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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/71/7107169.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_7107169
loop_
_publ_author_name
'Amol M. Vibhute'
'Rajesh G. Gonnade'
'R. S. Swathi'
'Kana M. Sureshan'
_publ_section_title
;
 Strength from weakness: opportunistic CH - O hydrogen bonds
 differentially dictate the conformational fate in solid and solution
 states
;
_journal_name_full               Chem.Commun.
_journal_page_first              717
_journal_paper_doi               10.1039/c1cc15051k
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C19 H24 O7'
_chemical_formula_sum            'C19 H24 O7'
_chemical_formula_weight         364.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.937(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.438(2)
_cell_length_b                   8.4112(9)
_cell_length_c                   10.6083(11)
_cell_measurement_reflns_used    3907
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.63
_cell_volume                     1762.0(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8369
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.03
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker sadabs'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.9898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2726
_reflns_number_total             3102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15051k.txt
_cod_data_source_block           kmsb104
_cod_original_cell_volume        1762.1(3)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7107169
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.15572(7) 0.69501(17) -0.10375(14) 0.0161(4) Uani 1 1 d .
O2 O 0.26052(7) 0.67166(17) 0.04240(14) 0.0158(4) Uani 1 1 d .
O3 O 0.35553(7) 0.41487(18) 0.07718(14) 0.0171(4) Uani 1 1 d .
O4 O 0.28802(8) 0.17980(18) 0.18546(15) 0.0198(4) Uani 1 1 d .
H4 H 0.3199 0.1964 0.2490 0.030 Uiso 1 1 calc R
O5 O 0.14233(7) 0.25983(18) 0.16638(14) 0.0188(4) Uani 1 1 d .
O6 O 0.07929(7) 0.42378(18) 0.00478(14) 0.0173(4) Uani 1 1 d .
O7 O 0.37886(8) 0.2496(2) -0.07276(15) 0.0246(4) Uani 1 1 d .
C1 C 0.17207(10) 0.5301(3) -0.0835(2) 0.0147(5) Uani 1 1 d .
H1 H 0.1551 0.4679 -0.1634 0.018 Uiso 1 1 calc R
C2 C 0.24972(11) 0.5358(3) -0.0428(2) 0.0160(5) Uani 1 1 d .
H2 H 0.2669 0.5579 -0.1191 0.019 Uiso 1 1 calc R
C3 C 0.28385(10) 0.3875(3) 0.0270(2) 0.0153(5) Uani 1 1 d .
H3 H 0.2782 0.3024 -0.0380 0.018 Uiso 1 1 calc R
C4 C 0.25642(11) 0.3265(3) 0.1386(2) 0.0160(5) Uani 1 1 d .
H4A H 0.2642 0.4049 0.2092 0.019 Uiso 1 1 calc R
C5 C 0.18158(10) 0.3050(3) 0.0790(2) 0.0155(5) Uani 1 1 d .
H5 H 0.1744 0.2287 0.0070 0.019 Uiso 1 1 calc R
C6 C 0.14907(10) 0.4620(3) 0.0294(2) 0.0150(5) Uani 1 1 d .
H6 H 0.1601 0.5387 0.1013 0.018 Uiso 1 1 calc R
C7 C 0.39780(11) 0.3323(3) 0.0237(2) 0.0175(5) Uani 1 1 d .
C8 C 0.46982(11) 0.3502(3) 0.0961(2) 0.0170(5) Uani 1 1 d .
C9 C 0.49053(11) 0.4386(3) 0.2103(2) 0.0222(5) Uani 1 1 d .
H9 H 0.4587 0.4924 0.2431 0.027 Uiso 1 1 calc R
C10 C 0.55842(11) 0.4464(3) 0.2750(2) 0.0248(6) Uani 1 1 d .
H10 H 0.5723 0.5061 0.3511 0.030 Uiso 1 1 calc R
C11 C 0.60587(12) 0.3655(3) 0.2267(2) 0.0266(6) Uani 1 1 d .
H11 H 0.6514 0.3693 0.2715 0.032 Uiso 1 1 calc R
C12 C 0.58571(12) 0.2793(3) 0.1123(3) 0.0288(6) Uani 1 1 d .
H12 H 0.6177 0.2264 0.0793 0.035 Uiso 1 1 calc R
C13 C 0.51788(11) 0.2719(3) 0.0473(2) 0.0247(6) Uani 1 1 d .
H13 H 0.5043 0.2140 -0.0298 0.030 Uiso 1 1 calc R
C14 C 0.07457(11) 0.3255(3) 0.1134(2) 0.0186(5) Uani 1 1 d .
C15 C 0.02451(12) 0.1949(3) 0.0629(2) 0.0246(6) Uani 1 1 d .
H15A H -0.0187 0.2405 0.0209 0.037 Uiso 1 1 calc R
H15B H 0.0201 0.1293 0.1343 0.037 Uiso 1 1 calc R
H15C H 0.0401 0.1315 0.0013 0.037 Uiso 1 1 calc R
C16 C 0.05646(12) 0.4236(3) 0.2185(2) 0.0250(6) Uani 1 1 d .
H16A H 0.0865 0.5130 0.2392 0.037 Uiso 1 1 calc R
H16B H 0.0607 0.3596 0.2951 0.037 Uiso 1 1 calc R
H16C H 0.0107 0.4607 0.1881 0.037 Uiso 1 1 calc R
C17 C 0.20959(10) 0.7859(3) -0.0186(2) 0.0167(5) Uani 1 1 d .
C18 C 0.23809(11) 0.9006(3) -0.1006(2) 0.0192(5) Uani 1 1 d .
H18A H 0.2749 0.9588 -0.0455 0.029 Uiso 1 1 calc R
H18B H 0.2033 0.9733 -0.1438 0.029 Uiso 1 1 calc R
H18C H 0.2541 0.8424 -0.1645 0.029 Uiso 1 1 calc R
C19 C 0.18354(11) 0.8701(3) 0.0845(2) 0.0191(5) Uani 1 1 d .
H19A H 0.1684 0.7929 0.1373 0.029 Uiso 1 1 calc R
H19B H 0.1465 0.9381 0.0432 0.029 Uiso 1 1 calc R
H19C H 0.2192 0.9327 0.1384 0.029 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
C1 O1 C17 107.92(15)
C2 O2 C17 105.73(15)
C7 O3 C3 117.66(16)
C4 O4 H4 109.5
C5 O5 C14 106.59(15)
C6 O6 C14 104.71(15)
O1 C1 C6 112.27(17)
O1 C1 C2 101.32(16)
C6 C1 C2 107.45(17)
O1 C1 H1 111.8
C6 C1 H1 111.8
C2 C1 H1 111.8
O2 C2 C3 111.61(16)
O2 C2 C1 100.50(16)
C3 C2 C1 114.94(18)
O2 C2 H2 109.8
C3 C2 H2 109.8
C1 C2 H2 109.8
O3 C3 C4 107.99(16)
O3 C3 C2 110.06(17)
C4 C3 C2 116.03(17)
O3 C3 H3 107.5
C4 C3 H3 107.5
C2 C3 H3 107.5
O4 C4 C5 111.30(17)
O4 C4 C3 109.84(17)
C5 C4 C3 104.58(17)
O4 C4 H4A 110.3
C5 C4 H4A 110.3
C3 C4 H4A 110.3
O5 C5 C4 116.11(17)
O5 C5 C6 100.90(16)
C4 C5 C6 110.42(18)
O5 C5 H5 109.7
C4 C5 H5 109.7
C6 C5 H5 109.7
O6 C6 C1 116.36(17)
O6 C6 C5 101.35(16)
C1 C6 C5 114.18(17)
O6 C6 H6 108.2
C1 C6 H6 108.2
C5 C6 H6 108.2
O7 C7 O3 123.5(2)
O7 C7 C8 123.6(2)
O3 C7 C8 112.92(18)
C13 C8 C9 119.5(2)
C13 C8 C7 117.5(2)
C9 C8 C7 123.0(2)
C10 C9 C8 119.9(2)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 120.1(2)
C9 C10 H10 119.9
C11 C10 H10 119.9
C12 C11 C10 120.2(2)
C12 C11 H11 119.9
C10 C11 H11 119.9
C13 C12 C11 119.7(2)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C8 120.5(2)
C12 C13 H13 119.8
C8 C13 H13 119.8
O6 C14 O5 105.78(16)
O6 C14 C15 108.29(18)
O5 C14 C15 110.57(19)
O6 C14 C16 110.91(19)
O5 C14 C16 108.15(18)
C15 C14 C16 112.91(19)
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
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O2 C17 O1 105.84(16)
O2 C17 C19 109.61(17)
O1 C17 C19 110.21(17)
O2 C17 C18 110.05(17)
O1 C17 C18 108.78(17)
C19 C17 C18 112.16(19)
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
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.430(3)
O1 C17 1.449(3)
O2 C2 1.438(3)
O2 C17 1.442(3)
O3 C7 1.343(3)
O3 C3 1.442(2)
O4 C4 1.422(3)
O4 H4 0.8200
O5 C5 1.425(3)
O5 C14 1.462(3)
O6 C6 1.419(2)
O6 C14 1.441(3)
O7 C7 1.215(3)
C1 C6 1.508(3)
C1 C2 1.534(3)
C1 H1 0.9800
C2 C3 1.524(3)
C2 H2 0.9800
C3 C4 1.524(3)
C3 H3 0.9800
C4 C5 1.508(3)
C4 H4A 0.9800
C5 C6 1.511(3)
C5 H5 0.9800
C6 H6 0.9800
C7 C8 1.482(3)
C8 C13 1.389(3)
C8 C9 1.391(3)
C9 C10 1.382(3)
C9 H9 0.9300
C10 C11 1.386(3)
C10 H10 0.9300
C11 C12 1.383(4)
C11 H11 0.9300
C12 C13 1.382(3)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.503(3)
C14 C16 1.507(3)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 C19 1.510(3)
C17 C18 1.512(3)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182250
