#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/82/2218287.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218287
loop_
_publ_author_name
'Jin, Shu'
'Miao, Xiaoqin'
_publ_section_title
;
 3-O-Ethyl-<small>L</small>-ascorbic acid
;
_journal_coeditor_code           XU2411
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o860
_journal_paper_doi               10.1107/S1600536808009963
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H12 O6'
_chemical_formula_moiety         'C8 H12 O6'
_chemical_formula_sum            'C8 H12 O6'
_chemical_formula_weight         204.18
_chemical_melting_point          385
_chemical_name_systematic
;
3-O-Ethyl-L-ascorbic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6690(9)
_cell_length_b                   11.939(2)
_cell_length_c                   16.794(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     936.2(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1973
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.259
_refine_ls_extinction_coef       0.121(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1024
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0395
_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/[σ²(Fo²)+(0.1P)²+1.3P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                882
_reflns_number_total             1024
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2411.cif
_cod_data_source_block           I
_cod_database_code               2218287
_cod_database_fobs_code          2218287
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.5474(6) 0.5579(2) 0.82156(13) 0.0513(7) Uani d . 1
C C1 0.6281(17) 0.6421(5) 0.9472(3) 0.0896(18) Uani d . 1
H H1A 0.5996 0.6352 1.0036 0.134 Uiso calc R 1
H H1B 0.5371 0.7093 0.9285 0.134 Uiso calc R 1
H H1C 0.8295 0.6455 0.9359 0.134 Uiso calc R 1
O O2 0.1035(7) 0.3667(2) 0.85756(15) 0.0563(8) Uani d D 1
H H2A 0.027(12) 0.305(2) 0.851(3) 0.084 Uiso d D 1
C C2 0.5046(14) 0.5463(4) 0.90741(19) 0.0664(14) Uani d . 1
H H2B 0.3016 0.5418 0.9192 0.080 Uiso calc R 1
H H2C 0.5953 0.4782 0.9262 0.080 Uiso calc R 1
C C3 0.4076(7) 0.4855(2) 0.77537(18) 0.0385(8) Uani d . 1
O O3 -0.0350(7) 0.2854(2) 0.69573(15) 0.0555(7) Uani d . 1
C C4 0.2202(8) 0.4033(3) 0.78834(19) 0.0401(8) Uani d . 1
O O4 0.2730(6) 0.41543(19) 0.65249(13) 0.0451(7) Uani d . 1
C C5 0.1347(8) 0.3595(3) 0.7110(2) 0.0419(8) Uani d . 1
O O5 0.0863(5) 0.64292(19) 0.67658(15) 0.0419(6) Uani d . 1
H H5A 0.088(11) 0.671(3) 0.727(3) 0.063 Uiso d . 1
O O6 0.3693(6) 0.7318(2) 0.53918(14) 0.0466(7) Uani d . 1
H H6A 0.213(11) 0.729(4) 0.511(3) 0.070 Uiso d . 1
C C6 0.4518(7) 0.4996(2) 0.68745(17) 0.0355(8) Uani d . 1
H H6B 0.6523 0.4838 0.6744 0.043 Uiso calc R 1
C C7 0.3734(7) 0.6151(3) 0.65672(17) 0.0329(7) Uani d . 1
H H7A 0.5026 0.6705 0.6804 0.039 Uiso calc R 1
C C8 0.4004(9) 0.6198(3) 0.56722(18) 0.0427(9) Uani d . 1
H H8A 0.5861 0.5910 0.5514 0.051 Uiso calc R 1
H H8B 0.2544 0.5729 0.5432 0.051 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0599(17) 0.0583(14) 0.0356(11) -0.0134(14) -0.0067(13) 0.0078(11)
C1 0.122(5) 0.091(3) 0.056(3) -0.020(4) 0.007(3) -0.013(2)
O2 0.0731(19) 0.0566(14) 0.0391(12) -0.0154(17) 0.0083(14) 0.0088(12)
C2 0.096(4) 0.068(2) 0.0350(16) -0.016(3) -0.005(2) 0.0046(17)
C3 0.0394(17) 0.0395(15) 0.0365(15) 0.0018(17) -0.0037(15) 0.0049(13)
O3 0.0678(17) 0.0441(13) 0.0544(14) -0.0087(15) -0.0043(15) 0.0031(11)
C4 0.0452(19) 0.0366(16) 0.0385(16) 0.0016(15) 0.0020(16) 0.0092(13)
O4 0.0605(16) 0.0383(12) 0.0364(11) -0.0028(12) 0.0032(12) 0.0020(9)
C5 0.0473(19) 0.0352(15) 0.0432(18) 0.0034(18) 0.0011(17) 0.0056(14)
O5 0.0367(13) 0.0485(12) 0.0406(12) 0.0064(12) 0.0060(11) 0.0020(10)
O6 0.0455(14) 0.0504(13) 0.0440(13) -0.0009(13) -0.0044(12) 0.0163(11)
C6 0.0328(16) 0.0358(15) 0.0378(15) 0.0055(15) 0.0032(14) 0.0039(13)
C7 0.0293(15) 0.0367(15) 0.0326(15) -0.0029(14) 0.0023(13) 0.0023(12)
C8 0.054(2) 0.0394(16) 0.0345(16) 0.0045(19) 0.0078(17) 0.0044(14)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C2 116.5(3)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C4 O2 H2A 110(4)
C1 C2 O1 109.1(4)
C1 C2 H2B 109.9
O1 C2 H2B 109.9
C1 C2 H2C 109.9
O1 C2 H2C 109.9
H2B C2 H2C 108.3
O1 C3 C4 134.8(3)
O1 C3 C6 115.7(3)
C4 C3 C6 109.5(3)
C3 C4 O2 129.9(3)
C3 C4 C5 107.4(3)
O2 C4 C5 122.6(3)
C5 O4 C6 109.1(2)
O3 C5 O4 121.1(3)
O3 C5 C4 129.0(3)
O4 C5 C4 109.9(3)
C7 O5 H5A 107(3)
C8 O6 H6A 103(4)
O4 C6 C3 104.2(2)
O4 C6 C7 111.0(3)
C3 C6 C7 113.8(3)
O4 C6 H6B 109.2
C3 C6 H6B 109.2
C7 C6 H6B 109.2
O5 C7 C8 107.7(3)
O5 C7 C6 111.1(3)
C8 C7 C6 110.7(3)
O5 C7 H7A 109.1
C8 C7 H7A 109.1
C6 C7 H7A 109.1
O6 C8 C7 110.8(3)
O6 C8 H8A 109.5
C7 C8 H8A 109.5
O6 C8 H8B 109.5
C7 C8 H8B 109.5
H8A C8 H8B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.332(4)
O1 C2 1.462(4)
C1 C2 1.444(7)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
O2 C4 1.356(4)
O2 H2A 0.83(3)
C2 H2B 0.9700
C2 H2C 0.9700
C3 C4 1.332(5)
C3 C6 1.500(4)
O3 C5 1.215(4)
C4 C5 1.456(5)
O4 C5 1.353(4)
O4 C6 1.432(4)
O5 C7 1.421(4)
O5 H5A 0.91(4)
O6 C8 1.425(4)
O6 H6A 0.87(5)
C6 C7 1.516(4)
C6 H6B 0.9800
C7 C8 1.510(4)
C7 H7A 0.9800
C8 H8A 0.9700
C8 H8B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O5 3_546 0.83(3) 2.06(3) 2.873(3) 168(5) yes
O5 H5A O3 3_556 0.91(5) 1.90(4) 2.748(4) 154(4) yes
O6 H6A O6 4_466 0.87(5) 1.87(5) 2.715(4) 163(4) yes
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
C3 O1 C2 C1 -169.9(4)
C2 O1 C3 C4 3.1(6)
C2 O1 C3 C6 179.3(3)
O1 C3 C4 O2 1.1(6)
C6 C3 C4 O2 -175.3(3)
O1 C3 C4 C5 176.8(4)
C6 C3 C4 C5 0.4(4)
C6 O4 C5 O3 178.3(3)
C6 O4 C5 C4 -1.0(4)
C3 C4 C5 O3 -178.9(4)
O2 C4 C5 O3 -2.8(6)
C3 C4 C5 O4 0.3(4)
O2 C4 C5 O4 176.4(3)
C5 O4 C6 C3 1.1(3)
C5 O4 C6 C7 -121.7(3)
O1 C3 C6 O4 -178.1(3)
C4 C3 C6 O4 -0.9(4)
O1 C3 C6 C7 -57.1(4)
C4 C3 C6 C7 120.0(3)
O4 C6 C7 O5 61.3(3)
C3 C6 C7 O5 -55.8(4)
O4 C6 C7 C8 -58.3(4)
C3 C6 C7 C8 -175.4(3)
O5 C7 C8 O6 67.1(4)
C6 C7 C8 O6 -171.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194515
