# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1766
_audit_block_doi                 10.5517/ccdc.csd.cc1zj9rk
_database_code_depnum_ccdc_archive 'CCDC 1832929'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-05-03 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         ?
_chemical_formula_sum            'C99 H100 N2 O3'
_chemical_formula_weight         1365.80

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   13.339(5)
_cell_length_b                   18.203(6)
_cell_length_c                   18.304(7)
_cell_angle_alpha                106.445(4)
_cell_angle_beta                 110.829(6)
_cell_angle_gamma                95.262(6)
_cell_volume                     3891(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    2246

_cell_measurement_theta_min      3.1

_cell_measurement_theta_max      24.1


_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08

_exptl_crystal_size_mid          0.08

_exptl_crystal_size_min          0.02

_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.731

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   
;J́acobson, R. (1998) Private communication\'
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku CrystalClear-SM Expert 2.1 b29
;

_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            43494
_diffrn_reflns_av_unetI/netI     0.1873
_diffrn_reflns_av_R_equivalents  0.1612
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             13591
_reflns_number_gt                5423
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_structure_solution    SHELXS-97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.1157P)²+1.2475P] 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_number_reflns         13591
_refine_ls_number_parameters     958
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.2317
_refine_ls_R_factor_gt           0.0936
_refine_ls_wR_factor_ref         0.2860
_refine_ls_wR_factor_gt          0.2036
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.030
_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 1.0144(4) 0.6499(3) 0.3746(4) 0.0401(14) Uani 1 1 d . . . . .
N1 N 1.0727(3) 0.6363(3) 0.4455(3) 0.0381(12) Uani 1 1 d . . . . .
C2 C 1.1140(4) 0.5706(3) 0.4236(4) 0.0400(14) Uani 1 1 d . . . . .
C3 C 1.1783(4) 0.5349(3) 0.4771(3) 0.0376(13) Uani 1 1 d . . . . .
C4 C 1.2149(4) 0.4709(3) 0.4410(4) 0.0405(14) Uani 1 1 d . . . . .
C5 C 1.1938(4) 0.4470(3) 0.3557(3) 0.0383(14) Uani 1 1 d . . . . .
C6 C 1.1271(4) 0.4813(3) 0.3027(3) 0.0384(13) Uani 1 1 d . . . . .
C7 C 1.0822(4) 0.5426(3) 0.3374(3) 0.0374(13) Uani 1 1 d . . . . .
C8 C 1.0113(4) 0.5917(3) 0.3055(3) 0.0377(13) Uani 1 1 d . . . . .
C9 C 0.9255(4) 0.5812(3) 0.2244(3) 0.0407(14) Uani 1 1 d . . . . .
C10 C 0.8804(4) 0.5117(3) 0.1601(4) 0.0451(15) Uani 1 1 d . . . . .
H1 H 0.911497 0.467558 0.165310 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7913(5) 0.5025(4) 0.0877(4) 0.0511(16) Uani 1 1 d . . . . .
H2 H 0.763387 0.453027 0.044486 0.061 Uiso 1 1 calc R U . . .
C12 C 0.7430(5) 0.5642(4) 0.0779(4) 0.0508(16) Uani 1 1 d . . . . .
C13 C 0.7877(5) 0.6356(3) 0.1428(4) 0.0480(15) Uani 1 1 d . . . . .
H3 H 0.754197 0.678722 0.137258 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8771(4) 0.6470(3) 0.2141(3) 0.0421(14) Uani 1 1 d . . . . .
C15 C 0.9336(4) 0.7267(3) 0.2832(3) 0.0391(13) Uani 1 1 d . . . . .
C16 C 0.8710(4) 0.7923(3) 0.2962(4) 0.0401(14) Uani 1 1 d . . . . .
C17 C 0.8187(4) 0.8349(3) 0.2464(3) 0.0384(13) Uani 1 1 d . . . . .
C18 C 0.7720(4) 0.8950(3) 0.2815(3) 0.0382(13) Uani 1 1 d . . . . .
C19 C 0.7861(4) 0.9157(3) 0.3642(4) 0.0379(13) Uani 1 1 d . . . . .
C20 C 0.8416(4) 0.8746(3) 0.4161(3) 0.0371(13) Uani 1 1 d . . . . .
C21 C 0.8811(4) 0.8122(3) 0.3780(3) 0.0348(13) Uani 1 1 d . . . . .
N2 N 0.9382(3) 0.7645(3) 0.4200(3) 0.0376(11) Uani 1 1 d . . . . .
C22 C 0.9624(4) 0.7149(3) 0.3660(3) 0.0352(13) Uani 1 1 d . . . . .
C23 C 0.6458(6) 0.5562(4) -0.0005(4) 0.078(2) Uani 1 1 d . . . . .
H4 H 0.607570 0.501035 -0.028630 0.117 Uiso 1 1 calc R U . . .
H5 H 0.671403 0.574735 -0.037430 0.117 Uiso 1 1 calc R U . . .
H6 H 0.595333 0.587670 0.013827 0.117 Uiso 1 1 calc R U . . .
C24 C 1.0431(4) 0.7588(3) 0.2800(3) 0.0396(14) Uani 1 1 d . . . . .
C25 C 1.0757(5) 0.7239(3) 0.2180(4) 0.0485(15) Uani 1 1 d . . . . .
H7 H 1.031052 0.676390 0.175548 0.058 Uiso 1 1 calc R U . . .
C26 C 1.1722(5) 0.7561(4) 0.2154(4) 0.0509(16) Uani 1 1 d . . . . .
H8 H 1.192058 0.730751 0.171203 0.061 Uiso 1 1 calc R U . . .
C27 C 1.2406(5) 0.8257(4) 0.2773(4) 0.0513(16) Uani 1 1 d . . . . .
C28 C 1.2079(5) 0.8607(4) 0.3401(4) 0.0534(16) Uani 1 1 d . . . . .
H9 H 1.252579 0.908074 0.382861 0.064 Uiso 1 1 calc R U . . .
C29 C 1.1108(4) 0.8279(3) 0.3418(4) 0.0461(15) Uani 1 1 d . . . . .
H10 H 1.090450 0.852950 0.385809 0.055 Uiso 1 1 calc R U . . .
C30 C 1.3450(5) 0.8631(4) 0.2751(5) 0.072(2) Uani 1 1 d . . . . .
H11 H 1.327807 0.872406 0.222200 0.108 Uiso 1 1 calc R U . . .
H12 H 1.396604 0.827957 0.280414 0.108 Uiso 1 1 calc R U . . .
H13 H 1.378130 0.913034 0.321095 0.108 Uiso 1 1 calc R U . . .
C31 C 1.2084(4) 0.5705(3) 0.5679(3) 0.0365(13) Uani 1 1 d . . . . .
C32 C 1.1377(5) 0.5565(4) 0.6045(4) 0.0591(18) Uani 1 1 d . . . . .
H14 H 1.065528 0.526149 0.570298 0.071 Uiso 1 1 calc R U . . .
C33 C 1.1689(5) 0.5853(4) 0.6886(4) 0.0603(18) Uani 1 1 d . . . . .
H15 H 1.118433 0.572964 0.711429 0.072 Uiso 1 1 calc R U . . .
C34 C 1.2710(5) 0.6317(3) 0.7414(4) 0.0477(15) Uani 1 1 d . . . . .
C35 C 1.3399(5) 0.6477(4) 0.7040(4) 0.0597(18) Uani 1 1 d . . . . .
H16 H 1.410168 0.681175 0.737866 0.072 Uiso 1 1 calc R U . . .
C36 C 1.3107(5) 0.6173(3) 0.6199(4) 0.0508(16) Uani 1 1 d . . . . .
H17 H 1.361711 0.628727 0.597233 0.061 Uiso 1 1 calc R U . . .
C37 C 1.3075(5) 0.6609(4) 0.8327(4) 0.0670(19) Uani 1 1 d . . . . .
H18 H 1.243853 0.648990 0.846370 0.080 Uiso 1 1 calc R U . . .
H19 H 1.332465 0.718650 0.853123 0.080 Uiso 1 1 calc R U . . .
C38 C 1.4005(6) 0.6261(6) 0.8789(4) 0.097(3) Uani 1 1 d . . . . .
H20 H 1.375738 0.569130 0.860803 0.146 Uiso 1 1 calc R U . . .
H21 H 1.420478 0.648788 0.938831 0.146 Uiso 1 1 calc R U . . .
H22 H 1.464496 0.638305 0.866561 0.146 Uiso 1 1 calc R U . . .
C39 C 1.2784(4) 0.4311(3) 0.4987(3) 0.0413(14) Uani 1 1 d . . . . .
C40 C 1.2306(4) 0.3989(3) 0.5413(3) 0.0464(15) Uani 1 1 d . . . . .
H23 H 1.153967 0.394454 0.526844 0.056 Uiso 1 1 calc R U . . .
C41 C 1.2901(5) 0.3730(3) 0.6040(4) 0.0466(15) Uani 1 1 d . . . . .
H24 H 1.253940 0.352738 0.632752 0.056 Uiso 1 1 calc R U . . .
C42 C 1.4018(4) 0.3758(3) 0.6263(3) 0.0412(14) Uani 1 1 d . . . . .
C43 C 1.4477(5) 0.4021(3) 0.5791(4) 0.0478(15) Uani 1 1 d . . . . .
H25 H 1.522662 0.401579 0.589657 0.057 Uiso 1 1 calc R U . . .
C44 C 1.3881(4) 0.4292(3) 0.5168(4) 0.0468(15) Uani 1 1 d . . . . .
H26 H 1.423105 0.446840 0.485909 0.056 Uiso 1 1 calc R U . . .
C45 C 1.4670(5) 0.3546(3) 0.7019(4) 0.0489(15) Uani 1 1 d . . . . .
C46 C 1.4660(7) 0.4145(4) 0.7781(4) 0.087(2) Uani 1 1 d . . . . .
H27 H 1.492431 0.467333 0.780037 0.130 Uiso 1 1 calc R U . . .
H28 H 1.514075 0.405544 0.828087 0.130 Uiso 1 1 calc R U . . .
H29 H 1.390993 0.409400 0.775596 0.130 Uiso 1 1 calc R U . . .
C47 C 1.5872(5) 0.3556(4) 0.7127(5) 0.076(2) Uani 1 1 d . . . . .
H30 H 1.588966 0.316770 0.663905 0.114 Uiso 1 1 calc R U . . .
H31 H 1.626580 0.342934 0.762501 0.114 Uiso 1 1 calc R U . . .
H32 H 1.622426 0.407902 0.718715 0.114 Uiso 1 1 calc R U . . .
C48 C 1.4184(5) 0.2727(3) 0.6946(4) 0.0569(17) Uani 1 1 d . . . . .
H33 H 1.342421 0.269884 0.689652 0.085 Uiso 1 1 calc R U . . .
H34 H 1.461751 0.261128 0.744125 0.085 Uiso 1 1 calc R U . . .
H35 H 1.419605 0.234399 0.645154 0.085 Uiso 1 1 calc R U . . .
C49 C 1.2479(4) 0.3866(3) 0.3194(3) 0.0413(14) Uani 1 1 d . . . . .
C50 C 1.3262(5) 0.4095(3) 0.2919(4) 0.0520(16) Uani 1 1 d . . . . .
H36 H 1.350002 0.463667 0.302377 0.062 Uiso 1 1 calc R U . . .
C51 C 1.3701(5) 0.3562(4) 0.2503(4) 0.0551(16) Uani 1 1 d . . . . .
H37 H 1.423132 0.373549 0.231905 0.066 Uiso 1 1 calc R U . . .
C52 C 1.3371(5) 0.2760(4) 0.2346(4) 0.0480(15) Uani 1 1 d . . . . .
C53 C 1.2622(5) 0.2528(3) 0.2633(4) 0.0534(16) Uani 1 1 d . . . . .
H38 H 1.240144 0.198800 0.254371 0.064 Uiso 1 1 calc R U . . .
C54 C 1.2185(5) 0.3077(4) 0.3052(4) 0.0548(16) Uani 1 1 d . . . . .
H39 H 1.166757 0.290410 0.324802 0.066 Uiso 1 1 calc R U . . .
O1 O 1.3814(3) 0.2265(3) 0.1902(3) 0.0623(12) Uani 1 1 d . . . . .
C55 C 1.3363(6) 0.1446(4) 0.1638(4) 0.074(2) Uani 1 1 d . . . . .
H40 H 1.358946 0.126829 0.211849 0.111 Uiso 1 1 calc R U . . .
H41 H 1.362959 0.115695 0.123085 0.111 Uiso 1 1 calc R U . . .
H42 H 1.255958 0.135198 0.138330 0.111 Uiso 1 1 calc R U . . .
C56 C 1.1113(4) 0.4610(3) 0.2149(3) 0.0406(14) Uani 1 1 d . . . . .
C57 C 1.0709(5) 0.3853(4) 0.1579(4) 0.0537(16) Uani 1 1 d . . . . .
H43 H 1.052968 0.343485 0.175509 0.064 Uiso 1 1 calc R U . . .
C58 C 1.0564(5) 0.3700(4) 0.0771(4) 0.0660(19) Uani 1 1 d . . . . .
H44 H 1.025885 0.317931 0.039111 0.079 Uiso 1 1 calc R U . . .
C59 C 1.0846(6) 0.4273(5) 0.0496(4) 0.074(2) Uani 1 1 d . . . . .
H45 H 1.076221 0.415470 -0.006524 0.088 Uiso 1 1 calc R U . . .
C60 C 1.1262(5) 0.5039(5) 0.1055(5) 0.069(2) Uani 1 1 d . . . . .
H46 H 1.145974 0.544896 0.087373 0.082 Uiso 1 1 calc R U . . .
C61 C 1.1385(4) 0.5201(4) 0.1858(4) 0.0493(15) Uani 1 1 d . . . . .
H47 H 1.166150 0.572684 0.223000 0.059 Uiso 1 1 calc R U . . .
C62 C 0.8107(5) 0.8209(3) 0.1604(3) 0.0418(14) Uani 1 1 d . . . . .
C63 C 0.7113(5) 0.7948(3) 0.0920(4) 0.0538(16) Uani 1 1 d . . . . .
H48 H 0.644889 0.788412 0.099981 0.065 Uiso 1 1 calc R U . . .
C64 C 0.7071(6) 0.7780(4) 0.0123(4) 0.0633(19) Uani 1 1 d . . . . .
H49 H 0.638134 0.760041 -0.033796 0.076 Uiso 1 1 calc R U . . .
C65 C 0.8020(7) 0.7870(4) -0.0007(4) 0.068(2) Uani 1 1 d . . . . .
H50 H 0.799157 0.773718 -0.055539 0.082 Uiso 1 1 calc R U . . .
C66 C 0.9017(6) 0.8155(4) 0.0669(4) 0.0643(19) Uani 1 1 d . . . . .
H51 H 0.967616 0.823778 0.058632 0.077 Uiso 1 1 calc R U . . .
C67 C 0.9058(5) 0.8318(3) 0.1459(4) 0.0483(15) Uani 1 1 d . . . . .
H52 H 0.975032 0.850963 0.191726 0.058 Uiso 1 1 calc R U . . .
C68 C 0.7037(4) 0.9371(3) 0.2297(3) 0.0414(14) Uani 1 1 d . . . . .
C69 C 0.5924(5) 0.9283(3) 0.2130(4) 0.0503(16) Uani 1 1 d . . . . .
H53 H 0.560549 0.894922 0.234182 0.060 Uiso 1 1 calc R U . . .
C70 C 0.5271(5) 0.9668(4) 0.1666(4) 0.0578(17) Uani 1 1 d . . . . .
H54 H 0.451028 0.959650 0.155576 0.069 Uiso 1 1 calc R U . . .
C71 C 0.5726(5) 1.0154(4) 0.1362(4) 0.0601(18) Uani 1 1 d . . . . .
C72 C 0.6828(5) 1.0260(4) 0.1515(4) 0.0597(17) Uani 1 1 d . . . . .
H55 H 0.714354 1.059909 0.130697 0.072 Uiso 1 1 calc R U . . .
C73 C 0.7463(5) 0.9862(4) 0.1979(4) 0.0531(16) Uani 1 1 d . . . . .
H56 H 0.822120 0.992903 0.208120 0.064 Uiso 1 1 calc R U . . .
O2 O 0.4996(4) 1.0514(3) 0.0903(3) 0.0823(15) Uani 1 1 d . . . . .
C74 C 0.5457(7) 1.1108(5) 0.0671(6) 0.102(3) Uani 1 1 d . . . . .
H57 H 0.597393 1.152989 0.117150 0.153 Uiso 1 1 calc R U . . .
H58 H 0.486738 1.132127 0.035578 0.153 Uiso 1 1 calc R U . . .
H59 H 0.584356 1.088025 0.032536 0.153 Uiso 1 1 calc R U . . .
C75 C 0.7415(4) 0.9838(3) 0.3994(3) 0.0391(14) Uani 1 1 d . . . . .
C76 C 0.6533(4) 0.9740(3) 0.4218(3) 0.0439(14) Uani 1 1 d . . . . .
H60 H 0.625704 0.923847 0.421516 0.053 Uiso 1 1 calc R U . . .
C77 C 0.6051(4) 1.0356(3) 0.4444(3) 0.0448(15) Uani 1 1 d . . . . .
H61 H 0.544405 1.026692 0.458854 0.054 Uiso 1 1 calc R U . . .
C78 C 0.6425(4) 1.1102(3) 0.4468(3) 0.0421(14) Uani 1 1 d . . . . .
C79 C 0.7332(4) 1.1202(3) 0.4270(3) 0.0456(15) Uani 1 1 d . . . . .
H62 H 0.762501 1.170720 0.429097 0.055 Uiso 1 1 calc R U . . .
C80 C 0.7813(4) 1.0590(3) 0.4046(3) 0.0442(14) Uani 1 1 d . . . . .
H63 H 0.843708 1.068380 0.392178 0.053 Uiso 1 1 calc R U . . .
C81 C 0.5840(5) 1.1782(3) 0.4634(4) 0.0501(16) Uani 1 1 d . . . . .
C82 C 0.5013(5) 1.1605(4) 0.4985(5) 0.0672(19) Uani 1 1 d . . . . .
H64 H 0.538879 1.151736 0.551026 0.101 Uiso 1 1 calc R U . . .
H65 H 0.445706 1.113373 0.458858 0.101 Uiso 1 1 calc R U . . .
H66 H 0.465755 1.204947 0.508295 0.101 Uiso 1 1 calc R U . . .
C83 C 0.6657(5) 1.2532(3) 0.5217(4) 0.0618(18) Uani 1 1 d . . . . .
H67 H 0.626805 1.295869 0.530565 0.093 Uiso 1 1 calc R U . . .
H68 H 0.717001 1.265862 0.497571 0.093 Uiso 1 1 calc R U . . .
H69 H 0.706523 1.246811 0.575041 0.093 Uiso 1 1 calc R U . . .
C84 C 0.5222(6) 1.1880(4) 0.3795(5) 0.084(2) Uani 1 1 d . . . . .
H70 H 0.469235 1.139196 0.341186 0.126 Uiso 1 1 calc R U . . .
H71 H 0.574613 1.200522 0.356210 0.126 Uiso 1 1 calc R U . . .
H72 H 0.483114 1.230734 0.387469 0.126 Uiso 1 1 calc R U . . .
C85 C 0.8589(4) 0.8955(3) 0.5044(3) 0.0355(13) Uani 1 1 d . . . . .
C86 C 0.8104(5) 0.8429(3) 0.5308(4) 0.0463(15) Uani 1 1 d . . . . .
H73 H 0.766460 0.793438 0.492142 0.056 Uiso 1 1 calc R U . . .
C87 C 0.8263(5) 0.8626(3) 0.6129(4) 0.0483(15) Uani 1 1 d . . . . .
H74 H 0.790501 0.826865 0.629515 0.058 Uiso 1 1 calc R U . . .
C88 C 0.8925(5) 0.9325(3) 0.6722(3) 0.0423(14) Uani 1 1 d . . . . .
C89 C 0.9414(4) 0.9830(3) 0.6445(4) 0.0452(14) Uani 1 1 d . . . . .
H75 H 0.988936 1.031098 0.683658 0.054 Uiso 1 1 calc R U . . .
C90 C 0.9235(4) 0.9659(3) 0.5625(4) 0.0428(14) Uani 1 1 d . . . . .
H76 H 0.956068 1.002999 0.545620 0.051 Uiso 1 1 calc R U . . .
C91 C 0.9105(5) 0.9530(4) 0.7618(4) 0.0600(17) Uani 1 1 d . . . . .
H77 H 0.984520 0.986801 0.797066 0.072 Uiso 1 1 calc R U . . .
H78 H 0.906944 0.904513 0.775949 0.072 Uiso 1 1 calc R U . . .
C92 C 0.8256(6) 0.9951(4) 0.7792(4) 0.081(2) Uani 1 1 d . . . . .
H79 H 0.835207 1.046246 0.772028 0.122 Uiso 1 1 calc R U . . .
H80 H 0.833883 1.002636 0.836408 0.122 Uiso 1 1 calc R U . . .
H81 H 0.752125 0.963867 0.740593 0.122 Uiso 1 1 calc R U . . .
C93 C 1.0948(8) 0.7858(6) 0.7211(6) 0.125(3) Uani 1 1 d . . . . .
H82 H 1.166217 0.770855 0.737343 0.188 Uiso 1 1 calc R U . . .
H83 H 1.057706 0.774785 0.755593 0.188 Uiso 1 1 calc R U . . .
H84 H 1.105816 0.841892 0.728869 0.188 Uiso 1 1 calc R U . . .
C94 C 1.0259(7) 0.7397(6) 0.6318(6) 0.104(3) Uani 1 1 d . . . . .
H85 H 1.019183 0.683272 0.624717 0.125 Uiso 1 1 calc R U . . .
H86 H 0.951298 0.750598 0.618579 0.125 Uiso 1 1 calc R U . . .
O3 O 1.0617(4) 0.7531(3) 0.5759(3) 0.0594(13) Uani 1 1 d . . . . .
C95 C 1.3023(11) 0.7626(8) 1.0366(7) 0.184(5) Uani 1 1 d D U . . .
H87 H 1.332407 0.759134 1.092454 0.276 Uiso 1 1 calc R U . . .
H88 H 1.264506 0.710233 0.995857 0.276 Uiso 1 1 calc R U . . .
H89 H 1.362160 0.783648 1.024058 0.276 Uiso 1 1 calc R U . . .
C96 C 1.2216(12) 0.8163(9) 1.0325(9) 0.235(7) Uani 1 1 d D U . . .
H90 H 1.164307 0.794848 1.047939 0.282 Uiso 1 1 calc R U . . .
H91 H 1.261406 0.867846 1.075980 0.282 Uiso 1 1 calc R U . . .
C97 C 1.1671(13) 0.8304(8) 0.9566(9) 0.241(8) Uani 1 1 d D U . . .
H92 H 1.129185 0.778681 0.912898 0.290 Uiso 1 1 calc R U . . .
H93 H 1.224586 0.853064 0.942023 0.290 Uiso 1 1 calc R U . . .
C98 C 1.0843(10) 0.8823(8) 0.9510(8) 0.204(6) Uani 1 1 d D U . . .
H94 H 1.031076 0.865767 0.892458 0.245 Uiso 1 1 calc R U . . .
H95 H 1.043117 0.873362 0.984367 0.245 Uiso 1 1 calc R U . . .
C99 C 1.1308(16) 0.9687(8) 0.9797(12) 0.298(10) Uani 1 1 d D U . . .
H96 H 1.070959 0.997084 0.973622 0.447 Uiso 1 1 calc R U . . .
H97 H 1.181899 0.986552 1.038233 0.447 Uiso 1 1 calc R U . . .
H98 H 1.169825 0.978937 0.946073 0.447 Uiso 1 1 calc R U . . .
H99 H 1.080(4) 0.666(3) 0.494(3) 0.027(15) Uiso 1 1 d . . . . .
H100 H 1.023(7) 0.775(6) 0.553(6) 0.13(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.361(7) . ?
C1 C8 1.386(7) . ?
C1 C22 1.444(7) . ?
N1 C2 1.378(7) . ?
C2 C7 1.400(7) . ?
C2 C3 1.408(7) . ?
C3 C4 1.389(7) . ?
C3 C31 1.487(7) . ?
C4 C5 1.411(7) . ?
C4 C39 1.505(7) . ?
C5 C6 1.398(7) . ?
C5 C49 1.497(7) . ?
C6 C7 1.414(7) . ?
C6 C56 1.473(7) . ?
C7 C8 1.447(7) . ?
C8 C9 1.463(7) . ?
C9 C10 1.365(7) . ?
C9 C14 1.438(7) . ?
C10 C11 1.384(7) . ?
C11 C12 1.368(8) . ?
C12 C13 1.392(8) . ?
C12 C23 1.512(8) . ?
C13 C14 1.364(7) . ?
C14 C15 1.535(7) . ?
C15 C22 1.507(7) . ?
C15 C16 1.531(7) . ?
C15 C24 1.549(7) . ?
C16 C21 1.389(7) . ?
C16 C17 1.403(7) . ?
C17 C18 1.417(7) . ?
C17 C62 1.485(7) . ?
C18 C19 1.390(7) . ?
C18 C68 1.497(7) . ?
C19 C20 1.420(7) . ?
C19 C75 1.504(7) . ?
C20 C21 1.405(7) . ?
C20 C85 1.477(7) . ?
C21 N2 1.417(6) . ?
N2 C22 1.294(6) . ?
C24 C25 1.370(7) . ?
C24 C29 1.391(7) . ?
C25 C26 1.386(8) . ?
C26 C27 1.400(8) . ?
C27 C28 1.382(8) . ?
C27 C30 1.512(8) . ?
C28 C29 1.390(8) . ?
C31 C36 1.378(7) . ?
C31 C32 1.380(7) . ?
C32 C33 1.367(8) . ?
C33 C34 1.376(8) . ?
C34 C35 1.381(8) . ?
C34 C37 1.477(8) . ?
C35 C36 1.370(8) . ?
C37 C38 1.534(9) . ?
C39 C40 1.378(7) . ?
C39 C44 1.387(7) . ?
C40 C41 1.378(7) . ?
C41 C42 1.390(7) . ?
C42 C43 1.381(8) . ?
C42 C45 1.526(7) . ?
C43 C44 1.386(7) . ?
C45 C46 1.513(9) . ?
C45 C48 1.518(8) . ?
C45 C47 1.542(8) . ?
C49 C54 1.378(7) . ?
C49 C50 1.389(8) . ?
C50 C51 1.366(8) . ?
C51 C52 1.400(8) . ?
C52 O1 1.358(7) . ?
C52 C53 1.368(8) . ?
C53 C54 1.386(8) . ?
O1 C55 1.426(7) . ?
C56 C57 1.388(8) . ?
C56 C61 1.402(8) . ?
C57 C58 1.362(9) . ?
C58 C59 1.358(9) . ?
C59 C60 1.395(10) . ?
C60 C61 1.360(8) . ?
C62 C63 1.385(8) . ?
C62 C67 1.394(8) . ?
C63 C64 1.382(8) . ?
C64 C65 1.372(9) . ?
C65 C66 1.381(9) . ?
C66 C67 1.370(8) . ?
C68 C73 1.377(7) . ?
C68 C69 1.390(7) . ?
C69 C70 1.376(8) . ?
C70 C71 1.372(8) . ?
C71 C72 1.379(8) . ?
C71 O2 1.388(7) . ?
C72 C73 1.384(8) . ?
O2 C74 1.433(8) . ?
C75 C80 1.387(7) . ?
C75 C76 1.388(7) . ?
C76 C77 1.380(7) . ?
C77 C78 1.387(7) . ?
C78 C79 1.391(7) . ?
C78 C81 1.538(8) . ?
C79 C80 1.372(7) . ?
C81 C83 1.506(8) . ?
C81 C82 1.513(8) . ?
C81 C84 1.534(9) . ?
C85 C90 1.374(7) . ?
C85 C86 1.393(7) . ?
C86 C87 1.373(7) . ?
C87 C88 1.381(8) . ?
C88 C89 1.384(7) . ?
C88 C91 1.498(8) . ?
C89 C90 1.368(7) . ?
C91 C92 1.500(9) . ?
C93 C94 1.495(11) . ?
C94 O3 1.341(9) . ?
C95 C96 1.516(8) . ?
C96 C97 1.427(9) . ?
C97 C98 1.514(8) . ?
C98 C99 1.502(9) . ?

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 C8 110.7(5) . . ?
N1 C1 C22 128.4(5) . . ?
C8 C1 C22 120.9(5) . . ?
C1 N1 C2 107.7(5) . . ?
N1 C2 C7 109.5(5) . . ?
N1 C2 C3 127.1(5) . . ?
C7 C2 C3 123.3(5) . . ?
C4 C3 C2 116.9(5) . . ?
C4 C3 C31 124.4(5) . . ?
C2 C3 C31 118.6(5) . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 C39 115.9(5) . . ?
C5 C4 C39 123.5(5) . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 C49 117.3(5) . . ?
C4 C5 C49 120.8(5) . . ?
C5 C6 C7 118.0(5) . . ?
C5 C6 C56 122.3(5) . . ?
C7 C6 C56 119.5(5) . . ?
C2 C7 C6 118.8(5) . . ?
C2 C7 C8 105.8(5) . . ?
C6 C7 C8 135.2(5) . . ?
C1 C8 C7 105.8(5) . . ?
C1 C8 C9 118.4(5) . . ?
C7 C8 C9 133.8(5) . . ?
C10 C9 C14 117.1(5) . . ?
C10 C9 C8 124.8(5) . . ?
C14 C9 C8 117.8(5) . . ?
C9 C10 C11 122.9(6) . . ?
C12 C11 C10 120.6(6) . . ?
C11 C12 C13 117.4(5) . . ?
C11 C12 C23 121.9(6) . . ?
C13 C12 C23 120.8(6) . . ?
C14 C13 C12 123.4(6) . . ?
C13 C14 C9 118.6(5) . . ?
C13 C14 C15 124.4(5) . . ?
C9 C14 C15 117.0(5) . . ?
C22 C15 C16 98.8(4) . . ?
C22 C15 C14 108.5(4) . . ?
C16 C15 C14 121.2(4) . . ?
C22 C15 C24 106.9(4) . . ?
C16 C15 C24 110.0(4) . . ?
C14 C15 C24 110.0(4) . . ?
C21 C16 C17 120.3(5) . . ?
C21 C16 C15 106.2(5) . . ?
C17 C16 C15 133.3(5) . . ?
C16 C17 C18 117.2(5) . . ?
C16 C17 C62 123.7(5) . . ?
C18 C17 C62 119.0(5) . . ?
C19 C18 C17 121.4(5) . . ?
C19 C18 C68 117.9(5) . . ?
C17 C18 C68 120.7(5) . . ?
C18 C19 C20 121.8(5) . . ?
C18 C19 C75 118.8(5) . . ?
C20 C19 C75 119.4(5) . . ?
C21 C20 C19 115.4(5) . . ?
C21 C20 C85 121.4(5) . . ?
C19 C20 C85 123.2(5) . . ?
C16 C21 C20 123.6(5) . . ?
C16 C21 N2 113.0(5) . . ?
C20 C21 N2 123.3(5) . . ?
C22 N2 C21 105.5(4) . . ?
N2 C22 C1 128.5(5) . . ?
N2 C22 C15 116.0(5) . . ?
C1 C22 C15 115.5(5) . . ?
C25 C24 C29 117.8(5) . . ?
C25 C24 C15 123.4(5) . . ?
C29 C24 C15 118.8(5) . . ?
C24 C25 C26 121.8(6) . . ?
C25 C26 C27 120.7(6) . . ?
C28 C27 C26 117.6(5) . . ?
C28 C27 C30 120.6(6) . . ?
C26 C27 C30 121.8(6) . . ?
C27 C28 C29 121.1(6) . . ?
C28 C29 C24 121.1(6) . . ?
C36 C31 C32 116.8(5) . . ?
C36 C31 C3 120.9(5) . . ?
C32 C31 C3 122.2(5) . . ?
C33 C32 C31 121.7(5) . . ?
C32 C33 C34 122.0(6) . . ?
C33 C34 C35 115.9(6) . . ?
C33 C34 C37 122.7(6) . . ?
C35 C34 C37 121.3(6) . . ?
C36 C35 C34 122.6(6) . . ?
C35 C36 C31 120.9(5) . . ?
C34 C37 C38 114.4(6) . . ?
C40 C39 C44 116.3(5) . . ?
C40 C39 C4 120.3(5) . . ?
C44 C39 C4 123.2(5) . . ?
C41 C40 C39 122.3(5) . . ?
C40 C41 C42 121.5(5) . . ?
C43 C42 C41 116.0(5) . . ?
C43 C42 C45 124.1(5) . . ?
C41 C42 C45 119.8(5) . . ?
C42 C43 C44 122.3(5) . . ?
C43 C44 C39 121.2(5) . . ?
C46 C45 C48 110.1(5) . . ?
C46 C45 C42 107.9(5) . . ?
C48 C45 C42 111.6(4) . . ?
C46 C45 C47 108.6(5) . . ?
C48 C45 C47 106.6(5) . . ?
C42 C45 C47 112.0(5) . . ?
C54 C49 C50 117.1(5) . . ?
C54 C49 C5 123.7(5) . . ?
C50 C49 C5 118.9(5) . . ?
C51 C50 C49 121.8(6) . . ?
C50 C51 C52 120.3(6) . . ?
O1 C52 C53 124.7(6) . . ?
O1 C52 C51 116.7(5) . . ?
C53 C52 C51 118.6(6) . . ?
C52 C53 C54 120.4(6) . . ?
C49 C54 C53 121.8(6) . . ?
C52 O1 C55 116.8(5) . . ?
C57 C56 C61 116.9(6) . . ?
C57 C56 C6 123.7(5) . . ?
C61 C56 C6 119.5(5) . . ?
C58 C57 C56 121.3(6) . . ?
C59 C58 C57 121.6(7) . . ?
C58 C59 C60 118.6(7) . . ?
C61 C60 C59 120.2(7) . . ?
C60 C61 C56 121.4(6) . . ?
C63 C62 C67 117.5(5) . . ?
C63 C62 C17 122.5(5) . . ?
C67 C62 C17 120.0(5) . . ?
C64 C63 C62 121.1(6) . . ?
C65 C64 C63 120.5(6) . . ?
C64 C65 C66 119.3(6) . . ?
C67 C66 C65 120.2(6) . . ?
C66 C67 C62 121.4(6) . . ?
C73 C68 C69 117.2(5) . . ?
C73 C68 C18 123.1(5) . . ?
C69 C68 C18 119.8(5) . . ?
C70 C69 C68 121.6(5) . . ?
C71 C70 C69 119.5(5) . . ?
C70 C71 C72 120.8(5) . . ?
C70 C71 O2 114.9(6) . . ?
C72 C71 O2 124.4(6) . . ?
C71 C72 C73 118.5(6) . . ?
C68 C73 C72 122.5(5) . . ?
C71 O2 C74 116.9(5) . . ?
C80 C75 C76 116.8(5) . . ?
C80 C75 C19 120.8(5) . . ?
C76 C75 C19 122.2(5) . . ?
C77 C76 C75 121.3(5) . . ?
C76 C77 C78 121.9(5) . . ?
C77 C78 C79 116.5(5) . . ?
C77 C78 C81 123.2(5) . . ?
C79 C78 C81 120.1(5) . . ?
C80 C79 C78 121.6(5) . . ?
C79 C80 C75 121.8(5) . . ?
C83 C81 C82 109.7(5) . . ?
C83 C81 C84 109.2(5) . . ?
C82 C81 C84 108.3(5) . . ?
C83 C81 C78 110.9(5) . . ?
C82 C81 C78 111.7(5) . . ?
C84 C81 C78 107.0(5) . . ?
C90 C85 C86 118.3(5) . . ?
C90 C85 C20 121.7(5) . . ?
C86 C85 C20 120.0(5) . . ?
C87 C86 C85 119.9(5) . . ?
C86 C87 C88 122.4(5) . . ?
C87 C88 C89 116.5(5) . . ?
C87 C88 C91 122.0(5) . . ?
C89 C88 C91 121.6(5) . . ?
C90 C89 C88 122.2(5) . . ?
C89 C90 C85 120.7(5) . . ?
C88 C91 C92 110.9(5) . . ?
O3 C94 C93 116.6(8) . . ?
C97 C96 C95 119.5(10) . . ?
C96 C97 C98 120.1(10) . . ?
C99 C98 C97 115.8(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
C8 C1 N1 C2 3.4(6) . . . . ?
C22 C1 N1 C2 -175.2(5) . . . . ?
C1 N1 C2 C7 0.6(6) . . . . ?
C1 N1 C2 C3 -179.4(5) . . . . ?
N1 C2 C3 C4 -177.2(5) . . . . ?
C7 C2 C3 C4 2.8(7) . . . . ?
N1 C2 C3 C31 -0.8(8) . . . . ?
C7 C2 C3 C31 179.2(5) . . . . ?
C2 C3 C4 C5 4.2(7) . . . . ?
C31 C3 C4 C5 -171.9(5) . . . . ?
C2 C3 C4 C39 -176.9(4) . . . . ?
C31 C3 C4 C39 7.0(7) . . . . ?
C3 C4 C5 C6 -6.3(7) . . . . ?
C39 C4 C5 C6 174.8(5) . . . . ?
C3 C4 C5 C49 170.1(5) . . . . ?
C39 C4 C5 C49 -8.8(7) . . . . ?
C4 C5 C6 C7 1.3(7) . . . . ?
C49 C5 C6 C7 -175.3(5) . . . . ?
C4 C5 C6 C56 175.3(5) . . . . ?
C49 C5 C6 C56 -1.2(7) . . . . ?
N1 C2 C7 C6 172.2(4) . . . . ?
C3 C2 C7 C6 -7.8(7) . . . . ?
N1 C2 C7 C8 -4.0(5) . . . . ?
C3 C2 C7 C8 176.0(5) . . . . ?
C5 C6 C7 C2 5.5(7) . . . . ?
C56 C6 C7 C2 -168.7(5) . . . . ?
C5 C6 C7 C8 -179.6(5) . . . . ?
C56 C6 C7 C8 6.2(9) . . . . ?
N1 C1 C8 C7 -5.8(6) . . . . ?
C22 C1 C8 C7 172.9(4) . . . . ?
N1 C1 C8 C9 160.3(4) . . . . ?
C22 C1 C8 C9 -21.0(7) . . . . ?
C2 C7 C8 C1 5.9(5) . . . . ?
C6 C7 C8 C1 -169.5(6) . . . . ?
C2 C7 C8 C9 -157.1(6) . . . . ?
C6 C7 C8 C9 27.6(10) . . . . ?
C1 C8 C9 C10 -150.1(5) . . . . ?
C7 C8 C9 C10 11.2(9) . . . . ?
C1 C8 C9 C14 23.3(7) . . . . ?
C7 C8 C9 C14 -175.4(5) . . . . ?
C14 C9 C10 C11 -0.7(8) . . . . ?
C8 C9 C10 C11 172.8(5) . . . . ?
C9 C10 C11 C12 -0.7(9) . . . . ?
C10 C11 C12 C13 0.6(9) . . . . ?
C10 C11 C12 C23 179.9(6) . . . . ?
C11 C12 C13 C14 1.1(9) . . . . ?
C23 C12 C13 C14 -178.2(6) . . . . ?
C12 C13 C14 C9 -2.5(8) . . . . ?
C12 C13 C14 C15 174.6(5) . . . . ?
C10 C9 C14 C13 2.2(8) . . . . ?
C8 C9 C14 C13 -171.7(5) . . . . ?
C10 C9 C14 C15 -175.1(5) . . . . ?
C8 C9 C14 C15 11.0(7) . . . . ?
C13 C14 C15 C22 138.5(5) . . . . ?
C9 C14 C15 C22 -44.3(6) . . . . ?
C13 C14 C15 C16 25.4(8) . . . . ?
C9 C14 C15 C16 -157.4(5) . . . . ?
C13 C14 C15 C24 -104.9(6) . . . . ?
C9 C14 C15 C24 72.3(6) . . . . ?
C22 C15 C16 C21 5.4(5) . . . . ?
C14 C15 C16 C21 123.4(5) . . . . ?
C24 C15 C16 C21 -106.3(5) . . . . ?
C22 C15 C16 C17 179.8(5) . . . . ?
C14 C15 C16 C17 -62.2(8) . . . . ?
C24 C15 C16 C17 68.1(7) . . . . ?
C21 C16 C17 C18 -3.6(7) . . . . ?
C15 C16 C17 C18 -177.4(5) . . . . ?
C21 C16 C17 C62 175.9(5) . . . . ?
C15 C16 C17 C62 2.2(9) . . . . ?
C16 C17 C18 C19 5.9(7) . . . . ?
C62 C17 C18 C19 -173.7(5) . . . . ?
C16 C17 C18 C68 -173.0(5) . . . . ?
C62 C17 C18 C68 7.4(7) . . . . ?
C17 C18 C19 C20 -4.3(8) . . . . ?
C68 C18 C19 C20 174.6(5) . . . . ?
C17 C18 C19 C75 175.6(5) . . . . ?
C68 C18 C19 C75 -5.5(7) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C75 C19 C20 C21 -179.6(4) . . . . ?
C18 C19 C20 C85 179.5(5) . . . . ?
C75 C19 C20 C85 -0.4(7) . . . . ?
C17 C16 C21 C20 -0.3(8) . . . . ?
C15 C16 C21 C20 175.0(5) . . . . ?
C17 C16 C21 N2 -178.6(4) . . . . ?
C15 C16 C21 N2 -3.3(6) . . . . ?
C19 C20 C21 C16 2.0(7) . . . . ?
C85 C20 C21 C16 -177.2(5) . . . . ?
C19 C20 C21 N2 -179.9(4) . . . . ?
C85 C20 C21 N2 0.9(7) . . . . ?
C16 C21 N2 C22 -0.8(5) . . . . ?
C20 C21 N2 C22 -179.1(5) . . . . ?
C21 N2 C22 C1 -175.7(5) . . . . ?
C21 N2 C22 C15 4.9(5) . . . . ?
N1 C1 C22 N2 -16.9(9) . . . . ?
C8 C1 C22 N2 164.6(5) . . . . ?
N1 C1 C22 C15 162.4(5) . . . . ?
C8 C1 C22 C15 -16.0(7) . . . . ?
C16 C15 C22 N2 -6.6(5) . . . . ?
C14 C15 C22 N2 -133.9(5) . . . . ?
C24 C15 C22 N2 107.6(5) . . . . ?
C16 C15 C22 C1 173.9(4) . . . . ?
C14 C15 C22 C1 46.7(6) . . . . ?
C24 C15 C22 C1 -71.9(5) . . . . ?
C22 C15 C24 C25 124.4(5) . . . . ?
C16 C15 C24 C25 -129.3(5) . . . . ?
C14 C15 C24 C25 6.7(7) . . . . ?
C22 C15 C24 C29 -57.5(6) . . . . ?
C16 C15 C24 C29 48.8(6) . . . . ?
C14 C15 C24 C29 -175.2(5) . . . . ?
C29 C24 C25 C26 -0.8(8) . . . . ?
C15 C24 C25 C26 177.4(5) . . . . ?
C24 C25 C26 C27 0.7(9) . . . . ?
C25 C26 C27 C28 -0.4(9) . . . . ?
C25 C26 C27 C30 -178.6(5) . . . . ?
C26 C27 C28 C29 0.2(8) . . . . ?
C30 C27 C28 C29 178.5(5) . . . . ?
C27 C28 C29 C24 -0.4(8) . . . . ?
C25 C24 C29 C28 0.6(8) . . . . ?
C15 C24 C29 C28 -177.6(5) . . . . ?
C4 C3 C31 C36 75.8(7) . . . . ?
C2 C3 C31 C36 -100.3(6) . . . . ?
C4 C3 C31 C32 -102.1(7) . . . . ?
C2 C3 C31 C32 81.8(7) . . . . ?
C36 C31 C32 C33 -2.4(9) . . . . ?
C3 C31 C32 C33 175.6(6) . . . . ?
C31 C32 C33 C34 2.0(10) . . . . ?
C32 C33 C34 C35 0.4(9) . . . . ?
C32 C33 C34 C37 -177.7(6) . . . . ?
C33 C34 C35 C36 -2.4(9) . . . . ?
C37 C34 C35 C36 175.8(6) . . . . ?
C34 C35 C36 C31 2.0(9) . . . . ?
C32 C31 C36 C35 0.4(8) . . . . ?
C3 C31 C36 C35 -177.6(5) . . . . ?
C33 C34 C37 C38 112.5(7) . . . . ?
C35 C34 C37 C38 -65.5(8) . . . . ?
C3 C4 C39 C40 60.0(7) . . . . ?
C5 C4 C39 C40 -121.0(6) . . . . ?
C3 C4 C39 C44 -115.4(6) . . . . ?
C5 C4 C39 C44 63.6(7) . . . . ?
C44 C39 C40 C41 6.0(8) . . . . ?
C4 C39 C40 C41 -169.6(5) . . . . ?
C39 C40 C41 C42 -2.0(9) . . . . ?
C40 C41 C42 C43 -3.3(8) . . . . ?
C40 C41 C42 C45 173.6(5) . . . . ?
C41 C42 C43 C44 4.3(8) . . . . ?
C45 C42 C43 C44 -172.5(5) . . . . ?
C42 C43 C44 C39 -0.1(9) . . . . ?
C40 C39 C44 C43 -5.0(8) . . . . ?
C4 C39 C44 C43 170.5(5) . . . . ?
C43 C42 C45 C46 112.2(7) . . . . ?
C41 C42 C45 C46 -64.5(7) . . . . ?
C43 C42 C45 C48 -126.7(6) . . . . ?
C41 C42 C45 C48 56.7(7) . . . . ?
C43 C42 C45 C47 -7.4(8) . . . . ?
C41 C42 C45 C47 176.0(5) . . . . ?
C6 C5 C49 C54 -109.2(6) . . . . ?
C4 C5 C49 C54 74.3(7) . . . . ?
C6 C5 C49 C50 65.5(7) . . . . ?
C4 C5 C49 C50 -111.1(6) . . . . ?
C54 C49 C50 C51 2.1(9) . . . . ?
C5 C49 C50 C51 -172.9(5) . . . . ?
C49 C50 C51 C52 -0.5(9) . . . . ?
C50 C51 C52 O1 177.6(5) . . . . ?
C50 C51 C52 C53 -1.3(9) . . . . ?
O1 C52 C53 C54 -177.4(5) . . . . ?
C51 C52 C53 C54 1.5(9) . . . . ?
C50 C49 C54 C53 -1.9(9) . . . . ?
C5 C49 C54 C53 172.8(5) . . . . ?
C52 C53 C54 C49 0.2(9) . . . . ?
C53 C52 O1 C55 7.8(8) . . . . ?
C51 C52 O1 C55 -171.1(5) . . . . ?
C5 C6 C56 C57 57.6(7) . . . . ?
C7 C6 C56 C57 -128.5(6) . . . . ?
C5 C6 C56 C61 -122.1(6) . . . . ?
C7 C6 C56 C61 51.9(7) . . . . ?
C61 C56 C57 C58 -1.3(8) . . . . ?
C6 C56 C57 C58 179.1(5) . . . . ?
C56 C57 C58 C59 2.5(10) . . . . ?
C57 C58 C59 C60 -2.0(10) . . . . ?
C58 C59 C60 C61 0.4(10) . . . . ?
C59 C60 C61 C56 0.7(9) . . . . ?
C57 C56 C61 C60 -0.3(8) . . . . ?
C6 C56 C61 C60 179.4(5) . . . . ?
C16 C17 C62 C63 115.9(6) . . . . ?
C18 C17 C62 C63 -64.6(7) . . . . ?
C16 C17 C62 C67 -62.3(7) . . . . ?
C18 C17 C62 C67 117.2(6) . . . . ?
C67 C62 C63 C64 2.0(8) . . . . ?
C17 C62 C63 C64 -176.2(5) . . . . ?
C62 C63 C64 C65 -0.2(9) . . . . ?
C63 C64 C65 C66 -2.1(10) . . . . ?
C64 C65 C66 C67 2.4(10) . . . . ?
C65 C66 C67 C62 -0.5(9) . . . . ?
C63 C62 C67 C66 -1.7(8) . . . . ?
C17 C62 C67 C66 176.6(5) . . . . ?
C19 C18 C68 C73 113.8(6) . . . . ?
C17 C18 C68 C73 -67.3(7) . . . . ?
C19 C18 C68 C69 -65.2(7) . . . . ?
C17 C18 C68 C69 113.7(6) . . . . ?
C73 C68 C69 C70 0.1(9) . . . . ?
C18 C68 C69 C70 179.2(5) . . . . ?
C68 C69 C70 C71 -0.4(10) . . . . ?
C69 C70 C71 C72 0.2(10) . . . . ?
C69 C70 C71 O2 -179.9(6) . . . . ?
C70 C71 C72 C73 0.3(10) . . . . ?
O2 C71 C72 C73 -179.6(6) . . . . ?
C69 C68 C73 C72 0.4(9) . . . . ?
C18 C68 C73 C72 -178.6(6) . . . . ?
C71 C72 C73 C68 -0.6(10) . . . . ?
C70 C71 O2 C74 171.6(7) . . . . ?
C72 C71 O2 C74 -8.5(10) . . . . ?
C18 C19 C75 C80 -63.4(7) . . . . ?
C20 C19 C75 C80 116.4(6) . . . . ?
C18 C19 C75 C76 111.2(6) . . . . ?
C20 C19 C75 C76 -68.9(7) . . . . ?
C80 C75 C76 C77 2.8(8) . . . . ?
C19 C75 C76 C77 -172.1(5) . . . . ?
C75 C76 C77 C78 -0.6(8) . . . . ?
C76 C77 C78 C79 -1.5(8) . . . . ?
C76 C77 C78 C81 173.8(5) . . . . ?
C77 C78 C79 C80 1.4(8) . . . . ?
C81 C78 C79 C80 -174.1(5) . . . . ?
C78 C79 C80 C75 0.8(9) . . . . ?
C76 C75 C80 C79 -2.9(8) . . . . ?
C19 C75 C80 C79 172.0(5) . . . . ?
C77 C78 C81 C83 137.7(6) . . . . ?
C79 C78 C81 C83 -47.2(7) . . . . ?
C77 C78 C81 C82 15.0(8) . . . . ?
C79 C78 C81 C82 -169.8(5) . . . . ?
C77 C78 C81 C84 -103.3(6) . . . . ?
C79 C78 C81 C84 71.8(7) . . . . ?
C21 C20 C85 C90 114.3(6) . . . . ?
C19 C20 C85 C90 -64.9(7) . . . . ?
C21 C20 C85 C86 -64.8(7) . . . . ?
C19 C20 C85 C86 116.0(6) . . . . ?
C90 C85 C86 C87 1.1(8) . . . . ?
C20 C85 C86 C87 -179.7(5) . . . . ?
C85 C86 C87 C88 -2.3(9) . . . . ?
C86 C87 C88 C89 1.0(9) . . . . ?
C86 C87 C88 C91 -179.2(6) . . . . ?
C87 C88 C89 C90 1.5(8) . . . . ?
C91 C88 C89 C90 -178.4(5) . . . . ?
C88 C89 C90 C85 -2.7(8) . . . . ?
C86 C85 C90 C89 1.3(8) . . . . ?
C20 C85 C90 C89 -177.8(5) . . . . ?
C87 C88 C91 C92 -89.5(7) . . . . ?
C89 C88 C91 C92 90.4(7) . . . . ?
C95 C96 C97 C98 178.5(13) . . . . ?
C96 C97 C98 C99 85.4(19) . . . . ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057


_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1580599'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-05-03 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         ?
_chemical_formula_sum            'C56 H47 N3 O5 S'
_chemical_formula_weight         874.02

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.816(5)
_cell_length_b                   28.030(8)
_cell_length_c                   12.060(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.633(7)
_cell_angle_gamma                90
_cell_volume                     4588(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123

_cell_measurement_reflns_used    8218

_cell_measurement_theta_min      3.0

_cell_measurement_theta_max      25.3


_exptl_crystal_description       Block

_exptl_crystal_colour            Red

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.847

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku CrystalClear-SM Expert 2.1 b29
;

_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            48650
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.002
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8068
_reflns_number_gt                6415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_structure_solution    SIR-97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0461P)²+1.5038P] 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_number_reflns         8068
_refine_ls_number_parameters     708
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.047
_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
N1 N 0.10356(8) 0.24276(4) 0.52256(10) 0.0219(3) Uani 1 1 d . . . . .
C1 C 0.05068(10) 0.28354(5) 0.46613(12) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.11125(10) 0.32262(5) 0.50202(12) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.20635(10) 0.30579(5) 0.58796(12) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.29447(10) 0.32895(5) 0.66335(12) 0.0226(3) Uani 1 1 d . . . . .
C5 C 0.37375(10) 0.30111(5) 0.74000(12) 0.0238(3) Uani 1 1 d . . . . .
C6 C 0.36802(10) 0.25069(5) 0.73613(12) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.28113(10) 0.22696(5) 0.66250(12) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.20015(10) 0.25580(5) 0.59523(12) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.06346(10) 0.19611(5) 0.50425(12) 0.0225(3) Uani 1 1 d . . . . .
C10 C 0.02415(10) 0.17436(5) 0.39053(12) 0.0249(3) Uani 1 1 d . . . . .
C11 C -0.01993(11) 0.12987(5) 0.37330(13) 0.0291(3) Uani 1 1 d . . . . .
H1 H -0.048039 0.115771 0.295195 0.035 Uiso 1 1 calc R U . . .
C12 C -0.02170(11) 0.10670(5) 0.47326(13) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.01827(11) 0.12642(5) 0.58820(13) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.017274 0.109426 0.655851 0.036 Uiso 1 1 calc R U . . .
C14 C 0.05960(10) 0.17135(5) 0.60213(13) 0.0252(3) Uani 1 1 d . . . . .
H3 H 0.085900 0.185618 0.680117 0.030 Uiso 1 1 calc R U . . .
N2 N 0.03080(10) 0.19641(5) 0.28307(11) 0.0337(3) Uani 1 1 d . . . . .
O1 O -0.03393(11) 0.18639(5) 0.18448(10) 0.0573(4) Uani 1 1 d . . . . .
O2 O 0.10051(9) 0.22257(4) 0.29707(10) 0.0400(3) Uani 1 1 d . . . . .
N3 N -0.06828(10) 0.05937(5) 0.45673(12) 0.0394(3) Uani 1 1 d . . . . .
O3 O -0.11043(9) 0.04443(4) 0.35323(10) 0.0452(3) Uani 1 1 d . . . . .
O4 O -0.06302(11) 0.03766(4) 0.54717(11) 0.0613(4) Uani 1 1 d . . . . .
C15 C -0.05568(10) 0.28042(4) 0.38880(12) 0.0232(3) Uani 1 1 d . . . . .
C16 C -0.09910(11) 0.29745(5) 0.27178(14) 0.0372(4) Uani 1 1 d D U . . .
H4 H -0.064783 0.311428 0.228202 0.045 Uiso 1 1 calc R U . A 1
S1 S -0.22508(9) 0.28954(4) 0.21648(13) 0.0467(3) Uani 0.668(3) 1 d D . P B 1
C17 C -0.2191(5) 0.26229(16) 0.3508(5) 0.057(2) Uani 0.668(3) 1 d D U P B 1
H49 H -0.273621 0.250766 0.365527 0.068 Uiso 0.668(3) 1 calc R U P B 1
C18 C -0.12576(11) 0.26063(5) 0.42751(14) 0.0306(3) Uani 1 1 d D U . . .
H5 H -0.106593 0.246712 0.505452 0.037 Uiso 1 1 calc R U . B 1
C19 C -0.1916(9) 0.2934(2) 0.2142(10) 0.069(4) Uani 0.332(3) 1 d D U P B 2
H50 H -0.229051 0.304538 0.134459 0.083 Uiso 0.332(3) 1 calc R U P B 2
S2 S -0.2378(2) 0.26375(8) 0.3070(3) 0.0470(8) Uani 0.332(3) 1 d D . P B 2
C20 C 0.08104(10) 0.37172(5) 0.45626(12) 0.0215(3) Uani 1 1 d . . . . .
C21 C -0.00368(10) 0.39274(5) 0.45781(12) 0.0255(3) Uani 1 1 d . . . . .
H6 H -0.042435 0.375751 0.491092 0.031 Uiso 1 1 calc R U . . .
C22 C -0.03215(11) 0.43824(5) 0.41129(13) 0.0282(3) Uani 1 1 d . . . . .
H7 H -0.090541 0.451663 0.412740 0.034 Uiso 1 1 calc R U . . .
C23 C 0.02272(11) 0.46462(5) 0.36261(12) 0.0274(3) Uani 1 1 d . . . . .
C24 C 0.10760(11) 0.44358(5) 0.36148(13) 0.0276(3) Uani 1 1 d . . . . .
H8 H 0.146738 0.460776 0.329103 0.033 Uiso 1 1 calc R U . . .
C25 C 0.13592(10) 0.39805(5) 0.40671(12) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.193740 0.384475 0.403981 0.029 Uiso 1 1 calc R U . . .
C26 C -0.00861(13) 0.51389(5) 0.31153(15) 0.0379(4) Uani 1 1 d . . . . .
H10 H -0.049989 0.511552 0.224786 0.057 Uiso 1 1 calc R U . . .
H11 H 0.049870 0.533100 0.323653 0.057 Uiso 1 1 calc R U . . .
H12 H -0.046072 0.529046 0.352952 0.057 Uiso 1 1 calc R U . . .
C27 C 0.30424(10) 0.38185(5) 0.66432(13) 0.0260(3) Uani 1 1 d . . . . .
C28 C 0.24800(11) 0.41069(5) 0.70602(14) 0.0325(4) Uani 1 1 d . . . . .
H13 H 0.200068 0.396696 0.729724 0.039 Uiso 1 1 calc R U . . .
C29 C 0.26146(13) 0.45963(6) 0.71318(17) 0.0469(5) Uani 1 1 d . . . . .
H14 H 0.223791 0.479023 0.743372 0.056 Uiso 1 1 calc R U . . .
C30 C 0.32924(14) 0.48025(6) 0.6767(2) 0.0586(6) Uani 1 1 d . . . . .
H15 H 0.338571 0.513834 0.682204 0.070 Uiso 1 1 calc R U . . .
C31 C 0.38386(13) 0.45225(6) 0.6319(2) 0.0527(5) Uani 1 1 d . . . . .
H16 H 0.429376 0.466652 0.604751 0.063 Uiso 1 1 calc R U . . .
C32 C 0.37209(11) 0.40314(6) 0.62681(15) 0.0358(4) Uani 1 1 d . . . . .
H17 H 0.410581 0.383898 0.597507 0.043 Uiso 1 1 calc R U . . .
C33 C 0.4686(4) 0.3232(3) 0.8223(6) 0.0240(12) Uani 0.707(5) 1 d D . P C 1
C34 C 0.4704(3) 0.35544(19) 0.9114(5) 0.0274(10) Uani 0.707(5) 1 d D . P C 1
H51 H 0.410838 0.361986 0.920523 0.033 Uiso 0.707(5) 1 calc R U P C 1
C35 C 0.5565(3) 0.37837(11) 0.9873(3) 0.0284(8) Uani 0.707(5) 1 d D . P C 1
H52 H 0.555655 0.399941 1.047677 0.034 Uiso 0.707(5) 1 calc R U P C 1
C36 C 0.6430(2) 0.36930(13) 0.9737(3) 0.0266(8) Uani 0.707(5) 1 d D . P C 1
C37 C 0.6441(2) 0.33639(13) 0.8882(3) 0.0275(8) Uani 0.707(5) 1 d D . P C 1
H53 H 0.704074 0.329335 0.880675 0.033 Uiso 0.707(5) 1 calc R U P C 1
C38 C 0.5579(3) 0.3138(2) 0.8140(5) 0.0249(8) Uani 0.707(5) 1 d D . P C 1
H54 H 0.559683 0.291408 0.755877 0.030 Uiso 0.707(5) 1 calc R U P C 1
O5 O 0.73265(17) 0.39022(7) 1.03948(17) 0.0389(7) Uani 0.707(5) 1 d D . P C 1
C39 C 0.7381(3) 0.42218(11) 1.1337(3) 0.0440(8) Uani 0.707(5) 1 d D . P C 1
H55 H 0.805338 0.434573 1.173373 0.066 Uiso 0.707(5) 1 calc R U P C 1
H56 H 0.692275 0.448737 1.099470 0.066 Uiso 0.707(5) 1 calc R U P C 1
H57 H 0.720340 0.405234 1.193214 0.066 Uiso 0.707(5) 1 calc R U P C 1
C40 C 0.4592(7) 0.3291(6) 0.8370(12) 0.015(3) Uani 0.293(5) 1 d D . P C 2
C41 C 0.4441(6) 0.3576(4) 0.9220(10) 0.021(2) Uani 0.293(5) 1 d D . P C 2
H58 H 0.379899 0.360413 0.920968 0.025 Uiso 0.293(5) 1 calc R U P C 2
C42 C 0.5223(6) 0.3822(3) 1.0088(7) 0.0290(19) Uani 0.293(5) 1 d D . P C 2
H59 H 0.511635 0.401374 1.067379 0.035 Uiso 0.293(5) 1 calc R U P C 2
C43 C 0.6156(6) 0.3783(2) 1.0093(7) 0.0281(19) Uani 0.293(5) 1 d D . P C 2
C44 C 0.6326(5) 0.3493(3) 0.9270(8) 0.025(2) Uani 0.293(5) 1 d D . P C 2
H60 H 0.697065 0.346236 0.928904 0.030 Uiso 0.293(5) 1 calc R U P C 2
C45 C 0.5539(7) 0.3245(5) 0.8413(10) 0.026(2) Uani 0.293(5) 1 d D . P C 2
H61 H 0.565254 0.304187 0.785062 0.031 Uiso 0.293(5) 1 calc R U P C 2
O6 O 0.6868(4) 0.40441(18) 1.0978(4) 0.0457(18) Uani 0.293(5) 1 d D . P C 2
C46 C 0.7793(6) 0.4083(3) 1.0882(10) 0.051(2) Uani 0.293(5) 1 d D . P C 2
H62 H 0.824364 0.427493 1.155478 0.077 Uiso 0.293(5) 1 calc R U P C 2
H63 H 0.807191 0.376377 1.091160 0.077 Uiso 0.293(5) 1 calc R U P C 2
H64 H 0.769819 0.423635 1.011314 0.077 Uiso 0.293(5) 1 calc R U P C 2
C47 C 0.45416(10) 0.22078(5) 0.81238(13) 0.0248(3) Uani 1 1 d . . . . .
C48 C 0.48480(11) 0.21873(5) 0.93693(13) 0.0318(3) Uani 1 1 d . . . . .
H18 H 0.455704 0.239374 0.975817 0.038 Uiso 1 1 calc R U . . .
C49 C 0.55735(11) 0.18696(6) 1.00552(14) 0.0346(4) Uani 1 1 d . . . . .
H19 H 0.576773 0.186233 1.090743 0.041 Uiso 1 1 calc R U . . .
C50 C 0.60258(10) 0.15608(5) 0.95316(14) 0.0309(3) Uani 1 1 d . . . . .
C51 C 0.57405(11) 0.15977(6) 0.82847(15) 0.0334(4) Uani 1 1 d . . . . .
H20 H 0.605043 0.140068 0.789964 0.040 Uiso 1 1 calc R U . . .
C52 C 0.50164(10) 0.19144(5) 0.75925(14) 0.0294(3) Uani 1 1 d . . . . .
H21 H 0.484102 0.193186 0.674465 0.035 Uiso 1 1 calc R U . . .
C53 C 0.67433(12) 0.11745(6) 1.02694(16) 0.0430(4) Uani 1 1 d D . . . .
C54 C 0.7155(3) 0.12660(16) 1.1633(2) 0.0672(13) Uani 0.800(10) 1 d D . P D 1
H22 H 0.660945 0.131113 1.188633 0.101 Uiso 0.800(10) 1 calc R U P D 1
H23 H 0.755324 0.099220 1.206289 0.101 Uiso 0.800(10) 1 calc R U P D 1
H24 H 0.756638 0.155331 1.182462 0.101 Uiso 0.800(10) 1 calc R U P D 1
C55 C 0.7586(3) 0.11048(17) 0.9878(5) 0.0529(10) Uani 0.800(10) 1 d D . P D 1
H25 H 0.802644 0.085485 1.037289 0.079 Uiso 0.800(10) 1 calc R U P D 1
H26 H 0.732395 0.101028 0.902431 0.079 Uiso 0.800(10) 1 calc R U P D 1
H27 H 0.795335 0.140403 0.998355 0.079 Uiso 0.800(10) 1 calc R U P D 1
C56 C 0.6137(2) 0.06993(10) 1.0037(5) 0.0535(10) Uani 0.800(10) 1 d D . P D 1
H28 H 0.558871 0.073961 1.028694 0.080 Uiso 0.800(10) 1 calc R U P D 1
H29 H 0.587853 0.062054 0.917353 0.080 Uiso 0.800(10) 1 calc R U P D 1
H30 H 0.656580 0.044067 1.050587 0.080 Uiso 0.800(10) 1 calc R U P D 1
C57 C 0.7394(14) 0.1020(8) 0.9596(19) 0.065(7) Uani 0.200(10) 1 d D U P D 2
H31 H 0.768585 0.130329 0.939327 0.098 Uiso 0.200(10) 1 calc R U P D 2
H32 H 0.791979 0.080875 1.011708 0.098 Uiso 0.200(10) 1 calc R U P D 2
H33 H 0.698843 0.085099 0.885066 0.098 Uiso 0.200(10) 1 calc R U P D 2
C58 C 0.7480(9) 0.1463(5) 1.1392(13) 0.070(4) Uani 0.200(10) 1 d D U P D 2
H34 H 0.779417 0.171584 1.111005 0.105 Uiso 0.200(10) 1 calc R U P D 2
H35 H 0.711769 0.160597 1.183330 0.105 Uiso 0.200(10) 1 calc R U P D 2
H36 H 0.798633 0.124706 1.193064 0.105 Uiso 0.200(10) 1 calc R U P D 2
C59 C 0.6249(9) 0.0790(5) 1.0639(16) 0.057(4) Uani 0.200(10) 1 d D U P D 2
H37 H 0.673697 0.055134 1.110777 0.085 Uiso 0.200(10) 1 calc R U P D 2
H38 H 0.592575 0.092216 1.113773 0.085 Uiso 0.200(10) 1 calc R U P D 2
H39 H 0.575523 0.063867 0.991802 0.085 Uiso 0.200(10) 1 calc R U P D 2
C60 C 0.27920(10) 0.17379(5) 0.65431(13) 0.0239(3) Uani 1 1 d . . . . .
C61 C 0.29728(10) 0.14500(5) 0.75515(13) 0.0268(3) Uani 1 1 d . . . . .
H40 H 0.306355 0.159288 0.830310 0.032 Uiso 1 1 calc R U . . .
C62 C 0.30223(11) 0.09578(5) 0.74738(15) 0.0321(3) Uani 1 1 d . . . . .
H41 H 0.315190 0.076924 0.817567 0.039 Uiso 1 1 calc R U . . .
C63 C 0.28858(12) 0.07355(5) 0.63890(15) 0.0352(4) Uani 1 1 d . . . . .
C64 C 0.26827(12) 0.10232(5) 0.53754(15) 0.0347(4) Uani 1 1 d . . . . .
H42 H 0.257003 0.087898 0.461847 0.042 Uiso 1 1 calc R U . . .
C65 C 0.26416(10) 0.15155(5) 0.54486(13) 0.0281(3) Uani 1 1 d . . . . .
H43 H 0.250954 0.170355 0.474537 0.034 Uiso 1 1 calc R U . . .
C66 C 0.30090(15) 0.02034(6) 0.63133(19) 0.0513(5) Uani 1 1 d . . . . .
H44 H 0.247464 0.007914 0.557188 0.062 Uiso 1 1 calc R U . . .
H45 H 0.295169 0.004755 0.701888 0.062 Uiso 1 1 calc R U . . .
C67 C 0.39968(17) 0.00781(8) 0.6290(3) 0.0903(9) Uani 1 1 d . . . . .
H46 H 0.402880 0.020434 0.554849 0.135 Uiso 1 1 calc R U . . .
H47 H 0.407348 -0.026950 0.630905 0.135 Uiso 1 1 calc R U . . .
H48 H 0.452661 0.021833 0.699611 0.135 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
N1 C8 1.3944(17) . ?
N1 C1 1.3987(17) . ?
N1 C9 1.4165(18) . ?
C1 C2 1.3716(19) . ?
C1 C15 1.477(2) . ?
C2 C3 1.4530(19) . ?
C2 C20 1.4835(19) . ?
C3 C8 1.4090(19) . ?
C3 C4 1.4146(19) . ?
C4 C5 1.4045(19) . ?
C4 C27 1.489(2) . ?
C5 C6 1.415(2) . ?
C5 C33 1.492(5) . ?
C5 C40 1.549(8) . ?
C6 C7 1.404(2) . ?
C6 C47 1.4954(19) . ?
C7 C8 1.4039(19) . ?
C7 C60 1.493(2) . ?
C9 C14 1.390(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.384(2) . ?
C10 N2 1.4744(19) . ?
C11 C12 1.379(2) . ?
C12 C13 1.385(2) . ?
C12 N3 1.4715(19) . ?
C13 C14 1.381(2) . ?
N2 O2 1.2219(17) . ?
N2 O1 1.2239(17) . ?
N3 O4 1.2239(18) . ?
N3 O3 1.2241(17) . ?
C15 C16 1.380(2) . ?
C15 C18 1.411(2) . ?
C16 C19 1.269(12) . ?
C16 S1 1.7263(19) . ?
S1 C17 1.761(6) . ?
C17 C18 1.321(7) . ?
C18 S2 1.715(3) . ?
C19 S2 1.740(9) . ?
C20 C21 1.394(2) . ?
C20 C25 1.397(2) . ?
C21 C22 1.389(2) . ?
C22 C23 1.391(2) . ?
C23 C24 1.394(2) . ?
C23 C26 1.508(2) . ?
C24 C25 1.385(2) . ?
C27 C32 1.391(2) . ?
C27 C28 1.392(2) . ?
C28 C29 1.384(2) . ?
C29 C30 1.375(3) . ?
C30 C31 1.383(3) . ?
C31 C32 1.386(2) . ?
C33 C38 1.391(5) . ?
C33 C34 1.395(5) . ?
C34 C35 1.394(5) . ?
C35 C36 1.380(4) . ?
C36 O5 1.376(4) . ?
C36 C37 1.388(4) . ?
C37 C38 1.384(5) . ?
O5 C39 1.424(4) . ?
C40 C41 1.387(8) . ?
C40 C45 1.389(8) . ?
C41 C42 1.392(8) . ?
C42 C43 1.385(7) . ?
C43 O6 1.372(7) . ?
C43 C44 1.382(7) . ?
C44 C45 1.395(8) . ?
O6 C46 1.424(8) . ?
C47 C48 1.385(2) . ?
C47 C52 1.394(2) . ?
C48 C49 1.386(2) . ?
C49 C50 1.391(2) . ?
C50 C51 1.393(2) . ?
C50 C53 1.528(2) . ?
C51 C52 1.385(2) . ?
C53 C59 1.470(8) . ?
C53 C55 1.514(3) . ?
C53 C54 1.529(3) . ?
C53 C57 1.551(9) . ?
C53 C56 1.568(3) . ?
C53 C58 1.580(8) . ?
C60 C61 1.393(2) . ?
C60 C65 1.395(2) . ?
C61 C62 1.387(2) . ?
C62 C63 1.389(2) . ?
C63 C64 1.393(2) . ?
C63 C66 1.510(2) . ?
C64 C65 1.385(2) . ?
C66 C67 1.517(3) . ?

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
C8 N1 C1 108.97(11) . . ?
C8 N1 C9 126.93(11) . . ?
C1 N1 C9 124.09(11) . . ?
C2 C1 N1 109.34(12) . . ?
C2 C1 C15 130.09(12) . . ?
N1 C1 C15 120.43(11) . . ?
C1 C2 C3 106.89(12) . . ?
C1 C2 C20 124.18(12) . . ?
C3 C2 C20 128.92(12) . . ?
C8 C3 C4 118.86(12) . . ?
C8 C3 C2 107.37(11) . . ?
C4 C3 C2 133.68(13) . . ?
C5 C4 C3 118.74(12) . . ?
C5 C4 C27 119.67(12) . . ?
C3 C4 C27 121.58(12) . . ?
C4 C5 C6 120.65(12) . . ?
C4 C5 C33 121.6(3) . . ?
C6 C5 C33 117.7(3) . . ?
C4 C5 C40 115.5(6) . . ?
C6 C5 C40 123.4(7) . . ?
C7 C6 C5 121.43(12) . . ?
C7 C6 C47 117.60(12) . . ?
C5 C6 C47 120.96(12) . . ?
C8 C7 C6 116.56(12) . . ?
C8 C7 C60 123.19(12) . . ?
C6 C7 C60 120.20(12) . . ?
N1 C8 C7 129.50(12) . . ?
N1 C8 C3 107.32(11) . . ?
C7 C8 C3 123.14(12) . . ?
C14 C9 C10 118.23(13) . . ?
C14 C9 N1 119.07(12) . . ?
C10 C9 N1 122.65(12) . . ?
C11 C10 C9 121.76(13) . . ?
C11 C10 N2 116.08(12) . . ?
C9 C10 N2 122.12(13) . . ?
C12 C11 C10 117.80(13) . . ?
C11 C12 C13 122.44(14) . . ?
C11 C12 N3 118.59(13) . . ?
C13 C12 N3 118.97(13) . . ?
C14 C13 C12 118.46(14) . . ?
C13 C14 C9 121.27(13) . . ?
O2 N2 O1 124.18(13) . . ?
O2 N2 C10 118.74(12) . . ?
O1 N2 C10 117.08(13) . . ?
O4 N3 O3 124.25(13) . . ?
O4 N3 C12 117.95(13) . . ?
O3 N3 C12 117.80(13) . . ?
C16 C15 C18 111.77(13) . . ?
C16 C15 C1 124.53(13) . . ?
C18 C15 C1 123.68(13) . . ?
C19 C16 C15 119.1(5) . . ?
C15 C16 S1 109.83(13) . . ?
C16 S1 C17 93.0(3) . . ?
C18 C17 S1 108.2(5) . . ?
C17 C18 C15 117.2(3) . . ?
C15 C18 S2 106.89(16) . . ?
C16 C19 S2 107.9(8) . . ?
C18 S2 C19 94.2(5) . . ?
C21 C20 C25 117.64(13) . . ?
C21 C20 C2 121.76(12) . . ?
C25 C20 C2 120.58(12) . . ?
C22 C21 C20 120.81(13) . . ?
C21 C22 C23 121.62(14) . . ?
C22 C23 C24 117.47(13) . . ?
C22 C23 C26 121.54(14) . . ?
C24 C23 C26 120.98(14) . . ?
C25 C24 C23 121.20(13) . . ?
C24 C25 C20 121.26(13) . . ?
C32 C27 C28 118.92(14) . . ?
C32 C27 C4 120.34(13) . . ?
C28 C27 C4 120.71(13) . . ?
C29 C28 C27 120.40(16) . . ?
C30 C29 C28 120.14(17) . . ?
C29 C30 C31 120.21(16) . . ?
C30 C31 C32 119.89(17) . . ?
C31 C32 C27 120.39(16) . . ?
C38 C33 C34 116.9(4) . . ?
C38 C33 C5 122.8(4) . . ?
C34 C33 C5 120.2(4) . . ?
C35 C34 C33 122.3(4) . . ?
C36 C35 C34 119.1(3) . . ?
O5 C36 C35 125.5(3) . . ?
O5 C36 C37 114.6(3) . . ?
C35 C36 C37 119.9(3) . . ?
C38 C37 C36 120.1(3) . . ?
C37 C38 C33 121.6(3) . . ?
C36 O5 C39 117.5(4) . . ?
C41 C40 C45 119.1(6) . . ?
C41 C40 C5 121.6(7) . . ?
C45 C40 C5 119.3(7) . . ?
C40 C41 C42 120.6(6) . . ?
C43 C42 C41 119.5(5) . . ?
O6 C43 C44 124.6(8) . . ?
O6 C43 C42 114.6(7) . . ?
C44 C43 C42 120.8(5) . . ?
C43 C44 C45 119.2(5) . . ?
C40 C45 C44 120.8(6) . . ?
C43 O6 C46 116.2(9) . . ?
C48 C47 C52 117.88(13) . . ?
C48 C47 C6 121.19(13) . . ?
C52 C47 C6 120.77(13) . . ?
C47 C48 C49 120.83(14) . . ?
C48 C49 C50 121.90(15) . . ?
C49 C50 C51 116.79(14) . . ?
C49 C50 C53 121.71(15) . . ?
C51 C50 C53 121.35(14) . . ?
C52 C51 C50 121.65(14) . . ?
C51 C52 C47 120.86(14) . . ?
C59 C53 C50 112.4(5) . . ?
C55 C53 C50 112.2(2) . . ?
C55 C53 C54 109.5(3) . . ?
C50 C53 C54 113.07(16) . . ?
C59 C53 C57 116.4(9) . . ?
C50 C53 C57 109.0(9) . . ?
C55 C53 C56 108.6(3) . . ?
C50 C53 C56 106.44(16) . . ?
C54 C53 C56 106.7(2) . . ?
C59 C53 C58 111.9(6) . . ?
C50 C53 C58 102.5(5) . . ?
C57 C53 C58 103.3(8) . . ?
C61 C60 C65 117.97(13) . . ?
C61 C60 C7 121.91(13) . . ?
C65 C60 C7 120.03(13) . . ?
C62 C61 C60 120.95(14) . . ?
C61 C62 C63 121.23(14) . . ?
C62 C63 C64 117.74(14) . . ?
C62 C63 C66 121.66(15) . . ?
C64 C63 C66 120.52(16) . . ?
C65 C64 C63 121.35(15) . . ?
C64 C65 C60 120.74(14) . . ?
C63 C66 C67 111.78(16) . . ?

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
C8 N1 C1 C2 -0.53(15) . . . . ?
C9 N1 C1 C2 -179.15(12) . . . . ?
C8 N1 C1 C15 -176.58(12) . . . . ?
C9 N1 C1 C15 4.80(19) . . . . ?
N1 C1 C2 C3 -1.61(15) . . . . ?
C15 C1 C2 C3 173.93(13) . . . . ?
N1 C1 C2 C20 177.38(12) . . . . ?
C15 C1 C2 C20 -7.1(2) . . . . ?
C1 C2 C3 C8 3.13(15) . . . . ?
C20 C2 C3 C8 -175.79(13) . . . . ?
C1 C2 C3 C4 -173.33(15) . . . . ?
C20 C2 C3 C4 7.8(2) . . . . ?
C8 C3 C4 C5 2.00(19) . . . . ?
C2 C3 C4 C5 178.15(14) . . . . ?
C8 C3 C4 C27 -177.11(13) . . . . ?
C2 C3 C4 C27 -1.0(2) . . . . ?
C3 C4 C5 C6 4.2(2) . . . . ?
C27 C4 C5 C6 -176.70(13) . . . . ?
C3 C4 C5 C33 -179.6(3) . . . . ?
C27 C4 C5 C33 -0.5(3) . . . . ?
C3 C4 C5 C40 -168.4(6) . . . . ?
C27 C4 C5 C40 10.7(6) . . . . ?
C4 C5 C6 C7 -4.6(2) . . . . ?
C33 C5 C6 C7 179.0(3) . . . . ?
C40 C5 C6 C7 167.4(6) . . . . ?
C4 C5 C6 C47 176.50(13) . . . . ?
C33 C5 C6 C47 0.2(3) . . . . ?
C40 C5 C6 C47 -11.5(6) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C47 C6 C7 C8 177.67(12) . . . . ?
C5 C6 C7 C60 176.12(13) . . . . ?
C47 C6 C7 C60 -4.98(19) . . . . ?
C1 N1 C8 C7 -175.45(13) . . . . ?
C9 N1 C8 C7 3.1(2) . . . . ?
C1 N1 C8 C3 2.52(14) . . . . ?
C9 N1 C8 C3 -178.91(12) . . . . ?
C6 C7 C8 N1 -174.58(13) . . . . ?
C60 C7 C8 N1 8.2(2) . . . . ?
C6 C7 C8 C3 7.7(2) . . . . ?
C60 C7 C8 C3 -169.52(13) . . . . ?
C4 C3 C8 N1 173.64(12) . . . . ?
C2 C3 C8 N1 -3.44(15) . . . . ?
C4 C3 C8 C7 -8.2(2) . . . . ?
C2 C3 C8 C7 174.68(12) . . . . ?
C8 N1 C9 C14 63.34(19) . . . . ?
C1 N1 C9 C14 -118.29(15) . . . . ?
C8 N1 C9 C10 -119.00(15) . . . . ?
C1 N1 C9 C10 59.36(19) . . . . ?
C14 C9 C10 C11 1.6(2) . . . . ?
N1 C9 C10 C11 -176.13(13) . . . . ?
C14 C9 C10 N2 -175.82(13) . . . . ?
N1 C9 C10 N2 6.5(2) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
N2 C10 C11 C12 175.80(13) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C10 C11 C12 N3 179.98(13) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
N3 C12 C13 C14 -178.41(14) . . . . ?
C12 C13 C14 C9 -1.5(2) . . . . ?
C10 C9 C14 C13 0.1(2) . . . . ?
N1 C9 C14 C13 177.85(13) . . . . ?
C11 C10 N2 O2 -148.54(14) . . . . ?
C9 C10 N2 O2 29.0(2) . . . . ?
C11 C10 N2 O1 30.2(2) . . . . ?
C9 C10 N2 O1 -152.31(15) . . . . ?
C11 C12 N3 O4 174.72(16) . . . . ?
C13 C12 N3 O4 -5.6(2) . . . . ?
C11 C12 N3 O3 -5.8(2) . . . . ?
C13 C12 N3 O3 173.91(15) . . . . ?
C2 C1 C15 C16 57.3(2) . . . . ?
N1 C1 C15 C16 -127.62(13) . . . . ?
C2 C1 C15 C18 -120.94(15) . . . . ?
N1 C1 C15 C18 54.18(17) . . . . ?
C18 C15 C16 C19 -0.7(3) . . . . ?
C1 C15 C16 C19 -179.1(3) . . . . ?
C18 C15 C16 S1 1.52(12) . . . . ?
C1 C15 C16 S1 -176.87(11) . . . . ?
C15 C16 S1 C17 -0.88(12) . . . . ?
C16 S1 C17 C18 -0.02(19) . . . . ?
S1 C17 C18 C15 0.9(3) . . . . ?
C16 C15 C18 C17 -1.7(2) . . . . ?
C1 C15 C18 C17 176.74(19) . . . . ?
C16 C15 C18 S2 2.74(12) . . . . ?
C1 C15 C18 S2 -178.85(13) . . . . ?
C15 C16 C19 S2 -1.7(4) . . . . ?
C15 C18 S2 C19 -3.1(2) . . . . ?
C16 C19 S2 C18 2.9(4) . . . . ?
C1 C2 C20 C21 52.04(19) . . . . ?
C3 C2 C20 C21 -129.21(15) . . . . ?
C1 C2 C20 C25 -126.17(15) . . . . ?
C3 C2 C20 C25 52.6(2) . . . . ?
C25 C20 C21 C22 0.1(2) . . . . ?
C2 C20 C21 C22 -178.11(13) . . . . ?
C20 C21 C22 C23 -0.6(2) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C21 C22 C23 C26 179.66(13) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
C26 C23 C24 C25 -179.05(13) . . . . ?
C23 C24 C25 C20 -0.7(2) . . . . ?
C21 C20 C25 C24 0.5(2) . . . . ?
C2 C20 C25 C24 178.74(12) . . . . ?
C5 C4 C27 C32 64.72(19) . . . . ?
C3 C4 C27 C32 -116.17(16) . . . . ?
C5 C4 C27 C28 -113.35(16) . . . . ?
C3 C4 C27 C28 65.76(19) . . . . ?
C32 C27 C28 C29 -1.8(2) . . . . ?
C4 C27 C28 C29 176.29(14) . . . . ?
C27 C28 C29 C30 1.4(3) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C29 C30 C31 C32 -1.7(3) . . . . ?
C30 C31 C32 C27 1.2(3) . . . . ?
C28 C27 C32 C31 0.5(2) . . . . ?
C4 C27 C32 C31 -177.58(15) . . . . ?
C4 C5 C33 C38 -118.5(6) . . . . ?
C6 C5 C33 C38 57.8(7) . . . . ?
C4 C5 C33 C34 60.4(6) . . . . ?
C6 C5 C33 C34 -123.3(4) . . . . ?
C38 C33 C34 C35 1.5(6) . . . . ?
C5 C33 C34 C35 -177.5(6) . . . . ?
C33 C34 C35 C36 0.6(4) . . . . ?
C34 C35 C36 O5 178.1(3) . . . . ?
C34 C35 C36 C37 -2.4(5) . . . . ?
O5 C36 C37 C38 -178.3(4) . . . . ?
C35 C36 C37 C38 2.1(6) . . . . ?
C36 C37 C38 C33 0.0(8) . . . . ?
C34 C33 C38 C37 -1.7(8) . . . . ?
C5 C33 C38 C37 177.2(6) . . . . ?
C35 C36 O5 C39 3.3(4) . . . . ?
C37 C36 O5 C39 -176.3(3) . . . . ?
C4 C5 C40 C41 58.7(11) . . . . ?
C6 C5 C40 C41 -113.7(8) . . . . ?
C4 C5 C40 C45 -123.2(12) . . . . ?
C6 C5 C40 C45 64.4(15) . . . . ?
C45 C40 C41 C42 1.4(10) . . . . ?
C5 C40 C41 C42 179.5(14) . . . . ?
C40 C41 C42 C43 0.6(8) . . . . ?
C41 C42 C43 O6 179.3(7) . . . . ?
C41 C42 C43 C44 -2.1(12) . . . . ?
O6 C43 C44 C45 179.9(9) . . . . ?
C42 C43 C44 C45 1.4(13) . . . . ?
C41 C40 C45 C44 -2.1(17) . . . . ?
C5 C40 C45 C44 179.8(12) . . . . ?
C43 C44 C45 C40 0.7(17) . . . . ?
C44 C43 O6 C46 12.2(10) . . . . ?
C42 C43 O6 C46 -169.2(6) . . . . ?
C7 C6 C47 C48 -108.85(16) . . . . ?
C5 C6 C47 C48 70.06(19) . . . . ?
C7 C6 C47 C52 66.51(18) . . . . ?
C5 C6 C47 C52 -114.58(16) . . . . ?
C52 C47 C48 C49 -2.8(2) . . . . ?
C6 C47 C48 C49 172.69(14) . . . . ?
C47 C48 C49 C50 0.2(2) . . . . ?
C48 C49 C50 C51 2.3(2) . . . . ?
C48 C49 C50 C53 -173.25(15) . . . . ?
C49 C50 C51 C52 -2.3(2) . . . . ?
C53 C50 C51 C52 173.31(14) . . . . ?
C50 C51 C52 C47 -0.3(2) . . . . ?
C48 C47 C52 C51 2.8(2) . . . . ?
C6 C47 C52 C51 -172.68(13) . . . . ?
C49 C50 C53 C59 69.9(8) . . . . ?
C51 C50 C53 C59 -105.5(8) . . . . ?
C49 C50 C53 C55 -143.2(3) . . . . ?
C51 C50 C53 C55 41.5(3) . . . . ?
C49 C50 C53 C54 -18.7(3) . . . . ?
C51 C50 C53 C54 165.9(3) . . . . ?
C49 C50 C53 C57 -159.5(9) . . . . ?
C51 C50 C53 C57 25.1(9) . . . . ?
C49 C50 C53 C56 98.1(3) . . . . ?
C51 C50 C53 C56 -77.2(3) . . . . ?
C49 C50 C53 C58 -50.5(8) . . . . ?
C51 C50 C53 C58 134.2(8) . . . . ?
C8 C7 C60 C61 -121.34(15) . . . . ?
C6 C7 C60 C61 61.49(18) . . . . ?
C8 C7 C60 C65 62.14(19) . . . . ?
C6 C7 C60 C65 -115.03(15) . . . . ?
C65 C60 C61 C62 1.3(2) . . . . ?
C7 C60 C61 C62 -175.25(13) . . . . ?
C60 C61 C62 C63 -0.5(2) . . . . ?
C61 C62 C63 C64 -0.9(2) . . . . ?
C61 C62 C63 C66 175.60(15) . . . . ?
C62 C63 C64 C65 1.6(2) . . . . ?
C66 C63 C64 C65 -175.01(15) . . . . ?
C63 C64 C65 C60 -0.8(2) . . . . ?
C61 C60 C65 C64 -0.7(2) . . . . ?
C7 C60 C65 C64 175.95(13) . . . . ?
C62 C63 C66 C67 -100.9(2) . . . . ?
C64 C63 C66 C67 75.5(2) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037


_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_9A
_database_code_depnum_ccdc_archive 'CCDC 1580597'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-05-03 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         ?
_chemical_formula_sum            'C47 H44 Cl3 N O'
_chemical_formula_weight         745.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.365(2)
_cell_length_b                   13.805(2)
_cell_length_c                   25.674(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.439(4)
_cell_angle_gamma                90
_cell_volume                     4024.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    143

_cell_measurement_reflns_used    4766

_cell_measurement_theta_min      3.0

_cell_measurement_theta_max      25.3


_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.264
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.885

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   
;J́acobson, R. (1998) Private communication\'
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku CrystalClear-SM Expert 2.1 b29
;

_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            42923
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.056
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7079
_reflns_number_gt                4660
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_structure_solution    SIR-97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0886P)²+4.1511P] 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_number_reflns         7079
_refine_ls_number_parameters     503
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.210
_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
N1 N 0.1358(2) -0.11732(18) 0.74616(9) 0.0317(6) Uani 1 1 d . . . . .
H1 H 0.070188 -0.124923 0.727124 0.038 Uiso 1 1 calc R U . . .
C1 C 0.2355(3) -0.1720(2) 0.74262(11) 0.0324(7) Uani 1 1 d . . . . .
H2 H 0.244333 -0.223735 0.718695 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3208(2) -0.1421(2) 0.77814(11) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.2706(2) -0.0606(2) 0.80550(10) 0.0252(6) Uani 1 1 d . . . . .
C4 C 0.3113(2) 0.0056(2) 0.84459(10) 0.0239(6) Uani 1 1 d . . . . .
C5 C 0.2347(2) 0.0787(2) 0.86058(10) 0.0246(6) Uani 1 1 d . . . . .
C6 C 0.1189(2) 0.0896(2) 0.83696(11) 0.0252(6) Uani 1 1 d . . . . .
C7 C 0.0774(2) 0.0244(2) 0.79882(10) 0.0250(6) Uani 1 1 d . . . . .
C8 C 0.1548(2) -0.0485(2) 0.78434(10) 0.0263(6) Uani 1 1 d . . . . .
C9 C 0.4354(2) -0.1924(2) 0.78450(11) 0.0275(6) Uani 1 1 d . . . . .
C10 C 0.4886(3) -0.2139(2) 0.83286(11) 0.0325(7) Uani 1 1 d . . . . .
H3 H 0.450490 -0.195470 0.863557 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5959(3) -0.2617(2) 0.83737(12) 0.0343(7) Uani 1 1 d . . . . .
H4 H 0.631297 -0.273610 0.870948 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6519(3) -0.2922(2) 0.79342(12) 0.0361(7) Uani 1 1 d . . . . .
C13 C 0.5974(3) -0.2743(2) 0.74518(12) 0.0359(7) Uani 1 1 d . . . . .
H5 H 0.633040 -0.296902 0.714651 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4920(3) -0.2242(2) 0.74051(11) 0.0323(7) Uani 1 1 d . . . . .
H6 H 0.457639 -0.211378 0.706835 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7707(3) -0.3409(3) 0.79762(16) 0.0595(11) Uani 1 1 d . . . . .
H7 H 0.762092 -0.409400 0.788272 0.089 Uiso 1 1 calc R U . . .
H8 H 0.803153 -0.335440 0.833475 0.089 Uiso 1 1 calc R U . . .
H9 H 0.824012 -0.309388 0.773835 0.089 Uiso 1 1 calc R U . . .
C16 C 0.4333(2) -0.0018(2) 0.86801(11) 0.0277(7) Uani 1 1 d . . . . .
C17 C 0.4536(3) -0.0298(2) 0.91963(11) 0.0338(7) Uani 1 1 d . . . . .
H10 H 0.388814 -0.044534 0.940427 0.041 Uiso 1 1 calc R U . . .
C18 C 0.5671(3) -0.0366(3) 0.94108(13) 0.0473(9) Uani 1 1 d . . . . .
H11 H 0.579949 -0.057376 0.976130 0.057 Uiso 1 1 calc R U . . .
C19 C 0.6619(3) -0.0129(3) 0.91137(15) 0.0550(11) Uani 1 1 d . . . . .
H12 H 0.739823 -0.016530 0.926197 0.066 Uiso 1 1 calc R U . . .
C20 C 0.6432(3) 0.0158(3) 0.86042(14) 0.0480(9) Uani 1 1 d . . . . .
H13 H 0.708215 0.032377 0.840121 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5297(3) 0.0205(2) 0.83862(12) 0.0341(7) Uani 1 1 d . . . . .
H14 H 0.517524 0.039255 0.803192 0.041 Uiso 1 1 calc R U . . .
C22 C 0.2738(2) 0.1453(2) 0.90417(10) 0.0254(6) Uani 1 1 d . . . . .
C23 C 0.3770(3) 0.1989(2) 0.90330(11) 0.0297(7) Uani 1 1 d . . . . .
H15 H 0.423693 0.194874 0.873550 0.036 Uiso 1 1 calc R U . . .
C24 C 0.4144(3) 0.2582(2) 0.94459(12) 0.0360(8) Uani 1 1 d . . . . .
H16 H 0.486079 0.293305 0.943102 0.043 Uiso 1 1 calc R U . . .
C25 C 0.3462(3) 0.2657(2) 0.98783(12) 0.0387(8) Uani 1 1 d . . . . .
C26 C 0.2422(3) 0.2143(2) 0.98926(12) 0.0381(8) Uani 1 1 d . . . . .
H17 H 0.194357 0.220303 1.018540 0.046 Uiso 1 1 calc R U . . .
C27 C 0.2073(3) 0.1544(2) 0.94862(11) 0.0300(7) Uani 1 1 d . . . . .
H18 H 0.136396 0.118404 0.950765 0.036 Uiso 1 1 calc R U . . .
O1 O 0.3746(2) 0.32166(19) 1.03068(9) 0.0575(7) Uani 1 1 d . . . . .
C28 C 0.4899(4) 0.3600(4) 1.03449(17) 0.0793(15) Uani 1 1 d . . . . .
H19 H 0.547125 0.307590 1.030920 0.119 Uiso 1 1 calc R U . . .
H20 H 0.503085 0.391427 1.068482 0.119 Uiso 1 1 calc R U . . .
H21 H 0.499554 0.407738 1.006722 0.119 Uiso 1 1 calc R U . . .
C29 C 0.0444(2) 0.1728(2) 0.85253(10) 0.0262(6) Uani 1 1 d . . . . .
C30 C -0.0643(2) 0.1595(2) 0.87467(12) 0.0320(7) Uani 1 1 d . . . . .
H22 H -0.095867 0.096046 0.877148 0.038 Uiso 1 1 calc R U . . .
C31 C -0.1273(3) 0.2377(2) 0.89318(12) 0.0376(8) Uani 1 1 d . . . . .
H23 H -0.201289 0.226338 0.907958 0.045 Uiso 1 1 calc R U . . .
C32 C -0.0851(3) 0.3326(2) 0.89069(12) 0.0370(8) Uani 1 1 d . . . . .
C33 C 0.0212(3) 0.3459(2) 0.86650(11) 0.0345(7) Uani 1 1 d . . . . .
H24 H 0.051397 0.409614 0.862820 0.041 Uiso 1 1 calc R U . . .
C34 C 0.0839(3) 0.2679(2) 0.84764(11) 0.0300(7) Uani 1 1 d . . . . .
H25 H 0.155582 0.279621 0.830986 0.036 Uiso 1 1 calc R U . . .
C35 C -0.1527(3) 0.4161(3) 0.91509(14) 0.0507(10) Uani 1 1 d . . . . .
C36 C -0.2753(4) 0.4253(3) 0.88867(18) 0.0712(13) Uani 1 1 d . . . . .
H26 H -0.267861 0.439981 0.851608 0.107 Uiso 1 1 calc R U . . .
H27 H -0.318518 0.477628 0.905185 0.107 Uiso 1 1 calc R U . . .
H28 H -0.318127 0.364221 0.892275 0.107 Uiso 1 1 calc R U . . .
C37 C -0.1629(5) 0.3955(4) 0.97327(16) 0.0917(18) Uani 1 1 d . . . . .
H29 H -0.208157 0.335896 0.977791 0.138 Uiso 1 1 calc R U . . .
H30 H -0.202982 0.449650 0.989671 0.138 Uiso 1 1 calc R U . . .
H31 H -0.083939 0.387735 0.989635 0.138 Uiso 1 1 calc R U . . .
C38 C -0.0883(4) 0.5132(3) 0.90974(19) 0.0717(13) Uani 1 1 d . . . . .
H32 H -0.009942 0.508864 0.927073 0.108 Uiso 1 1 calc R U . . .
H33 H -0.133468 0.564635 0.925995 0.108 Uiso 1 1 calc R U . . .
H34 H -0.080280 0.528055 0.872727 0.108 Uiso 1 1 calc R U . . .
C39 C -0.0410(2) 0.0280(2) 0.77120(11) 0.0291(7) Uani 1 1 d . . . . .
C40 C -0.1157(3) -0.0522(2) 0.77294(13) 0.0363(7) Uani 1 1 d . . . . .
H35 H -0.092022 -0.106849 0.793320 0.044 Uiso 1 1 calc R U . . .
C41 C -0.2229(3) -0.0539(3) 0.74576(14) 0.0443(9) Uani 1 1 d . . . . .
H36 H -0.271691 -0.109530 0.747787 0.053 Uiso 1 1 calc R U . . .
C42 C -0.2604(3) 0.0235(3) 0.71574(15) 0.0474(9) Uani 1 1 d . . . . .
C43 C -0.1868(3) 0.1036(3) 0.71389(14) 0.0473(9) Uani 1 1 d . . . . .
H37 H -0.210771 0.157790 0.693266 0.057 Uiso 1 1 calc R U . . .
C44 C -0.0790(3) 0.1064(2) 0.74139(13) 0.0387(8) Uani 1 1 d . . . . .
H38 H -0.030953 0.162599 0.739738 0.046 Uiso 1 1 calc R U . . .
C45 C -0.3773(4) 0.0199(3) 0.68480(19) 0.0727(14) Uani 1 1 d . . . . .
H39 H -0.436119 -0.014501 0.705334 0.087 Uiso 1 1 calc R U . . .
H40 H -0.406175 0.086691 0.678370 0.087 Uiso 1 1 calc R U . . .
C46 C -0.3651(5) -0.0302(4) 0.6344(2) 0.104(2) Uani 1 1 d . . . . .
H41 H -0.307550 0.004218 0.613855 0.156 Uiso 1 1 calc R U . . .
H42 H -0.441461 -0.031231 0.615150 0.156 Uiso 1 1 calc R U . . .
H43 H -0.338203 -0.096773 0.640715 0.156 Uiso 1 1 calc R U . . .
C47 C 0.1037(3) -0.1427(3) 0.91458(14) 0.0594(11) Uani 1 1 d D U . . .
H44 H 0.120038 -0.087911 0.890420 0.071 Uiso 0.541(4) 1 calc R U P A 1
H45 H 0.140484 -0.093648 0.891638 0.071 Uiso 0.459(4) 1 calc R U P A 2
Cl1 Cl -0.0172(3) -0.2157(3) 0.88916(10) 0.1030(11) Uani 0.541(4) 1 d D U P A 1
Cl2 Cl 0.2233(3) -0.2284(2) 0.91675(14) 0.0947(10) Uani 0.541(4) 1 d D U P A 1
Cl3 Cl 0.0761(4) -0.1017(3) 0.97366(16) 0.1235(15) Uani 0.541(4) 1 d D U P A 1
Cl4 Cl 0.1497(5) -0.1138(3) 0.98043(14) 0.1012(14) Uani 0.459(4) 1 d D U P A 2
Cl5 Cl 0.1495(5) -0.2485(2) 0.89647(16) 0.1089(13) Uani 0.459(4) 1 d D U P A 2
Cl6 Cl -0.0467(2) -0.1262(4) 0.90831(16) 0.1194(16) Uani 0.459(4) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.368(4) . ?
N1 C8 1.375(4) . ?
C1 C2 1.366(4) . ?
C2 C3 1.455(4) . ?
C2 C9 1.480(4) . ?
C3 C8 1.412(4) . ?
C3 C4 1.420(4) . ?
C4 C5 1.405(4) . ?
C4 C16 1.491(4) . ?
C5 C6 1.433(4) . ?
C5 C22 1.501(4) . ?
C6 C7 1.397(4) . ?
C6 C29 1.493(4) . ?
C7 C8 1.398(4) . ?
C7 C39 1.495(4) . ?
C9 C10 1.389(4) . ?
C9 C14 1.394(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.385(4) . ?
C12 C13 1.383(4) . ?
C12 C15 1.508(5) . ?
C13 C14 1.384(4) . ?
C16 C17 1.391(4) . ?
C16 C21 1.391(4) . ?
C17 C18 1.383(4) . ?
C18 C19 1.386(5) . ?
C19 C20 1.374(5) . ?
C20 C21 1.386(4) . ?
C22 C23 1.388(4) . ?
C22 C27 1.401(4) . ?
C23 C24 1.392(4) . ?
C24 C25 1.384(5) . ?
C25 O1 1.371(4) . ?
C25 C26 1.381(5) . ?
C26 C27 1.376(4) . ?
O1 C28 1.413(5) . ?
C29 C30 1.394(4) . ?
C29 C34 1.394(4) . ?
C30 C31 1.390(4) . ?
C31 C32 1.397(5) . ?
C32 C33 1.393(5) . ?
C32 C35 1.534(5) . ?
C33 C34 1.390(4) . ?
C35 C36 1.528(5) . ?
C35 C37 1.530(6) . ?
C35 C38 1.537(6) . ?
C39 C44 1.384(4) . ?
C39 C40 1.398(4) . ?
C40 C41 1.378(4) . ?
C41 C42 1.375(5) . ?
C42 C43 1.388(5) . ?
C42 C45 1.520(5) . ?
C43 C44 1.388(4) . ?
C45 C46 1.480(7) . ?
C47 Cl5 1.625(5) . ?
C47 Cl3 1.661(5) . ?
C47 Cl6 1.725(4) . ?
C47 Cl4 1.793(5) . ?
C47 Cl2 1.801(4) . ?
C47 Cl1 1.805(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 108.8(2) . . ?
C2 C1 N1 110.8(3) . . ?
C1 C2 C3 105.9(2) . . ?
C1 C2 C9 121.9(3) . . ?
C3 C2 C9 132.1(2) . . ?
C8 C3 C4 117.7(3) . . ?
C8 C3 C2 106.5(2) . . ?
C4 C3 C2 135.7(3) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C16 120.5(2) . . ?
C3 C4 C16 120.7(2) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 C22 119.4(2) . . ?
C6 C5 C22 119.2(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C29 120.3(2) . . ?
C5 C6 C29 119.2(2) . . ?
C6 C7 C8 116.9(2) . . ?
C6 C7 C39 125.5(3) . . ?
C8 C7 C39 117.5(2) . . ?
N1 C8 C7 127.2(2) . . ?
N1 C8 C3 108.0(2) . . ?
C7 C8 C3 124.7(3) . . ?
C10 C9 C14 117.3(3) . . ?
C10 C9 C2 123.1(3) . . ?
C14 C9 C2 119.5(3) . . ?
C11 C10 C9 121.6(3) . . ?
C12 C11 C10 120.6(3) . . ?
C13 C12 C11 118.2(3) . . ?
C13 C12 C15 120.6(3) . . ?
C11 C12 C15 121.2(3) . . ?
C12 C13 C14 121.3(3) . . ?
C13 C14 C9 121.0(3) . . ?
C17 C16 C21 118.4(3) . . ?
C17 C16 C4 121.2(3) . . ?
C21 C16 C4 120.4(3) . . ?
C18 C17 C16 120.8(3) . . ?
C17 C18 C19 119.9(3) . . ?
C20 C19 C18 120.0(3) . . ?
C19 C20 C21 120.1(3) . . ?
C20 C21 C16 120.8(3) . . ?
C23 C22 C27 116.8(3) . . ?
C23 C22 C5 122.5(2) . . ?
C27 C22 C5 120.6(3) . . ?
C22 C23 C24 122.2(3) . . ?
C25 C24 C23 119.5(3) . . ?
O1 C25 C26 116.1(3) . . ?
O1 C25 C24 124.4(3) . . ?
C26 C25 C24 119.5(3) . . ?
C27 C26 C25 120.6(3) . . ?
C26 C27 C22 121.5(3) . . ?
C25 O1 C28 116.9(3) . . ?
C30 C29 C34 117.1(3) . . ?
C30 C29 C6 122.0(3) . . ?
C34 C29 C6 120.8(3) . . ?
C31 C30 C29 121.0(3) . . ?
C30 C31 C32 121.9(3) . . ?
C33 C32 C31 116.8(3) . . ?
C33 C32 C35 122.8(3) . . ?
C31 C32 C35 120.4(3) . . ?
C34 C33 C32 121.3(3) . . ?
C33 C34 C29 121.8(3) . . ?
C36 C35 C37 110.1(4) . . ?
C36 C35 C32 110.2(3) . . ?
C37 C35 C32 108.6(3) . . ?
C36 C35 C38 108.5(3) . . ?
C37 C35 C38 107.8(4) . . ?
C32 C35 C38 111.7(3) . . ?
C44 C39 C40 117.5(3) . . ?
C44 C39 C7 122.8(3) . . ?
C40 C39 C7 119.6(3) . . ?
C41 C40 C39 121.5(3) . . ?
C42 C41 C40 121.1(3) . . ?
C41 C42 C43 117.7(3) . . ?
C41 C42 C45 120.7(3) . . ?
C43 C42 C45 121.6(3) . . ?
C42 C43 C44 121.7(3) . . ?
C39 C44 C43 120.4(3) . . ?
C46 C45 C42 111.1(4) . . ?
Cl5 C47 Cl6 114.8(3) . . ?
Cl5 C47 Cl4 112.7(3) . . ?
Cl6 C47 Cl4 107.9(3) . . ?
Cl3 C47 Cl2 111.5(3) . . ?
Cl3 C47 Cl1 110.5(3) . . ?
Cl2 C47 Cl1 101.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 0.8(3) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C2 C9 176.7(3) . . . . ?
C1 C2 C3 C8 1.1(3) . . . . ?
C9 C2 C3 C8 -176.4(3) . . . . ?
C1 C2 C3 C4 -176.7(3) . . . . ?
C9 C2 C3 C4 5.8(6) . . . . ?
C8 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C5 178.2(3) . . . . ?
C8 C3 C4 C16 -178.9(3) . . . . ?
C2 C3 C4 C16 -1.3(5) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C16 C4 C5 C6 177.3(3) . . . . ?
C3 C4 C5 C22 176.2(2) . . . . ?
C16 C4 C5 C22 -4.3(4) . . . . ?
C4 C5 C6 C7 2.9(4) . . . . ?
C22 C5 C6 C7 -175.5(2) . . . . ?
C4 C5 C6 C29 -175.4(2) . . . . ?
C22 C5 C6 C29 6.1(4) . . . . ?
C5 C6 C7 C8 -1.8(4) . . . . ?
C29 C6 C7 C8 176.6(2) . . . . ?
C5 C6 C7 C39 -179.7(3) . . . . ?
C29 C6 C7 C39 -1.4(4) . . . . ?
C1 N1 C8 C7 177.1(3) . . . . ?
C1 N1 C8 C3 -0.1(3) . . . . ?
C6 C7 C8 N1 -176.5(3) . . . . ?
C39 C7 C8 N1 1.6(4) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C39 C7 C8 C3 178.3(3) . . . . ?
C4 C3 C8 N1 177.6(2) . . . . ?
C2 C3 C8 N1 -0.6(3) . . . . ?
C4 C3 C8 C7 0.4(4) . . . . ?
C2 C3 C8 C7 -177.8(3) . . . . ?
C1 C2 C9 C10 -136.1(3) . . . . ?
C3 C2 C9 C10 41.0(5) . . . . ?
C1 C2 C9 C14 40.9(4) . . . . ?
C3 C2 C9 C14 -141.9(3) . . . . ?
C14 C9 C10 C11 2.5(5) . . . . ?
C2 C9 C10 C11 179.6(3) . . . . ?
C9 C10 C11 C12 -2.0(5) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C15 177.7(3) . . . . ?
C11 C12 C13 C14 2.4(5) . . . . ?
C15 C12 C13 C14 -175.8(3) . . . . ?
C12 C13 C14 C9 -1.8(5) . . . . ?
C10 C9 C14 C13 -0.6(4) . . . . ?
C2 C9 C14 C13 -177.9(3) . . . . ?
C5 C4 C16 C17 69.3(4) . . . . ?
C3 C4 C16 C17 -111.2(3) . . . . ?
C5 C4 C16 C21 -110.0(3) . . . . ?
C3 C4 C16 C21 69.5(4) . . . . ?
C21 C16 C17 C18 -0.8(5) . . . . ?
C4 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 1.6(5) . . . . ?
C17 C18 C19 C20 -1.0(6) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C19 C20 C21 C16 1.2(5) . . . . ?
C17 C16 C21 C20 -0.6(5) . . . . ?
C4 C16 C21 C20 178.7(3) . . . . ?
C4 C5 C22 C23 55.1(4) . . . . ?
C6 C5 C22 C23 -126.4(3) . . . . ?
C4 C5 C22 C27 -123.5(3) . . . . ?
C6 C5 C22 C27 55.0(4) . . . . ?
C27 C22 C23 C24 0.7(4) . . . . ?
C5 C22 C23 C24 -178.0(3) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C24 C25 O1 179.8(3) . . . . ?
C23 C24 C25 C26 -0.1(5) . . . . ?
O1 C25 C26 C27 -178.6(3) . . . . ?
C24 C25 C26 C27 1.3(5) . . . . ?
C25 C26 C27 C22 -1.6(5) . . . . ?
C23 C22 C27 C26 0.6(4) . . . . ?
C5 C22 C27 C26 179.3(3) . . . . ?
C26 C25 O1 C28 168.4(3) . . . . ?
C24 C25 O1 C28 -11.5(5) . . . . ?
C7 C6 C29 C30 61.8(4) . . . . ?
C5 C6 C29 C30 -119.9(3) . . . . ?
C7 C6 C29 C34 -121.3(3) . . . . ?
C5 C6 C29 C34 57.1(4) . . . . ?
C34 C29 C30 C31 -2.9(4) . . . . ?
C6 C29 C30 C31 174.1(3) . . . . ?
C29 C30 C31 C32 -0.2(5) . . . . ?
C30 C31 C32 C33 2.9(4) . . . . ?
C30 C31 C32 C35 -175.5(3) . . . . ?
C31 C32 C33 C34 -2.4(4) . . . . ?
C35 C32 C33 C34 176.0(3) . . . . ?
C32 C33 C34 C29 -0.7(4) . . . . ?
C30 C29 C34 C33 3.4(4) . . . . ?
C6 C29 C34 C33 -173.7(3) . . . . ?
C33 C32 C35 C36 120.1(4) . . . . ?
C31 C32 C35 C36 -61.6(4) . . . . ?
C33 C32 C35 C37 -119.3(4) . . . . ?
C31 C32 C35 C37 59.0(4) . . . . ?
C33 C32 C35 C38 -0.5(4) . . . . ?
C31 C32 C35 C38 177.8(3) . . . . ?
C6 C7 C39 C44 59.9(4) . . . . ?
C8 C7 C39 C44 -118.1(3) . . . . ?
C6 C7 C39 C40 -123.3(3) . . . . ?
C8 C7 C39 C40 58.7(4) . . . . ?
C44 C39 C40 C41 0.5(5) . . . . ?
C7 C39 C40 C41 -176.5(3) . . . . ?
C39 C40 C41 C42 0.1(5) . . . . ?
C40 C41 C42 C43 -0.2(5) . . . . ?
C40 C41 C42 C45 178.4(4) . . . . ?
C41 C42 C43 C44 -0.3(6) . . . . ?
C45 C42 C43 C44 -178.9(4) . . . . ?
C40 C39 C44 C43 -0.9(5) . . . . ?
C7 C39 C44 C43 175.9(3) . . . . ?
C42 C43 C44 C39 0.9(5) . . . . ?
C41 C42 C45 C46 -83.2(5) . . . . ?
C43 C42 C45 C46 95.4(5) . . . . ?

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.055


_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_8I
_database_code_depnum_ccdc_archive 'CCDC 1580596'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-05-03 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         ?
_chemical_formula_sum            'C50 H41 Cl3 F3 N O3 S'
_chemical_formula_weight         899.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.7851(11)
_cell_length_b                   10.7442(14)
_cell_length_c                   22.106(3)
_cell_angle_alpha                103.099(7)
_cell_angle_beta                 95.707(7)
_cell_angle_gamma                98.173(7)
_cell_volume                     2219.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123

_cell_measurement_reflns_used    4655

_cell_measurement_theta_min      3.0

_cell_measurement_theta_max      25.4


_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.310
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.857

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   
;J́acobson, R. (1998) Private communication\'
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku CrystalClear-SM Expert 2.1 b29
;

_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            20535
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.044
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             7672
_reflns_number_gt                6440
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_structure_solution    SIR-97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0827P)²+3.2370P] 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_number_reflns         7672
_refine_ls_number_parameters     619
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.156
_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
N1 N 0.5096(2) 0.3082(2) 0.13714(10) 0.0267(5) Uani 1 1 d . . . . .
C1 C 0.5460(3) 0.3579(3) 0.08149(13) 0.0284(6) Uani 1 1 d . . . . .
H1 H 0.483261 0.418166 0.072634 0.034 Uiso 1 1 calc R U . . .
H2 H 0.536557 0.285089 0.043931 0.034 Uiso 1 1 calc R U . . .
C2 C 0.6988(3) 0.4293(3) 0.09840(12) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.762695 0.368310 0.082426 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7162(3) 0.4596(3) 0.16978(12) 0.0251(6) Uani 1 1 d . . . . .
C4 C 0.8230(3) 0.5426(3) 0.21245(12) 0.0267(6) Uani 1 1 d . . . . .
C5 C 0.8085(3) 0.5645(3) 0.27662(13) 0.0308(6) Uani 1 1 d . . . . .
C6 C 0.6892(3) 0.5031(3) 0.29654(12) 0.0339(7) Uani 1 1 d D . . . .
C7 C 0.5824(3) 0.4183(3) 0.25296(13) 0.0289(6) Uani 1 1 d . . . . .
C8 C 0.6026(3) 0.3950(3) 0.19006(12) 0.0259(6) Uani 1 1 d . . . . .
S1 S 0.51180(7) 0.14949(7) 0.12852(3) 0.02613(19) Uani 1 1 d . . . . .
O1 O 0.4736(2) 0.11778(19) 0.18475(9) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.4297(2) 0.08583(19) 0.06949(9) 0.0324(5) Uani 1 1 d . . . . .
C9 C 0.6866(3) 0.1296(3) 0.12403(13) 0.0280(6) Uani 1 1 d . . . . .
C10 C 0.7751(3) 0.1402(3) 0.17857(14) 0.0332(7) Uani 1 1 d . . . . .
H4 H 0.740326 0.152507 0.217751 0.040 Uiso 1 1 calc R U . . .
C11 C 0.9144(3) 0.1328(3) 0.17564(15) 0.0376(7) Uani 1 1 d . . . . .
H5 H 0.974116 0.136651 0.212869 0.045 Uiso 1 1 calc R U . . .
C12 C 0.9685(3) 0.1198(3) 0.11897(15) 0.0359(7) Uani 1 1 d . . . . .
C13 C 0.8775(3) 0.1081(3) 0.06466(14) 0.0335(7) Uani 1 1 d . . . . .
H6 H 0.912862 0.097773 0.025657 0.040 Uiso 1 1 calc R U . . .
C14 C 0.7364(3) 0.1110(3) 0.06591(13) 0.0304(6) Uani 1 1 d . . . . .
H7 H 0.675201 0.100604 0.028305 0.036 Uiso 1 1 calc R U . . .
C15 C 1.1218(4) 0.1180(4) 0.11706(17) 0.0445(8) Uani 1 1 d . . . . .
H8 H 1.165159 0.197113 0.106676 0.067 Uiso 1 1 calc R U . . .
H9 H 1.133968 0.042094 0.085132 0.067 Uiso 1 1 calc R U . . .
H10 H 1.166040 0.113611 0.158122 0.067 Uiso 1 1 calc R U . . .
C16 C 0.7236(3) 0.5479(3) 0.07189(12) 0.0261(6) Uani 1 1 d . . . . .
C17 C 0.6532(3) 0.6507(3) 0.09022(13) 0.0320(7) Uani 1 1 d . . . . .
H11 H 0.587068 0.645459 0.118621 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6783(3) 0.7617(3) 0.06746(14) 0.0334(7) Uani 1 1 d . . . . .
H12 H 0.631058 0.832283 0.080916 0.040 Uiso 1 1 calc R U . . .
C19 C 0.7722(4) 0.7681(3) 0.02536(15) 0.0385(8) Uani 1 1 d . . . . .
H13 H 0.788554 0.842749 0.009141 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8427(3) 0.6662(3) 0.00658(14) 0.0370(7) Uani 1 1 d . . . . .
H14 H 0.908377 0.671794 -0.022011 0.044 Uiso 1 1 calc R U . . .
C21 C 0.8183(3) 0.5562(3) 0.02924(12) 0.0284(6) Uani 1 1 d . . . . .
H15 H 0.866141 0.486061 0.015660 0.034 Uiso 1 1 calc R U . . .
C22 C 0.9459(3) 0.6051(3) 0.18875(12) 0.0272(6) Uani 1 1 d . . . . .
C23 C 1.0365(3) 0.5302(3) 0.15922(13) 0.0295(6) Uani 1 1 d . . . . .
H16 H 1.022551 0.439608 0.156469 0.035 Uiso 1 1 calc R U . . .
C24 C 1.1466(3) 0.5853(3) 0.13380(13) 0.0317(7) Uani 1 1 d . . . . .
H17 H 1.208183 0.532283 0.114912 0.038 Uiso 1 1 calc R U . . .
C25 C 1.1687(3) 0.7165(3) 0.13533(14) 0.0345(7) Uani 1 1 d . . . . .
C26 C 1.0786(3) 0.7921(3) 0.16578(16) 0.0379(7) Uani 1 1 d . . . . .
H18 H 1.092196 0.882504 0.168070 0.045 Uiso 1 1 calc R U . . .
C27 C 0.9704(3) 0.7383(3) 0.19256(14) 0.0332(7) Uani 1 1 d . . . . .
H19 H 0.912159 0.792259 0.213703 0.040 Uiso 1 1 calc R U . . .
C28 C 1.2843(4) 0.7768(4) 0.10509(17) 0.0457(8) Uani 1 1 d . . . . .
H20 H 1.351709 0.717791 0.096810 0.069 Uiso 1 1 calc R U . . .
H21 H 1.331242 0.859144 0.133319 0.069 Uiso 1 1 calc R U . . .
H22 H 1.244952 0.792545 0.065531 0.069 Uiso 1 1 calc R U . . .
C29 C 0.9187(3) 0.6569(3) 0.32449(13) 0.0319(7) Uani 1 1 d . . . . .
C30 C 0.8884(4) 0.7712(3) 0.36017(15) 0.0390(7) Uani 1 1 d . . . . .
H47 H 0.798290 0.792812 0.353039 0.047 Uiso 1 1 calc R U . . .
C31 C 0.9879(4) 0.8539(3) 0.40599(16) 0.0473(9) Uani 1 1 d . . . . .
H48 H 0.965321 0.931096 0.430517 0.057 Uiso 1 1 calc R U . . .
C32 C 1.1194(4) 0.8250(4) 0.41620(16) 0.0481(9) Uani 1 1 d . . . . .
C33 C 1.1523(4) 0.7129(4) 0.38007(17) 0.0546(10) Uani 1 1 d . . . . .
H49 H 1.243440 0.693115 0.386299 0.066 Uiso 1 1 calc R U . . .
C34 C 1.0516(4) 0.6297(4) 0.33480(16) 0.0466(9) Uani 1 1 d . . . . .
H50 H 1.074369 0.552570 0.310380 0.056 Uiso 1 1 calc R U . . .
C35 C 1.2218(5) 0.9116(5) 0.4672(2) 0.0666(12) Uani 1 1 d . . . . .
F1 F 1.2065(4) 1.0343(3) 0.47923(19) 0.1365(16) Uani 1 1 d . U . . .
F2 F 1.2138(5) 0.8841(4) 0.52103(14) 0.1363(16) Uani 1 1 d . U . . .
F3 F 1.3512(4) 0.9131(4) 0.45711(18) 0.1289(13) Uani 1 1 d . U . . .
C36 C 0.4497(3) 0.3643(3) 0.27286(13) 0.0311(7) Uani 1 1 d . . . . .
C37 C 0.3250(3) 0.3934(3) 0.24842(14) 0.0360(7) Uani 1 1 d . . . . .
H23 H 0.325865 0.444876 0.218690 0.043 Uiso 1 1 calc R U . . .
C38 C 0.1997(4) 0.3487(3) 0.26662(15) 0.0406(8) Uani 1 1 d . . . . .
H24 H 0.115300 0.369462 0.249595 0.049 Uiso 1 1 calc R U . . .
C39 C 0.1984(3) 0.2728(3) 0.31023(15) 0.0408(8) Uani 1 1 d . . . . .
C40 C 0.3201(4) 0.2401(3) 0.33386(14) 0.0404(8) Uani 1 1 d . . . . .
H25 H 0.318569 0.185336 0.362103 0.048 Uiso 1 1 calc R U . . .
C41 C 0.4455(3) 0.2881(3) 0.31597(13) 0.0343(7) Uani 1 1 d . . . . .
H26 H 0.529950 0.268440 0.333590 0.041 Uiso 1 1 calc R U . . .
O3 O 0.0677(3) 0.2349(3) 0.32518(12) 0.0597(7) Uani 1 1 d . . . . .
C43 C 0.0581(5) 0.1468(6) 0.3649(3) 0.0907(18) Uani 1 1 d . . . . .
H29 H 0.089708 0.066876 0.344821 0.136 Uiso 1 1 calc R U . . .
H30 H -0.038875 0.126409 0.372114 0.136 Uiso 1 1 calc R U . . .
H31 H 0.116945 0.186742 0.405143 0.136 Uiso 1 1 calc R U . . .
C44 C 0.6665(7) 0.5440(6) 0.3641(3) 0.040(2) Uani 0.568(10) 1 d D . P A 1
C45 C 0.7487(9) 0.5029(7) 0.4083(2) 0.046(2) Uani 0.568(10) 1 d D . P A 1
H33 H 0.815459 0.450001 0.395229 0.055 Uiso 0.568(10) 1 calc R U P A 1
C46 C 0.7334(10) 0.5393(10) 0.4717(3) 0.060(3) Uani 0.568(10) 1 d D . P A 1
C47 C 0.6358(10) 0.6166(11) 0.4896(3) 0.066(3) Uani 0.568(10) 1 d D . P A 1
H34 H 0.624181 0.640988 0.532570 0.079 Uiso 0.568(10) 1 calc R U P A 1
C48 C 0.5546(9) 0.6592(9) 0.4461(3) 0.062(3) Uani 0.568(10) 1 d D . P A 1
H35 H 0.491138 0.715579 0.459519 0.075 Uiso 0.568(10) 1 calc R U P A 1
C49 C 0.5662(8) 0.6190(9) 0.3822(3) 0.046(2) Uani 0.568(10) 1 d D . P A 1
H36 H 0.506462 0.642756 0.351680 0.055 Uiso 0.568(10) 1 calc R U P A 1
C50 C 0.8234(11) 0.4952(12) 0.5186(4) 0.112(4) Uani 0.568(10) 1 d D . P A 1
H37 H 0.901756 0.564764 0.538481 0.168 Uiso 0.568(10) 1 calc R U P A 1
H38 H 0.858969 0.418367 0.497518 0.168 Uiso 0.568(10) 1 calc R U P A 1
H39 H 0.768379 0.473658 0.550697 0.168 Uiso 0.568(10) 1 calc R U P A 1
C51 C 0.6934(8) 0.5183(7) 0.3667(3) 0.038(3) Uani 0.432(10) 1 d D . P A 2
C52 C 0.6075(9) 0.5958(9) 0.3980(3) 0.038(3) Uani 0.432(10) 1 d D . P A 2
H40 H 0.547283 0.635941 0.375050 0.046 Uiso 0.432(10) 1 calc R U P A 2
C53 C 0.6088(11) 0.6152(11) 0.4624(3) 0.047(3) Uani 0.432(10) 1 d D . P A 2
C54 C 0.6961(12) 0.5552(12) 0.4953(3) 0.058(4) Uani 0.432(10) 1 d D . P A 2
H41 H 0.697086 0.567834 0.539307 0.069 Uiso 0.432(10) 1 calc R U P A 2
C55 C 0.7817(11) 0.4771(11) 0.4650(4) 0.057(3) Uani 0.432(10) 1 d D . P A 2
H42 H 0.841638 0.437069 0.488092 0.069 Uiso 0.432(10) 1 calc R U P A 2
C56 C 0.7797(12) 0.4572(11) 0.3996(3) 0.044(3) Uani 0.432(10) 1 d D . P A 2
H43 H 0.836985 0.402429 0.378288 0.053 Uiso 0.432(10) 1 calc R U P A 2
C57 C 0.5148(11) 0.6997(11) 0.4949(4) 0.076(4) Uani 0.432(10) 1 d D . P A 2
H44 H 0.481299 0.664542 0.528946 0.115 Uiso 0.432(10) 1 calc R U P A 2
H45 H 0.435198 0.701870 0.464739 0.115 Uiso 0.432(10) 1 calc R U P A 2
H46 H 0.566693 0.787811 0.512121 0.115 Uiso 0.432(10) 1 calc R U P A 2
C58 C 0.5158(4) 0.9415(4) 0.28245(16) 0.0510(9) Uani 1 1 d . . . . .
H32 H 0.497830 1.010178 0.260264 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.61156(16) 0.84064(17) 0.23798(6) 0.0976(5) Uani 1 1 d . . . . .
Cl2 Cl 0.35591(14) 0.85862(16) 0.29086(7) 0.0940(5) Uani 1 1 d . . . . .
Cl3 Cl 0.61085(12) 1.01770(11) 0.35588(5) 0.0681(3) 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
N1 C8 1.456(3) . ?
N1 C1 1.502(3) . ?
N1 S1 1.676(2) . ?
C1 C2 1.549(4) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 C16 1.518(4) . ?
C2 C3 1.524(4) . ?
C2 H3 1.0000 . ?
C3 C4 1.391(4) . ?
C3 C8 1.392(4) . ?
C4 C5 1.409(4) . ?
C4 C22 1.493(4) . ?
C5 C6 1.416(4) . ?
C5 C29 1.503(4) . ?
C6 C7 1.407(4) . ?
C6 C44 1.507(6) . ?
C6 C51 1.519(6) . ?
C7 C8 1.395(4) . ?
C7 C36 1.494(4) . ?
S1 O2 1.430(2) . ?
S1 O1 1.431(2) . ?
S1 C9 1.763(3) . ?
C9 C10 1.385(4) . ?
C9 C14 1.402(4) . ?
C10 C11 1.384(4) . ?
C10 H4 0.9500 . ?
C11 C12 1.394(4) . ?
C11 H5 0.9500 . ?
C12 C13 1.392(5) . ?
C12 C15 1.508(5) . ?
C13 C14 1.388(4) . ?
C13 H6 0.9500 . ?
C14 H7 0.9500 . ?
C15 H8 0.9800 . ?
C15 H9 0.9800 . ?
C15 H10 0.9800 . ?
C16 C17 1.389(4) . ?
C16 C21 1.394(4) . ?
C17 C18 1.396(4) . ?
C17 H11 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H12 0.9500 . ?
C19 C20 1.383(5) . ?
C19 H13 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H14 0.9500 . ?
C21 H15 0.9500 . ?
C22 C23 1.393(4) . ?
C22 C27 1.399(4) . ?
C23 C24 1.385(4) . ?
C23 H16 0.9500 . ?
C24 C25 1.387(4) . ?
C24 H17 0.9500 . ?
C25 C26 1.402(5) . ?
C25 C28 1.511(4) . ?
C26 C27 1.383(4) . ?
C26 H18 0.9500 . ?
C27 H19 0.9500 . ?
C28 H20 0.9800 . ?
C28 H21 0.9800 . ?
C28 H22 0.9800 . ?
C29 C34 1.381(5) . ?
C29 C30 1.390(4) . ?
C30 C31 1.384(5) . ?
C30 H47 0.9500 . ?
C31 C32 1.375(6) . ?
C31 H48 0.9500 . ?
C32 C33 1.384(6) . ?
C32 C35 1.475(5) . ?
C33 C34 1.385(5) . ?
C33 H49 0.9500 . ?
C34 H50 0.9500 . ?
C35 F2 1.296(6) . ?
C35 F3 1.306(6) . ?
C35 F1 1.318(6) . ?
C36 C37 1.390(5) . ?
C36 C41 1.390(4) . ?
C37 C38 1.383(5) . ?
C37 H23 0.9500 . ?
C38 C39 1.397(5) . ?
C38 H24 0.9500 . ?
C39 C40 1.375(5) . ?
C39 O3 1.381(4) . ?
C40 C41 1.392(4) . ?
C40 H25 0.9500 . ?
C41 H26 0.9500 . ?
O3 C43 1.430(5) . ?
C43 H29 0.9800 . ?
C43 H30 0.9800 . ?
C43 H31 0.9800 . ?
C44 C49 1.389(7) . ?
C44 C45 1.390(7) . ?
C45 C46 1.396(7) . ?
C45 H33 0.9500 . ?
C46 C47 1.382(7) . ?
C46 C50 1.496(7) . ?
C47 C48 1.384(7) . ?
C47 H34 0.9500 . ?
C48 C49 1.402(7) . ?
C48 H35 0.9500 . ?
C49 H36 0.9500 . ?
C50 H37 0.9800 . ?
C50 H38 0.9800 . ?
C50 H39 0.9800 . ?
C51 C52 1.388(7) . ?
C51 C56 1.388(8) . ?
C52 C53 1.391(7) . ?
C52 H40 0.9500 . ?
C53 C54 1.385(8) . ?
C53 C57 1.503(7) . ?
C54 C55 1.383(7) . ?
C54 H41 0.9500 . ?
C55 C56 1.409(7) . ?
C55 H42 0.9500 . ?
C56 H43 0.9500 . ?
C57 H44 0.9800 . ?
C57 H45 0.9800 . ?
C57 H46 0.9800 . ?
C58 Cl1 1.734(4) . ?
C58 Cl2 1.735(4) . ?
C58 Cl3 1.747(4) . ?
C58 H32 1.0000 . ?

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
C8 N1 C1 104.4(2) . . ?
C8 N1 S1 115.95(18) . . ?
C1 N1 S1 114.07(18) . . ?
N1 C1 C2 106.7(2) . . ?
N1 C1 H1 110.4 . . ?
C2 C1 H1 110.4 . . ?
N1 C1 H2 110.4 . . ?
C2 C1 H2 110.4 . . ?
H1 C1 H2 108.6 . . ?
C16 C2 C3 114.3(2) . . ?
C16 C2 C1 112.4(2) . . ?
C3 C2 C1 101.3(2) . . ?
C16 C2 H3 109.5 . . ?
C3 C2 H3 109.5 . . ?
C1 C2 H3 109.5 . . ?
C4 C3 C8 121.0(2) . . ?
C4 C3 C2 128.4(2) . . ?
C8 C3 C2 110.5(2) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C22 119.2(2) . . ?
C5 C4 C22 123.1(3) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 C29 119.8(3) . . ?
C6 C5 C29 119.5(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 C44 119.1(3) . . ?
C5 C6 C44 119.2(3) . . ?
C7 C6 C51 122.1(3) . . ?
C5 C6 C51 116.3(3) . . ?
C8 C7 C6 116.7(3) . . ?
C8 C7 C36 121.8(3) . . ?
C6 C7 C36 121.3(2) . . ?
C3 C8 C7 122.5(3) . . ?
C3 C8 N1 110.8(2) . . ?
C7 C8 N1 126.6(2) . . ?
O2 S1 O1 119.92(12) . . ?
O2 S1 N1 105.95(12) . . ?
O1 S1 N1 107.02(12) . . ?
O2 S1 C9 108.99(13) . . ?
O1 S1 C9 108.02(13) . . ?
N1 S1 C9 106.13(13) . . ?
C10 C9 C14 120.7(3) . . ?
C10 C9 S1 119.4(2) . . ?
C14 C9 S1 119.7(2) . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H4 120.2 . . ?
C9 C10 H4 120.2 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H5 119.5 . . ?
C12 C11 H5 119.5 . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 C15 121.3(3) . . ?
C11 C12 C15 120.4(3) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H6 119.1 . . ?
C12 C13 H6 119.1 . . ?
C13 C14 C9 118.4(3) . . ?
C13 C14 H7 120.8 . . ?
C9 C14 H7 120.8 . . ?
C12 C15 H8 109.5 . . ?
C12 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
C12 C15 H10 109.5 . . ?
H8 C15 H10 109.5 . . ?
H9 C15 H10 109.5 . . ?
C17 C16 C21 118.8(3) . . ?
C17 C16 C2 120.5(3) . . ?
C21 C16 C2 120.7(3) . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H11 119.6 . . ?
C18 C17 H11 119.6 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H12 120.3 . . ?
C17 C18 H12 120.3 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H13 119.9 . . ?
C20 C19 H13 119.9 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H14 119.8 . . ?
C21 C20 H14 119.8 . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 H15 119.9 . . ?
C16 C21 H15 119.9 . . ?
C23 C22 C27 117.9(3) . . ?
C23 C22 C4 120.3(3) . . ?
C27 C22 C4 121.7(3) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H16 119.4 . . ?
C22 C23 H16 119.4 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 H17 119.3 . . ?
C25 C24 H17 119.3 . . ?
C24 C25 C26 117.4(3) . . ?
C24 C25 C28 121.9(3) . . ?
C26 C25 C28 120.6(3) . . ?
C27 C26 C25 121.5(3) . . ?
C27 C26 H18 119.2 . . ?
C25 C26 H18 119.2 . . ?
C26 C27 C22 120.5(3) . . ?
C26 C27 H19 119.7 . . ?
C22 C27 H19 119.7 . . ?
C25 C28 H20 109.5 . . ?
C25 C28 H21 109.5 . . ?
H20 C28 H21 109.5 . . ?
C25 C28 H22 109.5 . . ?
H20 C28 H22 109.5 . . ?
H21 C28 H22 109.5 . . ?
C34 C29 C30 118.3(3) . . ?
C34 C29 C5 121.1(3) . . ?
C30 C29 C5 120.5(3) . . ?
C31 C30 C29 120.7(3) . . ?
C31 C30 H47 119.7 . . ?
C29 C30 H47 119.7 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H48 119.8 . . ?
C30 C31 H48 119.8 . . ?
C31 C32 C33 119.7(3) . . ?
C31 C32 C35 119.3(4) . . ?
C33 C32 C35 120.9(4) . . ?
C32 C33 C34 119.7(4) . . ?
C32 C33 H49 120.2 . . ?
C34 C33 H49 120.2 . . ?
C29 C34 C33 121.3(3) . . ?
C29 C34 H50 119.4 . . ?
C33 C34 H50 119.4 . . ?
F2 C35 F3 106.7(5) . . ?
F2 C35 F1 102.5(4) . . ?
F3 C35 F1 104.7(4) . . ?
F2 C35 C32 113.3(4) . . ?
F3 C35 C32 114.1(4) . . ?
F1 C35 C32 114.5(4) . . ?
C37 C36 C41 118.3(3) . . ?
C37 C36 C7 118.9(3) . . ?
C41 C36 C7 122.8(3) . . ?
C38 C37 C36 121.2(3) . . ?
C38 C37 H23 119.4 . . ?
C36 C37 H23 119.4 . . ?
C37 C38 C39 119.4(3) . . ?
C37 C38 H24 120.3 . . ?
C39 C38 H24 120.3 . . ?
C40 C39 O3 125.4(3) . . ?
C40 C39 C38 120.4(3) . . ?
O3 C39 C38 114.2(3) . . ?
C39 C40 C41 119.3(3) . . ?
C39 C40 H25 120.3 . . ?
C41 C40 H25 120.3 . . ?
C36 C41 C40 121.3(3) . . ?
C36 C41 H26 119.3 . . ?
C40 C41 H26 119.3 . . ?
C39 O3 C43 116.6(3) . . ?
O3 C43 H29 109.5 . . ?
O3 C43 H30 109.5 . . ?
H29 C43 H30 109.5 . . ?
O3 C43 H31 109.5 . . ?
H29 C43 H31 109.5 . . ?
H30 C43 H31 109.5 . . ?
C49 C44 C45 120.6(5) . . ?
C49 C44 C6 121.6(6) . . ?
C45 C44 C6 117.7(6) . . ?
C44 C45 C46 120.2(6) . . ?
C44 C45 H33 119.9 . . ?
C46 C45 H33 119.9 . . ?
C47 C46 C45 118.9(5) . . ?
C47 C46 C50 121.5(6) . . ?
C45 C46 C50 119.6(6) . . ?
C46 C47 C48 121.3(5) . . ?
C46 C47 H34 119.3 . . ?
C48 C47 H34 119.3 . . ?
C47 C48 C49 119.9(5) . . ?
C47 C48 H35 120.1 . . ?
C49 C48 H35 120.1 . . ?
C44 C49 C48 118.9(5) . . ?
C44 C49 H36 120.5 . . ?
C48 C49 H36 120.5 . . ?
C46 C50 H37 109.5 . . ?
C46 C50 H38 109.5 . . ?
H37 C50 H38 109.5 . . ?
C46 C50 H39 109.5 . . ?
H37 C50 H39 109.5 . . ?
H38 C50 H39 109.5 . . ?
C52 C51 C56 120.0(5) . . ?
C52 C51 C6 118.2(6) . . ?
C56 C51 C6 121.7(6) . . ?
C51 C52 C53 120.7(6) . . ?
C51 C52 H40 119.6 . . ?
C53 C52 H40 119.6 . . ?
C54 C53 C52 119.2(5) . . ?
C54 C53 C57 121.3(6) . . ?
C52 C53 C57 119.5(6) . . ?
C55 C54 C53 120.9(6) . . ?
C55 C54 H41 119.6 . . ?
C53 C54 H41 119.6 . . ?
C54 C55 C56 119.8(6) . . ?
C54 C55 H42 120.1 . . ?
C56 C55 H42 120.1 . . ?
C51 C56 C55 119.3(6) . . ?
C51 C56 H43 120.3 . . ?
C55 C56 H43 120.3 . . ?
C53 C57 H44 109.5 . . ?
C53 C57 H45 109.5 . . ?
H44 C57 H45 109.5 . . ?
C53 C57 H46 109.5 . . ?
H44 C57 H46 109.5 . . ?
H45 C57 H46 109.5 . . ?
Cl1 C58 Cl2 112.1(2) . . ?
Cl1 C58 Cl3 110.4(2) . . ?
Cl2 C58 Cl3 110.4(2) . . ?
Cl1 C58 H32 108.0 . . ?
Cl2 C58 H32 108.0 . . ?
Cl3 C58 H32 108.0 . . ?

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
C8 N1 C1 C2 25.5(3) . . . . ?
S1 N1 C1 C2 -102.1(2) . . . . ?
N1 C1 C2 C16 -143.9(2) . . . . ?
N1 C1 C2 C3 -21.5(3) . . . . ?
C16 C2 C3 C4 -46.3(4) . . . . ?
C1 C2 C3 C4 -167.4(3) . . . . ?
C16 C2 C3 C8 131.0(3) . . . . ?
C1 C2 C3 C8 9.9(3) . . . . ?
C8 C3 C4 C5 -3.4(4) . . . . ?
C2 C3 C4 C5 173.6(3) . . . . ?
C8 C3 C4 C22 177.2(3) . . . . ?
C2 C3 C4 C22 -5.7(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C22 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C5 C29 -178.0(3) . . . . ?
C22 C4 C5 C29 1.4(4) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C29 C5 C6 C7 178.6(3) . . . . ?
C4 C5 C6 C44 -170.7(4) . . . . ?
C29 C5 C6 C44 7.6(6) . . . . ?
C4 C5 C6 C51 171.7(5) . . . . ?
C29 C5 C6 C51 -10.0(6) . . . . ?
C5 C6 C7 C8 2.2(4) . . . . ?
C44 C6 C7 C8 173.1(4) . . . . ?
C51 C6 C7 C8 -168.8(5) . . . . ?
C5 C6 C7 C36 -173.4(3) . . . . ?
C44 C6 C7 C36 -2.4(5) . . . . ?
C51 C6 C7 C36 15.6(6) . . . . ?
C4 C3 C8 C7 6.1(4) . . . . ?
C2 C3 C8 C7 -171.4(3) . . . . ?
C4 C3 C8 N1 -176.5(2) . . . . ?
C2 C3 C8 N1 5.9(3) . . . . ?
C6 C7 C8 C3 -5.3(4) . . . . ?
C36 C7 C8 C3 170.2(3) . . . . ?
C6 C7 C8 N1 177.8(3) . . . . ?
C36 C7 C8 N1 -6.7(5) . . . . ?
C1 N1 C8 C3 -19.7(3) . . . . ?
S1 N1 C8 C3 106.7(2) . . . . ?
C1 N1 C8 C7 157.5(3) . . . . ?
S1 N1 C8 C7 -76.1(3) . . . . ?
C8 N1 S1 O2 -171.69(19) . . . . ?
C1 N1 S1 O2 -50.3(2) . . . . ?
C8 N1 S1 O1 59.3(2) . . . . ?
C1 N1 S1 O1 -179.33(18) . . . . ?
C8 N1 S1 C9 -55.9(2) . . . . ?
C1 N1 S1 C9 65.5(2) . . . . ?
O2 S1 C9 C10 -157.1(2) . . . . ?
O1 S1 C9 C10 -25.3(3) . . . . ?
N1 S1 C9 C10 89.2(3) . . . . ?
O2 S1 C9 C14 26.6(3) . . . . ?
O1 S1 C9 C14 158.4(2) . . . . ?
N1 S1 C9 C14 -87.1(2) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
S1 C9 C10 C11 -176.0(2) . . . . ?
C9 C10 C11 C12 2.5(5) . . . . ?
C10 C11 C12 C13 -3.0(5) . . . . ?
C10 C11 C12 C15 177.2(3) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C15 C12 C13 C14 -179.3(3) . . . . ?
C12 C13 C14 C9 1.7(4) . . . . ?
C10 C9 C14 C13 -2.3(4) . . . . ?
S1 C9 C14 C13 173.9(2) . . . . ?
C3 C2 C16 C17 -52.8(4) . . . . ?
C1 C2 C16 C17 61.9(3) . . . . ?
C3 C2 C16 C21 126.6(3) . . . . ?
C1 C2 C16 C21 -118.7(3) . . . . ?
C21 C16 C17 C18 -1.3(4) . . . . ?
C2 C16 C17 C18 178.1(3) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C18 C19 C20 C21 0.9(5) . . . . ?
C19 C20 C21 C16 -0.9(5) . . . . ?
C17 C16 C21 C20 1.1(4) . . . . ?
C2 C16 C21 C20 -178.3(3) . . . . ?
C3 C4 C22 C23 -66.2(4) . . . . ?
C5 C4 C22 C23 114.5(3) . . . . ?
C3 C4 C22 C27 110.6(3) . . . . ?
C5 C4 C22 C27 -68.7(4) . . . . ?
C27 C22 C23 C24 -0.7(4) . . . . ?
C4 C22 C23 C24 176.3(3) . . . . ?
C22 C23 C24 C25 -1.7(4) . . . . ?
C23 C24 C25 C26 2.4(4) . . . . ?
C23 C24 C25 C28 -177.1(3) . . . . ?
C24 C25 C26 C27 -0.9(5) . . . . ?
C28 C25 C26 C27 178.6(3) . . . . ?
C25 C26 C27 C22 -1.4(5) . . . . ?
C23 C22 C27 C26 2.1(4) . . . . ?
C4 C22 C27 C26 -174.8(3) . . . . ?
C4 C5 C29 C34 -66.4(4) . . . . ?
C6 C5 C29 C34 115.2(4) . . . . ?
C4 C5 C29 C30 114.5(3) . . . . ?
C6 C5 C29 C30 -63.8(4) . . . . ?
C34 C29 C30 C31 -1.7(5) . . . . ?
C5 C29 C30 C31 177.4(3) . . . . ?
C29 C30 C31 C32 1.0(5) . . . . ?
C30 C31 C32 C33 0.5(6) . . . . ?
C30 C31 C32 C35 -177.3(4) . . . . ?
C31 C32 C33 C34 -1.2(6) . . . . ?
C35 C32 C33 C34 176.4(4) . . . . ?
C30 C29 C34 C33 0.9(5) . . . . ?
C5 C29 C34 C33 -178.2(3) . . . . ?
C32 C33 C34 C29 0.6(6) . . . . ?
C31 C32 C35 F2 86.6(6) . . . . ?
C33 C32 C35 F2 -91.1(5) . . . . ?
C31 C32 C35 F3 -151.1(4) . . . . ?
C33 C32 C35 F3 31.2(6) . . . . ?
C31 C32 C35 F1 -30.5(6) . . . . ?
C33 C32 C35 F1 151.8(5) . . . . ?
C8 C7 C36 C37 -57.1(4) . . . . ?
C6 C7 C36 C37 118.2(3) . . . . ?
C8 C7 C36 C41 124.3(3) . . . . ?
C6 C7 C36 C41 -60.4(4) . . . . ?
C41 C36 C37 C38 0.4(4) . . . . ?
C7 C36 C37 C38 -178.2(3) . . . . ?
C36 C37 C38 C39 -0.1(5) . . . . ?
C37 C38 C39 C40 -1.5(5) . . . . ?
C37 C38 C39 O3 179.4(3) . . . . ?
O3 C39 C40 C41 -178.3(3) . . . . ?
C38 C39 C40 C41 2.8(5) . . . . ?
C37 C36 C41 C40 0.9(4) . . . . ?
C7 C36 C41 C40 179.5(3) . . . . ?
C39 C40 C41 C36 -2.5(5) . . . . ?
C40 C39 O3 C43 -4.8(6) . . . . ?
C38 C39 O3 C43 174.2(4) . . . . ?
C7 C6 C44 C49 -65.5(6) . . . . ?
C5 C6 C44 C49 105.7(6) . . . . ?
C7 C6 C44 C45 113.9(5) . . . . ?
C5 C6 C44 C45 -74.9(6) . . . . ?
C49 C44 C45 C46 -1.4(10) . . . . ?
C6 C44 C45 C46 179.2(6) . . . . ?
C44 C45 C46 C47 -0.1(13) . . . . ?
C44 C45 C46 C50 -179.5(8) . . . . ?
C45 C46 C47 C48 -0.6(16) . . . . ?
C50 C46 C47 C48 178.7(11) . . . . ?
C46 C47 C48 C49 2.9(17) . . . . ?
C45 C44 C49 C48 3.7(11) . . . . ?
C6 C44 C49 C48 -176.9(7) . . . . ?
C47 C48 C49 C44 -4.4(15) . . . . ?
C7 C6 C51 C52 -79.1(6) . . . . ?
C5 C6 C51 C52 109.5(5) . . . . ?
C7 C6 C51 C56 100.8(7) . . . . ?
C5 C6 C51 C56 -70.6(7) . . . . ?
C56 C51 C52 C53 1.3(11) . . . . ?
C6 C51 C52 C53 -178.8(7) . . . . ?
C51 C52 C53 C54 -0.6(15) . . . . ?
C51 C52 C53 C57 179.9(8) . . . . ?
C52 C53 C54 C55 0.2(19) . . . . ?
C57 C53 C54 C55 179.7(11) . . . . ?
C53 C54 C55 C56 -0.5(19) . . . . ?
C52 C51 C56 C55 -1.5(13) . . . . ?
C6 C51 C56 C55 178.6(8) . . . . ?
C54 C55 C56 C51 1.2(17) . . . . ?

_refine_diff_density_max         0.904
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.063


_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1580598'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-05-03 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         ?
_chemical_formula_sum            'C44 H40 N2 O3 S'
_chemical_formula_weight         676.84

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.744(3)
_cell_length_b                   9.8309(15)
_cell_length_c                   25.091(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.077(5)
_cell_angle_gamma                90
_cell_volume                     3627.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123

_cell_measurement_reflns_used    7457

_cell_measurement_theta_min      3.0

_cell_measurement_theta_max      25.4


_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.15

_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.870

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku CrystalClear-SM Expert 2.1 b29
;

_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            38207
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6376
_reflns_number_gt                5034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_structure_solution    SIR-97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0601P)²+2.7644P] 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_number_reflns         6376
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
N1 N 0.03260(11) 0.45935(18) 0.82543(7) 0.0248(4) Uani 1 1 d . . . . .
C1 C -0.04174(14) 0.4260(2) 0.85414(8) 0.0255(5) Uani 1 1 d . . . . .
H1 H -0.103390 0.440000 0.841685 0.031 Uiso 1 1 calc R U . . .
C2 C -0.01465(14) 0.3710(2) 0.90211(8) 0.0234(4) Uani 1 1 d . . . . .
C3 C 0.08493(14) 0.3720(2) 0.90559(8) 0.0212(4) Uani 1 1 d . . . . .
C4 C 0.15708(13) 0.3328(2) 0.94201(8) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.24673(14) 0.3571(2) 0.92831(8) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.26267(13) 0.4201(2) 0.87908(8) 0.0220(4) Uani 1 1 d . . . . .
N2 N 0.19396(11) 0.45575(17) 0.84349(6) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.11139(13) 0.4296(2) 0.85768(8) 0.0215(4) Uani 1 1 d . . . . .
S1 S 0.02750(4) 0.55040(6) 0.76879(2) 0.02716(15) Uani 1 1 d . . . . .
O1 O 0.08204(11) 0.48376(17) 0.73210(6) 0.0344(4) Uani 1 1 d . . . . .
O2 O -0.06747(10) 0.56901(17) 0.75590(6) 0.0374(4) Uani 1 1 d . . . . .
C8 C 0.07933(14) 0.7040(2) 0.78890(8) 0.0249(5) Uani 1 1 d . . . . .
C9 C 0.04732(16) 0.7743(2) 0.83152(9) 0.0341(5) Uani 1 1 d . . . . .
H2 H -0.001891 0.739613 0.849876 0.041 Uiso 1 1 calc R U . . .
C10 C 0.08809(17) 0.8953(3) 0.84677(9) 0.0375(6) Uani 1 1 d . . . . .
H3 H 0.066732 0.943723 0.876145 0.045 Uiso 1 1 calc R U . . .
C11 C 0.15970(16) 0.9484(2) 0.82032(9) 0.0306(5) Uani 1 1 d . . . . .
C12 C 0.19100(16) 0.8754(2) 0.77791(9) 0.0312(5) Uani 1 1 d . . . . .
H4 H 0.240270 0.909819 0.759533 0.037 Uiso 1 1 calc R U . . .
C13 C 0.15139(15) 0.7538(2) 0.76223(8) 0.0302(5) Uani 1 1 d . . . . .
H5 H 0.173348 0.704246 0.733291 0.036 Uiso 1 1 calc R U . . .
C14 C 0.20206(19) 1.0826(3) 0.83648(10) 0.0435(6) Uani 1 1 d . . . . .
H6 H 0.268426 1.073633 0.839163 0.065 Uiso 1 1 calc R U . . .
H7 H 0.181556 1.110093 0.871190 0.065 Uiso 1 1 calc R U . . .
H8 H 0.183815 1.151558 0.809622 0.065 Uiso 1 1 calc R U . . .
C15 C -0.08190(14) 0.3263(2) 0.93970(8) 0.0241(5) Uani 1 1 d . . . . .
C16 C -0.06955(14) 0.3447(2) 0.99489(8) 0.0263(5) Uani 1 1 d . . . . .
H9 H -0.013703 0.380433 1.010098 0.032 Uiso 1 1 calc R U . . .
C17 C -0.13777(15) 0.3113(2) 1.02772(9) 0.0301(5) Uani 1 1 d . . . . .
H10 H -0.127636 0.324559 1.065174 0.036 Uiso 1 1 calc R U . . .
C18 C -0.22073(15) 0.2590(2) 1.00736(10) 0.0312(5) Uani 1 1 d . . . . .
C19 C -0.23294(15) 0.2412(2) 0.95256(10) 0.0335(5) Uani 1 1 d . . . . .
H11 H -0.289104 0.206210 0.937470 0.040 Uiso 1 1 calc R U . . .
C20 C -0.16499(15) 0.2732(2) 0.91933(9) 0.0290(5) Uani 1 1 d . . . . .
H12 H -0.175152 0.258758 0.881946 0.035 Uiso 1 1 calc R U . . .
C21 C -0.29399(18) 0.2219(3) 1.04394(11) 0.0433(6) Uani 1 1 d . . . . .
H13 H -0.273361 0.145362 1.066690 0.065 Uiso 1 1 calc R U . . .
H14 H -0.349454 0.196117 1.022483 0.065 Uiso 1 1 calc R U . . .
H15 H -0.306682 0.300304 1.066378 0.065 Uiso 1 1 calc R U . . .
C22 C 0.14180(13) 0.2618(2) 0.99301(8) 0.0228(4) Uani 1 1 d . . . . .
C23 C 0.16672(14) 0.3214(2) 1.04229(8) 0.0273(5) Uani 1 1 d . . . . .
H16 H 0.189732 0.411655 1.043898 0.033 Uiso 1 1 calc R U . . .
C24 C 0.15786(15) 0.2486(3) 1.08896(9) 0.0370(6) Uani 1 1 d . . . . .
H17 H 0.173844 0.289764 1.122568 0.044 Uiso 1 1 calc R U . . .
C25 C 0.12574(16) 0.1158(3) 1.08684(10) 0.0404(6) Uani 1 1 d . . . . .
H18 H 0.121526 0.065466 1.118897 0.049 Uiso 1 1 calc R U . . .
C26 C 0.09997(16) 0.0568(3) 1.03825(10) 0.0365(6) Uani 1 1 d . . . . .
H19 H 0.077283 -0.033672 1.036753 0.044 Uiso 1 1 calc R U . . .
C27 C 0.10732(14) 0.1301(2) 0.99168(9) 0.0283(5) Uani 1 1 d . . . . .
H20 H 0.088508 0.089882 0.958291 0.034 Uiso 1 1 calc R U . . .
C28 C 0.32269(13) 0.3120(2) 0.96709(8) 0.0225(4) Uani 1 1 d . . . . .
C29 C 0.37761(14) 0.4036(2) 0.99678(8) 0.0284(5) Uani 1 1 d . . . . .
H21 H 0.372216 0.498276 0.989578 0.034 Uiso 1 1 calc R U . . .
C30 C 0.43997(15) 0.3584(3) 1.03664(9) 0.0330(5) Uani 1 1 d . . . . .
H22 H 0.477285 0.422006 1.056484 0.040 Uiso 1 1 calc R U . . .
C31 C 0.44827(14) 0.2201(3) 1.04782(8) 0.0314(5) Uani 1 1 d . . . . .
C32 C 0.39628(15) 0.1274(2) 1.01775(8) 0.0305(5) Uani 1 1 d . . . . .
H23 H 0.403053 0.032680 1.024325 0.037 Uiso 1 1 calc R U . . .
C33 C 0.33412(14) 0.1739(2) 0.97787(8) 0.0270(5) Uani 1 1 d . . . . .
H24 H 0.298327 0.109818 0.957327 0.032 Uiso 1 1 calc R U . . .
O3 O 0.50935(11) 0.1856(2) 1.08925(6) 0.0446(5) Uani 1 1 d . . . . .
C34 C 0.5113(2) 0.0473(3) 1.10592(10) 0.0536(8) Uani 1 1 d . . . . .
H25 H 0.450835 0.020482 1.116013 0.080 Uiso 1 1 calc R U . . .
H26 H 0.555484 0.036530 1.136698 0.080 Uiso 1 1 calc R U . . .
H27 H 0.528921 -0.010447 1.076539 0.080 Uiso 1 1 calc R U . . .
C35 C 0.35423(14) 0.4522(2) 0.86049(8) 0.0239(4) Uani 1 1 d . . . . .
C36 C 0.42811(15) 0.3645(2) 0.86576(8) 0.0302(5) Uani 1 1 d . . . . .
H28 H 0.423231 0.281604 0.884788 0.036 Uiso 1 1 calc R U . . .
C37 C 0.50915(15) 0.3966(3) 0.84353(9) 0.0360(6) Uani 1 1 d . . . . .
H29 H 0.558318 0.334061 0.847228 0.043 Uiso 1 1 calc R U . . .
C38 C 0.52027(15) 0.5176(3) 0.81602(9) 0.0355(6) Uani 1 1 d . . . . .
C39 C 0.44624(15) 0.6055(3) 0.81116(9) 0.0324(5) Uani 1 1 d . . . . .
H30 H 0.451566 0.689283 0.792767 0.039 Uiso 1 1 calc R U . . .
C40 C 0.36490(15) 0.5734(2) 0.83260(8) 0.0275(5) Uani 1 1 d . . . . .
H31 H 0.315352 0.635121 0.828232 0.033 Uiso 1 1 calc R U . . .
C41 C 0.60952(16) 0.5568(3) 0.79186(10) 0.0484(7) Uani 1 1 d . . . . .
C42 C 0.6844(3) 0.4654(7) 0.8068(3) 0.172(3) Uani 1 1 d . . . . .
H32 H 0.673494 0.377266 0.789283 0.258 Uiso 1 1 calc R U . . .
H33 H 0.689105 0.452908 0.845667 0.258 Uiso 1 1 calc R U . . .
H34 H 0.741202 0.504390 0.795606 0.258 Uiso 1 1 calc R U . . .
C43 C 0.6389(3) 0.7025(5) 0.81393(17) 0.1032(16) Uani 1 1 d . . . . .
H35 H 0.648498 0.698926 0.852955 0.155 Uiso 1 1 calc R U . . .
H36 H 0.590837 0.768464 0.803819 0.155 Uiso 1 1 calc R U . . .
H37 H 0.695359 0.730241 0.798672 0.155 Uiso 1 1 calc R U . . .
C44 C 0.5939(2) 0.5805(5) 0.73337(12) 0.0921(15) Uani 1 1 d . . . . .
H38 H 0.650021 0.614381 0.719307 0.138 Uiso 1 1 calc R U . . .
H39 H 0.545436 0.647810 0.726712 0.138 Uiso 1 1 calc R U . . .
H40 H 0.576125 0.494900 0.715543 0.138 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
N1 C1 1.393(3) . ?
N1 C7 1.399(3) . ?
N1 S1 1.6767(17) . ?
C1 C2 1.354(3) . ?
C2 C3 1.465(3) . ?
C2 C15 1.483(3) . ?
C3 C4 1.406(3) . ?
C3 C7 1.409(3) . ?
C4 C5 1.410(3) . ?
C4 C22 1.489(3) . ?
C5 C6 1.417(3) . ?
C5 C28 1.498(3) . ?
C6 N2 1.348(3) . ?
C6 C35 1.493(3) . ?
N2 C7 1.318(3) . ?
S1 O1 1.4243(16) . ?
S1 O2 1.4264(17) . ?
S1 C8 1.750(2) . ?
C8 C9 1.384(3) . ?
C8 C13 1.385(3) . ?
C9 C10 1.374(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.389(3) . ?
C11 C14 1.503(3) . ?
C12 C13 1.376(3) . ?
C15 C20 1.395(3) . ?
C15 C16 1.396(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.385(3) . ?
C18 C21 1.511(3) . ?
C19 C20 1.385(3) . ?
C22 C27 1.390(3) . ?
C22 C23 1.394(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.389(4) . ?
C25 C26 1.379(4) . ?
C26 C27 1.384(3) . ?
C28 C33 1.392(3) . ?
C28 C29 1.392(3) . ?
C29 C30 1.383(3) . ?
C30 C31 1.392(4) . ?
C31 O3 1.369(3) . ?
C31 C32 1.380(3) . ?
C32 C33 1.386(3) . ?
O3 C34 1.422(4) . ?
C35 C36 1.388(3) . ?
C35 C40 1.396(3) . ?
C36 C37 1.390(3) . ?
C37 C38 1.391(4) . ?
C38 C39 1.391(3) . ?
C38 C41 1.537(3) . ?
C39 C40 1.385(3) . ?
C41 C42 1.452(5) . ?
C41 C44 1.488(4) . ?
C41 C43 1.585(5) . ?

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 N1 C7 107.66(16) . . ?
C1 N1 S1 125.07(14) . . ?
C7 N1 S1 125.97(14) . . ?
C2 C1 N1 111.14(18) . . ?
C1 C2 C3 106.35(18) . . ?
C1 C2 C15 121.03(18) . . ?
C3 C2 C15 132.61(18) . . ?
C4 C3 C7 114.96(18) . . ?
C4 C3 C2 138.23(19) . . ?
C7 C3 C2 106.81(17) . . ?
C3 C4 C5 118.33(18) . . ?
C3 C4 C22 122.23(18) . . ?
C5 C4 C22 119.39(17) . . ?
C4 C5 C6 120.22(18) . . ?
C4 C5 C28 117.54(17) . . ?
C6 C5 C28 122.23(18) . . ?
N2 C6 C5 121.85(18) . . ?
N2 C6 C35 113.06(17) . . ?
C5 C6 C35 125.08(18) . . ?
C7 N2 C6 115.81(17) . . ?
N2 C7 N1 123.24(18) . . ?
N2 C7 C3 128.77(18) . . ?
N1 C7 C3 107.97(17) . . ?
O1 S1 O2 120.17(10) . . ?
O1 S1 N1 108.00(9) . . ?
O2 S1 N1 104.18(9) . . ?
O1 S1 C8 109.15(10) . . ?
O2 S1 C8 110.87(10) . . ?
N1 S1 C8 102.93(9) . . ?
C9 C8 C13 120.8(2) . . ?
C9 C8 S1 119.19(17) . . ?
C13 C8 S1 120.00(17) . . ?
C10 C9 C8 118.7(2) . . ?
C9 C10 C11 121.7(2) . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 C14 121.1(2) . . ?
C12 C11 C14 120.4(2) . . ?
C13 C12 C11 120.7(2) . . ?
C12 C13 C8 119.6(2) . . ?
C20 C15 C16 117.47(19) . . ?
C20 C15 C2 119.18(19) . . ?
C16 C15 C2 123.15(19) . . ?
C17 C16 C15 120.7(2) . . ?
C16 C17 C18 121.8(2) . . ?
C19 C18 C17 117.4(2) . . ?
C19 C18 C21 121.6(2) . . ?
C17 C18 C21 121.0(2) . . ?
C20 C19 C18 121.4(2) . . ?
C19 C20 C15 121.3(2) . . ?
C27 C22 C23 119.04(19) . . ?
C27 C22 C4 119.58(18) . . ?
C23 C22 C4 121.25(19) . . ?
C24 C23 C22 119.8(2) . . ?
C23 C24 C25 120.4(2) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C27 119.6(2) . . ?
C26 C27 C22 121.0(2) . . ?
C33 C28 C29 118.01(19) . . ?
C33 C28 C5 119.31(18) . . ?
C29 C28 C5 122.40(19) . . ?
C30 C29 C28 120.7(2) . . ?
C29 C30 C31 120.3(2) . . ?
O3 C31 C32 124.1(2) . . ?
O3 C31 C30 116.0(2) . . ?
C32 C31 C30 119.8(2) . . ?
C31 C32 C33 119.4(2) . . ?
C32 C33 C28 121.8(2) . . ?
C31 O3 C34 117.3(2) . . ?
C36 C35 C40 117.5(2) . . ?
C36 C35 C6 124.03(19) . . ?
C40 C35 C6 118.27(19) . . ?
C35 C36 C37 120.8(2) . . ?
C36 C37 C38 121.9(2) . . ?
C37 C38 C39 117.1(2) . . ?
C37 C38 C41 123.0(2) . . ?
C39 C38 C41 119.9(2) . . ?
C40 C39 C38 121.3(2) . . ?
C39 C40 C35 121.4(2) . . ?
C42 C41 C44 114.4(4) . . ?
C42 C41 C38 113.5(3) . . ?
C44 C41 C38 110.6(2) . . ?
C42 C41 C43 106.6(4) . . ?
C44 C41 C43 102.9(3) . . ?
C38 C41 C43 108.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 -2.7(2) . . . . ?
S1 N1 C1 C2 -170.23(15) . . . . ?
N1 C1 C2 C3 1.6(2) . . . . ?
N1 C1 C2 C15 -179.53(18) . . . . ?
C1 C2 C3 C4 180.0(2) . . . . ?
C15 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C7 0.0(2) . . . . ?
C15 C2 C3 C7 -178.7(2) . . . . ?
C7 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C5 -178.5(2) . . . . ?
C7 C3 C4 C22 -175.78(18) . . . . ?
C2 C3 C4 C22 4.2(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C22 C4 C5 C6 177.74(18) . . . . ?
C3 C4 C5 C28 -178.71(18) . . . . ?
C22 C4 C5 C28 -1.4(3) . . . . ?
C4 C5 C6 N2 -1.6(3) . . . . ?
C28 C5 C6 N2 177.43(18) . . . . ?
C4 C5 C6 C35 179.34(19) . . . . ?
C28 C5 C6 C35 -1.6(3) . . . . ?
C5 C6 N2 C7 0.7(3) . . . . ?
C35 C6 N2 C7 179.86(17) . . . . ?
C6 N2 C7 N1 -179.70(18) . . . . ?
C6 N2 C7 C3 1.5(3) . . . . ?
C1 N1 C7 N2 -176.45(19) . . . . ?
S1 N1 C7 N2 -9.0(3) . . . . ?
C1 N1 C7 C3 2.6(2) . . . . ?
S1 N1 C7 C3 169.99(15) . . . . ?
C4 C3 C7 N2 -2.6(3) . . . . ?
C2 C3 C7 N2 177.4(2) . . . . ?
C4 C3 C7 N1 178.42(17) . . . . ?
C2 C3 C7 N1 -1.6(2) . . . . ?
C1 N1 S1 O1 -134.92(17) . . . . ?
C7 N1 S1 O1 59.75(19) . . . . ?
C1 N1 S1 O2 -6.1(2) . . . . ?
C7 N1 S1 O2 -171.41(17) . . . . ?
C1 N1 S1 C8 109.71(18) . . . . ?
C7 N1 S1 C8 -55.62(19) . . . . ?
O1 S1 C8 C9 -168.55(17) . . . . ?
O2 S1 C8 C9 56.9(2) . . . . ?
N1 S1 C8 C9 -54.01(19) . . . . ?
O1 S1 C8 C13 11.5(2) . . . . ?
O2 S1 C8 C13 -123.06(18) . . . . ?
N1 S1 C8 C13 126.05(18) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
S1 C8 C9 C10 -179.56(18) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C14 178.4(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C14 C11 C12 C13 -178.7(2) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
S1 C8 C13 C12 179.21(17) . . . . ?
C1 C2 C15 C20 33.5(3) . . . . ?
C3 C2 C15 C20 -148.0(2) . . . . ?
C1 C2 C15 C16 -141.1(2) . . . . ?
C3 C2 C15 C16 37.4(3) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C2 C15 C16 C17 174.6(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C16 C17 C18 C21 179.4(2) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C21 C18 C19 C20 -178.9(2) . . . . ?
C18 C19 C20 C15 -0.8(4) . . . . ?
C16 C15 C20 C19 0.6(3) . . . . ?
C2 C15 C20 C19 -174.3(2) . . . . ?
C3 C4 C22 C27 67.4(3) . . . . ?
C5 C4 C22 C27 -109.8(2) . . . . ?
C3 C4 C22 C23 -116.7(2) . . . . ?
C5 C4 C22 C23 66.1(3) . . . . ?
C27 C22 C23 C24 0.7(3) . . . . ?
C4 C22 C23 C24 -175.2(2) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 -1.9(3) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C25 C26 C27 C22 1.1(3) . . . . ?
C23 C22 C27 C26 -1.9(3) . . . . ?
C4 C22 C27 C26 174.2(2) . . . . ?
C4 C5 C28 C33 64.2(3) . . . . ?
C6 C5 C28 C33 -114.8(2) . . . . ?
C4 C5 C28 C29 -109.6(2) . . . . ?
C6 C5 C28 C29 71.3(3) . . . . ?
C33 C28 C29 C30 -1.6(3) . . . . ?
C5 C28 C29 C30 172.34(19) . . . . ?
C28 C29 C30 C31 -0.3(3) . . . . ?
C29 C30 C31 O3 -177.64(19) . . . . ?
C29 C30 C31 C32 2.3(3) . . . . ?
O3 C31 C32 C33 177.7(2) . . . . ?
C30 C31 C32 C33 -2.2(3) . . . . ?
C31 C32 C33 C28 0.2(3) . . . . ?
C29 C28 C33 C32 1.7(3) . . . . ?
C5 C28 C33 C32 -172.44(19) . . . . ?
C32 C31 O3 C34 -7.5(3) . . . . ?
C30 C31 O3 C34 172.4(2) . . . . ?
N2 C6 C35 C36 -136.5(2) . . . . ?
C5 C6 C35 C36 42.6(3) . . . . ?
N2 C6 C35 C40 38.6(3) . . . . ?
C5 C6 C35 C40 -142.3(2) . . . . ?
C40 C35 C36 C37 -0.6(3) . . . . ?
C6 C35 C36 C37 174.6(2) . . . . ?
C35 C36 C37 C38 1.0(3) . . . . ?
C36 C37 C38 C39 -0.6(3) . . . . ?
C36 C37 C38 C41 178.9(2) . . . . ?
C37 C38 C39 C40 -0.3(3) . . . . ?
C41 C38 C39 C40 -179.8(2) . . . . ?
C38 C39 C40 C35 0.8(3) . . . . ?
C36 C35 C40 C39 -0.3(3) . . . . ?
C6 C35 C40 C39 -175.74(19) . . . . ?
C37 C38 C41 C42 -8.2(5) . . . . ?
C39 C38 C41 C42 171.3(4) . . . . ?
C37 C38 C41 C44 122.0(3) . . . . ?
C39 C38 C41 C44 -58.5(4) . . . . ?
C37 C38 C41 C43 -126.1(3) . . . . ?
C39 C38 C41 C43 53.4(3) . . . . ?

_refine_diff_density_max         0.876
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.049


_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?
