# Electronic Supplementary Material (ESI) for Energy & Environmental 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_3S
_database_code_depnum_ccdc_archive 'CCDC 1061738'
_audit_update_record             
;
2015-04-25 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 O3'
_chemical_formula_weight         168.19

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.0223(6)
_cell_length_b                   35.5424(15)
_cell_length_c                   9.3818(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.650(3)
_cell_angle_gamma                90.00
_cell_volume                     2640.2(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    66403
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.67

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 40 mm'
_diffrn_ambient_temperature      150(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  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and four ω scans with 2° steps (464 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            66403
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         25.67
_reflns_number_total             4985
_reflns_number_gt                3794
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by direct methods and subsequent Fourier-difference
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms bound to O atoms were found on a 
 difference Fourier map and all the others were introduced at calculated
 positions; all were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom (1.5 for CH₃). 
 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)+(0.0690P)²+0.4151P] 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         4985
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.042

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70614(15) 0.99743(3) 0.62059(13) 0.0362(3) Uani 1 1 d . . .
H1 H 0.7021 1.0130 0.5324 0.043 Uiso 1 1 d R . .
O2 O 0.68348(13) 0.96515(3) 0.87007(13) 0.0320(3) Uani 1 1 d . . .
H2 H 0.7009 0.9567 0.9754 0.038 Uiso 1 1 d R . .
O3 O 0.80687(14) 0.99977(3) 1.16139(13) 0.0341(3) Uani 1 1 d . . .
H3 H 0.8741 1.0117 1.2632 0.041 Uiso 1 1 d R . .
O4 O 0.52735(13) 0.88755(3) 0.76238(12) 0.0299(3) Uani 1 1 d . . .
H4 H 0.5604 0.9042 0.7025 0.036 Uiso 1 1 d R . .
O5 O 0.34778(13) 0.95742(3) 0.64781(13) 0.0300(3) Uani 1 1 d . . .
H5 H 0.4617 0.9564 0.7224 0.036 Uiso 1 1 d R . .
O6 O 0.02127(13) 0.95931(3) 0.53710(13) 0.0321(3) Uani 1 1 d . . .
H6 H -0.1018 0.9572 0.4831 0.038 Uiso 1 1 d R . .
O7 O 0.58728(16) 0.92100(3) 1.04585(14) 0.0398(3) Uani 1 1 d . . .
H7 H 0.5709 0.9060 0.9609 0.048 Uiso 1 1 d R . .
O8 O 0.67048(13) 0.95743(3) 1.32957(13) 0.0306(3) Uani 1 1 d . . .
H8 H 0.6758 0.9660 1.2380 0.037 Uiso 1 1 d R . .
O9 O 0.61603(16) 0.92306(3) 1.56304(14) 0.0388(3) Uani 1 1 d . . .
H9 H 0.6439 0.9495 1.5617 0.047 Uiso 1 1 d R . .
C1 C 0.76746(19) 1.01734(4) 0.76436(18) 0.0285(4) Uani 1 1 d . . .
C2 C 0.75622(18) 1.00042(4) 0.89151(19) 0.0276(3) Uani 1 1 d . . .
C3 C 0.82013(19) 1.01888(4) 1.03960(18) 0.0283(4) Uani 1 1 d . . .
C4 C 0.8935(2) 1.05395(4) 1.0596(2) 0.0318(4) Uani 1 1 d . . .
H4A H 0.9369 1.0664 1.1615 0.038 Uiso 1 1 calc R . .
C5 C 0.90431(19) 1.07128(5) 0.9321(2) 0.0306(4) Uani 1 1 d . . .
C6 C 0.84068(19) 1.05266(4) 0.78417(19) 0.0300(4) Uani 1 1 d . . .
H6A H 0.8473 1.0642 0.6960 0.036 Uiso 1 1 calc R . .
C7 C 0.9851(2) 1.10989(5) 0.9616(2) 0.0358(4) Uani 1 1 d . . .
H7A H 0.9128 1.1277 0.9819 0.043 Uiso 1 1 calc R . .
H7B H 1.0951 1.1087 1.0623 0.043 Uiso 1 1 calc R . .
C8 C 1.0151(2) 1.12619(5) 0.8286(2) 0.0416(4) Uani 1 1 d . . .
H8A H 0.9053 1.1295 0.7290 0.050 Uiso 1 1 calc R . .
H8B H 1.0837 1.1083 0.8036 0.050 Uiso 1 1 calc R . .
C9 C 1.1055(3) 1.16393(5) 0.8771(3) 0.0520(5) Uani 1 1 d . . .
H9A H 1.0369 1.1818 0.9000 0.078 Uiso 1 1 calc R . .
H9B H 1.1225 1.1736 0.7882 0.078 Uiso 1 1 calc R . .
H9C H 1.2152 1.1607 0.9745 0.078 Uiso 1 1 calc R . .
C10 C 0.35178(19) 0.88921(4) 0.68425(18) 0.0270(3) Uani 1 1 d . . .
C11 C 0.26892(19) 0.92359(4) 0.63687(18) 0.0264(3) Uani 1 1 d . . .
C12 C 0.09379(19) 0.92407(4) 0.57233(18) 0.0279(3) Uani 1 1 d . . .
C13 C 0.0050(2) 0.89108(4) 0.55323(19) 0.0308(4) Uani 1 1 d . . .
H13 H -0.1143 0.8919 0.5081 0.037 Uiso 1 1 calc R . .
C14 C 0.0880(2) 0.85666(4) 0.59916(19) 0.0317(4) Uani 1 1 d . . .
C15 C 0.2630(2) 0.85611(4) 0.66562(19) 0.0304(4) Uani 1 1 d . . .
H15 H 0.3220 0.8329 0.6984 0.036 Uiso 1 1 calc R . .
C16 C -0.0089(2) 0.82075(5) 0.5826(2) 0.0389(4) Uani 1 1 d . . .
H16A H -0.1269 0.8241 0.4958 0.047 Uiso 1 1 calc R . .
H16B H 0.0416 0.8002 0.5487 0.047 Uiso 1 1 calc R . .
C17 C -0.0096(4) 0.80936(7) 0.7364(3) 0.0737(7) Uani 1 1 d . . .
H17A H -0.0665 0.8293 0.7662 0.088 Uiso 1 1 calc R . .
H17B H 0.1086 0.8077 0.8246 0.088 Uiso 1 1 calc R . .
C18 C -0.0971(5) 0.77205(7) 0.7255(4) 0.0986(11) Uani 1 1 d . . .
H18A H -0.2159 0.7737 0.6421 0.148 Uiso 1 1 calc R . .
H18B H -0.0903 0.7663 0.8307 0.148 Uiso 1 1 calc R . .
H18C H -0.0414 0.7520 0.6968 0.148 Uiso 1 1 calc R . .
C19 C 0.5534(2) 0.90281(5) 1.15568(19) 0.0316(4) Uani 1 1 d . . .
C20 C 0.59487(19) 0.92233(4) 1.29777(19) 0.0278(4) Uani 1 1 d . . .
C21 C 0.56804(19) 0.90558(5) 1.41641(19) 0.0294(4) Uani 1 1 d . . .
C22 C 0.5004(2) 0.86964(5) 1.3932(2) 0.0336(4) Uani 1 1 d . . .
H22 H 0.4838 0.8582 1.4760 0.040 Uiso 1 1 calc R . .
C23 C 0.4567(2) 0.85014(5) 1.2500(2) 0.0342(4) Uani 1 1 d . . .
C24 C 0.4831(2) 0.86715(5) 1.1304(2) 0.0354(4) Uani 1 1 d . . .
H24 H 0.4528 0.8543 1.0314 0.042 Uiso 1 1 calc R . .
C25 C 0.3864(2) 0.81064(5) 1.2256(2) 0.0411(4) Uani 1 1 d . . .
H25A H 0.3576 0.8049 1.3127 0.049 Uiso 1 1 calc R . .
H25B H 0.2807 0.8095 1.1206 0.049 Uiso 1 1 calc R . .
C26 C 0.5054(4) 0.78121(6) 1.2265(5) 0.0992(11) Uani 1 1 d . . .
H26A H 0.6117 0.7824 1.3309 0.119 Uiso 1 1 calc R . .
H26B H 0.5329 0.7866 1.1383 0.119 Uiso 1 1 calc R . .
C27 C 0.4317(4) 0.74138(7) 1.2039(5) 0.1080(12) Uani 1 1 d . . .
H27A H 0.4164 0.7348 1.2975 0.162 Uiso 1 1 calc R . .
H27B H 0.5094 0.7234 1.1952 0.162 Uiso 1 1 calc R . .
H27C H 0.3224 0.7405 1.1047 0.162 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3823(18) . ?
O1 H1 0.9812 . ?
O2 C2 1.3842(18) . ?
O2 H2 0.9709 . ?
O3 C3 1.3830(18) . ?
O3 H3 0.9506 . ?
O4 C10 1.3916(18) . ?
O4 H4 0.9567 . ?
O5 C11 1.3757(17) . ?
O5 H5 0.9263 . ?
O6 C12 1.3778(18) . ?
O6 H6 0.9777 . ?
O7 C19 1.3695(19) . ?
O7 H7 0.9111 . ?
O8 C20 1.3841(18) . ?
O8 H8 0.9336 . ?
O9 C21 1.3765(19) . ?
O9 H9 0.9748 . ?
C1 C2 1.382(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.388(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.390(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(2) . ?
C5 C7 1.515(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.513(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.522(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.386(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.382(2) . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C14 C16 1.512(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.502(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.521(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.386(2) . ?
C19 C24 1.386(2) . ?
C20 C21 1.382(2) . ?
C21 C22 1.387(2) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(2) . ?
C23 C25 1.512(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.496(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.535(3) . ?
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
C1 O1 H1 111.7 . . ?
C2 O2 H2 107.4 . . ?
C3 O3 H3 110.2 . . ?
C10 O4 H4 105.1 . . ?
C11 O5 H5 111.7 . . ?
C12 O6 H6 110.2 . . ?
C19 O7 H7 112.3 . . ?
C20 O8 H8 109.5 . . ?
C21 O9 H9 112.5 . . ?
O1 C1 C2 117.30(13) . . ?
O1 C1 C6 122.38(14) . . ?
C2 C1 C6 120.31(14) . . ?
C1 C2 O2 119.64(13) . . ?
C1 C2 C3 119.41(14) . . ?
O2 C2 C3 120.95(14) . . ?
C4 C3 O3 123.83(14) . . ?
C4 C3 C2 120.32(14) . . ?
O3 C3 C2 115.84(13) . . ?
C3 C4 C5 120.66(15) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 118.85(15) . . ?
C6 C5 C7 123.12(15) . . ?
C4 C5 C7 118.03(14) . . ?
C5 C6 C1 120.45(15) . . ?
C5 C6 H6A 119.8 . . ?
C1 C6 H6A 119.8 . . ?
C8 C7 C5 117.15(14) . . ?
C8 C7 H7A 108.0 . . ?
C5 C7 H7A 108.0 . . ?
C8 C7 H7B 108.0 . . ?
C5 C7 H7B 108.0 . . ?
H7A C7 H7B 107.3 . . ?
C7 C8 C9 111.91(15) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 121.07(14) . . ?
C15 C10 O4 118.25(14) . . ?
C11 C10 O4 120.52(13) . . ?
O5 C11 C10 124.40(13) . . ?
O5 C11 C12 117.34(13) . . ?
C10 C11 C12 118.25(13) . . ?
O6 C12 C13 124.13(14) . . ?
O6 C12 C11 115.09(13) . . ?
C13 C12 C11 120.73(14) . . ?
C12 C13 C14 120.92(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 118.54(14) . . ?
C13 C14 C16 120.78(15) . . ?
C15 C14 C16 120.64(15) . . ?
C10 C15 C14 120.48(14) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C14 113.41(15) . . ?
C17 C16 H16A 108.9 . . ?
C14 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C14 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 114.33(19) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 C20 115.64(14) . . ?
O7 C19 C24 123.52(15) . . ?
C20 C19 C24 120.84(15) . . ?
C21 C20 O8 118.24(13) . . ?
C21 C20 C19 119.23(14) . . ?
O8 C20 C19 122.44(14) . . ?
O9 C21 C20 121.18(14) . . ?
O9 C21 C22 118.48(14) . . ?
C20 C21 C22 120.24(14) . . ?
C21 C22 C23 120.71(15) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 118.91(15) . . ?
C22 C23 C25 120.87(15) . . ?
C24 C23 C25 120.19(15) . . ?
C19 C24 C23 120.05(15) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C23 113.59(16) . . ?
C26 C25 H25A 108.8 . . ?
C23 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C23 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 C27 112.5(2) . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
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_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O5 0.98 1.85 2.8246(15) 169.5 3_676
O2 H2 O7 0.97 1.94 2.7032(15) 134.2 .
O2 H2 O3 0.97 2.17 2.7029(15) 113.2 .
O3 H3 O6 0.95 1.94 2.8837(15) 170.7 3_677
O4 H4 O9 0.96 1.74 2.6770(15) 163.8 1_554
O5 H5 O2 0.93 1.83 2.7461(15) 168.0 .
O6 H6 O8 0.98 1.86 2.8112(15) 163.6 1_454
O7 H7 O4 0.91 1.83 2.7203(15) 165.0 .
O8 H8 O3 0.93 2.04 2.8513(15) 144.0 .
O8 H8 O7 0.93 2.25 2.7219(15) 110.5 .
O9 H9 O1 0.97 1.80 2.7419(16) 162.8 1_556
####################################################################### 
# 
# 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_4H'
_database_code_depnum_ccdc_archive 'CCDC 1061739'
_audit_update_record             
;
2015-04-25 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 O2'
_chemical_formula_weight         152.19

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   18.8855(12)
_cell_length_b                   7.9784(6)
_cell_length_c                   11.2136(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1689.62(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    39599
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.67

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 30 mm'
_diffrn_ambient_temperature      150(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  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and three ω scans with 2° steps (325 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            39599
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.67
_reflns_number_total             1682
_reflns_number_gt                1537
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by direct methods and subsequent difference Fourier
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms bound to O atoms were found on a 
 difference Fourier map and all the others were introduced at calculated
 positions; all were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom. In the absence of 
 a suitable anomalous scatterer, the Friedel pairs have been merged.
 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)+(0.0520P)²+0.0594P] 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       ?
_chemical_absolute_configuration unk
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1682
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.091
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.029

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05273(7) 0.14603(19) 0.34518(14) 0.0427(4) Uani 1 1 d . . .
H1 H 0.0343 0.1899 0.2763 0.051 Uiso 1 1 d R . .
O2 O 0.46716(7) 0.4402(2) 0.51152(15) 0.0454(4) Uani 1 1 d . . .
H2 H 0.4639 0.5460 0.5209 0.054 Uiso 1 1 d R . .
O3 O 0.53213(8) 0.2682(2) 0.67274(14) 0.0442(4) Uani 1 1 d . . .
H3 H 0.5166 0.3383 0.6143 0.053 Uiso 1 1 d R . .
O4 O 0.95741(9) 0.2279(2) 0.51643(15) 0.0493(4) Uani 1 1 d . . .
H4 H 0.9944 0.1855 0.4816 0.059 Uiso 1 1 d R . .
C1 C 0.11812(10) 0.2234(3) 0.35352(19) 0.0376(4) Uani 1 1 d . . .
C2 C 0.14431(11) 0.3280(3) 0.26524(19) 0.0400(5) Uani 1 1 d . . .
H2A H 0.1169 0.3509 0.1961 0.048 Uiso 1 1 calc R . .
C3 C 0.21111(11) 0.3993(3) 0.2785(2) 0.0406(5) Uani 1 1 d . . .
H3A H 0.2290 0.4701 0.2175 0.049 Uiso 1 1 calc R . .
C4 C 0.25221(12) 0.3693(2) 0.3793(2) 0.0386(5) Uani 1 1 d . . .
C5 C 0.22381(12) 0.2661(3) 0.46718(19) 0.0418(5) Uani 1 1 d . . .
H5 H 0.2504 0.2457 0.5376 0.050 Uiso 1 1 calc R . .
C6 C 0.15798(11) 0.1924(3) 0.4548(2) 0.0401(5) Uani 1 1 d . . .
H6 H 0.1402 0.1209 0.5155 0.048 Uiso 1 1 calc R . .
C7 C 0.32546(11) 0.4436(3) 0.3930(2) 0.0428(5) Uani 1 1 d . . .
H7A H 0.3305 0.4898 0.4745 0.051 Uiso 1 1 calc R . .
H7B H 0.3310 0.5373 0.3359 0.051 Uiso 1 1 calc R . .
C8 C 0.38426(11) 0.3149(3) 0.3714(2) 0.0440(5) Uani 1 1 d . . .
H8A H 0.3770 0.2184 0.4256 0.053 Uiso 1 1 calc R . .
H8B H 0.3806 0.2731 0.2885 0.053 Uiso 1 1 calc R . .
C9 C 0.45812(12) 0.3849(3) 0.3911(2) 0.0461(5) Uani 1 1 d . . .
H9A H 0.4936 0.2973 0.3728 0.055 Uiso 1 1 calc R . .
H9B H 0.4661 0.4801 0.3361 0.055 Uiso 1 1 calc R . .
C10 C 0.60208(11) 0.2287(3) 0.65286(18) 0.0362(4) Uani 1 1 d . . .
C11 C 0.63857(11) 0.2892(3) 0.5541(2) 0.0413(5) Uani 1 1 d . . .
H11 H 0.6157 0.3609 0.4984 0.050 Uiso 1 1 calc R . .
C12 C 0.70893(12) 0.2432(3) 0.5379(2) 0.0426(5) Uani 1 1 d . . .
H12 H 0.7338 0.2846 0.4704 0.051 Uiso 1 1 calc R . .
C13 C 0.74405(12) 0.1384(2) 0.6176(2) 0.0392(5) Uani 1 1 d . . .
C14 C 0.70634(11) 0.0810(3) 0.7155(2) 0.0421(5) Uani 1 1 d . . .
H14 H 0.7291 0.0096 0.7715 0.050 Uiso 1 1 calc R . .
C15 C 0.63608(11) 0.1254(3) 0.73368(19) 0.0400(5) Uani 1 1 d . . .
H15 H 0.6114 0.0848 0.8016 0.048 Uiso 1 1 calc R . .
C16 C 0.82032(12) 0.0891(3) 0.5952(2) 0.0450(5) Uani 1 1 d . . .
H16A H 0.8316 0.1119 0.5106 0.054 Uiso 1 1 calc R . .
H16B H 0.8249 -0.0332 0.6079 0.054 Uiso 1 1 calc R . .
C17 C 0.87487(11) 0.1773(3) 0.67249(19) 0.0413(5) Uani 1 1 d . . .
H17A H 0.8660 0.2996 0.6711 0.050 Uiso 1 1 calc R . .
H17B H 0.8702 0.1383 0.7559 0.050 Uiso 1 1 calc R . .
C18 C 0.94921(11) 0.1427(3) 0.6286(2) 0.0451(5) Uani 1 1 d . . .
H18A H 0.9844 0.1846 0.6869 0.054 Uiso 1 1 calc R . .
H18B H 0.9564 0.0207 0.6181 0.054 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.384(2) . ?
O1 H1 0.9163 . ?
O2 C9 1.431(3) . ?
O2 H2 0.8527 . ?
O3 C10 1.376(2) . ?
O3 H3 0.9106 . ?
O4 C18 1.438(3) . ?
O4 H4 0.8695 . ?
C1 C6 1.385(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.392(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.532(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.383(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 C16 1.514(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 103.0 . . ?
C9 O2 H2 114.4 . . ?
C10 O3 H3 109.5 . . ?
C18 O4 H4 107.2 . . ?
O1 C1 C6 117.43(19) . . ?
O1 C1 C2 122.60(19) . . ?
C6 C1 C2 119.97(19) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 117.5(2) . . ?
C5 C4 C7 120.8(2) . . ?
C3 C4 C7 121.7(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C4 C7 C8 112.56(17) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 113.33(18) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O2 C9 C8 111.11(18) . . ?
O2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 C15 118.42(18) . . ?
O3 C10 C11 121.68(19) . . ?
C15 C10 C11 119.9(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 122.0(2) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 117.5(2) . . ?
C14 C13 C16 122.3(2) . . ?
C12 C13 C16 120.2(2) . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 120.0(2) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C16 C17 115.48(18) . . ?
C13 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
C13 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 111.04(19) . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O4 C18 C17 107.35(18) . . ?
O4 C18 H18A 110.2 . . ?
C17 C18 H18A 110.2 . . ?
O4 C18 H18B 110.2 . . ?
C17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.92 1.82 2.694(2) 158.4 4_554
O2 H2 O4 0.85 1.81 2.654(2) 171.3 3_465
O3 H3 O2 0.91 1.69 2.580(2) 164.6 .
O4 H4 O1 0.87 1.91 2.712(2) 152.5 1_655
