# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_160530noda
_database_code_depnum_ccdc_archive 'CCDC 1498994'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C52 H54 N2 O5'
_chemical_formula_moiety         'C52 H54 N2 O5'
_chemical_formula_weight         787.01
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.8070(2)
_cell_length_b                   27.0000(5)
_cell_length_c                   28.2406(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     8240.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    48391
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      68.11
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3360.00
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_T_max  0.969

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            97960
_diffrn_reflns_av_R_equivalents  0.1012
_diffrn_reflns_theta_max         68.223
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             15026
_reflns_number_gt                7097
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.2217
_refine_ls_wR_factor_gt          0.1752
_refine_ls_number_restraints     40
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         15026
_refine_ls_number_parameters     1067
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1121P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.006
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(16)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5991(5) 0.3138(2) 0.59071(19) 0.0570(14) Uani 1 1 d . . . . .
H1 H 0.5749 0.3367 0.6085 0.068 Uiso 1 1 calc R U . . .
O2 O 0.5664(5) 0.38502(19) 0.65398(19) 0.0629(15) Uani 1 1 d . . . . .
O3 O 0.9033(5) 0.35173(19) 0.56764(17) 0.0556(14) Uani 1 1 d . . . . .
O4 O 0.3569(5) 0.35169(19) 0.81359(18) 0.0594(14) Uani 1 1 d . . . . .
O5 O 0.9775(5) 0.3291(2) 0.65769(19) 0.0641(15) Uani 1 1 d . . . . .
H5 H 0.9701 0.3393 0.6297 0.077 Uiso 1 1 calc R U . . .
O6 O 0.7335(5) 0.3400(2) 0.73866(19) 0.0625(15) Uani 1 1 d . . . . .
O7 O 0.3063(5) 0.3831(2) 0.72818(19) 0.0635(15) Uani 1 1 d . . . . .
H7 H 0.3014 0.3707 0.7554 0.076 Uiso 1 1 calc R U . . .
O8 O 0.6006(6) 0.2716(2) 0.7810(2) 0.0661(15) Uani 1 1 d . . . . .
H8 H 0.6575 0.2899 0.7706 0.23(9) Uiso 1 1 calc R . . . .
N9 N 0.7287(6) 0.3139(2) 0.5889(2) 0.0483(15) Uani 1 1 d . . . . .
N10 N 0.4135(6) 0.3658(2) 0.7057(2) 0.0519(16) Uani 1 1 d . . . . .
N11 N 0.8589(6) 0.3232(2) 0.6781(2) 0.0525(16) Uani 1 1 d . . . . .
N12 N 0.4881(6) 0.2975(2) 0.7795(2) 0.0545(17) Uani 1 1 d . . . . .
C13 C 0.4850(8) 0.3996(3) 0.6831(3) 0.055(2) Uani 1 1 d . . . . .
C14 C 0.6130(7) 0.2984(3) 0.4681(3) 0.052(2) Uani 1 1 d . . . . .
H14 H 0.5392 0.3175 0.4690 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7285(7) 0.3219(3) 0.4715(2) 0.0459(18) Uani 1 1 d . . . . .
C16 C 0.432(2) 0.6034(5) 0.7335(5) 0.170(10) Uani 1 1 d . . . . .
H16 H 0.4769 0.6152 0.7602 0.204 Uiso 1 1 calc R U . . .
C17 C 0.7885(8) 0.3495(3) 0.5652(3) 0.0465(19) Uani 1 1 d . . . . .
C18 C 0.6065(8) 0.2481(3) 0.4635(3) 0.056(2) Uani 1 1 d . . . . .
H18 H 0.5278 0.2327 0.4607 0.067 Uiso 1 1 calc R U . . .
C19 C 0.7890(7) 0.2716(3) 0.6113(3) 0.0494(19) Uani 1 1 d . . . . .
H19 H 0.8754 0.2697 0.5987 0.059 Uiso 1 1 calc R U . . .
C20 C 0.7366(7) 0.3783(3) 0.4805(3) 0.0462(19) Uani 1 1 d . . . . .
C21 C 0.7156(7) 0.3846(3) 0.5350(2) 0.0462(19) Uani 1 1 d . . . . .
H21A H 0.7376 0.4189 0.5440 0.055 Uiso 1 1 calc R U . . .
H21B H 0.6266 0.3799 0.5419 0.055 Uiso 1 1 calc R U . . .
C22 C 0.4759(7) 0.3103(3) 0.9049(3) 0.050(2) Uani 1 1 d . . . . .
C23 C 0.5374(7) 0.3314(3) 0.8592(3) 0.056(2) Uani 1 1 d . . . . .
H23A H 0.5586 0.3666 0.8645 0.067 Uiso 1 1 calc R U . . .
H23B H 0.6154 0.3132 0.8531 0.067 Uiso 1 1 calc R U . . .
C24 C 0.3425(8) 0.4638(3) 0.6251(3) 0.055(2) Uani 1 1 d . . . . .
C25 C 0.4556(8) 0.3275(3) 0.8159(3) 0.053(2) Uani 1 1 d . . . . .
C26 C 1.0447(7) 0.3199(3) 0.7803(3) 0.054(2) Uani 1 1 d . . . . .
H26 H 1.0905 0.3319 0.7540 0.064 Uiso 1 1 calc R U . . .
C27 C 0.8589(7) 0.3997(3) 0.4619(3) 0.0470(19) Uani 1 1 d . . . . .
C28 C 0.9586(7) 0.3507(3) 0.8022(3) 0.052(2) Uani 1 1 d . . . . .
C29 C 0.8273(8) 0.3507(3) 0.7161(3) 0.054(2) Uani 1 1 d . . . . .
C30 C 0.4035(8) 0.2835(3) 0.7426(3) 0.055(2) Uani 1 1 d . . . . .
H30 H 0.3182 0.2902 0.7546 0.066 Uiso 1 1 calc R U . . .
C31 C 0.4463(8) 0.2555(3) 0.8934(3) 0.054(2) Uani 1 1 d . . . . .
C32 C 0.9025(8) 0.3855(3) 0.4168(3) 0.061(2) Uani 1 1 d . . . . .
H32 H 0.8574 0.3616 0.3992 0.073 Uiso 1 1 calc R U . . .
C33 C 0.8327(7) 0.2926(3) 0.4716(3) 0.051(2) Uani 1 1 d . . . . .
H33 H 0.9116 0.3077 0.4752 0.061 Uiso 1 1 calc R U . . .
C34 C 0.7975(7) 0.2768(3) 0.6652(3) 0.051(2) Uani 1 1 d . . . . .
H34 H 0.7113 0.2779 0.6780 0.062 Uiso 1 1 calc R U . . .
C35 C 1.0347(9) 0.4537(3) 0.4670(3) 0.070(3) Uani 1 1 d . . . . .
H35 H 1.0806 0.4772 0.4848 0.084 Uiso 1 1 calc R U . . .
C36 C 0.8283(8) 0.4281(3) 0.8091(3) 0.056(2) Uani 1 1 d . . . . .
C37 C 0.3617(7) 0.3401(3) 0.9206(3) 0.055(2) Uani 1 1 d . . . . .
C38 C 0.2276(8) 0.4564(3) 0.6446(3) 0.063(2) Uani 1 1 d . . . . .
H38 H 0.2105 0.4682 0.6756 0.075 Uiso 1 1 calc R U . . .
C39 C 0.7112(9) 0.2194(3) 0.4627(3) 0.060(2) Uani 1 1 d . . . . .
H39 H 0.7046 0.1845 0.4594 0.072 Uiso 1 1 calc R U . . .
C40 C 0.4183(8) 0.3130(3) 0.6966(3) 0.053(2) Uani 1 1 d . . . . .
H40 H 0.5012 0.3051 0.6828 0.063 Uiso 1 1 calc R U . . .
C41 C 1.2442(8) 0.4589(3) 0.8201(3) 0.064(2) Uani 1 1 d . . . . .
H41 H 1.3116 0.4507 0.8403 0.077 Uiso 1 1 calc R U . . .
C42 C 0.6321(7) 0.4073(3) 0.4548(3) 0.049(2) Uani 1 1 d . . . . .
C43 C 1.0766(8) 0.4393(3) 0.4234(3) 0.062(2) Uani 1 1 d . . . . .
H43 H 1.1513 0.4524 0.4109 0.074 Uiso 1 1 calc R U . . .
C44 C 0.4740(8) 0.4525(3) 0.6964(3) 0.059(2) Uani 1 1 d . . . . .
H44A H 0.5524 0.4630 0.7116 0.070 Uiso 1 1 calc R U . . .
H44B H 0.4076 0.4557 0.7204 0.070 Uiso 1 1 calc R U . . .
C45 C 0.6753(9) 0.4854(4) 0.6323(3) 0.071(3) Uani 1 1 d . . . . .
H45 H 0.6904 0.4628 0.6575 0.085 Uiso 1 1 calc R U . . .
C46 C 0.5675(8) 0.3148(3) 0.9460(3) 0.055(2) Uani 1 1 d . . . . .
C47 C 0.9318(7) 0.4023(3) 0.7816(3) 0.052(2) Uani 1 1 d . . . . .
C48 C 0.5583(9) 0.5017(3) 0.6246(3) 0.061(2) Uani 1 1 d . . . . .
C49 C 1.0000(8) 0.2535(3) 0.8341(3) 0.069(2) Uani 1 1 d . . . . .
H49 H 1.0137 0.2204 0.8443 0.083 Uiso 1 1 calc R U . . .
C50 C 0.5972(8) 0.3954(3) 0.4088(3) 0.062(2) Uani 1 1 d . . . . .
H50 H 0.6355 0.3684 0.3930 0.075 Uiso 1 1 calc R U . . .
C51 C 0.5776(8) 0.4477(3) 0.4756(3) 0.061(2) Uani 1 1 d . . . . .
H51 H 0.6032 0.4573 0.5064 0.073 Uiso 1 1 calc R U . . .
C52 C 0.9266(8) 0.4344(3) 0.4854(3) 0.060(2) Uani 1 1 d . . . . .
H52 H 0.8986 0.4457 0.5154 0.072 Uiso 1 1 calc R U . . .
C53 C 0.9047(7) 0.3951(3) 0.7287(3) 0.0498(19) Uani 1 1 d . . . . .
H53A H 0.8621 0.4251 0.7168 0.060 Uiso 1 1 calc R U . . .
H53B H 0.9846 0.3926 0.7117 0.060 Uiso 1 1 calc R U . . .
C54 C 1.1460(8) 0.4261(3) 0.8152(3) 0.059(2) Uani 1 1 d . . . . .
H54 H 1.1470 0.3958 0.8323 0.071 Uiso 1 1 calc R U . . .
C55 C 0.7242(8) 0.2237(3) 0.5982(3) 0.061(2) Uani 1 1 d . . . . .
H55A H 0.7209 0.2204 0.5633 0.073 Uiso 1 1 calc R U . . .
H55B H 0.6383 0.2243 0.6104 0.073 Uiso 1 1 calc R U . . .
C56 C 0.3660(8) 0.4454(3) 0.5798(3) 0.061(2) Uani 1 1 d . . . . .
H56 H 0.4456 0.4497 0.5661 0.073 Uiso 1 1 calc R U . . .
C57 C 0.6441(9) 0.4771(3) 0.8611(4) 0.073(3) Uani 1 1 d . . . . .
H57 H 0.5819 0.4941 0.8785 0.088 Uiso 1 1 calc R U . . .
C58 C 1.0646(8) 0.2725(3) 0.7963(3) 0.062(2) Uani 1 1 d . . . . .
H58 H 1.1244 0.2524 0.7808 0.074 Uiso 1 1 calc R U . . .
C59 C 0.3232(8) 0.2424(3) 0.6507(3) 0.064(2) Uani 1 1 d . . . . .
H59A H 0.2542 0.2334 0.6293 0.077 Uiso 1 1 calc R U . . .
H59B H 0.4018 0.2339 0.6347 0.077 Uiso 1 1 calc R U . . .
C60 C 0.8255(8) 0.2412(3) 0.4668(3) 0.059(2) Uani 1 1 d . . . . .
H60 H 0.8985 0.2216 0.4663 0.070 Uiso 1 1 calc R U . . .
C61 C 0.3623(9) 0.3919(3) 0.9212(3) 0.069(2) Uani 1 1 d . . . . .
H61 H 0.4326 0.4090 0.9093 0.083 Uiso 1 1 calc R U . . .
C62 C 1.1445(9) 0.5149(3) 0.7663(3) 0.069(2) Uani 1 1 d . . . . .
H62 H 1.1424 0.5455 0.7497 0.083 Uiso 1 1 calc R U . . .
C63 C 0.5069(9) 0.4228(4) 0.3857(3) 0.070(3) Uani 1 1 d . . . . .
H63 H 0.4827 0.4139 0.3545 0.084 Uiso 1 1 calc R U . . .
C64 C 0.9148(9) 0.2832(4) 0.8569(3) 0.077(3) Uani 1 1 d . . . . .
H64 H 0.8699 0.2710 0.8834 0.093 Uiso 1 1 calc R U . . .
C65 C 1.2442(9) 0.5038(3) 0.7955(3) 0.065(2) Uani 1 1 d . . . . .
H65 H 1.3112 0.5263 0.7986 0.078 Uiso 1 1 calc R U . . .
C66 C 1.0465(8) 0.4808(3) 0.7613(3) 0.063(2) Uani 1 1 d . . . . .
H66 H 0.9793 0.4882 0.7408 0.076 Uiso 1 1 calc R U . . .
C67 C 0.4516(8) 0.4630(4) 0.4078(4) 0.076(3) Uani 1 1 d . . . . .
H67 H 0.3904 0.4821 0.3920 0.091 Uiso 1 1 calc R U . . .
C68 C 0.3220(9) 0.1936(3) 0.8541(3) 0.066(2) Uani 1 1 d . . . . .
H68 H 0.2500 0.1855 0.8364 0.079 Uiso 1 1 calc R U . . .
C69 C 0.3196(8) 0.2979(3) 0.6607(3) 0.064(2) Uani 1 1 d . . . . .
H69A H 0.2369 0.3070 0.6730 0.077 Uiso 1 1 calc R U . . .
H69B H 0.3330 0.3163 0.6308 0.077 Uiso 1 1 calc R U . . .
C70 C 0.7100(8) 0.4343(3) 0.7909(3) 0.062(2) Uani 1 1 d . . . . .
H70 H 0.6909 0.4218 0.7604 0.074 Uiso 1 1 calc R U . . .
C71 C 0.8514(8) 0.4469(3) 0.8538(3) 0.072(3) Uani 1 1 d . . . . .
H71 H 0.9318 0.4432 0.8669 0.087 Uiso 1 1 calc R U . . .
C72 C 0.4104(8) 0.2281(3) 0.7314(3) 0.062(2) Uani 1 1 d . . . . .
H72A H 0.4932 0.2201 0.7184 0.074 Uiso 1 1 calc R U . . .
H72B H 0.3993 0.2089 0.7610 0.074 Uiso 1 1 calc R U . . .
C73 C 0.4452(7) 0.4892(3) 0.6549(3) 0.055(2) Uani 1 1 d . . . . .
C74 C 0.4010(11) 0.5378(3) 0.6772(4) 0.079(3) Uani 1 1 d . . . . .
C75 C 0.8017(9) 0.1838(3) 0.6721(3) 0.072(3) Uani 1 1 d . . . . .
H75A H 0.8505 0.1556 0.6845 0.086 Uiso 1 1 calc R U . . .
H75B H 0.7177 0.1820 0.6860 0.086 Uiso 1 1 calc R U . . .
C76 C 0.6180(9) 0.4588(3) 0.8172(4) 0.071(3) Uani 1 1 d . . . . .
H76 H 0.5374 0.4627 0.8043 0.086 Uiso 1 1 calc R U . . .
C77 C 0.5288(8) 0.2186(3) 0.9054(3) 0.067(2) Uani 1 1 d . . . . .
H77 H 0.6018 0.2266 0.9225 0.080 Uiso 1 1 calc R U . . .
C78 C 0.3126(9) 0.2132(3) 0.6962(3) 0.069(3) Uani 1 1 d . . . . .
H78A H 0.2297 0.2187 0.7102 0.083 Uiso 1 1 calc R U . . .
H78B H 0.3209 0.1774 0.6891 0.083 Uiso 1 1 calc R U . . .
C79 C 0.1591(9) 0.4154(4) 0.5745(4) 0.078(3) Uani 1 1 d . . . . .
H79 H 0.0945 0.4001 0.5571 0.093 Uiso 1 1 calc R U . . .
C80 C 0.3425(8) 0.2428(3) 0.8670(3) 0.067(2) Uani 1 1 d . . . . .
H80 H 0.2854 0.2677 0.8577 0.080 Uiso 1 1 calc R U . . .
C81 C 0.8624(8) 0.2319(3) 0.6866(3) 0.065(2) Uani 1 1 d . . . . .
H81A H 0.9500 0.2316 0.6764 0.077 Uiso 1 1 calc R U . . .
H81B H 0.8610 0.2346 0.7216 0.077 Uiso 1 1 calc R U . . .
C82 C 0.2745(10) 0.4207(3) 0.5545(3) 0.072(3) Uani 1 1 d . . . . .
H82 H 0.2913 0.4077 0.5239 0.087 Uiso 1 1 calc R U . . .
C83 C 0.5054(9) 0.1696(3) 0.8923(4) 0.074(3) Uani 1 1 d . . . . .
H83 H 0.5617 0.1443 0.9015 0.088 Uiso 1 1 calc R U . . .
C84 C 0.5408(9) 0.5351(3) 0.5874(3) 0.070(3) Uani 1 1 d . . . . .
H84 H 0.4603 0.5480 0.5820 0.084 Uiso 1 1 calc R U . . .
C85 C 0.6796(9) 0.3401(3) 0.9431(3) 0.070(2) Uani 1 1 d . . . . .
H85 H 0.7015 0.3562 0.9144 0.084 Uiso 1 1 calc R U . . .
C86 C 0.7609(10) 0.4710(3) 0.8804(4) 0.078(3) Uani 1 1 d . . . . .
H86 H 0.7791 0.4830 0.9112 0.094 Uiso 1 1 calc R U . . .
C87 C 0.7931(8) 0.1800(3) 0.6192(3) 0.062(2) Uani 1 1 d . . . . .
H87A H 0.7498 0.1490 0.6106 0.074 Uiso 1 1 calc R U . . .
H87B H 0.8775 0.1786 0.6057 0.074 Uiso 1 1 calc R U . . .
C88 C 0.4024(9) 0.1572(4) 0.8662(3) 0.068(2) Uani 1 1 d . . . . .
H88 H 0.3879 0.1238 0.8569 0.082 Uiso 1 1 calc R U . . .
C89 C 0.2650(10) 0.4186(3) 0.9382(4) 0.082(3) Uani 1 1 d . . . . .
H89 H 0.2683 0.4537 0.9388 0.099 Uiso 1 1 calc R U . . .
C90 C 0.4879(9) 0.4745(4) 0.4533(4) 0.077(3) Uani 1 1 d . . . . .
H90 H 0.4499 0.5014 0.4694 0.092 Uiso 1 1 calc R U . . .
C91 C 0.8955(8) 0.3317(3) 0.8405(3) 0.070(2) Uani 1 1 d . . . . .
H91 H 0.8369 0.3520 0.8562 0.084 Uiso 1 1 calc R U . . .
C92 C 1.0081(8) 0.4052(3) 0.3979(3) 0.067(2) Uani 1 1 d . . . . .
H92 H 1.0345 0.3954 0.3672 0.080 Uiso 1 1 calc R U . . .
C93 C 0.6362(13) 0.5498(4) 0.5583(4) 0.086(3) Uani 1 1 d . . . . .
H93 H 0.6205 0.5715 0.5325 0.103 Uiso 1 1 calc R U . . .
C94 C 0.7294(11) 0.3211(4) 1.0236(4) 0.085(3) Uani 1 1 d . . . . .
H94 H 0.7851 0.3226 1.0496 0.102 Uiso 1 1 calc R U . . .
C95 C 0.7508(13) 0.5334(4) 0.5665(5) 0.094(4) Uani 1 1 d . . . . .
H95 H 0.8170 0.5437 0.5467 0.112 Uiso 1 1 calc R U . . .
C96 C 0.7597(9) 0.3423(4) 0.9813(4) 0.077(3) Uani 1 1 d . . . . .
H96 H 0.8369 0.3587 0.9780 0.092 Uiso 1 1 calc R U . . .
C97 C 0.5389(9) 0.2939(3) 0.9897(3) 0.068(2) Uani 1 1 d . . . . .
H97 H 0.4627 0.2766 0.9930 0.081 Uiso 1 1 calc R U . . .
C98 C 0.7739(10) 0.5010(4) 0.6042(4) 0.089(3) Uani 1 1 d . . . . .
H98 H 0.8556 0.4898 0.6105 0.107 Uiso 1 1 calc R U . . .
C99 C 0.2579(9) 0.3171(3) 0.9398(4) 0.083(3) Uani 1 1 d . . . . .
H99 H 0.2554 0.2819 0.9414 0.100 Uiso 1 1 calc R U . . .
C100 C 0.1371(9) 0.4321(4) 0.6195(4) 0.078(3) Uani 1 1 d . . . . .
H100 H 0.0583 0.4269 0.6335 0.094 Uiso 1 1 calc R U . . .
C101 C 0.6154(11) 0.2971(4) 1.0281(4) 0.081(3) Uani 1 1 d . . . . .
H101 H 0.5914 0.2831 1.0576 0.097 Uiso 1 1 calc R U . . .
C102 C 0.4651(14) 0.5587(4) 0.7134(4) 0.107(4) Uani 1 1 d . . . . .
H102 H 0.5355 0.5418 0.7254 0.129 Uiso 1 1 calc R U . . .
C103 C 1.0475(7) 0.4365(3) 0.7862(3) 0.054(2) Uani 1 1 d . . . . .
C105 C 0.3026(12) 0.5649(4) 0.6587(5) 0.112(4) Uani 1 1 d . . . . .
H105 H 0.2569 0.5526 0.6325 0.134 Uiso 1 1 calc R U . . .
C106 C 0.1615(11) 0.3940(4) 0.9545(4) 0.107(4) Uani 1 1 d . . . . .
H106 H 0.0912 0.4123 0.9646 0.128 Uiso 1 1 calc R U . . .
C107 C 0.2717(17) 0.6105(5) 0.6790(7) 0.158(8) Uani 1 1 d . . . . .
H107 H 0.2024 0.6282 0.6671 0.189 Uiso 1 1 calc R U . . .
C108 C 0.1599(10) 0.3436(4) 0.9563(5) 0.111(4) Uani 1 1 d . . . . .
H108 H 0.0902 0.3269 0.9691 0.134 Uiso 1 1 calc R U . . .
C114 C 0.339(3) 0.6305(6) 0.7159(9) 0.192(13) Uani 1 1 d . . . . .
H114 H 0.3198 0.6623 0.7284 0.230 Uiso 1 1 calc R U . . .
O201 O 0.9079(13) 0.6137(5) 0.7811(5) 0.191(5) Uani 1 1 d D . . . .
C202 C 0.8104(15) 0.5743(6) 0.7827(6) 0.150(6) Uani 1 1 d D . . . .
H20A H 0.8396 0.5458 0.8017 0.180 Uiso 1 1 calc R U . . .
H20B H 0.7340 0.5874 0.7974 0.180 Uiso 1 1 calc R U . . .
C203 C 0.7855(15) 0.5587(10) 0.7340(8) 0.236(13) Uani 1 1 d D . . . .
H20C H 0.6983 0.5659 0.7257 0.283 Uiso 1 1 calc R U . . .
H20D H 0.7992 0.5226 0.7308 0.283 Uiso 1 1 calc R U . . .
C204 C 0.871(2) 0.5863(8) 0.7016(7) 0.208(10) Uani 1 1 d D . . . .
H20E H 0.8261 0.5981 0.6731 0.250 Uiso 1 1 calc R U . . .
H20F H 0.9406 0.5650 0.6915 0.250 Uiso 1 1 calc R U . . .
C205 C 0.918(2) 0.6309(6) 0.7319(7) 0.219(11) Uani 1 1 d D . . . .
H20G H 1.0047 0.6391 0.7240 0.263 Uiso 1 1 calc R U . . .
H20H H 0.8659 0.6606 0.7267 0.263 Uiso 1 1 calc R U . . .
O206 O 0.049(2) 0.6444(10) 0.6164(8) 0.356(11) Uani 1 1 d D U . . .
C207 C 0.007(3) 0.5937(11) 0.6018(10) 0.321(14) Uani 1 1 d D U . . .
H20I H 0.0352 0.5685 0.6248 0.386 Uiso 1 1 calc R U . . .
H20J H -0.0848 0.5924 0.5999 0.386 Uiso 1 1 calc R U . . .
C208 C 0.063(3) 0.5850(12) 0.5544(10) 0.333(14) Uani 1 1 d D U . . .
H20K H 0.0067 0.5966 0.5290 0.400 Uiso 1 1 calc R U . . .
H20L H 0.0797 0.5493 0.5496 0.400 Uiso 1 1 calc R U . . .
C209 C 0.182(3) 0.6145(14) 0.5541(11) 0.374(16) Uani 1 1 d D U . . .
H20M H 0.2033 0.6253 0.5217 0.449 Uiso 1 1 calc R U . . .
H20N H 0.2513 0.5946 0.5670 0.449 Uiso 1 1 calc R U . . .
C210 C 0.154(3) 0.6602(11) 0.5869(12) 0.381(16) Uani 1 1 d D U . . .
H21C H 0.2266 0.6684 0.6068 0.458 Uiso 1 1 calc R U . . .
H21D H 0.1319 0.6896 0.5677 0.458 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXD Version 2013/2 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N9 1.402(7) . ?
O1 H1 0.8400 . ?
O2 C13 1.267(9) . ?
O3 C17 1.244(8) . ?
O4 C25 1.253(9) . ?
O5 N11 1.414(8) . ?
O5 H5 0.8400 . ?
O6 C29 1.232(9) . ?
O7 N10 1.402(7) . ?
O7 H7 0.8400 . ?
O8 N12 1.402(8) . ?
O8 H8 0.8400 . ?
N9 C17 1.337(9) . ?
N9 C19 1.458(9) . ?
N10 C13 1.353(10) . ?
N10 C40 1.449(9) . ?
N11 C29 1.349(10) . ?
N11 C34 1.462(9) . ?
N12 C25 1.354(10) . ?
N12 C30 1.438(10) . ?
C13 C44 1.483(11) . ?
C14 C18 1.367(10) . ?
C14 C15 1.403(10) . ?
C14 H14 0.9500 . ?
C15 C33 1.377(10) . ?
C15 C20 1.547(10) . ?
C16 C114 1.34(3) . ?
C16 C102 1.380(16) . ?
C16 H16 0.9500 . ?
C17 C21 1.498(10) . ?
C18 C39 1.372(11) . ?
C18 H18 0.9500 . ?
C19 C55 1.516(10) . ?
C19 C34 1.529(10) . ?
C19 H19 1.0000 . ?
C20 C27 1.535(10) . ?
C20 C42 1.553(10) . ?
C20 C21 1.567(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C46 1.529(11) . ?
C22 C37 1.539(11) . ?
C22 C31 1.547(10) . ?
C22 C23 1.560(11) . ?
C23 C25 1.513(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C38 1.373(11) . ?
C24 C56 1.395(11) . ?
C24 C73 1.553(11) . ?
C26 C58 1.374(10) . ?
C26 C28 1.392(10) . ?
C26 H26 0.9500 . ?
C27 C52 1.363(10) . ?
C27 C32 1.409(11) . ?
C28 C91 1.377(11) . ?
C28 C47 1.539(11) . ?
C29 C53 1.506(10) . ?
C30 C72 1.530(10) . ?
C30 C40 1.533(10) . ?
C30 H30 1.0000 . ?
C31 C77 1.379(11) . ?
C31 C80 1.390(11) . ?
C32 C92 1.368(11) . ?
C32 H32 0.9500 . ?
C33 C60 1.397(10) . ?
C33 H33 0.9500 . ?
C34 C81 1.527(10) . ?
C34 H34 1.0000 . ?
C35 C43 1.366(12) . ?
C35 C52 1.381(11) . ?
C35 H35 0.9500 . ?
C36 C71 1.385(11) . ?
C36 C70 1.387(11) . ?
C36 C47 1.529(11) . ?
C37 C99 1.391(11) . ?
C37 C61 1.400(11) . ?
C38 C100 1.375(13) . ?
C38 H38 0.9500 . ?
C39 C60 1.373(11) . ?
C39 H39 0.9500 . ?
C40 C69 1.526(11) . ?
C40 H40 1.0000 . ?
C41 C54 1.388(11) . ?
C41 C65 1.399(12) . ?
C41 H41 0.9500 . ?
C42 C51 1.372(10) . ?
C42 C50 1.390(11) . ?
C43 C92 1.383(11) . ?
C43 H43 0.9500 . ?
C44 C73 1.564(11) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C48 1.356(12) . ?
C45 C98 1.394(13) . ?
C45 H45 0.9500 . ?
C46 C97 1.393(11) . ?
C46 C85 1.394(11) . ?
C47 C53 1.536(10) . ?
C47 C103 1.560(11) . ?
C48 C84 1.396(12) . ?
C48 C73 1.530(11) . ?
C49 C58 1.375(11) . ?
C49 C64 1.382(12) . ?
C49 H49 0.9500 . ?
C50 C63 1.387(11) . ?
C50 H50 0.9500 . ?
C51 C90 1.364(11) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C103 1.373(11) . ?
C54 H54 0.9500 . ?
C55 C87 1.517(11) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 C82 1.390(11) . ?
C56 H56 0.9500 . ?
C57 C76 1.366(12) . ?
C57 C86 1.385(13) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C59 C78 1.512(11) . ?
C59 C69 1.527(11) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 H60 0.9500 . ?
C61 C89 1.362(12) . ?
C61 H61 0.9500 . ?
C62 C65 1.388(12) . ?
C62 C66 1.411(11) . ?
C62 H62 0.9500 . ?
C63 C67 1.388(13) . ?
C63 H63 0.9500 . ?
C64 C91 1.404(12) . ?
C64 H64 0.9500 . ?
C65 H65 0.9500 . ?
C66 C103 1.386(11) . ?
C66 H66 0.9500 . ?
C67 C90 1.379(13) . ?
C67 H67 0.9500 . ?
C68 C88 1.358(11) . ?
C68 C80 1.395(11) . ?
C68 H68 0.9500 . ?
C69 H69A 0.9900 . ?
C69 H69B 0.9900 . ?
C70 C76 1.406(11) . ?
C70 H70 0.9500 . ?
C71 C86 1.394(12) . ?
C71 H71 0.9500 . ?
C72 C78 1.506(11) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.532(12) . ?
C74 C102 1.358(15) . ?
C74 C105 1.393(15) . ?
C75 C87 1.500(11) . ?
C75 C81 1.511(11) . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
C76 H76 0.9500 . ?
C77 C83 1.399(12) . ?
C77 H77 0.9500 . ?
C78 H78A 0.9900 . ?
C78 H78B 0.9900 . ?
C79 C100 1.367(13) . ?
C79 C82 1.377(13) . ?
C79 H79 0.9500 . ?
C80 H80 0.9500 . ?
C81 H81A 0.9900 . ?
C81 H81B 0.9900 . ?
C82 H82 0.9500 . ?
C83 C88 1.375(12) . ?
C83 H83 0.9500 . ?
C84 C93 1.378(13) . ?
C84 H84 0.9500 . ?
C85 C96 1.384(12) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C87 H87A 0.9900 . ?
C87 H87B 0.9900 . ?
C88 H88 0.9500 . ?
C89 C106 1.379(14) . ?
C89 H89 0.9500 . ?
C90 H90 0.9500 . ?
C91 H91 0.9500 . ?
C92 H92 0.9500 . ?
C93 C95 1.337(15) . ?
C93 H93 0.9500 . ?
C94 C96 1.363(13) . ?
C94 C101 1.398(14) . ?
C94 H94 0.9500 . ?
C95 C98 1.399(15) . ?
C95 H95 0.9500 . ?
C96 H96 0.9500 . ?
C97 C101 1.367(12) . ?
C97 H97 0.9500 . ?
C98 H98 0.9500 . ?
C99 C108 1.361(12) . ?
C99 H99 0.9500 . ?
C100 H100 0.9500 . ?
C101 H101 0.9500 . ?
C102 H102 0.9500 . ?
C105 C107 1.399(16) . ?
C105 H105 0.9500 . ?
C106 C108 1.362(13) . ?
C106 H106 0.9500 . ?
C107 C114 1.38(3) . ?
C107 H107 0.9500 . ?
C108 H108 0.9500 . ?
C114 H114 0.9500 . ?
O201 C205 1.468(17) . ?
O201 C202 1.498(15) . ?
C202 C203 1.462(18) . ?
C202 H20A 0.9900 . ?
C202 H20B 0.9900 . ?
C203 C204 1.50(2) . ?
C203 H20C 0.9900 . ?
C203 H20D 0.9900 . ?
C204 C205 1.56(2) . ?
C204 H20E 0.9900 . ?
C204 H20F 0.9900 . ?
C205 H20G 0.9900 . ?
C205 H20H 0.9900 . ?
O206 C210 1.472(19) . ?
O206 C207 1.501(18) . ?
C207 C208 1.49(2) . ?
C207 H20I 0.9900 . ?
C207 H20J 0.9900 . ?
C208 C209 1.51(2) . ?
C208 H20K 0.9900 . ?
C208 H20L 0.9900 . ?
C209 C210 1.57(2) . ?
C209 H20M 0.9900 . ?
C209 H20N 0.9900 . ?
C210 H21C 0.9900 . ?
C210 H21D 0.9900 . ?

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
N9 O1 H1 109.5 . . ?
N11 O5 H5 109.5 . . ?
N10 O7 H7 109.5 . . ?
N12 O8 H8 109.5 . . ?
C17 N9 O1 120.1(6) . . ?
C17 N9 C19 124.3(6) . . ?
O1 N9 C19 115.4(6) . . ?
C13 N10 O7 117.4(6) . . ?
C13 N10 C40 124.0(7) . . ?
O7 N10 C40 116.0(6) . . ?
C29 N11 O5 119.4(6) . . ?
C29 N11 C34 123.7(7) . . ?
O5 N11 C34 114.0(6) . . ?
C25 N12 O8 120.0(7) . . ?
C25 N12 C30 122.8(7) . . ?
O8 N12 C30 116.2(6) . . ?
O2 C13 N10 119.5(8) . . ?
O2 C13 C44 121.3(8) . . ?
N10 C13 C44 119.0(8) . . ?
C18 C14 C15 120.0(8) . . ?
C18 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C33 C15 C14 118.0(7) . . ?
C33 C15 C20 121.2(7) . . ?
C14 C15 C20 120.4(7) . . ?
C114 C16 C102 121(2) . . ?
C114 C16 H16 119.4 . . ?
C102 C16 H16 119.4 . . ?
O3 C17 N9 119.3(7) . . ?
O3 C17 C21 121.6(7) . . ?
N9 C17 C21 119.0(7) . . ?
C14 C18 C39 121.4(8) . . ?
C14 C18 H18 119.3 . . ?
C39 C18 H18 119.3 . . ?
N9 C19 C55 110.8(6) . . ?
N9 C19 C34 112.8(6) . . ?
C55 C19 C34 110.4(6) . . ?
N9 C19 H19 107.6 . . ?
C55 C19 H19 107.6 . . ?
C34 C19 H19 107.6 . . ?
C27 C20 C15 111.3(6) . . ?
C27 C20 C42 106.1(5) . . ?
C15 C20 C42 112.2(6) . . ?
C27 C20 C21 114.9(6) . . ?
C15 C20 C21 105.1(5) . . ?
C42 C20 C21 107.4(6) . . ?
C17 C21 C20 114.5(6) . . ?
C17 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C17 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C46 C22 C37 105.0(6) . . ?
C46 C22 C31 111.6(6) . . ?
C37 C22 C31 113.2(6) . . ?
C46 C22 C23 108.9(6) . . ?
C37 C22 C23 112.9(6) . . ?
C31 C22 C23 105.3(6) . . ?
C25 C23 C22 113.2(6) . . ?
C25 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C25 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C38 C24 C56 118.7(8) . . ?
C38 C24 C73 119.5(8) . . ?
C56 C24 C73 121.6(7) . . ?
O4 C25 N12 119.6(7) . . ?
O4 C25 C23 120.2(7) . . ?
N12 C25 C23 120.2(7) . . ?
C58 C26 C28 121.0(8) . . ?
C58 C26 H26 119.5 . . ?
C28 C26 H26 119.5 . . ?
C52 C27 C32 116.6(7) . . ?
C52 C27 C20 123.7(7) . . ?
C32 C27 C20 119.6(7) . . ?
C91 C28 C26 117.1(8) . . ?
C91 C28 C47 122.8(7) . . ?
C26 C28 C47 119.9(7) . . ?
O6 C29 N11 119.5(8) . . ?
O6 C29 C53 121.4(8) . . ?
N11 C29 C53 119.1(7) . . ?
N12 C30 C72 112.0(7) . . ?
N12 C30 C40 114.4(6) . . ?
C72 C30 C40 109.2(6) . . ?
N12 C30 H30 106.9 . . ?
C72 C30 H30 106.9 . . ?
C40 C30 H30 106.9 . . ?
C77 C31 C80 118.4(8) . . ?
C77 C31 C22 120.3(7) . . ?
C80 C31 C22 121.0(7) . . ?
C92 C32 C27 121.7(8) . . ?
C92 C32 H32 119.2 . . ?
C27 C32 H32 119.2 . . ?
C15 C33 C60 121.7(8) . . ?
C15 C33 H33 119.2 . . ?
C60 C33 H33 119.2 . . ?
N11 C34 C81 111.9(6) . . ?
N11 C34 C19 110.7(6) . . ?
C81 C34 C19 110.4(6) . . ?
N11 C34 H34 107.9 . . ?
C81 C34 H34 107.9 . . ?
C19 C34 H34 107.9 . . ?
C43 C35 C52 120.8(8) . . ?
C43 C35 H35 119.6 . . ?
C52 C35 H35 119.6 . . ?
C71 C36 C70 117.3(8) . . ?
C71 C36 C47 119.9(7) . . ?
C70 C36 C47 122.8(8) . . ?
C99 C37 C61 116.5(8) . . ?
C99 C37 C22 121.7(7) . . ?
C61 C37 C22 121.5(8) . . ?
C24 C38 C100 120.4(9) . . ?
C24 C38 H38 119.8 . . ?
C100 C38 H38 119.8 . . ?
C18 C39 C60 119.9(7) . . ?
C18 C39 H39 120.0 . . ?
C60 C39 H39 120.0 . . ?
N10 C40 C69 110.9(7) . . ?
N10 C40 C30 111.0(6) . . ?
C69 C40 C30 110.5(7) . . ?
N10 C40 H40 108.1 . . ?
C69 C40 H40 108.1 . . ?
C30 C40 H40 108.1 . . ?
C54 C41 C65 120.1(9) . . ?
C54 C41 H41 120.0 . . ?
C65 C41 H41 120.0 . . ?
C51 C42 C50 117.8(7) . . ?
C51 C42 C20 120.9(7) . . ?
C50 C42 C20 121.2(7) . . ?
C35 C43 C92 118.7(8) . . ?
C35 C43 H43 120.6 . . ?
C92 C43 H43 120.6 . . ?
C13 C44 C73 115.9(7) . . ?
C13 C44 H44A 108.3 . . ?
C73 C44 H44A 108.3 . . ?
C13 C44 H44B 108.3 . . ?
C73 C44 H44B 108.3 . . ?
H44A C44 H44B 107.4 . . ?
C48 C45 C98 121.5(10) . . ?
C48 C45 H45 119.2 . . ?
C98 C45 H45 119.2 . . ?
C97 C46 C85 116.3(8) . . ?
C97 C46 C22 119.8(8) . . ?
C85 C46 C22 123.9(7) . . ?
C36 C47 C53 114.3(6) . . ?
C36 C47 C28 111.0(6) . . ?
C53 C47 C28 106.8(6) . . ?
C36 C47 C103 106.0(6) . . ?
C53 C47 C103 108.0(6) . . ?
C28 C47 C103 110.8(6) . . ?
C45 C48 C84 117.2(9) . . ?
C45 C48 C73 125.6(8) . . ?
C84 C48 C73 117.1(8) . . ?
C58 C49 C64 119.0(8) . . ?
C58 C49 H49 120.5 . . ?
C64 C49 H49 120.5 . . ?
C63 C50 C42 120.5(9) . . ?
C63 C50 H50 119.7 . . ?
C42 C50 H50 119.7 . . ?
C90 C51 C42 122.1(9) . . ?
C90 C51 H51 119.0 . . ?
C42 C51 H51 119.0 . . ?
C27 C52 C35 122.0(8) . . ?
C27 C52 H52 119.0 . . ?
C35 C52 H52 119.0 . . ?
C29 C53 C47 115.9(6) . . ?
C29 C53 H53A 108.3 . . ?
C47 C53 H53A 108.3 . . ?
C29 C53 H53B 108.3 . . ?
C47 C53 H53B 108.3 . . ?
H53A C53 H53B 107.4 . . ?
C103 C54 C41 121.5(8) . . ?
C103 C54 H54 119.2 . . ?
C41 C54 H54 119.2 . . ?
C19 C55 C87 110.0(7) . . ?
C19 C55 H55A 109.7 . . ?
C87 C55 H55A 109.7 . . ?
C19 C55 H55B 109.7 . . ?
C87 C55 H55B 109.7 . . ?
H55A C55 H55B 108.2 . . ?
C82 C56 C24 120.8(9) . . ?
C82 C56 H56 119.6 . . ?
C24 C56 H56 119.6 . . ?
C76 C57 C86 120.1(8) . . ?
C76 C57 H57 119.9 . . ?
C86 C57 H57 119.9 . . ?
C26 C58 C49 121.5(8) . . ?
C26 C58 H58 119.2 . . ?
C49 C58 H58 119.2 . . ?
C78 C59 C69 110.7(7) . . ?
C78 C59 H59A 109.5 . . ?
C69 C59 H59A 109.5 . . ?
C78 C59 H59B 109.5 . . ?
C69 C59 H59B 109.5 . . ?
H59A C59 H59B 108.1 . . ?
C39 C60 C33 119.0(8) . . ?
C39 C60 H60 120.5 . . ?
C33 C60 H60 120.5 . . ?
C89 C61 C37 121.9(9) . . ?
C89 C61 H61 119.1 . . ?
C37 C61 H61 119.1 . . ?
C65 C62 C66 120.0(8) . . ?
C65 C62 H62 120.0 . . ?
C66 C62 H62 120.0 . . ?
C50 C63 C67 120.6(9) . . ?
C50 C63 H63 119.7 . . ?
C67 C63 H63 119.7 . . ?
C49 C64 C91 119.0(9) . . ?
C49 C64 H64 120.5 . . ?
C91 C64 H64 120.5 . . ?
C62 C65 C41 118.9(8) . . ?
C62 C65 H65 120.5 . . ?
C41 C65 H65 120.5 . . ?
C103 C66 C62 120.4(8) . . ?
C103 C66 H66 119.8 . . ?
C62 C66 H66 119.8 . . ?
C90 C67 C63 118.2(9) . . ?
C90 C67 H67 120.9 . . ?
C63 C67 H67 120.9 . . ?
C88 C68 C80 121.5(9) . . ?
C88 C68 H68 119.2 . . ?
C80 C68 H68 119.2 . . ?
C59 C69 C40 111.6(7) . . ?
C59 C69 H69A 109.3 . . ?
C40 C69 H69A 109.3 . . ?
C59 C69 H69B 109.3 . . ?
C40 C69 H69B 109.3 . . ?
H69A C69 H69B 108.0 . . ?
C36 C70 C76 120.9(9) . . ?
C36 C70 H70 119.5 . . ?
C76 C70 H70 119.5 . . ?
C36 C71 C86 122.4(9) . . ?
C36 C71 H71 118.8 . . ?
C86 C71 H71 118.8 . . ?
C78 C72 C30 111.3(7) . . ?
C78 C72 H72A 109.4 . . ?
C30 C72 H72A 109.4 . . ?
C78 C72 H72B 109.4 . . ?
C30 C72 H72B 109.4 . . ?
H72A C72 H72B 108.0 . . ?
C48 C73 C74 106.8(6) . . ?
C48 C73 C24 111.4(6) . . ?
C74 C73 C24 112.2(8) . . ?
C48 C73 C44 113.6(7) . . ?
C74 C73 C44 107.2(7) . . ?
C24 C73 C44 105.7(6) . . ?
C102 C74 C105 116.9(11) . . ?
C102 C74 C73 120.4(12) . . ?
C105 C74 C73 122.4(10) . . ?
C87 C75 C81 110.8(7) . . ?
C87 C75 H75A 109.5 . . ?
C81 C75 H75A 109.5 . . ?
C87 C75 H75B 109.5 . . ?
C81 C75 H75B 109.5 . . ?
H75A C75 H75B 108.1 . . ?
C57 C76 C70 120.2(9) . . ?
C57 C76 H76 119.9 . . ?
C70 C76 H76 119.9 . . ?
C31 C77 C83 120.1(9) . . ?
C31 C77 H77 119.9 . . ?
C83 C77 H77 119.9 . . ?
C72 C78 C59 111.6(7) . . ?
C72 C78 H78A 109.3 . . ?
C59 C78 H78A 109.3 . . ?
C72 C78 H78B 109.3 . . ?
C59 C78 H78B 109.3 . . ?
H78A C78 H78B 108.0 . . ?
C100 C79 C82 120.3(9) . . ?
C100 C79 H79 119.9 . . ?
C82 C79 H79 119.9 . . ?
C31 C80 C68 120.2(8) . . ?
C31 C80 H80 119.9 . . ?
C68 C80 H80 119.9 . . ?
C75 C81 C34 112.1(7) . . ?
C75 C81 H81A 109.2 . . ?
C34 C81 H81A 109.2 . . ?
C75 C81 H81B 109.2 . . ?
C34 C81 H81B 109.2 . . ?
H81A C81 H81B 107.9 . . ?
C79 C82 C56 118.9(9) . . ?
C79 C82 H82 120.5 . . ?
C56 C82 H82 120.5 . . ?
C88 C83 C77 121.3(9) . . ?
C88 C83 H83 119.4 . . ?
C77 C83 H83 119.4 . . ?
C93 C84 C48 122.3(10) . . ?
C93 C84 H84 118.8 . . ?
C48 C84 H84 118.8 . . ?
C96 C85 C46 121.3(9) . . ?
C96 C85 H85 119.4 . . ?
C46 C85 H85 119.4 . . ?
C57 C86 C71 118.9(9) . . ?
C57 C86 H86 120.5 . . ?
C71 C86 H86 120.5 . . ?
C75 C87 C55 111.5(7) . . ?
C75 C87 H87A 109.3 . . ?
C55 C87 H87A 109.3 . . ?
C75 C87 H87B 109.3 . . ?
C55 C87 H87B 109.3 . . ?
H87A C87 H87B 108.0 . . ?
C68 C88 C83 118.4(9) . . ?
C68 C88 H88 120.8 . . ?
C83 C88 H88 120.8 . . ?
C61 C89 C106 119.4(9) . . ?
C61 C89 H89 120.3 . . ?
C106 C89 H89 120.3 . . ?
C51 C90 C67 120.8(10) . . ?
C51 C90 H90 119.6 . . ?
C67 C90 H90 119.6 . . ?
C28 C91 C64 122.3(9) . . ?
C28 C91 H91 118.8 . . ?
C64 C91 H91 118.8 . . ?
C32 C92 C43 120.1(9) . . ?
C32 C92 H92 119.9 . . ?
C43 C92 H92 119.9 . . ?
C95 C93 C84 119.5(11) . . ?
C95 C93 H93 120.2 . . ?
C84 C93 H93 120.2 . . ?
C96 C94 C101 119.1(10) . . ?
C96 C94 H94 120.4 . . ?
C101 C94 H94 120.4 . . ?
C93 C95 C98 120.4(11) . . ?
C93 C95 H95 119.8 . . ?
C98 C95 H95 119.8 . . ?
C94 C96 C85 121.0(10) . . ?
C94 C96 H96 119.5 . . ?
C85 C96 H96 119.5 . . ?
C101 C97 C46 122.9(9) . . ?
C101 C97 H97 118.5 . . ?
C46 C97 H97 118.5 . . ?
C45 C98 C95 119.0(10) . . ?
C45 C98 H98 120.5 . . ?
C95 C98 H98 120.5 . . ?
C108 C99 C37 121.7(9) . . ?
C108 C99 H99 119.2 . . ?
C37 C99 H99 119.2 . . ?
C79 C100 C38 120.8(9) . . ?
C79 C100 H100 119.6 . . ?
C38 C100 H100 119.6 . . ?
C97 C101 C94 119.3(10) . . ?
C97 C101 H101 120.3 . . ?
C94 C101 H101 120.3 . . ?
C74 C102 C16 122.9(16) . . ?
C74 C102 H102 118.5 . . ?
C16 C102 H102 118.5 . . ?
C54 C103 C66 119.0(8) . . ?
C54 C103 C47 123.4(7) . . ?
C66 C103 C47 117.5(7) . . ?
C74 C105 C107 119.5(15) . . ?
C74 C105 H105 120.3 . . ?
C107 C105 H105 120.3 . . ?
C108 C106 C89 120.1(10) . . ?
C108 C106 H106 119.9 . . ?
C89 C106 H106 119.9 . . ?
C114 C107 C105 121.9(19) . . ?
C114 C107 H107 119.0 . . ?
C105 C107 H107 119.0 . . ?
C99 C108 C106 120.3(10) . . ?
C99 C108 H108 119.9 . . ?
C106 C108 H108 119.9 . . ?
C16 C114 C107 117.5(16) . . ?
C16 C114 H114 121.3 . . ?
C107 C114 H114 121.3 . . ?
C205 O201 C202 107.7(15) . . ?
C203 C202 O201 107.9(15) . . ?
C203 C202 H20A 110.1 . . ?
O201 C202 H20A 110.1 . . ?
C203 C202 H20B 110.1 . . ?
O201 C202 H20B 110.1 . . ?
H20A C202 H20B 108.4 . . ?
C202 C203 C204 108.5(16) . . ?
C202 C203 H20C 110.0 . . ?
C204 C203 H20C 110.0 . . ?
C202 C203 H20D 110.0 . . ?
C204 C203 H20D 110.0 . . ?
H20C C203 H20D 108.4 . . ?
C203 C204 C205 104.4(16) . . ?
C203 C204 H20E 110.9 . . ?
C205 C204 H20E 110.9 . . ?
C203 C204 H20F 110.9 . . ?
C205 C204 H20F 110.9 . . ?
H20E C204 H20F 108.9 . . ?
O201 C205 C204 104.5(14) . . ?
O201 C205 H20G 110.9 . . ?
C204 C205 H20G 110.9 . . ?
O201 C205 H20H 110.9 . . ?
C204 C205 H20H 110.9 . . ?
H20G C205 H20H 108.9 . . ?
C210 O206 C207 110.1(17) . . ?
C208 C207 O206 105.5(18) . . ?
C208 C207 H20I 110.6 . . ?
O206 C207 H20I 110.6 . . ?
C208 C207 H20J 110.6 . . ?
O206 C207 H20J 110.6 . . ?
H20I C207 H20J 108.8 . . ?
C207 C208 C209 105.5(19) . . ?
C207 C208 H20K 110.6 . . ?
C209 C208 H20K 110.6 . . ?
C207 C208 H20L 110.6 . . ?
C209 C208 H20L 110.6 . . ?
H20K C208 H20L 108.8 . . ?
C208 C209 C210 104.2(18) . . ?
C208 C209 H20M 110.9 . . ?
C210 C209 H20M 110.9 . . ?
C208 C209 H20N 110.9 . . ?
C210 C209 H20N 110.9 . . ?
H20M C209 H20N 108.9 . . ?
O206 C210 C209 104.7(18) . . ?
O206 C210 H21C 110.8 . . ?
C209 C210 H21C 110.8 . . ?
O206 C210 H21D 110.8 . . ?
C209 C210 H21D 110.8 . . ?
H21C C210 H21D 108.9 . . ?

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
O7 N10 C13 O2 -164.7(6) . . . . ?
C40 N10 C13 O2 -4.0(11) . . . . ?
O7 N10 C13 C44 20.9(10) . . . . ?
C40 N10 C13 C44 -178.5(7) . . . . ?
C18 C14 C15 C33 -2.3(11) . . . . ?
C18 C14 C15 C20 -175.4(7) . . . . ?
O1 N9 C17 O3 173.2(6) . . . . ?
C19 N9 C17 O3 -11.1(11) . . . . ?
O1 N9 C17 C21 -8.9(10) . . . . ?
C19 N9 C17 C21 166.8(6) . . . . ?
C15 C14 C18 C39 1.0(12) . . . . ?
C17 N9 C19 C55 -131.8(7) . . . . ?
O1 N9 C19 C55 44.2(8) . . . . ?
C17 N9 C19 C34 103.9(8) . . . . ?
O1 N9 C19 C34 -80.1(8) . . . . ?
C33 C15 C20 C27 32.0(9) . . . . ?
C14 C15 C20 C27 -155.1(7) . . . . ?
C33 C15 C20 C42 150.7(7) . . . . ?
C14 C15 C20 C42 -36.4(9) . . . . ?
C33 C15 C20 C21 -93.0(8) . . . . ?
C14 C15 C20 C21 80.0(8) . . . . ?
O3 C17 C21 C20 67.0(9) . . . . ?
N9 C17 C21 C20 -110.8(7) . . . . ?
C27 C20 C21 C17 -76.4(8) . . . . ?
C15 C20 C21 C17 46.3(8) . . . . ?
C42 C20 C21 C17 165.9(6) . . . . ?
C46 C22 C23 C25 178.5(6) . . . . ?
C37 C22 C23 C25 -65.3(9) . . . . ?
C31 C22 C23 C25 58.7(8) . . . . ?
O8 N12 C25 O4 177.6(6) . . . . ?
C30 N12 C25 O4 -13.7(11) . . . . ?
O8 N12 C25 C23 -2.9(10) . . . . ?
C30 N12 C25 C23 165.8(7) . . . . ?
C22 C23 C25 O4 65.6(9) . . . . ?
C22 C23 C25 N12 -113.9(8) . . . . ?
C15 C20 C27 C52 -139.2(7) . . . . ?
C42 C20 C27 C52 98.5(8) . . . . ?
C21 C20 C27 C52 -20.0(10) . . . . ?
C15 C20 C27 C32 44.6(9) . . . . ?
C42 C20 C27 C32 -77.7(8) . . . . ?
C21 C20 C27 C32 163.8(7) . . . . ?
C58 C26 C28 C91 0.5(11) . . . . ?
C58 C26 C28 C47 -175.9(7) . . . . ?
O5 N11 C29 O6 -167.9(6) . . . . ?
C34 N11 C29 O6 -8.5(11) . . . . ?
O5 N11 C29 C53 14.7(10) . . . . ?
C34 N11 C29 C53 174.2(6) . . . . ?
C25 N12 C30 C72 -134.9(8) . . . . ?
O8 N12 C30 C72 34.2(9) . . . . ?
C25 N12 C30 C40 100.1(8) . . . . ?
O8 N12 C30 C40 -90.8(8) . . . . ?
C46 C22 C31 C77 -24.0(10) . . . . ?
C37 C22 C31 C77 -142.3(8) . . . . ?
C23 C22 C31 C77 93.9(8) . . . . ?
C46 C22 C31 C80 162.3(7) . . . . ?
C37 C22 C31 C80 44.0(10) . . . . ?
C23 C22 C31 C80 -79.8(9) . . . . ?
C52 C27 C32 C92 0.7(11) . . . . ?
C20 C27 C32 C92 177.1(7) . . . . ?
C14 C15 C33 C60 2.5(11) . . . . ?
C20 C15 C33 C60 175.6(7) . . . . ?
C29 N11 C34 C81 -92.3(9) . . . . ?
O5 N11 C34 C81 68.1(8) . . . . ?
C29 N11 C34 C19 144.0(7) . . . . ?
O5 N11 C34 C19 -55.6(8) . . . . ?
N9 C19 C34 N11 -54.9(8) . . . . ?
C55 C19 C34 N11 -179.4(6) . . . . ?
N9 C19 C34 C81 -179.5(6) . . . . ?
C55 C19 C34 C81 56.0(9) . . . . ?
C46 C22 C37 C99 -98.8(9) . . . . ?
C31 C22 C37 C99 23.3(11) . . . . ?
C23 C22 C37 C99 142.8(8) . . . . ?
C46 C22 C37 C61 74.0(9) . . . . ?
C31 C22 C37 C61 -164.0(7) . . . . ?
C23 C22 C37 C61 -44.5(10) . . . . ?
C56 C24 C38 C100 -1.3(12) . . . . ?
C73 C24 C38 C100 -177.1(7) . . . . ?
C14 C18 C39 C60 0.2(12) . . . . ?
C13 N10 C40 C69 -95.0(9) . . . . ?
O7 N10 C40 C69 65.9(8) . . . . ?
C13 N10 C40 C30 141.8(7) . . . . ?
O7 N10 C40 C30 -57.3(9) . . . . ?
N12 C30 C40 N10 -53.0(9) . . . . ?
C72 C30 C40 N10 -179.4(7) . . . . ?
N12 C30 C40 C69 -176.4(6) . . . . ?
C72 C30 C40 C69 57.2(9) . . . . ?
C27 C20 C42 C51 -95.2(8) . . . . ?
C15 C20 C42 C51 143.1(7) . . . . ?
C21 C20 C42 C51 28.1(9) . . . . ?
C27 C20 C42 C50 80.0(8) . . . . ?
C15 C20 C42 C50 -41.7(9) . . . . ?
C21 C20 C42 C50 -156.7(7) . . . . ?
C52 C35 C43 C92 0.4(13) . . . . ?
O2 C13 C44 C73 60.5(10) . . . . ?
N10 C13 C44 C73 -125.1(8) . . . . ?
C37 C22 C46 C97 65.3(9) . . . . ?
C31 C22 C46 C97 -57.7(9) . . . . ?
C23 C22 C46 C97 -173.5(7) . . . . ?
C37 C22 C46 C85 -113.0(8) . . . . ?
C31 C22 C46 C85 124.0(8) . . . . ?
C23 C22 C46 C85 8.2(10) . . . . ?
C71 C36 C47 C53 -165.3(7) . . . . ?
C70 C36 C47 C53 13.9(11) . . . . ?
C71 C36 C47 C28 73.8(9) . . . . ?
C70 C36 C47 C28 -106.9(8) . . . . ?
C71 C36 C47 C103 -46.5(10) . . . . ?
C70 C36 C47 C103 132.7(8) . . . . ?
C91 C28 C47 C36 -0.1(10) . . . . ?
C26 C28 C47 C36 176.0(7) . . . . ?
C91 C28 C47 C53 -125.3(8) . . . . ?
C26 C28 C47 C53 50.8(9) . . . . ?
C91 C28 C47 C103 117.4(8) . . . . ?
C26 C28 C47 C103 -66.5(9) . . . . ?
C98 C45 C48 C84 -0.3(13) . . . . ?
C98 C45 C48 C73 -176.5(8) . . . . ?
C51 C42 C50 C63 -2.3(11) . . . . ?
C20 C42 C50 C63 -177.6(7) . . . . ?
C50 C42 C51 C90 3.0(12) . . . . ?
C20 C42 C51 C90 178.3(8) . . . . ?
C32 C27 C52 C35 -2.1(11) . . . . ?
C20 C27 C52 C35 -178.4(7) . . . . ?
C43 C35 C52 C27 1.6(13) . . . . ?
O6 C29 C53 C47 44.7(10) . . . . ?
N11 C29 C53 C47 -137.9(7) . . . . ?
C36 C47 C53 C29 -82.7(8) . . . . ?
C28 C47 C53 C29 40.5(9) . . . . ?
C103 C47 C53 C29 159.6(6) . . . . ?
C65 C41 C54 C103 0.4(12) . . . . ?
N9 C19 C55 C87 176.3(6) . . . . ?
C34 C19 C55 C87 -58.1(8) . . . . ?
C38 C24 C56 C82 1.1(12) . . . . ?
C73 C24 C56 C82 176.9(7) . . . . ?
C28 C26 C58 C49 0.4(13) . . . . ?
C64 C49 C58 C26 -1.1(13) . . . . ?
C18 C39 C60 C33 0.0(12) . . . . ?
C15 C33 C60 C39 -1.4(12) . . . . ?
C99 C37 C61 C89 -2.0(13) . . . . ?
C22 C37 C61 C89 -175.1(9) . . . . ?
C42 C50 C63 C67 1.2(13) . . . . ?
C58 C49 C64 C91 0.9(14) . . . . ?
C66 C62 C65 C41 -1.1(12) . . . . ?
C54 C41 C65 C62 0.2(12) . . . . ?
C65 C62 C66 C103 1.4(13) . . . . ?
C50 C63 C67 C90 -0.7(13) . . . . ?
C78 C59 C69 C40 54.8(10) . . . . ?
N10 C40 C69 C59 -179.9(7) . . . . ?
C30 C40 C69 C59 -56.5(9) . . . . ?
C71 C36 C70 C76 0.2(12) . . . . ?
C47 C36 C70 C76 -179.1(8) . . . . ?
C70 C36 C71 C86 0.3(13) . . . . ?
C47 C36 C71 C86 179.5(8) . . . . ?
N12 C30 C72 C78 174.3(6) . . . . ?
C40 C30 C72 C78 -58.0(9) . . . . ?
C45 C48 C73 C74 115.5(10) . . . . ?
C84 C48 C73 C74 -60.7(10) . . . . ?
C45 C48 C73 C24 -121.7(9) . . . . ?
C84 C48 C73 C24 62.1(9) . . . . ?
C45 C48 C73 C44 -2.5(11) . . . . ?
C84 C48 C73 C44 -178.7(7) . . . . ?
C38 C24 C73 C48 -170.6(7) . . . . ?
C56 C24 C73 C48 13.7(10) . . . . ?
C38 C24 C73 C74 -51.0(10) . . . . ?
C56 C24 C73 C74 133.3(8) . . . . ?
C38 C24 C73 C44 65.6(9) . . . . ?
C56 C24 C73 C44 -110.1(8) . . . . ?
C13 C44 C73 C48 -78.4(9) . . . . ?
C13 C44 C73 C74 163.9(8) . . . . ?
C13 C44 C73 C24 44.1(9) . . . . ?
C48 C73 C74 C102 -74.2(10) . . . . ?
C24 C73 C74 C102 163.5(8) . . . . ?
C44 C73 C74 C102 47.9(10) . . . . ?
C48 C73 C74 C105 99.2(10) . . . . ?
C24 C73 C74 C105 -23.1(11) . . . . ?
C44 C73 C74 C105 -138.7(9) . . . . ?
C86 C57 C76 C70 -0.9(14) . . . . ?
C36 C70 C76 C57 0.2(13) . . . . ?
C80 C31 C77 C83 -2.0(12) . . . . ?
C22 C31 C77 C83 -175.9(8) . . . . ?
C30 C72 C78 C59 57.5(9) . . . . ?
C69 C59 C78 C72 -55.1(10) . . . . ?
C77 C31 C80 C68 1.6(12) . . . . ?
C22 C31 C80 C68 175.4(8) . . . . ?
C88 C68 C80 C31 -0.9(13) . . . . ?
C87 C75 C81 C34 54.5(10) . . . . ?
N11 C34 C81 C75 -178.2(7) . . . . ?
C19 C34 C81 C75 -54.4(9) . . . . ?
C100 C79 C82 C56 -3.0(13) . . . . ?
C24 C56 C82 C79 1.0(12) . . . . ?
C31 C77 C83 C88 1.9(13) . . . . ?
C45 C48 C84 C93 2.4(12) . . . . ?
C73 C48 C84 C93 178.9(8) . . . . ?
C97 C46 C85 C96 2.7(12) . . . . ?
C22 C46 C85 C96 -179.0(8) . . . . ?
C76 C57 C86 C71 1.3(14) . . . . ?
C36 C71 C86 C57 -1.0(14) . . . . ?
C81 C75 C87 C55 -56.5(9) . . . . ?
C19 C55 C87 C75 58.7(9) . . . . ?
C80 C68 C88 C83 0.7(13) . . . . ?
C77 C83 C88 C68 -1.2(13) . . . . ?
C37 C61 C89 C106 -1.4(16) . . . . ?
C42 C51 C90 C67 -2.6(14) . . . . ?
C63 C67 C90 C51 1.4(14) . . . . ?
C26 C28 C91 C64 -0.7(12) . . . . ?
C47 C28 C91 C64 175.5(8) . . . . ?
C49 C64 C91 C28 0.0(14) . . . . ?
C27 C32 C92 C43 1.3(13) . . . . ?
C35 C43 C92 C32 -1.8(13) . . . . ?
C48 C84 C93 C95 -2.6(14) . . . . ?
C84 C93 C95 C98 0.7(15) . . . . ?
C101 C94 C96 C85 -0.2(15) . . . . ?
C46 C85 C96 C94 -2.3(14) . . . . ?
C85 C46 C97 C101 -0.6(12) . . . . ?
C22 C46 C97 C101 -179.0(8) . . . . ?
C48 C45 C98 C95 -1.4(14) . . . . ?
C93 C95 C98 C45 1.3(15) . . . . ?
C61 C37 C99 C108 2.8(15) . . . . ?
C22 C37 C99 C108 175.9(10) . . . . ?
C82 C79 C100 C38 2.9(14) . . . . ?
C24 C38 C100 C79 -0.7(14) . . . . ?
C46 C97 C101 C94 -1.9(14) . . . . ?
C96 C94 C101 C97 2.3(15) . . . . ?
C105 C74 C102 C16 3.6(15) . . . . ?
C73 C74 C102 C16 177.3(9) . . . . ?
C114 C16 C102 C74 -5(2) . . . . ?
C41 C54 C103 C66 -0.1(12) . . . . ?
C41 C54 C103 C47 -176.5(7) . . . . ?
C62 C66 C103 C54 -0.8(12) . . . . ?
C62 C66 C103 C47 175.8(7) . . . . ?
C36 C47 C103 C54 104.8(8) . . . . ?
C53 C47 C103 C54 -132.2(8) . . . . ?
C28 C47 C103 C54 -15.6(10) . . . . ?
C36 C47 C103 C66 -71.6(9) . . . . ?
C53 C47 C103 C66 51.3(9) . . . . ?
C28 C47 C103 C66 167.9(7) . . . . ?
C102 C74 C105 C107 -2.5(14) . . . . ?
C73 C74 C105 C107 -176.2(9) . . . . ?
C61 C89 C106 C108 4.0(18) . . . . ?
C74 C105 C107 C114 2.5(19) . . . . ?
C37 C99 C108 C106 -0.2(19) . . . . ?
C89 C106 C108 C99 -3(2) . . . . ?
C102 C16 C114 C107 4(3) . . . . ?
C105 C107 C114 C16 -3(3) . . . . ?
C205 O201 C202 C203 14.6(18) . . . . ?
O201 C202 C203 C204 3(2) . . . . ?
C202 C203 C204 C205 -17(2) . . . . ?
C202 O201 C205 C204 -24.9(18) . . . . ?
C203 C204 C205 O201 26(2) . . . . ?
C210 O206 C207 C208 -16(3) . . . . ?
O206 C207 C208 C209 29(4) . . . . ?
C207 C208 C209 C210 -31(4) . . . . ?
C207 O206 C210 C209 -3(4) . . . . ?
C208 C209 C210 O206 21(4) . . . . ?



#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_160524Noda
_database_code_depnum_ccdc_archive 'CCDC 1498995'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H18 Cu F6 N10 O8 S2'
_chemical_formula_moiety         'C20 H18 Cu F6 N10 O8 S2'
_chemical_formula_weight         768.08
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.3568(6)
_cell_length_b                   10.0126(8)
_cell_length_c                   10.8607(9)
_cell_angle_alpha                110.106(8)
_cell_angle_beta                 95.309(7)
_cell_angle_gamma                106.922(8)
_cell_volume                     702.02(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4504
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      68.06
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.002
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             387.00
_exptl_absorpt_coefficient_mu    3.472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8326
_diffrn_reflns_av_R_equivalents  0.1232
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_min         4.439
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2514
_reflns_number_gt                1615
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1724
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2514
_refine_ls_number_parameters     214
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0745P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.18
_refine_diff_density_min         -0.89
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cu1 Cu 0.5000 0.5000 0.5000 0.0351(4) Uani 1 2 d S . P . .
S1 S 0.3460(2) 0.12073(16) 0.24471(14) 0.0372(4) Uani 1 1 d . . . . .
F3 F 0.2153(5) 0.0074(4) -0.0156(3) 0.0577(11) Uani 1 1 d . . . . .
F4 F 0.2447(5) 0.2404(4) 0.0819(3) 0.0556(10) Uani 1 1 d . . . . .
F5 F 0.4990(5) 0.1778(4) 0.0523(3) 0.0573(10) Uani 1 1 d . . . . .
O2 O 0.2433(5) 0.4776(4) 0.4113(4) 0.0362(10) Uani 1 1 d . . . . .
O6 O 0.4273(6) 0.0032(4) 0.2290(4) 0.0452(11) Uani 1 1 d . . . . .
O7 O 0.4770(5) 0.2711(4) 0.3326(4) 0.0408(10) Uani 1 1 d . . . . .
O8 O 0.1490(5) 0.0886(4) 0.2643(4) 0.0422(10) Uani 1 1 d . . . . .
N9 N 0.3715(7) 0.3886(5) 0.6091(4) 0.0341(11) Uani 1 1 d . . . . .
N10 N 0.0435(6) 0.3087(5) 0.4793(4) 0.0311(11) Uani 1 1 d . . . . .
N11 N -0.0875(8) 0.3803(6) 0.0863(7) 0.0635(18) Uani 1 1 d . . . . .
N23 N -0.1350(10) 0.3389(7) -0.0318(6) 0.087(2) Uani 1 1 d . . . . .
N24 N -0.0218(7) 0.4415(5) 0.2124(5) 0.0446(14) Uani 1 1 d . . . . .
C12 C 0.0811(8) 0.3793(6) 0.3966(5) 0.0305(13) Uani 1 1 d . . . . .
C14 C 0.1800(8) 0.3115(6) 0.5823(5) 0.0342(14) Uani 1 1 d . . . . .
C15 C 0.0872(8) 0.2235(6) 0.6480(6) 0.0364(14) Uani 1 1 d . . . . .
C16 C -0.0815(8) 0.3380(6) 0.2810(5) 0.0368(14) Uani 1 1 d . . . . .
H16A H -0.1109 0.2321 0.2178 0.044 Uiso 1 1 calc R U . . .
H16B H -0.2003 0.3463 0.3142 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3259(9) 0.1371(7) 0.0837(6) 0.0435(16) Uani 1 1 d . . . . .
C18 C -0.1464(8) 0.1928(6) 0.4617(6) 0.0385(15) Uani 1 1 d . . . . .
H18A H -0.1715 0.1009 0.3798 0.046 Uiso 1 1 calc R U . . .
H18B H -0.2538 0.2327 0.4558 0.046 Uiso 1 1 calc R U . . .
C19 C -0.1253(9) 0.1578(7) 0.5887(6) 0.0451(16) Uani 1 1 d . . . . .
H19A H -0.1980 0.2054 0.6522 0.054 Uiso 1 1 calc R U . . .
H19B H -0.1745 0.0471 0.5654 0.054 Uiso 1 1 calc R U . . .
C20 C 0.4779(9) 0.3754(6) 0.7113(5) 0.0397(15) Uani 1 1 d . . . . .
H20 H 0.6144 0.4279 0.7351 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1978(9) 0.2129(7) 0.7510(6) 0.0448(16) Uani 1 1 d . . . . .
H21 H 0.1399 0.1549 0.7994 0.054 Uiso 1 1 calc R U . . .
C22 C 0.3983(9) 0.2903(7) 0.7819(6) 0.0435(16) Uani 1 1 d . . . . .
H22 H 0.4796 0.2843 0.8516 0.052 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cu1 O2 1.953(3) . ?
Cu1 O2 1.953(3) 2_666 ?
Cu1 N9 2.011(5) 2_666 ?
Cu1 N9 2.011(5) . ?
Cu1 O7 2.332(4) 2_666 ?
Cu1 O7 2.332(4) . ?
S1 O6 1.436(4) . ?
S1 O8 1.443(4) . ?
S1 O7 1.451(3) . ?
S1 C17 1.809(6) . ?
F3 C17 1.330(6) . ?
F4 C17 1.341(6) . ?
F5 C17 1.334(7) . ?
O2 C12 1.262(6) . ?
N9 C14 1.342(6) . ?
N9 C20 1.365(6) . ?
N10 C12 1.322(6) . ?
N10 C14 1.420(6) . ?
N10 C18 1.480(6) . ?
N11 N23 1.186(7) . ?
N11 N24 1.270(7) . ?
N24 C16 1.467(7) . ?
C12 C16 1.502(7) . ?
C14 C15 1.387(7) . ?
C15 C21 1.374(7) . ?
C15 C19 1.489(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 C19 1.540(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C22 1.378(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 . 2_666 ?
O2 Cu1 N9 90.93(16) . 2_666 ?
O2 Cu1 N9 89.07(16) 2_666 2_666 ?
O2 Cu1 N9 89.07(16) . . ?
O2 Cu1 N9 90.93(16) 2_666 . ?
N9 Cu1 N9 180.0(3) 2_666 . ?
O2 Cu1 O7 91.03(14) . 2_666 ?
O2 Cu1 O7 88.97(14) 2_666 2_666 ?
N9 Cu1 O7 90.32(16) 2_666 2_666 ?
N9 Cu1 O7 89.68(16) . 2_666 ?
O2 Cu1 O7 88.97(14) . . ?
O2 Cu1 O7 91.03(14) 2_666 . ?
N9 Cu1 O7 89.68(16) 2_666 . ?
N9 Cu1 O7 90.32(16) . . ?
O7 Cu1 O7 180.0 2_666 . ?
O6 S1 O8 116.7(3) . . ?
O6 S1 O7 114.2(2) . . ?
O8 S1 O7 113.9(2) . . ?
O6 S1 C17 104.9(3) . . ?
O8 S1 C17 103.1(3) . . ?
O7 S1 C17 101.6(3) . . ?
C12 O2 Cu1 128.6(3) . . ?
S1 O7 Cu1 144.8(2) . . ?
C14 N9 C20 114.3(5) . . ?
C14 N9 Cu1 124.0(4) . . ?
C20 N9 Cu1 121.4(4) . . ?
C12 N10 C14 126.8(5) . . ?
C12 N10 C18 123.4(4) . . ?
C14 N10 C18 109.1(4) . . ?
N23 N11 N24 172.2(7) . . ?
N11 N24 C16 113.8(5) . . ?
O2 C12 N10 123.4(5) . . ?
O2 C12 C16 119.9(5) . . ?
N10 C12 C16 116.7(5) . . ?
N9 C14 C15 126.0(5) . . ?
N9 C14 N10 123.5(5) . . ?
C15 C14 N10 110.4(5) . . ?
C21 C15 C14 118.4(5) . . ?
C21 C15 C19 132.2(5) . . ?
C14 C15 C19 109.4(5) . . ?
N24 C16 C12 108.7(4) . . ?
N24 C16 H16A 110.0 . . ?
C12 C16 H16A 110.0 . . ?
N24 C16 H16B 110.0 . . ?
C12 C16 H16B 110.0 . . ?
H16A C16 H16B 108.3 . . ?
F3 C17 F5 107.0(5) . . ?
F3 C17 F4 106.4(5) . . ?
F5 C17 F4 107.5(5) . . ?
F3 C17 S1 112.2(5) . . ?
F5 C17 S1 111.8(4) . . ?
F4 C17 S1 111.5(4) . . ?
N10 C18 C19 103.8(4) . . ?
N10 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
N10 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C15 C19 C18 104.8(5) . . ?
C15 C19 H19A 110.8 . . ?
C18 C19 H19A 110.8 . . ?
C15 C19 H19B 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
N9 C20 C22 123.6(5) . . ?
N9 C20 H20 118.2 . . ?
C22 C20 H20 118.2 . . ?
C15 C21 C22 117.6(6) . . ?
C15 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
C20 C22 C21 119.9(5) . . ?
C20 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?

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
O6 S1 O7 Cu1 -140.2(4) . . . . ?
O8 S1 O7 Cu1 -2.6(5) . . . . ?
C17 S1 O7 Cu1 107.5(4) . . . . ?
Cu1 O2 C12 N10 26.5(8) . . . . ?
Cu1 O2 C12 C16 -153.9(4) . . . . ?
C14 N10 C12 O2 -10.5(9) . . . . ?
C18 N10 C12 O2 -179.7(5) . . . . ?
C14 N10 C12 C16 169.8(5) . . . . ?
C18 N10 C12 C16 0.7(8) . . . . ?
C20 N9 C14 C15 -0.1(9) . . . . ?
Cu1 N9 C14 C15 174.6(4) . . . . ?
C20 N9 C14 N10 -179.5(5) . . . . ?
Cu1 N9 C14 N10 -4.7(8) . . . . ?
C12 N10 C14 N9 -0.3(9) . . . . ?
C18 N10 C14 N9 170.1(5) . . . . ?
C12 N10 C14 C15 -179.7(5) . . . . ?
C18 N10 C14 C15 -9.4(6) . . . . ?
N9 C14 C15 C21 0.4(9) . . . . ?
N10 C14 C15 C21 179.8(5) . . . . ?
N9 C14 C15 C19 179.8(6) . . . . ?
N10 C14 C15 C19 -0.8(7) . . . . ?
N11 N24 C16 C12 145.8(5) . . . . ?
O2 C12 C16 N24 -7.3(7) . . . . ?
N10 C12 C16 N24 172.3(5) . . . . ?
O6 S1 C17 F3 58.5(5) . . . . ?
O8 S1 C17 F3 -64.1(5) . . . . ?
O7 S1 C17 F3 177.7(4) . . . . ?
O6 S1 C17 F5 -61.8(5) . . . . ?
O8 S1 C17 F5 175.6(4) . . . . ?
O7 S1 C17 F5 57.4(5) . . . . ?
O6 S1 C17 F4 177.8(4) . . . . ?
O8 S1 C17 F4 55.1(5) . . . . ?
O7 S1 C17 F4 -63.1(5) . . . . ?
C12 N10 C18 C19 -174.3(5) . . . . ?
C14 N10 C18 C19 15.0(6) . . . . ?
C21 C15 C19 C18 -170.7(6) . . . . ?
C14 C15 C19 C18 10.0(7) . . . . ?
N10 C18 C19 C15 -14.8(6) . . . . ?
C14 N9 C20 C22 0.3(9) . . . . ?
Cu1 N9 C20 C22 -174.6(5) . . . . ?
C14 C15 C21 C22 -0.8(9) . . . . ?
C19 C15 C21 C22 -180.0(6) . . . . ?
N9 C20 C22 C21 -0.7(10) . . . . ?
C15 C21 C22 C20 1.0(9) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_160413amemiya
_database_code_depnum_ccdc_archive 'CCDC 1498996'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H13 Cl F3 N5 O2'
_chemical_formula_moiety         'C19 H13 Cl F3 N5 O2'
_chemical_formula_weight         435.79
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.7343(3)
_cell_length_b                   12.0336(3)
_cell_length_c                   28.9712(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3742.28(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20122
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      68.27
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776.00
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_T_max  0.792

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            42774
_diffrn_reflns_av_R_equivalents  0.1480
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.051
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6841
_reflns_number_gt                4658
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1069
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6841
_refine_ls_number_parameters     541
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1173 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(17)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.04498(16) -0.16646(13) 0.56770(6) 0.0310(4) Uani 1 1 d . . . . .
Cl2 Cl 0.84583(16) 0.86301(14) 0.67591(6) 0.0320(4) Uani 1 1 d . . . . .
F1 F 0.3589(3) 0.4601(3) 0.66594(12) 0.0312(10) Uani 1 1 d . . . . .
F2 F 0.5598(4) 0.2080(3) 0.74647(12) 0.0377(11) Uani 1 1 d . . . . .
F3 F 0.3302(4) 0.6357(3) 0.65774(12) 0.0390(11) Uani 1 1 d . . . . .
F4 F 0.1753(4) 0.5306(3) 0.67533(13) 0.0355(10) Uani 1 1 d . . . . .
F5 F 0.6087(4) 0.0376(3) 0.73102(13) 0.0405(11) Uani 1 1 d . . . . .
F6 F 0.7528(4) 0.1570(3) 0.74452(12) 0.0387(11) Uani 1 1 d . . . . .
O7 O 0.5361(4) -0.0302(4) 0.63621(16) 0.0377(13) Uani 1 1 d . . . . .
O8 O 0.7350(4) 0.0998(4) 0.65192(14) 0.0290(12) Uani 1 1 d . . . . .
H8 H 0.7268 0.1012 0.6231 0.035 Uiso 1 1 calc R U . . .
O9 O 0.1602(4) 0.5978(4) 0.58476(15) 0.0296(12) Uani 1 1 d . . . . .
H9 H 0.1895 0.6621 0.5878 0.036 Uiso 1 1 calc R U . . .
O10 O 0.3499(4) 0.7266(4) 0.56495(15) 0.0292(11) Uani 1 1 d . . . . .
N11 N 0.6291(5) 0.4762(5) 0.55556(18) 0.0251(14) Uani 1 1 d . . . . .
N12 N 0.5450(5) 0.6618(4) 0.55968(17) 0.0218(13) Uani 1 1 d . . . . .
N13 N 0.3567(5) 0.0199(4) 0.67019(18) 0.0232(13) Uani 1 1 d . . . . .
N14 N 0.3535(5) 0.4908(4) 0.52180(18) 0.0263(14) Uani 1 1 d . . . . .
N17 N 0.2672(5) 0.1976(5) 0.68983(18) 0.0267(15) Uani 1 1 d . . . . .
N18 N 0.3850(5) 0.3918(5) 0.51527(19) 0.0289(15) Uani 1 1 d . . . . .
N19 N 0.4086(6) 0.3039(5) 0.50431(19) 0.0379(17) Uani 1 1 d . . . . .
N21 N 0.5740(6) 0.1453(6) 0.5739(2) 0.0457(18) Uani 1 1 d . . . . .
N58 N 0.6183(7) 0.1059(7) 0.5426(2) 0.065(2) Uani 1 1 d . . . . .
N59 N 0.5178(5) 0.2049(5) 0.6024(2) 0.0360(17) Uani 1 1 d . . . . .
C15 C 0.2594(6) 0.0890(6) 0.6876(2) 0.0234(16) Uani 1 1 d . . . . .
C16 C 0.1977(6) 0.4055(6) 0.5931(2) 0.0192(15) Uani 1 1 d . . . . .
C20 C 0.1969(6) 0.0108(5) 0.5633(2) 0.0218(16) Uani 1 1 d . . . . .
H20 H 0.2584 -0.0398 0.5527 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2782(7) 0.5365(6) 0.6498(2) 0.0276(17) Uani 1 1 d . . . . .
C23 C 0.0554(7) 0.0772(6) 0.7174(2) 0.0296(18) Uani 1 1 d . . . . .
H23 H -0.0162 0.0371 0.7271 0.035 Uiso 1 1 calc R U . . .
C24 C 0.2238(6) 0.1227(5) 0.5681(2) 0.0222(16) Uani 1 1 d . . . . .
H24 H 0.3043 0.1494 0.5601 0.027 Uiso 1 1 calc R U . . .
C25 C 0.0791(6) -0.0254(5) 0.5744(2) 0.0225(16) Uani 1 1 d . . . . .
C26 C 0.8528(6) 0.4646(6) 0.5444(2) 0.0264(16) Uani 1 1 d . . . . .
H26 H 0.9246 0.4192 0.5412 0.032 Uiso 1 1 calc R U . . .
C27 C 0.6455(6) 0.5857(6) 0.5545(2) 0.0229(16) Uani 1 1 d . . . . .
C28 C 0.1341(6) 0.1967(6) 0.5844(2) 0.0223(16) Uani 1 1 d . . . . .
C29 C 0.0165(6) 0.1575(6) 0.5960(2) 0.0231(16) Uani 1 1 d . . . . .
H29 H -0.0447 0.2069 0.6078 0.028 Uiso 1 1 calc R U . . .
C30 C -0.0111(6) 0.0457(5) 0.5902(2) 0.0223(16) Uani 1 1 d . . . . .
H30 H -0.0921 0.0186 0.5971 0.027 Uiso 1 1 calc R U . . .
C31 C 0.7577(6) 0.6426(6) 0.5488(2) 0.0243(16) Uani 1 1 d . . . . .
C32 C 0.4224(6) 0.6464(6) 0.5652(2) 0.0261(16) Uani 1 1 d . . . . .
C33 C 0.6473(6) 0.1729(6) 0.6723(2) 0.0256(16) Uani 1 1 d . . . . .
C34 C 0.1639(7) 0.2482(6) 0.7062(2) 0.0278(17) Uani 1 1 d . . . . .
H34 H 0.1645 0.3269 0.7085 0.033 Uiso 1 1 calc R U . . .
C35 C 0.4689(7) 0.0439(6) 0.6525(2) 0.0278(17) Uani 1 1 d . . . . .
C36 C 0.2501(6) 0.5192(6) 0.5984(2) 0.0227(16) Uani 1 1 d . . . . .
C37 C 0.7374(6) 0.4181(6) 0.5501(2) 0.0239(16) Uani 1 1 d . . . . .
H37 H 0.7324 0.3393 0.5502 0.029 Uiso 1 1 calc R U . . .
C39 C 0.6911(6) 0.2892(6) 0.6687(2) 0.0220(16) Uani 1 1 d . . . . .
C40 C 0.3745(6) 0.5270(6) 0.5703(2) 0.0237(16) Uani 1 1 d . . . . .
H40 H 0.4398 0.4795 0.5850 0.028 Uiso 1 1 calc R U . . .
C41 C 0.7510(7) 0.4999(6) 0.6701(2) 0.0250(17) Uani 1 1 d . . . . .
C42 C 0.9007(6) 0.6473(6) 0.6603(2) 0.0247(16) Uani 1 1 d . . . . .
H42 H 0.9819 0.6721 0.6523 0.030 Uiso 1 1 calc R U . . .
C43 C 0.6611(6) 0.5772(6) 0.6823(2) 0.0293(18) Uani 1 1 d . . . . .
H43 H 0.5792 0.5535 0.6899 0.035 Uiso 1 1 calc R U . . .
C44 C 0.5919(6) 0.7771(6) 0.5532(2) 0.0302(18) Uani 1 1 d . . . . .
H44A H 0.5677 0.8248 0.5795 0.036 Uiso 1 1 calc R U . . .
H44B H 0.5583 0.8098 0.5244 0.036 Uiso 1 1 calc R U . . .
C45 C 0.7213(6) 0.3833(6) 0.6692(2) 0.0269(17) Uani 1 1 d . . . . .
C46 C 0.1673(6) 0.3112(6) 0.5895(2) 0.0233(16) Uani 1 1 d . . . . .
C47 C 0.8627(6) 0.5798(6) 0.5434(2) 0.0273(17) Uani 1 1 d . . . . .
H47 H 0.9414 0.6143 0.5389 0.033 Uiso 1 1 calc R U . . .
C48 C 0.6907(6) 0.6880(6) 0.6833(2) 0.0283(18) Uani 1 1 d . . . . .
H48 H 0.6287 0.7412 0.6911 0.034 Uiso 1 1 calc R U . . .
C49 C 0.1578(6) 0.0230(6) 0.7009(2) 0.0256(17) Uani 1 1 d . . . . .
C50 C 0.5166(6) 0.1647(6) 0.6511(2) 0.0245(17) Uani 1 1 d . . . . .
H50 H 0.4585 0.2124 0.6694 0.029 Uiso 1 1 calc R U . . .
C51 C 0.6421(7) 0.1449(6) 0.7240(2) 0.0306(17) Uani 1 1 d . . . . .
C52 C 0.8098(6) 0.7227(5) 0.6730(2) 0.0244(16) Uani 1 1 d . . . . .
C53 C 0.0586(7) 0.1931(6) 0.7196(2) 0.0311(18) Uani 1 1 d . . . . .
H53 H -0.0118 0.2334 0.7303 0.037 Uiso 1 1 calc R U . . .
C54 C 0.1876(6) -0.0977(6) 0.6942(2) 0.0341(19) Uani 1 1 d . . . . .
H54A H 0.1245 -0.1339 0.6743 0.041 Uiso 1 1 calc R U . . .
H54B H 0.1904 -0.1369 0.7243 0.041 Uiso 1 1 calc R U . . .
C55 C 0.3155(6) -0.0986(6) 0.6710(2) 0.0308(18) Uani 1 1 d . . . . .
H55A H 0.3749 -0.1446 0.6889 0.037 Uiso 1 1 calc R U . . .
H55B H 0.3095 -0.1286 0.6393 0.037 Uiso 1 1 calc R U . . .
C56 C 0.8720(6) 0.5362(6) 0.6593(2) 0.0282(18) Uani 1 1 d . . . . .
H56 H 0.9342 0.4835 0.6512 0.034 Uiso 1 1 calc R U . . .
C57 C 0.7341(6) 0.7651(6) 0.5504(2) 0.0279(17) Uani 1 1 d . . . . .
H57A H 0.7668 0.8018 0.5223 0.034 Uiso 1 1 calc R U . . .
H57B H 0.7743 0.7987 0.5778 0.034 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl1 C25 1.747(6) . ?
Cl2 C52 1.734(7) . ?
F1 C22 1.347(7) . ?
F2 C51 1.333(7) . ?
F3 C22 1.338(7) . ?
F4 C22 1.332(7) . ?
F5 C51 1.356(7) . ?
F6 C51 1.336(7) . ?
O7 C35 1.241(7) . ?
O8 C33 1.416(7) . ?
O8 H8 0.8400 . ?
O9 C36 1.408(7) . ?
O9 H9 0.8400 . ?
O10 C32 1.240(7) . ?
N11 C27 1.330(8) . ?
N11 C37 1.366(8) . ?
N12 C32 1.338(8) . ?
N12 C27 1.423(8) . ?
N12 C44 1.487(8) . ?
N13 C35 1.340(8) . ?
N13 C15 1.427(8) . ?
N13 C55 1.493(8) . ?
N14 N18 1.253(7) . ?
N14 C40 1.489(7) . ?
N17 C15 1.311(8) . ?
N17 C34 1.350(8) . ?
N18 N19 1.134(7) . ?
N21 N58 1.128(8) . ?
N21 N59 1.251(8) . ?
N59 C50 1.491(8) . ?
C15 C49 1.403(9) . ?
C16 C46 1.186(8) . ?
C16 C36 1.487(9) . ?
C20 C25 1.376(8) . ?
C20 C24 1.384(8) . ?
C20 H20 0.9500 . ?
C22 C36 1.532(9) . ?
C23 C49 1.364(9) . ?
C23 C53 1.397(9) . ?
C23 H23 0.9500 . ?
C24 C28 1.395(8) . ?
C24 H24 0.9500 . ?
C25 C30 1.371(8) . ?
C26 C37 1.369(8) . ?
C26 C47 1.390(9) . ?
C26 H26 0.9500 . ?
C27 C31 1.395(8) . ?
C28 C29 1.389(8) . ?
C28 C46 1.430(8) . ?
C29 C30 1.389(8) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C47 1.366(9) . ?
C31 C57 1.497(9) . ?
C32 C40 1.534(8) . ?
C33 C39 1.480(9) . ?
C33 C50 1.536(8) . ?
C33 C51 1.537(8) . ?
C34 C53 1.367(8) . ?
C34 H34 0.9500 . ?
C35 C50 1.541(9) . ?
C36 C40 1.566(8) . ?
C37 H37 0.9500 . ?
C39 C45 1.179(9) . ?
C40 H40 1.0000 . ?
C41 C43 1.386(9) . ?
C41 C56 1.406(9) . ?
C41 C45 1.438(9) . ?
C42 C56 1.373(8) . ?
C42 C52 1.382(8) . ?
C42 H42 0.9500 . ?
C43 C48 1.371(9) . ?
C43 H43 0.9500 . ?
C44 C57 1.536(8) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C47 H47 0.9500 . ?
C48 C52 1.378(9) . ?
C48 H48 0.9500 . ?
C49 C54 1.500(9) . ?
C50 H50 1.0000 . ?
C53 H53 0.9500 . ?
C54 C55 1.529(9) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 H56 0.9500 . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?

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
C33 O8 H8 109.5 . . ?
C36 O9 H9 109.5 . . ?
C27 N11 C37 113.1(6) . . ?
C32 N12 C27 131.9(6) . . ?
C32 N12 C44 118.5(6) . . ?
C27 N12 C44 109.3(5) . . ?
C35 N13 C15 131.8(6) . . ?
C35 N13 C55 118.6(6) . . ?
C15 N13 C55 109.5(5) . . ?
N18 N14 C40 112.3(5) . . ?
C15 N17 C34 114.5(6) . . ?
N19 N18 N14 172.1(7) . . ?
N58 N21 N59 167.5(9) . . ?
N21 N59 C50 116.3(7) . . ?
N17 C15 C49 126.9(7) . . ?
N17 C15 N13 123.5(7) . . ?
C49 C15 N13 109.6(6) . . ?
C46 C16 C36 173.7(7) . . ?
C25 C20 C24 118.5(6) . . ?
C25 C20 H20 120.7 . . ?
C24 C20 H20 120.7 . . ?
F4 C22 F3 107.3(5) . . ?
F4 C22 F1 107.7(6) . . ?
F3 C22 F1 106.3(6) . . ?
F4 C22 C36 111.7(6) . . ?
F3 C22 C36 111.8(6) . . ?
F1 C22 C36 111.8(5) . . ?
C49 C23 C53 118.2(7) . . ?
C49 C23 H23 120.9 . . ?
C53 C23 H23 120.9 . . ?
C20 C24 C28 120.7(6) . . ?
C20 C24 H24 119.6 . . ?
C28 C24 H24 119.6 . . ?
C30 C25 C20 121.9(6) . . ?
C30 C25 Cl1 119.7(5) . . ?
C20 C25 Cl1 118.4(5) . . ?
C37 C26 C47 118.7(7) . . ?
C37 C26 H26 120.7 . . ?
C47 C26 H26 120.7 . . ?
N11 C27 C31 127.1(7) . . ?
N11 C27 N12 122.4(6) . . ?
C31 C27 N12 110.6(6) . . ?
C29 C28 C24 119.5(6) . . ?
C29 C28 C46 121.9(7) . . ?
C24 C28 C46 118.5(6) . . ?
C30 C29 C28 119.6(6) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C25 C30 C29 119.7(6) . . ?
C25 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C47 C31 C27 117.1(7) . . ?
C47 C31 C57 133.5(7) . . ?
C27 C31 C57 109.5(6) . . ?
O10 C32 N12 120.6(6) . . ?
O10 C32 C40 121.2(6) . . ?
N12 C32 C40 118.1(6) . . ?
O8 C33 C39 110.2(6) . . ?
O8 C33 C50 113.6(5) . . ?
C39 C33 C50 108.8(6) . . ?
O8 C33 C51 107.2(6) . . ?
C39 C33 C51 106.7(5) . . ?
C50 C33 C51 110.1(6) . . ?
N17 C34 C53 124.1(7) . . ?
N17 C34 H34 118.0 . . ?
C53 C34 H34 118.0 . . ?
O7 C35 N13 120.8(7) . . ?
O7 C35 C50 118.3(6) . . ?
N13 C35 C50 120.8(6) . . ?
O9 C36 C16 109.2(5) . . ?
O9 C36 C22 108.5(5) . . ?
C16 C36 C22 107.4(5) . . ?
O9 C36 C40 113.4(5) . . ?
C16 C36 C40 108.9(5) . . ?
C22 C36 C40 109.2(5) . . ?
N11 C37 C26 125.0(7) . . ?
N11 C37 H37 117.5 . . ?
C26 C37 H37 117.5 . . ?
C45 C39 C33 174.5(8) . . ?
N14 C40 C32 103.4(5) . . ?
N14 C40 C36 110.2(5) . . ?
C32 C40 C36 113.1(5) . . ?
N14 C40 H40 110.0 . . ?
C32 C40 H40 110.0 . . ?
C36 C40 H40 110.0 . . ?
C43 C41 C56 119.4(7) . . ?
C43 C41 C45 120.3(7) . . ?
C56 C41 C45 120.3(7) . . ?
C56 C42 C52 119.1(6) . . ?
C56 C42 H42 120.4 . . ?
C52 C42 H42 120.4 . . ?
C48 C43 C41 119.8(7) . . ?
C48 C43 H43 120.1 . . ?
C41 C43 H43 120.1 . . ?
N12 C44 C57 104.8(6) . . ?
N12 C44 H44A 110.8 . . ?
C57 C44 H44A 110.8 . . ?
N12 C44 H44B 110.8 . . ?
C57 C44 H44B 110.8 . . ?
H44A C44 H44B 108.9 . . ?
C39 C45 C41 176.9(8) . . ?
C16 C46 C28 178.3(8) . . ?
C31 C47 C26 119.0(7) . . ?
C31 C47 H47 120.5 . . ?
C26 C47 H47 120.5 . . ?
C43 C48 C52 120.3(7) . . ?
C43 C48 H48 119.8 . . ?
C52 C48 H48 119.8 . . ?
C23 C49 C15 116.9(7) . . ?
C23 C49 C54 132.8(7) . . ?
C15 C49 C54 110.3(6) . . ?
N59 C50 C33 110.5(5) . . ?
N59 C50 C35 109.6(5) . . ?
C33 C50 C35 110.7(6) . . ?
N59 C50 H50 108.7 . . ?
C33 C50 H50 108.7 . . ?
C35 C50 H50 108.7 . . ?
F2 C51 F6 108.1(6) . . ?
F2 C51 F5 107.1(6) . . ?
F6 C51 F5 105.8(6) . . ?
F2 C51 C33 112.1(6) . . ?
F6 C51 C33 112.1(6) . . ?
F5 C51 C33 111.3(6) . . ?
C48 C52 C42 120.9(7) . . ?
C48 C52 Cl2 119.4(6) . . ?
C42 C52 Cl2 119.6(5) . . ?
C34 C53 C23 119.4(7) . . ?
C34 C53 H53 120.3 . . ?
C23 C53 H53 120.3 . . ?
C49 C54 C55 104.7(6) . . ?
C49 C54 H54A 110.8 . . ?
C55 C54 H54A 110.8 . . ?
C49 C54 H54B 110.8 . . ?
C55 C54 H54B 110.8 . . ?
H54A C54 H54B 108.9 . . ?
N13 C55 C54 105.5(6) . . ?
N13 C55 H55A 110.6 . . ?
C54 C55 H55A 110.6 . . ?
N13 C55 H55B 110.6 . . ?
C54 C55 H55B 110.6 . . ?
H55A C55 H55B 108.8 . . ?
C42 C56 C41 120.3(7) . . ?
C42 C56 H56 119.8 . . ?
C41 C56 H56 119.8 . . ?
C31 C57 C44 105.2(5) . . ?
C31 C57 H57A 110.7 . . ?
C44 C57 H57A 110.7 . . ?
C31 C57 H57B 110.7 . . ?
C44 C57 H57B 110.7 . . ?
H57A C57 H57B 108.8 . . ?

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
N58 N21 N59 C50 180(3) . . . . ?
C34 N17 C15 C49 -1.1(10) . . . . ?
C34 N17 C15 N13 178.3(5) . . . . ?
C35 N13 C15 N17 -1.4(11) . . . . ?
C55 N13 C15 N17 -178.0(6) . . . . ?
C35 N13 C15 C49 178.1(6) . . . . ?
C55 N13 C15 C49 1.4(7) . . . . ?
C25 C20 C24 C28 1.1(10) . . . . ?
C24 C20 C25 C30 -0.6(10) . . . . ?
C24 C20 C25 Cl1 179.3(5) . . . . ?
C37 N11 C27 C31 -0.2(9) . . . . ?
C37 N11 C27 N12 -179.8(5) . . . . ?
C32 N12 C27 N11 -1.7(10) . . . . ?
C44 N12 C27 N11 -175.5(5) . . . . ?
C32 N12 C27 C31 178.7(6) . . . . ?
C44 N12 C27 C31 4.9(7) . . . . ?
C20 C24 C28 C29 -0.2(10) . . . . ?
C20 C24 C28 C46 178.9(6) . . . . ?
C24 C28 C29 C30 -1.4(9) . . . . ?
C46 C28 C29 C30 179.6(6) . . . . ?
C20 C25 C30 C29 -0.9(10) . . . . ?
Cl1 C25 C30 C29 179.2(5) . . . . ?
C28 C29 C30 C25 1.9(9) . . . . ?
N11 C27 C31 C47 0.4(10) . . . . ?
N12 C27 C31 C47 -180.0(5) . . . . ?
N11 C27 C31 C57 -179.2(6) . . . . ?
N12 C27 C31 C57 0.4(7) . . . . ?
C27 N12 C32 O10 -173.6(6) . . . . ?
C44 N12 C32 O10 -0.2(9) . . . . ?
C27 N12 C32 C40 4.8(10) . . . . ?
C44 N12 C32 C40 178.1(5) . . . . ?
C15 N17 C34 C53 0.1(10) . . . . ?
C15 N13 C35 O7 -174.7(6) . . . . ?
C55 N13 C35 O7 1.7(10) . . . . ?
C15 N13 C35 C50 4.0(11) . . . . ?
C55 N13 C35 C50 -179.6(6) . . . . ?
F4 C22 C36 O9 56.0(7) . . . . ?
F3 C22 C36 O9 -64.3(7) . . . . ?
F1 C22 C36 O9 176.7(5) . . . . ?
F4 C22 C36 C16 -62.0(7) . . . . ?
F3 C22 C36 C16 177.8(6) . . . . ?
F1 C22 C36 C16 58.7(7) . . . . ?
F4 C22 C36 C40 -180.0(6) . . . . ?
F3 C22 C36 C40 59.8(7) . . . . ?
F1 C22 C36 C40 -59.2(7) . . . . ?
C27 N11 C37 C26 0.5(9) . . . . ?
C47 C26 C37 N11 -0.9(10) . . . . ?
N18 N14 C40 C32 140.8(6) . . . . ?
N18 N14 C40 C36 -98.0(7) . . . . ?
O10 C32 C40 N14 90.5(7) . . . . ?
N12 C32 C40 N14 -87.8(7) . . . . ?
O10 C32 C40 C36 -28.7(9) . . . . ?
N12 C32 C40 C36 153.0(5) . . . . ?
O9 C36 C40 N14 -68.9(7) . . . . ?
C16 C36 C40 N14 52.9(7) . . . . ?
C22 C36 C40 N14 170.0(5) . . . . ?
O9 C36 C40 C32 46.3(7) . . . . ?
C16 C36 C40 C32 168.2(5) . . . . ?
C22 C36 C40 C32 -74.8(7) . . . . ?
C56 C41 C43 C48 0.5(10) . . . . ?
C45 C41 C43 C48 179.6(6) . . . . ?
C32 N12 C44 C57 177.4(5) . . . . ?
C27 N12 C44 C57 -7.8(7) . . . . ?
C27 C31 C47 C26 -0.8(9) . . . . ?
C57 C31 C47 C26 178.7(7) . . . . ?
C37 C26 C47 C31 1.1(9) . . . . ?
C41 C43 C48 C52 -1.2(10) . . . . ?
C53 C23 C49 C15 0.4(9) . . . . ?
C53 C23 C49 C54 179.2(7) . . . . ?
N17 C15 C49 C23 0.9(10) . . . . ?
N13 C15 C49 C23 -178.5(5) . . . . ?
N17 C15 C49 C54 -178.2(6) . . . . ?
N13 C15 C49 C54 2.3(8) . . . . ?
N21 N59 C50 C33 69.5(8) . . . . ?
N21 N59 C50 C35 -52.7(8) . . . . ?
O8 C33 C50 N59 -66.8(8) . . . . ?
C39 C33 C50 N59 56.4(7) . . . . ?
C51 C33 C50 N59 173.1(5) . . . . ?
O8 C33 C50 C35 54.8(7) . . . . ?
C39 C33 C50 C35 178.0(5) . . . . ?
C51 C33 C50 C35 -65.4(7) . . . . ?
O7 C35 C50 N59 69.5(8) . . . . ?
N13 C35 C50 N59 -109.3(7) . . . . ?
O7 C35 C50 C33 -52.6(8) . . . . ?
N13 C35 C50 C33 128.6(7) . . . . ?
O8 C33 C51 F2 -178.8(5) . . . . ?
C39 C33 C51 F2 63.1(7) . . . . ?
C50 C33 C51 F2 -54.8(8) . . . . ?
O8 C33 C51 F6 59.5(7) . . . . ?
C39 C33 C51 F6 -58.6(7) . . . . ?
C50 C33 C51 F6 -176.5(6) . . . . ?
O8 C33 C51 F5 -58.8(7) . . . . ?
C39 C33 C51 F5 -176.9(6) . . . . ?
C50 C33 C51 F5 65.2(7) . . . . ?
C43 C48 C52 C42 1.9(11) . . . . ?
C43 C48 C52 Cl2 -178.4(5) . . . . ?
C56 C42 C52 C48 -1.9(10) . . . . ?
C56 C42 C52 Cl2 178.3(5) . . . . ?
N17 C34 C53 C23 1.1(11) . . . . ?
C49 C23 C53 C34 -1.3(10) . . . . ?
C23 C49 C54 C55 176.1(7) . . . . ?
C15 C49 C54 C55 -5.0(8) . . . . ?
C35 N13 C55 C54 178.3(6) . . . . ?
C15 N13 C55 C54 -4.5(7) . . . . ?
C49 C54 C55 N13 5.6(7) . . . . ?
C52 C42 C56 C41 1.3(10) . . . . ?
C43 C41 C56 C42 -0.6(10) . . . . ?
C45 C41 C56 C42 -179.7(6) . . . . ?
C47 C31 C57 C44 175.2(7) . . . . ?
C27 C31 C57 C44 -5.2(7) . . . . ?
N12 C44 C57 C31 7.8(7) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O8 H8 N21 . . . 2.898(8) 0.840 2.238 135.6 no
O8 H8 N59 . . . 3.015(7) 0.840 2.637 108.9 no
O9 H9 Cl1 . . 1_565 3.134(5) 0.840 2.646 118.4 no
O9 H9 F3 . . . 2.830(6) 0.840 2.547 101.0 no
O9 H9 O10 . . . 2.623(6) 0.840 2.001 130.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


