# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DB1_120B_5
_database_code_depnum_ccdc_archive 'CCDC 1051641'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 O6 S Ca, 0.3(C4 H10)'
_chemical_formula_sum            'C15.19 H10.98 Ca O6 S'
_chemical_formula_weight         361.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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)/n

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

_cell_length_a                   11.8013(12)
_cell_length_b                   5.5827(6)
_cell_length_c                   22.723(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.092(2)
_cell_angle_gamma                90.00
_cell_volume                     1473.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4607
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      32.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             745
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17056
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         32.15
_reflns_number_total             5125
_reflns_number_gt                4332
_reflns_threshold_expression     >2sigma(I)

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

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


 The butane solvate site was modeled with two parts with total occupancy of
 0.3.  The SHELXL restraints used were:
DFIX 1.55 .005 C41A C42A C42A C43A C43A C44A
DFIX 2.53 .005 C41A C43A C42A C44A
DFIX 1.55 .005 C41B C42B C42B C43B C43B C44B
DFIX 2.53 .005 C41B C43B C42B C44B
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+3.5000P] 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         5125
_refine_ls_number_parameters     234
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.63783(3) 0.24423(7) 0.222873(17) 0.00879(9) Uani 1 1 d . . .
S1 S 0.40115(4) 0.03640(9) 0.10805(2) 0.00916(10) Uani 1 1 d . . .
O1 O 0.26576(13) 0.4753(3) -0.17171(7) 0.0122(3) Uani 1 1 d . . .
O2 O 0.26177(13) 0.0841(3) -0.19080(6) 0.0116(3) Uani 1 1 d . . .
O3 O 0.41854(14) -0.2184(3) 0.11215(7) 0.0129(3) Uani 1 1 d . . .
O4 O 0.49592(13) 0.1958(3) 0.13092(7) 0.0124(3) Uani 1 1 d . . .
O5 O -0.01431(13) 0.4762(3) 0.24494(7) 0.0135(3) Uani 1 1 d . . .
O6 O -0.04358(14) 0.0815(3) 0.25390(7) 0.0148(3) Uani 1 1 d . . .
C1 C 0.27611(17) 0.2609(4) -0.15515(9) 0.0100(3) Uani 1 1 d . . .
C2 C 0.30225(18) 0.2075(4) -0.08910(9) 0.0105(3) Uani 1 1 d . . .
C3 C 0.35575(19) 0.3805(4) -0.04976(9) 0.0125(4) Uani 1 1 d . . .
H3 H 0.3731 0.5328 -0.0646 0.015 Uiso 1 1 calc R . .
C4 C 0.38409(19) 0.3329(4) 0.01096(9) 0.0128(4) Uani 1 1 d . . .
H4 H 0.4211 0.4507 0.0378 0.015 Uiso 1 1 calc R . .
C5 C 0.35719(17) 0.1088(4) 0.03165(9) 0.0101(3) Uani 1 1 d . . .
C6 C 0.2998(2) -0.0633(4) -0.00671(9) 0.0143(4) Uani 1 1 d . . .
H6 H 0.2794 -0.2127 0.0085 0.017 Uiso 1 1 calc R . .
C7 C 0.27283(19) -0.0140(4) -0.06754(9) 0.0137(4) Uani 1 1 d . . .
H7 H 0.2345 -0.1306 -0.0943 0.016 Uiso 1 1 calc R . .
C8 C 0.28380(18) 0.1089(4) 0.14322(9) 0.0105(3) Uani 1 1 d . . .
C9 C 0.28144(18) 0.3287(4) 0.17217(9) 0.0114(4) Uani 1 1 d . . .
H9 H 0.3413 0.4426 0.1723 0.014 Uiso 1 1 calc R . .
C10 C 0.18884(18) 0.3764(4) 0.20083(9) 0.0113(4) Uani 1 1 d . . .
H10 H 0.1847 0.5260 0.2203 0.014 Uiso 1 1 calc R . .
C11 C 0.10213(17) 0.2075(4) 0.20137(9) 0.0100(3) Uani 1 1 d . . .
C12 C 0.00597(17) 0.2597(4) 0.23614(9) 0.0104(3) Uani 1 1 d . . .
C13 C 0.10561(18) -0.0106(4) 0.17190(9) 0.0126(4) Uani 1 1 d . . .
H13 H 0.0463 -0.1254 0.1723 0.015 Uiso 1 1 calc R . .
C14 C 0.19604(19) -0.0599(4) 0.14189(9) 0.0128(4) Uani 1 1 d . . .
H14 H 0.1981 -0.2062 0.1208 0.015 Uiso 1 1 calc R . .
C41A C -0.019(2) 0.468(4) 0.0697(8) 0.039(5) Uiso 0.162(6) 1 d PD A 1
H41A H -0.0008 0.5364 0.1099 0.058 Uiso 0.162(6) 1 calc PR A 1
H41B H 0.0431 0.3590 0.0634 0.058 Uiso 0.162(6) 1 calc PR A 1
H41C H -0.0914 0.3790 0.0654 0.058 Uiso 0.162(6) 1 calc PR A 1
C42A C -0.0304(19) 0.672(3) 0.0228(8) 0.045(5) Uiso 0.162(6) 1 d PD A 1
H42A H -0.0915 0.7843 0.0297 0.055 Uiso 0.162(6) 1 calc PR A 1
H42B H 0.0429 0.7615 0.0269 0.055 Uiso 0.162(6) 1 calc PR A 1
C43A C -0.0605(16) 0.564(5) -0.0408(7) 0.082(11) Uiso 0.162(6) 1 d PD A 1
H43A H -0.0975 0.6881 -0.0690 0.098 Uiso 0.162(6) 1 calc PR A 1
H43B H -0.1154 0.4302 -0.0409 0.098 Uiso 0.162(6) 1 calc PR A 1
C44A C 0.0505(19) 0.473(4) -0.0610(10) 0.040(5) Uiso 0.162(6) 1 d PD A 1
H44A H 0.0314 0.4093 -0.1017 0.059 Uiso 0.162(6) 1 calc PR A 1
H44B H 0.0853 0.3465 -0.0339 0.059 Uiso 0.162(6) 1 calc PR A 1
H44C H 0.1050 0.6059 -0.0603 0.059 Uiso 0.162(6) 1 calc PR A 1
C41B C -0.012(5) 0.779(5) -0.003(3) 0.086(16) Uiso 0.115(6) 1 d PD B 2
H41D H 0.0152 0.8999 -0.0288 0.129 Uiso 0.115(6) 1 calc PR B 2
H41E H 0.0084 0.8284 0.0387 0.129 Uiso 0.115(6) 1 calc PR B 2
H41F H -0.0957 0.7633 -0.0140 0.129 Uiso 0.115(6) 1 calc PR B 2
C42B C 0.045(5) 0.535(6) -0.012(2) 0.10(2) Uiso 0.115(6) 1 d PD B 2
H42C H 0.0176 0.4749 -0.0529 0.124 Uiso 0.115(6) 1 calc PR B 2
H42D H 0.1300 0.5553 -0.0067 0.124 Uiso 0.115(6) 1 calc PR B 2
C43B C 0.016(4) 0.353(5) 0.0344(16) 0.063(11) Uiso 0.115(6) 1 d PD B 2
H43C H -0.0565 0.4015 0.0477 0.076 Uiso 0.115(6) 1 calc PR B 2
H43D H 0.0779 0.3496 0.0698 0.076 Uiso 0.115(6) 1 calc PR B 2
C44B C 0.001(7) 0.101(6) 0.006(3) 0.11(2) Uiso 0.115(6) 1 d PD B 2
H44D H -0.0271 -0.0109 0.0332 0.161 Uiso 0.115(6) 1 calc PR B 2
H44E H 0.0749 0.0445 -0.0028 0.161 Uiso 0.115(6) 1 calc PR B 2
H44F H -0.0551 0.1085 -0.0317 0.161 Uiso 0.115(6) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ca1 O6 2.2949(16) 2 ?
Ca1 O5 2.2961(16) 2_545 ?
Ca1 O1 2.3585(16) 3_665 ?
Ca1 O2 2.3660(16) 3_655 ?
Ca1 O2 2.4290(16) 4_666 ?
Ca1 O4 2.4530(16) . ?
S1 O3 1.4381(16) . ?
S1 O4 1.4524(16) . ?
S1 C8 1.763(2) . ?
S1 C5 1.769(2) . ?
O1 C1 1.254(3) . ?
O1 Ca1 2.3586(15) 3_665 ?
O1 Ca1 2.8726(16) 4_565 ?
O2 C1 1.269(2) . ?
O2 Ca1 2.3660(16) 3_655 ?
O2 Ca1 2.4290(16) 4_565 ?
O5 C12 1.255(3) . ?
O5 Ca1 2.2960(16) 2 ?
O6 C12 1.256(2) . ?
O6 Ca1 2.2949(16) 2_545 ?
C1 C2 1.508(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.396(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 C14 1.397(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 C13 1.394(3) . ?
C11 C12 1.520(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C41A C42A 1.548(5) . ?
C41A H41A 0.9800 . ?
C41A H41B 0.9800 . ?
C41A H41C 0.9800 . ?
C42A C43A 1.547(5) . ?
C42A H42A 0.9900 . ?
C42A H42B 0.9900 . ?
C43A C44A 1.548(5) . ?
C43A H43A 0.9900 . ?
C43A H43B 0.9900 . ?
C44A H44A 0.9800 . ?
C44A H44B 0.9800 . ?
C44A H44C 0.9800 . ?
C41B C42B 1.550(5) . ?
C41B H41D 0.9800 . ?
C41B H41E 0.9800 . ?
C41B H41F 0.9800 . ?
C42B C43B 1.549(5) . ?
C42B H42C 0.9900 . ?
C42B H42D 0.9900 . ?
C43B C44B 1.550(5) . ?
C43B H43C 0.9900 . ?
C43B H43D 0.9900 . ?
C44B H44D 0.9800 . ?
C44B H44E 0.9800 . ?
C44B H44F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Ca1 O5 95.80(6) 2 2_545 ?
O6 Ca1 O1 82.16(6) 2 3_665 ?
O5 Ca1 O1 167.89(6) 2_545 3_665 ?
O6 Ca1 O2 174.59(6) 2 3_655 ?
O5 Ca1 O2 88.48(6) 2_545 3_655 ?
O1 Ca1 O2 92.96(5) 3_665 3_655 ?
O6 Ca1 O2 74.82(6) 2 4_666 ?
O5 Ca1 O2 109.02(6) 2_545 4_666 ?
O1 Ca1 O2 82.06(5) 3_665 4_666 ?
O2 Ca1 O2 106.93(4) 3_655 4_666 ?
O6 Ca1 O4 90.01(6) 2 . ?
O5 Ca1 O4 79.79(6) 2_545 . ?
O1 Ca1 O4 88.26(5) 3_665 . ?
O2 Ca1 O4 87.49(5) 3_655 . ?
O2 Ca1 O4 162.93(6) 4_666 . ?
O3 S1 O4 119.40(10) . . ?
O3 S1 C8 108.19(10) . . ?
O4 S1 C8 108.29(9) . . ?
O3 S1 C5 107.67(10) . . ?
O4 S1 C5 106.63(9) . . ?
C8 S1 C5 105.89(10) . . ?
C1 O1 Ca1 138.72(13) . 3_665 ?
C1 O1 Ca1 81.51(12) . 4_565 ?
Ca1 O1 Ca1 95.77(5) 3_665 4_565 ?
C1 O2 Ca1 141.36(13) . 3_655 ?
C1 O2 Ca1 101.70(12) . 4_565 ?
Ca1 O2 Ca1 108.67(6) 3_655 4_565 ?
S1 O4 Ca1 137.76(9) . . ?
C12 O5 Ca1 145.86(14) . 2 ?
C12 O6 Ca1 174.58(15) . 2_545 ?
O1 C1 O2 123.75(18) . . ?
O1 C1 C2 118.65(18) . . ?
O2 C1 C2 117.55(18) . . ?
C3 C2 C7 120.17(18) . . ?
C3 C2 C1 119.55(18) . . ?
C7 C2 C1 120.28(18) . . ?
C4 C3 C2 120.64(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.57(19) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.59(18) . . ?
C6 C5 S1 118.95(16) . . ?
C4 C5 S1 119.43(16) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 119.75(19) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C9 C8 C14 121.85(19) . . ?
C9 C8 S1 119.86(16) . . ?
C14 C8 S1 118.28(15) . . ?
C10 C9 C8 118.09(19) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 120.85(19) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C13 C11 C10 120.23(18) . . ?
C13 C11 C12 120.30(18) . . ?
C10 C11 C12 119.43(18) . . ?
O5 C12 O6 126.81(19) . . ?
O5 C12 C11 116.60(18) . . ?
O6 C12 C11 116.58(18) . . ?
C14 C13 C11 119.87(19) . . ?
C14 C13 H13 120.1 . . ?
C11 C13 H13 120.1 . . ?
C13 C14 C8 119.07(19) . . ?
C13 C14 H14 120.5 . . ?
C8 C14 H14 120.5 . . ?
C42A C41A H41A 109.5 . . ?
C42A C41A H41B 109.5 . . ?
H41A C41A H41B 109.5 . . ?
C42A C41A H41C 109.5 . . ?
H41A C41A H41C 109.5 . . ?
H41B C41A H41C 109.5 . . ?
C43A C42A C41A 109.6(5) . . ?
C43A C42A H42A 109.7 . . ?
C41A C42A H42A 109.7 . . ?
C43A C42A H42B 109.7 . . ?
C41A C42A H42B 109.7 . . ?
H42A C42A H42B 108.2 . . ?
C42A C43A C44A 109.7(5) . . ?
C42A C43A H43A 109.7 . . ?
C44A C43A H43A 109.7 . . ?
C42A C43A H43B 109.7 . . ?
C44A C43A H43B 109.7 . . ?
H43A C43A H43B 108.2 . . ?
C43A C44A H44A 109.5 . . ?
C43A C44A H44B 109.5 . . ?
H44A C44A H44B 109.5 . . ?
C43A C44A H44C 109.5 . . ?
H44A C44A H44C 109.5 . . ?
H44B C44A H44C 109.5 . . ?
C42B C41B H41D 109.5 . . ?
C42B C41B H41E 109.5 . . ?
H41D C41B H41E 109.5 . . ?
C42B C41B H41F 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
C43B C42B C41B 109.5(5) . . ?
C43B C42B H42C 109.8 . . ?
C41B C42B H42C 109.8 . . ?
C43B C42B H42D 109.8 . . ?
C41B C42B H42D 109.8 . . ?
H42C C42B H42D 108.2 . . ?
C42B C43B C44B 109.4(5) . . ?
C42B C43B H43C 109.8 . . ?
C44B C43B H43C 109.8 . . ?
C42B C43B H43D 109.8 . . ?
C44B C43B H43D 109.8 . . ?
H43C C43B H43D 108.2 . . ?
C43B C44B H44D 109.5 . . ?
C43B C44B H44E 109.5 . . ?
H44D C44B H44E 109.5 . . ?
C43B C44B H44F 109.5 . . ?
H44D C44B H44F 109.5 . . ?
H44E C44B H44F 109.5 . . ?

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
O3 S1 O4 Ca1 -49.80(17) . . . . ?
C8 S1 O4 Ca1 74.51(15) . . . . ?
C5 S1 O4 Ca1 -171.94(12) . . . . ?
O6 Ca1 O4 S1 -108.30(14) 2 . . . ?
O5 Ca1 O4 S1 -12.41(13) 2_545 . . . ?
O1 Ca1 O4 S1 169.54(14) 3_665 . . . ?
O2 Ca1 O4 S1 76.50(14) 3_655 . . . ?
O2 Ca1 O4 S1 -135.21(16) 4_666 . . . ?
Ca1 O1 C1 O2 -69.3(3) 3_665 . . . ?
Ca1 O1 C1 O2 19.79(19) 4_565 . . . ?
Ca1 O1 C1 C2 113.3(2) 3_665 . . . ?
Ca1 O1 C1 C2 -157.56(17) 4_565 . . . ?
Ca1 O2 C1 O1 117.6(2) 3_655 . . . ?
Ca1 O2 C1 O1 -23.9(2) 4_565 . . . ?
Ca1 O2 C1 C2 -65.0(3) 3_655 . . . ?
Ca1 O2 C1 C2 153.52(15) 4_565 . . . ?
O1 C1 C2 C3 -24.0(3) . . . . ?
O2 C1 C2 C3 158.43(19) . . . . ?
O1 C1 C2 C7 155.9(2) . . . . ?
O2 C1 C2 C7 -21.7(3) . . . . ?
C7 C2 C3 C4 2.2(3) . . . . ?
C1 C2 C3 C4 -177.88(19) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C3 C4 C5 S1 175.71(16) . . . . ?
O3 S1 C5 C6 27.2(2) . . . . ?
O4 S1 C5 C6 156.48(17) . . . . ?
C8 S1 C5 C6 -88.33(19) . . . . ?
O3 S1 C5 C4 -150.63(17) . . . . ?
O4 S1 C5 C4 -21.4(2) . . . . ?
C8 S1 C5 C4 93.82(18) . . . . ?
C4 C5 C6 C7 2.6(3) . . . . ?
S1 C5 C6 C7 -175.15(17) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C3 C2 C7 C6 -1.6(3) . . . . ?
C1 C2 C7 C6 178.5(2) . . . . ?
O3 S1 C8 C9 147.99(17) . . . . ?
O4 S1 C8 C9 17.24(19) . . . . ?
C5 S1 C8 C9 -96.81(18) . . . . ?
O3 S1 C8 C14 -31.00(19) . . . . ?
O4 S1 C8 C14 -161.75(16) . . . . ?
C5 S1 C8 C14 84.20(18) . . . . ?
C14 C8 C9 C10 0.7(3) . . . . ?
S1 C8 C9 C10 -178.23(16) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C13 -1.5(3) . . . . ?
C9 C10 C11 C12 176.45(19) . . . . ?
Ca1 O5 C12 O6 -11.9(4) 2 . . . ?
Ca1 O5 C12 C11 169.39(17) 2 . . . ?
Ca1 O6 C12 O5 125.2(15) 2_545 . . . ?
Ca1 O6 C12 C11 -56.1(16) 2_545 . . . ?
C13 C11 C12 O5 -157.8(2) . . . . ?
C10 C11 C12 O5 24.3(3) . . . . ?
C13 C11 C12 O6 23.4(3) . . . . ?
C10 C11 C12 O6 -154.5(2) . . . . ?
C10 C11 C13 C14 0.1(3) . . . . ?
C12 C11 C13 C14 -177.84(19) . . . . ?
C11 C13 C14 C8 1.7(3) . . . . ?
C9 C8 C14 C13 -2.1(3) . . . . ?
S1 C8 C14 C13 176.87(16) . . . . ?
C41A C42A C43A C44A -81.7(19) . . . . ?
C41B C42B C43B C44B 144(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        32.15
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.107
####################################################################### 
# 
# 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_DB1_156B
_database_code_depnum_ccdc_archive 'CCDC 1051643'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14.60 H9.36 Ca O6 S'
_chemical_formula_sum            'C14.60 H9.36 Ca O6 S'

_chemical_formula_weight         352.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   11.7292(13)
_cell_length_b                   5.5685(6)
_cell_length_c                   22.792(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.493(2)
_cell_angle_gamma                90.00
_cell_volume                     1463.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_process_details   'SADABS, SHELDRICK (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13980
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         30.49
_reflns_number_total             4406
_reflns_number_gt                3715
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+2.4000P] 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         4406
_refine_ls_number_parameters     221
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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
Ca1 Ca 0.637486(18) -0.24380(4) 0.222220(9) 0.00821(5) Uani 1 1 d . . .
S1 S 0.39917(2) -0.03549(5) 0.107138(11) 0.00876(6) Uani 1 1 d . . .
O1 O 0.26084(7) -0.08443(15) -0.19076(3) 0.01107(18) Uani 1 1 d . . .
O2 O 0.26461(7) -0.47580(15) -0.17203(3) 0.01203(18) Uani 1 1 d . . .
O3 O -0.04233(7) -0.08085(16) 0.25482(4) 0.01427(19) Uani 1 1 d . . .
O4 O -0.01357(7) -0.47637(15) 0.24585(4) 0.01292(19) Uani 1 1 d . . .
O5 O 0.41621(7) 0.22042(15) 0.11108(4) 0.01287(19) Uani 1 1 d . . .
O6 O 0.49514(7) -0.19452(15) 0.13020(3) 0.01188(18) Uani 1 1 d . . .
C1 C 0.35455(10) -0.1085(2) 0.03111(5) 0.0102(2) Uani 1 1 d . . .
C2 C 0.38241(10) -0.3326(2) 0.01067(5) 0.0125(2) Uani 1 1 d . . .
H2 H 0.4200 -0.4502 0.0376 0.015 Uiso 1 1 calc R . .
C3 C 0.35388(10) -0.3802(2) -0.05007(5) 0.0124(2) Uani 1 1 d . . .
H3 H 0.3720 -0.5324 -0.0648 0.015 Uiso 1 1 calc R . .
C4 C 0.29938(9) -0.2082(2) -0.08941(5) 0.0096(2) Uani 1 1 d . . .
C5 C 0.26898(11) 0.0122(2) -0.06798(5) 0.0143(3) Uani 1 1 d . . .
H5 H 0.2301 0.1286 -0.0949 0.017 Uiso 1 1 calc R . .
C6 C 0.29539(11) 0.0621(2) -0.00742(5) 0.0143(3) Uani 1 1 d . . .
H6 H 0.2733 0.2109 0.0076 0.017 Uiso 1 1 calc R . .
C7 C 0.27457(9) -0.2614(2) -0.15530(5) 0.0091(2) Uani 1 1 d . . .
C8 C 0.28174(9) -0.1088(2) 0.14223(5) 0.0101(2) Uani 1 1 d . . .
C9 C 0.19304(10) 0.0595(2) 0.14080(5) 0.0125(2) Uani 1 1 d . . .
H9 H 0.1942 0.2058 0.1195 0.015 Uiso 1 1 calc R . .
C10 C 0.10297(10) 0.0098(2) 0.17102(5) 0.0127(2) Uani 1 1 d . . .
H10 H 0.0430 0.1242 0.1713 0.015 Uiso 1 1 calc R . .
C11 C 0.10079(9) -0.2080(2) 0.20092(5) 0.0097(2) Uani 1 1 d . . .
C12 C 0.18833(10) -0.3764(2) 0.20040(5) 0.0106(2) Uani 1 1 d . . .
H12 H 0.1851 -0.5260 0.2201 0.013 Uiso 1 1 calc R . .
C13 C 0.28073(10) -0.3282(2) 0.17139(5) 0.0107(2) Uani 1 1 d . . .
H13 H 0.3412 -0.4418 0.1715 0.013 Uiso 1 1 calc R . .
C14 C 0.00606(9) -0.2594(2) 0.23671(5) 0.0104(2) Uani 1 1 d . . .
C21 C 0.0374(16) -0.4486(9) 0.0128(8) 0.170 Uiso 0.09 1 d PD . .
H21A H -0.0004 -0.5932 -0.0060 0.255 Uiso 0.09 1 calc PR . .
H21B H 0.0271 -0.4411 0.0545 0.255 Uiso 0.09 1 calc PR . .
H21C H 0.1204 -0.4539 0.0113 0.255 Uiso 0.09 1 calc PR . .
C22 C -0.0174(11) -0.2239(8) -0.0209(7) 0.170 Uiso 0.09 1 d PD . .
H22A H -0.0997 -0.2114 -0.0165 0.204 Uiso 0.09 1 calc PR . .
H22B H -0.0151 -0.2406 -0.0639 0.204 Uiso 0.09 1 calc PR . .
C23 C 0.0476(7) 0.0075(6) 0.0034(9) 0.170 Uiso 0.09 1 d PD . .
H23A H 0.0777 -0.0112 0.0466 0.204 Uiso 0.09 1 calc PR . .
H23B H 0.1145 0.0326 -0.0169 0.204 Uiso 0.09 1 calc PR . .
C24 C -0.0331(7) 0.2289(6) -0.0069(7) 0.170 Uiso 0.09 1 d PD . .
H24A H -0.0696 0.2538 0.0286 0.204 Uiso 0.09 1 calc PR . .
H24B H -0.0955 0.1994 -0.0416 0.204 Uiso 0.09 1 calc PR . .
C25 C 0.0349(7) 0.4576(8) -0.0181(3) 0.170 Uiso 0.09 1 d PD . .
H25A H 0.0164 0.5004 -0.0609 0.204 Uiso 0.09 1 calc PR . .
H25B H 0.1192 0.4259 -0.0076 0.204 Uiso 0.09 1 calc PR . .
C26 C 0.0026(9) 0.6698(9) 0.0199(3) 0.170 Uiso 0.09 1 d PD . .
H26A H -0.0585 0.7685 -0.0045 0.204 Uiso 0.09 1 calc PR . .
H26B H 0.0715 0.7728 0.0326 0.204 Uiso 0.09 1 calc PR . .
C27 C -0.0414(9) 0.574(3) 0.0757(3) 0.170 Uiso 0.09 1 d PD . .
H27A H -0.0624 0.7090 0.0990 0.255 Uiso 0.09 1 calc PR . .
H27B H 0.0199 0.4792 0.1002 0.255 Uiso 0.09 1 calc PR . .
H27C H -0.1096 0.4718 0.0630 0.255 Uiso 0.09 1 calc PR . .


_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
Ca1 O4 2.2902(9) 2 ?
Ca1 O3 2.2923(9) 2_545 ?
Ca1 O2 2.3544(9) 3_645 ?
Ca1 O1 2.3640(9) 3_655 ?
Ca1 O1 2.4284(8) 4_656 ?
Ca1 O6 2.4467(8) . ?
Ca1 O2 2.8668(8) 4_656 ?
Ca1 C7 2.9571(10) 4_656 ?
Ca1 Ca1 3.8865(4) 2_645 ?
Ca1 Ca1 3.8865(4) 2_655 ?
S1 O5 1.4395(9) . ?
S1 O6 1.4532(8) . ?
S1 C8 1.7620(12) . ?
S1 C1 1.7640(11) . ?
O1 C7 1.2659(14) . ?
O1 Ca1 2.3640(9) 3_655 ?
O1 Ca1 2.4283(8) 4 ?
O2 C7 1.2525(14) . ?
O2 Ca1 2.3545(9) 3_645 ?
O2 Ca1 2.8668(8) 4 ?
O3 C14 1.2515(14) . ?
O3 Ca1 2.2923(9) 2 ?
O4 C14 1.2545(14) . ?
O4 Ca1 2.2901(9) 2_545 ?
C1 C6 1.3905(16) . ?
C1 C2 1.3911(17) . ?
C2 C3 1.3894(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3857(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3911(17) . ?
C4 C7 1.5061(15) . ?
C5 C6 1.3866(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 Ca1 2.9570(10) 4 ?
C8 C13 1.3920(16) . ?
C8 C9 1.3962(16) . ?
C9 C10 1.3899(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3936(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3920(16) . ?
C11 C14 1.5206(16) . ?
C12 C13 1.3945(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C21 C22 1.546(8) . ?
C21 C24 1.994(10) 1_545 ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.547(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.546(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.548(7) . ?
C24 C21 1.994(10) 1_565 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.552(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.553(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ca1 O3 95.53(3) 2 2_545 ?
O4 Ca1 O2 168.38(3) 2 3_645 ?
O3 Ca1 O2 82.46(3) 2_545 3_645 ?
O4 Ca1 O1 88.74(3) 2 3_655 ?
O3 Ca1 O1 174.71(3) 2_545 3_655 ?
O2 Ca1 O1 92.74(3) 3_645 3_655 ?
O4 Ca1 O1 108.35(3) 2 4_656 ?
O3 Ca1 O1 74.54(3) 2_545 4_656 ?
O2 Ca1 O1 82.23(3) 3_645 4_656 ?
O1 Ca1 O1 107.09(2) 3_655 4_656 ?
O4 Ca1 O6 79.98(3) 2 . ?
O3 Ca1 O6 90.17(3) 2_545 . ?
O2 Ca1 O6 88.57(3) 3_645 . ?
O1 Ca1 O6 87.50(3) 3_655 . ?
O1 Ca1 O6 163.02(3) 4_656 . ?
O4 Ca1 O2 73.65(3) 2 4_656 ?
O3 Ca1 O2 110.96(3) 2_545 4_656 ?
O2 Ca1 O2 117.793(19) 3_645 4_656 ?
O1 Ca1 O2 73.22(3) 3_655 4_656 ?
O1 Ca1 O2 48.70(3) 4_656 4_656 ?
O6 Ca1 O2 147.36(3) . 4_656 ?
O4 Ca1 C7 87.77(3) 2 4_656 ?
O3 Ca1 C7 89.78(3) 2_545 4_656 ?
O2 Ca1 C7 103.63(3) 3_645 4_656 ?
O1 Ca1 C7 93.51(3) 3_655 4_656 ?
O1 Ca1 C7 24.78(3) 4_656 4_656 ?
O6 Ca1 C7 167.69(3) . 4_656 ?
O2 Ca1 C7 24.78(3) 4_656 4_656 ?
O4 Ca1 Ca1 142.65(2) 2 2_645 ?
O3 Ca1 Ca1 70.68(2) 2_545 2_645 ?
O2 Ca1 Ca1 47.22(2) 3_645 2_645 ?
O1 Ca1 Ca1 107.61(2) 3_655 2_645 ?
O1 Ca1 Ca1 35.26(2) 4_656 2_645 ?
O6 Ca1 Ca1 132.58(2) . 2_645 ?
O2 Ca1 Ca1 79.237(19) 4_656 2_645 ?
C7 Ca1 Ca1 58.61(2) 4_656 2_645 ?
O4 Ca1 Ca1 82.14(2) 2 2_655 ?
O3 Ca1 Ca1 147.37(2) 2_545 2_655 ?
O2 Ca1 Ca1 105.73(2) 3_645 2_655 ?
O1 Ca1 Ca1 36.367(18) 3_655 2_655 ?
O1 Ca1 Ca1 75.39(2) 4_656 2_655 ?
O6 Ca1 Ca1 121.06(2) . 2_655 ?
O2 Ca1 Ca1 37.071(17) 4_656 2_655 ?
C7 Ca1 Ca1 57.67(2) 4_656 2_655 ?
Ca1 Ca1 Ca1 91.515(12) 2_645 2_655 ?
O5 S1 O6 119.41(5) . . ?
O5 S1 C8 108.18(5) . . ?
O6 S1 C8 108.22(5) . . ?
O5 S1 C1 107.62(5) . . ?
O6 S1 C1 106.65(5) . . ?
C8 S1 C1 106.01(5) . . ?
C7 O1 Ca1 141.52(7) . 3_655 ?
C7 O1 Ca1 101.68(7) . 4 ?
Ca1 O1 Ca1 108.38(3) 3_655 4 ?
C7 O2 Ca1 138.90(8) . 3_645 ?
C7 O2 Ca1 81.65(6) . 4 ?
Ca1 O2 Ca1 95.71(3) 3_645 4 ?
C14 O3 Ca1 174.04(8) . 2 ?
C14 O4 Ca1 145.63(8) . 2_545 ?
S1 O6 Ca1 137.82(5) . . ?
C6 C1 C2 121.45(10) . . ?
C6 C1 S1 119.18(9) . . ?
C2 C1 S1 119.34(8) . . ?
C3 C2 C1 118.43(10) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 120.79(11) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.00(10) . . ?
C3 C4 C7 119.47(10) . . ?
C5 C4 C7 120.53(10) . . ?
C6 C5 C4 120.08(11) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.15(11) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O2 C7 O1 123.61(10) . . ?
O2 C7 C4 118.77(10) . . ?
O1 C7 C4 117.57(10) . . ?
O2 C7 Ca1 73.58(6) . 4 ?
O1 C7 Ca1 53.53(5) . 4 ?
C4 C7 Ca1 155.86(7) . 4 ?
C13 C8 C9 121.95(11) . . ?
C13 C8 S1 119.70(9) . . ?
C9 C8 S1 118.34(9) . . ?
C10 C9 C8 119.03(11) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.92(11) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.18(11) . . ?
C12 C11 C14 119.34(10) . . ?
C10 C11 C14 120.42(10) . . ?
C11 C12 C13 120.84(11) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 118.04(11) . . ?
C8 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
O3 C14 O4 127.03(11) . . ?
O3 C14 C11 116.56(10) . . ?
O4 C14 C11 116.39(10) . . ?
C22 C21 C24 120.0(9) . 1_545 ?
C22 C21 H21A 109.5 . . ?
C24 C21 H21A 12.9 1_545 . ?
C22 C21 H21B 109.5 . . ?
C24 C21 H21B 97.9 1_545 . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
C24 C21 H21C 109.8 1_545 . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 C22 C23 111.3(7) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 111.2(6) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C25 111.2(6) . . ?
C23 C24 C21 117.9(7) . 1_565 ?
C25 C24 C21 24.7(6) . 1_565 ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C21 C24 H24A 85.1 1_565 . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C21 C24 H24B 123.1 1_565 . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 110.4(6) . . ?
C24 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
C24 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 C27 110.2(6) . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
O5 S1 O6 Ca1 50.54(9) . . . . ?
C8 S1 O6 Ca1 -73.70(8) . . . . ?
C1 S1 O6 Ca1 172.63(7) . . . . ?
O4 Ca1 O6 S1 11.93(7) 2 . . . ?
O3 Ca1 O6 S1 107.52(8) 2_545 . . . ?
O2 Ca1 O6 S1 -170.03(8) 3_645 . . . ?
O1 Ca1 O6 S1 -77.23(8) 3_655 . . . ?
O1 Ca1 O6 S1 132.98(9) 4_656 . . . ?
O2 Ca1 O6 S1 -24.37(11) 4_656 . . . ?
C7 Ca1 O6 S1 17.8(2) 4_656 . . . ?
Ca1 Ca1 O6 S1 170.98(6) 2_645 . . . ?
Ca1 Ca1 O6 S1 -62.49(8) 2_655 . . . ?
O5 S1 C1 C6 -27.69(11) . . . . ?
O6 S1 C1 C6 -156.94(10) . . . . ?
C8 S1 C1 C6 87.89(11) . . . . ?
O5 S1 C1 C2 150.33(9) . . . . ?
O6 S1 C1 C2 21.07(11) . . . . ?
C8 S1 C1 C2 -94.10(10) . . . . ?
C6 C1 C2 C3 2.58(18) . . . . ?
S1 C1 C2 C3 -175.39(9) . . . . ?
C1 C2 C3 C4 0.25(18) . . . . ?
C2 C3 C4 C5 -2.22(18) . . . . ?
C2 C3 C4 C7 177.21(11) . . . . ?
C3 C4 C5 C6 1.40(18) . . . . ?
C7 C4 C5 C6 -178.02(11) . . . . ?
C4 C5 C6 C1 1.36(19) . . . . ?
C2 C1 C6 C5 -3.39(18) . . . . ?
S1 C1 C6 C5 174.58(10) . . . . ?
Ca1 O2 C7 O1 69.17(15) 3_645 . . . ?
Ca1 O2 C7 O1 -19.95(10) 4 . . . ?
Ca1 O2 C7 C4 -113.44(11) 3_645 . . . ?
Ca1 O2 C7 C4 157.44(9) 4 . . . ?
Ca1 O2 C7 Ca1 89.12(9) 3_645 . . 4 ?
Ca1 O1 C7 O2 -117.04(12) 3_655 . . . ?
Ca1 O1 C7 O2 24.01(12) 4 . . . ?
Ca1 O1 C7 C4 65.55(15) 3_655 . . . ?
Ca1 O1 C7 C4 -153.40(8) 4 . . . ?
Ca1 O1 C7 Ca1 -141.05(13) 3_655 . . 4 ?
C3 C4 C7 O2 24.93(16) . . . . ?
C5 C4 C7 O2 -155.65(11) . . . . ?
C3 C4 C7 O1 -157.53(11) . . . . ?
C5 C4 C7 O1 21.90(16) . . . . ?
C3 C4 C7 Ca1 140.80(16) . . . 4 ?
C5 C4 C7 Ca1 -39.8(2) . . . 4 ?
O5 S1 C8 C13 -147.72(9) . . . . ?
O6 S1 C8 C13 -17.00(10) . . . . ?
C1 S1 C8 C13 97.09(9) . . . . ?
O5 S1 C8 C9 31.00(10) . . . . ?
O6 S1 C8 C9 161.71(8) . . . . ?
C1 S1 C8 C9 -84.19(10) . . . . ?
C13 C8 C9 C10 2.13(16) . . . . ?
S1 C8 C9 C10 -176.55(8) . . . . ?
C8 C9 C10 C11 -1.54(16) . . . . ?
C9 C10 C11 C12 -0.27(16) . . . . ?
C9 C10 C11 C14 176.93(10) . . . . ?
C10 C11 C12 C13 1.58(16) . . . . ?
C14 C11 C12 C13 -175.65(10) . . . . ?
C9 C8 C13 C12 -0.85(16) . . . . ?
S1 C8 C13 C12 177.81(8) . . . . ?
C11 C12 C13 C8 -1.01(16) . . . . ?
Ca1 O3 C14 O4 -118.8(7) 2 . . . ?
Ca1 O3 C14 C11 62.7(8) 2 . . . ?
Ca1 O4 C14 O3 13.9(2) 2_545 . . . ?
Ca1 O4 C14 C11 -167.61(8) 2_545 . . . ?
C12 C11 C14 O3 153.57(10) . . . . ?
C10 C11 C14 O3 -23.65(14) . . . . ?
C12 C11 C14 O4 -25.10(14) . . . . ?
C10 C11 C14 O4 157.68(10) . . . . ?
C24 C21 C22 C23 177.4(13) 1_545 . . . ?
C21 C22 C23 C24 -153.5(15) . . . . ?
C22 C23 C24 C25 -147.1(12) . . . . ?
C22 C23 C24 C21 -173.3(13) . . . 1_565 ?
C23 C24 C25 C26 -133.5(11) . . . . ?
C21 C24 C25 C26 -22.7(11) 1_565 . . . ?
C24 C25 C26 C27 24.9(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.49
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_DB1_120B_1
_database_code_depnum_ccdc_archive 'CCDC 1051644'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Ca O6 S, 0.13(C6 H14)'
_chemical_formula_sum            'C14.63 H9.47 Ca O6 S'

_chemical_formula_weight         353.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  ' -P 2yn'

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

_cell_length_a                   11.7150(6)
_cell_length_b                   5.5679(3)
_cell_length_c                   22.8208(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5320(10)
_cell_angle_gamma                90.00
_cell_volume                     1463.48(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             725
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'sADABS, Sheldrick (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18014
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         32.93
_reflns_number_total             5206
_reflns_number_gt                5021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+7.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5206
_refine_ls_number_parameters     219
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca -0.13745(4) 0.24358(8) 0.277932(18) 0.00721(9) Uani 1 1 d . . .
S1 S 0.10095(4) 0.03536(9) 0.39303(2) 0.00741(10) Uani 1 1 d . . .
O1 O 0.08355(15) -0.2205(3) 0.38907(7) 0.0116(3) Uani 1 1 d . . .
O2 O 0.00490(14) 0.1945(3) 0.37009(7) 0.0105(3) Uani 1 1 d . . .
O3 O 0.23571(15) 0.4767(3) 0.67200(7) 0.0106(3) Uani 1 1 d . . .
O4 O 0.23927(14) 0.0851(3) 0.69086(7) 0.0097(3) Uani 1 1 d . . .
O5 O 0.51327(15) 0.4766(3) 0.25391(8) 0.0122(3) Uani 1 1 d . . .
O6 O 0.54238(15) 0.0808(3) 0.24482(8) 0.0130(3) Uani 1 1 d . . .
C1 C 0.20110(19) 0.2085(4) 0.58947(9) 0.0081(3) Uani 1 1 d . . .
C2 C 0.1465(2) 0.3807(4) 0.55011(10) 0.0118(4) Uani 1 1 d . . .
H2 H 0.1286 0.5331 0.5648 0.014 Uiso 1 1 calc R . .
C3 C 0.1179(2) 0.3325(4) 0.48936(10) 0.0122(4) Uani 1 1 d . . .
H3 H 0.0801 0.4500 0.4624 0.015 Uiso 1 1 calc R . .
C4 C 0.14579(19) 0.1087(4) 0.46905(9) 0.0085(3) Uani 1 1 d . . .
C5 C 0.2053(2) -0.0621(4) 0.50746(10) 0.0139(4) Uani 1 1 d . . .
H5 H 0.2274 -0.2109 0.4925 0.017 Uiso 1 1 calc R . .
C6 C 0.2321(2) -0.0117(4) 0.56816(10) 0.0133(4) Uani 1 1 d . . .
H6 H 0.2716 -0.1276 0.5950 0.016 Uiso 1 1 calc R . .
C7 C 0.22560(18) 0.2619(4) 0.65520(9) 0.0084(3) Uani 1 1 d . . .
C8 C 0.39936(18) 0.2080(4) 0.29898(9) 0.0083(3) Uani 1 1 d . . .
C9 C 0.31160(19) 0.3767(4) 0.29973(10) 0.0092(4) Uani 1 1 d . . .
H9 H 0.3146 0.5266 0.2802 0.011 Uiso 1 1 calc R . .
C10 C 0.21960(19) 0.3278(4) 0.32884(10) 0.0098(4) Uani 1 1 d . . .
H10 H 0.1590 0.4412 0.3288 0.012 Uiso 1 1 calc R . .
C11 C 0.21875(19) 0.1087(4) 0.35791(9) 0.0086(3) Uani 1 1 d . . .
C12 C 0.3071(2) -0.0600(4) 0.35928(10) 0.0121(4) Uani 1 1 d . . .
H12 H 0.3057 -0.2065 0.3805 0.014 Uiso 1 1 calc R . .
C13 C 0.39738(19) -0.0103(4) 0.32908(10) 0.0113(4) Uani 1 1 d . . .
H13 H 0.4576 -0.1245 0.3289 0.014 Uiso 1 1 calc R . .
C14 C 0.49374(18) 0.2587(4) 0.26326(10) 0.0094(4) Uani 1 1 d . . .
C101 C -0.018(9) 1.122(7) -0.022(4) 0.089(10) Uiso 0.105(4) 1 d PD . .
H10A H 0.0261 1.2650 -0.0064 0.133 Uiso 0.105(4) 1 calc PR . .
H10B H -0.0984 1.1372 -0.0169 0.133 Uiso 0.105(4) 1 calc PR . .
H10C H -0.0154 1.1068 -0.0649 0.133 Uiso 0.105(4) 1 calc PR . .
C102 C 0.037(7) 0.899(7) 0.011(3) 0.089(10) Uiso 0.105(4) 1 d PD . .
H10D H 0.1154 0.8766 0.0013 0.107 Uiso 0.105(4) 1 calc PR . .
H10E H 0.0458 0.9283 0.0540 0.107 Uiso 0.105(4) 1 calc PR . .
C103 C -0.030(5) 0.677(7) -0.004(4) 0.089(10) Uiso 0.105(4) 1 d PD . .
H10F H -0.0782 0.6950 -0.0441 0.107 Uiso 0.105(4) 1 calc PR . .
H10G H -0.0828 0.6572 0.0248 0.107 Uiso 0.105(4) 1 calc PR . .
C104 C 0.043(4) 0.451(7) -0.003(3) 0.089(10) Uiso 0.105(4) 1 d PD . .
H10H H 0.1145 0.4672 0.0273 0.107 Uiso 0.105(4) 1 calc PR . .
H10I H 0.0668 0.4312 -0.0425 0.107 Uiso 0.105(4) 1 calc PR . .
C105 C -0.024(5) 0.228(7) 0.010(3) 0.089(10) Uiso 0.105(4) 1 d PD . .
H10J H -0.0128 0.2044 0.0539 0.107 Uiso 0.105(4) 1 calc PR . .
H10K H -0.1075 0.2512 -0.0052 0.107 Uiso 0.105(4) 1 calc PR . .
C106 C 0.018(7) 0.004(7) -0.018(3) 0.089(10) Uiso 0.105(4) 1 d PD . .
H10L H -0.0247 -0.1366 -0.0083 0.133 Uiso 0.105(4) 1 calc PR . .
H10M H 0.1013 -0.0189 -0.0035 0.133 Uiso 0.105(4) 1 calc PR . .
H10N H 0.0045 0.0240 -0.0618 0.133 Uiso 0.105(4) 1 calc PR . .


_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
Ca1 O5 2.2894(17) 2_545 ?
Ca1 O6 2.2907(17) 2 ?
Ca1 O3 2.3530(17) 3_566 ?
Ca1 O4 2.3642(17) 3_556 ?
Ca1 O4 2.4279(17) 4_565 ?
Ca1 O2 2.4488(17) . ?
Ca1 O3 2.8713(18) 4_565 ?
S1 O1 1.4395(17) . ?
S1 O2 1.4525(17) . ?
S1 C11 1.766(2) . ?
S1 C4 1.766(2) . ?
O3 C7 1.255(3) . ?
O3 Ca1 2.3529(17) 3_566 ?
O3 Ca1 2.8712(18) 4_666 ?
O4 C7 1.269(3) . ?
O4 Ca1 2.3642(17) 3_556 ?
O4 Ca1 2.4279(17) 4_666 ?
O5 C14 1.260(3) . ?
O5 Ca1 2.2894(17) 2 ?
O6 C14 1.253(3) . ?
O6 Ca1 2.2907(17) 2_545 ?
C1 C2 1.387(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.505(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.395(3) . ?
C8 C13 1.398(3) . ?
C8 C14 1.515(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C101 C102 1.527(10) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C102 C103 1.47(4) . ?
C102 H10D 0.9900 . ?
C102 H10E 0.9900 . ?
C103 C104 1.522(10) . ?
C103 H10F 0.9900 . ?
C103 H10G 0.9900 . ?
C104 C105 1.529(10) . ?
C104 H10H 0.9900 . ?
C104 H10I 0.9900 . ?
C105 C106 1.526(10) . ?
C105 H10J 0.9900 . ?
C105 H10K 0.9900 . ?
C106 H10L 0.9800 . ?
C106 H10M 0.9800 . ?
C106 H10N 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Ca1 O6 95.56(6) 2_545 2 ?
O5 Ca1 O3 168.40(6) 2_545 3_566 ?
O6 Ca1 O3 82.46(6) 2 3_566 ?
O5 Ca1 O4 88.72(6) 2_545 3_556 ?
O6 Ca1 O4 174.72(6) 2 3_556 ?
O3 Ca1 O4 92.72(6) 3_566 3_556 ?
O5 Ca1 O4 108.23(6) 2_545 4_565 ?
O6 Ca1 O4 74.55(6) 2 4_565 ?
O3 Ca1 O4 82.35(6) 3_566 4_565 ?
O4 Ca1 O4 107.05(4) 3_556 4_565 ?
O5 Ca1 O2 80.07(6) 2_545 . ?
O6 Ca1 O2 90.19(6) 2 . ?
O3 Ca1 O2 88.49(6) 3_566 . ?
O4 Ca1 O2 87.52(6) 3_556 . ?
O4 Ca1 O2 163.05(6) 4_565 . ?
O5 Ca1 O3 73.52(6) 2_545 4_565 ?
O6 Ca1 O3 110.95(6) 2 4_565 ?
O3 Ca1 O3 117.89(4) 3_566 4_565 ?
O4 Ca1 O3 73.20(5) 3_556 4_565 ?
O4 Ca1 O3 48.69(5) 4_565 4_565 ?
O2 Ca1 O3 147.33(5) . 4_565 ?
O1 S1 O2 119.31(10) . . ?
O1 S1 C11 108.29(10) . . ?
O2 S1 C11 108.27(10) . . ?
O1 S1 C4 107.68(10) . . ?
O2 S1 C4 106.55(10) . . ?
C11 S1 C4 105.99(10) . . ?
S1 O2 Ca1 137.63(10) . . ?
C7 O3 Ca1 138.75(15) . 3_566 ?
C7 O3 Ca1 81.68(13) . 4_666 ?
Ca1 O3 Ca1 95.61(5) 3_566 4_666 ?
C7 O4 Ca1 141.49(14) . 3_556 ?
C7 O4 Ca1 101.92(13) . 4_666 ?
Ca1 O4 Ca1 108.36(6) 3_556 4_666 ?
C14 O5 Ca1 145.55(15) . 2 ?
C14 O6 Ca1 173.59(16) . 2_545 ?
C2 C1 C6 120.1(2) . . ?
C2 C1 C7 119.36(19) . . ?
C6 C1 C7 120.54(19) . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 S1 119.28(17) . . ?
C5 C4 S1 119.08(17) . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O3 C7 O4 123.4(2) . . ?
O3 C7 C1 118.89(19) . . ?
O4 C7 C1 117.70(19) . . ?
C9 C8 C13 120.1(2) . . ?
C9 C8 C14 119.52(19) . . ?
C13 C8 C14 120.38(19) . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 122.2(2) . . ?
C10 C11 S1 119.62(17) . . ?
C12 C11 S1 118.20(17) . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O6 C14 O5 126.6(2) . . ?
O6 C14 C8 117.0(2) . . ?
O5 C14 C8 116.34(19) . . ?
C102 C101 H10A 109.5 . . ?
C102 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C102 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C103 C102 C101 115(3) . . ?
C103 C102 H10D 108.6 . . ?
C101 C102 H10D 108.6 . . ?
C103 C102 H10E 108.6 . . ?
C101 C102 H10E 108.6 . . ?
H10D C102 H10E 107.6 . . ?
C102 C103 C104 115(3) . . ?
C102 C103 H10F 108.5 . . ?
C104 C103 H10F 108.5 . . ?
C102 C103 H10G 108.5 . . ?
C104 C103 H10G 108.5 . . ?
H10F C103 H10G 107.5 . . ?
C103 C104 C105 111.7(10) . . ?
C103 C104 H10H 109.3 . . ?
C105 C104 H10H 109.3 . . ?
C103 C104 H10I 109.3 . . ?
C105 C104 H10I 109.3 . . ?
H10H C104 H10I 107.9 . . ?
C106 C105 C104 111.2(10) . . ?
C106 C105 H10J 109.4 . . ?
C104 C105 H10J 109.4 . . ?
C106 C105 H10K 109.4 . . ?
C104 C105 H10K 109.4 . . ?
H10J C105 H10K 108.0 . . ?
C105 C106 H10L 109.5 . . ?
C105 C106 H10M 109.5 . . ?
H10L C106 H10M 109.5 . . ?
C105 C106 H10N 109.5 . . ?
H10L C106 H10N 109.5 . . ?
H10M C106 H10N 109.5 . . ?

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
O1 S1 O2 Ca1 -50.81(18) . . . . ?
C11 S1 O2 Ca1 73.55(16) . . . . ?
C4 S1 O2 Ca1 -172.82(13) . . . . ?
O5 Ca1 O2 S1 -11.88(14) 2_545 . . . ?
O6 Ca1 O2 S1 -107.49(15) 2 . . . ?
O3 Ca1 O2 S1 170.05(15) 3_566 . . . ?
O4 Ca1 O2 S1 77.26(15) 3_556 . . . ?
O4 Ca1 O2 S1 -132.88(18) 4_565 . . . ?
O3 Ca1 O2 S1 24.4(2) 4_565 . . . ?
C6 C1 C2 C3 2.7(4) . . . . ?
C7 C1 C2 C3 -177.0(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -2.7(4) . . . . ?
C2 C3 C4 S1 175.42(18) . . . . ?
O1 S1 C4 C3 -150.15(18) . . . . ?
O2 S1 C4 C3 -21.0(2) . . . . ?
C11 S1 C4 C3 94.1(2) . . . . ?
O1 S1 C4 C5 28.0(2) . . . . ?
O2 S1 C4 C5 157.08(19) . . . . ?
C11 S1 C4 C5 -87.7(2) . . . . ?
C3 C4 C5 C6 3.4(4) . . . . ?
S1 C4 C5 C6 -174.69(19) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
C7 C1 C6 C5 177.7(2) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
Ca1 O3 C7 O4 -69.2(3) 3_566 . . . ?
Ca1 O3 C7 O4 19.9(2) 4_666 . . . ?
Ca1 O3 C7 C1 113.6(2) 3_566 . . . ?
Ca1 O3 C7 C1 -157.42(18) 4_666 . . . ?
Ca1 O4 C7 O3 117.5(2) 3_556 . . . ?
Ca1 O4 C7 O3 -24.0(2) 4_666 . . . ?
Ca1 O4 C7 C1 -65.2(3) 3_556 . . . ?
Ca1 O4 C7 C1 153.34(15) 4_666 . . . ?
C2 C1 C7 O3 -25.1(3) . . . . ?
C6 C1 C7 O3 155.2(2) . . . . ?
C2 C1 C7 O4 157.5(2) . . . . ?
C6 C1 C7 O4 -22.2(3) . . . . ?
C13 C8 C9 C10 -1.8(3) . . . . ?
C14 C8 C9 C10 175.6(2) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C9 C10 C11 S1 -177.69(17) . . . . ?
O1 S1 C11 C10 147.60(18) . . . . ?
O2 S1 C11 C10 16.9(2) . . . . ?
C4 S1 C11 C10 -97.09(19) . . . . ?
O1 S1 C11 C12 -30.9(2) . . . . ?
O2 S1 C11 C12 -161.61(18) . . . . ?
C4 S1 C11 C12 84.4(2) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
S1 C11 C12 C13 176.57(18) . . . . ?
C11 C12 C13 C8 1.2(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C14 C8 C13 C12 -176.8(2) . . . . ?
Ca1 O6 C14 O5 121.9(14) 2_545 . . . ?
Ca1 O6 C14 C8 -60.0(15) 2_545 . . . ?
Ca1 O5 C14 O6 -14.6(4) 2 . . . ?
Ca1 O5 C14 C8 167.26(18) 2 . . . ?
C9 C8 C14 O6 -153.5(2) . . . . ?
C13 C8 C14 O6 23.9(3) . . . . ?
C9 C8 C14 O5 24.8(3) . . . . ?
C13 C8 C14 O5 -157.7(2) . . . . ?
C101 C102 C103 C104 146(4) . . . . ?
C102 C103 C104 C105 153(5) . . . . ?
C103 C104 C105 C106 151(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        32.93
_diffrn_measured_fraction_theta_full 0.949
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_DB1_120B4
_database_code_depnum_ccdc_archive 'CCDC 1051645'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15.58 H11.80 Ca O6 S'
_chemical_formula_sum            'C15.58 H11.80 Ca O6 S'

_chemical_formula_weight         367.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   11.8767(11)
_cell_length_b                   5.5769(5)
_cell_length_c                   22.486(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8930(10)
_cell_angle_gamma                90.00
_cell_volume                     1467.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             757
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_process_details   'SADABS, SHELDRICK (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15135
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         30.63
_reflns_number_total             4505
_reflns_number_gt                3883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+1.9691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4505
_refine_ls_number_parameters     221
_refine_ls_number_restraints     319
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.59630(3) 0.74417(6) 0.041608(16) 0.00637(9) Uani 1 1 d U . .
S1 S 0.88397(4) 0.53388(8) 0.10242(2) 0.00724(11) Uani 1 1 d U . .
O1 O 1.40465(12) 0.5814(3) 0.02671(6) 0.0098(3) Uani 1 1 d U . .
O2 O 1.37065(13) 0.9718(3) 0.03024(6) 0.0113(3) Uani 1 1 d U . .
O3 O 0.80386(12) 0.6954(3) 0.06651(6) 0.0099(3) Uani 1 1 d U . .
O4 O 0.86886(12) 0.2793(3) 0.09538(6) 0.0106(3) Uani 1 1 d U . .
O5 O 0.88713(13) 0.9723(3) 0.38011(6) 0.0116(3) Uani 1 1 d U . .
O6 O 0.89872(13) 0.5794(3) 0.40022(6) 0.0133(3) Uani 1 1 d U . .
C1 C 1.34236(16) 0.7577(3) 0.03549(8) 0.0081(3) Uani 1 1 d U . .
C2 C 1.23040(16) 0.7048(3) 0.05528(8) 0.0083(3) Uani 1 1 d U . .
C3 C 1.14507(17) 0.8775(4) 0.04795(9) 0.0112(4) Uani 1 1 d U . .
H3 H 1.1593 1.0302 0.0321 0.013 Uiso 1 1 calc R . .
C4 C 1.03923(16) 0.8299(4) 0.06353(9) 0.0107(3) Uani 1 1 d U . .
H4 H 0.9809 0.9484 0.0586 0.013 Uiso 1 1 calc R . .
C5 C 1.02066(16) 0.6056(3) 0.08647(8) 0.0084(3) Uani 1 1 d U . .
C6 C 1.10623(17) 0.4332(4) 0.09629(10) 0.0124(4) Uani 1 1 d U . .
H6 H 1.0928 0.2830 0.1137 0.015 Uiso 1 1 calc R . .
C7 C 1.21150(17) 0.4832(4) 0.08029(10) 0.0123(4) Uani 1 1 d U . .
H7 H 1.2706 0.3663 0.0864 0.015 Uiso 1 1 calc R . .
C8 C 0.88968(16) 0.6058(3) 0.17910(8) 0.0080(3) Uani 1 1 d U . .
C9 C 0.84930(16) 0.8260(4) 0.19511(8) 0.0094(3) Uani 1 1 d U . .
H9 H 0.8194 0.9404 0.1652 0.011 Uiso 1 1 calc R . .
C10 C 0.85395(16) 0.8742(3) 0.25632(8) 0.0085(3) Uani 1 1 d U . .
H10 H 0.8278 1.0244 0.2685 0.010 Uiso 1 1 calc R . .
C11 C 0.89645(16) 0.7050(3) 0.29980(8) 0.0078(3) Uani 1 1 d U . .
C12 C 0.89453(16) 0.7564(3) 0.36581(8) 0.0081(3) Uani 1 1 d U . .
C13 C 0.93669(17) 0.4855(4) 0.28267(9) 0.0111(4) Uani 1 1 d U . .
H13 H 0.9657 0.3701 0.3125 0.013 Uiso 1 1 calc R . .
C14 C 0.93438(17) 0.4355(4) 0.22195(9) 0.0105(4) Uani 1 1 d U . .
H14 H 0.9629 0.2874 0.2099 0.013 Uiso 1 1 calc R . .
C1P C 0.2707(14) -0.214(3) 0.2436(8) 0.069(4) Uiso 0.316(4) 1 d PDU . .
H1P1 H 0.2360 -0.3739 0.2432 0.103 Uiso 0.316(4) 1 calc PR . .
H1P2 H 0.3339 -0.2025 0.2778 0.103 Uiso 0.316(4) 1 calc PR . .
H1P3 H 0.2998 -0.1888 0.2059 0.103 Uiso 0.316(4) 1 calc PR . .
C2P C 0.1814(17) -0.025(4) 0.2498(13) 0.127(9) Uiso 0.316(4) 1 d PDU . .
H2P1 H 0.1861 0.0195 0.2928 0.152 Uiso 0.316(4) 1 calc PR . .
H2P2 H 0.1040 -0.0891 0.2349 0.152 Uiso 0.316(4) 1 calc PR . .
C3P C 0.203(3) 0.196(3) 0.2130(12) 0.257(14) Uiso 0.316(4) 1 d PDU . .
H3P1 H 0.1302 0.2834 0.1998 0.308 Uiso 0.316(4) 1 calc PR . .
H3P2 H 0.2337 0.1470 0.1767 0.308 Uiso 0.316(4) 1 calc PR . .
C4P C 0.2892(19) 0.361(4) 0.2529(14) 0.142(10) Uiso 0.316(4) 1 d PDU . .
H4P1 H 0.3109 0.2904 0.2937 0.171 Uiso 0.316(4) 1 calc PR . .
H4P2 H 0.3592 0.3791 0.2349 0.171 Uiso 0.316(4) 1 calc PR . .
C5P C 0.2322(17) 0.604(3) 0.2570(9) 0.084(5) Uiso 0.316(4) 1 d PDU . .
H5P1 H 0.1670 0.5860 0.2780 0.126 Uiso 0.316(4) 1 calc PR . .
H5P2 H 0.2057 0.6662 0.2162 0.126 Uiso 0.316(4) 1 calc PR . .
H5P3 H 0.2875 0.7161 0.2793 0.126 Uiso 0.316(4) 1 calc PR . .


_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
Ca1 O6 2.2764(15) 2_655 ?
Ca1 O5 2.3060(14) 2_645 ?
Ca1 O2 2.3435(14) 3_775 ?
Ca1 O1 2.3773(14) 3_765 ?
Ca1 O1 2.4196(15) 1_455 ?
Ca1 O3 2.4474(14) . ?
Ca1 O2 2.9366(16) 1_455 ?
Ca1 C1 2.9965(19) 1_455 ?
Ca1 Ca1 3.8315(7) 3_665 ?
Ca1 Ca1 3.9251(8) 3_675 ?
S1 O4 1.4362(14) . ?
S1 O3 1.4508(14) . ?
S1 C8 1.7601(19) . ?
S1 C5 1.7675(19) . ?
O1 C1 1.266(2) . ?
O1 Ca1 2.3773(14) 3_765 ?
O1 Ca1 2.4197(15) 1_655 ?
O2 C1 1.251(2) . ?
O2 Ca1 2.3435(14) 3_775 ?
O2 Ca1 2.9366(16) 1_655 ?
O5 C12 1.253(2) . ?
O5 Ca1 2.3059(14) 2_655 ?
O6 C12 1.250(2) . ?
O6 Ca1 2.2764(15) 2_645 ?
C1 C2 1.502(3) . ?
C1 Ca1 2.9965(19) 1_655 ?
C2 C3 1.387(3) . ?
C2 C7 1.392(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.387(3) . ?
C8 C9 1.388(3) . ?
C8 C14 1.392(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.390(3) . ?
C11 C13 1.392(3) . ?
C11 C12 1.516(3) . ?
C13 C14 1.389(3) . ?
C1P C2P 1.520(10) . ?
C2P C3P 1.531(10) . ?
C3P C4P 1.543(10) . ?
C4P C5P 1.526(9) . ?

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
O6 Ca1 O5 96.37(5) 2_655 2_645 ?
O6 Ca1 O2 81.38(5) 2_655 3_775 ?
O5 Ca1 O2 165.55(5) 2_645 3_775 ?
O6 Ca1 O1 174.45(5) 2_655 3_765 ?
O5 Ca1 O1 88.93(5) 2_645 3_765 ?
O2 Ca1 O1 93.08(5) 3_775 3_765 ?
O6 Ca1 O1 108.57(5) 2_655 1_455 ?
O5 Ca1 O1 79.28(5) 2_645 1_455 ?
O2 Ca1 O1 115.03(5) 3_775 1_455 ?
O1 Ca1 O1 73.98(5) 3_765 1_455 ?
O6 Ca1 O3 91.95(5) 2_655 . ?
O5 Ca1 O3 78.57(5) 2_645 . ?
O2 Ca1 O3 87.22(5) 3_775 . ?
O1 Ca1 O3 87.46(5) 3_765 . ?
O1 Ca1 O3 151.23(5) 1_455 . ?
O6 Ca1 O2 68.18(5) 2_655 1_455 ?
O5 Ca1 O2 107.91(5) 2_645 1_455 ?
O2 Ca1 O2 84.62(5) 3_775 1_455 ?
O1 Ca1 O2 111.77(4) 3_765 1_455 ?
O1 Ca1 O2 47.73(4) 1_455 1_455 ?
O3 Ca1 O2 159.43(5) . 1_455 ?
O6 Ca1 C1 86.11(5) 2_655 1_455 ?
O5 Ca1 C1 90.28(5) 2_645 1_455 ?
O2 Ca1 C1 103.75(5) 3_775 1_455 ?
O1 Ca1 C1 95.54(5) 3_765 1_455 ?
O1 Ca1 C1 24.16(5) 1_455 1_455 ?
O3 Ca1 C1 168.41(5) . 1_455 ?
O2 Ca1 C1 24.32(4) 1_455 1_455 ?
O6 Ca1 Ca1 144.95(4) 2_655 3_665 ?
O5 Ca1 Ca1 82.58(4) 2_645 3_665 ?
O2 Ca1 Ca1 107.48(4) 3_775 3_665 ?
O1 Ca1 Ca1 37.37(3) 3_765 3_665 ?
O1 Ca1 Ca1 36.61(3) 1_455 3_665 ?
O3 Ca1 Ca1 121.74(4) . 3_665 ?
O2 Ca1 Ca1 78.78(3) 1_455 3_665 ?
C1 Ca1 Ca1 58.92(4) 1_455 3_665 ?
O6 Ca1 Ca1 68.43(4) 2_655 3_675 ?
O5 Ca1 Ca1 143.93(4) 2_645 3_675 ?
O2 Ca1 Ca1 48.15(4) 3_775 3_675 ?
O1 Ca1 Ca1 108.03(4) 3_765 3_675 ?
O1 Ca1 Ca1 75.48(4) 1_455 3_675 ?
O3 Ca1 Ca1 132.18(4) . 3_675 ?
O2 Ca1 Ca1 36.47(3) 1_455 3_675 ?
C1 Ca1 Ca1 57.33(4) 1_455 3_675 ?
Ca1 Ca1 Ca1 91.934(17) 3_665 3_675 ?
O4 S1 O3 119.66(9) . . ?
O4 S1 C8 108.43(9) . . ?
O3 S1 C8 108.36(9) . . ?
O4 S1 C5 107.64(9) . . ?
O3 S1 C5 106.50(9) . . ?
C8 S1 C5 105.37(9) . . ?
C1 O1 Ca1 139.10(12) . 3_765 ?
C1 O1 Ca1 104.37(12) . 1_655 ?
Ca1 O1 Ca1 106.02(5) 3_765 1_655 ?
C1 O2 Ca1 142.14(13) . 3_775 ?
C1 O2 Ca1 80.52(11) . 1_655 ?
Ca1 O2 Ca1 95.38(5) 3_775 1_655 ?
S1 O3 Ca1 137.29(9) . . ?
C12 O5 Ca1 145.80(13) . 2_655 ?
C12 O6 Ca1 176.90(14) . 2_645 ?
O2 C1 O1 123.53(18) . . ?
O2 C1 C2 118.76(17) . . ?
O1 C1 C2 117.67(17) . . ?
O2 C1 Ca1 75.16(11) . 1_655 ?
O1 C1 Ca1 51.47(9) . 1_655 ?
C2 C1 Ca1 156.44(13) . 1_655 ?
C3 C2 C7 119.95(18) . . ?
C3 C2 C1 119.62(17) . . ?
C7 C2 C1 120.43(17) . . ?
C2 C3 C4 120.82(18) . . ?
C5 C4 C3 118.42(18) . . ?
C4 C5 C6 121.69(18) . . ?
C4 C5 S1 119.37(14) . . ?
C6 C5 S1 118.93(15) . . ?
C7 C6 C5 119.17(18) . . ?
C6 C7 C2 119.86(18) . . ?
C9 C8 C14 122.13(17) . . ?
C9 C8 S1 119.92(14) . . ?
C14 C8 S1 117.95(14) . . ?
C8 C9 C10 118.02(17) . . ?
C11 C10 C9 120.77(17) . . ?
C10 C11 C13 120.19(17) . . ?
C10 C11 C12 119.70(17) . . ?
C13 C11 C12 120.06(17) . . ?
O6 C12 O5 126.66(18) . . ?
O6 C12 C11 116.80(17) . . ?
O5 C12 C11 116.53(17) . . ?
C14 C13 C11 119.91(18) . . ?
C13 C14 C8 118.97(18) . . ?
C1P C2P C3P 109.1(9) . . ?
C2P C3P C4P 108.7(9) . . ?
C5P C4P C3P 107.8(9) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.63
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_DB1_156B
_database_code_depnum_ccdc_archive 'CCDC 1051646'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14.50 H9.34 Ca O6 S'
_chemical_formula_sum            'C14.50 H9.34 Ca O6 S'
_chemical_formula_weight         351.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   11.7073(10)
_cell_length_b                   5.5647(5)
_cell_length_c                   22.830(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5860(10)
_cell_angle_gamma                90.00
_cell_volume                     1462.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             721
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16777
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         30.51
_reflns_number_total             4434
_reflns_number_gt                3850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+1.0966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4434
_refine_ls_number_parameters     218
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.63729(3) 0.25666(5) 0.221920(13) 0.00722(8) Uani 1 1 d . . .
S1 S 0.39846(3) 0.46493(7) 0.106737(16) 0.00777(9) Uani 1 1 d . . .
O1 O 0.26426(10) 0.0231(2) -0.17208(5) 0.0110(2) Uani 1 1 d . . .
O2 O 0.26053(10) 0.4149(2) -0.19089(5) 0.0102(2) Uani 1 1 d . . .
O3 O 0.41539(10) 0.7209(2) 0.11051(5) 0.0115(2) Uani 1 1 d . . .
O4 O 0.49480(10) 0.3061(2) 0.12965(5) 0.0106(2) Uani 1 1 d . . .
O5 O -0.01289(10) 0.0241(2) 0.24639(5) 0.0124(2) Uani 1 1 d . . .
O6 O -0.04196(10) 0.4196(2) 0.25535(5) 0.0132(2) Uani 1 1 d . . .
C11 C 0.10083(13) 0.2925(3) 0.20110(7) 0.0086(3) Uani 1 1 d . . .
C2 C 0.29868(13) 0.2915(3) -0.08959(7) 0.0087(3) Uani 1 1 d . . .
C9 C 0.19234(14) 0.5596(3) 0.14051(7) 0.0110(3) Uani 1 1 d . . .
H9 H 0.1932 0.7055 0.1190 0.013 Uiso 1 1 calc R . .
C3 C 0.26760(14) 0.5120(3) -0.06835(7) 0.0120(3) Uani 1 1 d . . .
H3 H 0.2283 0.6281 -0.0953 0.014 Uiso 1 1 calc R . .
C10 C 0.10262(14) 0.5103(3) 0.17100(7) 0.0112(3) Uani 1 1 d . . .
H10 H 0.0426 0.6248 0.1714 0.013 Uiso 1 1 calc R . .
C4 C 0.29424(14) 0.5621(3) -0.00763(7) 0.0118(3) Uani 1 1 d . . .
H4 H 0.2722 0.7109 0.0074 0.014 Uiso 1 1 calc R . .
C6 C 0.38210(14) 0.1674(3) 0.01042(7) 0.0108(3) Uani 1 1 d . . .
H6 H 0.4201 0.0502 0.0374 0.013 Uiso 1 1 calc R . .
C13 C 0.18857(14) 0.1242(3) 0.20044(7) 0.0103(3) Uani 1 1 d . . .
H13 H 0.1856 -0.0255 0.2201 0.012 Uiso 1 1 calc R . .
C14 C 0.28046(13) 0.1722(3) 0.17132(7) 0.0099(3) Uani 1 1 d . . .
H14 H 0.3411 0.0586 0.1714 0.012 Uiso 1 1 calc R . .
C1 C 0.27420(13) 0.2382(3) -0.15538(7) 0.0087(3) Uani 1 1 d . . .
C7 C 0.35396(14) 0.1191(3) -0.05017(7) 0.0107(3) Uani 1 1 d . . .
H7 H 0.3726 -0.0329 -0.0648 0.013 Uiso 1 1 calc R . .
C12 C 0.00659(13) 0.2410(3) 0.23699(7) 0.0093(3) Uani 1 1 d . . .
C5 C 0.35353(13) 0.3908(3) 0.03067(7) 0.0089(3) Uani 1 1 d . . .
C8 C 0.28117(13) 0.3913(3) 0.14203(7) 0.0085(3) Uani 1 1 d . . .
C1P C -0.0267(9) 1.015(2) 0.0515(4) 0.072(4) Uani 0.334(9) 1 d PD . .
H1P1 H -0.0099 1.1186 0.0868 0.108 Uiso 0.334(9) 1 calc PR . .
H1P2 H -0.0019 0.8505 0.0625 0.108 Uiso 0.334(9) 1 calc PR . .
H1P3 H -0.1103 1.0172 0.0356 0.108 Uiso 0.334(9) 1 calc PR . .
C2P C 0.0360(19) 1.104(4) 0.0063(7) 0.067(6) Uani 0.167(5) 1 d PD . .
H2P1 H 0.1195 1.1058 0.0246 0.081 Uiso 0.167(5) 1 calc PR . .
H2P2 H 0.0123 1.2730 -0.0017 0.081 Uiso 0.167(5) 1 calc PR . .


_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
Ca1 O6 2.2902(12) 2_545 ?
Ca1 O5 2.2907(12) 2 ?
Ca1 O1 2.3513(12) 3_655 ?
Ca1 O2 2.3632(12) 3_665 ?
Ca1 O2 2.4289(12) 4_666 ?
Ca1 O4 2.4504(11) . ?
Ca1 O1 2.8716(12) 4_666 ?
Ca1 C1 2.9609(16) 4_666 ?
Ca1 Ca1 3.8868(5) 2_645 ?
Ca1 Ca1 3.8868(5) 2_655 ?
S1 O3 1.4386(12) . ?
S1 O4 1.4525(12) . ?
S1 C8 1.7633(15) . ?
S1 C5 1.7682(16) . ?
O1 C1 1.2553(19) . ?
O1 Ca1 2.3514(12) 3_655 ?
O1 Ca1 2.8716(12) 4_565 ?
O2 C1 1.2656(19) . ?
O2 Ca1 2.3633(12) 3_665 ?
O2 Ca1 2.4289(12) 4_565 ?
O5 C12 1.2538(19) . ?
O5 Ca1 2.2906(12) 2_545 ?
O6 C12 1.2549(19) . ?
O6 Ca1 2.2901(12) 2 ?
C11 C13 1.392(2) . ?
C11 C10 1.395(2) . ?
C11 C12 1.518(2) . ?
C2 C7 1.391(2) . ?
C2 C3 1.392(2) . ?
C2 C1 1.506(2) . ?
C9 C10 1.390(2) . ?
C9 C8 1.395(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.390(2) . ?
C6 C7 1.388(2) . ?
C6 C5 1.388(2) . ?
C13 C14 1.391(2) . ?
C14 C8 1.391(2) . ?
C1 Ca1 2.9609(16) 4_565 ?
C1P C2P 1.457(15) . ?
C2P C1P 1.462(15) 3_575 ?

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
O6 Ca1 O5 95.51(4) 2_545 2 ?
O6 Ca1 O1 82.54(4) 2_545 3_655 ?
O5 Ca1 O1 168.44(4) 2 3_655 ?
O6 Ca1 O2 174.78(4) 2_545 3_665 ?
O5 Ca1 O2 88.76(4) 2 3_665 ?
O1 Ca1 O2 92.69(4) 3_655 3_665 ?
O6 Ca1 O2 74.53(4) 2_545 4_666 ?
O5 Ca1 O2 108.24(4) 2 4_666 ?
O1 Ca1 O2 82.31(4) 3_655 4_666 ?
O2 Ca1 O2 107.00(3) 3_665 4_666 ?
O6 Ca1 O4 90.21(4) 2_545 . ?
O5 Ca1 O4 80.02(4) 2 . ?
O1 Ca1 O4 88.58(4) 3_655 . ?
O2 Ca1 O4 87.57(4) 3_665 . ?
O2 Ca1 O4 163.07(4) 4_666 . ?
O6 Ca1 O1 110.91(4) 2_545 4_666 ?
O5 Ca1 O1 73.57(4) 2 4_666 ?
O1 Ca1 O1 117.81(3) 3_655 4_666 ?
O2 Ca1 O1 73.16(4) 3_665 4_666 ?
O2 Ca1 O1 48.67(4) 4_666 4_666 ?
O4 Ca1 O1 147.32(4) . 4_666 ?
O6 Ca1 C1 89.72(4) 2_545 4_666 ?
O5 Ca1 C1 87.71(4) 2 4_666 ?
O1 Ca1 C1 103.64(4) 3_655 4_666 ?
O2 Ca1 C1 93.45(4) 3_665 4_666 ?
O2 Ca1 C1 24.73(4) 4_666 4_666 ?
O4 Ca1 C1 167.66(4) . 4_666 ?
O1 Ca1 C1 24.80(4) 4_666 4_666 ?
O6 Ca1 Ca1 70.65(3) 2_545 2_645 ?
O5 Ca1 Ca1 142.52(3) 2 2_645 ?
O1 Ca1 Ca1 47.32(3) 3_655 2_645 ?
O2 Ca1 Ca1 107.58(3) 3_665 2_645 ?
O2 Ca1 Ca1 35.24(3) 4_666 2_645 ?
O4 Ca1 Ca1 132.66(3) . 2_645 ?
O1 Ca1 Ca1 79.20(3) 4_666 2_645 ?
C1 Ca1 Ca1 58.54(3) 4_666 2_645 ?
O6 Ca1 Ca1 147.26(3) 2_545 2_655 ?
O5 Ca1 Ca1 82.14(3) 2 2_655 ?
O1 Ca1 Ca1 105.67(3) 3_655 2_655 ?
O2 Ca1 Ca1 36.37(3) 3_665 2_655 ?
O2 Ca1 Ca1 75.28(3) 4_666 2_655 ?
O4 Ca1 Ca1 121.12(3) . 2_655 ?
O1 Ca1 Ca1 37.01(2) 4_666 2_655 ?
C1 Ca1 Ca1 57.61(3) 4_666 2_655 ?
Ca1 Ca1 Ca1 91.425(14) 2_645 2_655 ?
O3 S1 O4 119.44(7) . . ?
O3 S1 C8 108.24(7) . . ?
O4 S1 C8 108.20(7) . . ?
O3 S1 C5 107.62(7) . . ?
O4 S1 C5 106.44(7) . . ?
C8 S1 C5 106.17(7) . . ?
C1 O1 Ca1 138.77(10) . 3_655 ?
C1 O1 Ca1 81.59(9) . 4_565 ?
Ca1 O1 Ca1 95.66(4) 3_655 4_565 ?
C1 O2 Ca1 141.39(10) . 3_665 ?
C1 O2 Ca1 101.88(9) . 4_565 ?
Ca1 O2 Ca1 108.39(4) 3_665 4_565 ?
S1 O4 Ca1 137.63(7) . . ?
C12 O5 Ca1 145.65(11) . 2_545 ?
C12 O6 Ca1 173.70(11) . 2 ?
C13 C11 C10 120.08(14) . . ?
C13 C11 C12 119.32(14) . . ?
C10 C11 C12 120.54(14) . . ?
C7 C2 C3 120.19(14) . . ?
C7 C2 C1 119.36(14) . . ?
C3 C2 C1 120.45(14) . . ?
C10 C9 C8 118.90(14) . . ?
C2 C3 C4 119.89(15) . . ?
C9 C10 C11 119.96(14) . . ?
C5 C4 C3 118.93(15) . . ?
C7 C6 C5 118.54(15) . . ?
C14 C13 C11 120.85(14) . . ?
C13 C14 C8 118.15(14) . . ?
O1 C1 O2 123.53(14) . . ?
O1 C1 C2 118.73(14) . . ?
O2 C1 C2 117.69(14) . . ?
O1 C1 Ca1 73.62(9) . 4_565 ?
O2 C1 Ca1 53.39(8) . 4_565 ?
C2 C1 Ca1 155.85(10) . 4_565 ?
C6 C7 C2 120.54(15) . . ?
O5 C12 O6 126.69(15) . . ?
O5 C12 C11 116.58(14) . . ?
O6 C12 C11 116.71(14) . . ?
C6 C5 C4 121.83(14) . . ?
C6 C5 S1 119.31(12) . . ?
C4 C5 S1 118.81(12) . . ?
C14 C8 C9 122.01(14) . . ?
C14 C8 S1 119.81(12) . . ?
C9 C8 S1 118.17(12) . . ?
C1P C2P C1P 121.5(13) . 3_575 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_DB1_120B2
_database_code_depnum_ccdc_archive 'CCDC 1051647'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15.31 H11.50 Ca O6 S'
_chemical_formula_sum            'C15.31 H11.50 Ca O6 S'
_chemical_formula_weight         363.5

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   11.6426(8)
_cell_length_b                   5.5574(4)
_cell_length_c                   22.8446(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.6810(10)
_cell_angle_gamma                90.00
_cell_volume                     1452.50(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16471
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         30.42
_reflns_number_total             4365
_reflns_number_gt                4041
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+1.4244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4365
_refine_ls_number_parameters     218
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.63725(2) -0.25855(4) 0.221255(11) 0.00766(7) Uani 1 1 d . . .
S1 S 0.39739(3) -0.46701(6) 0.106089(13) 0.00781(8) Uani 1 1 d . . .
O1 O 0.75956(8) -0.08773(18) 0.30892(4) 0.01047(18) Uani 1 1 d . . .
O2 O 0.76333(9) -0.47921(18) 0.32817(4) 0.01136(19) Uani 1 1 d . . .
O3 O 0.51274(9) 0.47435(18) 0.25310(5) 0.01263(19) Uani 1 1 d . . .
O4 O 0.54161(9) 0.07891(19) 0.24366(5) 0.0134(2) Uani 1 1 d . . .
O5 O 0.41423(9) -0.72328(18) 0.10967(4) 0.01150(19) Uani 1 1 d . . .
O6 O 0.49453(8) -0.30891(19) 0.12907(4) 0.01071(18) Uani 1 1 d . . .
C1 C 0.77313(11) -0.2643(2) 0.34464(6) 0.0087(2) Uani 1 1 d . . .
C2 C 0.29730(11) -0.2903(2) -0.08989(6) 0.0084(2) Uani 1 1 d . . .
C3 C 0.26526(12) -0.5109(2) -0.06885(6) 0.0120(2) Uani 1 1 d . . .
H3 H 0.2253 -0.6263 -0.0959 0.014 Uiso 1 1 calc R . .
C4 C 0.29170(12) -0.5620(2) -0.00832(6) 0.0122(2) Uani 1 1 d . . .
H4 H 0.2690 -0.7110 0.0065 0.015 Uiso 1 1 calc R . .
C5 C 0.35195(11) -0.3917(2) 0.03031(6) 0.0088(2) Uani 1 1 d . . .
C6 C 0.38114(12) -0.1679(3) 0.01029(6) 0.0113(2) Uani 1 1 d . . .
H6 H 0.4196 -0.0512 0.0374 0.014 Uiso 1 1 calc R . .
C7 C 0.35291(12) -0.1183(2) -0.05027(6) 0.0111(2) Uani 1 1 d . . .
H7 H 0.3717 0.0342 -0.0647 0.013 Uiso 1 1 calc R . .
C8 C 0.28003(11) -0.3932(2) 0.14147(6) 0.0089(2) Uani 1 1 d . . .
C9 C 0.19084(12) -0.5614(2) 0.14017(6) 0.0116(2) Uani 1 1 d . . .
H9 H 0.1912 -0.7073 0.1185 0.014 Uiso 1 1 calc R . .
C10 C 0.10135(12) -0.5121(2) 0.17107(6) 0.0115(2) Uani 1 1 d . . .
H10 H 0.0410 -0.6267 0.1715 0.014 Uiso 1 1 calc R . .
C11 C 0.10016(11) -0.2948(2) 0.20137(6) 0.0092(2) Uani 1 1 d . . .
C12 C 0.49323(11) 0.2567(2) 0.26234(6) 0.0096(2) Uani 1 1 d . . .
C13 C 0.18832(11) -0.1257(2) 0.20036(6) 0.0099(2) Uani 1 1 d . . .
H13 H 0.1857 0.0243 0.2200 0.012 Uiso 1 1 calc R . .
C14 C 0.28006(11) -0.1745(2) 0.17088(6) 0.0100(2) Uani 1 1 d . . .
H14 H 0.3411 -0.0612 0.1709 0.012 Uiso 1 1 calc R . .
C1P C -0.0205(4) -0.0254(10) 0.04959(18) 0.0858(17) Uani 0.874(9) 1 d PD . .
H1P1 H -0.0687 0.0537 0.0748 0.129 Uiso 0.874(9) 1 calc PR . .
H1P2 H 0.0616 -0.0222 0.0696 0.129 Uiso 0.874(9) 1 calc PR . .
H1P3 H -0.0460 -0.1926 0.0425 0.129 Uiso 0.874(9) 1 calc PR . .
C2P C -0.0316(5) 0.0876(18) -0.0010(4) 0.080(3) Uani 0.437(4) 1 d PD . .
H2P1 H -0.0071 0.2554 0.0091 0.096 Uiso 0.437(4) 1 calc PR . .
H2P2 H -0.1166 0.0938 -0.0169 0.096 Uiso 0.437(4) 1 calc PR . .


_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
Ca1 O3 2.2858(10) 1_545 ?
Ca1 O4 2.2870(10) . ?
Ca1 O2 2.3472(10) 2_655 ?
Ca1 O1 2.3605(10) 2_645 ?
Ca1 O1 2.4254(10) . ?
Ca1 O6 2.4448(10) . ?
Ca1 O2 2.8802(11) . ?
Ca1 C1 2.9658(13) . ?
Ca1 Ca1 3.8809(4) 2_645 ?
Ca1 Ca1 3.8809(4) 2_655 ?
S1 O5 1.4379(10) . ?
S1 O6 1.4514(10) . ?
S1 C8 1.7600(13) . ?
S1 C5 1.7641(13) . ?
O1 C1 1.2672(16) . ?
O1 Ca1 2.3605(10) 2_655 ?
O2 C1 1.2511(16) . ?
O2 Ca1 2.3472(10) 2_645 ?
O3 C12 1.2557(16) . ?
O3 Ca1 2.2858(10) 1_565 ?
O4 C12 1.2509(17) . ?
C1 C2 1.5007(18) 4_656 ?
C2 C7 1.3908(18) . ?
C2 C3 1.3926(18) . ?
C2 C1 1.5007(18) 4 ?
C3 C4 1.3892(18) . ?
C4 C5 1.3919(18) . ?
C5 C6 1.3891(18) . ?
C6 C7 1.3891(18) . ?
C8 C14 1.3888(18) . ?
C8 C9 1.3934(18) . ?
C9 C10 1.3898(18) . ?
C10 C11 1.3935(18) . ?
C11 C13 1.3949(18) . ?
C11 C12 1.5119(18) 2_545 ?
C12 C11 1.5118(18) 2 ?
C13 C14 1.3910(18) . ?
C1P C2P 1.301(10) . ?
C2P C1P 1.402(9) 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
O3 Ca1 O4 95.60(4) 1_545 . ?
O3 Ca1 O2 168.81(4) 1_545 2_655 ?
O4 Ca1 O2 82.49(4) . 2_655 ?
O3 Ca1 O1 88.67(4) 1_545 2_645 ?
O4 Ca1 O1 174.96(4) . 2_645 ?
O2 Ca1 O1 92.81(4) 2_655 2_645 ?
O3 Ca1 O1 107.54(4) 1_545 . ?
O4 Ca1 O1 74.33(4) . . ?
O2 Ca1 O1 82.64(4) 2_655 . ?
O1 Ca1 O1 106.96(2) 2_645 . ?
O3 Ca1 O6 80.21(4) 1_545 . ?
O4 Ca1 O6 90.31(4) . . ?
O2 Ca1 O6 88.76(4) 2_655 . ?
O1 Ca1 O6 87.78(3) 2_645 . ?
O1 Ca1 O6 163.21(4) . . ?
O3 Ca1 O2 72.98(3) 1_545 . ?
O4 Ca1 O2 110.61(3) . . ?
O2 Ca1 O2 118.05(2) 2_655 . ?
O1 Ca1 O2 73.18(3) 2_645 . ?
O1 Ca1 O2 48.51(3) . . ?
O6 Ca1 O2 147.14(3) . . ?
O3 Ca1 C1 87.05(4) 1_545 . ?
O4 Ca1 C1 89.55(4) . . ?
O2 Ca1 C1 103.92(4) 2_655 . ?
O1 Ca1 C1 93.35(3) 2_645 . ?
O1 Ca1 C1 24.68(3) . . ?
O6 Ca1 C1 167.19(4) . . ?
O2 Ca1 C1 24.66(3) . . ?
O3 Ca1 Ca1 81.75(3) 1_545 2_645 ?
O4 Ca1 Ca1 146.96(3) . 2_645 ?
O2 Ca1 Ca1 105.86(3) 2_655 2_645 ?
O1 Ca1 Ca1 36.38(2) 2_645 2_645 ?
O1 Ca1 Ca1 75.16(3) . 2_645 ?
O6 Ca1 Ca1 121.24(3) . 2_645 ?
O2 Ca1 Ca1 37.03(2) . 2_645 ?
C1 Ca1 Ca1 57.48(3) . 2_645 ?
O3 Ca1 Ca1 141.85(3) 1_545 2_655 ?
O4 Ca1 Ca1 70.37(3) . 2_655 ?
O2 Ca1 Ca1 47.64(3) 2_655 2_655 ?
O1 Ca1 Ca1 107.74(3) 2_645 2_655 ?
O1 Ca1 Ca1 35.26(2) . 2_655 ?
O6 Ca1 Ca1 133.05(3) . 2_655 ?
O2 Ca1 Ca1 79.13(2) . 2_655 ?
C1 Ca1 Ca1 58.52(3) . 2_655 ?
Ca1 Ca1 Ca1 91.450(12) 2_645 2_655 ?
O5 S1 O6 119.35(6) . . ?
O5 S1 C8 108.30(6) . . ?
O6 S1 C8 108.19(6) . . ?
O5 S1 C5 107.68(6) . . ?
O6 S1 C5 106.45(6) . . ?
C8 S1 C5 106.15(6) . . ?
C1 O1 Ca1 141.14(9) . 2_655 ?
C1 O1 Ca1 102.29(8) . . ?
Ca1 O1 Ca1 108.36(4) 2_655 . ?
C1 O2 Ca1 138.63(9) . 2_645 ?
C1 O2 Ca1 81.51(8) . . ?
Ca1 O2 Ca1 95.33(3) 2_645 . ?
C12 O3 Ca1 145.50(9) . 1_565 ?
C12 O4 Ca1 173.13(10) . . ?
S1 O6 Ca1 137.77(6) . . ?
O2 C1 O1 123.50(12) . . ?
O2 C1 C2 118.85(12) . 4_656 ?
O1 C1 C2 117.60(12) . 4_656 ?
O2 C1 Ca1 73.84(7) . . ?
O1 C1 Ca1 53.04(7) . . ?
C2 C1 Ca1 155.99(9) 4_656 . ?
C7 C2 C3 120.16(12) . . ?
C7 C2 C1 119.23(12) . 4 ?
C3 C2 C1 120.61(12) . 4 ?
C4 C3 C2 119.97(12) . . ?
C3 C4 C5 118.99(12) . . ?
C6 C5 C4 121.70(12) . . ?
C6 C5 S1 119.24(10) . . ?
C4 C5 S1 119.01(10) . . ?
C7 C6 C5 118.57(12) . . ?
C6 C7 C2 120.50(12) . . ?
C14 C8 C9 122.07(12) . . ?
C14 C8 S1 119.70(10) . . ?
C9 C8 S1 118.22(10) . . ?
C10 C9 C8 118.87(12) . . ?
C9 C10 C11 120.04(12) . . ?
C10 C11 C13 120.04(12) . . ?
C10 C11 C12 120.72(12) . 2_545 ?
C13 C11 C12 119.19(12) . 2_545 ?
O4 C12 O3 126.63(13) . . ?
O4 C12 C11 116.91(12) . 2 ?
O3 C12 C11 116.45(12) . 2 ?
C14 C13 C11 120.67(12) . . ?
C8 C14 C13 118.26(12) . . ?
C1P C2P C1P 126.7(7) . 3 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.42
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_CaSDB_butane
_database_code_depnum_ccdc_archive 'CCDC 1427863'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Ca O6 S, 0.18(C4 H10)'
_chemical_formula_sum            'C14.72 H9.79 Ca O6 S'
_chemical_formula_weight         354.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   11.6884(5)
_cell_length_b                   5.5643(2)
_cell_length_c                   22.8159(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.691(4)
_cell_angle_gamma                90
_cell_volume                     1458.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9130
_cell_measurement_theta_min      3.5970
_cell_measurement_theta_max      33.5160

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_min  0.95067
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4962

_diffrn_reflns_number            26543
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.518
_diffrn_reflns_theta_max         33.845
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5563
_reflns_number_gt                4776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_orient_matrix_UB_11      -0.0569898000
_diffrn_orient_matrix_UB_12      -0.0078427000
_diffrn_orient_matrix_UB_13      -0.0172249000
_diffrn_orient_matrix_UB_21      -0.0119169000
_diffrn_orient_matrix_UB_22      0.1183569000
_diffrn_orient_matrix_UB_23      0.0087325000
_diffrn_orient_matrix_UB_31      0.0206387000
_diffrn_orient_matrix_UB_32      0.0466906000
_diffrn_orient_matrix_UB_33      -0.0250416000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8714  179.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8714   37.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega -110.00  -56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8089 -179.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00    6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8089  -57.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8714   19.0000  -60.0000 121

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8714   37.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega -110.00  -56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8089 -179.0000  -30.0000 54

;
_diffrn_measurement_method       'ω scans'

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0330P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5563
_refine_ls_number_parameters     236
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.001

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
Ca1 Ca -0.13742(2) 0.75633(4) 0.27818(2) 0.00731(6) Uani 1 1 d . . . . .
S1 S 0.10145(3) 0.96454(5) 0.39330(2) 0.00772(6) Uani 1 1 d . . . . .
O1 O 0.23970(8) 0.91505(17) 0.69092(4) 0.01017(17) Uani 1 1 d . . . . .
O2 O 0.23621(8) 0.52343(17) 0.67212(4) 0.01094(17) Uani 1 1 d . . . . .
O3 O 0.54211(9) 0.91879(18) 0.24461(4) 0.01308(18) Uani 1 1 d . . . . .
O4 O 0.51296(8) 0.52383(17) 0.25348(4) 0.01210(18) Uani 1 1 d . . . . .
O5 O 0.08446(9) 1.22059(17) 0.38950(4) 0.01123(17) Uani 1 1 d . . . . .
O6 O 0.00494(8) 0.80562(17) 0.37030(4) 0.01047(17) Uani 1 1 d . . . . .
C1 C 0.14670(11) 0.8909(2) 0.46929(5) 0.0086(2) Uani 1 1 d . . . . .
C2 C 0.20595(12) 1.0620(2) 0.50775(6) 0.0120(2) Uani 1 1 d . . . . .
H2 H 0.2278 1.2111 0.4928 0.014 Uiso 1 1 calc R U . . .
C3 C 0.23276(12) 1.0122(2) 0.56837(6) 0.0121(2) Uani 1 1 d . . . . .
H3 H 0.2722 1.1283 0.5953 0.015 Uiso 1 1 calc R U . . .
C4 C 0.20170(11) 0.7914(2) 0.58960(5) 0.0086(2) Uani 1 1 d . . . . .
C5 C 0.14677(12) 0.6188(2) 0.55025(6) 0.0117(2) Uani 1 1 d . . . . .
H5 H 0.1287 0.4663 0.5649 0.014 Uiso 1 1 calc R U . . .
C6 C 0.11802(12) 0.6670(2) 0.48962(6) 0.0114(2) Uani 1 1 d . . . . .
H6 H 0.0796 0.5499 0.4626 0.014 Uiso 1 1 calc R U . . .
C7 C 0.22619(10) 0.7384(2) 0.65525(5) 0.0084(2) Uani 1 1 d . . . . .
C8 C 0.21873(11) 0.8908(2) 0.35811(5) 0.0087(2) Uani 1 1 d . . . . .
C9 C 0.30779(12) 1.0591(2) 0.35955(6) 0.0112(2) Uani 1 1 d . . . . .
H9 H 0.3071 1.2051 0.3811 0.013 Uiso 1 1 calc R U . . .
C10 C 0.39763(11) 1.0098(2) 0.32897(6) 0.0111(2) Uani 1 1 d . . . . .
H10 H 0.4576 1.1245 0.3285 0.013 Uiso 1 1 calc R U . . .
C11 C 0.39952(11) 0.7918(2) 0.29902(6) 0.0090(2) Uani 1 1 d . . . . .
C12 C 0.31163(11) 0.6232(2) 0.29972(6) 0.0100(2) Uani 1 1 d . . . . .
H12 H 0.3146 0.4732 0.2801 0.012 Uiso 1 1 calc R U . . .
C13 C 0.21940(11) 0.6721(2) 0.32884(6) 0.0100(2) Uani 1 1 d . . . . .
H13 H 0.1586 0.5588 0.3287 0.012 Uiso 1 1 calc R U . . .
C14 C 0.49352(11) 0.7410(2) 0.26289(6) 0.0088(2) Uani 1 1 d . . . . .
C1B C 0.5205(14) 0.783(3) 0.5143(9) 0.081(7) Uani 0.179(4) 1 d D U P . .
H1B1 H 0.4800 0.9328 0.5010 0.121 Uiso 0.179(4) 1 calc R U P . .
H1B2 H 0.5150 0.7521 0.5560 0.121 Uiso 0.179(4) 1 calc R U P . .
H1B3 H 0.6026 0.7963 0.5108 0.121 Uiso 0.179(4) 1 calc R U P . .
C2B C 0.467(2) 0.584(3) 0.4770(9) 0.085(7) Uani 0.179(4) 1 d D U P . .
H2B1 H 0.4709 0.6188 0.4349 0.103 Uiso 0.179(4) 1 calc R U P . .
H2B2 H 0.3834 0.5746 0.4800 0.103 Uiso 0.179(4) 1 calc R U P . .
C3B C 0.522(2) 0.344(3) 0.4936(11) 0.099(8) Uani 0.179(4) 1 d D U P . .
H3B1 H 0.5018 0.2317 0.4596 0.119 Uiso 0.179(4) 1 calc R U P . .
H3B2 H 0.6080 0.3624 0.5023 0.119 Uiso 0.179(4) 1 calc R U P . .
C4B C 0.4821(18) 0.244(6) 0.5468(12) 0.175(15) Uani 0.179(4) 1 d D U P . .
H4B1 H 0.5192 0.0876 0.5570 0.262 Uiso 0.179(4) 1 calc R U P . .
H4B2 H 0.5034 0.3542 0.5805 0.262 Uiso 0.179(4) 1 calc R U P . .
H4B3 H 0.3973 0.2238 0.5379 0.262 Uiso 0.179(4) 1 calc R U P . .


_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
Ca1 O4 2.2898(10) 2 ?
Ca1 O3 2.2922(10) 2_545 ?
Ca1 O2 2.3512(10) 3_566 ?
Ca1 O1 2.3627(10) 3_576 ?
Ca1 O1 2.4239(10) 4_575 ?
Ca1 O6 2.4421(10) . ?
Ca1 O2 2.8659(10) 4_575 ?
S1 O5 1.4389(10) . ?
S1 O6 1.4526(10) . ?
S1 C8 1.7608(13) . ?
S1 C1 1.7646(13) . ?
O1 C7 1.2672(15) . ?
O1 Ca1 2.3628(10) 3_576 ?
O1 Ca1 2.4239(10) 4_676 ?
O2 C7 1.2552(15) . ?
O2 Ca1 2.3512(10) 3_566 ?
O2 Ca1 2.8659(10) 4_676 ?
O3 C14 1.2503(15) . ?
O3 Ca1 2.2922(10) 2 ?
O4 C14 1.2554(15) . ?
O4 Ca1 2.2899(10) 2_545 ?
C1 C2 1.3895(17) . ?
C1 C6 1.3918(18) . ?
C2 C3 1.3881(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3930(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3884(17) . ?
C4 C7 1.5012(17) . ?
C5 C6 1.3879(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 Ca1 2.9580(13) 4_676 ?
C8 C13 1.3890(17) . ?
C8 C9 1.3959(17) . ?
C9 C10 1.3918(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3942(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3935(17) . ?
C11 C14 1.5174(17) . ?
C12 C13 1.3941(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C1B C2B 1.465(16) . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C1B H1B3 0.9800 . ?
C2B C3B 1.501(15) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C4B 1.490(18) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
C4B H4B3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ca1 O3 95.57(4) 2 2_545 ?
O4 Ca1 O2 168.55(4) 2 3_566 ?
O3 Ca1 O2 82.52(3) 2_545 3_566 ?
O4 Ca1 O1 88.70(3) 2 3_576 ?
O3 Ca1 O1 174.84(4) 2_545 3_576 ?
O2 Ca1 O1 92.73(3) 3_566 3_576 ?
O4 Ca1 O1 108.11(3) 2 4_575 ?
O3 Ca1 O1 74.34(3) 2_545 4_575 ?
O2 Ca1 O1 82.33(3) 3_566 4_575 ?
O1 Ca1 O1 107.10(2) 3_576 4_575 ?
O4 Ca1 O6 80.05(3) 2 . ?
O3 Ca1 O6 90.29(4) 2_545 . ?
O2 Ca1 O6 88.65(3) 3_566 . ?
O1 Ca1 O6 87.59(3) 3_576 . ?
O1 Ca1 O6 163.02(3) 4_575 . ?
O4 Ca1 O2 73.36(3) 2 4_575 ?
O3 Ca1 O2 110.78(3) 2_545 4_575 ?
O2 Ca1 O2 117.91(2) 3_566 4_575 ?
O1 Ca1 O2 73.20(3) 3_576 4_575 ?
O1 Ca1 O2 48.75(3) 4_575 4_575 ?
O6 Ca1 O2 147.23(3) . 4_575 ?
O5 S1 O6 119.46(6) . . ?
O5 S1 C8 108.27(6) . . ?
O6 S1 C8 108.16(6) . . ?
O5 S1 C1 107.58(6) . . ?
O6 S1 C1 106.54(6) . . ?
C8 S1 C1 106.09(6) . . ?
C7 O1 Ca1 141.47(8) . 3_576 ?
C7 O1 Ca1 101.92(8) . 4_676 ?
Ca1 O1 Ca1 108.35(4) 3_576 4_676 ?
C7 O2 Ca1 138.80(8) . 3_566 ?
C7 O2 Ca1 81.70(7) . 4_676 ?
Ca1 O2 Ca1 95.63(3) 3_566 4_676 ?
C14 O3 Ca1 173.74(9) . 2 ?
C14 O4 Ca1 145.63(9) . 2_545 ?
S1 O6 Ca1 137.62(6) . . ?
C2 C1 C6 121.71(11) . . ?
C2 C1 S1 119.00(10) . . ?
C6 C1 S1 119.24(9) . . ?
C3 C2 C1 119.09(12) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.83(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.28(12) . . ?
C5 C4 C7 119.27(11) . . ?
C3 C4 C7 120.44(11) . . ?
C6 C5 C4 120.54(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.46(12) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O2 C7 O1 123.29(11) . . ?
O2 C7 C4 118.88(11) . . ?
O1 C7 C4 117.79(11) . . ?
O2 C7 Ca1 73.47(7) . 4_676 ?
O1 C7 Ca1 53.30(6) . 4_676 ?
C4 C7 Ca1 156.01(8) . 4_676 ?
C13 C8 C9 121.90(11) . . ?
C13 C8 S1 119.84(9) . . ?
C9 C8 S1 118.25(9) . . ?
C10 C9 C8 118.98(11) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.95(12) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.09(11) . . ?
C12 C11 C14 119.37(11) . . ?
C10 C11 C14 120.47(11) . . ?
C11 C12 C13 120.72(11) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 118.30(11) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
O3 C14 O4 126.63(12) . . ?
O3 C14 C11 116.96(11) . . ?
O4 C14 C11 116.39(11) . . ?
C2B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
C2B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
C1B C2B C3B 114.0(15) . . ?
C1B C2B H2B1 108.8 . . ?
C3B C2B H2B1 108.7 . . ?
C1B C2B H2B2 108.8 . . ?
C3B C2B H2B2 108.8 . . ?
H2B1 C2B H2B2 107.7 . . ?
C4B C3B C2B 110.6(16) . . ?
C4B C3B H3B1 109.5 . . ?
C2B C3B H3B1 109.6 . . ?
C4B C3B H3B2 109.5 . . ?
C2B C3B H3B2 109.6 . . ?
H3B1 C3B H3B2 108.1 . . ?
C3B C4B H4B1 109.5 . . ?
C3B C4B H4B2 109.4 . . ?
H4B1 C4B H4B2 109.5 . . ?
C3B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?

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
O5 S1 O6 Ca1 51.13(10) . . . . ?
C8 S1 O6 Ca1 -73.21(9) . . . . ?
C1 S1 O6 Ca1 173.11(8) . . . . ?
O5 S1 C1 C2 -27.46(12) . . . . ?
O6 S1 C1 C2 -156.68(10) . . . . ?
C8 S1 C1 C2 88.24(11) . . . . ?
O5 S1 C1 C6 149.91(10) . . . . ?
O6 S1 C1 C6 20.70(12) . . . . ?
C8 S1 C1 C6 -94.38(11) . . . . ?
C6 C1 C2 C3 -2.8(2) . . . . ?
S1 C1 C2 C3 174.48(11) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C2 C3 C4 C7 -177.76(12) . . . . ?
C3 C4 C5 C6 -2.5(2) . . . . ?
C7 C4 C5 C6 176.91(12) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C2 C1 C6 C5 2.0(2) . . . . ?
S1 C1 C6 C5 -175.31(10) . . . . ?
Ca1 O2 C7 O1 69.23(18) 3_566 . . . ?
Ca1 O2 C7 O1 -19.85(12) 4_676 . . . ?
Ca1 O2 C7 C4 -113.31(13) 3_566 . . . ?
Ca1 O2 C7 C4 157.61(11) 4_676 . . . ?
Ca1 O2 C7 Ca1 89.08(11) 3_566 . . 4_676 ?
Ca1 O1 C7 O2 -117.47(14) 3_576 . . . ?
Ca1 O1 C7 O2 23.95(14) 4_676 . . . ?
Ca1 O1 C7 C4 65.05(17) 3_576 . . . ?
Ca1 O1 C7 C4 -153.53(9) 4_676 . . . ?
Ca1 O1 C7 Ca1 -141.42(14) 3_576 . . 4_676 ?
C5 C4 C7 O2 25.13(18) . . . . ?
C3 C4 C7 O2 -155.43(12) . . . . ?
C5 C4 C7 O1 -157.27(12) . . . . ?
C3 C4 C7 O1 22.17(18) . . . . ?
C5 C4 C7 Ca1 141.25(17) . . . 4_676 ?
C3 C4 C7 Ca1 -39.3(3) . . . 4_676 ?
O5 S1 C8 C13 -147.63(10) . . . . ?
O6 S1 C8 C13 -16.84(12) . . . . ?
C1 S1 C8 C13 97.14(11) . . . . ?
O5 S1 C8 C9 30.99(12) . . . . ?
O6 S1 C8 C9 161.78(10) . . . . ?
C1 S1 C8 C9 -84.24(11) . . . . ?
C13 C8 C9 C10 2.4(2) . . . . ?
S1 C8 C9 C10 -176.23(10) . . . . ?
C8 C9 C10 C11 -1.9(2) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C9 C10 C11 C14 176.86(12) . . . . ?
C10 C11 C12 C13 1.73(19) . . . . ?
C14 C11 C12 C13 -175.24(12) . . . . ?
C9 C8 C13 C12 -0.74(19) . . . . ?
S1 C8 C13 C12 177.83(10) . . . . ?
C11 C12 C13 C8 -1.32(19) . . . . ?
Ca1 O4 C14 O3 14.9(3) 2_545 . . . ?
Ca1 O4 C14 C11 -166.60(11) 2_545 . . . ?
C12 C11 C14 O3 153.59(12) . . . . ?
C10 C11 C14 O3 -23.36(18) . . . . ?
C12 C11 C14 O4 -25.10(18) . . . . ?
C10 C11 C14 O4 157.95(12) . . . . ?
C1B C2B C3B C4B 79(2) . . . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.084

