# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1040388'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
_cell_length_a                   7.8956(4)
_cell_length_b                   9.6557(3)
_cell_length_c                   14.9160(6)
_cell_angle_alpha                77.311(3)
_cell_angle_beta                 81.835(4)
_cell_angle_gamma                86.214(3)
_cell_volume                     1097.43(4)
_cell_measurement_reflns_used    6458
_cell_measurement_theta_min      2.3010
_cell_measurement_theta_max      29.0590
_cell_oxdiff_length_a            7.8956(4)
_cell_oxdiff_length_b            9.6557(3)
_cell_oxdiff_length_c            14.9160(6)
_cell_oxdiff_angle_alpha         77.311(3)
_cell_oxdiff_angle_beta          81.835(4)
_cell_oxdiff_angle_gamma         86.214(3)
_cell_oxdiff_volume              1097.43(8)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C18 H33 N2 O8 S2'
_chemical_formula_moiety         'C10 H26 N2, 0.5(C16 H6 O12 S4), 2(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         469.60


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_max          0.360
_exptl_absorpt_correction_T_min  0.97075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    0.290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.72
_montpellier_reflns_completeness_maxres 86.85
_montpellier_reflns_redundancy_maxres 2.94

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.63 5.3 65.01 0.023 99.8 99.81
1 1.63 1.30 4.1 35.30 0.034 100.0 99.90
2 1.30 1.13 3.7 28.56 0.033 100.0 99.94
3 1.13 1.03 3.0 18.76 0.041 100.0 99.95
4 1.03 0.96 2.8 13.89 0.050 100.0 99.96
5 0.96 0.90 2.6 10.95 0.062 100.0 99.97
6 0.90 0.86 2.4 9.48 0.069 100.0 99.97
7 0.86 0.82 2.3 7.82 0.084 100.0 99.98
8 0.82 0.78 2.0 6.95 0.095 93.8 99.24
9 0.78 0.72 1.3 5.26 0.080 41.3 86.85
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0824545000
_diffrn_orient_matrix_UB_12      0.0249365000
_diffrn_orient_matrix_UB_13      0.0001357000
_diffrn_orient_matrix_UB_21      0.0322593000
_diffrn_orient_matrix_UB_22      -0.0314879000
_diffrn_orient_matrix_UB_23      -0.0380024000
_diffrn_orient_matrix_UB_31      -0.0201907000
_diffrn_orient_matrix_UB_32      0.0637491000
_diffrn_orient_matrix_UB_33      -0.0311959000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00   44.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -       15.4892  -19.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega   49.00   88.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -       15.4892  179.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   15.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -       15.4892  -57.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega  -82.00   -5.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.2704  -57.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega  -86.00  -51.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.2704  151.0000  -49.2221 35

#__ type_ start__ end____ width___ exp.time_
  6 omega  -47.00    8.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.2704  -77.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   88.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -       15.4892  179.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega  -33.00   51.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.2704   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega  -85.00    3.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.2704  -38.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 10 omega  -84.00  -59.00   1.0000   46.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.2704  -57.0000    0.0000 25

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            15468
_reflns_number_total             5259
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0422
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5259 
# Theoretical number of reflections is about 12102 


_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         29.386
_diffrn_measured_fraction_theta_max 0.869

_diffrn_reflns_theta_full        25.272
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -12
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   1.72
_oxford_diffrn_Wilson_scale      0.42

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.48
_refine_diff_density_max         0.48


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4468
_refine_ls_number_restraints     55
_refine_ls_number_parameters     311
_oxford_refine_ls_R_factor_ref   0.0433
_refine_ls_wR_factor_ref         0.0461
_refine_ls_goodness_of_fit_ref   1.0815
_refine_ls_shift/su_max          0.0005449
_refine_ls_shift/su_mean         0.0000280


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5259
_refine_ls_R_factor_all          0.0528
_refine_ls_wR_factor_all         0.0511

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4468
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_gt          0.0461

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.35 2.33 6.20 1.57 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.61657(6) 0.15861(5) 0.32011(3) 0.0170 1.0000 Uani . . . . . .
O2 O 0.7055(2) 0.18188(17) 0.22519(11) 0.0295 1.0000 Uani . . . . . .
O3 O 0.7140(2) 0.06849(16) 0.38561(11) 0.0270 1.0000 Uani . . . . . .
O4 O 0.4431(2) 0.11503(19) 0.32542(15) 0.0354 1.0000 Uani . . . . . .
C5 C 0.5986(2) 0.33030(19) 0.34708(13) 0.0156 1.0000 Uani . . . . . .
C6 C 0.5342(2) 0.34913(19) 0.43644(13) 0.0146 1.0000 Uani . . . . . .
C7 C 0.5311(2) 0.48841(19) 0.45461(12) 0.0135 1.0000 Uani . . . . . .
C8 C 0.5895(2) 0.60555(19) 0.38254(13) 0.0145 1.0000 Uani . . . . . .
C9 C 0.6431(3) 0.5805(2) 0.29319(13) 0.0157 1.0000 Uani . . . . . .
C10 C 0.6491(3) 0.4448(2) 0.27655(13) 0.0169 1.0000 Uani . . . . . .
H101 H 0.6877 0.4303 0.2172 0.0210 1.0000 Uiso R . . . . .
S11 S 0.70347(7) 0.72093(5) 0.19664(3) 0.0190 1.0000 Uani . . . . . .
O12 O 0.5566(2) 0.82015(17) 0.18737(11) 0.0298 1.0000 Uani . . . . . .
O13 O 0.7444(2) 0.65586(17) 0.11713(11) 0.0291 1.0000 Uani . . . . . .
O14 O 0.8494(2) 0.78476(19) 0.21875(12) 0.0323 1.0000 Uani . . . . . .
C15 C 0.5905(3) 0.7428(2) 0.40453(14) 0.0178 1.0000 Uani . . . . . .
C16 C 0.5314(3) 0.76409(19) 0.49005(14) 0.0168 1.0000 Uani . . . . . .
H161 H 0.5336 0.8552 0.5018 0.0211 1.0000 Uiso R . . . . .
H151 H 0.6339 0.8188 0.3586 0.0229 1.0000 Uiso R . . . . .
O17 O 0.0016(2) 1.03768(18) 0.17325(13) 0.0300 1.0000 Uani D . . . . .
H171 H -0.045(4) 0.964(3) 0.184(2) 0.0466 1.0000 Uiso D . . . . .
H172 H -0.072(4) 1.089(3) 0.193(2) 0.0462 1.0000 Uiso D . . . . .
O18 O 0.2648(3) 0.1129(2) 1.03129(12) 0.0357 1.0000 Uani D . . . . .
H181 H 0.252(5) 0.186(3) 0.992(2) 0.0543 1.0000 Uiso D . . . . .
H182 H 0.181(4) 0.103(4) 1.070(2) 0.0542 1.0000 Uiso D . . . . .
N19 N 0.2555(3) 0.9137(2) 0.28546(14) 0.0256 1.0000 Uani D . . . . .
C20 C 0.1703(3) 0.7903(2) 0.35051(16) 0.0243 1.0000 Uani D . . . . .
C21 C 0.0782(3) 0.8315(2) 0.43699(16) 0.0250 1.0000 Uani . . . . . .
C22 C 0.0104(3) 0.6994(2) 0.50537(17) 0.0267 1.0000 Uani . . . . . .
C23 C -0.0611(3) 0.7264(3) 0.60015(17) 0.0285 1.0000 Uani . . . . . .
C24 C -0.1161(3) 0.5902(3) 0.66818(17) 0.0297 1.0000 Uani . . . . . .
C25 C -0.1466(3) 0.6039(3) 0.76846(17) 0.0323 1.0000 Uani . . . . . .
C26 C -0.2099(4) 0.4681(3) 0.83364(18) 0.0368 1.0000 Uani . . . . . .
C27 C -0.2021(6) 0.4674(3) 0.9345(2) 0.0546 1.0000 Uani D U . . . .
C280 C -0.3385(6) 0.3650(5) 1.0004(3) 0.0374 0.624(8) Uani D U P 1 1 .
C281 C -0.1943(8) 0.3063(7) 0.9966(4) 0.0302 0.376(8) Uani D U P 1 2 .
C290 C -0.2795(7) 0.2153(5) 0.9944(3) 0.0330 0.624(8) Uani D U P 1 1 .
C291 C -0.3786(9) 0.2692(7) 1.0077(5) 0.0303 0.376(8) Uani D U P 1 2 .
N30 N -0.3914(3) 0.1152(2) 1.06752(14) 0.0308 1.0000 Uani D U . . . .
H262 H -0.1396 0.3889 0.8176 0.0449 1.0000 Uiso R . . . . .
H261 H -0.3287 0.4574 0.8263 0.0450 1.0000 Uiso R . . . . .
H252 H -0.2319 0.6792 0.7746 0.0410 1.0000 Uiso R . . . . .
H251 H -0.0401 0.6275 0.7862 0.0410 1.0000 Uiso R . . . . .
H242 H -0.2217 0.5611 0.6519 0.0370 1.0000 Uiso R . . . . .
H241 H -0.0261 0.5177 0.6621 0.0370 1.0000 Uiso R . . . . .
H232 H 0.0275 0.7679 0.6240 0.0360 1.0000 Uiso R . . . . .
H231 H -0.1592 0.7926 0.5940 0.0360 1.0000 Uiso R . . . . .
H222 H 0.1055 0.6300 0.5134 0.0339 1.0000 Uiso R . . . . .
H221 H -0.0783 0.6615 0.4796 0.0339 1.0000 Uiso R . . . . .
H212 H -0.0162 0.8973 0.4205 0.0322 1.0000 Uiso R . . . . .
H211 H 0.1570 0.8767 0.4647 0.0320 1.0000 Uiso R . . . . .
H202 H 0.2571 0.7167 0.3678 0.0310 1.0000 Uiso R . . . . .
H201 H 0.0870 0.7554 0.3194 0.0310 1.0000 Uiso R . . . . .
H193 H 0.180(3) 0.968(2) 0.2544(17) 0.0398 1.0000 Uiso D . . . . .
H191 H 0.305(3) 0.966(3) 0.3157(16) 0.0401 1.0000 Uiso D . . . . .
H192 H 0.337(3) 0.882(2) 0.2462(16) 0.0401 1.0000 Uiso D . . . . .
H2801 H -0.2943 0.3607 1.0570 0.2754 0.624(8) Uiso R . P 1 1 .
H2802 H -0.4538 0.4004 1.0054 0.2754 0.624(8) Uiso R . P 1 1 .
H2901 H -0.1643 0.1812 0.9836 0.1544 0.624(8) Uiso R . P 1 1 .
H2902 H -0.3340 0.2187 0.9411 0.1544 0.624(8) Uiso R . P 1 1 .
H2811 H -0.1388 0.2998 1.0500 0.0600 0.376(8) Uiso R . P 1 2 .
H2812 H -0.1373 0.2441 0.9599 0.0600 0.376(8) Uiso R . P 1 2 .
H2911 H -0.4302 0.3282 1.0480 0.0600 0.376(8) Uiso R . P 1 2 .
H2912 H -0.4325 0.2882 0.9530 0.0600 0.376(8) Uiso R . P 1 2 .
H271 H -0.2507 0.5550 0.9470 0.0658 0.624(8) Uiso R . P 1 1 .
H272 H -0.0854 0.4589 0.9446 0.0658 0.624(8) Uiso R . P 1 1 .
H273 H -0.3044 0.5106 0.9595 0.0658 0.376(8) Uiso R . P 1 2 .
H274 H -0.1067 0.5195 0.9389 0.0658 0.376(8) Uiso R . P 1 2 .
H301 H -0.3782 0.0300 1.0446 0.0369 0.624(8) Uiso . . P 1 1 .
H302 H -0.3399 0.1011 1.1229 0.0369 0.624(8) Uiso . . P 1 1 .
H303 H -0.5096 0.1387 1.0803 0.0369 0.376(8) Uiso . . P 1 1 .
H304 H -0.5081 0.0914 1.0847 0.0369 0.376(8) Uiso . . P 1 2 .
H305 H -0.3352 0.0979 1.1215 0.0369 0.5000 Uiso . . . 1 2 .
H306 H -0.3375 0.0579 1.0265 0.0369 0.5000 Uiso . . . 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.557(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.4650(17) yes
S1 . O3 . 1.4336(16) yes
S1 . O4 . 1.4460(17) yes
S1 . C5 . 1.7821(18) yes
C5 . C6 . 1.404(3) yes
C5 . C10 . 1.384(3) yes
C6 . C16 2_666 1.433(3) yes
C6 . C7 . 1.427(2) yes
C7 . C7 2_666 1.433(4) yes
C7 . C8 . 1.429(3) yes
C8 . C9 . 1.408(3) yes
C8 . C15 . 1.434(2) yes
C9 . C10 . 1.383(3) yes
C9 . S11 . 1.781(2) yes
C10 . H101 . 0.932 no
S11 . O12 . 1.4566(18) yes
S11 . O13 . 1.4483(16) yes
S11 . O14 . 1.4516(17) yes
C15 . C16 . 1.349(3) yes
C15 . H151 . 0.933 no
C16 . H161 . 0.936 no
O17 . H171 . 0.80(2) no
O17 . H172 . 0.81(2) no
O18 . H181 . 0.82(2) no
O18 . H182 . 0.81(2) no
N19 . C20 . 1.492(3) yes
N19 . H193 . 0.88(2) no
N19 . H191 . 0.88(2) no
N19 . H192 . 0.89(2) no
C20 . C21 . 1.507(3) yes
C20 . H202 . 0.973 no
C20 . H201 . 0.973 no
C21 . C22 . 1.522(3) yes
C21 . H212 . 0.970 no
C21 . H211 . 0.968 no
C22 . C23 . 1.517(3) yes
C22 . H222 . 0.975 no
C22 . H221 . 0.971 no
C23 . C24 . 1.521(3) yes
C23 . H232 . 0.972 no
C23 . H231 . 0.972 no
C24 . C25 . 1.514(3) yes
C24 . H242 . 0.975 no
C24 . H241 . 0.974 no
C25 . C26 . 1.517(3) yes
C25 . H252 . 0.968 no
C25 . H251 . 0.971 no
C26 . C27 . 1.514(4) yes
C26 . H262 . 0.968 no
C26 . H261 . 0.975 no
C27 . C280 . 1.586(5) yes
C27 . H271 . 0.950 no
C27 . H272 . 0.950 no
C27 . C281 . 1.629(7) yes
C27 . H273 . 0.950 no
C27 . H274 . 0.950 no
C280 . C290 . 1.507(6) yes
C280 . H2801 . 0.950 no
C280 . H2802 . 0.950 no
C281 . C291 . 1.499(9) yes
C281 . H2811 . 0.950 no
C281 . H2812 . 0.950 no
C290 . N30 . 1.511(4) yes
C290 . H2901 . 0.950 no
C290 . H2902 . 0.950 no
C291 . N30 . 1.558(6) yes
C291 . H2911 . 0.950 no
C291 . H2912 . 0.950 no
N30 . H301 . 0.952 no
N30 . H302 . 0.952 no
N30 . H303 . 0.948 no
N30 . H304 . 0.950 no
N30 . H305 . 0.952 no
N30 . H306 . 0.952 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 112.57(10) yes
O2 . S1 . O4 . 111.90(11) yes
O3 . S1 . O4 . 113.90(11) yes
O2 . S1 . C5 . 104.39(9) yes
O3 . S1 . C5 . 107.37(9) yes
O4 . S1 . C5 . 105.89(10) yes
S1 . C5 . C6 . 121.26(14) yes
S1 . C5 . C10 . 117.65(14) yes
C6 . C5 . C10 . 121.08(17) yes
C16 2_666 C6 . C5 . 123.26(16) yes
C16 2_666 C6 . C7 . 118.30(17) yes
C5 . C6 . C7 . 118.42(17) yes
C7 2_666 C7 . C6 . 120.1(2) yes
C7 2_666 C7 . C8 . 119.6(2) yes
C6 . C7 . C8 . 120.30(16) yes
C7 . C8 . C9 . 118.26(16) yes
C7 . C8 . C15 . 118.56(17) yes
C9 . C8 . C15 . 123.18(17) yes
C8 . C9 . C10 . 121.03(17) yes
C8 . C9 . S11 . 121.93(14) yes
C10 . C9 . S11 . 117.04(15) yes
C5 . C10 . C9 . 120.73(17) yes
C5 . C10 . H101 . 119.7 no
C9 . C10 . H101 . 119.6 no
C9 . S11 . O12 . 106.93(9) yes
C9 . S11 . O13 . 106.17(9) yes
O12 . S11 . O13 . 111.86(10) yes
C9 . S11 . O14 . 106.23(10) yes
O12 . S11 . O14 . 111.99(11) yes
O13 . S11 . O14 . 113.12(11) yes
C8 . C15 . C16 . 121.55(18) yes
C8 . C15 . H151 . 119.0 no
C16 . C15 . H151 . 119.4 no
C6 2_666 C16 . C15 . 121.81(17) yes
C6 2_666 C16 . H161 . 119.0 no
C15 . C16 . H161 . 119.2 no
H171 . O17 . H172 . 102(4) no
H181 . O18 . H182 . 110(4) no
C20 . N19 . H193 . 110.2(15) no
C20 . N19 . H191 . 111.2(15) no
H193 . N19 . H191 . 108.6(18) no
C20 . N19 . H192 . 109.5(15) no
H193 . N19 . H192 . 109.7(18) no
H191 . N19 . H192 . 107.6(18) no
N19 . C20 . C21 . 111.68(18) yes
N19 . C20 . H202 . 108.7 no
C21 . C20 . H202 . 108.9 no
N19 . C20 . H201 . 108.7 no
C21 . C20 . H201 . 108.4 no
H202 . C20 . H201 . 110.5 no
C20 . C21 . C22 . 109.60(19) yes
C20 . C21 . H212 . 108.9 no
C22 . C21 . H212 . 109.8 no
C20 . C21 . H211 . 109.2 no
C22 . C21 . H211 . 109.6 no
H212 . C21 . H211 . 109.6 no
C21 . C22 . C23 . 113.55(19) yes
C21 . C22 . H222 . 107.7 no
C23 . C22 . H222 . 107.8 no
C21 . C22 . H221 . 108.8 no
C23 . C22 . H221 . 109.3 no
H222 . C22 . H221 . 109.7 no
C22 . C23 . C24 . 111.9(2) yes
C22 . C23 . H232 . 108.4 no
C24 . C23 . H232 . 108.8 no
C22 . C23 . H231 . 109.1 no
C24 . C23 . H231 . 109.1 no
H232 . C23 . H231 . 109.6 no
C23 . C24 . C25 . 114.0(2) yes
C23 . C24 . H242 . 108.4 no
C25 . C24 . H242 . 108.6 no
C23 . C24 . H241 . 108.0 no
C25 . C24 . H241 . 108.2 no
H242 . C24 . H241 . 109.6 no
C24 . C25 . C26 . 112.4(2) yes
C24 . C25 . H252 . 108.8 no
C26 . C25 . H252 . 108.4 no
C24 . C25 . H251 . 109.1 no
C26 . C25 . H251 . 108.7 no
H252 . C25 . H251 . 109.5 no
C25 . C26 . C27 . 113.2(2) yes
C25 . C26 . H262 . 108.6 no
C27 . C26 . H262 . 108.3 no
C25 . C26 . H261 . 108.6 no
C27 . C26 . H261 . 108.1 no
H262 . C26 . H261 . 110.1 no
C26 . C27 . C280 . 111.1(3) yes
C26 . C27 . H271 . 108.4 no
C280 . C27 . H271 . 98.2 no
C26 . C27 . H272 . 108.4 no
C280 . C27 . H272 . 120.4 no
H271 . C27 . H272 . 109.5 no
C26 . C27 . C281 . 111.6(3) yes
C26 . C27 . H273 . 109.4 no
C281 . C27 . H273 . 105.5 no
C26 . C27 . H274 . 109.1 no
C281 . C27 . H274 . 111.7 no
H273 . C27 . H274 . 109.5 no
C27 . C280 . C290 . 107.0(3) yes
C27 . C280 . H2801 . 97.7 no
C290 . C280 . H2801 . 94.2 no
C27 . C280 . H2802 . 116.4 no
C290 . C280 . H2802 . 126.0 no
H2801 . C280 . H2802 . 109.5 no
C27 . C281 . C291 . 100.6(5) yes
C27 . C281 . H2811 . 112.7 no
C291 . C281 . H2811 . 119.8 no
C27 . C281 . H2812 . 109.9 no
C291 . C281 . H2812 . 103.7 no
H2811 . C281 . H2812 . 109.5 no
C280 . C290 . N30 . 107.8(4) yes
C280 . C290 . H2901 . 126.5 no
N30 . C290 . H2901 . 114.0 no
C280 . C290 . H2902 . 92.8 no
N30 . C290 . H2902 . 101.4 no
H2901 . C290 . H2902 . 109.5 no
C281 . C291 . N30 . 106.4(5) yes
C281 . C291 . H2911 . 101.5 no
N30 . C291 . H2911 . 104.8 no
C281 . C291 . H2912 . 116.8 no
N30 . C291 . H2912 . 116.3 no
H2911 . C291 . H2912 . 109.5 no
C290 . N30 . H301 . 102.3 no
C290 . N30 . H302 . 106.5 no
H301 . N30 . H302 . 109.1 no
C290 . N30 . H303 . 119.5 no
H301 . N30 . H303 . 109.4 no
H302 . N30 . H303 . 109.5 no
C291 . N30 . H304 . 110.0 no
C291 . N30 . H305 . 115.1 no
H304 . N30 . H305 . 109.3 no
C291 . N30 . H306 . 103.6 no
H304 . N30 . H306 . 109.3 no
H305 . N30 . H306 . 109.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C15 . H151 . O14 . 122.67(6) 0.933 2.564 3.167(4) yes
O17 . H171 . O14 1_455 176(4) 0.799 1.904 2.701(4) yes
O17 . H172 . O2 1_465 163(4) 0.808 1.962 2.745(4) yes
O18 . H181 . O13 2_666 169(4) 0.824 1.968 2.783(4) yes
O18 . H182 . O17 1_546 168(4) 0.813 1.958 2.757(4) yes
C23 . H231 . O4 2_566 146.62(7) 0.972 2.590 3.443(4) yes
C20 . H201 . O14 1_455 153.93(6) 0.973 2.529 3.430(4) yes
N19 . H193 . O17 . 164(2) 0.877 1.978 2.830(4) yes
N19 . H191 . O4 1_565 155(2) 0.885 1.906 2.732(4) yes
N19 . H192 . O12 . 163(2) 0.892 1.948 2.814(4) yes
N30 . H301 . O18 2_557 157.31(14) 0.952 2.055 2.957(4) yes
N30 . H302 . O2 1_456 146.60(14) 0.952 1.944 2.788(4) yes
N30 . H303 . O18 1_455 137.96(13) 0.948 2.068 2.844(4) yes
N30 . H304 . O18 1_455 140.82(13) 0.950 2.044 2.844(4) yes
N30 . H305 . O2 1_456 142.84(14) 0.952 1.969 2.788(4) yes
N30 . H306 . O18 2_557 161.74(13) 0.952 2.038 2.957(4) yes


####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1040389'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
_cell_length_a                   19.4827(5)
_cell_length_b                   7.7013(2)
_cell_length_c                   30.1416(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.758(2)
_cell_angle_gamma                90
_cell_volume                     4427.63(11)
_cell_measurement_reflns_used    5367
_cell_measurement_theta_min      2.1370
_cell_measurement_theta_max      28.8650
_cell_oxdiff_length_a            19.4702(9)
_cell_oxdiff_length_b            7.7046(3)
_cell_oxdiff_length_c            30.1459(14)
_cell_oxdiff_angle_alpha         90.001(3)
_cell_oxdiff_angle_beta          101.739(4)
_cell_oxdiff_angle_gamma         89.994(4)
_cell_oxdiff_volume              4427.6(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/c '
_symmetry_space_group_name_Hall  '-I 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1
-x+1/2,y+1/2,-z+1

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C36 H66 N4 O16 S4'
_chemical_formula_moiety         'C16 H6 O12 S4, 2(C10 H26 N2), 4(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         939.21


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_max          0.500
_exptl_absorpt_correction_T_min  0.99251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2008
_exptl_absorpt_coefficient_mu    0.287
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.73
_montpellier_reflns_completeness_maxres 87.50
_montpellier_reflns_redundancy_maxres 2.40

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.71 3.9 52.49 0.021 99.5 99.46
1 1.70 1.33 3.2 30.67 0.027 100.0 99.73
2 1.33 1.16 2.9 25.22 0.028 100.0 99.82
3 1.16 1.05 2.5 16.97 0.037 100.0 99.86
4 1.05 0.97 2.4 12.26 0.054 100.0 99.89
5 0.97 0.91 2.2 9.72 0.055 100.0 99.91
6 0.91 0.86 2.0 7.78 0.073 100.0 99.92
7 0.86 0.83 1.9 7.04 0.078 100.0 99.93
8 0.83 0.79 1.7 6.20 0.093 98.2 99.74
9 0.79 0.73 1.2 4.18 0.084 41.9 87.50
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0148556000
_diffrn_orient_matrix_UB_12      0.0567455000
_diffrn_orient_matrix_UB_13      -0.0140152000
_diffrn_orient_matrix_UB_21      -0.0336191000
_diffrn_orient_matrix_UB_22      0.0127778000
_diffrn_orient_matrix_UB_23      -0.0139599000
_diffrn_orient_matrix_UB_31      -0.0057976000
_diffrn_orient_matrix_UB_32      0.0713580000
_diffrn_orient_matrix_UB_33      0.0136454000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   56.00   1.0000   91.0300
omega____ theta____ kappa____ phi______ frames
    -       17.7668 -100.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   88.00   1.0000   91.0300
omega____ theta____ kappa____ phi______ frames
    -       17.7668   19.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega  -55.00   59.00   1.0000   91.0300
omega____ theta____ kappa____ phi______ frames
    -       17.7668  -19.0000  150.0000 114

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   22.00   1.0000   91.0300
omega____ theta____ kappa____ phi______ frames
    -       17.7668   77.0000 -120.0000 34

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            12680
_reflns_number_total             5162
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0438
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5162 
# Theoretical number of reflections is about 11839 


_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         29.059
_diffrn_measured_fraction_theta_max 0.872

_diffrn_reflns_theta_full        25.281
_diffrn_measured_fraction_theta_full 0.960


_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       41
_reflns_limit_h_min              -25
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              41

_oxford_diffrn_Wilson_B_factor   1.81
_oxford_diffrn_Wilson_scale      0.42

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.64
_refine_diff_density_max         1.62


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     22
_refine_ls_number_parameters     301
_oxford_refine_ls_R_factor_ref   0.0746
_refine_ls_wR_factor_ref         0.0767
_refine_ls_goodness_of_fit_ref   1.0486
_refine_ls_shift/su_max          0.0009738
_refine_ls_shift/su_mean         0.0000676


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5162
_refine_ls_R_factor_all          0.0885
_refine_ls_wR_factor_all         0.0830

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4256
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_gt          0.0767

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 18.1 17.9 17.5 6.36 1.75 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.41729(3) 0.74509(10) 0.65875(2) 0.0235 1.0000 Uani . . . . . .
O2 O 0.40466(12) 0.6970(5) 0.61098(8) 0.0596 1.0000 Uani . . . . . .
O3 O 0.45871(11) 0.6137(3) 0.68642(8) 0.0359 1.0000 Uani . . . . . .
O4 O 0.44558(12) 0.9155(3) 0.66808(10) 0.0452 1.0000 Uani . . . . . .
C5 C 0.33275(12) 0.7417(4) 0.67321(8) 0.0219 1.0000 Uani . . . . . .
C6 C 0.32444(12) 0.7547(4) 0.71836(8) 0.0191 1.0000 Uani . . . . . .
C7 C 0.25507(12) 0.7447(4) 0.72707(8) 0.0179 1.0000 Uani . . . . . .
C8 C 0.19584(12) 0.7246(4) 0.69045(8) 0.0192 1.0000 Uani . . . . . .
C9 C 0.20780(12) 0.7182(4) 0.64593(8) 0.0211 1.0000 Uani . . . . . .
C10 C 0.27537(13) 0.7262(4) 0.63771(9) 0.0229 1.0000 Uani . . . . . .
H101 H 0.2825 0.7196 0.6085 0.0283 1.0000 Uiso R . . . . .
S11 S 0.13796(3) 0.69322(10) 0.59782(2) 0.0239 1.0000 Uani . . . . . .
O12 O 0.08915(11) 0.8360(3) 0.59804(7) 0.0353 1.0000 Uani . . . . . .
O13 O 0.17025(10) 0.6984(3) 0.55845(7) 0.0362 1.0000 Uani . . . . . .
O14 O 0.10635(11) 0.5266(3) 0.60366(7) 0.0365 1.0000 Uani . . . . . .
C15 C 0.12745(12) 0.7119(4) 0.70095(9) 0.0225 1.0000 Uani . . . . . .
C16 C 0.11782(12) 0.7226(4) 0.74404(9) 0.0232 1.0000 Uani . . . . . .
H161 H 0.0722 0.7130 0.7495 0.0274 1.0000 Uiso R . . . . .
H151 H 0.0886 0.6960 0.6770 0.0270 1.0000 Uiso R . . . . .
O17 O 0.56467(12) 0.7040(3) 0.48605(8) 0.0377 1.0000 Uani D . . . . .
H171 H 0.6009(16) 0.734(6) 0.5030(14) 0.0570 1.0000 Uiso D . . . . .
H172 H 0.561(3) 0.777(5) 0.4661(13) 0.0571 1.0000 Uiso D . . . . .
O18 O 0.47314(13) 1.0889(4) 0.58976(10) 0.0496 1.0000 Uani D . . . . .
H181 H 0.5117(16) 1.044(7) 0.5920(19) 0.0751 1.0000 Uiso D . . . . .
H182 H 0.449(2) 1.030(6) 0.6033(17) 0.0752 1.0000 Uiso D . . . . .
N19 N 0.44559(14) 0.6630(4) 0.52997(9) 0.0369 1.0000 Uani D . . . . .
C20 C 0.3905(3) 0.7453(8) 0.49502(14) 0.0682 1.0000 Uani D . . . . .
C21 C 0.3156(3) 0.6616(7) 0.49804(15) 0.0627 1.0000 Uani . . . . . .
C22 C 0.2569(3) 0.7272(8) 0.46296(16) 0.0686 1.0000 Uani . . . . . .
C23 C 0.2647(2) 0.6970(6) 0.41433(14) 0.0505 1.0000 Uani . . . . . .
C24 C 0.1994(2) 0.7312(6) 0.37943(15) 0.0529 1.0000 Uani . . . . . .
C25 C 0.2109(2) 0.7282(6) 0.33149(14) 0.0490 1.0000 Uani . . . . . .
C26 C 0.1429(2) 0.7473(6) 0.29677(15) 0.0507 1.0000 Uani . . . . . .
C27 C 0.1525(2) 0.7626(6) 0.24889(15) 0.0505 1.0000 Uani . . . . . .
C28 C 0.0828(2) 0.7871(6) 0.21461(15) 0.0519 1.0000 Uani . . . . . .
C29 C 0.0954(2) 0.8362(6) 0.16928(14) 0.0484 1.0000 Uani D . . . . .
N30 N 0.03086(17) 0.8918(5) 0.13902(12) 0.0482 1.0000 Uani D . . . . .
H301 H 0.0043(14) 0.797(3) 0.1296(11) 0.0727 1.0000 Uiso D . . . . .
H303 H 0.0416(13) 0.953(4) 0.1151(9) 0.0732 1.0000 Uiso D . . . . .
H302 H 0.0070(14) 0.960(4) 0.1550(8) 0.0728 1.0000 Uiso D . . . . .
H292 H 0.1296 0.9329 0.1724 0.0581 1.0000 Uiso R . . . . .
H291 H 0.1140 0.7364 0.1560 0.0581 1.0000 Uiso R . . . . .
H282 H 0.0570 0.8821 0.2253 0.0615 1.0000 Uiso R . . . . .
H281 H 0.0557 0.6803 0.2118 0.0616 1.0000 Uiso R . . . . .
H272 H 0.1761 0.6585 0.2410 0.0608 1.0000 Uiso R . . . . .
H271 H 0.1827 0.8631 0.2474 0.0611 1.0000 Uiso R . . . . .
H262 H 0.1198 0.8537 0.3044 0.0614 1.0000 Uiso R . . . . .
H261 H 0.1127 0.6451 0.2988 0.0609 1.0000 Uiso R . . . . .
H252 H 0.2329 0.6186 0.3262 0.0588 1.0000 Uiso R . . . . .
H251 H 0.2429 0.8223 0.3278 0.0585 1.0000 Uiso R . . . . .
H242 H 0.1651 0.6403 0.3816 0.0638 1.0000 Uiso R . . . . .
H241 H 0.1802 0.8446 0.3855 0.0639 1.0000 Uiso R . . . . .
H232 H 0.3021 0.7753 0.4090 0.0607 1.0000 Uiso R . . . . .
H231 H 0.2793 0.5761 0.4122 0.0619 1.0000 Uiso R . . . . .
H222 H 0.2519 0.8536 0.4672 0.0830 1.0000 Uiso R . . . . .
H221 H 0.2143 0.6676 0.4663 0.0828 1.0000 Uiso R . . . . .
H212 H 0.3045 0.6824 0.5280 0.0751 1.0000 Uiso R . . . . .
H211 H 0.3185 0.5365 0.4931 0.0752 1.0000 Uiso R . . . . .
H202 H 0.3900 0.8666 0.4998 0.0823 1.0000 Uiso R . . . . .
H201 H 0.4001 0.7235 0.4653 0.0817 1.0000 Uiso R . . . . .
H193 H 0.4393(14) 0.693(4) 0.5570(7) 0.0557 1.0000 Uiso D . . . . .
H191 H 0.4876(10) 0.698(4) 0.5264(9) 0.0561 1.0000 Uiso D . . . . .
H192 H 0.4421(14) 0.548(3) 0.5267(9) 0.0555 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.194(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.458(2) yes
S1 . O3 . 1.448(2) yes
S1 . O4 . 1.429(3) yes
S1 . C5 . 1.788(2) yes
C5 . C6 . 1.406(3) yes
C5 . C10 . 1.386(3) yes
C6 . C16 4_566 1.436(3) yes
C6 . C7 . 1.430(3) yes
C7 . C7 4_566 1.438(4) yes
C7 . C8 . 1.433(3) yes
C8 . C9 . 1.409(3) yes
C8 . C15 . 1.434(3) yes
C9 . C10 . 1.390(3) yes
C9 . S11 . 1.785(3) yes
C10 . H101 . 0.920 no
S11 . O12 . 1.455(2) yes
S11 . O13 . 1.452(2) yes
S11 . O14 . 1.450(3) yes
C15 . C16 . 1.352(3) yes
C15 . H151 . 0.943 no
C16 . H161 . 0.939 no
O17 . H171 . 0.816(19) no
O17 . H172 . 0.814(19) no
O18 . H181 . 0.817(19) no
O18 . H182 . 0.823(19) no
N19 . C20 . 1.485(5) yes
N19 . H193 . 0.878(19) no
N19 . H191 . 0.889(19) no
N19 . H192 . 0.890(19) no
C20 . C21 . 1.614(7) yes
C20 . H202 . 0.945 no
C20 . H201 . 0.967 no
C21 . C22 . 1.480(7) yes
C21 . H212 . 0.984 no
C21 . H211 . 0.978 no
C22 . C23 . 1.522(6) yes
C22 . H222 . 0.989 no
C22 . H221 . 0.970 no
C23 . C24 . 1.500(6) yes
C23 . H232 . 0.984 no
C23 . H231 . 0.979 no
C24 . C25 . 1.507(6) yes
C24 . H242 . 0.979 no
C24 . H241 . 0.982 no
C25 . C26 . 1.520(6) yes
C25 . H252 . 0.974 no
C25 . H251 . 0.978 no
C26 . C27 . 1.498(6) yes
C26 . H262 . 0.984 no
C26 . H261 . 0.992 no
C27 . C28 . 1.541(5) yes
C27 . H272 . 0.977 no
C27 . H271 . 0.978 no
C28 . C29 . 1.485(6) yes
C28 . H282 . 0.979 no
C28 . H281 . 0.972 no
C29 . N30 . 1.460(5) yes
C29 . H292 . 0.990 no
C29 . H291 . 0.970 no
N30 . H301 . 0.908(19) no
N30 . H303 . 0.922(19) no
N30 . H302 . 0.905(19) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 110.69(17) yes
O2 . S1 . O4 . 114.10(19) yes
O3 . S1 . O4 . 112.40(15) yes
O2 . S1 . C5 . 104.98(13) yes
O3 . S1 . C5 . 106.40(13) yes
O4 . S1 . C5 . 107.65(14) yes
S1 . C5 . C6 . 121.89(18) yes
S1 . C5 . C10 . 116.82(18) yes
C6 . C5 . C10 . 121.3(2) yes
C16 4_566 C6 . C5 . 123.1(2) yes
C16 4_566 C6 . C7 . 118.6(2) yes
C5 . C6 . C7 . 118.2(2) yes
C7 4_566 C7 . C6 . 119.6(3) yes
C7 4_566 C7 . C8 . 120.0(3) yes
C6 . C7 . C8 . 120.5(2) yes
C7 . C8 . C9 . 118.3(2) yes
C7 . C8 . C15 . 118.4(2) yes
C9 . C8 . C15 . 123.3(2) yes
C8 . C9 . C10 . 121.0(2) yes
C8 . C9 . S11 . 122.07(18) yes
C10 . C9 . S11 . 116.92(19) yes
C9 . C10 . C5 . 120.7(2) yes
C9 . C10 . H101 . 120.0 no
C5 . C10 . H101 . 119.3 no
C9 . S11 . O12 . 107.80(13) yes
C9 . S11 . O13 . 105.99(11) yes
O12 . S11 . O13 . 112.04(14) yes
C9 . S11 . O14 . 105.61(13) yes
O12 . S11 . O14 . 111.98(14) yes
O13 . S11 . O14 . 112.88(14) yes
C8 . C15 . C16 . 121.7(2) yes
C8 . C15 . H151 . 118.5 no
C16 . C15 . H151 . 119.8 no
C6 4_566 C16 . C15 . 121.7(2) yes
C6 4_566 C16 . H161 . 119.2 no
C15 . C16 . H161 . 119.1 no
H171 . O17 . H172 . 101(5) no
H181 . O18 . H182 . 110(5) no
C20 . N19 . H193 . 109.1(15) no
C20 . N19 . H191 . 109.6(15) no
H193 . N19 . H191 . 109.8(17) no
C20 . N19 . H192 . 108.6(15) no
H193 . N19 . H192 . 110.0(17) no
H191 . N19 . H192 . 109.8(17) no
N19 . C20 . C21 . 108.7(4) yes
N19 . C20 . H202 . 110.0 no
C21 . C20 . H202 . 110.5 no
N19 . C20 . H201 . 109.5 no
C21 . C20 . H201 . 109.3 no
H202 . C20 . H201 . 108.8 no
C20 . C21 . C22 . 113.5(4) yes
C20 . C21 . H212 . 110.9 no
C22 . C21 . H212 . 108.5 no
C20 . C21 . H211 . 107.8 no
C22 . C21 . H211 . 106.7 no
H212 . C21 . H211 . 109.2 no
C21 . C22 . C23 . 114.9(4) yes
C21 . C22 . H222 . 109.0 no
C23 . C22 . H222 . 107.8 no
C21 . C22 . H221 . 108.5 no
C23 . C22 . H221 . 106.4 no
H222 . C22 . H221 . 110.2 no
C22 . C23 . C24 . 114.3(4) yes
C22 . C23 . H232 . 106.6 no
C24 . C23 . H232 . 109.2 no
C22 . C23 . H231 . 107.2 no
C24 . C23 . H231 . 109.7 no
H232 . C23 . H231 . 109.6 no
C23 . C24 . C25 . 113.5(3) yes
C23 . C24 . H242 . 108.6 no
C25 . C24 . H242 . 106.9 no
C23 . C24 . H241 . 109.0 no
C25 . C24 . H241 . 109.2 no
H242 . C24 . H241 . 109.5 no
C24 . C25 . C26 . 112.3(3) yes
C24 . C25 . H252 . 109.0 no
C26 . C25 . H252 . 108.8 no
C24 . C25 . H251 . 108.8 no
C26 . C25 . H251 . 109.7 no
H252 . C25 . H251 . 108.1 no
C25 . C26 . C27 . 114.1(3) yes
C25 . C26 . H262 . 107.1 no
C27 . C26 . H262 . 108.3 no
C25 . C26 . H261 . 109.0 no
C27 . C26 . H261 . 108.4 no
H262 . C26 . H261 . 109.9 no
C26 . C27 . C28 . 112.9(3) yes
C26 . C27 . H272 . 109.2 no
C28 . C27 . H272 . 109.3 no
C26 . C27 . H271 . 107.5 no
C28 . C27 . H271 . 109.2 no
H272 . C27 . H271 . 108.7 no
C27 . C28 . C29 . 111.1(3) yes
C27 . C28 . H282 . 108.2 no
C29 . C28 . H282 . 107.8 no
C27 . C28 . H281 . 110.1 no
C29 . C28 . H281 . 109.0 no
H282 . C28 . H281 . 110.7 no
C28 . C29 . N30 . 111.5(3) yes
C28 . C29 . H292 . 109.8 no
N30 . C29 . H292 . 108.4 no
C28 . C29 . H291 . 108.9 no
N30 . C29 . H291 . 108.7 no
H292 . C29 . H291 . 109.5 no
C29 . N30 . H301 . 108.9(16) no
C29 . N30 . H303 . 109.6(16) no
H301 . N30 . H303 . 112.1(17) no
C29 . N30 . H302 . 108.1(16) no
H301 . N30 . H302 . 108.4(17) no
H303 . N30 . H302 . 109.8(17) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O17 . H171 . O13 7_564 162(5) 0.816 1.992 2.780(5) yes
O17 . H172 . O18 2_676 162(5) 0.814 1.974 2.761(5) yes
O18 . H181 . O14 7_564 170(6) 0.817 1.885 2.694(5) yes
O18 . H182 . O4 . 143(5) 0.823 2.154 2.857(5) yes
N30 . H301 . O18 3_444 155(3) 0.908 2.019 2.869(5) yes
N30 . H303 . O12 5_574 145(3) 0.922 1.987 2.790(5) yes
N30 . H302 . O3 3_454 177(3) 0.905 1.881 2.785(5) yes
C29 . H291 . O14 5_564 154.73(10) 0.970 2.552 3.454(5) yes
C26 . H262 . O3 8_555 169.86(11) 0.984 2.569 3.542(5) yes
C26 . H261 . O4 8_545 159.77(13) 0.992 2.423 3.371(5) yes
N19 . H193 . O2 . 161(3) 0.878 1.886 2.731(5) yes
N19 . H191 . O17 . 149(3) 0.889 2.116 2.913(5) yes
N19 . H192 . O17 2_666 175(3) 0.890 1.980 2.868(5) yes


####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1040390'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
_cell_length_a                   9.7673(3)
_cell_length_b                   9.8143(3)
_cell_length_c                   10.2046(4)
_cell_angle_alpha                94.880(3)
_cell_angle_beta                 96.822(3)
_cell_angle_gamma                95.184(3)
_cell_volume                     962.75(6)
_cell_measurement_reflns_used    6434
_cell_measurement_theta_min      2.0870
_cell_measurement_theta_max      32.3350
_cell_oxdiff_length_a            9.7673(3)
_cell_oxdiff_length_b            9.8143(3)
_cell_oxdiff_length_c            10.2046(4)
_cell_oxdiff_angle_alpha         94.880(3)
_cell_oxdiff_angle_beta          96.822(3)
_cell_oxdiff_angle_gamma         95.184(3)
_cell_oxdiff_volume              962.75(6)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            1

_chemical_formula_sum            'C28.7552 H49.5104 N8 O14 S4'
_chemical_formula_moiety         
'C16 H6 O12 S4, 2(H2 O), 2(C H6 N3), 0.6224(C10 H26 N2), 0.1888(C12 H30 N2), 0.1888(C12 H30 N2)'
_chemical_compound_source        ?
_chemical_formula_weight         859.59


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_max          0.550
_exptl_absorpt_correction_T_min  0.90587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             454.041
_exptl_absorpt_coefficient_mu    0.322
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.66
_montpellier_reflns_completeness_maxres 90.46
_montpellier_reflns_redundancy_maxres 2.33

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.47 3.3 57.36 0.019 100.0 100.00
1 1.47 1.17 3.1 36.85 0.023 100.0 100.00
2 1.17 1.02 2.9 25.82 0.027 100.0 100.00
3 1.02 0.93 2.5 18.35 0.041 100.0 100.00
4 0.93 0.86 2.3 14.16 0.049 100.0 100.00
5 0.86 0.81 2.1 12.35 0.053 100.0 100.00
6 0.81 0.77 2.0 9.36 0.067 100.0 100.00
7 0.77 0.73 1.8 9.16 0.062 100.0 100.00
8 0.73 0.71 1.8 7.60 0.075 100.0 100.00
9 0.71 0.66 1.4 6.09 0.083 48.9 90.46
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0134280000
_diffrn_orient_matrix_UB_12      0.0704381000
_diffrn_orient_matrix_UB_13      0.0242412000
_diffrn_orient_matrix_UB_21      0.0699076000
_diffrn_orient_matrix_UB_22      -0.0099463000
_diffrn_orient_matrix_UB_23      0.0212029000
_diffrn_orient_matrix_UB_31      0.0183709000
_diffrn_orient_matrix_UB_32      0.0159899000
_diffrn_orient_matrix_UB_33      -0.0625279000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   91.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -       26.1732   77.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   68.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -       26.1732 -100.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   63.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -       26.1732   77.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega  -42.00   53.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -       26.1732  -77.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -89.00   30.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -      -26.9544    0.0000   60.0000 119

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   96.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -       26.1732   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00   30.00   1.0000   42.4400
omega____ theta____ kappa____ phi______ frames
    -       26.1732  -57.0000 -180.0000 73

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            14777
_reflns_number_total             6345
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0400
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6345 
# Theoretical number of reflections is about 14043 


_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         32.590
_diffrn_measured_fraction_theta_max 0.905

_diffrn_reflns_theta_full        27.702
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   1.44
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.76
_refine_diff_density_max         1.53


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         5557
_refine_ls_number_restraints     55
_refine_ls_number_parameters     241
_oxford_refine_ls_R_factor_ref   0.0586
_refine_ls_wR_factor_ref         0.0649
_refine_ls_goodness_of_fit_ref   0.9213
_refine_ls_shift/su_max          0.0007593
_refine_ls_shift/su_mean         0.0000241


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6345
_refine_ls_R_factor_all          0.0675
_refine_ls_wR_factor_all         0.0698

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5557
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_gt          0.0649

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 9.36 1.96 6.12 1.10 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.02676(19) 0.75855(17) 0.98101(18) 0.0187 1.0000 Uani . . . . . .
C2 C 0.08311(19) 0.70163(17) 0.87783(18) 0.0184 1.0000 Uani . . . . . .
C3 C 0.08457(17) 0.55552(16) 0.85356(16) 0.0154 1.0000 Uani . . . . . .
C4 C 0.13972(17) 0.49306(17) 0.74528(17) 0.0164 1.0000 Uani . . . . . .
C5 C 0.14779(18) 0.35230(17) 0.73058(17) 0.0170 1.0000 Uani . . . . . .
C6 C 0.09743(18) 0.26893(16) 0.82124(17) 0.0162 1.0000 Uani . . . . . .
C7 C 0.03452(17) 0.32445(16) 0.92790(17) 0.0157 1.0000 Uani . . . . . .
C8 C 0.02981(17) 0.46976(16) 0.94470(16) 0.0142 1.0000 Uani . . . . . .
S9 S 0.20640(4) 0.59134(4) 0.62417(4) 0.0170 1.0000 Uani . . . . . .
O10 O 0.09141(15) 0.65989(16) 0.56482(15) 0.0252 1.0000 Uani . . . . . .
O11 O 0.31754(15) 0.68980(15) 0.69489(15) 0.0250 1.0000 Uani . . . . . .
O12 O 0.25802(17) 0.49448(15) 0.53149(15) 0.0277 1.0000 Uani . . . . . .
S13 S 0.11913(5) 0.09053(4) 0.79813(4) 0.0183 1.0000 Uani . . . . . .
O14 O 0.1985(2) 0.07694(16) 0.68697(18) 0.0354 1.0000 Uani . . . . . .
O15 O 0.19068(16) 0.05378(14) 0.92036(15) 0.0259 1.0000 Uani . . . . . .
O16 O -0.02057(16) 0.01837(14) 0.76695(16) 0.0269 1.0000 Uani . . . . . .
N17 N -0.17053(19) 0.7466(2) 0.6564(2) 0.0317 1.0000 Uani . . . . . .
N18 N -0.4023(2) 0.6775(2) 0.6378(2) 0.0333 1.0000 Uani . . . . . .
N19 N -0.3039(2) 0.8498(2) 0.7977(2) 0.0385 1.0000 Uani . . . . . .
C20 C -0.2927(2) 0.7570(2) 0.6987(2) 0.0242 1.0000 Uani . . . . . .
O21 O 0.4379(3) 0.8984(4) 0.8885(4) 0.0927 1.0000 Uani . . . . . .
N22 N 0.1870(2) -0.0983(2) 0.4584(2) 0.0341 1.0000 Uani D . . . . .
H51 H 0.1827 0.3099 0.6596 0.0500 1.0000 Uiso R . . . . .
H21 H 0.1262 0.7631 0.8179 0.0500 1.0000 Uiso R . . . . .
H11 H 0.0307 0.8577 0.9959 0.0500 1.0000 Uiso R . . . . .
H181 H -0.4813 0.6762 0.6602 0.0500 1.0000 Uiso R . . . . .
H182 H -0.3926 0.6234 0.5715 0.0500 1.0000 Uiso R . . . . .
H191 H -0.2324 0.9015 0.8455 0.0500 1.0000 Uiso R . . . . .
H192 H -0.3746 0.8559 0.8186 0.0500 1.0000 Uiso R . . . . .
H172 H -0.1560 0.6822 0.5963 0.0500 1.0000 Uiso R . . . . .
H171 H -0.0982 0.7969 0.6963 0.0500 1.0000 Uiso R . . . . .
H211 H 0.3743 0.8327 0.8269 0.0500 1.0000 Uiso R . . . . .
H212 H 0.3791 0.9640 0.8954 0.0500 1.0000 Uiso R . . . . .
H221 H 0.1375 -0.0738 0.3969 0.0500 1.0000 Uiso . . . . . .
H222 H 0.1847 -0.0413 0.5319 0.0500 1.0000 Uiso . . . . . .
H223 H 0.1469 -0.1675 0.4809 0.0500 1.0000 Uiso . . . . . .
C282 C 0.5226(7) -0.4233(7) 0.0199(8) 0.0358(10) 0.3775(18) Uiso D . P . 2 .
C272 C 0.4894(12) -0.3694(12) 0.1507(11) 0.0670(10) 0.3775(18) Uiso D . P . 2 .
C262 C 0.346(2) -0.368(2) 0.168(2) 0.0670(10) 0.1888(9) Uiso D . P . 2 .
C252 C 0.321(3) -0.307(2) 0.300(2) 0.0670(10) 0.1888(9) Uiso D . P . 2 .
C253 C 0.477(2) -0.169(2) 0.297(2) 0.0670(10) 0.1888(9) Uiso D . P . 2 .
C263 C 0.484(3) -0.229(2) 0.161(2) 0.0670(10) 0.1888(9) Uiso D . P . 2 .
C241 C 0.2967(4) -0.2452(5) 0.2872(4) 0.0338(3) 0.6225(18) Uiso . . P . 1 .
C231 C 0.3276(4) -0.1398(4) 0.4078(4) 0.0265(3) 0.6225(18) Uiso . . P . 1 .
C271 C 0.5177(4) -0.4539(4) 0.0656(4) 0.0295(3) 0.6225(18) Uiso . . P . 1 .
C251 C 0.4262(4) -0.2968(4) 0.2398(4) 0.0347(3) 0.6225(18) Uiso . . P . 1 .
C261 C 0.3923(5) -0.3980(5) 0.1161(4) 0.0382(3) 0.6225(18) Uiso . . P . 1 .
C242 C 0.3369(12) -0.1667(12) 0.3225(12) 0.0670(10) 0.3775(18) Uiso D . P . 2 .
C232 C 0.3218(12) -0.0828(13) 0.4488(12) 0.0670(10) 0.3775(18) Uiso D . P . 2 .
H2321 H 0.3737 -0.1168 0.5215 0.0830 0.3776(18) Uiso R . P . 2 .
H2322 H 0.3529 0.0112 0.4448 0.0830 0.3776(18) Uiso R . P . 2 .
H2311 H 0.3813 -0.1777 0.4768 0.0319 0.6224(18) Uiso R . P . 1 .
H2312 H 0.3782 -0.0601 0.3845 0.0319 0.6224(18) Uiso R . P . 1 .
H2421 H 0.2961 -0.2577 0.3259 0.0830 0.1888(9) Uiso R . P . 2 .
H2422 H 0.2890 -0.1267 0.2512 0.0830 0.1888(9) Uiso R . P . 2 .
H2423 H 0.4277 -0.1407 0.3027 0.0830 0.1888(9) Uiso R . P . 2 .
H2424 H 0.2708 -0.1365 0.2582 0.0830 0.1888(9) Uiso R . P . 2 .
H2531 H 0.5201 -0.2246 0.3575 0.0830 0.1888(9) Uiso R . P . 2 .
H2532 H 0.5225 -0.0785 0.3100 0.0830 0.1888(9) Uiso R . P . 2 .
H2631 H 0.5661 -0.1871 0.1332 0.0830 0.1888(9) Uiso R . P . 2 .
H2632 H 0.4056 -0.2085 0.1052 0.0830 0.1888(9) Uiso R . P . 2 .
H2511 H 0.4731 -0.3412 0.3085 0.0418 0.6224(18) Uiso R . P . 1 .
H2512 H 0.4847 -0.2204 0.2204 0.0418 0.6224(18) Uiso R . P . 1 .
H2411 H 0.2400 -0.3215 0.3094 0.0407 0.6224(18) Uiso R . P . 1 .
H2412 H 0.2482 -0.2044 0.2169 0.0407 0.6224(18) Uiso R . P . 1 .
H2611 H 0.3325 -0.4731 0.1360 0.0460 0.6224(18) Uiso R . P . 1 .
H2612 H 0.3460 -0.3526 0.0478 0.0460 0.6224(18) Uiso R . P . 1 .
H2711 H 0.5596 -0.5063 0.1305 0.0355 0.6224(18) Uiso R . P . 1 .
H2712 H 0.5814 -0.3787 0.0527 0.0355 0.6224(18) Uiso R . P . 1 .
H2821 H 0.6204 -0.4103 0.0219 0.0456 0.3776(18) Uiso R . P . 2 .
H2822 H 0.4802 -0.3711 -0.0450 0.0456 0.3776(18) Uiso R . P . 2 .
H2721 H 0.5575 -0.3928 0.2172 0.0830 0.1888(9) Uiso R . P . 2 .
H2722 H 0.4012 -0.4128 0.1623 0.0830 0.1888(9) Uiso R . P . 2 .
H2723 H 0.5304 -0.4240 0.2142 0.0830 0.1888(9) Uiso R . P . 2 .
H2724 H 0.5300 -0.2771 0.1689 0.0830 0.1888(9) Uiso R . P . 2 .
H2521 H 0.3836 -0.3412 0.3652 0.0830 0.1888(9) Uiso R . P . 2 .
H2522 H 0.2288 -0.3366 0.3117 0.0830 0.1888(9) Uiso R . P . 2 .
H2621 H 0.3051 -0.4606 0.1562 0.0830 0.1888(9) Uiso R . P . 2 .
H2622 H 0.3025 -0.3174 0.1028 0.0830 0.1888(9) Uiso R . P . 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.882(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C7 2_567 1.435(2) yes
C1 . C2 . 1.348(2) yes
C1 . H11 . 0.968 no
C2 . C3 . 1.436(2) yes
C2 . H21 . 0.997 no
C3 . C4 . 1.405(2) yes
C3 . C8 . 1.425(2) yes
C4 . C5 . 1.387(2) yes
C4 . S9 . 1.7784(17) yes
C5 . C6 . 1.390(2) yes
C5 . H51 . 0.920 no
C6 . C7 . 1.406(2) yes
C6 . S13 . 1.7818(17) yes
C7 . C8 . 1.427(2) yes
C8 . C8 2_567 1.439(3) yes
S9 . O10 . 1.4578(15) yes
S9 . O11 . 1.4624(14) yes
S9 . O12 . 1.4489(15) yes
S13 . O14 . 1.4514(16) yes
S13 . O15 . 1.4455(15) yes
S13 . O16 . 1.4658(15) yes
N17 . C20 . 1.325(3) yes
N17 . H172 . 0.875 no
N17 . H171 . 0.862 no
N18 . C20 . 1.323(3) yes
N18 . H181 . 0.830 no
N18 . H182 . 0.844 no
N19 . C20 . 1.323(3) yes
N19 . H191 . 0.892 no
N19 . H192 . 0.753 no
O21 . H211 . 0.982 no
O21 . H212 . 0.904 no
N22 . H221 . 0.813 no
N22 . H222 . 0.901 no
N22 . H223 . 0.817 no
N22 . C231 . 1.597(4) yes
C282 . C282 2_645 1.535(14) yes
C282 . C272 . 1.477(12) yes
C282 . H2821 . 0.950 no
C282 . H2822 . 0.950 no
C272 . C262 . 1.44(2) yes
C272 . C263 . 1.374(19) yes
C272 . H2721 . 0.950 no
C272 . H2722 . 0.950 no
C272 . H2723 . 0.950 no
C272 . H2724 . 0.950 no
C262 . C252 . 1.48(2) yes
C262 . C263 . 1.84(3) yes
C262 . H2722 . 0.732 no
C262 . H2621 . 0.950 no
C262 . H2622 . 0.950 no
C252 . C242 . 1.37(2) yes
C252 . H2421 . 0.618 no
C252 . H2521 . 0.950 no
C252 . H2522 . 0.950 no
C253 . C263 . 1.47(2) yes
C253 . C242 . 1.42(2) yes
C253 . H2423 . 0.581 no
C253 . H2531 . 0.950 no
C253 . H2532 . 0.950 no
C263 . H2631 . 0.950 no
C263 . H2632 . 0.950 no
C263 . H2724 . 0.677 no
C241 . C231 . 1.522(6) yes
C241 . C251 . 1.519(6) yes
C241 . H2411 . 0.950 no
C241 . H2412 . 0.950 no
C231 . H2311 . 0.950 no
C231 . H2312 . 0.950 no
C271 . C271 2_645 1.535(8) yes
C271 . C261 . 1.514(6) yes
C271 . H2711 . 0.950 no
C271 . H2712 . 0.950 no
C251 . C261 . 1.522(6) yes
C251 . H2511 . 0.950 no
C251 . H2512 . 0.950 no
C261 . H2611 . 0.950 no
C261 . H2612 . 0.950 no
C242 . C232 . 1.499(15) yes
C242 . H2421 . 0.950 no
C242 . H2422 . 0.950 no
C242 . H2423 . 0.950 no
C242 . H2424 . 0.950 no
C232 . H2321 . 0.950 no
C232 . H2322 . 0.950 no
H2721 . H2723 . 0.383 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 2_567 C1 . C2 . 121.39(15) yes
C7 2_567 C1 . H11 . 119.3 no
C2 . C1 . H11 . 119.3 no
C1 . C2 . C3 . 121.78(15) yes
C1 . C2 . H21 . 118.8 no
C3 . C2 . H21 . 119.4 no
C2 . C3 . C4 . 123.08(15) yes
C2 . C3 . C8 . 118.60(15) yes
C4 . C3 . C8 . 118.31(14) yes
C3 . C4 . C5 . 121.19(15) yes
C3 . C4 . S9 . 121.50(12) yes
C5 . C4 . S9 . 117.29(13) yes
C4 . C5 . C6 . 120.48(15) yes
C4 . C5 . H51 . 122.1 no
C6 . C5 . H51 . 117.4 no
C5 . C6 . C7 . 120.99(15) yes
C5 . C6 . S13 . 117.21(13) yes
C7 . C6 . S13 . 121.80(12) yes
C1 2_567 C7 . C6 . 122.95(15) yes
C1 2_567 C7 . C8 . 118.74(15) yes
C6 . C7 . C8 . 118.31(14) yes
C8 2_567 C8 . C7 . 119.67(18) yes
C8 2_567 C8 . C3 . 119.71(17) yes
C7 . C8 . C3 . 120.61(14) yes
C4 . S9 . O10 . 106.27(8) yes
C4 . S9 . O11 . 106.57(8) yes
O10 . S9 . O11 . 111.79(9) yes
C4 . S9 . O12 . 106.16(8) yes
O10 . S9 . O12 . 113.57(10) yes
O11 . S9 . O12 . 111.89(9) yes
C6 . S13 . O14 . 105.00(8) yes
C6 . S13 . O15 . 107.39(8) yes
O14 . S13 . O15 . 113.39(11) yes
C6 . S13 . O16 . 106.27(8) yes
O14 . S13 . O16 . 111.95(11) yes
O15 . S13 . O16 . 112.21(9) yes
C20 . N17 . H172 . 123.1 no
C20 . N17 . H171 . 119.9 no
H172 . N17 . H171 . 116.4 no
C20 . N18 . H181 . 124.7 no
C20 . N18 . H182 . 118.7 no
H181 . N18 . H182 . 116.6 no
C20 . N19 . H191 . 124.4 no
C20 . N19 . H192 . 118.0 no
H191 . N19 . H192 . 117.4 no
N17 . C20 . N18 . 119.25(19) yes
N17 . C20 . N19 . 119.6(2) yes
N18 . C20 . N19 . 121.1(2) yes
H211 . O21 . H212 . 96.5 no
H221 . N22 . H222 . 109.4 no
H221 . N22 . H223 . 107.2 no
H222 . N22 . H223 . 98.8 no
H221 . N22 . C231 . 109.1 no
H222 . N22 . C231 . 123.3 no
H223 . N22 . C231 . 107.6 no
C282 2_645 C282 . C272 . 115.4(9) yes
C282 2_645 C282 . H2821 . 107.3 no
C272 . C282 . H2821 . 107.5 no
C282 2_645 C282 . H2822 . 109.1 no
C272 . C282 . H2822 . 107.9 no
H2821 . C282 . H2822 . 109.5 no
C282 . C272 . C262 . 117.8(12) yes
C282 . C272 . C263 . 112.4(12) yes
C262 . C272 . C263 . 82.0(16) yes
C282 . C272 . H2721 . 108.5 no
C262 . C272 . H2721 . 123.0 no
C263 . C272 . H2721 . 109.8 no
C282 . C272 . H2722 . 107.6 no
C262 . C272 . H2722 . 27.1 no
C263 . C272 . H2722 . 109.0 no
H2721 . C272 . H2722 . 109.5 no
C282 . C272 . H2723 . 107.0 no
C262 . C272 . H2723 . 107.6 no
C263 . C272 . H2723 . 128.4 no
H2721 . C272 . H2723 . 23.3 no
H2722 . C272 . H2723 . 88.5 no
C282 . C272 . H2724 . 108.2 no
C262 . C272 . H2724 . 106.6 no
C263 . C272 . H2724 . 26.7 no
H2721 . C272 . H2724 . 87.4 no
H2722 . C272 . H2724 . 132.4 no
H2723 . C272 . H2724 . 109.5 no
C272 . C262 . C252 . 114.5(18) yes
C272 . C262 . C263 . 47.6(10) yes
C252 . C262 . C263 . 90.5(16) yes
C272 . C262 . H2722 . 36.2 no
C252 . C262 . H2722 . 120.5 no
C263 . C262 . H2722 . 83.7 no
C272 . C262 . H2621 . 107.5 no
C252 . C262 . H2621 . 108.5 no
C263 . C262 . H2621 . 154.4 no
H2722 . C262 . H2621 . 71.9 no
C272 . C262 . H2622 . 108.5 no
C252 . C262 . H2622 . 108.3 no
C263 . C262 . H2622 . 79.1 no
H2722 . C262 . H2622 . 128.1 no
H2621 . C262 . H2622 . 109.5 no
C262 . C252 . C242 . 117.5(19) yes
C262 . C252 . H2421 . 140.7 no
C242 . C252 . H2421 . 36.8 no
C262 . C252 . H2521 . 108.1 no
C242 . C252 . H2521 . 107.3 no
H2421 . C252 . H2521 . 108.9 no
C262 . C252 . H2522 . 107.4 no
C242 . C252 . H2522 . 106.9 no
H2421 . C252 . H2522 . 71.9 no
H2521 . C252 . H2522 . 109.5 no
C263 . C253 . C242 . 111.6(18) yes
C263 . C253 . H2423 . 114.9 no
C242 . C253 . H2423 . 28.2 no
C263 . C253 . H2531 . 108.6 no
C242 . C253 . H2531 . 107.2 no
H2423 . C253 . H2531 . 126.7 no
C263 . C253 . H2532 . 110.1 no
C242 . C253 . H2532 . 109.9 no
H2423 . C253 . H2532 . 83.2 no
H2531 . C253 . H2532 . 109.5 no
C253 . C263 . C272 . 113.8(18) yes
C253 . C263 . C262 . 93.2(16) yes
C272 . C263 . C262 . 50.5(10) yes
C253 . C263 . H2631 . 107.2 no
C272 . C263 . H2631 . 109.0 no
C262 . C263 . H2631 . 156.5 no
C253 . C263 . H2632 . 108.2 no
C272 . C263 . H2632 . 109.2 no
C262 . C263 . H2632 . 73.5 no
H2631 . C263 . H2632 . 109.5 no
C253 . C263 . H2724 . 104.3 no
C272 . C263 . H2724 . 39.1 no
C262 . C263 . H2724 . 87.4 no
H2631 . C263 . H2724 . 76.7 no
H2632 . C263 . H2724 . 142.8 no
C231 . C241 . C251 . 113.3(3) yes
C231 . C241 . H2411 . 108.5 no
C251 . C241 . H2411 . 108.5 no
C231 . C241 . H2412 . 108.6 no
C251 . C241 . H2412 . 108.5 no
H2411 . C241 . H2412 . 109.5 no
C241 . C231 . N22 . 110.6(3) yes
C241 . C231 . H2311 . 109.2 no
N22 . C231 . H2311 . 109.2 no
C241 . C231 . H2312 . 109.2 no
N22 . C231 . H2312 . 109.2 no
H2311 . C231 . H2312 . 109.5 no
C271 2_645 C271 . C261 . 113.2(4) yes
C271 2_645 C271 . H2711 . 108.5 no
C261 . C271 . H2711 . 108.5 no
C271 2_645 C271 . H2712 . 108.6 no
C261 . C271 . H2712 . 108.5 no
H2711 . C271 . H2712 . 109.5 no
C241 . C251 . C261 . 112.0(4) yes
C241 . C251 . H2511 . 108.8 no
C261 . C251 . H2511 . 108.9 no
C241 . C251 . H2512 . 108.8 no
C261 . C251 . H2512 . 108.9 no
H2511 . C251 . H2512 . 109.5 no
C251 . C261 . C271 . 114.2(4) yes
C251 . C261 . H2611 . 108.3 no
C271 . C261 . H2611 . 108.3 no
C251 . C261 . H2612 . 108.3 no
C271 . C261 . H2612 . 108.3 no
H2611 . C261 . H2612 . 109.5 no
C253 . C242 . C252 . 88.3(15) yes
C253 . C242 . C232 . 113.7(12) yes
C252 . C242 . C232 . 126.8(14) yes
C253 . C242 . H2421 . 109.9 no
C252 . C242 . H2421 . 23.0 no
C232 . C242 . H2421 . 108.8 no
C253 . C242 . H2422 . 107.0 no
C252 . C242 . H2422 . 110.6 no
C232 . C242 . H2422 . 108.0 no
H2421 . C242 . H2422 . 109.5 no
C253 . C242 . H2423 . 16.8 no
C252 . C242 . H2423 . 104.4 no
C232 . C242 . H2423 . 106.2 no
H2421 . C242 . H2423 . 126.5 no
H2422 . C242 . H2423 . 96.4 no
C253 . C242 . H2424 . 119.3 no
C252 . C242 . H2424 . 105.0 no
C232 . C242 . H2424 . 104.4 no
H2421 . C242 . H2424 . 99.5 no
H2422 . C242 . H2424 . 13.1 no
H2423 . C242 . H2424 . 109.5 no
C242 . C232 . N22 . 104.7(9) yes
C242 . C232 . H2321 . 109.9 no
N22 . C232 . H2321 . 111.1 no
C242 . C232 . H2322 . 110.9 no
N22 . C232 . H2322 . 110.8 no
H2321 . C232 . H2322 . 109.5 no
C242 . H2421 . C252 . 120.2 no
C242 . H2423 . C253 . 135.1 no
C272 . H2721 . H2723 . 78.4 no
C272 . H2722 . C262 . 116.6 no
C272 . H2723 . H2721 . 78.4 no
C272 . H2724 . C263 . 114.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C2 . H21 . O11 . 120.70(5) 0.997 2.497 3.125(11) yes
C1 . H11 . O15 1_565 132.14(5) 0.968 2.595 3.323(11) yes
N18 . H181 . O11 1_455 172.06(8) 0.830 2.051 2.875(11) yes
N18 . H182 . O12 2_566 147.89(7) 0.844 2.136 2.886(11) yes
N19 . H191 . O15 2_567 127.35(7) 0.892 2.372 2.998(11) yes
N19 . H191 . O16 1_565 128.53(6) 0.892 2.522 3.156(11) yes
N19 . H192 . O21 1_455 172.58(10) 0.753 2.106 2.854(11) yes
N17 . H172 . O12 2_566 142.69(6) 0.875 2.167 2.912(11) yes
N17 . H171 . O16 1_565 141.49(6) 0.862 2.264 2.987(11) yes
O21 . H211 . O11 . 158.46(10) 0.982 1.857 2.793(11) yes
O21 . H212 . O15 1_565 158.92(11) 0.904 2.144 3.005(11) yes
N22 . H221 . O16 2_556 176.08(18) 0.813 2.051 2.863(11) yes
N22 . H222 . O14 . 174.44(16) 0.901 1.865 2.763(11) yes
N22 . H223 . O10 1_545 166.11(15) 0.817 2.022 2.821(11) yes
C232 . H2312 . C253 . 127.6(11) 0.934 1.760 2.445(11) yes
C253 . H2512 . C272 . 146.4(17) 0.906 1.578 2.385(11) yes
C253 . H2512 . C261 . 138.0(14) 0.906 2.038 2.778(11) yes
C262 . H2611 . C282 2_645 122.1(11) 1.047 2.467 3.151(11) yes
C262 . H2722 . C282 . 127(2) 0.732 1.984 2.495(11) yes
C262 . H2722 . C282 2_645 137(2) 0.732 2.575 3.151(11) yes
C262 . H2722 . C271 . 142(2) 0.732 1.647 2.270(11) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 07/07/14 at 15:14:09
#
#LIST     12                                                                    
BLOCK SCALE C(1,X'S, U'S) UNTIL N(22), 
CONT C(282,X'S,U[ISO],OCC) UNTIL C(232) 
EQUIVALENCE  C(231,U[ISO]) C(241,U[ISO]) 
CONT C(251,U[ISO]) C(261,U[ISO]) C(271,U[ISO]) 
EQUIVALENCE C(232,U[ISO]) C(242,U[ISO])  C(272,U[ISO]) C(282,U[ISO]) 
CONT C(252,U[ISO]) C(253,U[ISO]) C(262,U[ISO]) C(263,U[ISO]) 
EQUIVALENCE  C(231,OCC) C(241,OCC) C(251,OCC) C(261,OCC) C(271,OCC) 
CONT C(232,OCC) C(242,OCC)  C(272,OCC) C(282,OCC) 
CONT C(252,OCC) C(253,OCC) C(262,OCC) C(263,OCC) 
CONT H(2311,OCC) H(2312,OCC) H(2411,OCC) H(2412,OCC) 
CONT H(2511,OCC) H(2512,OCC) H(2611,OCC) H(2612,OCC) 
CONT H(2711,OCC) H(2712,OCC) 
CONT H(2321,OCC) H(2322,OCC) 
CONT  H(2421,OCC) H(2422,OCC)  H(2423,OCC) H(2424,OCC) 
CONT H(2521,OCC) H(2522,OCC) H(2531,OCC) H(2532,OCC) 
CONT H(2621,OCC) H(2622,OCC) H(2631,OCC) H(2632,OCC) 
CONT  H(2721,OCC) H(2722,OCC)  H(2723,OCC) H(2724,OCC)
CONT  H(2821,OCC) H(2822,OCC) 
WEIGHT -1 C(232,OCC) C(242,OCC)  C(272,OCC) C(282,OCC)
CONT H(2321,OCC) H(2322,OCC) H(2821,OCC) H(2822,OCC) 
WEIGHT -0.50 C(252,OCC) C(253,OCC) C(262,OCC) C(263,OCC) 
CONT  H(2421,OCC) H(2422,OCC)  H(2423,OCC) H(2424,OCC) 
CONT H(2721,OCC) H(2722,OCC)  H(2723,OCC) H(2724,OCC)
CONT H(2621,OCC) H(2622,OCC) H(2631,OCC) H(2632,OCC) 
CONT H(2521,OCC) H(2522,OCC) H(2531,OCC) H(2532,OCC) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE N   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE N   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE N   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE O   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (   232,X'S) H   (  2321,X'S)  H   (  2322,X'S) 
RIDE C   (   242,X'S) H(2421,X'S)  H(2422,X'S) H(2423,X'S) H(2424,X'S) 
RIDE C   (   252,X'S) H   (  2521,X'S)  H   (  2522,X'S) 
RIDE C   (   253,X'S) H   (  2531,X'S)  H   (  2532,X'S) 
RIDE C   (   262,X'S) H   (  2621,X'S)  H   (  2622,X'S) 
RIDE C   (   263,X'S) H   (  2631,X'S)  H   (  2632,X'S) 
RIDE C   (   272,X'S) H(2721,X'S)  H(2722,X'S) H(2723,X'S) H(2724,X'S) 
RIDE C   (   282,X'S) H   (  2821,X'S)  H   (  2822,X'S) 
RIDE C   (   231,X'S) H   (  2311,X'S)  H   (  2312,X'S) 
RIDE C   (   241,X'S) H   (  2411,X'S)  H   (  2412,X'S) 
RIDE C   (   251,X'S) H   (  2511,X'S)  H   (  2512,X'S) 
RIDE C   (   261,X'S) H   (  2611,X'S)  H   (  2612,X'S) 
RIDE C   (   271,X'S) H   (  2711,X'S)  H   (  2712,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 07/07/14 at 15:14:09
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
DIST 1.5,0.03=C(232) TO C(242), C(242) TO C(252), C(242) TO C(253), 
CONT C(252) TO C(262), C(253) TO C(263), C(262) TO C(272), C(263) TO C(272), 
CONT C(272) TO C(282), N(22) TO C(232) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   SHIFTLIMIT   START (DO NOT REMOVE THIS LINE) 
LIMIT      0.1000000 C(232,X) 
LIMIT      0.1000000 C(232,Y)
LIMIT      0.1000000 C(232,Z) 
LIMIT      0.01000000 OCC 
REM   SHIFTLIMIT   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
