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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/82/7228201.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_7228201
loop_
_publ_author_name
'Amarasekara, Ananda S.'
'Ha, Uyen'
'Fonari, Marina S.'
'Bejagam, Shabari Nath'
'Margetić, Davor'
_publ_section_title
;
 Sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of
 renewable keto acids with paraformaldehyde: synthesis of a new dispiro
 bis-lactone ring system
 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione
;
_journal_issue                   39
_journal_name_full               'RSC Adv.'
_journal_page_first              23917
_journal_paper_doi               10.1039/C7RA02303K
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C11 H14 O6'
_chemical_formula_weight         242.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-10 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.085(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.326(3)
_cell_length_b                   5.8596(15)
_cell_length_c                   17.227(4)
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.38
_cell_volume                     1034.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      215(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15211
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.206
_diffrn_reflns_theta_min         2.188
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       prizm
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0419P)²+0.4495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2129
_reflns_number_total             3061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ra02303k2.cif
_cod_data_source_block           ASA_90-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi scan' changed to
'multi-scan' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7228201
_shelx_shelxl_version_number     2014/7
_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. 
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05076(15) 0.7674(3) 0.41756(8) 0.0405(5) Uani 0.880(4) 1 d D P A 1
C2 C 0.1018(2) 0.7553(5) 0.48408(13) 0.0312(7) Uani 0.880(4) 1 d D P A 1
O3 O 0.02679(16) 0.7320(4) 0.54301(12) 0.0334(7) Uani 0.880(4) 1 d D P A 1
O1' O -0.0776(8) 0.787(3) 0.5140(7) 0.064(5) Uiso 0.120(4) 1 d D P A 2
C2' C 0.0338(7) 0.740(6) 0.5357(4) 0.09(2) Uiso 0.120(4) 1 d D P A 2
O3' O 0.1141(6) 0.756(6) 0.4788(4) 0.103(12) Uiso 0.120(4) 1 d D P A 2
C4 C 0.10903(17) 0.7304(4) 0.61702(10) 0.0327(4) Uani 1 1 d D . . .
C5 C 0.24792(16) 0.6729(3) 0.59991(9) 0.0252(3) Uani 1 1 d D . . .
C6 C 0.24538(18) 0.7591(3) 0.51544(9) 0.0297(4) Uani 1 1 d D . . .
C7 C 0.27080(18) 0.4134(3) 0.60406(11) 0.0298(4) Uani 1 1 d . . . .
O8 O 0.40140(12) 0.3566(2) 0.59423(7) 0.0299(3) Uani 1 1 d . . . .
C9 C 0.48899(19) 0.4442(3) 0.65725(10) 0.0295(4) Uani 1 1 d . . . .
C10 C 0.49145(16) 0.7065(3) 0.65632(9) 0.0242(3) Uani 1 1 d . . . .
C11 C 0.35214(16) 0.7888(3) 0.65747(9) 0.0235(3) Uani 1 1 d . . . .
O12 O 0.32426(13) 0.9312(2) 0.70370(7) 0.0341(3) Uani 1 1 d . . . .
C13 C 0.54685(17) 0.7923(3) 0.58252(10) 0.0263(4) Uani 1 1 d . . . .
O14 O 0.68140(12) 0.7324(2) 0.58586(7) 0.0345(3) Uani 1 1 d . . . .
C15 C 0.7534(2) 0.8241(4) 0.65360(11) 0.0374(4) Uani 1 1 d . . . .
O16 O 0.71176(12) 0.7344(2) 0.72205(7) 0.0358(3) Uani 1 1 d . . . .
C17 C 0.58016(18) 0.7990(3) 0.72722(10) 0.0305(4) Uani 1 1 d . . . .
H4B H 0.1025(19) 0.881(4) 0.6399(11) 0.032(5) Uiso 1 1 d . . . .
H4A H 0.074(2) 0.608(4) 0.6501(13) 0.046(6) Uiso 1 1 d . . . .
H6B H 0.2950(19) 0.664(3) 0.4845(11) 0.033(5) Uiso 1 1 d . . . .
H6A H 0.279(2) 0.917(4) 0.5131(12) 0.041(6) Uiso 1 1 d . . . .
H7B H 0.215(2) 0.336(4) 0.5638(13) 0.041(6) Uiso 1 1 d . . . .
H7A H 0.2485(18) 0.364(3) 0.6555(12) 0.032(5) Uiso 1 1 d . . . .
H9B H 0.4633(18) 0.391(3) 0.7083(12) 0.033(5) Uiso 1 1 d . . . .
H9A H 0.577(2) 0.390(3) 0.6504(11) 0.033(5) Uiso 1 1 d . . . .
H13B H 0.5048(18) 0.716(3) 0.5345(10) 0.024(5) Uiso 1 1 d . . . .
H13A H 0.5327(17) 0.959(3) 0.5777(10) 0.025(5) Uiso 1 1 d . . . .
H15B H 0.842(2) 0.781(4) 0.6531(13) 0.046(6) Uiso 1 1 d . . . .
H15A H 0.738(2) 0.991(4) 0.6527(13) 0.049(7) Uiso 1 1 d . . . .
H17B H 0.573(2) 0.967(4) 0.7285(12) 0.041(6) Uiso 1 1 d . . . .
H17A H 0.5562(19) 0.734(3) 0.7756(12) 0.032(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
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
O1 C2 O3 119.6(2)
O1 C2 C6 129.3(2)
O3 C2 C6 111.01(16)
C2 O3 C4 109.48(17)
O1' C2' O3' 113.9(8)
O1' C2' C4 131.3(10)
O3' C2' C4 112.3(6)
C2' O3' C6 108.2(5)
O3 C4 C5 107.07(15)
C2' C4 C5 102.4(4)
C11 C5 C4 112.13(13)
C11 C5 C6 113.33(14)
C4 C5 C6 101.66(14)
C11 C5 C7 108.48(14)
C4 C5 C7 110.45(15)
C6 C5 C7 110.70(14)
O3' C6 C5 108.7(5)
C2 C6 C5 103.57(16)
O8 C7 C5 111.64(14)
C7 O8 C9 110.42(13)
O8 C9 C10 111.28(14)
C11 C10 C17 110.55(13)
C11 C10 C9 107.47(14)
C17 C10 C9 110.75(14)
C11 C10 C13 110.83(13)
C17 C10 C13 107.21(14)
C9 C10 C13 110.05(14)
O12 C11 C10 121.93(15)
O12 C11 C5 121.77(15)
C10 C11 C5 116.23(13)
O14 C13 C10 110.19(13)
C15 O14 C13 110.55(14)
O16 C15 O14 111.50(16)
C15 O16 C17 110.24(14)
O16 C17 C10 109.71(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.203(2)
C2 O3 1.358(3)
C2 C6 1.514(3)
O3 C4 1.442(2)
O1' C2' 1.196(6)
C2' O3' 1.363(5)
C2' C4 1.517(6)
O3' C6 1.424(5)
C4 C5 1.537(2)
C5 C11 1.530(2)
C5 C6 1.538(2)
C5 C7 1.539(2)
C7 O8 1.419(2)
O8 C9 1.420(2)
C9 C10 1.537(2)
C10 C11 1.520(2)
C10 C17 1.533(2)
C10 C13 1.541(2)
C11 O12 1.2123(19)
C13 O14 1.427(2)
O14 C15 1.411(2)
C15 O16 1.406(2)
O16 C17 1.424(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
O1 C2 O3 C4 -177.7(2)
C6 C2 O3 C4 3.0(3)
O1' C2' O3' C6 164(3)
C4 C2' O3' C6 0(4)
C2 O3 C4 C5 -19.2(3)
O1' C2' C4 C5 -177(3)
O3' C2' C4 C5 -16(3)
O3 C4 C5 C11 147.91(17)
C2' C4 C5 C11 144.9(14)
O3 C4 C5 C6 26.5(2)
C2' C4 C5 C6 23.5(14)
O3 C4 C5 C7 -91.0(2)
C2' C4 C5 C7 -94.0(14)
C2' O3' C6 C5 17(3)
O1 C2 C6 C5 -165.1(3)
O3 C2 C6 C5 14.1(3)
C11 C5 C6 O3' -146.0(14)
C4 C5 C6 O3' -25.5(14)
C7 C5 C6 O3' 91.9(14)
C11 C5 C6 C2 -144.27(17)
C4 C5 C6 C2 -23.7(2)
C7 C5 C6 C2 93.60(19)
C11 C5 C7 O8 -52.37(18)
C4 C5 C7 O8 -175.64(13)
C6 C5 C7 O8 72.56(19)
C5 C7 O8 C9 64.84(18)
C7 O8 C9 C10 -66.90(18)
O8 C9 C10 C11 55.86(17)
O8 C9 C10 C17 176.71(14)
O8 C9 C10 C13 -64.92(19)
C17 C10 C11 O12 8.7(2)
C9 C10 C11 O12 129.68(17)
C13 C10 C11 O12 -110.03(17)
C17 C10 C11 C5 -168.19(14)
C9 C10 C11 C5 -47.21(17)
C13 C10 C11 C5 73.08(18)
C4 C5 C11 O12 -8.8(2)
C6 C5 C11 O12 105.54(18)
C7 C5 C11 O12 -131.09(16)
C4 C5 C11 C10 168.05(14)
C6 C5 C11 C10 -77.56(18)
C7 C5 C11 C10 45.80(17)
C11 C10 C13 O14 174.46(14)
C17 C10 C13 O14 53.73(18)
C9 C10 C13 O14 -66.80(18)
C10 C13 O14 C15 -57.84(19)
C13 O14 C15 O16 62.7(2)
O14 C15 O16 C17 -63.9(2)
C15 O16 C17 C10 60.3(2)
C11 C10 C17 O16 -175.69(13)
C9 C10 C17 O16 65.31(19)
C13 C10 C17 O16 -54.78(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203479
