#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:48:41 +0100 (vie 25 de mar de 2016) $
#$Revision: 179765 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/61/7006121.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_7006121
loop_
_publ_author_name
'Chisholm, Malcolm H.'
'Gallucci, Judith C.'
'Yin, Hongfeng'
_publ_section_title
;
 18-membered cyclic esters derived from glycolide and lactide:
 preparations, structures and coordination to sodium ions.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4811
_journal_page_last               4821
_journal_paper_doi               10.1039/b709081a
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H24 O12'
_chemical_formula_sum            'C18 H24 O12'
_chemical_formula_weight         432.37
_chemical_name_common            'Chisholm 1498'
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-01-31T13:00:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.048(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4322(10)
_cell_length_b                   16.513(2)
_cell_length_c                   14.964(2)
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     2080.7(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.105626
_diffrn_orient_matrix_UB_12      -0.539368E-1
_diffrn_orient_matrix_UB_13      0.61782E-2
_diffrn_orient_matrix_UB_21      -0.76003E-2
_diffrn_orient_matrix_UB_22      0.80641E-2
_diffrn_orient_matrix_UB_23      -0.59537E-1
_diffrn_orient_matrix_UB_31      0.262092E-1
_diffrn_orient_matrix_UB_32      -0.604833E-1
_diffrn_orient_matrix_UB_33      -0.115381E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34054
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'wedge-shaped fragment'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+0.2267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                3455
_reflns_number_total             4751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709081a.txt
_cod_data_source_block           Chisholm1498
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7006121
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48085(10) 0.11097(5) 0.17942(6) 0.0316(2) Uani 1 1 d . . .
O2 O 0.35295(9) 0.23013(5) 0.18801(5) 0.0285(2) Uani 1 1 d . . .
O3 O 0.57546(11) 0.27738(6) 0.08016(6) 0.0387(2) Uani 1 1 d . . .
O4 O 0.45644(9) 0.21419(5) -0.03745(5) 0.0248(2) Uani 1 1 d . . .
O5 O 0.87213(10) 0.18253(6) -0.05541(6) 0.0402(3) Uani 1 1 d . . .
O6 O 0.67952(9) 0.11003(5) 0.00539(5) 0.0257(2) Uani 1 1 d . . .
O7 O 0.86594(10) 0.15118(5) 0.15590(6) 0.0335(2) Uani 1 1 d . . .
O8 O 0.98151(9) 0.02802(5) 0.15755(6) 0.0300(2) Uani 1 1 d . . .
O9 O 1.00592(12) 0.08945(7) 0.38668(7) 0.0491(3) Uani 1 1 d . . .
O10 O 0.83269(9) 0.00957(5) 0.30835(6) 0.0279(2) Uani 1 1 d . . .
O11 O 0.46812(10) 0.06348(6) 0.39366(6) 0.0389(2) Uani 1 1 d . . .
O12 O 0.65567(9) 0.13791(5) 0.33124(5) 0.0282(2) Uani 1 1 d . . .
C1 C 0.45739(13) 0.17289(8) 0.21852(8) 0.0247(3) Uani 1 1 d . . .
C2 C 0.31092(14) 0.22552(8) 0.09324(8) 0.0273(3) Uani 1 1 d . . .
H2 H 0.2707 0.1701 0.0772 0.033 Uiso 1 1 calc R . .
C3 C 0.18366(16) 0.28793(9) 0.07228(9) 0.0390(3) Uani 1 1 d . . .
H3A H 0.0903 0.2756 0.1061 0.059 Uiso 1 1 calc R . .
H3B H 0.1541 0.2869 0.0081 0.059 Uiso 1 1 calc R . .
H3C H 0.224 0.3418 0.089 0.059 Uiso 1 1 calc R . .
C4 C 0.46293(14) 0.24308(7) 0.04622(8) 0.0257(3) Uani 1 1 d . . .
C5 C 0.60281(13) 0.22436(8) -0.08326(8) 0.0275(3) Uani 1 1 d . . .
H5 H 0.6361 0.2825 -0.0803 0.033 Uiso 1 1 calc R . .
C6 C 0.56669(16) 0.20065(9) -0.17948(9) 0.0366(3) Uani 1 1 d . . .
H6A H 0.523 0.1457 -0.182 0.055 Uiso 1 1 calc R . .
H6B H 0.6645 0.2024 -0.212 0.055 Uiso 1 1 calc R . .
H6C H 0.489 0.2385 -0.2071 0.055 Uiso 1 1 calc R . .
C7 C 0.73450(14) 0.17187(7) -0.04188(8) 0.0262(3) Uani 1 1 d . . .
C8 C 0.79497(14) 0.05216(7) 0.04027(8) 0.0274(3) Uani 1 1 d . . .
H8 H 0.8737 0.0412 -0.0059 0.033 Uiso 1 1 calc R . .
C9 C 0.70456(17) -0.02484(8) 0.05835(10) 0.0394(3) Uani 1 1 d . . .
H9A H 0.6298 -0.0147 0.105 0.059 Uiso 1 1 calc R . .
H9B H 0.7795 -0.0673 0.0783 0.059 Uiso 1 1 calc R . .
H9C H 0.646 -0.0423 0.0034 0.059 Uiso 1 1 calc R . .
C10 C 0.88097(13) 0.08554(8) 0.12379(8) 0.0260(3) Uani 1 1 d . . .
C11 C 1.06977(14) 0.04801(8) 0.24010(9) 0.0313(3) Uani 1 1 d . . .
H11 H 1.1251 0.101 0.2329 0.038 Uiso 1 1 calc R . .
C12 C 1.19272(15) -0.01837(9) 0.25452(10) 0.0405(4) Uani 1 1 d . . .
H12A H 1.1391 -0.0707 0.2594 0.061 Uiso 1 1 calc R . .
H12B H 1.2571 -0.0077 0.3097 0.061 Uiso 1 1 calc R . .
H12C H 1.2615 -0.0196 0.2038 0.061 Uiso 1 1 calc R . .
C13 C 0.96532(15) 0.05315(8) 0.31971(9) 0.0316(3) Uani 1 1 d . . .
C14 C 0.72805(14) 0.00650(8) 0.38279(8) 0.0295(3) Uani 1 1 d . . .
H14 H 0.7914 0.0168 0.4401 0.035 Uiso 1 1 calc R . .
C15 C 0.65611(18) -0.07682(9) 0.38522(11) 0.0447(4) Uani 1 1 d . . .
H15A H 0.5932 -0.0868 0.3293 0.067 Uiso 1 1 calc R . .
H15B H 0.5874 -0.0807 0.4358 0.067 Uiso 1 1 calc R . .
H15C H 0.7409 -0.1173 0.3921 0.067 Uiso 1 1 calc R . .
C16 C 0.60139(14) 0.07115(8) 0.36976(8) 0.0258(3) Uani 1 1 d . . .
C17 C 0.54001(14) 0.19918(8) 0.30594(8) 0.0263(3) Uani 1 1 d . . .
H17 H 0.4611 0.2045 0.3531 0.032 Uiso 1 1 calc R . .
C18 C 0.62993(15) 0.27768(8) 0.29689(9) 0.0321(3) Uani 1 1 d . . .
H18A H 0.6889 0.2899 0.3535 0.048 Uiso 1 1 calc R . .
H18B H 0.5548 0.3216 0.2822 0.048 Uiso 1 1 calc R . .
H18C H 0.7044 0.2724 0.2491 0.048 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 O2 C2 114.52(9) . . ?
C4 O4 C5 114.00(9) . . ?
C7 O6 C8 116.78(9) . . ?
C10 O8 C11 116.26(10) . . ?
C13 O10 C14 117.32(10) . . ?
C16 O12 C17 116.73(9) . . ?
O1 C1 O2 123.47(11) . . ?
O1 C1 C17 125.88(11) . . ?
O2 C1 C17 110.64(10) . . ?
O2 C2 C3 107.61(10) . . ?
O2 C2 C4 105.96(9) . . ?
C3 C2 C4 112.38(11) . . ?
O2 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C4 C2 H2 110.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 O4 123.96(11) . . ?
O3 C4 C2 124.26(11) . . ?
O4 C4 C2 111.77(10) . . ?
O4 C5 C6 106.68(9) . . ?
O4 C5 C7 111.32(9) . . ?
C6 C5 C7 110.38(11) . . ?
O4 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C7 C5 H5 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 O6 124.43(11) . . ?
O5 C7 C5 122.74(11) . . ?
O6 C7 C5 112.67(10) . . ?
O6 C8 C9 106.53(10) . . ?
O6 C8 C10 110.00(10) . . ?
C9 C8 C10 112.43(11) . . ?
O6 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C10 C8 H8 109.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O7 C10 O8 124.36(12) . . ?
O7 C10 C8 127.24(11) . . ?
O8 C10 C8 108.39(10) . . ?
O8 C11 C12 105.86(10) . . ?
O8 C11 C13 112.87(10) . . ?
C12 C11 C13 110.42(11) . . ?
O8 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C13 C11 H11 109.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O9 C13 O10 125.12(13) . . ?
O9 C13 C11 121.99(12) . . ?
O10 C13 C11 112.76(11) . . ?
O10 C14 C15 108.13(11) . . ?
O10 C14 C16 109.16(10) . . ?
C15 C14 C16 111.40(11) . . ?
O10 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C16 C14 H14 109.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O11 C16 O12 124.16(11) . . ?
O11 C16 C14 123.39(12) . . ?
O12 C16 C14 112.43(10) . . ?
O12 C17 C18 106.85(9) . . ?
O12 C17 C1 107.44(10) . . ?
C18 C17 C1 112.26(10) . . ?
O12 C17 H17 110.1 . . ?
C18 C17 H17 110.1 . . ?
C1 C17 H17 110.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 1.1997(14) . ?
O2 C1 1.3545(14) . ?
O2 C2 1.4454(14) . ?
O3 C4 1.1949(14) . ?
O4 C4 1.3383(15) . ?
O4 C5 1.4530(13) . ?
O5 C7 1.2016(14) . ?
O6 C7 1.3390(14) . ?
O6 C8 1.4419(14) . ?
O7 C10 1.1950(15) . ?
O8 C10 1.3530(14) . ?
O8 C11 1.4462(15) . ?
O9 C13 1.2018(16) . ?
O10 C13 1.3331(15) . ?
O10 C14 1.4582(15) . ?
O11 C16 1.2039(14) . ?
O12 C16 1.3361(15) . ?
O12 C17 1.4418(14) . ?
C1 C17 1.5127(17) . ?
C2 C3 1.5088(17) . ?
C2 C4 1.5225(17) . ?
C2 H2 1 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C5 C6 1.5075(18) . ?
C5 C7 1.5148(17) . ?
C5 H5 1 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C8 C9 1.5143(18) . ?
C8 C10 1.5150(17) . ?
C8 H8 1 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C11 C12 1.5163(18) . ?
C11 C13 1.521(2) . ?
C11 H11 1 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C14 C15 1.5049(19) . ?
C14 C16 1.5153(17) . ?
C14 H14 1 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C17 C18 1.5115(18) . ?
C17 H17 1 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O2 C1 O1 -19.80(16) . . . . ?
C2 O2 C1 C17 159.02(9) . . . . ?
C1 O2 C2 C3 174.88(10) . . . . ?
C1 O2 C2 C4 -64.71(13) . . . . ?
C5 O4 C4 O3 3.00(17) . . . . ?
C5 O4 C4 C2 -175.93(9) . . . . ?
O2 C2 C4 O3 -20.48(16) . . . . ?
C3 C2 C4 O3 96.78(14) . . . . ?
O2 C2 C4 O4 158.45(9) . . . . ?
C3 C2 C4 O4 -84.29(13) . . . . ?
C4 O4 C5 C6 -171.53(10) . . . . ?
C4 O4 C5 C7 67.99(13) . . . . ?
C8 O6 C7 O5 -1.29(17) . . . . ?
C8 O6 C7 C5 174.25(10) . . . . ?
O4 C5 C7 O5 -163.68(12) . . . . ?
C6 C5 C7 O5 78.04(16) . . . . ?
O4 C5 C7 O6 20.69(14) . . . . ?
C6 C5 C7 O6 -97.59(12) . . . . ?
C7 O6 C8 C9 -158.87(10) . . . . ?
C7 O6 C8 C10 79.02(12) . . . . ?
C11 O8 C10 O7 2.77(17) . . . . ?
C11 O8 C10 C8 -177.53(9) . . . . ?
O6 C8 C10 O7 -3.81(17) . . . . ?
C9 C8 C10 O7 -122.34(14) . . . . ?
O6 C8 C10 O8 176.51(9) . . . . ?
C9 C8 C10 O8 57.97(13) . . . . ?
C10 O8 C11 C12 -170.10(10) . . . . ?
C10 O8 C11 C13 69.00(14) . . . . ?
C14 O10 C13 O9 0.68(18) . . . . ?
C14 O10 C13 C11 176.61(10) . . . . ?
O8 C11 C13 O9 -159.33(12) . . . . ?
C12 C11 C13 O9 82.40(16) . . . . ?
O8 C11 C13 O10 24.59(15) . . . . ?
C12 C11 C13 O10 -93.68(13) . . . . ?
C13 O10 C14 C15 -144.12(11) . . . . ?
C13 O10 C14 C16 94.53(12) . . . . ?
C17 O12 C16 O11 -9.08(17) . . . . ?
C17 O12 C16 C14 172.67(9) . . . . ?
O10 C14 C16 O11 147.10(11) . . . . ?
C15 C14 C16 O11 27.76(17) . . . . ?
O10 C14 C16 O12 -34.63(14) . . . . ?
C15 C14 C16 O12 -153.97(11) . . . . ?
C16 O12 C17 C18 159.55(10) . . . . ?
C16 O12 C17 C1 -79.79(12) . . . . ?
O1 C1 C17 O12 2.27(16) . . . . ?
O2 C1 C17 O12 -176.50(9) . . . . ?
O1 C1 C17 C18 119.46(13) . . . . ?
O2 C1 C17 C18 -59.32(13) . . . . ?
