# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sporormiellin
_audit_creation_date             2014-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H14 O7'
_chemical_formula_sum            'C16 H14 O7'
_chemical_formula_weight         318.27
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.2831(2)
_cell_length_b                   12.4744(3)
_cell_length_c                   16.0184(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1455.31(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5702
_cell_measurement_temperature    173.0(3)
_cell_measurement_theta_max      62.8100
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11414
_diffrn_reflns_theta_full        62.70
_diffrn_reflns_theta_max         62.70
_diffrn_reflns_theta_min         4.49
_diffrn_ambient_temperature      173.0(3)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0181821000
_diffrn_orient_matrix_UB_12      0.0557835000
_diffrn_orient_matrix_UB_13      -0.0854182000
_diffrn_orient_matrix_UB_21      0.0193630000
_diffrn_orient_matrix_UB_22      -0.1091780000
_diffrn_orient_matrix_UB_23      -0.0440851000
_diffrn_orient_matrix_UB_31      -0.2098096000
_diffrn_orient_matrix_UB_32      -0.0149470000
_diffrn_orient_matrix_UB_33      0.0033834000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2189
_reflns_number_total             2308
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.3648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.08) H7(0.048) H8(0.054) H16A(0.094) H16B(0.094) H16C(0.094)
 H9(0.054) H2(0.056) H15A(0.069) H15B(0.069) H3A(0.043) H1A(0.094) H1B(0.094)
 H1C(0.094)
 Fixed X: H3(0.6738) H7(0.7741) H8(0.7562) H16A(0.395) H16B(0.3339)
 H16C(0.2691) H9(0.7025) H2(0.921) H15A(1.0407) H15B(1.0473) H3A(0.5759)
 H1A(0.7253) H1B(0.7099) H1C(0.8947)
 Fixed Y: H3(0.565) H7(0.2501) H8(0.4189) H16A(0.3427) H16B(0.4018)
 H16C(0.284) H9(0.5688) H2(0.0063) H15A(0.171) H15B(0.149) H3A(0.0657)
 H1A(0.0601) H1B(-0.0513) H1C(-0.0174)
 Fixed Z: H3(0.3826) H7(0.6108) H8(0.6704) H16A(0.0167) H16B(0.0985)
 H16C(0.0816) H9(0.5905) H2(0.2407) H15A(0.2444) H15B(0.1475) H3A(0.2403)
 H1A(0.093) H1B(0.1379) H1C(0.0952)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.7486(2) 0.19870(11) 0.45879(8) 0.0366(4) Uani 1 1 d . . .
O4 O 0.6795(2) 0.45937(11) 0.30216(9) 0.0437(4) Uani 1 1 d . . .
O1 O 0.7256(2) 0.09300(10) 0.34741(9) 0.0400(4) Uani 1 1 d . . .
C11 C 0.7127(3) 0.39171(16) 0.44062(12) 0.0325(5) Uani 1 1 d . . .
O6 O 0.5301(2) 0.29351(13) 0.11769(9) 0.0500(5) Uani 1 1 d . . .
C10 C 0.6991(3) 0.49249(16) 0.47897(14) 0.0377(5) Uani 1 1 d . . .
O3 O 0.6727(3) 0.58126(12) 0.43221(11) 0.0531(5) Uani 1 1 d . . .
H3 H 0.6738 0.5650 0.3826 0.080 Uiso 1 1 calc R . .
C14 C 0.7272(3) 0.19208(16) 0.37644(12) 0.0335(5) Uani 1 1 d . . .
O5 O 0.3667(2) 0.2594(2) 0.23120(11) 0.0748(7) Uani 1 1 d . . .
C5 C 0.5081(3) 0.26166(18) 0.19514(13) 0.0392(5) Uani 1 1 d . . .
C13 C 0.7072(3) 0.27248(16) 0.32125(12) 0.0322(4) Uani 1 1 d . . .
C7 C 0.7554(3) 0.31053(18) 0.57791(14) 0.0403(5) Uani 1 1 d . . .
H7 H 0.7741 0.2501 0.6108 0.048 Uiso 1 1 calc R . .
C8 C 0.7435(3) 0.41159(19) 0.61287(14) 0.0448(6) Uani 1 1 d . . .
H8 H 0.7562 0.4189 0.6704 0.054 Uiso 1 1 calc R . .
C16 C 0.3683(4) 0.3339(2) 0.07499(18) 0.0626(8) Uani 1 1 d . . .
H16A H 0.3950 0.3427 0.0167 0.094 Uiso 1 1 calc R . .
H16B H 0.3339 0.4018 0.0985 0.094 Uiso 1 1 calc R . .
H16C H 0.2691 0.2840 0.0816 0.094 Uiso 1 1 calc R . .
C6 C 0.7385(3) 0.30283(16) 0.49260(13) 0.0340(5) Uani 1 1 d . . .
C9 C 0.7133(3) 0.50201(19) 0.56518(15) 0.0452(6) Uani 1 1 d . . .
H9 H 0.7025 0.5688 0.5905 0.054 Uiso 1 1 calc R . .
C2 C 0.8533(3) 0.0589(2) 0.20718(15) 0.0469(6) Uani 1 1 d . . .
H2 H 0.9210 0.0063 0.2407 0.056 Uiso 1 1 calc R . .
O7 O 0.8376(2) 0.24366(13) 0.18151(9) 0.0450(4) Uani 1 1 d . . .
C15 C 0.9665(4) 0.1571(2) 0.19524(19) 0.0578(7) Uani 1 1 d . . .
H15A H 1.0407 0.1710 0.2444 0.069 Uiso 1 1 calc R . .
H15B H 1.0473 0.1490 0.1475 0.069 Uiso 1 1 calc R . .
C3 C 0.6906(3) 0.10131(16) 0.25633(12) 0.0361(5) Uani 1 1 d . . .
H3A H 0.5759 0.0657 0.2403 0.043 Uiso 1 1 calc R . .
C1 C 0.7899(4) 0.0079(2) 0.12581(17) 0.0628(8) Uani 1 1 d . . .
H1A H 0.7253 0.0601 0.0930 0.094 Uiso 1 1 calc R . .
H1B H 0.7099 -0.0513 0.1379 0.094 Uiso 1 1 calc R . .
H1C H 0.8947 -0.0174 0.0952 0.094 Uiso 1 1 calc R . .
C12 C 0.6991(3) 0.38054(16) 0.34928(13) 0.0334(5) Uani 1 1 d . . .
C4 C 0.6863(3) 0.22494(16) 0.23576(12) 0.0344(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0536(10) 0.0286(7) 0.0275(7) 0.0062(5) -0.0048(6) 0.0016(6)
O4 0.0555(10) 0.0341(7) 0.0414(8) 0.0155(6) -0.0021(8) -0.0015(7)
O1 0.0593(11) 0.0284(7) 0.0323(7) 0.0035(6) -0.0004(7) -0.0004(7)
C11 0.0317(11) 0.0314(10) 0.0344(10) 0.0042(8) -0.0016(9) -0.0058(9)
O6 0.0584(11) 0.0537(10) 0.0378(8) 0.0195(7) -0.0113(8) -0.0093(8)
C10 0.0360(12) 0.0298(10) 0.0472(12) 0.0012(9) -0.0011(10) -0.0058(10)
O3 0.0756(12) 0.0278(7) 0.0558(10) 0.0046(7) -0.0003(10) -0.0029(8)
C14 0.0384(12) 0.0312(10) 0.0310(10) 0.0029(8) -0.0023(9) 0.0006(9)
O5 0.0357(10) 0.145(2) 0.0431(9) 0.0176(11) 0.0012(8) 0.0074(12)
C5 0.0439(13) 0.0422(12) 0.0314(11) 0.0046(9) -0.0061(10) -0.0057(10)
C13 0.0336(11) 0.0330(10) 0.0300(9) 0.0075(8) -0.0015(8) -0.0050(9)
C7 0.0461(13) 0.0426(12) 0.0321(10) 0.0057(9) -0.0047(9) -0.0030(10)
C8 0.0473(14) 0.0531(14) 0.0339(10) -0.0066(10) -0.0037(10) -0.0067(11)
C16 0.078(2) 0.0483(14) 0.0616(16) 0.0232(13) -0.0341(16) -0.0121(14)
C6 0.0348(12) 0.0318(11) 0.0355(10) 0.0021(9) -0.0038(9) -0.0028(9)
C9 0.0468(15) 0.0400(11) 0.0487(13) -0.0107(10) 0.0010(11) -0.0126(11)
C2 0.0436(14) 0.0524(14) 0.0447(13) -0.0020(11) 0.0020(11) 0.0053(11)
O7 0.0401(9) 0.0562(9) 0.0388(8) 0.0110(7) 0.0070(7) -0.0065(8)
C15 0.0467(15) 0.0618(16) 0.0648(16) -0.0018(13) 0.0054(14) -0.0016(13)
C3 0.0420(12) 0.0372(11) 0.0289(10) -0.0023(8) 0.0001(10) -0.0011(10)
C1 0.0621(19) 0.0648(16) 0.0614(16) -0.0235(13) 0.0198(14) -0.0061(15)
C12 0.0298(11) 0.0338(10) 0.0366(10) 0.0086(8) -0.0020(9) -0.0030(10)
C4 0.0341(11) 0.0397(11) 0.0293(9) 0.0058(8) 0.0016(9) -0.0054(10)

_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
O2 C14 1.331(2) . ?
O2 C6 1.409(2) . ?
O4 C12 1.248(2) . ?
O1 C14 1.321(2) . ?
O1 C3 1.485(2) . ?
C11 C10 1.403(3) . ?
C11 C6 1.399(3) . ?
C11 C12 1.473(3) . ?
O6 C5 1.312(3) . ?
O6 C16 1.453(3) . ?
C10 O3 1.351(3) . ?
C10 C9 1.390(3) . ?
C14 C13 1.345(3) . ?
O5 C5 1.181(3) . ?
C5 C4 1.523(3) . ?
C13 C12 1.422(3) . ?
C13 C4 1.500(3) . ?
C7 C8 1.382(3) . ?
C7 C6 1.375(3) . ?
C8 C9 1.380(3) . ?
C2 C15 1.489(4) . ?
C2 C3 1.518(3) . ?
C2 C1 1.522(4) . ?
O7 C15 1.448(3) . ?
O7 C4 1.422(3) . ?
C3 C4 1.577(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
C14 O2 C6 115.60(16) . . ?
C14 O1 C3 106.39(15) . . ?
C10 C11 C12 120.99(18) . . ?
C6 C11 C10 117.32(18) . . ?
C6 C11 C12 121.68(18) . . ?
C5 O6 C16 116.8(2) . . ?
O3 C10 C11 120.13(19) . . ?
O3 C10 C9 119.44(19) . . ?
C9 C10 C11 120.43(19) . . ?
O2 C14 C13 128.17(19) . . ?
O1 C14 O2 114.08(17) . . ?
O1 C14 C13 117.75(18) . . ?
O6 C5 C4 113.00(19) . . ?
O5 C5 O6 125.2(2) . . ?
O5 C5 C4 121.80(19) . . ?
C14 C13 C12 120.25(18) . . ?
C14 C13 C4 108.44(18) . . ?
C12 C13 C4 131.21(17) . . ?
C6 C7 C8 117.4(2) . . ?
C9 C8 C7 122.1(2) . . ?
C11 C6 O2 120.57(18) . . ?
C7 C6 O2 116.20(18) . . ?
C7 C6 C11 123.23(19) . . ?
C8 C9 C10 119.5(2) . . ?
C15 C2 C3 102.2(2) . . ?
C15 C2 C1 113.7(2) . . ?
C3 C2 C1 110.7(2) . . ?
C4 O7 C15 106.68(17) . . ?
O7 C15 C2 105.9(2) . . ?
O1 C3 C2 110.56(19) . . ?
O1 C3 C4 106.08(15) . . ?
C2 C3 C4 104.36(18) . . ?
O4 C12 C11 122.28(19) . . ?
O4 C12 C13 124.11(18) . . ?
C13 C12 C11 113.61(17) . . ?
C5 C4 C3 113.59(18) . . ?
C13 C4 C5 110.94(18) . . ?
C13 C4 C3 101.18(15) . . ?
O7 C4 C5 110.48(16) . . ?
O7 C4 C13 114.48(17) . . ?
O7 C4 C3 105.84(17) . . ?

_database_code_depnum_ccdc_archive 'CCDC 990532'
