# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_STAN-DBA
_database_code_depnum_ccdc_archive 'CCDC 1863937'
_audit_update_record             
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H33 N2 O, C7 H5 O4'
_chemical_formula_sum            'C28 H38 N2 O5'
_chemical_formula_weight         482.60

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                   8.8708(18)
_cell_length_b                   15.609(3)
_cell_length_c                   18.593(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.01(3)
_cell_angle_gamma                90
_cell_volume                     2574.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11259
_cell_measurement_theta_min      3.4048
_cell_measurement_theta_max      27.4739

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8957
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9574
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.174
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9574
_reflns_number_gt                9453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 _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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.1231P] 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 4302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         9574
_refine_ls_number_parameters     674
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.6687(3) 0.62401(15) 0.92622(11) 0.0253(5) Uani 1 1 d D . . . .
H1B H 0.755(2) 0.607(2) 0.9391(17) 0.023(9) Uiso 1 1 d D . . . .
O2 O -0.2494(3) 0.97206(15) 0.42609(11) 0.0249(5) Uani 1 1 d D . . . .
H2A H -0.338(3) 0.983(4) 0.439(3) 0.086(19) Uiso 1 1 d D . . . .
O3 O 0.5250(3) 0.52638(18) 0.52724(13) 0.0397(7) Uani 1 1 d . . . . .
O4 O 0.4695(3) 0.53909(17) 0.41085(14) 0.0369(6) Uani 1 1 d . . . . .
O5 O 0.7837(3) 0.5708(2) 0.57406(14) 0.0470(7) Uani 1 1 d D . . . .
H5A H 0.694(3) 0.551(3) 0.571(2) 0.056 Uiso 1 1 d D U . . .
O6 O 0.6685(3) 0.58542(19) 0.32187(14) 0.0453(7) Uani 1 1 d D . . . .
H6 H 0.585(3) 0.567(3) 0.339(2) 0.054 Uiso 1 1 d D U . . .
O7 O -0.0723(3) 0.55539(17) -0.02636(13) 0.0379(6) Uani 1 1 d . . . . .
O8 O -0.0952(3) 0.55864(16) 0.09242(13) 0.0331(6) Uani 1 1 d . . . . .
O9 O 0.1273(3) 0.52087(17) 0.17341(13) 0.0364(6) Uani 1 1 d D . . . .
H9 H 0.042(3) 0.540(3) 0.159(2) 0.053(14) Uiso 1 1 d D . . . .
O10 O 0.1732(3) 0.51093(17) -0.08403(13) 0.0347(6) Uani 1 1 d D . . . .
H10 H 0.081(2) 0.521(3) -0.077(3) 0.071(17) Uiso 1 1 d D . . . .
N1 N -0.2110(3) 0.96159(18) 0.60275(15) 0.0254(6) Uani 1 1 d D . . . .
H1A H -0.293(3) 0.9911(19) 0.5914(17) 0.024(9) Uiso 1 1 d D . . . .
N2 N -0.1153(3) 0.93224(18) 0.55215(14) 0.0248(6) Uani 1 1 d D . . . .
H2 H -0.137(5) 0.936(3) 0.5056(9) 0.053(13) Uiso 1 1 d D . . . .
N3 N 0.6435(3) 0.63986(17) 0.10186(14) 0.0224(6) Uani 1 1 d D . . . .
H3 H 0.732(2) 0.617(2) 0.0975(19) 0.027 Uiso 1 1 d D U . . .
N4 N 0.5446(3) 0.66584(17) 0.05196(14) 0.0219(6) Uani 1 1 d D . . . .
H4 H 0.563(4) 0.654(2) 0.0065(9) 0.026 Uiso 1 1 d D U . . .
C1 C -0.1515(4) 0.9481(2) 0.66767(18) 0.0272(7) Uani 1 1 d . . . . .
H1 H -0.196895 0.962823 0.712279 0.033 Uiso 1 1 calc R U . . .
C2 C -0.0122(4) 0.9091(2) 0.65899(17) 0.0240(7) Uani 1 1 d . . . . .
C3 C 0.0076(4) 0.89968(19) 0.58542(17) 0.0228(7) Uani 1 1 d . . . . .
C4 C 0.1397(4) 0.8585(2) 0.55027(17) 0.0248(7) Uani 1 1 d . . . . .
H4A H 0.176867 0.895294 0.510723 0.030 Uiso 1 1 calc R U . . .
H4B H 0.109356 0.802648 0.529526 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2670(4) 0.8446(2) 0.60633(17) 0.0223(7) Uani 1 1 d . . . . .
H5 H 0.314668 0.901797 0.614909 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2090(3) 0.81207(19) 0.68033(15) 0.0196(6) Uani 1 1 d . . . . .
C7 C 0.1041(4) 0.8809(2) 0.71290(17) 0.0260(7) Uani 1 1 d . . . . .
H7A H 0.053164 0.857332 0.755925 0.031 Uiso 1 1 calc R U . . .
H7B H 0.164842 0.930931 0.728168 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1202(4) 0.7282(2) 0.67156(17) 0.0267(7) Uani 1 1 d . . . . .
H8A H 0.093857 0.705549 0.719096 0.040 Uiso 1 1 calc R U . . .
H8B H 0.182232 0.686191 0.645850 0.040 Uiso 1 1 calc R U . . .
H8C H 0.027869 0.739215 0.644132 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3889(4) 0.7867(2) 0.57430(17) 0.0305(8) Uani 1 1 d . . . . .
H9A H 0.343186 0.731007 0.561131 0.037 Uiso 1 1 calc R U . . .
H9B H 0.428097 0.813331 0.529747 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5200(4) 0.7710(2) 0.62595(17) 0.0317(8) Uani 1 1 d . . . . .
H10A H 0.575817 0.825170 0.633392 0.038 Uiso 1 1 calc R U . . .
H10B H 0.590241 0.728912 0.604377 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4646(4) 0.7371(2) 0.69893(16) 0.0202(6) Uani 1 1 d . . . . .
H11 H 0.413500 0.680745 0.690988 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3480(4) 0.8007(2) 0.73048(16) 0.0207(6) Uani 1 1 d . . . . .
H12 H 0.399477 0.857723 0.731670 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3038(4) 0.7808(2) 0.80929(16) 0.0271(7) Uani 1 1 d . . . . .
H13A H 0.244768 0.829302 0.828804 0.033 Uiso 1 1 calc R U . . .
H13B H 0.238604 0.729297 0.810143 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4415(4) 0.7652(2) 0.85777(16) 0.0267(7) Uani 1 1 d . . . . .
H14A H 0.499589 0.819045 0.862642 0.032 Uiso 1 1 calc R U . . .
H14B H 0.407173 0.747819 0.906286 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5423(3) 0.69604(19) 0.82683(16) 0.0199(6) Uani 1 1 d . . . . .
C16 C 0.5947(4) 0.7238(2) 0.75167(16) 0.0231(7) Uani 1 1 d . . . . .
H16 H 0.646854 0.780191 0.757177 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4551(4) 0.6108(2) 0.82416(18) 0.0285(7) Uani 1 1 d . . . . .
H17A H 0.416248 0.597270 0.872180 0.043 Uiso 1 1 calc R U . . .
H17B H 0.522730 0.564912 0.808242 0.043 Uiso 1 1 calc R U . . .
H17C H 0.370779 0.615919 0.790364 0.043 Uiso 1 1 calc R U . . .
C18 C 0.7154(4) 0.6575(2) 0.73227(18) 0.0315(8) Uani 1 1 d . . . . .
H18A H 0.790129 0.681918 0.698459 0.038 Uiso 1 1 calc R U . . .
H18B H 0.669417 0.606038 0.710182 0.038 Uiso 1 1 calc R U . . .
C19 C 0.7906(4) 0.6350(2) 0.80602(17) 0.0269(7) Uani 1 1 d . . . . .
H19A H 0.791547 0.572253 0.813494 0.032 Uiso 1 1 calc R U . . .
H19B H 0.895757 0.656220 0.807334 0.032 Uiso 1 1 calc R U . . .
C20 C 0.6948(4) 0.67961(19) 0.86520(17) 0.0228(7) Uani 1 1 d . . . . .
C21 C 0.7730(4) 0.7607(2) 0.8922(2) 0.0369(8) Uani 1 1 d . . . . .
H21A H 0.713787 0.785960 0.931345 0.055 Uiso 1 1 calc R U . . .
H21B H 0.781569 0.802013 0.852733 0.055 Uiso 1 1 calc R U . . .
H21C H 0.873911 0.746211 0.909952 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5916(4) 0.6604(2) 0.16716(17) 0.0216(7) Uani 1 1 d . . . . .
H22 H 0.640407 0.648764 0.211575 0.026 Uiso 1 1 calc R U . . .
C23 C 0.4546(3) 0.7015(2) 0.15889(15) 0.0197(6) Uani 1 1 d . . . . .
C24 C 0.4262(3) 0.7031(2) 0.08497(16) 0.0210(6) Uani 1 1 d . . . . .
C25 C 0.2883(4) 0.7385(2) 0.05163(15) 0.0213(6) Uani 1 1 d . . . . .
H25A H 0.250804 0.698600 0.014291 0.026 Uiso 1 1 calc R U . . .
H25B H 0.311611 0.793924 0.028304 0.026 Uiso 1 1 calc R U . . .
C26 C 0.1666(3) 0.75148(19) 0.10953(16) 0.0198(6) Uani 1 1 d . . . . .
H26 H 0.133015 0.693155 0.124970 0.024 Uiso 1 1 calc R U . . .
C27 C 0.2292(3) 0.79750(19) 0.17806(15) 0.0177(6) Uani 1 1 d . . . . .
C28 C 0.3464(3) 0.7372(2) 0.21321(16) 0.0215(6) Uani 1 1 d . . . . .
H28A H 0.403304 0.769215 0.250296 0.026 Uiso 1 1 calc R U . . .
H28B H 0.293214 0.689405 0.237335 0.026 Uiso 1 1 calc R U . . .
C29 C 0.3040(3) 0.8828(2) 0.15743(16) 0.0221(6) Uani 1 1 d . . . . .
H29A H 0.390314 0.871719 0.125924 0.033 Uiso 1 1 calc R U . . .
H29B H 0.338447 0.912174 0.201036 0.033 Uiso 1 1 calc R U . . .
H29C H 0.230808 0.919029 0.132189 0.033 Uiso 1 1 calc R U . . .
C30 C 0.0975(3) 0.81059(19) 0.23233(15) 0.0185(6) Uani 1 1 d . . . . .
H30 H 0.062968 0.751680 0.245576 0.022 Uiso 1 1 calc R U . . .
C31 C -0.0411(3) 0.85513(19) 0.19936(16) 0.0183(6) Uani 1 1 d . . . . .
H31 H -0.011863 0.914449 0.184609 0.022 Uiso 1 1 calc R U . . .
C32 C -0.0960(4) 0.8068(2) 0.13328(16) 0.0249(7) Uani 1 1 d . . . . .
H32A H -0.181307 0.838390 0.111398 0.030 Uiso 1 1 calc R U . . .
H32B H -0.133131 0.749652 0.147990 0.030 Uiso 1 1 calc R U . . .
C33 C 0.0291(4) 0.7961(2) 0.07740(17) 0.0259(7) Uani 1 1 d . . . . .
H33A H -0.009365 0.762010 0.036420 0.031 Uiso 1 1 calc R U . . .
H33B H 0.059056 0.853103 0.058953 0.031 Uiso 1 1 calc R U . . .
C34 C 0.1501(3) 0.8524(2) 0.30365(16) 0.0235(7) Uani 1 1 d . . . . .
H34A H 0.230501 0.816725 0.325191 0.028 Uiso 1 1 calc R U . . .
H34B H 0.193618 0.909442 0.293034 0.028 Uiso 1 1 calc R U . . .
C35 C 0.0220(4) 0.8629(2) 0.35840(16) 0.0222(7) Uani 1 1 d . . . . .
H35A H -0.010266 0.805760 0.375584 0.027 Uiso 1 1 calc R U . . .
H35B H 0.059055 0.895823 0.400345 0.027 Uiso 1 1 calc R U . . .
C36 C -0.1130(3) 0.90943(19) 0.32512(16) 0.0189(6) Uani 1 1 d . . . . .
C37 C -0.1630(3) 0.86110(19) 0.25710(15) 0.0187(6) Uani 1 1 d . . . . .
H37 H -0.185566 0.801024 0.272371 0.022 Uiso 1 1 calc R U . . .
C38 C -0.0704(4) 1.00242(19) 0.30767(16) 0.0231(7) Uani 1 1 d . . . . .
H38A H -0.039218 1.031700 0.351869 0.035 Uiso 1 1 calc R U . . .
H38B H -0.157674 1.031931 0.286936 0.035 Uiso 1 1 calc R U . . .
H38C H 0.012940 1.003007 0.273078 0.035 Uiso 1 1 calc R U . . .
C39 C -0.3151(3) 0.9026(2) 0.23819(16) 0.0249(7) Uani 1 1 d . . . . .
H39A H -0.383369 0.860559 0.215244 0.030 Uiso 1 1 calc R U . . .
H39B H -0.300793 0.951664 0.205103 0.030 Uiso 1 1 calc R U . . .
C40 C -0.3798(4) 0.9332(2) 0.31153(17) 0.0268(7) Uani 1 1 d . . . . .
H40A H -0.396590 0.995860 0.310972 0.032 Uiso 1 1 calc R U . . .
H40B H -0.476867 0.904354 0.321693 0.032 Uiso 1 1 calc R U . . .
C41 C -0.2614(4) 0.9092(2) 0.36898(16) 0.0217(7) Uani 1 1 d . . . . .
C42 C -0.3015(4) 0.8239(2) 0.40417(18) 0.0320(8) Uani 1 1 d . . . . .
H42A H -0.220093 0.806603 0.436687 0.048 Uiso 1 1 calc R U . . .
H42B H -0.315015 0.780187 0.366920 0.048 Uiso 1 1 calc R U . . .
H42C H -0.395297 0.830263 0.431518 0.048 Uiso 1 1 calc R U . . .
C43 C 0.5609(4) 0.5461(2) 0.46400(19) 0.0277(7) Uani 1 1 d . . . . .
C44 C 0.7156(4) 0.5776(2) 0.44889(17) 0.0231(7) Uani 1 1 d . . . . .
C45 C 0.8197(4) 0.5887(2) 0.50516(18) 0.0283(8) Uani 1 1 d . . . . .
C46 C 0.9649(4) 0.6178(2) 0.4912(2) 0.0354(9) Uani 1 1 d . . . . .
H46 H 1.034026 0.626538 0.529556 0.043 Uiso 1 1 calc R U . . .
C47 C 1.0071(4) 0.6338(2) 0.4219(2) 0.0393(9) Uani 1 1 d . . . . .
H47 H 1.106729 0.653129 0.412524 0.047 Uiso 1 1 calc R U . . .
C48 C 0.9097(4) 0.6227(2) 0.3654(2) 0.0366(9) Uani 1 1 d . . . . .
H48 H 0.941859 0.634023 0.317602 0.044 Uiso 1 1 calc R U . . .
C49 C 0.7638(4) 0.5949(2) 0.37861(19) 0.0292(8) Uani 1 1 d . . . . .
C50 C -0.0195(4) 0.5454(2) 0.03603(18) 0.0257(7) Uani 1 1 d . . . . .
C51 C 0.1396(4) 0.51712(19) 0.04349(17) 0.0221(7) Uani 1 1 d . . . . .
C52 C 0.2073(4) 0.5070(2) 0.11211(18) 0.0257(7) Uani 1 1 d . . . . .
C53 C 0.3570(4) 0.4838(2) 0.1184(2) 0.0306(8) Uani 1 1 d . . . . .
H53 H 0.402305 0.478609 0.164542 0.037 Uiso 1 1 calc R U . . .
C54 C 0.4403(4) 0.4682(2) 0.0568(2) 0.0344(8) Uani 1 1 d . . . . .
H54 H 0.543038 0.451919 0.061169 0.041 Uiso 1 1 calc R U . . .
C55 C 0.3782(4) 0.4758(2) -0.0102(2) 0.0315(8) Uani 1 1 d . . . . .
H55 H 0.437003 0.463508 -0.051694 0.038 Uiso 1 1 calc R U . . .
C56 C 0.2294(4) 0.5013(2) -0.01755(17) 0.0251(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.447(4) . ?
O1 H1B 0.847(14) . ?
O2 C41 1.450(4) . ?
O2 H2A 0.845(15) . ?
O3 C43 1.257(4) . ?
O4 C43 1.283(4) . ?
O5 C45 1.350(4) . ?
O5 H5A 0.853(14) . ?
O6 C49 1.360(4) . ?
O6 H6 0.859(14) . ?
O7 C50 1.260(4) . ?
O8 C50 1.262(4) . ?
O9 C52 1.360(4) . ?
O9 H9 0.860(14) . ?
O10 C56 1.341(4) . ?
O10 H10 0.848(14) . ?
N1 C1 1.334(4) . ?
N1 N2 1.347(4) . ?
N1 H1A 0.890(14) . ?
N2 C3 1.352(4) . ?
N2 H2 0.888(14) . ?
N3 C22 1.338(4) . ?
N3 N4 1.340(4) . ?
N3 H3 0.871(14) . ?
N4 C24 1.349(4) . ?
N4 H4 0.882(14) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(5) . ?
C2 C7 1.504(4) . ?
C3 C4 1.488(4) . ?
C4 C5 1.552(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C9 1.530(5) . ?
C5 C6 1.554(4) . ?
C5 H5 1.0000 . ?
C6 C8 1.537(4) . ?
C6 C7 1.545(4) . ?
C6 C12 1.556(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.528(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.537(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.529(4) . ?
C11 C12 1.550(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.549(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.537(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.515(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.535(4) . ?
C15 C17 1.540(4) . ?
C15 C20 1.550(4) . ?
C16 C18 1.532(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.564(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.555(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.529(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(4) . ?
C23 C28 1.501(4) . ?
C24 C25 1.477(4) . ?
C25 C26 1.538(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C33 1.526(4) . ?
C26 C27 1.564(4) . ?
C26 H26 1.0000 . ?
C27 C29 1.537(4) . ?
C27 C28 1.547(4) . ?
C27 C30 1.557(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.539(4) . ?
C30 C34 1.550(4) . ?
C30 H30 1.0000 . ?
C31 C32 1.521(4) . ?
C31 C37 1.527(4) . ?
C31 H31 1.0000 . ?
C32 C33 1.530(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.534(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.530(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C38 1.534(4) . ?
C36 C37 1.538(4) . ?
C36 C41 1.549(4) . ?
C37 C39 1.538(4) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.554(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.544(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.525(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.485(5) . ?
C44 C49 1.401(5) . ?
C44 C45 1.406(4) . ?
C45 C46 1.390(5) . ?
C46 C47 1.366(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.370(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.387(5) . ?
C48 H48 0.9500 . ?
C50 C51 1.485(5) . ?
C51 C56 1.409(4) . ?
C51 C52 1.419(4) . ?
C52 C53 1.381(5) . ?
C53 C54 1.386(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.367(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.386(5) . ?
C55 H55 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
C20 O1 H1B 105(2) . . ?
C41 O2 H2A 106(4) . . ?
C45 O5 H5A 104(3) . . ?
C49 O6 H6 106(3) . . ?
C52 O9 H9 105(3) . . ?
C56 O10 H10 103(3) . . ?
C1 N1 N2 109.2(3) . . ?
C1 N1 H1A 128(2) . . ?
N2 N1 H1A 122(2) . . ?
N1 N2 C3 108.4(3) . . ?
N1 N2 H2 121(3) . . ?
C3 N2 H2 130(3) . . ?
C22 N3 N4 109.3(3) . . ?
C22 N3 H3 120(2) . . ?
N4 N3 H3 131(2) . . ?
N3 N4 C24 109.0(2) . . ?
N3 N4 H4 119(2) . . ?
C24 N4 H4 132(2) . . ?
N1 C1 C2 108.4(3) . . ?
N1 C1 H1 125.8 . . ?
C2 C1 H1 125.8 . . ?
C1 C2 C3 105.9(3) . . ?
C1 C2 C7 131.5(3) . . ?
C3 C2 C7 122.6(3) . . ?
N2 C3 C2 108.0(3) . . ?
N2 C3 C4 126.6(3) . . ?
C2 C3 C4 125.4(3) . . ?
C3 C4 C5 109.8(3) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C9 C5 C4 109.6(3) . . ?
C9 C5 C6 112.7(3) . . ?
C4 C5 C6 113.5(2) . . ?
C9 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C6 C5 H5 106.9 . . ?
C8 C6 C7 109.0(3) . . ?
C8 C6 C12 111.9(2) . . ?
C7 C6 C12 108.7(2) . . ?
C8 C6 C5 110.8(2) . . ?
C7 C6 C5 108.6(2) . . ?
C12 C6 C5 107.8(2) . . ?
C2 C7 C6 110.8(3) . . ?
C2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C5 112.8(3) . . ?
C10 C9 H9A 109.0 . . ?
C5 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C5 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 111.5(3) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C16 C11 C10 111.8(3) . . ?
C16 C11 C12 110.4(2) . . ?
C10 C11 C12 109.1(3) . . ?
C16 C11 H11 108.5 . . ?
C10 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C13 C12 C11 113.5(2) . . ?
C13 C12 C6 112.9(2) . . ?
C11 C12 C6 112.0(2) . . ?
C13 C12 H12 105.9 . . ?
C11 C12 H12 105.9 . . ?
C6 C12 H12 105.9 . . ?
C14 C13 C12 112.7(3) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 111.0(3) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 108.9(3) . . ?
C14 C15 C17 109.3(3) . . ?
C16 C15 C17 111.5(3) . . ?
C14 C15 C20 117.3(3) . . ?
C16 C15 C20 101.6(2) . . ?
C17 C15 C20 108.1(2) . . ?
C11 C16 C18 117.9(3) . . ?
C11 C16 C15 113.2(3) . . ?
C18 C16 C15 103.6(2) . . ?
C11 C16 H16 107.2 . . ?
C18 C16 H16 107.2 . . ?
C15 C16 H16 107.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 104.0(2) . . ?
C16 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C16 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 109.0 . . ?
C20 C19 C18 106.7(2) . . ?
C20 C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C18 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O1 C20 C21 108.2(3) . . ?
O1 C20 C15 108.7(2) . . ?
C21 C20 C15 114.2(3) . . ?
O1 C20 C19 112.0(2) . . ?
C21 C20 C19 110.8(3) . . ?
C15 C20 C19 103.0(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 . . ?
N3 C22 C23 108.2(3) . . ?
N3 C22 H22 125.9 . . ?
C23 C22 H22 125.9 . . ?
C22 C23 C24 106.1(3) . . ?
C22 C23 C28 131.3(3) . . ?
C24 C23 C28 122.6(3) . . ?
N4 C24 C23 107.4(3) . . ?
N4 C24 C25 127.9(3) . . ?
C23 C24 C25 124.7(3) . . ?
C24 C25 C26 109.7(2) . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C33 C26 C25 110.3(2) . . ?
C33 C26 C27 113.1(2) . . ?
C25 C26 C27 112.4(2) . . ?
C33 C26 H26 106.8 . . ?
C25 C26 H26 106.8 . . ?
C27 C26 H26 106.8 . . ?
C29 C27 C28 110.0(2) . . ?
C29 C27 C30 111.8(2) . . ?
C28 C27 C30 108.1(2) . . ?
C29 C27 C26 110.4(2) . . ?
C28 C27 C26 107.6(2) . . ?
C30 C27 C26 108.8(2) . . ?
C23 C28 C27 111.8(2) . . ?
C23 C28 H28A 109.3 . . ?
C27 C28 H28A 109.3 . . ?
C23 C28 H28B 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C34 113.0(2) . . ?
C31 C30 C27 113.6(2) . . ?
C34 C30 C27 112.6(2) . . ?
C31 C30 H30 105.6 . . ?
C34 C30 H30 105.6 . . ?
C27 C30 H30 105.6 . . ?
C32 C31 C37 111.8(2) . . ?
C32 C31 C30 110.7(2) . . ?
C37 C31 C30 108.3(2) . . ?
C32 C31 H31 108.7 . . ?
C37 C31 H31 108.7 . . ?
C30 C31 H31 108.7 . . ?
C31 C32 C33 111.7(3) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C26 C33 C32 111.4(3) . . ?
C26 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C26 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C30 112.9(3) . . ?
C35 C34 H34A 109.0 . . ?
C30 C34 H34A 109.0 . . ?
C35 C34 H34B 109.0 . . ?
C30 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C36 C35 C34 111.2(2) . . ?
C36 C35 H35A 109.4 . . ?
C34 C35 H35A 109.4 . . ?
C36 C35 H35B 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C35 C36 C38 110.0(3) . . ?
C35 C36 C37 109.0(2) . . ?
C38 C36 C37 111.2(2) . . ?
C35 C36 C41 116.8(2) . . ?
C38 C36 C41 108.9(2) . . ?
C37 C36 C41 100.8(2) . . ?
C31 C37 C39 119.1(2) . . ?
C31 C37 C36 113.8(2) . . ?
C39 C37 C36 103.5(2) . . ?
C31 C37 H37 106.5 . . ?
C39 C37 H37 106.5 . . ?
C36 C37 H37 106.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 104.6(2) . . ?
C37 C39 H39A 110.8 . . ?
C40 C39 H39A 110.8 . . ?
C37 C39 H39B 110.8 . . ?
C40 C39 H39B 110.8 . . ?
H39A C39 H39B 108.9 . . ?
C41 C40 C39 106.3(2) . . ?
C41 C40 H40A 110.5 . . ?
C39 C40 H40A 110.5 . . ?
C41 C40 H40B 110.5 . . ?
C39 C40 H40B 110.5 . . ?
H40A C40 H40B 108.7 . . ?
O2 C41 C42 107.1(2) . . ?
O2 C41 C40 113.1(3) . . ?
C42 C41 C40 110.5(3) . . ?
O2 C41 C36 108.8(2) . . ?
C42 C41 C36 115.3(3) . . ?
C40 C41 C36 102.3(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O3 C43 O4 122.6(3) . . ?
O3 C43 C44 119.5(3) . . ?
O4 C43 C44 117.8(3) . . ?
C49 C44 C45 118.0(3) . . ?
C49 C44 C43 121.5(3) . . ?
C45 C44 C43 120.5(3) . . ?
O5 C45 C46 117.7(3) . . ?
O5 C45 C44 121.6(3) . . ?
C46 C45 C44 120.7(3) . . ?
C47 C46 C45 119.3(3) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C46 C47 C48 121.8(3) . . ?
C46 C47 H47 119.1 . . ?
C48 C47 H47 119.1 . . ?
C47 C48 C49 119.5(3) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
O6 C49 C48 118.5(3) . . ?
O6 C49 C44 120.8(3) . . ?
C48 C49 C44 120.7(3) . . ?
O7 C50 O8 123.2(3) . . ?
O7 C50 C51 118.4(3) . . ?
O8 C50 C51 118.5(3) . . ?
C56 C51 C52 117.7(3) . . ?
C56 C51 C50 121.0(3) . . ?
C52 C51 C50 121.3(3) . . ?
O9 C52 C53 118.2(3) . . ?
O9 C52 C51 121.0(3) . . ?
C53 C52 C51 120.8(3) . . ?
C52 C53 C54 119.2(3) . . ?
C52 C53 H53 120.4 . . ?
C54 C53 H53 120.4 . . ?
C55 C54 C53 121.6(3) . . ?
C55 C54 H54 119.2 . . ?
C53 C54 H54 119.2 . . ?
C54 C55 C56 119.8(3) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
O10 C56 C55 118.4(3) . . ?
O10 C56 C51 120.9(3) . . ?
C55 C56 C51 120.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 -0.2(4) . . . . ?
C22 N3 N4 C24 -0.5(3) . . . . ?
N2 N1 C1 C2 0.3(4) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C7 178.9(3) . . . . ?
N1 N2 C3 C2 0.0(4) . . . . ?
N1 N2 C3 C4 178.3(3) . . . . ?
C1 C2 C3 N2 0.2(4) . . . . ?
C7 C2 C3 N2 -179.1(3) . . . . ?
C1 C2 C3 C4 -178.2(3) . . . . ?
C7 C2 C3 C4 2.6(5) . . . . ?
N2 C3 C4 C5 170.1(3) . . . . ?
C2 C3 C4 C5 -11.8(4) . . . . ?
C3 C4 C5 C9 168.7(3) . . . . ?
C3 C4 C5 C6 41.8(3) . . . . ?
C9 C5 C6 C8 -68.3(3) . . . . ?
C4 C5 C6 C8 57.0(3) . . . . ?
C9 C5 C6 C7 172.1(3) . . . . ?
C4 C5 C6 C7 -62.7(3) . . . . ?
C9 C5 C6 C12 54.4(3) . . . . ?
C4 C5 C6 C12 179.7(3) . . . . ?
C1 C2 C7 C6 158.6(3) . . . . ?
C3 C2 C7 C6 -22.3(4) . . . . ?
C8 C6 C7 C2 -70.9(3) . . . . ?
C12 C6 C7 C2 166.9(3) . . . . ?
C5 C6 C7 C2 49.8(3) . . . . ?
C4 C5 C9 C10 179.1(3) . . . . ?
C6 C5 C9 C10 -53.5(4) . . . . ?
C5 C9 C10 C11 53.6(4) . . . . ?
C9 C10 C11 C16 -178.2(3) . . . . ?
C9 C10 C11 C12 -55.9(4) . . . . ?
C16 C11 C12 C13 -47.4(3) . . . . ?
C10 C11 C12 C13 -170.6(3) . . . . ?
C16 C11 C12 C6 -176.7(2) . . . . ?
C10 C11 C12 C6 60.1(3) . . . . ?
C8 C6 C12 C13 -66.1(3) . . . . ?
C7 C6 C12 C13 54.4(3) . . . . ?
C5 C6 C12 C13 171.9(3) . . . . ?
C8 C6 C12 C11 63.5(3) . . . . ?
C7 C6 C12 C11 -176.1(3) . . . . ?
C5 C6 C12 C11 -58.5(3) . . . . ?
C11 C12 C13 C14 48.3(4) . . . . ?
C6 C12 C13 C14 177.1(3) . . . . ?
C12 C13 C14 C15 -54.2(4) . . . . ?
C13 C14 C15 C16 59.1(4) . . . . ?
C13 C14 C15 C17 -63.0(3) . . . . ?
C13 C14 C15 C20 173.6(3) . . . . ?
C10 C11 C16 C18 -63.0(4) . . . . ?
C12 C11 C16 C18 175.4(3) . . . . ?
C10 C11 C16 C15 175.9(3) . . . . ?
C12 C11 C16 C15 54.3(3) . . . . ?
C14 C15 C16 C11 -60.7(3) . . . . ?
C17 C15 C16 C11 60.0(3) . . . . ?
C20 C15 C16 C11 175.0(3) . . . . ?
C14 C15 C16 C18 170.4(3) . . . . ?
C17 C15 C16 C18 -68.9(3) . . . . ?
C20 C15 C16 C18 46.1(3) . . . . ?
C11 C16 C18 C19 -159.1(3) . . . . ?
C15 C16 C18 C19 -33.2(3) . . . . ?
C16 C18 C19 C20 7.8(3) . . . . ?
C14 C15 C20 O1 82.4(3) . . . . ?
C16 C15 C20 O1 -159.1(2) . . . . ?
C17 C15 C20 O1 -41.7(3) . . . . ?
C14 C15 C20 C21 -38.5(4) . . . . ?
C16 C15 C20 C21 80.1(3) . . . . ?
C17 C15 C20 C21 -162.5(3) . . . . ?
C14 C15 C20 C19 -158.7(3) . . . . ?
C16 C15 C20 C19 -40.2(3) . . . . ?
C17 C15 C20 C19 77.2(3) . . . . ?
C18 C19 C20 O1 136.6(3) . . . . ?
C18 C19 C20 C21 -102.5(3) . . . . ?
C18 C19 C20 C15 20.0(3) . . . . ?
N4 N3 C22 C23 -0.3(3) . . . . ?
N3 C22 C23 C24 1.0(3) . . . . ?
N3 C22 C23 C28 179.2(3) . . . . ?
N3 N4 C24 C23 1.1(3) . . . . ?
N3 N4 C24 C25 -177.8(3) . . . . ?
C22 C23 C24 N4 -1.3(3) . . . . ?
C28 C23 C24 N4 -179.7(3) . . . . ?
C22 C23 C24 C25 177.7(3) . . . . ?
C28 C23 C24 C25 -0.8(5) . . . . ?
N4 C24 C25 C26 164.4(3) . . . . ?
C23 C24 C25 C26 -14.3(4) . . . . ?
C24 C25 C26 C33 174.4(3) . . . . ?
C24 C25 C26 C27 47.1(3) . . . . ?
C33 C26 C27 C29 -70.7(3) . . . . ?
C25 C26 C27 C29 55.1(3) . . . . ?
C33 C26 C27 C28 169.2(2) . . . . ?
C25 C26 C27 C28 -65.0(3) . . . . ?
C33 C26 C27 C30 52.3(3) . . . . ?
C25 C26 C27 C30 178.1(2) . . . . ?
C22 C23 C28 C27 165.2(3) . . . . ?
C24 C23 C28 C27 -16.8(4) . . . . ?
C29 C27 C28 C23 -73.4(3) . . . . ?
C30 C27 C28 C23 164.3(2) . . . . ?
C26 C27 C28 C23 46.9(3) . . . . ?
C29 C27 C30 C31 69.7(3) . . . . ?
C28 C27 C30 C31 -169.0(2) . . . . ?
C26 C27 C30 C31 -52.4(3) . . . . ?
C29 C27 C30 C34 -60.3(3) . . . . ?
C28 C27 C30 C34 61.0(3) . . . . ?
C26 C27 C30 C34 177.5(2) . . . . ?
C34 C30 C31 C32 -175.0(3) . . . . ?
C27 C30 C31 C32 55.2(3) . . . . ?
C34 C30 C31 C37 -52.1(3) . . . . ?
C27 C30 C31 C37 178.0(2) . . . . ?
C37 C31 C32 C33 -176.5(2) . . . . ?
C30 C31 C32 C33 -55.7(3) . . . . ?
C25 C26 C33 C32 177.9(3) . . . . ?
C27 C26 C33 C32 -55.2(3) . . . . ?
C31 C32 C33 C26 56.2(4) . . . . ?
C31 C30 C34 C35 51.5(3) . . . . ?
C27 C30 C34 C35 -178.1(2) . . . . ?
C30 C34 C35 C36 -52.6(3) . . . . ?
C34 C35 C36 C38 -66.8(3) . . . . ?
C34 C35 C36 C37 55.3(3) . . . . ?
C34 C35 C36 C41 168.5(3) . . . . ?
C32 C31 C37 C39 -57.4(4) . . . . ?
C30 C31 C37 C39 -179.6(2) . . . . ?
C32 C31 C37 C36 -180.0(2) . . . . ?
C30 C31 C37 C36 57.8(3) . . . . ?
C35 C36 C37 C31 -60.2(3) . . . . ?
C38 C36 C37 C31 61.2(3) . . . . ?
C41 C36 C37 C31 176.4(2) . . . . ?
C35 C36 C37 C39 169.0(2) . . . . ?
C38 C36 C37 C39 -69.6(3) . . . . ?
C41 C36 C37 C39 45.6(3) . . . . ?
C31 C37 C39 C40 -156.3(3) . . . . ?
C36 C37 C39 C40 -28.8(3) . . . . ?
C37 C39 C40 C41 0.8(3) . . . . ?
C39 C40 C41 O2 143.8(3) . . . . ?
C39 C40 C41 C42 -96.2(3) . . . . ?
C39 C40 C41 C36 27.0(3) . . . . ?
C35 C36 C41 O2 77.9(3) . . . . ?
C38 C36 C41 O2 -47.3(3) . . . . ?
C37 C36 C41 O2 -164.3(2) . . . . ?
C35 C36 C41 C42 -42.3(4) . . . . ?
C38 C36 C41 C42 -167.5(3) . . . . ?
C37 C36 C41 C42 75.5(3) . . . . ?
C35 C36 C41 C40 -162.2(3) . . . . ?
C38 C36 C41 C40 72.6(3) . . . . ?
C37 C36 C41 C40 -44.4(3) . . . . ?
O3 C43 C44 C49 175.6(3) . . . . ?
O4 C43 C44 C49 -3.3(5) . . . . ?
O3 C43 C44 C45 -2.6(5) . . . . ?
O4 C43 C44 C45 178.4(3) . . . . ?
C49 C44 C45 O5 -177.8(3) . . . . ?
C43 C44 C45 O5 0.6(5) . . . . ?
C49 C44 C45 C46 1.4(5) . . . . ?
C43 C44 C45 C46 179.7(3) . . . . ?
O5 C45 C46 C47 177.7(3) . . . . ?
C44 C45 C46 C47 -1.5(5) . . . . ?
C45 C46 C47 C48 0.6(5) . . . . ?
C46 C47 C48 C49 0.3(5) . . . . ?
C47 C48 C49 O6 179.1(3) . . . . ?
C47 C48 C49 C44 -0.3(5) . . . . ?
C45 C44 C49 O6 -179.9(3) . . . . ?
C43 C44 C49 O6 1.8(5) . . . . ?
C45 C44 C49 C48 -0.5(5) . . . . ?
C43 C44 C49 C48 -178.8(3) . . . . ?
O7 C50 C51 C56 -0.3(5) . . . . ?
O8 C50 C51 C56 179.9(3) . . . . ?
O7 C50 C51 C52 178.2(3) . . . . ?
O8 C50 C51 C52 -1.6(5) . . . . ?
C56 C51 C52 O9 -179.7(3) . . . . ?
C50 C51 C52 O9 1.7(5) . . . . ?
C56 C51 C52 C53 1.0(4) . . . . ?
C50 C51 C52 C53 -177.5(3) . . . . ?
O9 C52 C53 C54 179.1(3) . . . . ?
C51 C52 C53 C54 -1.6(5) . . . . ?
C52 C53 C54 C55 0.4(5) . . . . ?
C53 C54 C55 C56 1.4(5) . . . . ?
C54 C55 C56 O10 177.8(3) . . . . ?
C54 C55 C56 C51 -2.0(5) . . . . ?
C52 C51 C56 O10 -179.0(3) . . . . ?
C50 C51 C56 O10 -0.4(5) . . . . ?
C52 C51 C56 C55 0.8(4) . . . . ?
C50 C51 C56 C55 179.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.888(14) 1.87(2) 2.701(4) 155(4) . yes
N1 H1A O4 0.890(14) 1.732(16) 2.605(4) 166(3) 2_556 yes
N4 H4 O1 0.882(14) 1.822(18) 2.665(3) 159(3) 1_554 yes
N3 H3 O8 0.871(14) 1.781(15) 2.648(3) 174(4) 1_655 yes
O1 H1B O7 0.847(14) 1.845(15) 2.684(3) 171(3) 1_656 yes
O2 H2A O3 0.845(15) 1.893(18) 2.729(3) 170(6) 2_556 yes
O5 H5A O3 0.853(14) 1.75(2) 2.550(4) 154(4) . yes
O6 H6 O4 0.859(14) 1.74(3) 2.525(4) 152(5) . yes
O9 H9 O8 0.860(14) 1.76(2) 2.551(3) 152(4) . yes
O10 H10 O7 0.848(14) 1.73(3) 2.525(4) 155(5) . yes

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_STAN-GA-CH3CN-H2O
_database_code_depnum_ccdc_archive 'CCDC 1863940'
_audit_update_record             
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C21 H32.5 N2 O, C3.5 H2.5 O2.5, H0.5 O0.25, C2 H3 N'
_chemical_formula_sum            'C26.50 H38.50 N3 O3.75'
_chemical_formula_weight         459.10

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   32.061(3)
_cell_length_b                   11.0501(9)
_cell_length_c                   7.0657(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.859(3)
_cell_angle_gamma                90
_cell_volume                     2497.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3226
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.35

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             994
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1117 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8767.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11229
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5681
_reflns_number_gt                3855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+1.5918P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5681
_refine_ls_number_parameters     332
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.025
_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 0.08401(8) 0.4464(3) 0.0477(4) 0.0352(7) Uani 1 1 d D . . . .
H1 H 0.0814(15) 0.5205(17) 0.074(7) 0.047(16) Uiso 1 1 d D . . . .
O2 O 0.4817(2) 1.2528(4) 0.3616(8) 0.114(2) Uani 1 1 d . . . . .
O3 O 0.46453(10) 0.8103(3) 0.1994(5) 0.0394(8) Uani 1 1 d D . . . .
H3 H 0.4525(14) 0.850(4) 0.108(5) 0.053(16) Uiso 1 1 d D . . . .
O4 O 0.500000 0.6918(4) 0.500000 0.0440(12) Uani 1 2 d DS T P . .
H4 H 0.5213(18) 0.667(8) 0.567(12) 0.04(3) Uiso 0.5 1 d D . P . .
O5 O 0.000000 1.1170(13) 0.000000 0.091(4) Uani 0.5 2 d DS T P . .
H5A H -0.013(5) 1.184(7) -0.02(3) 0.137 Uiso 0.5 1 d D U P . .
N1 N 0.43382(10) 0.5577(3) 0.3438(5) 0.0318(7) Uani 1 1 d D U . . .
H1A H 0.4578(13) 0.596(7) 0.360(12) 0.038 Uiso 0.5 1 d D U P . .
N2 N 0.42742(10) 0.4372(3) 0.3519(5) 0.0325(8) Uani 1 1 d D U . . .
H2 H 0.4460(11) 0.379(3) 0.360(6) 0.039 Uiso 1 1 d D U . . .
N3 N 0.08128(17) 0.7118(5) 0.1080(8) 0.0724(15) Uani 1 1 d . . . . .
C1 C 0.39653(12) 0.6117(4) 0.3208(6) 0.0313(8) Uani 1 1 d . U . . .
H1B H 0.392149 0.696648 0.312632 0.026(10) Uiso 1 1 calc R . . . .
C2 C 0.36524(12) 0.5251(4) 0.3108(6) 0.0290(9) Uani 1 1 d . U . . .
C3 C 0.38590(11) 0.4158(4) 0.3311(5) 0.0285(9) Uani 1 1 d . . . . .
C4 C 0.36528(13) 0.2952(4) 0.3281(7) 0.0350(11) Uani 1 1 d . . . . .
H4A H 0.377576 0.244871 0.433604 0.042 Uiso 1 1 calc R U . . .
H4B H 0.369846 0.253414 0.207311 0.042 Uiso 1 1 calc R U . . .
C5 C 0.31808(12) 0.3113(4) 0.3486(6) 0.0288(9) Uani 1 1 d . . . . .
H5 H 0.314485 0.334124 0.483508 0.035 Uiso 1 1 calc R U . . .
C6 C 0.29826(11) 0.4138(4) 0.2221(5) 0.0254(9) Uani 1 1 d . . . . .
C7 C 0.31829(11) 0.5345(4) 0.2855(6) 0.0298(10) Uani 1 1 d . . . . .
H7A H 0.310595 0.597367 0.189562 0.036 Uiso 1 1 calc R U . . .
H7B H 0.307214 0.559724 0.406840 0.036 Uiso 1 1 calc R U . . .
C8 C 0.30585(11) 0.3926(4) 0.0116(6) 0.0281(9) Uani 1 1 d . . . . .
H8A H 0.292386 0.457113 -0.065536 0.042 Uiso 1 1 calc R U . . .
H8B H 0.294025 0.314217 -0.028949 0.042 Uiso 1 1 calc R U . . .
H8C H 0.335968 0.392820 -0.004687 0.042 Uiso 1 1 calc R U . . .
C9 C 0.25056(11) 0.4193(4) 0.2527(6) 0.0255(9) Uani 1 1 d . . . . .
H9 H 0.248557 0.434923 0.391157 0.031 Uiso 1 1 calc R U . . .
C10 C 0.22808(12) 0.2970(4) 0.2125(6) 0.0289(9) Uani 1 1 d . . . . .
H10 H 0.230517 0.274968 0.076468 0.035 Uiso 1 1 calc R U . . .
C11 C 0.24906(12) 0.1985(4) 0.3377(6) 0.0341(10) Uani 1 1 d . . . . .
H11A H 0.244608 0.216115 0.472263 0.041 Uiso 1 1 calc R U . . .
H11B H 0.235843 0.119534 0.305431 0.041 Uiso 1 1 calc R U . . .
C12 C 0.29583(12) 0.1901(4) 0.3129(6) 0.0330(10) Uani 1 1 d . . . . .
H12A H 0.300201 0.162711 0.182293 0.040 Uiso 1 1 calc R U . . .
H12B H 0.308346 0.128954 0.401954 0.040 Uiso 1 1 calc R U . . .
C13 C 0.22843(12) 0.5255(4) 0.1508(7) 0.0321(10) Uani 1 1 d . . . . .
H13A H 0.232138 0.518952 0.013186 0.039 Uiso 1 1 calc R U . . .
H13B H 0.241800 0.601825 0.196448 0.039 Uiso 1 1 calc R U . . .
C14 C 0.18124(11) 0.5316(4) 0.1814(6) 0.0310(10) Uani 1 1 d . . . . .
H14A H 0.177294 0.551020 0.315777 0.037 Uiso 1 1 calc R U . . .
H14B H 0.168178 0.596912 0.101863 0.037 Uiso 1 1 calc R U . . .
C15 C 0.16009(11) 0.4125(4) 0.1303(5) 0.0255(9) Uani 1 1 d . . . . .
C16 C 0.18212(11) 0.3119(4) 0.2477(6) 0.0297(10) Uani 1 1 d . . . . .
H16 H 0.180942 0.335566 0.383798 0.036 Uiso 1 1 calc R U . . .
C17 C 0.16122(12) 0.3893(4) -0.0845(5) 0.0301(9) Uani 1 1 d . . . . .
H17A H 0.190304 0.388614 -0.119231 0.045 Uiso 1 1 calc R U . . .
H17B H 0.145858 0.453606 -0.154705 0.045 Uiso 1 1 calc R U . . .
H17C H 0.148217 0.310978 -0.116162 0.045 Uiso 1 1 calc R U . . .
C18 C 0.15286(12) 0.2016(4) 0.2157(7) 0.0360(11) Uani 1 1 d . . . . .
H18A H 0.154888 0.147077 0.327116 0.043 Uiso 1 1 calc R U . . .
H18B H 0.159869 0.155358 0.102076 0.043 Uiso 1 1 calc R U . . .
C19 C 0.10843(13) 0.2578(4) 0.1871(7) 0.0373(11) Uani 1 1 d . . . . .
H19A H 0.094456 0.230532 0.065348 0.045 Uiso 1 1 calc R U . . .
H19B H 0.091110 0.233121 0.291335 0.045 Uiso 1 1 calc R U . . .
C20 C 0.11416(12) 0.3971(4) 0.1867(6) 0.0321(10) Uani 1 1 d . . . . .
C21 C 0.10616(13) 0.4515(5) 0.3781(6) 0.0443(12) Uani 1 1 d . . . . .
H21A H 0.077411 0.433755 0.408407 0.066 Uiso 1 1 calc R U . . .
H21B H 0.110179 0.539370 0.373577 0.066 Uiso 1 1 calc R U . . .
H21C H 0.125707 0.416623 0.475819 0.066 Uiso 1 1 calc R U . . .
C22 C 0.500000 1.1995(7) 0.500000 0.058(2) Uani 1 2 d S T P . .
C23 C 0.500000 1.0643(6) 0.500000 0.0336(14) Uani 1 2 d S T P . .
C24 C 0.48224(12) 1.0028(4) 0.3442(6) 0.0300(10) Uani 1 1 d . . . . .
H24 H 0.470277 1.046218 0.237986 0.036 Uiso 1 1 calc R U . . .
C25 C 0.48202(12) 0.8783(4) 0.3442(6) 0.0286(10) Uani 1 1 d . . . . .
C26 C 0.500000 0.8152(5) 0.500000 0.0291(13) Uani 1 2 d S T P . .
C27 C 0.07266(17) 0.8101(6) 0.1268(8) 0.0556(14) Uani 1 1 d . . . . .
C28 C 0.0655(3) 0.9378(6) 0.1502(10) 0.099(3) Uani 1 1 d . . . . .
H28A H 0.066941 0.978706 0.027761 0.149 Uiso 1 1 calc R U . . .
H28B H 0.086958 0.971101 0.241106 0.149 Uiso 1 1 calc R U . . .
H28C H 0.037840 0.950432 0.197722 0.149 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 C20 1.438(5) . ?
O1 H1 0.845(14) . ?
O2 C22 1.253(6) . ?
O3 C25 1.360(5) . ?
O3 H3 0.852(14) . ?
O4 C26 1.364(7) . ?
O4 H4 0.850(14) . ?
O4 H4 0.850(14) 2_656 ?
O5 H5A 0.858(15) . ?
O5 H5A 0.858(15) 2 ?
N1 C1 1.337(5) . ?
N1 N2 1.349(5) . ?
N1 H1A 0.877(14) . ?
N2 C3 1.350(5) . ?
N2 H2 0.880(14) . ?
N3 C27 1.131(7) . ?
C1 C2 1.385(6) . ?
C1 H1B 0.9500 . ?
C2 C3 1.380(6) . ?
C2 C7 1.507(5) . ?
C3 C4 1.488(6) . ?
C4 C5 1.540(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.530(6) . ?
C5 C6 1.552(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.534(6) . ?
C6 C8 1.541(5) . ?
C6 C9 1.560(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C13 1.527(6) . ?
C9 C10 1.549(5) . ?
C9 H9 1.0000 . ?
C10 C16 1.519(5) . ?
C10 C11 1.530(6) . ?
C10 H10 1.0000 . ?
C11 C12 1.524(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.544(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.513(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.531(6) . ?
C15 C17 1.542(5) . ?
C15 C20 1.561(5) . ?
C16 C18 1.545(6) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.555(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.549(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.517(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.493(10) . ?
C23 C24 1.383(5) 2_656 ?
C23 C24 1.383(5) . ?
C24 C25 1.375(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(5) . ?
C27 C28 1.440(9) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 H1 107(4) . . ?
C25 O3 H3 115(4) . . ?
C26 O4 H4 109(7) . . ?
C26 O4 H4 109(6) . 2_656 ?
H4 O4 H4 142(10) . 2_656 ?
H5A O5 H5A 60(10) . 2 ?
C1 N1 N2 108.0(3) . . ?
C1 N1 H1A 125(6) . . ?
N2 N1 H1A 127(6) . . ?
C3 N2 N1 108.7(3) . . ?
C3 N2 H2 122(3) . . ?
N1 N2 H2 129(3) . . ?
N1 C1 C2 109.7(4) . . ?
N1 C1 H1B 125.2 . . ?
C2 C1 H1B 125.2 . . ?
C3 C2 C1 105.0(3) . . ?
C3 C2 C7 122.7(4) . . ?
C1 C2 C7 132.3(4) . . ?
N2 C3 C2 108.7(4) . . ?
N2 C3 C4 126.3(4) . . ?
C2 C3 C4 125.0(3) . . ?
C3 C4 C5 109.5(3) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C12 C5 C4 109.5(3) . . ?
C12 C5 C6 112.0(3) . . ?
C4 C5 C6 113.4(3) . . ?
C12 C5 H5 107.2 . . ?
C4 C5 H5 107.2 . . ?
C6 C5 H5 107.2 . . ?
C7 C6 C8 108.9(3) . . ?
C7 C6 C5 108.6(3) . . ?
C8 C6 C5 111.1(3) . . ?
C7 C6 C9 108.7(3) . . ?
C8 C6 C9 111.1(3) . . ?
C5 C6 C9 108.4(3) . . ?
C2 C7 C6 111.7(3) . . ?
C2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 112.9(3) . . ?
C13 C9 C6 113.2(3) . . ?
C10 C9 C6 112.9(3) . . ?
C13 C9 H9 105.7 . . ?
C10 C9 H9 105.7 . . ?
C6 C9 H9 105.7 . . ?
C16 C10 C11 112.1(3) . . ?
C16 C10 C9 108.7(3) . . ?
C11 C10 C9 109.5(3) . . ?
C16 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C12 C11 C10 112.0(3) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C5 112.3(4) . . ?
C11 C12 H12A 109.1 . . ?
C5 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C5 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C9 C13 C14 113.3(3) . . ?
C9 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C9 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 110.9(3) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 108.6(3) . . ?
C14 C15 C17 109.8(3) . . ?
C16 C15 C17 111.8(3) . . ?
C14 C15 C20 116.7(3) . . ?
C16 C15 C20 101.0(3) . . ?
C17 C15 C20 108.6(3) . . ?
C10 C16 C15 114.0(3) . . ?
C10 C16 C18 118.5(4) . . ?
C15 C16 C18 103.9(3) . . ?
C10 C16 H16 106.6 . . ?
C15 C16 H16 106.6 . . ?
C18 C16 H16 106.6 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 104.2(4) . . ?
C16 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C16 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C20 C19 C18 106.8(3) . . ?
C20 C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C18 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O1 C20 C21 108.2(3) . . ?
O1 C20 C19 107.7(3) . . ?
C21 C20 C19 111.4(4) . . ?
O1 C20 C15 112.7(3) . . ?
C21 C20 C15 113.8(3) . . ?
C19 C20 C15 102.9(3) . . ?
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 . . ?
O2 C22 O2 123.8(9) . 2_656 ?
O2 C22 C23 118.1(4) . . ?
O2 C22 C23 118.1(4) 2_656 . ?
C24 C23 C24 121.1(6) 2_656 . ?
C24 C23 C22 119.4(3) 2_656 . ?
C24 C23 C22 119.4(3) . . ?
C25 C24 C23 119.6(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
O3 C25 C24 123.7(4) . . ?
O3 C25 C26 116.4(4) . . ?
C24 C25 C26 119.9(4) . . ?
O4 C26 C25 120.0(3) . 2_656 ?
O4 C26 C25 120.0(3) . . ?
C25 C26 C25 120.0(5) 2_656 . ?
N3 C27 C28 175.0(7) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.9(5) . . . . ?
N2 N1 C1 C2 -1.0(5) . . . . ?
N1 C1 C2 C3 0.6(5) . . . . ?
N1 C1 C2 C7 -179.8(4) . . . . ?
N1 N2 C3 C2 -0.5(5) . . . . ?
N1 N2 C3 C4 178.9(4) . . . . ?
C1 C2 C3 N2 -0.1(5) . . . . ?
C7 C2 C3 N2 -179.7(4) . . . . ?
C1 C2 C3 C4 -179.5(4) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
N2 C3 C4 C5 166.8(4) . . . . ?
C2 C3 C4 C5 -13.8(6) . . . . ?
C3 C4 C5 C12 170.7(4) . . . . ?
C3 C4 C5 C6 44.8(5) . . . . ?
C12 C5 C6 C7 172.3(3) . . . . ?
C4 C5 C6 C7 -63.1(4) . . . . ?
C12 C5 C6 C8 -67.9(4) . . . . ?
C4 C5 C6 C8 56.6(4) . . . . ?
C12 C5 C6 C9 54.4(4) . . . . ?
C4 C5 C6 C9 178.9(3) . . . . ?
C3 C2 C7 C6 -18.3(6) . . . . ?
C1 C2 C7 C6 162.2(4) . . . . ?
C8 C6 C7 C2 -74.3(4) . . . . ?
C5 C6 C7 C2 46.7(4) . . . . ?
C9 C6 C7 C2 164.5(3) . . . . ?
C7 C6 C9 C13 56.2(4) . . . . ?
C8 C6 C9 C13 -63.7(4) . . . . ?
C5 C6 C9 C13 174.1(3) . . . . ?
C7 C6 C9 C10 -174.1(3) . . . . ?
C8 C6 C9 C10 66.1(4) . . . . ?
C5 C6 C9 C10 -56.2(4) . . . . ?
C13 C9 C10 C16 -50.5(4) . . . . ?
C6 C9 C10 C16 179.6(3) . . . . ?
C13 C9 C10 C11 -173.2(3) . . . . ?
C6 C9 C10 C11 56.9(4) . . . . ?
C16 C10 C11 C12 -175.8(4) . . . . ?
C9 C10 C11 C12 -55.1(5) . . . . ?
C10 C11 C12 C5 55.4(5) . . . . ?
C4 C5 C12 C11 178.0(3) . . . . ?
C6 C5 C12 C11 -55.3(5) . . . . ?
C10 C9 C13 C14 50.4(5) . . . . ?
C6 C9 C13 C14 -179.8(3) . . . . ?
C9 C13 C14 C15 -53.4(5) . . . . ?
C13 C14 C15 C16 56.4(4) . . . . ?
C13 C14 C15 C17 -66.2(4) . . . . ?
C13 C14 C15 C20 169.7(3) . . . . ?
C11 C10 C16 C15 178.1(4) . . . . ?
C9 C10 C16 C15 56.9(4) . . . . ?
C11 C10 C16 C18 -59.2(5) . . . . ?
C9 C10 C16 C18 179.6(3) . . . . ?
C14 C15 C16 C10 -60.9(4) . . . . ?
C17 C15 C16 C10 60.5(5) . . . . ?
C20 C15 C16 C10 175.8(3) . . . . ?
C14 C15 C16 C18 168.7(3) . . . . ?
C17 C15 C16 C18 -69.9(4) . . . . ?
C20 C15 C16 C18 45.4(4) . . . . ?
C10 C16 C18 C19 -158.9(4) . . . . ?
C15 C16 C18 C19 -31.2(4) . . . . ?
C16 C18 C19 C20 4.7(5) . . . . ?
C18 C19 C20 O1 142.1(3) . . . . ?
C18 C19 C20 C21 -99.4(4) . . . . ?
C18 C19 C20 C15 22.9(4) . . . . ?
C14 C15 C20 O1 85.1(4) . . . . ?
C16 C15 C20 O1 -157.4(3) . . . . ?
C17 C15 C20 O1 -39.7(5) . . . . ?
C14 C15 C20 C21 -38.6(5) . . . . ?
C16 C15 C20 C21 78.9(5) . . . . ?
C17 C15 C20 C21 -163.3(4) . . . . ?
C14 C15 C20 C19 -159.3(4) . . . . ?
C16 C15 C20 C19 -41.7(4) . . . . ?
C17 C15 C20 C19 76.0(4) . . . . ?
O2 C22 C23 C24 -176.2(4) . . . 2_656 ?
O2 C22 C23 C24 3.8(4) 2_656 . . 2_656 ?
O2 C22 C23 C24 3.8(4) . . . . ?
O2 C22 C23 C24 -176.2(4) 2_656 . . . ?
C24 C23 C24 C25 0.3(3) 2_656 . . . ?
C22 C23 C24 C25 -179.7(3) . . . . ?
C23 C24 C25 O3 178.6(3) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
O3 C25 C26 O4 1.1(4) . . . . ?
C24 C25 C26 O4 -179.7(3) . . . . ?
O3 C25 C26 C25 -178.9(4) . . . 2_656 ?
C24 C25 C26 C25 0.3(3) . . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N3 0.845(14) 2.128(17) 2.966(7) 171(5) . yes
N1 H1A O3 0.877(14) 2.64(7) 3.152(5) 118(6) . yes
N1 H1A O4 0.877(14) 1.94(4) 2.757(4) 155(8) . yes
O3 H3 O1 0.852(14) 1.882(19) 2.714(4) 165(5) 4 yes
O4 H4 N1 0.850(14) 1.95(4) 2.757(4) 158(9) 2_656 yes
N2 H2 O2 0.880(14) 1.800(16) 2.678(6) 175(5) 1_545 yes

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_STAN-DHA
_database_code_depnum_ccdc_archive 'CCDC 1863938'
_audit_update_record             
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H32 N2 O, C7 H6 O4'
_chemical_formula_sum            'C28 H38 N2 O5'
_chemical_formula_weight         482.60

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                   9.6635(3)
_cell_length_b                   23.4950(6)
_cell_length_c                   11.8249(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.7610(10)
_cell_angle_gamma                90
_cell_volume                     2457.19(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9262
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      74.56

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42525
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.733
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             9891
_reflns_number_gt                9715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.985

_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0486P)²+0.5059P] 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 4583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         9891
_refine_ls_number_parameters     677
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C 0.2123(2) 0.71127(9) -0.38098(19) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.153085 0.678409 -0.385354 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3175(2) 0.73483(9) -0.27103(18) 0.0171(4) Uani 1 1 d . . . . .
C3 C 0.3757(2) 0.78151(9) -0.30824(18) 0.0182(4) Uani 1 1 d . . . . .
C4 C 0.4954(2) 0.81998(9) -0.22497(18) 0.0198(4) Uani 1 1 d . . . . .
H4A H 0.468306 0.860067 -0.249835 0.024 Uiso 1 1 calc R U . . .
H4B H 0.592654 0.811563 -0.230818 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5112(2) 0.81104(8) -0.09143(18) 0.0174(4) Uani 1 1 d . . . . .
H5 H 0.418709 0.827521 -0.085939 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5176(2) 0.74704(8) -0.05482(18) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.3659(2) 0.71858(9) -0.13751(17) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.376948 0.676712 -0.129333 0.021 Uiso 1 1 calc R U . . .
H7B H 0.286813 0.730206 -0.109039 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6466(2) 0.71608(9) -0.07471(19) 0.0209(4) Uani 1 1 d . . . . .
H8A H 0.650679 0.676323 -0.048493 0.031 Uiso 1 1 calc R U . . .
H8B H 0.742979 0.734780 -0.025832 0.031 Uiso 1 1 calc R U . . .
H8C H 0.628248 0.717456 -0.162439 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5368(2) 0.74429(8) 0.08224(18) 0.0149(4) Uani 1 1 d . . . . .
H9 H 0.446387 0.763910 0.085036 0.018 Uiso 1 1 calc R U . . .
C10 C 0.6756(2) 0.77792(9) 0.17003(18) 0.0163(4) Uani 1 1 d . . . . .
H10 H 0.769048 0.761133 0.166848 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6628(3) 0.84036(9) 0.12956(19) 0.0233(4) Uani 1 1 d . . . . .
H11A H 0.573960 0.857879 0.137554 0.028 Uiso 1 1 calc R U . . .
H11B H 0.754101 0.861287 0.184377 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6462(3) 0.84548(9) -0.00385(19) 0.0227(4) Uani 1 1 d . . . . .
H12A H 0.739724 0.831660 -0.009984 0.027 Uiso 1 1 calc R U . . .
H12B H 0.632556 0.885999 -0.028932 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5341(2) 0.68302(8) 0.12907(18) 0.0169(4) Uani 1 1 d . . . . .
H13A H 0.437286 0.664718 0.076044 0.020 Uiso 1 1 calc R U . . .
H13B H 0.616902 0.660842 0.121284 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5517(2) 0.68102(9) 0.26480(18) 0.0168(4) Uani 1 1 d . . . . .
H14A H 0.463123 0.699313 0.271607 0.020 Uiso 1 1 calc R U . . .
H14B H 0.555587 0.640890 0.291464 0.020 Uiso 1 1 calc R U . . .
C15 C 0.6964(2) 0.71177(8) 0.34926(18) 0.0153(4) Uani 1 1 d . . . . .
C16 C 0.6853(2) 0.77349(8) 0.30148(18) 0.0168(4) Uani 1 1 d . . . . .
H16 H 0.589353 0.789773 0.300784 0.020 Uiso 1 1 calc R U . . .
C17 C 0.8365(2) 0.68091(9) 0.34873(18) 0.0176(4) Uani 1 1 d . . . . .
H17A H 0.834225 0.681667 0.265126 0.026 Uiso 1 1 calc R U . . .
H17B H 0.836463 0.641339 0.374916 0.026 Uiso 1 1 calc R U . . .
H17C H 0.928159 0.700058 0.405804 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8161(3) 0.80470(9) 0.40370(19) 0.0209(4) Uani 1 1 d . . . . .
H18A H 0.793972 0.845821 0.404088 0.025 Uiso 1 1 calc R U . . .
H18B H 0.911740 0.799950 0.392715 0.025 Uiso 1 1 calc R U . . .
C19 C 0.8257(2) 0.77574(9) 0.52397(19) 0.0209(4) Uani 1 1 d . . . . .
H19A H 0.791705 0.802318 0.572583 0.025 Uiso 1 1 calc R U . . .
H19B H 0.931187 0.764328 0.575058 0.025 Uiso 1 1 calc R U . . .
C20 C 0.7213(2) 0.72244(9) 0.48623(18) 0.0180(4) Uani 1 1 d . . . . .
C21 C 0.5756(3) 0.73265(11) 0.5043(2) 0.0268(5) Uani 1 1 d . . . . .
H21A H 0.600113 0.741219 0.591412 0.040 Uiso 1 1 calc R U . . .
H21B H 0.512243 0.698465 0.480135 0.040 Uiso 1 1 calc R U . . .
H21C H 0.520803 0.764818 0.453054 0.040 Uiso 1 1 calc R U . . .
C22 C 0.3241(2) 0.55234(9) 0.82806(19) 0.0205(4) Uani 1 1 d . . . . .
H22 H 0.268556 0.584565 0.834798 0.025 Uiso 1 1 calc R U . . .
C23 C 0.3155(2) 0.52924(9) 0.71576(18) 0.0189(4) Uani 1 1 d . . . . .
C24 C 0.4128(2) 0.48363(9) 0.74938(19) 0.0186(4) Uani 1 1 d . . . . .
C25 C 0.4486(2) 0.44650(9) 0.66266(18) 0.0198(4) Uani 1 1 d . . . . .
H25A H 0.447574 0.406064 0.685873 0.024 Uiso 1 1 calc R U . . .
H25B H 0.550742 0.455594 0.667124 0.024 Uiso 1 1 calc R U . . .
C26 C 0.3299(2) 0.45640(8) 0.53035(18) 0.0170(4) Uani 1 1 d . . . . .
H26 H 0.233438 0.438848 0.525543 0.020 Uiso 1 1 calc R U . . .
C27 C 0.2967(2) 0.52074(8) 0.49755(17) 0.0149(4) Uani 1 1 d . . . . .
C28 C 0.2272(2) 0.54639(9) 0.58368(19) 0.0189(4) Uani 1 1 d . . . . .
H28A H 0.226018 0.588413 0.577238 0.023 Uiso 1 1 calc R U . . .
H28B H 0.121376 0.533213 0.556719 0.023 Uiso 1 1 calc R U . . .
C29 C 0.4423(2) 0.55331(9) 0.51716(19) 0.0207(4) Uani 1 1 d . . . . .
H29A H 0.512790 0.550618 0.604103 0.031 Uiso 1 1 calc R U . . .
H29B H 0.418163 0.593380 0.494921 0.031 Uiso 1 1 calc R U . . .
H29C H 0.489028 0.536732 0.464982 0.031 Uiso 1 1 calc R U . . .
C30 C 0.1780(2) 0.52498(8) 0.36151(17) 0.0143(4) Uani 1 1 d . . . . .
H30 H 0.085316 0.505212 0.359288 0.017 Uiso 1 1 calc R U . . .
C31 C 0.2270(2) 0.49257(8) 0.27009(18) 0.0158(4) Uani 1 1 d . . . . .
H31 H 0.322473 0.509935 0.272249 0.019 Uiso 1 1 calc R U . . .
C32 C 0.2567(3) 0.42983(9) 0.30752(19) 0.0214(4) Uani 1 1 d . . . . .
H32A H 0.161779 0.411691 0.302053 0.026 Uiso 1 1 calc R U . . .
H32B H 0.291096 0.409814 0.249775 0.026 Uiso 1 1 calc R U . . .
C33 C 0.3769(3) 0.42426(9) 0.43911(19) 0.0220(4) Uani 1 1 d . . . . .
H33A H 0.474023 0.439651 0.442942 0.026 Uiso 1 1 calc R U . . .
H33B H 0.391950 0.383544 0.462442 0.026 Uiso 1 1 calc R U . . .
C34 C 0.1294(2) 0.58668(9) 0.31859(18) 0.0170(4) Uani 1 1 d . . . . .
H34A H 0.086102 0.604019 0.373447 0.020 Uiso 1 1 calc R U . . .
H34B H 0.219945 0.608995 0.327143 0.020 Uiso 1 1 calc R U . . .
C35 C 0.0120(2) 0.59073(9) 0.18358(18) 0.0169(4) Uani 1 1 d . . . . .
H35A H -0.083977 0.572897 0.176512 0.020 Uiso 1 1 calc R U . . .
H35B H -0.008487 0.631240 0.159620 0.020 Uiso 1 1 calc R U . . .
C36 C 0.0702(2) 0.56068(8) 0.09593(17) 0.0145(4) Uani 1 1 d . . . . .
C37 C 0.1050(2) 0.49837(8) 0.14016(18) 0.0159(4) Uani 1 1 d . . . . .
H37 H 0.010123 0.482235 0.141845 0.019 Uiso 1 1 calc R U . . .
C38 C 0.2111(2) 0.59138(9) 0.09628(18) 0.0179(4) Uani 1 1 d . . . . .
H38A H 0.292033 0.589862 0.179436 0.027 Uiso 1 1 calc R U . . .
H38B H 0.186007 0.631177 0.071802 0.027 Uiso 1 1 calc R U . . .
H38C H 0.244864 0.572636 0.037810 0.027 Uiso 1 1 calc R U . . .
C39 C 0.1305(2) 0.46832(9) 0.03531(19) 0.0201(4) Uani 1 1 d . . . . .
H39A H 0.107469 0.427194 0.033549 0.024 Uiso 1 1 calc R U . . .
H39B H 0.236216 0.473050 0.044136 0.024 Uiso 1 1 calc R U . . .
C40 C 0.0191(2) 0.49845(9) -0.08226(19) 0.0201(4) Uani 1 1 d . . . . .
H40A H -0.064911 0.472503 -0.129990 0.024 Uiso 1 1 calc R U . . .
H40B H 0.071611 0.509843 -0.135359 0.024 Uiso 1 1 calc R U . . .
C41 C -0.0430(2) 0.55184(9) -0.04052(18) 0.0174(4) Uani 1 1 d . . . . .
C42 C -0.2057(2) 0.54256(10) -0.0563(2) 0.0255(5) Uani 1 1 d . . . . .
H42A H -0.269130 0.534718 -0.143364 0.038 Uiso 1 1 calc R U . . .
H42B H -0.242687 0.576820 -0.030124 0.038 Uiso 1 1 calc R U . . .
H42C H -0.210167 0.510174 -0.005658 0.038 Uiso 1 1 calc R U . . .
C49 C 0.1738(2) 0.78439(9) 0.25065(19) 0.0191(4) Uani 1 1 d . . . . .
C50 C 0.1318(2) 0.79099(9) 0.11635(18) 0.0164(4) Uani 1 1 d . . . . .
C51 C 0.0549(2) 0.74734(8) 0.03404(19) 0.0167(4) Uani 1 1 d . . . . .
H51 H 0.030918 0.713095 0.064935 0.020 Uiso 1 1 calc R U . . .
C52 C 0.0136(2) 0.75371(9) -0.09154(19) 0.0178(4) Uani 1 1 d . . . . .
C53 C 0.0442(2) 0.80512(9) -0.13680(19) 0.0205(4) Uani 1 1 d . . . . .
H53 H 0.013632 0.810185 -0.223222 0.025 Uiso 1 1 calc R U . . .
C54 C 0.1185(2) 0.84837(9) -0.0568(2) 0.0208(4) Uani 1 1 d . . . . .
H54 H 0.137153 0.883269 -0.088688 0.025 Uiso 1 1 calc R U . . .
C55 C 0.1667(2) 0.84159(9) 0.07082(19) 0.0186(4) Uani 1 1 d . . . . .
C56 C 0.6558(2) 0.48572(9) 0.19880(19) 0.0182(4) Uani 1 1 d . . . . .
C57 C 0.7430(2) 0.48068(9) 0.33355(18) 0.0166(4) Uani 1 1 d . . . . .
C58 C 0.8232(2) 0.43042(9) 0.38316(19) 0.0188(4) Uani 1 1 d . . . . .
C59 C 0.8955(3) 0.42455(9) 0.5110(2) 0.0227(4) Uani 1 1 d . . . . .
H59 H 0.945122 0.389876 0.545493 0.027 Uiso 1 1 calc R U . . .
C60 C 0.8954(3) 0.46877(10) 0.58807(19) 0.0231(4) Uani 1 1 d . . . . .
H60 H 0.945497 0.464240 0.675063 0.028 Uiso 1 1 calc R U . . .
C61 C 0.8227(2) 0.52007(9) 0.53948(19) 0.0191(4) Uani 1 1 d . . . . .
C62 C 0.7443(2) 0.52519(9) 0.41314(19) 0.0173(4) Uani 1 1 d . . . . .
H62 H 0.690502 0.559278 0.379674 0.021 Uiso 1 1 calc R U . . .
H4 H 0.545(4) 0.4585(13) 0.928(3) 0.028(7) Uiso 1 1 d . . . . .
H2 H 0.322(3) 0.8060(12) -0.484(3) 0.020(6) Uiso 1 1 d . . . . .
N1 N 0.2065(2) 0.74128(8) -0.47897(16) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.3074(2) 0.78415(8) -0.43158(16) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.4206(2) 0.52300(8) 0.92382(16) 0.0212(4) Uani 1 1 d . . . . .
N4 N 0.4732(2) 0.48061(8) 0.87386(16) 0.0198(4) Uani 1 1 d . . . . .
O1 O 0.79756(19) 0.67443(7) 0.56326(13) 0.0230(3) Uani 1 1 d D . . . .
H1A H 0.842(4) 0.6889(14) 0.6344(18) 0.046(10) Uiso 1 1 d D . . . .
O2 O -0.04212(19) 0.60039(6) -0.11618(13) 0.0225(3) Uani 1 1 d D . . . .
H2A H -0.073(3) 0.5881(13) -0.1884(16) 0.030(7) Uiso 1 1 d D . . . .
O8 O 0.57354(18) 0.53140(7) 0.16145(13) 0.0232(3) Uani 1 1 d D . . . .
H8 H 0.516(4) 0.5308(17) 0.0835(15) 0.049(10) Uiso 1 1 d D . . . .
O7 O 0.65977(19) 0.44787(7) 0.12642(14) 0.0237(3) Uani 1 1 d . . . . .
O9 O 0.83317(19) 0.38634(7) 0.31238(14) 0.0249(3) Uani 1 1 d D . . . .
H9A H 0.777(3) 0.3955(14) 0.2382(16) 0.041(9) Uiso 1 1 d D . . . .
O10 O 0.83102(19) 0.56285(7) 0.62063(14) 0.0251(3) Uani 1 1 d D . . . .
H10A H 0.807(3) 0.5945(8) 0.582(3) 0.032(8) Uiso 1 1 d D . . . .
O3 O 0.24775(19) 0.82166(7) 0.32541(14) 0.0253(3) Uani 1 1 d . . . . .
O4 O 0.12756(19) 0.73778(7) 0.28419(13) 0.0237(3) Uani 1 1 d D . . . .
H4C H 0.152(4) 0.7367(18) 0.3626(14) 0.055(11) Uiso 1 1 d D . . . .
O6 O -0.0580(2) 0.71159(7) -0.17503(14) 0.0243(3) Uani 1 1 d D . . . .
H6 H -0.041(4) 0.6799(9) -0.138(3) 0.047(10) Uiso 1 1 d D . . . .
O5 O 0.24490(19) 0.88510(7) 0.14478(15) 0.0260(3) Uani 1 1 d D . . . .
H5A H 0.256(4) 0.8738(15) 0.2166(18) 0.047(10) Uiso 1 1 d 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
C1 N1 1.338(3) . ?
C1 C2 1.402(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 C7 1.504(3) . ?
C3 N2 1.338(3) . ?
C3 C4 1.485(3) . ?
C4 C5 1.538(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.530(3) . ?
C5 C6 1.559(3) . ?
C5 H5 1.0000 . ?
C6 C8 1.541(3) . ?
C6 C7 1.548(3) . ?
C6 C9 1.557(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.542(2) . ?
C9 C13 1.547(3) . ?
C9 H9 1.0000 . ?
C10 C16 1.523(3) . ?
C10 C11 1.533(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.545(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.533(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.538(3) . ?
C15 C16 1.544(3) . ?
C15 C20 1.559(3) . ?
C16 C18 1.538(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.545(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.556(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O1 1.450(2) . ?
C20 C21 1.527(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N3 1.333(3) . ?
C22 C23 1.406(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 C28 1.502(3) . ?
C24 N4 1.349(3) . ?
C24 C25 1.490(3) . ?
C25 C26 1.540(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C33 1.528(3) . ?
C26 C27 1.562(3) . ?
C26 H26 1.0000 . ?
C27 C29 1.535(3) . ?
C27 C28 1.550(3) . ?
C27 C30 1.558(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.544(3) . ?
C30 C34 1.545(3) . ?
C30 H30 1.0000 . ?
C31 C37 1.519(3) . ?
C31 C32 1.533(3) . ?
C31 H31 1.0000 . ?
C32 C33 1.526(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.544(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.536(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C38 1.539(3) . ?
C36 C37 1.545(3) . ?
C36 C41 1.556(3) . ?
C37 C39 1.531(3) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.545(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.554(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 O2 1.452(2) . ?
C41 C42 1.523(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C49 O3 1.245(3) . ?
C49 O4 1.303(3) . ?
C49 C50 1.480(3) . ?
C50 C55 1.401(3) . ?
C50 C51 1.403(3) . ?
C51 C52 1.382(3) . ?
C51 H51 0.9500 . ?
C52 O6 1.372(3) . ?
C52 C53 1.400(3) . ?
C53 C54 1.377(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.397(3) . ?
C54 H54 0.9500 . ?
C55 O5 1.360(3) . ?
C56 O7 1.246(3) . ?
C56 O8 1.302(3) . ?
C56 C57 1.477(3) . ?
C57 C62 1.404(3) . ?
C57 C58 1.404(3) . ?
C58 O9 1.359(3) . ?
C58 C59 1.394(3) . ?
C59 C60 1.382(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.397(3) . ?
C60 H60 0.9500 . ?
C61 O10 1.369(3) . ?
C61 C62 1.381(3) . ?
C62 H62 0.9500 . ?
N1 N2 1.356(3) . ?
N2 H2 0.86(3) . ?
N3 N4 1.357(3) . ?
N4 H4 0.90(3) . ?
O1 H1A 0.846(14) . ?
O2 H2A 0.834(14) . ?
O8 H8 0.863(14) . ?
O9 H9A 0.853(14) . ?
O10 H10A 0.854(14) . ?
O4 H4C 0.861(14) . ?
O6 H6 0.848(14) . ?
O5 H5A 0.853(14) . ?

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
N1 C1 C2 110.91(19) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C3 C2 C1 104.71(18) . . ?
C3 C2 C7 122.73(18) . . ?
C1 C2 C7 132.55(19) . . ?
N2 C3 C2 107.36(18) . . ?
N2 C3 C4 127.20(19) . . ?
C2 C3 C4 125.42(18) . . ?
C3 C4 C5 109.04(17) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C12 C5 C4 109.12(16) . . ?
C12 C5 C6 113.24(17) . . ?
C4 C5 C6 113.15(16) . . ?
C12 C5 H5 107.0 . . ?
C4 C5 H5 107.0 . . ?
C6 C5 H5 107.0 . . ?
C8 C6 C7 108.54(16) . . ?
C8 C6 C9 112.02(16) . . ?
C7 C6 C9 108.97(15) . . ?
C8 C6 C5 110.90(17) . . ?
C7 C6 C5 108.65(16) . . ?
C9 C6 C5 107.69(15) . . ?
C2 C7 C6 111.63(17) . . ?
C2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C13 111.81(15) . . ?
C10 C9 C6 112.71(15) . . ?
C13 C9 C6 113.53(15) . . ?
C10 C9 H9 106.0 . . ?
C13 C9 H9 106.0 . . ?
C6 C9 H9 106.0 . . ?
C16 C10 C11 110.37(17) . . ?
C16 C10 C9 109.35(16) . . ?
C11 C10 C9 109.95(16) . . ?
C16 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C12 C11 C10 111.11(17) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C5 111.34(17) . . ?
C11 C12 H12A 109.4 . . ?
C5 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C5 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C9 112.93(16) . . ?
C14 C13 H13A 109.0 . . ?
C9 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C9 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 110.65(16) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C17 110.39(16) . . ?
C14 C15 C16 107.08(15) . . ?
C17 C15 C16 111.89(16) . . ?
C14 C15 C20 118.12(16) . . ?
C17 C15 C20 108.20(15) . . ?
C16 C15 C20 100.84(15) . . ?
C10 C16 C18 117.57(17) . . ?
C10 C16 C15 113.84(16) . . ?
C18 C16 C15 104.25(15) . . ?
C10 C16 H16 106.8 . . ?
C18 C16 H16 106.8 . . ?
C15 C16 H16 106.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 103.82(17) . . ?
C16 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C16 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C18 C19 C20 107.38(16) . . ?
C18 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
C18 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
O1 C20 C21 107.33(17) . . ?
O1 C20 C19 109.84(17) . . ?
C21 C20 C19 111.17(18) . . ?
O1 C20 C15 110.74(15) . . ?
C21 C20 C15 113.95(17) . . ?
C19 C20 C15 103.79(16) . . ?
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 . . ?
N3 C22 C23 110.97(19) . . ?
N3 C22 H22 124.5 . . ?
C23 C22 H22 124.5 . . ?
C24 C23 C22 104.75(18) . . ?
C24 C23 C28 123.08(19) . . ?
C22 C23 C28 132.2(2) . . ?
N4 C24 C23 107.54(18) . . ?
N4 C24 C25 127.01(19) . . ?
C23 C24 C25 125.40(19) . . ?
C24 C25 C26 109.04(17) . . ?
C24 C25 H25A 109.9 . . ?
C26 C25 H25A 109.9 . . ?
C24 C25 H25B 109.9 . . ?
C26 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C33 C26 C25 109.34(16) . . ?
C33 C26 C27 113.13(16) . . ?
C25 C26 C27 113.15(16) . . ?
C33 C26 H26 106.9 . . ?
C25 C26 H26 106.9 . . ?
C27 C26 H26 106.9 . . ?
C29 C27 C28 108.70(16) . . ?
C29 C27 C30 111.89(16) . . ?
C28 C27 C30 108.67(15) . . ?
C29 C27 C26 111.14(16) . . ?
C28 C27 C26 108.26(16) . . ?
C30 C27 C26 108.10(15) . . ?
C23 C28 C27 111.33(17) . . ?
C23 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
C23 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C34 111.79(15) . . ?
C31 C30 C27 112.69(15) . . ?
C34 C30 C27 113.53(16) . . ?
C31 C30 H30 106.0 . . ?
C34 C30 H30 106.0 . . ?
C27 C30 H30 106.0 . . ?
C37 C31 C32 110.92(16) . . ?
C37 C31 C30 109.41(16) . . ?
C32 C31 C30 110.31(16) . . ?
C37 C31 H31 108.7 . . ?
C32 C31 H31 108.7 . . ?
C30 C31 H31 108.7 . . ?
C33 C32 C31 110.73(17) . . ?
C33 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C32 C33 C26 110.94(17) . . ?
C32 C33 H33A 109.5 . . ?
C26 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C26 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C30 113.39(16) . . ?
C35 C34 H34A 108.9 . . ?
C30 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C30 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 110.67(15) . . ?
C36 C35 H35A 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C35 C36 C38 110.30(16) . . ?
C35 C36 C37 107.21(15) . . ?
C38 C36 C37 111.81(16) . . ?
C35 C36 C41 117.73(16) . . ?
C38 C36 C41 108.48(15) . . ?
C37 C36 C41 100.99(15) . . ?
C31 C37 C39 117.74(17) . . ?
C31 C37 C36 113.67(16) . . ?
C39 C37 C36 104.29(15) . . ?
C31 C37 H37 106.8 . . ?
C39 C37 H37 106.8 . . ?
C36 C37 H37 106.8 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 103.67(16) . . ?
C37 C39 H39A 111.0 . . ?
C40 C39 H39A 111.0 . . ?
C37 C39 H39B 111.0 . . ?
C40 C39 H39B 111.0 . . ?
H39A C39 H39B 109.0 . . ?
C39 C40 C41 107.60(16) . . ?
C39 C40 H40A 110.2 . . ?
C41 C40 H40A 110.2 . . ?
C39 C40 H40B 110.2 . . ?
C41 C40 H40B 110.2 . . ?
H40A C40 H40B 108.5 . . ?
O2 C41 C42 107.39(17) . . ?
O2 C41 C40 109.86(17) . . ?
C42 C41 C40 110.93(17) . . ?
O2 C41 C36 110.97(16) . . ?
C42 C41 C36 113.97(17) . . ?
C40 C41 C36 103.71(16) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O3 C49 O4 122.96(19) . . ?
O3 C49 C50 121.25(19) . . ?
O4 C49 C50 115.80(18) . . ?
C55 C50 C51 119.73(18) . . ?
C55 C50 C49 119.79(18) . . ?
C51 C50 C49 120.47(18) . . ?
C52 C51 C50 120.61(18) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
O6 C52 C51 122.60(18) . . ?
O6 C52 C53 118.04(18) . . ?
C51 C52 C53 119.36(19) . . ?
C54 C53 C52 120.38(19) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C53 C54 C55 120.9(2) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
O5 C55 C54 117.78(19) . . ?
O5 C55 C50 123.24(18) . . ?
C54 C55 C50 118.98(19) . . ?
O7 C56 O8 122.61(19) . . ?
O7 C56 C57 121.46(19) . . ?
O8 C56 C57 115.92(18) . . ?
C62 C57 C58 119.48(18) . . ?
C62 C57 C56 120.70(18) . . ?
C58 C57 C56 119.81(18) . . ?
O9 C58 C59 117.64(19) . . ?
O9 C58 C57 123.20(18) . . ?
C59 C58 C57 119.16(19) . . ?
C60 C59 C58 120.5(2) . . ?
C60 C59 H59 119.7 . . ?
C58 C59 H59 119.7 . . ?
C59 C60 C61 120.75(19) . . ?
C59 C60 H60 119.6 . . ?
C61 C60 H60 119.6 . . ?
O10 C61 C62 123.08(19) . . ?
O10 C61 C60 117.86(18) . . ?
C62 C61 C60 119.06(19) . . ?
C61 C62 C57 120.87(19) . . ?
C61 C62 H62 119.6 . . ?
C57 C62 H62 119.6 . . ?
C1 N1 N2 105.15(17) . . ?
C3 N2 N1 111.88(17) . . ?
C3 N2 H2 131.3(19) . . ?
N1 N2 H2 116.5(19) . . ?
C22 N3 N4 105.44(17) . . ?
C24 N4 N3 111.30(18) . . ?
C24 N4 H4 132(2) . . ?
N3 N4 H4 116(2) . . ?
C20 O1 H1A 104(2) . . ?
C41 O2 H2A 106(2) . . ?
C56 O8 H8 113(3) . . ?
C58 O9 H9A 105(2) . . ?
C61 O10 H10A 110(2) . . ?
C49 O4 H4C 112(3) . . ?
C52 O6 H6 109(3) . . ?
C55 O5 H5A 103(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9A O7 0.853(14) 1.83(2) 2.601(2) 150(3) . yes
O10 H10A O1 0.854(14) 1.889(18) 2.695(2) 157(3) . yes
O6 H6 O2 0.848(14) 1.885(19) 2.692(2) 158(4) . yes
O5 H5A O3 0.853(14) 1.80(2) 2.596(2) 154(4) . yes
O4 H4C N1 0.861(14) 1.732(15) 2.590(2) 174(4) 1_556 yes
O4 H4C N2 0.861(14) 2.55(3) 3.286(2) 145(4) 1_556 yes
N4 H4 O7 0.90(3) 2.17(3) 2.902(2) 138(3) 1_556 yes
N2 H2 O3 0.86(3) 2.11(3) 2.834(2) 142(2) 1_554 yes
O1 H1A O6 0.846(14) 2.131(16) 2.968(2) 170(3) 1_656 yes
O2 H2A O10 0.834(14) 2.150(14) 2.982(2) 175(3) 1_454 yes
O8 H8 N3 0.863(14) 1.746(15) 2.602(2) 172(4) 1_554 yes
O8 H8 N4 0.863(14) 2.62(3) 3.357(2) 144(3) 1_554 yes

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_STAN-PHA
_database_code_depnum_ccdc_archive 'CCDC 1863939'
_audit_update_record             
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H32 N2 O, C8 H6 O4'
_chemical_formula_sum            'C29 H38 N2 O5'
_chemical_formula_weight         494.61

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                   7.8660(5)
_cell_length_b                   11.3879(8)
_cell_length_c                   29.2351(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.638(2)
_cell_angle_gamma                90
_cell_volume                     2606.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6148
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.72

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5862
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1633 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.7862.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19245
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             8760
_reflns_number_gt                6766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.899

_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0544P)²+0.2599P] 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 2371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8760
_refine_ls_number_parameters     687
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.971
_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 0.9766(4) 0.8513(3) 0.16498(10) 0.0319(8) Uani 1 1 d D . . . .
H1A H 1.042(5) 0.873(5) 0.1881(11) 0.060(18) Uiso 1 1 d D . . . .
O2 O 0.0991(4) 0.7716(3) 0.32100(9) 0.0361(8) Uani 1 1 d D . . . .
H2A H 0.003(3) 0.759(4) 0.3060(12) 0.032(13) Uiso 1 1 d D . . . .
O3 O 0.8343(3) 0.7092(3) 0.75409(9) 0.0288(8) Uani 1 1 d . . . . .
O4 O 0.7277(4) 0.7642(3) 0.81841(10) 0.0334(9) Uani 1 1 d D . . . .
H4C H 0.823(4) 0.801(5) 0.824(2) 0.08(2) Uiso 1 1 d D . . . .
O5 O 0.7890(4) 0.4574(3) 0.76947(10) 0.0369(9) Uani 1 1 d . . . . .
O6 O 0.6676(4) 0.4145(4) 0.69974(11) 0.0478(10) Uani 1 1 d D . . . .
H6 H 0.757(5) 0.375(5) 0.696(2) 0.10(3) Uiso 1 1 d D . . . .
O7 O 0.1933(4) 0.2399(3) 0.73720(10) 0.0372(9) Uani 1 1 d . . . . .
O8 O 0.2781(4) 0.2266(3) 0.81184(10) 0.0427(9) Uani 1 1 d D . . . .
H8 H 0.190(5) 0.263(5) 0.818(2) 0.08(2) Uiso 1 1 d D . . . .
O9 O 0.1615(3) -0.0204(3) 0.74418(9) 0.0272(7) Uani 1 1 d . . . . .
O10 O 0.2723(4) -0.0778(3) 0.68061(10) 0.0327(8) Uani 1 1 d D . . . .
H10A H 0.169(3) -0.101(5) 0.6745(16) 0.049(16) Uiso 1 1 d D . . . .
N1 N 0.0152(4) 0.8553(4) -0.14844(12) 0.0310(9) Uani 1 1 d . . . . .
N2 N 0.1518(4) 0.9138(4) -0.16145(12) 0.0266(9) Uani 1 1 d D . . . .
H2 H 0.148(5) 0.938(4) -0.1900(7) 0.029(13) Uiso 1 1 d D . . . .
N3 N 0.9826(4) 0.8221(4) 0.64958(12) 0.0298(9) Uani 1 1 d . . . . .
N4 N 0.8439(5) 0.7618(4) 0.66050(12) 0.0290(9) Uani 1 1 d D . . . .
H4 H 0.839(5) 0.740(4) 0.6889(7) 0.036(14) Uiso 1 1 d D . . . .
C1 C 0.0527(5) 0.8335(4) -0.10383(14) 0.0281(11) Uani 1 1 d . . . . .
H1 H -0.018837 0.793234 -0.085736 0.034 Uiso 1 1 calc R U . . .
C2 C 0.2108(5) 0.8782(4) -0.08767(14) 0.0247(10) Uani 1 1 d . . . . .
C3 C 0.2720(5) 0.9304(4) -0.12558(13) 0.0240(10) Uani 1 1 d . . . . .
C4 C 0.4429(5) 0.9832(4) -0.12648(14) 0.0272(11) Uani 1 1 d . . . . .
H4A H 0.432907 1.058200 -0.142255 0.033 Uiso 1 1 calc R U . . .
H4B H 0.513952 0.932229 -0.143159 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5263(5) 1.0011(4) -0.07715(13) 0.0222(10) Uani 1 1 d . . . . .
H5 H 0.470207 1.068801 -0.064427 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5011(5) 0.8942(4) -0.04475(13) 0.0231(10) Uani 1 1 d . . . . .
C7 C 0.3086(5) 0.8795(5) -0.04085(14) 0.0279(11) Uani 1 1 d . . . . .
H7A H 0.288735 0.806671 -0.025025 0.033 Uiso 1 1 calc R U . . .
H7B H 0.268265 0.943677 -0.022949 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5712(5) 0.7802(4) -0.06353(14) 0.0278(10) Uani 1 1 d . . . . .
H8A H 0.563883 0.718412 -0.041474 0.042 Uiso 1 1 calc R U . . .
H8B H 0.688281 0.791404 -0.069130 0.042 Uiso 1 1 calc R U . . .
H8C H 0.505129 0.759449 -0.091735 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5895(5) 0.9256(4) 0.00389(13) 0.0227(10) Uani 1 1 d . . . . .
H9 H 0.537925 0.999892 0.012315 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7814(5) 0.9517(4) 0.00286(13) 0.0215(9) Uani 1 1 d . . . . .
H10 H 0.837599 0.881464 -0.007822 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8061(5) 1.0525(4) -0.03029(14) 0.0289(11) Uani 1 1 d . . . . .
H11A H 0.927272 1.062339 -0.032861 0.035 Uiso 1 1 calc R U . . .
H11B H 0.764262 1.124435 -0.017631 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7143(5) 1.0333(4) -0.07840(14) 0.0264(10) Uani 1 1 d . . . . .
H12A H 0.722188 1.104397 -0.096319 0.032 Uiso 1 1 calc R U . . .
H12B H 0.771242 0.970958 -0.093587 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5527(5) 0.8381(4) 0.04157(13) 0.0296(11) Uani 1 1 d . . . . .
H13A H 0.430205 0.833420 0.043058 0.036 Uiso 1 1 calc R U . . .
H13B H 0.592398 0.760902 0.033512 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6388(5) 0.8724(4) 0.08895(14) 0.0286(11) Uani 1 1 d . . . . .
H14A H 0.617209 0.812163 0.111098 0.034 Uiso 1 1 calc R U . . .
H14B H 0.590008 0.945405 0.098721 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8322(5) 0.8875(4) 0.08783(13) 0.0234(10) Uani 1 1 d . . . . .
C16 C 0.8595(5) 0.9810(4) 0.05145(13) 0.0237(10) Uani 1 1 d . . . . .
H16 H 0.801416 1.052088 0.060700 0.028 Uiso 1 1 calc R U . . .
C17 C 0.9128(5) 0.7690(4) 0.07725(15) 0.0345(11) Uani 1 1 d . . . . .
H17A H 0.876375 0.746644 0.046162 0.052 Uiso 1 1 calc R U . . .
H17B H 0.877316 0.710385 0.097916 0.052 Uiso 1 1 calc R U . . .
H17C H 1.034968 0.775896 0.081052 0.052 Uiso 1 1 calc R U . . .
C18 C 1.0519(5) 1.0066(5) 0.05933(14) 0.0313(12) Uani 1 1 d . . . . .
H18A H 1.076614 1.086026 0.050043 0.038 Uiso 1 1 calc R U . . .
H18B H 1.116023 0.952011 0.042196 0.038 Uiso 1 1 calc R U . . .
C19 C 1.0960(5) 0.9904(5) 0.11153(14) 0.0318(12) Uani 1 1 d . . . . .
H19A H 1.129067 1.064857 0.125859 0.038 Uiso 1 1 calc R U . . .
H19B H 1.189965 0.935544 0.117473 0.038 Uiso 1 1 calc R U . . .
C20 C 0.9329(5) 0.9420(4) 0.13101(14) 0.0252(10) Uani 1 1 d . . . . .
C21 C 0.8393(5) 1.0383(4) 0.15382(14) 0.0345(12) Uani 1 1 d . . . . .
H21A H 0.914216 1.073076 0.177982 0.052 Uiso 1 1 calc R U . . .
H21B H 0.741476 1.005756 0.166454 0.052 Uiso 1 1 calc R U . . .
H21C H 0.802719 1.097184 0.131492 0.052 Uiso 1 1 calc R U . . .
C22 C 0.9475(5) 0.8518(4) 0.60582(14) 0.0273(11) Uani 1 1 d . . . . .
H22 H 1.021015 0.893588 0.588791 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7860(5) 0.8123(4) 0.58870(14) 0.0249(10) Uani 1 1 d . . . . .
C24 C 0.7235(5) 0.7558(4) 0.62478(13) 0.0253(11) Uani 1 1 d . . . . .
C25 C 0.5553(5) 0.6933(5) 0.62271(13) 0.0283(11) Uani 1 1 d . . . . .
H25A H 0.497434 0.713581 0.649434 0.034 Uiso 1 1 calc R U . . .
H25B H 0.573951 0.609107 0.622939 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4435(5) 0.7287(4) 0.57856(13) 0.0230(10) Uani 1 1 d . . . . .
H26 H 0.401636 0.808351 0.583447 0.028 Uiso 1 1 calc R U . . .
C27 C 0.5422(5) 0.7329(4) 0.53457(12) 0.0200(9) Uani 1 1 d . . . . .
C28 C 0.6862(5) 0.8259(4) 0.54251(14) 0.0261(11) Uani 1 1 d . . . . .
H28A H 0.762966 0.818426 0.518669 0.031 Uiso 1 1 calc R U . . .
H28B H 0.636189 0.903838 0.540212 0.031 Uiso 1 1 calc R U . . .
C29 C 0.6249(5) 0.6135(4) 0.52634(13) 0.0229(9) Uani 1 1 d . . . . .
H29A H 0.674162 0.615200 0.497580 0.034 Uiso 1 1 calc R U . . .
H29B H 0.539614 0.553068 0.525515 0.034 Uiso 1 1 calc R U . . .
H29C H 0.712551 0.597750 0.550782 0.034 Uiso 1 1 calc R U . . .
C30 C 0.4147(5) 0.7690(4) 0.49376(13) 0.0202(10) Uani 1 1 d . . . . .
H30 H 0.369761 0.845451 0.502158 0.024 Uiso 1 1 calc R U . . .
C31 C 0.2587(5) 0.6883(4) 0.48586(13) 0.0217(9) Uani 1 1 d . . . . .
H31 H 0.297074 0.609565 0.478065 0.026 Uiso 1 1 calc R U . . .
C32 C 0.1680(5) 0.6806(5) 0.52969(13) 0.0298(11) Uani 1 1 d . . . . .
H32A H 0.114682 0.755676 0.534849 0.036 Uiso 1 1 calc R U . . .
H32B H 0.078194 0.622137 0.525405 0.036 Uiso 1 1 calc R U . . .
C33 C 0.2871(5) 0.6489(4) 0.57194(14) 0.0292(11) Uani 1 1 d . . . . .
H33A H 0.324660 0.568287 0.569189 0.035 Uiso 1 1 calc R U . . .
H33B H 0.224877 0.653977 0.598912 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4984(5) 0.7904(4) 0.44871(13) 0.0244(10) Uani 1 1 d . . . . .
H34A H 0.588149 0.848489 0.454453 0.029 Uiso 1 1 calc R U . . .
H34B H 0.550892 0.717986 0.439764 0.029 Uiso 1 1 calc R U . . .
C35 C 0.3720(5) 0.8328(4) 0.40878(14) 0.0266(11) Uani 1 1 d . . . . .
H35A H 0.329331 0.909958 0.415831 0.032 Uiso 1 1 calc R U . . .
H35B H 0.430108 0.839169 0.381112 0.032 Uiso 1 1 calc R U . . .
C36 C 0.2221(5) 0.7469(4) 0.40053(13) 0.0225(10) Uani 1 1 d . . . . .
C37 C 0.1400(5) 0.7349(4) 0.44606(13) 0.0226(10) Uani 1 1 d . . . . .
H37 H 0.108051 0.814485 0.454695 0.027 Uiso 1 1 calc R U . . .
C38 C 0.2856(5) 0.6311(4) 0.38282(14) 0.0306(11) Uani 1 1 d . . . . .
H38A H 0.365182 0.596178 0.405898 0.046 Uiso 1 1 calc R U . . .
H38B H 0.341225 0.644844 0.355516 0.046 Uiso 1 1 calc R U . . .
H38C H 0.190641 0.578987 0.375859 0.046 Uiso 1 1 calc R U . . .
C39 C -0.0282(5) 0.6695(5) 0.43219(14) 0.0335(12) Uani 1 1 d . . . . .
H39A H -0.115824 0.693063 0.451462 0.040 Uiso 1 1 calc R U . . .
H39B H -0.011951 0.585285 0.434768 0.040 Uiso 1 1 calc R U . . .
C40 C -0.0777(5) 0.7055(5) 0.38172(15) 0.0405(14) Uani 1 1 d . . . . .
H40A H -0.084838 0.636774 0.361998 0.049 Uiso 1 1 calc R U . . .
H40B H -0.187483 0.744894 0.378674 0.049 Uiso 1 1 calc R U . . .
C41 C 0.0636(5) 0.7889(5) 0.36843(14) 0.0301(11) Uani 1 1 d . . . . .
C42 C 0.0159(6) 0.9164(5) 0.37383(16) 0.0427(13) Uani 1 1 d . . . . .
H42A H -0.088157 0.932839 0.354901 0.064 Uiso 1 1 calc R U . . .
H42B H 0.105615 0.965557 0.364610 0.064 Uiso 1 1 calc R U . . .
H42C H -0.000207 0.931812 0.405399 0.064 Uiso 1 1 calc R U . . .
C43 C 0.7185(5) 0.7114(4) 0.77867(14) 0.0221(10) Uani 1 1 d . . . . .
C44 C 0.5475(5) 0.6598(4) 0.76457(13) 0.0201(10) Uani 1 1 d . . . . .
C45 C 0.5285(5) 0.5524(4) 0.74174(13) 0.0211(10) Uani 1 1 d . . . . .
C46 C 0.6769(5) 0.4708(4) 0.73887(14) 0.0261(11) Uani 1 1 d . . . . .
C47 C 0.3664(5) 0.5145(4) 0.72406(14) 0.0274(11) Uani 1 1 d . . . . .
H47 H 0.353340 0.442961 0.708749 0.033 Uiso 1 1 calc R U . . .
C48 C 0.2248(5) 0.5842(5) 0.72947(15) 0.0290(12) Uani 1 1 d . . . . .
H48 H 0.116747 0.559212 0.717638 0.035 Uiso 1 1 calc R U . . .
C49 C 0.2431(5) 0.6893(4) 0.75209(14) 0.0256(10) Uani 1 1 d . . . . .
H49 H 0.147841 0.735824 0.755389 0.031 Uiso 1 1 calc R U . . .
C50 C 0.4034(5) 0.7264(4) 0.77003(14) 0.0253(10) Uani 1 1 d . . . . .
H50 H 0.414675 0.797073 0.785988 0.030 Uiso 1 1 calc R U . . .
C51 C 0.2931(5) 0.2051(4) 0.76819(14) 0.0247(10) Uani 1 1 d . . . . .
C52 C 0.4510(5) 0.1380(4) 0.76113(14) 0.0257(10) Uani 1 1 d . . . . .
C53 C 0.4447(5) 0.0381(4) 0.73365(14) 0.0242(10) Uani 1 1 d . . . . .
C54 C 0.2781(5) -0.0213(4) 0.71954(13) 0.0220(10) Uani 1 1 d . . . . .
C55 C 0.5961(5) -0.0159(5) 0.72376(15) 0.0304(11) Uani 1 1 d . . . . .
H55 H 0.592217 -0.081774 0.704885 0.036 Uiso 1 1 calc R U . . .
C56 C 0.7512(6) 0.0281(5) 0.74185(17) 0.0392(13) Uani 1 1 d . . . . .
H56 H 0.851837 -0.007645 0.734956 0.047 Uiso 1 1 calc R U . . .
C57 C 0.7576(6) 0.1246(5) 0.77001(19) 0.0437(14) Uani 1 1 d . . . . .
H57 H 0.862694 0.152869 0.782707 0.052 Uiso 1 1 calc R U . . .
C58 C 0.6086(5) 0.1802(5) 0.77971(16) 0.0339(12) Uani 1 1 d . . . . .
H58 H 0.614109 0.245926 0.798684 0.041 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 C20 1.451(5) . ?
O1 H1A 0.846(14) . ?
O2 C41 1.454(5) . ?
O2 H2A 0.849(14) . ?
O3 C43 1.215(4) . ?
O4 C43 1.304(5) . ?
O4 H4C 0.855(14) . ?
O5 C46 1.203(5) . ?
O6 C46 1.307(5) . ?
O6 H6 0.855(14) . ?
O7 C51 1.206(5) . ?
O8 C51 1.316(5) . ?
O8 H8 0.851(14) . ?
O9 C54 1.221(5) . ?
O10 C54 1.304(5) . ?
O10 H10A 0.854(14) . ?
N1 C1 1.332(5) . ?
N1 N2 1.350(5) . ?
N2 C3 1.354(5) . ?
N2 H2 0.875(14) . ?
N3 C22 1.326(5) . ?
N3 N4 1.354(5) . ?
N4 C24 1.341(5) . ?
N4 H4 0.871(14) . ?
C1 C2 1.384(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(6) . ?
C2 C7 1.503(5) . ?
C3 C4 1.475(6) . ?
C4 C5 1.538(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.527(5) . ?
C5 C6 1.566(6) . ?
C5 H5 0.9800 . ?
C6 C8 1.533(6) . ?
C6 C7 1.539(5) . ?
C6 C9 1.561(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C13 1.534(6) . ?
C9 C10 1.542(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.526(6) . ?
C10 C16 1.528(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.532(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.532(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.535(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C17 1.535(6) . ?
C15 C16 1.535(6) . ?
C15 C20 1.552(6) . ?
C16 C18 1.536(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.543(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.555(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.512(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.393(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(6) . ?
C23 C28 1.502(6) . ?
C24 C25 1.498(6) . ?
C25 C26 1.543(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C33 1.526(6) . ?
C26 C27 1.567(5) . ?
C26 H26 0.9800 . ?
C27 C29 1.536(6) . ?
C27 C30 1.537(5) . ?
C27 C28 1.551(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.533(6) . ?
C30 C34 1.548(5) . ?
C30 H30 0.9800 . ?
C31 C37 1.515(5) . ?
C31 C32 1.529(5) . ?
C31 H31 0.9800 . ?
C32 C33 1.519(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.535(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.533(6) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C38 1.519(6) . ?
C36 C37 1.542(5) . ?
C36 C41 1.560(6) . ?
C37 C39 1.537(6) . ?
C37 H37 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.544(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.541(6) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.512(7) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.489(6) . ?
C44 C50 1.386(6) . ?
C44 C45 1.394(6) . ?
C45 C47 1.396(6) . ?
C45 C46 1.501(6) . ?
C47 C48 1.390(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.369(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.383(6) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C52 1.490(6) . ?
C52 C53 1.391(6) . ?
C52 C58 1.389(6) . ?
C53 C55 1.396(6) . ?
C53 C54 1.496(6) . ?
C55 C56 1.375(6) . ?
C55 H55 0.9300 . ?
C56 C57 1.371(8) . ?
C56 H56 0.9300 . ?
C57 C58 1.386(7) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 H1A 115(4) . . ?
C41 O2 H2A 106(3) . . ?
C43 O4 H4C 112(4) . . ?
C46 O6 H6 114(4) . . ?
C51 O8 H8 118(4) . . ?
C54 O10 H10A 107(3) . . ?
C1 N1 N2 105.2(3) . . ?
N1 N2 C3 111.4(3) . . ?
N1 N2 H2 118(3) . . ?
C3 N2 H2 130(3) . . ?
C22 N3 N4 105.1(4) . . ?
C24 N4 N3 111.5(4) . . ?
C24 N4 H4 129(3) . . ?
N3 N4 H4 119(3) . . ?
N1 C1 C2 111.8(4) . . ?
N1 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
C3 C2 C1 104.8(4) . . ?
C3 C2 C7 122.5(4) . . ?
C1 C2 C7 132.6(4) . . ?
N2 C3 C2 106.8(4) . . ?
N2 C3 C4 127.6(4) . . ?
C2 C3 C4 125.3(4) . . ?
C3 C4 C5 110.0(3) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C12 C5 C4 109.5(3) . . ?
C12 C5 C6 112.4(3) . . ?
C4 C5 C6 113.4(3) . . ?
C12 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C6 C5 H5 107.1 . . ?
C8 C6 C7 109.0(4) . . ?
C8 C6 C9 112.1(3) . . ?
C7 C6 C9 108.1(3) . . ?
C8 C6 C5 111.7(3) . . ?
C7 C6 C5 108.3(3) . . ?
C9 C6 C5 107.6(3) . . ?
C2 C7 C6 110.7(3) . . ?
C2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 113.2(3) . . ?
C13 C9 C6 114.0(3) . . ?
C10 C9 C6 112.0(3) . . ?
C13 C9 H9 105.6 . . ?
C10 C9 H9 105.6 . . ?
C6 C9 H9 105.6 . . ?
C11 C10 C16 111.2(3) . . ?
C11 C10 C9 110.1(3) . . ?
C16 C10 C9 109.2(3) . . ?
C11 C10 H10 108.8 . . ?
C16 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C10 C11 C12 113.4(4) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C5 C12 C11 112.5(3) . . ?
C5 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C5 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C9 112.7(4) . . ?
C14 C13 H13A 109.1 . . ?
C9 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C9 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 111.1(3) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C17 C15 C14 109.6(4) . . ?
C17 C15 C16 112.5(3) . . ?
C14 C15 C16 107.4(3) . . ?
C17 C15 C20 109.1(3) . . ?
C14 C15 C20 117.1(3) . . ?
C16 C15 C20 101.0(3) . . ?
C10 C16 C18 118.7(3) . . ?
C10 C16 C15 114.9(4) . . ?
C18 C16 C15 103.3(3) . . ?
C10 C16 H16 106.3 . . ?
C18 C16 H16 106.3 . . ?
C15 C16 H16 106.3 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 104.4(3) . . ?
C16 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C16 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C18 C19 C20 106.9(3) . . ?
C18 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
C18 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
O1 C20 C21 107.9(3) . . ?
O1 C20 C15 109.9(4) . . ?
C21 C20 C15 114.6(4) . . ?
O1 C20 C19 110.8(3) . . ?
C21 C20 C19 111.1(4) . . ?
C15 C20 C19 102.6(3) . . ?
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 . . ?
N3 C22 C23 111.1(4) . . ?
N3 C22 H22 124.4 . . ?
C23 C22 H22 124.4 . . ?
C24 C23 C22 105.0(4) . . ?
C24 C23 C28 123.1(4) . . ?
C22 C23 C28 131.9(4) . . ?
N4 C24 C23 107.3(4) . . ?
N4 C24 C25 127.5(4) . . ?
C23 C24 C25 125.1(4) . . ?
C24 C25 C26 109.8(4) . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C33 C26 C25 109.7(3) . . ?
C33 C26 C27 111.9(3) . . ?
C25 C26 C27 114.0(3) . . ?
C33 C26 H26 107.0 . . ?
C25 C26 H26 107.0 . . ?
C27 C26 H26 107.0 . . ?
C29 C27 C30 111.6(3) . . ?
C29 C27 C28 108.3(3) . . ?
C30 C27 C28 110.2(3) . . ?
C29 C27 C26 110.7(3) . . ?
C30 C27 C26 107.9(3) . . ?
C28 C27 C26 108.2(3) . . ?
C23 C28 C27 111.9(3) . . ?
C23 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C23 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C27 114.1(3) . . ?
C31 C30 C34 111.5(3) . . ?
C27 C30 C34 113.8(3) . . ?
C31 C30 H30 105.5 . . ?
C27 C30 H30 105.5 . . ?
C34 C30 H30 105.5 . . ?
C37 C31 C32 111.1(3) . . ?
C37 C31 C30 109.2(3) . . ?
C32 C31 C30 109.9(3) . . ?
C37 C31 H31 108.8 . . ?
C32 C31 H31 108.8 . . ?
C30 C31 H31 108.8 . . ?
C33 C32 C31 113.2(3) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C26 112.7(4) . . ?
C32 C33 H33A 109.0 . . ?
C26 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C26 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 C30 113.5(3) . . ?
C35 C34 H34A 108.9 . . ?
C30 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C30 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 110.5(4) . . ?
C36 C35 H35A 109.6 . . ?
C34 C35 H35A 109.6 . . ?
C36 C35 H35B 109.6 . . ?
C34 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C38 C36 C35 109.5(3) . . ?
C38 C36 C37 113.4(4) . . ?
C35 C36 C37 107.6(3) . . ?
C38 C36 C41 109.4(3) . . ?
C35 C36 C41 117.1(4) . . ?
C37 C36 C41 99.7(3) . . ?
C31 C37 C39 118.8(4) . . ?
C31 C37 C36 114.5(3) . . ?
C39 C37 C36 103.8(3) . . ?
C31 C37 H37 106.3 . . ?
C39 C37 H37 106.3 . . ?
C36 C37 H37 106.3 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 104.7(4) . . ?
C37 C39 H39A 110.8 . . ?
C40 C39 H39A 110.8 . . ?
C37 C39 H39B 110.8 . . ?
C40 C39 H39B 110.8 . . ?
H39A C39 H39B 108.9 . . ?
C41 C40 C39 106.5(3) . . ?
C41 C40 H40A 110.4 . . ?
C39 C40 H40A 110.4 . . ?
C41 C40 H40B 110.4 . . ?
C39 C40 H40B 110.4 . . ?
H40A C40 H40B 108.6 . . ?
O2 C41 C42 107.6(4) . . ?
O2 C41 C40 111.5(4) . . ?
C42 C41 C40 111.9(4) . . ?
O2 C41 C36 108.4(3) . . ?
C42 C41 C36 115.1(4) . . ?
C40 C41 C36 102.3(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O3 C43 O4 123.9(4) . . ?
O3 C43 C44 122.5(4) . . ?
O4 C43 C44 113.5(3) . . ?
C50 C44 C45 119.0(4) . . ?
C50 C44 C43 118.6(4) . . ?
C45 C44 C43 122.0(4) . . ?
C44 C45 C47 120.0(4) . . ?
C44 C45 C46 121.5(4) . . ?
C47 C45 C46 118.3(4) . . ?
O5 C46 O6 124.2(4) . . ?
O5 C46 C45 123.7(4) . . ?
O6 C46 C45 112.1(4) . . ?
C48 C47 C45 119.6(4) . . ?
C48 C47 H47 120.2 . . ?
C45 C47 H47 120.2 . . ?
C49 C48 C47 120.5(4) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C48 C49 C50 119.9(4) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C49 C50 C44 121.0(4) . . ?
C49 C50 H50 119.5 . . ?
C44 C50 H50 119.5 . . ?
O7 C51 O8 123.6(4) . . ?
O7 C51 C52 123.7(4) . . ?
O8 C51 C52 112.6(4) . . ?
C53 C52 C58 119.3(4) . . ?
C53 C52 C51 121.1(4) . . ?
C58 C52 C51 119.5(4) . . ?
C52 C53 C55 119.8(4) . . ?
C52 C53 C54 120.6(4) . . ?
C55 C53 C54 119.1(4) . . ?
O9 C54 O10 123.7(4) . . ?
O9 C54 C53 121.5(4) . . ?
O10 C54 C53 114.7(3) . . ?
C56 C55 C53 120.2(5) . . ?
C56 C55 H55 119.9 . . ?
C53 C55 H55 119.9 . . ?
C57 C56 C55 120.1(5) . . ?
C57 C56 H56 119.9 . . ?
C55 C56 H56 119.9 . . ?
C56 C57 C58 120.5(5) . . ?
C56 C57 H57 119.8 . . ?
C58 C57 H57 119.8 . . ?
C57 C58 C52 120.1(5) . . ?
C57 C58 H58 119.9 . . ?
C52 C58 H58 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O5 0.846(14) 1.97(2) 2.800(4) 165(5) 2_756 yes
O2 H2A O7 0.849(14) 1.908(16) 2.747(4) 169(4) 2_556 yes
O4 H4C N1 0.855(14) 1.76(2) 2.588(5) 163(6) 1_656 yes
O6 H6 O2 0.855(14) 1.73(2) 2.570(4) 165(7) 2_646 yes
O8 H8 O1 0.851(14) 1.751(17) 2.599(4) 173(7) 2_646 yes
O10 H10A N3 0.854(14) 1.80(2) 2.628(5) 163(5) 1_445 yes
N2 H2 O9 0.875(14) 1.996(15) 2.867(5) 174(4) 1_564 yes
N4 H4 O3 0.871(14) 1.942(16) 2.809(4) 173(5) . yes

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048

