# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1987991'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C59 H56 Cl N3 O14 S'
_chemical_formula_sum            'C59 H56 Cl N3 O14 S'
_chemical_formula_weight         1098.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.23660(10)
_cell_length_b                   35.3229(3)
_cell_length_c                   14.56840(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.5220(10)
_cell_angle_gamma                90
_cell_volume                     2682.24(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    26240
_cell_measurement_theta_min      3.9400
_cell_measurement_theta_max      73.2940

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    1.590
_shelx_estimated_absorpt_T_min   0.513
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_reflns_number            48369
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.944
_diffrn_reflns_theta_max         73.534
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             10328
_reflns_number_gt                9914
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.954

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0400P)²+1.3455P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4408 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10328
_refine_ls_number_parameters     914
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7201(7) 0.70875(10) 0.6644(2) 0.0272(7) Uani 1 1 d . . . . .
H1 H 0.895743 0.711931 0.697000 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5505(7) 0.68621(10) 0.7242(2) 0.0276(7) Uani 1 1 d . . . . .
H2 H 0.365920 0.690915 0.702888 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6026(7) 0.64384(10) 0.7256(2) 0.0282(7) Uani 1 1 d . . . . .
H3 H 0.771462 0.639120 0.761981 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6167(7) 0.62929(9) 0.6276(2) 0.0270(7) Uani 1 1 d . . . . .
H4 H 0.448308 0.631175 0.589182 0.032 Uiso 1 1 calc R U . A 1
C5 C 0.8271(7) 0.65231(10) 0.5877(2) 0.0273(7) Uani 1 1 d . . . . .
H5 H 0.984489 0.652017 0.632439 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8975(7) 0.63975(11) 0.4946(2) 0.0305(7) Uani 1 1 d . . . . .
H6A H 0.952924 0.612948 0.496980 0.037 Uiso 1 1 calc R U . . .
H6B H 0.747938 0.642217 0.447968 0.037 Uiso 1 1 calc R U . . .
C7 C 0.8232(8) 0.78210(10) 0.6081(3) 0.0321(8) Uani 1 1 d . . . . .
C8 C 0.8666(10) 0.78481(13) 0.5167(3) 0.0499(11) Uani 1 1 d . . . . .
H8 H 0.769893 0.769679 0.472041 0.060 Uiso 1 1 calc R U . . .
C9 C 1.0498(12) 0.80935(13) 0.4896(4) 0.0605(14) Uani 1 1 d . . . . .
H9 H 1.074700 0.811233 0.426034 0.073 Uiso 1 1 calc R U . . .
C10 C 1.1979(9) 0.83125(11) 0.5526(4) 0.0556(13) Uani 1 1 d . . . . .
C11 C 1.4009(11) 0.85769(15) 0.5219(6) 0.085(2) Uani 1 1 d . . . . .
H11A H 1.334970 0.883677 0.519592 0.102 Uiso 1 1 calc R U . . .
H11B H 1.444342 0.850187 0.460587 0.102 Uiso 1 1 calc R U . . .
H11C H 1.554658 0.856331 0.565829 0.102 Uiso 1 1 calc R U . . .
C12 C 1.1556(11) 0.82765(12) 0.6442(4) 0.0598(14) Uani 1 1 d . . . . .
H12 H 1.257072 0.842027 0.689122 0.072 Uiso 1 1 calc R U . . .
C13 C 0.9686(9) 0.80356(11) 0.6724(3) 0.0453(10) Uani 1 1 d . . . . .
H13 H 0.941227 0.801901 0.735832 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4255(7) 0.72066(11) 0.8554(2) 0.0309(7) Uani 1 1 d . . . . .
C15 C 0.5178(7) 0.73183(11) 0.9516(2) 0.0313(7) Uani 1 1 d . . . . .
C16 C 0.7410(8) 0.71745(13) 0.9971(3) 0.0418(9) Uani 1 1 d . . . . .
H16 H 0.847004 0.700857 0.966218 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8091(9) 0.72752(15) 1.0887(3) 0.0483(11) Uani 1 1 d . . . . .
H17 H 0.959641 0.717152 1.120689 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6612(8) 0.75220(15) 1.1330(2) 0.0470(10) Uani 1 1 d . . . . .
H18 H 0.709375 0.758947 1.195373 0.056 Uiso 1 1 calc R U . . .
C19 C 0.4410(9) 0.76735(14) 1.0867(3) 0.0473(10) Uani 1 1 d . . . . .
H19 H 0.339229 0.784744 1.117108 0.057 Uiso 1 1 calc R U . . .
C20 C 0.3699(8) 0.75710(12) 0.9965(2) 0.0388(8) Uani 1 1 d . . . . .
H20 H 0.218619 0.767442 0.964844 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5042(9) 0.60984(15) 0.8583(3) 0.0496(11) Uani 1 1 d . . . . .
H21A H 0.621596 0.628266 0.891695 0.060 Uiso 1 1 calc R U . . .
H21B H 0.603661 0.586652 0.847915 0.060 Uiso 1 1 calc R U . . .
C22 C 0.2924(8) 0.60034(12) 0.9161(3) 0.0379(9) Uani 1 1 d . . . . .
C23 C 0.1964(9) 0.62765(15) 0.9717(3) 0.0475(10) Uani 1 1 d . . . . .
H23 H 0.255791 0.652974 0.968328 0.057 Uiso 1 1 calc R U . . .
C24 C 0.0184(9) 0.61918(17) 1.0314(3) 0.0567(13) Uani 1 1 d . . . . .
H24 H -0.044357 0.638492 1.068626 0.068 Uiso 1 1 calc R U . . .
C25 C -0.0699(10) 0.58257(18) 1.0374(4) 0.0642(16) Uani 1 1 d . . . . .
H25 H -0.192119 0.576479 1.079261 0.077 Uiso 1 1 calc R U . . .
C26 C 0.0197(11) 0.55518(16) 0.9828(5) 0.079(2) Uani 1 1 d . . . . .
H26 H -0.040801 0.529929 0.986677 0.095 Uiso 1 1 calc R U . . .
C27 C 0.1984(11) 0.56389(14) 0.9218(4) 0.0620(14) Uani 1 1 d . . . . .
H27 H 0.256901 0.544631 0.883420 0.074 Uiso 1 1 calc R U . . .
C28 C 1.0456(7) 0.69134(11) 0.4078(2) 0.0299(7) Uani 1 1 d . . . . .
C29 C 1.2724(7) 0.71757(11) 0.4092(2) 0.0345(8) Uani 1 1 d . . . . .
H29A H 1.431756 0.702460 0.409895 0.041 Uiso 1 1 calc R U . . .
H29B H 1.283065 0.733017 0.466161 0.041 Uiso 1 1 calc R U . . .
N1 N 0.774(3) 0.5340(2) 0.7559(5) 0.058(3) Uani 0.507(5) 1 d D . P B 1
N2 N 0.8168(19) 0.5053(2) 0.8013(6) 0.059(2) Uani 0.507(5) 1 d D . P B 1
N3 N 0.883(2) 0.4815(3) 0.8505(7) 0.077(3) Uani 0.507(5) 1 d D . P B 1
O4 O 0.711(3) 0.5914(5) 0.6343(14) 0.034(3) Uani 0.507(5) 1 d D U P B 1
O8 O 0.375(3) 0.5613(4) 0.5410(10) 0.034(3) Uani 0.507(5) 1 d D . P B 1
O11 O 0.322(5) 0.5853(7) 0.3456(13) 0.047(4) Uani 0.507(5) 1 d D . P B 1
O14 O 0.644(3) 0.5815(6) 0.2559(15) 0.080(5) Uani 0.507(5) 1 d D . P B 1
C30 C 0.506(3) 0.5654(4) 0.6311(13) 0.033(4) Uani 0.507(5) 1 d D . P B 1
H30 H 0.380910 0.574278 0.674063 0.040 Uiso 0.507(5) 1 calc R U P B 1
C31 C 0.618(2) 0.5273(3) 0.6658(8) 0.042(2) Uani 0.507(5) 1 d D . P B 1
H31 H 0.478112 0.508616 0.673157 0.050 Uiso 0.507(5) 1 calc R U P B 1
C32 C 0.794(3) 0.5132(3) 0.5966(10) 0.046(4) Uani 0.507(5) 1 d D . P B 1
H32 H 0.925790 0.533439 0.591682 0.056 Uiso 0.507(5) 1 calc R U P B 1
C33 C 0.648(3) 0.5097(5) 0.5012(12) 0.041(5) Uani 0.507(5) 1 d D . P B 1
H33 H 0.510762 0.490053 0.501832 0.049 Uiso 0.507(5) 1 calc R U P B 1
C34 C 0.532(5) 0.5476(6) 0.4723(12) 0.034(4) Uani 0.507(5) 1 d D . P B 1
H34 H 0.675340 0.566007 0.468372 0.041 Uiso 0.507(5) 1 calc R U P B 1
C35 C 0.375(4) 0.5476(6) 0.3818(13) 0.047(5) Uani 0.507(5) 1 d D . P B 1
H35A H 0.465757 0.532952 0.337041 0.056 Uiso 0.507(5) 1 calc R U P B 1
H35B H 0.209819 0.534620 0.388638 0.056 Uiso 0.507(5) 1 calc R U P B 1
O9 O 0.9308(14) 0.47994(18) 0.6256(5) 0.0520(17) Uani 0.507(5) 1 d D . P B 1
C36 C 0.784(2) 0.4466(3) 0.6367(8) 0.058(3) Uani 0.507(5) 1 d D . P B 1
H36A H 0.700397 0.438152 0.576419 0.070 Uiso 0.507(5) 1 calc R U P B 1
H36B H 0.649990 0.451546 0.678565 0.070 Uiso 0.507(5) 1 calc R U P B 1
C37 C 0.969(3) 0.4164(4) 0.6775(9) 0.052(3) Uani 0.507(5) 1 d D . P B 1
C38 C 1.217(2) 0.4132(3) 0.6540(9) 0.063(3) Uani 0.507(5) 1 d D . P B 1
H38 H 1.276419 0.430060 0.609697 0.075 Uiso 0.507(5) 1 calc R U P B 1
C39 C 1.381(2) 0.3860(3) 0.6938(10) 0.074(3) Uani 0.507(5) 1 d D . P B 1
H39 H 1.554405 0.384960 0.679714 0.089 Uiso 0.507(5) 1 calc R U P B 1
C40 C 1.291(3) 0.3604(4) 0.7541(11) 0.077(4) Uani 0.507(5) 1 d D . P B 1
H40 H 1.403974 0.341812 0.782624 0.093 Uiso 0.507(5) 1 calc R U P B 1
C41 C 1.036(4) 0.3615(5) 0.7735(13) 0.091(6) Uani 0.507(5) 1 d D . P B 1
H41 H 0.971436 0.342499 0.811238 0.109 Uiso 0.507(5) 1 calc R U P B 1
C42 C 0.876(3) 0.3904(3) 0.7373(9) 0.076(4) Uani 0.507(5) 1 d D . P B 1
H42 H 0.705308 0.392348 0.753494 0.091 Uiso 0.507(5) 1 calc R U P B 1
C58 C 0.453(5) 0.5978(5) 0.276(2) 0.051(6) Uani 0.507(5) 1 d D . P B 1
C59 C 0.387(6) 0.6368(5) 0.2427(18) 0.063(7) Uani 0.507(5) 1 d D . P B 1
H59A H 0.526679 0.654131 0.263888 0.076 Uiso 0.507(5) 1 calc R U P B 1
H59B H 0.228320 0.644975 0.266955 0.076 Uiso 0.507(5) 1 calc R U P B 1
H59C H 0.364018 0.636779 0.175135 0.076 Uiso 0.507(5) 1 calc R U P B 1
N101 N 0.624(2) 0.5237(2) 0.7344(7) 0.0448(19) Uani 0.493(5) 1 d D . P B 2
N102 N 0.545(2) 0.4951(3) 0.7715(6) 0.067(3) Uani 0.493(5) 1 d D . P B 2
N103 N 0.487(3) 0.4704(3) 0.8175(8) 0.093(4) Uani 0.493(5) 1 d D . P B 2
O104 O 0.662(3) 0.5887(5) 0.6226(12) 0.022(2) Uani 0.493(5) 1 d D U P B 2
O108 O 0.328(3) 0.5667(5) 0.5164(10) 0.031(3) Uani 0.493(5) 1 d D . P B 2
O111 O 0.310(4) 0.5922(6) 0.3232(12) 0.039(3) Uani 0.493(5) 1 d D . P B 2
O114 O 0.605(5) 0.5774(7) 0.2279(16) 0.113(10) Uani 0.493(5) 1 d D . P B 2
C130 C 0.439(3) 0.5660(4) 0.6096(12) 0.025(3) Uani 0.493(5) 1 d D . P B 2
H130 H 0.310163 0.575408 0.650617 0.030 Uiso 0.493(5) 1 calc R U P B 2
C131 C 0.511(2) 0.5253(3) 0.6364(8) 0.034(2) Uani 0.493(5) 1 d D . P B 2
H131 H 0.352773 0.509346 0.629730 0.041 Uiso 0.493(5) 1 calc R U P B 2
C132 C 0.704(3) 0.5092(3) 0.5732(10) 0.035(3) Uani 0.493(5) 1 d D . P B 2
H132 H 0.867793 0.523897 0.580773 0.042 Uiso 0.493(5) 1 calc R U P B 2
C133 C 0.580(4) 0.5126(5) 0.4747(13) 0.036(3) Uani 0.493(5) 1 d D . P B 2
H133 H 0.438737 0.493752 0.461876 0.043 Uiso 0.493(5) 1 calc R U P B 2
C134 C 0.490(4) 0.5526(6) 0.4499(11) 0.027(4) Uani 0.493(5) 1 d D . P B 2
H134 H 0.641876 0.569591 0.447803 0.033 Uiso 0.493(5) 1 calc R U P B 2
C135 C 0.329(4) 0.5536(6) 0.3577(12) 0.036(3) Uani 0.493(5) 1 d D . P B 2
H13A H 0.409142 0.537340 0.312979 0.043 Uiso 0.493(5) 1 calc R U P B 2
H13B H 0.155709 0.543609 0.364726 0.043 Uiso 0.493(5) 1 calc R U P B 2
O109 O 0.7497(11) 0.47064(15) 0.5994(5) 0.0402(15) Uani 0.493(5) 1 d D . P B 2
C136 C 1.006(2) 0.4567(3) 0.5947(7) 0.052(2) Uani 0.493(5) 1 d D . P B 2
H13C H 1.130058 0.477773 0.605100 0.063 Uiso 0.493(5) 1 calc R U P B 2
H13D H 1.022465 0.446041 0.532699 0.063 Uiso 0.493(5) 1 calc R U P B 2
C137 C 1.066(3) 0.4262(3) 0.6675(9) 0.043(3) Uani 0.493(5) 1 d D . P B 2
C138 C 1.121(2) 0.3900(3) 0.6405(7) 0.051(2) Uani 0.493(5) 1 d D . P B 2
H138 H 1.126920 0.384433 0.577006 0.061 Uiso 0.493(5) 1 calc R U P B 2
C139 C 1.167(3) 0.3617(3) 0.7062(9) 0.062(3) Uani 0.493(5) 1 d D . P B 2
H139 H 1.206671 0.336714 0.687928 0.075 Uiso 0.493(5) 1 calc R U P B 2
C140 C 1.155(3) 0.3704(4) 0.8002(10) 0.059(4) Uani 0.493(5) 1 d D . P B 2
H140 H 1.189286 0.351347 0.845893 0.070 Uiso 0.493(5) 1 calc R U P B 2
C141 C 1.095(2) 0.4065(3) 0.8253(7) 0.055(3) Uani 0.493(5) 1 d D . P B 2
H141 H 1.083830 0.412421 0.888401 0.066 Uiso 0.493(5) 1 calc R U P B 2
C142 C 1.0491(19) 0.4342(3) 0.7588(6) 0.049(2) Uani 0.493(5) 1 d D . P B 2
H142 H 1.005783 0.459114 0.776551 0.059 Uiso 0.493(5) 1 calc R U P B 2
C158 C 0.477(7) 0.6011(8) 0.262(3) 0.070(9) Uani 0.493(5) 1 d D . P B 2
C159 C 0.431(7) 0.6412(7) 0.232(2) 0.065(7) Uani 0.493(5) 1 d D . P B 2
H15A H 0.509265 0.658295 0.279253 0.078 Uiso 0.493(5) 1 calc R U P B 2
H15B H 0.245986 0.645923 0.222249 0.078 Uiso 0.493(5) 1 calc R U P B 2
H15C H 0.507514 0.645589 0.173753 0.078 Uiso 0.493(5) 1 calc R U P B 2
C43 C 0.7984(8) 0.46809(12) 0.3861(3) 0.0447(10) Uani 1 1 d . . . . .
C44 C 1.0526(9) 0.42828(11) 0.3023(3) 0.0403(9) Uani 1 1 d . . . . .
H44A H 0.895963 0.412585 0.302192 0.048 Uiso 1 1 calc R U . . .
H44B H 1.197540 0.414029 0.334451 0.048 Uiso 1 1 calc R U . . .
C45 C 1.1075(8) 0.43663(11) 0.2040(3) 0.0385(9) Uani 1 1 d . . . . .
H45 H 1.261349 0.453330 0.202924 0.046 Uiso 1 1 calc R U . . .
C46 C 1.1477(8) 0.39946(11) 0.1551(3) 0.0371(8) Uani 1 1 d . . . . .
C47 C 1.3352(9) 0.37256(13) 0.1750(3) 0.0484(11) Uani 1 1 d . . . . .
H47 H 1.463575 0.376131 0.224930 0.058 Uiso 1 1 calc R U . . .
C48 C 1.3340(10) 0.34000(13) 0.1209(3) 0.0506(11) Uani 1 1 d . . . . .
H48 H 1.464400 0.321491 0.133139 0.061 Uiso 1 1 calc R U . . .
C49 C 1.1446(10) 0.33453(13) 0.0496(3) 0.0489(11) Uani 1 1 d . . . . .
H49 H 1.144270 0.312023 0.013868 0.059 Uiso 1 1 calc R U . . .
C50 C 0.9543(9) 0.36146(14) 0.0293(3) 0.0484(10) Uani 1 1 d . . . . .
H50 H 0.824770 0.357639 -0.020107 0.058 Uiso 1 1 calc R U . . .
C51 C 0.9569(8) 0.39429(12) 0.0829(3) 0.0379(8) Uani 1 1 d . . . . .
C52 C 0.7906(8) 0.42789(12) 0.0767(3) 0.0405(9) Uani 1 1 d . . . . .
C53 C 0.5791(10) 0.43676(15) 0.0166(3) 0.0534(11) Uani 1 1 d . . . . .
H53 H 0.518123 0.419509 -0.030567 0.064 Uiso 1 1 calc R U . . .
C54 C 0.4569(10) 0.47107(15) 0.0259(4) 0.0586(13) Uani 1 1 d . . . . .
H54 H 0.309449 0.477188 -0.014568 0.070 Uiso 1 1 calc R U . . .
C55 C 0.5477(10) 0.49671(13) 0.0937(4) 0.0528(11) Uani 1 1 d . . . . .
H55 H 0.463483 0.520337 0.098632 0.063 Uiso 1 1 calc R U . . .
C56 C 0.7605(9) 0.48802(11) 0.1544(3) 0.0446(10) Uani 1 1 d . . . . .
H56 H 0.823086 0.505552 0.200635 0.054 Uiso 1 1 calc R U . . .
C57 C 0.8803(8) 0.45327(11) 0.1463(3) 0.0389(9) Uani 1 1 d . . . . .
O1 O 0.7345(5) 0.69050(7) 0.57750(15) 0.0284(5) Uani 1 1 d . . . . .
O2 O 0.6043(5) 0.69935(7) 0.81775(15) 0.0304(5) Uani 1 1 d . . . . .
O3 O 0.4067(5) 0.62562(7) 0.77070(16) 0.0315(5) Uani 1 1 d . . . . .
O5 O 1.1050(5) 0.66387(7) 0.47092(16) 0.0299(5) Uani 1 1 d . . . . .
O6 O 0.2204(5) 0.72890(8) 0.81657(18) 0.0388(6) Uani 1 1 d . . . . .
O7 O 0.8486(5) 0.69405(9) 0.36086(18) 0.0392(6) Uani 1 1 d . . . . .
O10 O 0.8067(6) 0.50254(8) 0.4257(3) 0.0532(9) Uani 1 1 d . . . . .
O12 O 0.6246(6) 0.44643(9) 0.3848(3) 0.0705(12) Uani 1 1 d . . . . .
O13 O 1.0170(5) 0.46382(7) 0.3502(2) 0.0397(6) Uani 1 1 d . . . . .
S1 S 0.56898(17) 0.75420(2) 0.64422(6) 0.03241(19) Uani 1 1 d . . . . .
Cl1 Cl 1.2469(2) 0.74790(3) 0.31172(6) 0.0445(2) 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
C1 O1 1.429(4) . ?
C1 C2 1.526(5) . ?
C1 S1 1.801(4) . ?
C2 O2 1.442(4) . ?
C2 C3 1.521(5) . ?
C3 O3 1.424(4) . ?
C3 C4 1.526(5) . ?
C4 O4 1.43(2) . ?
C4 O104 1.458(17) . ?
C4 C5 1.528(5) . ?
C5 O1 1.437(4) . ?
C5 C6 1.506(5) . ?
C6 O5 1.448(4) . ?
C7 C8 1.375(6) . ?
C7 C13 1.377(5) . ?
C7 S1 1.776(4) . ?
C8 C9 1.379(7) . ?
C9 C10 1.380(8) . ?
C10 C12 1.379(8) . ?
C10 C11 1.514(7) . ?
C12 C13 1.389(7) . ?
C14 O6 1.200(5) . ?
C14 O2 1.357(5) . ?
C14 C15 1.492(5) . ?
C15 C16 1.384(6) . ?
C15 C20 1.386(6) . ?
C16 C17 1.393(5) . ?
C17 C18 1.368(7) . ?
C18 C19 1.385(7) . ?
C19 C20 1.381(5) . ?
C21 O3 1.441(4) . ?
C21 C22 1.494(6) . ?
C22 C27 1.384(7) . ?
C22 C23 1.385(6) . ?
C23 C24 1.367(7) . ?
C24 C25 1.379(8) . ?
C25 C26 1.364(9) . ?
C26 C27 1.386(8) . ?
C28 O7 1.185(4) . ?
C28 O5 1.352(4) . ?
C28 C29 1.505(5) . ?
C29 Cl1 1.774(4) . ?
N1 N2 1.221(10) . ?
N1 C31 1.498(14) . ?
N2 N3 1.137(11) . ?
O4 C30 1.408(15) . ?
O8 C30 1.430(14) . ?
O8 C34 1.436(15) . ?
O11 C58 1.349(18) . ?
O11 C35 1.448(16) . ?
O14 C58 1.214(18) . ?
C30 C31 1.535(15) . ?
C31 C32 1.513(15) . ?
C32 O9 1.419(13) . ?
C32 C33 1.525(16) . ?
C33 O10 1.464(18) . ?
C33 C34 1.514(16) . ?
C34 C35 1.485(16) . ?
O9 C36 1.423(11) . ?
C36 C37 1.521(14) . ?
C37 C38 1.381(14) . ?
C37 C42 1.386(15) . ?
C38 C39 1.379(15) . ?
C39 C40 1.376(17) . ?
C40 C41 1.39(2) . ?
C41 C42 1.394(17) . ?
C58 C59 1.491(18) . ?
N101 N102 1.236(12) . ?
N101 C131 1.492(13) . ?
N102 N103 1.158(12) . ?
O104 C130 1.415(15) . ?
O108 C130 1.424(13) . ?
O108 C134 1.438(15) . ?
O111 C158 1.35(2) . ?
O111 C135 1.452(15) . ?
O114 C158 1.20(2) . ?
C130 C131 1.528(14) . ?
C131 C132 1.539(13) . ?
C132 O109 1.428(11) . ?
C132 C133 1.521(15) . ?
C133 O10 1.484(19) . ?
C133 C134 1.523(17) . ?
C134 C135 1.515(16) . ?
O109 C136 1.437(11) . ?
C136 C137 1.522(13) . ?
C137 C142 1.370(15) . ?
C137 C138 1.376(14) . ?
C138 C139 1.390(14) . ?
C139 C140 1.411(17) . ?
C140 C141 1.373(18) . ?
C141 C142 1.383(13) . ?
C158 C159 1.49(2) . ?
C43 O12 1.188(5) . ?
C43 O13 1.313(5) . ?
C43 O10 1.345(5) . ?
C44 O13 1.457(4) . ?
C44 C45 1.517(6) . ?
C45 C57 1.508(6) . ?
C45 C46 1.518(5) . ?
C46 C47 1.377(6) . ?
C46 C51 1.391(6) . ?
C47 C48 1.394(6) . ?
C48 C49 1.379(7) . ?
C49 C50 1.389(7) . ?
C50 C51 1.397(6) . ?
C51 C52 1.470(6) . ?
C52 C53 1.381(6) . ?
C52 C57 1.400(6) . ?
C53 C54 1.383(7) . ?
C54 C55 1.390(8) . ?
C55 C56 1.388(7) . ?
C56 C57 1.389(6) . ?

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
O1 C1 C2 110.7(3) . . ?
O1 C1 S1 108.5(2) . . ?
C2 C1 S1 106.7(2) . . ?
O2 C2 C3 106.6(3) . . ?
O2 C2 C1 107.4(3) . . ?
C3 C2 C1 114.1(3) . . ?
O3 C3 C2 108.3(3) . . ?
O3 C3 C4 112.4(3) . . ?
C2 C3 C4 110.1(3) . . ?
O4 C4 C3 107.4(8) . . ?
O104 C4 C3 113.6(7) . . ?
O4 C4 C5 105.5(8) . . ?
O104 C4 C5 112.2(7) . . ?
C3 C4 C5 106.1(3) . . ?
O1 C5 C6 107.0(3) . . ?
O1 C5 C4 106.9(3) . . ?
C6 C5 C4 115.7(3) . . ?
O5 C6 C5 107.2(3) . . ?
C8 C7 C13 119.2(4) . . ?
C8 C7 S1 121.6(3) . . ?
C13 C7 S1 119.0(3) . . ?
C7 C8 C9 120.4(4) . . ?
C8 C9 C10 121.6(5) . . ?
C12 C10 C9 117.3(4) . . ?
C12 C10 C11 121.7(6) . . ?
C9 C10 C11 121.0(6) . . ?
C10 C12 C13 121.8(4) . . ?
C7 C13 C12 119.7(4) . . ?
O6 C14 O2 124.4(3) . . ?
O6 C14 C15 124.9(4) . . ?
O2 C14 C15 110.6(3) . . ?
C16 C15 C20 119.7(3) . . ?
C16 C15 C14 122.4(4) . . ?
C20 C15 C14 117.9(3) . . ?
C15 C16 C17 119.4(4) . . ?
C18 C17 C16 120.7(4) . . ?
C17 C18 C19 119.9(4) . . ?
C20 C19 C18 119.8(4) . . ?
C19 C20 C15 120.4(4) . . ?
O3 C21 C22 111.5(3) . . ?
C27 C22 C23 117.5(4) . . ?
C27 C22 C21 122.0(4) . . ?
C23 C22 C21 120.3(4) . . ?
C24 C23 C22 121.8(5) . . ?
C23 C24 C25 120.0(5) . . ?
C26 C25 C24 119.4(5) . . ?
C25 C26 C27 120.5(5) . . ?
C22 C27 C26 120.7(5) . . ?
O7 C28 O5 125.5(3) . . ?
O7 C28 C29 126.9(3) . . ?
O5 C28 C29 107.6(3) . . ?
C28 C29 Cl1 111.2(2) . . ?
N2 N1 C31 113.5(8) . . ?
N3 N2 N1 170.2(12) . . ?
C30 O4 C4 110.5(13) . . ?
C30 O8 C34 114.7(13) . . ?
C58 O11 C35 118.8(18) . . ?
O4 C30 O8 113.2(15) . . ?
O4 C30 C31 107.1(13) . . ?
O8 C30 C31 110.3(12) . . ?
N1 C31 C32 108.7(10) . . ?
N1 C31 C30 108.0(9) . . ?
C32 C31 C30 107.9(10) . . ?
O9 C32 C31 113.3(11) . . ?
O9 C32 C33 113.5(11) . . ?
C31 C32 C33 110.4(11) . . ?
O10 C33 C34 100.7(12) . . ?
O10 C33 C32 115.3(13) . . ?
C34 C33 C32 109.6(12) . . ?
O8 C34 C35 108.3(16) . . ?
O8 C34 C33 110.2(14) . . ?
C35 C34 C33 114.8(16) . . ?
O11 C35 C34 113.0(15) . . ?
C32 O9 C36 117.2(9) . . ?
O9 C36 C37 107.2(9) . . ?
C38 C37 C42 119.9(11) . . ?
C38 C37 C36 122.6(11) . . ?
C42 C37 C36 117.4(11) . . ?
C39 C38 C37 121.0(11) . . ?
C40 C39 C38 119.4(12) . . ?
C39 C40 C41 120.3(13) . . ?
C40 C41 C42 119.8(14) . . ?
C37 C42 C41 119.3(12) . . ?
O14 C58 O11 121(2) . . ?
O14 C58 C59 122(2) . . ?
O11 C58 C59 115.5(15) . . ?
N102 N101 C131 109.3(10) . . ?
N103 N102 N101 170.5(13) . . ?
C130 O104 C4 115.4(13) . . ?
C130 O108 C134 115.0(12) . . ?
C158 O111 C135 114.9(18) . . ?
O104 C130 O108 111.9(14) . . ?
O104 C130 C131 108.5(12) . . ?
O108 C130 C131 109.3(10) . . ?
N101 C131 C130 110.1(9) . . ?
N101 C131 C132 109.8(9) . . ?
C130 C131 C132 110.8(10) . . ?
O109 C132 C133 111.9(11) . . ?
O109 C132 C131 107.2(9) . . ?
C133 C132 C131 107.0(12) . . ?
O10 C133 C132 98.5(11) . . ?
O10 C133 C134 110.6(15) . . ?
C132 C133 C134 113.0(12) . . ?
O108 C134 C135 106.1(14) . . ?
O108 C134 C133 110.7(15) . . ?
C135 C134 C133 111.4(14) . . ?
O111 C135 C134 110.0(14) . . ?
C132 O109 C136 116.6(8) . . ?
O109 C136 C137 109.9(9) . . ?
C142 C137 C138 120.2(10) . . ?
C142 C137 C136 120.2(10) . . ?
C138 C137 C136 119.5(11) . . ?
C137 C138 C139 120.0(10) . . ?
C138 C139 C140 119.4(10) . . ?
C141 C140 C139 119.5(12) . . ?
C140 C141 C142 120.1(10) . . ?
C137 C142 C141 120.8(9) . . ?
O114 C158 O111 122(2) . . ?
O114 C158 C159 128(2) . . ?
O111 C158 C159 109(2) . . ?
O12 C43 O13 128.0(4) . . ?
O12 C43 O10 125.6(4) . . ?
O13 C43 O10 106.3(3) . . ?
O13 C44 C45 109.2(3) . . ?
C57 C45 C44 113.0(4) . . ?
C57 C45 C46 102.3(3) . . ?
C44 C45 C46 108.8(3) . . ?
C47 C46 C51 120.9(4) . . ?
C47 C46 C45 128.8(4) . . ?
C51 C46 C45 110.3(4) . . ?
C46 C47 C48 119.1(5) . . ?
C49 C48 C47 120.4(4) . . ?
C48 C49 C50 120.9(4) . . ?
C49 C50 C51 118.8(4) . . ?
C46 C51 C50 120.0(4) . . ?
C46 C51 C52 108.6(4) . . ?
C50 C51 C52 131.4(4) . . ?
C53 C52 C57 120.5(4) . . ?
C53 C52 C51 131.1(4) . . ?
C57 C52 C51 108.5(4) . . ?
C52 C53 C54 119.2(5) . . ?
C53 C54 C55 120.7(5) . . ?
C56 C55 C54 120.5(4) . . ?
C55 C56 C57 118.9(5) . . ?
C56 C57 C52 120.3(4) . . ?
C56 C57 C45 129.5(4) . . ?
C52 C57 C45 110.2(3) . . ?
C1 O1 C5 112.2(2) . . ?
C14 O2 C2 118.7(3) . . ?
C3 O3 C21 112.0(3) . . ?
C28 O5 C6 117.1(3) . . ?
C43 O10 C33 118.8(7) . . ?
C43 O10 C133 115.3(8) . . ?
C43 O13 C44 116.5(3) . . ?
C7 S1 C1 102.29(17) . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1987992'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: This value represents the accessible observable data available for this crystal.
;
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          3 Report
RESPONSE: These atoms are part of a disordered group, and were not stable to refinement with anisotropic thermal parameters.
;
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: Several bad reflections have been omitted from the refinement. 
;
_vrf_PLAT089_shelx               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.62 Note
RESPONSE: The extra parameters required for the disordered groups has pushed this ratio to slightly below the desired threshold.
;
_vrf_PLAT987_shelx               
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: The molecule stereochemistry is known from the synthesis and cannot be a racemate.
;
# Added during the CSD deposition process: Tuesday 03 March 2020 01:42 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H46 Cl N3 O14'
_chemical_formula_sum            'C44 H46 Cl N3 O14'
_chemical_formula_weight         876.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1104(2)
_cell_length_b                   19.5548(6)
_cell_length_c                   27.2321(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4318.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    164(2)
_cell_measurement_reflns_used    17308
_cell_measurement_theta_min      6.7
_cell_measurement_theta_max      72.7

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.389
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'ABSCOR, Higashi (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      164(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
;
 Rigaku MM007 rotating anode
;
_diffrn_radiation_monochromator  
;
Rigaku VariMax-HF Confocal Optical System
;
_diffrn_measurement_device_type  
;  
Rigaku Spider 
;
_diffrn_measurement_device_details 'Curved image plate'
_diffrn_measurement_method       ω-scans
_diffrn_measurement_details      '551 images in steps of 1°'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            34329
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         6.654
_diffrn_reflns_theta_max         58.931
_diffrn_reflns_theta_full        58.931
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6132
_reflns_number_gt                4550
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.987

_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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess (Rigaku, 1998)'
_computing_data_reduction        'FSProcess (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1173P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.101(9)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6132
_refine_ls_number_parameters     528
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.098
_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 0.6387(5) 0.68626(19) 0.49958(12) 0.0525(10) Uani 1 1 d . . . . .
O2 O 0.6056(5) 0.80082(19) 0.48834(13) 0.0585(11) Uani 1 1 d . . . . .
O3 O 0.4560(5) 0.77578(19) 0.39599(13) 0.0560(10) Uani 1 1 d . . . . .
O4 O 0.5651(4) 0.64843(19) 0.35369(12) 0.0512(10) Uani 1 1 d . . . . .
O5 O 0.5250(5) 0.53758(18) 0.42595(12) 0.0510(9) Uani 1 1 d . . . . .
O7 O 0.5043(6) 0.9282(2) 0.66724(18) 0.0802(13) Uani 1 1 d . . . . .
O8 O 0.6710(7) 0.8309(3) 0.36267(17) 0.0851(15) Uani 1 1 d . . . . .
O10 O 0.7100(5) 0.4458(2) 0.42376(13) 0.0556(10) Uani 1 1 d . . . . .
O11 O 0.2633(5) 0.3640(2) 0.37882(15) 0.0678(12) Uani 1 1 d . . . . .
O12 O 0.3943(7) 0.3291(3) 0.47364(18) 0.0904(16) Uani 1 1 d . . . . .
H12X H 0.411561 0.286785 0.473243 0.108 Uiso 1 1 calc R U . . .
O13 O 0.8707(6) 0.4003(2) 0.50625(16) 0.0794(14) Uani 1 1 d . . . . .
O14 O 0.9817(9) 0.3059(3) 0.53789(19) 0.110(2) Uani 1 1 d . . . . .
N1 N 0.3764(8) 0.4915(3) 0.3397(2) 0.0765(16) Uani 1 1 d . . . . .
N2 N 0.2959(8) 0.4631(3) 0.3075(2) 0.0771(16) Uani 1 1 d . . . . .
N3 N 0.2140(10) 0.4457(4) 0.2757(2) 0.108(2) Uani 1 1 d . . . . .
C1 C 0.5396(8) 0.7372(3) 0.47576(18) 0.0486(14) Uani 1 1 d . . . . .
H1 H 0.421004 0.733397 0.485436 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5625(7) 0.7286(3) 0.42057(19) 0.0505(14) Uani 1 1 d . . . . .
H2 H 0.679703 0.738380 0.411612 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5168(8) 0.6567(3) 0.40381(17) 0.0493(13) Uani 1 1 d . . . . .
H3 H 0.394668 0.650707 0.406460 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6017(7) 0.6021(3) 0.43434(18) 0.0450(13) Uani 1 1 d . . . . .
H4 H 0.721349 0.599661 0.425593 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5819(8) 0.6176(3) 0.48939(18) 0.0503(14) Uani 1 1 d . . . . .
H5 H 0.463500 0.612982 0.499096 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6891(9) 0.5709(3) 0.5214(2) 0.0663(18) Uani 1 1 d . . . . .
H6A H 0.733711 0.533396 0.500912 0.080 Uiso 1 1 calc R U . A 1
H6B H 0.783321 0.597456 0.534426 0.080 Uiso 1 1 calc R U . A 1
C7 C 0.5708(7) 0.8272(3) 0.5345(2) 0.0537(15) Uani 1 1 d . . . . .
C8 C 0.5205(7) 0.7897(3) 0.5745(2) 0.0503(13) Uani 1 1 d . . . . .
H8 H 0.502439 0.741873 0.571342 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4956(7) 0.8221(3) 0.6202(2) 0.0552(14) Uani 1 1 d . . . . .
H9 H 0.461622 0.796144 0.647852 0.066 Uiso 1 1 calc R U . . .
C10 C 0.5208(7) 0.8914(3) 0.6245(2) 0.0592(15) Uani 1 1 d . . . . .
C11 C 0.5684(8) 0.9286(3) 0.5840(3) 0.0680(18) Uani 1 1 d . . . . .
H11 H 0.583347 0.976601 0.586881 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5947(8) 0.8974(3) 0.5394(2) 0.0587(15) Uani 1 1 d . . . . .
H12 H 0.629148 0.923709 0.511892 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4589(11) 0.8905(4) 0.7106(3) 0.095(2) Uani 1 1 d . . . . .
H13A H 0.347883 0.871570 0.706393 0.114 Uiso 1 1 calc R U . . .
H13B H 0.460452 0.921008 0.739093 0.114 Uiso 1 1 calc R U . . .
H13C H 0.537536 0.853075 0.715708 0.114 Uiso 1 1 calc R U . . .
C14 C 0.5247(10) 0.8218(3) 0.3651(2) 0.0650(17) Uani 1 1 d . . . . .
C15 C 0.3979(5) 0.8562(2) 0.33430(15) 0.0661(17) Uani 1 1 d G . . . .
C16 C 0.2333(6) 0.8364(2) 0.33582(19) 0.1126(19) Uani 1 1 d G . . . .
H16 H 0.198485 0.802335 0.358398 0.135 Uiso 1 1 calc R U . . .
C17 C 0.1198(5) 0.8666(3) 0.3043(2) 0.1126(19) Uani 1 1 d G . . . .
H17 H 0.007302 0.853055 0.305341 0.135 Uiso 1 1 calc R U . . .
C18 C 0.1707(6) 0.9165(3) 0.2713(2) 0.1126(19) Uani 1 1 d G . . . .
H18 H 0.093128 0.937045 0.249729 0.135 Uiso 1 1 calc R U . . .
C19 C 0.3353(7) 0.9362(2) 0.26975(17) 0.092(2) Uani 1 1 d G . . . .
H19 H 0.370138 0.970315 0.247173 0.110 Uiso 1 1 calc R U . . .
C20 C 0.4489(5) 0.9061(2) 0.30127(18) 0.082(2) Uani 1 1 d G . . . .
H20 H 0.561324 0.919596 0.300230 0.098 Uiso 1 1 calc R U . . .
C21 C 0.4307(8) 0.6559(3) 0.31878(18) 0.0569(15) Uani 1 1 d . . . . .
H21A H 0.366992 0.697945 0.325861 0.068 Uiso 1 1 calc R U . . .
H21B H 0.355345 0.616176 0.320817 0.068 Uiso 1 1 calc R U . . .
C22 C 0.5073(8) 0.6600(3) 0.26845(18) 0.0577(15) Uani 1 1 d . . . . .
C23 C 0.4861(10) 0.6065(4) 0.2350(2) 0.077(2) Uani 1 1 d . . . . .
H23 H 0.424208 0.567320 0.244319 0.092 Uiso 1 1 calc R U . . .
C24 C 0.5552(12) 0.6099(6) 0.1879(3) 0.108(3) Uani 1 1 d . . . . .
H24 H 0.538824 0.573573 0.165312 0.130 Uiso 1 1 calc R U . . .
C25 C 0.6452(12) 0.6651(6) 0.1747(3) 0.105(3) Uani 1 1 d . . . . .
H25 H 0.694985 0.666568 0.143176 0.126 Uiso 1 1 calc R U . . .
C26 C 0.6662(10) 0.7206(5) 0.2072(3) 0.094(2) Uani 1 1 d . . . . .
H26 H 0.724931 0.760379 0.197383 0.113 Uiso 1 1 calc R U . . .
C27 C 0.5982(9) 0.7155(4) 0.2542(2) 0.0730(19) Uani 1 1 d . . . . .
H27 H 0.615678 0.751623 0.276881 0.088 Uiso 1 1 calc R U . . .
C30 C 0.6083(8) 0.4901(3) 0.39613(19) 0.0550(15) Uani 1 1 d . . . . .
H30 H 0.677084 0.515201 0.371541 0.066 Uiso 1 1 calc R U . . .
C31 C 0.4793(8) 0.4464(3) 0.3691(2) 0.0584(15) Uani 1 1 d . . . . .
H31 H 0.537867 0.413948 0.346722 0.070 Uiso 1 1 calc R U . . .
C32 C 0.3766(8) 0.4051(3) 0.4058(2) 0.0605(16) Uani 1 1 d . . . . .
H32 H 0.314348 0.437049 0.427678 0.073 Uiso 1 1 calc R U . . .
C33 C 0.4891(9) 0.3609(3) 0.4366(2) 0.0646(17) Uani 1 1 d . . . . .
H33 H 0.540281 0.324965 0.415296 0.078 Uiso 1 1 calc R U . . .
C34 C 0.6238(8) 0.4036(3) 0.4599(2) 0.0601(16) Uani 1 1 d . . . . .
H34 H 0.573899 0.433906 0.485504 0.072 Uiso 1 1 calc R U . . .
C35 C 0.7456(9) 0.3583(3) 0.4832(2) 0.0683(18) Uani 1 1 d . . . . .
H35A H 0.691130 0.329178 0.508119 0.082 Uiso 1 1 calc R U . . .
H35B H 0.796597 0.328237 0.458227 0.082 Uiso 1 1 calc R U . . .
C36A C 0.110(2) 0.3588(10) 0.4045(8) 0.064(3) Uiso 0.429(17) 1 d . U P B 1
H36A H 0.058018 0.404429 0.406599 0.077 Uiso 0.429(17) 1 calc R U P B 1
H36B H 0.130441 0.342206 0.438318 0.077 Uiso 0.429(17) 1 calc R U P B 1
C37A C 0.000(3) 0.3112(7) 0.3787(7) 0.0704(19) Uiso 0.429(17) 1 d G U P B 1
C38A C 0.000(3) 0.2428(8) 0.3927(6) 0.121(5) Uani 0.429(17) 1 d G . P B 1
H38A H 0.065033 0.228348 0.419807 0.145 Uiso 0.429(17) 1 calc R U P B 1
C39A C -0.095(3) 0.1957(6) 0.3672(8) 0.121(5) Uani 0.429(17) 1 d G . P B 1
H39A H -0.095235 0.148954 0.376736 0.145 Uiso 0.429(17) 1 calc R U P B 1
C40A C -0.191(2) 0.2169(8) 0.3275(8) 0.121(5) Uani 0.429(17) 1 d G . P B 1
H40A H -0.255623 0.184619 0.310058 0.145 Uiso 0.429(17) 1 calc R U P B 1
C41A C -0.191(2) 0.2852(9) 0.3135(6) 0.121(5) Uani 0.429(17) 1 d G . P B 1
H41A H -0.255743 0.299677 0.286450 0.145 Uiso 0.429(17) 1 calc R U P B 1
C42A C -0.095(3) 0.3324(6) 0.3391(7) 0.121(5) Uani 0.429(17) 1 d G . P B 1
H42A H -0.095475 0.379072 0.329519 0.145 Uiso 0.429(17) 1 calc R U P B 1
C36B C 0.0966(16) 0.3779(7) 0.3859(6) 0.064(3) Uiso 0.571(17) 1 d . U P B 2
H36C H 0.061261 0.415624 0.364062 0.077 Uiso 0.571(17) 1 calc R U P B 2
H36D H 0.076593 0.391787 0.420318 0.077 Uiso 0.571(17) 1 calc R U P B 2
C37B C 0.0010(19) 0.3140(5) 0.3742(5) 0.0704(19) Uiso 0.571(17) 1 d G U P B 2
C38B C 0.0288(17) 0.2557(6) 0.4023(5) 0.101(3) Uani 0.571(17) 1 d G . P B 2
H38B H 0.107111 0.256717 0.428192 0.121 Uiso 0.571(17) 1 calc R U P B 2
C39B C -0.0581(16) 0.1960(5) 0.3924(5) 0.101(3) Uani 0.571(17) 1 d G . P B 2
H39B H -0.039061 0.156195 0.411519 0.121 Uiso 0.571(17) 1 calc R U P B 2
C40B C -0.1727(15) 0.1946(5) 0.3544(5) 0.101(3) Uani 0.571(17) 1 d G . P B 2
H40B H -0.232011 0.153776 0.347657 0.121 Uiso 0.571(17) 1 calc R U P B 2
C41B C -0.2005(14) 0.2529(7) 0.3264(4) 0.101(3) Uani 0.571(17) 1 d G . P B 2
H41B H -0.278792 0.251880 0.300469 0.121 Uiso 0.571(17) 1 calc R U P B 2
C42B C -0.1136(18) 0.3126(5) 0.3363(5) 0.101(3) Uani 0.571(17) 1 d G . P B 2
H42B H -0.132622 0.352404 0.317142 0.121 Uiso 0.571(17) 1 calc R U P B 2
C43 C 0.9850(11) 0.3674(4) 0.5329(2) 0.082(2) Uani 1 1 d . . . . .
C44 C 1.1145(12) 0.4143(4) 0.5520(3) 0.102(3) Uani 1 1 d . . . . .
H44A H 1.198443 0.387724 0.569500 0.123 Uiso 1 1 calc R U . . .
H44B H 1.064437 0.447386 0.574526 0.123 Uiso 1 1 calc R U . . .
H44C H 1.166008 0.438668 0.524534 0.123 Uiso 1 1 calc R U . . .
O6A O 0.602(2) 0.5439(6) 0.5595(4) 0.0983(19) Uani 0.583(5) 1 d D U P C 1
O9A O 0.8269(14) 0.4983(5) 0.5939(3) 0.0983(19) Uani 0.583(5) 1 d D U P C 1
C28A C 0.672(2) 0.5035(7) 0.5927(4) 0.081(3) Uani 0.583(5) 1 d D U P C 1
C29A C 0.577(2) 0.4712(8) 0.6303(6) 0.116(5) Uiso 0.583(5) 1 d D U P C 1
H29A H 0.633599 0.477318 0.662213 0.140 Uiso 0.583(5) 1 calc R U P C 1
H29B H 0.570892 0.421550 0.623514 0.140 Uiso 0.583(5) 1 calc R U P C 1
Cl1A Cl 0.3719(6) 0.5046(3) 0.63502(16) 0.1092(16) Uani 0.583(5) 1 d D . P C 1
O6B O 0.597(3) 0.5721(8) 0.5708(5) 0.0983(19) Uani 0.417(5) 1 d D . P C 2
O9B O 0.4502(19) 0.4877(7) 0.5585(4) 0.0983(19) Uani 0.417(5) 1 d D . P C 2
C28B C 0.504(2) 0.5279(9) 0.5882(5) 0.073(5) Uani 0.417(5) 1 d D . P C 2
C29B C 0.469(7) 0.5426(18) 0.6398(12) 0.116(5) Uiso 0.211(7) 1 d D U P C 2
H29C H 0.397052 0.583349 0.641962 0.140 Uiso 0.211(7) 1 calc R U P C 2
H29D H 0.573723 0.553286 0.656856 0.140 Uiso 0.211(7) 1 calc R U P C 2
Cl1B Cl 0.3693(19) 0.4710(5) 0.6703(4) 0.082(2) Uiso 0.211(7) 1 d D U P C 2
C29C C 0.408(6) 0.557(2) 0.6341(18) 0.116(5) Uiso 0.206(7) 1 d D U P D 3
H29E H 0.337386 0.589563 0.620405 0.140 Uiso 0.2058 1 d . U P D 3
H29F H 0.492749 0.572641 0.654737 0.140 Uiso 0.2058 1 d . U P D 3
Cl1C Cl 0.298(2) 0.4838(6) 0.6592(5) 0.082(2) Uiso 0.206(7) 1 d D U P D 3


_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 C1 1.434(6) . ?
O1 C5 1.446(6) . ?
O2 C7 1.388(7) . ?
O2 C1 1.398(6) . ?
O3 C14 1.353(7) . ?
O3 C2 1.431(6) . ?
O4 C3 1.429(6) . ?
O4 C21 1.454(6) . ?
O5 C30 1.406(6) . ?
O5 C4 1.425(6) . ?
O7 C10 1.374(7) . ?
O7 C13 1.440(9) . ?
O8 C14 1.202(8) . ?
O10 C30 1.414(7) . ?
O10 C34 1.463(6) . ?
O11 C36B 1.392(13) . ?
O11 C32 1.425(7) . ?
O11 C36A 1.427(18) . ?
O12 C33 1.412(7) . ?
O12 H12X 0.8400 . ?
O13 C43 1.341(9) . ?
O13 C35 1.448(8) . ?
O14 C43 1.210(8) . ?
N1 N2 1.226(8) . ?
N1 C31 1.455(8) . ?
N2 N3 1.143(8) . ?
C1 C2 1.524(8) . ?
C1 H1 1.0000 . ?
C2 C3 1.523(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.519(7) . ?
C3 H3 1.0000 . ?
C4 C5 1.538(7) . ?
C4 H4 1.0000 . ?
C5 C6 1.532(8) . ?
C5 H5 1.0000 . ?
C6 O6A 1.363(13) . ?
C6 O6B 1.542(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.375(8) . ?
C7 C12 1.392(8) . ?
C8 C9 1.411(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(9) . ?
C11 C12 1.377(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.487(8) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.507(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.368(9) . ?
C22 C23 1.399(8) . ?
C23 C24 1.401(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.352(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.410(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(10) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C30 C31 1.539(8) . ?
C30 H30 1.0000 . ?
C31 C32 1.532(8) . ?
C31 H31 1.0000 . ?
C32 C33 1.510(9) . ?
C32 H32 1.0000 . ?
C33 C34 1.515(9) . ?
C33 H33 1.0000 . ?
C34 C35 1.471(9) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36A C37A 1.471(18) . ?
C36A H36A 0.9900 . ?
C36A H36B 0.9900 . ?
C37A C38A 1.3900 . ?
C37A C42A 1.3900 . ?
C38A C39A 1.3900 . ?
C38A H38A 0.9500 . ?
C39A C40A 1.3900 . ?
C39A H39A 0.9500 . ?
C40A C41A 1.3900 . ?
C40A H40A 0.9500 . ?
C41A C42A 1.3900 . ?
C41A H41A 0.9500 . ?
C42A H42A 0.9500 . ?
C36B C37B 1.504(13) . ?
C36B H36C 0.9900 . ?
C36B H36D 0.9900 . ?
C37B C38B 1.3900 . ?
C37B C42B 1.3900 . ?
C38B C39B 1.3900 . ?
C38B H38B 0.9500 . ?
C39B C40B 1.3900 . ?
C39B H39B 0.9500 . ?
C40B C41B 1.3900 . ?
C40B H40B 0.9500 . ?
C41B C42B 1.3900 . ?
C41B H41B 0.9500 . ?
C42B H42B 0.9500 . ?
C43 C44 1.489(11) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
O6A C28A 1.329(15) . ?
O9A C28A 1.262(14) . ?
C28A C29A 1.428(19) . ?
C29A Cl1A 1.791(17) . ?
C29A H29A 0.9900 . ?
C29A H29B 0.9900 . ?
O6B C28B 1.242(18) . ?
O9B C28B 1.210(15) . ?
C28B C29B 1.46(3) . ?
C29B Cl1B 1.82(3) . ?
C29B H29C 0.9900 . ?
C29B H29D 0.9900 . ?
C29C Cl1C 1.82(3) . ?
C29C H29E 0.9316 . ?
C29C H29F 0.9404 . ?

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
C1 O1 C5 112.2(4) . . ?
C7 O2 C1 118.4(4) . . ?
C14 O3 C2 118.2(5) . . ?
C3 O4 C21 114.0(4) . . ?
C30 O5 C4 117.8(4) . . ?
C10 O7 C13 116.7(5) . . ?
C30 O10 C34 115.2(4) . . ?
C36B O11 C32 116.5(6) . . ?
C32 O11 C36A 110.4(7) . . ?
C33 O12 H12X 109.5 . . ?
C43 O13 C35 116.5(5) . . ?
N2 N1 C31 115.2(5) . . ?
N3 N2 N1 170.4(8) . . ?
O2 C1 O1 107.0(4) . . ?
O2 C1 C2 107.1(4) . . ?
O1 C1 C2 107.5(5) . . ?
O2 C1 H1 111.7 . . ?
O1 C1 H1 111.7 . . ?
C2 C1 H1 111.7 . . ?
O3 C2 C3 108.0(4) . . ?
O3 C2 C1 108.5(5) . . ?
C3 C2 C1 111.6(4) . . ?
O3 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
O4 C3 C4 108.6(4) . . ?
O4 C3 C2 108.9(4) . . ?
C4 C3 C2 112.0(4) . . ?
O4 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
O5 C4 C3 109.7(4) . . ?
O5 C4 C5 106.6(4) . . ?
C3 C4 C5 110.3(4) . . ?
O5 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
O1 C5 C6 105.3(4) . . ?
O1 C5 C4 109.7(4) . . ?
C6 C5 C4 112.1(5) . . ?
O1 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
O6A C6 C5 111.7(8) . . ?
C5 C6 O6B 102.3(9) . . ?
O6A C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
O6A C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 O2 125.4(5) . . ?
C8 C7 C12 119.5(5) . . ?
O2 C7 C12 115.1(5) . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O7 C10 C9 125.1(6) . . ?
O7 C10 C11 115.4(6) . . ?
C9 C10 C11 119.5(6) . . ?
C10 C11 C12 121.2(6) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 119.9(6) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 O3 122.6(6) . . ?
O8 C14 C15 125.8(6) . . ?
O3 C14 C15 111.5(6) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C14 121.4(4) . . ?
C20 C15 C14 118.4(4) . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O4 C21 C22 106.9(5) . . ?
O4 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O4 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
C27 C22 C23 118.3(6) . . ?
C27 C22 C21 121.6(6) . . ?
C23 C22 C21 120.1(6) . . ?
C22 C23 C24 120.7(7) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.9(8) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.9(7) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 118.1(8) . . ?
C27 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
C22 C27 C26 122.0(7) . . ?
C22 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
O5 C30 O10 112.2(4) . . ?
O5 C30 C31 108.4(5) . . ?
O10 C30 C31 108.1(5) . . ?
O5 C30 H30 109.4 . . ?
O10 C30 H30 109.4 . . ?
C31 C30 H30 109.4 . . ?
N1 C31 C32 111.6(5) . . ?
N1 C31 C30 108.5(5) . . ?
C32 C31 C30 110.5(5) . . ?
N1 C31 H31 108.7 . . ?
C32 C31 H31 108.7 . . ?
C30 C31 H31 108.7 . . ?
O11 C32 C33 110.7(5) . . ?
O11 C32 C31 108.1(5) . . ?
C33 C32 C31 109.6(5) . . ?
O11 C32 H32 109.5 . . ?
C33 C32 H32 109.5 . . ?
C31 C32 H32 109.5 . . ?
O12 C33 C32 108.6(6) . . ?
O12 C33 C34 109.5(5) . . ?
C32 C33 C34 110.6(5) . . ?
O12 C33 H33 109.4 . . ?
C32 C33 H33 109.4 . . ?
C34 C33 H33 109.4 . . ?
O10 C34 C35 108.0(5) . . ?
O10 C34 C33 111.9(4) . . ?
C35 C34 C33 109.5(5) . . ?
O10 C34 H34 109.2 . . ?
C35 C34 H34 109.2 . . ?
C33 C34 H34 109.2 . . ?
O13 C35 C34 108.5(5) . . ?
O13 C35 H35A 110.0 . . ?
C34 C35 H35A 110.0 . . ?
O13 C35 H35B 110.0 . . ?
C34 C35 H35B 110.0 . . ?
H35A C35 H35B 108.4 . . ?
O11 C36A C37A 109.9(15) . . ?
O11 C36A H36A 109.7 . . ?
C37A C36A H36A 109.7 . . ?
O11 C36A H36B 109.7 . . ?
C37A C36A H36B 109.7 . . ?
H36A C36A H36B 108.2 . . ?
C38A C37A C42A 120.0 . . ?
C38A C37A C36A 118.5(13) . . ?
C42A C37A C36A 121.4(13) . . ?
C37A C38A C39A 120.0 . . ?
C37A C38A H38A 120.0 . . ?
C39A C38A H38A 120.0 . . ?
C40A C39A C38A 120.0 . . ?
C40A C39A H39A 120.0 . . ?
C38A C39A H39A 120.0 . . ?
C39A C40A C41A 120.0 . . ?
C39A C40A H40A 120.0 . . ?
C41A C40A H40A 120.0 . . ?
C40A C41A C42A 120.0 . . ?
C40A C41A H41A 120.0 . . ?
C42A C41A H41A 120.0 . . ?
C41A C42A C37A 120.0 . . ?
C41A C42A H42A 120.0 . . ?
C37A C42A H42A 120.0 . . ?
O11 C36B C37B 108.1(11) . . ?
O11 C36B H36C 110.1 . . ?
C37B C36B H36C 110.1 . . ?
O11 C36B H36D 110.1 . . ?
C37B C36B H36D 110.1 . . ?
H36C C36B H36D 108.4 . . ?
C38B C37B C42B 120.0 . . ?
C38B C37B C36B 118.8(9) . . ?
C42B C37B C36B 121.2(9) . . ?
C37B C38B C39B 120.0 . . ?
C37B C38B H38B 120.0 . . ?
C39B C38B H38B 120.0 . . ?
C40B C39B C38B 120.0 . . ?
C40B C39B H39B 120.0 . . ?
C38B C39B H39B 120.0 . . ?
C39B C40B C41B 120.0 . . ?
C39B C40B H40B 120.0 . . ?
C41B C40B H40B 120.0 . . ?
C40B C41B C42B 120.0 . . ?
C40B C41B H41B 120.0 . . ?
C42B C41B H41B 120.0 . . ?
C41B C42B C37B 120.0 . . ?
C41B C42B H42B 120.0 . . ?
C37B C42B H42B 120.0 . . ?
O14 C43 O13 121.5(8) . . ?
O14 C43 C44 126.0(8) . . ?
O13 C43 C44 112.4(7) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C28A O6A C6 121.9(14) . . ?
O9A C28A O6A 119.4(13) . . ?
O9A C28A C29A 118.9(12) . . ?
O6A C28A C29A 121.4(15) . . ?
C28A C29A Cl1A 113.0(11) . . ?
C28A C29A H29A 109.0 . . ?
Cl1A C29A H29A 109.0 . . ?
C28A C29A H29B 109.0 . . ?
Cl1A C29A H29B 109.0 . . ?
H29A C29A H29B 107.8 . . ?
C28B O6B C6 128.2(13) . . ?
O9B C28B O6B 114.5(14) . . ?
O9B C28B C29B 135(2) . . ?
O6B C28B C29B 110.2(18) . . ?
C28B C29B Cl1B 112(2) . . ?
C28B C29B H29C 109.2 . . ?
Cl1B C29B H29C 109.2 . . ?
C28B C29B H29D 109.2 . . ?
Cl1B C29B H29D 109.2 . . ?
H29C C29B H29D 107.9 . . ?
Cl1C C29C H29E 112.9 . . ?
Cl1C C29C H29F 112.8 . . ?
H29E C29C H29F 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O2 C1 O1 -77.8(6) . . . . ?
C7 O2 C1 C2 167.1(5) . . . . ?
C5 O1 C1 O2 179.8(4) . . . . ?
C5 O1 C1 C2 -65.4(5) . . . . ?
C14 O3 C2 C3 -117.1(5) . . . . ?
C14 O3 C2 C1 121.9(5) . . . . ?
O2 C1 C2 O3 -69.2(6) . . . . ?
O1 C1 C2 O3 176.1(4) . . . . ?
O2 C1 C2 C3 172.0(5) . . . . ?
O1 C1 C2 C3 57.3(6) . . . . ?
C21 O4 C3 C4 137.6(5) . . . . ?
C21 O4 C3 C2 -100.3(5) . . . . ?
O3 C2 C3 O4 70.0(5) . . . . ?
C1 C2 C3 O4 -170.9(4) . . . . ?
O3 C2 C3 C4 -169.9(4) . . . . ?
C1 C2 C3 C4 -50.8(6) . . . . ?
C30 O5 C4 C3 104.5(5) . . . . ?
C30 O5 C4 C5 -136.1(5) . . . . ?
O4 C3 C4 O5 -74.4(5) . . . . ?
C2 C3 C4 O5 165.4(4) . . . . ?
O4 C3 C4 C5 168.5(5) . . . . ?
C2 C3 C4 C5 48.3(6) . . . . ?
C1 O1 C5 C6 -174.5(4) . . . . ?
C1 O1 C5 C4 64.7(6) . . . . ?
O5 C4 C5 O1 -172.9(4) . . . . ?
C3 C4 C5 O1 -53.9(6) . . . . ?
O5 C4 C5 C6 70.5(6) . . . . ?
C3 C4 C5 C6 -170.5(5) . . . . ?
O1 C5 C6 O6A 108.4(7) . . . . ?
C4 C5 C6 O6A -132.4(7) . . . . ?
O1 C5 C6 O6B 85.0(8) . . . . ?
C4 C5 C6 O6B -155.8(8) . . . . ?
C1 O2 C7 C8 20.8(8) . . . . ?
C1 O2 C7 C12 -160.9(5) . . . . ?
O2 C7 C8 C9 177.3(5) . . . . ?
C12 C7 C8 C9 -0.9(9) . . . . ?
C7 C8 C9 C10 0.4(9) . . . . ?
C13 O7 C10 C9 0.7(9) . . . . ?
C13 O7 C10 C11 -178.4(6) . . . . ?
C8 C9 C10 O7 -178.4(6) . . . . ?
C8 C9 C10 C11 0.7(9) . . . . ?
O7 C10 C11 C12 177.8(6) . . . . ?
C9 C10 C11 C12 -1.4(10) . . . . ?
C10 C11 C12 C7 0.9(10) . . . . ?
C8 C7 C12 C11 0.2(9) . . . . ?
O2 C7 C12 C11 -178.2(5) . . . . ?
C2 O3 C14 O8 -10.7(8) . . . . ?
C2 O3 C14 C15 167.2(4) . . . . ?
O8 C14 C15 C16 172.3(6) . . . . ?
O3 C14 C15 C16 -5.4(6) . . . . ?
O8 C14 C15 C20 -3.5(8) . . . . ?
O3 C14 C15 C20 178.7(4) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
C14 C15 C16 C17 -175.8(5) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
C14 C15 C20 C19 175.9(5) . . . . ?
C3 O4 C21 C22 168.8(4) . . . . ?
O4 C21 C22 C27 -69.1(7) . . . . ?
O4 C21 C22 C23 111.0(7) . . . . ?
C27 C22 C23 C24 -0.6(11) . . . . ?
C21 C22 C23 C24 179.4(7) . . . . ?
C22 C23 C24 C25 0.9(13) . . . . ?
C23 C24 C25 C26 -2.2(14) . . . . ?
C24 C25 C26 C27 3.1(13) . . . . ?
C23 C22 C27 C26 1.6(11) . . . . ?
C21 C22 C27 C26 -178.4(7) . . . . ?
C25 C26 C27 C22 -2.8(12) . . . . ?
C4 O5 C30 O10 91.9(5) . . . . ?
C4 O5 C30 C31 -148.8(4) . . . . ?
C34 O10 C30 O5 60.9(6) . . . . ?
C34 O10 C30 C31 -58.6(5) . . . . ?
N2 N1 C31 C32 -75.0(7) . . . . ?
N2 N1 C31 C30 163.0(6) . . . . ?
O5 C30 C31 N1 59.4(6) . . . . ?
O10 C30 C31 N1 -178.7(4) . . . . ?
O5 C30 C31 C32 -63.2(6) . . . . ?
O10 C30 C31 C32 58.7(6) . . . . ?
C36B O11 C32 C33 123.7(9) . . . . ?
C36A O11 C32 C33 95.9(11) . . . . ?
C36B O11 C32 C31 -116.3(10) . . . . ?
C36A O11 C32 C31 -144.1(11) . . . . ?
N1 C31 C32 O11 61.1(6) . . . . ?
C30 C31 C32 O11 -178.1(5) . . . . ?
N1 C31 C32 C33 -178.2(5) . . . . ?
C30 C31 C32 C33 -57.4(6) . . . . ?
O11 C32 C33 O12 -67.3(6) . . . . ?
C31 C32 C33 O12 173.5(5) . . . . ?
O11 C32 C33 C34 172.5(5) . . . . ?
C31 C32 C33 C34 53.3(6) . . . . ?
C30 O10 C34 C35 177.0(5) . . . . ?
C30 O10 C34 C33 56.4(6) . . . . ?
O12 C33 C34 O10 -171.3(5) . . . . ?
C32 C33 C34 O10 -51.7(6) . . . . ?
O12 C33 C34 C35 69.0(7) . . . . ?
C32 C33 C34 C35 -171.3(5) . . . . ?
C43 O13 C35 C34 174.7(5) . . . . ?
O10 C34 C35 O13 59.3(6) . . . . ?
C33 C34 C35 O13 -178.6(5) . . . . ?
C32 O11 C36A C37A -174.7(12) . . . . ?
O11 C36A C37A C38A 92.8(18) . . . . ?
O11 C36A C37A C42A -83.1(19) . . . . ?
C42A C37A C38A C39A 0.0 . . . . ?
C36A C37A C38A C39A -176(2) . . . . ?
C37A C38A C39A C40A 0.0 . . . . ?
C38A C39A C40A C41A 0.0 . . . . ?
C39A C40A C41A C42A 0.0 . . . . ?
C40A C41A C42A C37A 0.0 . . . . ?
C38A C37A C42A C41A 0.0 . . . . ?
C36A C37A C42A C41A 176(2) . . . . ?
C32 O11 C36B C37B -155.0(9) . . . . ?
O11 C36B C37B C38B 62.1(14) . . . . ?
O11 C36B C37B C42B -118.0(12) . . . . ?
C42B C37B C38B C39B 0.0 . . . . ?
C36B C37B C38B C39B 179.9(15) . . . . ?
C37B C38B C39B C40B 0.0 . . . . ?
C38B C39B C40B C41B 0.0 . . . . ?
C39B C40B C41B C42B 0.0 . . . . ?
C40B C41B C42B C37B 0.0 . . . . ?
C38B C37B C42B C41B 0.0 . . . . ?
C36B C37B C42B C41B -179.9(15) . . . . ?
C35 O13 C43 O14 -1.1(10) . . . . ?
C35 O13 C43 C44 175.9(6) . . . . ?
C5 C6 O6A C28A -178.0(10) . . . . ?
C6 O6A C28A O9A 11.4(18) . . . . ?
C6 O6A C28A C29A -175.2(11) . . . . ?
O9A C28A C29A Cl1A 161.4(11) . . . . ?
O6A C28A C29A Cl1A -12.1(18) . . . . ?
C5 C6 O6B C28B 102(2) . . . . ?
C6 O6B C28B O9B -18(3) . . . . ?
C6 O6B C28B C29B 168(3) . . . . ?
O9B C28B C29B Cl1B 21(6) . . . . ?
O6B C28B C29B Cl1B -168(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
O12 H12X O14 0.84 1.92 2.751(8) 168.6 4_456 yes

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene / Petroleum ether'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1987993'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT241_shelx               
;
PROBLEM: High   MainMol Ueq as Compared to Neighbors of        C35 Check
RESPONSE: Arises because of libration of the benzyl group, with C35 being beside the pivot point
;
_vrf_PLAT242_shelx               
;
PROBLEM: Low    MainMol Ueq as Compared to Neighbors of        C36 Check
RESPONSE: Arises because of libration of the benzyl group, with C36 being the pivot point
;
_vrf_PLAT906_shelx               
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.504 Check
RESPONSE: Large K factor only observed for weakest model-based amplitudes. Deemed acceptable
;
# Added during the CSD deposition process: Tuesday 03 March 2020 01:42 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H45 N3 O14'
_chemical_formula_sum            'C43 H45 N3 O14'
_chemical_formula_weight         827.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.0833(2)
_cell_length_b                   18.7876(7)
_cell_length_c                   26.8116(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4071.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10222
_cell_measurement_theta_min      4.6320
_cell_measurement_theta_max      72.7210

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.852
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_reflns_number            64624
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         4.051
_diffrn_reflns_theta_max         74.658
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8176
_reflns_number_gt                6651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+0.8821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 2388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8176
_refine_ls_number_parameters     548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.5190(5) 0.7589(2) 0.01721(17) 0.0341(9) Uani 1 1 d . . . . .
H1 H 0.399560 0.763024 0.007902 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5434(5) 0.7675(2) 0.07281(16) 0.0333(8) Uani 1 1 d . . . . .
H2 H 0.659509 0.754873 0.082203 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5034(4) 0.8436(2) 0.08954(15) 0.0330(8) Uani 1 1 d . . . . .
H3 H 0.381613 0.851954 0.086671 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5951(4) 0.8983(2) 0.05787(16) 0.0329(8) Uani 1 1 d . . . . .
H4 H 0.716565 0.896100 0.064839 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5615(4) 0.8820(2) 0.00254(16) 0.0319(8) Uani 1 1 d . . . . .
H5 H 0.440263 0.885870 -0.004439 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6568(5) 0.9302(2) -0.03238(16) 0.0338(8) Uani 1 1 d . . . . .
C7 C 0.5475(4) 0.6656(2) -0.04318(16) 0.0347(9) Uani 1 1 d . . . . .
C8 C 0.4875(5) 0.7061(2) -0.08224(17) 0.0373(9) Uani 1 1 d . . . . .
H8 H 0.461151 0.754887 -0.077331 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4658(5) 0.6746(2) -0.12903(17) 0.0391(9) Uani 1 1 d . . . . .
H9 H 0.425324 0.702408 -0.156007 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5027(5) 0.6037(2) -0.13651(18) 0.0417(10) Uani 1 1 d . . . . .
C11 C 0.5579(5) 0.5631(2) -0.0964(2) 0.0445(11) Uani 1 1 d . . . . .
H11 H 0.580680 0.513910 -0.101028 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5801(5) 0.5936(2) -0.05004(19) 0.0408(10) Uani 1 1 d . . . . .
H12 H 0.617527 0.565492 -0.022858 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4564(8) 0.6117(3) -0.2241(2) 0.0604(14) Uani 1 1 d . . . . .
H13A H 0.342741 0.629615 -0.221757 0.072 Uiso 1 1 calc R U . . .
H13B H 0.468304 0.583151 -0.254461 0.072 Uiso 1 1 calc R U . . .
H13C H 0.533429 0.651963 -0.225270 0.072 Uiso 1 1 calc R U . . .
C14 C 0.4892(5) 0.6686(2) 0.12723(17) 0.0384(9) Uani 1 1 d . . . . .
C15 C 0.3550(5) 0.6338(2) 0.15597(17) 0.0382(9) Uani 1 1 d . . . . .
C16 C 0.1888(5) 0.6520(2) 0.14933(19) 0.0431(10) Uani 1 1 d . . . . .
H16 H 0.159405 0.686028 0.124704 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0667(6) 0.6210(2) 0.1782(2) 0.0512(12) Uani 1 1 d . . . . .
H17 H -0.045873 0.633920 0.173544 0.061 Uiso 1 1 calc R U . . .
C18 C 0.1097(7) 0.5707(3) 0.2141(2) 0.0528(12) Uani 1 1 d . . . . .
H18 H 0.026350 0.548957 0.233865 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2751(7) 0.5522(3) 0.2209(2) 0.0552(13) Uani 1 1 d . . . . .
H19 H 0.304279 0.517973 0.245444 0.066 Uiso 1 1 calc R U . . .
C20 C 0.3974(6) 0.5835(3) 0.19191(19) 0.0478(11) Uani 1 1 d . . . . .
H20 H 0.509963 0.570577 0.196607 0.057 Uiso 1 1 calc R U . . .
C21 C 0.4166(5) 0.8473(3) 0.17550(17) 0.0415(10) Uani 1 1 d . . . . .
H21A H 0.346625 0.805515 0.167783 0.050 Uiso 1 1 calc R U . . .
H21B H 0.347188 0.890677 0.173492 0.050 Uiso 1 1 calc R U . . .
C22 C 0.4902(5) 0.8403(3) 0.22681(17) 0.0433(10) Uani 1 1 d . . . . .
C23 C 0.4740(6) 0.8943(3) 0.26187(19) 0.0501(11) Uani 1 1 d . . . . .
H23 H 0.417116 0.936859 0.253405 0.060 Uiso 1 1 calc R U . . .
C24 C 0.5415(8) 0.8861(3) 0.3098(2) 0.0592(13) Uani 1 1 d . . . . .
H24 H 0.531766 0.923478 0.333428 0.071 Uiso 1 1 calc R U . . .
C25 C 0.6216(7) 0.8242(3) 0.3227(2) 0.0601(14) Uani 1 1 d . . . . .
H25 H 0.664674 0.818569 0.355414 0.072 Uiso 1 1 calc R U . . .
C26 C 0.6397(7) 0.7699(3) 0.2878(2) 0.0606(14) Uani 1 1 d . . . . .
H26 H 0.696585 0.727364 0.296395 0.073 Uiso 1 1 calc R U . . .
C27 C 0.5737(7) 0.7784(3) 0.2404(2) 0.0521(12) Uani 1 1 d . . . . .
H27 H 0.585900 0.741186 0.216623 0.062 Uiso 1 1 calc R U . . .
C28 C 0.6303(7) 1.0212(3) -0.09246(19) 0.0492(11) Uani 1 1 d . . . . .
H28A H 0.699227 1.056016 -0.074850 0.059 Uiso 1 1 calc R U . . .
H28B H 0.544523 1.046233 -0.111460 0.059 Uiso 1 1 calc R U . . .
H28C H 0.699281 0.993393 -0.115311 0.059 Uiso 1 1 calc R U . . .
C29 C 0.6292(5) 1.0107(2) 0.10032(16) 0.0350(8) Uani 1 1 d . . . . .
H29 H 0.684316 0.979796 0.125703 0.042 Uiso 1 1 calc R U . . .
C30 C 0.5125(5) 1.0623(2) 0.12641(16) 0.0393(9) Uani 1 1 d . . . . .
H30 H 0.577565 1.092174 0.150232 0.047 Uiso 1 1 calc R U . . .
C31 C 0.4304(5) 1.1107(2) 0.08784(17) 0.0400(9) Uani 1 1 d . . . . .
H31 H 0.366931 1.080994 0.063532 0.048 Uiso 1 1 calc R U . . .
C32 C 0.5640(6) 1.1514(2) 0.06038(17) 0.0413(9) Uani 1 1 d . . . . .
H32 H 0.625388 1.182898 0.084078 0.050 Uiso 1 1 calc R U . . .
C33 C 0.6825(5) 1.0976(2) 0.03671(17) 0.0382(9) Uani 1 1 d . . . . .
H33 H 0.621873 1.069028 0.011095 0.046 Uiso 1 1 calc R U . . .
C34 C 0.8244(6) 1.1362(2) 0.01223(19) 0.0448(10) Uani 1 1 d . . . . .
H34A H 0.782747 1.168073 -0.014362 0.054 Uiso 1 1 calc R U . . .
H34B H 0.884522 1.165321 0.037097 0.054 Uiso 1 1 calc R U . . .
C35 C 0.1660(6) 1.1664(3) 0.0866(2) 0.0597(15) Uani 1 1 d . . . . .
H35A H 0.121726 1.119647 0.075955 0.072 Uiso 1 1 calc R U . . .
H35B H 0.185860 1.195588 0.056442 0.072 Uiso 1 1 calc R U . . .
C36 C 0.0439(6) 1.2031(3) 0.12033(18) 0.0452(10) Uani 1 1 d . . . . .
C37 C -0.0289(7) 1.1659(3) 0.1592(2) 0.0635(14) Uani 1 1 d . . . . .
H37 H 0.000202 1.117630 0.165112 0.076 Uiso 1 1 calc R U . . .
C38 C -0.1435(8) 1.1991(4) 0.1894(2) 0.0705(17) Uani 1 1 d . . . . .
H38 H -0.192176 1.173813 0.216338 0.085 Uiso 1 1 calc R U . . .
C39 C -0.1865(7) 1.2669(4) 0.1808(2) 0.0652(16) Uani 1 1 d . . . . .
H39 H -0.263003 1.289813 0.202382 0.078 Uiso 1 1 calc R U . . .
C40 C -0.1216(8) 1.3037(3) 0.1412(3) 0.0666(16) Uani 1 1 d . . . . .
H40 H -0.156929 1.351073 0.134815 0.080 Uiso 1 1 calc R U . . .
C41 C -0.0044(7) 1.2721(3) 0.1104(2) 0.0590(13) Uani 1 1 d . . . . .
H41 H 0.041421 1.297481 0.083004 0.071 Uiso 1 1 calc R U . . .
C42 C 1.0488(6) 1.1048(3) -0.0403(2) 0.0526(12) Uani 1 1 d . . . . .
C43 C 1.1483(8) 1.0446(4) -0.0600(2) 0.0674(16) Uani 1 1 d . . . . .
H43A H 1.190706 1.056782 -0.093169 0.081 Uiso 1 1 calc R U . . .
H43B H 1.078573 1.002016 -0.062394 0.081 Uiso 1 1 calc R U . . .
H43C H 1.241189 1.035134 -0.037483 0.081 Uiso 1 1 calc R U . . .
N1 N 0.3898(5) 1.0206(2) 0.15458(16) 0.0494(10) Uani 1 1 d . . . . .
N2 N 0.3311(5) 1.0508(2) 0.19162(16) 0.0502(10) Uani 1 1 d . . . . .
N3 N 0.2701(6) 1.0709(3) 0.22702(17) 0.0642(13) Uani 1 1 d . . . . .
O1 O 0.6171(3) 0.81137(14) -0.00793(11) 0.0330(6) Uani 1 1 d . . . . .
O2 O 0.5830(3) 0.69215(15) 0.00426(12) 0.0371(6) Uani 1 1 d . . . . .
O3 O 0.4283(3) 0.72154(15) 0.09809(11) 0.0361(6) Uani 1 1 d . . . . .
O4 O 0.5529(3) 0.85195(16) 0.14057(11) 0.0364(6) Uani 1 1 d . . . . .
O5 O 0.5333(3) 0.96805(14) 0.06787(11) 0.0338(6) Uani 1 1 d . . . . .
O6 O 0.8032(3) 0.92805(17) -0.03797(12) 0.0416(7) Uani 1 1 d . . . . .
O7 O 0.5529(4) 0.97399(16) -0.05656(11) 0.0401(7) Uani 1 1 d . . . . .
O8 O 0.4923(4) 0.56857(18) -0.18143(14) 0.0527(8) Uani 1 1 d . . . . .
O9 O 0.6337(4) 0.65343(19) 0.12969(15) 0.0539(9) Uani 1 1 d . . . . .
O10 O 0.7505(3) 1.05022(16) 0.07415(12) 0.0370(7) Uani 1 1 d . . . . .
O11 O 0.3191(4) 1.15666(18) 0.11375(11) 0.0426(7) Uani 1 1 d . . . . .
O12 O 0.4933(5) 1.1929(2) 0.02103(14) 0.0559(9) Uani 1 1 d . . . . .
H12X H 0.504(9) 1.241(4) 0.025(2) 0.07(2) Uiso 1 1 d . . . . .
O13 O 0.9331(4) 1.08278(18) -0.00871(14) 0.0509(8) Uani 1 1 d . . . . .
O14 O 1.0637(6) 1.1666(2) -0.05173(18) 0.0824(14) 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
C1 O2 1.401(5) . ?
C1 O1 1.433(5) . ?
C1 C2 1.512(6) . ?
C2 O3 1.440(5) . ?
C2 C3 1.533(5) . ?
C3 O4 1.434(5) . ?
C3 C4 1.524(6) . ?
C4 O5 1.429(5) . ?
C4 C5 1.539(6) . ?
C5 O1 1.429(4) . ?
C5 C6 1.514(6) . ?
C6 O6 1.194(5) . ?
C6 O7 1.342(5) . ?
C7 C8 1.383(6) . ?
C7 C12 1.390(6) . ?
C7 O2 1.396(5) . ?
C8 C9 1.398(6) . ?
C9 C10 1.380(6) . ?
C10 O8 1.376(6) . ?
C10 C11 1.392(7) . ?
C11 C12 1.382(7) . ?
C13 O8 1.432(7) . ?
C14 O9 1.205(5) . ?
C14 O3 1.357(5) . ?
C14 C15 1.483(6) . ?
C15 C20 1.393(6) . ?
C15 C16 1.397(6) . ?
C16 C17 1.382(7) . ?
C17 C18 1.393(7) . ?
C18 C19 1.393(8) . ?
C19 C20 1.388(7) . ?
C21 O4 1.449(5) . ?
C21 C22 1.505(6) . ?
C22 C23 1.390(7) . ?
C22 C27 1.393(7) . ?
C23 C24 1.404(7) . ?
C24 C25 1.374(8) . ?
C25 C26 1.392(9) . ?
C26 C27 1.389(7) . ?
C28 O7 1.451(6) . ?
C29 O5 1.415(5) . ?
C29 O10 1.415(5) . ?
C29 C30 1.521(6) . ?
C30 N1 1.472(6) . ?
C30 C31 1.529(6) . ?
C31 O11 1.427(5) . ?
C31 C32 1.514(7) . ?
C32 O12 1.431(5) . ?
C32 C33 1.531(6) . ?
C33 O10 1.449(5) . ?
C33 C34 1.507(6) . ?
C34 O13 1.447(6) . ?
C35 O11 1.447(5) . ?
C35 C36 1.507(6) . ?
C36 C41 1.380(7) . ?
C36 C37 1.387(8) . ?
C37 C38 1.378(8) . ?
C38 C39 1.342(9) . ?
C39 C40 1.370(9) . ?
C40 C41 1.391(8) . ?
C42 O14 1.206(7) . ?
C42 O13 1.328(6) . ?
C42 C43 1.486(8) . ?
N1 N2 1.239(6) . ?
N2 N3 1.134(6) . ?

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
O2 C1 O1 107.1(3) . . ?
O2 C1 C2 106.9(3) . . ?
O1 C1 C2 108.5(3) . . ?
O3 C2 C1 108.4(3) . . ?
O3 C2 C3 106.6(3) . . ?
C1 C2 C3 111.1(3) . . ?
O4 C3 C4 108.8(3) . . ?
O4 C3 C2 108.8(3) . . ?
C4 C3 C2 111.2(3) . . ?
O5 C4 C3 110.1(3) . . ?
O5 C4 C5 107.5(3) . . ?
C3 C4 C5 108.5(3) . . ?
O1 C5 C6 105.9(3) . . ?
O1 C5 C4 108.6(3) . . ?
C6 C5 C4 112.8(3) . . ?
O6 C6 O7 125.5(4) . . ?
O6 C6 C5 124.2(4) . . ?
O7 C6 C5 110.3(3) . . ?
C8 C7 C12 120.1(4) . . ?
C8 C7 O2 124.5(4) . . ?
C12 C7 O2 115.4(4) . . ?
C7 C8 C9 119.4(4) . . ?
C10 C9 C8 120.8(4) . . ?
O8 C10 C9 125.3(5) . . ?
O8 C10 C11 115.6(4) . . ?
C9 C10 C11 119.1(4) . . ?
C12 C11 C10 120.6(4) . . ?
C11 C12 C7 119.9(4) . . ?
O9 C14 O3 123.8(4) . . ?
O9 C14 C15 125.2(4) . . ?
O3 C14 C15 110.9(3) . . ?
C20 C15 C16 119.4(4) . . ?
C20 C15 C14 118.6(4) . . ?
C16 C15 C14 121.9(4) . . ?
C17 C16 C15 120.8(4) . . ?
C16 C17 C18 119.6(5) . . ?
C17 C18 C19 120.0(5) . . ?
C20 C19 C18 120.3(5) . . ?
C19 C20 C15 120.0(5) . . ?
O4 C21 C22 107.2(3) . . ?
C23 C22 C27 118.6(5) . . ?
C23 C22 C21 121.1(5) . . ?
C27 C22 C21 120.3(5) . . ?
C22 C23 C24 120.1(5) . . ?
C25 C24 C23 120.4(5) . . ?
C24 C25 C26 120.0(5) . . ?
C27 C26 C25 119.4(5) . . ?
C26 C27 C22 121.4(5) . . ?
O5 C29 O10 111.8(3) . . ?
O5 C29 C30 107.7(3) . . ?
O10 C29 C30 108.9(3) . . ?
N1 C30 C29 108.4(4) . . ?
N1 C30 C31 111.8(4) . . ?
C29 C30 C31 109.7(3) . . ?
O11 C31 C32 112.4(4) . . ?
O11 C31 C30 107.7(3) . . ?
C32 C31 C30 108.7(3) . . ?
O12 C32 C31 110.4(4) . . ?
O12 C32 C33 107.7(4) . . ?
C31 C32 C33 108.3(4) . . ?
O10 C33 C34 108.0(4) . . ?
O10 C33 C32 110.8(4) . . ?
C34 C33 C32 109.8(4) . . ?
O13 C34 C33 107.3(4) . . ?
O11 C35 C36 108.4(4) . . ?
C41 C36 C37 120.0(5) . . ?
C41 C36 C35 120.0(5) . . ?
C37 C36 C35 119.9(5) . . ?
C38 C37 C36 119.9(6) . . ?
C39 C38 C37 120.2(6) . . ?
C38 C39 C40 120.9(6) . . ?
C39 C40 C41 120.4(6) . . ?
C36 C41 C40 118.6(5) . . ?
O14 C42 O13 122.1(5) . . ?
O14 C42 C43 126.1(5) . . ?
O13 C42 C43 111.7(5) . . ?
N2 N1 C30 115.2(4) . . ?
N3 N2 N1 171.9(6) . . ?
C5 O1 C1 111.8(3) . . ?
C7 O2 C1 118.0(3) . . ?
C14 O3 C2 118.4(3) . . ?
C3 O4 C21 113.5(3) . . ?
C29 O5 C4 116.4(3) . . ?
C6 O7 C28 115.2(4) . . ?
C10 O8 C13 116.1(4) . . ?
C29 O10 C33 113.7(3) . . ?
C31 O11 C35 111.7(3) . . ?
C42 O13 C34 117.3(4) . . ?

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
O12 H12X O14 0.92(7) 1.93(7) 2.822(6) 162(6) 4_475 yes

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.051

