# Electronic Supplementary Material (ESI) for ChemComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2216699'
loop_
_audit_author_name
_audit_author_address
'Ayaka Kikuchi'
;Department of Materials Chemistry, Faculty of Engineering, Shinshu University
Japan
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         348.40

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.28(2)
_cell_length_b                   8.194(8)
_cell_length_c                   22.20(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.876(12)
_cell_angle_gamma                90
_cell_volume                     3483.(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    148
_cell_measurement_theta_min      2.0698
_cell_measurement_theta_max      21.9964
_cell_measurement_temperature    88.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.230
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.980

_exptl_special_details           
;
;

_diffrn_ambient_temperature      88.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       ω

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9409
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_full        27.14
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       28

_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.
;

_reflns_number_total             3758
_reflns_number_gt                1854
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1687
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         3758
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0753P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0030(4)

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'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.08237(11) 0.4281(3) 1.03674(9) 0.0792(7) Uani d . 1 . .
O O2 0.19324(10) -0.0935(2) 1.00514(9) 0.0736(6) Uani d . 1 . .
N N1 0.15205(10) 0.1830(3) 0.87374(10) 0.0559(6) Uani d . 1 . .
N N2 0.15468(11) 0.1228(3) 0.93633(10) 0.0599(6) Uani d . 1 . .
N N3 0.09165(11) 0.4128(2) 0.88292(10) 0.0543(6) Uani d . 1 . .
N N4 0.09884(12) 0.3518(3) 0.94657(11) 0.0603(6) Uani d . 1 . .
C C1 0.15808(17) 0.5543(4) 0.70026(15) 0.0683(8) Uani d . 1 . .
H H1A 0.1592 0.5976 0.6611 0.082 Uiso calc R 1 . .
C C2 0.10586(16) 0.4505(4) 0.69484(13) 0.0670(8) Uani d . 1 . .
H H2 0.0707 0.4216 0.6519 0.08 Uiso calc R 1 . .
C C3 0.10393(14) 0.3872(3) 0.75173(13) 0.0612(7) Uani d . 1 . .
H H3 0.0673 0.3154 0.7478 0.073 Uiso calc R 1 . .
C C4 0.15538(13) 0.4282(3) 0.81460(11) 0.0484(6) Uani d . 1 . .
C C5 0.15445(13) 0.3604(3) 0.87687(12) 0.0523(7) Uani d . 1 . .
H H5 0.1971 0.3968 0.917 0.063 Uiso calc R 1 . .
C C6 0.09893(13) 0.1780(3) 0.95200(13) 0.0569(7) Uani d . 1 . .
H H6 0.1124 0.1507 1.0 0.068 Uiso calc R 1 . .
C C7 0.02845(14) 0.1020(3) 0.91065(13) 0.0549(7) Uani d . 1 . .
C C8 -0.02342(16) 0.1254(4) 0.93122(17) 0.0765(9) Uani d . 1 . .
H H8 -0.0136 0.1874 0.9705 0.092 Uiso calc R 1 . .
C C9 -0.08862(19) 0.0610(4) 0.8961(2) 0.0893(10) Uani d . 1 . .
H H9 -0.1239 0.0806 0.9106 0.107 Uiso calc R 1 . .
C C10 -0.10335(18) -0.0305(4) 0.8408(2) 0.0877(10) Uani d . 1 . .
H H10 -0.1485 -0.0769 0.8169 0.105 Uiso calc R 1 . .
C C11 0.09240(19) 0.5917(3) 0.89298(17) 0.0796(9) Uani d . 1 . .
H H11A 0.0603 0.6467 0.8511 0.095 Uiso calc R 1 . .
H H11B 0.14 0.6359 0.907 0.095 Uiso calc R 1 . .
C C12 0.06882(16) 0.6176(4) 0.94683(14) 0.0670(8) Uani d . 1 . .
H H12A 0.0951 0.708 0.9769 0.08 Uiso calc R 1 . .
H H12B 0.0183 0.6431 0.9272 0.08 Uiso calc R 1 . .
C C13 0.08378(13) 0.4606(4) 0.98359(14) 0.0601(7) Uani d . 1 . .
C C14 0.21772(15) 0.1117(4) 0.87636(16) 0.0755(9) Uani d . 1 . .
H H14A 0.2132 0.0909 0.8307 0.091 Uiso calc R 1 . .
H H14B 0.2578 0.1856 0.9 0.091 Uiso calc R 1 . .
C C15 0.2266(2) -0.0424(4) 0.91350(19) 0.0720(9) Uani d . 1 . .
C C16 0.19148(13) -0.0130(3) 0.95800(13) 0.0533(6) Uani d . 1 . .
C C17 -0.0516(2) -0.0560(4) 0.81921(18) 0.0909(10) Uani d . 1 . .
H H17 -0.0613 -0.1196 0.7804 0.109 Uiso calc R 1 . .
C C18 0.01349(17) 0.0110(4) 0.85435(17) 0.0763(9) Uani d . 1 . .
H H18 0.0486 -0.0059 0.8394 0.092 Uiso calc R 1 . .
C C19 0.20741(13) 0.5325(3) 0.81921(13) 0.0584(7) Uani d . 1 . .
H H23 0.2429 0.5613 0.862 0.07 Uiso calc R 1 . .
C C20 0.20908(15) 0.5966(4) 0.76227(14) 0.0693(8) Uani d . 1 . .
H H21 0.2453 0.6696 0.766 0.083 Uiso calc R 1 . .
H H22 0.2685(16) -0.082(3) 0.9361(14) 0.074(9) Uiso d . 1 . .
H H24 0.197(2) -0.122(5) 0.8772(19) 0.129(15) Uiso d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.223(3) ?
O2 C16 . 1.224(3) ?
N1 N2 . 1.452(3) ?
N1 C5 . 1.455(4) ?
N1 C14 . 1.492(3) ?
N2 C16 . 1.324(3) ?
N2 C6 . 1.447(3) ?
N3 N4 . 1.442(3) ?
N3 C5 . 1.464(3) ?
N3 C11 . 1.482(4) ?
N4 C13 . 1.342(3) ?
N4 C6 . 1.429(4) ?
C1 C2 . 1.362(4) ?
C1 C20 . 1.374(4) ?
C1 H1A . 0.95 ?
C2 C3 . 1.383(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.388(4) ?
C3 H3 . 0.95 ?
C4 C19 . 1.367(3) ?
C4 C5 . 1.498(3) ?
C5 H5 . 1.0 ?
C6 C7 . 1.509(4) ?
C6 H6 . 1.0 ?
C7 C18 . 1.368(4) ?
C7 C8 . 1.380(4) ?
C8 C9 . 1.366(5) ?
C8 H8 . 0.95 ?
C9 C10 . 1.354(5) ?
C9 H9 . 0.95 ?
C10 C17 . 1.395(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.500(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.482(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C14 C15 . 1.474(4) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.495(4) ?
C15 H22 . 0.87(3) ?
C15 H24 . 1.02(4) ?
C17 C18 . 1.373(5) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 C20 . 1.384(3) ?
C19 H23 . 0.95 ?
C20 H21 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C5 . . 107.94(19) ?
N2 N1 C14 . . 100.66(19) ?
C5 N1 C14 . . 112.1(2) ?
C16 N2 C6 . . 126.3(2) ?
C16 N2 N1 . . 113.8(2) ?
C6 N2 N1 . . 115.5(2) ?
N4 N3 C5 . . 106.12(19) ?
N4 N3 C11 . . 101.85(19) ?
C5 N3 C11 . . 110.7(2) ?
C13 N4 C6 . . 127.0(2) ?
C13 N4 N3 . . 114.7(2) ?
C6 N4 N3 . . 115.04(19) ?
C2 C1 C20 . . 120.2(3) ?
C2 C1 H1A . . 119.9 ?
C20 C1 H1A . . 119.9 ?
C1 C2 C3 . . 120.1(3) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.2(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C19 C4 C3 . . 119.0(2) ?
C19 C4 C5 . . 119.9(2) ?
C3 C4 C5 . . 121.1(2) ?
N1 C5 N3 . . 106.41(19) ?
N1 C5 C4 . . 109.9(2) ?
N3 C5 C4 . . 110.9(2) ?
N1 C5 H5 . . 109.9 ?
N3 C5 H5 . . 109.9 ?
C4 C5 H5 . . 109.9 ?
N4 C6 N2 . . 105.2(2) ?
N4 C6 C7 . . 113.3(2) ?
N2 C6 C7 . . 115.2(2) ?
N4 C6 H6 . . 107.6 ?
N2 C6 H6 . . 107.6 ?
C7 C6 H6 . . 107.6 ?
C18 C7 C8 . . 118.5(3) ?
C18 C7 C6 . . 123.6(2) ?
C8 C7 C6 . . 117.9(3) ?
C9 C8 C7 . . 121.1(3) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C10 C9 C8 . . 120.5(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C17 . . 119.3(3) ?
C9 C10 H10 . . 120.4 ?
C17 C10 H10 . . 120.4 ?
N3 C11 C12 . . 105.9(2) ?
N3 C11 H11A . . 110.5 ?
C12 C11 H11A . . 110.5 ?
N3 C11 H11B . . 110.5 ?
C12 C11 H11B . . 110.5 ?
H11A C11 H11B . . 108.7 ?
C13 C12 C11 . . 104.5(2) ?
C13 C12 H12A . . 110.9 ?
C11 C12 H12A . . 110.9 ?
C13 C12 H12B . . 110.9 ?
C11 C12 H12B . . 110.9 ?
H12A C12 H12B . . 108.9 ?
O1 C13 N4 . . 124.0(3) ?
O1 C13 C12 . . 129.1(2) ?
N4 C13 C12 . . 106.9(2) ?
C15 C14 N1 . . 104.3(2) ?
C15 C14 H14A . . 110.9 ?
N1 C14 H14A . . 110.9 ?
C15 C14 H14B . . 110.9 ?
N1 C14 H14B . . 110.9 ?
H14A C14 H14B . . 108.9 ?
C14 C15 C16 . . 104.6(3) ?
C14 C15 H22 . . 119.1(19) ?
C16 C15 H22 . . 111.1(18) ?
C14 C15 H24 . . 103.(2) ?
C16 C15 H24 . . 108.(2) ?
H22 C15 H24 . . 111.(3) ?
O2 C16 N2 . . 123.8(2) ?
O2 C16 C15 . . 129.8(3) ?
N2 C16 C15 . . 106.4(2) ?
C18 C17 C10 . . 119.8(3) ?
C18 C17 H17 . . 120.1 ?
C10 C17 H17 . . 120.1 ?
C7 C18 C17 . . 120.8(3) ?
C7 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C4 C19 C20 . . 120.8(2) ?
C4 C19 H23 . . 119.6 ?
C20 C19 H23 . . 119.6 ?
C1 C20 C19 . . 119.7(3) ?
C1 C20 H21 . . 120.2 ?
C19 C20 H21 . . 120.2 ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2216702'
loop_
_audit_author_name
_audit_author_address
'Kimiya Sukegawa'
;Department of Materials Chemistry, Faculty of Engineering, Shinshu University
Japan
;
_audit_update_record             
;
2022-11-01 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         376.45
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.660(2)
_cell_length_b                   13.2963(15)
_cell_length_c                   7.8585(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1949.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    228
_cell_measurement_theta_min      3.3487
_cell_measurement_theta_max      22.3726
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.320
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8906
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9

_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.
;

_reflns_number_total             3305
_reflns_number_gt                2686
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1136
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_restrained_S_all      1.253
_refine_ls_number_reflns         3305
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.5(17)

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'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.04406(12) 0.45571(15) 0.4754(3) 0.0908(7) Uani d . 1 . .
O O2 0.20259(11) 0.55169(15) 0.8930(3) 0.0798(6) Uani d . 1 . .
N N1 0.04151(9) 0.71953(13) 0.4927(2) 0.0450(4) Uani d . 1 . .
N N2 0.07511(9) 0.62193(13) 0.4872(2) 0.0470(5) Uani d . 1 . .
N N3 0.13358(11) 0.65577(14) 0.7419(2) 0.0553(5) Uani d . 1 . .
N N4 0.09560(11) 0.75065(14) 0.7567(2) 0.0494(5) Uani d . 1 . .
C C1 -0.07622(16) 1.0278(2) 0.7329(4) 0.0719(8) Uani d . 1 . .
H H1 -0.0976 1.0905 0.7474 0.086 Uiso calc R 1 . .
C C2 -0.11450(15) 0.9425(2) 0.7683(3) 0.0663(8) Uani d . 1 . .
H H2 -0.1615 0.9483 0.8064 0.08 Uiso calc R 1 . .
C C3 -0.08433(13) 0.8470(2) 0.7484(3) 0.0566(6) Uani d . 1 . .
C C4 -0.01379(12) 0.84068(17) 0.6918(3) 0.0465(6) Uani d . 1 . .
C C5 0.02501(12) 0.74119(17) 0.6741(3) 0.0452(5) Uani d . 1 . .
H H5 -0.0029 0.6864 0.725 0.054 Uiso calc R 1 . .
C C6 0.14376(12) 0.61411(18) 0.5723(3) 0.0479(6) Uani d . 1 . .
H H6 0.1547 0.5424 0.5853 0.058 Uiso calc R 1 . .
C C7 0.20354(11) 0.66083(17) 0.4687(3) 0.0473(5) Uani d . 1 . .
C C8 0.21344(13) 0.76388(19) 0.4661(4) 0.0619(7) Uani d . 1 . .
H H8 0.1854 0.8046 0.5355 0.074 Uiso calc R 1 . .
C C9 0.26429(15) 0.8071(2) 0.3619(5) 0.0756(8) Uani d . 1 . .
H H9 0.2697 0.8766 0.3596 0.091 Uiso calc R 1 . .
C C10 0.30616(15) 0.7484(3) 0.2633(4) 0.0768(9) Uani d . 1 . .
H H10 0.3408 0.7777 0.194 0.092 Uiso calc R 1 . .
C C11 -0.00694(17) 1.0222(2) 0.6765(4) 0.0706(8) Uani d . 1 . .
H H11 0.0189 1.0803 0.6524 0.085 Uiso calc R 1 . .
C C12 0.02378(14) 0.9290(2) 0.6562(3) 0.0594(7) Uani d . 1 . .
H H12 0.0708 0.9247 0.6176 0.071 Uiso calc R 1 . .
C C13 0.02861(15) 0.5443(2) 0.4629(4) 0.0653(7) Uani d . 1 . .
C C14 -0.04259(14) 0.5904(2) 0.4149(4) 0.0725(8) Uani d . 1 . .
H H14A -0.0777 0.5813 0.5046 0.087 Uiso calc R 1 . .
H H14B -0.061 0.5614 0.3103 0.087 Uiso calc R 1 . .
C C15 -0.02389(12) 0.7012(2) 0.3913(3) 0.0601(7) Uani d . 1 . .
H H15A -0.0152 0.7159 0.2721 0.072 Uiso calc R 1 . .
H H15B -0.0628 0.7435 0.431 0.072 Uiso calc R 1 . .
C C16 0.0882(2) 0.7605(2) 0.9439(4) 0.0801(9) Uani d . 1 . .
H H16A 0.0957 0.8298 0.9782 0.096 Uiso calc R 1 . .
H H16B 0.0406 0.7402 0.9795 0.096 Uiso calc R 1 . .
C C17 0.14131(18) 0.6965(2) 1.0202(4) 0.0860(11) Uani d . 1 . .
H H17A 0.1214 0.6609 1.117 0.103 Uiso calc R 1 . .
H H17B 0.1821 0.7358 1.0584 0.103 Uiso calc R 1 . .
C C18 0.16349(12) 0.62358(18) 0.8831(3) 0.0495(6) Uani d . 1 . .
C C19 0.29804(13) 0.6463(3) 0.2644(4) 0.0727(9) Uani d . 1 . .
H H19 0.3273 0.6072 0.1951 0.087 Uiso calc R 1 . .
C C20 0.24692(13) 0.59897(19) 0.3670(4) 0.0575(6) Uani d . 1 . .
C C21 0.2393(2) 0.4861(2) 0.3628(5) 0.0966(11) Uani d . 1 . .
H H21A 0.2696 0.4591 0.2753 0.145 Uiso calc R 1 . .
H H21B 0.1903 0.4688 0.3394 0.145 Uiso calc R 1 . .
H H21C 0.2531 0.4587 0.4709 0.145 Uiso calc R 1 . .
C C22 -0.12950(15) 0.7547(2) 0.7867(4) 0.0792(9) Uani d . 1 . .
H H22A -0.1376 0.7178 0.6835 0.119 Uiso calc R 1 . .
H H22B -0.1746 0.7752 0.8339 0.119 Uiso calc R 1 . .
H H22C -0.1048 0.7127 0.8668 0.119 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.216(3) ?
O2 C18 . 1.205(3) ?
N1 N2 . 1.442(2) ?
N1 C15 . 1.478(3) ?
N1 C5 . 1.486(3) ?
N2 C13 . 1.362(3) ?
N2 C6 . 1.449(3) ?
N3 C18 . 1.314(3) ?
N3 N4 . 1.452(2) ?
N3 C6 . 1.455(3) ?
N4 C5 . 1.474(3) ?
N4 C16 . 1.484(4) ?
C1 C2 . 1.369(4) ?
C1 C11 . 1.369(4) ?
C1 H1 . 0.93 ?
C2 C3 . 1.399(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.392(3) ?
C3 C22 . 1.519(4) ?
C4 C12 . 1.396(3) ?
C4 C5 . 1.514(3) ?
C5 H5 . 0.98 ?
C6 C7 . 1.514(3) ?
C6 H6 . 0.98 ?
C7 C8 . 1.383(3) ?
C7 C20 . 1.404(3) ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.349(4) ?
C9 H9 . 0.93 ?
C10 C19 . 1.366(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 C14 . 1.511(4) ?
C14 C15 . 1.526(4) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 C17 . 1.437(4) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.508(4) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C19 C20 . 1.399(4) ?
C19 H19 . 0.93 ?
C20 C21 . 1.507(4) ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C15 . . 101.24(17) ?
N2 N1 C5 . . 107.05(16) ?
C15 N1 C5 . . 112.20(17) ?
C13 N2 N1 . . 114.16(18) ?
C13 N2 C6 . . 125.0(2) ?
N1 N2 C6 . . 115.81(16) ?
C18 N3 N4 . . 115.01(18) ?
C18 N3 C6 . . 126.43(18) ?
N4 N3 C6 . . 117.90(17) ?
N3 N4 C5 . . 109.08(17) ?
N3 N4 C16 . . 101.65(17) ?
C5 N4 C16 . . 111.2(2) ?
C2 C1 C11 . . 120.9(3) ?
C2 C1 H1 . . 119.6 ?
C11 C1 H1 . . 119.6 ?
C1 C2 C3 . . 121.3(2) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C4 C3 C2 . . 118.1(2) ?
C4 C3 C22 . . 122.7(2) ?
C2 C3 C22 . . 119.2(2) ?
C3 C4 C12 . . 119.2(2) ?
C3 C4 C5 . . 122.3(2) ?
C12 C4 C5 . . 118.4(2) ?
N4 C5 N1 . . 104.69(16) ?
N4 C5 C4 . . 108.19(17) ?
N1 C5 C4 . . 110.90(18) ?
N4 C5 H5 . . 111.0 ?
N1 C5 H5 . . 111.0 ?
C4 C5 H5 . . 111.0 ?
N2 C6 N3 . . 106.26(17) ?
N2 C6 C7 . . 111.93(19) ?
N3 C6 C7 . . 115.6(2) ?
N2 C6 H6 . . 107.6 ?
N3 C6 H6 . . 107.6 ?
C7 C6 H6 . . 107.6 ?
C8 C7 C20 . . 119.7(2) ?
C8 C7 C6 . . 120.9(2) ?
C20 C7 C6 . . 119.4(2) ?
C9 C8 C7 . . 120.9(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C10 C9 C8 . . 119.9(3) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C19 . . 120.4(3) ?
C9 C10 H10 . . 119.8 ?
C19 C10 H10 . . 119.8 ?
C1 C11 C12 . . 118.8(3) ?
C1 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
C11 C12 C4 . . 121.7(2) ?
C11 C12 H12 . . 119.2 ?
C4 C12 H12 . . 119.2 ?
O1 C13 N2 . . 124.9(3) ?
O1 C13 C14 . . 128.4(3) ?
N2 C13 C14 . . 106.7(2) ?
C13 C14 C15 . . 102.8(2) ?
C13 C14 H14A . . 111.2 ?
C15 C14 H14A . . 111.2 ?
C13 C14 H14B . . 111.2 ?
C15 C14 H14B . . 111.2 ?
H14A C14 H14B . . 109.1 ?
N1 C15 C14 . . 106.4(2) ?
N1 C15 H15A . . 110.4 ?
C14 C15 H15A . . 110.4 ?
N1 C15 H15B . . 110.4 ?
C14 C15 H15B . . 110.4 ?
H15A C15 H15B . . 108.6 ?
C17 C16 N4 . . 107.3(2) ?
C17 C16 H16A . . 110.3 ?
N4 C16 H16A . . 110.3 ?
C17 C16 H16B . . 110.3 ?
N4 C16 H16B . . 110.3 ?
H16A C16 H16B . . 108.5 ?
C16 C17 C18 . . 105.8(2) ?
C16 C17 H17A . . 110.6 ?
C18 C17 H17A . . 110.6 ?
C16 C17 H17B . . 110.6 ?
C18 C17 H17B . . 110.6 ?
H17A C17 H17B . . 108.7 ?
O2 C18 N3 . . 124.8(2) ?
O2 C18 C17 . . 129.1(2) ?
N3 C18 C17 . . 106.11(19) ?
C10 C19 C20 . . 121.8(3) ?
C10 C19 H19 . . 119.1 ?
C20 C19 H19 . . 119.1 ?
C19 C20 C7 . . 117.2(2) ?
C19 C20 C21 . . 120.0(2) ?
C7 C20 C21 . . 122.8(2) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C3 C22 H22A . . 109.5 ?
C3 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C3 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?

####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2216703'
loop_
_audit_author_name
_audit_author_address
'Kimiya Sukegawa'
;Department of Materials Chemistry, Faculty of Engineering, Shinshu University
Japan
;
_audit_update_record             
;
2022-11-01 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H38 Cl2 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         665.63

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   12.1570(17)
_cell_length_b                   12.4397(18)
_cell_length_c                   13.855(2)
_cell_angle_alpha                65.487(2)
_cell_angle_beta                 84.060(2)
_cell_angle_gamma                62.571(2)
_cell_volume                     1682.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1355
_cell_measurement_theta_min      2.3615
_cell_measurement_theta_max      20.6075
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.310
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700

_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7931
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         24.89
_diffrn_reflns_theta_full        24.89
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_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.
;

_reflns_number_total             5752
_reflns_number_gt                2449
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1188
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_restrained_S_all      0.919
_refine_ls_number_reflns         5752
_refine_ls_number_parameters     452
_refine_ls_number_restraints     672
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0.045(14)

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.3491(4) 0.7870(4) 0.1131(4) 0.0906(12) Uani d U 1.0 A 4
H H1 1.4188 0.8037 0.1077 0.109 Uiso calc R 1.0 A 4
C C2 1.2665(4) 0.8467(4) 0.0270(3) 0.0846(12) Uani d U 1.0 A 4
H H2 1.2784 0.9056 -0.0387 0.102 Uiso calc R 1.0 A 4
C C3 1.1620(3) 0.8233(3) 0.0324(3) 0.0655(9) Uani d U 1.0 A 4
C C4 1.1459(3) 0.7335(3) 0.1308(2) 0.0544(8) Uani d U 1.0 A 4
C C5 1.0403(3) 0.7110(3) 0.1341(2) 0.0536(8) Uani d U 1.0 A 4
C C6 1.0229(3) 0.6147(3) 0.2384(2) 0.0532(8) Uani d U 1.0 A 4
H H6 1.1069 0.538 0.2716 0.064 Uiso calc R 1.0 A 4
C C7 0.7702(2) 0.6980(3) 0.2925(2) 0.0495(8) Uani d U 1.0 A 4
H H7 0.786 0.6239 0.3647 0.059 Uiso calc R 1.0 A 4
C C8 0.6335(3) 0.7972(3) 0.2645(2) 0.0541(8) Uani d U 1.0 A 4
C C9 0.5427(3) 0.7800(3) 0.3334(3) 0.0597(8) Uani d U 1.0 A 4
C C10 0.5692(3) 0.6675(3) 0.4311(3) 0.0719(10) Uani d U 1.0 A 4
H H10 0.6525 0.5987 0.4545 0.086 Uiso calc R 1.0 A 4
C C11 0.4759(4) 0.6568(4) 0.4924(3) 0.0958(12) Uani d U 1.0 A 4
H H11 0.4951 0.5809 0.5581 0.115 Uiso calc R 1.0 A 4
C C12 0.3531(4) 0.7559(5) 0.4595(4) 0.1099(14) Uani d U 1.0 A 4
H H12 0.2893 0.7465 0.5027 0.132 Uiso calc R 1.0 A 4
C C13 1.3330(3) 0.7006(4) 0.2104(3) 0.0818(11) Uani d U 1.0 A 4
H H13 1.3909 0.6599 0.2712 0.098 Uiso calc R 1.0 A 4
C C14 1.2340(3) 0.6742(3) 0.2185(3) 0.0660(9) Uani d U 1.0 A 4
H H14 1.2248 0.6144 0.2851 0.079 Uiso calc R 1.0 A 4
C C15 1.0208(3) 0.6339(3) 0.4120(2) 0.0557(8) Uani d U 1.0 A 4
C C16 0.9296(3) 0.7272(3) 0.4575(2) 0.0554(8) Uani d U 1.0 A 4
H H16 0.907 0.6793 0.5282 0.066 Uiso calc R 1.0 A 4
C C17 0.8165(3) 0.8207(3) 0.3717(2) 0.0539(8) Uani d U 1.0 A 4
H H17 0.7379 0.8231 0.4028 0.065 Uiso calc R 1.0 A 4
C C18 0.7569(3) 0.5583(3) 0.2128(3) 0.0601(8) Uani d U 1.0 A 4
H H18 0.6987 0.5528 0.2691 0.072 Uiso calc R 1.0 A 4
C C19 0.8672(3) 0.4205(3) 0.2338(3) 0.0695(9) Uani d U 1.0 A 4
H H19 0.8631 0.3494 0.3011 0.083 Uiso calc R 1.0 A 4
C C20 0.8553(4) 0.3986(4) 0.1366(4) 0.0965(12) Uani d U 1.0 A 4
H H20 0.9337 0.3314 0.1231 0.116 Uiso calc R 1.0 A 4
C C21 0.8060(4) 0.5379(5) 0.0502(3) 0.1075(13) Uani d U 1.0 A 4
H H21A 0.7808 0.5449 -0.0187 0.129 Uiso calc R 1.0 A 4
H H21B 0.8647 0.5754 0.0403 0.129 Uiso calc R 1.0 A 4
C C22 0.6959(3) 0.5976(4) 0.1056(3) 0.0836(11) Uani d U 1.0 A 4
H H22 0.6409 0.6953 0.0655 0.1 Uiso calc R 1.0 A 4
C C23 0.6316(3) 0.5083(4) 0.1254(3) 0.0962(12) Uani d U 1.0 A 4
H H23A 0.585 0.5038 0.1888 0.115 Uiso calc R 1.0 A 4
H H23B 0.5738 0.5417 0.0626 0.115 Uiso calc R 1.0 A 4
C C24 0.7416(3) 0.3724(4) 0.1439(4) 0.1060(13) Uani d U 1.0 A 4
H H24A 0.7368 0.3437 0.0884 0.127 Uiso calc R 1.0 A 4
H H24B 0.7448 0.3038 0.215 0.127 Uiso calc R 1.0 A 4
C C25 0.9806(3) 0.4375(4) 0.2399(2) 0.0650(9) Uani d U 1.0 A 4
C C26 0.5986(3) 0.9081(3) 0.1692(3) 0.0671(9) Uani d U 1.0 A 4
H H26 0.6601 0.9174 0.1229 0.08 Uiso calc R 1.0 A 4
C C27 0.4751(4) 1.0074(3) 0.1389(3) 0.0890(12) Uani d U 1.0 A 4
H H27 0.4533 1.0836 0.073 0.107 Uiso calc R 1.0 A 4
C C28 0.3863(4) 0.9946(4) 0.2041(4) 0.0973(13) Uani d U 1.0 A 4
H H28 0.3026 1.0631 0.1839 0.117 Uiso calc R 1.0 A 4
C C29 0.4162(3) 0.8820(4) 0.3007(3) 0.0755(10) Uani d U 1.0 A 4
C C30 0.3239(4) 0.8643(5) 0.3679(4) 0.1037(14) Uani d U 1.0 A 4
H H30 0.2395 0.9309 0.3473 0.124 Uiso calc R 1.0 A 4
C C31 0.8145(3) 0.9559(3) 0.3335(2) 0.0660(9) Uani d U 1.0 A 4
H H31 0.7693 1.0218 0.2609 0.079 Uiso calc R 1.0 A 4
C C32 0.9524(3) 0.9183(3) 0.3440(2) 0.0712(10) Uani d U 1.0 A 4
H H32A 1.0007 0.8741 0.2975 0.085 Uiso calc R 1.0 A 4
H H32B 0.9668 0.9948 0.3321 0.085 Uiso calc R 1.0 A 4
C C33 0.9757(3) 0.8219(3) 0.4611(2) 0.0666(9) Uani d U 1.0 A 4
H H33 1.0637 0.777 0.4938 0.08 Uiso calc R 1.0 A 4
C C34 0.8799(3) 0.9115(3) 0.5105(3) 0.0788(10) Uani d U 1.0 A 4
H H34A 0.9124 0.9627 0.5266 0.095 Uiso calc R 1.0 A 4
H H34B 0.8558 0.8588 0.5768 0.095 Uiso calc R 1.0 A 4
C C35 0.7688(3) 1.0045(3) 0.4221(3) 0.0796(10) Uani d U 1.0 A 4
H H35A 0.6931 0.9954 0.4478 0.096 Uiso calc R 1.0 A 4
H H35B 0.7502 1.0987 0.3971 0.096 Uiso calc R 1.0 A 4
C C36 0.9569(3) 0.7762(3) 0.0460(2) 0.0652(9) Uani d U 1.0 A 4
H H36 0.8871 0.7602 0.0493 0.078 Uiso calc R 1.0 A 4
C C37 0.9729(3) 0.8682(3) -0.0509(3) 0.0753(10) Uani d U 1.0 A 4
H H37 0.9133 0.9149 -0.1116 0.09 Uiso calc R 1.0 A 4
C C38 1.0732(4) 0.8881(3) -0.0554(3) 0.0783(11) Uani d U 1.0 A 4
H H38 1.0843 0.9484 -0.1207 0.094 Uiso calc R 1.0 A 4
N N1 0.9433(2) 0.5618(2) 0.22800(18) 0.0549(7) Uani d U 1.0 A 4
N N2 0.8107(2) 0.6471(2) 0.20872(18) 0.0520(6) Uani d U 1.0 A 4
N N3 0.9706(2) 0.6740(2) 0.31317(18) 0.0504(6) Uani d U 1.0 A 4
N N4 0.8419(2) 0.7703(2) 0.28646(17) 0.0500(6) Uani d U 1.0 A 4
O O1 1.12645(19) 0.5444(2) 0.45062(15) 0.0711(7) Uani d U 1.0 A 4
O O2 1.0905(2) 0.3558(2) 0.24996(19) 0.0903(8) Uani d U 1.0 A 4
C C1A 0.3794(18) 0.2396(13) 0.2623(8) 0.161(5) Uani d PDU 0.455(6) B 1
H H1A1 0.4266 0.1454 0.2727 0.193 Uiso calc PR 0.455(6) B 1
H H1A2 0.2942 0.2811 0.2273 0.193 Uiso calc PR 0.455(6) B 1
Cl Cl1A 0.3837(4) 0.2626(7) 0.3760(4) 0.145(2) Uani d PDU 0.455(6) B 1
Cl Cl2A 0.4547(8) 0.3270(9) 0.2053(7) 0.230(3) Uani d PU 0.455(6) B 1
C C1B 0.3817(14) 0.2785(15) 0.2729(7) 0.177(5) Uani d PDU 0.545(6) B 2
H H1B1 0.359 0.3579 0.2865 0.212 Uiso calc PR 0.545(6) B 2
H H1B2 0.3059 0.2932 0.2379 0.212 Uiso calc PR 0.545(6) B 2
Cl Cl1B 0.4193(4) 0.1439(7) 0.3949(3) 0.180(2) Uani d PDU 0.545(6) B 2
Cl Cl2B 0.4921(3) 0.2724(5) 0.1820(4) 0.1317(15) Uani d PDU 0.545(6) B 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.346(4) ?
C1 C13 . 1.395(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.417(5) ?
C2 H2 . 0.95 ?
C3 C38 . 1.397(4) ?
C3 C4 . 1.423(4) ?
C4 C14 . 1.402(4) ?
C4 C5 . 1.428(4) ?
C5 C36 . 1.360(4) ?
C5 C6 . 1.517(4) ?
C6 N1 . 1.443(4) ?
C6 N3 . 1.445(3) ?
C6 H6 . 1.0 ?
C7 N2 . 1.482(3) ?
C7 N4 . 1.490(3) ?
C7 C8 . 1.510(4) ?
C7 H7 . 1.0 ?
C8 C26 . 1.375(4) ?
C8 C9 . 1.416(4) ?
C9 C10 . 1.414(4) ?
C9 C29 . 1.432(4) ?
C10 C11 . 1.368(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.391(5) ?
C11 H11 . 0.95 ?
C12 C30 . 1.337(5) ?
C12 H12 . 0.95 ?
C13 C14 . 1.368(4) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 O1 . 1.227(3) ?
C15 N3 . 1.350(3) ?
C15 C16 . 1.500(4) ?
C16 C33 . 1.539(4) ?
C16 C17 . 1.541(4) ?
C16 H16 . 1.0 ?
C17 N4 . 1.498(3) ?
C17 C31 . 1.528(4) ?
C17 H17 . 1.0 ?
C18 N2 . 1.501(4) ?
C18 C22 . 1.512(4) ?
C18 C19 . 1.540(4) ?
C18 H18 . 1.0 ?
C19 C25 . 1.504(4) ?
C19 C20 . 1.513(5) ?
C19 H19 . 1.0 ?
C20 C21 . 1.505(5) ?
C20 C24 . 1.544(5) ?
C20 H20 . 1.0 ?
C21 C22 . 1.508(5) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 C23 . 1.557(5) ?
C22 H22 . 1.0 ?
C23 C24 . 1.530(4) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 O2 . 1.227(3) ?
C25 N1 . 1.336(4) ?
C26 C27 . 1.395(4) ?
C26 H26 . 0.95 ?
C27 C28 . 1.358(5) ?
C27 H27 . 0.95 ?
C28 C29 . 1.400(5) ?
C28 H28 . 0.95 ?
C29 C30 . 1.420(5) ?
C30 H30 . 0.95 ?
C31 C32 . 1.524(4) ?
C31 C35 . 1.533(4) ?
C31 H31 . 1.0 ?
C32 C33 . 1.523(4) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 C34 . 1.530(4) ?
C33 H33 . 1.0 ?
C34 C35 . 1.546(4) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C35 H35A . 0.99 ?
C35 H35B . 0.99 ?
C36 C37 . 1.423(4) ?
C36 H36 . 0.95 ?
C37 C38 . 1.342(5) ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?
N1 N2 . 1.440(3) ?
N3 N4 . 1.429(3) ?
C1A Cl2A . 1.643(17) ?
C1A Cl1A . 1.724(11) ?
C1A H1A1 . 0.99 ?
C1A H1A2 . 0.99 ?
C1B Cl1B . 1.725(9) ?
C1B Cl2B . 1.740(11) ?
C1B H1B1 . 0.99 ?
C1B H1B2 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C13 . . 120.3(4) ?
C2 C1 H1 . . 119.9 ?
C13 C1 H1 . . 119.9 ?
C1 C2 C3 . . 121.1(4) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C38 C3 C2 . . 121.7(3) ?
C38 C3 C4 . . 119.3(3) ?
C2 C3 C4 . . 118.9(4) ?
C14 C4 C3 . . 117.9(3) ?
C14 C4 C5 . . 124.3(3) ?
C3 C4 C5 . . 117.8(3) ?
C36 C5 C4 . . 120.4(3) ?
C36 C5 C6 . . 121.3(3) ?
C4 C5 C6 . . 118.2(3) ?
N1 C6 N3 . . 106.0(2) ?
N1 C6 C5 . . 114.8(3) ?
N3 C6 C5 . . 112.4(2) ?
N1 C6 H6 . . 107.8 ?
N3 C6 H6 . . 107.8 ?
C5 C6 H6 . . 107.8 ?
N2 C7 N4 . . 106.1(2) ?
N2 C7 C8 . . 108.1(2) ?
N4 C7 C8 . . 108.4(2) ?
N2 C7 H7 . . 111.3 ?
N4 C7 H7 . . 111.3 ?
C8 C7 H7 . . 111.3 ?
C26 C8 C9 . . 120.0(3) ?
C26 C8 C7 . . 117.8(3) ?
C9 C8 C7 . . 122.2(3) ?
C10 C9 C8 . . 124.0(3) ?
C10 C9 C29 . . 118.3(3) ?
C8 C9 C29 . . 117.7(3) ?
C11 C10 C9 . . 120.6(3) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.7(4) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C30 C12 C11 . . 120.8(4) ?
C30 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C14 C13 C1 . . 120.3(4) ?
C14 C13 H13 . . 119.9 ?
C1 C13 H13 . . 119.9 ?
C13 C14 C4 . . 121.5(3) ?
C13 C14 H14 . . 119.3 ?
C4 C14 H14 . . 119.3 ?
O1 C15 N3 . . 124.4(3) ?
O1 C15 C16 . . 128.1(3) ?
N3 C15 C16 . . 107.2(3) ?
C15 C16 C33 . . 111.3(3) ?
C15 C16 C17 . . 104.4(2) ?
C33 C16 C17 . . 103.1(2) ?
C15 C16 H16 . . 112.5 ?
C33 C16 H16 . . 112.5 ?
C17 C16 H16 . . 112.5 ?
N4 C17 C31 . . 112.9(2) ?
N4 C17 C16 . . 107.2(2) ?
C31 C17 C16 . . 103.1(2) ?
N4 C17 H17 . . 111.1 ?
C31 C17 H17 . . 111.1 ?
C16 C17 H17 . . 111.1 ?
N2 C18 C22 . . 112.8(2) ?
N2 C18 C19 . . 107.2(2) ?
C22 C18 C19 . . 102.1(3) ?
N2 C18 H18 . . 111.4 ?
C22 C18 H18 . . 111.4 ?
C19 C18 H18 . . 111.4 ?
C25 C19 C20 . . 112.7(3) ?
C25 C19 C18 . . 104.2(3) ?
C20 C19 C18 . . 104.0(3) ?
C25 C19 H19 . . 111.8 ?
C20 C19 H19 . . 111.8 ?
C18 C19 H19 . . 111.8 ?
C21 C20 C19 . . 101.5(3) ?
C21 C20 C24 . . 101.7(3) ?
C19 C20 C24 . . 107.6(3) ?
C21 C20 H20 . . 114.8 ?
C19 C20 H20 . . 114.8 ?
C24 C20 H20 . . 114.8 ?
C20 C21 C22 . . 95.1(3) ?
C20 C21 H21A . . 112.7 ?
C22 C21 H21A . . 112.7 ?
C20 C21 H21B . . 112.7 ?
C22 C21 H21B . . 112.7 ?
H21A C21 H21B . . 110.2 ?
C21 C22 C18 . . 102.5(3) ?
C21 C22 C23 . . 101.8(3) ?
C18 C22 C23 . . 106.6(3) ?
C21 C22 H22 . . 114.8 ?
C18 C22 H22 . . 114.8 ?
C23 C22 H22 . . 114.8 ?
C24 C23 C22 . . 103.0(3) ?
C24 C23 H23A . . 111.2 ?
C22 C23 H23A . . 111.2 ?
C24 C23 H23B . . 111.2 ?
C22 C23 H23B . . 111.2 ?
H23A C23 H23B . . 109.1 ?
C23 C24 C20 . . 102.9(3) ?
C23 C24 H24A . . 111.2 ?
C20 C24 H24A . . 111.2 ?
C23 C24 H24B . . 111.2 ?
C20 C24 H24B . . 111.2 ?
H24A C24 H24B . . 109.1 ?
O2 C25 N1 . . 123.6(3) ?
O2 C25 C19 . . 127.8(3) ?
N1 C25 C19 . . 108.5(3) ?
C8 C26 C27 . . 121.7(3) ?
C8 C26 H26 . . 119.2 ?
C27 C26 H26 . . 119.2 ?
C28 C27 C26 . . 119.6(3) ?
C28 C27 H27 . . 120.2 ?
C26 C27 H27 . . 120.2 ?
C27 C28 C29 . . 121.0(4) ?
C27 C28 H28 . . 119.5 ?
C29 C28 H28 . . 119.5 ?
C28 C29 C30 . . 121.9(4) ?
C28 C29 C9 . . 119.9(3) ?
C30 C29 C9 . . 118.2(4) ?
C12 C30 C29 . . 121.5(4) ?
C12 C30 H30 . . 119.3 ?
C29 C30 H30 . . 119.3 ?
C32 C31 C17 . . 102.7(2) ?
C32 C31 C35 . . 101.0(3) ?
C17 C31 C35 . . 107.2(3) ?
C32 C31 H31 . . 114.8 ?
C17 C31 H31 . . 114.8 ?
C35 C31 H31 . . 114.8 ?
C33 C32 C31 . . 94.5(2) ?
C33 C32 H32A . . 112.8 ?
C31 C32 H32A . . 112.8 ?
C33 C32 H32B . . 112.8 ?
C31 C32 H32B . . 112.8 ?
H32A C32 H32B . . 110.3 ?
C32 C33 C34 . . 101.5(3) ?
C32 C33 C16 . . 101.5(3) ?
C34 C33 C16 . . 108.3(3) ?
C32 C33 H33 . . 114.6 ?
C34 C33 H33 . . 114.6 ?
C16 C33 H33 . . 114.6 ?
C33 C34 C35 . . 102.8(3) ?
C33 C34 H34A . . 111.2 ?
C35 C34 H34A . . 111.2 ?
C33 C34 H34B . . 111.2 ?
C35 C34 H34B . . 111.2 ?
H34A C34 H34B . . 109.1 ?
C31 C35 C34 . . 103.3(3) ?
C31 C35 H35A . . 111.1 ?
C34 C35 H35A . . 111.1 ?
C31 C35 H35B . . 111.1 ?
C34 C35 H35B . . 111.1 ?
H35A C35 H35B . . 109.1 ?
C5 C36 C37 . . 120.9(3) ?
C5 C36 H36 . . 119.6 ?
C37 C36 H36 . . 119.6 ?
C38 C37 C36 . . 119.2(3) ?
C38 C37 H37 . . 120.4 ?
C36 C37 H37 . . 120.4 ?
C37 C38 C3 . . 122.3(3) ?
C37 C38 H38 . . 118.8 ?
C3 C38 H38 . . 118.8 ?
C25 N1 N2 . . 116.0(3) ?
C25 N1 C6 . . 125.9(3) ?
N2 N1 C6 . . 118.1(2) ?
N1 N2 C7 . . 109.3(2) ?
N1 N2 C18 . . 104.0(2) ?
C7 N2 C18 . . 112.5(2) ?
C15 N3 N4 . . 116.2(2) ?
C15 N3 C6 . . 127.8(3) ?
N4 N3 C6 . . 114.9(2) ?
N3 N4 C7 . . 107.0(2) ?
N3 N4 C17 . . 103.1(2) ?
C7 N4 C17 . . 112.3(2) ?
Cl2A C1A Cl1A . . 89.5(8) ?
Cl2A C1A H1A1 . . 113.7 ?
Cl1A C1A H1A1 . . 113.7 ?
Cl2A C1A H1A2 . . 113.7 ?
Cl1A C1A H1A2 . . 113.7 ?
H1A1 C1A H1A2 . . 111.0 ?
Cl1B C1B Cl2B . . 118.7(9) ?
Cl1B C1B H1B1 . . 107.6 ?
Cl2B C1B H1B1 . . 107.6 ?
Cl1B C1B H1B2 . . 107.6 ?
Cl2B C1B H1B2 . . 107.6 ?
H1B1 C1B H1B2 . . 107.1 ?

####################################################################### 
# 
# 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_220804_16AK158close_7
_database_code_depnum_ccdc_archive 'CCDC 2216732'
loop_
_audit_author_name
_audit_author_address
'Kimiya Sukegawa'
;Department of Materials Chemistry, Faculty of Engineering, Shinshu University
Japan
;
_audit_update_record             
;
2022-11-01 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C76 H72 N8 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         1161.41

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.3011(11)
_cell_length_b                   13.3310(5)
_cell_length_c                   22.1748(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.356(3)
_cell_angle_gamma                90
_cell_volume                     7012.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5941
_cell_measurement_theta_min      2.3958
_cell_measurement_theta_max      21.8837
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.310
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464

_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
The unit cell contains 8 trichloromethane molecules which have been treated 
as a diffuse contribution to the overall scattering without specific atom 
positions by SQUEEZE/PLATON. 
;


_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            24058
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             6160
_reflns_number_gt                3914
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1509
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_number_reflns         6160
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.29125(7) 0.61380(11) 0.54610(6) 0.0799(4) Uani d . . . 1 . .
O O2 0.42174(7) 0.81161(11) 0.54155(6) 0.0897(5) Uani d . . . 1 . .
N N1 0.36866(7) 0.73830(11) 0.44802(7) 0.0548(4) Uani d . . . 1 . .
N N2 0.33764(6) 0.75912(10) 0.38091(6) 0.0495(4) Uani d . . . 1 . .
N N3 0.27681(6) 0.62085(11) 0.38209(6) 0.0511(4) Uani d . . . 1 . .
N N4 0.30667(7) 0.61209(11) 0.45019(7) 0.0559(4) Uani d . . . 1 . .
C C1 0.42938(12) 0.2714(2) 0.53532(16) 0.1018(9) Uani d . . . 1 . .
H H1 0.436003 0.206439 0.554082 0.122000 Uiso calc U . R 1 . .
C C2 0.45228(10) 0.29726(17) 0.49130(13) 0.0839(7) Uani d . . . 1 . .
H H3 0.475136 0.250205 0.479468 0.101000 Uiso calc U . R 1 . .
C C3 0.44313(9) 0.39264(15) 0.46230(10) 0.0660(5) Uani d . . . 1 . .
C C4 0.40914(8) 0.46365(14) 0.48037(9) 0.0608(5) Uani d . . . 1 . .
C C5 0.40048(8) 0.56059(14) 0.45079(8) 0.0558(5) Uani d . . . 1 . .
C C6 0.36596(8) 0.63774(14) 0.47104(9) 0.0565(5) Uani d . . . 1 . .
H H33 0.380434 0.640127 0.519112 0.068000 Uiso calc U . R 1 . .
C C7 0.27764(8) 0.72876(13) 0.36527(8) 0.0499(5) Uani d . . . 1 . .
H H31 0.260273 0.769603 0.391324 0.060000 Uiso calc U . R 1 . .
C C8 0.24581(8) 0.74651(13) 0.29413(8) 0.0493(5) Uani d . . . 1 . .
C C9 0.30304(8) 0.62494(14) 0.25558(9) 0.0573(5) Uani d . . . 1 . .
H H17 0.325527 0.608293 0.298516 0.069000 Uiso calc U . R 1 . .
C C10 0.31321(10) 0.57907(16) 0.20577(10) 0.0702(6) Uani d . . . 1 . .
H H18 0.342870 0.531436 0.214587 0.084000 Uiso calc U . R 1 . .
C C11 0.28073(12) 0.60093(19) 0.14188(10) 0.0800(7) Uani d . . . 1 . .
H H2 0.288006 0.567791 0.107654 0.096000 Uiso calc U . R 1 . .
C C12 0.46712(9) 0.41999(18) 0.41646(11) 0.0733(6) Uani d . . . 1 . .
H H4 0.489998 0.373036 0.404559 0.088000 Uiso calc U . R 1 . .
C C13 0.45835(9) 0.51237(17) 0.38863(10) 0.0693(6) Uani d . . . 1 . .
H H36 0.474745 0.529357 0.357413 0.083000 Uiso calc U . R 1 . .
C C14 0.42487(8) 0.58257(15) 0.40631(9) 0.0609(5) Uani d . . . 1 . .
H H5 0.419091 0.647000 0.386783 0.073000 Uiso calc U . R 1 . .
C C15 0.27352(9) 0.60938(14) 0.48691(9) 0.0582(5) Uani d . . . 1 . .
C C16 0.21460(9) 0.58854(14) 0.44305(8) 0.0568(5) Uani d . . . 1 . .
H H32 0.186897 0.638974 0.447431 0.068000 Uiso calc U . R 1 . .
C C17 0.19741(10) 0.48022(16) 0.45091(10) 0.0751(6) Uani d . . . 1 . .
H H6 0.204643 0.459291 0.496391 0.090000 Uiso calc U . R 1 . .
C C18 0.13651(11) 0.46536(19) 0.40538(11) 0.0887(7) Uani d . . . 1 . .
H H8 0.112074 0.521150 0.409294 0.106000 Uiso calc U . R 1 . .
H H7 0.120874 0.401219 0.414239 0.106000 Uiso calc U . R 1 . .
C C19 0.14208(11) 0.4643(2) 0.33806(12) 0.0947(8) Uani d . . . 1 . .
H H9 0.129265 0.399579 0.315934 0.114000 Uiso calc U . R 1 . .
H H10 0.120141 0.519478 0.310831 0.114000 Uiso calc U . R 1 . .
C C20 0.20580(10) 0.47935(17) 0.35372(11) 0.0795(7) Uani d . . . 1 . .
H H13 0.219996 0.457611 0.318956 0.095000 Uiso calc U . R 1 . .
C C21 0.23006(12) 0.42076(17) 0.41658(13) 0.0890(7) Uani d . . . 1 . .
H H12 0.219705 0.348830 0.411728 0.107000 Uiso calc U . R 1 . .
H H11 0.271412 0.428407 0.436936 0.107000 Uiso calc U . R 1 . .
C C22 0.21850(8) 0.58748(14) 0.37464(8) 0.0571(5) Uani d . . . 1 . .
H H14 0.189798 0.633439 0.345148 0.069000 Uiso calc U . R 1 . .
C C23 0.20225(9) 0.81349(15) 0.27792(10) 0.0657(5) Uani d . . . 1 . .
H H20 0.193015 0.846015 0.311071 0.079000 Uiso calc U . R 1 . .
C C24 0.17066(10) 0.83552(17) 0.21322(11) 0.0792(7) Uani d . . . 1 . .
H H19 0.140584 0.882462 0.203225 0.095000 Uiso calc U . R 1 . .
C C25 0.18303(10) 0.79026(17) 0.16571(11) 0.0762(6) Uani d . . . 1 . .
H H15 0.161782 0.806166 0.122239 0.091000 Uiso calc U . R 1 . .
C C26 0.22693(9) 0.71968(15) 0.17925(9) 0.0599(5) Uani d . . . 1 . .
C C27 0.23906(12) 0.66927(18) 0.12923(10) 0.0767(7) Uani d . . . 1 . .
H H16 0.217271 0.684086 0.085755 0.092000 Uiso calc U . R 1 . .
C C28 0.34322(8) 0.87061(13) 0.37560(8) 0.0538(5) Uani d . . . 1 . .
H H30 0.305359 0.903548 0.359528 0.065000 Uiso calc U . R 1 . .
C C29 0.37842(10) 0.90119(14) 0.33551(10) 0.0704(6) Uani d . . . 1 . .
H H29 0.370013 0.863451 0.294253 0.084000 Uiso calc U . R 1 . .
C C30 0.37462(11) 1.01551(15) 0.32833(10) 0.0830(7) Uani d . . . 1 . .
H H21 0.335131 1.038669 0.316560 0.100000 Uiso calc U . R 1 . .
H H28 0.389864 1.038514 0.295191 0.100000 Uiso calc U . R 1 . .
C C31 0.41082(12) 1.05389(17) 0.39526(12) 0.0947(8) Uani d . . . 1 . .
H H23 0.443517 1.092967 0.393483 0.114000 Uiso calc U . R 1 . .
H H22 0.388406 1.096055 0.414225 0.114000 Uiso calc U . R 1 . .
C C32 0.42971(11) 0.95666(18) 0.43328(11) 0.0875(7) Uani d . . . 1 . .
H H25 0.463377 0.963664 0.473455 0.105000 Uiso calc U . R 1 . .
C C33 0.37822(9) 0.90893(15) 0.44283(9) 0.0625(5) Uani d . . . 1 . .
H H24 0.356761 0.958789 0.458978 0.075000 Uiso calc U . R 1 . .
C C34 0.39254(9) 0.81720(15) 0.48438(9) 0.0624(5) Uani d . . . 1 . .
C C35 0.43815(11) 0.88807(19) 0.38305(14) 0.0942(8) Uani d . . . 1 . .
H H27 0.446546 0.818056 0.398251 0.113000 Uiso calc U . R 1 . .
H H26 0.467161 0.913053 0.366197 0.113000 Uiso calc U . R 1 . .
C C36 0.38621(9) 0.43438(17) 0.52736(10) 0.0760(6) Uani d . . . 1 . .
H H35 0.363945 0.480357 0.540986 0.091000 Uiso calc U . R 1 . .
C C37 0.39599(11) 0.3393(2) 0.55360(14) 0.0983(8) Uani d . . . 1 . .
H H34 0.379707 0.319962 0.584518 0.118000 Uiso calc U . R 1 . .
C C38 0.25956(8) 0.69694(13) 0.24445(8) 0.0492(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 . 1.232(2) ?
O2 C34 . 1.228(2) ?
N1 C34 . 1.335(2) ?
N1 C6 . 1.444(2) ?
N1 N2 . 1.4474(18) ?
N2 C7 . 1.491(2) ?
N2 C28 . 1.501(2) ?
N3 N4 . 1.4392(19) ?
N3 C7 . 1.488(2) ?
N3 C22 . 1.494(2) ?
N4 C15 . 1.358(2) ?
N4 C6 . 1.448(2) ?
C1 C2 . 1.342(4) ?
C1 C37 . 1.391(4) ?
C1 H1 . 0.950000 ?
C2 C3 . 1.407(3) ?
C2 H3 . 0.950000 ?
C3 C12 . 1.402(3) ?
C3 C4 . 1.427(3) ?
C4 C36 . 1.413(3) ?
C4 C5 . 1.431(3) ?
C5 C14 . 1.365(3) ?
C5 C6 . 1.515(3) ?
C6 H33 . 1.000000 ?
C7 C8 . 1.520(2) ?
C7 H31 . 1.000000 ?
C8 C23 . 1.366(3) ?
C8 C38 . 1.428(2) ?
C9 C10 . 1.363(3) ?
C9 C38 . 1.416(3) ?
C9 H17 . 0.950000 ?
C10 C11 . 1.399(3) ?
C10 H18 . 0.950000 ?
C11 C27 . 1.347(3) ?
C11 H2 . 0.950000 ?
C12 C13 . 1.361(3) ?
C12 H4 . 0.950000 ?
C13 C14 . 1.406(3) ?
C13 H36 . 0.950000 ?
C14 H5 . 0.950000 ?
C15 C16 . 1.496(3) ?
C16 C17 . 1.535(3) ?
C16 C22 . 1.554(2) ?
C16 H32 . 1.000000 ?
C17 C21 . 1.526(3) ?
C17 C18 . 1.533(3) ?
C17 H6 . 1.000000 ?
C18 C19 . 1.548(3) ?
C18 H8 . 0.990000 ?
C18 H7 . 0.990000 ?
C19 C20 . 1.540(3) ?
C19 H9 . 0.990000 ?
C19 H10 . 0.990000 ?
C20 C22 . 1.514(3) ?
C20 C21 . 1.528(3) ?
C20 H13 . 1.000000 ?
C21 H12 . 0.990000 ?
C21 H11 . 0.990000 ?
C22 H14 . 1.000000 ?
C23 C24 . 1.409(3) ?
C23 H20 . 0.950000 ?
C24 C25 . 1.342(3) ?
C24 H19 . 0.950000 ?
C25 C26 . 1.406(3) ?
C25 H15 . 0.950000 ?
C26 C27 . 1.419(3) ?
C26 C38 . 1.426(2) ?
C27 H16 . 0.950000 ?
C28 C29 . 1.517(3) ?
C28 C33 . 1.533(2) ?
C28 H30 . 1.000000 ?
C29 C35 . 1.522(3) ?
C29 C30 . 1.532(3) ?
C29 H29 . 1.000000 ?
C30 C31 . 1.536(3) ?
C30 H21 . 0.990000 ?
C30 H28 . 0.990000 ?
C31 C32 . 1.529(3) ?
C31 H23 . 0.990000 ?
C31 H22 . 0.990000 ?
C32 C35 . 1.512(3) ?
C32 C33 . 1.530(3) ?
C32 H25 . 1.000000 ?
C33 C34 . 1.498(3) ?
C33 H24 . 1.000000 ?
C35 H27 . 0.990000 ?
C35 H26 . 0.990000 ?
C36 C37 . 1.381(3) ?
C36 H35 . 0.950000 ?
C37 H34 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C34 N1 C6 . . 125.79(15) ?
C34 N1 N2 . . 116.07(15) ?
C6 N1 N2 . . 117.77(13) ?
N1 N2 C7 . . 109.34(13) ?
N1 N2 C28 . . 103.78(12) ?
C7 N2 C28 . . 111.51(13) ?
N4 N3 C7 . . 107.06(12) ?
N4 N3 C22 . . 103.28(12) ?
C7 N3 C22 . . 111.08(14) ?
C15 N4 N3 . . 115.03(16) ?
C15 N4 C6 . . 127.02(15) ?
N3 N4 C6 . . 115.04(13) ?
C2 C1 C37 . . 120.3(2) ?
C2 C1 H1 . . 119.900000 ?
C37 C1 H1 . . 119.900000 ?
C1 C2 C3 . . 121.4(2) ?
C1 C2 H3 . . 119.300000 ?
C3 C2 H3 . . 119.300000 ?
C12 C3 C2 . . 121.5(2) ?
C12 C3 C4 . . 119.11(19) ?
C2 C3 C4 . . 119.4(2) ?
C36 C4 C3 . . 117.78(18) ?
C36 C4 C5 . . 123.42(19) ?
C3 C4 C5 . . 118.79(18) ?
C14 C5 C4 . . 119.30(18) ?
C14 C5 C6 . . 121.37(17) ?
C4 C5 C6 . . 119.29(17) ?
N1 C6 N4 . . 106.10(14) ?
N1 C6 C5 . . 114.98(15) ?
N4 C6 C5 . . 112.63(15) ?
N1 C6 H33 . . 107.600000 ?
N4 C6 H33 . . 107.600000 ?
C5 C6 H33 . . 107.600000 ?
N3 C7 N2 . . 107.83(14) ?
N3 C7 C8 . . 111.23(14) ?
N2 C7 C8 . . 109.16(14) ?
N3 C7 H31 . . 109.500000 ?
N2 C7 H31 . . 109.500000 ?
C8 C7 H31 . . 109.500000 ?
C23 C8 C38 . . 119.36(17) ?
C23 C8 C7 . . 117.57(16) ?
C38 C8 C7 . . 123.07(16) ?
C10 C9 C38 . . 121.15(18) ?
C10 C9 H17 . . 119.400000 ?
C38 C9 H17 . . 119.400000 ?
C9 C10 C11 . . 121.1(2) ?
C9 C10 H18 . . 119.400000 ?
C11 C10 H18 . . 119.400000 ?
C27 C11 C10 . . 119.6(2) ?
C27 C11 H2 . . 120.200000 ?
C10 C11 H2 . . 120.200000 ?
C13 C12 C3 . . 121.4(2) ?
C13 C12 H4 . . 119.300000 ?
C3 C12 H4 . . 119.300000 ?
C12 C13 C14 . . 119.7(2) ?
C12 C13 H36 . . 120.200000 ?
C14 C13 H36 . . 120.200000 ?
C5 C14 C13 . . 121.74(19) ?
C5 C14 H5 . . 119.100000 ?
C13 C14 H5 . . 119.100000 ?
O1 C15 N4 . . 124.4(2) ?
O1 C15 C16 . . 127.81(18) ?
N4 C15 C16 . . 107.39(15) ?
C15 C16 C17 . . 111.00(16) ?
C15 C16 C22 . . 104.42(15) ?
C17 C16 C22 . . 102.65(15) ?
C15 C16 H32 . . 112.700000 ?
C17 C16 H32 . . 112.700000 ?
C22 C16 H32 . . 112.700000 ?
C21 C17 C18 . . 101.47(19) ?
C21 C17 C16 . . 102.01(16) ?
C18 C17 C16 . . 107.83(18) ?
C21 C17 H6 . . 114.700000 ?
C18 C17 H6 . . 114.700000 ?
C16 C17 H6 . . 114.700000 ?
C17 C18 C19 . . 103.20(18) ?
C17 C18 H8 . . 111.100000 ?
C19 C18 H8 . . 111.100000 ?
C17 C18 H7 . . 111.100000 ?
C19 C18 H7 . . 111.100000 ?
H8 C18 H7 . . 109.100000 ?
C20 C19 C18 . . 102.76(19) ?
C20 C19 H9 . . 111.200000 ?
C18 C19 H9 . . 111.200000 ?
C20 C19 H10 . . 111.200000 ?
C18 C19 H10 . . 111.200000 ?
H9 C19 H10 . . 109.100000 ?
C22 C20 C21 . . 103.42(17) ?
C22 C20 C19 . . 106.68(19) ?
C21 C20 C19 . . 101.31(19) ?
C22 C20 H13 . . 114.700000 ?
C21 C20 H13 . . 114.700000 ?
C19 C20 H13 . . 114.700000 ?
C17 C21 C20 . . 94.25(18) ?
C17 C21 H12 . . 112.900000 ?
C20 C21 H12 . . 112.900000 ?
C17 C21 H11 . . 112.900000 ?
C20 C21 H11 . . 112.900000 ?
H12 C21 H11 . . 110.300000 ?
N3 C22 C20 . . 114.43(16) ?
N3 C22 C16 . . 106.56(14) ?
C20 C22 C16 . . 103.23(15) ?
N3 C22 H14 . . 110.800000 ?
C20 C22 H14 . . 110.800000 ?
C16 C22 H14 . . 110.800000 ?
C8 C23 C24 . . 121.6(2) ?
C8 C23 H20 . . 119.200000 ?
C24 C23 H20 . . 119.200000 ?
C25 C24 C23 . . 120.1(2) ?
C25 C24 H19 . . 120.000000 ?
C23 C24 H19 . . 120.000000 ?
C24 C25 C26 . . 121.04(19) ?
C24 C25 H15 . . 119.500000 ?
C26 C25 H15 . . 119.500000 ?
C25 C26 C27 . . 121.3(2) ?
C25 C26 C38 . . 119.63(18) ?
C27 C26 C38 . . 119.1(2) ?
C11 C27 C26 . . 121.6(2) ?
C11 C27 H16 . . 119.200000 ?
C26 C27 H16 . . 119.200000 ?
N2 C28 C29 . . 113.73(14) ?
N2 C28 C33 . . 106.98(14) ?
C29 C28 C33 . . 102.84(16) ?
N2 C28 H30 . . 111.000000 ?
C29 C28 H30 . . 111.000000 ?
C33 C28 H30 . . 111.000000 ?
C28 C29 C35 . . 101.96(17) ?
C28 C29 C30 . . 107.45(17) ?
C35 C29 C30 . . 101.39(18) ?
C28 C29 H29 . . 114.800000 ?
C35 C29 H29 . . 114.800000 ?
C30 C29 H29 . . 114.800000 ?
C29 C30 C31 . . 103.67(18) ?
C29 C30 H21 . . 111.000000 ?
C31 C30 H21 . . 111.000000 ?
C29 C30 H28 . . 111.000000 ?
C31 C30 H28 . . 111.000000 ?
H21 C30 H28 . . 109.000000 ?
C32 C31 C30 . . 102.55(18) ?
C32 C31 H23 . . 111.300000 ?
C30 C31 H23 . . 111.300000 ?
C32 C31 H22 . . 111.300000 ?
C30 C31 H22 . . 111.300000 ?
H23 C31 H22 . . 109.200000 ?
C35 C32 C31 . . 101.75(19) ?
C35 C32 C33 . . 101.29(17) ?
C31 C32 C33 . . 108.1(2) ?
C35 C32 H25 . . 114.700000 ?
C31 C32 H25 . . 114.700000 ?
C33 C32 H25 . . 114.700000 ?
C34 C33 C32 . . 112.92(19) ?
C34 C33 C28 . . 105.10(15) ?
C32 C33 C28 . . 103.63(16) ?
C34 C33 H24 . . 111.600000 ?
C32 C33 H24 . . 111.600000 ?
C28 C33 H24 . . 111.600000 ?
O2 C34 N1 . . 124.00(19) ?
O2 C34 C33 . . 127.94(18) ?
N1 C34 C33 . . 108.05(16) ?
C32 C35 C29 . . 94.59(18) ?
C32 C35 H27 . . 112.800000 ?
C29 C35 H27 . . 112.800000 ?
C32 C35 H26 . . 112.800000 ?
C29 C35 H26 . . 112.800000 ?
H27 C35 H26 . . 110.300000 ?
C37 C36 C4 . . 120.3(2) ?
C37 C36 H35 . . 119.800000 ?
C4 C36 H35 . . 119.800000 ?
C36 C37 C1 . . 120.8(2) ?
C36 C37 H34 . . 119.600000 ?
C1 C37 H34 . . 119.600000 ?
C9 C38 C26 . . 117.50(17) ?
C9 C38 C8 . . 124.23(16) ?
C26 C38 C8 . . 118.26(18) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C34 N1 N2 C7 . . . . -119.65(17) ?
C6 N1 N2 C7 . . . . 53.75(19) ?
C34 N1 N2 C28 . . . . -0.6(2) ?
C6 N1 N2 C28 . . . . 172.84(15) ?
C7 N3 N4 C15 . . . . 97.79(17) ?
C22 N3 N4 C15 . . . . -19.53(18) ?
C7 N3 N4 C6 . . . . -64.29(18) ?
C22 N3 N4 C6 . . . . 178.39(14) ?
C37 C1 C2 C3 . . . . -0.3(4) ?
C1 C2 C3 C12 . . . . 179.8(2) ?
C1 C2 C3 C4 . . . . 0.5(3) ?
C12 C3 C4 C36 . . . . -179.11(18) ?
C2 C3 C4 C36 . . . . 0.3(3) ?
C12 C3 C4 C5 . . . . 0.3(3) ?
C2 C3 C4 C5 . . . . 179.62(18) ?
C36 C4 C5 C14 . . . . 179.26(19) ?
C3 C4 C5 C14 . . . . -0.1(3) ?
C36 C4 C5 C6 . . . . 1.2(3) ?
C3 C4 C5 C6 . . . . -178.14(17) ?
C34 N1 C6 N4 . . . . 122.39(19) ?
N2 N1 C6 N4 . . . . -50.30(19) ?
C34 N1 C6 C5 . . . . -112.4(2) ?
N2 N1 C6 C5 . . . . 74.9(2) ?
C15 N4 C6 N1 . . . . -103.93(19) ?
N3 N4 C6 N1 . . . . 55.63(18) ?
C15 N4 C6 C5 . . . . 129.44(18) ?
N3 N4 C6 C5 . . . . -70.99(18) ?
C14 C5 C6 N1 . . . . -9.5(3) ?
C4 C5 C6 N1 . . . . 168.54(16) ?
C14 C5 C6 N4 . . . . 112.22(19) ?
C4 C5 C6 N4 . . . . -69.7(2) ?
N4 N3 C7 N2 . . . . 61.63(16) ?
C22 N3 C7 N2 . . . . 173.70(12) ?
N4 N3 C7 C8 . . . . -178.70(14) ?
C22 N3 C7 C8 . . . . -66.63(17) ?
N1 N2 C7 N3 . . . . -56.59(16) ?
C28 N2 C7 N3 . . . . -170.77(12) ?
N1 N2 C7 C8 . . . . -177.56(13) ?
C28 N2 C7 C8 . . . . 68.26(17) ?
N3 C7 C8 C23 . . . . 122.98(18) ?
N2 C7 C8 C23 . . . . -118.14(18) ?
N3 C7 C8 C38 . . . . -57.2(2) ?
N2 C7 C8 C38 . . . . 61.7(2) ?
C38 C9 C10 C11 . . . . -0.5(3) ?
C9 C10 C11 C27 . . . . 0.8(3) ?
C2 C3 C12 C13 . . . . -179.8(2) ?
C4 C3 C12 C13 . . . . -0.5(3) ?
C3 C12 C13 C14 . . . . 0.5(3) ?
C4 C5 C14 C13 . . . . 0.1(3) ?
C6 C5 C14 C13 . . . . 178.11(18) ?
C12 C13 C14 C5 . . . . -0.3(3) ?
N3 N4 C15 O1 . . . . -171.20(16) ?
C6 N4 C15 O1 . . . . -11.6(3) ?
N3 N4 C15 C16 . . . . 15.2(2) ?
C6 N4 C15 C16 . . . . 174.74(16) ?
O1 C15 C16 C17 . . . . -67.4(2) ?
N4 C15 C16 C17 . . . . 105.93(17) ?
O1 C15 C16 C22 . . . . -177.36(19) ?
N4 C15 C16 C22 . . . . -4.01(19) ?
C15 C16 C17 C21 . . . . -74.5(2) ?
C22 C16 C17 C21 . . . . 36.6(2) ?
C15 C16 C17 C18 . . . . 179.10(16) ?
C22 C16 C17 C18 . . . . -69.83(19) ?
C21 C17 C18 C19 . . . . -35.4(2) ?
C16 C17 C18 C19 . . . . 71.4(2) ?
C17 C18 C19 C20 . . . . -0.3(2) ?
C18 C19 C20 C22 . . . . -72.1(2) ?
C18 C19 C20 C21 . . . . 35.7(2) ?
C18 C17 C21 C20 . . . . 56.30(19) ?
C16 C17 C21 C20 . . . . -55.0(2) ?
C22 C20 C21 C17 . . . . 54.0(2) ?
C19 C20 C21 C17 . . . . -56.4(2) ?
N4 N3 C22 C20 . . . . -98.25(17) ?
C7 N3 C22 C20 . . . . 147.29(16) ?
N4 N3 C22 C16 . . . . 15.15(17) ?
C7 N3 C22 C16 . . . . -99.30(16) ?
C21 C20 C22 N3 . . . . 82.70(19) ?
C19 C20 C22 N3 . . . . -170.92(15) ?
C21 C20 C22 C16 . . . . -32.7(2) ?
C19 C20 C22 C16 . . . . 73.7(2) ?
C15 C16 C22 N3 . . . . -7.34(18) ?
C17 C16 C22 N3 . . . . -123.25(16) ?
C15 C16 C22 C20 . . . . 113.53(17) ?
C17 C16 C22 C20 . . . . -2.4(2) ?
C38 C8 C23 C24 . . . . -0.4(3) ?
C7 C8 C23 C24 . . . . 179.38(18) ?
C8 C23 C24 C25 . . . . 0.1(3) ?
C23 C24 C25 C26 . . . . 0.7(3) ?
C24 C25 C26 C27 . . . . 178.0(2) ?
C24 C25 C26 C38 . . . . -1.1(3) ?
C10 C11 C27 C26 . . . . -0.3(3) ?
C25 C26 C27 C11 . . . . -179.4(2) ?
C38 C26 C27 C11 . . . . -0.3(3) ?
N1 N2 C28 C29 . . . . 112.44(17) ?
C7 N2 C28 C29 . . . . -129.97(17) ?
N1 N2 C28 C33 . . . . -0.39(18) ?
C7 N2 C28 C33 . . . . 117.20(15) ?
N2 C28 C29 C35 . . . . -80.13(19) ?
C33 C28 C29 C35 . . . . 35.17(19) ?
N2 C28 C29 C30 . . . . 173.71(16) ?
C33 C28 C29 C30 . . . . -71.0(2) ?
C28 C29 C30 C31 . . . . 72.8(2) ?
C35 C29 C30 C31 . . . . -33.7(2) ?
C29 C30 C31 C32 . . . . -1.5(3) ?
C30 C31 C32 C35 . . . . 36.5(3) ?
C30 C31 C32 C33 . . . . -69.6(2) ?
C35 C32 C33 C34 . . . . 78.3(2) ?
C31 C32 C33 C34 . . . . -175.18(17) ?
C35 C32 C33 C28 . . . . -34.8(2) ?
C31 C32 C33 C28 . . . . 71.6(2) ?
N2 C28 C33 C34 . . . . 1.1(2) ?
C29 C28 C33 C34 . . . . -119.00(17) ?
N2 C28 C33 C32 . . . . 119.79(17) ?
C29 C28 C33 C32 . . . . -0.3(2) ?
C6 N1 C34 O2 . . . . 9.7(3) ?
N2 N1 C34 O2 . . . . -177.49(19) ?
C6 N1 C34 C33 . . . . -171.51(17) ?
N2 N1 C34 C33 . . . . 1.3(2) ?
C32 C33 C34 O2 . . . . 65.0(3) ?
C28 C33 C34 O2 . . . . 177.3(2) ?
C32 C33 C34 N1 . . . . -113.7(2) ?
C28 C33 C34 N1 . . . . -1.4(2) ?
C31 C32 C35 C29 . . . . -56.4(2) ?
C33 C32 C35 C29 . . . . 55.03(19) ?
C28 C29 C35 C32 . . . . -55.82(18) ?
C30 C29 C35 C32 . . . . 55.00(19) ?
C3 C4 C36 C37 . . . . -1.1(3) ?
C5 C4 C36 C37 . . . . 179.6(2) ?
C4 C36 C37 C1 . . . . 1.3(4) ?
C2 C1 C37 C36 . . . . -0.6(4) ?
C10 C9 C38 C26 . . . . -0.1(3) ?
C10 C9 C38 C8 . . . . 178.75(18) ?
C25 C26 C38 C9 . . . . 179.62(18) ?
C27 C26 C38 C9 . . . . 0.5(3) ?
C25 C26 C38 C8 . . . . 0.7(3) ?
C27 C26 C38 C8 . . . . -178.43(17) ?
C23 C8 C38 C9 . . . . -178.78(18) ?
C7 C8 C38 C9 . . . . 1.4(3) ?
C23 C8 C38 C26 . . . . 0.0(3) ?
C7 C8 C38 C26 . . . . -179.77(16) ?




