . ?
C6 C7 1.444(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.408(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(3) . ?
C13 C14 1.376(2) . ?
C13 C17 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(2) . ?
C16 C18 1.383(2) . ?
C16 C19 1.516(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9800 . ?
C19 C20 1.536(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.503(2) . ?
C21 C22 1.467(2) . ?
C22 C23 1.390(3) . ?
C22 C27 1.387(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.366(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.380(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.396(2) . ?
C28 C33 1.387(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.363(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.381(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.380(3) . ?
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
C1 N1 C13 125.73(14) . . ?
C12 N1 C1 108.86(13) . . ?
C12 N1 C13 125.37(14) . . ?
N3 N2 C19 111.94(14) . . ?
N3 N2 C28 118.80(14) . . ?
C28 N2 C19 124.16(14) . . ?
C21 N3 N2 109.17(14) . . ?
N1 C1 C6 108.68(15) . . ?
C2 C1 N1 129.04(15) . . ?
C2 C1 C6 122.24(16) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.50(18) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.30(18) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.90(18) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.83(14) . . ?
C5 C6 C1 118.75(17) . . ?
C5 C6 C7 134.38(17) . . ?
C8 C7 C6 134.06(17) . . ?
C8 C7 C12 119.13(17) . . ?
C12 C7 C6 106.71(14) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.97(18) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.86(19) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.26(18) . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C7 108.91(15) . . ?
N1 C12 C11 129.10(16) . . ?
C11 C12 C7 121.97(16) . . ?
C14 C13 N1 120.01(15) . . ?
C14 C13 C17 120.14(15) . . ?
C17 C13 N1 119.83(15) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.66(16) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.01(16) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C19 119.75(15) . . ?
C18 C16 C15 118.53(15) . . ?
C18 C16 C19 121.72(15) . . ?
C13 C17 H17 120.2 . . ?
C13 C17 C18 119.68(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C18 C17 120.93(16) . . ?
C16 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
N2 C19 C16 113.16(14) . . ?
N2 C19 H19 109.4 . . ?
N2 C19 C20 101.54(13) . . ?
C16 C19 H19 109.4 . . ?
C16 C19 C20 113.78(15) . . ?
C20 C19 H19 109.4 . . ?
C19 C20 H20A 111.3 . . ?
C19 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
C21 C20 C19 102.43(14) . . ?
C21 C20 H20A 111.3 . . ?
C21 C20 H20B 111.3 . . ?
N3 C21 C20 113.30(15) . . ?
N3 C21 C22 122.00(16) . . ?
C22 C21 C20 124.54(16) . . ?
C23 C22 C21 121.83(17) . . ?
C27 C22 C21 119.94(17) . . ?
C27 C22 C23 118.22(17) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.5(2) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.6(2) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.7(2) . . ?
C26 C27 H27 119.6 . . ?
C29 C28 N2 121.04(17) . . ?
C33 C28 N2 120.71(16) . . ?
C33 C28 C29 118.20(17) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.11(19) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.3 . . ?
C31 C30 C29 121.46(19) . . ?
C31 C30 H30 119.3 . . ?
C30 C31 H31 120.7 . . ?
C30 C31 C32 118.7(2) . . ?
C32 C31 H31 120.7 . . ?
C31 C32 H32 119.5 . . ?
C33 C32 C31 121.0(2) . . ?
C33 C32 H32 119.5 . . ?
C28 C33 H33 119.8 . . ?
C32 C33 C28 120.45(18) . . ?
C32 C33 H33 119.8 . . ?

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 178.44(18) . . . . ?
N1 C1 C6 C5 -178.52(16) . . . . ?
N1 C1 C6 C7 -0.45(19) . . . . ?
N1 C13 C14 C15 177.71(17) . . . . ?
N1 C13 C17 C18 -176.78(16) . . . . ?
N2 N3 C21 C20 0.1(2) . . . . ?
N2 N3 C21 C22 -175.51(14) . . . . ?
N2 C19 C20 C21 -11.27(17) . . . . ?
N2 C28 C29 C30 173.98(18) . . . . ?
N2 C28 C33 C32 -174.54(19) . . . . ?
N3 N2 C19 C16 134.95(15) . . . . ?
N3 N2 C19 C20 12.60(18) . . . . ?
N3 N2 C28 C29 172.69(16) . . . . ?
N3 N2 C28 C33 -10.1(3) . . . . ?
N3 C21 C22 C23 -2.8(3) . . . . ?
N3 C21 C22 C27 177.07(17) . . . . ?
C1 N1 C12 C7 -0.9(2) . . . . ?
C1 N1 C12 C11 177.64(19) . . . . ?
C1 N1 C13 C14 71.9(2) . . . . ?
C1 N1 C13 C17 -109.3(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C6 C7 C8 -176.4(2) . . . . ?
C1 C6 C7 C12 -0.12(19) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C7 177.51(16) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -177.4(2) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C5 C6 C7 C12 177.5(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C7 C8 C9 176.0(2) . . . . ?
C6 C7 C12 N1 0.7(2) . . . . ?
C6 C7 C12 C11 -178.06(18) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C7 C12 N1 177.61(17) . . . . ?
C8 C7 C12 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 N1 -177.2(2) . . . . ?
C10 C11 C12 C7 1.2(3) . . . . ?
C12 N1 C1 C2 -176.91(18) . . . . ?
C12 N1 C1 C6 0.9(2) . . . . ?
C12 N1 C13 C14 -110.7(2) . . . . ?
C12 N1 C13 C17 68.2(2) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C13 N1 C1 C2 0.9(3) . . . . ?
C13 N1 C1 C6 178.65(16) . . . . ?
C13 N1 C12 C7 -178.74(16) . . . . ?
C13 N1 C12 C11 -0.2(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C13 C17 C18 C16 -0.9(3) . . . . ?
C14 C13 C17 C18 2.1(3) . . . . ?
C14 C15 C16 C18 2.2(3) . . . . ?
C14 C15 C16 C19 -178.68(18) . . . . ?
C15 C16 C18 C17 -1.2(3) . . . . ?
C15 C16 C19 N2 138.87(18) . . . . ?
C15 C16 C19 C20 -105.9(2) . . . . ?
C16 C19 C20 C21 -133.19(15) . . . . ?
C17 C13 C14 C15 -1.1(3) . . . . ?
C18 C16 C19 N2 -42.0(2) . . . . ?
C18 C16 C19 C20 73.2(2) . . . . ?
C19 N2 N3 C21 -8.54(19) . . . . ?
C19 N2 C28 C29 20.0(3) . . . . ?
C19 N2 C28 C33 -162.79(17) . . . . ?
C19 C16 C18 C17 179.65(17) . . . . ?
C19 C20 C21 N3 7.63(19) . . . . ?
C19 C20 C21 C22 -176.88(15) . . . . ?
C20 C21 C22 C23 -177.91(17) . . . . ?
C20 C21 C22 C27 1.9(3) . . . . ?
C21 C22 C23 C24 178.27(18) . . . . ?
C21 C22 C27 C26 -179.24(19) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C24 C25 C26 C27 -1.3(4) . . . . ?
C25 C26 C27 C22 0.8(4) . . . . ?
C27 C22 C23 C24 -1.6(3) . . . . ?
C28 N2 N3 C21 -164.36(15) . . . . ?
C28 N2 C19 C16 -70.8(2) . . . . ?
C28 N2 C19 C20 166.90(15) . . . . ?
C28 C29 C30 C31 1.5(3) . . . . ?
C29 C28 C33 C32 2.7(3) . . . . ?
C29 C30 C31 C32 1.0(3) . . . . ?
C30 C31 C32 C33 -1.6(4) . . . . ?
C31 C32 C33 C28 -0.3(3) . . . . ?
C33 C28 C29 C30 -3.3(3) . . . . ?

_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 13.998
_oxdiff_exptl_absorpt_empirical_full_min 0.480
