# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2a_2(S)-1a
_database_code_depnum_ccdc_archive 'CCDC 2057487'
loop_
_audit_author_name
_audit_author_address
'Koichi Kodama'
;Saitama University
Japan
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C63 H52 N2 O4'
_chemical_formula_weight         901.06

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0606(15)
_cell_length_b                   20.736(3)
_cell_length_c                   22.810(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4758.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3333
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      21.68

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22966
_diffrn_reflns_av_unetI/netI     0.1168
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.327
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8364
_reflns_number_gt                5316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         8364
_refine_ls_number_parameters     644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_restrained_S_all      0.794
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9851(3) 0.33039(11) 0.28567(11) 0.0296(7) Uani 1 1 d . . . . .
O2 O 0.8819(3) -0.12482(13) 0.30343(13) 0.0331(7) Uani 1 1 d . . . . .
H52 H 0.939(4) -0.141(2) 0.273(2) 0.063(16) Uiso 1 1 d . . . . .
O3 O 0.7589(3) 0.28006(14) 0.24295(12) 0.0361(7) Uani 1 1 d . . . . .
N2 N 0.3862(3) 0.05257(16) 0.67302(14) 0.0262(8) Uani 1 1 d . . . . .
H49 H 0.389(4) 0.0962(18) 0.6826(15) 0.032(11) Uiso 1 1 d . . . . .
N1 N 0.6110(3) 0.05339(16) 0.66493(14) 0.0267(8) Uani 1 1 d . . . . .
O4 O 0.6551(3) -0.22093(15) 0.33280(14) 0.0435(8) Uani 1 1 d . . . . .
H50 H 0.739(6) -0.226(3) 0.340(2) 0.10(2) Uiso 1 1 d . . . . .
C2 C 1.0143(4) -0.17367(17) 0.47109(18) 0.0288(10) Uani 1 1 d . . . . .
C3 C 0.7584(4) 0.22286(18) 0.39593(17) 0.0247(10) Uani 1 1 d . . . . .
C4 C 0.6896(4) -0.12661(19) 0.39246(17) 0.0271(10) Uani 1 1 d . . . . .
C5 C 0.4975(4) 0.02229(17) 0.65964(15) 0.0220(9) Uani 1 1 d . . . . .
C64 C 0.8324(4) -0.14305(17) 0.40353(17) 0.0253(10) Uani 1 1 d . . . . .
C6 C 0.8077(4) 0.23651(16) 0.33798(16) 0.0237(9) Uani 1 1 d . . . . .
C7 C 0.9670(4) 0.04359(18) 0.34234(16) 0.0266(10) Uani 1 1 d . . . . .
H1 H 0.909477 0.008767 0.351722 0.032 Uiso 1 1 calc R U . . .
C8 C 1.0002(4) 0.15837(17) 0.32668(15) 0.0233(9) Uani 1 1 d . . . . .
C9 C 0.9243(4) -0.14066(18) 0.35865(18) 0.0269(10) Uani 1 1 d . . . . .
C10 C 0.9493(4) 0.22304(18) 0.32200(16) 0.0237(9) Uani 1 1 d . . . . .
C11 C 1.0320(4) 0.27095(18) 0.29933(16) 0.0259(10) Uani 1 1 d . . . . .
C12 C 0.9182(4) 0.10486(17) 0.34149(15) 0.0247(10) Uani 1 1 d . . . . .
H2 H 0.827407 0.112033 0.350968 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8073(4) -0.01411(18) 0.69227(17) 0.0252(9) Uani 1 1 d . . . . .
C14 C 0.4922(4) -0.04583(17) 0.63973(16) 0.0214(9) Uani 1 1 d . . . . .
C15 C 0.6205(4) 0.22769(18) 0.40827(17) 0.0270(9) Uani 1 1 d . . . . .
C16 C 0.6330(4) -0.06924(18) 0.41685(16) 0.0269(9) Uani 1 1 d . . . . .
C17 C 0.7187(4) 0.26031(18) 0.29740(18) 0.0285(10) Uani 1 1 d . . . . .
C18 C 1.1347(4) 0.14482(18) 0.31282(15) 0.0250(9) Uani 1 1 d . . . . .
C19 C 0.8768(4) -0.16129(18) 0.46081(17) 0.0248(9) Uani 1 1 d . . . . .
C20 C 1.2177(4) 0.19636(18) 0.29420(17) 0.0300(10) Uani 1 1 d . . . . .
H3 H 1.309096 0.188674 0.286431 0.036 Uiso 1 1 calc R U . . .
C21 C 1.1034(4) -0.16815(17) 0.42396(18) 0.0312(10) Uani 1 1 d . . . . .
H19 H 1.195560 -0.175091 0.430576 0.037 Uiso 1 1 calc R U . . .
C22 C 0.8447(4) 0.20573(17) 0.44253(17) 0.0276(10) Uani 1 1 d . . . . .
H4 H 0.937444 0.202431 0.435384 0.033 Uiso 1 1 calc R U . . .
C23 C 1.1668(4) 0.25655(18) 0.28748(17) 0.0298(10) Uani 1 1 d . . . . .
H5 H 1.223628 0.290154 0.274370 0.036 Uiso 1 1 calc R U . . .
C24 C 1.0608(4) -0.15308(18) 0.36906(19) 0.0297(10) Uani 1 1 d . . . . .
H20 H 1.122645 -0.150876 0.337645 0.036 Uiso 1 1 calc R U . . .
C25 C 0.1956(4) 0.03826(19) 0.60637(16) 0.0261(10) Uani 1 1 d . . . . .
C26 C 0.8319(4) -0.18754(18) 0.56269(18) 0.0355(11) Uani 1 1 d . . . . .
H21 H 0.769953 -0.193063 0.593708 0.043 Uiso 1 1 calc R U . . .
C27 C 1.1002(4) 0.03120(19) 0.32966(17) 0.0314(10) Uani 1 1 d . . . . .
H6 H 1.133376 -0.011675 0.331004 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5798(4) 0.26530(18) 0.30945(18) 0.0312(11) Uani 1 1 d . . . . .
H7 H 0.520464 0.280463 0.280124 0.037 Uiso 1 1 calc R U . . .
C29 C 1.1830(4) 0.08118(19) 0.31527(17) 0.0317(10) Uani 1 1 d . . . . .
H8 H 1.273861 0.072822 0.306863 0.038 Uiso 1 1 calc R U . . .
C30 C 0.1630(4) 0.05419(18) 0.71544(17) 0.0330(10) Uani 1 1 d . . . . .
H25 H 0.200827 0.044074 0.753954 0.049 Uiso 1 1 calc R U . . .
H26 H 0.073505 0.035814 0.712574 0.049 Uiso 1 1 calc R U . . .
H27 H 0.158247 0.101090 0.710559 0.049 Uiso 1 1 calc R U . . .
C31 C 0.2511(4) 0.02548(18) 0.66745(17) 0.0250(9) Uani 1 1 d . . . . .
H28 H 0.256271 -0.022221 0.673485 0.030 Uiso 1 1 calc R U . . .
C32 C 0.5331(4) 0.24827(17) 0.36298(18) 0.0305(10) Uani 1 1 d . . . . .
H9 H 0.440248 0.250102 0.370395 0.037 Uiso 1 1 calc R U . . .
C33 C 0.4955(4) -0.05518(19) 0.40779(17) 0.0317(10) Uani 1 1 d . . . . .
C34 C 0.8100(4) 0.00256(19) 0.75121(17) 0.0289(10) Uani 1 1 d . . . . .
H39 H 0.768604 0.041249 0.764030 0.035 Uiso 1 1 calc R U . . .
C35 C 0.9336(4) -0.0929(2) 0.77365(19) 0.0357(11) Uani 1 1 d . . . . .
H40 H 0.975646 -0.120096 0.801597 0.043 Uiso 1 1 calc R U . . .
C36 C 0.4574(4) -0.06073(19) 0.58249(17) 0.0306(10) Uani 1 1 d . . . . .
H34 H 0.441809 -0.027264 0.554895 0.037 Uiso 1 1 calc R U . . .
C37 C 0.7428(4) 0.02931(18) 0.64671(17) 0.0278(10) Uani 1 1 d . . . . .
H44 H 0.731474 0.003928 0.609772 0.033 Uiso 1 1 calc R U . . .
C38 C 0.8728(4) -0.03706(18) 0.79118(17) 0.0296(10) Uani 1 1 d . . . . .
H41 H 0.873819 -0.025410 0.831459 0.036 Uiso 1 1 calc R U . . .
C39 C 0.5736(4) 0.2135(2) 0.46530(18) 0.0371(11) Uani 1 1 d . . . . .
H10 H 0.480953 0.215255 0.473157 0.044 Uiso 1 1 calc R U . . .
C40 C 0.7966(4) 0.19384(19) 0.49773(18) 0.0352(11) Uani 1 1 d . . . . .
H11 H 0.856471 0.183085 0.528431 0.042 Uiso 1 1 calc R U . . .
C41 C 0.5185(4) -0.09500(18) 0.67949(17) 0.0298(10) Uani 1 1 d . . . . .
H35 H 0.545232 -0.084894 0.718362 0.036 Uiso 1 1 calc R U . . .
C42 C 0.6597(4) 0.1974(2) 0.50925(19) 0.0374(11) Uani 1 1 d . . . . .
H12 H 0.627075 0.188689 0.547510 0.045 Uiso 1 1 calc R U . . .
C43 C 0.7877(4) -0.16910(18) 0.50822(17) 0.0308(10) Uani 1 1 d . . . . .
H22 H 0.695564 -0.161468 0.502299 0.037 Uiso 1 1 calc R U . . .
C44 C 0.5057(5) -0.15814(18) 0.66247(19) 0.0388(11) Uani 1 1 d . . . . .
H36 H 0.522057 -0.191776 0.689805 0.047 Uiso 1 1 calc R U . . .
C45 C 0.2033(4) 0.0988(2) 0.58160(17) 0.0341(11) Uani 1 1 d . . . . .
H29 H 0.244518 0.132818 0.602733 0.041 Uiso 1 1 calc R U . . .
C46 C 0.7095(4) -0.02354(19) 0.44866(17) 0.0325(10) Uani 1 1 d . . . . .
H13 H 0.800915 -0.031884 0.455850 0.039 Uiso 1 1 calc R U . . .
C47 C 0.4456(4) -0.1245(2) 0.56582(18) 0.0359(11) Uani 1 1 d . . . . .
H37 H 0.421319 -0.134939 0.526706 0.043 Uiso 1 1 calc R U . . .
C48 C 1.0562(5) -0.19205(18) 0.52815(18) 0.0356(11) Uani 1 1 d . . . . .
H23 H 1.147731 -0.200150 0.535290 0.043 Uiso 1 1 calc R U . . .
C49 C 0.6538(4) 0.03245(19) 0.46919(18) 0.0372(11) Uani 1 1 d . . . . .
H14 H 0.707215 0.062545 0.489935 0.045 Uiso 1 1 calc R U . . .
C50 C 0.8294(4) 0.08774(19) 0.63319(19) 0.0407(12) Uani 1 1 d . . . . .
H45 H 0.784378 0.115208 0.604411 0.061 Uiso 1 1 calc R U . . .
H46 H 0.914763 0.073293 0.617187 0.061 Uiso 1 1 calc R U . . .
H47 H 0.844772 0.112302 0.669262 0.061 Uiso 1 1 calc R U . . .
C51 C 0.9670(5) -0.19825(19) 0.5729(2) 0.0395(12) Uani 1 1 d . . . . .
H24 H 0.996760 -0.209839 0.611035 0.047 Uiso 1 1 calc R U . . .
C52 C 0.4187(4) -0.0985(2) 0.37450(18) 0.0367(11) Uani 1 1 d . . . . .
H15 H 0.326749 -0.090162 0.368780 0.044 Uiso 1 1 calc R U . . .
C53 C 0.4689(4) -0.1729(2) 0.6056(2) 0.0389(12) Uani 1 1 d . . . . .
H38 H 0.459761 -0.216724 0.594058 0.047 Uiso 1 1 calc R U . . .
C54 C 0.8707(4) -0.07025(18) 0.67463(18) 0.0340(10) Uani 1 1 d . . . . .
H42 H 0.871215 -0.081873 0.634349 0.041 Uiso 1 1 calc R U . . .
C55 C 0.1347(4) -0.0111(2) 0.5751(2) 0.0385(11) Uani 1 1 d . . . . .
H30 H 0.128626 -0.053070 0.591583 0.046 Uiso 1 1 calc R U . . .
C56 C 0.6093(4) -0.1655(2) 0.35940(18) 0.0337(10) Uani 1 1 d . . . . .
C57 C 0.4414(4) 0.0027(2) 0.43082(19) 0.0404(12) Uani 1 1 d . . . . .
H16 H 0.349403 0.011483 0.425785 0.048 Uiso 1 1 calc R U . . .
C58 C 0.9333(5) -0.1094(2) 0.7151(2) 0.0430(12) Uani 1 1 d . . . . .
H43 H 0.976184 -0.147791 0.702615 0.052 Uiso 1 1 calc R U . . .
C59 C 0.4737(4) -0.1519(2) 0.35052(18) 0.0380(11) Uani 1 1 d . . . . .
H17 H 0.420685 -0.180249 0.327641 0.046 Uiso 1 1 calc R U . . .
C60 C 0.5185(5) 0.0458(2) 0.45989(19) 0.0433(12) Uani 1 1 d . . . . .
H18 H 0.481112 0.084920 0.473937 0.052 Uiso 1 1 calc R U . . .
C61 C 0.1514(5) 0.1108(2) 0.52609(19) 0.0479(13) Uani 1 1 d . . . . .
H31 H 0.157931 0.152589 0.509349 0.058 Uiso 1 1 calc R U . . .
C62 C 0.0825(5) 0.0011(3) 0.5196(2) 0.0553(15) Uani 1 1 d . . . . .
H32 H 0.041150 -0.032798 0.498318 0.066 Uiso 1 1 calc R U . . .
C63 C 0.0901(5) 0.0613(3) 0.4953(2) 0.0568(15) Uani 1 1 d . . . . .
H33 H 0.053630 0.069228 0.457608 0.068 Uiso 1 1 calc R U . . .
H48 H 0.607(4) 0.0967(19) 0.6773(16) 0.038(12) Uiso 1 1 d . . . . .
H51 H 0.857(6) 0.303(3) 0.245(2) 0.12(2) 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 C11 1.356(4) . ?
O2 C9 1.370(4) . ?
O2 H52 0.96(5) . ?
O3 C17 1.369(4) . ?
O3 H51 1.10(6) . ?
N2 C5 1.320(4) . ?
N2 C31 1.476(5) . ?
N2 H49 0.93(4) . ?
N1 C5 1.317(5) . ?
N1 C37 1.476(5) . ?
N1 H48 0.94(4) . ?
O4 C56 1.379(5) . ?
O4 H50 0.87(6) . ?
C2 C21 1.405(5) . ?
C2 C48 1.420(5) . ?
C2 C19 1.427(5) . ?
C3 C22 1.418(5) . ?
C3 C15 1.419(5) . ?
C3 C6 1.440(5) . ?
C4 C56 1.368(5) . ?
C4 C16 1.431(5) . ?
C4 C64 1.498(5) . ?
C5 C14 1.485(5) . ?
C64 C9 1.380(5) . ?
C64 C19 1.432(5) . ?
C6 C17 1.379(5) . ?
C6 C10 1.497(5) . ?
C7 C12 1.362(5) . ?
C7 C27 1.395(5) . ?
C7 H1 0.9500 . ?
C8 C18 1.417(5) . ?
C8 C12 1.424(5) . ?
C8 C10 1.439(5) . ?
C9 C24 1.417(5) . ?
C10 C11 1.395(5) . ?
C11 C23 1.414(5) . ?
C12 H2 0.9500 . ?
C13 C54 1.387(5) . ?
C13 C34 1.388(5) . ?
C13 C37 1.520(5) . ?
C14 C36 1.387(5) . ?
C14 C41 1.390(5) . ?
C15 C39 1.415(5) . ?
C15 C32 1.422(5) . ?
C16 C46 1.420(5) . ?
C16 C33 1.429(5) . ?
C17 C28 1.428(5) . ?
C18 C29 1.407(5) . ?
C18 C20 1.421(5) . ?
C19 C43 1.414(5) . ?
C20 C23 1.358(5) . ?
C20 H3 0.9500 . ?
C21 C24 1.360(5) . ?
C21 H19 0.9500 . ?
C22 C40 1.371(5) . ?
C22 H4 0.9500 . ?
C23 H5 0.9500 . ?
C24 H20 0.9500 . ?
C25 C45 1.378(5) . ?
C25 C55 1.389(5) . ?
C25 C31 1.524(5) . ?
C26 C43 1.374(5) . ?
C26 C51 1.396(6) . ?
C26 H21 0.9500 . ?
C27 C29 1.369(5) . ?
C27 H6 0.9500 . ?
C28 C32 1.355(5) . ?
C28 H7 0.9500 . ?
C29 H8 0.9500 . ?
C30 C31 1.529(5) . ?
C30 H25 0.9800 . ?
C30 H26 0.9800 . ?
C30 H27 0.9800 . ?
C31 H28 1.0000 . ?
C32 H9 0.9500 . ?
C33 C52 1.408(5) . ?
C33 C57 1.419(5) . ?
C34 C38 1.380(5) . ?
C34 H39 0.9500 . ?
C35 C58 1.377(6) . ?
C35 C38 1.370(5) . ?
C35 H40 0.9500 . ?
C36 C47 1.381(5) . ?
C36 H34 0.9500 . ?
C37 C50 1.524(5) . ?
C37 H44 1.0000 . ?
C38 H41 0.9500 . ?
C39 C42 1.367(5) . ?
C39 H10 0.9500 . ?
C40 C42 1.404(6) . ?
C40 H11 0.9500 . ?
C41 C44 1.372(5) . ?
C41 H35 0.9500 . ?
C42 H12 0.9500 . ?
C43 H22 0.9500 . ?
C44 C53 1.383(6) . ?
C44 H36 0.9500 . ?
C45 C61 1.392(5) . ?
C45 H29 0.9500 . ?
C46 C49 1.372(5) . ?
C46 H13 0.9500 . ?
C47 C53 1.374(5) . ?
C47 H37 0.9500 . ?
C48 C51 1.366(6) . ?
C48 H23 0.9500 . ?
C49 C60 1.405(6) . ?
C49 H14 0.9500 . ?
C50 H45 0.9800 . ?
C50 H46 0.9800 . ?
C50 H47 0.9800 . ?
C51 H24 0.9500 . ?
C52 C59 1.353(6) . ?
C52 H15 0.9500 . ?
C53 H38 0.9500 . ?
C54 C58 1.381(5) . ?
C54 H42 0.9500 . ?
C55 C62 1.395(6) . ?
C55 H30 0.9500 . ?
C56 C59 1.408(6) . ?
C57 C60 1.356(6) . ?
C57 H16 0.9500 . ?
C58 H43 0.9500 . ?
C59 H17 0.9500 . ?
C60 H18 0.9500 . ?
C61 C63 1.387(6) . ?
C61 H31 0.9500 . ?
C62 C63 1.367(7) . ?
C62 H32 0.9500 . ?
C63 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H52 113(3) . . ?
C17 O3 H51 110(3) . . ?
C5 N2 C31 125.5(3) . . ?
C5 N2 H49 119(2) . . ?
C31 N2 H49 115(2) . . ?
C5 N1 C37 126.0(3) . . ?
C5 N1 H48 117(2) . . ?
C37 N1 H48 116(2) . . ?
C56 O4 H50 110(4) . . ?
C21 C2 C48 122.3(4) . . ?
C21 C2 C19 118.6(4) . . ?
C48 C2 C19 119.1(4) . . ?
C22 C3 C15 117.9(4) . . ?
C22 C3 C6 121.8(4) . . ?
C15 C3 C6 120.3(4) . . ?
C56 C4 C16 118.0(4) . . ?
C56 C4 C64 121.7(4) . . ?
C16 C4 C64 120.3(4) . . ?
N1 C5 N2 118.8(3) . . ?
N1 C5 C14 121.7(4) . . ?
N2 C5 C14 119.5(4) . . ?
C9 C64 C19 118.5(3) . . ?
C9 C64 C4 120.6(3) . . ?
C19 C64 C4 120.9(3) . . ?
C17 C6 C3 117.6(4) . . ?
C17 C6 C10 121.4(3) . . ?
C3 C6 C10 121.0(3) . . ?
C12 C7 C27 121.0(4) . . ?
C12 C7 H1 119.5 . . ?
C27 C7 H1 119.5 . . ?
C18 C8 C12 116.9(3) . . ?
C18 C8 C10 120.5(3) . . ?
C12 C8 C10 122.5(3) . . ?
O2 C9 C64 118.8(3) . . ?
O2 C9 C24 120.0(4) . . ?
C64 C9 C24 121.2(4) . . ?
C11 C10 C8 118.6(3) . . ?
C11 C10 C6 121.7(3) . . ?
C8 C10 C6 119.6(3) . . ?
O1 C11 C10 121.6(3) . . ?
O1 C11 C23 118.8(3) . . ?
C10 C11 C23 119.5(4) . . ?
C7 C12 C8 121.4(3) . . ?
C7 C12 H2 119.3 . . ?
C8 C12 H2 119.3 . . ?
C54 C13 C34 118.7(4) . . ?
C54 C13 C37 119.7(3) . . ?
C34 C13 C37 121.5(3) . . ?
C36 C14 C41 119.9(3) . . ?
C36 C14 C5 120.6(3) . . ?
C41 C14 C5 119.4(3) . . ?
C39 C15 C32 121.6(4) . . ?
C39 C15 C3 119.6(4) . . ?
C32 C15 C3 118.8(4) . . ?
C46 C16 C33 117.5(4) . . ?
C46 C16 C4 122.5(4) . . ?
C33 C16 C4 119.9(4) . . ?
O3 C17 C6 121.6(3) . . ?
O3 C17 C28 116.2(4) . . ?
C6 C17 C28 122.1(4) . . ?
C29 C18 C8 120.4(4) . . ?
C29 C18 C20 120.9(4) . . ?
C8 C18 C20 118.6(3) . . ?
C43 C19 C2 117.9(4) . . ?
C43 C19 C64 122.1(4) . . ?
C2 C19 C64 120.0(4) . . ?
C23 C20 C18 120.2(4) . . ?
C23 C20 H3 119.9 . . ?
C18 C20 H3 119.9 . . ?
C24 C21 C2 121.5(4) . . ?
C24 C21 H19 119.3 . . ?
C2 C21 H19 119.3 . . ?
C40 C22 C3 121.2(4) . . ?
C40 C22 H4 119.4 . . ?
C3 C22 H4 119.4 . . ?
C20 C23 C11 122.3(4) . . ?
C20 C23 H5 118.8 . . ?
C11 C23 H5 118.8 . . ?
C21 C24 C9 120.1(4) . . ?
C21 C24 H20 119.9 . . ?
C9 C24 H20 119.9 . . ?
C45 C25 C55 119.0(4) . . ?
C45 C25 C31 120.8(4) . . ?
C55 C25 C31 120.2(4) . . ?
C43 C26 C51 120.7(4) . . ?
C43 C26 H21 119.6 . . ?
C51 C26 H21 119.6 . . ?
C29 C27 C7 119.6(4) . . ?
C29 C27 H6 120.2 . . ?
C7 C27 H6 120.2 . . ?
C32 C28 C17 119.6(4) . . ?
C32 C28 H7 120.2 . . ?
C17 C28 H7 120.2 . . ?
C27 C29 C18 120.6(4) . . ?
C27 C29 H8 119.7 . . ?
C18 C29 H8 119.7 . . ?
C31 C30 H25 109.5 . . ?
C31 C30 H26 109.5 . . ?
H25 C30 H26 109.5 . . ?
C31 C30 H27 109.5 . . ?
H25 C30 H27 109.5 . . ?
H26 C30 H27 109.5 . . ?
N2 C31 C25 110.5(3) . . ?
N2 C31 C30 108.9(3) . . ?
C25 C31 C30 112.0(3) . . ?
N2 C31 H28 108.5 . . ?
C25 C31 H28 108.5 . . ?
C30 C31 H28 108.5 . . ?
C28 C32 C15 121.2(4) . . ?
C28 C32 H9 119.4 . . ?
C15 C32 H9 119.4 . . ?
C52 C33 C57 122.0(4) . . ?
C52 C33 C16 118.6(4) . . ?
C57 C33 C16 119.4(4) . . ?
C38 C34 C13 120.0(4) . . ?
C38 C34 H39 120.0 . . ?
C13 C34 H39 120.0 . . ?
C58 C35 C38 119.4(4) . . ?
C58 C35 H40 120.3 . . ?
C38 C35 H40 120.3 . . ?
C47 C36 C14 119.6(4) . . ?
C47 C36 H34 120.2 . . ?
C14 C36 H34 120.2 . . ?
N1 C37 C50 107.6(3) . . ?
N1 C37 C13 113.0(3) . . ?
C50 C37 C13 111.4(3) . . ?
N1 C37 H44 108.2 . . ?
C50 C37 H44 108.2 . . ?
C13 C37 H44 108.2 . . ?
C34 C38 C35 121.0(4) . . ?
C34 C38 H41 119.5 . . ?
C35 C38 H41 119.5 . . ?
C42 C39 C15 120.9(4) . . ?
C42 C39 H10 119.5 . . ?
C15 C39 H10 119.5 . . ?
C22 C40 C42 120.5(4) . . ?
C22 C40 H11 119.7 . . ?
C42 C40 H11 119.7 . . ?
C44 C41 C14 119.8(4) . . ?
C44 C41 H35 120.1 . . ?
C14 C41 H35 120.1 . . ?
C39 C42 C40 119.8(4) . . ?
C39 C42 H12 120.1 . . ?
C40 C42 H12 120.1 . . ?
C26 C43 C19 121.2(4) . . ?
C26 C43 H22 119.4 . . ?
C19 C43 H22 119.4 . . ?
C41 C44 C53 120.2(4) . . ?
C41 C44 H36 119.9 . . ?
C53 C44 H36 119.9 . . ?
C25 C45 C61 120.9(4) . . ?
C25 C45 H29 119.5 . . ?
C61 C45 H29 119.5 . . ?
C49 C46 C16 121.2(4) . . ?
C49 C46 H13 119.4 . . ?
C16 C46 H13 119.4 . . ?
C53 C47 C36 120.2(4) . . ?
C53 C47 H37 119.9 . . ?
C36 C47 H37 119.9 . . ?
C51 C48 C2 121.0(4) . . ?
C51 C48 H23 119.5 . . ?
C2 C48 H23 119.5 . . ?
C46 C49 C60 120.7(4) . . ?
C46 C49 H14 119.6 . . ?
C60 C49 H14 119.6 . . ?
C37 C50 H45 109.5 . . ?
C37 C50 H46 109.5 . . ?
H45 C50 H46 109.5 . . ?
C37 C50 H47 109.5 . . ?
H45 C50 H47 109.5 . . ?
H46 C50 H47 109.5 . . ?
C48 C51 C26 119.9(4) . . ?
C48 C51 H24 120.0 . . ?
C26 C51 H24 120.0 . . ?
C59 C52 C33 121.1(4) . . ?
C59 C52 H15 119.5 . . ?
C33 C52 H15 119.5 . . ?
C47 C53 C44 120.2(4) . . ?
C47 C53 H38 119.9 . . ?
C44 C53 H38 119.9 . . ?
C58 C54 C13 120.6(4) . . ?
C58 C54 H42 119.7 . . ?
C13 C54 H42 119.7 . . ?
C25 C55 C62 119.9(4) . . ?
C25 C55 H30 120.1 . . ?
C62 C55 H30 120.1 . . ?
C4 C56 O4 122.5(4) . . ?
C4 C56 C59 122.2(4) . . ?
O4 C56 C59 115.3(4) . . ?
C60 C57 C33 121.2(4) . . ?
C60 C57 H16 119.4 . . ?
C33 C57 H16 119.4 . . ?
C35 C58 C54 120.3(4) . . ?
C35 C58 H43 119.9 . . ?
C54 C58 H43 119.9 . . ?
C52 C59 C56 120.1(4) . . ?
C52 C59 H17 119.9 . . ?
C56 C59 H17 119.9 . . ?
C57 C60 C49 119.9(4) . . ?
C57 C60 H18 120.1 . . ?
C49 C60 H18 120.1 . . ?
C63 C61 C45 119.7(4) . . ?
C63 C61 H31 120.2 . . ?
C45 C61 H31 120.2 . . ?
C63 C62 C55 120.8(4) . . ?
C63 C62 H32 119.6 . . ?
C55 C62 H32 119.6 . . ?
C62 C63 C61 119.7(4) . . ?
C62 C63 H33 120.1 . . ?
C61 C63 H33 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
C37 N1 C5 N2 -173.8(3) . . . . ?
C37 N1 C5 C14 6.9(6) . . . . ?
C31 N2 C5 N1 177.6(4) . . . . ?
C31 N2 C5 C14 -3.0(5) . . . . ?
C56 C4 C64 C9 69.2(5) . . . . ?
C16 C4 C64 C9 -111.1(4) . . . . ?
C56 C4 C64 C19 -111.0(4) . . . . ?
C16 C4 C64 C19 68.6(5) . . . . ?
C22 C3 C6 C17 -172.3(3) . . . . ?
C15 C3 C6 C17 6.3(5) . . . . ?
C22 C3 C6 C10 9.9(5) . . . . ?
C15 C3 C6 C10 -171.6(3) . . . . ?
C19 C64 C9 O2 178.4(3) . . . . ?
C4 C64 C9 O2 -1.9(5) . . . . ?
C19 C64 C9 C24 -2.8(6) . . . . ?
C4 C64 C9 C24 176.9(4) . . . . ?
C18 C8 C10 C11 4.8(5) . . . . ?
C12 C8 C10 C11 -171.1(3) . . . . ?
C18 C8 C10 C6 -178.8(3) . . . . ?
C12 C8 C10 C6 5.3(5) . . . . ?
C17 C6 C10 C11 57.5(5) . . . . ?
C3 C6 C10 C11 -124.7(4) . . . . ?
C17 C6 C10 C8 -118.7(4) . . . . ?
C3 C6 C10 C8 59.1(5) . . . . ?
C8 C10 C11 O1 170.2(3) . . . . ?
C6 C10 C11 O1 -6.1(5) . . . . ?
C8 C10 C11 C23 -6.7(5) . . . . ?
C6 C10 C11 C23 177.1(4) . . . . ?
C27 C7 C12 C8 1.1(6) . . . . ?
C18 C8 C12 C7 0.1(5) . . . . ?
C10 C8 C12 C7 176.2(3) . . . . ?
N1 C5 C14 C36 -101.5(5) . . . . ?
N2 C5 C14 C36 79.2(5) . . . . ?
N1 C5 C14 C41 80.4(5) . . . . ?
N2 C5 C14 C41 -98.9(4) . . . . ?
C22 C3 C15 C39 -1.9(6) . . . . ?
C6 C3 C15 C39 179.4(3) . . . . ?
C22 C3 C15 C32 176.6(3) . . . . ?
C6 C3 C15 C32 -2.1(5) . . . . ?
C56 C4 C16 C46 -175.9(4) . . . . ?
C64 C4 C16 C46 4.4(5) . . . . ?
C56 C4 C16 C33 1.9(5) . . . . ?
C64 C4 C16 C33 -177.8(3) . . . . ?
C3 C6 C17 O3 174.1(3) . . . . ?
C10 C6 C17 O3 -8.1(6) . . . . ?
C3 C6 C17 C28 -6.4(5) . . . . ?
C10 C6 C17 C28 171.4(3) . . . . ?
C12 C8 C18 C29 -1.5(5) . . . . ?
C10 C8 C18 C29 -177.6(3) . . . . ?
C12 C8 C18 C20 176.1(3) . . . . ?
C10 C8 C18 C20 -0.1(5) . . . . ?
C21 C2 C19 C43 178.0(3) . . . . ?
C48 C2 C19 C43 -1.1(6) . . . . ?
C21 C2 C19 C64 -0.6(6) . . . . ?
C48 C2 C19 C64 -179.7(3) . . . . ?
C9 C64 C19 C43 -175.7(4) . . . . ?
C4 C64 C19 C43 4.6(6) . . . . ?
C9 C64 C19 C2 2.8(5) . . . . ?
C4 C64 C19 C2 -176.9(3) . . . . ?
C29 C18 C20 C23 174.6(4) . . . . ?
C8 C18 C20 C23 -2.9(6) . . . . ?
C48 C2 C21 C24 177.3(4) . . . . ?
C19 C2 C21 C24 -1.8(6) . . . . ?
C15 C3 C22 C40 0.3(5) . . . . ?
C6 C3 C22 C40 179.0(4) . . . . ?
C18 C20 C23 C11 1.0(6) . . . . ?
O1 C11 C23 C20 -173.0(4) . . . . ?
C10 C11 C23 C20 3.9(6) . . . . ?
C2 C21 C24 C9 1.9(6) . . . . ?
O2 C9 C24 C21 179.3(3) . . . . ?
C64 C9 C24 C21 0.5(6) . . . . ?
C12 C7 C27 C29 -1.0(6) . . . . ?
O3 C17 C28 C32 -178.3(3) . . . . ?
C6 C17 C28 C32 2.2(6) . . . . ?
C7 C27 C29 C18 -0.4(6) . . . . ?
C8 C18 C29 C27 1.6(6) . . . . ?
C20 C18 C29 C27 -175.8(4) . . . . ?
C5 N2 C31 C25 -88.4(4) . . . . ?
C5 N2 C31 C30 148.2(4) . . . . ?
C45 C25 C31 N2 -47.7(5) . . . . ?
C55 C25 C31 N2 133.2(4) . . . . ?
C45 C25 C31 C30 73.9(5) . . . . ?
C55 C25 C31 C30 -105.2(4) . . . . ?
C17 C28 C32 C15 2.3(6) . . . . ?
C39 C15 C32 C28 176.1(4) . . . . ?
C3 C15 C32 C28 -2.3(6) . . . . ?
C46 C16 C33 C52 177.6(3) . . . . ?
C4 C16 C33 C52 -0.3(5) . . . . ?
C46 C16 C33 C57 -0.4(5) . . . . ?
C4 C16 C33 C57 -178.3(3) . . . . ?
C54 C13 C34 C38 -1.2(6) . . . . ?
C37 C13 C34 C38 -178.1(3) . . . . ?
C41 C14 C36 C47 1.8(6) . . . . ?
C5 C14 C36 C47 -176.3(4) . . . . ?
C5 N1 C37 C50 153.3(4) . . . . ?
C5 N1 C37 C13 -83.3(5) . . . . ?
C54 C13 C37 N1 137.0(4) . . . . ?
C34 C13 C37 N1 -46.1(5) . . . . ?
C54 C13 C37 C50 -101.7(4) . . . . ?
C34 C13 C37 C50 75.1(5) . . . . ?
C13 C34 C38 C35 0.3(6) . . . . ?
C58 C35 C38 C34 0.7(6) . . . . ?
C32 C15 C39 C42 -176.2(4) . . . . ?
C3 C15 C39 C42 2.3(6) . . . . ?
C3 C22 C40 C42 1.0(6) . . . . ?
C36 C14 C41 C44 -2.2(6) . . . . ?
C5 C14 C41 C44 175.9(4) . . . . ?
C15 C39 C42 C40 -1.0(6) . . . . ?
C22 C40 C42 C39 -0.7(6) . . . . ?
C51 C26 C43 C19 0.9(6) . . . . ?
C2 C19 C43 C26 0.5(6) . . . . ?
C64 C19 C43 C26 179.0(4) . . . . ?
C14 C41 C44 C53 1.1(7) . . . . ?
C55 C25 C45 C61 -0.2(6) . . . . ?
C31 C25 C45 C61 -179.3(4) . . . . ?
C33 C16 C46 C49 -0.9(5) . . . . ?
C4 C16 C46 C49 177.0(4) . . . . ?
C14 C36 C47 C53 -0.4(6) . . . . ?
C21 C2 C48 C51 -178.7(4) . . . . ?
C19 C2 C48 C51 0.3(6) . . . . ?
C16 C46 C49 C60 0.8(6) . . . . ?
C2 C48 C51 C26 1.1(6) . . . . ?
C43 C26 C51 C48 -1.7(6) . . . . ?
C57 C33 C52 C59 176.7(4) . . . . ?
C16 C33 C52 C59 -1.2(6) . . . . ?
C36 C47 C53 C44 -0.7(7) . . . . ?
C41 C44 C53 C47 0.3(7) . . . . ?
C34 C13 C54 C58 1.2(6) . . . . ?
C37 C13 C54 C58 178.1(4) . . . . ?
C45 C25 C55 C62 0.0(6) . . . . ?
C31 C25 C55 C62 179.1(4) . . . . ?
C16 C4 C56 O4 178.3(4) . . . . ?
C64 C4 C56 O4 -2.0(6) . . . . ?
C16 C4 C56 C59 -2.1(6) . . . . ?
C64 C4 C56 C59 177.5(4) . . . . ?
C52 C33 C57 C60 -176.1(4) . . . . ?
C16 C33 C57 C60 1.8(6) . . . . ?
C38 C35 C58 C54 -0.8(7) . . . . ?
C13 C54 C58 C35 -0.2(7) . . . . ?
C33 C52 C59 C56 1.0(6) . . . . ?
C4 C56 C59 C52 0.7(6) . . . . ?
O4 C56 C59 C52 -179.7(4) . . . . ?
C33 C57 C60 C49 -2.0(6) . . . . ?
C46 C49 C60 C57 0.7(6) . . . . ?
C25 C45 C61 C63 0.5(7) . . . . ?
C25 C55 C62 C63 -0.2(7) . . . . ?
C55 C62 C63 C61 0.5(7) . . . . ?
C45 C61 C63 C62 -0.7(7) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_benzamidine_nitrophenol
_database_code_depnum_ccdc_archive 'CCDC 2057488'
loop_
_audit_author_name
_audit_author_address
'Koichi Kodama'
;Saitama University
Japan
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_weight         259.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.4244(13)
_cell_length_b                   5.0509(7)
_cell_length_c                   13.2982(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.928(2)
_cell_angle_gamma                90
_cell_volume                     621.54(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2516
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.51

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2944
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.877
_reflns_number_total             1955
_reflns_number_gt                1891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_max     0.781
_reflns_Friedel_fraction_full    0.759

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1093P)²+0.0564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.1(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1955
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.3862(2) 0.9414(5) 0.61032(15) 0.0296(5) Uani 1 1 d . . . . .
N5 N 1.0316(2) 0.1974(5) 0.74160(19) 0.0258(6) Uani 1 1 d . . . . .
N1 N 0.5732(3) 0.3346(5) 0.58942(19) 0.0249(6) Uani 1 1 d . . . . .
O2 O 0.9443(2) 0.0772(5) 0.67494(16) 0.0363(6) Uani 1 1 d . . . . .
O3 O 1.0410(2) 0.1506(5) 0.83369(15) 0.0372(6) Uani 1 1 d . . . . .
C2 C 1.1134(3) 0.4385(6) 0.6041(2) 0.0236(6) Uani 1 1 d . . . . .
H1 H 1.0469 0.3410 0.5553 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6861(3) 0.4815(6) 0.7604(2) 0.0241(7) Uani 1 1 d . . . . .
C15 C 1.2009(3) 0.6234(7) 0.5726(2) 0.0238(6) Uani 1 1 d . . . . .
H2 H 1.1935 0.6537 0.5013 0.029 Uiso 1 1 calc R U . . .
C4 C 1.1222(3) 0.3935(6) 0.7088(2) 0.0236(7) Uani 1 1 d . . . . .
N4 N 0.7439(3) 0.6556(5) 0.6021(2) 0.0273(6) Uani 1 1 d . . . . .
C6 C 1.3027(3) 0.7721(6) 0.6426(2) 0.0236(7) Uani 1 1 d . . . . .
C7 C 0.6663(3) 0.4914(6) 0.6466(2) 0.0218(6) Uani 1 1 d . . . . .
C8 C 1.2192(3) 0.5361(7) 0.7807(2) 0.0321(8) Uani 1 1 d . . . . .
H3 H 1.2244 0.5045 0.8518 0.039 Uiso 1 1 calc R U . . .
C9 C 1.3074(3) 0.7228(7) 0.7488(2) 0.0329(8) Uani 1 1 d . . . . .
H4 H 1.3725 0.8206 0.7984 0.040 Uiso 1 1 calc R U . . .
C10 C 0.7842(4) 0.6453(9) 0.8209(3) 0.0438(9) Uani 1 1 d . . . . .
H5 H 0.8386 0.7685 0.7897 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7242(4) 0.4601(9) 0.9724(2) 0.0420(9) Uani 1 1 d . . . . .
H6 H 0.7365 0.4540 1.0449 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6068(5) 0.3068(9) 0.8070(3) 0.0509(11) Uani 1 1 d . . . . .
H7 H 0.5385 0.1929 0.7666 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8041(5) 0.6320(10) 0.9265(3) 0.0519(11) Uani 1 1 d . . . . .
H8 H 0.8736 0.7428 0.9674 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6268(6) 0.2973(11) 0.9134(3) 0.0636(14) Uani 1 1 d . . . . .
H9 H 0.5721 0.1762 0.9453 0.076 Uiso 1 1 calc R U . . .
H10 H 0.813(4) 0.780(8) 0.638(3) 0.028(8) Uiso 1 1 d . . . . .
H13 H 0.512(4) 0.222(9) 0.615(3) 0.043(11) Uiso 1 1 d . . . . .
H12 H 0.572(4) 0.355(8) 0.521(3) 0.040(10) Uiso 1 1 d . . . . .
H11 H 0.721(5) 0.670(10) 0.530(4) 0.053(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
O1 C6 1.289(4) . ?
N5 O3 1.234(3) . ?
N5 O2 1.247(3) . ?
N5 C4 1.429(4) . ?
N1 C7 1.313(4) . ?
N1 H13 0.92(5) . ?
N1 H12 0.92(4) . ?
C2 C15 1.364(4) . ?
C2 C4 1.397(4) . ?
C2 H1 0.9500 . ?
C3 C12 1.377(5) . ?
C3 C10 1.380(5) . ?
C3 C7 1.489(4) . ?
C15 C6 1.419(4) . ?
C15 H2 0.9500 . ?
C4 C8 1.392(4) . ?
N4 C7 1.318(4) . ?
N4 H10 0.96(4) . ?
N4 H11 0.94(5) . ?
C6 C9 1.426(4) . ?
C8 C9 1.377(5) . ?
C8 H3 0.9500 . ?
C9 H4 0.9500 . ?
C10 C13 1.383(5) . ?
C10 H5 0.9500 . ?
C11 C13 1.366(6) . ?
C11 C14 1.364(6) . ?
C11 H6 0.9500 . ?
C12 C14 1.393(5) . ?
C12 H7 0.9500 . ?
C13 H8 0.9500 . ?
C14 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N5 O2 121.7(2) . . ?
O3 N5 C4 120.1(2) . . ?
O2 N5 C4 118.2(2) . . ?
C7 N1 H13 124(3) . . ?
C7 N1 H12 113(2) . . ?
H13 N1 H12 123(4) . . ?
C15 C2 C4 119.5(3) . . ?
C15 C2 H1 120.3 . . ?
C4 C2 H1 120.3 . . ?
C12 C3 C10 118.8(3) . . ?
C12 C3 C7 120.3(3) . . ?
C10 C3 C7 120.9(3) . . ?
C2 C15 C6 122.3(2) . . ?
C2 C15 H2 118.8 . . ?
C6 C15 H2 118.8 . . ?
C8 C4 C2 120.6(3) . . ?
C8 C4 N5 120.1(3) . . ?
C2 C4 N5 119.4(3) . . ?
C7 N4 H10 124(2) . . ?
C7 N4 H11 118(3) . . ?
H10 N4 H11 117(4) . . ?
O1 C6 C15 120.8(3) . . ?
O1 C6 C9 122.6(3) . . ?
C15 C6 C9 116.6(3) . . ?
N1 C7 N4 119.1(3) . . ?
N1 C7 C3 120.6(3) . . ?
N4 C7 C3 120.3(3) . . ?
C9 C8 C4 119.9(3) . . ?
C9 C8 H3 120.0 . . ?
C4 C8 H3 120.0 . . ?
C8 C9 C6 121.2(3) . . ?
C8 C9 H4 119.4 . . ?
C6 C9 H4 119.4 . . ?
C3 C10 C13 120.7(3) . . ?
C3 C10 H5 119.7 . . ?
C13 C10 H5 119.7 . . ?
C13 C11 C14 119.6(3) . . ?
C13 C11 H6 120.2 . . ?
C14 C11 H6 120.2 . . ?
C3 C12 C14 119.9(3) . . ?
C3 C12 H7 120.0 . . ?
C14 C12 H7 120.0 . . ?
C11 C13 C10 120.3(3) . . ?
C11 C13 H8 119.9 . . ?
C10 C13 H8 119.9 . . ?
C11 C14 C12 120.7(4) . . ?
C11 C14 H9 119.7 . . ?
C12 C14 H9 119.7 . . ?

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
C4 C2 C15 C6 0.6(5) . . . . ?
C15 C2 C4 C8 0.2(5) . . . . ?
C15 C2 C4 N5 -179.3(3) . . . . ?
O3 N5 C4 C8 -1.4(4) . . . . ?
O2 N5 C4 C8 178.7(3) . . . . ?
O3 N5 C4 C2 178.1(3) . . . . ?
O2 N5 C4 C2 -1.8(4) . . . . ?
C2 C15 C6 O1 178.5(3) . . . . ?
C2 C15 C6 C9 -1.3(5) . . . . ?
C12 C3 C7 N1 0.1(5) . . . . ?
C10 C3 C7 N1 179.8(3) . . . . ?
C12 C3 C7 N4 -178.9(3) . . . . ?
C10 C3 C7 N4 0.8(5) . . . . ?
C2 C4 C8 C9 -0.1(5) . . . . ?
N5 C4 C8 C9 179.3(3) . . . . ?
C4 C8 C9 C6 -0.7(5) . . . . ?
O1 C6 C9 C8 -178.4(3) . . . . ?
C15 C6 C9 C8 1.3(5) . . . . ?
C12 C3 C10 C13 0.9(6) . . . . ?
C7 C3 C10 C13 -178.8(4) . . . . ?
C10 C3 C12 C14 -0.2(7) . . . . ?
C7 C3 C12 C14 179.5(4) . . . . ?
C14 C11 C13 C10 1.4(7) . . . . ?
C3 C10 C13 C11 -1.5(7) . . . . ?
C13 C11 C14 C12 -0.8(8) . . . . ?
C3 C12 C14 C11 0.2(8) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2c_(R)-1a
_database_code_depnum_ccdc_archive 'CCDC 2057489'
loop_
_audit_author_name
_audit_author_address
'Koichi Kodama'
;Saitama University
Japan
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H44 N2 O2'
_chemical_formula_weight         584.77

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.6751(15)
_cell_length_b                   12.6375(17)
_cell_length_c                   23.647(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3190.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6062
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18184
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7201
_reflns_number_gt                5929
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         7201
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.13878(16) 0.19887(12) 1.01621(7) 0.0267(4) Uani 1 1 d . . . . .
H1 H -0.196(4) 0.218(3) 0.9926(15) 0.085(13) Uiso 1 1 d . . . . .
O2 O 0.18458(16) 0.21892(12) 1.03331(6) 0.0308(4) Uani 1 1 d . . . . .
C1 C -0.0079(2) 0.06567(16) 1.05327(8) 0.0211(4) Uani 1 1 d . . . . .
N1 N 0.1612(2) 0.09453(16) 0.94107(8) 0.0277(4) Uani 1 1 d . . . . .
H2 H 0.105(3) 0.049(2) 0.9438(11) 0.052(9) Uiso 1 1 d . . . . .
H3 H 0.170(3) 0.142(2) 0.9736(11) 0.043(7) Uiso 1 1 d . . . . .
C2 C 0.0393(2) 0.14116(16) 1.09731(9) 0.0219(5) Uani 1 1 d . . . . .
C3 C -0.0977(2) 0.09811(16) 1.01467(8) 0.0210(5) Uani 1 1 d . . . . .
C4 C 0.0354(2) -0.04136(17) 1.05130(9) 0.0238(5) Uani 1 1 d . . . . .
C5 C 0.1688(2) -0.07152(16) 0.85512(8) 0.0218(5) Uani 1 1 d . . . . .
H4 H 0.126821 -0.075777 0.892850 0.026 Uiso 1 1 calc R U . . .
N2 N 0.3100(2) 0.17598(17) 0.88882(9) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.334(3) 0.216(2) 0.9191(12) 0.049(8) Uiso 1 1 d . . . . .
H6 H 0.347(3) 0.185(2) 0.8540(12) 0.053(9) Uiso 1 1 d . . . . .
C6 C -0.0101(2) -0.11219(17) 1.00934(9) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.2170(2) 0.10845(16) 0.89242(9) 0.0225(5) Uani 1 1 d . . . . .
C8 C -0.0129(2) 0.13909(18) 1.15272(9) 0.0243(5) Uani 1 1 d . . . . .
C9 C 0.0904(2) -0.14469(17) 0.81565(9) 0.0229(5) Uani 1 1 d . . . . .
C10 C 0.1679(2) -0.38734(17) 0.90673(9) 0.0271(5) Uani 1 1 d . . . . .
H7 H 0.235308 -0.411530 0.929571 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1785(2) -0.28844(17) 0.88085(9) 0.0245(5) Uani 1 1 d . . . . .
C12 C -0.1443(2) 0.02625(17) 0.97381(9) 0.0244(5) Uani 1 1 d . . . . .
H8 H -0.206594 0.049174 0.947870 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0253(2) 0.21376(18) 1.19419(9) 0.0266(5) Uani 1 1 d . . . . .
C14 C 0.1710(2) 0.04847(17) 0.84017(8) 0.0247(5) Uani 1 1 d . . . . .
C15 C 0.0817(2) -0.25215(17) 0.84614(9) 0.0221(5) Uani 1 1 d . . . . .
C16 C -0.1016(2) -0.07462(18) 0.97106(9) 0.0257(5) Uani 1 1 d . . . . .
H9 H -0.133799 -0.120895 0.942921 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1325(2) 0.21485(17) 1.08387(9) 0.0239(5) Uani 1 1 d . . . . .
C18 C -0.0227(2) -0.31779(17) 0.83910(9) 0.0253(5) Uani 1 1 d . . . . .
H10 H -0.089233 -0.295087 0.815328 0.030 Uiso 1 1 calc R U . . .
C19 C -0.0404(2) -0.09548(18) 0.80720(9) 0.0273(5) Uani 1 1 d . . . . .
H11 H -0.087126 -0.137830 0.778984 0.033 Uiso 1 1 calc R U . . .
H12 H -0.087009 -0.098875 0.843350 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0642(2) -0.45168(17) 0.90070(9) 0.0266(5) Uani 1 1 d . . . . .
C21 C -0.1072(2) 0.0648(2) 1.16822(10) 0.0325(6) Uani 1 1 d . . . . .
H13 H -0.136036 0.015065 1.141054 0.039 Uiso 1 1 calc R U . . .
C22 C -0.0291(2) 0.2105(2) 1.24912(10) 0.0358(6) Uani 1 1 d . . . . .
H14 H -0.003105 0.260240 1.276878 0.043 Uiso 1 1 calc R U . . .
C23 C 0.3002(2) -0.11634(18) 0.86452(10) 0.0277(5) Uani 1 1 d . . . . .
H15 H 0.342576 -0.125754 0.827623 0.033 Uiso 1 1 calc R U . . .
H16 H 0.350167 -0.066027 0.887340 0.033 Uiso 1 1 calc R U . . .
C24 C 0.0330(2) -0.21779(19) 1.00757(11) 0.0335(6) Uani 1 1 d . . . . .
H17 H 0.002538 -0.264429 0.979225 0.040 Uiso 1 1 calc R U . . .
C25 C 0.1184(2) 0.28840(19) 1.17908(9) 0.0306(5) Uani 1 1 d . . . . .
H18 H 0.144756 0.339617 1.205967 0.037 Uiso 1 1 calc R U . . .
C26 C 0.1701(2) 0.28777(18) 1.12699(9) 0.0298(5) Uani 1 1 d . . . . .
H19 H 0.233959 0.337708 1.118604 0.036 Uiso 1 1 calc R U . . .
C27 C -0.0317(2) -0.41510(18) 0.86591(9) 0.0287(5) Uani 1 1 d . . . . .
H20 H -0.104244 -0.457391 0.860444 0.034 Uiso 1 1 calc R U . . .
C28 C 0.1243(2) -0.08131(19) 1.09064(11) 0.0334(6) Uani 1 1 d . . . . .
H21 H 0.157226 -0.036003 1.119045 0.040 Uiso 1 1 calc R U . . .
C29 C -0.0351(3) 0.01952(18) 0.78731(10) 0.0350(6) Uani 1 1 d . . . . .
H22 H 0.007101 0.023015 0.750079 0.042 Uiso 1 1 calc R U . . .
H23 H -0.121334 0.047011 0.782710 0.042 Uiso 1 1 calc R U . . .
C30 C 0.2926(2) -0.22252(19) 0.89505(11) 0.0340(6) Uani 1 1 d . . . . .
H24 H 0.368490 -0.264044 0.885774 0.041 Uiso 1 1 calc R U . . .
H25 H 0.293321 -0.209321 0.936315 0.041 Uiso 1 1 calc R U . . .
C31 C 0.0353(2) 0.08795(18) 0.82944(9) 0.0298(5) Uani 1 1 d . . . . .
H26 H -0.010919 0.088603 0.865726 0.036 Uiso 1 1 calc R U . . .
H27 H 0.038445 0.161493 0.815091 0.036 Uiso 1 1 calc R U . . .
C32 C 0.2536(3) 0.0745(2) 0.78904(9) 0.0357(6) Uani 1 1 d . . . . .
H28 H 0.250496 0.150705 0.781581 0.054 Uiso 1 1 calc R U . . .
H29 H 0.222960 0.035914 0.755849 0.054 Uiso 1 1 calc R U . . .
H30 H 0.340204 0.053420 0.796973 0.054 Uiso 1 1 calc R U . . .
C33 C -0.1572(3) 0.0638(2) 1.22150(11) 0.0433(7) Uani 1 1 d . . . . .
H31 H -0.219273 0.012912 1.230870 0.052 Uiso 1 1 calc R U . . .
C34 C 0.0554(3) -0.55544(18) 0.93281(9) 0.0336(6) Uani 1 1 d . . . . .
H32 H 0.142378 -0.575126 0.944495 0.040 Uiso 1 1 calc R U . . .
C35 C 0.1487(3) -0.16697(19) 0.75704(9) 0.0336(6) Uani 1 1 d . . . . .
H33 H 0.236432 -0.188130 0.761705 0.050 Uiso 1 1 calc R U . . .
H34 H 0.144437 -0.102849 0.733810 0.050 Uiso 1 1 calc R U . . .
H35 H 0.102253 -0.224060 0.738419 0.050 Uiso 1 1 calc R U . . .
C36 C 0.1175(2) -0.2532(2) 1.04595(12) 0.0420(7) Uani 1 1 d . . . . .
H36 H 0.146116 -0.324342 1.044447 0.050 Uiso 1 1 calc R U . . .
C37 C 0.1628(3) -0.1844(2) 1.08797(13) 0.0434(7) Uani 1 1 d . . . . .
H37 H 0.221244 -0.210040 1.115011 0.052 Uiso 1 1 calc R U . . .
C38 C -0.1180(3) 0.1370(2) 1.26254(11) 0.0456(7) Uani 1 1 d . . . . .
H38 H -0.153131 0.135350 1.299438 0.055 Uiso 1 1 calc R U . . .
C39 C -0.0214(4) -0.5415(2) 0.98683(11) 0.0547(9) Uani 1 1 d . . . . .
H39 H -0.108113 -0.523941 0.976939 0.082 Uiso 1 1 calc R U . . .
H40 H 0.014524 -0.484233 1.009569 0.082 Uiso 1 1 calc R U . . .
H41 H -0.019971 -0.607456 1.008637 0.082 Uiso 1 1 calc R U . . .
C40 C 0.0044(3) -0.64623(19) 0.89780(12) 0.0512(8) Uani 1 1 d . . . . .
H42 H -0.082686 -0.631404 0.887377 0.077 Uiso 1 1 calc R U . . .
H43 H 0.008052 -0.711723 0.919930 0.077 Uiso 1 1 calc R U . . .
H44 H 0.054914 -0.654257 0.863455 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.347(3) . ?
O2 C17 1.319(3) . ?
C1 C3 1.385(3) . ?
C1 C4 1.430(3) . ?
C1 C2 1.500(3) . ?
N1 C7 1.307(3) . ?
C2 C17 1.399(3) . ?
C2 C8 1.424(3) . ?
C3 C12 1.416(3) . ?
C4 C28 1.421(3) . ?
C4 C6 1.422(3) . ?
C5 C23 1.529(3) . ?
C5 C14 1.557(3) . ?
C5 C9 1.558(3) . ?
N2 C7 1.312(3) . ?
C6 C24 1.412(3) . ?
C6 C16 1.414(3) . ?
C7 C14 1.530(3) . ?
C8 C13 1.421(3) . ?
C8 C21 1.425(3) . ?
C9 C15 1.540(3) . ?
C9 C19 1.542(3) . ?
C9 C35 1.545(3) . ?
C10 C20 1.382(3) . ?
C10 C11 1.396(3) . ?
C11 C15 1.397(3) . ?
C11 C30 1.513(3) . ?
C12 C16 1.355(3) . ?
C13 C25 1.416(3) . ?
C13 C22 1.423(3) . ?
C14 C32 1.532(3) . ?
C14 C31 1.553(3) . ?
C15 C18 1.399(3) . ?
C17 C26 1.432(3) . ?
C18 C27 1.387(3) . ?
C19 C29 1.529(3) . ?
C20 C27 1.392(3) . ?
C20 C34 1.518(3) . ?
C21 C33 1.368(3) . ?
C22 C38 1.366(4) . ?
C23 C30 1.526(3) . ?
C24 C36 1.356(4) . ?
C25 C26 1.350(3) . ?
C28 C37 1.368(3) . ?
C29 C31 1.518(3) . ?
C33 C38 1.404(4) . ?
C34 C40 1.516(3) . ?
C34 C39 1.528(4) . ?
C36 C37 1.406(4) . ?

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
C3 C1 C4 118.83(19) . . ?
C3 C1 C2 120.13(18) . . ?
C4 C1 C2 121.01(19) . . ?
C17 C2 C8 119.96(19) . . ?
C17 C2 C1 120.32(18) . . ?
C8 C2 C1 119.71(19) . . ?
O1 C3 C1 119.15(19) . . ?
O1 C3 C12 120.67(19) . . ?
C1 C3 C12 120.18(19) . . ?
C28 C4 C6 117.5(2) . . ?
C28 C4 C1 122.0(2) . . ?
C6 C4 C1 120.5(2) . . ?
C23 C5 C14 112.33(19) . . ?
C23 C5 C9 111.10(18) . . ?
C14 C5 C9 116.76(17) . . ?
C24 C6 C16 121.6(2) . . ?
C24 C6 C4 120.3(2) . . ?
C16 C6 C4 118.1(2) . . ?
N1 C7 N2 119.3(2) . . ?
N1 C7 C14 119.8(2) . . ?
N2 C7 C14 120.8(2) . . ?
C13 C8 C2 120.7(2) . . ?
C13 C8 C21 117.6(2) . . ?
C2 C8 C21 121.7(2) . . ?
C15 C9 C19 111.18(18) . . ?
C15 C9 C35 106.48(18) . . ?
C19 C9 C35 108.77(18) . . ?
C15 C9 C5 106.00(16) . . ?
C19 C9 C5 108.96(17) . . ?
C35 C9 C5 115.43(18) . . ?
C20 C10 C11 123.1(2) . . ?
C10 C11 C15 119.5(2) . . ?
C10 C11 C30 117.4(2) . . ?
C15 C11 C30 123.0(2) . . ?
C16 C12 C3 121.2(2) . . ?
C25 C13 C8 118.0(2) . . ?
C25 C13 C22 122.4(2) . . ?
C8 C13 C22 119.6(2) . . ?
C7 C14 C32 110.28(19) . . ?
C7 C14 C31 105.77(18) . . ?
C32 C14 C31 109.80(18) . . ?
C7 C14 C5 107.70(16) . . ?
C32 C14 C5 113.38(18) . . ?
C31 C14 C5 109.62(19) . . ?
C11 C15 C18 117.7(2) . . ?
C11 C15 C9 121.3(2) . . ?
C18 C15 C9 121.0(2) . . ?
C12 C16 C6 121.1(2) . . ?
O2 C17 C2 122.08(19) . . ?
O2 C17 C26 120.2(2) . . ?
C2 C17 C26 117.76(19) . . ?
C27 C18 C15 121.7(2) . . ?
C29 C19 C9 112.9(2) . . ?
C10 C20 C27 117.1(2) . . ?
C10 C20 C34 120.4(2) . . ?
C27 C20 C34 122.5(2) . . ?
C33 C21 C8 121.2(2) . . ?
C38 C22 C13 121.0(3) . . ?
C30 C23 C5 110.23(19) . . ?
C36 C24 C6 120.6(2) . . ?
C26 C25 C13 120.9(2) . . ?
C25 C26 C17 122.6(2) . . ?
C18 C27 C20 120.9(2) . . ?
C37 C28 C4 120.6(2) . . ?
C31 C29 C19 110.99(19) . . ?
C11 C30 C23 115.0(2) . . ?
C29 C31 C14 112.7(2) . . ?
C21 C33 C38 121.0(3) . . ?
C40 C34 C20 113.74(19) . . ?
C40 C34 C39 110.5(2) . . ?
C20 C34 C39 110.6(2) . . ?
C24 C36 C37 119.9(2) . . ?
C28 C37 C36 121.2(2) . . ?
C22 C38 C33 119.6(2) . . ?

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
C3 C1 C2 C17 -81.7(3) . . . . ?
C4 C1 C2 C17 100.3(2) . . . . ?
C3 C1 C2 C8 97.1(2) . . . . ?
C4 C1 C2 C8 -81.0(3) . . . . ?
C4 C1 C3 O1 -179.88(19) . . . . ?
C2 C1 C3 O1 2.0(3) . . . . ?
C4 C1 C3 C12 -0.6(3) . . . . ?
C2 C1 C3 C12 -178.67(19) . . . . ?
C3 C1 C4 C28 -177.9(2) . . . . ?
C2 C1 C4 C28 0.2(3) . . . . ?
C3 C1 C4 C6 1.9(3) . . . . ?
C2 C1 C4 C6 179.99(19) . . . . ?
C28 C4 C6 C24 -0.2(3) . . . . ?
C1 C4 C6 C24 180.0(2) . . . . ?
C28 C4 C6 C16 177.9(2) . . . . ?
C1 C4 C6 C16 -1.9(3) . . . . ?
C17 C2 C8 C13 2.3(3) . . . . ?
C1 C2 C8 C13 -176.38(19) . . . . ?
C17 C2 C8 C21 -179.5(2) . . . . ?
C1 C2 C8 C21 1.7(3) . . . . ?
C23 C5 C9 C15 60.7(2) . . . . ?
C14 C5 C9 C15 -168.67(18) . . . . ?
C23 C5 C9 C19 -179.52(18) . . . . ?
C14 C5 C9 C19 -48.9(2) . . . . ?
C23 C5 C9 C35 -56.8(2) . . . . ?
C14 C5 C9 C35 73.7(3) . . . . ?
C20 C10 C11 C15 -1.3(3) . . . . ?
C20 C10 C11 C30 175.0(2) . . . . ?
O1 C3 C12 C16 178.5(2) . . . . ?
C1 C3 C12 C16 -0.8(3) . . . . ?
C2 C8 C13 C25 -1.4(3) . . . . ?
C21 C8 C13 C25 -179.5(2) . . . . ?
C2 C8 C13 C22 179.5(2) . . . . ?
C21 C8 C13 C22 1.3(3) . . . . ?
N1 C7 C14 C32 -177.9(2) . . . . ?
N2 C7 C14 C32 3.8(3) . . . . ?
N1 C7 C14 C31 63.4(3) . . . . ?
N2 C7 C14 C31 -114.8(2) . . . . ?
N1 C7 C14 C5 -53.7(3) . . . . ?
N2 C7 C14 C5 128.0(2) . . . . ?
C23 C5 C14 C7 -67.1(2) . . . . ?
C9 C5 C14 C7 162.92(18) . . . . ?
C23 C5 C14 C32 55.2(2) . . . . ?
C9 C5 C14 C32 -74.8(3) . . . . ?
C23 C5 C14 C31 178.31(18) . . . . ?
C9 C5 C14 C31 48.3(2) . . . . ?
C10 C11 C15 C18 0.2(3) . . . . ?
C30 C11 C15 C18 -175.9(2) . . . . ?
C10 C11 C15 C9 -178.62(19) . . . . ?
C30 C11 C15 C9 5.3(3) . . . . ?
C19 C9 C15 C11 -150.1(2) . . . . ?
C35 C9 C15 C11 91.5(2) . . . . ?
C5 C9 C15 C11 -31.9(3) . . . . ?
C19 C9 C15 C18 31.1(3) . . . . ?
C35 C9 C15 C18 -87.2(2) . . . . ?
C5 C9 C15 C18 149.4(2) . . . . ?
C3 C12 C16 C6 0.8(3) . . . . ?
C24 C6 C16 C12 178.7(2) . . . . ?
C4 C6 C16 C12 0.5(3) . . . . ?
C8 C2 C17 O2 179.2(2) . . . . ?
C1 C2 C17 O2 -2.1(3) . . . . ?
C8 C2 C17 C26 -1.3(3) . . . . ?
C1 C2 C17 C26 177.41(19) . . . . ?
C11 C15 C18 C27 0.7(3) . . . . ?
C9 C15 C18 C27 179.52(19) . . . . ?
C15 C9 C19 C29 169.25(18) . . . . ?
C35 C9 C19 C29 -73.8(2) . . . . ?
C5 C9 C19 C29 52.8(2) . . . . ?
C11 C10 C20 C27 1.5(3) . . . . ?
C11 C10 C20 C34 -176.3(2) . . . . ?
C13 C8 C21 C33 -1.5(3) . . . . ?
C2 C8 C21 C33 -179.7(2) . . . . ?
C25 C13 C22 C38 -179.5(2) . . . . ?
C8 C13 C22 C38 -0.4(4) . . . . ?
C14 C5 C23 C30 163.72(17) . . . . ?
C9 C5 C23 C30 -63.4(2) . . . . ?
C16 C6 C24 C36 -177.6(2) . . . . ?
C4 C6 C24 C36 0.4(3) . . . . ?
C8 C13 C25 C26 -0.7(3) . . . . ?
C22 C13 C25 C26 178.4(2) . . . . ?
C13 C25 C26 C17 1.7(4) . . . . ?
O2 C17 C26 C25 178.8(2) . . . . ?
C2 C17 C26 C25 -0.7(4) . . . . ?
C15 C18 C27 C20 -0.6(3) . . . . ?
C10 C20 C27 C18 -0.5(3) . . . . ?
C34 C20 C27 C18 177.2(2) . . . . ?
C6 C4 C28 C37 -0.5(3) . . . . ?
C1 C4 C28 C37 179.3(2) . . . . ?
C9 C19 C29 C31 -58.9(3) . . . . ?
C10 C11 C30 C23 178.8(2) . . . . ?
C15 C11 C30 C23 -5.1(3) . . . . ?
C5 C23 C30 C11 33.1(3) . . . . ?
C19 C29 C31 C14 57.8(3) . . . . ?
C7 C14 C31 C29 -167.18(18) . . . . ?
C32 C14 C31 C29 73.8(2) . . . . ?
C5 C14 C31 C29 -51.3(2) . . . . ?
C8 C21 C33 C38 0.8(4) . . . . ?
C10 C20 C34 C40 -137.9(3) . . . . ?
C27 C20 C34 C40 44.4(3) . . . . ?
C10 C20 C34 C39 97.0(3) . . . . ?
C27 C20 C34 C39 -80.7(3) . . . . ?
C6 C24 C36 C37 0.0(4) . . . . ?
C4 C28 C37 C36 1.0(4) . . . . ?
C24 C36 C37 C28 -0.8(4) . . . . ?
C13 C22 C38 C33 -0.4(4) . . . . ?
C21 C33 C38 C22 0.2(4) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.040

