# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_klim1705
_audit_block_doi                 10.5517/ccdc.csd.cc1yv9lp
_database_code_depnum_ccdc_archive 'CCDC 1812743'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov' 'Chem. Dept. of Moscow State Univ.'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 octahydro-7,3a,9-propane[1,2,3]triylcyclohepta[b]furo[2,3-c]furan-2,4-dione
;
_chemical_name_common            ?
_chemical_melting_point          453(1)
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_preparation       methanol

_cell_length_a                   6.6447(2)
_cell_length_b                   11.9625(3)
_cell_length_c                   14.7769(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.428(2)
_cell_angle_gamma                90
_cell_volume                     1151.29(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0915

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.94746(13) 0.28076(7) 0.26397(5) 0.0440(2) Uani 1 1 d . . . . .
C2 C 1.00556(18) 0.38918(10) 0.27206(8) 0.0443(3) Uani 1 1 d . . . . .
O2 O 1.11153(15) 0.42422(9) 0.34143(7) 0.0623(3) Uani 1 1 d . . . . .
C3 C 0.91637(19) 0.45163(10) 0.18474(8) 0.0442(3) Uani 1 1 d . . . . .
H3A H 1.0201 0.4661 0.1484 0.053 Uiso 1 1 calc R U . . .
H3B H 0.8562 0.5220 0.1984 0.053 Uiso 1 1 calc R U . . .
C3A C 0.75315(16) 0.37201(8) 0.13489(8) 0.0358(3) Uani 1 1 d . . . . .
C4 C 0.55871(18) 0.38236(10) 0.17414(8) 0.0443(3) Uani 1 1 d . . . . .
O4 O 0.46173(16) 0.46587(8) 0.18021(8) 0.0667(3) Uani 1 1 d . . . . .
O5 O 0.50237(13) 0.28237(7) 0.20130(7) 0.0503(2) Uani 1 1 d . . . . .
C5A C 0.64012(17) 0.19413(9) 0.18024(9) 0.0422(3) Uani 1 1 d . . . . .
H5A H 0.6720 0.1424 0.2326 0.051 Uiso 1 1 calc R U . . .
C6 C 0.53435(17) 0.13101(10) 0.09523(9) 0.0464(3) Uani 1 1 d . . . . .
H6A H 0.3911 0.1227 0.0991 0.056 Uiso 1 1 calc R U . . .
H6B H 0.5931 0.0565 0.0983 0.056 Uiso 1 1 calc R U . . .
C7 C 0.54155(18) 0.17921(10) -0.00052(9) 0.0490(3) Uani 1 1 d . . . . .
H7 H 0.4283 0.1441 -0.0437 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7383(2) 0.14612(12) -0.03281(10) 0.0532(3) Uani 1 1 d . . . . .
H8A H 0.7667 0.0678 -0.0189 0.064 Uiso 1 1 calc R U . . .
H8B H 0.7173 0.1552 -0.0992 0.064 Uiso 1 1 calc R U . . .
C9 C 0.92366(19) 0.21564(10) 0.01269(9) 0.0471(3) Uani 1 1 d . . . . .
H9 H 1.0418 0.1922 -0.0132 0.057 Uiso 1 1 calc R U . . .
C10 C 0.97899(16) 0.20093(9) 0.11734(9) 0.0416(3) Uani 1 1 d . . . . .
H10A H 0.9832 0.1216 0.1312 0.050 Uiso 1 1 calc R U . . .
H10B H 1.1159 0.2305 0.1392 0.050 Uiso 1 1 calc R U . . .
C10A C 0.83327(15) 0.25707(9) 0.17067(7) 0.0347(2) Uani 1 1 d . . . . .
C11 C 0.8813(2) 0.33868(11) -0.01108(9) 0.0497(3) Uani 1 1 d . . . . .
H11A H 0.8517 0.3483 -0.0776 0.060 Uiso 1 1 calc R U . . .
H11B H 1.0014 0.3831 0.0143 0.060 Uiso 1 1 calc R U . . .
C12 C 0.69848(18) 0.37781(9) 0.02892(8) 0.0427(3) Uani 1 1 d . . . . .
H12 H 0.6688 0.4558 0.0107 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5091(2) 0.30610(11) -0.01184(9) 0.0495(3) Uani 1 1 d . . . . .
H13A H 0.3967 0.3277 0.0175 0.059 Uiso 1 1 calc R U . . .
H13B H 0.4684 0.3229 -0.0771 0.059 Uiso 1 1 calc R U . . .


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 C2 1.3517(14) . ?
O1 C10A 1.4636(13) . ?
C2 O2 1.1984(15) . ?
C2 C3 1.5071(17) . ?
C3 C3A 1.5198(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4 1.5224(16) . ?
C3A C10A 1.5303(14) . ?
C3A C12 1.5373(16) . ?
C4 O4 1.2017(15) . ?
C4 O5 1.3386(15) . ?
O5 C5A 1.4703(14) . ?
C5A C6 1.5140(17) . ?
C5A C10A 1.5185(14) . ?
C5A H5A 0.9800 . ?
C6 C7 1.537(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.5296(18) . ?
C7 C13 1.5377(18) . ?
C7 H7 0.9800 . ?
C8 C9 1.5274(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.5264(18) . ?
C9 C10 1.5272(18) . ?
C9 H9 0.9800 . ?
C10 C10A 1.5205(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5260(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.5434(17) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C2 O1 C10A 110.78(8) . . ?
O2 C2 O1 121.36(12) . . ?
O2 C2 C3 128.58(11) . . ?
O1 C2 C3 110.05(10) . . ?
C2 C3 C3A 103.07(9) . . ?
C2 C3 H3A 111.2 . . ?
C3A C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C3A C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C3 C3A C4 110.02(9) . . ?
C3 C3A C10A 103.28(9) . . ?
C4 C3A C10A 101.82(9) . . ?
C3 C3A C12 117.86(9) . . ?
C4 C3A C12 109.71(9) . . ?
C10A C3A C12 112.85(9) . . ?
O4 C4 O5 122.31(11) . . ?
O4 C4 C3A 127.17(12) . . ?
O5 C4 C3A 110.51(9) . . ?
C4 O5 C5A 110.81(9) . . ?
O5 C5A C6 109.12(9) . . ?
O5 C5A C10A 103.71(8) . . ?
C6 C5A C10A 115.59(10) . . ?
O5 C5A H5A 109.4 . . ?
C6 C5A H5A 109.4 . . ?
C10A C5A H5A 109.4 . . ?
C5A C6 C7 118.85(10) . . ?
C5A C6 H6A 107.6 . . ?
C7 C6 H6A 107.6 . . ?
C5A C6 H6B 107.6 . . ?
C7 C6 H6B 107.6 . . ?
H6A C6 H6B 107.0 . . ?
C8 C7 C13 109.37(11) . . ?
C8 C7 C6 111.98(11) . . ?
C13 C7 C6 116.18(10) . . ?
C8 C7 H7 106.2 . . ?
C13 C7 H7 106.2 . . ?
C6 C7 H7 106.2 . . ?
C9 C8 C7 112.73(10) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C11 C9 C10 109.91(10) . . ?
C11 C9 C8 109.14(11) . . ?
C10 C9 C8 113.22(11) . . ?
C11 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C10A C10 C9 115.07(9) . . ?
C10A C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C10A C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
O1 C10A C5A 107.35(9) . . ?
O1 C10A C10 108.01(9) . . ?
C5A C10A C10 117.78(9) . . ?
O1 C10A C3A 103.38(8) . . ?
C5A C10A C3A 103.59(8) . . ?
C10 C10A C3A 115.56(9) . . ?
C9 C11 C12 109.35(10) . . ?
C9 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C9 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C3A 109.58(9) . . ?
C11 C12 C13 109.17(10) . . ?
C3A C12 C13 112.48(10) . . ?
C11 C12 H12 108.5 . . ?
C3A C12 H12 108.5 . . ?
C13 C12 H12 108.5 . . ?
C7 C13 C12 114.85(10) . . ?
C7 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C7 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?

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
C10A O1 C2 O2 -175.44(11) . . . . ?
C10A O1 C2 C3 5.17(13) . . . . ?
O2 C2 C3 C3A -164.78(13) . . . . ?
O1 C2 C3 C3A 14.56(13) . . . . ?
C2 C3 C3A C4 80.96(11) . . . . ?
C2 C3 C3A C10A -27.10(11) . . . . ?
C2 C3 C3A C12 -152.27(10) . . . . ?
C3 C3A C4 O4 55.67(16) . . . . ?
C10A C3A C4 O4 164.69(13) . . . . ?
C12 C3A C4 O4 -75.55(15) . . . . ?
C3 C3A C4 O5 -125.41(10) . . . . ?
C10A C3A C4 O5 -16.38(12) . . . . ?
C12 C3A C4 O5 103.38(11) . . . . ?
O4 C4 O5 C5A 176.13(12) . . . . ?
C3A C4 O5 C5A -2.85(13) . . . . ?
C4 O5 C5A C6 -102.55(11) . . . . ?
C4 O5 C5A C10A 21.17(12) . . . . ?
O5 C5A C6 C7 83.18(12) . . . . ?
C10A C5A C6 C7 -33.19(15) . . . . ?
C5A C6 C7 C8 84.52(13) . . . . ?
C5A C6 C7 C13 -42.14(15) . . . . ?
C13 C7 C8 C9 52.13(15) . . . . ?
C6 C7 C8 C9 -78.13(14) . . . . ?
C7 C8 C9 C11 -60.09(15) . . . . ?
C7 C8 C9 C10 62.67(15) . . . . ?
C11 C9 C10 C10A 49.04(13) . . . . ?
C8 C9 C10 C10A -73.29(13) . . . . ?
C2 O1 C10A C5A -131.68(10) . . . . ?
C2 O1 C10A C10 100.36(10) . . . . ?
C2 O1 C10A C3A -22.57(11) . . . . ?
O5 C5A C10A O1 78.76(10) . . . . ?
C6 C5A C10A O1 -161.86(9) . . . . ?
O5 C5A C10A C10 -159.19(9) . . . . ?
C6 C5A C10A C10 -39.80(14) . . . . ?
O5 C5A C10A C3A -30.20(11) . . . . ?
C6 C5A C10A C3A 89.18(11) . . . . ?
C9 C10 C10A O1 -154.32(9) . . . . ?
C9 C10 C10A C5A 83.96(13) . . . . ?
C9 C10 C10A C3A -39.16(13) . . . . ?
C3 C3A C10A O1 30.23(10) . . . . ?
C4 C3A C10A O1 -83.89(9) . . . . ?
C12 C3A C10A O1 158.59(9) . . . . ?
C3 C3A C10A C5A 142.13(9) . . . . ?
C4 C3A C10A C5A 28.00(11) . . . . ?
C12 C3A C10A C5A -89.52(11) . . . . ?
C3 C3A C10A C10 -87.55(11) . . . . ?
C4 C3A C10A C10 158.33(9) . . . . ?
C12 C3A C10A C10 40.81(12) . . . . ?
C10 C9 C11 C12 -61.79(13) . . . . ?
C8 C9 C11 C12 62.93(13) . . . . ?
C9 C11 C12 C3A 64.37(12) . . . . ?
C9 C11 C12 C13 -59.22(13) . . . . ?
C3 C3A C12 C11 67.18(13) . . . . ?
C4 C3A C12 C11 -165.90(9) . . . . ?
C10A C3A C12 C11 -53.12(12) . . . . ?
C3 C3A C12 C13 -171.19(10) . . . . ?
C4 C3A C12 C13 -44.27(12) . . . . ?
C10A C3A C12 C13 68.51(12) . . . . ?
C8 C7 C13 C12 -49.60(15) . . . . ?
C6 C7 C13 C12 78.35(14) . . . . ?
C11 C12 C13 C7 53.99(14) . . . . ?
C3A C12 C13 C7 -67.87(14) . . . . ?

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
C6 H6B O2 0.97 2.54 3.4146(15) 149.8 2_745
C10 H10A O2 0.97 2.50 3.4402(16) 164.1 2_745
C10 H10B O5 0.97 2.62 3.5879(14) 172.3 1_655
############################################################################### 

_audit_creation_method           SHELXL--2013

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_measurement_reflns_used    12363
_cell_measurement_theta_min      4.795
_cell_measurement_theta_max      73.083

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.863
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.043
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9144
_exptl_absorpt_correction_T_max  0.9578
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
;
 63 runs, 1692 frames, detector distance = 42 mm  
;
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_reflns_number            12363
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.795
_diffrn_reflns_theta_max         73.083
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2254
_reflns_number_gt                2042
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X--AREA      (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA      (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA      (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97     (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL--2013 (Sheldrick,  2013)'
_computing_molecular_graphics    'Ortep--3     (Farrugia,   1997)'
_computing_publication_material  'WinGX        (Farrugia,   1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.2227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2254
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_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.
;

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ryb1903
_audit_block_doi                 10.5517/ccdc.csd.cc235h2w
_database_code_depnum_ccdc_archive 'CCDC 1941687'
loop_
_audit_author_name
_audit_author_address
'Victor  Rybakov'
;Moscow State University, Chemistry Department
Russia
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;

_vrf_PLAT026_I                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        28% Check 
RESPONSE: Pure diffraction data. See: _diffrn_reflns_theta_max   63.201 
;

_chemical_name_systematic        
Octahydro-8,4a,10-(epipropane[1,2,3]triyl)cyclohepta[2,3]furo[3,4-b]pyran-2,5-dione
_chemical_name_common            ?
_chemical_melting_point_gt       490.6
_chemical_melting_point_lt       491.4
_chemical_formula_moiety         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_preparation       Methanol

_cell_length_a                   10.4928(9)
_cell_length_b                   7.4635(8)
_cell_length_c                   16.0005(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.678(2)
_cell_angle_gamma                90
_cell_volume                     1244.55(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.2001
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0773

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7634(4) 0.3698(6) -0.0471(3) 0.0627(14) Uani 1 1 d . . . . .
H1A H 0.8219 0.4312 -0.0801 0.075 Uiso 1 1 calc R U . . .
H1B H 0.6878 0.3389 -0.0852 0.075 Uiso 1 1 calc R U . . .
C2 C 0.7236(5) 0.4994(6) 0.0153(3) 0.0711(15) Uani 1 1 d . . . . .
H2 H 0.6586 0.5805 -0.0126 0.085 Uiso 1 1 calc R U . . .
O2 O 0.8382(3) 0.6057(4) 0.0505(2) 0.0682(10) Uani 1 1 d . . . . .
C3 C 0.6736(4) 0.4174(6) 0.0944(3) 0.0553(13) Uani 1 1 d . . . . .
C4 C 0.5947(4) 0.2525(7) 0.0853(3) 0.0809(16) Uani 1 1 d . . . . .
H4A H 0.5341 0.2636 0.0350 0.097 Uiso 1 1 calc R U . . .
H4B H 0.5455 0.2447 0.1329 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6705(6) 0.0733(7) 0.0798(4) 0.0873(17) Uani 1 1 d . . . . .
H5 H 0.6112 -0.0258 0.0861 0.105 Uiso 1 1 calc R U . . .
C6 C 0.7250(5) 0.0485(7) -0.0040(4) 0.1003(19) Uani 1 1 d . . . . .
H6A H 0.6562 0.0566 -0.0499 0.120 Uiso 1 1 calc R U . . .
H6B H 0.7635 -0.0695 -0.0058 0.120 Uiso 1 1 calc R U . . .
C7 C 0.8278(5) 0.1943(6) -0.0150(4) 0.0792(17) Uani 1 1 d . . . . .
H7 H 0.8749 0.1514 -0.0604 0.095 Uiso 1 1 calc R U . . .
C8 C 0.9254(5) 0.2080(6) 0.0614(4) 0.0781(16) Uani 1 1 d . . . . .
H8A H 0.9787 0.3125 0.0556 0.094 Uiso 1 1 calc R U . . .
H8B H 0.9805 0.1033 0.0636 0.094 Uiso 1 1 calc R U . . .
C9 C 0.8667(5) 0.2220(6) 0.1440(3) 0.0683(15) Uani 1 1 d . . . . .
H9 H 0.9372 0.2106 0.1895 0.082 Uiso 1 1 calc R U . . .
C10 C 0.7761(5) 0.0645(6) 0.1522(4) 0.0774(16) Uani 1 1 d . . . . .
H10A H 0.8224 -0.0477 0.1506 0.093 Uiso 1 1 calc R U . . .
H10B H 0.7401 0.0715 0.2052 0.093 Uiso 1 1 calc R U . . .
C11 C 0.7992(4) 0.4025(5) 0.1570(3) 0.0466(11) Uani 1 1 d . . . . .
C12 C 0.7766(5) 0.4277(6) 0.2488(3) 0.0730(15) Uani 1 1 d . . . . .
H12A H 0.7262 0.3284 0.2662 0.088 Uiso 1 1 calc R U . . .
H12B H 0.8583 0.4281 0.2840 0.088 Uiso 1 1 calc R U . . .
C13 C 0.7066(5) 0.6025(7) 0.2604(3) 0.0873(17) Uani 1 1 d . . . . .
H13A H 0.6754 0.6009 0.3152 0.105 Uiso 1 1 calc R U . . .
H13B H 0.7674 0.7004 0.2604 0.105 Uiso 1 1 calc R U . . .
C14 C 0.5953(6) 0.6394(7) 0.1946(4) 0.0712(16) Uani 1 1 d . . . . .
O14 O 0.5112(4) 0.7410(5) 0.2072(2) 0.1031(14) Uani 1 1 d . . . . .
O15 O 0.5901(3) 0.5607(4) 0.1201(2) 0.0777(11) Uani 1 1 d . . . . .
C16 C 0.8812(5) 0.5551(6) 0.1271(4) 0.0564(13) Uani 1 1 d . . . . .
O16 O 0.9738(4) 0.6192(5) 0.1658(2) 0.0899(12) Uani 1 1 d . . . . .


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
C1 C2 1.485(6) . ?
C1 C7 1.535(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O2 1.495(5) . ?
C2 C3 1.552(6) . ?
C2 H2 0.9800 . ?
O2 C16 1.312(5) . ?
C3 O15 1.470(5) . ?
C3 C4 1.481(6) . ?
C3 C11 1.564(5) . ?
C4 C5 1.563(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.508(6) . ?
C5 C6 1.529(7) . ?
C5 H5 0.9800 . ?
C6 C7 1.557(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.504(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.525(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.528(6) . ?
C9 C11 1.547(6) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(5) . ?
C11 C16 1.536(6) . ?
C12 C13 1.519(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.505(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O14 1.199(5) . ?
C14 O15 1.324(6) . ?
C16 O16 1.189(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 118.5(4) . . ?
C2 C1 H1A 107.7 . . ?
C7 C1 H1A 107.7 . . ?
C2 C1 H1B 107.7 . . ?
C7 C1 H1B 107.7 . . ?
H1A C1 H1B 107.1 . . ?
C1 C2 O2 108.8(4) . . ?
C1 C2 C3 116.1(4) . . ?
O2 C2 C3 103.6(4) . . ?
C1 C2 H2 109.3 . . ?
O2 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C16 O2 C2 111.9(4) . . ?
O15 C3 C4 106.7(4) . . ?
O15 C3 C2 102.1(3) . . ?
C4 C3 C2 119.1(4) . . ?
O15 C3 C11 111.0(4) . . ?
C4 C3 C11 115.1(4) . . ?
C2 C3 C11 102.1(4) . . ?
C3 C4 C5 115.7(4) . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C10 C5 C6 110.6(5) . . ?
C10 C5 C4 109.1(4) . . ?
C6 C5 C4 113.5(5) . . ?
C10 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
C5 C6 C7 110.4(4) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C1 116.5(4) . . ?
C8 C7 C6 111.8(4) . . ?
C1 C7 C6 110.5(5) . . ?
C8 C7 H7 105.7 . . ?
C1 C7 H7 105.7 . . ?
C6 C7 H7 105.7 . . ?
C7 C8 C9 113.8(4) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 109.9(4) . . ?
C8 C9 C11 114.4(4) . . ?
C10 C9 C11 111.0(4) . . ?
C8 C9 H9 107.0 . . ?
C10 C9 H9 107.0 . . ?
C11 C9 H9 107.0 . . ?
C5 C10 C9 108.0(4) . . ?
C5 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
C5 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C12 C11 C16 111.3(4) . . ?
C12 C11 C9 111.2(4) . . ?
C16 C11 C9 108.8(4) . . ?
C12 C11 C3 113.1(4) . . ?
C16 C11 C3 102.1(4) . . ?
C9 C11 C3 109.9(3) . . ?
C13 C12 C11 110.9(4) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 114.7(4) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
O14 C14 O15 118.6(5) . . ?
O14 C14 C13 121.6(6) . . ?
O15 C14 C13 119.8(5) . . ?
C14 O15 C3 127.6(4) . . ?
O16 C16 O2 122.7(5) . . ?
O16 C16 C11 126.1(5) . . ?
O2 C16 C11 111.1(5) . . ?

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
C7 C1 C2 O2 81.0(5) . . . . ?
C7 C1 C2 C3 -35.4(6) . . . . ?
C1 C2 O2 C16 -105.1(4) . . . . ?
C3 C2 O2 C16 19.1(4) . . . . ?
C1 C2 C3 O15 -154.5(4) . . . . ?
O2 C2 C3 O15 86.3(4) . . . . ?
C1 C2 C3 C4 -37.3(6) . . . . ?
O2 C2 C3 C4 -156.6(4) . . . . ?
C1 C2 C3 C11 90.6(5) . . . . ?
O2 C2 C3 C11 -28.6(4) . . . . ?
O15 C3 C4 C5 -165.8(4) . . . . ?
C2 C3 C4 C5 79.5(5) . . . . ?
C11 C3 C4 C5 -42.1(6) . . . . ?
C3 C4 C5 C10 51.2(6) . . . . ?
C3 C4 C5 C6 -72.6(6) . . . . ?
C10 C5 C6 C7 -58.2(5) . . . . ?
C4 C5 C6 C7 64.8(7) . . . . ?
C2 C1 C7 C8 -41.8(6) . . . . ?
C2 C1 C7 C6 87.2(5) . . . . ?
C5 C6 C7 C8 49.8(6) . . . . ?
C5 C6 C7 C1 -81.7(5) . . . . ?
C1 C7 C8 C9 79.1(6) . . . . ?
C6 C7 C8 C9 -49.3(6) . . . . ?
C7 C8 C9 C10 55.2(5) . . . . ?
C7 C8 C9 C11 -70.5(6) . . . . ?
C6 C5 C10 C9 64.0(5) . . . . ?
C4 C5 C10 C9 -61.5(5) . . . . ?
C8 C9 C10 C5 -61.1(5) . . . . ?
C11 C9 C10 C5 66.6(5) . . . . ?
C8 C9 C11 C12 -164.1(4) . . . . ?
C10 C9 C11 C12 70.8(5) . . . . ?
C8 C9 C11 C16 -41.2(6) . . . . ?
C10 C9 C11 C16 -166.3(4) . . . . ?
C8 C9 C11 C3 69.8(5) . . . . ?
C10 C9 C11 C3 -55.3(5) . . . . ?
O15 C3 C11 C12 39.4(5) . . . . ?
C4 C3 C11 C12 -81.9(5) . . . . ?
C2 C3 C11 C12 147.6(4) . . . . ?
O15 C3 C11 C16 -80.3(4) . . . . ?
C4 C3 C11 C16 158.4(4) . . . . ?
C2 C3 C11 C16 27.9(4) . . . . ?
O15 C3 C11 C9 164.4(4) . . . . ?
C4 C3 C11 C9 43.1(5) . . . . ?
C2 C3 C11 C9 -87.4(4) . . . . ?
C16 C11 C12 C13 60.3(5) . . . . ?
C9 C11 C12 C13 -178.2(4) . . . . ?
C3 C11 C12 C13 -53.9(5) . . . . ?
C11 C12 C13 C14 44.5(6) . . . . ?
C12 C13 C14 O14 158.7(5) . . . . ?
C12 C13 C14 O15 -22.4(7) . . . . ?
O14 C14 O15 C3 -172.3(5) . . . . ?
C13 C14 O15 C3 8.8(7) . . . . ?
C4 C3 O15 C14 108.9(5) . . . . ?
C2 C3 O15 C14 -125.4(5) . . . . ?
C11 C3 O15 C14 -17.2(6) . . . . ?
C2 O2 C16 O16 178.0(5) . . . . ?
C2 O2 C16 C11 -0.4(5) . . . . ?
C12 C11 C16 O16 42.5(7) . . . . ?
C9 C11 C16 O16 -80.3(6) . . . . ?
C3 C11 C16 O16 163.5(5) . . . . ?
C12 C11 C16 O2 -139.2(4) . . . . ?
C9 C11 C16 O2 97.9(4) . . . . ?
C3 C11 C16 O2 -18.2(5) . . . . ?
############################################################################## 

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_measurement_reflns_used    9152
_cell_measurement_theta_min      4.242
_cell_measurement_theta_max      63.201

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.828
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.083
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D. (1983). Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.8662
_exptl_absorpt_correction_T_max  0.9099

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
;
 45 runs, 1254 frames, detector distance = 42 mm   
;
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_reflns_number            9152
_diffrn_reflns_av_unetI/netI     0.2151
_diffrn_reflns_av_R_equivalents  0.0813 # before absorption correction
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.242
_diffrn_reflns_theta_max         63.201
_diffrn_reflns_theta_full        63.201
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1981
_reflns_number_gt                556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0087P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1981
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.693
_refine_ls_restrained_S_all      0.693
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_Klim1810
_audit_block_doi                 10.5517/ccdc.csd.cc235h1v
_database_code_depnum_ccdc_archive 'CCDC 1941686'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Moscow State University
Russia
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;

_chemical_name_systematic        
'hexahydro-7,3a,9-propane[1,2,3]triylcyclohepta[2,3]furo[3,4-d][1,3,2]dioxathiol-4-one 2,2-dioxide'
_chemical_name_common            ?
_chemical_melting_point_gt       462.8
_chemical_melting_point_lt       463.6
_chemical_formula_moiety         'C12 H14 O6 S'
_chemical_formula_sum            'C12 H14 O6 S'
_chemical_formula_weight         286.29

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_preparation       'Ethyl acetate'

_cell_length_a                   12.4516(5)
_cell_length_b                   7.6976(2)
_cell_length_c                   13.8142(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.596(3)
_cell_angle_gamma                90
_cell_volume                     1203.92(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0877

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.28979(4) -0.18391(5) 0.40666(3) 0.05158(15) Uani 1 1 d . . . . .
O21 O 0.21420(16) -0.32485(18) 0.39671(15) 0.0813(5) Uani 1 1 d . . . . .
O22 O 0.39542(14) -0.1722(2) 0.49785(12) 0.0872(5) Uani 1 1 d . . . . .
O1 O 0.21646(11) -0.01180(15) 0.38830(9) 0.0533(3) Uani 1 1 d . . . . .
O3 O 0.31813(10) -0.17159(13) 0.30509(9) 0.0470(3) Uani 1 1 d . . . . .
C3A C 0.24192(12) -0.04411(18) 0.23207(11) 0.0382(3) Uani 1 1 d . . . . .
C4 C 0.11786(14) -0.1189(2) 0.16988(13) 0.0470(4) Uani 1 1 d . . . . .
O41 O 0.09273(12) -0.25586(17) 0.12490(11) 0.0676(4) Uani 1 1 d . . . . .
O5 O 0.03827(9) -0.00691(15) 0.17253(10) 0.0555(3) Uani 1 1 d . . . . .
C5A C 0.09480(14) 0.1504(2) 0.23182(14) 0.0470(4) Uani 1 1 d . . . . .
H5A H 0.0560 0.1845 0.2778 0.056 Uiso 1 1 calc R U . . .
C6 C 0.08336(15) 0.2967(2) 0.15435(15) 0.0517(4) Uani 1 1 d . . . . .
H6A H 0.0860 0.4056 0.1907 0.062 Uiso 1 1 calc R U . . .
H6B H 0.0055 0.2883 0.0961 0.062 Uiso 1 1 calc R U . . .
C7 C 0.17400(15) 0.3081(2) 0.10572(14) 0.0474(4) Uani 1 1 d . . . . .
H7 H 0.1375 0.3797 0.0416 0.057 Uiso 1 1 calc R U . . .
C8 C 0.28698(16) 0.4027(2) 0.17820(15) 0.0522(4) Uani 1 1 d . . . . .
H8A H 0.3288 0.4400 0.1362 0.063 Uiso 1 1 calc R U . . .
H8B H 0.2659 0.5058 0.2068 0.063 Uiso 1 1 calc R U . . .
C9 C 0.36845(15) 0.2907(2) 0.26963(14) 0.0495(4) Uani 1 1 d . . . . .
H9 H 0.4396 0.3585 0.3106 0.059 Uiso 1 1 calc R U . . .
C10 C 0.31379(15) 0.2341(2) 0.34554(13) 0.0478(4) Uani 1 1 d . . . . .
H10A H 0.3760 0.1914 0.4108 0.057 Uiso 1 1 calc R U . . .
H10B H 0.2788 0.3347 0.3634 0.057 Uiso 1 1 calc R U . . .
C10A C 0.22024(13) 0.09428(19) 0.30009(12) 0.0398(3) Uani 1 1 d . . . . .
C11 C 0.40562(14) 0.1302(2) 0.22615(15) 0.0527(4) Uani 1 1 d . . . . .
H11A H 0.4593 0.0600 0.2846 0.063 Uiso 1 1 calc R U . . .
H11B H 0.4462 0.1652 0.1827 0.063 Uiso 1 1 calc R U . . .
C12 C 0.29551(14) 0.0241(2) 0.15918(12) 0.0445(3) Uani 1 1 d . . . . .
H12 H 0.3191 -0.0747 0.1277 0.053 Uiso 1 1 calc R U . . .
C13 C 0.20641(16) 0.1354(2) 0.06929(13) 0.0506(4) Uani 1 1 d . . . . .
H13A H 0.2389 0.1599 0.0179 0.061 Uiso 1 1 calc R U . . .
H13B H 0.1348 0.0684 0.0332 0.061 Uiso 1 1 calc R U . . .


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
S2 O22 1.3949(16) . ?
S2 O21 1.4051(15) . ?
S2 O1 1.5685(12) . ?
S2 O3 1.5856(12) . ?
O1 C10A 1.4838(17) . ?
O3 C3A 1.4436(17) . ?
C3A C12 1.515(2) . ?
C3A C10A 1.517(2) . ?
C3A C4 1.533(2) . ?
C4 O41 1.198(2) . ?
C4 O5 1.325(2) . ?
O5 C5A 1.467(2) . ?
C5A C10A 1.513(2) . ?
C5A C6 1.519(2) . ?
C5A H5A 0.9800 . ?
C6 C7 1.538(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.530(2) . ?
C7 C13 1.533(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.517(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.528(2) . ?
C9 C10 1.532(2) . ?
C9 H9 0.9800 . ?
C10 C10A 1.517(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.532(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.537(2) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
O22 S2 O21 118.65(11) . . ?
O22 S2 O1 110.99(9) . . ?
O21 S2 O1 108.37(8) . . ?
O22 S2 O3 108.77(9) . . ?
O21 S2 O3 110.26(9) . . ?
O1 S2 O3 97.78(6) . . ?
C10A O1 S2 112.48(9) . . ?
C3A O3 S2 109.60(9) . . ?
O3 C3A C12 110.91(11) . . ?
O3 C3A C10A 106.21(11) . . ?
C12 C3A C10A 114.18(12) . . ?
O3 C3A C4 110.62(12) . . ?
C12 C3A C4 112.18(13) . . ?
C10A C3A C4 102.30(12) . . ?
O41 C4 O5 123.37(16) . . ?
O41 C4 C3A 127.30(16) . . ?
O5 C4 C3A 109.33(13) . . ?
C4 O5 C5A 111.20(11) . . ?
O5 C5A C10A 104.08(12) . . ?
O5 C5A C6 109.64(15) . . ?
C10A C5A C6 114.87(13) . . ?
O5 C5A H5A 109.4 . . ?
C10A C5A H5A 109.4 . . ?
C6 C5A H5A 109.4 . . ?
C5A C6 C7 118.65(13) . . ?
C5A C6 H6A 107.7 . . ?
C7 C6 H6A 107.7 . . ?
C5A C6 H6B 107.7 . . ?
C7 C6 H6B 107.7 . . ?
H6A C6 H6B 107.1 . . ?
C8 C7 C13 109.38(14) . . ?
C8 C7 C6 112.54(15) . . ?
C13 C7 C6 115.82(13) . . ?
C8 C7 H7 106.1 . . ?
C13 C7 H7 106.1 . . ?
C6 C7 H7 106.1 . . ?
C9 C8 C7 112.84(13) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C11 109.85(15) . . ?
C8 C9 C10 113.44(14) . . ?
C11 C9 C10 109.44(13) . . ?
C8 C9 H9 108.0 . . ?
C11 C9 H9 108.0 . . ?
C10 C9 H9 108.0 . . ?
C10A C10 C9 113.70(13) . . ?
C10A C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C10A C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O1 C10A C5A 106.96(11) . . ?
O1 C10A C10 109.39(12) . . ?
C5A C10A C10 118.10(13) . . ?
O1 C10A C3A 101.36(11) . . ?
C5A C10A C3A 102.60(12) . . ?
C10 C10A C3A 116.78(12) . . ?
C9 C11 C12 109.10(12) . . ?
C9 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C9 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C3A C12 C11 108.33(13) . . ?
C3A C12 C13 111.15(13) . . ?
C11 C12 C13 110.76(14) . . ?
C3A C12 H12 108.9 . . ?
C11 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
C7 C13 C12 114.74(13) . . ?
C7 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C7 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?

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
O22 S2 O1 C10A 105.39(13) . . . . ?
O21 S2 O1 C10A -122.64(12) . . . . ?
O3 S2 O1 C10A -8.20(11) . . . . ?
O22 S2 O3 C3A -130.38(12) . . . . ?
O21 S2 O3 C3A 97.91(11) . . . . ?
O1 S2 O3 C3A -15.01(10) . . . . ?
S2 O3 C3A C12 157.18(10) . . . . ?
S2 O3 C3A C10A 32.59(13) . . . . ?
S2 O3 C3A C4 -77.67(13) . . . . ?
O3 C3A C4 O41 -48.3(2) . . . . ?
C12 C3A C4 O41 76.1(2) . . . . ?
C10A C3A C4 O41 -161.06(17) . . . . ?
O3 C3A C4 O5 131.72(13) . . . . ?
C12 C3A C4 O5 -103.87(15) . . . . ?
C10A C3A C4 O5 18.93(16) . . . . ?
O41 C4 O5 C5A -179.06(17) . . . . ?
C3A C4 O5 C5A 0.95(17) . . . . ?
C4 O5 C5A C10A -20.65(17) . . . . ?
C4 O5 C5A C6 102.70(15) . . . . ?
O5 C5A C6 C7 -83.80(18) . . . . ?
C10A C5A C6 C7 32.9(2) . . . . ?
C5A C6 C7 C8 -84.15(19) . . . . ?
C5A C6 C7 C13 42.7(2) . . . . ?
C13 C7 C8 C9 -52.90(18) . . . . ?
C6 C7 C8 C9 77.33(18) . . . . ?
C7 C8 C9 C11 60.40(18) . . . . ?
C7 C8 C9 C10 -62.43(19) . . . . ?
C8 C9 C10 C10A 73.88(18) . . . . ?
C11 C9 C10 C10A -49.19(18) . . . . ?
S2 O1 C10A C5A 133.72(11) . . . . ?
S2 O1 C10A C10 -97.28(13) . . . . ?
S2 O1 C10A C3A 26.63(14) . . . . ?
O5 C5A C10A O1 -75.11(14) . . . . ?
C6 C5A C10A O1 165.02(14) . . . . ?
O5 C5A C10A C10 161.09(12) . . . . ?
C6 C5A C10A C10 41.22(19) . . . . ?
O5 C5A C10A C3A 31.10(14) . . . . ?
C6 C5A C10A C3A -88.78(16) . . . . ?
C9 C10 C10A O1 151.66(13) . . . . ?
C9 C10 C10A C5A -85.76(17) . . . . ?
C9 C10 C10A C3A 37.36(19) . . . . ?
O3 C3A C10A O1 -35.48(14) . . . . ?
C12 C3A C10A O1 -158.02(12) . . . . ?
C4 C3A C10A O1 80.55(13) . . . . ?
O3 C3A C10A C5A -145.95(11) . . . . ?
C12 C3A C10A C5A 91.51(14) . . . . ?
C4 C3A C10A C5A -29.92(14) . . . . ?
O3 C3A C10A C10 83.25(15) . . . . ?
C12 C3A C10A C10 -39.29(18) . . . . ?
C4 C3A C10A C10 -160.72(13) . . . . ?
C8 C9 C11 C12 -60.98(17) . . . . ?
C10 C9 C11 C12 64.19(18) . . . . ?
O3 C3A C12 C11 -67.83(15) . . . . ?
C10A C3A C12 C11 52.11(16) . . . . ?
C4 C3A C12 C11 167.91(13) . . . . ?
O3 C3A C12 C13 170.27(12) . . . . ?
C10A C3A C12 C13 -69.79(17) . . . . ?
C4 C3A C12 C13 46.01(17) . . . . ?
C9 C11 C12 C3A -65.41(17) . . . . ?
C9 C11 C12 C13 56.74(17) . . . . ?
C8 C7 C13 C12 49.19(18) . . . . ?
C6 C7 C13 C12 -79.24(19) . . . . ?
C3A C12 C13 C7 67.96(18) . . . . ?
C11 C12 C13 C7 -52.52(18) . . . . ?
############################################################################

_audit_creation_method           SHELXL-2013

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_measurement_reflns_used    12950
_cell_measurement_theta_min      3.904
_cell_measurement_theta_max      72.968

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.619
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.622
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.262
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.7141
_exptl_absorpt_correction_T_max  0.7696
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
;
 65 runs, 1727 frames, detector distance = 42 mm  
;
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_reflns_number            12950
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0330 # before absorption correction
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.904
_diffrn_reflns_theta_max         72.968
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2386
_reflns_number_gt                2132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X--AREA      (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA      (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA      (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97     (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL--2013 (Sheldrick,  2013)'
_computing_molecular_graphics    'Ortep--3     (Farrugia,   1997)'
_computing_publication_material  'WinGX        (Farrugia,   1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.3370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2386
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_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.
;

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

