# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_zjun1
_database_code_depnum_ccdc_archive 'CCDC 1057054'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_audit_creation_date             2014-01-10
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        'gliomasolide B'
_chemical_formula_moiety         'C24 H42 O10'
_chemical_formula_sum            'C24 H42 O10'
_chemical_formula_weight         490.58
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

_space_group_IT_number           5

_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'

_cell_length_a                   24.385(5)
_cell_length_b                   5.3330(11)
_cell_length_c                   19.745(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.23(3)
_cell_angle_gamma                90.00
_cell_volume                     2565.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5244
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9390
_cell_measurement_theta_min      4.4750
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7032
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         4.48
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.9730
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -115.00  -12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -75.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   77.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega   81.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega  118.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega   83.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   28.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   32.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 12 omega   33.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
 13 omega   58.00  130.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000    0.0000 72
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0553083000
_diffrn_orient_matrix_UB_12      0.0485151000
_diffrn_orient_matrix_UB_13      0.0415438000
_diffrn_orient_matrix_UB_21      0.0449669000
_diffrn_orient_matrix_UB_22      -0.1218927000
_diffrn_orient_matrix_UB_23      0.0456178000
_diffrn_orient_matrix_UB_31      0.0318269000
_diffrn_orient_matrix_UB_32      0.2574463000
_diffrn_orient_matrix_UB_33      0.0137898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3273
_reflns_number_total             3391
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+1.4844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11870(11) 0.5056(4) 0.63191(10) 0.0566(6) Uani 1 1 d . . .
O2 O 0.13100(10) 0.9149(4) 0.65246(10) 0.0537(5) Uani 1 1 d . . .
O4 O 0.11305(5) 0.1208(3) 0.85707(8) 0.0311(4) Uani 1 1 d . . .
H4 H 0.0794 0.1548 0.8543 0.047 Uiso 1 1 calc R . .
O5 O 0.21208(6) 0.2444(4) 0.92480(8) 0.0374(4) Uani 1 1 d . . .
H5 H 0.2450 0.2079 0.9345 0.056 Uiso 1 1 calc R . .
O21 O 0.31802(5) 0.1617(3) 0.85544(7) 0.0232(3) Uani 1 1 d . . .
O22 O 0.30779(6) 0.1174(4) 0.99185(7) 0.0341(4) Uani 1 1 d . . .
H22 H 0.2985 0.0050 1.0189 0.051 Uiso 1 1 calc R . .
O23 O 0.41349(7) 0.3192(4) 1.03388(10) 0.0438(5) Uani 1 1 d . . .
H23 H 0.3892 0.4047 1.0521 0.066 Uiso 1 1 calc R . .
O24 O 0.48147(7) 0.4194(4) 0.92272(12) 0.0532(6) Uani 1 1 d . . .
H24 H 0.5133 0.3866 0.9379 0.080 Uiso 1 1 calc R . .
O25 O 0.39548(6) -0.0951(3) 0.85746(8) 0.0304(4) Uani 1 1 d . . .
O26 O 0.51062(6) -0.1792(4) 0.85585(12) 0.0511(5) Uani 1 1 d . . .
H26 H 0.4876 -0.2828 0.8696 0.077 Uiso 1 1 calc R . .
C1 C 0.12400(10) 0.7047(5) 0.67205(13) 0.0377(6) Uani 1 1 d . . .
C2 C 0.12336(8) 0.6372(5) 0.74495(12) 0.0312(5) Uani 1 1 d . . .
H2 H 0.1154 0.7631 0.7772 0.037 Uiso 1 1 calc R . .
C3 C 0.13363(8) 0.4051(5) 0.76624(11) 0.0281(5) Uani 1 1 d . . .
H3 H 0.1345 0.2751 0.7334 0.034 Uiso 1 1 calc R . .
C4 C 0.14393(8) 0.3370(5) 0.83967(11) 0.0281(5) Uani 1 1 d . . .
H4A H 0.1330 0.4809 0.8686 0.034 Uiso 1 1 calc R . .
C5 C 0.20514(8) 0.2810(5) 0.85344(10) 0.0266(5) Uani 1 1 d . . .
H5A H 0.2267 0.4323 0.8407 0.032 Uiso 1 1 calc R . .
C6 C 0.22633(8) 0.0553(4) 0.81398(10) 0.0244(4) Uani 1 1 d . . .
H6A H 0.2034 0.0338 0.7719 0.029 Uiso 1 1 calc R . .
H6B H 0.2225 -0.0979 0.8417 0.029 Uiso 1 1 calc R . .
C7 C 0.28656(8) 0.0842(4) 0.79537(10) 0.0231(4) Uani 1 1 d . B .
H7 H 0.3006 -0.0818 0.7800 0.028 Uiso 1 1 calc R . .
C8 C 0.29540(9) 0.2776(5) 0.74033(11) 0.0333(5) Uani 1 1 d . . .
H8BC H 0.2866 0.4447 0.7588 0.040 Uiso 0.25 1 calc PR A 2
H8BD H 0.3349 0.2783 0.7306 0.040 Uiso 0.25 1 calc PR A 2
H8AA H 0.3338 0.3379 0.7439 0.040 Uiso 0.75 1 calc PR A 1
H8AB H 0.2710 0.4230 0.7473 0.040 Uiso 0.75 1 calc PR A 1
C9A C 0.2637(5) 0.246(3) 0.6749(6) 0.038(3) Uiso 0.25 1 d P B 2
H9AA H 0.2776 0.0953 0.6520 0.045 Uiso 0.25 1 calc PR B 2
H9AB H 0.2249 0.2145 0.6850 0.045 Uiso 0.25 1 calc PR B 2
C9 C 0.28346(16) 0.1678(8) 0.66824(15) 0.0334(7) Uani 0.75 1 d PD B 1
H9A H 0.3099 0.0312 0.6600 0.040 Uiso 0.75 1 calc PR B 1
H9B H 0.2461 0.0948 0.6660 0.040 Uiso 0.75 1 calc PR B 1
C10A C 0.2654(6) 0.450(2) 0.6291(6) 0.043(3) Uiso 0.25 1 d PD B 2
H10A H 0.3042 0.5035 0.6285 0.052 Uiso 0.25 1 calc PR B 2
H10B H 0.2451 0.5887 0.6499 0.052 Uiso 0.25 1 calc PR B 2
C10 C 0.28773(16) 0.3670(9) 0.61235(16) 0.0422(9) Uani 0.75 1 d P B 1
H10C H 0.3193 0.4782 0.6234 0.051 Uiso 0.75 1 calc PR B 1
H10D H 0.2946 0.2829 0.5688 0.051 Uiso 0.75 1 calc PR B 1
C11 C 0.23526(15) 0.5259(7) 0.60451(16) 0.0389(8) Uani 0.75 1 d P B 1
H11A H 0.2441 0.6883 0.5832 0.047 Uiso 0.75 1 calc PR B 1
H11B H 0.2211 0.5608 0.6499 0.047 Uiso 0.75 1 calc PR B 1
C11A C 0.2450(4) 0.436(3) 0.5558(6) 0.052(3) Uiso 0.25 1 d PD B 2
H11C H 0.2514 0.5967 0.5322 0.062 Uiso 0.25 1 calc PR B 2
H11D H 0.2637 0.2998 0.5316 0.062 Uiso 0.25 1 calc PR B 2
C12 C 0.18928(13) 0.3876(7) 0.55955(15) 0.0550(8) Uani 1 1 d D . .
H12A H 0.2007 0.3794 0.5120 0.066 Uiso 0.75 1 calc PR B 1
H12B H 0.1850 0.2137 0.5761 0.066 Uiso 0.75 1 calc PR B 1
H12C H 0.1884 0.2788 0.6001 0.066 Uiso 0.25 1 calc PR B 2
H12D H 0.1826 0.2723 0.5208 0.066 Uiso 0.25 1 calc PR B 2
C13 C 0.13600(12) 0.5204(6) 0.56208(12) 0.0476(7) Uani 1 1 d . B .
H13A H 0.1421 0.7008 0.5507 0.057 Uiso 0.35 1 calc PR C 2
H13 H 0.1378 0.6966 0.5449 0.057 Uiso 0.40 1 calc PR C 1
H13B H 0.1420 0.7008 0.5506 0.057 Uiso 0.25 1 calc PR C 3
C14A C 0.0970(4) 0.415(2) 0.5113(4) 0.044(2) Uiso 0.35 1 d PD B 2
H14A H 0.0932 0.2337 0.5213 0.053 Uiso 0.35 1 calc PR B 2
H14B H 0.0609 0.4929 0.5181 0.053 Uiso 0.35 1 calc PR B 2
C14 C 0.0854(4) 0.359(2) 0.5260(5) 0.037(2) Uiso 0.40 1 d P B 1
H14C H 0.0845 0.1879 0.5457 0.045 Uiso 0.40 1 calc PR B 1
H14D H 0.0500 0.4416 0.5339 0.045 Uiso 0.40 1 calc PR B 1
C14B C 0.0834(7) 0.441(4) 0.5306(9) 0.049(4) Uiso 0.25 1 d P B 3
H14E H 0.0777 0.2643 0.5440 0.058 Uiso 0.25 1 calc PR B 3
H14F H 0.0544 0.5404 0.5520 0.058 Uiso 0.25 1 calc PR B 3
C15 C 0.0947(4) 0.3424(19) 0.4490(4) 0.0509(19) Uiso 0.40 1 d PD B 1
H15A H 0.0939 0.5135 0.4295 0.061 Uiso 0.40 1 calc PR B 1
H15B H 0.1314 0.2700 0.4417 0.061 Uiso 0.40 1 calc PR B 1
C15A C 0.1083(4) 0.438(2) 0.4402(4) 0.054(2) Uiso 0.35 1 d PD B 2
H15C H 0.1425 0.3444 0.4316 0.065 Uiso 0.35 1 calc PR B 2
H15D H 0.1152 0.6167 0.4301 0.065 Uiso 0.35 1 calc PR B 2
C15B C 0.0727(5) 0.454(3) 0.4593(6) 0.051(3) Uiso 0.25 1 d P B 3
H15E H 0.0402 0.3490 0.4479 0.061 Uiso 0.25 1 calc PR B 3
H15F H 0.1043 0.3788 0.4367 0.061 Uiso 0.25 1 calc PR B 3
C16 C 0.0523(3) 0.1863(19) 0.4134(4) 0.0533(19) Uiso 0.40 1 d PD B 1
H16A H 0.0157 0.2540 0.4234 0.064 Uiso 0.40 1 calc PR B 1
H16B H 0.0545 0.0140 0.4320 0.064 Uiso 0.40 1 calc PR B 1
C16A C 0.0623(4) 0.341(2) 0.3903(5) 0.063(2) Uiso 0.35 1 d PD B 2
H16C H 0.0289 0.4425 0.3969 0.076 Uiso 0.35 1 calc PR B 2
H16D H 0.0738 0.3713 0.3435 0.076 Uiso 0.35 1 calc PR B 2
C16B C 0.0623(5) 0.722(3) 0.4278(6) 0.047(3) Uiso 0.25 1 d P B 3
H16E H 0.0316 0.8017 0.4511 0.057 Uiso 0.25 1 calc PR B 3
H16F H 0.0954 0.8261 0.4366 0.057 Uiso 0.25 1 calc PR B 3
C17 C 0.0568(4) 0.173(2) 0.3383(4) 0.063(2) Uiso 0.40 1 d PD B 1
H17A H 0.0924 0.0942 0.3283 0.076 Uiso 0.40 1 calc PR B 1
H17B H 0.0572 0.3455 0.3201 0.076 Uiso 0.40 1 calc PR B 1
C17A C 0.0474(5) 0.066(2) 0.3970(6) 0.070(3) Uiso 0.35 1 d PD B 2
H17C H 0.0813 -0.0366 0.3986 0.084 Uiso 0.35 1 calc PR B 2
H17D H 0.0285 0.0392 0.4399 0.084 Uiso 0.35 1 calc PR B 2
C17B C 0.0493(7) 0.720(4) 0.3555(8) 0.077(4) Uiso 0.25 1 d P B 3
H17E H 0.0812 0.6532 0.3317 0.092 Uiso 0.25 1 calc PR B 3
H17F H 0.0179 0.6066 0.3461 0.092 Uiso 0.25 1 calc PR B 3
C18 C 0.0121(4) 0.030(2) 0.3015(5) 0.071(2) Uiso 0.40 1 d PD B 1
H18A H 0.0238 -0.0139 0.2561 0.107 Uiso 0.40 1 calc PR B 1
H18B H -0.0211 0.1331 0.2978 0.107 Uiso 0.40 1 calc PR B 1
H18C H 0.0043 -0.1241 0.3266 0.107 Uiso 0.40 1 calc PR B 1
C18A C 0.0105(5) -0.017(3) 0.3382(6) 0.069(3) Uiso 0.35 1 d PD B 2
H18D H 0.0326 -0.0488 0.2987 0.103 Uiso 0.35 1 calc PR B 2
H18E H -0.0165 0.1142 0.3273 0.103 Uiso 0.35 1 calc PR B 2
H18F H -0.0086 -0.1717 0.3503 0.103 Uiso 0.35 1 calc PR B 2
C18B C 0.0360(8) 0.966(4) 0.3286(9) 0.074(4) Uiso 0.25 1 d P B 3
H18G H 0.0384 0.9636 0.2792 0.111 Uiso 0.25 1 calc PR B 3
H18H H 0.0618 1.0894 0.3480 0.111 Uiso 0.25 1 calc PR B 3
H18I H -0.0015 1.0107 0.3404 0.111 Uiso 0.25 1 calc PR B 3
C21 C 0.34608(8) -0.0344(4) 0.88919(11) 0.0244(5) Uani 1 1 d . . .
H21 H 0.3219 -0.1860 0.8890 0.029 Uiso 1 1 calc R . .
C22 C 0.35749(8) 0.0481(5) 0.96205(11) 0.0274(5) Uani 1 1 d . . .
H22A H 0.3742 -0.0950 0.9882 0.033 Uiso 1 1 calc R . .
C23 C 0.39701(9) 0.2686(5) 0.96522(12) 0.0325(5) Uani 1 1 d . . .
H23A H 0.3790 0.4201 0.9445 0.039 Uiso 1 1 calc R . .
C24 C 0.44814(9) 0.2040(5) 0.92750(13) 0.0334(5) Uani 1 1 d . . .
H24A H 0.4691 0.0703 0.9529 0.040 Uiso 1 1 calc R . .
C25 C 0.43353(8) 0.1112(5) 0.85606(12) 0.0332(5) Uani 1 1 d . . .
H25 H 0.4163 0.2517 0.8293 0.040 Uiso 1 1 calc R . .
C26 C 0.48281(10) 0.0157(6) 0.81954(15) 0.0478(7) Uani 1 1 d . . .
H26A H 0.4706 -0.0473 0.7743 0.057 Uiso 1 1 calc R . .
H26B H 0.5086 0.1563 0.8129 0.057 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.328(3) . ?
O1 C13 1.460(3) . ?
O2 C1 1.200(4) . ?
O4 C4 1.427(3) . ?
O5 C5 1.426(3) . ?
O21 C7 1.448(2) . ?
O21 C21 1.404(3) . ?
O22 C22 1.417(3) . ?
O23 C23 1.425(3) . ?
O24 C24 1.412(3) . ?
O25 C21 1.417(2) . ?
O25 C25 1.440(3) . ?
O26 C26 1.420(3) . ?
C1 C2 1.484(3) . ?
C2 C3 1.328(4) . ?
C3 C4 1.506(3) . ?
C4 C5 1.536(3) . ?
C5 C6 1.534(3) . ?
C6 C7 1.536(3) . ?
C7 C8 1.520(3) . ?
C8 C9A 1.489(11) . ?
C8 C9 1.556(4) . ?
C9A C10A 1.414(17) . ?
C9 C10 1.538(5) . ?
C10A C11A 1.514(13) . ?
C10 C11 1.538(6) . ?
C11 C12 1.585(5) . ?
C11A C12 1.389(11) . ?
C12 C13 1.482(4) . ?
C13 C14A 1.467(9) . ?
C13 C14 1.645(9) . ?
C13 C14B 1.467(16) . ?
C14A C15A 1.447(12) . ?
C14 C15 1.549(13) . ?
C14B C15B 1.42(2) . ?
C15 C16 1.483(11) . ?
C15A C16A 1.551(12) . ?
C15B C16B 1.573(19) . ?
C16 C17 1.493(10) . ?
C16A C17A 1.520(13) . ?
C16B C17B 1.450(19) . ?
C17 C18 1.494(12) . ?
C17A C18A 1.508(13) . ?
C17B C18B 1.44(3) . ?
C21 C22 1.520(3) . ?
C22 C23 1.520(3) . ?
C23 C24 1.517(3) . ?
C24 C25 1.524(4) . ?
C25 C26 1.513(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 119.7(2) . . ?
C21 O21 C7 114.16(17) . . ?
C21 O25 C25 113.17(18) . . ?
O1 C1 C2 112.4(2) . . ?
O2 C1 O1 124.5(2) . . ?
O2 C1 C2 123.1(2) . . ?
C3 C2 C1 121.6(2) . . ?
C2 C3 C4 123.5(2) . . ?
O4 C4 C3 110.91(18) . . ?
O4 C4 C5 108.58(18) . . ?
C3 C4 C5 109.99(17) . . ?
O5 C5 C4 106.19(16) . . ?
O5 C5 C6 111.41(19) . . ?
C6 C5 C4 114.00(18) . . ?
C5 C6 C7 112.76(18) . . ?
O21 C7 C6 108.29(15) . . ?
O21 C7 C8 107.88(17) . . ?
C8 C7 C6 113.76(17) . . ?
C7 C8 C9 111.8(2) . . ?
C9A C8 C7 117.5(5) . . ?
C9A C8 C9 24.7(5) . . ?
C10A C9A C8 116.2(10) . . ?
C10 C9 C8 112.4(3) . . ?
C9A C10A C11A 123.9(11) . . ?
C11 C10 C9 111.9(3) . . ?
C10 C11 C12 111.6(3) . . ?
C12 C11A C10A 104.1(9) . . ?
C11A C12 C11 43.2(5) . . ?
C11A C12 C13 140.7(7) . . ?
C13 C12 C11 111.1(3) . . ?
O1 C13 C12 107.0(2) . . ?
O1 C13 C14A 114.9(5) . . ?
O1 C13 C14 98.1(4) . . ?
O1 C13 C14B 96.0(8) . . ?
C12 C13 C14 112.2(4) . . ?
C14A C13 C12 109.8(5) . . ?
C14A C13 C14 17.7(4) . . ?
C14B C13 C12 127.0(8) . . ?
C14B C13 C14A 21.0(7) . . ?
C14B C13 C14 15.4(7) . . ?
C15A C14A C13 119.2(8) . . ?
C15 C14 C13 108.6(7) . . ?
C15B C14B C13 121.8(14) . . ?
C16 C15 C14 111.8(7) . . ?
C14A C15A C16A 115.3(9) . . ?
C14B C15B C16B 117.2(13) . . ?
C15 C16 C17 114.9(7) . . ?
C17A C16A C15A 115.8(9) . . ?
C17B C16B C15B 114.2(12) . . ?
C16 C17 C18 115.2(8) . . ?
C18A C17A C16A 110.8(10) . . ?
C18B C17B C16B 113.2(15) . . ?
O21 C21 O25 111.56(17) . . ?
O21 C21 C22 107.54(18) . . ?
O25 C21 C22 110.93(16) . . ?
O22 C22 C21 109.91(16) . . ?
O22 C22 C23 109.4(2) . . ?
C21 C22 C23 110.82(18) . . ?
O23 C23 C22 109.9(2) . . ?
O23 C23 C24 107.66(17) . . ?
C24 C23 C22 109.6(2) . . ?
O24 C24 C23 109.5(2) . . ?
O24 C24 C25 108.5(2) . . ?
C23 C24 C25 111.18(18) . . ?
O25 C25 C24 110.97(18) . . ?
O25 C25 C26 106.0(2) . . ?
C26 C25 C24 112.9(2) . . ?
O26 C26 C25 112.2(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O26 0.84 1.90 2.715(2) 164.0 3_455
O5 H5 O22 0.84 1.93 2.724(2) 157.0 .
O22 H22 O5 0.84 1.80 2.639(3) 172.0 4_547
O23 H23 O4 0.84 2.13 2.784(2) 134.1 4_557
O24 H24 O23 0.84 1.88 2.722(2) 176.1 2_657
O26 H26 O24 0.84 1.91 2.628(3) 142.3 1_545

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 19.5(3) . . . . ?
O1 C13 C14A C15A 175.2(8) . . . . ?
O1 C13 C14 C15 -179.2(6) . . . . ?
O1 C13 C14B C15B 170.7(15) . . . . ?
O2 C1 C2 C3 -157.5(3) . . . . ?
O4 C4 C5 O5 -64.4(2) . . . . ?
O4 C4 C5 C6 58.7(2) . . . . ?
O5 C5 C6 C7 -92.1(2) . . . . ?
O21 C7 C8 C9A -175.8(7) . . . . ?
O21 C7 C8 C9 157.6(2) . . . . ?
O21 C21 C22 O22 55.4(2) . . . . ?
O21 C21 C22 C23 -65.7(2) . . . . ?
O22 C22 C23 O23 67.2(2) . . . . ?
O22 C22 C23 C24 -174.64(17) . . . . ?
O23 C23 C24 O24 -68.2(2) . . . . ?
O23 C23 C24 C25 172.0(2) . . . . ?
O24 C24 C25 O25 -174.81(17) . . . . ?
O24 C24 C25 C26 66.3(3) . . . . ?
O25 C21 C22 O22 177.66(18) . . . . ?
O25 C21 C22 C23 56.6(2) . . . . ?
O25 C25 C26 O26 -64.9(3) . . . . ?
C1 O1 C13 C12 103.4(3) . . . . ?
C1 O1 C13 C14A -134.5(6) . . . . ?
C1 O1 C13 C14 -140.3(4) . . . . ?
C1 O1 C13 C14B -125.0(8) . . . . ?
C1 C2 C3 C4 168.1(2) . . . . ?
C2 C3 C4 O4 133.7(2) . . . . ?
C2 C3 C4 C5 -106.2(2) . . . . ?
C3 C4 C5 O5 174.1(2) . . . . ?
C3 C4 C5 C6 -62.9(3) . . . . ?
C4 C5 C6 C7 147.77(18) . . . . ?
C5 C6 C7 O21 48.2(2) . . . . ?
C5 C6 C7 C8 -71.7(2) . . . . ?
C6 C7 C8 C9A -55.6(7) . . . . ?
C6 C7 C8 C9 -82.2(3) . . . . ?
C7 O21 C21 O25 80.1(2) . . . . ?
C7 O21 C21 C22 -158.01(15) . . . . ?
C7 C8 C9A C10A 169.6(9) . . . . ?
C7 C8 C9 C10 175.4(3) . . . . ?
C8 C9A C10A C11A 168.2(11) . . . . ?
C8 C9 C10 C11 -81.1(4) . . . . ?
C9A C8 C9 C10 66.9(12) . . . . ?
C9A C10A C11A C12 62.9(17) . . . . ?
C9 C8 C9A C10A -107.7(16) . . . . ?
C9 C10 C11 C12 -81.8(3) . . . . ?
C10A C11A C12 C11 29.2(6) . . . . ?
C10A C11A C12 C13 91.1(11) . . . . ?
C10 C11 C12 C11A -46.7(9) . . . . ?
C10 C11 C12 C13 170.1(3) . . . . ?
C11 C12 C13 O1 -64.4(3) . . . . ?
C11 C12 C13 C14A 170.2(5) . . . . ?
C11 C12 C13 C14 -170.9(4) . . . . ?
C11 C12 C13 C14B -175.9(10) . . . . ?
C11A C12 C13 O1 -104.8(8) . . . . ?
C11A C12 C13 C14A 129.9(9) . . . . ?
C11A C12 C13 C14 148.7(9) . . . . ?
C11A C12 C13 C14B 143.7(12) . . . . ?
C12 C13 C14A C15A -64.2(11) . . . . ?
C12 C13 C14 C15 -67.1(7) . . . . ?
C12 C13 C14B C15B -72.8(18) . . . . ?
C13 O1 C1 O2 16.9(4) . . . . ?
C13 O1 C1 C2 -160.0(2) . . . . ?
C13 C14A C15A C16A -174.8(9) . . . . ?
C13 C14 C15 C16 176.7(7) . . . . ?
C13 C14B C15B C16B -73.9(18) . . . . ?
C14A C13 C14 C15 18.5(19) . . . . ?
C14A C13 C14B C15B -34(2) . . . . ?
C14A C15A C16A C17A -60.0(13) . . . . ?
C14 C13 C14A C15A -165(3) . . . . ?
C14 C13 C14B C15B -91(4) . . . . ?
C14 C15 C16 C17 177.0(8) . . . . ?
C14B C13 C14A C15A 148(4) . . . . ?
C14B C13 C14 C15 98(4) . . . . ?
C14B C15B C16B C17B -177.4(13) . . . . ?
C15 C16 C17 C18 -176.1(9) . . . . ?
C15A C16A C17A C18A -169.2(9) . . . . ?
C15B C16B C17B C18B 175.7(14) . . . . ?
C21 O21 C7 C6 99.04(19) . . . . ?
C21 O21 C7 C8 -137.42(18) . . . . ?
C21 O25 C25 C24 58.2(2) . . . . ?
C21 O25 C25 C26 -178.87(18) . . . . ?
C21 C22 C23 O23 -171.43(18) . . . . ?
C21 C22 C23 C24 -53.3(2) . . . . ?
C22 C23 C24 O24 172.26(18) . . . . ?
C22 C23 C24 C25 52.4(3) . . . . ?
C23 C24 C25 O25 -54.3(3) . . . . ?
C23 C24 C25 C26 -173.2(2) . . . . ?
C24 C25 C26 O26 56.8(3) . . . . ?
C25 O25 C21 O21 60.6(2) . . . . ?
C25 O25 C21 C22 -59.3(2) . . . . ?

####################################################################### 
# 
# 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_zjun2cult
_database_code_depnum_ccdc_archive 'CCDC 1057055'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_audit_creation_date             2014-09-18
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        'gliomasolide A'
_chemical_formula_moiety         'C18 H32 O4'
_chemical_formula_sum            'C18 H32 O4'
_chemical_formula_weight         312.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 O4 H30'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.42511(18)
_cell_length_b                   7.6161(2)
_cell_length_c                   21.7672(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.546(3)
_cell_angle_gamma                90.00
_cell_volume                     899.05(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      75.6320
_cell_measurement_theta_min      6.1140
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4417
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         6.10
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.8605
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   33.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -90.00    7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  112.0000  -47.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega -114.00  -11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega   44.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  8 omega   86.00  133.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega  143.00  171.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00  145.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -15.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
 12 omega   49.00  137.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00  130.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000  150.0000 95
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1989745000
_diffrn_orient_matrix_UB_12      0.1433231000
_diffrn_orient_matrix_UB_13      -0.0049049000
_diffrn_orient_matrix_UB_21      0.0176549000
_diffrn_orient_matrix_UB_22      -0.0370320000
_diffrn_orient_matrix_UB_23      -0.0692876000
_diffrn_orient_matrix_UB_31      -0.2019834000
_diffrn_orient_matrix_UB_32      0.1379461000
_diffrn_orient_matrix_UB_33      -0.0135856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2686
_reflns_number_total             2760
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4447(3) 0.4013(2) 0.24258(6) 0.0218(3) Uani 1 1 d . . .
O2 O 0.0417(3) 0.4076(3) 0.26479(7) 0.0320(4) Uani 1 1 d . . .
O4 O 0.8656(3) 0.3333(2) 0.44810(7) 0.0211(3) Uani 1 1 d . . .
H4 H 0.8379 0.2248 0.4488 0.047(10) Uiso 1 1 calc R . .
O7 O 0.8486(3) 0.9771(2) 0.45522(7) 0.0222(3) Uani 1 1 d . . .
H7 H 0.9338 0.9448 0.4860 0.039(8) Uiso 1 1 calc R . .
C1 C 0.2563(4) 0.3925(3) 0.28051(10) 0.0215(4) Uani 1 1 d . . .
C2 C 0.3383(4) 0.3726(3) 0.34562(9) 0.0204(4) Uani 1 1 d . . .
H2 H 0.2206 0.3384 0.3749 0.024 Uiso 1 1 calc R . .
C3 C 0.5690(4) 0.4006(3) 0.36479(9) 0.0209(4) Uani 1 1 d . . .
H3 H 0.6938 0.4055 0.3350 0.025 Uiso 1 1 calc R . .
C4 C 0.6427(4) 0.4250(3) 0.43133(9) 0.0206(4) Uani 1 1 d . . .
H4A H 0.5062 0.3840 0.4578 0.025 Uiso 1 1 calc R . .
C5 C 0.6935(4) 0.6214(3) 0.44364(9) 0.0201(4) Uani 1 1 d . . .
H5A H 0.5501 0.6910 0.4285 0.024 Uiso 1 1 calc R . .
H5B H 0.7120 0.6406 0.4885 0.024 Uiso 1 1 calc R . .
C6 C 0.9271(4) 0.6871(3) 0.41223(10) 0.0202(5) Uani 1 1 d . . .
H6A H 1.0731 0.6549 0.4381 0.024 Uiso 1 1 calc R . .
H6B H 0.9413 0.6264 0.3723 0.024 Uiso 1 1 calc R . .
C7 C 0.9295(4) 0.8851(3) 0.40130(9) 0.0213(4) Uani 1 1 d . . .
H7A H 1.1022 0.9220 0.3929 0.026 Uiso 1 1 calc R . .
C8 C 0.7631(4) 0.9416(3) 0.34744(10) 0.0231(5) Uani 1 1 d . . .
H8A H 0.7320 1.0693 0.3505 0.028 Uiso 1 1 calc R . .
H8B H 0.6026 0.8807 0.3502 0.028 Uiso 1 1 calc R . .
C9 C 0.8720(4) 0.9020(3) 0.28497(9) 0.0248(4) Uani 1 1 d . . .
H9A H 0.9255 0.7778 0.2839 0.030 Uiso 1 1 calc R . .
H9B H 1.0190 0.9767 0.2793 0.030 Uiso 1 1 calc R . .
C10 C 0.6842(4) 0.9357(3) 0.23203(9) 0.0259(5) Uani 1 1 d . . .
H10A H 0.5952 1.0465 0.2401 0.031 Uiso 1 1 calc R . .
H10B H 0.7739 0.9509 0.1934 0.031 Uiso 1 1 calc R . .
C11 C 0.4964(4) 0.7874(3) 0.22352(10) 0.0250(5) Uani 1 1 d . . .
H11A H 0.4603 0.7377 0.2643 0.030 Uiso 1 1 calc R . .
H11B H 0.3411 0.8371 0.2061 0.030 Uiso 1 1 calc R . .
C12 C 0.5814(4) 0.6394(3) 0.18178(9) 0.0233(5) Uani 1 1 d . . .
H12A H 0.5927 0.6844 0.1393 0.028 Uiso 1 1 calc R . .
H12B H 0.7481 0.6007 0.1955 0.028 Uiso 1 1 calc R . .
C13 C 0.4070(4) 0.4821(3) 0.18193(10) 0.0223(4) Uani 1 1 d . . .
H13 H 0.2327 0.5238 0.1772 0.027 Uiso 1 1 calc R . .
C14 C 0.4571(4) 0.3432(3) 0.13364(10) 0.0251(5) Uani 1 1 d . . .
H14A H 0.4680 0.4008 0.0930 0.030 Uiso 1 1 calc R . .
H14B H 0.6184 0.2876 0.1433 0.030 Uiso 1 1 calc R . .
C15 C 0.2598(4) 0.2016(3) 0.12985(10) 0.0243(5) Uani 1 1 d . . .
H15A H 0.0992 0.2568 0.1191 0.029 Uiso 1 1 calc R . .
H15B H 0.2457 0.1462 0.1708 0.029 Uiso 1 1 calc R . .
C16 C 0.3136(4) 0.0593(3) 0.08257(11) 0.0273(5) Uani 1 1 d . . .
H16A H 0.3336 0.1152 0.0420 0.033 Uiso 1 1 calc R . .
H16B H 0.4715 0.0014 0.0942 0.033 Uiso 1 1 calc R . .
C17 C 0.1127(4) -0.0795(4) 0.07704(10) 0.0295(5) Uani 1 1 d . . .
H17A H -0.0459 -0.0212 0.0665 0.035 Uiso 1 1 calc R . .
H17B H 0.0956 -0.1373 0.1174 0.035 Uiso 1 1 calc R . .
C18 C 0.1625(5) -0.2199(4) 0.02873(13) 0.0411(7) Uani 1 1 d . . .
H18A H 0.1660 -0.1652 -0.0120 0.062 Uiso 1 1 calc R . .
H18B H 0.0317 -0.3085 0.0292 0.062 Uiso 1 1 calc R . .
H18C H 0.3219 -0.2758 0.0380 0.062 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.333(2) . ?
O1 C13 1.466(3) . ?
O2 C1 1.210(3) . ?
O4 C4 1.435(3) . ?
O7 C7 1.445(3) . ?
C1 C2 1.482(3) . ?
C2 C3 1.326(3) . ?
C3 C4 1.504(3) . ?
C4 C5 1.543(3) . ?
C5 C6 1.540(3) . ?
C6 C7 1.527(3) . ?
C7 C8 1.522(3) . ?
C8 C9 1.527(3) . ?
C9 C10 1.539(3) . ?
C10 C11 1.529(3) . ?
C11 C12 1.527(3) . ?
C12 C13 1.526(3) . ?
C13 C14 1.521(3) . ?
C14 C15 1.520(3) . ?
C15 C16 1.528(3) . ?
C16 C17 1.521(3) . ?
C17 C18 1.529(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 119.21(15) . . ?
O1 C1 C2 112.48(17) . . ?
O2 C1 O1 124.62(19) . . ?
O2 C1 C2 122.80(19) . . ?
C3 C2 C1 122.74(19) . . ?
C2 C3 C4 123.17(18) . . ?
O4 C4 C3 112.66(17) . . ?
O4 C4 C5 106.40(17) . . ?
C3 C4 C5 109.17(18) . . ?
C6 C5 C4 112.52(17) . . ?
C7 C6 C5 113.63(17) . . ?
O7 C7 C6 110.38(17) . . ?
O7 C7 C8 107.55(17) . . ?
C8 C7 C6 113.07(18) . . ?
C7 C8 C9 113.22(18) . . ?
C8 C9 C10 111.68(19) . . ?
C11 C10 C9 113.14(18) . . ?
C12 C11 C10 114.01(19) . . ?
C13 C12 C11 112.39(18) . . ?
O1 C13 C12 105.06(17) . . ?
O1 C13 C14 107.86(18) . . ?
C14 C13 C12 114.96(18) . . ?
C15 C14 C13 113.12(18) . . ?
C14 C15 C16 113.14(18) . . ?
C17 C16 C15 113.37(19) . . ?
C16 C17 C18 113.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O7 0.84 1.89 2.719(2) 167.6 1_545
O7 H7 O4 0.84 1.97 2.803(2) 171.1 2_756

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 14.3(3) . . . . ?
O1 C13 C14 C15 70.8(2) . . . . ?
O2 C1 C2 C3 -162.3(2) . . . . ?
O4 C4 C5 C6 52.8(2) . . . . ?
O7 C7 C8 C9 161.94(18) . . . . ?
C1 O1 C13 C12 118.3(2) . . . . ?
C1 O1 C13 C14 -118.6(2) . . . . ?
C1 C2 C3 C4 164.4(2) . . . . ?
C2 C3 C4 O4 137.9(2) . . . . ?
C2 C3 C4 C5 -104.2(2) . . . . ?
C3 C4 C5 C6 -69.0(2) . . . . ?
C4 C5 C6 C7 157.03(17) . . . . ?
C5 C6 C7 O7 44.3(2) . . . . ?
C5 C6 C7 C8 -76.2(2) . . . . ?
C6 C7 C8 C9 -75.9(2) . . . . ?
C7 C8 C9 C10 171.66(19) . . . . ?
C8 C9 C10 C11 -78.9(2) . . . . ?
C9 C10 C11 C12 -87.1(2) . . . . ?
C10 C11 C12 C13 171.55(17) . . . . ?
C11 C12 C13 O1 -71.2(2) . . . . ?
C11 C12 C13 C14 170.38(18) . . . . ?
C12 C13 C14 C15 -172.43(18) . . . . ?
C13 O1 C1 O2 18.3(3) . . . . ?
C13 O1 C1 C2 -158.2(2) . . . . ?
C13 C14 C15 C16 -178.43(19) . . . . ?
C14 C15 C16 C17 -178.07(19) . . . . ?
C15 C16 C17 C18 178.6(2) . . . . ?

####################################################################### 
# 
# 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_zjun3cult
_database_code_depnum_ccdc_archive 'CCDC 1057056'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        'gliomasolide C'
_chemical_formula_moiety         'C18 H32 O6, C5 H5 N'
_chemical_formula_sum            'C23 H37 N O6'
_chemical_formula_weight         423.54
_chemical_absolute_configuration ad
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

_space_group_IT_number           5

_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'

_cell_length_a                   26.5127(8)
_cell_length_b                   5.33762(15)
_cell_length_c                   16.6627(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.282(3)
_cell_angle_gamma                90.00
_cell_volume                     2357.42(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2769
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.4040
_cell_measurement_theta_min      5.3190
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6545
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.46
_diffrn_reflns_theta_min         4.22
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   29.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7522   37.0000  120.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00   34.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7522   19.0000   30.0000 116

#__ type_ start__ end____ width___ exp.time_
  3 omega   70.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7522   37.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega   86.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   45.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   85.00  158.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   45.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega   48.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -94.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7522 -125.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega   32.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -94.0000  -30.0000 76

#__ type_ start__ end____ width___ exp.time_
  9 omega   47.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7522 -125.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00   88.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -30.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega   51.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -94.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00   71.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -30.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -30.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   29.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633  -94.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 15 omega   96.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7633   81.0000  110.0000 82
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0180239000
_diffrn_orient_matrix_UB_12      0.1619256000
_diffrn_orient_matrix_UB_13      -0.0703678000
_diffrn_orient_matrix_UB_21      0.0230136000
_diffrn_orient_matrix_UB_22      0.1896492000
_diffrn_orient_matrix_UB_23      0.0601024000
_diffrn_orient_matrix_UB_31      0.0501912000
_diffrn_orient_matrix_UB_32      -0.1453086000
_diffrn_orient_matrix_UB_33      0.0001438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3759
_reflns_number_total             4164
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(19)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.3891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1043
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O1(0.75) O1A(0.25) O2(0.75) O2A(0.25) O4(0.75) H4(0.75) O4A(0.25)
 H4A(0.25) O5(0.75) H5(0.75) O5A(0.25) H5A(0.25) H6A(0.25) H6B(0.75) H7B(0.75)
 H7A(0.25) C1(0.75) C1A(0.25) C2(0.75) H2(0.75) C2A(0.25) H2A(0.25) C3(0.75)
 H3(0.75) C3A(0.25) H3A(0.25) C4(0.75) H4B(0.75) C4A(0.25) H4AA(0.25) C5(0.75)
 H5B(0.75) C5A(0.25) H5AA(0.25) H6AA(0.75) H6BB(0.25) H13(0.75) H13A(0.25)
3.a Riding coordinates:
 O6(H6A,H6B), O7(H7B,H7A)
3.b Ternary CH refined with riding coordinates:
 C4(H4B), C4A(H4AA), C5(H5B), C5A(H5AA), C6(H6AA), C6(H6BB), C7(H7), C13(H13),
 C13(H13A)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C2A(H2A), C3(H3), C3A(H3A), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S),
 C6S(H6S)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4A(H4A), O5(H5), O5A(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.20925(8) 0.0846(4) 0.19991(12) 0.0366(5) Uiso 0.75 d A 1 .
O1A O 0.1935(2) 0.0201(13) 0.2046(4) 0.0378(14) Uiso 0.25 d A 2 .
O2 O 0.20430(10) -0.3160(6) 0.24290(16) 0.0480(6) Uiso 0.75 d A 1 .
O2A O 0.2090(3) -0.4004(18) 0.2188(5) 0.061(2) Uiso 0.25 d A 2 .
O4 O 0.14666(10) 0.2884(5) 0.45477(16) 0.0391(8) Uiso 0.75 d A 1 .
H4 H 0.1425 0.3511 0.5004 0.059 Uiso 0.75 calc A 1 GR
O4A O 0.1389(3) 0.3445(14) 0.4535(4) 0.0294(19) Uiso 0.25 d A 2 .
H4A H 0.1100 0.3765 0.4706 0.044 Uiso 0.25 calc A 2 GR
O5 O 0.05908(11) 0.0678(6) 0.52321(18) 0.0322(9) Uiso 0.75 d A 1 .
H5 H 0.0485 0.2086 0.5078 0.048 Uiso 0.75 calc A 1 GR
O5A O 0.0673(3) 0.0675(19) 0.5168(6) 0.036(3) Uiso 0.25 d A 2 .
H5A H 0.0364 0.0319 0.5151 0.054 Uiso 0.25 calc A 2 GR
O6 O 0.00770(5) -0.1433(2) 0.38065(8) 0.0339(3) Uani 1 d . . .
H6A H 0.0123 -0.2858 0.4024 0.051 Uiso 0.25 d B 1 R
H6B H -0.0115 -0.0592 0.4106 0.051 Uiso 0.75 d B 2 R
O7 O 0.02042(5) 0.3733(2) 0.41087(8) 0.0371(3) Uani 1 d . . .
H7B H 0.0034 0.4950 0.3915 0.056 Uiso 0.75 d C 2 R
H7A H 0.0001 0.2709 0.4321 0.056 Uiso 0.25 d C 1 R
C1 C 0.20107(10) -0.0941(7) 0.25501(17) 0.0332(6) Uiso 0.75 d A 1 .
C1A C 0.1963(4) -0.209(3) 0.2476(6) 0.044(2) Uiso 0.25 d A 2 .
C2 C 0.18555(9) 0.0295(5) 0.32973(15) 0.0313(5) Uiso 0.75 d A 1 .
H2 H 0.1905 0.2049 0.3355 0.038 Uiso 0.75 calc A 1 R
C2A C 0.1806(3) -0.1682(15) 0.3313(4) 0.0341(16) Uiso 0.25 d A 2 .
H2A H 0.1821 -0.3058 0.3674 0.041 Uiso 0.25 calc A 2 R
C3 C 0.16496(8) -0.0971(5) 0.38903(14) 0.0310(5) Uiso 0.75 d A 1 .
H3 H 0.1664 -0.2748 0.3875 0.037 Uiso 0.75 calc A 1 R
C3A C 0.1644(3) 0.0505(14) 0.3584(4) 0.0292(14) Uiso 0.25 d A 2 .
H3A H 0.1657 0.1916 0.3238 0.035 Uiso 0.25 calc A 2 R
C4 C 0.13954(11) 0.0246(6) 0.4586(2) 0.0345(8) Uiso 0.75 d A 1 .
H4B H 0.1561 -0.0378 0.5093 0.041 Uiso 0.75 calc A 1 R
C4A C 0.1437(3) 0.087(2) 0.4424(6) 0.035(2) Uiso 0.25 d A 2 .
H4AA H 0.1671 0.0131 0.4840 0.042 Uiso 0.25 calc A 2 R
C5 C 0.08356(13) -0.0544(7) 0.4586(2) 0.0304(10) Uiso 0.75 d A 1 .
H5B H 0.0829 -0.2380 0.4706 0.036 Uiso 0.75 calc A 1 R
C5A C 0.0910(5) -0.031(2) 0.4467(7) 0.037(3) Uiso 0.25 d A 2 .
H5AA H 0.0965 -0.2132 0.4574 0.045 Uiso 0.25 calc A 2 R
C6 C 0.05514(7) -0.0174(4) 0.37644(12) 0.0345(4) Uani 1 d . . .
H6AA H 0.0752 -0.1049 0.3347 0.041 Uiso 0.75 calc A 1 R
H6BB H 0.0731 -0.1017 0.3317 0.041 Uiso 0.25 calc A 2 R
C7 C 0.04736(7) 0.2506(4) 0.34842(12) 0.0357(4) Uani 1 d A . .
H7 H 0.0810 0.3329 0.3426 0.043 Uiso 1 calc . . R
C8 C 0.01772(8) 0.2678(4) 0.26840(12) 0.0401(4) Uani 1 d . . .
H8A H -0.0170 0.2068 0.2770 0.048 Uiso 1 calc A . R
H8B H 0.0153 0.4464 0.2528 0.048 Uiso 1 calc . . R
C9 C 0.03965(8) 0.1221(4) 0.19856(12) 0.0422(5) Uani 1 d A . .
H9A H 0.0154 0.1297 0.1526 0.051 Uiso 1 calc . . R
H9B H 0.0430 -0.0558 0.2146 0.051 Uiso 1 calc . . R
C10 C 0.09085(8) 0.2148(4) 0.17056(13) 0.0426(5) Uani 1 d . . .
H10A H 0.0873 0.3890 0.1508 0.051 Uiso 1 calc A . R
H10B H 0.1149 0.2163 0.2168 0.051 Uiso 1 calc . . R
C11 C 0.11218(8) 0.0524(5) 0.10414(12) 0.0475(5) Uani 1 d A . .
H11A H 0.0880 0.0528 0.0580 0.057 Uiso 1 calc . . R
H11B H 0.1149 -0.1221 0.1239 0.057 Uiso 1 calc . . R
C12 C 0.16404(8) 0.1346(5) 0.07446(13) 0.0477(5) Uani 1 d . . .
H12A H 0.1656 0.0970 0.0164 0.057 Uiso 1 calc A . R
H12B H 0.1668 0.3186 0.0807 0.057 Uiso 1 calc . . R
C13 C 0.20921(9) 0.0149(4) 0.11625(12) 0.0444(5) Uani 1 d A . .
H13 H 0.2081 -0.1714 0.1102 0.053 Uiso 0.75 calc D 1 R
H13A H 0.2086 -0.1654 0.1000 0.053 Uiso 0.25 calc D 2 R
C14 C 0.25930(8) 0.1183(5) 0.08779(14) 0.0480(5) Uani 1 d . . .
H14A H 0.2594 0.1103 0.0284 0.058 Uiso 1 calc A . R
H14B H 0.2616 0.2970 0.1033 0.058 Uiso 1 calc . . R
C15 C 0.30580(9) -0.0165(4) 0.12045(13) 0.0471(5) Uani 1 d A . .
H15A H 0.3044 -0.1946 0.1039 0.056 Uiso 1 calc . . R
H15B H 0.3060 -0.0105 0.1798 0.056 Uiso 1 calc . . R
C16 C 0.35426(9) 0.1006(5) 0.09038(14) 0.0491(5) Uani 1 d . . .
H16A H 0.3517 0.1131 0.0312 0.059 Uiso 1 calc A . R
H16B H 0.3569 0.2731 0.1119 0.059 Uiso 1 calc . . R
C17 C 0.40222(9) -0.0393(5) 0.11279(15) 0.0533(6) Uani 1 d A . .
H17A H 0.4004 -0.2108 0.0902 0.064 Uiso 1 calc . . R
H17B H 0.4051 -0.0538 0.1720 0.064 Uiso 1 calc . . R
C18 C 0.44904(10) 0.0929(7) 0.08156(19) 0.0731(8) Uani 1 d . . .
H18A H 0.4470 0.1009 0.0228 0.110 Uiso 1 calc A . GR
H18B H 0.4793 -0.0006 0.0983 0.110 Uiso 1 calc . . GR
H18C H 0.4508 0.2631 0.1035 0.110 Uiso 1 calc . . GR
N1S N 0.14994(7) 0.5304(4) 0.60372(11) 0.0453(4) Uani 1 d . . .
C2S C 0.10922(8) 0.6056(5) 0.64122(13) 0.0454(5) Uani 1 d . . .
H2S H 0.0783 0.5217 0.6300 0.054 Uiso 1 calc . . R
C3S C 0.10941(10) 0.8003(5) 0.69601(14) 0.0566(6) Uani 1 d . . .
H3S H 0.0792 0.8487 0.7215 0.068 Uiso 1 calc . . R
C4S C 0.15387(11) 0.9221(5) 0.71281(15) 0.0593(7) Uani 1 d . . .
H4S H 0.1550 1.0580 0.7496 0.071 Uiso 1 calc . . R
C5S C 0.19665(10) 0.8448(5) 0.67575(16) 0.0610(7) Uani 1 d . . .
H5S H 0.2281 0.9244 0.6870 0.073 Uiso 1 calc . . R
C6S C 0.19343(9) 0.6484(5) 0.62140(14) 0.0540(6) Uani 1 d . . .
H6S H 0.2232 0.5953 0.5957 0.065 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.345(4) . ?
O1 C13 1.443(3) . ?
O1A C1A 1.417(16) . ?
O1A C13 1.539(6) . ?
O2 C1 1.205(4) . ?
O2A C1A 1.181(19) . ?
O4 C4 1.422(4) . ?
O4A C4A 1.393(13) . ?
O5 C5 1.427(5) . ?
O5A C5A 1.437(15) . ?
O6 C6 1.429(2) . ?
O7 C7 1.433(2) . ?
C1 C2 1.476(4) . ?
C1A C2A 1.481(13) . ?
C2 C3 1.325(4) . ?
C2A C3A 1.327(11) . ?
C3 C4 1.502(4) . ?
C3A C4A 1.526(12) . ?
C4 C5 1.543(5) . ?
C4A C5A 1.538(16) . ?
C5 C6 1.561(4) . ?
C5A C6 1.493(12) . ?
C6 C7 1.517(3) . ?
C7 C8 1.535(3) . ?
C8 C9 1.525(3) . ?
C9 C10 1.527(3) . ?
C10 C11 1.525(3) . ?
C11 C12 1.536(3) . ?
C12 C13 1.513(3) . ?
C13 C14 1.524(3) . ?
C14 C15 1.518(3) . ?
C15 C16 1.523(3) . ?
C16 C17 1.514(3) . ?
C17 C18 1.529(4) . ?
N1S C2S 1.322(3) . ?
N1S C6S 1.341(3) . ?
C2S C3S 1.383(4) . ?
C3S C4S 1.369(4) . ?
C4S C5S 1.367(4) . ?
C5S C6S 1.387(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 118.7(2) . . ?
C1A O1A C13 117.1(7) . . ?
O1 C1 C2 108.1(3) . . ?
O2 C1 O1 124.7(3) . . ?
O2 C1 C2 127.1(3) . . ?
O1A C1A C2A 109.7(11) . . ?
O2A C1A O1A 123.7(9) . . ?
O2A C1A C2A 126.7(12) . . ?
C3 C2 C1 121.9(2) . . ?
C3A C2A C1A 123.4(9) . . ?
C2 C3 C4 123.7(3) . . ?
C2A C3A C4A 123.4(8) . . ?
O4 C4 C3 109.4(3) . . ?
O4 C4 C5 113.5(3) . . ?
C3 C4 C5 109.3(2) . . ?
O4A C4A C3A 106.5(8) . . ?
O4A C4A C5A 108.1(8) . . ?
C3A C4A C5A 109.6(7) . . ?
O5 C5 C4 109.2(3) . . ?
O5 C5 C6 112.7(3) . . ?
C4 C5 C6 114.2(3) . . ?
O5A C5A C4A 107.6(9) . . ?
O5A C5A C6 109.7(9) . . ?
C6 C5A C4A 120.5(9) . . ?
O6 C6 C5 107.8(2) . . ?
O6 C6 C5A 119.0(5) . . ?
O6 C6 C7 110.15(15) . . ?
C5A C6 C5 11.3(5) . . ?
C5A C6 C7 111.5(5) . . ?
C7 C6 C5 116.67(19) . . ?
O7 C7 C6 105.90(16) . . ?
O7 C7 C8 110.46(16) . . ?
C6 C7 C8 112.76(16) . . ?
C9 C8 C7 115.84(18) . . ?
C8 C9 C10 115.11(17) . . ?
C11 C10 C9 112.59(17) . . ?
C10 C11 C12 114.88(19) . . ?
C13 C12 C11 115.86(19) . . ?
O1 C13 O1A 20.9(2) . . ?
O1 C13 C12 108.62(18) . . ?
O1 C13 C14 103.03(19) . . ?
C12 C13 O1A 101.8(3) . . ?
C12 C13 C14 112.97(19) . . ?
C14 C13 O1A 123.2(3) . . ?
C15 C14 C13 115.1(2) . . ?
C14 C15 C16 111.84(19) . . ?
C17 C16 C15 115.2(2) . . ?
C16 C17 C18 111.8(2) . . ?
C2S N1S C6S 117.5(2) . . ?
N1S C2S C3S 123.3(2) . . ?
C4S C3S C2S 118.8(2) . . ?
C5S C4S C3S 118.9(2) . . ?
C4S C5S C6S 118.9(2) . . ?
N1S C6S C5S 122.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 N1S 0.84 1.98 2.798(3) 165.6 .
O4A H4A O5A 0.84 2.15 2.643(11) 117.1 .
O5 H5 O7 0.84 1.97 2.670(4) 140.0 .
O5A H5A O6 0.84 2.31 2.880(10) 125.1 2_556
O6 H6A O7 0.85 1.84 2.6492(18) 159.2 1_545
O6 H6B O5A 0.85 2.05 2.880(10) 166.6 2_556
O7 H7B O6 0.85 1.94 2.6492(18) 139.8 1_565
O7 H7A O5 0.85 2.06 2.900(3) 169.6 2_556

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 165.7(2) . . . . ?
O1 C13 C14 C15 69.9(2) . . . . ?
O1A C1A C2A C3A 2.7(12) . . . . ?
O1A C13 C14 C15 64.1(4) . . . . ?
O2 C1 C2 C3 -11.6(5) . . . . ?
O2A C1A C2A C3A -176.5(9) . . . . ?
O4 C4 C5 O5 -55.8(4) . . . . ?
O4 C4 C5 C6 71.4(3) . . . . ?
O4A C4A C5A O5A -48.0(11) . . . . ?
O4A C4A C5A C6 78.7(11) . . . . ?
O5 C5 C6 O6 -66.1(3) . . . . ?
O5 C5 C6 C5A 124(3) . . . . ?
O5 C5 C6 C7 58.3(4) . . . . ?
O5A C5A C6 O6 -58.3(10) . . . . ?
O5A C5A C6 C5 -48(2) . . . . ?
O5A C5A C6 C7 71.5(9) . . . . ?
O6 C6 C7 O7 65.91(18) . . . . ?
O6 C6 C7 C8 -55.0(2) . . . . ?
O7 C7 C8 C9 -174.13(16) . . . . ?
C1 O1 C13 O1A 38.9(7) . . . . ?
C1 O1 C13 C12 112.8(2) . . . . ?
C1 O1 C13 C14 -127.1(2) . . . . ?
C1 C2 C3 C4 -167.6(2) . . . . ?
C1A O1A C13 O1 -120.6(11) . . . . ?
C1A O1A C13 C12 127.9(6) . . . . ?
C1A O1A C13 C14 -104.3(7) . . . . ?
C1A C2A C3A C4A 174.4(8) . . . . ?
C2 C3 C4 O4 -6.8(4) . . . . ?
C2 C3 C4 C5 118.0(3) . . . . ?
C2A C3A C4A O4A 170.1(7) . . . . ?
C2A C3A C4A C5A -73.2(10) . . . . ?
C3 C4 C5 O5 -178.1(3) . . . . ?
C3 C4 C5 C6 -51.0(4) . . . . ?
C3A C4A C5A O5A -163.7(9) . . . . ?
C3A C4A C5A C6 -37.0(12) . . . . ?
C4 C5 C6 O6 168.5(2) . . . . ?
C4 C5 C6 C5A -2(3) . . . . ?
C4 C5 C6 C7 -67.0(3) . . . . ?
C4A C5A C6 O6 175.9(7) . . . . ?
C4A C5A C6 C5 -174(4) . . . . ?
C4A C5A C6 C7 -54.2(10) . . . . ?
C5 C6 C7 O7 -57.4(2) . . . . ?
C5 C6 C7 C8 -178.3(2) . . . . ?
C5A C6 C7 O7 -68.4(5) . . . . ?
C5A C6 C7 C8 170.7(5) . . . . ?
C6 C7 C8 C9 -55.8(2) . . . . ?
C7 C8 C9 C10 -65.2(2) . . . . ?
C8 C9 C10 C11 176.55(19) . . . . ?
C9 C10 C11 C12 -179.15(18) . . . . ?
C10 C11 C12 C13 91.8(3) . . . . ?
C11 C12 C13 O1 -62.4(3) . . . . ?
C11 C12 C13 O1A -41.9(4) . . . . ?
C11 C12 C13 C14 -176.03(19) . . . . ?
C12 C13 C14 C15 -173.07(19) . . . . ?
C13 O1 C1 O2 16.8(4) . . . . ?
C13 O1 C1 C2 -160.7(2) . . . . ?
C13 O1A C1A O2A -1.4(13) . . . . ?
C13 O1A C1A C2A 179.3(6) . . . . ?
C13 C14 C15 C16 -179.03(19) . . . . ?
C14 C15 C16 C17 -173.65(19) . . . . ?
C15 C16 C17 C18 -179.0(2) . . . . ?
N1S C2S C3S C4S -0.2(4) . . . . ?
C2S N1S C6S C5S -1.0(3) . . . . ?
C2S C3S C4S C5S -0.9(4) . . . . ?
C3S C4S C5S C6S 1.0(4) . . . . ?
C4S C5S C6S N1S -0.1(4) . . . . ?
C6S N1S C2S C3S 1.1(3) . . . . ?

_olex2_date_sample_data_collection 2014-12-10
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour Deposition'
