# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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#  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. 
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data_7663sadabs
_database_code_depnum_ccdc_archive 'CCDC 885364'
_audit_block_code                HUG-HC-124-01
_audit_creation_date             2012-01-12
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
Title
;
_chemical_compound_source        pentane,
_chemical_formula_moiety         'C8 H10 O4'
_chemical_formula_sum            'C8 H10 O4'
_chemical_formula_weight         170.16

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.6342(3)
_cell_length_b                   7.2435(3)
_cell_length_c                   9.0416(4)
_cell_angle_alpha                101.074(2)
_cell_angle_beta                 109.754(2)
_cell_angle_gamma                99.9640(10)
_cell_volume                     387.76(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6679


_cell_measurement_temperature    100
_cell_measurement_theta_max      66.3804
_cell_measurement_theta_min      5.3994
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.91608
_exptl_absorpt_correction_T_min  0.63958

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -2.00 0.1290
-1.00 -1.00 2.00 0.2910
-2.00 -2.00 1.00 0.2340
1.00 -1.00 0.00 0.0590
-1.00 1.00 0.00 0.0280
1.00 2.00 1.00 0.2100
-1.00 -2.00 1.00 0.2310
1.00 1.00 -2.00 0.3240
5.00 8.00 -1.00 0.2530
2.00 7.00 8.00 0.2510

_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.087
_exptl_special_details           
;
Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8319
_diffrn_reflns_theta_full        61.12
_diffrn_reflns_theta_max         61.12
_diffrn_reflns_theta_min         5.40

_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_voltage           40.0
_reflns_number_gt                1134
_reflns_number_total             1167
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.2010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0828

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

The minimum and maximum estimated transmissions from the multi-scan
scaling are 0.6056 and 0.9523 (SADABS).

Highest peak ?
Deepest hole ?

_iucr_refine_instructions_details

_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
O4 O 0.86220(16) 0.69695(15) 1.09987(12) 0.0215(3) Uani 1 1 d . . .
O1 O 0.51681(16) 0.73750(14) 0.57926(12) 0.0177(3) Uani 1 1 d . . .
O2 O 0.85853(16) 0.70806(15) 0.61711(12) 0.0214(3) Uani 1 1 d . . .
O3 O 1.09502(17) 0.80711(18) 0.98637(14) 0.0319(3) Uani 1 1 d . . .
C2 C 0.7080(2) 0.6757(2) 0.82447(17) 0.0154(3) Uani 1 1 d . . .
C1 C 0.7134(2) 0.70928(19) 0.66878(18) 0.0160(3) Uani 1 1 d . . .
C4 C 0.4817(2) 0.6944(2) 0.82311(17) 0.0160(3) Uani 1 1 d . . .
H4 H 0.4690 0.7535 0.9255 0.019 Uiso 1 1 calc R . .
C5 C 0.3746(2) 0.7594(2) 0.67277(17) 0.0166(3) Uani 1 1 d . . .
H5 H 0.2253 0.6743 0.6088 0.020 Uiso 1 1 calc R . .
C7 C 0.9120(2) 0.7349(2) 0.97591(18) 0.0166(3) Uani 1 1 d . . .
C6 C 0.3642(2) 0.9683(2) 0.71186(19) 0.0203(4) Uani 1 1 d . . .
H6A H 0.5097 1.0501 0.7797 0.030 Uiso 1 1 calc R . .
H6B H 0.2662 0.9820 0.7684 0.030 Uiso 1 1 calc R . .
H6C H 0.3101 1.0059 0.6124 0.030 Uiso 1 1 calc R . .
C3 C 0.5203(2) 0.4983(2) 0.79628(18) 0.0172(3) Uani 1 1 d . . .
H3A H 0.4466 0.4112 0.6870 0.021 Uiso 1 1 calc R . .
H3B H 0.5361 0.4352 0.8835 0.021 Uiso 1 1 calc R . .
C8 C 1.0422(2) 0.7481(2) 1.25731(18) 0.0226(4) Uani 1 1 d . . .
H8A H 1.1533 0.6821 1.2493 0.034 Uiso 1 1 calc R . .
H8B H 0.9871 0.7100 1.3353 0.034 Uiso 1 1 calc R . .
H8C H 1.1059 0.8862 1.2920 0.034 Uiso 1 1 calc R . .

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
O4 0.0178(5) 0.0285(6) 0.0147(6) 0.0075(4) 0.0033(4) 0.0018(4)
O1 0.0180(5) 0.0213(6) 0.0154(5) 0.0055(4) 0.0072(4) 0.0063(4)
O2 0.0193(6) 0.0254(6) 0.0214(6) 0.0049(4) 0.0118(5) 0.0039(4)
O3 0.0167(6) 0.0503(8) 0.0232(6) 0.0086(5) 0.0061(5) -0.0003(5)
C2 0.0155(7) 0.0154(7) 0.0162(8) 0.0036(6) 0.0074(6) 0.0042(6)
C1 0.0163(7) 0.0121(7) 0.0167(8) 0.0012(5) 0.0054(6) 0.0014(5)
C4 0.0147(7) 0.0180(7) 0.0154(8) 0.0033(6) 0.0074(6) 0.0027(6)
C5 0.0135(7) 0.0200(8) 0.0158(8) 0.0029(6) 0.0064(6) 0.0036(6)
C7 0.0182(8) 0.0147(7) 0.0179(8) 0.0034(6) 0.0081(6) 0.0052(6)
C6 0.0188(8) 0.0207(8) 0.0199(8) 0.0048(6) 0.0053(6) 0.0062(6)
C3 0.0173(7) 0.0169(8) 0.0168(8) 0.0043(6) 0.0073(6) 0.0017(6)
C8 0.0219(8) 0.0268(8) 0.0154(8) 0.0056(6) 0.0025(6) 0.0069(6)

_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
O4 C7 1.3335(18) . ?
O4 C8 1.4440(17) . ?
O1 C1 1.3565(17) . ?
O1 C5 1.4729(17) . ?
O2 C1 1.2044(18) . ?
O3 C7 1.2001(18) . ?
C2 C1 1.485(2) . ?
C2 C4 1.5262(19) . ?
C2 C7 1.487(2) . ?
C2 C3 1.5403(19) . ?
C4 C5 1.511(2) . ?
C4 C3 1.475(2) . ?
C5 C6 1.506(2) . ?

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
C7 O4 C8 117.16(11) . . ?
C1 O1 C5 112.16(11) . . ?
C1 C2 C4 105.84(11) . . ?
C1 C2 C7 121.53(12) . . ?
C1 C2 C3 112.16(12) . . ?
C4 C2 C3 57.52(9) . . ?
C7 C2 C4 123.27(12) . . ?
C7 C2 C3 119.85(12) . . ?
O1 C1 C2 109.67(12) . . ?
O2 C1 O1 120.98(13) . . ?
O2 C1 C2 129.31(13) . . ?
C5 C4 C2 105.84(11) . . ?
C3 C4 C2 61.72(9) . . ?
C3 C4 C5 116.82(12) . . ?
O1 C5 C4 104.93(11) . . ?
O1 C5 C6 109.17(11) . . ?
C6 C5 C4 113.00(12) . . ?
O4 C7 C2 110.01(12) . . ?
O3 C7 O4 124.57(13) . . ?
O3 C7 C2 125.41(14) . . ?
C4 C3 C2 60.76(9) . . ?