#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:59:25 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033012.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_4033012
loop_
_publ_author_name
'Padiyar, Laxmansingh T.'
'Zulueta, Medel Manuel L.'
'Sabbavarapu, Narayana Murthy'
'Hung, Shang-Cheng'
_publ_section_title
;
 Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate
 and Its Application in the Synthesis of Chiral Inositol Phosphates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11418
_journal_page_last               11430
_journal_paper_doi               10.1021/acs.joc.7b01919
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H18 O9'
_chemical_formula_sum            'C17 H18 O9'
_chemical_formula_weight         366.31
_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_update_record
;
2012-11-01 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.341
_cell_length_b                   10.055
_cell_length_c                   21.981
_cell_measurement_reflns_used    4158
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3376
_cell_measurement_theta_min      2.9197
_cell_volume                     1622.500
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.4875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0560077
_diffrn_orient_matrix_UB_12      -0.0383895
_diffrn_orient_matrix_UB_13      -0.0195699
_diffrn_orient_matrix_UB_21      -0.0678522
_diffrn_orient_matrix_UB_22      -0.00304
_diffrn_orient_matrix_UB_23      0.0229397
_diffrn_orient_matrix_UB_31      -0.0399215
_diffrn_orient_matrix_UB_32      0.0590769
_diffrn_orient_matrix_UB_33      -0.0115285
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17313
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.99844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_coef       0.0100(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0333P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                3624
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01919_si_002.cif
_cod_data_source_block           i13181
_cod_depositor_comments          'Adding full bibliography for 4033012.cif.'
_cod_original_cell_volume        1622.5
_cod_database_code               4033012
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_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
O1 O 0.86571(15) 0.66052(11) 0.80123(5) 0.0160(2) Uani 1 1 d
O5 O 0.92405(14) 0.88737(11) 0.79608(5) 0.0155(2) Uani 1 1 d
O3 O 1.01264(14) 0.74671(10) 0.71742(5) 0.0146(2) Uani 1 1 d
O2 O 0.75732(16) 0.53717(10) 0.68589(5) 0.0170(2) Uani 1 1 d
O6 O 0.43761(15) 0.82479(12) 0.76862(5) 0.0181(3) Uani 1 1 d
O4 O 0.62110(15) 0.94435(10) 0.66786(5) 0.0137(2) Uani 1 1 d
O7 O 0.78482(16) 1.00914(12) 0.58588(5) 0.0203(3) Uani 1 1 d
O8 O 0.46606(16) 1.02081(10) 0.51744(5) 0.0163(2) Uani 1 1 d
O9 O 0.4780(2) 1.22329(12) 0.55928(6) 0.0307(3) Uani 1 1 d
C4 C 0.7851(2) 0.91134(15) 0.70009(7) 0.0134(3) Uani 1 1 d
C3 C 0.8446(2) 0.76946(15) 0.68466(8) 0.0132(3) Uani 1 1 d
C7 C 0.9854(2) 0.75809(16) 0.78033(7) 0.0157(3) Uani 1 1 d
C5 C 0.7495(2) 0.91721(15) 0.76823(7) 0.0143(3) Uani 1 1 d
C2 C 0.7051(2) 0.66752(15) 0.70489(7) 0.0135(3) Uani 1 1 d
C1 C 0.6873(2) 0.67725(16) 0.77372(7) 0.0141(3) Uani 1 1 d
C6 C 0.6154(2) 0.81332(16) 0.79249(7) 0.0150(3) Uani 1 1 d
C8 C 0.6428(2) 0.98091(15) 0.60896(7) 0.0134(3) Uani 1 1 d
C9 C 0.4598(2) 0.96584(15) 0.57745(7) 0.0139(3) Uani 1 1 d
C16 C 0.4730(2) 1.15482(16) 0.51450(8) 0.0203(4) Uani 1 1 d
C17 C 0.4713(3) 1.2020(2) 0.45015(9) 0.0286(4) Uani 1 1 d
C10 C 0.4232(2) 0.81907(16) 0.57189(7) 0.0138(3) Uani 1 1 d
C11 C 0.2793(2) 0.76242(17) 0.60309(7) 0.0159(3) Uani 1 1 d
C12 C 0.2512(2) 0.62594(16) 0.60018(8) 0.0191(3) Uani 1 1 d
C13 C 0.3672(2) 0.54668(17) 0.56659(8) 0.0206(4) Uani 1 1 d
C14 C 0.5130(2) 0.60357(17) 0.53599(9) 0.0223(4) Uani 1 1 d
C15 C 0.5410(2) 0.73960(16) 0.53852(8) 0.0188(3) Uani 1 1 d
H4 H 0.882(2) 0.9744(16) 0.6912(7) 0.009(4) Uiso 1 1 d
H3 H 0.869(2) 0.7629(16) 0.6429(8) 0.005(4) Uiso 1 1 d
H7 H 1.101(2) 0.7429(15) 0.8002(7) 0.004(4) Uiso 1 1 d
H5 H 0.715(2) 1.0074(16) 0.7812(7) 0.005(4) Uiso 1 1 d
H2A H 0.865(3) 0.525(2) 0.7001(10) 0.040(6) Uiso 1 1 d
H2 H 0.593(2) 0.6861(16) 0.6856(7) 0.008(4) Uiso 1 1 d
H6A H 0.388(3) 0.889(2) 0.7848(11) 0.037(6) Uiso 1 1 d
H1 H 0.613(2) 0.6058(17) 0.7884(8) 0.015(4) Uiso 1 1 d
H6 H 0.614(2) 0.8189(16) 0.8357(8) 0.006(4) Uiso 1 1 d
H9 H 0.365(2) 1.0100(17) 0.6027(8) 0.012(4) Uiso 1 1 d
H17A H 0.382(5) 1.157(3) 0.4278(15) 0.090(11) Uiso 1 1 d
H17B H 0.580(5) 1.181(4) 0.4331(15) 0.090(11) Uiso 1 1 d
H17C H 0.442(4) 1.290(3) 0.4488(11) 0.053(7) Uiso 1 1 d
H11 H 0.201(3) 0.817(2) 0.6267(9) 0.022(5) Uiso 1 1 d
H12 H 0.149(3) 0.586(2) 0.6229(9) 0.026(5) Uiso 1 1 d
H13 H 0.351(3) 0.450(2) 0.5660(8) 0.020(5) Uiso 1 1 d
H14 H 0.597(3) 0.547(2) 0.5126(9) 0.027(5) Uiso 1 1 d
H15 H 0.639(3) 0.7777(18) 0.5172(8) 0.020(5) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C7 O1 C1 110.45(11)
C7 O5 C5 111.52(12)
C7 O3 C3 110.88(11)
C2 O2 H2A 105.8(15)
C6 O6 H6A 108.3(17)
C8 O4 C4 115.81(12)
C16 O8 C9 115.52(12)
O4 C4 C5 109.44(12)
O4 C4 C3 110.21(12)
C5 C4 C3 107.66(12)
O4 C4 H4 111.4(10)
C5 C4 H4 107.3(10)
C3 C4 H4 110.7(10)
O3 C3 C2 108.85(12)
O3 C3 C4 106.29(12)
C2 C3 C4 111.88(13)
O3 C3 H3 108.3(10)
C2 C3 H3 111.6(10)
C4 C3 H3 109.7(10)
O1 C7 O3 110.94(12)
O1 C7 O5 111.36(12)
O3 C7 O5 111.15(12)
O1 C7 H7 107.1(9)
O3 C7 H7 107.8(9)
O5 C7 H7 108.3(9)
O5 C5 C4 104.80(12)
O5 C5 C6 106.23(12)
C4 C5 C6 115.27(13)
O5 C5 H5 107.1(10)
C4 C5 H5 111.4(9)
C6 C5 H5 111.3(10)
O2 C2 C3 110.71(12)
O2 C2 C1 111.89(12)
C3 C2 C1 107.84(13)
O2 C2 H2 106.5(10)
C3 C2 H2 108.9(10)
C1 C2 H2 111.0(10)
O1 C1 C2 109.22(12)
O1 C1 C6 107.68(12)
C2 C1 C6 110.90(13)
O1 C1 H1 106.6(11)
C2 C1 H1 109.6(11)
C6 C1 H1 112.7(11)
O6 C6 C1 107.04(13)
O6 C6 C5 114.15(13)
C1 C6 C5 107.20(13)
O6 C6 H6 110.8(10)
C1 C6 H6 109.1(10)
C5 C6 H6 108.4(10)
O7 C8 O4 124.99(14)
O7 C8 C9 127.04(14)
O4 C8 C9 107.71(12)
O8 C9 C10 108.04(12)
O8 C9 C8 110.68(12)
C10 C9 C8 107.01(13)
O8 C9 H9 111.4(10)
C10 C9 H9 111.1(10)
C8 C9 H9 108.5(10)
O9 C16 O8 122.27(16)
O9 C16 C17 126.46(16)
O8 C16 C17 111.26(15)
C16 C17 H17A 110(2)
C16 C17 H17B 108(2)
H17A C17 H17B 106(3)
C16 C17 H17C 110.0(15)
H17A C17 H17C 107(3)
H17B C17 H17C 115(3)
C11 C10 C15 120.09(15)
C11 C10 C9 120.00(14)
C15 C10 C9 119.78(14)
C10 C11 C12 119.85(16)
C10 C11 H11 119.8(12)
C12 C11 H11 120.4(12)
C13 C12 C11 120.22(17)
C13 C12 H12 120.1(12)
C11 C12 H12 119.7(12)
C12 C13 C14 119.81(16)
C12 C13 H13 120.3(11)
C14 C13 H13 119.8(11)
C15 C14 C13 120.17(16)
C15 C14 H14 120.0(12)
C13 C14 H14 119.9(12)
C14 C15 C10 119.85(16)
C14 C15 H15 119.8(11)
C10 C15 H15 120.3(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3948(19)
O1 C1 1.4522(18)
O5 C7 1.4185(19)
O5 C5 1.4515(19)
O3 C7 1.4019(19)
O3 C3 1.4466(18)
O2 C2 1.4280(18)
O2 H2A 0.86(3)
O6 C6 1.4116(19)
O6 H6A 0.82(2)
O4 C8 1.3553(19)
O4 C4 1.4359(18)
O7 C8 1.193(2)
O8 C16 1.3499(19)
O8 C9 1.4309(19)
O9 C16 1.202(2)
C4 C5 1.522(2)
C4 C3 1.530(2)
C4 H4 0.974(17)
C3 C2 1.515(2)
C3 H3 0.938(17)
C7 H7 0.969(16)
C5 C6 1.531(2)
C5 H5 0.984(16)
C2 C1 1.522(2)
C2 H2 0.948(17)
C1 C6 1.523(2)
C1 H1 0.957(19)
C6 H6 0.950(17)
C8 C9 1.519(2)
C9 C10 1.505(2)
C9 H9 0.993(18)
C16 C17 1.492(3)
C17 H17A 0.94(4)
C17 H17B 0.90(4)
C17 H17C 0.91(3)
C10 C11 1.382(2)
C10 C15 1.387(2)
C11 C12 1.389(2)
C11 H11 0.95(2)
C12 C13 1.380(3)
C12 H12 0.99(2)
C13 C14 1.388(3)
C13 H13 0.98(2)
C14 C15 1.384(2)
C14 H14 0.98(2)
C15 H15 0.94(2)
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
C8 O4 C4 C5 161.52(12)
C8 O4 C4 C3 -80.27(16)
C7 O3 C3 C2 -59.72(15)
C7 O3 C3 C4 60.95(15)
O4 C4 C3 O3 178.22(11)
C5 C4 C3 O3 -62.48(15)
O4 C4 C3 C2 -63.09(16)
C5 C4 C3 C2 56.21(16)
C1 O1 C7 O3 -62.99(15)
C1 O1 C7 O5 61.38(16)
C3 O3 C7 O1 63.51(15)
C3 O3 C7 O5 -60.98(15)
C5 O5 C7 O1 -62.11(16)
C5 O5 C7 O3 62.14(15)
C7 O5 C5 C4 -61.88(15)
C7 O5 C5 C6 60.59(15)
O4 C4 C5 O5 -177.95(11)
C3 C4 C5 O5 62.26(15)
O4 C4 C5 C6 65.66(16)
C3 C4 C5 C6 -54.13(17)
O3 C3 C2 O2 -67.23(16)
C4 C3 C2 O2 175.61(13)
O3 C3 C2 C1 55.48(16)
C4 C3 C2 C1 -61.68(16)
C7 O1 C1 C2 59.32(16)
C7 O1 C1 C6 -61.18(15)
O2 C2 C1 O1 66.52(16)
C3 C2 C1 O1 -55.47(15)
O2 C2 C1 C6 -174.97(12)
C3 C2 C1 C6 63.04(16)
O1 C1 C6 O6 -176.41(11)
C2 C1 C6 O6 64.15(16)
O1 C1 C6 C5 60.71(15)
C2 C1 C6 C5 -58.74(16)
O5 C5 C6 O6 -178.26(12)
C4 C5 C6 O6 -62.69(18)
O5 C5 C6 C1 -59.90(15)
C4 C5 C6 C1 55.67(17)
C4 O4 C8 O7 -13.5(2)
C4 O4 C8 C9 161.04(12)
C16 O8 C9 C10 171.29(13)
C16 O8 C9 C8 -71.84(17)
O7 C8 C9 O8 -14.0(2)
O4 C8 C9 O8 171.63(11)
O7 C8 C9 C10 103.50(18)
O4 C8 C9 C10 -70.87(15)
C9 O8 C16 O9 1.8(2)
C9 O8 C16 C17 -177.63(15)
O8 C9 C10 C11 -126.20(15)
C8 C9 C10 C11 114.59(15)
O8 C9 C10 C15 57.89(18)
C8 C9 C10 C15 -61.33(18)
C15 C10 C11 C12 -1.0(2)
C9 C10 C11 C12 -176.92(15)
C10 C11 C12 C13 0.4(2)
C11 C12 C13 C14 0.5(3)
C12 C13 C14 C15 -0.8(3)
C13 C14 C15 C10 0.2(3)
C11 C10 C15 C14 0.7(2)
C9 C10 C15 C14 176.62(16)
