# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shimq_220425_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2byqdf
_database_code_depnum_ccdc_archive 'CCDC 2173515'
loop_
_audit_author_name
_audit_author_address
'Maoqing Shi'
;Sun Yat sen University
China
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2022-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H26 N4 O2'
_chemical_formula_sum            'C29 H26 N4 O2'
_chemical_formula_weight         462.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   12.0222(2)
_cell_length_b                   8.7354(2)
_cell_length_c                   22.4535(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.2750(10)
_cell_angle_gamma                90
_cell_volume                     2348.05(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10018
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.1530
_cell_measurement_theta_min      3.9300
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15430
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.300
_diffrn_reflns_theta_min         3.954
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(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 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     97.00 172.00   0.50    0.05    --  104.88 104.00 159.00  150
  2  ω    107.00 175.00   0.50    0.05    --  104.88  61.00 120.00  136
  3  ω     30.00 114.00   0.50    0.05    --   45.56  57.00-120.00  168
  4  ω    -12.00  31.00   0.50    0.05    --  -45.56  19.00-150.00   86
  5  ω    -75.00 -28.00   0.50    0.05    -- -100.00  77.00 -30.00   94
  6  ω    -69.00 -27.00   0.50    0.05    -- -100.00  61.00 -30.00   84
  7  ω    -62.00 -29.00   0.50    0.05    -- -100.00  61.00 -60.00   66
  8  ω    -68.00 -28.00   0.50    0.05    -- -100.00  61.00-180.00   80
  9  ω    -50.00 -23.00   0.50    0.05    --  -45.56 125.00-180.00   54
 10  ω   -153.00-128.00   0.50    0.05    -- -100.00-104.00  57.00   50
 11  ω   -161.00-123.00   0.50    0.05    -- -100.00 -15.00-150.00   76
 12  ω   -111.00 -80.00   0.50    0.05    -- -100.00 -15.00-150.00   62
 13  ω    -97.00 -27.00   0.50    0.05    -- -100.00 104.00 159.00  140
 14  ω    -65.00 -40.00   0.50    0.05    --  -45.56 104.00 159.00   50
 15  ω     32.00  57.00   0.50    0.05    --  104.88 -61.00-180.00   50
 16  ω     42.00  67.00   0.50    0.05    --  104.88 -61.00  60.00   50
 17  ω     32.00  59.00   0.50    0.05    --  104.88 -61.00  90.00   54
 18  ω     36.00  72.00   0.50    0.05    --  104.88 -61.00  30.00   72
 19  ω     38.00  72.00   0.50    0.05    --  104.88 -61.00 -60.00   68
 20  ω     -8.00  42.00   0.50    0.05    --   45.56 -38.00 -60.00  100
 21  ω      3.00  84.00   0.50    0.05    --   45.56-104.00  57.00  162
 22  ω     69.00 100.00   0.50    0.05    --  104.88-104.00  57.00   62
 23  ω     80.00 105.00   0.50    0.05    --  104.88 -94.00  60.00   50
 24  ω     46.00  88.00   0.50    0.05    --  104.88 -94.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1079637000
_diffrn_orient_matrix_UB_12      0.0531786000
_diffrn_orient_matrix_UB_13      -0.0364354000
_diffrn_orient_matrix_UB_21      -0.0506205000
_diffrn_orient_matrix_UB_22      -0.1606719000
_diffrn_orient_matrix_UB_23      0.0058743000
_diffrn_orient_matrix_UB_31      -0.0483586000
_diffrn_orient_matrix_UB_32      0.0495200000
_diffrn_orient_matrix_UB_33      0.0582084000
_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                4098
_reflns_number_total             4632
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00127(17)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.065
_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)+(0.0458P)²+0.6865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1041
_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 Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C34(H34), C21(H21), C3(H3), C30(H30), C4(H4), C33(H33),
 C32(H32), C31(H31), C14(H14), C18(H18), C17(H17), C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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
O35 O 0.43884(7) 0.09415(10) 0.58292(4) 0.0236(2) Uani 1 1 d . . . . .
O26 O 0.22581(8) 0.19600(12) 0.72314(4) 0.0312(2) Uani 1 1 d . . . . .
N19 N 0.21259(8) 0.25114(12) 0.57845(5) 0.0183(2) Uani 1 1 d . . . . .
N10 N 0.39984(9) 0.26910(12) 0.69132(5) 0.0199(2) Uani 1 1 d . . . . .
N9 N 0.53017(8) 0.31451(12) 0.55927(4) 0.0175(2) Uani 1 1 d . . . . .
N23 N 0.18300(8) 0.33637(12) 0.52786(5) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.53825(10) 0.46536(14) 0.58126(5) 0.0171(2) Uani 1 1 d . . . . .
C8 C 0.45609(10) 0.23066(14) 0.58818(5) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.46418(10) 0.48694(14) 0.62532(5) 0.0174(3) Uani 1 1 d . . . . .
C22 C 0.13846(10) 0.23540(15) 0.48813(6) 0.0213(3) Uani 1 1 d . . . . .
C20 C 0.18896(10) 0.09871(15) 0.56971(6) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.26815(10) 0.33500(15) 0.62821(5) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.40193(10) 0.33956(14) 0.63161(5) 0.0177(3) Uani 1 1 d . . . . .
C29 C 0.72174(10) 0.21990(14) 0.55726(5) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.60839(10) 0.57989(15) 0.56463(5) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.658540 0.562947 0.534978 0.024 Uiso 1 1 calc R U . . .
C5 C 0.46181(10) 0.62698(15) 0.65415(6) 0.0212(3) Uani 1 1 d . . . . .
H5 H 0.413755 0.642688 0.684893 0.025 Uiso 1 1 calc R U . . .
C34 C 0.81747(11) 0.29553(15) 0.54295(6) 0.0212(3) Uani 1 1 d . . . . .
H34 H 0.813239 0.365744 0.510514 0.025 Uiso 1 1 calc R U . . .
C28 C 0.61022(10) 0.24579(15) 0.52179(6) 0.0196(3) Uani 1 1 d . . . . .
H28A H 0.620320 0.314156 0.487537 0.024 Uiso 1 1 calc R U . . .
H28B H 0.580563 0.146850 0.505752 0.024 Uiso 1 1 calc R U . . .
C21 C 0.14055(10) 0.08733(15) 0.51206(6) 0.0231(3) Uani 1 1 d . . . . .
H21 H 0.113714 -0.003337 0.492270 0.028 Uiso 1 1 calc R U . . .
C13 C 0.49039(11) 0.20174(16) 0.72714(5) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.60277(11) 0.72107(15) 0.59298(6) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.648720 0.802732 0.581806 0.027 Uiso 1 1 calc R U . . .
C30 C 0.72909(11) 0.11965(15) 0.60577(6) 0.0228(3) Uani 1 1 d . . . . .
H30 H 0.663896 0.069142 0.616559 0.027 Uiso 1 1 calc R U . . .
C12 C 0.28643(11) 0.24992(15) 0.68859(6) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.53113(11) 0.74481(15) 0.63736(6) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.529310 0.841801 0.656385 0.028 Uiso 1 1 calc R U . . .
C33 C 0.91961(11) 0.26897(16) 0.57591(6) 0.0246(3) Uani 1 1 d . . . . .
H33 H 0.984668 0.321155 0.565890 0.029 Uiso 1 1 calc R U . . .
C27 C 0.21248(11) 0.48966(16) 0.63552(6) 0.0230(3) Uani 1 1 d . . . . .
H27A H 0.226804 0.556214 0.601928 0.035 Uiso 1 1 calc R U . . .
H27B H 0.243050 0.537012 0.673077 0.035 Uiso 1 1 calc R U . . .
H27C H 0.131778 0.475247 0.636248 0.035 Uiso 1 1 calc R U . . .
C32 C 0.92649(11) 0.16668(16) 0.62323(6) 0.0269(3) Uani 1 1 d . . . . .
H32 H 0.996407 0.147061 0.645176 0.032 Uiso 1 1 calc R U . . .
C31 C 0.83106(12) 0.09309(16) 0.63844(6) 0.0264(3) Uani 1 1 d . . . . .
H31 H 0.835352 0.024240 0.671320 0.032 Uiso 1 1 calc R U . . .
C24 C 0.21027(11) -0.02696(16) 0.61431(7) 0.0275(3) Uani 1 1 d . . . . .
H24A H 0.289382 -0.026916 0.629415 0.041 Uiso 1 1 calc R U . . .
H24B H 0.191126 -0.125512 0.595180 0.041 Uiso 1 1 calc R U . . .
H24C H 0.164290 -0.010978 0.647615 0.041 Uiso 1 1 calc R U . . .
C14 C 0.47827(13) 0.05639(17) 0.75066(6) 0.0294(3) Uani 1 1 d . . . . .
H14 H 0.408812 0.004161 0.744850 0.035 Uiso 1 1 calc R U . . .
C18 C 0.59202(12) 0.27801(18) 0.73568(6) 0.0295(3) Uani 1 1 d . . . . .
H18 H 0.599682 0.377759 0.719712 0.035 Uiso 1 1 calc R U . . .
C25 C 0.08898(12) 0.28782(17) 0.42793(6) 0.0292(3) Uani 1 1 d . . . . .
H25A H 0.007642 0.295205 0.427944 0.044 Uiso 1 1 calc R U . . .
H25B H 0.107419 0.214132 0.397427 0.044 Uiso 1 1 calc R U . . .
H25C H 0.119497 0.388419 0.419018 0.044 Uiso 1 1 calc R U . . .
C17 C 0.68228(13) 0.2078(2) 0.76766(6) 0.0360(4) Uani 1 1 d . . . . .
H17 H 0.752124 0.259141 0.773176 0.043 Uiso 1 1 calc R U . . .
C16 C 0.67092(14) 0.0642(2) 0.79137(6) 0.0383(4) Uani 1 1 d . . . . .
H16 H 0.732608 0.016801 0.813591 0.046 Uiso 1 1 calc R U . . .
C15 C 0.56937(15) -0.01127(19) 0.78280(7) 0.0393(4) Uani 1 1 d . . . . .
H15 H 0.562024 -0.110672 0.799147 0.047 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
O35 C8 1.2142(15) . ?
O26 C12 1.2078(16) . ?
N19 N23 1.3773(15) . ?
N19 C20 1.3718(16) . ?
N19 C11 1.4471(16) . ?
N10 C7 1.4775(15) . ?
N10 C13 1.4202(17) . ?
N10 C12 1.3695(16) . ?
N9 C1 1.4074(16) . ?
N9 C8 1.3628(16) . ?
N9 C28 1.4641(15) . ?
N23 C22 1.3314(17) . ?
C1 C6 1.4033(17) . ?
C1 C2 1.3818(17) . ?
C8 C7 1.5481(17) . ?
C6 C7 1.5024(17) . ?
C6 C5 1.3855(18) . ?
C22 C21 1.3999(19) . ?
C22 C25 1.4977(19) . ?
C20 C21 1.3732(19) . ?
C20 C24 1.4921(19) . ?
C11 C7 1.6036(17) . ?
C11 C12 1.5439(17) . ?
C11 C27 1.5232(18) . ?
C29 C34 1.3900(18) . ?
C29 C28 1.5122(17) . ?
C29 C30 1.3940(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3924(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.3979(19) . ?
C34 H34 0.9500 . ?
C34 C33 1.3936(19) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C21 H21 0.9500 . ?
C13 C14 1.388(2) . ?
C13 C18 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3912(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.3890(19) . ?
C4 H4 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.385(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C31 1.385(2) . ?
C31 H31 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.388(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C16 1.374(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.385(3) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N23 N19 C11 115.41(10) . . ?
C20 N19 N23 111.86(10) . . ?
C20 N19 C11 132.59(11) . . ?
C13 N10 C7 127.62(10) . . ?
C12 N10 C7 96.33(9) . . ?
C12 N10 C13 133.06(11) . . ?
C1 N9 C28 123.90(10) . . ?
C8 N9 C1 111.29(10) . . ?
C8 N9 C28 123.11(10) . . ?
C22 N23 N19 104.59(10) . . ?
C6 C1 N9 110.20(10) . . ?
C2 C1 N9 127.39(11) . . ?
C2 C1 C6 122.39(11) . . ?
O35 C8 N9 126.50(11) . . ?
O35 C8 C7 125.92(11) . . ?
N9 C8 C7 107.51(10) . . ?
C1 C6 C7 107.76(10) . . ?
C5 C6 C1 119.32(11) . . ?
C5 C6 C7 132.91(11) . . ?
N23 C22 C21 111.29(11) . . ?
N23 C22 C25 120.27(12) . . ?
C21 C22 C25 128.35(12) . . ?
N19 C20 C21 105.63(11) . . ?
N19 C20 C24 126.69(12) . . ?
C21 C20 C24 127.67(12) . . ?
N19 C11 C7 116.04(10) . . ?
N19 C11 C12 116.91(11) . . ?
N19 C11 C27 110.85(10) . . ?
C12 C11 C7 84.78(9) . . ?
C27 C11 C7 114.93(10) . . ?
C27 C11 C12 111.16(10) . . ?
N10 C7 C8 111.03(10) . . ?
N10 C7 C6 119.50(10) . . ?
N10 C7 C11 86.11(8) . . ?
C8 C7 C11 115.65(10) . . ?
C6 C7 C8 103.02(9) . . ?
C6 C7 C11 121.53(10) . . ?
C34 C29 C28 121.33(11) . . ?
C34 C29 C30 119.00(12) . . ?
C30 C29 C28 119.66(11) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.47(11) . . ?
C3 C2 H2 121.3 . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.06(12) . . ?
C4 C5 H5 120.5 . . ?
C29 C34 H34 119.8 . . ?
C29 C34 C33 120.40(12) . . ?
C33 C34 H34 119.8 . . ?
N9 C28 C29 110.88(10) . . ?
N9 C28 H28A 109.5 . . ?
N9 C28 H28B 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
C22 C21 H21 126.7 . . ?
C20 C21 C22 106.62(12) . . ?
C20 C21 H21 126.7 . . ?
C14 C13 N10 119.52(13) . . ?
C14 C13 C18 120.52(13) . . ?
C18 C13 N10 119.87(12) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.25(12) . . ?
C4 C3 H3 119.4 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.46(12) . . ?
C31 C30 H30 119.8 . . ?
O26 C12 N10 132.54(12) . . ?
O26 C12 C11 134.92(12) . . ?
N10 C12 C11 92.36(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.47(12) . . ?
C3 C4 H4 119.8 . . ?
C34 C33 H33 119.9 . . ?
C32 C33 C34 120.15(13) . . ?
C32 C33 H33 119.9 . . ?
C11 C27 H27A 109.5 . . ?
C11 C27 H27B 109.5 . . ?
C11 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C32 H32 120.1 . . ?
C33 C32 C31 119.75(12) . . ?
C31 C32 H32 120.1 . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.21(13) . . ?
C32 C31 H31 119.9 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.83(15) . . ?
C15 C14 H14 120.6 . . ?
C13 C18 H18 120.2 . . ?
C17 C18 C13 119.70(15) . . ?
C17 C18 H18 120.2 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.20(16) . . ?
C16 C17 H17 119.9 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.89(14) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.86(15) . . ?
C16 C15 H15 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O35 C8 C7 N10 43.49(16) . . . . ?
O35 C8 C7 C6 172.57(12) . . . . ?
O35 C8 C7 C11 -52.48(16) . . . . ?
N19 N23 C22 C21 -0.87(13) . . . . ?
N19 N23 C22 C25 175.99(11) . . . . ?
N19 C20 C21 C22 0.71(13) . . . . ?
N19 C11 C7 N10 -121.95(11) . . . . ?
N19 C11 C7 C8 -10.46(15) . . . . ?
N19 C11 C7 C6 115.55(12) . . . . ?
N19 C11 C12 O26 -63.3(2) . . . . ?
N19 C11 C12 N10 121.45(11) . . . . ?
N10 C13 C14 C15 176.50(12) . . . . ?
N10 C13 C18 C17 -176.07(12) . . . . ?
N9 C1 C6 C7 -1.04(13) . . . . ?
N9 C1 C6 C5 177.92(10) . . . . ?
N9 C1 C2 C3 -179.38(11) . . . . ?
N9 C8 C7 N10 -133.65(10) . . . . ?
N9 C8 C7 C6 -4.57(12) . . . . ?
N9 C8 C7 C11 130.38(11) . . . . ?
N23 N19 C20 C21 -1.31(13) . . . . ?
N23 N19 C20 C24 179.56(11) . . . . ?
N23 N19 C11 C7 -91.36(12) . . . . ?
N23 N19 C11 C12 170.91(10) . . . . ?
N23 N19 C11 C27 42.12(13) . . . . ?
N23 C22 C21 C20 0.11(14) . . . . ?
C1 N9 C8 O35 -172.88(12) . . . . ?
C1 N9 C8 C7 4.23(13) . . . . ?
C1 N9 C28 C29 69.41(14) . . . . ?
C1 C6 C7 N10 126.96(11) . . . . ?
C1 C6 C7 C8 3.32(12) . . . . ?
C1 C6 C7 C11 -128.23(11) . . . . ?
C1 C6 C5 C4 1.82(18) . . . . ?
C1 C2 C3 C4 1.47(18) . . . . ?
C8 N9 C1 C6 -2.13(14) . . . . ?
C8 N9 C1 C2 176.75(12) . . . . ?
C8 N9 C28 C29 -94.45(13) . . . . ?
C6 C1 C2 C3 -0.63(18) . . . . ?
C6 C5 C4 C3 -1.00(19) . . . . ?
C20 N19 N23 C22 1.36(13) . . . . ?
C20 N19 C11 C7 83.70(15) . . . . ?
C20 N19 C11 C12 -14.02(18) . . . . ?
C20 N19 C11 C27 -142.82(13) . . . . ?
C11 N19 N23 C22 177.45(10) . . . . ?
C11 N19 C20 C21 -176.51(12) . . . . ?
C11 N19 C20 C24 4.4(2) . . . . ?
C7 N10 C13 C14 -129.32(13) . . . . ?
C7 N10 C13 C18 47.22(19) . . . . ?
C7 N10 C12 O26 179.27(15) . . . . ?
C7 N10 C12 C11 -5.25(10) . . . . ?
C7 C6 C5 C4 -179.54(12) . . . . ?
C7 C11 C12 O26 -179.88(17) . . . . ?
C7 C11 C12 N10 4.83(9) . . . . ?
C29 C34 C33 C32 0.06(19) . . . . ?
C29 C30 C31 C32 0.3(2) . . . . ?
C2 C1 C6 C7 -179.98(11) . . . . ?
C2 C1 C6 C5 -1.02(18) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C5 C6 C7 N10 -51.80(19) . . . . ?
C5 C6 C7 C8 -175.44(13) . . . . ?
C5 C6 C7 C11 53.02(18) . . . . ?
C34 C29 C28 N9 -116.38(12) . . . . ?
C34 C29 C30 C31 -1.48(19) . . . . ?
C34 C33 C32 C31 -1.3(2) . . . . ?
C28 N9 C1 C6 -167.65(10) . . . . ?
C28 N9 C1 C2 11.23(19) . . . . ?
C28 N9 C8 O35 -7.23(19) . . . . ?
C28 N9 C8 C7 169.89(10) . . . . ?
C28 C29 C34 C33 -179.43(11) . . . . ?
C28 C29 C30 C31 179.25(11) . . . . ?
C13 N10 C7 C8 51.35(16) . . . . ?
C13 N10 C7 C6 -68.30(17) . . . . ?
C13 N10 C7 C11 167.38(12) . . . . ?
C13 N10 C12 O26 18.5(3) . . . . ?
C13 N10 C12 C11 -166.02(13) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C13 C18 C17 C16 -0.7(2) . . . . ?
C30 C29 C34 C33 1.31(18) . . . . ?
C30 C29 C28 N9 62.88(15) . . . . ?
C12 N10 C7 C8 -110.96(11) . . . . ?
C12 N10 C7 C6 129.38(11) . . . . ?
C12 N10 C7 C11 5.07(10) . . . . ?
C12 N10 C13 C14 26.3(2) . . . . ?
C12 N10 C13 C18 -157.19(14) . . . . ?
C12 C11 C7 N10 -4.48(9) . . . . ?
C12 C11 C7 C8 107.00(11) . . . . ?
C12 C11 C7 C6 -126.99(11) . . . . ?
C33 C32 C31 C30 1.1(2) . . . . ?
C27 C11 C7 N10 106.45(11) . . . . ?
C27 C11 C7 C8 -142.07(11) . . . . ?
C27 C11 C7 C6 -16.06(15) . . . . ?
C27 C11 C12 O26 65.4(2) . . . . ?
C27 C11 C12 N10 -109.91(11) . . . . ?
C24 C20 C21 C22 179.84(12) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C18 C17 C16 C15 0.7(2) . . . . ?
C25 C22 C21 C20 -176.44(12) . . . . ?
C17 C16 C15 C14 -0.2(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 2.289
_oxdiff_exptl_absorpt_empirical_full_min 0.337
####################################################################### 
# 
# 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_20221026-smq-2_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2dm7t3
_database_code_depnum_ccdc_archive 'CCDC 2223035'
loop_
_audit_author_name
_audit_author_address
shi
;Sun Yat sen University
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2022-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 Cl N4 O2'
_chemical_formula_sum            'C29 H29 Cl N4 O2'
_chemical_formula_weight         501.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.9599(5)
_cell_length_b                   11.0330(3)
_cell_length_c                   11.8000(5)
_cell_angle_alpha                86.694(3)
_cell_angle_beta                 71.741(4)
_cell_angle_gamma                86.666(3)
_cell_volume                     1228.24(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10157
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3240
_cell_measurement_theta_min      3.9410
_shelx_estimated_absorpt_T_max   0.852
_shelx_estimated_absorpt_T_min   0.628
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12880
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.346
_diffrn_reflns_theta_min         3.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 132.00   0.50    0.08    --  105.22 125.00-150.00   74
  2  ω    137.00 170.00   0.50    0.08    --  105.22 125.00-150.00   66
  3  ω     28.00  63.00   0.50    0.08    --   44.84 -57.00   0.00   70
  4  ω    -26.00  13.00   0.50    0.08    --   44.84 -43.00 136.00   78
  5  ω     18.00  45.00   0.50    0.08    --   44.84 -43.00 136.00   54
  6  ω     43.00  96.00   0.50    0.08    --   44.84-125.00   0.00  106
  7  ω     80.00 112.00   0.50    0.08    --  105.22-125.00 120.00   64
  8  ω     34.00  75.00   0.50    0.08    --  105.22-125.00 120.00   82
  9  ω     52.00 110.00   0.50    0.08    --  105.22-125.00  30.00  116
 10  ω     87.00 112.00   0.50    0.08    --  105.22-125.00 -30.00   50
 11  ω     33.00  63.00   0.50    0.08    --  105.22 -94.00  60.00   60
 12  ω     43.00  68.00   0.50    0.08    --  105.22-125.00 -30.00   50
 13  ω     86.00 111.00   0.50    0.08    --  105.22-125.00 -90.00   50
 14  ω     37.00  99.00   0.50    0.08    --  105.22-125.00-120.00  124
 15  ω     40.00 102.00   0.50    0.08    --  105.22 -94.00-120.00  124
 16  ω     69.00  96.00   0.50    0.08    --  105.22 -94.00  60.00   54
 17  ω     32.00  70.00   0.50    0.08    --  105.22 -61.00  90.00   76
 18  ω     39.00  68.00   0.50    0.08    --  105.22 -61.00 150.00   58
 19  ω     32.00  64.00   0.50    0.08    --  105.22 -61.00   0.00   64
 20  ω     44.00  69.00   0.50    0.08    --  105.22 -61.00 -90.00   50
 21  ω     80.00 111.00   0.50    0.08    --  105.22  15.00  30.00   62
 22  ω    135.00 176.00   0.50    0.08    --  105.22  15.00  30.00   82
 23  ω     86.00 162.00   0.50    0.08    --  105.22  43.00 -72.00  152
 24  ω     28.00 116.00   0.50    0.08    --   44.84  43.00 -72.00  176
 25  ω     -7.00  31.00   0.50    0.08    --  -44.84  19.00  60.00   76
 26  ω    -98.00 -73.00   0.50    0.08    -- -100.00  77.00  90.00   50
 27  ω    -46.00  29.00   0.50    0.08    --  -44.84  43.00 -72.00  150
 28  ω    -94.00 -41.00   0.50    0.08    -- -100.00  77.00-180.00  106
 29  ω   -175.00 -75.00   0.50    0.08    -- -100.00 -15.00-150.00  200
 30  ω   -130.00-104.00   0.50    0.08    -- -100.00 -77.00-120.00   52
 31  ω   -103.00 -74.00   0.50    0.08    -- -100.00 -77.00-120.00   58
 32  ω   -149.00 -82.00   0.50    0.08    -- -100.00 -45.00   0.00  134
 33  ω   -143.00-104.00   0.50    0.08    -- -100.00 -45.00  90.00   78
 34  ω   -168.00-104.00   0.50    0.08    -- -100.00 -43.00 136.00  128
 35  ω   -119.00 -28.00   0.50    0.08    --  -44.84 -43.00 136.00  182
 36  ω   -107.00 -27.00   0.50    0.08    -- -100.00 105.00 -58.41  160
 37  ω    -64.00 -35.00   0.50    0.08    -- -100.00 125.00 120.00   58
 38  ω   -105.00 -77.00   0.50    0.08    -- -100.00 125.00 120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0935321000
_diffrn_orient_matrix_UB_12      0.0745131000
_diffrn_orient_matrix_UB_13      -0.0631115000
_diffrn_orient_matrix_UB_21      0.1114741000
_diffrn_orient_matrix_UB_22      0.0978988000
_diffrn_orient_matrix_UB_23      -0.0391711000
_diffrn_orient_matrix_UB_31      0.0734970000
_diffrn_orient_matrix_UB_32      -0.0667894000
_diffrn_orient_matrix_UB_33      -0.1158255000
_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                4534
_reflns_number_total             4815
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0841
_refine_ls_restrained_S_all      1.039
_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)+(0.0500P)²+13.4077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.2461
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C23(H23), C15(H15), C26(H26), C21(H21), C22(H22), C3(H3A), C25(H25),
 C28(H28), C12(H12), C19(H19), C20(H20), C13(H13), C29(H29), C14(H14)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 0.80203(14) 0.89652(11) 0.17876(12) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.5467(4) 0.1609(3) 0.4428(3) 0.0192(7) Uani 1 1 d . . . . .
O1 O 0.3592(4) 0.0450(3) 0.4496(3) 0.0227(8) Uani 1 1 d . . . . .
H1 H 0.4003 -0.0219 0.4581 0.034 Uiso 1 1 calc R U . . .
N4 N 0.7510(4) 0.2519(4) 0.3047(3) 0.0158(8) Uani 1 1 d . . . . .
N2 N 0.3110(4) 0.2425(3) 0.2623(3) 0.0155(8) Uani 1 1 d . . . . .
N3 N 0.4700(4) 0.4529(3) 0.3252(4) 0.0177(8) Uani 1 1 d . . . . .
H3 H 0.3799 0.4683 0.3634 0.021 Uiso 1 1 calc R U . . .
N1 N 0.2405(4) 0.3512(4) 0.2476(4) 0.0174(8) Uani 1 1 d . . . . .
C11 C 0.6108(5) 0.2952(4) 0.1831(4) 0.0155(9) Uani 1 1 d . . . . .
C16 C 0.7411(5) 0.2463(4) 0.1893(4) 0.0158(9) Uani 1 1 d . . . . .
C24 C 0.5553(5) 0.5525(4) 0.2863(4) 0.0179(9) Uani 1 1 d . . . . .
C10 C 0.5164(5) 0.3262(4) 0.3083(4) 0.0152(9) Uani 1 1 d . . . . .
C18 C 0.8718(5) 0.2206(4) 0.4574(4) 0.0164(9) Uani 1 1 d . . . . .
C23 C 0.8807(5) 0.3430(4) 0.4758(4) 0.0183(10) Uani 1 1 d . . . . .
H23 H 0.8729 0.4025 0.4164 0.022 Uiso 1 1 calc R U . . .
C15 C 0.8433(5) 0.2028(4) 0.0884(4) 0.0191(10) Uani 1 1 d . . . . .
H15 H 0.9305 0.1665 0.0928 0.023 Uiso 1 1 calc R U . . .
C26 C 0.7789(5) 0.6509(5) 0.2137(5) 0.0224(10) Uani 1 1 d . . . . .
H26 H 0.8793 0.6456 0.1859 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6098(5) 0.2731(4) 0.3869(4) 0.0160(9) Uani 1 1 d . . . . .
H9 H 0.6107 0.3315 0.4484 0.019 Uiso 1 1 calc R U . . .
C21 C 0.9136(5) 0.2920(5) 0.6668(4) 0.0218(10) Uani 1 1 d . . . . .
H21 H 0.9267 0.3165 0.7383 0.026 Uiso 1 1 calc R U . . .
C22 C 0.9008(5) 0.3793(5) 0.5792(5) 0.0215(10) Uani 1 1 d . . . . .
H22 H 0.9059 0.4631 0.5909 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2784(5) 0.2851(4) 0.4703(4) 0.0196(10) Uani 1 1 d . . . . .
H7A H 0.2225 0.3563 0.4543 0.029 Uiso 1 1 calc R U . . .
H7B H 0.3292 0.3063 0.5249 0.029 Uiso 1 1 calc R U . . .
H7C H 0.2154 0.2189 0.5069 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2289(5) 0.2181(4) 0.1127(4) 0.0203(10) Uani 1 1 d . . . . .
H3A H 0.2061 0.1851 0.0488 0.024 Uiso 1 1 calc R U . . .
C25 C 0.7026(5) 0.5466(4) 0.2489(4) 0.0194(10) Uani 1 1 d . . . . .
H25 H 0.7516 0.4700 0.2474 0.023 Uiso 1 1 calc R U . . .
C28 C 0.5623(5) 0.7715(4) 0.2573(4) 0.0215(10) Uani 1 1 d . . . . .
H28 H 0.5145 0.8490 0.2616 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5846(5) 0.3105(4) 0.0747(4) 0.0200(10) Uani 1 1 d . . . . .
H12 H 0.4988 0.3493 0.0698 0.024 Uiso 1 1 calc R U . . .
C19 C 0.8849(5) 0.1343(4) 0.5452(4) 0.0194(10) Uani 1 1 d . . . . .
H19 H 0.8787 0.0505 0.5341 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3059(5) 0.1613(4) 0.1810(4) 0.0170(9) Uani 1 1 d . . . . .
C20 C 0.9070(5) 0.1705(5) 0.6487(4) 0.0226(10) Uani 1 1 d . . . . .
H20 H 0.9176 0.1111 0.7072 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6863(6) 0.2679(5) -0.0270(4) 0.0232(11) Uani 1 1 d . . . . .
H13 H 0.6689 0.2755 -0.1019 0.028 Uiso 1 1 calc R U . . .
C17 C 0.8554(5) 0.1775(4) 0.3438(4) 0.0187(10) Uani 1 1 d . . . . .
H17A H 0.9478 0.1796 0.2801 0.022 Uiso 1 1 calc R U . . .
H17B H 0.8263 0.0923 0.3567 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3850(5) 0.2442(4) 0.3529(4) 0.0161(9) Uani 1 1 d . . . . .
C29 C 0.4854(5) 0.6675(4) 0.2896(4) 0.0208(10) Uani 1 1 d . . . . .
H29 H 0.3850 0.6737 0.3140 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8132(5) 0.2143(5) -0.0194(4) 0.0221(10) Uani 1 1 d . . . . .
H14 H 0.8811 0.1848 -0.0895 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4562(5) 0.1234(4) 0.3784(4) 0.0181(10) Uani 1 1 d . . . . .
H8 H 0.5128 0.0851 0.3024 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1912(5) 0.3354(4) 0.1578(4) 0.0193(10) Uani 1 1 d . . . . .
C1 C 0.3738(6) 0.0362(4) 0.1656(5) 0.0224(10) Uani 1 1 d . . . . .
H1A H 0.4770 0.0415 0.1405 0.034 Uiso 1 1 calc R U . . .
H1B H 0.3466 -0.0040 0.1047 0.034 Uiso 1 1 calc R U . . .
H1C H 0.3424 -0.0109 0.2416 0.034 Uiso 1 1 calc R U . . .
C27 C 0.7076(5) 0.7626(4) 0.2193(4) 0.0198(10) Uani 1 1 d . . . . .
C5 C 0.1071(6) 0.4348(5) 0.1158(5) 0.0270(11) Uani 1 1 d . . . . .
H5A H 0.0631 0.4895 0.1810 0.040 Uiso 1 1 calc R U . . .
H5B H 0.0333 0.3994 0.0909 0.040 Uiso 1 1 calc R U . . .
H5C H 0.1698 0.4805 0.0481 0.040 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
Cl1 C27 1.759(5) . ?
O2 C9 1.449(5) . ?
O2 C8 1.439(6) . ?
O1 H1 0.8400 . ?
O1 C8 1.376(6) . ?
N4 C16 1.401(6) . ?
N4 C9 1.451(6) . ?
N4 C17 1.457(6) . ?
N2 N1 1.384(5) . ?
N2 C2 1.364(6) . ?
N2 C6 1.478(6) . ?
N3 H3 0.8800 . ?
N3 C24 1.395(6) . ?
N3 C10 1.451(6) . ?
N1 C4 1.323(6) . ?
C11 C16 1.399(7) . ?
C11 C10 1.528(6) . ?
C11 C12 1.382(7) . ?
C16 C15 1.391(7) . ?
C24 C25 1.392(7) . ?
C24 C29 1.408(7) . ?
C10 C9 1.576(6) . ?
C10 C6 1.568(6) . ?
C18 C23 1.392(7) . ?
C18 C19 1.398(7) . ?
C18 C17 1.507(7) . ?
C23 H23 0.9500 . ?
C23 C22 1.380(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.393(7) . ?
C26 H26 0.9500 . ?
C26 C25 1.387(7) . ?
C26 C27 1.380(7) . ?
C9 H9 1.0000 . ?
C21 H21 0.9500 . ?
C21 C22 1.402(7) . ?
C21 C20 1.377(7) . ?
C22 H22 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.532(6) . ?
C3 H3A 0.9500 . ?
C3 C2 1.379(7) . ?
C3 C4 1.413(7) . ?
C25 H25 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.385(7) . ?
C28 C27 1.374(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(7) . ?
C2 C1 1.497(6) . ?
C20 H20 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.391(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C6 C8 1.532(6) . ?
C29 H29 0.9500 . ?
C14 H14 0.9500 . ?
C8 H8 1.0000 . ?
C4 C5 1.497(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 108.4(3) . . ?
C8 O1 H1 109.5 . . ?
C16 N4 C9 108.5(4) . . ?
C16 N4 C17 121.7(4) . . ?
C9 N4 C17 119.8(4) . . ?
N1 N2 C6 114.0(4) . . ?
C2 N2 N1 111.2(4) . . ?
C2 N2 C6 134.5(4) . . ?
C24 N3 H3 117.1 . . ?
C24 N3 C10 125.9(4) . . ?
C10 N3 H3 117.1 . . ?
C4 N1 N2 105.2(4) . . ?
C16 C11 C10 109.3(4) . . ?
C12 C11 C16 120.7(4) . . ?
C12 C11 C10 130.0(4) . . ?
C11 C16 N4 111.3(4) . . ?
C15 C16 N4 127.8(4) . . ?
C15 C16 C11 120.9(4) . . ?
N3 C24 C29 116.7(4) . . ?
C25 C24 N3 125.0(4) . . ?
C25 C24 C29 118.2(4) . . ?
N3 C10 C11 116.0(4) . . ?
N3 C10 C9 115.4(4) . . ?
N3 C10 C6 109.6(4) . . ?
C11 C10 C9 101.3(4) . . ?
C11 C10 C6 111.9(4) . . ?
C6 C10 C9 101.6(3) . . ?
C23 C18 C19 118.8(4) . . ?
C23 C18 C17 122.4(4) . . ?
C19 C18 C17 118.8(4) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.9(4) . . ?
C22 C23 H23 119.5 . . ?
C16 C15 H15 121.2 . . ?
C16 C15 C14 117.6(5) . . ?
C14 C15 H15 121.2 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C27 C26 C25 119.5(5) . . ?
O2 C9 N4 111.9(4) . . ?
O2 C9 C10 106.0(4) . . ?
O2 C9 H9 110.9 . . ?
N4 C9 C10 106.0(4) . . ?
N4 C9 H9 110.9 . . ?
C10 C9 H9 110.9 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.7(5) . . ?
C23 C22 C21 119.8(5) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
C2 C3 H3A 127.2 . . ?
C2 C3 C4 105.6(4) . . ?
C4 C3 H3A 127.2 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25 119.5 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0(4) . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(5) . . ?
C13 C12 H12 120.6 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19 119.8 . . ?
N2 C2 C3 106.7(4) . . ?
N2 C2 C1 127.1(4) . . ?
C3 C2 C1 126.2(4) . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
N4 C17 C18 112.2(4) . . ?
N4 C17 H17A 109.2 . . ?
N4 C17 H17B 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N2 C6 C10 111.0(4) . . ?
N2 C6 C7 108.5(4) . . ?
N2 C6 C8 115.9(4) . . ?
C7 C6 C10 112.8(4) . . ?
C7 C6 C8 108.1(4) . . ?
C8 C6 C10 100.5(4) . . ?
C24 C29 H29 119.8 . . ?
C28 C29 C24 120.4(5) . . ?
C28 C29 H29 119.8 . . ?
C15 C14 C13 121.7(5) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
O2 C8 C6 102.2(4) . . ?
O2 C8 H8 111.0 . . ?
O1 C8 O2 109.8(4) . . ?
O1 C8 C6 111.6(4) . . ?
O1 C8 H8 111.0 . . ?
C6 C8 H8 111.0 . . ?
N1 C4 C3 111.3(4) . . ?
N1 C4 C5 120.8(4) . . ?
C3 C4 C5 127.9(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C26 C27 Cl1 120.3(4) . . ?
C28 C27 Cl1 118.8(4) . . ?
C28 C27 C26 120.9(5) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C16 C15 C14 -175.5(5) . . . . ?
N2 N1 C4 C3 -0.3(5) . . . . ?
N2 N1 C4 C5 179.7(4) . . . . ?
N2 C6 C8 O2 165.6(4) . . . . ?
N2 C6 C8 O1 -77.2(5) . . . . ?
N3 C24 C25 C26 -178.8(5) . . . . ?
N3 C24 C29 C28 177.2(4) . . . . ?
N3 C10 C9 O2 130.0(4) . . . . ?
N3 C10 C9 N4 -110.9(4) . . . . ?
N3 C10 C6 N2 80.2(4) . . . . ?
N3 C10 C6 C7 -41.9(5) . . . . ?
N3 C10 C6 C8 -156.7(4) . . . . ?
N1 N2 C2 C3 -0.7(5) . . . . ?
N1 N2 C2 C1 177.7(4) . . . . ?
N1 N2 C6 C10 -70.2(5) . . . . ?
N1 N2 C6 C7 54.3(5) . . . . ?
N1 N2 C6 C8 176.0(4) . . . . ?
C11 C16 C15 C14 2.6(7) . . . . ?
C11 C10 C9 O2 -103.9(4) . . . . ?
C11 C10 C9 N4 15.2(4) . . . . ?
C11 C10 C6 N2 -50.0(5) . . . . ?
C11 C10 C6 C7 -172.0(4) . . . . ?
C11 C10 C6 C8 73.2(4) . . . . ?
C11 C12 C13 C14 -1.8(7) . . . . ?
C16 N4 C9 O2 95.4(4) . . . . ?
C16 N4 C9 C10 -19.7(5) . . . . ?
C16 N4 C17 C18 165.4(4) . . . . ?
C16 C11 C10 N3 119.8(4) . . . . ?
C16 C11 C10 C9 -5.9(5) . . . . ?
C16 C11 C10 C6 -113.4(4) . . . . ?
C16 C11 C12 C13 4.8(7) . . . . ?
C16 C15 C14 C13 0.4(7) . . . . ?
C24 N3 C10 C11 -46.0(6) . . . . ?
C24 N3 C10 C9 72.2(6) . . . . ?
C24 N3 C10 C6 -173.9(4) . . . . ?
C10 N3 C24 C25 -15.0(7) . . . . ?
C10 N3 C24 C29 167.3(4) . . . . ?
C10 C11 C16 N4 -6.0(5) . . . . ?
C10 C11 C16 C15 175.7(4) . . . . ?
C10 C11 C12 C13 -176.3(5) . . . . ?
C10 C6 C8 O2 45.9(4) . . . . ?
C10 C6 C8 O1 163.1(4) . . . . ?
C18 C23 C22 C21 0.5(7) . . . . ?
C18 C19 C20 C21 1.2(7) . . . . ?
C23 C18 C19 C20 -0.3(7) . . . . ?
C23 C18 C17 N4 -44.2(6) . . . . ?
C9 O2 C8 O1 -159.1(4) . . . . ?
C9 O2 C8 C6 -40.5(4) . . . . ?
C9 N4 C16 C11 16.6(5) . . . . ?
C9 N4 C16 C15 -165.2(5) . . . . ?
C9 N4 C17 C18 -52.9(6) . . . . ?
C9 C10 C6 N2 -157.3(4) . . . . ?
C9 C10 C6 C7 80.7(4) . . . . ?
C9 C10 C6 C8 -34.2(4) . . . . ?
C22 C21 C20 C19 -1.3(7) . . . . ?
C7 C6 C8 O2 -72.5(4) . . . . ?
C7 C6 C8 O1 44.8(5) . . . . ?
C25 C24 C29 C28 -0.6(7) . . . . ?
C25 C26 C27 Cl1 178.4(4) . . . . ?
C25 C26 C27 C28 -1.1(8) . . . . ?
C12 C11 C16 N4 173.1(4) . . . . ?
C12 C11 C16 C15 -5.2(7) . . . . ?
C12 C11 C10 N3 -59.2(7) . . . . ?
C12 C11 C10 C9 175.1(5) . . . . ?
C12 C11 C10 C6 67.6(6) . . . . ?
C12 C13 C14 C15 -0.8(8) . . . . ?
C19 C18 C23 C22 -0.6(7) . . . . ?
C19 C18 C17 N4 138.7(4) . . . . ?
C2 N2 N1 C4 0.6(5) . . . . ?
C2 N2 C6 C10 102.7(6) . . . . ?
C2 N2 C6 C7 -132.8(5) . . . . ?
C2 N2 C6 C8 -11.1(7) . . . . ?
C2 C3 C4 N1 -0.1(6) . . . . ?
C2 C3 C4 C5 179.9(5) . . . . ?
C20 C21 C22 C23 0.4(7) . . . . ?
C17 N4 C16 C11 162.0(4) . . . . ?
C17 N4 C16 C15 -19.8(7) . . . . ?
C17 N4 C9 O2 -50.8(5) . . . . ?
C17 N4 C9 C10 -165.9(4) . . . . ?
C17 C18 C23 C22 -177.7(4) . . . . ?
C17 C18 C19 C20 177.0(4) . . . . ?
C6 N2 N1 C4 175.2(4) . . . . ?
C6 N2 C2 C3 -173.7(5) . . . . ?
C6 N2 C2 C1 4.7(8) . . . . ?
C6 C10 C9 O2 11.6(4) . . . . ?
C6 C10 C9 N4 130.6(4) . . . . ?
C29 C24 C25 C26 -1.1(7) . . . . ?
C29 C28 C27 Cl1 179.9(4) . . . . ?
C29 C28 C27 C26 -0.7(8) . . . . ?
C8 O2 C9 N4 -97.4(4) . . . . ?
C8 O2 C9 C10 17.7(5) . . . . ?
C4 C3 C2 N2 0.5(5) . . . . ?
C4 C3 C2 C1 -177.9(5) . . . . ?
C27 C26 C25 C24 2.0(7) . . . . ?
C27 C28 C29 C24 1.5(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 2.848
_oxdiff_exptl_absorpt_empirical_full_min 0.546
####################################################################### 
# 
# 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_20220902-smq-f-47_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2d4nhq
_database_code_depnum_ccdc_archive 'CCDC 2209013'
loop_
_audit_author_name
_audit_author_address
shimaoqing
;Sun Yat sen University
China
;
_audit_update_record             
;
2022-09-23 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H26 N4 O2'
_chemical_formula_sum            'C33 H26 N4 O2'
_chemical_formula_weight         510.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   13.1778(4)
_cell_length_b                   14.3635(4)
_cell_length_c                   13.5804(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.473(3)
_cell_angle_gamma                90
_cell_volume                     2554.10(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8331
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3760
_cell_measurement_theta_min      4.4500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15240
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.695
_diffrn_reflns_theta_min         4.432
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  48.00   0.50    0.09    --   44.97 -70.00  21.00  150
  2  ω     68.00  93.00   0.50    0.37    --  105.71 -94.00  60.00   50
  3  ω     32.00  74.00   0.50    0.37    --  105.71 -70.00  21.00   84
  4  ω     40.00  72.00   0.50    0.37    --  105.71 -61.00  30.00   64
  5  ω     39.00  70.00   0.50    0.37    --  105.71 -61.00 -30.00   62
  6  ω     83.00 154.00   0.50    0.37    --  105.71  15.00 -60.00  142
  7  ω    145.00 172.00   0.50    0.37    --  105.71  45.00 -90.00   54
  8  ω    101.00 127.00   0.50    0.37    --  105.71  45.00 -90.00   52
  9  ω    112.00 137.00   0.50    0.37    --  105.71  70.00 152.00   50
 10  ω     46.00  71.00   0.50    0.09    --   44.97  70.00 152.00   50
 11  ω    -11.00  28.00   0.50    0.09    --  -44.97  70.00 152.00   78
 12  ω    -24.00  33.00   0.50    0.09    --  -44.97  19.00 150.00  114
 13  ω    -82.00 -26.00   0.50    0.37    -- -100.00  70.00 152.00  112
 14  ω    -64.00 -27.00   0.50    0.37    -- -100.00  61.00   0.00   74
 15  ω    -69.00 -39.00   0.50    0.37    -- -100.00  61.00 -30.00   60
 16  ω    -66.00 -40.00   0.50    0.37    -- -100.00  61.00 -60.00   52
 17  ω    -68.00 -27.00   0.50    0.37    -- -100.00  61.00-120.00   82
 18  ω    -69.00 -27.00   0.50    0.37    -- -100.00  61.00-150.00   84
 19  ω    -24.00  29.00   0.50    0.09    --  -44.97  19.00 -30.00  106
 20  ω    -68.00 -27.00   0.50    0.37    -- -100.00  61.00 120.00   82
 21  ω   -167.00-115.00   0.50    0.37    -- -100.00 -30.00  60.00  104
 22  ω   -175.00 -95.00   0.50    0.37    -- -100.00 -30.00  90.00  160
 23  ω   -158.00 -98.00   0.50    0.37    -- -100.00 -70.00  21.00  120
 24  ω   -106.00 -46.00   0.50    0.09    --  -44.97 -70.00  21.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1158436000
_diffrn_orient_matrix_UB_12      -0.0044473000
_diffrn_orient_matrix_UB_13      0.0326318000
_diffrn_orient_matrix_UB_21      0.0087444000
_diffrn_orient_matrix_UB_22      -0.0850321000
_diffrn_orient_matrix_UB_23      -0.0675846000
_diffrn_orient_matrix_UB_31      0.0193714000
_diffrn_orient_matrix_UB_32      0.0651490000
_diffrn_orient_matrix_UB_33      -0.0859503000
_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                4171
_reflns_number_total             4962
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.048
_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)+(0.1013P)²+0.9588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1628
_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 Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C2(H2), C6(H6), C25(H25), C3(H3), C12(H12), C13(H13),
 C26(H26), C5(H5), C32(H32), C29(H29), C33(H33), C27(H27), C28(H28), C4(H4),
 C23(H23), C19(H19), C22(H22), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_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
O1 O 0.68275(10) 0.65194(9) 0.19045(9) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.97660(10) 0.58347(9) 0.35991(10) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.96664(11) 0.80810(10) 0.33396(11) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.81918(11) 0.65415(10) 0.38020(11) 0.0213(3) Uani 1 1 d . . . . .
N1 N 0.64260(12) 0.80217(10) 0.23281(11) 0.0223(3) Uani 1 1 d . . . . .
N4 N 1.02651(12) 0.78661(11) 0.41977(11) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.76353(14) 0.59969(12) 0.44174(13) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.79622(13) 0.86816(12) 0.45862(13) 0.0224(4) Uani 1 1 d . . . . .
H11 H 0.8519 0.8420 0.5000 0.027 Uiso 1 1 calc R U . . .
C15 C 0.67305(13) 0.86255(12) 0.31311(13) 0.0205(4) Uani 1 1 d . . . . .
C7 C 0.91304(14) 0.64402(12) 0.34806(13) 0.0215(4) Uani 1 1 d . . . . .
C16 C 0.69880(14) 0.72201(12) 0.24002(13) 0.0216(4) Uani 1 1 d . . . . .
C14 C 0.63115(14) 0.94692(12) 0.33506(14) 0.0233(4) Uani 1 1 d . . . . .
H14 H 0.5759 0.9734 0.2933 0.028 Uiso 1 1 calc R U . . .
C10 C 0.75596(13) 0.82402(12) 0.37266(13) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.66587(15) 0.62756(13) 0.45911(14) 0.0254(4) Uani 1 1 d . . . . .
H2 H 0.6368 0.6828 0.4295 0.030 Uiso 1 1 calc R U . . .
C9 C 0.78779(13) 0.73776(11) 0.32264(13) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.90095(13) 0.73568(12) 0.28643(13) 0.0209(4) Uani 1 1 d . . . . .
C6 C 0.80716(15) 0.51912(13) 0.48616(14) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.8743 0.5007 0.4754 0.031 Uiso 1 1 calc R U . . .
C24 C 0.91662(14) 0.72454(12) 0.17803(13) 0.0226(4) Uani 1 1 d . . . . .
C30 C 0.96970(14) 0.90061(12) 0.31155(13) 0.0233(4) Uani 1 1 d . . . . .
C18 C 0.45368(15) 0.80000(14) 0.19056(13) 0.0264(4) Uani 1 1 d . . . . .
C25 C 0.85078(15) 0.75815(12) 0.09863(14) 0.0255(4) Uani 1 1 d . . . . .
H25 H 0.7904 0.7902 0.1107 0.031 Uiso 1 1 calc R U . . .
C3 C 0.61153(16) 0.57433(14) 0.51976(15) 0.0302(4) Uani 1 1 d . . . . .
H3 H 0.5450 0.5933 0.5320 0.036 Uiso 1 1 calc R U . . .
C12 C 0.75257(14) 0.95242(13) 0.48284(14) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.7777 0.9832 0.5426 0.030 Uiso 1 1 calc R U . . .
C13 C 0.67331(14) 0.99181(12) 0.42122(14) 0.0253(4) Uani 1 1 d . . . . .
H13 H 0.6470 1.0506 0.4379 0.030 Uiso 1 1 calc R U . . .
C26 C 0.87258(16) 0.74527(13) 0.00209(15) 0.0291(4) Uani 1 1 d . . . . .
H26 H 0.8266 0.7678 -0.0515 0.035 Uiso 1 1 calc R U . . .
C5 C 0.75073(16) 0.46677(14) 0.54604(15) 0.0312(4) Uani 1 1 d . . . . .
H5 H 0.7794 0.4116 0.5761 0.037 Uiso 1 1 calc R U . . .
C31 C 0.90869(15) 0.94664(13) 0.22576(14) 0.0259(4) Uani 1 1 d . . . . .
H31A H 0.9343 0.9270 0.1640 0.039 Uiso 1 1 calc R U . . .
H31B H 0.9149 1.0144 0.2326 0.039 Uiso 1 1 calc R U . . .
H31C H 0.8368 0.9287 0.2244 0.039 Uiso 1 1 calc R U . . .
C32 C 1.03587(15) 0.93976(13) 0.38485(14) 0.0271(4) Uani 1 1 d . . . . .
H32 H 1.0553 1.0034 0.3909 0.032 Uiso 1 1 calc R U . . .
C17 C 0.55677(14) 0.82029(13) 0.15687(13) 0.0246(4) Uani 1 1 d . . . . .
H17A H 0.5651 0.7817 0.0979 0.030 Uiso 1 1 calc R U . . .
H17B H 0.5588 0.8864 0.1367 0.030 Uiso 1 1 calc R U . . .
C29 C 1.00596(14) 0.67922(13) 0.15798(15) 0.0269(4) Uani 1 1 d . . . . .
H29 H 1.0519 0.6559 0.2112 0.032 Uiso 1 1 calc R U . . .
C33 C 1.06911(15) 0.86695(13) 0.44923(15) 0.0288(4) Uani 1 1 d . . . . .
H33 H 1.1164 0.8743 0.5069 0.035 Uiso 1 1 calc R U . . .
C27 C 0.96127(17) 0.69963(14) -0.01690(15) 0.0316(5) Uani 1 1 d . . . . .
H27 H 0.9757 0.6903 -0.0832 0.038 Uiso 1 1 calc R U . . .
C28 C 1.02836(16) 0.66785(15) 0.06149(16) 0.0326(5) Uani 1 1 d . . . . .
H28 H 1.0901 0.6381 0.0491 0.039 Uiso 1 1 calc R U . . .
C4 C 0.65312(17) 0.49349(15) 0.56290(15) 0.0333(5) Uani 1 1 d . . . . .
H4 H 0.6150 0.4566 0.6037 0.040 Uiso 1 1 calc R U . . .
C23 C 0.38724(15) 0.87172(16) 0.20692(15) 0.0331(5) Uani 1 1 d . . . . .
H23 H 0.4068 0.9344 0.1971 0.040 Uiso 1 1 calc R U . . .
C19 C 0.42388(18) 0.70823(16) 0.20429(15) 0.0356(5) Uani 1 1 d . . . . .
H19 H 0.4687 0.6583 0.1939 0.043 Uiso 1 1 calc R U . . .
C22 C 0.29234(17) 0.8528(2) 0.23747(17) 0.0451(6) Uani 1 1 d . . . . .
H22 H 0.2479 0.9025 0.2496 0.054 Uiso 1 1 calc R U . . .
C20 C 0.3274(2) 0.69030(19) 0.23348(16) 0.0466(6) Uani 1 1 d . . . . .
H20 H 0.3062 0.6279 0.2419 0.056 Uiso 1 1 calc R U . . .
C21 C 0.26269(18) 0.7628(2) 0.25013(18) 0.0494(7) Uani 1 1 d . . . . .
H21 H 0.1974 0.7502 0.2704 0.059 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
O1 C16 1.216(2) . ?
O2 C7 1.206(2) . ?
N3 N4 1.367(2) . ?
N3 C8 1.457(2) . ?
N3 C30 1.365(2) . ?
N2 C1 1.409(2) . ?
N2 C7 1.365(2) . ?
N2 C9 1.467(2) . ?
N1 C15 1.415(2) . ?
N1 C16 1.366(2) . ?
N1 C17 1.466(2) . ?
N4 C33 1.325(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.398(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.381(3) . ?
C11 C12 1.395(3) . ?
C15 C14 1.378(2) . ?
C15 C10 1.398(2) . ?
C7 C8 1.559(2) . ?
C16 C9 1.546(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.395(3) . ?
C10 C9 1.496(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C9 C8 1.622(2) . ?
C8 C24 1.518(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(3) . ?
C24 C25 1.392(3) . ?
C24 C29 1.399(3) . ?
C30 C31 1.493(3) . ?
C30 C32 1.368(3) . ?
C18 C17 1.510(3) . ?
C18 C23 1.386(3) . ?
C18 C19 1.394(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C33 1.401(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C29 H29 0.9500 . ?
C29 C28 1.385(3) . ?
C33 H33 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.382(3) . ?
C28 H28 0.9500 . ?
C4 H4 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.388(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.398(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.366(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(4) . ?
C21 H21 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
N4 N3 C8 118.26(14) . . ?
C30 N3 N4 112.41(14) . . ?
C30 N3 C8 128.86(15) . . ?
C1 N2 C9 129.50(15) . . ?
C7 N2 C1 132.95(15) . . ?
C7 N2 C9 97.36(13) . . ?
C15 N1 C17 124.23(15) . . ?
C16 N1 C15 110.91(15) . . ?
C16 N1 C17 124.68(15) . . ?
C33 N4 N3 104.17(14) . . ?
C2 C1 N2 119.56(16) . . ?
C2 C1 C6 120.50(17) . . ?
C6 C1 N2 119.93(17) . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 117.92(17) . . ?
C12 C11 H11 121.0 . . ?
C14 C15 N1 128.30(16) . . ?
C14 C15 C10 121.93(16) . . ?
C10 C15 N1 109.77(15) . . ?
O2 C7 N2 132.46(17) . . ?
O2 C7 C8 135.12(17) . . ?
N2 C7 C8 92.31(13) . . ?
O1 C16 N1 126.78(17) . . ?
O1 C16 C9 126.40(16) . . ?
N1 C16 C9 106.82(14) . . ?
C15 C14 H14 121.4 . . ?
C15 C14 C13 117.16(17) . . ?
C13 C14 H14 121.4 . . ?
C11 C10 C15 120.54(16) . . ?
C11 C10 C9 131.58(16) . . ?
C15 C10 C9 107.82(15) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.52(18) . . ?
C3 C2 H2 120.2 . . ?
N2 C9 C16 114.36(14) . . ?
N2 C9 C10 120.86(14) . . ?
N2 C9 C8 86.15(12) . . ?
C16 C9 C8 115.17(14) . . ?
C10 C9 C16 102.84(14) . . ?
C10 C9 C8 117.86(14) . . ?
N3 C8 C7 110.22(14) . . ?
N3 C8 C9 111.91(13) . . ?
N3 C8 C24 111.47(14) . . ?
C7 C8 C9 83.95(12) . . ?
C24 C8 C7 114.51(14) . . ?
C24 C8 C9 121.75(14) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.75(18) . . ?
C5 C6 H6 120.6 . . ?
C25 C24 C8 125.00(16) . . ?
C25 C24 C29 118.38(17) . . ?
C29 C24 C8 116.59(16) . . ?
N3 C30 C31 125.33(16) . . ?
N3 C30 C32 105.69(16) . . ?
C32 C30 C31 128.95(17) . . ?
C23 C18 C17 120.76(18) . . ?
C23 C18 C19 119.26(19) . . ?
C19 C18 C17 119.98(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.59(18) . . ?
C26 C25 H25 119.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.60(19) . . ?
C4 C3 H3 119.7 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.02(17) . . ?
C13 C12 H12 119.5 . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.35(17) . . ?
C12 C13 H13 119.3 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.47(19) . . ?
C27 C26 H26 119.8 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.11(18) . . ?
C4 C5 H5 119.4 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32 127.0 . . ?
C30 C32 C33 106.02(16) . . ?
C33 C32 H32 127.0 . . ?
N1 C17 C18 113.70(15) . . ?
N1 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C24 C29 H29 119.6 . . ?
C28 C29 C24 120.87(19) . . ?
C28 C29 H29 119.6 . . ?
N4 C33 C32 111.69(17) . . ?
N4 C33 H33 124.2 . . ?
C32 C33 H33 124.2 . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.42(18) . . ?
C28 C27 H27 120.3 . . ?
C29 C28 H28 119.9 . . ?
C27 C28 C29 120.24(19) . . ?
C27 C28 H28 119.9 . . ?
C3 C4 C5 119.51(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C18 C23 H23 119.7 . . ?
C18 C23 C22 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 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
O1 C16 C9 N2 -34.2(2) . . . . ?
O1 C16 C9 C10 -167.12(17) . . . . ?
O1 C16 C9 C8 63.3(2) . . . . ?
O2 C7 C8 N3 -76.2(2) . . . . ?
O2 C7 C8 C9 172.7(2) . . . . ?
O2 C7 C8 C24 50.4(3) . . . . ?
N3 N4 C33 C32 1.2(2) . . . . ?
N3 C8 C24 C25 -103.12(19) . . . . ?
N3 C8 C24 C29 74.94(19) . . . . ?
N3 C30 C32 C33 -0.5(2) . . . . ?
N2 C1 C2 C3 -179.75(17) . . . . ?
N2 C1 C6 C5 -179.83(16) . . . . ?
N2 C7 C8 N3 107.56(15) . . . . ?
N2 C7 C8 C9 -3.59(12) . . . . ?
N2 C7 C8 C24 -125.82(15) . . . . ?
N2 C9 C8 N3 -106.04(14) . . . . ?
N2 C9 C8 C7 3.35(11) . . . . ?
N2 C9 C8 C24 118.50(16) . . . . ?
N1 C15 C14 C13 177.80(17) . . . . ?
N1 C15 C10 C11 -176.82(15) . . . . ?
N1 C15 C10 C9 5.75(19) . . . . ?
N1 C16 C9 N2 146.44(15) . . . . ?
N1 C16 C9 C10 13.54(17) . . . . ?
N1 C16 C9 C8 -116.01(15) . . . . ?
N4 N3 C8 C7 0.6(2) . . . . ?
N4 N3 C8 C9 92.17(17) . . . . ?
N4 N3 C8 C24 -127.69(16) . . . . ?
N4 N3 C30 C31 -176.65(17) . . . . ?
N4 N3 C30 C32 1.3(2) . . . . ?
C1 N2 C7 O2 2.7(3) . . . . ?
C1 N2 C7 C8 179.13(18) . . . . ?
C1 N2 C9 C16 -63.3(2) . . . . ?
C1 N2 C9 C10 60.4(2) . . . . ?
C1 N2 C9 C8 -179.23(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C11 C10 C9 N2 42.5(3) . . . . ?
C11 C10 C9 C16 171.47(18) . . . . ?
C11 C10 C9 C8 -60.7(2) . . . . ?
C11 C12 C13 C14 2.9(3) . . . . ?
C15 N1 C16 O1 169.81(17) . . . . ?
C15 N1 C16 C9 -10.86(19) . . . . ?
C15 N1 C17 C18 -78.2(2) . . . . ?
C15 C14 C13 C12 -1.1(3) . . . . ?
C15 C10 C9 N2 -140.47(16) . . . . ?
C15 C10 C9 C16 -11.50(18) . . . . ?
C15 C10 C9 C8 116.38(16) . . . . ?
C7 N2 C1 C2 -178.10(18) . . . . ?
C7 N2 C1 C6 2.9(3) . . . . ?
C7 N2 C9 C16 112.11(15) . . . . ?
C7 N2 C9 C10 -124.19(17) . . . . ?
C7 N2 C9 C8 -3.83(13) . . . . ?
C7 C8 C24 C25 130.91(18) . . . . ?
C7 C8 C24 C29 -51.0(2) . . . . ?
C16 N1 C15 C14 -175.97(17) . . . . ?
C16 N1 C15 C10 3.5(2) . . . . ?
C16 N1 C17 C18 96.5(2) . . . . ?
C16 C9 C8 N3 138.81(15) . . . . ?
C16 C9 C8 C7 -111.81(15) . . . . ?
C16 C9 C8 C24 3.3(2) . . . . ?
C14 C15 C10 C11 2.7(3) . . . . ?
C14 C15 C10 C9 -174.73(16) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C10 C15 C14 C13 -1.6(3) . . . . ?
C10 C9 C8 N3 17.1(2) . . . . ?
C10 C9 C8 C7 126.44(15) . . . . ?
C10 C9 C8 C24 -118.41(18) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C9 N2 C1 C2 -4.3(3) . . . . ?
C9 N2 C1 C6 176.71(16) . . . . ?
C9 N2 C7 O2 -172.4(2) . . . . ?
C9 N2 C7 C8 3.98(13) . . . . ?
C9 C8 C24 C25 32.5(2) . . . . ?
C9 C8 C24 C29 -149.43(16) . . . . ?
C8 N3 N4 C33 -174.45(15) . . . . ?
C8 N3 C30 C31 -4.7(3) . . . . ?
C8 N3 C30 C32 173.23(17) . . . . ?
C8 C24 C25 C26 179.25(17) . . . . ?
C8 C24 C29 C28 -178.31(17) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C24 C29 C28 C27 -1.4(3) . . . . ?
C30 N3 N4 C33 -1.6(2) . . . . ?
C30 N3 C8 C7 -170.93(16) . . . . ?
C30 N3 C8 C9 -79.4(2) . . . . ?
C30 N3 C8 C24 60.8(2) . . . . ?
C30 C32 C33 N4 -0.5(2) . . . . ?
C18 C23 C22 C21 -1.1(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C25 C24 C29 C28 -0.1(3) . . . . ?
C25 C26 C27 C28 -0.6(3) . . . . ?
C12 C11 C10 C15 -0.9(3) . . . . ?
C12 C11 C10 C9 175.79(17) . . . . ?
C26 C27 C28 C29 1.7(3) . . . . ?
C31 C30 C32 C33 177.37(19) . . . . ?
C17 N1 C15 C14 -0.6(3) . . . . ?
C17 N1 C15 C10 178.89(16) . . . . ?
C17 N1 C16 O1 -5.5(3) . . . . ?
C17 N1 C16 C9 173.79(15) . . . . ?
C17 C18 C23 C22 179.71(18) . . . . ?
C17 C18 C19 C20 -178.66(17) . . . . ?
C29 C24 C25 C26 1.2(3) . . . . ?
C23 C18 C17 N1 109.7(2) . . . . ?
C23 C18 C19 C20 0.5(3) . . . . ?
C23 C22 C21 C20 0.6(3) . . . . ?
C19 C18 C17 N1 -71.2(2) . . . . ?
C19 C18 C23 C22 0.6(3) . . . . ?
C19 C20 C21 C22 0.5(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 3.535
_oxdiff_exptl_absorpt_empirical_full_min 0.571
####################################################################### 
# 
# 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_pre_20221129-smq-1_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2dm81c
_database_code_depnum_ccdc_archive 'CCDC 2223042'
loop_
_audit_author_name
_audit_author_address
shi
;Sun Yat sen University
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2022-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H28 N4 O2'
_chemical_formula_sum            'C34 H28 N4 O2'
_chemical_formula_weight         524.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.84990(10)
_cell_length_b                   16.04180(10)
_cell_length_c                   19.52990(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.4500(10)
_cell_angle_gamma                90
_cell_volume                     5278.82(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    32643
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.4350
_cell_measurement_theta_min      2.2450
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40763
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.668
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     77.00  82.00   0.50    0.50    --  105.85 -70.00  90.00   10
  2  ω     28.00  33.00   0.50    0.13    --   44.84 -70.00  90.00   10
  3  ω    -23.00 -18.00   0.50    0.13    --  -44.84  70.00   0.00   10
  4  ω    -23.00 -18.00   0.50    0.13    --  -44.84  70.00  90.00   10
  5  ω    -79.00 -74.00   0.50    0.50    -- -100.00  70.00   0.00   10
  6  ω    -79.00 -74.00   0.50    0.50    -- -100.00  70.00  90.00   10
  7  ω     67.00 118.00   0.50    0.33    --   44.84 144.00 104.00  102
  8  ω   -168.00 -72.00   0.50    1.00    -- -100.00-140.00 137.00  192
  9  ω   -174.00-147.00   0.50    1.00    -- -100.00   5.00-164.00   54
 10  ω     38.00 125.00   0.50    1.00    --  105.85-144.00  50.00  174
 11  ω    150.00 175.00   0.50    1.00    --  105.85  -5.00  19.00   50
 12  ω    -24.00  17.00   0.50    0.33    --  -44.84  19.00 -30.00   82
 13  ω    -16.00  63.00   0.50    0.33    --   44.84 -57.00-120.00  158
 14  ω     -8.00  25.00   0.50    0.33    --   44.84 -19.00 -90.00   66
 15  ω    -69.00 -42.00   0.50    1.00    -- -100.00  61.00  60.00   54
 16  ω   -160.00 -87.00   0.50    1.00    -- -100.00 -94.00 -30.00  146
 17  ω     58.00 111.00   0.50    1.00    --  105.85-125.00 -30.00  106
 18  ω    120.00 163.00   0.50    1.00    --  105.85  61.00 -60.00   86
 19  ω     66.00  91.00   0.50    0.33    --   44.84 144.00 104.00   50
 20  ω     87.00 113.00   0.50    0.25    --   44.84  38.00 -30.00   52
 21  ω     -3.00  31.00   0.50    0.25    --  -44.84  19.00  90.00   68
 22  ω     53.00 116.00   0.50    0.25    --   44.84  57.00-150.00  126
 23  ω   -112.00 -85.00   0.50    0.50    -- -100.00 -45.00-120.00   54
 24  ω   -168.00-129.00   0.50    0.50    -- -100.00 -30.00 150.00   78
 25  ω   -126.00 -82.00   0.50    0.50    -- -100.00 -30.00 150.00   88
 26  ω   -160.00-120.00   0.50    0.50    -- -100.00 -45.00-120.00   80
 27  ω     33.00  59.00   0.50    0.50    --  105.85-125.00   0.00   52
 28  ω     57.00  87.00   0.50    0.50    --  105.85 -94.00 -90.00   60
 29  ω     33.00  73.00   0.50    0.50    --  105.85 -61.00  60.00   80
 30  ω    113.00 168.00   0.50    0.50    --  105.85  30.00  60.00  110
 31  ω     42.00  67.00   0.50    0.50    --  105.85 -61.00  90.00   50
 32  ω     40.00  66.00   0.50    0.50    --  105.85 -61.00 -60.00   52
 33  ω     75.00 107.00   0.50    0.50    --  105.85 -77.00 150.00   64
 34  ω     65.00 111.00   0.50    0.50    --  105.85-125.00   0.00   92
 35  ω     42.00  69.00   0.50    0.50    --  105.85 -61.00-180.00   54
 36  ω    -80.00 -55.00   0.50    0.25    --  -44.84 127.00 -64.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0201347000
_diffrn_orient_matrix_UB_12      -0.0022200000
_diffrn_orient_matrix_UB_13      0.0767476000
_diffrn_orient_matrix_UB_21      -0.0890066000
_diffrn_orient_matrix_UB_22      0.0066132000
_diffrn_orient_matrix_UB_23      -0.0178096000
_diffrn_orient_matrix_UB_31      -0.0056921000
_diffrn_orient_matrix_UB_32      -0.0958274000
_diffrn_orient_matrix_UB_33      -0.0030484000
_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                10252
_reflns_number_total             10510
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         10510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.146
_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)+(0.0266P)²+3.6824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0943
_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 Secondary CH2 refined with riding coordinates:
 C62(H62A,H62B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C44(H44), C22(H22), C57(H57), C11(H11), C52(H52), C24(H24), C61(H61),
 C53(H53), C15(H15), C6(H6), C50(H50), C51(H51), C25(H25), C36(H36), C23(H23),
 C19(H19), C64(H64), C2(H2), C59(H59), C60(H60), C58(H58), C5(H5), C40(H40),
 C30(H30), C68(H68), C34(H34), C16(H16), C37(H37), C32(H32), C65(H65), C31(H31),
  C4(H4), C66(H66), C3(H3), C38(H38), C67(H67), C18(H18), C33(H33), C39(H39),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C10(H10A,H10B,H10C), C43(H43A,H43B,H43C), C13(H13A,H13B,
 H13C)
;
_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
O1 O 0.97010(6) 0.90402(6) 0.33193(5) 0.0204(2) Uani 1 1 d . . . . .
O2 O 0.74033(6) 0.84911(6) 0.27345(5) 0.0199(2) Uani 1 1 d . . . . .
O3 O 1.47662(6) 0.88900(6) 0.20296(5) 0.0210(2) Uani 1 1 d . . . . .
O4 O 1.23925(6) 0.84271(6) 0.25508(5) 0.0210(2) Uani 1 1 d . . . . .
N8 N 1.53746(6) 0.76850(7) 0.16524(6) 0.0163(2) Uani 1 1 d . . . . .
N6 N 1.33095(6) 0.66691(7) 0.28001(6) 0.0152(2) Uani 1 1 d . . . . .
N3 N 0.82877(6) 0.80860(7) 0.36146(6) 0.0151(2) Uani 1 1 d . . . . .
N7 N 1.33017(6) 0.80146(7) 0.17057(6) 0.0154(2) Uani 1 1 d . . . . .
N2 N 0.83346(6) 0.67327(7) 0.25456(6) 0.0145(2) Uani 1 1 d . . . . .
N5 N 1.25179(6) 0.65244(7) 0.26704(6) 0.0162(2) Uani 1 1 d . . . . .
N4 N 1.03758(6) 0.78704(7) 0.36970(6) 0.0167(2) Uani 1 1 d . . . . .
N1 N 0.75464(6) 0.65792(7) 0.26777(6) 0.0160(2) Uani 1 1 d . . . . .
C26 C 1.01714(8) 0.70463(8) 0.38681(6) 0.0156(3) Uani 1 1 d . . . . .
C1 C 0.81142(8) 0.85274(8) 0.42237(7) 0.0164(3) Uani 1 1 d . . . . .
C56 C 1.31467(8) 0.84360(8) 0.10827(7) 0.0160(3) Uani 1 1 d . . . . .
C12 C 0.87221(8) 0.60273(8) 0.23351(7) 0.0163(3) Uani 1 1 d . . . . .
C27 C 0.97324(8) 0.83035(8) 0.34586(6) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.79655(8) 0.81252(8) 0.29673(7) 0.0151(3) Uani 1 1 d . . . . .
C21 C 0.93579(8) 0.69164(8) 0.37580(6) 0.0150(3) Uani 1 1 d . . . . .
C49 C 1.43068(8) 0.67914(8) 0.15829(6) 0.0148(3) Uani 1 1 d . . . . .
C47 C 1.29612(8) 0.80574(8) 0.23404(7) 0.0160(3) Uani 1 1 d . . . . .
C41 C 1.36230(8) 0.74997(8) 0.26660(7) 0.0153(3) Uani 1 1 d . . . . .
C35 C 1.40325(8) 0.78557(8) 0.32962(7) 0.0183(3) Uani 1 1 d . . . . .
C54 C 1.51222(8) 0.68777(8) 0.14690(6) 0.0150(3) Uani 1 1 d . . . . .
C42 C 1.36974(8) 0.59588(8) 0.30056(7) 0.0168(3) Uani 1 1 d . . . . .
C44 C 1.31324(8) 0.53448(9) 0.30166(7) 0.0183(3) Uani 1 1 d . . . . .
H44 H 1.3210 0.4778 0.3141 0.022 Uiso 1 1 calc R U . . .
C48 C 1.40262(8) 0.75747(8) 0.19244(7) 0.0146(3) Uani 1 1 d . . . . .
C45 C 1.24154(8) 0.57186(8) 0.28076(7) 0.0170(3) Uani 1 1 d . . . . .
C22 C 0.90273(8) 0.61416(8) 0.38817(7) 0.0168(3) Uani 1 1 d . . . . .
H22 H 0.8475 0.6049 0.3818 0.020 Uiso 1 1 calc R U . . .
C55 C 1.47559(8) 0.81531(8) 0.18872(7) 0.0159(3) Uani 1 1 d . . . . .
C20 C 0.90333(7) 0.76806(8) 0.34151(6) 0.0143(3) Uani 1 1 d . . . . .
C9 C 0.74484(8) 0.57733(8) 0.25383(7) 0.0165(3) Uani 1 1 d . . . . .
C63 C 1.62571(8) 0.82845(9) 0.07780(7) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.90498(8) 0.79030(8) 0.20354(7) 0.0171(3) Uani 1 1 d . . . . .
C29 C 1.12613(8) 0.84503(9) 0.45901(7) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.86383(8) 0.75718(8) 0.26662(7) 0.0147(3) Uani 1 1 d . . . . .
C57 C 1.24961(8) 0.89706(9) 0.10215(7) 0.0197(3) Uani 1 1 d . . . . .
H57 H 1.2159 0.9068 0.1401 0.024 Uiso 1 1 calc R U . . .
C11 C 0.81641(8) 0.54057(9) 0.23267(7) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.8244 0.4839 0.2203 0.022 Uiso 1 1 calc R U . . .
C52 C 1.52038(8) 0.54692(9) 0.11127(7) 0.0199(3) Uani 1 1 d . . . . .
H52 H 1.5506 0.5006 0.0961 0.024 Uiso 1 1 calc R U . . .
C24 C 1.03336(8) 0.56351(9) 0.41973(7) 0.0204(3) Uani 1 1 d . . . . .
H24 H 1.0663 0.5186 0.4339 0.024 Uiso 1 1 calc R U . . .
C61 C 1.36412(8) 0.82961(9) 0.05266(7) 0.0192(3) Uani 1 1 d . . . . .
H61 H 1.4086 0.7935 0.0571 0.023 Uiso 1 1 calc R U . . .
C53 C 1.55831(8) 0.62285(9) 0.12321(7) 0.0179(3) Uani 1 1 d . . . . .
H53 H 1.6135 0.6296 0.1154 0.021 Uiso 1 1 calc R U . . .
C15 C 0.85603(9) 0.81342(9) 0.14860(7) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.8000 0.8129 0.1537 0.025 Uiso 1 1 calc R U . . .
C6 C 0.85970(8) 0.84230(9) 0.47984(7) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.9050 0.8071 0.4779 0.024 Uiso 1 1 calc R U . . .
C50 C 1.39323(8) 0.60411(9) 0.14474(7) 0.0171(3) Uani 1 1 d . . . . .
H50 H 1.3377 0.5979 0.1514 0.020 Uiso 1 1 calc R U . . .
C51 C 1.43928(8) 0.53764(9) 0.12102(7) 0.0196(3) Uani 1 1 d . . . . .
H51 H 1.4148 0.4855 0.1115 0.023 Uiso 1 1 calc R U . . .
C25 C 1.06714(8) 0.64159(9) 0.40899(7) 0.0186(3) Uani 1 1 d . . . . .
H25 H 1.1222 0.6512 0.4166 0.022 Uiso 1 1 calc R U . . .
C62 C 1.61660(8) 0.80205(9) 0.15193(7) 0.0195(3) Uani 1 1 d . . . . .
H62A H 1.6569 0.7592 0.1631 0.023 Uiso 1 1 calc R U . . .
H62B H 1.6262 0.8507 0.1821 0.023 Uiso 1 1 calc R U . . .
C36 C 1.35424(9) 0.81585(9) 0.38129(7) 0.0225(3) Uani 1 1 d . . . . .
H36 H 1.2985 0.8182 0.3741 0.027 Uiso 1 1 calc R U . . .
C46 C 1.16187(8) 0.53174(9) 0.27297(8) 0.0222(3) Uani 1 1 d . . . . .
H46A H 1.1210 0.5750 0.2691 0.033 Uiso 1 1 calc R U . . .
H46B H 1.1513 0.4969 0.3131 0.033 Uiso 1 1 calc R U . . .
H46C H 1.1611 0.4971 0.2316 0.033 Uiso 1 1 calc R U . . .
C23 C 0.95270(8) 0.54976(9) 0.41023(7) 0.0198(3) Uani 1 1 d . . . . .
H23 H 0.9312 0.4961 0.4188 0.024 Uiso 1 1 calc R U . . .
C19 C 0.98683(9) 0.79241(9) 0.19566(7) 0.0218(3) Uani 1 1 d . . . . .
H19 H 1.0206 0.7780 0.2330 0.026 Uiso 1 1 calc R U . . .
C64 C 1.57697(9) 0.89091(9) 0.05089(8) 0.0225(3) Uani 1 1 d . . . . .
H64 H 1.5385 0.9167 0.0792 0.027 Uiso 1 1 calc R U . . .
C10 C 0.66535(8) 0.53683(9) 0.26124(8) 0.0215(3) Uani 1 1 d . . . . .
H10A H 0.6658 0.5007 0.3017 0.032 Uiso 1 1 calc R U . . .
H10B H 0.6537 0.5034 0.2204 0.032 Uiso 1 1 calc R U . . .
H10C H 0.6246 0.5799 0.2664 0.032 Uiso 1 1 calc R U . . .
C2 C 0.74517(9) 0.90466(9) 0.42493(7) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.7124 0.9121 0.3856 0.027 Uiso 1 1 calc R U . . .
C59 C 1.28371(9) 0.92165(10) -0.01619(7) 0.0240(3) Uani 1 1 d . . . . .
H59 H 1.2728 0.9481 -0.0587 0.029 Uiso 1 1 calc R U . . .
C60 C 1.34812(9) 0.86873(9) -0.00938(7) 0.0223(3) Uani 1 1 d . . . . .
H60 H 1.3817 0.8591 -0.0474 0.027 Uiso 1 1 calc R U . . .
C58 C 1.23508(9) 0.93571(10) 0.03978(8) 0.0236(3) Uani 1 1 d . . . . .
H58 H 1.1911 0.9724 0.0352 0.028 Uiso 1 1 calc R U . . .
C5 C 0.84112(9) 0.88378(10) 0.54014(7) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.8739 0.8767 0.5795 0.029 Uiso 1 1 calc R U . . .
C40 C 1.48493(9) 0.78372(9) 0.34031(8) 0.0229(3) Uani 1 1 d . . . . .
H40 H 1.5189 0.7643 0.3051 0.028 Uiso 1 1 calc R U . . .
C43 C 1.45678(8) 0.58908(9) 0.31460(7) 0.0204(3) Uani 1 1 d . . . . .
H43A H 1.4862 0.6154 0.2773 0.031 Uiso 1 1 calc R U . . .
H43B H 1.4717 0.5302 0.3179 0.031 Uiso 1 1 calc R U . . .
H43C H 1.4696 0.6172 0.3578 0.031 Uiso 1 1 calc R U . . .
C13 C 0.95876(8) 0.59714(9) 0.21816(8) 0.0207(3) Uani 1 1 d . . . . .
H13A H 0.9699 0.6276 0.1758 0.031 Uiso 1 1 calc R U . . .
H13B H 0.9738 0.5385 0.2126 0.031 Uiso 1 1 calc R U . . .
H13C H 0.9894 0.6216 0.2560 0.031 Uiso 1 1 calc R U . . .
C30 C 1.07975(9) 0.90653(9) 0.48930(8) 0.0245(3) Uani 1 1 d . . . . .
H30 H 1.0413 0.9354 0.4625 0.029 Uiso 1 1 calc R U . . .
C68 C 1.68193(9) 0.79170(9) 0.03564(8) 0.0244(3) Uani 1 1 d . . . . .
H68 H 1.7152 0.7488 0.0531 0.029 Uiso 1 1 calc R U . . .
C28 C 1.11517(8) 0.82490(9) 0.38379(7) 0.0201(3) Uani 1 1 d . . . . .
H28A H 1.1203 0.8767 0.3567 0.024 Uiso 1 1 calc R U . . .
H28B H 1.1575 0.7861 0.3693 0.024 Uiso 1 1 calc R U . . .
C34 C 1.18191(9) 0.80359(9) 0.49895(8) 0.0238(3) Uani 1 1 d . . . . .
H34 H 1.2138 0.7613 0.4792 0.029 Uiso 1 1 calc R U . . .
C16 C 0.88888(10) 0.83714(9) 0.08667(8) 0.0265(3) Uani 1 1 d . . . . .
H16 H 0.8554 0.8533 0.0496 0.032 Uiso 1 1 calc R U . . .
C37 C 1.38671(11) 0.84265(9) 0.44324(8) 0.0282(3) Uani 1 1 d . . . . .
H37 H 1.3531 0.8633 0.4782 0.034 Uiso 1 1 calc R U . . .
C32 C 1.14502(10) 0.88466(10) 0.59721(8) 0.0279(3) Uani 1 1 d . . . . .
H32 H 1.1516 0.8981 0.6443 0.033 Uiso 1 1 calc R U . . .
C65 C 1.58423(9) 0.91564(10) -0.01676(8) 0.0258(3) Uani 1 1 d . . . . .
H65 H 1.5503 0.9577 -0.0347 0.031 Uiso 1 1 calc R U . . .
C31 C 1.08905(9) 0.92613(10) 0.55793(8) 0.0290(3) Uani 1 1 d . . . . .
H31 H 1.0570 0.9681 0.5780 0.035 Uiso 1 1 calc R U . . .
C4 C 0.77531(9) 0.93536(10) 0.54334(8) 0.0264(3) Uani 1 1 d . . . . .
H4 H 0.7629 0.9636 0.5847 0.032 Uiso 1 1 calc R U . . .
C66 C 1.64089(10) 0.87927(10) -0.05834(8) 0.0277(3) Uani 1 1 d . . . . .
H66 H 1.6462 0.8967 -0.1046 0.033 Uiso 1 1 calc R U . . .
C3 C 0.72770(9) 0.94547(10) 0.48578(8) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.6825 0.9808 0.4879 0.034 Uiso 1 1 calc R U . . .
C38 C 1.46768(11) 0.83924(10) 0.45387(8) 0.0308(4) Uani 1 1 d . . . . .
H38 H 1.4897 0.8567 0.4964 0.037 Uiso 1 1 calc R U . . .
C67 C 1.68962(9) 0.81742(10) -0.03195(8) 0.0286(3) Uani 1 1 d . . . . .
H67 H 1.7286 0.7924 -0.0602 0.034 Uiso 1 1 calc R U . . .
C18 C 1.01945(10) 0.81561(10) 0.13326(8) 0.0273(3) Uani 1 1 d . . . . .
H18 H 1.0754 0.8166 0.1280 0.033 Uiso 1 1 calc R U . . .
C33 C 1.19138(10) 0.82360(10) 0.56786(8) 0.0286(3) Uani 1 1 d . . . . .
H33 H 1.2299 0.7951 0.5948 0.034 Uiso 1 1 calc R U . . .
C39 C 1.51701(10) 0.81035(9) 0.40252(8) 0.0283(3) Uani 1 1 d . . . . .
H39 H 1.5728 0.8087 0.4098 0.034 Uiso 1 1 calc R U . . .
C17 C 0.97042(10) 0.83730(10) 0.07886(8) 0.0285(3) Uani 1 1 d . . . . .
H17 H 0.9928 0.8523 0.0361 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
O1 C27 1.2137(17) . ?
O2 C7 1.2008(16) . ?
O3 C55 1.2144(17) . ?
O4 C47 1.2020(17) . ?
N8 C54 1.4085(17) . ?
N8 C55 1.3670(17) . ?
N8 C62 1.4632(17) . ?
N6 N5 1.3756(15) . ?
N6 C41 1.4577(17) . ?
N6 C42 1.3720(17) . ?
N3 C1 1.4168(17) . ?
N3 C7 1.3734(17) . ?
N3 C20 1.4700(16) . ?
N7 C56 1.4143(17) . ?
N7 C47 1.3717(17) . ?
N7 C48 1.4707(16) . ?
N2 N1 1.3771(15) . ?
N2 C12 1.3711(17) . ?
N2 C8 1.4586(17) . ?
N5 C45 1.3316(18) . ?
N4 C26 1.4071(17) . ?
N4 C27 1.3664(17) . ?
N4 C28 1.4657(17) . ?
N1 C9 1.3312(18) . ?
C26 C21 1.4014(18) . ?
C26 C25 1.3836(19) . ?
C1 C6 1.3911(19) . ?
C1 C2 1.3939(19) . ?
C56 C57 1.3964(19) . ?
C56 C61 1.3923(19) . ?
C12 C11 1.3706(19) . ?
C12 C13 1.4939(18) . ?
C27 C20 1.5464(18) . ?
C7 C8 1.5588(18) . ?
C21 C22 1.3841(19) . ?
C21 C20 1.4983(18) . ?
C49 C54 1.4005(18) . ?
C49 C48 1.5008(18) . ?
C49 C50 1.3837(19) . ?
C47 C41 1.5612(18) . ?
C41 C35 1.5177(18) . ?
C41 C48 1.6092(18) . ?
C35 C36 1.396(2) . ?
C35 C40 1.391(2) . ?
C54 C53 1.3810(19) . ?
C42 C44 1.3701(19) . ?
C42 C43 1.4939(18) . ?
C44 H44 0.9500 . ?
C44 C45 1.4065(19) . ?
C48 C55 1.5425(18) . ?
C45 C46 1.4955(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.3985(19) . ?
C20 C8 1.6117(17) . ?
C9 C11 1.4073(19) . ?
C9 C10 1.4967(18) . ?
C63 C62 1.517(2) . ?
C63 C64 1.396(2) . ?
C63 C68 1.391(2) . ?
C14 C8 1.5146(18) . ?
C14 C15 1.3983(19) . ?
C14 C19 1.389(2) . ?
C29 C30 1.393(2) . ?
C29 C28 1.5140(19) . ?
C29 C34 1.386(2) . ?
C57 H57 0.9500 . ?
C57 C58 1.387(2) . ?
C11 H11 0.9500 . ?
C52 H52 0.9500 . ?
C52 C53 1.394(2) . ?
C52 C51 1.389(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(2) . ?
C24 C23 1.388(2) . ?
C61 H61 0.9500 . ?
C61 C60 1.389(2) . ?
C53 H53 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(2) . ?
C50 H50 0.9500 . ?
C50 C51 1.3997(19) . ?
C51 H51 0.9500 . ?
C25 H25 0.9500 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C36 H36 0.9500 . ?
C36 C37 1.392(2) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C23 H23 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.391(2) . ?
C64 H64 0.9500 . ?
C64 C65 1.386(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.391(2) . ?
C59 H59 0.9500 . ?
C59 C60 1.384(2) . ?
C59 C58 1.390(2) . ?
C60 H60 0.9500 . ?
C58 H58 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.385(2) . ?
C40 H40 0.9500 . ?
C40 C39 1.393(2) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C30 H30 0.9500 . ?
C30 C31 1.384(2) . ?
C68 H68 0.9500 . ?
C68 C67 1.390(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C34 H34 0.9500 . ?
C34 C33 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.380(2) . ?
C32 H32 0.9500 . ?
C32 C31 1.382(2) . ?
C32 C33 1.380(2) . ?
C65 H65 0.9500 . ?
C65 C66 1.387(2) . ?
C31 H31 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.385(2) . ?
C66 H66 0.9500 . ?
C66 C67 1.385(2) . ?
C3 H3 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.387(2) . ?
C67 H67 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.385(2) . ?
C33 H33 0.9500 . ?
C39 H39 0.9500 . ?
C17 H17 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
C54 N8 C62 124.53(11) . . ?
C55 N8 C54 111.15(11) . . ?
C55 N8 C62 123.78(11) . . ?
N5 N6 C41 118.25(10) . . ?
C42 N6 N5 111.88(11) . . ?
C42 N6 C41 129.74(11) . . ?
C1 N3 C20 128.76(11) . . ?
C7 N3 C1 131.86(11) . . ?
C7 N3 C20 96.24(10) . . ?
C56 N7 C48 128.78(11) . . ?
C47 N7 C56 132.67(11) . . ?
C47 N7 C48 96.53(10) . . ?
N1 N2 C8 118.19(10) . . ?
C12 N2 N1 111.77(11) . . ?
C12 N2 C8 130.00(11) . . ?
C45 N5 N6 104.70(11) . . ?
C26 N4 C28 124.37(11) . . ?
C27 N4 C26 111.32(11) . . ?
C27 N4 C28 123.88(12) . . ?
C9 N1 N2 104.69(11) . . ?
C21 C26 N4 110.14(11) . . ?
C25 C26 N4 127.69(12) . . ?
C25 C26 C21 122.13(13) . . ?
C6 C1 N3 119.60(12) . . ?
C6 C1 C2 120.43(13) . . ?
C2 C1 N3 119.95(12) . . ?
C57 C56 N7 120.44(12) . . ?
C61 C56 N7 119.11(12) . . ?
C61 C56 C57 120.43(13) . . ?
N2 C12 C13 125.28(12) . . ?
C11 C12 N2 106.01(12) . . ?
C11 C12 C13 128.66(13) . . ?
O1 C27 N4 127.19(13) . . ?
O1 C27 C20 125.80(12) . . ?
N4 C27 C20 106.99(11) . . ?
O2 C7 N3 132.52(13) . . ?
O2 C7 C8 135.20(12) . . ?
N3 C7 C8 92.16(10) . . ?
C26 C21 C20 107.46(11) . . ?
C22 C21 C26 120.08(12) . . ?
C22 C21 C20 131.83(12) . . ?
C54 C49 C48 107.50(11) . . ?
C50 C49 C54 120.14(12) . . ?
C50 C49 C48 131.96(12) . . ?
O4 C47 N7 132.37(13) . . ?
O4 C47 C41 135.41(12) . . ?
N7 C47 C41 92.12(10) . . ?
N6 C41 C47 109.78(10) . . ?
N6 C41 C35 111.18(11) . . ?
N6 C41 C48 112.72(10) . . ?
C47 C41 C48 84.02(9) . . ?
C35 C41 C47 115.69(11) . . ?
C35 C41 C48 120.61(11) . . ?
C36 C35 C41 116.70(12) . . ?
C40 C35 C41 123.84(13) . . ?
C40 C35 C36 119.28(13) . . ?
C49 C54 N8 110.19(11) . . ?
C53 C54 N8 127.52(12) . . ?
C53 C54 C49 122.25(12) . . ?
N6 C42 C43 125.38(12) . . ?
C44 C42 N6 105.79(12) . . ?
C44 C42 C43 128.75(12) . . ?
C42 C44 H44 126.7 . . ?
C42 C44 C45 106.52(12) . . ?
C45 C44 H44 126.7 . . ?
N7 C48 C49 122.43(11) . . ?
N7 C48 C41 86.67(9) . . ?
N7 C48 C55 110.97(10) . . ?
C49 C48 C41 118.30(11) . . ?
C49 C48 C55 103.22(10) . . ?
C55 C48 C41 115.46(10) . . ?
N5 C45 C44 111.09(12) . . ?
N5 C45 C46 121.00(12) . . ?
C44 C45 C46 127.91(13) . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C23 118.36(12) . . ?
C23 C22 H22 120.8 . . ?
O3 C55 N8 127.02(13) . . ?
O3 C55 C48 125.77(12) . . ?
N8 C55 C48 107.20(11) . . ?
N3 C20 C27 110.60(11) . . ?
N3 C20 C21 123.59(11) . . ?
N3 C20 C8 86.60(9) . . ?
C27 C20 C8 115.39(10) . . ?
C21 C20 C27 103.24(10) . . ?
C21 C20 C8 117.62(11) . . ?
N1 C9 C11 111.21(12) . . ?
N1 C9 C10 120.76(12) . . ?
C11 C9 C10 128.03(13) . . ?
C64 C63 C62 119.74(13) . . ?
C68 C63 C62 121.40(13) . . ?
C68 C63 C64 118.86(13) . . ?
C15 C14 C8 116.49(12) . . ?
C19 C14 C8 124.05(12) . . ?
C19 C14 C15 119.25(13) . . ?
C30 C29 C28 119.89(13) . . ?
C34 C29 C30 118.73(13) . . ?
C34 C29 C28 121.38(13) . . ?
N2 C8 C7 109.34(10) . . ?
N2 C8 C20 112.86(10) . . ?
N2 C8 C14 110.77(10) . . ?
C7 C8 C20 83.82(9) . . ?
C14 C8 C7 116.49(11) . . ?
C14 C8 C20 120.77(11) . . ?
C56 C57 H57 120.6 . . ?
C58 C57 C56 118.87(13) . . ?
C58 C57 H57 120.6 . . ?
C12 C11 C9 106.32(12) . . ?
C12 C11 H11 126.8 . . ?
C9 C11 H11 126.8 . . ?
C53 C52 H52 119.3 . . ?
C51 C52 H52 119.3 . . ?
C51 C52 C53 121.38(13) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C23 C24 C25 121.59(13) . . ?
C56 C61 H61 120.2 . . ?
C60 C61 C56 119.63(13) . . ?
C60 C61 H61 120.2 . . ?
C54 C53 C52 117.17(12) . . ?
C54 C53 H53 121.4 . . ?
C52 C53 H53 121.4 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.32(14) . . ?
C16 C15 H15 119.8 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.45(13) . . ?
C5 C6 H6 120.3 . . ?
C49 C50 H50 120.9 . . ?
C49 C50 C51 118.21(12) . . ?
C51 C50 H50 120.9 . . ?
C52 C51 C50 120.82(13) . . ?
C52 C51 H51 119.6 . . ?
C50 C51 H51 119.6 . . ?
C26 C25 C24 117.12(12) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
N8 C62 C63 111.80(11) . . ?
N8 C62 H62A 109.3 . . ?
N8 C62 H62B 109.3 . . ?
C63 C62 H62A 109.3 . . ?
C63 C62 H62B 109.3 . . ?
H62A C62 H62B 107.9 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.34(15) . . ?
C37 C36 H36 119.8 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.69(13) . . ?
C24 C23 H23 119.7 . . ?
C14 C19 H19 119.9 . . ?
C14 C19 C18 120.19(14) . . ?
C18 C19 H19 119.9 . . ?
C63 C64 H64 119.7 . . ?
C65 C64 C63 120.56(14) . . ?
C65 C64 H64 119.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.14(13) . . ?
C3 C2 H2 120.4 . . ?
C60 C59 H59 120.3 . . ?
C60 C59 C58 119.40(13) . . ?
C58 C59 H59 120.3 . . ?
C61 C60 H60 119.7 . . ?
C59 C60 C61 120.52(13) . . ?
C59 C60 H60 119.7 . . ?
C57 C58 C59 121.15(14) . . ?
C57 C58 H58 119.4 . . ?
C59 C58 H58 119.4 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.64(14) . . ?
C4 C5 H5 119.7 . . ?
C35 C40 H40 120.0 . . ?
C35 C40 C39 120.08(15) . . ?
C39 C40 H40 120.0 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.81(14) . . ?
C31 C30 H30 119.6 . . ?
C63 C68 H68 119.8 . . ?
C67 C68 C63 120.36(14) . . ?
C67 C68 H68 119.8 . . ?
N4 C28 C29 111.86(11) . . ?
N4 C28 H28A 109.2 . . ?
N4 C28 H28B 109.2 . . ?
C29 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C29 C34 H34 119.8 . . ?
C29 C34 C33 120.38(14) . . ?
C33 C34 H34 119.8 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.99(14) . . ?
C17 C16 H16 120.0 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.01(15) . . ?
C38 C37 H37 120.0 . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C33 C32 C31 119.81(14) . . ?
C64 C65 H65 119.9 . . ?
C64 C65 C66 120.27(14) . . ?
C66 C65 H65 119.9 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 119.99(14) . . ?
C32 C31 H31 120.0 . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.47(14) . . ?
C3 C4 H4 120.3 . . ?
C65 C66 H66 120.2 . . ?
C67 C66 C65 119.51(14) . . ?
C67 C66 H66 120.2 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.88(14) . . ?
C4 C3 H3 119.6 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.13(14) . . ?
C39 C38 H38 119.9 . . ?
C68 C67 H67 119.8 . . ?
C66 C67 C68 120.44(14) . . ?
C66 C67 H67 119.8 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.11(15) . . ?
C17 C18 H18 119.9 . . ?
C34 C33 H33 119.9 . . ?
C32 C33 C34 120.28(14) . . ?
C32 C33 H33 119.9 . . ?
C40 C39 H39 119.9 . . ?
C38 C39 C40 120.15(15) . . ?
C38 C39 H39 119.9 . . ?
C16 C17 C18 120.12(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 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
O1 C27 C20 N3 -36.15(18) . . . . ?
O1 C27 C20 C21 -170.23(13) . . . . ?
O1 C27 C20 C8 60.07(17) . . . . ?
O2 C7 C8 N2 -79.62(19) . . . . ?
O2 C7 C8 C20 168.28(16) . . . . ?
O2 C7 C8 C14 46.9(2) . . . . ?
O4 C47 C41 N6 77.56(19) . . . . ?
O4 C47 C41 C35 -49.2(2) . . . . ?
O4 C47 C41 C48 -170.42(16) . . . . ?
N8 C54 C53 C52 177.13(12) . . . . ?
N6 N5 C45 C44 -0.59(14) . . . . ?
N6 N5 C45 C46 179.78(12) . . . . ?
N6 C41 C35 C36 -76.73(15) . . . . ?
N6 C41 C35 C40 98.31(15) . . . . ?
N6 C41 C48 N7 103.32(11) . . . . ?
N6 C41 C48 C49 -22.05(16) . . . . ?
N6 C41 C48 C55 -145.01(11) . . . . ?
N6 C42 C44 C45 0.46(15) . . . . ?
N3 C1 C6 C5 -178.09(13) . . . . ?
N3 C1 C2 C3 178.04(14) . . . . ?
N3 C7 C8 N2 104.10(11) . . . . ?
N3 C7 C8 C20 -7.99(9) . . . . ?
N3 C7 C8 C14 -129.40(11) . . . . ?
N3 C20 C8 N2 -100.94(11) . . . . ?
N3 C20 C8 C7 7.47(9) . . . . ?
N3 C20 C8 C14 124.71(12) . . . . ?
N7 C56 C57 C58 -178.40(13) . . . . ?
N7 C56 C61 C60 178.11(12) . . . . ?
N7 C47 C41 N6 -105.97(11) . . . . ?
N7 C47 C41 C35 127.23(12) . . . . ?
N7 C47 C41 C48 6.05(9) . . . . ?
N7 C48 C55 O3 37.70(18) . . . . ?
N7 C48 C55 N8 -141.07(11) . . . . ?
N2 N1 C9 C11 0.71(14) . . . . ?
N2 N1 C9 C10 -179.21(11) . . . . ?
N2 C12 C11 C9 -0.05(15) . . . . ?
N5 N6 C41 C47 -3.89(15) . . . . ?
N5 N6 C41 C35 125.40(12) . . . . ?
N5 N6 C41 C48 -95.64(13) . . . . ?
N5 N6 C42 C44 -0.87(15) . . . . ?
N5 N6 C42 C43 176.18(12) . . . . ?
N4 C26 C21 C22 178.87(11) . . . . ?
N4 C26 C21 C20 6.94(14) . . . . ?
N4 C26 C25 C24 -177.03(12) . . . . ?
N4 C27 C20 N3 142.40(11) . . . . ?
N4 C27 C20 C21 8.33(13) . . . . ?
N4 C27 C20 C8 -121.38(11) . . . . ?
N1 N2 C12 C11 0.50(15) . . . . ?
N1 N2 C12 C13 -177.09(12) . . . . ?
N1 N2 C8 C7 2.70(15) . . . . ?
N1 N2 C8 C20 94.09(13) . . . . ?
N1 N2 C8 C14 -126.99(12) . . . . ?
N1 C9 C11 C12 -0.42(16) . . . . ?
C26 N4 C27 O1 173.93(13) . . . . ?
C26 N4 C27 C20 -4.60(14) . . . . ?
C26 N4 C28 C29 -73.94(16) . . . . ?
C26 C21 C22 C23 -1.36(19) . . . . ?
C26 C21 C20 N3 -135.27(12) . . . . ?
C26 C21 C20 C27 -9.10(13) . . . . ?
C26 C21 C20 C8 119.23(12) . . . . ?
C1 N3 C7 O2 -7.0(3) . . . . ?
C1 N3 C7 C8 169.46(13) . . . . ?
C1 N3 C20 C27 -54.18(17) . . . . ?
C1 N3 C20 C21 68.72(18) . . . . ?
C1 N3 C20 C8 -170.07(13) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C56 N7 C47 O4 5.7(3) . . . . ?
C56 N7 C47 C41 -170.99(13) . . . . ?
C56 N7 C48 C49 -66.58(18) . . . . ?
C56 N7 C48 C41 171.71(13) . . . . ?
C56 N7 C48 C55 55.68(17) . . . . ?
C56 C57 C58 C59 0.4(2) . . . . ?
C56 C61 C60 C59 0.3(2) . . . . ?
C12 N2 N1 C9 -0.75(14) . . . . ?
C12 N2 C8 C7 -174.68(12) . . . . ?
C12 N2 C8 C20 -83.30(16) . . . . ?
C12 N2 C8 C14 55.62(17) . . . . ?
C27 N4 C26 C21 -1.39(15) . . . . ?
C27 N4 C26 C25 176.28(13) . . . . ?
C27 N4 C28 C29 97.84(15) . . . . ?
C27 C20 C8 N2 147.84(11) . . . . ?
C27 C20 C8 C7 -103.75(11) . . . . ?
C27 C20 C8 C14 13.49(17) . . . . ?
C7 N3 C1 C6 -173.19(13) . . . . ?
C7 N3 C1 C2 8.4(2) . . . . ?
C7 N3 C20 C27 107.40(11) . . . . ?
C7 N3 C20 C21 -129.70(13) . . . . ?
C7 N3 C20 C8 -8.49(10) . . . . ?
C21 C26 C25 C24 0.39(19) . . . . ?
C21 C22 C23 C24 0.3(2) . . . . ?
C21 C20 C8 N2 25.53(15) . . . . ?
C21 C20 C8 C7 133.95(11) . . . . ?
C21 C20 C8 C14 -108.82(14) . . . . ?
C49 C54 C53 C52 -0.5(2) . . . . ?
C49 C48 C55 O3 170.55(13) . . . . ?
C49 C48 C55 N8 -8.22(13) . . . . ?
C49 C50 C51 C52 -0.1(2) . . . . ?
C47 N7 C56 C57 -5.9(2) . . . . ?
C47 N7 C56 C61 175.48(13) . . . . ?
C47 N7 C48 C49 128.15(13) . . . . ?
C47 N7 C48 C41 6.44(10) . . . . ?
C47 N7 C48 C55 -109.59(11) . . . . ?
C47 C41 C35 C36 49.36(16) . . . . ?
C47 C41 C35 C40 -135.60(14) . . . . ?
C47 C41 C48 N7 -5.65(9) . . . . ?
C47 C41 C48 C49 -131.01(12) . . . . ?
C47 C41 C48 C55 106.03(11) . . . . ?
C41 N6 N5 C45 177.18(11) . . . . ?
C41 N6 C42 C44 -176.59(12) . . . . ?
C41 N6 C42 C43 0.5(2) . . . . ?
C41 C35 C36 C37 174.25(13) . . . . ?
C41 C35 C40 C39 -173.66(13) . . . . ?
C41 C48 C55 O3 -58.82(17) . . . . ?
C41 C48 C55 N8 122.41(12) . . . . ?
C35 C41 C48 N7 -122.03(12) . . . . ?
C35 C41 C48 C49 112.60(14) . . . . ?
C35 C41 C48 C55 -10.36(17) . . . . ?
C35 C36 C37 C38 -0.1(2) . . . . ?
C35 C40 C39 C38 -0.4(2) . . . . ?
C54 N8 C55 O3 -173.35(13) . . . . ?
C54 N8 C55 C48 5.40(14) . . . . ?
C54 N8 C62 C63 77.63(16) . . . . ?
C54 C49 C48 N7 133.93(12) . . . . ?
C54 C49 C48 C41 -120.76(12) . . . . ?
C54 C49 C48 C55 8.14(13) . . . . ?
C54 C49 C50 C51 1.33(19) . . . . ?
C42 N6 N5 C45 0.91(14) . . . . ?
C42 N6 C41 C47 171.60(12) . . . . ?
C42 N6 C41 C35 -59.10(17) . . . . ?
C42 N6 C41 C48 79.86(16) . . . . ?
C42 C44 C45 N5 0.09(16) . . . . ?
C42 C44 C45 C46 179.68(13) . . . . ?
C48 N7 C56 C57 -165.86(13) . . . . ?
C48 N7 C56 C61 15.6(2) . . . . ?
C48 N7 C47 O4 170.02(15) . . . . ?
C48 N7 C47 C41 -6.63(10) . . . . ?
C48 C49 C54 N8 -5.44(14) . . . . ?
C48 C49 C54 C53 172.53(12) . . . . ?
C48 C49 C50 C51 -170.44(13) . . . . ?
C48 C41 C35 C36 148.00(12) . . . . ?
C48 C41 C35 C40 -36.97(19) . . . . ?
C22 C21 C20 N3 54.1(2) . . . . ?
C22 C21 C20 C27 -179.72(13) . . . . ?
C22 C21 C20 C8 -51.39(19) . . . . ?
C55 N8 C54 C49 -0.08(15) . . . . ?
C55 N8 C54 C53 -177.91(13) . . . . ?
C55 N8 C62 C63 -93.23(15) . . . . ?
C20 N3 C1 C6 -18.1(2) . . . . ?
C20 N3 C1 C2 163.43(13) . . . . ?
C20 N3 C7 O2 -167.67(15) . . . . ?
C20 N3 C7 C8 8.77(10) . . . . ?
C20 C21 C22 C23 168.29(13) . . . . ?
C63 C64 C65 C66 -0.9(2) . . . . ?
C63 C68 C67 C66 -0.7(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C14 C19 C18 C17 0.5(2) . . . . ?
C29 C30 C31 C32 0.2(2) . . . . ?
C29 C34 C33 C32 0.3(2) . . . . ?
C8 N2 N1 C9 -178.60(11) . . . . ?
C8 N2 C12 C11 178.02(12) . . . . ?
C8 N2 C12 C13 0.4(2) . . . . ?
C8 C14 C15 C16 -174.08(13) . . . . ?
C8 C14 C19 C18 173.16(13) . . . . ?
C57 C56 C61 C60 -0.5(2) . . . . ?
C61 C56 C57 C58 0.2(2) . . . . ?
C53 C52 C51 C50 -1.5(2) . . . . ?
C15 C14 C8 N2 73.23(15) . . . . ?
C15 C14 C8 C7 -52.56(16) . . . . ?
C15 C14 C8 C20 -151.58(12) . . . . ?
C15 C14 C19 C18 -1.3(2) . . . . ?
C15 C16 C17 C18 -1.5(2) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?
C50 C49 C54 N8 -179.03(11) . . . . ?
C50 C49 C54 C53 -1.1(2) . . . . ?
C50 C49 C48 N7 -53.5(2) . . . . ?
C50 C49 C48 C41 51.78(19) . . . . ?
C50 C49 C48 C55 -179.32(14) . . . . ?
C51 C52 C53 C54 1.7(2) . . . . ?
C25 C26 C21 C22 1.0(2) . . . . ?
C25 C26 C21 C20 -170.89(12) . . . . ?
C25 C24 C23 C22 1.2(2) . . . . ?
C62 N8 C54 C49 -171.94(12) . . . . ?
C62 N8 C54 C53 10.2(2) . . . . ?
C62 N8 C55 O3 -1.4(2) . . . . ?
C62 N8 C55 C48 177.34(11) . . . . ?
C62 C63 C64 C65 -179.78(13) . . . . ?
C62 C63 C68 C67 -179.45(13) . . . . ?
C36 C35 C40 C39 1.3(2) . . . . ?
C36 C37 C38 C39 1.0(2) . . . . ?
C23 C24 C25 C26 -1.5(2) . . . . ?
C19 C14 C8 N2 -101.42(15) . . . . ?
C19 C14 C8 C7 132.79(14) . . . . ?
C19 C14 C8 C20 33.77(19) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C19 C18 C17 C16 0.9(2) . . . . ?
C64 C63 C62 N8 61.26(17) . . . . ?
C64 C63 C68 C67 0.5(2) . . . . ?
C64 C65 C66 C67 0.7(2) . . . . ?
C10 C9 C11 C12 179.49(13) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C60 C59 C58 C57 -0.6(2) . . . . ?
C58 C59 C60 C61 0.2(2) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
C40 C35 C36 C37 -1.0(2) . . . . ?
C43 C42 C44 C45 -176.45(13) . . . . ?
C13 C12 C11 C9 177.43(13) . . . . ?
C30 C29 C28 N4 -66.96(17) . . . . ?
C30 C29 C34 C33 -0.3(2) . . . . ?
C68 C63 C62 N8 -118.78(14) . . . . ?
C68 C63 C64 C65 0.3(2) . . . . ?
C28 N4 C26 C21 171.29(12) . . . . ?
C28 N4 C26 C25 -11.0(2) . . . . ?
C28 N4 C27 O1 1.2(2) . . . . ?
C28 N4 C27 C20 -177.32(11) . . . . ?
C28 C29 C30 C31 -179.73(14) . . . . ?
C28 C29 C34 C33 179.48(14) . . . . ?
C34 C29 C30 C31 0.1(2) . . . . ?
C34 C29 C28 N4 113.25(15) . . . . ?
C37 C38 C39 C40 -0.8(2) . . . . ?
C65 C66 C67 C68 0.1(2) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C33 C32 C31 C30 -0.2(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 1.466
_oxdiff_exptl_absorpt_empirical_full_min 0.778
