# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_b317
_database_code_depnum_ccdc_archive 'CCDC 1419114'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-MeOH
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H35 Cl N10 O8.50'
_chemical_formula_weight         827.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.5456(13)
_cell_length_b                   10.4106(10)
_cell_length_c                   27.394(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.946(2)
_cell_angle_gamma                90.00
_cell_volume                     3834.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    988
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      22.19

_exptl_crystal_description       ROD
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8901
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44183
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7521
_reflns_number_gt                5891
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1175P)²+8.2014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7521
_refine_ls_number_parameters     583
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_ref         0.2431
_refine_ls_wR_factor_gt          0.2289
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.110
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36672(18) 1.0056(3) 0.22018(10) 0.0391(7) Uani 1 1 d . . .
O2 O 0.11928(19) 0.9183(3) 0.44824(9) 0.0336(6) Uani 1 1 d . . .
O3 O -0.40655(18) 0.8643(3) 0.32130(9) 0.0338(6) Uani 1 1 d . . .
O4 O -0.25925(19) 0.7792(3) 0.06440(9) 0.0344(6) Uani 1 1 d . . .
O5 O 0.29559(18) 0.7157(2) 0.13827(9) 0.0293(6) Uani 1 1 d . . .
O6 O 0.1285(2) 0.6224(3) 0.36463(10) 0.0415(7) Uani 1 1 d . . .
O7 O 0.2780(2) 0.6148(3) 0.40939(9) 0.0349(6) Uani 1 1 d . . .
N1 N 0.2178(2) 1.0114(3) 0.25032(10) 0.0229(6) Uani 1 1 d D . .
H1N H 0.1514(13) 1.023(4) 0.2467(7) 0.028 Uiso 1 1 d D . .
N2 N 0.1742(2) 0.9739(3) 0.32680(10) 0.0220(6) Uani 1 1 d . . .
N3 N 0.0188(2) 0.9404(3) 0.37537(10) 0.0231(6) Uani 1 1 d D . .
H3N H 0.024(3) 0.945(4) 0.3428(7) 0.028 Uiso 1 1 d D . .
N4 N -0.1462(2) 0.9046(3) 0.35140(10) 0.0227(6) Uani 1 1 d . . .
N5 N -0.2777(2) 0.8523(3) 0.27425(10) 0.0245(6) Uani 1 1 d D . .
H5N H -0.2116(14) 0.861(4) 0.2760(14) 0.029 Uiso 1 1 d D . .
N6 N -0.2624(2) 0.8177(3) 0.19294(10) 0.0225(6) Uani 1 1 d . . .
N7 N -0.1334(2) 0.7771(3) 0.12837(10) 0.0242(6) Uani 1 1 d D . .
H7N H -0.126(3) 0.780(4) 0.1612(7) 0.029 Uiso 1 1 d D . .
N8 N 0.0347(2) 0.7479(3) 0.13553(10) 0.0212(6) Uani 1 1 d . . .
N9 N 0.1931(2) 0.6946(3) 0.19860(10) 0.0226(6) Uani 1 1 d D . .
H9N H 0.1285(14) 0.699(4) 0.2013(14) 0.027 Uiso 1 1 d D . .
N10 N 0.2160(2) 0.6570(3) 0.28119(10) 0.0219(6) Uani 1 1 d . . .
C1 C 0.2258(3) 1.0395(3) 0.16187(13) 0.0243(7) Uani 1 1 d . . .
C2 C 0.2872(3) 1.0469(4) 0.12465(14) 0.0313(8) Uani 1 1 d . . .
H2 H 0.3572 1.0398 0.1325 0.038 Uiso 1 1 calc R . .
C3 C 0.2465(3) 1.0644(4) 0.07629(14) 0.0375(9) Uani 1 1 d . . .
H3 H 0.2887 1.0694 0.0511 0.045 Uiso 1 1 calc R . .
C4 C 0.1454(3) 1.0747(4) 0.06467(13) 0.0332(9) Uani 1 1 d . . .
H4 H 0.1178 1.0858 0.0314 0.040 Uiso 1 1 calc R . .
C5 C 0.0836(3) 1.0688(4) 0.10143(13) 0.0323(9) Uani 1 1 d . . .
H5 H 0.0137 1.0775 0.0934 0.039 Uiso 1 1 calc R . .
C6 C 0.1235(3) 1.0504(3) 0.14973(12) 0.0253(7) Uani 1 1 d . . .
H6 H 0.0808 1.0452 0.1748 0.030 Uiso 1 1 calc R . .
C7 C 0.2764(2) 1.0179(3) 0.21289(13) 0.0255(8) Uani 1 1 d . . .
C8 C 0.2488(2) 0.9882(3) 0.30029(12) 0.0218(7) Uani 1 1 d . . .
C9 C 0.3488(3) 0.9820(3) 0.32087(13) 0.0289(8) Uani 1 1 d . . .
H9 H 0.4012 0.9925 0.3011 0.035 Uiso 1 1 calc R . .
C10 C 0.3686(3) 0.9602(4) 0.37067(14) 0.0326(9) Uani 1 1 d . . .
H10 H 0.4355 0.9545 0.3856 0.039 Uiso 1 1 calc R . .
C11 C 0.2912(3) 0.9465(3) 0.39894(13) 0.0286(8) Uani 1 1 d . . .
H11 H 0.3037 0.9328 0.4334 0.034 Uiso 1 1 calc R . .
C12 C 0.1948(3) 0.9534(3) 0.37533(12) 0.0252(8) Uani 1 1 d . . .
C13 C 0.1080(3) 0.9360(3) 0.40383(12) 0.0242(7) Uani 1 1 d . . .
C14 C -0.0767(3) 0.9235(3) 0.38937(12) 0.0233(7) Uani 1 1 d . . .
C15 C -0.0977(3) 0.9290(3) 0.43799(13) 0.0289(8) Uani 1 1 d . . .
H15 H -0.0462 0.9412 0.4644 0.035 Uiso 1 1 calc R . .
C16 C -0.1951(3) 0.9161(4) 0.44656(13) 0.0343(9) Uani 1 1 d . . .
H16 H -0.2119 0.9205 0.4792 0.041 Uiso 1 1 calc R . .
C17 C -0.2691(3) 0.8967(4) 0.40744(14) 0.0307(8) Uani 1 1 d . . .
H17 H -0.3368 0.8879 0.4127 0.037 Uiso 1 1 calc R . .
C18 C -0.2408(3) 0.8906(3) 0.36064(13) 0.0254(8) Uani 1 1 d . . .
C19 C -0.3178(3) 0.8686(3) 0.31745(13) 0.0271(8) Uani 1 1 d . . .
C20 C -0.3249(2) 0.8355(3) 0.22635(12) 0.0245(7) Uani 1 1 d . . .
C21 C -0.4282(3) 0.8384(3) 0.21449(14) 0.0294(8) Uani 1 1 d . . .
H21 H -0.4709 0.8493 0.2392 0.035 Uiso 1 1 calc R . .
C22 C -0.4662(3) 0.8250(4) 0.16569(15) 0.0331(9) Uani 1 1 d . . .
H22 H -0.5361 0.8270 0.1564 0.040 Uiso 1 1 calc R . .
C23 C -0.4029(3) 0.8087(4) 0.13041(13) 0.0299(8) Uani 1 1 d . . .
H23 H -0.4279 0.8004 0.0966 0.036 Uiso 1 1 calc R . .
C24 C -0.3014(3) 0.8047(3) 0.14584(13) 0.0251(8) Uani 1 1 d . . .
C25 C -0.2305(3) 0.7860(3) 0.10835(12) 0.0253(8) Uani 1 1 d . . .
C26 C -0.0482(2) 0.7637(3) 0.10467(12) 0.0228(7) Uani 1 1 d . . .
C27 C -0.0496(3) 0.7656(3) 0.05342(12) 0.0270(8) Uani 1 1 d . . .
H27 H -0.1103 0.7724 0.0322 0.032 Uiso 1 1 calc R . .
C28 C 0.0406(3) 0.7572(4) 0.03499(13) 0.0305(8) Uani 1 1 d . . .
H28 H 0.0426 0.7602 0.0005 0.037 Uiso 1 1 calc R . .
C29 C 0.1279(3) 0.7444(3) 0.06619(13) 0.0273(8) Uani 1 1 d . . .
H29 H 0.1905 0.7403 0.0539 0.033 Uiso 1 1 calc R . .
C30 C 0.1205(2) 0.7379(3) 0.11605(12) 0.0223(7) Uani 1 1 d . . .
C31 C 0.2131(2) 0.7157(3) 0.15158(12) 0.0220(7) Uani 1 1 d . . .
C32 C 0.2601(2) 0.6731(3) 0.24049(12) 0.0222(7) Uani 1 1 d . . .
C33 C 0.3638(3) 0.6694(3) 0.24116(13) 0.0262(8) Uani 1 1 d . . .
H33 H 0.3935 0.6787 0.2117 0.031 Uiso 1 1 calc R . .
C34 C 0.4214(3) 0.6519(3) 0.28559(14) 0.0297(8) Uani 1 1 d . . .
H34 H 0.4917 0.6483 0.2870 0.036 Uiso 1 1 calc R . .
C35 C 0.3765(3) 0.6397(3) 0.32828(13) 0.0267(8) Uani 1 1 d . . .
H35 H 0.4150 0.6306 0.3594 0.032 Uiso 1 1 calc R . .
C36 C 0.2738(2) 0.6411(3) 0.32389(12) 0.0232(7) Uani 1 1 d . . .
C37 C 0.2169(3) 0.6247(3) 0.36728(13) 0.0261(8) Uani 1 1 d . . .
C38 C 0.2296(3) 0.6060(4) 0.45337(14) 0.0413(10) Uani 1 1 d . . .
H38A H 0.1898 0.6834 0.4566 0.062 Uiso 1 1 calc R . .
H38B H 0.2800 0.5980 0.4821 0.062 Uiso 1 1 calc R . .
H38C H 0.1862 0.5304 0.4513 0.062 Uiso 1 1 calc R . .
C2X C -0.4802(13) 0.6488(11) 0.0064(8) 0.087(4) Uiso 0.25 1 d PD A -1
H2XA H -0.4185 0.6816 0.0254 0.105 Uiso 0.25 1 calc PR A -1
H2XB H -0.4994 0.7065 -0.0219 0.105 Uiso 0.25 1 calc PR A -1
Cl1 Cl -0.5746(5) 0.6350(7) 0.0430(3) 0.0660(15) Uani 0.25 1 d PDU A -1
Cl2 Cl -0.4649(4) 0.4930(7) -0.0129(2) 0.0838(15) Uani 0.25 1 d PDU A -1
C3X C -0.4730(11) 0.664(2) 0.0086(6) 0.087(4) Uiso 0.25 1 d PD B -2
H3XA H -0.4145 0.6916 0.0313 0.105 Uiso 0.25 1 calc PR B -2
H3XB H -0.4628 0.5742 -0.0016 0.105 Uiso 0.25 1 calc PR B -2
Cl3 Cl -0.5802(6) 0.6775(8) 0.0361(3) 0.0660(15) Uani 0.25 1 d PDU B -2
Cl4 Cl -0.4913(7) 0.7633(9) -0.0414(3) 0.0838(15) Uani 0.25 1 d PDU B -2
O1X O 0.4892(6) 1.2046(6) 0.0310(3) 0.054(2) Uani 0.50 1 d PDU C -1
H1X H 0.4475 1.2459 0.0119 0.081 Uiso 0.50 1 calc PR C -1
C1X C 0.4910(5) 1.0745(7) 0.0152(4) 0.050(2) Uani 0.50 1 d PDU C -1
H1XA H 0.5544 1.0567 0.0027 0.075 Uiso 0.50 1 calc PR C -1
H1XB H 0.4362 1.0597 -0.0110 0.075 Uiso 0.50 1 calc PR C -1
H1XC H 0.4835 1.0175 0.0430 0.075 Uiso 0.50 1 calc PR C -1
C2S C -0.0205(3) 0.7432(4) 0.26248(14) 0.0350(9) Uani 1 1 d . . .
H2SA H -0.0266 0.7562 0.2974 0.053 Uiso 1 1 calc R . .
H2SB H -0.0845 0.7608 0.2429 0.053 Uiso 1 1 calc R . .
H2SC H 0.0302 0.8015 0.2524 0.053 Uiso 1 1 calc R . .
O4S O 0.00798(18) 0.6137(3) 0.25469(9) 0.0308(6) Uani 1 1 d . . .
H4S H 0.0665 0.6018 0.2679 0.046 Uiso 1 1 calc R . .


_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 C7 1.223(4) . ?
O2 C13 1.222(4) . ?
O3 C19 1.221(4) . ?
O4 C25 1.222(4) . ?
O5 C31 1.216(4) . ?
O6 C37 1.191(4) . ?
O7 C37 1.339(4) . ?
O7 C38 1.442(5) . ?
N1 C7 1.372(4) . ?
N1 C8 1.403(4) . ?
N2 C8 1.323(4) . ?
N2 C12 1.342(4) . ?
N3 C13 1.357(4) . ?
N3 C14 1.404(4) . ?
N4 C14 1.330(4) . ?
N4 C18 1.344(4) . ?
N5 C19 1.370(5) . ?
N5 C20 1.399(4) . ?
N6 C20 1.332(4) . ?
N6 C24 1.340(4) . ?
N7 C25 1.366(4) . ?
N7 C26 1.397(4) . ?
N8 C26 1.332(4) . ?
N8 C30 1.341(4) . ?
N9 C31 1.366(4) . ?
N9 C32 1.392(4) . ?
N10 C36 1.337(4) . ?
N10 C32 1.337(4) . ?
C1 C6 1.391(5) . ?
C1 C2 1.393(5) . ?
C1 C7 1.497(5) . ?
C2 C3 1.384(5) . ?
C3 C4 1.372(6) . ?
C4 C5 1.387(5) . ?
C5 C6 1.380(5) . ?
C8 C9 1.405(5) . ?
C9 C10 1.377(5) . ?
C10 C11 1.385(5) . ?
C11 C12 1.387(5) . ?
C12 C13 1.499(5) . ?
C14 C15 1.396(5) . ?
C15 C16 1.374(5) . ?
C16 C17 1.391(5) . ?
C17 C18 1.383(5) . ?
C18 C19 1.497(5) . ?
C20 C21 1.399(5) . ?
C21 C22 1.380(5) . ?
C22 C23 1.378(5) . ?
C23 C24 1.390(5) . ?
C24 C25 1.501(5) . ?
C26 C27 1.402(5) . ?
C27 C28 1.380(5) . ?
C28 C29 1.379(5) . ?
C29 C30 1.383(5) . ?
C30 C31 1.510(5) . ?
C32 C33 1.403(5) . ?
C33 C34 1.376(5) . ?
C34 C35 1.388(5) . ?
C35 C36 1.382(5) . ?
C36 C37 1.502(5) . ?
C2X Cl1 1.724(10) . ?
C2X Cl2 1.726(10) . ?
C3X Cl4 1.711(10) . ?
C3X Cl3 1.720(10) . ?
O1X C1X 1.423(5) . ?
C2S O4S 1.425(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
C37 O7 C38 115.4(3) . . ?
C7 N1 C8 127.3(3) . . ?
C8 N2 C12 118.7(3) . . ?
C13 N3 C14 128.6(3) . . ?
C14 N4 C18 118.0(3) . . ?
C19 N5 C20 129.9(3) . . ?
C20 N6 C24 117.8(3) . . ?
C25 N7 C26 129.0(3) . . ?
C26 N8 C30 117.5(3) . . ?
C31 N9 C32 128.3(3) . . ?
C36 N10 C32 118.1(3) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 C7 124.5(3) . . ?
C2 C1 C7 116.5(3) . . ?
C3 C2 C1 120.3(4) . . ?
C4 C3 C2 120.2(4) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 120.1(4) . . ?
C5 C6 C1 120.2(3) . . ?
O1 C7 N1 122.1(3) . . ?
O1 C7 C1 120.3(3) . . ?
N1 C7 C1 117.7(3) . . ?
N2 C8 N1 113.4(3) . . ?
N2 C8 C9 122.6(3) . . ?
N1 C8 C9 124.0(3) . . ?
C10 C9 C8 117.9(3) . . ?
C9 C10 C11 120.1(3) . . ?
C10 C11 C12 117.9(3) . . ?
N2 C12 C11 122.8(3) . . ?
N2 C12 C13 116.9(3) . . ?
C11 C12 C13 120.3(3) . . ?
O2 C13 N3 125.0(3) . . ?
O2 C13 C12 121.7(3) . . ?
N3 C13 C12 113.4(3) . . ?
N4 C14 C15 123.0(3) . . ?
N4 C14 N3 113.1(3) . . ?
C15 C14 N3 123.8(3) . . ?
C16 C15 C14 118.0(3) . . ?
C15 C16 C17 120.0(3) . . ?
C18 C17 C16 117.8(3) . . ?
N4 C18 C17 123.1(3) . . ?
N4 C18 C19 117.2(3) . . ?
C17 C18 C19 119.7(3) . . ?
O3 C19 N5 124.5(3) . . ?
O3 C19 C18 122.4(3) . . ?
N5 C19 C18 113.0(3) . . ?
N6 C20 C21 123.0(3) . . ?
N6 C20 N5 113.9(3) . . ?
C21 C20 N5 123.1(3) . . ?
C22 C21 C20 117.9(3) . . ?
C23 C22 C21 120.1(3) . . ?
C22 C23 C24 117.8(3) . . ?
N6 C24 C23 123.4(3) . . ?
N6 C24 C25 117.5(3) . . ?
C23 C24 C25 119.2(3) . . ?
O4 C25 N7 124.7(3) . . ?
O4 C25 C24 121.8(3) . . ?
N7 C25 C24 113.5(3) . . ?
N8 C26 N7 113.4(3) . . ?
N8 C26 C27 123.1(3) . . ?
N7 C26 C27 123.5(3) . . ?
C28 C27 C26 117.4(3) . . ?
C29 C28 C27 120.7(3) . . ?
C28 C29 C30 117.2(3) . . ?
N8 C30 C29 124.0(3) . . ?
N8 C30 C31 116.6(3) . . ?
C29 C30 C31 119.4(3) . . ?
O5 C31 N9 125.3(3) . . ?
O5 C31 C30 121.9(3) . . ?
N9 C31 C30 112.8(3) . . ?
N10 C32 N9 113.3(3) . . ?
N10 C32 C33 122.2(3) . . ?
N9 C32 C33 124.5(3) . . ?
C34 C33 C32 118.3(3) . . ?
C33 C34 C35 119.9(3) . . ?
C36 C35 C34 117.7(3) . . ?
N10 C36 C35 123.7(3) . . ?
N10 C36 C37 113.9(3) . . ?
C35 C36 C37 122.5(3) . . ?
O6 C37 O7 124.2(3) . . ?
O6 C37 C36 124.2(3) . . ?
O7 C37 C36 111.6(3) . . ?
Cl1 C2X Cl2 103.0(7) . . ?
Cl4 C3X Cl3 104.7(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O4S 0.901(17) 2.35(2) 3.226(4) 163(3) 2
N3 H3N N2 0.904(18) 2.16(3) 2.645(4) 113(3) .
N5 H5N N4 0.895(18) 2.20(4) 2.651(4) 111(3) .
N7 H7N N6 0.893(18) 2.17(4) 2.666(4) 115(3) .
N9 H9N N8 0.888(18) 2.14(3) 2.646(4) 116(3) .
N9 H9N O4S 0.888(18) 2.48(3) 3.208(4) 139(3) .
O4S H4S N10 0.84 2.09 2.859(4) 151.2 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.600
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_c524
_database_code_depnum_ccdc_archive 'CCDC 1419115'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        21-H2O.cif
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 Cl2 N10 O9'
_chemical_formula_weight         857.66

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.4052(15)
_cell_length_b                   10.3199(12)
_cell_length_c                   28.307(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.870(2)
_cell_angle_gamma                90.00
_cell_volume                     3901.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3399
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.88

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6171
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22069
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6862
_reflns_number_gt                5599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0968P)²+10.1238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6862
_refine_ls_number_parameters     614
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.2280
_refine_ls_wR_factor_gt          0.2178
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1S C 0.0350(10) 0.1918(10) 0.4814(4) 0.079(4) Uani 0.451(2) 1 d PD A 1
H1S1 H 0.0036 0.2441 0.5044 0.094 Uiso 0.451(2) 1 calc PR A 1
H1S2 H 0.1067 0.2065 0.4857 0.094 Uiso 0.451(2) 1 calc PR A 1
Cl1 Cl 0.0097(4) 0.0288(5) 0.49069(18) 0.0731(13) Uani 0.451(2) 1 d PDU . 1
Cl2 Cl -0.0093(2) 0.2380(4) 0.42505(12) 0.0641(11) Uani 0.451(2) 1 d PDU A 1
C2S C -0.0520(17) 0.409(2) 0.5203(6) 0.079(4) Uani 0.304(5) 1 d PD B 2
H2S1 H -0.0785 0.3631 0.5463 0.094 Uiso 0.304(5) 1 calc PR B 2
H2S2 H 0.0059 0.4587 0.5327 0.094 Uiso 0.304(5) 1 calc PR B 2
Cl3 Cl -0.0175(7) 0.2986(8) 0.4773(4) 0.127(4) Uani 0.304(5) 1 d PDU B 2
Cl4 Cl -0.1430(4) 0.5124(6) 0.4934(2) 0.0633(19) Uani 0.304(5) 1 d PDU B 2
C3S C -0.0896(12) 0.497(3) 0.4970(9) 0.079(4) Uani 0.246(5) 1 d PD C 3
H3S1 H -0.0525 0.4651 0.4714 0.094 Uiso 0.246(5) 1 calc PR C 3
H3S2 H -0.0639 0.5809 0.5071 0.094 Uiso 0.246(5) 1 calc PR C 3
Cl5 Cl -0.0841(7) 0.3872(13) 0.5442(3) 0.117(4) Uani 0.246(5) 1 d PDU C 3
Cl6 Cl -0.2199(10) 0.5031(13) 0.4799(4) 0.132(5) Uani 0.246(5) 1 d PDU C 3
O1 O 0.8684(2) 0.5092(3) 0.18904(10) 0.0327(8) Uani 1 1 d . . .
O2 O 0.6123(2) 0.4126(3) 0.41252(9) 0.0292(7) Uani 1 1 d . . .
O3 O 0.0910(2) 0.3357(3) 0.29173(12) 0.0341(8) Uani 1 1 d . . .
O4 O 0.2582(2) 0.2491(4) 0.04481(11) 0.0381(8) Uani 1 1 d . . .
O5 O 0.8091(2) 0.1836(3) 0.12379(10) 0.0271(7) Uani 1 1 d . . .
O6 O 0.6217(2) 0.0972(3) 0.34441(10) 0.0258(7) Uani 1 1 d . . .
O7 O 0.7702(2) 0.1249(3) 0.38490(10) 0.0271(7) Uani 1 1 d . . .
N1 N 0.7180(2) 0.4867(3) 0.21961(11) 0.0166(7) Uani 1 1 d D . .
H1N H 0.6527(16) 0.475(4) 0.2136(14) 0.020 Uiso 1 1 d D . .
N2 N 0.6716(2) 0.4597(3) 0.29437(11) 0.0171(7) Uani 1 1 d . . .
N3 N 0.5153(3) 0.4030(3) 0.34216(11) 0.0216(7) Uani 1 1 d D . .
H3N H 0.516(3) 0.403(4) 0.3105(7) 0.026 Uiso 1 1 d D . .
N4 N 0.3511(3) 0.3632(3) 0.32024(12) 0.0216(7) Uani 1 1 d . . .
N5 N 0.2239(3) 0.3175(3) 0.24624(13) 0.0255(8) Uani 1 1 d D . .
H5N H 0.2902(15) 0.318(5) 0.2476(16) 0.031 Uiso 1 1 d D . .
N6 N 0.2442(2) 0.2858(3) 0.16812(12) 0.0215(7) Uani 1 1 d . . .
N7 N 0.3776(2) 0.2375(3) 0.10705(11) 0.0214(7) Uani 1 1 d D . .
H7N H 0.384(3) 0.236(4) 0.1387(7) 0.026 Uiso 1 1 d D . .
N8 N 0.5463(2) 0.2120(3) 0.11619(11) 0.0178(7) Uani 1 1 d . . .
N9 N 0.6973(2) 0.1777(3) 0.18082(11) 0.0181(7) Uani 1 1 d D . .
H9N H 0.6321(16) 0.176(4) 0.1839(15) 0.022 Uiso 1 1 d D . .
N10 N 0.7116(2) 0.1475(3) 0.26131(11) 0.0176(7) Uani 1 1 d . . .
C1 C 0.7244(3) 0.5180(4) 0.13454(14) 0.0198(8) Uani 1 1 d . . .
C2 C 0.6220(3) 0.5380(4) 0.12573(14) 0.0241(9) Uani 1 1 d . . .
H2 H 0.5819 0.5436 0.1509 0.029 Uiso 1 1 calc R . .
C3 C 0.5797(3) 0.5495(4) 0.08001(15) 0.0282(10) Uani 1 1 d . . .
H3 H 0.5112 0.5634 0.0744 0.034 Uiso 1 1 calc R . .
C4 C 0.6381(4) 0.5406(4) 0.04235(15) 0.0317(10) Uani 1 1 d . . .
H4 H 0.6089 0.5464 0.0114 0.038 Uiso 1 1 calc R . .
C5 C 0.7402(4) 0.5230(4) 0.05072(16) 0.0335(11) Uani 1 1 d . . .
H5 H 0.7800 0.5186 0.0254 0.040 Uiso 1 1 calc R . .
C6 C 0.7831(3) 0.5118(4) 0.09630(14) 0.0260(9) Uani 1 1 d . . .
H6 H 0.8519 0.5000 0.1017 0.031 Uiso 1 1 calc R . .
C7 C 0.7768(3) 0.5042(4) 0.18333(14) 0.0189(8) Uani 1 1 d . . .
C8 C 0.7483(3) 0.4730(3) 0.26812(13) 0.0172(8) Uani 1 1 d . . .
C9 C 0.8476(3) 0.4708(4) 0.28728(14) 0.0212(8) Uani 1 1 d . . .
H9 H 0.9000 0.4791 0.2680 0.025 Uiso 1 1 calc R . .
C10 C 0.8658(3) 0.4561(4) 0.33529(15) 0.0253(9) Uani 1 1 d . . .
H10 H 0.9314 0.4556 0.3490 0.030 Uiso 1 1 calc R . .
C11 C 0.7868(3) 0.4420(4) 0.36369(14) 0.0244(9) Uani 1 1 d . . .
H11 H 0.7978 0.4322 0.3964 0.029 Uiso 1 1 calc R . .
C12 C 0.6913(3) 0.4433(4) 0.34126(13) 0.0190(8) Uani 1 1 d . . .
C13 C 0.6030(3) 0.4185(4) 0.36931(13) 0.0215(9) Uani 1 1 d . . .
C14 C 0.4195(3) 0.3822(4) 0.35624(14) 0.0210(9) Uani 1 1 d . . .
C15 C 0.3955(3) 0.3851(4) 0.40330(15) 0.0268(9) Uani 1 1 d . . .
H15 H 0.4447 0.3989 0.4280 0.032 Uiso 1 1 calc R . .
C16 C 0.2978(4) 0.3671(4) 0.41200(15) 0.0311(10) Uani 1 1 d . . .
H16 H 0.2801 0.3669 0.4431 0.037 Uiso 1 1 calc R . .
C17 C 0.2255(4) 0.3491(4) 0.37519(16) 0.0316(10) Uani 1 1 d . . .
H17 H 0.1586 0.3381 0.3807 0.038 Uiso 1 1 calc R . .
C18 C 0.2559(3) 0.3481(4) 0.32968(15) 0.0254(9) Uani 1 1 d . . .
C19 C 0.1805(3) 0.3331(4) 0.28796(15) 0.0247(9) Uani 1 1 d . . .
C20 C 0.1790(3) 0.3053(4) 0.20058(15) 0.0236(9) Uani 1 1 d . . .
C21 C 0.0761(3) 0.3164(4) 0.18887(16) 0.0287(10) Uani 1 1 d . . .
H21 H 0.0323 0.3301 0.2122 0.034 Uiso 1 1 calc R . .
C22 C 0.0415(3) 0.3065(4) 0.14211(18) 0.0353(11) Uani 1 1 d . . .
H22 H -0.0267 0.3146 0.1333 0.042 Uiso 1 1 calc R . .
C23 C 0.1076(3) 0.2845(5) 0.10791(17) 0.0334(11) Uani 1 1 d . . .
H23 H 0.0849 0.2761 0.0761 0.040 Uiso 1 1 calc R . .
C24 C 0.2080(3) 0.2754(4) 0.12267(15) 0.0257(9) Uani 1 1 d . . .
C25 C 0.2829(3) 0.2525(4) 0.08701(15) 0.0247(9) Uani 1 1 d . . .
C26 C 0.4659(3) 0.2189(4) 0.08520(14) 0.0197(8) Uani 1 1 d . . .
C27 C 0.4711(3) 0.2090(4) 0.03657(14) 0.0254(9) Uani 1 1 d . . .
H27 H 0.4135 0.2114 0.0158 0.030 Uiso 1 1 calc R . .
C28 C 0.5644(3) 0.1955(4) 0.02000(14) 0.0288(10) Uani 1 1 d . . .
H28 H 0.5702 0.1880 -0.0124 0.035 Uiso 1 1 calc R . .
C29 C 0.6495(3) 0.1931(4) 0.05150(14) 0.0251(9) Uani 1 1 d . . .
H29 H 0.7132 0.1878 0.0409 0.030 Uiso 1 1 calc R . .
C30 C 0.6357(3) 0.1989(4) 0.09929(13) 0.0187(8) Uani 1 1 d . . .
C31 C 0.7235(3) 0.1872(4) 0.13527(13) 0.0186(8) Uani 1 1 d . . .
C32 C 0.7601(3) 0.1586(3) 0.22220(13) 0.0160(8) Uani 1 1 d . . .
C33 C 0.8642(3) 0.1522(4) 0.22255(14) 0.0211(8) Uani 1 1 d . . .
H33 H 0.8955 0.1583 0.1945 0.025 Uiso 1 1 calc R . .
C34 C 0.9190(3) 0.1368(4) 0.26523(14) 0.0233(9) Uani 1 1 d . . .
H34 H 0.9885 0.1327 0.2665 0.028 Uiso 1 1 calc R . .
C35 C 0.8709(3) 0.1271(4) 0.30646(14) 0.0217(9) Uani 1 1 d . . .
H35 H 0.9069 0.1176 0.3358 0.026 Uiso 1 1 calc R . .
C36 C 0.7678(3) 0.1322(4) 0.30266(13) 0.0186(8) Uani 1 1 d . . .
C37 C 0.7105(3) 0.1163(4) 0.34546(13) 0.0179(8) Uani 1 1 d . . .
C38 C 0.7241(4) 0.1121(5) 0.42884(15) 0.0326(10) Uani 1 1 d . . .
H38A H 0.6753 0.1795 0.4310 0.049 Uiso 1 1 calc R . .
H38B H 0.7743 0.1190 0.4550 0.049 Uiso 1 1 calc R . .
H38C H 0.6918 0.0292 0.4298 0.049 Uiso 1 1 calc R . .
O1W O 0.5004(2) 0.9305(3) 0.28352(10) 0.0230(6) Uani 1 1 d D . .
H1X H 0.546(2) 0.965(4) 0.3004(14) 0.028 Uiso 1 1 d D . .
H1Y H 0.513(3) 0.8532(15) 0.2803(16) 0.028 Uiso 1 1 d D . .
O2W O 0.4992(2) 0.1740(3) 0.23316(11) 0.0291(7) Uani 1 1 d D . .
H2X H 0.463(3) 0.110(3) 0.2347(17) 0.035 Uiso 1 1 d D . .
H2Y H 0.553(2) 0.168(5) 0.2492(15) 0.035 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1S Cl2 1.720(9) . ?
C1S Cl1 1.741(9) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
Cl1 Cl1 0.850(7) 3_556 ?
C2S Cl4 1.746(10) . ?
C2S Cl3 1.757(10) . ?
C2S H2S1 0.9700 . ?
C2S H2S2 0.9700 . ?
C3S Cl5 1.746(10) . ?
C3S Cl6 1.774(10) . ?
C3S H3S1 0.9700 . ?
C3S H3S2 0.9700 . ?
O1 C7 1.226(5) . ?
O2 C13 1.221(5) . ?
O3 C19 1.214(5) . ?
O4 C25 1.213(5) . ?
O5 C31 1.219(5) . ?
O6 C37 1.205(5) . ?
O7 C37 1.320(5) . ?
O7 C38 1.441(5) . ?
N1 C7 1.358(5) . ?
N1 C8 1.406(5) . ?
N1 H1N 0.886(19) . ?
N2 C8 1.325(5) . ?
N2 C12 1.342(5) . ?
N3 C13 1.358(5) . ?
N3 C14 1.393(5) . ?
N3 H3N 0.897(19) . ?
N4 C14 1.326(5) . ?
N4 C18 1.335(5) . ?
N5 C19 1.369(5) . ?
N5 C20 1.385(6) . ?
N5 H5N 0.89(2) . ?
N6 C20 1.336(5) . ?
N6 C24 1.340(5) . ?
N7 C25 1.355(5) . ?
N7 C26 1.394(5) . ?
N7 H7N 0.893(19) . ?
N8 C26 1.333(5) . ?
N8 C30 1.334(5) . ?
N9 C31 1.369(5) . ?
N9 C32 1.397(5) . ?
N9 H9N 0.886(19) . ?
N10 C32 1.335(5) . ?
N10 C36 1.347(5) . ?
C1 C2 1.390(6) . ?
C1 C6 1.393(6) . ?
C1 C7 1.502(5) . ?
C2 C3 1.373(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.394(5) . ?
C9 C10 1.369(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.503(6) . ?
C14 C15 1.397(6) . ?
C15 C16 1.367(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.496(6) . ?
C20 C21 1.396(6) . ?
C21 C22 1.368(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.502(6) . ?
C26 C27 1.388(6) . ?
C27 C28 1.380(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.495(5) . ?
C32 C33 1.397(5) . ?
C33 C34 1.369(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.377(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.498(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
O1W H1X 0.826(11) . ?
O1W H1Y 0.823(10) . ?
O2W H2X 0.820(11) . ?
O2W H2Y 0.822(10) . ?

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
Cl2 C1S Cl1 110.6(6) . . ?
Cl2 C1S H1S1 109.5 . . ?
Cl1 C1S H1S1 109.5 . . ?
Cl2 C1S H1S2 109.5 . . ?
Cl1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 108.1 . . ?
Cl1 Cl1 C1S 147.5(10) 3_556 . ?
Cl4 C2S Cl3 108.1(8) . . ?
Cl4 C2S H2S1 110.1 . . ?
Cl3 C2S H2S1 110.1 . . ?
Cl4 C2S H2S2 110.1 . . ?
Cl3 C2S H2S2 110.1 . . ?
H2S1 C2S H2S2 108.4 . . ?
Cl5 C3S Cl6 102.2(8) . . ?
Cl5 C3S H3S1 111.3 . . ?
Cl6 C3S H3S1 111.3 . . ?
Cl5 C3S H3S2 111.3 . . ?
Cl6 C3S H3S2 111.3 . . ?
H3S1 C3S H3S2 109.2 . . ?
C37 O7 C38 116.8(3) . . ?
C7 N1 C8 127.9(3) . . ?
C7 N1 H1N 120(3) . . ?
C8 N1 H1N 112(3) . . ?
C8 N2 C12 118.1(3) . . ?
C13 N3 C14 129.1(3) . . ?
C13 N3 H3N 119(3) . . ?
C14 N3 H3N 112(3) . . ?
C14 N4 C18 118.3(3) . . ?
C19 N5 C20 129.2(4) . . ?
C19 N5 H5N 117(3) . . ?
C20 N5 H5N 113(3) . . ?
C20 N6 C24 117.9(4) . . ?
C25 N7 C26 129.1(3) . . ?
C25 N7 H7N 116(3) . . ?
C26 N7 H7N 115(3) . . ?
C26 N8 C30 118.0(3) . . ?
C31 N9 C32 127.9(3) . . ?
C31 N9 H9N 115(3) . . ?
C32 N9 H9N 116(3) . . ?
C32 N10 C36 117.0(3) . . ?
C2 C1 C6 118.8(4) . . ?
C2 C1 C7 123.8(4) . . ?
C6 C1 C7 117.3(4) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 123.0(4) . . ?
O1 C7 C1 120.2(3) . . ?
N1 C7 C1 116.9(3) . . ?
N2 C8 C9 122.7(4) . . ?
N2 C8 N1 112.6(3) . . ?
C9 C8 N1 124.6(4) . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 117.1(4) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
N2 C12 C11 123.6(4) . . ?
N2 C12 C13 116.5(3) . . ?
C11 C12 C13 119.8(3) . . ?
O2 C13 N3 124.8(4) . . ?
O2 C13 C12 121.3(4) . . ?
N3 C13 C12 113.8(3) . . ?
N4 C14 N3 113.4(3) . . ?
N4 C14 C15 122.4(4) . . ?
N3 C14 C15 124.2(4) . . ?
C16 C15 C14 118.1(4) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 117.5(4) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
N4 C18 C17 123.2(4) . . ?
N4 C18 C19 116.6(4) . . ?
C17 C18 C19 120.2(4) . . ?
O3 C19 N5 125.0(4) . . ?
O3 C19 C18 122.3(4) . . ?
N5 C19 C18 112.6(4) . . ?
N6 C20 N5 113.4(3) . . ?
N6 C20 C21 122.7(4) . . ?
N5 C20 C21 123.9(4) . . ?
C22 C21 C20 118.1(4) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
C21 C22 C23 120.3(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 117.7(4) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
N6 C24 C23 123.4(4) . . ?
N6 C24 C25 116.7(4) . . ?
C23 C24 C25 119.9(4) . . ?
O4 C25 N7 125.2(4) . . ?
O4 C25 C24 121.7(4) . . ?
N7 C25 C24 113.1(3) . . ?
N8 C26 C27 122.9(4) . . ?
N8 C26 N7 112.6(3) . . ?
C27 C26 N7 124.4(3) . . ?
C28 C27 C26 117.9(4) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 120.2(4) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 117.2(4) . . ?
C30 C29 H29 121.4 . . ?
C28 C29 H29 121.4 . . ?
N8 C30 C29 123.7(4) . . ?
N8 C30 C31 116.3(3) . . ?
C29 C30 C31 120.0(4) . . ?
O5 C31 N9 124.9(4) . . ?
O5 C31 C30 121.7(3) . . ?
N9 C31 C30 113.4(3) . . ?
N10 C32 C33 123.1(3) . . ?
N10 C32 N9 113.9(3) . . ?
C33 C32 N9 122.9(3) . . ?
C34 C33 C32 118.2(4) . . ?
C34 C33 H33 120.9 . . ?
C32 C33 H33 120.9 . . ?
C33 C34 C35 119.9(4) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 117.9(4) . . ?
C36 C35 H35 121.1 . . ?
C34 C35 H35 121.1 . . ?
N10 C36 C35 123.8(4) . . ?
N10 C36 C37 115.4(3) . . ?
C35 C36 C37 120.8(3) . . ?
O6 C37 O7 124.0(4) . . ?
O6 C37 C36 124.9(3) . . ?
O7 C37 C36 111.2(3) . . ?
O7 C38 H38A 109.5 . . ?
O7 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O7 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
H1X O1W H1Y 109(5) . . ?
H2X O2W H2Y 114(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2W H2Y N10 0.822(10) 2.13(2) 2.903(4) 156(5) .
O2W H2X N2 0.820(11) 2.47(2) 3.231(4) 155(4) 2_645
O2W H2X O1W 0.820(11) 2.34(4) 2.888(4) 125(4) 1_545
O1W H1Y O2W 0.823(10) 1.892(17) 2.689(4) 163(5) 2_655
O1W H1X O6 0.826(11) 2.055(19) 2.845(4) 160(4) 1_565
N9 H9N O2W 0.886(19) 2.35(3) 3.148(5) 150(4) .
N9 H9N N8 0.886(19) 2.18(4) 2.634(4) 111(3) .
N7 H7N N6 0.893(19) 2.18(4) 2.639(5) 111(3) .
N1 H1N O1W 0.886(19) 2.11(2) 2.979(4) 166(4) 2_645

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_b669
_database_code_depnum_ccdc_archive 'CCDC 1419116'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        22-H2O.cif
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 Cl2 N10 O9'
_chemical_formula_weight         857.66

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   13.4675(16)
_cell_length_b                   10.3791(12)
_cell_length_c                   13.7432(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.610(2)
_cell_angle_gamma                90.00
_cell_volume                     1911.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2918
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.72

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   Mulyi-scan
_exptl_absorpt_correction_T_min  0.8684
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11236
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6546
_reflns_number_gt                5832
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0924P)²+0.2442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(16)
_refine_ls_number_reflns         6546
_refine_ls_number_parameters     597
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.089
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37575(19) 0.9947(3) 0.9021(2) 0.0326(7) Uani 1 1 d . . .
O2 O 0.1047(2) 0.9274(3) 1.35146(18) 0.0317(6) Uani 1 1 d . . .
O3 O -0.41593(19) 0.8261(3) 1.10714(19) 0.0293(6) Uani 1 1 d . . .
O4 O -0.25831(18) 0.7693(3) 0.59452(17) 0.0311(6) Uani 1 1 d . . .
O5 O 0.29127(18) 0.6822(3) 0.75481(17) 0.0232(6) Uani 1 1 d . . .
O6 O 0.10699(19) 0.6064(3) 1.20695(18) 0.0295(6) Uani 1 1 d . . .
O7 O 0.25682(19) 0.6003(3) 1.29265(17) 0.0278(6) Uani 1 1 d . . .
N1 N 0.2216(2) 0.9812(3) 0.9566(2) 0.0200(6) Uani 1 1 d D . .
H1N H 0.1630(17) 0.964(4) 0.934(3) 0.024 Uiso 1 1 d D . .
N2 N 0.1686(2) 0.9587(3) 1.1088(2) 0.0194(6) Uani 1 1 d . . .
N3 N 0.0080(2) 0.9150(3) 1.2050(2) 0.0220(7) Uani 1 1 d D . .
H3N H 0.011(3) 0.913(4) 1.1419(15) 0.026 Uiso 1 1 d D . .
N4 N -0.1566(2) 0.8695(3) 1.1619(2) 0.0213(6) Uani 1 1 d . . .
N5 N -0.2855(2) 0.8072(3) 1.0128(2) 0.0220(7) Uani 1 1 d D . .
H5N H -0.2236(15) 0.812(4) 1.016(3) 0.026 Uiso 1 1 d D . .
N6 N -0.2690(2) 0.7848(3) 0.8512(2) 0.0199(6) Uani 1 1 d . . .
N7 N -0.1373(2) 0.7588(3) 0.7240(2) 0.0216(6) Uani 1 1 d D . .
H7N H -0.128(3) 0.754(4) 0.7857(14) 0.026 Uiso 1 1 d D . .
N8 N 0.0300(2) 0.7268(3) 0.7419(2) 0.0190(6) Uani 1 1 d . . .
N9 N 0.1828(2) 0.6791(3) 0.8726(2) 0.0187(6) Uani 1 1 d D . .
H9N H 0.1209(16) 0.684(4) 0.884(3) 0.022 Uiso 1 1 d D . .
N10 N 0.1981(2) 0.6435(3) 1.0384(2) 0.0188(6) Uani 1 1 d . . .
C1 C 0.2378(3) 1.0179(3) 0.7837(3) 0.0216(8) Uani 1 1 d . . .
C2 C 0.2973(3) 1.0022(4) 0.7082(3) 0.0287(9) Uani 1 1 d . . .
H2 H 0.3656 0.9803 0.7226 0.034 Uiso 1 1 calc R . .
C3 C 0.2590(3) 1.0179(4) 0.6126(3) 0.0343(10) Uani 1 1 d . . .
H3 H 0.3009 1.0059 0.5616 0.041 Uiso 1 1 calc R . .
C4 C 0.1598(3) 1.0511(4) 0.5901(3) 0.0339(9) Uani 1 1 d . . .
H4 H 0.1331 1.0598 0.5239 0.041 Uiso 1 1 calc R . .
C5 C 0.1000(3) 1.0713(4) 0.6649(3) 0.0296(9) Uani 1 1 d . . .
H5 H 0.0323 1.0963 0.6501 0.035 Uiso 1 1 calc R . .
C6 C 0.1382(3) 1.0554(3) 0.7612(3) 0.0232(8) Uani 1 1 d . . .
H6 H 0.0968 1.0698 0.8123 0.028 Uiso 1 1 calc R . .
C7 C 0.2846(3) 0.9977(3) 0.8858(3) 0.0232(8) Uani 1 1 d . . .
C8 C 0.2474(3) 0.9659(3) 1.0572(3) 0.0217(8) Uani 1 1 d . . .
C9 C 0.3459(3) 0.9571(4) 1.1010(3) 0.0262(8) Uani 1 1 d . . .
H9 H 0.4008 0.9608 1.0627 0.031 Uiso 1 1 calc R . .
C10 C 0.3605(3) 0.9428(4) 1.2009(3) 0.0291(9) Uani 1 1 d . . .
H10 H 0.4264 0.9382 1.2325 0.035 Uiso 1 1 calc R . .
C11 C 0.2789(3) 0.9350(4) 1.2557(3) 0.0268(8) Uani 1 1 d . . .
H11 H 0.2877 0.9248 1.3247 0.032 Uiso 1 1 calc R . .
C12 C 0.1855(3) 0.9428(3) 1.2062(2) 0.0227(8) Uani 1 1 d . . .
C13 C 0.0961(3) 0.9287(3) 1.2618(3) 0.0246(8) Uani 1 1 d . . .
C14 C -0.0873(3) 0.8970(3) 1.2357(3) 0.0231(8) Uani 1 1 d . . .
C15 C -0.1092(3) 0.9086(3) 1.3324(3) 0.0256(8) Uani 1 1 d . . .
H15 H -0.0588 0.9295 1.3831 0.031 Uiso 1 1 calc R . .
C16 C -0.2075(3) 0.8885(4) 1.3522(3) 0.0284(9) Uani 1 1 d . . .
H16 H -0.2250 0.8940 1.4174 0.034 Uiso 1 1 calc R . .
C17 C -0.2799(3) 0.8605(4) 1.2762(3) 0.0267(8) Uani 1 1 d . . .
H17 H -0.3473 0.8465 1.2881 0.032 Uiso 1 1 calc R . .
C18 C -0.2509(3) 0.8536(3) 1.1831(3) 0.0210(8) Uani 1 1 d . . .
C19 C -0.3275(3) 0.8277(3) 1.0983(3) 0.0226(8) Uani 1 1 d . . .
C20 C -0.3324(3) 0.7944(3) 0.9186(2) 0.0209(7) Uani 1 1 d . . .
C21 C -0.4357(3) 0.7950(3) 0.8970(3) 0.0246(8) Uani 1 1 d . . .
H21 H -0.4791 0.8015 0.9473 0.030 Uiso 1 1 calc R . .
C22 C -0.4730(3) 0.7855(4) 0.7997(3) 0.0274(8) Uani 1 1 d . . .
H22 H -0.5430 0.7850 0.7823 0.033 Uiso 1 1 calc R . .
C23 C -0.4082(3) 0.7770(4) 0.7277(3) 0.0248(8) Uani 1 1 d . . .
H23 H -0.4324 0.7717 0.6606 0.030 Uiso 1 1 calc R . .
C24 C -0.3070(3) 0.7764(3) 0.7570(3) 0.0219(7) Uani 1 1 d . . .
C25 C -0.2328(3) 0.7675(3) 0.6825(3) 0.0213(7) Uani 1 1 d . . .
C26 C -0.0491(2) 0.7503(3) 0.6789(2) 0.0187(7) Uani 1 1 d . . .
C27 C -0.0432(3) 0.7682(3) 0.5795(2) 0.0225(8) Uani 1 1 d . . .
H27 H -0.1011 0.7858 0.5364 0.027 Uiso 1 1 calc R . .
C28 C 0.0498(3) 0.7594(4) 0.5452(3) 0.0254(8) Uani 1 1 d . . .
H28 H 0.0563 0.7702 0.4775 0.030 Uiso 1 1 calc R . .
C29 C 0.1332(3) 0.7350(3) 0.6095(2) 0.0236(8) Uani 1 1 d . . .
H29 H 0.1977 0.7294 0.5872 0.028 Uiso 1 1 calc R . .
C30 C 0.1198(2) 0.7189(3) 0.7072(2) 0.0185(7) Uani 1 1 d . . .
C31 C 0.2073(2) 0.6915(3) 0.7799(2) 0.0178(7) Uani 1 1 d . . .
C32 C 0.2457(3) 0.6521(3) 0.9581(2) 0.0175(7) Uani 1 1 d . . .
C39 C 0.3489(2) 0.6366(3) 0.9576(2) 0.0189(7) Uani 1 1 d . . .
H39 H 0.3799 0.6413 0.8985 0.023 Uiso 1 1 calc R . .
C34 C 0.4040(3) 0.6144(3) 1.0459(3) 0.0236(8) Uani 1 1 d . . .
H34 H 0.4743 0.6041 1.0485 0.028 Uiso 1 1 calc R . .
C35 C 0.3568(3) 0.6069(3) 1.1308(3) 0.0214(7) Uani 1 1 d . . .
H35 H 0.3937 0.5935 1.1924 0.026 Uiso 1 1 calc R . .
C36 C 0.2539(3) 0.6198(3) 1.1227(2) 0.0196(7) Uani 1 1 d . . .
C37 C 0.1962(3) 0.6088(3) 1.2097(3) 0.0214(7) Uani 1 1 d . . .
C38 C 0.2070(3) 0.5962(4) 1.3818(3) 0.0331(9) Uani 1 1 d . . .
H38A H 0.1812 0.6821 1.3952 0.050 Uiso 1 1 calc R . .
H38B H 0.2546 0.5692 1.4365 0.050 Uiso 1 1 calc R . .
H38C H 0.1516 0.5347 1.3738 0.050 Uiso 1 1 calc R . .
O1W O -0.0034(2) 0.4350(3) 0.0665(2) 0.0318(6) Uani 1 1 d D . .
H1A H 0.034(3) 0.469(4) 0.114(2) 0.038 Uiso 1 1 d D . .
H1B H 0.011(3) 0.357(2) 0.048(3) 0.038 Uiso 1 1 d D . .
O2W O 0.0174(2) 0.1842(3) 0.0190(2) 0.0384(7) Uani 1 1 d D . .
H2A H -0.037(2) 0.179(5) -0.017(3) 0.046 Uiso 1 1 d D . .
H2B H 0.050(3) 0.117(3) 0.035(3) 0.046 Uiso 1 1 d D . .
C1S C 0.4992(10) 0.6079(13) 0.4903(8) 0.091(4) Uani 0.547(4) 1 d PDU A 1
H1S1 H 0.5677 0.6199 0.5224 0.109 Uiso 0.547(4) 1 calc PR A 1
H1S2 H 0.4969 0.5223 0.4583 0.109 Uiso 0.547(4) 1 calc PR A 1
Cl1A Cl 0.4780(3) 0.7247(6) 0.3999(3) 0.124(2) Uani 0.547(4) 1 d PDU A 1
Cl1B Cl 0.4167(2) 0.6065(4) 0.58063(19) 0.0822(12) Uani 0.547(4) 1 d PDU A 1
C2S C 0.5311(11) 0.6766(8) 0.4448(14) 0.104(4) Uani 0.453(4) 1 d PDU A 2
H2S1 H 0.5976 0.7018 0.4761 0.124 Uiso 0.453(4) 1 calc PR A 2
H2S2 H 0.5358 0.6703 0.3735 0.124 Uiso 0.453(4) 1 calc PR A 2
Cl2A Cl 0.4997(5) 0.5245(5) 0.4891(7) 0.145(3) Uani 0.453(4) 1 d PDU A 2
Cl2B Cl 0.4445(5) 0.7975(5) 0.4666(6) 0.161(3) Uani 0.453(4) 1 d PDU 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
O1 C7 1.226(4) . ?
O2 C13 1.227(4) . ?
O3 C19 1.209(4) . ?
O4 C25 1.224(4) . ?
O5 C31 1.218(4) . ?
O6 C37 1.198(4) . ?
O7 C37 1.338(4) . ?
O7 C38 1.454(4) . ?
N1 C7 1.363(5) . ?
N1 C8 1.402(5) . ?
N1 H1N 0.837(19) . ?
N2 C8 1.335(5) . ?
N2 C12 1.346(4) . ?
N3 C13 1.362(5) . ?
N3 C14 1.402(5) . ?
N3 H3N 0.872(19) . ?
N4 C18 1.341(5) . ?
N4 C14 1.341(5) . ?
N5 C19 1.369(5) . ?
N5 C20 1.390(5) . ?
N5 H5N 0.832(19) . ?
N6 C20 1.324(4) . ?
N6 C24 1.347(4) . ?
N7 C25 1.358(4) . ?
N7 C26 1.396(4) . ?
N7 H7N 0.847(19) . ?
N8 C26 1.328(4) . ?
N8 C30 1.346(4) . ?
N9 C31 1.353(4) . ?
N9 C32 1.408(4) . ?
N9 H9N 0.863(19) . ?
N10 C32 1.332(4) . ?
N10 C36 1.341(5) . ?
C1 C2 1.381(5) . ?
C1 C6 1.402(5) . ?
C1 C7 1.495(5) . ?
C2 C3 1.374(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.404(5) . ?
C9 C10 1.375(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.496(5) . ?
C14 C15 1.395(5) . ?
C15 C16 1.393(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.504(5) . ?
C20 C21 1.394(5) . ?
C21 C22 1.385(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.502(5) . ?
C26 C27 1.389(5) . ?
C27 C28 1.383(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.384(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.382(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.496(5) . ?
C32 C39 1.400(5) . ?
C39 C34 1.378(5) . ?
C39 H39 0.9500 . ?
C34 C35 1.384(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.494(5) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O1W H1A 0.86(2) . ?
O1W H1B 0.87(2) . ?
O2W H2A 0.85(2) . ?
O2W H2B 0.85(2) . ?
C1S Cl1A 1.739(5) . ?
C1S Cl1B 1.746(5) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S Cl2B 1.758(5) . ?
C2S Cl2A 1.759(5) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 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
C37 O7 C38 115.2(3) . . ?
C7 N1 C8 127.4(3) . . ?
C7 N1 H1N 113(3) . . ?
C8 N1 H1N 118(3) . . ?
C8 N2 C12 117.9(3) . . ?
C13 N3 C14 127.8(3) . . ?
C13 N3 H3N 117(3) . . ?
C14 N3 H3N 115(3) . . ?
C18 N4 C14 117.8(3) . . ?
C19 N5 C20 128.7(3) . . ?
C19 N5 H5N 116(3) . . ?
C20 N5 H5N 115(3) . . ?
C20 N6 C24 117.8(3) . . ?
C25 N7 C26 129.1(3) . . ?
C25 N7 H7N 118(3) . . ?
C26 N7 H7N 113(3) . . ?
C26 N8 C30 118.2(3) . . ?
C31 N9 C32 128.5(3) . . ?
C31 N9 H9N 119(3) . . ?
C32 N9 H9N 112(3) . . ?
C32 N10 C36 116.9(3) . . ?
C2 C1 C6 118.6(3) . . ?
C2 C1 C7 117.8(3) . . ?
C6 C1 C7 123.6(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 N1 123.2(3) . . ?
O1 C7 C1 119.9(3) . . ?
N1 C7 C1 116.9(3) . . ?
N2 C8 N1 113.4(3) . . ?
N2 C8 C9 122.4(3) . . ?
N1 C8 C9 124.2(3) . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 117.5(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
N2 C12 C11 123.9(3) . . ?
N2 C12 C13 116.9(3) . . ?
C11 C12 C13 119.1(3) . . ?
O2 C13 N3 124.5(3) . . ?
O2 C13 C12 120.8(3) . . ?
N3 C13 C12 114.7(3) . . ?
N4 C14 C15 122.9(3) . . ?
N4 C14 N3 113.0(3) . . ?
C15 C14 N3 124.1(3) . . ?
C16 C15 C14 117.8(4) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
N4 C18 C17 123.8(4) . . ?
N4 C18 C19 116.5(3) . . ?
C17 C18 C19 119.7(3) . . ?
O3 C19 N5 125.3(3) . . ?
O3 C19 C18 122.1(3) . . ?
N5 C19 C18 112.5(3) . . ?
N6 C20 N5 113.2(3) . . ?
N6 C20 C21 123.3(3) . . ?
N5 C20 C21 123.5(3) . . ?
C22 C21 C20 117.8(3) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 117.7(3) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
N6 C24 C23 123.4(3) . . ?
N6 C24 C25 116.3(3) . . ?
C23 C24 C25 120.3(3) . . ?
O4 C25 N7 125.4(3) . . ?
O4 C25 C24 122.1(3) . . ?
N7 C25 C24 112.6(3) . . ?
N8 C26 C27 123.1(3) . . ?
N8 C26 N7 112.7(3) . . ?
C27 C26 N7 124.2(3) . . ?
C28 C27 C26 117.8(3) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 117.9(3) . . ?
C30 C29 H29 121.1 . . ?
C28 C29 H29 121.1 . . ?
N8 C30 C29 123.0(3) . . ?
N8 C30 C31 116.8(3) . . ?
C29 C30 C31 120.2(3) . . ?
O5 C31 N9 125.3(3) . . ?
O5 C31 C30 121.2(3) . . ?
N9 C31 C30 113.5(3) . . ?
N10 C32 C39 123.7(3) . . ?
N10 C32 N9 113.9(3) . . ?
C39 C32 N9 122.4(3) . . ?
C34 C39 C32 117.6(3) . . ?
C34 C39 H39 121.2 . . ?
C32 C39 H39 121.2 . . ?
C39 C34 C35 120.0(3) . . ?
C39 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 117.7(3) . . ?
C34 C35 H35 121.2 . . ?
C36 C35 H35 121.2 . . ?
N10 C36 C35 124.0(3) . . ?
N10 C36 C37 114.5(3) . . ?
C35 C36 C37 121.5(3) . . ?
O6 C37 O7 123.5(3) . . ?
O6 C37 C36 125.1(3) . . ?
O7 C37 C36 111.4(3) . . ?
O7 C38 H38A 109.5 . . ?
O7 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O7 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
H1A O1W H1B 118(4) . . ?
H2A O2W H2B 120(5) . . ?
Cl1A C1S Cl1B 116.2(4) . . ?
Cl1A C1S H1S1 108.2 . . ?
Cl1B C1S H1S1 108.2 . . ?
Cl1A C1S H1S2 108.2 . . ?
Cl1B C1S H1S2 108.2 . . ?
H1S1 C1S H1S2 107.4 . . ?
Cl2B C2S Cl2A 113.3(5) . . ?
Cl2B C2S H2S1 108.9 . . ?
Cl2A C2S H2S1 108.9 . . ?
Cl2B C2S H2S2 108.9 . . ?
Cl2A C2S H2S2 108.9 . . ?
H2S1 C2S H2S2 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1W 0.837(19) 2.17(2) 2.965(4) 159(3) 2_556
N5 H5N N4 0.832(19) 2.19(4) 2.632(4) 113(3) .
N7 H7N N6 0.847(19) 2.21(4) 2.623(4) 110(3) .
N9 H9N O2W 0.863(19) 2.40(2) 3.206(4) 156(3) 2_556
O1W H1A O6 0.86(2) 2.10(2) 2.922(4) 161(4) 1_554
O1W H1B O2W 0.87(2) 1.85(2) 2.705(4) 168(4) .
O2W H2A N10 0.85(2) 2.19(3) 2.962(4) 152(4) 2_546
O2W H2B O1W 0.85(2) 2.40(5) 2.840(4) 113(4) 2_545
O2W H2B N2 0.85(2) 2.44(2) 3.264(4) 166(5) 1_544

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_c522
_database_code_depnum_ccdc_archive 'CCDC 1419117'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        23-H2O.cif
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 Cl2 N10 O9'
_chemical_formula_weight         857.66

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   13.5062(16)
_cell_length_b                   10.3752(12)
_cell_length_c                   13.7885(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.675(3)
_cell_angle_gamma                90.00
_cell_volume                     1922.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1003
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.19

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11259
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6542
_reflns_number_gt                6052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0868P)²+0.6440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_number_reflns         6542
_refine_ls_number_parameters     585
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.097
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1S C 0.9892(18) 0.198(3) 1.0002(15) 0.250 Uiso 0.571(5) 1 d PD A 2
H1S1 H 0.9806 0.2882 0.9781 0.300 Uiso 0.571(5) 1 calc PR A 2
H1S2 H 1.0562 0.1908 1.0361 0.300 Uiso 0.571(5) 1 calc PR A 2
Cl1 Cl 0.9862(4) 0.0979(10) 0.8954(5) 0.209(4) Uani 0.571(5) 1 d PDU A 2
Cl2 Cl 0.8995(3) 0.1656(7) 1.0834(2) 0.147(2) Uani 0.571(5) 1 d PDU A 2
C2S C 1.0565(11) 0.0339(16) 0.944(2) 0.250 Uiso 0.429(5) 1 d PD A 1
H2S1 H 1.0748 0.0556 0.8783 0.300 Uiso 0.429(5) 1 calc PR A 1
H2S2 H 1.0819 0.1004 0.9918 0.300 Uiso 0.429(5) 1 calc PR A 1
Cl3 Cl 0.9294(6) 0.0039(11) 0.9462(9) 0.220(5) Uani 0.429(5) 1 d PDU A 1
Cl4 Cl 1.0911(6) -0.1209(14) 0.9802(7) 0.228(5) Uani 0.429(5) 1 d PDU A 1
O1W O 0.5188(2) 0.6131(3) 0.5234(2) 0.0432(7) Uani 1 1 d D . .
H1W H 0.548(3) 0.683(2) 0.523(3) 0.052 Uiso 1 1 d D . .
H1X H 0.4656(17) 0.614(4) 0.490(3) 0.052 Uiso 1 1 d D . .
O2W O 0.49451(18) 0.3612(3) 0.56637(19) 0.0351(6) Uani 1 1 d D . .
H2W H 0.536(2) 0.334(3) 0.609(2) 0.042 Uiso 1 1 d D . .
H2X H 0.511(3) 0.433(2) 0.547(3) 0.042 Uiso 1 1 d D . .
O1 O 0.87673(17) 0.8043(3) 0.40184(18) 0.0350(6) Uani 1 1 d . . .
O2 O 0.60536(18) 0.8666(2) 0.84906(16) 0.0312(6) Uani 1 1 d . . .
O3 O 0.08732(17) 0.9720(2) 0.60580(18) 0.0318(6) Uani 1 1 d . . .
O4 O 0.24383(16) 1.0199(3) 0.09386(16) 0.0317(6) Uani 1 1 d . . .
O5 O 0.79134(16) 1.1146(2) 0.25340(16) 0.0258(5) Uani 1 1 d . . .
O6 O 0.60523(17) 1.1884(3) 0.70339(17) 0.0315(6) Uani 1 1 d . . .
O7 O 0.75489(18) 1.1929(3) 0.78954(16) 0.0311(6) Uani 1 1 d . . .
N1 N 0.72359(19) 0.8150(3) 0.4559(2) 0.0229(6) Uani 1 1 d D . .
H1N H 0.6598(16) 0.826(3) 0.4361(19) 0.027 Uiso 1 1 d D . .
N2 N 0.67064(19) 0.8370(3) 0.60715(19) 0.0207(6) Uani 1 1 d . . .
N3 N 0.5096(2) 0.8802(3) 0.70293(19) 0.0224(6) Uani 1 1 d D . .
H3N H 0.518(3) 0.883(4) 0.6378(15) 0.027 Uiso 1 1 d D . .
N4 N 0.3461(2) 0.9268(2) 0.66035(19) 0.0219(6) Uani 1 1 d . . .
N5 N 0.2166(2) 0.9887(3) 0.5110(2) 0.0240(6) Uani 1 1 d D . .
H5N H 0.2819(15) 0.997(4) 0.517(3) 0.029 Uiso 1 1 d D . .
N6 N 0.23269(19) 1.0115(3) 0.34935(19) 0.0221(6) Uani 1 1 d . . .
N7 N 0.36361(19) 1.0378(3) 0.22267(19) 0.0230(6) Uani 1 1 d D . .
H7N H 0.370(3) 1.052(4) 0.2853(15) 0.028 Uiso 1 1 d D . .
N8 N 0.53085(18) 1.0695(2) 0.24009(18) 0.0194(5) Uani 1 1 d . . .
N9 N 0.68251(19) 1.1167(3) 0.37040(18) 0.0196(6) Uani 1 1 d D . .
H9N H 0.6188(15) 1.109(4) 0.376(3) 0.024 Uiso 1 1 d D . .
C1 C 0.7400(2) 0.7784(3) 0.2832(2) 0.0227(7) Uani 1 1 d . . .
N10 N 0.69693(19) 1.1525(2) 0.53497(18) 0.0196(5) Uani 1 1 d . . .
C2 C 0.6405(2) 0.7440(3) 0.2594(3) 0.0254(7) Uani 1 1 d . . .
H2 H 0.5980 0.7324 0.3096 0.030 Uiso 1 1 calc R . .
C3 C 0.6037(3) 0.7268(3) 0.1633(3) 0.0314(8) Uani 1 1 d . . .
H3 H 0.5361 0.7030 0.1479 0.038 Uiso 1 1 calc R . .
C4 C 0.6644(3) 0.7440(3) 0.0892(3) 0.0341(8) Uani 1 1 d . . .
H4 H 0.6383 0.7340 0.0230 0.041 Uiso 1 1 calc R . .
C5 C 0.7642(3) 0.7761(4) 0.1125(3) 0.0347(8) Uani 1 1 d . . .
H5 H 0.8065 0.7870 0.0620 0.042 Uiso 1 1 calc R . .
C6 C 0.8013(3) 0.7919(3) 0.2080(3) 0.0300(8) Uani 1 1 d . . .
H6 H 0.8697 0.8123 0.2231 0.036 Uiso 1 1 calc R . .
C7 C 0.7867(2) 0.8006(3) 0.3851(2) 0.0229(7) Uani 1 1 d . . .
C8 C 0.7492(2) 0.8298(3) 0.5559(2) 0.0220(7) Uani 1 1 d . . .
C9 C 0.8470(2) 0.8398(3) 0.5994(3) 0.0255(7) Uani 1 1 d . . .
H9 H 0.9018 0.8369 0.5612 0.031 Uiso 1 1 calc R . .
C10 C 0.8617(2) 0.8541(3) 0.6995(3) 0.0292(8) Uani 1 1 d . . .
H10 H 0.9274 0.8592 0.7312 0.035 Uiso 1 1 calc R . .
C11 C 0.7812(2) 0.8608(3) 0.7535(3) 0.0279(8) Uani 1 1 d . . .
H11 H 0.7900 0.8708 0.8223 0.033 Uiso 1 1 calc R . .
C12 C 0.6868(2) 0.8525(3) 0.7037(2) 0.0236(7) Uani 1 1 d . . .
C13 C 0.5981(2) 0.8661(3) 0.7601(2) 0.0244(7) Uani 1 1 d . . .
C14 C 0.4149(2) 0.8990(3) 0.7332(2) 0.0224(7) Uani 1 1 d . . .
C15 C 0.3933(3) 0.8872(3) 0.8294(2) 0.0258(7) Uani 1 1 d . . .
H15 H 0.4434 0.8653 0.8799 0.031 Uiso 1 1 calc R . .
C16 C 0.2958(3) 0.9084(4) 0.8489(2) 0.0314(8) Uani 1 1 d . . .
H16 H 0.2788 0.9034 0.9140 0.038 Uiso 1 1 calc R . .
C17 C 0.2236(3) 0.9367(3) 0.7743(3) 0.0290(8) Uani 1 1 d . . .
H17 H 0.1565 0.9508 0.7866 0.035 Uiso 1 1 calc R . .
C18 C 0.2519(2) 0.9439(3) 0.6809(2) 0.0230(7) Uani 1 1 d . . .
C19 C 0.1756(2) 0.9703(3) 0.5965(2) 0.0247(7) Uani 1 1 d . . .
C20 C 0.1702(2) 1.0030(3) 0.4173(2) 0.0213(7) Uani 1 1 d . . .
C21 C 0.0667(2) 1.0026(3) 0.3954(3) 0.0260(7) Uani 1 1 d . . .
H21 H 0.0234 0.9961 0.4454 0.031 Uiso 1 1 calc R . .
C22 C 0.0299(2) 1.0119(3) 0.2990(3) 0.0276(7) Uani 1 1 d . . .
H22 H -0.0399 1.0127 0.2820 0.033 Uiso 1 1 calc R . .
C23 C 0.0936(2) 1.0200(3) 0.2266(2) 0.0277(7) Uani 1 1 d . . .
H23 H 0.0690 1.0256 0.1597 0.033 Uiso 1 1 calc R . .
C24 C 0.1943(2) 1.0195(3) 0.2557(2) 0.0225(7) Uani 1 1 d . . .
C25 C 0.2684(2) 1.0263(3) 0.1820(2) 0.0222(7) Uani 1 1 d . . .
C26 C 0.4521(2) 1.0449(3) 0.1773(2) 0.0191(6) Uani 1 1 d . . .
C27 C 0.4575(2) 1.0268(3) 0.0783(2) 0.0233(7) Uani 1 1 d . . .
H27 H 0.3993 1.0107 0.0355 0.028 Uiso 1 1 calc R . .
C28 C 0.5503(2) 1.0331(3) 0.0438(2) 0.0247(7) Uani 1 1 d . . .
H28 H 0.5566 1.0197 -0.0235 0.030 Uiso 1 1 calc R . .
C29 C 0.6338(2) 1.0590(3) 0.1076(2) 0.0233(7) Uani 1 1 d . . .
H29 H 0.6981 1.0650 0.0855 0.028 Uiso 1 1 calc R . .
C30 C 0.6197(2) 1.0759(3) 0.2054(2) 0.0193(6) Uani 1 1 d . . .
C31 C 0.7073(2) 1.1047(3) 0.2785(2) 0.0194(6) Uani 1 1 d . . .
C32 C 0.7448(2) 1.1435(3) 0.4556(2) 0.0192(6) Uani 1 1 d . . .
C33 C 0.8480(2) 1.1586(3) 0.4567(2) 0.0221(7) Uani 1 1 d . . .
H33 H 0.8795 1.1528 0.3982 0.026 Uiso 1 1 calc R . .
C34 C 0.9027(2) 1.1821(3) 0.5445(2) 0.0246(7) Uani 1 1 d . . .
H34 H 0.9727 1.1933 0.5473 0.030 Uiso 1 1 calc R . .
C35 C 0.8553(2) 1.1893(3) 0.6284(2) 0.0238(7) Uani 1 1 d . . .
H35 H 0.8917 1.2031 0.6901 0.029 Uiso 1 1 calc R . .
C36 C 0.7525(2) 1.1758(3) 0.6200(2) 0.0211(7) Uani 1 1 d . . .
C37 C 0.6952(2) 1.1859(3) 0.7071(2) 0.0226(7) Uani 1 1 d . . .
C38 C 0.7060(3) 1.1938(4) 0.8787(2) 0.0342(8) Uani 1 1 d . . .
H38A H 0.6578 1.2646 0.8764 0.051 Uiso 1 1 calc R . .
H38B H 0.7558 1.2055 0.9347 0.051 Uiso 1 1 calc R . .
H38C H 0.6713 1.1117 0.8852 0.051 Uiso 1 1 calc R . .


_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
C1S Cl1 1.775(10) . ?
C1S Cl2 1.781(10) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S Cl4 1.732(11) . ?
C2S Cl3 1.748(11) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?
O1W H1W 0.822(11) . ?
O1W H1X 0.814(11) . ?
O2W H2W 0.818(11) . ?
O2W H2X 0.829(11) . ?
O1 C7 1.216(4) . ?
O2 C13 1.221(4) . ?
O3 C19 1.212(4) . ?
O4 C25 1.230(4) . ?
O5 C31 1.223(4) . ?
O6 C37 1.211(4) . ?
O7 C37 1.329(4) . ?
O7 C38 1.452(4) . ?
N1 C7 1.365(4) . ?
N1 C8 1.397(4) . ?
N1 H1N 0.885(19) . ?
N2 C8 1.333(4) . ?
N2 C12 1.337(4) . ?
N3 C13 1.374(4) . ?
N3 C14 1.397(4) . ?
N3 H3N 0.916(19) . ?
N4 C14 1.330(4) . ?
N4 C18 1.342(4) . ?
N5 C19 1.364(4) . ?
N5 C20 1.388(4) . ?
N5 H5N 0.881(19) . ?
N6 C20 1.325(4) . ?
N6 C24 1.346(4) . ?
N7 C25 1.356(4) . ?
N7 C26 1.405(4) . ?
N7 H7N 0.872(19) . ?
N8 C26 1.328(4) . ?
N8 C30 1.337(4) . ?
N9 C31 1.348(4) . ?
N9 C32 1.403(4) . ?
N9 H9N 0.876(19) . ?
C1 C6 1.397(5) . ?
C1 C2 1.398(5) . ?
C1 C7 1.500(5) . ?
N10 C32 1.328(4) . ?
N10 C36 1.350(4) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.400(4) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.498(5) . ?
C14 C15 1.392(5) . ?
C15 C16 1.386(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.502(5) . ?
C20 C21 1.400(4) . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.496(4) . ?
C26 C27 1.387(4) . ?
C27 C28 1.385(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.388(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.507(4) . ?
C32 C33 1.402(4) . ?
C33 C34 1.376(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.496(4) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C1S Cl2 116.9(8) . . ?
Cl1 C1S H1S1 108.1 . . ?
Cl2 C1S H1S1 108.1 . . ?
Cl1 C1S H1S2 108.1 . . ?
Cl2 C1S H1S2 108.1 . . ?
H1S1 C1S H1S2 107.3 . . ?
Cl4 C2S Cl3 93.9(8) . . ?
Cl4 C2S H2S1 112.9 . . ?
Cl3 C2S H2S1 112.9 . . ?
Cl4 C2S H2S2 112.9 . . ?
Cl3 C2S H2S2 112.9 . . ?
H2S1 C2S H2S2 110.4 . . ?
H1W O1W H1X 111.9(19) . . ?
H2W O2W H2X 110.7(19) . . ?
C37 O7 C38 115.8(3) . . ?
C7 N1 C8 127.4(3) . . ?
C7 N1 H1N 116.8(18) . . ?
C8 N1 H1N 115.4(17) . . ?
C8 N2 C12 118.3(3) . . ?
C13 N3 C14 127.9(3) . . ?
C13 N3 H3N 113(2) . . ?
C14 N3 H3N 119(2) . . ?
C14 N4 C18 118.4(3) . . ?
C19 N5 C20 129.4(3) . . ?
C19 N5 H5N 115(2) . . ?
C20 N5 H5N 116(2) . . ?
C20 N6 C24 118.1(3) . . ?
C25 N7 C26 129.4(3) . . ?
C25 N7 H7N 115(2) . . ?
C26 N7 H7N 116(2) . . ?
C26 N8 C30 117.7(3) . . ?
C31 N9 C32 128.4(3) . . ?
C31 N9 H9N 114(2) . . ?
C32 N9 H9N 117(2) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C7 117.1(3) . . ?
C2 C1 C7 124.4(3) . . ?
C32 N10 C36 117.0(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 N1 123.0(3) . . ?
O1 C7 C1 120.1(3) . . ?
N1 C7 C1 116.9(3) . . ?
N2 C8 N1 113.4(3) . . ?
N2 C8 C9 122.4(3) . . ?
N1 C8 C9 124.2(3) . . ?
C10 C9 C8 118.1(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N2 C12 C11 123.4(3) . . ?
N2 C12 C13 117.9(3) . . ?
C11 C12 C13 118.6(3) . . ?
O2 C13 N3 123.7(3) . . ?
O2 C13 C12 122.2(3) . . ?
N3 C13 C12 114.0(3) . . ?
N4 C14 C15 122.8(3) . . ?
N4 C14 N3 113.4(3) . . ?
C15 C14 N3 123.8(3) . . ?
C16 C15 C14 117.6(3) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 117.9(3) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
N4 C18 C17 123.0(3) . . ?
N4 C18 C19 116.9(3) . . ?
C17 C18 C19 120.0(3) . . ?
O3 C19 N5 125.3(3) . . ?
O3 C19 C18 121.8(3) . . ?
N5 C19 C18 112.9(3) . . ?
N6 C20 N5 113.9(3) . . ?
N6 C20 C21 122.7(3) . . ?
N5 C20 C21 123.4(3) . . ?
C22 C21 C20 117.7(3) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 117.1(3) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
N6 C24 C23 123.6(3) . . ?
N6 C24 C25 115.7(3) . . ?
C23 C24 C25 120.6(3) . . ?
O4 C25 N7 124.4(3) . . ?
O4 C25 C24 122.3(3) . . ?
N7 C25 C24 113.2(3) . . ?
N8 C26 C27 123.5(3) . . ?
N8 C26 N7 112.4(3) . . ?
C27 C26 N7 124.1(3) . . ?
C28 C27 C26 117.9(3) . . ?
C28 C27 H27 121.0 . . ?
C26 C27 H27 121.0 . . ?
C27 C28 C29 119.9(3) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 117.3(3) . . ?
C28 C29 H29 121.4 . . ?
C30 C29 H29 121.4 . . ?
N8 C30 C29 123.7(3) . . ?
N8 C30 C31 116.3(3) . . ?
C29 C30 C31 120.0(3) . . ?
O5 C31 N9 125.6(3) . . ?
O5 C31 C30 121.1(3) . . ?
N9 C31 C30 113.3(3) . . ?
N10 C32 C33 123.2(3) . . ?
N10 C32 N9 113.8(3) . . ?
C33 C32 N9 122.9(3) . . ?
C34 C33 C32 118.4(3) . . ?
C34 C33 H33 120.8 . . ?
C32 C33 H33 120.8 . . ?
C33 C34 C35 119.6(3) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 117.9(3) . . ?
C34 C35 H35 121.1 . . ?
C36 C35 H35 121.1 . . ?
N10 C36 C35 123.8(3) . . ?
N10 C36 C37 114.9(3) . . ?
C35 C36 C37 121.3(3) . . ?
O6 C37 O7 123.8(3) . . ?
O6 C37 C36 124.4(3) . . ?
O7 C37 C36 111.8(3) . . ?
O7 C38 H38A 109.5 . . ?
O7 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O7 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W O2W 0.822(11) 2.26(3) 2.854(4) 129(3) 2_656
O1W H1W N2 0.822(11) 2.51(2) 3.236(4) 148(4) .
O1W H1X N10 0.814(11) 2.22(2) 2.974(4) 153(5) 2_646
O2W H2W O6 0.818(11) 2.148(16) 2.909(4) 155(3) 1_545
O2W H2X O1W 0.829(11) 1.904(16) 2.707(4) 163(4) .
N1 H1N O2W 0.885(19) 2.11(2) 2.970(4) 163(2) 2_656
N3 H3N N2 0.916(19) 2.20(3) 2.692(4) 113(3) .
N5 H5N N4 0.881(19) 2.20(4) 2.645(4) 111(3) .
N7 H7N N6 0.872(19) 2.17(3) 2.620(4) 112(3) .
N9 H9N N8 0.876(19) 2.15(3) 2.634(3) 114(3) .
N9 H9N O1W 0.876(19) 2.43(2) 3.213(4) 150(3) 2_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_b641
_database_code_depnum_ccdc_archive 'CCDC 1419118'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        24-H2O
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 Cl2 N10 O9'
_chemical_formula_weight         857.66

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   13.4731(13)
_cell_length_b                   10.3806(10)
_cell_length_c                   13.7581(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.674(2)
_cell_angle_gamma                90.00
_cell_volume                     1914.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4074
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.28

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11324
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6438
_reflns_number_gt                5924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0912P)²+1.0270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.33(18)
_refine_ls_number_reflns         6438
_refine_ls_number_parameters     597
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62433(17) 0.0053(3) 0.09807(19) 0.0338(6) Uani 1 1 d . . .
O2 O 0.89454(19) 0.0723(3) -0.35080(18) 0.0326(6) Uani 1 1 d . . .
O3 O 1.41521(18) 0.1738(3) -0.10662(19) 0.0306(6) Uani 1 1 d . . .
O4 O 1.25787(17) 0.2289(3) 0.40573(17) 0.0310(6) Uani 1 1 d . . .
O5 O 0.70887(17) 0.3183(3) 0.24538(17) 0.0254(5) Uani 1 1 d . . .
O6 O 0.89336(18) 0.3939(3) -0.20607(18) 0.0307(6) Uani 1 1 d . . .
O7 O 0.74346(18) 0.3986(3) -0.29213(17) 0.0291(6) Uani 1 1 d . . .
N1 N 0.7780(2) 0.0184(3) 0.0437(2) 0.0215(6) Uani 1 1 d D . .
H1N H 0.8365(17) 0.034(4) 0.069(3) 0.026 Uiso 1 1 d D . .
N2 N 0.8309(2) 0.0410(3) -0.1085(2) 0.0210(6) Uani 1 1 d . . .
N3 N 0.9915(2) 0.0849(3) -0.2045(2) 0.0218(6) Uani 1 1 d D . .
H3N H 0.992(3) 0.091(4) -0.1422(15) 0.026 Uiso 1 1 d D . .
N4 N 1.1561(2) 0.1303(3) -0.1613(2) 0.0214(6) Uani 1 1 d . . .
N5 N 1.2849(2) 0.1923(3) -0.0122(2) 0.0221(6) Uani 1 1 d D . .
H5N H 1.2213(15) 0.192(4) -0.016(3) 0.027 Uiso 1 1 d D . .
N6 N 1.26844(19) 0.2150(3) 0.1495(2) 0.0214(6) Uani 1 1 d . . .
N7 N 1.1369(2) 0.2411(3) 0.2764(2) 0.0218(6) Uani 1 1 d D . .
H7N H 1.126(3) 0.243(4) 0.2150(15) 0.026 Uiso 1 1 d D . .
N8 N 0.96979(19) 0.2731(3) 0.2584(2) 0.0193(6) Uani 1 1 d . . .
N9 N 0.8173(2) 0.3204(3) 0.1276(2) 0.0193(6) Uani 1 1 d D . .
H9N H 0.8793(16) 0.321(4) 0.120(3) 0.023 Uiso 1 1 d D . .
N10 N 0.8018(2) 0.3565(3) -0.0378(2) 0.0193(6) Uani 1 1 d . . .
C1 C 0.7625(3) -0.0182(3) 0.2165(3) 0.0218(7) Uani 1 1 d . . .
C2 C 0.7017(3) -0.0033(4) 0.2922(3) 0.0303(8) Uani 1 1 d . . .
H2 H 0.6331 0.0174 0.2774 0.036 Uiso 1 1 calc R . .
C3 C 0.7398(3) -0.0181(4) 0.3876(3) 0.0373(9) Uani 1 1 d . . .
H3 H 0.6980 -0.0057 0.4385 0.045 Uiso 1 1 calc R . .
C4 C 0.8393(3) -0.0510(4) 0.4101(3) 0.0346(9) Uani 1 1 d . . .
H4 H 0.8660 -0.0601 0.4763 0.042 Uiso 1 1 calc R . .
C5 C 0.8991(3) -0.0706(3) 0.3357(3) 0.0299(8) Uani 1 1 d . . .
H5 H 0.9667 -0.0955 0.3507 0.036 Uiso 1 1 calc R . .
C6 C 0.8615(3) -0.0542(3) 0.2397(3) 0.0242(7) Uani 1 1 d . . .
H6 H 0.9034 -0.0676 0.1890 0.029 Uiso 1 1 calc R . .
C7 C 0.7151(3) 0.0025(3) 0.1140(3) 0.0248(7) Uani 1 1 d . . .
C8 C 0.7522(3) 0.0343(3) -0.0569(3) 0.0228(7) Uani 1 1 d . . .
C9 C 0.6539(3) 0.0418(4) -0.1006(3) 0.0277(8) Uani 1 1 d . . .
H9 H 0.5990 0.0367 -0.0623 0.033 Uiso 1 1 calc R . .
C10 C 0.6388(3) 0.0569(4) -0.2001(3) 0.0293(8) Uani 1 1 d . . .
H10 H 0.5729 0.0620 -0.2314 0.035 Uiso 1 1 calc R . .
C11 C 0.7203(3) 0.0647(3) -0.2553(3) 0.0277(8) Uani 1 1 d . . .
H11 H 0.7113 0.0749 -0.3242 0.033 Uiso 1 1 calc R . .
C12 C 0.8141(3) 0.0570(3) -0.2058(2) 0.0222(7) Uani 1 1 d . . .
C13 C 0.9035(3) 0.0711(3) -0.2619(3) 0.0244(7) Uani 1 1 d . . .
C14 C 1.0864(3) 0.1027(3) -0.2349(3) 0.0229(7) Uani 1 1 d . . .
C15 C 1.1083(3) 0.0916(3) -0.3314(3) 0.0257(8) Uani 1 1 d . . .
H15 H 1.0578 0.0708 -0.3820 0.031 Uiso 1 1 calc R . .
C16 C 1.2061(3) 0.1118(4) -0.3514(3) 0.0301(8) Uani 1 1 d . . .
H16 H 1.2231 0.1066 -0.4167 0.036 Uiso 1 1 calc R . .
C17 C 1.2789(3) 0.1396(4) -0.2758(3) 0.0271(8) Uani 1 1 d . . .
H17 H 1.3463 0.1533 -0.2879 0.033 Uiso 1 1 calc R . .
C18 C 1.2500(3) 0.1468(3) -0.1823(3) 0.0212(7) Uani 1 1 d . . .
C19 C 1.3267(3) 0.1722(3) -0.0978(3) 0.0244(8) Uani 1 1 d . . .
C20 C 1.3315(2) 0.2056(3) 0.0817(2) 0.0219(7) Uani 1 1 d . . .
C21 C 1.4355(2) 0.2050(3) 0.1037(3) 0.0246(7) Uani 1 1 d . . .
H21 H 1.4791 0.1987 0.0537 0.029 Uiso 1 1 calc R . .
C22 C 1.4720(2) 0.2140(4) 0.2013(3) 0.0287(8) Uani 1 1 d . . .
H22 H 1.5420 0.2145 0.2190 0.034 Uiso 1 1 calc R . .
C23 C 1.4075(2) 0.2223(3) 0.2729(3) 0.0259(7) Uani 1 1 d . . .
H23 H 1.4317 0.2275 0.3400 0.031 Uiso 1 1 calc R . .
C24 C 1.3068(2) 0.2225(3) 0.2434(2) 0.0221(7) Uani 1 1 d . . .
C25 C 1.2323(2) 0.2316(3) 0.3179(2) 0.0220(7) Uani 1 1 d . . .
C26 C 1.0486(2) 0.2497(3) 0.3215(2) 0.0192(7) Uani 1 1 d . . .
C27 C 1.0429(2) 0.2320(3) 0.4209(2) 0.0228(7) Uani 1 1 d . . .
H27 H 1.1010 0.2150 0.4639 0.027 Uiso 1 1 calc R . .
C28 C 0.9503(3) 0.2398(3) 0.4550(2) 0.0253(7) Uani 1 1 d . . .
H28 H 0.9437 0.2279 0.5226 0.030 Uiso 1 1 calc R . .
C29 C 0.8668(2) 0.2650(3) 0.3909(2) 0.0238(7) Uani 1 1 d . . .
H29 H 0.8024 0.2710 0.4132 0.029 Uiso 1 1 calc R . .
C30 C 0.8804(2) 0.2811(3) 0.2930(2) 0.0192(7) Uani 1 1 d . . .
C31 C 0.7926(2) 0.3085(3) 0.2200(2) 0.0192(7) Uani 1 1 d . . .
C32 C 0.7545(2) 0.3475(3) 0.0425(2) 0.0180(7) Uani 1 1 d . . .
C39 C 0.6511(2) 0.3626(3) 0.0422(2) 0.0201(7) Uani 1 1 d . . .
H39 H 0.6199 0.3573 0.1011 0.024 Uiso 1 1 calc R . .
C34 C 0.5961(3) 0.3852(3) -0.0458(3) 0.0250(7) Uani 1 1 d . . .
H34 H 0.5258 0.3958 -0.0484 0.030 Uiso 1 1 calc R . .
C35 C 0.6434(2) 0.3924(3) -0.1306(2) 0.0218(7) Uani 1 1 d . . .
H35 H 0.6065 0.4058 -0.1923 0.026 Uiso 1 1 calc R . .
C36 C 0.7460(2) 0.3795(3) -0.1225(2) 0.0203(7) Uani 1 1 d . . .
C37 C 0.8037(3) 0.3906(3) -0.2092(3) 0.0230(7) Uani 1 1 d . . .
C38 C 0.7927(3) 0.4019(4) -0.3811(3) 0.0334(9) Uani 1 1 d . . .
H38A H 0.8216 0.3172 -0.3922 0.050 Uiso 1 1 calc R . .
H38B H 0.8457 0.4668 -0.3749 0.050 Uiso 1 1 calc R . .
H38C H 0.7440 0.4238 -0.4363 0.050 Uiso 1 1 calc R . .
O1W O 1.00389(19) 0.5642(3) 0.9335(2) 0.0332(6) Uani 1 1 d D . .
H1A H 0.966(3) 0.530(4) 0.887(2) 0.040 Uiso 1 1 d D . .
H1B H 0.990(3) 0.638(3) 0.957(3) 0.040 Uiso 1 1 d D . .
O2W O 0.9828(2) 0.8157(3) 0.9795(2) 0.0408(7) Uani 1 1 d D . .
H2A H 1.034(2) 0.816(5) 1.019(3) 0.049 Uiso 1 1 d D . .
H2B H 0.949(3) 0.883(3) 0.980(4) 0.049 Uiso 1 1 d D . .
C1S C 0.5066(15) 0.4009(18) 0.5116(12) 0.142(5) Uani 0.560(5) 1 d PDU A 1
H1S1 H 0.5162 0.4861 0.5434 0.171 Uiso 0.560(5) 1 calc PR A 1
H1S2 H 0.4371 0.3978 0.4809 0.171 Uiso 0.560(5) 1 calc PR A 1
Cl1A Cl 0.5191(3) 0.2836(7) 0.6032(4) 0.136(2) Uani 0.560(5) 1 d PDU A 1
Cl1B Cl 0.5859(2) 0.3929(4) 0.4182(2) 0.0932(13) Uani 0.560(5) 1 d PDU A 1
C2S C 0.4684(14) 0.3267(12) 0.547(2) 0.154(6) Uani 0.440(5) 1 d PDU A 2
H2S1 H 0.4573 0.3351 0.6163 0.185 Uiso 0.440(5) 1 calc PR A 2
H2S2 H 0.4040 0.3013 0.5106 0.185 Uiso 0.440(5) 1 calc PR A 2
Cl2A Cl 0.5022(9) 0.4792(8) 0.5036(10) 0.224(5) Uani 0.440(5) 1 d PDU A 2
Cl2B Cl 0.5548(6) 0.2017(7) 0.5354(7) 0.184(4) Uani 0.440(5) 1 d PDU 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
O1 C7 1.221(4) . ?
O2 C13 1.217(4) . ?
O3 C19 1.211(4) . ?
O4 C25 1.224(4) . ?
O5 C31 1.217(4) . ?
O6 C37 1.205(4) . ?
O7 C37 1.336(4) . ?
O7 C38 1.449(4) . ?
N1 C7 1.358(5) . ?
N1 C8 1.404(4) . ?
N1 H1N 0.845(19) . ?
N2 C8 1.334(4) . ?
N2 C12 1.346(4) . ?
N3 C13 1.365(4) . ?
N3 C14 1.397(4) . ?
N3 H3N 0.859(19) . ?
N4 C18 1.337(4) . ?
N4 C14 1.342(4) . ?
N5 C19 1.370(4) . ?
N5 C20 1.386(4) . ?
N5 H5N 0.853(19) . ?
N6 C20 1.325(4) . ?
N6 C24 1.346(4) . ?
N7 C25 1.358(4) . ?
N7 C26 1.397(4) . ?
N7 H7N 0.844(19) . ?
N8 C26 1.326(4) . ?
N8 C30 1.341(4) . ?
N9 C31 1.352(4) . ?
N9 C32 1.404(4) . ?
N9 H9N 0.852(19) . ?
N10 C32 1.333(4) . ?
N10 C36 1.344(4) . ?
C1 C6 1.392(5) . ?
C1 C2 1.396(5) . ?
C1 C7 1.504(5) . ?
C2 C3 1.370(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.402(5) . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.501(5) . ?
C14 C15 1.393(5) . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.500(5) . ?
C20 C21 1.405(5) . ?
C21 C22 1.387(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.506(5) . ?
C26 C27 1.389(5) . ?
C27 C28 1.379(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.384(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.501(4) . ?
C32 C39 1.402(4) . ?
C39 C34 1.375(5) . ?
C39 H39 0.9500 . ?
C34 C35 1.386(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.491(5) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O1W H1A 0.85(2) . ?
O1W H1B 0.86(2) . ?
O2W H2A 0.84(2) . ?
O2W H2B 0.83(2) . ?
C1S Cl1A 1.748(5) . ?
C1S Cl1B 1.751(5) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S Cl2B 1.761(5) . ?
C2S Cl2A 1.765(5) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 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
C37 O7 C38 115.6(3) . . ?
C7 N1 C8 127.3(3) . . ?
C7 N1 H1N 111(3) . . ?
C8 N1 H1N 121(3) . . ?
C8 N2 C12 118.1(3) . . ?
C13 N3 C14 127.6(3) . . ?
C13 N3 H3N 120(3) . . ?
C14 N3 H3N 112(3) . . ?
C18 N4 C14 118.0(3) . . ?
C19 N5 C20 129.0(3) . . ?
C19 N5 H5N 116(3) . . ?
C20 N5 H5N 115(3) . . ?
C20 N6 C24 117.9(3) . . ?
C25 N7 C26 129.1(3) . . ?
C25 N7 H7N 119(3) . . ?
C26 N7 H7N 112(3) . . ?
C26 N8 C30 117.9(3) . . ?
C31 N9 C32 128.3(3) . . ?
C31 N9 H9N 117(3) . . ?
C32 N9 H9N 114(3) . . ?
C32 N10 C36 117.3(3) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C7 124.1(3) . . ?
C2 C1 C7 117.2(3) . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 123.6(3) . . ?
O1 C7 C1 119.8(3) . . ?
N1 C7 C1 116.6(3) . . ?
N2 C8 C9 122.4(3) . . ?
N2 C8 N1 113.4(3) . . ?
C9 C8 N1 124.1(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
N2 C12 C11 123.6(3) . . ?
N2 C12 C13 117.3(3) . . ?
C11 C12 C13 119.0(3) . . ?
O2 C13 N3 125.0(3) . . ?
O2 C13 C12 120.8(3) . . ?
N3 C13 C12 114.1(3) . . ?
N4 C14 C15 122.6(3) . . ?
N4 C14 N3 113.3(3) . . ?
C15 C14 N3 124.1(3) . . ?
C16 C15 C14 118.1(3) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 117.7(3) . . ?
C18 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
N4 C18 C17 123.7(3) . . ?
N4 C18 C19 116.7(3) . . ?
C17 C18 C19 119.6(3) . . ?
O3 C19 N5 125.2(3) . . ?
O3 C19 C18 122.3(3) . . ?
N5 C19 C18 112.5(3) . . ?
N6 C20 N5 113.6(3) . . ?
N6 C20 C21 122.9(3) . . ?
N5 C20 C21 123.4(3) . . ?
C22 C21 C20 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 117.5(3) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.2 . . ?
N6 C24 C23 123.8(3) . . ?
N6 C24 C25 116.0(3) . . ?
C23 C24 C25 120.2(3) . . ?
O4 C25 N7 125.3(3) . . ?
O4 C25 C24 121.9(3) . . ?
N7 C25 C24 112.7(3) . . ?
N8 C26 C27 123.4(3) . . ?
N8 C26 N7 112.5(3) . . ?
C27 C26 N7 124.1(3) . . ?
C28 C27 C26 117.9(3) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 117.7(3) . . ?
C28 C29 H29 121.2 . . ?
C30 C29 H29 121.2 . . ?
N8 C30 C29 123.1(3) . . ?
N8 C30 C31 116.8(3) . . ?
C29 C30 C31 120.1(3) . . ?
O5 C31 N9 125.7(3) . . ?
O5 C31 C30 121.0(3) . . ?
N9 C31 C30 113.3(3) . . ?
N10 C32 C39 123.2(3) . . ?
N10 C32 N9 114.0(3) . . ?
C39 C32 N9 122.8(3) . . ?
C34 C39 C32 118.1(3) . . ?
C34 C39 H39 121.0 . . ?
C32 C39 H39 121.0 . . ?
C39 C34 C35 119.9(3) . . ?
C39 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 117.8(3) . . ?
C36 C35 H35 121.1 . . ?
C34 C35 H35 121.1 . . ?
N10 C36 C35 123.8(3) . . ?
N10 C36 C37 114.5(3) . . ?
C35 C36 C37 121.6(3) . . ?
O6 C37 O7 123.5(3) . . ?
O6 C37 C36 125.0(3) . . ?
O7 C37 C36 111.5(3) . . ?
O7 C38 H38A 109.5 . . ?
O7 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O7 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
H1A O1W H1B 121(4) . . ?
H2A O2W H2B 114(5) . . ?
Cl1A C1S Cl1B 118.3(5) . . ?
Cl1A C1S H1S1 107.7 . . ?
Cl1B C1S H1S1 107.7 . . ?
Cl1A C1S H1S2 107.7 . . ?
Cl1B C1S H1S2 107.7 . . ?
H1S1 C1S H1S2 107.1 . . ?
Cl2B C2S Cl2A 115.9(5) . . ?
Cl2B C2S H2S1 108.3 . . ?
Cl2A C2S H2S1 108.3 . . ?
Cl2B C2S H2S2 108.3 . . ?
Cl2A C2S H2S2 108.3 . . ?
H2S1 C2S H2S2 107.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2W H2B N2 0.83(2) 2.52(3) 3.261(4) 149(4) 1_566
O2W H2B O1W 0.83(2) 2.28(4) 2.842(4) 125(4) 2_757
O2W H2A N10 0.84(2) 2.24(3) 2.964(4) 145(4) 2_756
O1W H1B O2W 0.86(2) 1.88(2) 2.708(4) 163(4) .
O1W H1A O6 0.85(2) 2.09(2) 2.910(4) 162(4) 1_556
N9 H9N O2W 0.852(19) 2.42(2) 3.197(4) 153(3) 2_746
N9 H9N N8 0.852(19) 2.21(4) 2.640(4) 111(3) .
N5 H5N N4 0.853(19) 2.19(4) 2.632(4) 112(3) .
N1 H1N O1W 0.845(19) 2.18(2) 2.962(4) 155(3) 2_746

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.063
