#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133655.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_7133655
loop_
_publ_author_name
'Kumar, Manoj'
'Singh, Shubham'
'Subramanian, Parthasarathi'
_publ_section_title
;
 Synthesis of dispiro-orthoester via an acetal oxo-carbenium ion.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12860
_journal_page_last               12863
_journal_paper_doi               10.1039/d4cc03031a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13 H14 O4'
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_chemical_name_systematic        Manoj
_chemical_properties_physical    'Heat-sensitive,Acid senstive'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-12 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6135(4)
_cell_length_b                   5.8166(2)
_cell_length_c                   16.6086(5)
_cell_measurement_reflns_used    8183
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.18
_cell_volume                     1121.20(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14371
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.177
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.8742.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_preparation       Acetone
_exptl_crystal_recrystallization_method 'Slow evporation'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0378
_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)+(0.0455P)²+0.6729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1790
_reflns_number_total             2065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03031a2.cif
_cod_data_source_block           10feba_o_0m
_cod_depositor_comments
;
Adding full bibliography for 7133655--7133659.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C26 H28 O8'
_cod_original_formula_weight         468.48
_cod_original_formula_moiety         '2(C13 H14 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               7133655
_shelx_shelxl_version_number     2018/3
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00B(H00D,H00E), C00C(H00F,H00G), C00D(H00H,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C00A(H00C), C00E(H00J), C00G(H00K), C00H(H00L)
;
_olex2_exptl_crystal_mounting_method 'Low temprature '
_olex2_submission_original_sample_id 'Manoj 6-5-7'
_olex2_submission_special_instructions 'No special instructions were received'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.34341(9) 0.53840(18) 0.36357(6) 0.0180(3) Uani 1 1 d . . . . .
O002 O 0.28235(8) 0.17831(17) 0.40215(6) 0.0174(3) Uani 1 1 d . . . . .
O003 O 0.46923(8) 0.25066(19) 0.40674(6) 0.0189(3) Uani 1 1 d . . . . .
O004 O 0.90596(10) 0.0625(3) 0.35666(8) 0.0373(4) Uani 1 1 d . . . . .
C005 C 0.61332(13) -0.0418(3) 0.40143(9) 0.0190(3) Uani 1 1 d . . . . .
H005 H 0.569943 -0.142695 0.431439 0.023 Uiso 1 1 calc R U . . .
C006 C 0.36549(12) 0.3033(3) 0.36202(9) 0.0161(3) Uani 1 1 d . . . . .
C007 C 0.47643(13) 0.0463(3) 0.28506(9) 0.0191(3) Uani 1 1 d . . . . .
H00A H 0.519604 0.030935 0.236429 0.023 Uiso 1 1 calc R U . . .
H00B H 0.444261 -0.101825 0.298869 0.023 Uiso 1 1 calc R U . . .
C008 C 0.72704(13) -0.0702(3) 0.40152(9) 0.0225(4) Uani 1 1 d . . . . .
H008 H 0.759798 -0.196521 0.427904 0.027 Uiso 1 1 calc R U . . .
C009 C 0.55223(12) 0.1450(3) 0.35529(9) 0.0167(3) Uani 1 1 d . . . . .
C00A C 0.18532(13) 0.6048(3) 0.45289(9) 0.0220(4) Uani 1 1 d . . . . .
H00C H 0.149902 0.717751 0.482929 0.026 Uiso 1 1 calc R U . . .
C00B C 0.31236(13) 0.6264(3) 0.44102(9) 0.0203(3) Uani 1 1 d . . . . .
H00D H 0.334524 0.786901 0.445191 0.024 Uiso 1 1 calc R U . . .
H00E H 0.354120 0.542434 0.483229 0.024 Uiso 1 1 calc R U . . .
C00C C 0.38300(13) 0.2288(3) 0.27546(9) 0.0198(3) Uani 1 1 d . . . . .
H00F H 0.408334 0.356366 0.242903 0.024 Uiso 1 1 calc R U . . .
H00G H 0.312790 0.165078 0.251203 0.024 Uiso 1 1 calc R U . . .
C00D C 0.16496(13) 0.2315(3) 0.37946(9) 0.0204(3) Uani 1 1 d . . . . .
H00H H 0.117007 0.099333 0.390350 0.024 Uiso 1 1 calc R U . . .
H00I H 0.159330 0.261236 0.321989 0.024 Uiso 1 1 calc R U . . .
C00E C 0.12038(13) 0.4355(3) 0.42343(9) 0.0225(4) Uani 1 1 d . . . . .
H00J H 0.041433 0.444037 0.430566 0.027 Uiso 1 1 calc R U . . .
C00F C 0.80196(13) 0.0928(3) 0.36104(9) 0.0245(4) Uani 1 1 d . . . . .
C00G C 0.63239(13) 0.3259(3) 0.32590(9) 0.0218(4) Uani 1 1 d . . . . .
H00K H 0.601146 0.462392 0.305753 0.026 Uiso 1 1 calc R U . . .
C00H C 0.74609(14) 0.3001(3) 0.32735(10) 0.0264(4) Uani 1 1 d . . . . .
H00L H 0.791479 0.415990 0.306528 0.032 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 O001 C00B 114.68(11) . . ?
C006 O002 C00D 115.40(11) . . ?
C006 O003 C009 110.60(10) . . ?
C008 C005 H005 118.5 . . ?
C008 C005 C009 122.94(14) . . ?
C009 C005 H005 118.5 . . ?
O001 C006 O002 111.81(12) . . ?
O001 C006 O003 110.75(12) . . ?
O001 C006 C00C 109.17(12) . . ?
O002 C006 O003 103.01(11) . . ?
O002 C006 C00C 114.87(12) . . ?
O003 C006 C00C 106.96(11) . . ?
H00A C007 H00B 109.3 . . ?
C009 C007 H00A 111.4 . . ?
C009 C007 H00B 111.4 . . ?
C00C C007 H00A 111.4 . . ?
C00C C007 H00B 111.4 . . ?
C00C C007 C009 101.79(12) . . ?
C005 C008 H008 119.2 . . ?
C005 C008 C00F 121.62(15) . . ?
C00F C008 H008 119.2 . . ?
O003 C009 C005 108.65(12) . . ?
O003 C009 C007 103.28(11) . . ?
O003 C009 C00G 109.20(12) . . ?
C005 C009 C007 111.34(13) . . ?
C005 C009 C00G 112.87(12) . . ?
C00G C009 C007 111.01(12) . . ?
C00B C00A H00C 117.8 . . ?
C00E C00A H00C 117.8 . . ?
C00E C00A C00B 124.33(14) . . ?
O001 C00B C00A 111.46(12) . . ?
O001 C00B H00D 109.3 . . ?
O001 C00B H00E 109.3 . . ?
C00A C00B H00D 109.3 . . ?
C00A C00B H00E 109.3 . . ?
H00D C00B H00E 108.0 . . ?
C006 C00C C007 102.63(12) . . ?
C006 C00C H00F 111.2 . . ?
C006 C00C H00G 111.2 . . ?
C007 C00C H00F 111.2 . . ?
C007 C00C H00G 111.2 . . ?
H00F C00C H00G 109.2 . . ?
O002 C00D H00H 109.1 . . ?
O002 C00D H00I 109.1 . . ?
O002 C00D C00E 112.65(12) . . ?
H00H C00D H00I 107.8 . . ?
C00E C00D H00H 109.1 . . ?
C00E C00D H00I 109.1 . . ?
C00A C00E C00D 124.62(14) . . ?
C00A C00E H00J 117.7 . . ?
C00D C00E H00J 117.7 . . ?
O004 C00F C008 122.44(17) . . ?
O004 C00F C00H 121.20(16) . . ?
C008 C00F C00H 116.35(13) . . ?
C009 C00G H00K 118.5 . . ?
C00H C00G C009 122.93(15) . . ?
C00H C00G H00K 118.5 . . ?
C00F C00H H00L 119.2 . . ?
C00G C00H C00F 121.63(15) . . ?
C00G C00H H00L 119.2 . . ?
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
O001 C006 1.3915(18) . ?
O001 C00B 1.4423(18) . ?
O002 C006 1.3971(18) . ?
O002 C00D 1.4350(17) . ?
O003 C006 1.4257(17) . ?
O003 C009 1.4478(17) . ?
O004 C00F 1.2254(19) . ?
C005 H005 0.9300 . ?
C005 C008 1.331(2) . ?
C005 C009 1.494(2) . ?
C006 C00C 1.522(2) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C009 1.546(2) . ?
C007 C00C 1.522(2) . ?
C008 H008 0.9300 . ?
C008 C00F 1.466(2) . ?
C009 C00G 1.498(2) . ?
C00A H00C 0.9300 . ?
C00A C00B 1.501(2) . ?
C00A C00E 1.323(2) . ?
C00B H00D 0.9700 . ?
C00B H00E 0.9700 . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00D H00H 0.9700 . ?
C00D H00I 0.9700 . ?
C00D C00E 1.496(2) . ?
C00E H00J 0.9300 . ?
C00F C00H 1.470(3) . ?
C00G H00K 0.9300 . ?
C00G C00H 1.328(2) . ?
C00H H00L 0.9300 . ?
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
O001 C006 C00C C007 143.67(12) . . . . ?
O002 C006 C00C C007 -89.84(14) . . . . ?
O002 C00D C00E C00A 26.6(2) . . . . ?
O003 C006 C00C C007 23.80(15) . . . . ?
O003 C009 C00G C00H 133.05(15) . . . . ?
O004 C00F C00H C00G 174.41(16) . . . . ?
C005 C008 C00F O004 -175.79(15) . . . . ?
C005 C008 C00F C00H 5.7(2) . . . . ?
C005 C009 C00G C00H 12.1(2) . . . . ?
C006 O001 C00B C00A -86.59(15) . . . . ?
C006 O002 C00D C00E -83.95(15) . . . . ?
C006 O003 C009 C005 -140.85(12) . . . . ?
C006 O003 C009 C007 -22.54(15) . . . . ?
C006 O003 C009 C00G 95.65(14) . . . . ?
C007 C009 C00G C00H -113.73(17) . . . . ?
C008 C005 C009 O003 -134.75(15) . . . . ?
C008 C005 C009 C007 112.15(16) . . . . ?
C008 C005 C009 C00G -13.5(2) . . . . ?
C008 C00F C00H C00G -7.1(2) . . . . ?
C009 O003 C006 O001 -119.45(13) . . . . ?
C009 O003 C006 O002 120.86(12) . . . . ?
C009 O003 C006 C00C -0.60(16) . . . . ?
C009 C005 C008 C00F 5.0(2) . . . . ?
C009 C007 C00C C006 -36.17(14) . . . . ?
C009 C00G C00H C00F -2.3(2) . . . . ?
C00B O001 C006 O002 45.12(15) . . . . ?
C00B O001 C006 O003 -69.14(15) . . . . ?
C00B O001 C006 C00C 173.34(11) . . . . ?
C00B C00A C00E C00D 5.0(3) . . . . ?
C00C C007 C009 O003 36.25(14) . . . . ?
C00C C007 C009 C005 152.67(12) . . . . ?
C00C C007 C009 C00G -80.67(14) . . . . ?
C00D O002 C006 O001 49.90(16) . . . . ?
C00D O002 C006 O003 168.86(11) . . . . ?
C00D O002 C006 C00C -75.22(16) . . . . ?
C00E C00A C00B O001 33.3(2) . . . . ?
