#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:58:30 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153968.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_7153968
loop_
_publ_author_name
'Pazos, G.'
'Pérez, M'
'Gándara, Z'
'Gómez, G'
'Fall, Y.'
_publ_section_title
;
 Synthesis of a chiral building block for highly functionalized polycyclic
 ethers.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7750
_journal_page_last               7757
_journal_paper_doi               10.1039/c4ob01439a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C23 H32 O9'
_chemical_formula_weight         452.49
_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                 107.545(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4323(13)
_cell_length_b                   9.4544(10)
_cell_length_c                   11.5317(13)
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.67
_cell_measurement_theta_min      2.84
_cell_volume                     1188.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6392
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0870
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1920P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2557
_refine_ls_wR_factor_ref         0.2876
_reflns_number_gt                2577
_reflns_number_total             4017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01439a2.cif
_cod_data_source_block           yf18131t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153968.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7153968
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
C1 C 1.1182(5) 0.3080(6) 0.8630(4) 0.0544(13) Uani 1 1 d .
H1 H 1.1523 0.2139 0.8580 0.065 Uiso 1 1 calc R
O2 O 1.1025(3) 0.3814(4) 0.7500(3) 0.0594(10) Uani 1 1 d .
C3 C 1.0317(5) 0.3065(6) 0.6449(5) 0.0577(13) Uani 1 1 d .
H3 H 1.0771 0.2263 0.6258 0.069 Uiso 1 1 calc R
C4 C 0.9954(6) 0.4108(7) 0.5424(5) 0.0695(16) Uani 1 1 d .
H4A H 0.9809 0.3641 0.4644 0.083 Uiso 1 1 calc R
H4B H 1.0578 0.4828 0.5509 0.083 Uiso 1 1 calc R
C5 C 0.8793(6) 0.4730(7) 0.5553(5) 0.0682(16) Uani 1 1 d .
O5 O 0.8280(5) 0.5781(5) 0.5117(4) 0.0929(16) Uani 1 1 d .
O6 O 0.8372(3) 0.3903(4) 0.6319(3) 0.0612(10) Uani 1 1 d .
C7 C 0.9089(5) 0.2611(6) 0.6581(5) 0.0563(13) Uani 1 1 d .
O7 O 0.8594(4) 0.1653(4) 0.5618(3) 0.0685(11) Uani 1 1 d .
C70 C 0.7433(8) 0.1128(10) 0.5503(7) 0.103(3) Uani 1 1 d .
H7A H 0.7455 0.0577 0.6209 0.154 Uiso 1 1 calc R
H7B H 0.7170 0.0542 0.4791 0.154 Uiso 1 1 calc R
H7C H 0.6870 0.1900 0.5428 0.154 Uiso 1 1 calc R
C8 C 0.9057(5) 0.2055(6) 0.7788(5) 0.0609(14) Uani 1 1 d .
H8A H 0.9305 0.1070 0.7869 0.073 Uiso 1 1 calc R
H8B H 0.8228 0.2114 0.7843 0.073 Uiso 1 1 calc R
C9 C 0.9919(5) 0.2919(5) 0.8802(4) 0.0542(13) Uani 1 1 d .
H9 H 0.9564 0.3862 0.8805 0.065 Uiso 1 1 calc R
O10 O 1.0046(4) 0.2266(4) 0.9946(3) 0.0607(10) Uani 1 1 d .
C11 C 1.0743(5) 0.3101(6) 1.0934(4) 0.0544(13) Uani 1 1 d .
H11 H 1.0375 0.4046 1.0860 0.065 Uiso 1 1 calc R
C12 C 1.2042(5) 0.3245(7) 1.0863(4) 0.0603(14) Uani 1 1 d .
H12 H 1.2422 0.2306 1.0948 0.072 Uiso 1 1 calc R
C13 C 1.2042(5) 0.3877(7) 0.9648(5) 0.0648(14) Uani 1 1 d .
H13A H 1.1794 0.4862 0.9611 0.078 Uiso 1 1 calc R
H13B H 1.2864 0.3837 0.9572 0.078 Uiso 1 1 calc R
C110 C 1.0660(6) 0.2434(7) 1.2109(5) 0.0663(16) Uani 1 1 d .
H10A H 1.0989 0.1482 1.2173 0.080 Uiso 1 1 calc R
H10B H 1.1163 0.2974 1.2794 0.080 Uiso 1 1 calc R
C111 C 0.9386(6) 0.2374(6) 1.2183(5) 0.0654(15) Uani 1 1 d .
H11A H 0.8854 0.1915 1.1464 0.078 Uiso 1 1 calc R
H11B H 0.9365 0.1832 1.2890 0.078 Uiso 1 1 calc R
O112 O 0.8970(4) 0.3783(4) 1.2270(3) 0.0690(11) Uani 1 1 d .
C113 C 0.7702(3) 0.3811(4) 1.2154(3) 0.0842(19) Uani 1 1 d .
H13C H 0.7487 0.4738 1.2387 0.101 Uiso 1 1 calc R
H13D H 0.7531 0.3122 1.2705 0.101 Uiso 1 1 calc R
C114 C 0.6900(3) 0.3482(4) 1.0842(3) 0.095(2) Uani 1 1 d RU
C115 C 0.5904(3) 0.2565(4) 1.0499(3) 0.145(4) Uani 1 1 d RU
H115 H 0.5698 0.2026 1.1083 0.174 Uiso 1 1 calc R
C116 C 0.5216(3) 0.2454(4) 0.9283(3) 0.128(3) Uani 1 1 d RU
H116 H 0.4550 0.1841 0.9053 0.153 Uiso 1 1 calc R
C117 C 0.5524(3) 0.3260(4) 0.8409(3) 0.151(4) Uani 1 1 d RU
C118 C 0.6520(3) 0.4177(4) 0.8752(3) 0.147(4) Uani 1 1 d RU
H118 H 0.6726 0.4716 0.8168 0.176 Uiso 1 1 calc R
C119 C 0.7208(3) 0.4287(4) 0.9969(3) 0.141(4) Uani 1 1 d RU
H119 H 0.7874 0.4901 1.0198 0.169 Uiso 1 1 calc R
O170 O 0.4842(8) 0.3180(11) 0.7110(8) 0.178(4) Uani 1 1 d .
C171 C 0.3821(10) 0.2599(17) 0.7034(18) 0.236(10) Uani 1 1 d .
H17A H 0.3722 0.1771 0.6532 0.354 Uiso 1 1 calc R
H17B H 0.3167 0.3251 0.6681 0.354 Uiso 1 1 calc R
H17C H 0.3801 0.2335 0.7832 0.354 Uiso 1 1 calc R
O120 O 1.2723(3) 0.4124(5) 1.1869(3) 0.0726(12) Uani 1 1 d .
C121 C 1.3977(6) 0.3999(11) 1.2161(7) 0.097(2) Uani 1 1 d .
H21A H 1.4359 0.4727 1.2746 0.116 Uiso 1 1 calc R
H21B H 1.4223 0.4153 1.1436 0.116 Uiso 1 1 calc R
O122 O 1.4406(5) 0.2645(10) 1.2660(6) 0.135(3) Uani 1 1 d .
C123 C 1.4231(11) 0.2341(19) 1.3799(10) 0.182(7) Uani 1 1 d .
H23A H 1.4231 0.3208 1.4233 0.273 Uiso 1 1 calc R
H23B H 1.4883 0.1743 1.4263 0.273 Uiso 1 1 calc R
H23C H 1.3460 0.1868 1.3672 0.273 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
O2 C1 C13 110.0(5)
O2 C1 C9 107.5(4)
C13 C1 C9 112.0(4)
C3 O2 C1 114.5(4)
O2 C3 C4 107.2(5)
O2 C3 C7 111.1(4)
C4 C3 C7 102.7(5)
C3 C4 C5 102.9(4)
O5 C5 O6 121.7(7)
O5 C5 C4 128.8(6)
O6 C5 C4 109.5(5)
C5 O6 C7 109.2(4)
O7 C7 O6 108.0(4)
O7 C7 C8 112.9(5)
O6 C7 C8 108.6(4)
O7 C7 C3 105.4(4)
O6 C7 C3 102.8(4)
C8 C7 C3 118.3(5)
C70 O7 C7 116.8(5)
C7 C8 C9 109.5(5)
O10 C9 C8 110.0(4)
O10 C9 C1 109.1(4)
C8 C9 C1 112.0(4)
C11 O10 C9 112.3(4)
O10 C11 C12 109.2(4)
O10 C11 C110 108.3(4)
C12 C11 C110 114.2(4)
O120 C12 C11 107.8(4)
O120 C12 C13 111.3(5)
C11 C12 C13 110.9(4)
C1 C13 C12 110.1(5)
C111 C110 C11 113.1(4)
O112 C111 C110 108.7(5)
C113 O112 C111 111.3(4)
O112 C113 C114 112.2(2)
C115 C114 C119 120.0
C115 C114 C113 126.7
C119 C114 C113 113.2
C116 C115 C114 120.0
C115 C116 C117 120.0
C116 C117 C118 120.0
C116 C117 O170 122.6(4)
C118 C117 O170 117.4(4)
C119 C118 C117 120.0
C118 C119 C114 120.0
C171 O170 C117 106.7(11)
C121 O120 C12 114.6(5)
O120 C121 O122 112.4(7)
C123 O122 C121 115.3(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.439(6)
C1 C13 1.489(8)
C1 C9 1.523(8)
O2 C3 1.426(6)
C3 C4 1.499(8)
C3 C7 1.519(8)
C4 C5 1.499(9)
C5 O5 1.186(8)
C5 O6 1.371(7)
O6 C7 1.451(7)
C7 O7 1.412(6)
C7 C8 1.498(7)
O7 C70 1.385(9)
C8 C9 1.520(7)
C9 O10 1.423(6)
O10 C11 1.418(6)
C11 C12 1.518(8)
C11 C110 1.524(7)
C12 O120 1.448(6)
C12 C13 1.523(8)
C110 C111 1.485(8)
C111 O112 1.428(7)
O112 C113 1.415(5)
C113 C114 1.5457
C114 C115 1.3900
C114 C119 1.3900
C115 C116 1.3900
C116 C117 1.3900
C117 C118 1.3900
C117 O170 1.468(9)
C118 C119 1.3900
O170 C171 1.269(11)
O120 C121 1.376(8)
C121 O122 1.429(12)
O122 C123 1.416(12)
