#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221744.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_2221744
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Jebas, Samuel Robinson'
'Rai, Sankappa'
'Shetty, Prakash'
'Isloor, Arun M'
_publ_section_title
;
 Redetermination of methyl
 3,4-O-isopropylidene-β-<small>D</small>-fucopyranoside
 monohydrate
;
_journal_coeditor_code           IS2405
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1002
_journal_page_last               o1003
_journal_paper_doi               10.1107/S1600536809012689
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C10 H18 O5 , H2 O'
_chemical_formula_sum            'C10 H20 O6'
_chemical_formula_weight         236.26
_chemical_name_common
;
Methyl 3,4-O-isopropylidene-β-D--
fucopyranoside monohydrate
;
_chemical_name_systematic        ?
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.58240(10)
_cell_length_b                   9.28340(10)
_cell_length_c                   14.6711(2)
_cell_measurement_reflns_used    9413
_cell_measurement_temperature    100
_cell_measurement_theta_max      41.56
_cell_measurement_theta_min      2.75
_cell_volume                     1168.90(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL  (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            64045
_diffrn_reflns_theta_full        37.50
_diffrn_reflns_theta_max         37.50
_diffrn_reflns_theta_min         2.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.0731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                3337
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2405.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221744
_cod_database_fobs_code          2221744
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.43844(6) 0.76639(5) 0.05482(3) 0.01206(8) Uani d . 1 . .
O O2 0.46299(6) 0.72835(6) -0.14722(3) 0.01333(9) Uani d . 1 . .
O O3 0.37807(7) 0.95475(6) -0.18528(3) 0.01399(9) Uani d . 1 . .
O O4 0.34767(7) 1.13634(6) -0.01512(4) 0.01634(10) Uani d D 1 . .
O O5 0.48979(6) 0.97492(6) 0.13084(3) 0.01364(9) Uani d . 1 . .
C C1 0.38958(8) 0.91139(7) 0.06752(4) 0.01172(10) Uani d . 1 . .
H H1A 0.2818 0.9145 0.0895 0.014 Uiso calc R 1 . .
C C2 0.33053(8) 0.68941(7) -0.00168(4) 0.01206(10) Uani d . 1 . .
H H2A 0.2268 0.6964 0.0259 0.014 Uiso calc R 1 . .
C C3 0.32312(8) 0.75401(7) -0.09665(4) 0.01172(10) Uani d . 1 . .
H H3A 0.2342 0.7132 -0.1296 0.014 Uiso calc R 1 . .
C C4 0.46232(8) 0.83123(7) -0.21980(4) 0.01328(10) Uani d . 1 . .
C C5 0.31314(7) 0.91860(7) -0.09849(4) 0.01160(10) Uani d . 1 . .
H H5A 0.2038 0.9487 -0.0961 0.014 Uiso calc R 1 . .
C C6 0.40456(8) 0.99275(7) -0.02236(4) 0.01164(10) Uani d . 1 . .
H H6A 0.5148 0.9961 -0.0396 0.014 Uiso calc R 1 . .
C C7 0.37798(10) 0.77431(9) -0.30350(5) 0.01941(13) Uani d . 1 . .
H H7A 0.2738 0.7469 -0.2871 0.029 Uiso calc R 1 . .
H H7B 0.4326 0.6920 -0.3269 0.029 Uiso calc R 1 . .
H H7C 0.3742 0.8481 -0.3493 0.029 Uiso calc R 1 . .
C C8 0.62911(9) 0.87289(9) -0.24007(5) 0.01995(13) Uani d . 1 . .
H H8A 0.6795 0.9026 -0.1848 0.030 Uiso calc R 1 . .
H H8B 0.6305 0.9508 -0.2831 0.030 Uiso calc R 1 . .
H H8C 0.6833 0.7917 -0.2653 0.030 Uiso calc R 1 . .
C C9 0.46504(9) 0.92419(8) 0.22239(4) 0.01716(12) Uani d . 1 . .
H H9A 0.5330 0.9749 0.2633 0.026 Uiso calc R 1 . .
H H9B 0.4870 0.8229 0.2253 0.026 Uiso calc R 1 . .
H H9C 0.3587 0.9409 0.2396 0.026 Uiso calc R 1 . .
C C10 0.37923(9) 0.53235(7) -0.00202(5) 0.01627(11) Uani d . 1 . .
H H10A 0.3747 0.4950 0.0589 0.024 Uiso calc R 1 . .
H H10B 0.4838 0.5243 -0.0247 0.024 Uiso calc R 1 . .
H H10C 0.3101 0.4784 -0.0405 0.024 Uiso calc R 1 . .
O O1W 0.57299(7) 0.26179(6) 0.08757(4) 0.01852(10) Uani d D 1 . .
H H1O4 0.4072(16) 1.1865(15) 0.0151(9) 0.032(4) Uiso d D 1 . .
H H1W1 0.6579(13) 0.2881(14) 0.0656(9) 0.030(4) Uiso d D 1 . .
H H2W1 0.5836(19) 0.1840(12) 0.1158(10) 0.041(4) Uiso d D 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 . . 110.92(5) ?
C4 O2 C3 . . 105.75(5) ?
C5 O3 C4 . . 108.68(5) ?
C6 O4 H1O4 . . 111.0(12) ?
C1 O5 C9 . . 113.06(5) ?
O5 C1 O1 . . 107.78(5) ?
O5 C1 C6 . . 108.30(5) ?
O1 C1 C6 . . 109.30(5) ?
O5 C1 H1A . . 110.5 ?
O1 C1 H1A . . 110.5 ?
C6 C1 H1A . . 110.5 ?
O1 C2 C10 . . 107.64(5) ?
O1 C2 C3 . . 111.14(5) ?
C10 C2 C3 . . 112.84(6) ?
O1 C2 H2A . . 108.4 ?
C10 C2 H2A . . 108.4 ?
C3 C2 H2A . . 108.4 ?
O2 C3 C2 . . 112.02(5) ?
O2 C3 C5 . . 101.77(5) ?
C2 C3 C5 . . 114.38(5) ?
O2 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
C5 C3 H3A . . 109.5 ?
O2 C4 O3 . . 105.70(5) ?
O2 C4 C8 . . 108.26(6) ?
O3 C4 C8 . . 109.83(6) ?
O2 C4 C7 . . 111.79(6) ?
O3 C4 C7 . . 108.67(6) ?
C8 C4 C7 . . 112.38(6) ?
O3 C5 C6 . . 110.18(5) ?
O3 C5 C3 . . 103.19(5) ?
C6 C5 C3 . . 114.08(5) ?
O3 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
C3 C5 H5A . . 109.7 ?
O4 C6 C1 . . 111.74(5) ?
O4 C6 C5 . . 107.46(5) ?
C1 C6 C5 . . 111.43(5) ?
O4 C6 H6A . . 108.7 ?
C1 C6 H6A . . 108.7 ?
C5 C6 H6A . . 108.7 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C8 H8A . . 109.5 ?
C4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O5 C9 H9A . . 109.5 ?
O5 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O5 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C2 C10 H10A . . 109.5 ?
C2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
H1W1 O1W H2W1 . . 110.4(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.4222(8) ?
O1 C2 . 1.4336(8) ?
O2 C4 . 1.4304(8) ?
O2 C3 . 1.4311(8) ?
O3 C5 . 1.4299(8) ?
O3 C4 . 1.4472(8) ?
O4 C6 . 1.4236(8) ?
O4 H1O4 . 0.821(9) ?
O5 C1 . 1.3966(8) ?
O5 C9 . 1.4389(8) ?
C1 C6 . 1.5251(9) ?
C1 H1A . 0.9800 ?
C2 C10 . 1.5168(10) ?
C2 C3 . 1.5183(9) ?
C2 H2A . 0.9800 ?
C3 C5 . 1.5306(9) ?
C3 H3A . 0.9800 ?
C4 C8 . 1.5123(10) ?
C4 C7 . 1.5202(10) ?
C5 C6 . 1.5287(9) ?
C5 H5A . 0.9800 ?
C6 H6A . 0.9800 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
O1W H1W1 . 0.834(8) ?
O1W H2W1 . 0.838(8) ?
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
O4 H1O4 O1W 1_565 0.821(9) 1.909(9) 2.7140(8) 166.4(16)
O1W H1W1 O4 4_565 0.834(8) 1.921(8) 2.7534(8) 175.6(14)
O1W H2W1 O5 1_545 0.838(8) 2.113(11) 2.8294(8) 143.3(15)
C9 H9C O3 2_575 0.96 2.51 3.4306(9) 161.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 O5 C1 O1 . . . . -72.50(7) ?
C9 O5 C1 C6 . . . . 169.36(6) ?
C2 O1 C1 O5 . . . . 173.54(5) ?
C2 O1 C1 C6 . . . . -68.96(6) ?
C1 O1 C2 C10 . . . . -172.91(5) ?
C1 O1 C2 C3 . . . . 63.06(7) ?
C4 O2 C3 C2 . . . . -161.33(5) ?
C4 O2 C3 C5 . . . . -38.71(6) ?
O1 C2 C3 O2 . . . . 70.09(7) ?
C10 C2 C3 O2 . . . . -50.94(7) ?
O1 C2 C3 C5 . . . . -45.05(8) ?
C10 C2 C3 C5 . . . . -166.08(6) ?
C3 O2 C4 O3 . . . . 29.57(7) ?
C3 O2 C4 C8 . . . . 147.20(6) ?
C3 O2 C4 C7 . . . . -88.49(7) ?
C5 O3 C4 O2 . . . . -7.19(7) ?
C5 O3 C4 C8 . . . . -123.77(6) ?
C5 O3 C4 C7 . . . . 112.93(6) ?
C4 O3 C5 C6 . . . . 106.03(6) ?
C4 O3 C5 C3 . . . . -16.15(7) ?
O2 C3 C5 O3 . . . . 33.37(6) ?
C2 C3 C5 O3 . . . . 154.36(5) ?
O2 C3 C5 C6 . . . . -86.15(6) ?
C2 C3 C5 C6 . . . . 34.84(8) ?
O5 C1 C6 O4 . . . . -66.61(7) ?
O1 C1 C6 O4 . . . . 176.22(5) ?
O5 C1 C6 C5 . . . . 173.15(5) ?
O1 C1 C6 C5 . . . . 55.99(7) ?
O3 C5 C6 O4 . . . . 82.09(6) ?
C3 C5 C6 O4 . . . . -162.42(5) ?
O3 C5 C6 C1 . . . . -155.19(5) ?
C3 C5 C6 C1 . . . . -39.69(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655768
