#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239352.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_2239352
loop_
_publ_author_name
'Pendrill, Robert'
'Eriksson, Lars'
'Widmalm, Göran'
_publ_section_title
;
 Methyl 4-O-benzyl-α-<small>L</small>-rhamnopyranoside
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o561
_journal_page_last               o562
_journal_paper_doi               10.1107/S1600536814007922
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H20 O5'
_chemical_formula_moiety         'C14 H20 O5'
_chemical_formula_sum            'C14 H20 O5'
_chemical_formula_weight         268.30
_chemical_name_systematic
;
Methyl 4-O-benzyl-α-L-rhamnopyranoside
;
_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           'Manual editing of cif file from SHELXL'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.53770(10)
_cell_length_b                   9.1848(2)
_cell_length_c                   23.2699(5)
_cell_measurement_reflns_used    4263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.20
_cell_measurement_theta_min      3.82
_cell_volume                     1397.30(5)
_computing_cell_refinement
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'Encifer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.5467
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur 3 with sapphire 3 CCD'
_diffrn_measurement_method       'ω scans at different φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9540
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.132
_refine_ls_abs_structure_details 'none; Friedel pairs merged'
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0346
_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)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                1407
_reflns_number_total             1665
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2708sup1.cf
_cod_data_source_block           I
_cod_database_code               2239352
_cod_database_fobs_code          2239352
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
_atom_site_symmetry_multiplicity
C C1 1.0867(3) 0.5237(2) 0.04789(8) 0.0370(5) Uani d . 1 1
H H1 1.1807 0.5419 0.0159 0.044 Uiso calc R 1 1
C C2 0.8931(3) 0.6130(2) 0.03845(8) 0.0317(5) Uani d . 1 1
H H2 0.8232 0.5790 0.0037 0.038 Uiso calc R 1 1
C C3 0.7515(3) 0.5959(2) 0.09008(8) 0.0273(4) Uani d . 1 1
H H3 0.7109 0.4935 0.0933 0.033 Uiso calc R 1 1
C C4 0.8644(3) 0.6397(2) 0.14447(8) 0.0282(4) Uani d . 1 1
H H4 0.8990 0.7435 0.1432 0.034 Uiso calc R 1 1
C C5 1.0597(3) 0.5481(2) 0.15042(8) 0.0314(4) Uani d . 1 1
H H5 1.0212 0.4456 0.1549 0.038 Uiso calc R 1 1
O O5 1.1851(2) 0.56299(17) 0.09964(6) 0.0382(4) Uani d . 1 1
C C6 1.1946(3) 0.5915(3) 0.20013(9) 0.0444(6) Uani d . 1 1
H H6A 1.3178 0.5347 0.1994 0.067 Uiso calc R 1 1
H H6B 1.1234 0.5747 0.2356 0.067 Uiso calc R 1 1
H H6C 1.2284 0.6929 0.1970 0.067 Uiso calc R 1 1
O O1 1.0298(2) 0.37637(17) 0.04700(6) 0.0458(4) Uani d . 1 1
C C7 1.1990(5) 0.2788(3) 0.04520(14) 0.0819(10) Uani d . 1 1
H H7A 1.2799 0.2985 0.0117 0.123 Uiso calc R 1 1
H H7B 1.1498 0.1804 0.0437 0.123 Uiso calc R 1 1
H H7C 1.2813 0.2918 0.0790 0.123 Uiso calc R 1 1
O O2 0.9419(2) 0.76226(15) 0.03268(6) 0.0444(4) Uani d . 1 1
H H2A 0.9920 0.7768 0.0009 0.067 Uiso calc R 1 1
O O3 0.5733(2) 0.68189(16) 0.08031(6) 0.0355(3) Uani d . 1 1
H H3A 0.4761 0.6461 0.0975 0.053 Uiso calc R 1 1
O O4 0.7372(2) 0.60980(15) 0.19307(5) 0.0337(3) Uani d . 1 1
C C40 0.7222(3) 0.7259(2) 0.23403(8) 0.0380(5) Uani d . 1 1
H H40A 0.6411 0.8049 0.2183 0.046 Uiso calc R 1 1
H H40B 0.8573 0.7630 0.2430 0.046 Uiso calc R 1 1
C C41 0.6222(3) 0.6670(2) 0.28745(8) 0.0355(5) Uani d . 1 1
C C42 0.4478(3) 0.7314(3) 0.31025(9) 0.0424(5) Uani d . 1 1
H H42 0.3947 0.8154 0.2937 0.051 Uiso calc R 1 1
C C43 0.3531(4) 0.6700(3) 0.35777(10) 0.0563(7) Uani d . 1 1
H H43 0.2358 0.7130 0.3727 0.068 Uiso calc R 1 1
C C44 0.4302(5) 0.5471(3) 0.38299(10) 0.0601(7) Uani d . 1 1
H H44 0.3630 0.5050 0.4141 0.072 Uiso calc R 1 1
C C45 0.6085(5) 0.4856(3) 0.36203(10) 0.0594(7) Uani d . 1 1
H H45 0.6650 0.4044 0.3799 0.071 Uiso calc R 1 1
C C46 0.7013(4) 0.5455(3) 0.31468(9) 0.0471(6) Uani d . 1 1
H H46 0.8205 0.5033 0.3006 0.057 Uiso calc R 1 1
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 0.0000 '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 0.0000 '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
O1 C1 O5 112.30(17)
O1 C1 C2 107.24(16)
O5 C1 C2 111.33(16)
O1 C1 H1 108.6
O5 C1 H1 108.6
C2 C1 H1 108.6
O2 C2 C1 110.35(16)
O2 C2 C3 108.14(15)
C1 C2 C3 109.60(15)
O2 C2 H2 109.6
C1 C2 H2 109.6
C3 C2 H2 109.6
O3 C3 C4 112.53(15)
O3 C3 C2 108.27(14)
C4 C3 C2 109.53(15)
O3 C3 H3 108.8
C4 C3 H3 108.8
C2 C3 H3 108.8
O4 C4 C3 108.97(13)
O4 C4 C5 107.88(14)
C3 C4 C5 109.51(15)
O4 C4 H4 110.1
C3 C4 H4 110.1
C5 C4 H4 110.1
O5 C5 C6 105.68(15)
O5 C5 C4 110.25(15)
C6 C5 C4 114.22(17)
O5 C5 H5 108.8
C6 C5 H5 108.8
C4 C5 H5 108.8
C1 O5 C5 114.51(14)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C1 O1 C7 113.7(2)
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C2 O2 H2A 109.5
C3 O3 H3A 109.5
C4 O4 C40 115.00(14)
O4 C40 C41 108.17(15)
O4 C40 H40A 110.1
C41 C40 H40A 110.1
O4 C40 H40B 110.1
C41 C40 H40B 110.1
H40A C40 H40B 108.4
C46 C41 C42 118.4(2)
C46 C41 C40 120.40(19)
C42 C41 C40 121.2(2)
C41 C42 C43 119.8(2)
C41 C42 H42 120.1
C43 C42 H42 120.1
C44 C43 C42 120.9(2)
C44 C43 H43 119.6
C42 C43 H43 119.6
C43 C44 C45 119.7(2)
C43 C44 H44 120.2
C45 C44 H44 120.2
C46 C45 C44 119.4(3)
C46 C45 H45 120.3
C44 C45 H45 120.3
C45 C46 C41 121.7(2)
C45 C46 H46 119.1
C41 C46 H46 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.404(3)
C1 O5 1.412(2)
C1 C2 1.524(3)
C1 H1 0.9800
C2 O2 1.414(2)
C2 C3 1.525(3)
C2 H2 0.9800
C3 O3 1.426(2)
C3 C4 1.519(2)
C3 H3 0.9800
C4 O4 1.431(2)
C4 C5 1.535(3)
C4 H4 0.9800
C5 O5 1.445(2)
C5 C6 1.508(3)
C5 H5 0.9800
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
O1 C7 1.424(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
O2 H2A 0.8200
O3 H3A 0.8200
O4 C40 1.433(2)
C40 C41 1.505(3)
C40 H40A 0.9700
C40 H40B 0.9700
C41 C46 1.383(3)
C41 C42 1.390(3)
C42 C43 1.387(3)
C42 H42 0.9300
C43 C44 1.369(4)
C43 H43 0.9300
C44 C45 1.384(4)
C44 H44 0.9300
C45 C46 1.373(3)
C45 H45 0.9300
C46 H46 0.9300
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 O3 3_565 0.82 2.00 2.813(2) 172 yes
O3 H3A O5 1_455 0.82 2.05 2.799(2) 151 yes
C7 H7C Cg 4_745 0.96 2.89 3.652(3) 137 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
_geom_torsion_publ_flag
O1 C1 C2 O2 -173.76(14) ?
O5 C1 C2 O2 63.0(2) ?
O1 C1 C2 C3 67.3(2) ?
O5 C1 C2 C3 -55.9(2) ?
O2 C2 C3 O3 58.98(19) ?
C1 C2 C3 O3 179.27(15) ?
O2 C2 C3 C4 -64.05(19) ?
C1 C2 C3 C4 56.2(2) ?
O3 C3 C4 O4 65.15(19) ?
C2 C3 C4 O4 -174.41(15) ?
O3 C3 C4 C5 -177.09(14) ?
C2 C3 C4 C5 -56.64(19) ?
O4 C4 C5 O5 174.32(14) ?
C3 C4 C5 O5 55.90(18) ?
O4 C4 C5 C6 -66.9(2) ?
C3 C4 C5 C6 174.69(16) ?
O1 C1 O5 C5 -62.6(2) ?
C2 C1 O5 C5 57.6(2) ?
C6 C5 O5 C1 178.65(18) ?
C4 C5 O5 C1 -57.5(2) ?
O5 C1 O1 C7 -67.8(2) no
C2 C1 O1 C7 169.56(19) ?
C3 C4 O4 C40 -132.63(17) ?
C5 C4 O4 C40 108.58(18) ?
C4 O4 C40 C41 -168.12(15) no
O4 C40 C41 C46 54.2(2) no
O4 C40 C41 C42 -124.9(2) no
C46 C41 C42 C43 -2.5(3) ?
C40 C41 C42 C43 176.6(2) ?
C41 C42 C43 C44 0.5(3) ?
C42 C43 C44 C45 2.2(4) ?
C43 C44 C45 C46 -2.8(4) ?
C44 C45 C46 C41 0.7(4) ?
C42 C41 C46 C45 1.9(3) ?
C40 C41 C46 C45 -177.2(2) ?
C40 O4 C4 H4 -11.7 no
C7 O1 C1 H1 52.3 no
