#------------------------------------------------------------------------------
#$Date: 2018-07-10 05:18:20 +0300 (Tue, 10 Jul 2018) $
#$Revision: 208937 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/25/2242548.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_2242548
loop_
_publ_author_name
'Minyaev, Mikhail E.'
'Roitershtein, Dmitrii M.'
'Vinogradov, Alexey A.'
'Ananyev, Ivan V.'
'Nifant'ev, Ilya E.'
_publ_section_title
;
 (2R,3R)-1,4-Dioxaspiro[4.4]nonane-2,3-dicarboxylic and
 (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylic acids
;
_journal_coeditor_code           EB2009
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1058
_journal_page_last               1062
_journal_paper_doi               10.1107/S2056989018009593
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H12 O6'
_chemical_formula_moiety         'C9 H12 O6'
_chemical_formula_sum            'C9 H12 O6'
_chemical_formula_weight         216.19
_chemical_name_common
'(2R,3R)-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylic acid'
_chemical_name_systematic
'(2R,3R)-1,4-Dioxaspiro[4.4]nonane-2,3-dicarboxylic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 92.885(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2930(8)
_cell_length_b                   5.3712(7)
_cell_length_c                   14.0916(17)
_cell_measurement_reflns_used    621
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     475.71(10)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_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  0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4142
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.895
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.8269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2455
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0310P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                1914
_reflns_number_total             2455
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eb2009sup1.cif
_cod_data_source_block           I
_cod_database_code               2242548
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_occupancy
O O1 0.3838(4) 0.5521(4) 0.45124(15) 0.0153(5) Uani d 1
H H1 0.271(6) 0.587(8) 0.468(3) 0.039(13) Uiso d 1
O O2 0.3808(3) 0.8867(4) 0.35486(14) 0.0156(5) Uani d 1
O O3 0.9421(3) 0.1722(4) 0.44956(14) 0.0133(5) Uani d 1
O O4 1.0688(3) 0.2205(4) 0.30548(14) 0.0141(5) Uani d 1
H H4 1.173(6) 0.144(7) 0.332(2) 0.026(10) Uiso d 1
O O5 0.7890(3) 0.7805(3) 0.30380(14) 0.0123(5) Uani d 1
O O6 0.6993(3) 0.4106(4) 0.23156(13) 0.0127(4) Uani d 1
C C1 0.4679(4) 0.7060(5) 0.38994(19) 0.0108(6) Uani d 1
C C2 0.6954(4) 0.6301(5) 0.3722(2) 0.0113(6) Uani d 1
H H2 0.782988 0.639980 0.433289 0.014 Uiso calc 1
C C3 0.7155(4) 0.3667(5) 0.33022(19) 0.0103(6) Uani d 1
H H3 0.591522 0.263933 0.348493 0.012 Uiso calc 1
C C4 0.9202(4) 0.2424(5) 0.3672(2) 0.0105(6) Uani d 1
C C5 0.7661(4) 0.6609(5) 0.2121(2) 0.0124(6) Uani d 1
C C6 0.6025(5) 0.7952(6) 0.1454(2) 0.0174(7) Uani d 1
H H6A 0.481549 0.683619 0.127887 0.021 Uiso calc 1
H H6B 0.547171 0.945453 0.176471 0.021 Uiso calc 1
C C7 0.7213(5) 0.8670(7) 0.0571(2) 0.0276(8) Uani d 1
H H7A 0.704227 0.737514 0.007304 0.033 Uiso calc 1
H H7B 0.669165 1.027909 0.030732 0.033 Uiso calc 1
C C8 0.9535(5) 0.8873(7) 0.0939(2) 0.0220(7) Uani d 1
H H8A 1.051505 0.869535 0.041494 0.026 Uiso calc 1
H H8B 0.981059 1.048463 0.126290 0.026 Uiso calc 1
C C9 0.9776(4) 0.6711(6) 0.1634(2) 0.0161(6) Uani d 1
H H9A 1.097196 0.700938 0.210352 0.019 Uiso calc 1
H H9B 1.003536 0.513540 0.129416 0.019 Uiso calc 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
C1 O1 H1 117(3)
C4 O4 H4 108(2)
C2 O5 C5 109.3(2)
C3 O6 C5 109.7(2)
O2 C1 O1 125.4(2)
O2 C1 C2 124.0(2)
O1 C1 C2 110.5(2)
O5 C2 C1 112.8(2)
O5 C2 C3 102.6(2)
C1 C2 C3 113.9(2)
O5 C2 H2 109.1
C1 C2 H2 109.1
C3 C2 H2 109.1
O6 C3 C4 115.5(2)
O6 C3 C2 102.8(2)
C4 C3 C2 110.9(2)
O6 C3 H3 109.1
C4 C3 H3 109.1
C2 C3 H3 109.1
O3 C4 O4 123.4(2)
O3 C4 C3 121.0(2)
O4 C4 C3 115.6(2)
O6 C5 O5 105.2(2)
O6 C5 C9 112.9(2)
O5 C5 C9 109.6(2)
O6 C5 C6 111.2(2)
O5 C5 C6 111.9(2)
C9 C5 C6 106.2(2)
C7 C6 C5 106.0(2)
C7 C6 H6A 110.5
C5 C6 H6A 110.5
C7 C6 H6B 110.5
C5 C6 H6B 110.5
H6A C6 H6B 108.7
C8 C7 C6 103.9(3)
C8 C7 H7A 111.0
C6 C7 H7A 111.0
C8 C7 H7B 111.0
C6 C7 H7B 111.0
H7A C7 H7B 109.0
C9 C8 C7 103.1(3)
C9 C8 H8A 111.1
C7 C8 H8A 111.1
C9 C8 H8B 111.1
C7 C8 H8B 111.1
H8A C8 H8B 109.1
C8 C9 C5 104.8(2)
C8 C9 H9A 110.8
C5 C9 H9A 110.8
C8 C9 H9B 110.8
C5 C9 H9B 110.8
H9A C9 H9B 108.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.325(3) y
O1 H1 0.78(4) ?
O2 C1 1.208(3) y
O3 C4 1.222(3) y
O4 C4 1.314(3) y
O4 H4 0.84(4) ?
O5 C2 1.409(3) y
O5 C5 1.443(3) y
O6 C3 1.409(3) y
O6 C5 1.439(3) y
C1 C2 1.521(4) y
C2 C3 1.541(4) y
C2 H2 1.0000 ?
C3 C4 1.519(4) y
C3 H3 1.0000 ?
C5 C9 1.529(4) y
C5 C6 1.539(4) y
C6 C7 1.533(4) y
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C8 1.529(4) y
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C9 1.522(4) y
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
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
O1 H1 O3 2_656 0.78(4) 1.87(4) 2.620(3) 159(4) yes
O4 H4 O2 1_645 0.84(4) 1.92(4) 2.723(3) 159(3) yes
C2 H2 O3 2_756 1.00 2.34 3.315(4) 165.6 .
C3 H3 O2 1_545 1.00 2.43 3.358(3) 154.9 .
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
C5 O5 C2 C1 -95.7(2)
C5 O5 C2 C3 27.4(3)
O2 C1 C2 O5 -5.2(4)
O1 C1 C2 O5 177.0(2)
O2 C1 C2 C3 -121.7(3)
O1 C1 C2 C3 60.5(3)
C5 O6 C3 C4 -95.4(3)
C5 O6 C3 C2 25.5(3)
O5 C2 C3 O6 -32.0(2)
C1 C2 C3 O6 90.3(3)
O5 C2 C3 C4 92.0(3)
C1 C2 C3 C4 -145.7(2)
O6 C3 C4 O3 -172.3(2)
C2 C3 C4 O3 71.3(3)
O6 C3 C4 O4 8.6(3)
C2 C3 C4 O4 -107.8(3)
C3 O6 C5 O5 -9.5(3)
C3 O6 C5 C9 110.0(2)
C3 O6 C5 C6 -130.8(2)
C2 O5 C5 O6 -12.6(3)
C2 O5 C5 C9 -134.3(2)
C2 O5 C5 C6 108.2(2)
O6 C5 C6 C7 -120.1(3)
O5 C5 C6 C7 122.6(3)
C9 C5 C6 C7 3.0(3)
C5 C6 C7 C8 -26.1(3)
C6 C7 C8 C9 39.3(3)
C7 C8 C9 C5 -37.6(3)
O6 C5 C9 C8 143.4(3)
O5 C5 C9 C8 -99.7(3)
C6 C5 C9 C8 21.4(3)

_cod_database_fobs_code 2242548
