#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/36/4023618.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023618
loop_
_publ_author_name
'Shankar D. Markad'
'Shijing Xia'
'Nicole L. Snyder'
'Bikash Surana'
'Martha D. Morton'
'Christopher M. Hadad'
'Mark W. Peczuh'
_publ_section_title
;
 Stereoselectivity in the Epoxidation of Carbohydrate-Based Oxepines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6341
_journal_page_last               6354
_journal_paper_doi               10.1021/jo800979a
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_sum            'C14 H24 O7'
_chemical_formula_weight         304.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 104.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1520(18)
_cell_length_b                   5.3065(11)
_cell_length_c                   16.311(3)
_cell_measurement_temperature    173(2)
_cell_volume                     766.4(3)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1365
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2981
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_coef       0.085(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1746
_refine_ls_R_factor_gt           0.0955
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2251
_refine_ls_wR_factor_ref         0.2732
_reflns_number_gt                1652
_reflns_number_total             2981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800979a-file001.cif
_cod_data_source_block           mp04
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023618
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.2382(5) 0.4735(13) 0.1321(3) 0.0346(12) Uani 1 1 d . . .
O2 O 0.2821(5) 0.5479(14) 0.0041(3) 0.0400(13) Uani 1 1 d . . .
O3 O 0.5704(6) 0.4464 0.0529(3) 0.0400(13) Uani 1 1 d D . .
H3 H 0.589(11) 0.282(10) 0.028(6) 0.10(4) Uiso 1 1 d D . .
O4 O 0.6819(5) 0.1963(14) 0.2170(3) 0.0349(12) Uani 1 1 d . . .
O5 O 0.5625(5) -0.1098(13) 0.2739(3) 0.0353(12) Uani 1 1 d . . .
O6 O 0.3256(5) 0.0828(13) 0.3243(3) 0.0324(12) Uani 1 1 d . . .
O7 O 0.1114(5) 0.3267(13) 0.3191(3) 0.0373(13) Uani 1 1 d . . .
C1 C 0.3151(8) 0.3838(17) 0.0726(4) 0.0329(17) Uani 1 1 d . . .
H1A H 0.2824 0.2085 0.0542 0.040 Uiso 1 1 calc R . .
C2 C 0.4854(8) 0.3938(17) 0.1117(4) 0.0325(16) Uani 1 1 d . . .
H2A H 0.5048 0.5325 0.1547 0.039 Uiso 1 1 calc R . .
C3 C 0.5412(7) 0.1451(18) 0.1591(4) 0.0313(17) Uani 1 1 d . . .
H3A H 0.5563 0.0164 0.1172 0.038 Uiso 1 1 calc R . .
C4 C 0.4484(8) 0.0286(16) 0.2152(4) 0.0323(17) Uani 1 1 d . . .
H4A H 0.3740 -0.0926 0.1806 0.039 Uiso 1 1 calc R . .
C5 C 0.3658(8) 0.2144(17) 0.2558(4) 0.0325(17) Uani 1 1 d . . .
H5A H 0.4329 0.3606 0.2784 0.039 Uiso 1 1 calc R . .
C6 C 0.2207(8) 0.3063(17) 0.1971(4) 0.0330(17) Uani 1 1 d . . .
H6A H 0.1591 0.1579 0.1708 0.040 Uiso 1 1 calc R . .
C7 C 0.1324(8) 0.526(2) -0.0475(5) 0.055(2) Uani 1 1 d . . .
H7A H 0.1169 0.6479 -0.0940 0.083 Uiso 1 1 calc R . .
H7B H 0.0606 0.5597 -0.0132 0.083 Uiso 1 1 calc R . .
H7C H 0.1163 0.3550 -0.0707 0.083 Uiso 1 1 calc R . .
C8 C 0.7070(7) 0.0019(16) 0.2807(4) 0.0302(16) Uani 1 1 d . . .
C9 C 0.8122(8) -0.1911(18) 0.2629(5) 0.043(2) Uani 1 1 d . . .
H9A H 0.7685 -0.2677 0.2074 0.065 Uiso 1 1 calc R . .
H9B H 0.8288 -0.3216 0.3068 0.065 Uiso 1 1 calc R . .
H9C H 0.9087 -0.1115 0.2627 0.065 Uiso 1 1 calc R . .
C10 C 0.7634(10) 0.1321(18) 0.3654(4) 0.049(2) Uani 1 1 d . . .
H10A H 0.6893 0.2582 0.3725 0.074 Uiso 1 1 calc R . .
H10B H 0.8599 0.2151 0.3675 0.074 Uiso 1 1 calc R . .
H10C H 0.7774 0.0074 0.4110 0.074 Uiso 1 1 calc R . .
C11 C 0.1306(9) 0.4610(18) 0.2464(4) 0.0389(18) Uani 1 1 d . . .
H11A H 0.1839 0.6216 0.2649 0.047 Uiso 1 1 calc R . .
H11B H 0.0302 0.5017 0.2089 0.047 Uiso 1 1 calc R . .
C12 C 0.2492(8) 0.2377(17) 0.3727(4) 0.0337(17) Uani 1 1 d . . .
C13 C 0.2005(9) 0.0594(19) 0.4340(4) 0.046(2) Uani 1 1 d . . .
H13A H 0.1351 -0.0721 0.4020 0.069 Uiso 1 1 calc R . .
H13B H 0.1451 0.1540 0.4681 0.069 Uiso 1 1 calc R . .
H13C H 0.2900 -0.0183 0.4714 0.069 Uiso 1 1 calc R . .
C14 C 0.3488(9) 0.4415(18) 0.4178(4) 0.0415(19) Uani 1 1 d . . .
H14A H 0.3785 0.5511 0.3765 0.062 Uiso 1 1 calc R . .
H14B H 0.4393 0.3672 0.4555 0.062 Uiso 1 1 calc R . .
H14C H 0.2946 0.5407 0.4514 0.062 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C6 118.1(5) . . ?
C1 O2 C7 114.0(6) . . ?
H3 O3 C2 107(6) . . ?
C3 O4 C8 107.2(5) . . ?
C8 O5 C4 110.1(5) . . ?
C12 O6 C5 113.8(5) . . ?
C12 O7 C11 113.5(5) . . ?
O2 C1 O1 107.2(5) . . ?
O2 C1 C2 107.8(5) . . ?
O1 C1 C2 109.4(5) . . ?
O3 C2 C1 113.8(5) . . ?
O3 C2 C3 109.8(6) . . ?
C1 C2 C3 110.6(6) . . ?
O4 C3 C4 103.1(5) . . ?
O4 C3 C2 107.4(5) . . ?
C4 C3 C2 118.7(6) . . ?
O5 C4 C5 114.1(5) . . ?
O5 C4 C3 100.8(5) . . ?
C5 C4 C3 114.7(6) . . ?
O6 C5 C4 106.3(6) . . ?
O6 C5 C6 106.9(5) . . ?
C4 C5 C6 113.3(5) . . ?
O1 C6 C5 115.3(5) . . ?
O1 C6 C11 103.6(6) . . ?
C5 C6 C11 110.2(5) . . ?
O5 C8 O4 105.4(5) . . ?
O5 C8 C9 109.4(6) . . ?
O4 C8 C9 110.2(5) . . ?
O5 C8 C10 110.9(6) . . ?
O4 C8 C10 106.6(5) . . ?
C9 C8 C10 113.9(6) . . ?
O7 C11 C6 111.3(6) . . ?
O7 C12 O6 109.3(5) . . ?
O7 C12 C14 113.7(6) . . ?
O6 C12 C14 111.5(5) . . ?
O7 C12 C13 104.4(5) . . ?
O6 C12 C13 105.6(6) . . ?
C14 C12 C13 111.9(6) . . ?
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 C1 1.419(8) . ?
O1 C6 1.422(8) . ?
O2 C1 1.388(8) . ?
O2 C7 1.420(8) . ?
O3 H3 1.0000(11) . ?
O3 C2 1.407(8) . ?
O4 C3 1.417(8) . ?
O4 C8 1.441(8) . ?
O5 C8 1.428(8) . ?
O5 C4 1.428(8) . ?
O6 C12 1.439(8) . ?
O6 C5 1.443(8) . ?
O7 C12 1.422(8) . ?
O7 C11 1.432(8) . ?
C1 C2 1.528(9) . ?
C2 C3 1.549(10) . ?
C3 C4 1.528(9) . ?
C4 C5 1.495(9) . ?
C5 C6 1.508(9) . ?
C6 C11 1.529(9) . ?
C8 C9 1.484(10) . ?
C8 C10 1.514(10) . ?
C12 C14 1.484(10) . ?
C12 C13 1.522(10) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658725
