# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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#
data_1

_exptl_special_details           
; 
 The crystal was placed in the cold stream of an Cryo-Industries of America
 open-flow nitrogen cryostat with a nominal stability of 0.1K. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.0540(15)
_cell_length_b                   16.853(2)
_cell_length_c                   23.794(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4031.5(9)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

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 0.0181 0.0091 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'
O 0.0492 0.0322 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'


_cell_formula_units_Z            4

# Given Formula = C44 H60 O15 
# Dc =      1.37 Fooo =   1784.00 Mu =      8.49 M =    828.95
# Found Formula = C43 H60 O16 
# Dc =      1.37 FOOO =   1784.00 Mu =      8.70 M =    832.94

_chemical_formula_sum            'C43 H60 O16'
_chemical_formula_moiety         'C42 H52 O13, C H4 O, 2(H2 O)'
_chemical_compound_source        'Chemical Synthesis'
_chemical_formula_weight         832.94


_cell_measurement_reflns_used    989
_cell_measurement_theta_min      9
_cell_measurement_theta_max      132
_cell_measurement_temperature    263

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1784
_exptl_absorpt_coefficient_mu    0.870

# Sheldrick geometric approximatio 0.92 0.92 
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9167
_exptl_absorpt_correction_T_max  0.9167
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      263
_diffrn_reflns_number            24449
_reflns_number_total             6950
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections without Friedels Law is 6950 
# Number of reflections with Friedels Law is 3984 
# Theoretical number of reflections is about 3575 


_diffrn_reflns_theta_min         3.213
_diffrn_reflns_theta_max         66.760
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        66.760
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   3.21
_oxford_diffrn_Wilson_scale      0.08

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

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.19


# 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>-93.0\s(I)
_refine_ls_number_reflns         6879
_refine_ls_number_restraints     0
_refine_ls_number_parameters     534
_oxford_refine_ls_R_factor_ref   0.0337
_refine_ls_wR_factor_ref         0.0922
_refine_ls_goodness_of_fit_ref   1.0046
_refine_ls_shift/su_max          0.0005014
_refine_ls_shift/su_mean         0.0000440


# The values computed from all data 
_oxford_reflns_number_all        6879
_refine_ls_R_factor_all          0.0337
_refine_ls_wR_factor_all         0.0922

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6780
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_gt          0.0918

_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_abs_structure_details 'Flack (1983), 2966 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.50P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
O1 O -0.79162(11) -0.51251(5) -0.36108(4) 0.0288 1.0000 Uani . . . . . .
C2 C -0.78922(14) -0.57775(8) -0.39720(6) 0.0257 1.0000 Uani . . . . . .
O3 O -0.67965(11) -0.63105(6) -0.38869(4) 0.0317 1.0000 Uani . . . . . .
C4 C -0.81504(16) -0.65913(8) -0.37651(7) 0.0323 1.0000 Uani . . . . . .
C5 C -0.84186(19) -0.67245(9) -0.31509(7) 0.0378 1.0000 Uani . . . . . .
C6 C -0.79728(19) -0.60290(9) -0.27931(6) 0.0363 1.0000 Uani . . . . . .
C7 C -0.84586(15) -0.52484(9) -0.30430(6) 0.0293 1.0000 Uani . . . . . .
C8 C -0.78831(15) -0.45447(9) -0.27074(6) 0.0294 1.0000 Uani . . . . . .
O9 O -0.71704(14) -0.46555(7) -0.23047(5) 0.0470 1.0000 Uani . . . . . .
C10 C -0.82826(15) -0.37104(8) -0.28801(6) 0.0271 1.0000 Uani . . . . . .
C11 C -0.96423(15) -0.37254(8) -0.31878(6) 0.0271 1.0000 Uani . . . . . .
C12 C -1.01848(16) -0.28725(9) -0.32119(6) 0.0321 1.0000 Uani . . . . . .
O13 O -1.08558(13) -0.26970(7) -0.37204(5) 0.0455 1.0000 Uani . . . . . .
C14 C -0.90380(16) -0.22973(9) -0.30894(6) 0.0306 1.0000 Uani . . . . . .
O15 O -0.95097(13) -0.15312(6) -0.31605(5) 0.0393 1.0000 Uani . . . . . .
O16 O -0.87125(13) -0.23851(6) -0.25060(4) 0.0375 1.0000 Uani . . . . . .
C17 C -0.83149(18) -0.31771(9) -0.23560(6) 0.0345 1.0000 Uani . . . . . .
H171 H -0.8975 -0.3374 -0.2093 0.0405 1.0000 Uiso R . . . . .
H172 H -0.7441 -0.3163 -0.2192 0.0397 1.0000 Uiso R . . . . .
C18 C -0.77258(15) -0.24594(8) -0.34128(5) 0.0267 1.0000 Uani . . . . . .
C19 C -0.72476(15) -0.33462(8) -0.32932(6) 0.0270 1.0000 Uani . . . . . .
C20 C -0.57833(17) -0.33758(10) -0.31118(8) 0.0406 1.0000 Uani . . . . . .
C21 C -0.48712(18) -0.28820(11) -0.34846(9) 0.0452 1.0000 Uani . . . . . .
C22 C -0.55309(18) -0.20964(10) -0.36904(8) 0.0423 1.0000 Uani . . . . . .
C23 C -0.66121(17) -0.18691(9) -0.32660(7) 0.0354 1.0000 Uani . . . . . .
O24 O -0.71130(13) -0.10890(6) -0.33789(6) 0.0453 1.0000 Uani . . . . . .
H231 H -0.6352 -0.1933 -0.2882 0.0411 1.0000 Uiso R . . . . .
C25 C -0.6336(2) -0.21977(10) -0.42178(7) 0.0427 1.0000 Uani . . . . . .
C26 C -0.77101(17) -0.24133(8) -0.40537(6) 0.0328 1.0000 Uani . . . . . .
O27 O -0.86210(14) -0.25672(7) -0.43726(4) 0.0449 1.0000 Uani . . . . . .
C28 C -0.5988(3) -0.20795(15) -0.47503(10) 0.0691 1.0000 Uani . . . . . .
H281 H -0.6616 -0.2157 -0.5048 0.0828 1.0000 Uiso R . . . . .
H282 H -0.5115 -0.1919 -0.4824 0.0836 1.0000 Uiso R . . . . .
H221 H -0.4867 -0.1674 -0.3715 0.0507 1.0000 Uiso R . . . . .
H211 H -0.4575 -0.3196 -0.3816 0.0545 1.0000 Uiso R . . . . .
H212 H -0.4105 -0.2743 -0.3264 0.0539 1.0000 Uiso R . . . . .
H201 H -0.5495 -0.3926 -0.3106 0.0503 1.0000 Uiso R . . . . .
H202 H -0.5740 -0.3174 -0.2732 0.0495 1.0000 Uiso R . . . . .
H191 H -0.7328 -0.3644 -0.3648 0.0315 1.0000 Uiso R . . . . .
H121 H -1.0819 -0.2811 -0.2915 0.0379 1.0000 Uiso R . . . . .
C29 C -1.06215(16) -0.43673(9) -0.29694(7) 0.0338 1.0000 Uani . . . . . .
C30 C -0.99941(16) -0.51946(9) -0.30692(7) 0.0343 1.0000 Uani . . . . . .
H301 H -1.0262 -0.5363 -0.3436 0.0417 1.0000 Uiso R . . . . .
H302 H -1.0333 -0.5552 -0.2804 0.0413 1.0000 Uiso R . . . . .
C31 C -1.1920(2) -0.43257(12) -0.32987(10) 0.0533 1.0000 Uani . . . . . .
H312 H -1.2495 -0.4782 -0.3186 0.0796 1.0000 Uiso R . . . . .
H311 H -1.1767 -0.4378 -0.3689 0.0779 1.0000 Uiso R . . . . .
H313 H -1.2402 -0.3840 -0.3213 0.0800 1.0000 Uiso R . . . . .
C32 C -1.0938(2) -0.42935(12) -0.23370(8) 0.0516 1.0000 Uani . . . . . .
H321 H -1.1595 -0.4681 -0.2240 0.0763 1.0000 Uiso R . . . . .
H323 H -1.1315 -0.3780 -0.2246 0.0760 1.0000 Uiso R . . . . .
H322 H -1.0138 -0.4373 -0.2097 0.0754 1.0000 Uiso R . . . . .
H111 H -0.9460 -0.3875 -0.3585 0.0308 1.0000 Uiso R . . . . .
H62 H -0.8369 -0.6072 -0.2423 0.0417 1.0000 Uiso R . . . . .
H61 H -0.6973 -0.6004 -0.2751 0.0410 1.0000 Uiso R . . . . .
H51 H -0.9376 -0.6819 -0.3113 0.0436 1.0000 Uiso R . . . . .
H52 H -0.7908 -0.7198 -0.3026 0.0449 1.0000 Uiso R . . . . .
C33 C -0.86447(19) -0.72256(9) -0.41607(7) 0.0401 1.0000 Uani . . . . . .
C34 C -0.94017(17) -0.68992(9) -0.46715(7) 0.0374 1.0000 Uani . . . . . .
C35 C -0.84879(16) -0.62739(9) -0.49564(6) 0.0303 1.0000 Uani . . . . . .
C36 C -0.80628(15) -0.55418(8) -0.45901(6) 0.0261 1.0000 Uani . . . . . .
C37 C -0.67113(15) -0.52618(8) -0.48404(5) 0.0263 1.0000 Uani . . . . . .
C38 C -0.69472(16) -0.50375(8) -0.54835(6) 0.0293 1.0000 Uani . . . . . .
C39 C -0.63829(19) -0.42028(9) -0.56025(7) 0.0384 1.0000 Uani . . . . . .
O40 O -0.66074(16) -0.40616(8) -0.61868(6) 0.0581 1.0000 Uani . . . . . .
C41 C -0.49112(19) -0.43182(10) -0.54687(7) 0.0401 1.0000 Uani . . . . . .
C42 C -0.46272(18) -0.51141(10) -0.57412(6) 0.0395 1.0000 Uani . . . . . .
C43 C -0.59189(17) -0.55302(9) -0.58040(6) 0.0328 1.0000 Uani . . . . . .
O44 O -0.60881(13) -0.61618(7) -0.60485(5) 0.0437 1.0000 Uani . . . . . .
C45 C -0.3465(2) -0.54142(13) -0.58973(8) 0.0533 1.0000 Uani . . . . . .
H451 H -0.3416 -0.5908 -0.6083 0.0641 1.0000 Uiso R . . . . .
H452 H -0.2661 -0.5149 -0.5824 0.0612 1.0000 Uiso R . . . . .
C46 C -0.47177(19) -0.43314(11) -0.48251(7) 0.0426 1.0000 Uani . . . . . .
C47 C -0.60003(18) -0.45911(9) -0.45240(6) 0.0367 1.0000 Uani . . . . . .
H472 H -0.6616 -0.4131 -0.4499 0.0428 1.0000 Uiso R . . . . .
H471 H -0.5764 -0.4759 -0.4140 0.0450 1.0000 Uiso R . . . . .
H462 H -0.3963 -0.4660 -0.4728 0.0502 1.0000 Uiso R . . . . .
H461 H -0.4454 -0.3784 -0.4686 0.0508 1.0000 Uiso R . . . . .
H411 H -0.4360 -0.3902 -0.5632 0.0475 1.0000 Uiso R . . . . .
H391 H -0.6772 -0.3786 -0.5392 0.0455 1.0000 Uiso R . . . . .
C48 C -0.84453(18) -0.51266(9) -0.56194(6) 0.0342 1.0000 Uani . . . . . .
C49 C -0.90015(17) -0.59621(10) -0.55210(6) 0.0362 1.0000 Uani . . . . . .
O50 O -0.87425(14) -0.64923(8) -0.59759(5) 0.0481 1.0000 Uani . . . . . .
H491 H -0.9945 -0.5880 -0.5505 0.0436 1.0000 Uiso R . . . . .
O51 O -0.91270(12) -0.46086(7) -0.52358(4) 0.0384 1.0000 Uani . . . . . .
C52 C -0.90712(17) -0.48653(9) -0.46614(6) 0.0323 1.0000 Uani . . . . . .
H521 H -0.9918 -0.5030 -0.4547 0.0367 1.0000 Uiso R . . . . .
H522 H -0.8789 -0.4414 -0.4442 0.0381 1.0000 Uiso R . . . . .
O53 O -0.87821(14) -0.48799(8) -0.61564(5) 0.0449 1.0000 Uani . . . . . .
H371 H -0.6125 -0.5717 -0.4814 0.0294 1.0000 Uiso R . . . . .
H351 H -0.7619 -0.6552 -0.5050 0.0354 1.0000 Uiso R . . . . .
C54 C -0.9647(2) -0.75959(11) -0.50754(9) 0.0519 1.0000 Uani . . . . . .
H541 H -1.0065 -0.8001 -0.4864 0.0759 1.0000 Uiso R . . . . .
H542 H -1.0224 -0.7454 -0.5379 0.0749 1.0000 Uiso R . . . . .
H543 H -0.8801 -0.7775 -0.5231 0.0762 1.0000 Uiso R . . . . .
C55 C -1.07515(19) -0.65797(12) -0.44811(8) 0.0477 1.0000 Uani . . . . . .
H552 H -1.1304 -0.7010 -0.4347 0.0708 1.0000 Uiso R . . . . .
H553 H -1.1254 -0.6292 -0.4770 0.0705 1.0000 Uiso R . . . . .
H551 H -1.0668 -0.6229 -0.4147 0.0711 1.0000 Uiso R . . . . .
H331 H -0.7868 -0.7531 -0.4294 0.0491 1.0000 Uiso R . . . . .
H332 H -0.9207 -0.7577 -0.3965 0.0473 1.0000 Uiso R . . . . .
O56 O -0.44043(16) -0.50415(11) -0.21396(9) 0.0781 1.0000 Uani . . . . . .
H562 H -0.4585 -0.5214 -0.2475 0.1167 1.0000 Uiso R . . . . .
H561 H -0.5210 -0.4956 -0.2087 0.1157 1.0000 Uiso R . . . . .
O57 O -1.1016(3) -0.66804(16) -0.67134(12) 0.1164 1.0000 Uani . . . . . .
O58 O -0.4587(2) -0.58539(19) -0.32087(10) 0.1092 1.0000 Uani . . . . . .
C59 C -0.3623(4) -0.6403(2) -0.34094(17) 0.1003 1.0000 Uani . . . . . .
H531 H -0.8176 -0.4552 -0.6207 0.0671 1.0000 Uiso R . . . . .
H401 H -0.6172 -0.3682 -0.6294 0.0866 1.0000 Uiso R . . . . .
H131 H -1.0196 -0.2678 -0.3947 0.0671 1.0000 Uiso R . . . . .
H571 H -1.0274 -0.6751 -0.6544 0.1754 1.0000 Uiso R . . . . .
H572 H -1.1003 -0.6213 -0.6850 0.1756 1.0000 Uiso R . . . . .
H151 H -0.8824 -0.1247 -0.3176 0.0581 1.0000 Uiso R . . . . .
H501 H -0.7930 -0.6453 -0.6034 0.0714 1.0000 Uiso R . . . . .
H241 H -0.6567 -0.0824 -0.3186 0.0670 1.0000 Uiso R . . . . .
H591 H -0.3397 -0.6252 -0.3785 0.1525 1.0000 Uiso R . . . . .
H581 H -0.5294 -0.5990 -0.3385 0.1627 1.0000 Uiso R . . . . .
H592 H -0.4048 -0.6917 -0.3426 0.1515 1.0000 Uiso R . . . . .
H593 H -0.2831 -0.6399 -0.3169 0.1502 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       140(30)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          3.42(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
O1 . C2 . 1.3957(17) yes
O1 . C7 . 1.4716(15) yes
C2 . O3 . 1.4357(17) yes
C2 . C4 . 1.4800(19) yes
C2 . C36 . 1.5331(18) yes
O3 . C4 . 1.4699(19) yes
C4 . C5 . 1.503(2) yes
C4 . C33 . 1.508(2) yes
C5 . C6 . 1.516(2) yes
C5 . H51 . 0.980 no
C5 . H52 . 0.994 no
C6 . C7 . 1.524(2) yes
C6 . H62 . 0.969 no
C6 . H61 . 1.011 no
C7 . C8 . 1.542(2) yes
C7 . C30 . 1.548(2) yes
C8 . O9 . 1.2110(19) yes
C8 . C10 . 1.519(2) yes
C10 . C11 . 1.551(2) yes
C10 . C17 . 1.5375(18) yes
C10 . C19 . 1.557(2) yes
C11 . C12 . 1.538(2) yes
C11 . C29 . 1.552(2) yes
C11 . H111 . 0.994 no
C12 . O13 . 1.4164(19) yes
C12 . C14 . 1.534(2) yes
C12 . H121 . 0.958 no
O13 . H131 . 0.856 no
C14 . O15 . 1.3857(18) yes
C14 . O16 . 1.4339(17) yes
C14 . C18 . 1.552(2) yes
O15 . H151 . 0.840 no
O16 . C17 . 1.4384(19) yes
C17 . H171 . 0.970 no
C17 . H172 . 0.962 no
C18 . C19 . 1.5955(19) yes
C18 . C23 . 1.538(2) yes
C18 . C26 . 1.5269(18) yes
C19 . C20 . 1.535(2) yes
C19 . H191 . 0.986 no
C20 . C21 . 1.523(3) yes
C20 . H201 . 0.971 no
C20 . H202 . 0.966 no
C21 . C22 . 1.560(2) yes
C21 . H211 . 0.994 no
C21 . H212 . 0.961 no
C22 . C23 . 1.532(2) yes
C22 . C25 . 1.503(3) yes
C22 . H221 . 0.977 no
C23 . O24 . 1.4333(19) yes
C23 . H231 . 0.958 no
O24 . H241 . 0.843 no
C25 . C26 . 1.481(2) yes
C25 . C28 . 1.329(3) yes
C26 . O27 . 1.217(2) yes
C28 . H281 . 0.957 no
C28 . H282 . 0.936 no
C29 . C30 . 1.549(2) yes
C29 . C31 . 1.524(3) yes
C29 . C32 . 1.543(2) yes
C30 . H301 . 0.957 no
C30 . H302 . 0.936 no
C31 . H312 . 0.998 no
C31 . H311 . 0.946 no
C31 . H313 . 0.972 no
C32 . H321 . 0.957 no
C32 . H323 . 0.970 no
C32 . H322 . 0.995 no
C33 . C34 . 1.536(3) yes
C33 . H331 . 0.987 no
C33 . H332 . 0.942 no
C34 . C35 . 1.554(2) yes
C34 . C54 . 1.537(2) yes
C34 . C55 . 1.529(3) yes
C35 . C36 . 1.5699(19) yes
C35 . C49 . 1.532(2) yes
C35 . H351 . 1.016 no
C36 . C37 . 1.5567(19) yes
C36 . C52 . 1.535(2) yes
C37 . C38 . 1.5941(18) yes
C37 . C47 . 1.535(2) yes
C37 . H371 . 0.970 no
C38 . C39 . 1.543(2) yes
C38 . C43 . 1.530(2) yes
C38 . C48 . 1.548(2) yes
C39 . O40 . 1.428(2) yes
C39 . C41 . 1.526(3) yes
C39 . H391 . 0.947 no
O40 . H401 . 0.817 no
C41 . C42 . 1.517(2) yes
C41 . C46 . 1.544(2) yes
C41 . H411 . 0.975 no
C42 . C43 . 1.483(2) yes
C42 . C45 . 1.326(3) yes
C43 . O44 . 1.2249(19) yes
C45 . H451 . 0.943 no
C45 . H452 . 0.940 no
C46 . C47 . 1.539(2) yes
C46 . H462 . 0.968 no
C46 . H461 . 1.016 no
C47 . H472 . 0.994 no
C47 . H471 . 0.984 no
C48 . C49 . 1.533(2) yes
C48 . O51 . 1.4369(19) yes
C48 . O53 . 1.3857(19) yes
C49 . O50 . 1.4273(19) yes
C49 . H491 . 0.960 no
O50 . H501 . 0.831 no
O51 . C52 . 1.4346(18) yes
C52 . H521 . 0.935 no
C52 . H522 . 0.966 no
O53 . H531 . 0.831 no
C54 . H541 . 0.947 no
C54 . H542 . 0.957 no
C54 . H543 . 0.976 no
C55 . H552 . 0.967 no
C55 . H553 . 0.982 no
C55 . H551 . 0.995 no
O56 . H562 . 0.869 no
O56 . H561 . 0.832 no
O57 . H571 . 0.855 no
O57 . H572 . 0.852 no
O58 . C59 . 1.422(4) yes
O58 . H581 . 0.856 no
C59 . H591 . 0.957 no
C59 . H592 . 0.968 no
C59 . H593 . 0.981 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
C2 . O1 . C7 . 117.42(10) yes
O1 . C2 . O3 . 114.78(11) yes
O1 . C2 . C4 . 121.47(12) yes
O3 . C2 . C4 . 60.53(9) yes
O1 . C2 . C36 . 112.62(11) yes
O3 . C2 . C36 . 112.54(11) yes
C4 . C2 . C36 . 122.65(12) yes
C2 . O3 . C4 . 61.23(9) yes
C2 . C4 . O3 . 58.25(9) yes
C2 . C4 . C5 . 119.55(13) yes
O3 . C4 . C5 . 113.94(13) yes
C2 . C4 . C33 . 120.45(13) yes
O3 . C4 . C33 . 114.22(13) yes
C5 . C4 . C33 . 116.22(13) yes
C4 . C5 . C6 . 112.18(12) yes
C4 . C5 . H51 . 106.9 no
C6 . C5 . H51 . 111.3 no
C4 . C5 . H52 . 108.5 no
C6 . C5 . H52 . 107.5 no
H51 . C5 . H52 . 110.5 no
C5 . C6 . C7 . 110.69(13) yes
C5 . C6 . H62 . 109.4 no
C7 . C6 . H62 . 106.7 no
C5 . C6 . H61 . 112.5 no
C7 . C6 . H61 . 108.8 no
H62 . C6 . H61 . 108.7 no
C6 . C7 . O1 . 111.18(11) yes
C6 . C7 . C8 . 109.97(12) yes
O1 . C7 . C8 . 103.16(11) yes
C6 . C7 . C30 . 112.70(13) yes
O1 . C7 . C30 . 108.93(12) yes
C8 . C7 . C30 . 110.49(12) yes
C7 . C8 . O9 . 120.87(13) yes
C7 . C8 . C10 . 118.20(12) yes
O9 . C8 . C10 . 120.88(14) yes
C8 . C10 . C11 . 110.22(12) yes
C8 . C10 . C17 . 109.10(11) yes
C11 . C10 . C17 . 111.95(12) yes
C8 . C10 . C19 . 111.03(12) yes
C11 . C10 . C19 . 107.31(11) yes
C17 . C10 . C19 . 107.20(12) yes
C10 . C11 . C12 . 108.35(12) yes
C10 . C11 . C29 . 114.35(12) yes
C12 . C11 . C29 . 116.02(12) yes
C10 . C11 . H111 . 106.8 no
C12 . C11 . H111 . 105.5 no
C29 . C11 . H111 . 105.0 no
C11 . C12 . O13 . 113.31(13) yes
C11 . C12 . C14 . 108.47(12) yes
O13 . C12 . C14 . 112.85(13) yes
C11 . C12 . H121 . 108.0 no
O13 . C12 . H121 . 106.9 no
C14 . C12 . H121 . 106.9 no
C12 . O13 . H131 . 100.2 no
C12 . C14 . O15 . 107.95(13) yes
C12 . C14 . O16 . 106.87(12) yes
O15 . C14 . O16 . 107.01(11) yes
C12 . C14 . C18 . 115.69(12) yes
O15 . C14 . C18 . 113.24(12) yes
O16 . C14 . C18 . 105.54(11) yes
C14 . O15 . H151 . 104.8 no
C14 . O16 . C17 . 113.55(10) yes
C10 . C17 . O16 . 110.30(11) yes
C10 . C17 . H171 . 109.7 no
O16 . C17 . H171 . 106.7 no
C10 . C17 . H172 . 109.0 no
O16 . C17 . H172 . 109.4 no
H171 . C17 . H172 . 111.8 no
C14 . C18 . C19 . 109.43(11) yes
C14 . C18 . C23 . 113.11(12) yes
C19 . C18 . C23 . 110.23(12) yes
C14 . C18 . C26 . 119.68(12) yes
C19 . C18 . C26 . 102.88(11) yes
C23 . C18 . C26 . 100.74(12) yes
C10 . C19 . C18 . 106.28(11) yes
C10 . C19 . C20 . 116.78(12) yes
C18 . C19 . C20 . 111.70(12) yes
C10 . C19 . H191 . 106.6 no
C18 . C19 . H191 . 107.4 no
C20 . C19 . H191 . 107.6 no
C19 . C20 . C21 . 113.32(14) yes
C19 . C20 . H201 . 108.8 no
C21 . C20 . H201 . 110.5 no
C19 . C20 . H202 . 107.1 no
C21 . C20 . H202 . 109.0 no
H201 . C20 . H202 . 108.0 no
C20 . C21 . C22 . 112.99(14) yes
C20 . C21 . H211 . 110.5 no
C22 . C21 . H211 . 109.3 no
C20 . C21 . H212 . 107.3 no
C22 . C21 . H212 . 107.7 no
H211 . C21 . H212 . 108.8 no
C21 . C22 . C23 . 107.87(14) yes
C21 . C22 . C25 . 113.25(14) yes
C23 . C22 . C25 . 101.34(14) yes
C21 . C22 . H221 . 110.3 no
C23 . C22 . H221 . 110.0 no
C25 . C22 . H221 . 113.6 no
C18 . C23 . C22 . 101.84(12) yes
C18 . C23 . O24 . 107.15(13) yes
C22 . C23 . O24 . 110.79(14) yes
C18 . C23 . H231 . 110.1 no
C22 . C23 . H231 . 114.1 no
O24 . C23 . H231 . 112.2 no
C23 . O24 . H241 . 98.9 no
C22 . C25 . C26 . 108.06(13) yes
C22 . C25 . C28 . 129.6(2) yes
C26 . C25 . C28 . 122.2(2) yes
C18 . C26 . C25 . 106.59(13) yes
C18 . C26 . O27 . 127.14(15) yes
C25 . C26 . O27 . 126.14(14) yes
C25 . C28 . H281 . 120.7 no
C25 . C28 . H282 . 118.0 no
H281 . C28 . H282 . 121.3 no
C11 . C29 . C30 . 108.52(12) yes
C11 . C29 . C31 . 109.81(13) yes
C30 . C29 . C31 . 108.14(14) yes
C11 . C29 . C32 . 113.66(14) yes
C30 . C29 . C32 . 107.82(13) yes
C31 . C29 . C32 . 108.73(16) yes
C7 . C30 . C29 . 116.92(13) yes
C7 . C30 . H301 . 107.5 no
C29 . C30 . H301 . 107.0 no
C7 . C30 . H302 . 107.3 no
C29 . C30 . H302 . 109.1 no
H301 . C30 . H302 . 108.8 no
C29 . C31 . H312 . 108.8 no
C29 . C31 . H311 . 111.2 no
H312 . C31 . H311 . 106.6 no
C29 . C31 . H313 . 111.0 no
H312 . C31 . H313 . 107.6 no
H311 . C31 . H313 . 111.4 no
C29 . C32 . H321 . 108.8 no
C29 . C32 . H323 . 111.7 no
H321 . C32 . H323 . 106.6 no
C29 . C32 . H322 . 112.5 no
H321 . C32 . H322 . 109.1 no
H323 . C32 . H322 . 107.9 no
C4 . C33 . C34 . 113.78(13) yes
C4 . C33 . H331 . 108.0 no
C34 . C33 . H331 . 109.0 no
C4 . C33 . H332 . 109.6 no
C34 . C33 . H332 . 108.6 no
H331 . C33 . H332 . 107.8 no
C33 . C34 . C35 . 107.16(13) yes
C33 . C34 . C54 . 107.49(14) yes
C35 . C34 . C54 . 109.87(13) yes
C33 . C34 . C55 . 109.37(15) yes
C35 . C34 . C55 . 114.54(14) yes
C54 . C34 . C55 . 108.19(15) yes
C34 . C35 . C36 . 116.85(12) yes
C34 . C35 . C49 . 114.57(13) yes
C36 . C35 . C49 . 108.00(12) yes
C34 . C35 . H351 . 106.9 no
C36 . C35 . H351 . 104.5 no
C49 . C35 . H351 . 104.9 no
C2 . C36 . C35 . 111.06(11) yes
C2 . C36 . C37 . 110.36(12) yes
C35 . C36 . C37 . 105.27(11) yes
C2 . C36 . C52 . 111.86(11) yes
C35 . C36 . C52 . 110.03(12) yes
C37 . C36 . C52 . 108.01(11) yes
C36 . C37 . C38 . 108.01(11) yes
C36 . C37 . C47 . 116.25(11) yes
C38 . C37 . C47 . 111.44(11) yes
C36 . C37 . H371 . 105.5 no
C38 . C37 . H371 . 109.8 no
C47 . C37 . H371 . 105.6 no
C37 . C38 . C39 . 109.73(12) yes
C37 . C38 . C43 . 104.44(12) yes
C39 . C38 . C43 . 98.91(12) yes
C37 . C38 . C48 . 108.80(12) yes
C39 . C38 . C48 . 114.08(13) yes
C43 . C38 . C48 . 120.07(12) yes
C38 . C39 . O40 . 105.80(13) yes
C38 . C39 . C41 . 101.66(13) yes
O40 . C39 . C41 . 112.19(15) yes
C38 . C39 . H391 . 115.3 no
O40 . C39 . H391 . 109.0 no
C41 . C39 . H391 . 112.6 no
C39 . O40 . H401 . 110.5 no
C39 . C41 . C42 . 101.89(14) yes
C39 . C41 . C46 . 109.34(14) yes
C42 . C41 . C46 . 112.80(15) yes
C39 . C41 . H411 . 112.1 no
C42 . C41 . H411 . 111.1 no
C46 . C41 . H411 . 109.5 no
C41 . C42 . C43 . 107.23(14) yes
C41 . C42 . C45 . 128.52(17) yes
C43 . C42 . C45 . 124.24(16) yes
C38 . C43 . C42 . 106.55(13) yes
C38 . C43 . O44 . 127.92(15) yes
C42 . C43 . O44 . 125.47(15) yes
C42 . C45 . H451 . 121.0 no
C42 . C45 . H452 . 121.6 no
H451 . C45 . H452 . 117.4 no
C41 . C46 . C47 . 111.12(14) yes
C41 . C46 . H462 . 110.1 no
C47 . C46 . H462 . 112.6 no
C41 . C46 . H461 . 110.1 no
C47 . C46 . H461 . 109.0 no
H462 . C46 . H461 . 103.7 no
C46 . C47 . C37 . 111.81(12) yes
C46 . C47 . H472 . 109.1 no
C37 . C47 . H472 . 108.3 no
C46 . C47 . H471 . 108.1 no
C37 . C47 . H471 . 110.8 no
H472 . C47 . H471 . 108.6 no
C38 . C48 . C49 . 114.34(13) yes
C38 . C48 . O51 . 105.82(12) yes
C49 . C48 . O51 . 106.68(13) yes
C38 . C48 . O53 . 113.65(13) yes
C49 . C48 . O53 . 109.09(13) yes
O51 . C48 . O53 . 106.68(13) yes
C48 . C49 . C35 . 109.02(12) yes
C48 . C49 . O50 . 113.12(13) yes
C35 . C49 . O50 . 112.87(14) yes
C48 . C49 . H491 . 103.5 no
C35 . C49 . H491 . 110.4 no
O50 . C49 . H491 . 107.5 no
C49 . O50 . H501 . 104.8 no
C48 . O51 . C52 . 113.78(11) yes
C36 . C52 . O51 . 110.80(12) yes
C36 . C52 . H521 . 110.4 no
O51 . C52 . H521 . 109.3 no
C36 . C52 . H522 . 109.4 no
O51 . C52 . H522 . 106.8 no
H521 . C52 . H522 . 110.1 no
C48 . O53 . H531 . 98.9 no
C34 . C54 . H541 . 106.9 no
C34 . C54 . H542 . 112.2 no
H541 . C54 . H542 . 108.1 no
C34 . C54 . H543 . 109.5 no
H541 . C54 . H543 . 111.5 no
H542 . C54 . H543 . 108.6 no
C34 . C55 . H552 . 110.1 no
C34 . C55 . H553 . 115.0 no
H552 . C55 . H553 . 107.8 no
C34 . C55 . H551 . 111.8 no
H552 . C55 . H551 . 103.4 no
H553 . C55 . H551 . 108.0 no
H562 . O56 . H561 . 89.6 no
H571 . O57 . H572 . 107.1 no
C59 . O58 . H581 . 103.2 no
O58 . C59 . H591 . 107.6 no
O58 . C59 . H592 . 107.2 no
H591 . C59 . H592 . 107.7 no
O58 . C59 . H593 . 110.7 no
H591 . C59 . H593 . 110.6 no
H592 . C59 . H593 . 112.8 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
C17 . H171 . C32 . 125.79(5) 0.970 2.575 3.240(2) yes
C28 . H282 . O27 2_544 126.02(7) 0.936 2.580 3.221(2) yes
C41 . H411 . O27 2_544 148.34(4) 0.975 2.585 3.453(2) yes
O56 . H562 . O58 . 163.29(9) 0.869 2.051 2.895(2) yes
O56 . H561 . O9 . 156.68(6) 0.832 2.100 2.883(2) yes
O56 . H561 . O53 4_345 121.24(5) 0.832 2.451 2.969(2) yes
O53 . H531 . C39 . 129.14(5) 0.831 2.381 2.976(2) yes
O53 . H531 . O40 . 162.44(6) 0.831 1.782 2.586(2) yes
O40 . H401 . O13 2_544 147.57(5) 0.817 2.346 3.066(2) yes
O40 . H401 . O15 2_544 137.61(5) 0.817 2.145 2.803(2) yes
O13 . H131 . C26 . 145.97(4) 0.856 2.551 3.296(2) yes
O13 . H131 . O27 . 172.60(5) 0.856 1.888 2.739(2) yes
O57 . H571 . O50 . 156.28(9) 0.855 2.096 2.899(2) yes
O57 . H572 . O56 4_344 169.49(8) 0.852 2.261 3.103(2) yes
O15 . H151 . C23 . 120.06(5) 0.840 2.468 2.979(2) yes
O15 . H151 . O24 . 151.24(5) 0.840 1.807 2.575(2) yes
O50 . H501 . O44 . 166.73(5) 0.831 1.916 2.732(2) yes
O24 . H241 . O56 3_454 165.28(8) 0.843 1.815 2.639(2) yes
O58 . H581 . O3 . 172.46(7) 0.856 2.000 2.851(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 22/08/13 at 11:08:10
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE O   (  13,X'S) H   ( 131,X'S) 
RIDE O   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE O   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 312,X'S) H   ( 311,X'S) H   ( 313,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 323,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE O   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) H   ( 452,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 472,X'S) H   ( 471,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE O   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE O   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) H   ( 543,X'S) 
RIDE C   (  55,X'S) H   ( 552,X'S) H   ( 553,X'S) H   ( 551,X'S) 
RIDE O   (  56,X'S) H   ( 562,X'S) H   ( 561,X'S) 
RIDE O   (  57,X'S) H   ( 571,X'S) H   ( 572,X'S) 
RIDE O   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) H   ( 592,X'S) H   ( 593,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 22/08/13 at 11:08:10
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 0 2 x .
0 5 2 x .
0 5 3 x .
0 4 1 x .
0 4 6 x .
0 0 6 x .
3 1 0 x .
0 1 5 x .
0 0 8 x .
-1 1 4 x .
1 1 4 x .
1 0 5 x .
2 2 4 x .
2 2 4 x .
0 1 9 x .
4 1 1 x .
-4 1 1 x .
0 4 4 x .
1 4 0 x .
3 2 3 x .
-3 2 3 x .
-2 2 4 x .
5 3 0 x .
3 2 1 x .
-3 2 1 x .
2 2 0 x .
0 5 1 x .
3 1 2 x .
-3 1 2 x .
4 0 0 x .
0 1 11 x .
-1 1 9 x .
-1 2 8 x .
3 0 4 x .
0 2 10 x .
2 1 2 x .
0 3 3 x .
-2 1 2 x .
0 1 10 x .
0 3 3 x .
0 3 3 x .
0 4 0 x .
0 1 8 x .
_database_code_depnum_ccdc_archive 'CCDC 1004083'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_exptl_special_details           
; 
 The crystal was placed in the cold stream of an Cryo-Industries of America open-flow nitrogen cryostat with a nominal stability of 0.1K. 
;
_refine_special_details          
; 
Disordered solvent molecules, located in a difference fourier map, were modeled as waters with occupancies of 0.5.
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   9.4979(8)
_cell_length_b                   13.0601(10)
_cell_length_c                   21.0823(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2615.1(4)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

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 0.0181 0.0091 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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 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'


_cell_formula_units_Z            4

# Given Formula = C28 H37 Cl1 O7 
# Dc =      1.32 Fooo =   1112.00 Mu =     16.69 M =    521.05
# Found Formula = C28 H37 Cl1 O7 
# Dc =      1.32 FOOO =   1112.00 Mu =     16.69 M =    521.05

_chemical_formula_sum            'C28 H37 Cl1 O7'
_chemical_formula_moiety         'C28 H37 Cl1 O7'
_chemical_compound_source        'Chemical Synthesis'
_chemical_formula_weight         521.05


_cell_measurement_reflns_used    996
_cell_measurement_theta_min      4
_cell_measurement_theta_max      71
_cell_measurement_temperature    263

_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    1.669

# Sheldrick geometric approximatio 0.85 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.92
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      263
_diffrn_reflns_number            21934
_reflns_number_total             4926
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 4926 
# Number of reflections with Friedels Law is 2866 
# Theoretical number of reflections is about 2550 


_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         71.521
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        69.375
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   4.04
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.43
_refine_diff_density_max         0.30


# 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>-3.0\s(I)
_refine_ls_number_reflns         4903
_refine_ls_number_restraints     0
_refine_ls_number_parameters     327
_oxford_refine_ls_R_factor_ref   0.0450
_refine_ls_wR_factor_ref         0.1271
_refine_ls_goodness_of_fit_ref   0.9531
_refine_ls_shift/su_max          0.0003854
_refine_ls_shift/su_mean         0.0000338


# The values computed from all data 
_oxford_reflns_number_all        4903
_refine_ls_R_factor_all          0.0450
_refine_ls_wR_factor_all         0.1271

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4529
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_gt          0.1245

_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_abs_structure_details 'Flack (1983), 2060 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.43P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
Cl1 Cl 1.14365(15) 0.19328(10) 0.55636(6) 0.1368 1.0000 Uani . . . . . .
O2 O 0.33528(15) 0.34226(9) 0.69555(6) 0.0462 1.0000 Uani . . . . . .
O3 O 0.16119(14) 0.40140(11) 0.76091(7) 0.0509 1.0000 Uani . . . . . .
O4 O 0.73410(15) 0.42798(12) 0.63013(7) 0.0543 1.0000 Uani . . . . . .
O5 O 0.28975(15) 0.37598(12) 0.85532(7) 0.0530 1.0000 Uani . . . . . .
O6 O 0.14525(17) 0.58509(13) 0.69481(8) 0.0638 1.0000 Uani . . . . . .
C7 C 0.39667(19) 0.47035(14) 0.77124(8) 0.0402 1.0000 Uani . . . . . .
O8 O 0.3040(2) 0.64122(13) 0.79811(8) 0.0677 1.0000 Uani . . . . . .
O9 O 0.95346(18) 0.36925(13) 0.60526(10) 0.0682 1.0000 Uani . . . . . .
C10 C 0.4521(2) 0.36323(14) 0.65428(9) 0.0440 1.0000 Uani . . . . . .
C11 C 0.28015(18) 0.43134(14) 0.72691(9) 0.0420 1.0000 Uani . . . . . .
C12 C 0.4210(2) 0.39042(15) 0.82345(9) 0.0457 1.0000 Uani . . . . . .
C13 C 0.49988(19) 0.47531(14) 0.66077(8) 0.0404 1.0000 Uani . . . . . .
C14 C 0.53513(19) 0.49390(14) 0.73258(9) 0.0403 1.0000 Uani . . . . . .
C15 C 0.2371(2) 0.50721(16) 0.67459(9) 0.0463 1.0000 Uani . . . . . .
C16 C 0.3753(2) 0.54920(13) 0.64539(9) 0.0421 1.0000 Uani . . . . . .
C17 C 0.6245(2) 0.49494(15) 0.61794(9) 0.0452 1.0000 Uani . . . . . .
C18 C 0.4521(2) 0.55064(17) 0.87192(10) 0.0530 1.0000 Uani . . . . . .
C19 C 0.3706(2) 0.56540(16) 0.81193(9) 0.0483 1.0000 Uani . . . . . .
C20 C 0.6672(2) 0.4518(2) 0.83488(10) 0.0604 1.0000 Uani . . . . . .
C21 C 0.1793(2) 0.33824(17) 0.81656(10) 0.0533 1.0000 Uani . . . . . .
C22 C 0.6607(2) 0.43649(19) 0.76219(9) 0.0536 1.0000 Uani . . . . . .
C23 C 0.3633(2) 0.58332(17) 0.57499(10) 0.0536 1.0000 Uani . . . . . .
C24 C 0.6299(2) 0.56667(17) 0.57301(9) 0.0522 1.0000 Uani . . . . . .
C25 C 0.5212(2) 0.44672(18) 0.86758(10) 0.0528 1.0000 Uani . . . . . .
C26 C 0.8408(2) 0.42292(18) 0.58151(11) 0.0577 1.0000 Uani . . . . . .
C27 C 0.2477(3) 0.6651(2) 0.56842(14) 0.0721 1.0000 Uani . . . . . .
C28 C 0.3319(3) 0.4956(2) 0.52902(11) 0.0692 1.0000 Uani . . . . . .
C29 C 0.2016(3) 0.22549(18) 0.79872(13) 0.0632 1.0000 Uani . . . . . .
C30 C 0.8869(2) 0.52790(18) 0.56324(11) 0.0583 1.0000 Uani . . . . . .
C31 C 0.7636(3) 0.5859(2) 0.53592(11) 0.0665 1.0000 Uani . . . . . .
C32 C 0.5054(2) 0.63221(19) 0.55792(12) 0.0606 1.0000 Uani . . . . . .
C33 C 0.4539(3) 0.6208(2) 0.91718(11) 0.0689 1.0000 Uani . . . . . .
C34 C 0.0455(3) 0.3527(3) 0.85427(13) 0.0739 1.0000 Uani . . . . . .
C35 C 1.0548(4) 0.2100(2) 0.62927(17) 0.0825 1.0000 Uani . . . . . .
C36 C 0.9252(3) 0.2671(2) 0.6227(2) 0.1029 1.0000 Uani . . . . . .
H101 H 0.5245 0.3161 0.6640 0.0528 1.0000 Uiso R . . . . .
H102 H 0.4250 0.3458 0.6121 0.0544 1.0000 Uiso R . . . . .
H121 H 0.4614 0.3243 0.8078 0.0526 1.0000 Uiso R . . . . .
H141 H 0.5529 0.5665 0.7364 0.0465 1.0000 Uiso R . . . . .
H151 H 0.1864 0.4661 0.6451 0.0540 1.0000 Uiso R . . . . .
H161 H 0.3993 0.6109 0.6677 0.0492 1.0000 Uiso R . . . . .
H201 H 0.7103 0.5175 0.8424 0.0723 1.0000 Uiso R . . . . .
H202 H 0.7258 0.3996 0.8524 0.0719 1.0000 Uiso R . . . . .
H221 H 0.7522 0.4592 0.7441 0.0637 1.0000 Uiso R . . . . .
H222 H 0.6560 0.3620 0.7517 0.0613 1.0000 Uiso R . . . . .
H251 H 0.5219 0.4154 0.9098 0.0624 1.0000 Uiso R . . . . .
H261 H 0.8042 0.3859 0.5441 0.0680 1.0000 Uiso R . . . . .
H271 H 0.2440 0.6909 0.5255 0.1049 1.0000 Uiso R . . . . .
H272 H 0.2624 0.7229 0.5961 0.1049 1.0000 Uiso R . . . . .
H273 H 0.1564 0.6404 0.5802 0.1048 1.0000 Uiso R . . . . .
H281 H 0.3142 0.5214 0.4888 0.1025 1.0000 Uiso R . . . . .
H282 H 0.4112 0.4522 0.5255 0.1023 1.0000 Uiso R . . . . .
H283 H 0.2543 0.4533 0.5414 0.1019 1.0000 Uiso R . . . . .
H291 H 0.2103 0.1830 0.8360 0.0921 1.0000 Uiso R . . . . .
H292 H 0.2784 0.2146 0.7696 0.0924 1.0000 Uiso R . . . . .
H293 H 0.1222 0.2013 0.7753 0.0928 1.0000 Uiso R . . . . .
H301 H 0.9132 0.5631 0.6028 0.0677 1.0000 Uiso R . . . . .
H302 H 0.9680 0.5249 0.5345 0.0680 1.0000 Uiso R . . . . .
H311 H 0.7885 0.6592 0.5346 0.0776 1.0000 Uiso R . . . . .
H312 H 0.7501 0.5589 0.4928 0.0775 1.0000 Uiso R . . . . .
H321 H 0.5113 0.7003 0.5789 0.0723 1.0000 Uiso R . . . . .
H322 H 0.5061 0.6476 0.5125 0.0725 1.0000 Uiso R . . . . .
H331 H 0.4995 0.6073 0.9543 0.0827 1.0000 Uiso R . . . . .
H332 H 0.4065 0.6819 0.9095 0.0806 1.0000 Uiso R . . . . .
H341 H 0.0513 0.3109 0.8927 0.1095 1.0000 Uiso R . . . . .
H342 H 0.0448 0.4232 0.8666 0.1094 1.0000 Uiso R . . . . .
H343 H -0.0337 0.3344 0.8282 0.1101 1.0000 Uiso R . . . . .
H351 H 1.1177 0.2481 0.6582 0.0986 1.0000 Uiso R . . . . .
H352 H 1.0380 0.1404 0.6452 0.0982 1.0000 Uiso R . . . . .
H361 H 0.8711 0.2679 0.6624 0.1210 1.0000 Uiso R . . . . .
H362 H 0.8690 0.2342 0.5893 0.1220 1.0000 Uiso R . . . . .
H61 H 0.1811 0.6147 0.7272 0.0964 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       20(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.5337(14)
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
Cl1 . C35 . 1.767(3) yes
O2 . C10 . 1.436(2) yes
O2 . C11 . 1.437(2) yes
O3 . C11 . 1.394(2) yes
O3 . C21 . 1.444(2) yes
O4 . C17 . 1.383(2) yes
O4 . C26 . 1.443(2) yes
O5 . C12 . 1.429(2) yes
O5 . C21 . 1.418(3) yes
O6 . C15 . 1.406(3) yes
O6 . H61 . 0.855 no
C7 . C11 . 1.535(3) yes
C7 . C12 . 1.534(2) yes
C7 . C14 . 1.577(2) yes
C7 . C19 . 1.529(3) yes
O8 . C19 . 1.210(3) yes
O9 . C26 . 1.374(3) yes
O9 . C36 . 1.410(3) yes
C10 . C13 . 1.539(2) yes
C10 . H101 . 0.945 no
C10 . H102 . 0.953 no
C11 . C15 . 1.538(3) yes
C12 . C25 . 1.520(3) yes
C12 . H121 . 1.001 no
C13 . C14 . 1.569(3) yes
C13 . C16 . 1.561(2) yes
C13 . C17 . 1.511(3) yes
C14 . C22 . 1.541(3) yes
C14 . H141 . 0.966 no
C15 . C16 . 1.550(3) yes
C15 . H151 . 0.953 no
C16 . C23 . 1.554(3) yes
C16 . H161 . 0.960 no
C17 . C24 . 1.333(3) yes
C18 . C19 . 1.496(3) yes
C18 . C25 . 1.510(3) yes
C18 . C33 . 1.323(3) yes
C20 . C22 . 1.547(3) yes
C20 . C25 . 1.550(3) yes
C20 . H201 . 0.965 no
C20 . H202 . 0.953 no
C21 . C29 . 1.534(3) yes
C21 . C34 . 1.511(3) yes
C22 . H221 . 0.994 no
C22 . H222 . 0.999 no
C23 . C27 . 1.538(3) yes
C23 . C28 . 1.530(3) yes
C23 . C32 . 1.536(3) yes
C24 . C31 . 1.512(3) yes
C24 . C32 . 1.494(3) yes
C25 . H251 . 0.980 no
C26 . C30 . 1.490(3) yes
C26 . H261 . 0.989 no
C27 . H271 . 0.966 no
C27 . H272 . 0.965 no
C27 . H273 . 0.958 no
C28 . H281 . 0.928 no
C28 . H282 . 0.946 no
C28 . H283 . 0.957 no
C29 . H291 . 0.965 no
C29 . H292 . 0.964 no
C29 . H293 . 0.955 no
C30 . C31 . 1.509(4) yes
C30 . H301 . 0.985 no
C30 . H302 . 0.980 no
C31 . H311 . 0.987 no
C31 . H312 . 0.983 no
C32 . H321 . 0.995 no
C32 . H322 . 0.979 no
C33 . H331 . 0.911 no
C33 . H332 . 0.930 no
C34 . H341 . 0.978 no
C34 . H342 . 0.955 no
C34 . H343 . 0.961 no
C35 . C36 . 1.445(5) yes
C35 . H351 . 0.989 no
C35 . H352 . 0.982 no
C36 . H361 . 0.982 no
C36 . H362 . 0.983 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
C10 . O2 . C11 . 113.94(13) yes
C11 . O3 . C21 . 118.77(15) yes
C17 . O4 . C26 . 115.18(16) yes
C12 . O5 . C21 . 114.85(15) yes
C15 . O6 . H61 . 108.7 no
C11 . C7 . C12 . 108.63(15) yes
C11 . C7 . C14 . 110.56(14) yes
C12 . C7 . C14 . 112.19(15) yes
C11 . C7 . C19 . 119.59(15) yes
C12 . C7 . C19 . 100.04(15) yes
C14 . C7 . C19 . 105.47(15) yes
C26 . O9 . C36 . 115.5(2) yes
O2 . C10 . C13 . 110.81(15) yes
O2 . C10 . H101 . 107.9 no
C13 . C10 . H101 . 112.7 no
O2 . C10 . H102 . 108.1 no
C13 . C10 . H102 . 112.9 no
H101 . C10 . H102 . 104.0 no
C7 . C11 . O2 . 106.61(14) yes
C7 . C11 . O3 . 111.37(15) yes
O2 . C11 . O3 . 107.74(15) yes
C7 . C11 . C15 . 114.47(15) yes
O2 . C11 . C15 . 106.77(15) yes
O3 . C11 . C15 . 109.52(14) yes
C7 . C12 . O5 . 107.20(15) yes
C7 . C12 . C25 . 101.79(16) yes
O5 . C12 . C25 . 108.79(16) yes
C7 . C12 . H121 . 114.1 no
O5 . C12 . H121 . 112.1 no
C25 . C12 . H121 . 112.3 no
C10 . C13 . C14 . 107.21(15) yes
C10 . C13 . C16 . 110.25(15) yes
C14 . C13 . C16 . 105.46(14) yes
C10 . C13 . C17 . 109.84(15) yes
C14 . C13 . C17 . 112.53(15) yes
C16 . C13 . C17 . 111.41(15) yes
C13 . C14 . C7 . 106.88(14) yes
C13 . C14 . C22 . 118.73(16) yes
C7 . C14 . C22 . 109.94(15) yes
C13 . C14 . H141 . 105.6 no
C7 . C14 . H141 . 107.1 no
C22 . C14 . H141 . 108.0 no
C11 . C15 . O6 . 114.42(17) yes
C11 . C15 . C16 . 106.74(14) yes
O6 . C15 . C16 . 112.95(16) yes
C11 . C15 . H151 . 103.9 no
O6 . C15 . H151 . 106.9 no
C16 . C15 . H151 . 111.6 no
C15 . C16 . C13 . 109.91(14) yes
C15 . C16 . C23 . 114.76(16) yes
C13 . C16 . C23 . 115.55(16) yes
C15 . C16 . H161 . 107.6 no
C13 . C16 . H161 . 103.7 no
C23 . C16 . H161 . 104.2 no
C13 . C17 . O4 . 111.79(15) yes
C13 . C17 . C24 . 125.04(19) yes
O4 . C17 . C24 . 123.17(18) yes
C19 . C18 . C25 . 106.83(17) yes
C19 . C18 . C33 . 121.8(2) yes
C25 . C18 . C33 . 131.4(2) yes
C7 . C19 . C18 . 106.61(16) yes
C7 . C19 . O8 . 127.87(19) yes
C18 . C19 . O8 . 125.41(19) yes
C22 . C20 . C25 . 113.55(18) yes
C22 . C20 . H201 . 107.2 no
C25 . C20 . H201 . 110.1 no
C22 . C20 . H202 . 108.3 no
C25 . C20 . H202 . 108.6 no
H201 . C20 . H202 . 108.9 no
O3 . C21 . O5 . 110.96(16) yes
O3 . C21 . C29 . 111.43(19) yes
O5 . C21 . C29 . 111.88(19) yes
O3 . C21 . C34 . 104.80(19) yes
O5 . C21 . C34 . 105.99(18) yes
C29 . C21 . C34 . 111.4(2) yes
C14 . C22 . C20 . 111.69(18) yes
C14 . C22 . H221 . 112.1 no
C20 . C22 . H221 . 107.8 no
C14 . C22 . H222 . 110.5 no
C20 . C22 . H222 . 110.3 no
H221 . C22 . H222 . 104.1 no
C16 . C23 . C27 . 109.72(19) yes
C16 . C23 . C28 . 113.86(17) yes
C27 . C23 . C28 . 108.9(2) yes
C16 . C23 . C32 . 106.18(17) yes
C27 . C23 . C32 . 108.52(18) yes
C28 . C23 . C32 . 109.5(2) yes
C17 . C24 . C31 . 121.1(2) yes
C17 . C24 . C32 . 121.55(19) yes
C31 . C24 . C32 . 117.35(19) yes
C20 . C25 . C12 . 107.96(17) yes
C20 . C25 . C18 . 112.17(19) yes
C12 . C25 . C18 . 101.53(17) yes
C20 . C25 . H251 . 114.6 no
C12 . C25 . H251 . 111.0 no
C18 . C25 . H251 . 108.9 no
O4 . C26 . O9 . 108.15(18) yes
O4 . C26 . C30 . 110.35(18) yes
O9 . C26 . C30 . 109.57(19) yes
O4 . C26 . H261 . 110.0 no
O9 . C26 . H261 . 108.4 no
C30 . C26 . H261 . 110.3 no
C23 . C27 . H271 . 110.7 no
C23 . C27 . H272 . 112.7 no
H271 . C27 . H272 . 107.4 no
C23 . C27 . H273 . 112.9 no
H271 . C27 . H273 . 109.0 no
H272 . C27 . H273 . 103.8 no
C23 . C28 . H281 . 110.0 no
C23 . C28 . H282 . 110.1 no
H281 . C28 . H282 . 106.8 no
C23 . C28 . H283 . 114.2 no
H281 . C28 . H283 . 108.6 no
H282 . C28 . H283 . 106.8 no
C21 . C29 . H291 . 111.3 no
C21 . C29 . H292 . 113.7 no
H291 . C29 . H292 . 111.6 no
C21 . C29 . H293 . 109.6 no
H291 . C29 . H293 . 107.3 no
H292 . C29 . H293 . 102.7 no
C26 . C30 . C31 . 109.4(2) yes
C26 . C30 . H301 . 106.6 no
C31 . C30 . H301 . 106.6 no
C26 . C30 . H302 . 110.7 no
C31 . C30 . H302 . 113.2 no
H301 . C30 . H302 . 110.0 no
C24 . C31 . C30 . 111.79(18) yes
C24 . C31 . H311 . 112.1 no
C30 . C31 . H311 . 108.2 no
C24 . C31 . H312 . 108.0 no
C30 . C31 . H312 . 105.9 no
H311 . C31 . H312 . 110.6 no
C23 . C32 . C24 . 114.04(17) yes
C23 . C32 . H321 . 108.4 no
C24 . C32 . H321 . 111.9 no
C23 . C32 . H322 . 108.7 no
C24 . C32 . H322 . 108.7 no
H321 . C32 . H322 . 104.6 no
C18 . C33 . H331 . 119.4 no
C18 . C33 . H332 . 117.6 no
H331 . C33 . H332 . 123.0 no
C21 . C34 . H341 . 108.5 no
C21 . C34 . H342 . 105.6 no
H341 . C34 . H342 . 108.2 no
C21 . C34 . H343 . 109.0 no
H341 . C34 . H343 . 112.2 no
H342 . C34 . H343 . 113.0 no
Cl1 . C35 . C36 . 112.8(3) yes
Cl1 . C35 . H351 . 108.1 no
C36 . C35 . H351 . 108.3 no
Cl1 . C35 . H352 . 105.2 no
C36 . C35 . H352 . 111.8 no
H351 . C35 . H352 . 110.6 no
C35 . C36 . O9 . 110.6(2) yes
C35 . C36 . H361 . 111.7 no
O9 . C36 . H361 . 108.1 no
C35 . C36 . H362 . 107.8 no
O9 . C36 . H362 . 109.2 no
H361 . C36 . H362 . 109.3 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
C35 . H351 . O2 1_655 158.50(8) 0.989 2.530 3.469(3) yes
C36 . H361 . O8 3_646 128.88(11) 0.982 2.489 3.199(3) yes
O6 . H61 . O8 . 160.28(6) 0.855 1.929 2.749(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 05/07/13 at 17:38:40
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE O   (   6,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) H   ( 273,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) H   ( 343,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 05/07/13 at 17:38:40
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1004084'
