 
data_vitamin-C
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C6 H8 O6' 
_chemical_formula_sum 
 'C6 H8 O6' 
_chemical_formula_weight          176.12 
 
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~/s/m061c~/s/m061c 6.1.1.4' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    'P 21' 
_symmetry_space_group_name_HALL    'P 2yb'

loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    6.4035(2) 
_cell_length_b                    6.2743(2) 
_cell_length_c                    17.1186(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  99.325(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      678.69(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     13693 
_cell_measurement_theta_min       2.41 
_cell_measurement_theta_max       27.49 

_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.48 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.21 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.724 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              368 
_exptl_absorpt_coefficient_mu     0.159 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.75  
_exptl_absorpt_correction_T_max   0.96
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2002)' 
  
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             22066 
_diffrn_reflns_av_R_equivalents   0.0203 
_diffrn_reflns_av_sigmaI/netI     0.0119 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          2.41 
_diffrn_reflns_theta_max          27.51 
_reflns_number_total              3126 
_reflns_number_gt                 2996 
_reflns_threshold_expression      I>2σ(I) 
 
_computing_data_collection        'COLLECT (Nonius, 1999)' 
_computing_cell_refinement        'PEAKREF (Schreurs, 2005)' 
_computing_data_reduction         'EVALCCD (Duisenberg et al., 2003)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_ccomputing_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)+(0.0538P)²+0.0826P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.3(6) 
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          3126 
_refine_ls_number_parameters      217 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0309 
_refine_ls_R_factor_gt            0.0292 
_refine_ls_wR_factor_ref          0.0771 
_refine_ls_wR_factor_gt           0.0755 
_refine_ls_goodness_of_fit_ref    1.090 
_refine_ls_restrained_S_all       1.089 
_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 
O1 O 0.39781(12) 0.49861(16) 0.11162(4) 0.01120(17) Uani 1 1 d . . . 
O2 O 0.21020(13) 0.50434(16) -0.01122(5) 0.01385(18) Uani 1 1 d . . . 
O3 O 0.63371(13) 0.50493(16) -0.06551(4) 0.01326(17) Uani 1 1 d . . . 
H3O H 0.5320 0.4607 -0.0956 0.020 Uiso 1 1 d R . . 
O4 O 0.94259(13) 0.48523(18) 0.09257(5) 0.01653(19) Uani 1 1 d . . . 
H4O H 1.0009 0.4854 0.0546 0.025 Uiso 1 1 d R . . 
O5 O 0.67233(13) 0.85859(15) 0.17342(5) 0.01296(18) Uani 1 1 d . . . 
H5O H 0.7851 0.8913 0.1673 0.019 Uiso 1 1 d R . . 
O6 O 0.57002(14) 0.45811(16) 0.31506(5) 0.01446(19) Uani 1 1 d . . . 
H6O H 0.4655 0.4300 0.3289 0.022 Uiso 1 1 d R . . 
C1 C 0.61786(17) 0.4784(2) 0.14677(6) 0.0100(2) Uani 1 1 d . . . 
H1 H 0.6406 0.3356 0.1727 0.012 Uiso 1 1 calc R . . 
C2 C 0.73366(17) 0.4861(2) 0.07739(6) 0.0106(2) Uani 1 1 d . . . 
C3 C 0.59266(16) 0.4945(2) 0.00996(6) 0.0094(2) Uani 1 1 d . . . 
C4 C 0.38264(17) 0.4993(2) 0.03163(6) 0.0098(2) Uani 1 1 d . . . 
C5 C 0.68191(18) 0.6512(2) 0.20866(6) 0.0103(2) Uani 1 1 d . . . 
H5 H 0.8304 0.6237 0.2351 0.012 Uiso 1 1 calc R . . 
C6 C 0.53869(19) 0.6545(2) 0.27139(7) 0.0119(2) Uani 1 1 d . . . 
H6A H 0.5745 0.7772 0.3074 0.014 Uiso 1 1 calc R . . 
H6B H 0.3889 0.6679 0.2461 0.014 Uiso 1 1 calc R . . 
O7 O 0.34847(12) -0.01930(17) 0.39271(5) 0.01270(18) Uani 1 1 d . . . 
O8 O 0.53659(12) -0.00282(16) 0.51525(5) 0.01386(18) Uani 1 1 d . . . 
O9 O 0.11558(12) 0.00690(15) 0.57012(4) 0.01223(17) Uani 1 1 d . . . 
H9O H 0.2281 -0.0260 0.6032 0.018 Uiso 1 1 d R . . 
O10 O -0.19665(12) 0.00290(17) 0.41156(5) 0.01378(18) Uani 1 1 d . . . 
H10O H -0.2508 -0.0027 0.4464 0.021 Uiso 1 1 d R . . 
O11 O 0.16048(14) 0.36279(15) 0.33256(5) 0.01448(18) Uani 1 1 d . . . 
H11O H 0.0966 0.4016 0.3718 0.022 Uiso 1 1 d R . . 
O12 O 0.08571(14) -0.04444(17) 0.18231(5) 0.0177(2) Uani 1 1 d . . . 
H12O H 0.1290 -0.0449 0.1368 0.027 Uiso 1 1 d R . . 
C7 C 0.12753(17) -0.0186(2) 0.35759(6) 0.0103(2) Uani 1 1 d . . . 
H7 H 0.0919 -0.1565 0.3293 0.012 Uiso 1 1 calc R . . 
C8 C 0.01281(17) -0.0054(2) 0.42724(6) 0.0099(2) Uani 1 1 d . . . 
C9 C 0.15418(16) -0.0023(2) 0.49452(6) 0.0091(2) Uani 1 1 d . . . 
C10 C 0.36413(17) -0.0077(2) 0.47247(6) 0.0102(2) Uani 1 1 d . . . 
C11 C 0.08166(18) 0.16587(19) 0.29867(7) 0.0106(2) Uani 1 1 d . . . 
H11 H -0.0749 0.1780 0.2818 0.013 Uiso 1 1 calc R . . 
C12 C 0.18588(19) 0.1347(2) 0.22560(7) 0.0125(2) Uani 1 1 d . . . 
H12A H 0.1681 0.2644 0.1922 0.015 Uiso 1 1 calc R . . 
H12B H 0.3391 0.1073 0.2414 0.015 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 C4 1.3570(12) . ? 
O1 C1 1.4453(12) . ? 
O2 C4 1.2231(13) . ? 
O3 C3 1.3611(12) . ? 
O3 H3O 0.8109 . ? 
O4 C2 1.3209(13) . ? 
O4 H4O 0.8000 . ? 
O5 C5 1.4312(15) . ? 
O5 H5O 0.7742 . ? 
O6 C6 1.4382(15) . ? 
O6 H6O 0.7663 . ? 
C1 C2 1.4994(13) . ? 
C1 C5 1.5249(16) . ? 
C1 H1 1.0000 . ? 
C2 C3 1.3463(15) . ? 
C3 C4 1.4522(14) . ? 
C5 C6 1.5211(15) . ? 
C5 H5 1.0000 . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
O7 C10 1.3547(13) . ? 
O7 C7 1.4448(12) . ? 
O8 C10 1.2227(14) . ? 
O9 C9 1.3575(12) . ? 
O9 H9O 0.8659 . ? 
O10 C8 1.3256(13) . ? 
O10 H10O 0.7377 . ? 
O11 C11 1.4223(15) . ? 
O11 H11O 0.8760 . ? 
O12 C12 1.4389(15) . ? 
O12 H12O 0.8679 . ? 
C7 C8 1.5007(13) . ? 
C7 C11 1.5320(16) . ? 
C7 H7 1.0000 . ? 
C8 C9 1.3447(15) . ? 
C9 C10 1.4545(14) . ? 
C11 C12 1.5227(15) . ? 
C11 H11 1.0000 . ? 
C12 H12A 0.9900 . ? 
C12 H12B 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 
C4 O1 C1 109.02(8) . . ? 
C3 O3 H3O 109.1 . . ? 
C2 O4 H4O 115.5 . . ? 
C5 O5 H5O 108.7 . . ? 
C6 O6 H6O 107.7 . . ? 
O1 C1 C2 103.97(8) . . ? 
O1 C1 C5 111.17(9) . . ? 
C2 C1 C5 114.56(10) . . ? 
O1 C1 H1 109.0 . . ? 
C2 C1 H1 109.0 . . ? 
C5 C1 H1 109.0 . . ? 
O4 C2 C3 133.32(10) . . ? 
O4 C2 C1 117.33(9) . . ? 
C3 C2 C1 109.35(9) . . ? 
C2 C3 O3 127.58(10) . . ? 
C2 C3 C4 107.58(9) . . ? 
O3 C3 C4 124.80(9) . . ? 
O2 C4 O1 121.02(9) . . ? 
O2 C4 C3 129.11(10) . . ? 
O1 C4 C3 109.87(9) . . ? 
O5 C5 C6 107.21(9) . . ? 
O5 C5 C1 111.42(9) . . ? 
C6 C5 C1 112.02(9) . . ? 
O5 C5 H5 108.7 . . ? 
C6 C5 H5 108.7 . . ? 
C1 C5 H5 108.7 . . ? 
O6 C6 C5 107.83(9) . . ? 
O6 C6 H6A 110.1 . . ? 
C5 C6 H6A 110.1 . . ? 
O6 C6 H6B 110.1 . . ? 
C5 C6 H6B 110.1 . . ? 
H6A C6 H6B 108.5 . . ? 
C10 O7 C7 109.08(8) . . ? 
C9 O9 H9O 110.6 . . ? 
C8 O10 H10O 115.3 . . ? 
C11 O11 H11O 112.1 . . ? 
C12 O12 H12O 106.5 . . ? 
O7 C7 C8 104.00(8) . . ? 
O7 C7 C11 110.28(9) . . ? 
C8 C7 C11 114.53(10) . . ? 
O7 C7 H7 109.3 . . ? 
C8 C7 H7 109.3 . . ? 
C11 C7 H7 109.3 . . ? 
O10 C8 C9 133.75(10) . . ? 
O10 C8 C7 116.80(9) . . ? 
C9 C8 C7 109.45(9) . . ? 
C8 C9 O9 128.01(10) . . ? 
C8 C9 C10 107.44(9) . . ? 
O9 C9 C10 124.55(9) . . ? 
O8 C10 O7 121.15(10) . . ? 
O8 C10 C9 128.83(10) . . ? 
O7 C10 C9 110.01(9) . . ? 
O11 C11 C12 105.82(9) . . ? 
O11 C11 C7 111.73(9) . . ? 
C12 C11 C7 112.40(9) . . ? 
O11 C11 H11 108.9 . . ? 
C12 C11 H11 108.9 . . ? 
C7 C11 H11 108.9 . . ? 
O12 C12 C11 107.76(9) . . ? 
O12 C12 H12A 110.2 . . ? 
C11 C12 H12A 110.2 . . ? 
O12 C12 H12B 110.2 . . ? 
C11 C12 H12B 110.2 . . ? 
H12A C12 H12B 108.5 . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              27.51 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.418 
_refine_diff_density_min   -0.415 
_refine_diff_density_rms    0.095 
