# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_exp_172
_database_code_depnum_ccdc_archive 'CCDC 2001015'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H29 N3 O2'
_chemical_formula_sum            'C36 H29 N3 O2'
_chemical_formula_weight         535.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_IT_number           14
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'

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

_cell_length_a                   16.3716(10)
_cell_length_b                   10.5483(7)
_cell_length_c                   16.5348(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.462(8)
_cell_angle_gamma                90.00
_cell_volume                     2837.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2148
_cell_measurement_theta_min      3.4780
_cell_measurement_theta_max      29.1430

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_min  0.78933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.5253
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15450
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         30.98
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0281939000
_diffrn_orient_matrix_UB_12      0.0409939000
_diffrn_orient_matrix_UB_13      0.0227808000
_diffrn_orient_matrix_UB_21      0.0295888000
_diffrn_orient_matrix_UB_22      -0.0493061000
_diffrn_orient_matrix_UB_23      0.0040787000
_diffrn_orient_matrix_UB_31      0.0151093000
_diffrn_orient_matrix_UB_32      0.0201099000
_diffrn_orient_matrix_UB_33      -0.0365074000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  59.00   1.00  100.00    --   22.21-101.00  77.00   33
  2  ω    -23.00   4.00   1.00  100.00    --   22.21-101.00  77.00   27
  3  ω     38.00  87.00   1.00  100.00    --   22.21 178.00  30.00   49
  4  ω     -4.00  87.00   1.00  100.00    --   22.21  77.00-180.00   91
  5  ω    -95.00 -41.00   1.00  100.00    --  -23.92-178.00 -90.00   54
;
_reflns_number_total             7609
_reflns_number_gt                3522
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7609
_refine_ls_number_parameters     408
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1815
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.27944(10) 0.44619(15) 0.26751(12) 0.0473(5) Uani 1 1 d . . .
O1 O 0.37372(10) 0.87820(14) 0.38551(11) 0.0613(5) Uani 1 1 d . . .
C1 C 0.34113(12) 0.65729(17) 0.23672(13) 0.0414(5) Uani 1 1 d . . .
C2 C 0.27128(12) 0.56176(18) 0.23968(13) 0.0415(5) Uani 1 1 d . . .
O2 O 0.24016(11) 0.93339(15) 0.44169(12) 0.0723(5) Uani 1 1 d . . .
N3 N 0.40501(9) 0.61108(15) 0.18813(11) 0.0442(4) Uani 1 1 d . C .
C3 C 0.19398(12) 0.61828(18) 0.21119(14) 0.0450(5) Uani 1 1 d . . .
N4 N 0.12340(10) 0.55827(16) 0.21008(13) 0.0548(5) Uani 1 1 d . . .
C4 C 0.20848(13) 0.75013(18) 0.19065(14) 0.0466(5) Uani 1 1 d . . .
C5 C 0.12968(13) 0.4343(2) 0.23781(15) 0.0510(6) Uani 1 1 d . . .
C6 C 0.20650(12) 0.37903(19) 0.26668(14) 0.0464(5) Uani 1 1 d . . .
C7 C 0.05771(15) 0.3624(2) 0.24010(19) 0.0696(8) Uani 1 1 d . . .
H7A H 0.0070 0.3971 0.2208 0.084 Uiso 1 1 calc R . .
C8 C 0.06182(16) 0.2418(2) 0.27053(19) 0.0728(8) Uani 1 1 d . . .
H8A H 0.0137 0.1953 0.2719 0.087 Uiso 1 1 calc R . .
C9 C 0.13692(16) 0.1876(2) 0.29948(18) 0.0661(7) Uani 1 1 d . . .
H9A H 0.1386 0.1057 0.3204 0.079 Uiso 1 1 calc R . .
C10 C 0.20823(15) 0.25432(19) 0.29736(16) 0.0574(6) Uani 1 1 d . . .
H10A H 0.2583 0.2171 0.3163 0.069 Uiso 1 1 calc R . .
C11 C 0.15315(14) 0.8455(2) 0.16356(16) 0.0599(7) Uani 1 1 d . . .
H11A H 0.0972 0.8282 0.1534 0.072 Uiso 1 1 calc R . .
C12 C 0.18261(15) 0.9655(2) 0.15204(17) 0.0637(7) Uani 1 1 d . . .
H12A H 0.1462 1.0301 0.1345 0.076 Uiso 1 1 calc R . .
C13 C 0.26616(15) 0.9914(2) 0.16630(16) 0.0590(6) Uani 1 1 d . . .
H13A H 0.2852 1.0730 0.1583 0.071 Uiso 1 1 calc R . .
C14 C 0.32134(14) 0.89647(19) 0.19237(15) 0.0532(6) Uani 1 1 d . . .
H14A H 0.3773 0.9140 0.2015 0.064 Uiso 1 1 calc R . .
C15 C 0.29270(12) 0.77509(18) 0.20483(14) 0.0443(5) Uani 1 1 d . . .
C16 C 0.48839(12) 0.6305(2) 0.23088(14) 0.0472(5) Uani 1 1 d . C .
C17 C 0.47739(12) 0.71409(19) 0.30452(13) 0.0413(5) Uani 1 1 d . . .
C18 C 0.39067(12) 0.67598(19) 0.32314(14) 0.0416(5) Uani 1 1 d . . .
C19 C 0.34698(13) 0.76722(19) 0.37441(14) 0.0462(5) Uani 1 1 d . . .
C20 C 0.27258(14) 0.7269(2) 0.40364(15) 0.0508(6) Uani 1 1 d . . .
C21 C 0.21976(14) 0.8129(2) 0.43213(15) 0.0539(6) Uani 1 1 d . . .
C22 C 0.13581(14) 0.7797(2) 0.45153(16) 0.0597(6) Uani 1 1 d . . .
C23 C 0.09810(16) 0.6678(3) 0.42362(19) 0.0830(9) Uani 1 1 d . . .
H23A H 0.1255 0.6123 0.3923 0.100 Uiso 1 1 calc R . .
C24 C 0.01990(19) 0.6383(4) 0.4421(2) 0.1009(11) Uani 1 1 d . . .
H24A H -0.0050 0.5630 0.4232 0.121 Uiso 1 1 calc R . .
C25 C -0.02115(19) 0.7200(4) 0.4883(3) 0.1059(12) Uani 1 1 d . . .
H25A H -0.0738 0.7001 0.5004 0.127 Uiso 1 1 calc R . .
C26 C 0.0153(2) 0.8298(3) 0.5162(2) 0.0958(11) Uani 1 1 d . . .
H26A H -0.0124 0.8846 0.5478 0.115 Uiso 1 1 calc R . .
C27 C 0.09405(17) 0.8612(3) 0.49800(18) 0.0776(8) Uani 1 1 d . . .
H27A H 0.1184 0.9367 0.5171 0.093 Uiso 1 1 calc R . .
C28 C 0.40432(15) 0.6461(2) 0.10170(14) 0.0582(6) Uani 1 1 d . . .
H28A H 0.3840 0.7318 0.0921 0.070 Uiso 1 1 calc R A 1
H28B H 0.3702 0.5884 0.0670 0.070 Uiso 1 1 calc R A 1
C30 C 0.53949(16) 0.6804(3) 0.16628(17) 0.0707(7) Uani 1 1 d . . .
H30A H 0.5946 0.6454 0.1736 0.085 Uiso 1 1 calc R B 1
H30B H 0.5430 0.7722 0.1682 0.085 Uiso 1 1 calc R B 1
C31 C 0.54548(12) 0.70360(18) 0.37397(14) 0.0443(5) Uani 1 1 d . . .
C32 C 0.60482(14) 0.7970(2) 0.38635(18) 0.0594(7) Uani 1 1 d . . .
C33 C 0.66942(16) 0.7860(3) 0.4476(2) 0.0811(9) Uani 1 1 d . . .
H33A H 0.7087 0.8498 0.4551 0.097 Uiso 1 1 calc R . .
C34 C 0.67593(18) 0.6818(3) 0.49742(19) 0.0841(9) Uani 1 1 d . . .
H34A H 0.7190 0.6753 0.5389 0.101 Uiso 1 1 calc R . .
C35 C 0.61826(17) 0.5873(3) 0.48544(18) 0.0802(8) Uani 1 1 d . . .
H35A H 0.6227 0.5160 0.5188 0.096 Uiso 1 1 calc R . .
C36 C 0.55346(14) 0.5970(3) 0.42425(16) 0.0606(7) Uani 1 1 d . . .
H18 H 0.3920(11) 0.5911(17) 0.3475(12) 0.041(5) Uiso 1 1 d . . .
H17 H 0.4761(12) 0.8002(18) 0.2874(12) 0.043(5) Uiso 1 1 d . . .
H20 H 0.2592(12) 0.6400(18) 0.3982(12) 0.041(5) Uiso 1 1 d . . .
C29 C 0.4931(2) 0.6360(4) 0.0862(2) 0.0622(9) Uani 0.75 1 d PU C 1
H29A H 0.5045 0.6902 0.0415 0.075 Uiso 0.75 1 calc PR C 1
H29B H 0.5073 0.5493 0.0742 0.075 Uiso 0.75 1 calc PR C 1
C29A C 0.4814(7) 0.7280(10) 0.1010(8) 0.068(3) Uani 0.25 1 d PU C 2
H29C H 0.5035 0.7206 0.0492 0.082 Uiso 0.25 1 calc PR C 2
H29D H 0.4688 0.8164 0.1100 0.082 Uiso 0.25 1 calc PR C 2
H16 H 0.5113(12) 0.5400(19) 0.2498(13) 0.055(6) Uiso 1 1 d . . .
H32 H 0.5996(14) 0.875(2) 0.3496(15) 0.071(7) Uiso 1 1 d . . .
H36 H 0.5131(16) 0.529(2) 0.4158(16) 0.084(8) Uiso 1 1 d . . .
H2 H 0.301(2) 0.940(3) 0.419(2) 0.132(12) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.305(2) . ?
N1 C6 1.387(2) . ?
O1 C19 1.256(2) . ?
C1 N3 1.472(3) . ?
C1 C2 1.529(3) . ?
C1 C15 1.535(3) . ?
C1 C18 1.574(3) . ?
C2 C3 1.430(3) . ?
O2 C21 1.319(3) . ?
O2 H2 1.10(4) . ?
N3 C28 1.475(3) . ?
N3 C16 1.479(3) . ?
C3 N4 1.316(2) . ?
C3 C4 1.457(3) . ?
N4 C5 1.386(3) . ?
C4 C11 1.393(3) . ?
C4 C15 1.397(3) . ?
C5 C7 1.405(3) . ?
C5 C6 1.419(3) . ?
C6 C10 1.409(3) . ?
C7 C8 1.367(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.391(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.367(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.387(3) . ?
C14 H14A 0.9300 . ?
C16 C30 1.523(3) . ?
C16 C17 1.530(3) . ?
C16 H16 1.06(2) . ?
C17 C31 1.512(3) . ?
C17 C18 1.540(3) . ?
C17 H17 0.951(18) . ?
C18 C19 1.514(3) . ?
C18 H18 0.981(18) . ?
C19 C20 1.425(3) . ?
C20 C21 1.372(3) . ?
C20 H20 0.944(18) . ?
C21 C22 1.488(3) . ?
C22 C27 1.383(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.385(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.376(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.361(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.396(4) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C28 C29 1.507(4) . ?
C28 C29A 1.530(11) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 C29A 1.446(12) . ?
C30 C29 1.524(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.383(3) . ?
C31 C36 1.396(3) . ?
C32 C33 1.385(4) . ?
C32 H32 1.02(2) . ?
C33 C34 1.370(4) . ?
C33 H33A 0.9300 . ?
C34 C35 1.372(4) . ?
C34 H34A 0.9300 . ?
C35 C36 1.385(3) . ?
C35 H35A 0.9300 . ?
C36 H36 0.97(2) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29A H29C 0.9700 . ?
C29A H29D 0.9700 . ?

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
C2 N1 C6 114.82(17) . . ?
N3 C1 C2 112.28(15) . . ?
N3 C1 C15 116.86(17) . . ?
C2 C1 C15 100.68(15) . . ?
N3 C1 C18 102.23(15) . . ?
C2 C1 C18 111.37(17) . . ?
C15 C1 C18 113.82(16) . . ?
N1 C2 C3 123.89(18) . . ?
N1 C2 C1 125.43(17) . . ?
C3 C2 C1 110.61(16) . . ?
C21 O2 H2 104.2(16) . . ?
C1 N3 C28 121.16(17) . . ?
C1 N3 C16 111.56(16) . . ?
C28 N3 C16 109.53(17) . . ?
N4 C3 C2 123.18(19) . . ?
N4 C3 C4 128.43(18) . . ?
C2 C3 C4 108.27(17) . . ?
C3 N4 C5 114.64(18) . . ?
C11 C4 C15 120.76(19) . . ?
C11 C4 C3 130.29(19) . . ?
C15 C4 C3 108.92(17) . . ?
N4 C5 C7 119.1(2) . . ?
N4 C5 C6 121.93(18) . . ?
C7 C5 C6 118.9(2) . . ?
N1 C6 C10 119.39(19) . . ?
N1 C6 C5 121.52(18) . . ?
C10 C6 C5 119.06(19) . . ?
C8 C7 C5 120.4(2) . . ?
C8 C7 H7A 119.8 . . ?
C5 C7 H7A 119.8 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C6 120.5(2) . . ?
C9 C10 H10A 119.8 . . ?
C6 C10 H10A 119.8 . . ?
C12 C11 C4 118.9(2) . . ?
C12 C11 H11A 120.5 . . ?
C4 C11 H11A 120.5 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C14 C15 C4 119.52(18) . . ?
C14 C15 C1 128.92(18) . . ?
C4 C15 C1 111.52(16) . . ?
N3 C16 C30 105.25(19) . . ?
N3 C16 C17 105.97(16) . . ?
C30 C16 C17 118.83(19) . . ?
N3 C16 H16 107.1(11) . . ?
C30 C16 H16 108.3(11) . . ?
C17 C16 H16 110.7(12) . . ?
C31 C17 C16 114.80(16) . . ?
C31 C17 C18 116.53(18) . . ?
C16 C17 C18 101.69(16) . . ?
C31 C17 H17 106.6(12) . . ?
C16 C17 H17 108.3(12) . . ?
C18 C17 H17 108.6(12) . . ?
C19 C18 C17 116.77(17) . . ?
C19 C18 C1 111.11(16) . . ?
C17 C18 C1 104.10(16) . . ?
C19 C18 H18 109.9(11) . . ?
C17 C18 H18 110.0(11) . . ?
C1 C18 H18 104.1(11) . . ?
O1 C19 C20 121.7(2) . . ?
O1 C19 C18 119.69(19) . . ?
C20 C19 C18 118.42(19) . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 121.8(12) . . ?
C19 C20 H20 117.0(12) . . ?
O2 C21 C20 121.1(2) . . ?
O2 C21 C22 115.3(2) . . ?
C20 C21 C22 123.5(2) . . ?
C27 C22 C23 118.9(2) . . ?
C27 C22 C21 120.0(2) . . ?
C23 C22 C21 121.0(2) . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C27 120.6(3) . . ?
C25 C26 H26A 119.7 . . ?
C27 C26 H26A 119.7 . . ?
C22 C27 C26 119.9(3) . . ?
C22 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?
N3 C28 C29 104.1(2) . . ?
N3 C28 C29A 103.4(5) . . ?
C29 C28 C29A 39.4(4) . . ?
N3 C28 H28A 110.9 . . ?
C29 C28 H28A 110.9 . . ?
C29A C28 H28A 74.9 . . ?
N3 C28 H28B 110.9 . . ?
C29 C28 H28B 110.9 . . ?
C29A C28 H28B 140.4 . . ?
H28A C28 H28B 108.9 . . ?
C29A C30 C16 106.0(5) . . ?
C29A C30 C29 40.2(5) . . ?
C16 C30 C29 104.1(2) . . ?
C29A C30 H30A 138.6 . . ?
C16 C30 H30A 110.9 . . ?
C29 C30 H30A 110.9 . . ?
C29A C30 H30B 73.1 . . ?
C16 C30 H30B 110.9 . . ?
C29 C30 H30B 110.9 . . ?
H30A C30 H30B 109.0 . . ?
C32 C31 C36 118.0(2) . . ?
C32 C31 C17 120.4(2) . . ?
C36 C31 C17 121.53(19) . . ?
C31 C32 C33 120.9(3) . . ?
C31 C32 H32 118.5(13) . . ?
C33 C32 H32 120.5(14) . . ?
C34 C33 C32 120.6(3) . . ?
C34 C33 H33A 119.7 . . ?
C32 C33 H33A 119.7 . . ?
C33 C34 C35 119.4(3) . . ?
C33 C34 H34A 120.3 . . ?
C35 C34 H34A 120.3 . . ?
C34 C35 C36 120.7(3) . . ?
C34 C35 H35A 119.7 . . ?
C36 C35 H35A 119.7 . . ?
C35 C36 C31 120.5(3) . . ?
C35 C36 H36 120.2(16) . . ?
C31 C36 H36 119.4(16) . . ?
C28 C29 C30 103.1(2) . . ?
C28 C29 H29A 111.1 . . ?
C30 C29 H29A 111.1 . . ?
C28 C29 H29B 111.1 . . ?
C30 C29 H29B 111.1 . . ?
H29A C29 H29B 109.1 . . ?
C30 C29A C28 105.8(6) . . ?
C30 C29A H29C 110.6 . . ?
C28 C29A H29C 110.6 . . ?
C30 C29A H29D 110.6 . . ?
C28 C29A H29D 110.6 . . ?
H29C C29A H29D 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.9(3) . . . . ?
C6 N1 C2 C1 177.66(19) . . . . ?
N3 C1 C2 N1 59.0(3) . . . . ?
C15 C1 C2 N1 -175.9(2) . . . . ?
C18 C1 C2 N1 -54.9(3) . . . . ?
N3 C1 C2 C3 -123.79(19) . . . . ?
C15 C1 C2 C3 1.2(2) . . . . ?
C18 C1 C2 C3 122.25(19) . . . . ?
C2 C1 N3 C28 95.5(2) . . . . ?
C15 C1 N3 C28 -20.1(3) . . . . ?
C18 C1 N3 C28 -145.06(18) . . . . ?
C2 C1 N3 C16 -133.28(18) . . . . ?
C15 C1 N3 C16 111.1(2) . . . . ?
C18 C1 N3 C16 -13.8(2) . . . . ?
N1 C2 C3 N4 -0.3(4) . . . . ?
C1 C2 C3 N4 -177.5(2) . . . . ?
N1 C2 C3 C4 175.9(2) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 N4 C5 -0.9(3) . . . . ?
C4 C3 N4 C5 -176.3(2) . . . . ?
N4 C3 C4 C11 -1.3(4) . . . . ?
C2 C3 C4 C11 -177.2(2) . . . . ?
N4 C3 C4 C15 176.7(2) . . . . ?
C2 C3 C4 C15 0.8(3) . . . . ?
C3 N4 C5 C7 179.2(2) . . . . ?
C3 N4 C5 C6 1.4(3) . . . . ?
C2 N1 C6 C10 -178.4(2) . . . . ?
C2 N1 C6 C5 -0.3(3) . . . . ?
N4 C5 C6 N1 -0.9(4) . . . . ?
C7 C5 C6 N1 -178.7(2) . . . . ?
N4 C5 C6 C10 177.2(2) . . . . ?
C7 C5 C6 C10 -0.5(3) . . . . ?
N4 C5 C7 C8 -177.1(2) . . . . ?
C6 C5 C7 C8 0.7(4) . . . . ?
C5 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C6 0.7(4) . . . . ?
N1 C6 C10 C9 178.0(2) . . . . ?
C5 C6 C10 C9 -0.2(4) . . . . ?
C15 C4 C11 C12 -0.9(4) . . . . ?
C3 C4 C11 C12 176.9(2) . . . . ?
C4 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C4 0.2(3) . . . . ?
C13 C14 C15 C1 -177.1(2) . . . . ?
C11 C4 C15 C14 0.5(4) . . . . ?
C3 C4 C15 C14 -177.7(2) . . . . ?
C11 C4 C15 C1 178.3(2) . . . . ?
C3 C4 C15 C1 0.0(3) . . . . ?
N3 C1 C15 C14 -61.4(3) . . . . ?
C2 C1 C15 C14 176.7(2) . . . . ?
C18 C1 C15 C14 57.5(3) . . . . ?
N3 C1 C15 C4 121.1(2) . . . . ?
C2 C1 C15 C4 -0.8(2) . . . . ?
C18 C1 C15 C4 -120.0(2) . . . . ?
C1 N3 C16 C30 -136.60(18) . . . . ?
C28 N3 C16 C30 0.3(2) . . . . ?
C1 N3 C16 C17 -9.9(2) . . . . ?
C28 N3 C16 C17 127.05(18) . . . . ?
N3 C16 C17 C31 156.34(17) . . . . ?
C30 C16 C17 C31 -85.6(3) . . . . ?
N3 C16 C17 C18 29.6(2) . . . . ?
C30 C16 C17 C18 147.6(2) . . . . ?
C31 C17 C18 C19 73.6(2) . . . . ?
C16 C17 C18 C19 -160.80(18) . . . . ?
C31 C17 C18 C1 -163.53(16) . . . . ?
C16 C17 C18 C1 -37.93(19) . . . . ?
N3 C1 C18 C19 158.67(16) . . . . ?
C2 C1 C18 C19 -81.2(2) . . . . ?
C15 C1 C18 C19 31.7(2) . . . . ?
N3 C1 C18 C17 32.17(18) . . . . ?
C2 C1 C18 C17 152.27(16) . . . . ?
C15 C1 C18 C17 -94.77(18) . . . . ?
C17 C18 C19 O1 14.4(3) . . . . ?
C1 C18 C19 O1 -104.8(2) . . . . ?
C17 C18 C19 C20 -170.33(19) . . . . ?
C1 C18 C19 C20 70.5(2) . . . . ?
O1 C19 C20 C21 11.8(4) . . . . ?
C18 C19 C20 C21 -163.4(2) . . . . ?
C19 C20 C21 O2 -7.5(4) . . . . ?
C19 C20 C21 C22 170.4(2) . . . . ?
O2 C21 C22 C27 -17.9(4) . . . . ?
C20 C21 C22 C27 164.2(3) . . . . ?
O2 C21 C22 C23 162.0(2) . . . . ?
C20 C21 C22 C23 -15.9(4) . . . . ?
C27 C22 C23 C24 0.0(5) . . . . ?
C21 C22 C23 C24 -179.9(3) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C23 C24 C25 C26 -0.3(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C23 C22 C27 C26 0.2(4) . . . . ?
C21 C22 C27 C26 -179.9(3) . . . . ?
C25 C26 C27 C22 -0.4(5) . . . . ?
C1 N3 C28 C29 154.3(2) . . . . ?
C16 N3 C28 C29 22.2(3) . . . . ?
C1 N3 C28 C29A 113.7(5) . . . . ?
C16 N3 C28 C29A -18.4(5) . . . . ?
N3 C16 C30 C29A 19.2(6) . . . . ?
C17 C16 C30 C29A -99.2(6) . . . . ?
N3 C16 C30 C29 -22.5(3) . . . . ?
C17 C16 C30 C29 -140.9(2) . . . . ?
C16 C17 C31 C32 102.7(2) . . . . ?
C18 C17 C31 C32 -138.6(2) . . . . ?
C16 C17 C31 C36 -73.4(3) . . . . ?
C18 C17 C31 C36 45.3(3) . . . . ?
C36 C31 C32 C33 -1.0(4) . . . . ?
C17 C31 C32 C33 -177.3(2) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C32 C33 C34 C35 0.8(4) . . . . ?
C33 C34 C35 C36 -0.6(4) . . . . ?
C34 C35 C36 C31 -0.4(4) . . . . ?
C32 C31 C36 C35 1.2(4) . . . . ?
C17 C31 C36 C35 177.4(2) . . . . ?
N3 C28 C29 C30 -35.6(3) . . . . ?
C29A C28 C29 C30 58.5(7) . . . . ?
C29A C30 C29 C28 -62.5(7) . . . . ?
C16 C30 C29 C28 35.8(3) . . . . ?
C16 C30 C29A C28 -30.8(8) . . . . ?
C29 C30 C29A C28 62.2(6) . . . . ?
N3 C28 C29A C30 30.5(8) . . . . ?
C29 C28 C29A C30 -65.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 2001017'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H31 Cl2 N5'
_chemical_formula_sum            'C42 H31 Cl2 N5'
_chemical_formula_weight         676.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   18.8279(12)
_cell_length_b                   18.8070(12)
_cell_length_c                   19.2105(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6802.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3216
_cell_measurement_theta_min      3.5840
_cell_measurement_theta_max      24.8020

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_min  0.66647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.5253
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25280
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         30.93
_reflns_number_total             9078
_reflns_number_gt                3762
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9078
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.2153
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.01811(5) 0.32226(7) 0.03859(5) 0.1085(4) Uani 1 1 d . . .
Cl2 Cl -0.21575(6) 0.15146(5) 0.55593(5) 0.1014(4) Uani 1 1 d . . .
N1 N -0.15683(13) 0.41664(13) 0.48409(11) 0.0609(6) Uani 1 1 d . . .
N2 N -0.26072(12) 0.33476(12) 0.31135(11) 0.0517(5) Uani 1 1 d . . .
N3 N -0.31765(13) 0.31346(13) 0.27319(12) 0.0600(6) Uani 1 1 d . . .
N4 N -0.30251(14) 0.43015(13) 0.52625(12) 0.0642(7) Uani 1 1 d . . .
N5 N -0.12921(12) 0.53435(12) 0.38112(12) 0.0566(6) Uani 1 1 d . . .
C1 C -0.4897(3) 0.3401(4) 0.0757(2) 0.123(2) Uani 1 1 d . . .
H1A H -0.5274 0.3356 0.0449 0.148 Uiso 1 1 calc R . .
C2 C -0.27599(16) 0.45748(14) 0.46876(14) 0.0546(7) Uani 1 1 d . . .
C3 C -0.3966(2) 0.4105(2) 0.12719(17) 0.0939(12) Uani 1 1 d . . .
H3A H -0.3714 0.4529 0.1302 0.113 Uiso 1 1 calc R . .
C4 C -0.16996(14) 0.43320(14) 0.31986(13) 0.0469(6) Uani 1 1 d . . .
C5 C -0.0669(2) 0.60197(17) 0.29714(18) 0.0848(11) Uani 1 1 d . . .
H5A H -0.0173 0.6060 0.2841 0.102 Uiso 1 1 calc R . .
H5B H -0.0961 0.6165 0.2580 0.102 Uiso 1 1 calc R . .
C6 C -0.12767(15) 0.48118(14) 0.26943(13) 0.0492(6) Uani 1 1 d . . .
C7 C -0.22942(14) 0.39524(14) 0.28526(13) 0.0485(6) Uani 1 1 d . . .
C8 C -0.08757(14) 0.44286(14) 0.21292(13) 0.0509(6) Uani 1 1 d . . .
C9 C -0.0821(3) 0.6455(2) 0.3581(3) 0.135(2) Uani 1 1 d . . .
H9A H -0.0987 0.6921 0.3439 0.162 Uiso 1 1 calc R . .
H9B H -0.0395 0.6515 0.3858 0.162 Uiso 1 1 calc R . .
C10 C -0.26467(15) 0.52060(14) 0.36561(14) 0.0525(7) Uani 1 1 d . . .
C11 C -0.20400(15) 0.45098(14) 0.44785(13) 0.0504(7) Uani 1 1 d . . .
C12 C -0.19102(14) 0.48806(14) 0.37858(13) 0.0485(6) Uani 1 1 d . . .
C13 C -0.31381(15) 0.49806(15) 0.41538(14) 0.0534(7) Uani 1 1 d . . .
C14 C -0.4534(3) 0.4042(3) 0.0794(2) 0.1195(17) Uani 1 1 d . . .
H14A H -0.4661 0.4423 0.0511 0.143 Uiso 1 1 calc R . .
C15 C -0.32172(15) 0.36082(17) 0.22143(14) 0.0569(7) Uani 1 1 d . . .
C16 C -0.24578(15) 0.29446(13) 0.37266(13) 0.0493(6) Uani 1 1 d . . .
C17 C -0.28857(17) 0.24536(16) 0.47933(15) 0.0619(8) Uani 1 1 d . . .
H17A H -0.3242 0.2411 0.5126 0.074 Uiso 1 1 calc R . .
C18 C -0.29801(16) 0.28856(15) 0.42215(15) 0.0564(7) Uani 1 1 d . . .
H18A H -0.3401 0.3139 0.4171 0.068 Uiso 1 1 calc R . .
C19 C -0.08438(17) 0.52654(16) 0.31861(15) 0.0590(7) Uani 1 1 d . . .
C20 C -0.06331(18) 0.42596(19) 0.09093(15) 0.0722(9) Uani 1 1 d . . .
H20A H -0.0708 0.4393 0.0449 0.087 Uiso 1 1 calc R . .
C21 C -0.28868(16) 0.56209(16) 0.31090(15) 0.0628(8) Uani 1 1 d . . .
H21A H -0.2567 0.5790 0.2779 0.075 Uiso 1 1 calc R . .
C22 C -0.18279(18) 0.38644(15) 0.54451(14) 0.0601(8) Uani 1 1 d . . .
C23 C -0.26789(16) 0.41196(17) 0.22724(14) 0.0569(7) Uani 1 1 d . . .
C24 C -0.09658(15) 0.46175(17) 0.14453(14) 0.0616(8) Uani 1 1 d . . .
H24A H -0.1261 0.4999 0.1339 0.074 Uiso 1 1 calc R . .
C25 C -0.18271(16) 0.25877(16) 0.38066(16) 0.0632(8) Uani 1 1 d . . .
H25A H -0.1470 0.2633 0.3475 0.076 Uiso 1 1 calc R . .
C26 C -0.04099(16) 0.38793(16) 0.22690(14) 0.0641(8) Uani 1 1 d . . .
H26A H -0.0326 0.3750 0.2729 0.077 Uiso 1 1 calc R . .
C27 C -0.25398(19) 0.39279(15) 0.56547(15) 0.0627(8) Uani 1 1 d . . .
C28 C -0.1363(2) 0.3448(2) 0.58556(17) 0.0810(10) Uani 1 1 d . . .
H28A H -0.0888 0.3406 0.5731 0.097 Uiso 1 1 calc R . .
C29 C -0.37836(17) 0.3539(2) 0.16936(15) 0.0706(9) Uani 1 1 d . . .
C30 C -0.2773(2) 0.35810(18) 0.62577(17) 0.0789(10) Uani 1 1 d . . .
H30A H -0.3242 0.3630 0.6401 0.095 Uiso 1 1 calc R . .
C31 C -0.17265(18) 0.21589(16) 0.43848(18) 0.0708(9) Uani 1 1 d . . .
H31A H -0.1298 0.1920 0.4447 0.085 Uiso 1 1 calc R . .
C32 C -0.38564(17) 0.51301(18) 0.40897(17) 0.0699(9) Uani 1 1 d . . .
H32A H -0.4180 0.4966 0.4419 0.084 Uiso 1 1 calc R . .
C33 C -0.40801(19) 0.5525(2) 0.35306(19) 0.0802(10) Uani 1 1 d . . .
H33A H -0.4562 0.5620 0.3475 0.096 Uiso 1 1 calc R . .
C34 C -0.36014(18) 0.57843(18) 0.30513(19) 0.0758(9) Uani 1 1 d . . .
H34A H -0.3759 0.6070 0.2687 0.091 Uiso 1 1 calc R . .
C35 C -0.13722(18) 0.60916(16) 0.39910(18) 0.0713(9) Uani 1 1 d . . .
H35A H -0.1298 0.6166 0.4485 0.086 Uiso 1 1 calc R . .
H35B H -0.1841 0.6263 0.3867 0.086 Uiso 1 1 calc R . .
C36 C -0.22617(18) 0.20873(16) 0.48665(15) 0.0624(8) Uani 1 1 d . . .
C37 C -0.00641(18) 0.35161(18) 0.17390(17) 0.0735(9) Uani 1 1 d . . .
H37A H 0.0250 0.3149 0.1841 0.088 Uiso 1 1 calc R . .
C38 C -0.41620(17) 0.2907(2) 0.16305(18) 0.0817(11) Uani 1 1 d . . .
H38A H -0.4042 0.2522 0.1910 0.098 Uiso 1 1 calc R . .
C39 C -0.01930(16) 0.37079(19) 0.10673(16) 0.0669(8) Uani 1 1 d . . .
C40 C -0.2323(3) 0.3176(2) 0.66337(18) 0.0914(12) Uani 1 1 d . . .
H40A H -0.2486 0.2941 0.7028 0.110 Uiso 1 1 calc R . .
C41 C -0.1610(3) 0.3106(2) 0.64334(18) 0.0952(12) Uani 1 1 d . . .
H41A H -0.1304 0.2826 0.6696 0.114 Uiso 1 1 calc R . .
C42 C -0.4712(2) 0.2841(3) 0.1161(2) 0.1101(16) Uani 1 1 d . . .
H42A H -0.4955 0.2412 0.1122 0.132 Uiso 1 1 calc R . .
H4 H -0.1366(11) 0.3978(11) 0.3409(10) 0.028(5) Uiso 1 1 d . . .
H6 H -0.1628(12) 0.5099(12) 0.2465(11) 0.035(6) Uiso 1 1 d . . .
H23 H -0.2570(13) 0.4496(13) 0.1958(13) 0.051(7) Uiso 1 1 d . . .
H19 H -0.0400(16) 0.4996(14) 0.3332(14) 0.064(8) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C39 1.744(3) . ?
Cl2 C36 1.723(3) . ?
N1 C11 1.300(3) . ?
N1 C22 1.382(3) . ?
N2 N3 1.359(3) . ?
N2 C7 1.376(3) . ?
N2 C16 1.429(3) . ?
N3 C15 1.337(4) . ?
N4 C2 1.317(3) . ?
N4 C27 1.377(4) . ?
N5 C12 1.454(3) . ?
N5 C35 1.457(4) . ?
N5 C19 1.475(3) . ?
C1 C42 1.355(7) . ?
C1 C14 1.387(7) . ?
C1 H1A 0.9300 . ?
C2 C11 1.419(4) . ?
C2 C13 1.463(4) . ?
C3 C29 1.380(5) . ?
C3 C14 1.413(6) . ?
C3 H3A 0.9300 . ?
C4 C7 1.485(4) . ?
C4 C6 1.545(4) . ?
C4 C12 1.579(3) . ?
C4 H4 1.00(2) . ?
C5 C9 1.457(5) . ?
C5 C19 1.513(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.506(4) . ?
C6 C19 1.512(4) . ?
C6 H6 0.96(2) . ?
C7 C23 1.366(4) . ?
C8 C24 1.371(4) . ?
C8 C26 1.382(4) . ?
C9 C35 1.470(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C21 1.385(4) . ?
C10 C13 1.396(4) . ?
C10 C12 1.536(4) . ?
C11 C12 1.522(4) . ?
C13 C32 1.387(4) . ?
C14 H14A 0.9300 . ?
C15 C23 1.402(4) . ?
C15 C29 1.468(4) . ?
C16 C25 1.373(4) . ?
C16 C18 1.372(4) . ?
C17 C36 1.369(4) . ?
C17 C18 1.378(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19 1.02(3) . ?
C20 C39 1.362(4) . ?
C20 C24 1.381(4) . ?
C20 H20A 0.9300 . ?
C21 C34 1.385(4) . ?
C21 H21A 0.9300 . ?
C22 C27 1.405(4) . ?
C22 C28 1.415(4) . ?
C23 H23 0.95(2) . ?
C24 H24A 0.9300 . ?
C25 C31 1.386(4) . ?
C25 H25A 0.9300 . ?
C26 C37 1.388(4) . ?
C26 H26A 0.9300 . ?
C27 C30 1.400(4) . ?
C28 C41 1.364(5) . ?
C28 H28A 0.9300 . ?
C29 C38 1.392(5) . ?
C30 C40 1.350(5) . ?
C30 H30A 0.9300 . ?
C31 C36 1.375(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.372(5) . ?
C32 H32A 0.9300 . ?
C33 C34 1.377(5) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C37 C39 1.362(4) . ?
C37 H37A 0.9300 . ?
C38 C42 1.378(5) . ?
C38 H38A 0.9300 . ?
C40 C41 1.402(6) . ?
C40 H40A 0.9300 . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C22 114.4(3) . . ?
N3 N2 C7 112.6(2) . . ?
N3 N2 C16 116.3(2) . . ?
C7 N2 C16 130.9(2) . . ?
C15 N3 N2 104.5(2) . . ?
C2 N4 C27 114.0(3) . . ?
C12 N5 C35 120.2(2) . . ?
C12 N5 C19 111.8(2) . . ?
C35 N5 C19 110.4(2) . . ?
C42 C1 C14 121.3(4) . . ?
C42 C1 H1A 119.3 . . ?
C14 C1 H1A 119.3 . . ?
N4 C2 C11 124.5(3) . . ?
N4 C2 C13 127.4(3) . . ?
C11 C2 C13 108.1(2) . . ?
C29 C3 C14 120.4(5) . . ?
C29 C3 H3A 119.8 . . ?
C14 C3 H3A 119.8 . . ?
C7 C4 C6 112.9(2) . . ?
C7 C4 C12 116.4(2) . . ?
C6 C4 C12 101.29(19) . . ?
C7 C4 H4 109.6(12) . . ?
C6 C4 H4 108.5(12) . . ?
C12 C4 H4 107.7(12) . . ?
C9 C5 C19 105.3(3) . . ?
C9 C5 H5A 110.7 . . ?
C19 C5 H5A 110.7 . . ?
C9 C5 H5B 110.7 . . ?
C19 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C8 C6 C19 116.8(2) . . ?
C8 C6 C4 115.5(2) . . ?
C19 C6 C4 102.4(2) . . ?
C8 C6 H6 106.5(13) . . ?
C19 C6 H6 109.9(13) . . ?
C4 C6 H6 105.1(14) . . ?
C23 C7 N2 105.1(2) . . ?
C23 C7 C4 130.9(3) . . ?
N2 C7 C4 123.9(2) . . ?
C24 C8 C26 117.3(3) . . ?
C24 C8 C6 120.3(2) . . ?
C26 C8 C6 122.4(2) . . ?
C5 C9 C35 108.0(3) . . ?
C5 C9 H9A 110.1 . . ?
C35 C9 H9A 110.1 . . ?
C5 C9 H9B 110.1 . . ?
C35 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C21 C10 C13 118.3(3) . . ?
C21 C10 C12 130.0(2) . . ?
C13 C10 C12 111.5(2) . . ?
N1 C11 C2 122.9(2) . . ?
N1 C11 C12 125.9(2) . . ?
C2 C11 C12 111.2(2) . . ?
N5 C12 C11 111.9(2) . . ?
N5 C12 C10 119.3(2) . . ?
C11 C12 C10 100.3(2) . . ?
N5 C12 C4 102.36(19) . . ?
C11 C12 C4 111.4(2) . . ?
C10 C12 C4 111.8(2) . . ?
C32 C13 C10 121.6(3) . . ?
C32 C13 C2 130.0(3) . . ?
C10 C13 C2 108.4(2) . . ?
C1 C14 C3 118.5(5) . . ?
C1 C14 H14A 120.7 . . ?
C3 C14 H14A 120.7 . . ?
N3 C15 C23 110.9(2) . . ?
N3 C15 C29 119.3(3) . . ?
C23 C15 C29 129.8(3) . . ?
C25 C16 C18 120.2(3) . . ?
C25 C16 N2 121.5(3) . . ?
C18 C16 N2 118.2(2) . . ?
C36 C17 C18 119.3(3) . . ?
C36 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
C16 C18 C17 120.5(3) . . ?
C16 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
N5 C19 C6 104.9(2) . . ?
N5 C19 C5 104.6(2) . . ?
C6 C19 C5 118.4(3) . . ?
N5 C19 H19 107.2(15) . . ?
C6 C19 H19 109.5(15) . . ?
C5 C19 H19 111.3(16) . . ?
C39 C20 C24 118.8(3) . . ?
C39 C20 H20A 120.6 . . ?
C24 C20 H20A 120.6 . . ?
C34 C21 C10 120.2(3) . . ?
C34 C21 H21A 119.9 . . ?
C10 C21 H21A 119.9 . . ?
N1 C22 C27 122.9(3) . . ?
N1 C22 C28 118.5(3) . . ?
C27 C22 C28 118.5(3) . . ?
C7 C23 C15 106.9(3) . . ?
C7 C23 H23 125.1(15) . . ?
C15 C23 H23 127.9(15) . . ?
C8 C24 C20 122.1(3) . . ?
C8 C24 H24A 118.9 . . ?
C20 C24 H24A 118.9 . . ?
C16 C25 C31 119.5(3) . . ?
C16 C25 H25A 120.2 . . ?
C31 C25 H25A 120.2 . . ?
C8 C26 C37 121.5(3) . . ?
C8 C26 H26A 119.2 . . ?
C37 C26 H26A 119.2 . . ?
N4 C27 C30 118.8(3) . . ?
N4 C27 C22 121.3(3) . . ?
C30 C27 C22 119.8(3) . . ?
C41 C28 C22 120.2(4) . . ?
C41 C28 H28A 119.9 . . ?
C22 C28 H28A 119.9 . . ?
C3 C29 C38 118.7(3) . . ?
C3 C29 C15 120.9(3) . . ?
C38 C29 C15 120.4(3) . . ?
C40 C30 C27 120.6(4) . . ?
C40 C30 H30A 119.7 . . ?
C27 C30 H30A 119.7 . . ?
C36 C31 C25 119.8(3) . . ?
C36 C31 H31A 120.1 . . ?
C25 C31 H31A 120.1 . . ?
C33 C32 C13 118.6(3) . . ?
C33 C32 H32A 120.7 . . ?
C13 C32 H32A 120.7 . . ?
C32 C33 C34 120.9(3) . . ?
C32 C33 H33A 119.5 . . ?
C34 C33 H33A 119.5 . . ?
C33 C34 C21 120.3(3) . . ?
C33 C34 H34A 119.9 . . ?
C21 C34 H34A 119.9 . . ?
N5 C35 C9 104.4(3) . . ?
N5 C35 H35A 110.9 . . ?
C9 C35 H35A 110.9 . . ?
N5 C35 H35B 110.9 . . ?
C9 C35 H35B 110.9 . . ?
H35A C35 H35B 108.9 . . ?
C17 C36 C31 120.7(3) . . ?
C17 C36 Cl2 119.4(3) . . ?
C31 C36 Cl2 119.8(3) . . ?
C39 C37 C26 118.8(3) . . ?
C39 C37 H37A 120.6 . . ?
C26 C37 H37A 120.6 . . ?
C42 C38 C29 121.2(4) . . ?
C42 C38 H38A 119.4 . . ?
C29 C38 H38A 119.4 . . ?
C37 C39 C20 121.4(3) . . ?
C37 C39 Cl1 120.0(3) . . ?
C20 C39 Cl1 118.5(2) . . ?
C30 C40 C41 120.4(3) . . ?
C30 C40 H40A 119.8 . . ?
C41 C40 H40A 119.8 . . ?
C28 C41 C40 120.4(4) . . ?
C28 C41 H41A 119.8 . . ?
C40 C41 H41A 119.8 . . ?
C1 C42 C38 119.8(5) . . ?
C1 C42 H42A 120.1 . . ?
C38 C42 H42A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C15 0.9(3) . . . . ?
C16 N2 N3 C15 177.5(2) . . . . ?
C27 N4 C2 C11 -0.8(4) . . . . ?
C27 N4 C2 C13 178.2(3) . . . . ?
C7 C4 C6 C8 -65.7(3) . . . . ?
C12 C4 C6 C8 169.1(2) . . . . ?
C7 C4 C6 C19 166.2(2) . . . . ?
C12 C4 C6 C19 41.1(3) . . . . ?
N3 N2 C7 C23 -1.0(3) . . . . ?
C16 N2 C7 C23 -177.0(3) . . . . ?
N3 N2 C7 C4 175.0(2) . . . . ?
C16 N2 C7 C4 -1.0(4) . . . . ?
C6 C4 C7 C23 -25.8(4) . . . . ?
C12 C4 C7 C23 90.7(3) . . . . ?
C6 C4 C7 N2 159.3(2) . . . . ?
C12 C4 C7 N2 -84.2(3) . . . . ?
C19 C6 C8 C24 -112.3(3) . . . . ?
C4 C6 C8 C24 127.2(3) . . . . ?
C19 C6 C8 C26 67.9(4) . . . . ?
C4 C6 C8 C26 -52.6(4) . . . . ?
C19 C5 C9 C35 -27.2(5) . . . . ?
C22 N1 C11 C2 0.5(4) . . . . ?
C22 N1 C11 C12 -178.6(2) . . . . ?
N4 C2 C11 N1 0.2(4) . . . . ?
C13 C2 C11 N1 -179.0(2) . . . . ?
N4 C2 C11 C12 179.5(2) . . . . ?
C13 C2 C11 C12 0.3(3) . . . . ?
C35 N5 C12 C11 -92.2(3) . . . . ?
C19 N5 C12 C11 136.0(2) . . . . ?
C35 N5 C12 C10 24.4(4) . . . . ?
C19 N5 C12 C10 -107.4(3) . . . . ?
C35 N5 C12 C4 148.4(3) . . . . ?
C19 N5 C12 C4 16.5(3) . . . . ?
N1 C11 C12 N5 -49.7(3) . . . . ?
C2 C11 C12 N5 131.1(2) . . . . ?
N1 C11 C12 C10 -177.3(3) . . . . ?
C2 C11 C12 C10 3.5(3) . . . . ?
N1 C11 C12 C4 64.2(3) . . . . ?
C2 C11 C12 C4 -115.0(2) . . . . ?
C21 C10 C12 N5 56.9(4) . . . . ?
C13 C10 C12 N5 -128.9(2) . . . . ?
C21 C10 C12 C11 179.4(3) . . . . ?
C13 C10 C12 C11 -6.4(3) . . . . ?
C21 C10 C12 C4 -62.3(4) . . . . ?
C13 C10 C12 C4 111.8(2) . . . . ?
C7 C4 C12 N5 -158.0(2) . . . . ?
C6 C4 C12 N5 -35.2(2) . . . . ?
C7 C4 C12 C11 82.3(3) . . . . ?
C6 C4 C12 C11 -155.0(2) . . . . ?
C7 C4 C12 C10 -29.1(3) . . . . ?
C6 C4 C12 C10 93.7(2) . . . . ?
C21 C10 C13 C32 3.5(4) . . . . ?
C12 C10 C13 C32 -171.4(2) . . . . ?
C21 C10 C13 C2 -178.1(2) . . . . ?
C12 C10 C13 C2 7.0(3) . . . . ?
N4 C2 C13 C32 -5.4(5) . . . . ?
C11 C2 C13 C32 173.7(3) . . . . ?
N4 C2 C13 C10 176.4(3) . . . . ?
C11 C2 C13 C10 -4.5(3) . . . . ?
C42 C1 C14 C3 -0.7(7) . . . . ?
C29 C3 C14 C1 -0.4(6) . . . . ?
N2 N3 C15 C23 -0.4(3) . . . . ?
N2 N3 C15 C29 -179.9(2) . . . . ?
N3 N2 C16 C25 118.7(3) . . . . ?
C7 N2 C16 C25 -65.5(4) . . . . ?
N3 N2 C16 C18 -57.4(3) . . . . ?
C7 N2 C16 C18 118.4(3) . . . . ?
C25 C16 C18 C17 -1.8(4) . . . . ?
N2 C16 C18 C17 174.4(2) . . . . ?
C36 C17 C18 C16 0.6(4) . . . . ?
C12 N5 C19 C6 9.4(3) . . . . ?
C35 N5 C19 C6 -127.2(3) . . . . ?
C12 N5 C19 C5 134.7(3) . . . . ?
C35 N5 C19 C5 -1.9(4) . . . . ?
C8 C6 C19 N5 -159.0(2) . . . . ?
C4 C6 C19 N5 -31.8(3) . . . . ?
C8 C6 C19 C5 84.8(3) . . . . ?
C4 C6 C19 C5 -147.9(3) . . . . ?
C9 C5 C19 N5 17.6(4) . . . . ?
C9 C5 C19 C6 133.9(4) . . . . ?
C13 C10 C21 C34 -2.1(4) . . . . ?
C12 C10 C21 C34 171.8(3) . . . . ?
C11 N1 C22 C27 -0.6(4) . . . . ?
C11 N1 C22 C28 176.7(3) . . . . ?
N2 C7 C23 C15 0.7(3) . . . . ?
C4 C7 C23 C15 -174.9(3) . . . . ?
N3 C15 C23 C7 -0.2(3) . . . . ?
C29 C15 C23 C7 179.2(3) . . . . ?
C26 C8 C24 C20 2.8(5) . . . . ?
C6 C8 C24 C20 -177.1(3) . . . . ?
C39 C20 C24 C8 -1.0(5) . . . . ?
C18 C16 C25 C31 1.0(4) . . . . ?
N2 C16 C25 C31 -175.0(3) . . . . ?
C24 C8 C26 C37 -2.1(5) . . . . ?
C6 C8 C26 C37 177.7(3) . . . . ?
C2 N4 C27 C30 -176.5(3) . . . . ?
C2 N4 C27 C22 0.7(4) . . . . ?
N1 C22 C27 N4 0.0(4) . . . . ?
C28 C22 C27 N4 -177.3(3) . . . . ?
N1 C22 C27 C30 177.2(3) . . . . ?
C28 C22 C27 C30 -0.1(4) . . . . ?
N1 C22 C28 C41 -176.1(3) . . . . ?
C27 C22 C28 C41 1.3(5) . . . . ?
C14 C3 C29 C38 0.9(5) . . . . ?
C14 C3 C29 C15 -177.1(3) . . . . ?
N3 C15 C29 C3 162.2(3) . . . . ?
C23 C15 C29 C3 -17.2(5) . . . . ?
N3 C15 C29 C38 -15.8(4) . . . . ?
C23 C15 C29 C38 164.8(3) . . . . ?
N4 C27 C30 C40 176.1(3) . . . . ?
C22 C27 C30 C40 -1.1(5) . . . . ?
C16 C25 C31 C36 0.9(5) . . . . ?
C10 C13 C32 C33 -1.7(4) . . . . ?
C2 C13 C32 C33 -179.7(3) . . . . ?
C13 C32 C33 C34 -1.6(5) . . . . ?
C32 C33 C34 C21 3.0(5) . . . . ?
C10 C21 C34 C33 -1.1(5) . . . . ?
C12 N5 C35 C9 -146.7(3) . . . . ?
C19 N5 C35 C9 -14.3(4) . . . . ?
C5 C9 C35 N5 25.8(5) . . . . ?
C18 C17 C36 C31 1.4(5) . . . . ?
C18 C17 C36 Cl2 -177.0(2) . . . . ?
C25 C31 C36 C17 -2.1(5) . . . . ?
C25 C31 C36 Cl2 176.3(2) . . . . ?
C8 C26 C37 C39 -0.3(5) . . . . ?
C3 C29 C38 C42 -0.4(5) . . . . ?
C15 C29 C38 C42 177.7(3) . . . . ?
C26 C37 C39 C20 2.2(5) . . . . ?
C26 C37 C39 Cl1 -175.3(3) . . . . ?
C24 C20 C39 C37 -1.5(5) . . . . ?
C24 C20 C39 Cl1 176.0(2) . . . . ?
C27 C30 C40 C41 1.2(5) . . . . ?
C22 C28 C41 C40 -1.2(5) . . . . ?
C30 C40 C41 C28 0.0(6) . . . . ?
C14 C1 C42 C38 1.3(7) . . . . ?
C29 C38 C42 C1 -0.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.842
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.044

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_exp_173
_database_code_depnum_ccdc_archive 'CCDC 2001016'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H31 N3 O3'
_chemical_formula_sum            'C37 H31 N3 O3'
_chemical_formula_weight         565.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_IT_number           14
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.8723(11)
_cell_length_b                   10.5836(6)
_cell_length_c                   17.0283(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.254(6)
_cell_angle_gamma                90.00
_cell_volume                     2947.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3492
_cell_measurement_theta_min      3.5900
_cell_measurement_theta_max      24.9010

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_min  0.77797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.5253
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24028
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         30.83
_reflns_number_total             7992
_reflns_number_gt                3822
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7992
_refine_ls_number_parameters     419
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.2069
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25270(11) 0.06617(15) 0.41330(10) 0.0703(5) Uani 1 1 d . . .
N1 N 0.27590(11) 0.55040(16) 0.24041(10) 0.0560(5) Uani 1 1 d . . .
C1 C 0.48433(13) 0.3718(2) 0.22715(12) 0.0546(5) Uani 1 1 d . C .
O2 O 0.37569(10) 0.11859(14) 0.36125(9) 0.0670(4) Uani 1 1 d . . .
N2 N 0.39985(11) 0.38924(15) 0.17750(9) 0.0536(4) Uani 1 1 d . C .
C2 C 0.26831(13) 0.43247(19) 0.21739(11) 0.0501(5) Uani 1 1 d . . .
C3 C 0.19185(13) 0.3670(2) 0.19568(11) 0.0522(5) Uani 1 1 d . . .
O3 O -0.05624(12) 0.32292(18) 0.49281(12) 0.0903(6) Uani 1 1 d . . .
N4 N 0.12153(12) 0.41967(18) 0.19771(10) 0.0619(5) Uani 1 1 d . . .
C4 C 0.39124(13) 0.3238(2) 0.30794(12) 0.0484(5) Uani 1 1 d . . .
C5 C 0.12745(15) 0.5448(2) 0.22153(13) 0.0599(6) Uani 1 1 d . . .
C6 C 0.05576(17) 0.6085(3) 0.22810(15) 0.0758(7) Uani 1 1 d . . .
H6A H 0.0059 0.5663 0.2161 0.091 Uiso 1 1 calc R . .
C7 C 0.0596(2) 0.7321(3) 0.25214(16) 0.0829(8) Uani 1 1 d . . .
H7A H 0.0121 0.7736 0.2559 0.100 Uiso 1 1 calc R . .
C8 C 0.1344(2) 0.7971(3) 0.27113(17) 0.0832(8) Uani 1 1 d . . .
H8A H 0.1362 0.8811 0.2875 0.100 Uiso 1 1 calc R . .
C9 C 0.20458(18) 0.7372(2) 0.26569(15) 0.0726(7) Uani 1 1 d . . .
H9A H 0.2539 0.7810 0.2780 0.087 Uiso 1 1 calc R . .
C10 C 0.20310(14) 0.6101(2) 0.24166(12) 0.0559(5) Uani 1 1 d . . .
C11 C 0.33886(13) 0.34147(18) 0.21808(11) 0.0497(5) Uani 1 1 d . . .
C12 C 0.29144(13) 0.22181(19) 0.18463(11) 0.0520(5) Uani 1 1 d . . .
C13 C 0.32104(15) 0.1045(2) 0.16872(13) 0.0615(6) Uani 1 1 d . . .
H13A H 0.3768 0.0924 0.1745 0.074 Uiso 1 1 calc R . .
C14 C 0.26666(17) 0.0057(2) 0.14414(14) 0.0694(6) Uani 1 1 d . . .
H14A H 0.2862 -0.0726 0.1327 0.083 Uiso 1 1 calc R . .
C15 C 0.18362(17) 0.0218(2) 0.13631(14) 0.0719(7) Uani 1 1 d . . .
H15A H 0.1482 -0.0459 0.1206 0.086 Uiso 1 1 calc R . .
C16 C 0.15322(15) 0.1375(2) 0.15164(13) 0.0654(6) Uani 1 1 d . . .
H16A H 0.0974 0.1485 0.1461 0.079 Uiso 1 1 calc R . .
C17 C 0.20719(14) 0.2375(2) 0.17546(12) 0.0543(5) Uani 1 1 d . . .
C18 C 0.35111(13) 0.23300(19) 0.35446(12) 0.0512(5) Uani 1 1 d . . .
C19 C 0.28429(14) 0.2731(2) 0.38346(12) 0.0532(5) Uani 1 1 d . . .
C20 C 0.23424(14) 0.1864(2) 0.40901(12) 0.0525(5) Uani 1 1 d . . .
C21 C 0.47601(13) 0.2883(2) 0.29863(11) 0.0497(5) Uani 1 1 d . . .
C22 C 0.54340(13) 0.30101(19) 0.37562(12) 0.0515(5) Uani 1 1 d . . .
C23 C 0.55049(15) 0.4090(2) 0.42396(14) 0.0682(6) Uani 1 1 d . . .
H23A H 0.5134 0.4748 0.4082 0.082 Uiso 1 1 calc R . .
C24 C 0.61144(17) 0.4203(3) 0.49485(16) 0.0870(9) Uani 1 1 d . . .
H24A H 0.6156 0.4936 0.5258 0.104 Uiso 1 1 calc R . .
C25 C 0.66572(19) 0.3227(3) 0.51917(16) 0.0894(9) Uani 1 1 d . . .
H25A H 0.7058 0.3287 0.5675 0.107 Uiso 1 1 calc R . .
C26 C 0.66065(18) 0.2170(3) 0.47227(18) 0.0861(8) Uani 1 1 d . . .
H26A H 0.6979 0.1515 0.4885 0.103 Uiso 1 1 calc R . .
C27 C 0.60017(15) 0.2065(2) 0.40037(15) 0.0670(6) Uani 1 1 d . . .
H27A H 0.5981 0.1346 0.3685 0.080 Uiso 1 1 calc R . .
C28 C 0.53235(18) 0.3207(3) 0.16907(15) 0.0765(7) Uani 1 1 d . . .
H28A H 0.5345 0.2292 0.1704 0.092 Uiso 1 1 calc R A 1
H28B H 0.5877 0.3538 0.1819 0.092 Uiso 1 1 calc R A 1
C30 C 0.39587(17) 0.3582(2) 0.09252(13) 0.0683(6) Uani 1 1 d . . .
H30A H 0.3610 0.4173 0.0562 0.082 Uiso 1 1 calc R B 1
H30B H 0.3751 0.2732 0.0796 0.082 Uiso 1 1 calc R B 1
C31 C 0.15831(14) 0.2224(2) 0.43129(12) 0.0546(5) Uani 1 1 d . . .
C32 C 0.12329(15) 0.3409(2) 0.41511(14) 0.0646(6) Uani 1 1 d . . .
H32A H 0.1486 0.4011 0.3897 0.077 Uiso 1 1 calc R . .
C33 C 0.05189(17) 0.3713(2) 0.43588(15) 0.0707(7) Uani 1 1 d . . .
H33A H 0.0295 0.4516 0.4247 0.085 Uiso 1 1 calc R . .
C34 C 0.01326(15) 0.2830(2) 0.47333(14) 0.0633(6) Uani 1 1 d . . .
C35 C 0.04724(17) 0.1655(2) 0.49095(15) 0.0704(7) Uani 1 1 d . . .
H35A H 0.0222 0.1063 0.5172 0.084 Uiso 1 1 calc R . .
C36 C 0.11852(15) 0.1354(2) 0.46962(14) 0.0661(6) Uani 1 1 d . . .
H36A H 0.1406 0.0550 0.4811 0.079 Uiso 1 1 calc R . .
C37 C -0.1061(2) 0.2310(4) 0.5186(3) 0.1258(13) Uani 1 1 d . . .
H37A H -0.1521 0.2719 0.5314 0.189 Uiso 1 1 calc R . .
H37B H -0.0747 0.1882 0.5657 0.189 Uiso 1 1 calc R . .
H37C H -0.1251 0.1708 0.4759 0.189 Uiso 1 1 calc R . .
H4 H 0.3936(12) 0.406(2) 0.3314(11) 0.049(5) Uiso 1 1 d . . .
H21 H 0.4730(12) 0.1979(18) 0.2797(10) 0.042(5) Uiso 1 1 d . . .
H19 H 0.2713(14) 0.360(2) 0.3802(12) 0.060(6) Uiso 1 1 d . . .
H1 H 0.5112(14) 0.458(2) 0.2523(12) 0.062(6) Uiso 1 1 d . . .
C29 C 0.4832(2) 0.3687(4) 0.0864(2) 0.0669(9) Uani 0.75 1 d PU C 1
H29A H 0.4971 0.4555 0.0775 0.080 Uiso 0.75 1 calc PR C 1
H29B H 0.4927 0.3166 0.0428 0.080 Uiso 0.75 1 calc PR C 1
C29A C 0.4768(10) 0.2896(16) 0.0969(9) 0.099(4) Uani 0.25 1 d PU C 2
H29C H 0.4678 0.1990 0.0942 0.119 Uiso 0.25 1 calc PR C 2
H29D H 0.4983 0.3142 0.0513 0.119 Uiso 0.25 1 calc PR C 2
H2 H 0.313(2) 0.064(3) 0.390(2) 0.130(11) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.308(2) . ?
O1 H2 1.17(4) . ?
N1 C2 1.305(3) . ?
N1 C10 1.386(3) . ?
C1 N2 1.479(3) . ?
C1 C28 1.524(3) . ?
C1 C21 1.538(3) . ?
C1 H1 1.06(2) . ?
O2 C18 1.276(2) . ?
O2 H2 1.40(4) . ?
N2 C11 1.464(3) . ?
N2 C30 1.469(3) . ?
C2 C3 1.430(3) . ?
C2 C11 1.529(3) . ?
C3 N4 1.319(3) . ?
C3 C17 1.452(3) . ?
O3 C34 1.362(3) . ?
O3 C37 1.424(3) . ?
N4 C5 1.382(3) . ?
C4 C18 1.508(3) . ?
C4 C21 1.524(3) . ?
C4 C11 1.578(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.413(3) . ?
C5 C10 1.417(3) . ?
C6 C7 1.368(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.402(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.367(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.405(3) . ?
C9 H9A 0.9300 . ?
C11 C12 1.531(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.401(3) . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16A 0.9300 . ?
C18 C19 1.403(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.94(2) . ?
C20 C31 1.473(3) . ?
C21 C22 1.515(3) . ?
C21 H21 1.007(18) . ?
C22 C27 1.377(3) . ?
C22 C23 1.396(3) . ?
C23 C24 1.385(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.375(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.365(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.392(4) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C28 C29A 1.390(15) . ?
C28 C29 1.533(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 C29 1.506(5) . ?
C30 C29A 1.531(15) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.386(3) . ?
C31 C36 1.393(3) . ?
C32 C33 1.375(3) . ?
C32 H32A 0.9300 . ?
C33 C34 1.382(3) . ?
C33 H33A 0.9300 . ?
C34 C35 1.371(3) . ?
C35 C36 1.377(3) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29A H29C 0.9700 . ?
C29A H29D 0.9700 . ?

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
C20 O1 H2 102.3(15) . . ?
C2 N1 C10 114.74(19) . . ?
N2 C1 C28 105.36(18) . . ?
N2 C1 C21 105.13(16) . . ?
C28 C1 C21 118.47(19) . . ?
N2 C1 H1 112.2(12) . . ?
C28 C1 H1 108.9(11) . . ?
C21 C1 H1 106.8(11) . . ?
C18 O2 H2 99.4(13) . . ?
C11 N2 C30 121.37(17) . . ?
C11 N2 C1 112.19(15) . . ?
C30 N2 C1 109.82(17) . . ?
N1 C2 C3 123.80(19) . . ?
N1 C2 C11 125.56(19) . . ?
C3 C2 C11 110.35(17) . . ?
N4 C3 C2 123.3(2) . . ?
N4 C3 C17 128.2(2) . . ?
C2 C3 C17 108.45(18) . . ?
C34 O3 C37 118.2(2) . . ?
C3 N4 C5 114.35(19) . . ?
C18 C4 C21 116.86(17) . . ?
C18 C4 C11 111.60(17) . . ?
C21 C4 C11 104.12(15) . . ?
C18 C4 H4 109.9(11) . . ?
C21 C4 H4 109.0(12) . . ?
C11 C4 H4 104.6(11) . . ?
N4 C5 C6 118.6(2) . . ?
N4 C5 C10 122.3(2) . . ?
C6 C5 C10 119.1(2) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
N1 C10 C9 119.2(2) . . ?
N1 C10 C5 121.6(2) . . ?
C9 C10 C5 119.2(2) . . ?
N2 C11 C2 114.54(16) . . ?
N2 C11 C12 118.29(16) . . ?
C2 C11 C12 100.58(16) . . ?
N2 C11 C4 101.99(16) . . ?
C2 C11 C4 109.33(16) . . ?
C12 C11 C4 112.29(16) . . ?
C13 C12 C17 119.2(2) . . ?
C13 C12 C11 129.2(2) . . ?
C17 C12 C11 111.49(17) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 119.0(2) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 C3 130.2(2) . . ?
C12 C17 C3 108.70(18) . . ?
O2 C18 C19 121.77(19) . . ?
O2 C18 C4 118.33(18) . . ?
C19 C18 C4 119.71(19) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 120.8(14) . . ?
C18 C19 H19 118.0(13) . . ?
O1 C20 C19 120.4(2) . . ?
O1 C20 C31 116.58(19) . . ?
C19 C20 C31 123.03(19) . . ?
C22 C21 C4 114.31(16) . . ?
C22 C21 C1 116.02(18) . . ?
C4 C21 C1 102.22(16) . . ?
C22 C21 H21 109.2(11) . . ?
C4 C21 H21 107.0(11) . . ?
C1 C21 H21 107.4(10) . . ?
C27 C22 C23 117.5(2) . . ?
C27 C22 C21 121.19(19) . . ?
C23 C22 C21 121.3(2) . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23A 119.3 . . ?
C22 C23 H23A 119.3 . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26A 119.8 . . ?
C27 C26 H26A 119.8 . . ?
C22 C27 C26 121.0(3) . . ?
C22 C27 H27A 119.5 . . ?
C26 C27 H27A 119.5 . . ?
C29A C28 C1 107.9(6) . . ?
C29A C28 C29 34.1(7) . . ?
C1 C28 C29 103.0(2) . . ?
C29A C28 H28A 78.3 . . ?
C1 C28 H28A 111.2 . . ?
C29 C28 H28A 111.2 . . ?
C29A C28 H28B 133.5 . . ?
C1 C28 H28B 111.2 . . ?
C29 C28 H28B 111.2 . . ?
H28A C28 H28B 109.1 . . ?
N2 C30 C29 104.0(2) . . ?
N2 C30 C29A 103.6(6) . . ?
C29 C30 C29A 33.2(6) . . ?
N2 C30 H30A 110.9 . . ?
C29 C30 H30A 110.9 . . ?
C29A C30 H30A 136.8 . . ?
N2 C30 H30B 110.9 . . ?
C29 C30 H30B 110.9 . . ?
C29A C30 H30B 80.8 . . ?
H30A C30 H30B 109.0 . . ?
C32 C31 C36 117.4(2) . . ?
C32 C31 C20 122.56(19) . . ?
C36 C31 C20 120.00(19) . . ?
C33 C32 C31 121.2(2) . . ?
C33 C32 H32A 119.4 . . ?
C31 C32 H32A 119.4 . . ?
C32 C33 C34 120.2(2) . . ?
C32 C33 H33A 119.9 . . ?
C34 C33 H33A 119.9 . . ?
O3 C34 C35 124.5(2) . . ?
O3 C34 C33 115.7(2) . . ?
C35 C34 C33 119.7(2) . . ?
C34 C35 C36 119.8(2) . . ?
C34 C35 H35A 120.1 . . ?
C36 C35 H35A 120.1 . . ?
C35 C36 C31 121.6(2) . . ?
C35 C36 H36A 119.2 . . ?
C31 C36 H36A 119.2 . . ?
O3 C37 H37A 109.5 . . ?
O3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C30 C29 C28 103.3(2) . . ?
C30 C29 H29A 111.1 . . ?
C28 C29 H29A 111.1 . . ?
C30 C29 H29B 111.1 . . ?
C28 C29 H29B 111.1 . . ?
H29A C29 H29B 109.1 . . ?
C28 C29A C30 109.3(9) . . ?
C28 C29A H29C 109.8 . . ?
C30 C29A H29C 109.8 . . ?
C28 C29A H29D 109.8 . . ?
C30 C29A H29D 109.8 . . ?
H29C C29A H29D 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C28 C1 N2 C11 135.05(19) . . . . ?
C21 C1 N2 C11 9.1(2) . . . . ?
C28 C1 N2 C30 -3.1(2) . . . . ?
C21 C1 N2 C30 -128.98(18) . . . . ?
C10 N1 C2 C3 -0.7(3) . . . . ?
C10 N1 C2 C11 -173.95(17) . . . . ?
N1 C2 C3 N4 -0.7(3) . . . . ?
C11 C2 C3 N4 173.43(18) . . . . ?
N1 C2 C3 C17 -178.56(18) . . . . ?
C11 C2 C3 C17 -4.4(2) . . . . ?
C2 C3 N4 C5 0.9(3) . . . . ?
C17 C3 N4 C5 178.31(18) . . . . ?
C3 N4 C5 C6 -178.02(19) . . . . ?
C3 N4 C5 C10 0.2(3) . . . . ?
N4 C5 C6 C7 179.5(2) . . . . ?
C10 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C2 N1 C10 C9 179.91(18) . . . . ?
C2 N1 C10 C5 1.8(3) . . . . ?
C8 C9 C10 N1 -177.0(2) . . . . ?
C8 C9 C10 C5 1.2(3) . . . . ?
N4 C5 C10 N1 -1.6(3) . . . . ?
C6 C5 C10 N1 176.58(19) . . . . ?
N4 C5 C10 C9 -179.76(19) . . . . ?
C6 C5 C10 C9 -1.5(3) . . . . ?
C30 N2 C11 C2 -95.2(2) . . . . ?
C1 N2 C11 C2 132.13(17) . . . . ?
C30 N2 C11 C12 23.1(3) . . . . ?
C1 N2 C11 C12 -109.51(19) . . . . ?
C30 N2 C11 C4 146.83(19) . . . . ?
C1 N2 C11 C4 14.2(2) . . . . ?
N1 C2 C11 N2 -51.7(3) . . . . ?
C3 C2 C11 N2 134.25(17) . . . . ?
N1 C2 C11 C12 -179.70(18) . . . . ?
C3 C2 C11 C12 6.3(2) . . . . ?
N1 C2 C11 C4 62.0(2) . . . . ?
C3 C2 C11 C4 -112.05(18) . . . . ?
C18 C4 C11 N2 -159.26(16) . . . . ?
C21 C4 C11 N2 -32.34(19) . . . . ?
C18 C4 C11 C2 79.1(2) . . . . ?
C21 C4 C11 C2 -153.96(17) . . . . ?
C18 C4 C11 C12 -31.6(2) . . . . ?
C21 C4 C11 C12 95.3(2) . . . . ?
N2 C11 C12 C13 53.0(3) . . . . ?
C2 C11 C12 C13 178.5(2) . . . . ?
C4 C11 C12 C13 -65.4(3) . . . . ?
N2 C11 C12 C17 -131.67(19) . . . . ?
C2 C11 C12 C17 -6.2(2) . . . . ?
C4 C11 C12 C17 109.93(19) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C14 175.0(2) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C15 C16 C17 C3 -179.5(2) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
C11 C12 C17 C16 -175.16(19) . . . . ?
C13 C12 C17 C3 179.85(17) . . . . ?
C11 C12 C17 C3 4.0(2) . . . . ?
N4 C3 C17 C16 1.6(4) . . . . ?
C2 C3 C17 C16 179.3(2) . . . . ?
N4 C3 C17 C12 -177.43(19) . . . . ?
C2 C3 C17 C12 0.3(2) . . . . ?
C21 C4 C18 O2 -21.4(3) . . . . ?
C11 C4 C18 O2 98.3(2) . . . . ?
C21 C4 C18 C19 163.49(18) . . . . ?
C11 C4 C18 C19 -76.9(2) . . . . ?
O2 C18 C19 C20 -10.4(3) . . . . ?
C4 C18 C19 C20 164.56(18) . . . . ?
C18 C19 C20 O1 6.1(3) . . . . ?
C18 C19 C20 C31 -172.96(18) . . . . ?
C18 C4 C21 C22 -72.4(2) . . . . ?
C11 C4 C21 C22 164.03(16) . . . . ?
C18 C4 C21 C1 161.42(17) . . . . ?
C11 C4 C21 C1 37.9(2) . . . . ?
N2 C1 C21 C22 -154.27(17) . . . . ?
C28 C1 C21 C22 88.4(3) . . . . ?
N2 C1 C21 C4 -29.2(2) . . . . ?
C28 C1 C21 C4 -146.5(2) . . . . ?
C4 C21 C22 C27 133.2(2) . . . . ?
C1 C21 C22 C27 -108.2(2) . . . . ?
C4 C21 C22 C23 -47.1(3) . . . . ?
C1 C21 C22 C23 71.6(3) . . . . ?
C27 C22 C23 C24 -1.0(4) . . . . ?
C21 C22 C23 C24 179.3(2) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C24 C25 C26 C27 -0.8(4) . . . . ?
C23 C22 C27 C26 2.0(4) . . . . ?
C21 C22 C27 C26 -178.2(2) . . . . ?
C25 C26 C27 C22 -1.2(4) . . . . ?
N2 C1 C28 C29A -10.2(8) . . . . ?
C21 C1 C28 C29A 107.0(8) . . . . ?
N2 C1 C28 C29 24.8(3) . . . . ?
C21 C1 C28 C29 142.0(2) . . . . ?
C11 N2 C30 C29 -154.1(2) . . . . ?
C1 N2 C30 C29 -20.4(3) . . . . ?
C11 N2 C30 C29A -119.9(7) . . . . ?
C1 N2 C30 C29A 13.8(7) . . . . ?
O1 C20 C31 C32 -167.4(2) . . . . ?
C19 C20 C31 C32 11.7(3) . . . . ?
O1 C20 C31 C36 12.1(3) . . . . ?
C19 C20 C31 C36 -168.8(2) . . . . ?
C36 C31 C32 C33 -0.2(3) . . . . ?
C20 C31 C32 C33 179.3(2) . . . . ?
C31 C32 C33 C34 -0.3(4) . . . . ?
C37 O3 C34 C35 -13.0(4) . . . . ?
C37 O3 C34 C33 169.4(3) . . . . ?
C32 C33 C34 O3 178.8(2) . . . . ?
C32 C33 C34 C35 1.1(4) . . . . ?
O3 C34 C35 C36 -179.0(2) . . . . ?
C33 C34 C35 C36 -1.5(4) . . . . ?
C34 C35 C36 C31 1.0(4) . . . . ?
C32 C31 C36 C35 -0.2(3) . . . . ?
C20 C31 C36 C35 -179.7(2) . . . . ?
N2 C30 C29 C28 35.5(3) . . . . ?
C29A C30 C29 C28 -57.9(10) . . . . ?
C29A C28 C29 C30 65.7(11) . . . . ?
C1 C28 C29 C30 -37.2(3) . . . . ?
C1 C28 C29A C30 19.3(13) . . . . ?
C29 C28 C29A C30 -67.5(11) . . . . ?
N2 C30 C29A C28 -20.7(12) . . . . ?
C29 C30 C29A C28 74.4(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
