#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/66/2216631.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_2216631
loop_
_publ_author_name
'Düpre, Nicole'
'Shen, Wei-Zheng'
'Sanz Miguel, Pablo J.'
'Müller, Jens'
_publ_section_title
3,5-Di-p-toluoyl-1,2-dideoxy-β-1-(imidazol-1-yl)-<small>D</small>-ribofuranose
_journal_coeditor_code           LH2551
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4693
_journal_page_last               o4693
_journal_paper_doi               10.1107/S1600536807056760
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C24 H24 N2 O5'
_chemical_formula_moiety         'C24 H24 N2 O5'
_chemical_formula_sum            'C24 H24 N2 O5'
_chemical_formula_weight         420.45
_chemical_name_systematic
;
3,5-Di-p-toluoyl-1,2-dideoxy-β-1-(imidazol-1-yl)-D-ribofuranose
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 116.25(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.436(3)
_cell_length_b                   5.3850(11)
_cell_length_c                   15.061(3)
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     1050.1(5)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Nonius, 2000)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker--Nonius Kappa CCD'
_diffrn_measurement_method       'profile fitled'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12891
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         N/A
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubes
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.339
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.2112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1726
_reflns_number_total             2647
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2551.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2216631
_cod_database_fobs_code          2216631
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
O O30 0.3603(2) 0.8395(6) 0.96544(19) 0.0222(7) Uani d . 1
N N29 0.1239(2) 1.0452(6) 0.9936(2) 0.0200(8) Uani d . 1
O O28 0.44002(19) 0.7940(6) 1.24729(19) 0.0221(7) Uani d . 1
O O27 0.4201(2) 0.9804(6) 0.8587(2) 0.0259(7) Uani d . 1
C C26 0.5335(3) 0.5234(8) 1.3793(3) 0.0200(9) Uani d . 1
C C25 0.0239(3) 0.8334(9) 0.8628(3) 0.0268(10) Uani d . 1
H H25A -0.0014 0.7064 0.8141 0.032 Uiso calc R 1
C C24 0.6206(3) 0.6745(9) 1.4091(3) 0.0267(11) Uani d . 1
H H24A 0.6179 0.822 1.3734 0.032 Uiso calc R 1
N N23 -0.0292(3) 1.0479(8) 0.8608(3) 0.0303(9) Uani d . 1
C C22 0.1929(3) 0.5296(8) 0.6379(3) 0.0242(10) Uani d . 1
H H22A 0.1737 0.5516 0.5694 0.029 Uiso calc R 1
C C21 0.2101(3) 1.1388(8) 1.0832(3) 0.0205(10) Uani d . 1
H H21A 0.1866 1.2855 1.1085 0.025 Uiso calc R 1
C C20 0.2901(3) 0.6638(8) 0.8066(3) 0.0196(9) Uani d . 1
C C19 0.0339(3) 1.1715(9) 0.9398(3) 0.0249(10) Uani d . 1
H H19A 0.0187 1.3304 0.9575 0.03 Uiso calc R 1
O O18 0.3571(2) 0.4591(6) 1.2656(2) 0.0262(7) Uani d . 1
C C17 0.1172(3) 0.8278(9) 0.9437(3) 0.0256(10) Uani d . 1
H H17A 0.1675 0.6995 0.962 0.031 Uiso calc R 1
C C16 0.7183(3) 0.3957(9) 1.5446(3) 0.0283(12) Uani d . 1
C C15 0.2466(3) 0.4697(8) 0.8370(3) 0.0214(9) Uani d . 1
H H15A 0.2654 0.4478 0.9054 0.026 Uiso calc R 1
C C14 0.5391(3) 0.3097(9) 1.4337(3) 0.0257(10) Uani d . 1
H H14A 0.48 0.2064 1.4147 0.031 Uiso calc R 1
C C13 0.3831(3) 1.0697(8) 1.1102(3) 0.0194(9) Uani d . 1
H H13A 0.4338 1.1726 1.1657 0.023 Uiso calc R 1
C C12 0.4342(3) 0.5834(8) 1.2935(3) 0.0209(10) Uani d . 1
C C11 0.8179(3) 0.3260(12) 1.6335(3) 0.0429(14) Uani d . 1
H H11A 0.8709 0.4508 1.6431 0.064 Uiso calc R 1
H H11B 0.8412 0.1632 1.6223 0.064 Uiso calc R 1
H H11C 0.8059 0.3188 1.6927 0.064 Uiso calc R 1
C C10 0.1487(3) 0.3368(9) 0.6677(3) 0.0245(10) Uani d . 1
C C9 0.1769(3) 0.3097(9) 0.7689(3) 0.0261(10) Uani d . 1
H H9A 0.1477 0.1794 0.7907 0.031 Uiso calc R 1
C C8 0.3638(3) 0.8416(9) 0.8767(3) 0.0220(9) Uani d . 1
C C7 0.3513(3) 0.8494(8) 1.1542(3) 0.0180(9) Uani d . 1
H H7A 0.3321 0.7032 1.1087 0.022 Uiso calc R 1
C C6 0.0724(3) 0.1619(9) 0.5931(3) 0.0337(12) Uani d . 1
H H6A 0.0619 0.2086 0.5265 0.051 Uiso calc R 1
H H6B 0.0064 0.1713 0.5969 0.051 Uiso calc R 1
H H6C 0.0991 -0.0082 0.6075 0.051 Uiso calc R 1
C C5 0.6310(3) 0.2462(9) 1.5159(3) 0.0299(11) Uani d . 1
H H5A 0.634 0.1001 1.5524 0.036 Uiso calc R 1
C C4 0.2640(3) 0.6893(9) 0.7056(3) 0.0266(10) Uani d . 1
H H4A 0.295 0.8159 0.6838 0.032 Uiso calc R 1
C C3 0.4296(3) 1.0075(9) 1.0408(3) 0.0234(10) Uani d . 1
H H3A 0.4392 1.1609 1.0096 0.028 Uiso calc R 1
H H3B 0.4979 0.9279 1.0779 0.028 Uiso calc R 1
C C2 0.7116(3) 0.6093(10) 1.4912(3) 0.0315(12) Uani d . 1
H H2A 0.7703 0.714 1.511 0.038 Uiso calc R 1
C C1 0.2577(3) 0.9476(9) 1.1657(3) 0.0199(9) Uani d . 1
H H1A 0.2082 0.8122 1.1576 0.024 Uiso calc R 1
H H1B 0.2792 1.0256 1.2314 0.024 Uiso calc R 1
O O31 0.2904(2) 1.2143(5) 1.05768(19) 0.0208(7) Uani d . 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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_publ_flag
C8 O30 C3 116.8(3) ?
C19 N29 C17 106.3(3) n
C19 N29 C21 124.9(4) ?
C17 N29 C21 128.7(3) ?
C12 O28 C7 116.1(3) ?
C14 C26 C24 118.9(4) ?
C14 C26 C12 118.3(4) ?
C24 C26 C12 122.7(4) ?
C17 C25 N23 111.0(4) n
C17 C25 H25A 124.5 ?
N23 C25 H25A 124.5 ?
C2 C24 C26 120.0(4) ?
C2 C24 H24A 120 ?
C26 C24 H24A 120 ?
C19 N23 C25 104.4(4) n
C4 C22 C10 121.5(4) ?
C4 C22 H22A 119.2 ?
C10 C22 H22A 119.2 ?
O31 C21 N29 108.0(3) ?
O31 C21 C1 106.5(3) ?
N29 C21 C1 114.4(4) ?
O31 C21 H21A 109.3 ?
N29 C21 H21A 109.3 ?
C1 C21 H21A 109.3 ?
C15 C20 C4 119.0(4) ?
C15 C20 C8 122.6(4) ?
C4 C20 C8 118.4(4) ?
N23 C19 N29 112.3(4) n
N23 C19 H19A 123.8 ?
N29 C19 H19A 123.8 ?
C25 C17 N29 105.9(4) n
C25 C17 H17A 127.1 ?
N29 C17 H17A 127.1 ?
C2 C16 C5 118.6(4) ?
C2 C16 C11 121.0(5) ?
C5 C16 C11 120.3(4) ?
C9 C15 C20 120.7(4) ?
C9 C15 H15A 119.6 ?
C20 C15 H15A 119.6 ?
C26 C14 C5 120.4(4) ?
C26 C14 H14A 119.8 ?
C5 C14 H14A 119.8 ?
O31 C13 C3 109.2(3) ?
O31 C13 C7 105.8(3) ?
C3 C13 C7 116.1(4) ?
O31 C13 H13A 108.5 ?
C3 C13 H13A 108.5 ?
C7 C13 H13A 108.5 ?
O18 C12 O28 123.0(4) ?
O18 C12 C26 124.9(4) ?
O28 C12 C26 112.1(4) ?
C16 C11 H11A 109.5 ?
C16 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C16 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C22 C10 C9 118.3(4) ?
C22 C10 C6 121.0(4) ?
C9 C10 C6 120.7(4) ?
C15 C9 C10 120.7(4) ?
C15 C9 H9A 119.6 ?
C10 C9 H9A 119.6 ?
O27 C8 O30 122.8(4) ?
O27 C8 C20 125.5(4) ?
O30 C8 C20 111.7(4) ?
O28 C7 C13 105.9(3) ?
O28 C7 C1 114.1(3) ?
C13 C7 C1 103.3(3) ?
O28 C7 H7A 111 ?
C13 C7 H7A 111 ?
C1 C7 H7A 111 ?
C10 C6 H6A 109.5 ?
C10 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C10 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
C16 C5 C14 120.5(4) ?
C16 C5 H5A 119.8 ?
C14 C5 H5A 119.8 ?
C22 C4 C20 119.7(4) ?
C22 C4 H4A 120.2 ?
C20 C4 H4A 120.2 ?
O30 C3 C13 108.4(3) ?
O30 C3 H3A 110 ?
C13 C3 H3A 110 ?
O30 C3 H3B 110 ?
C13 C3 H3B 110 ?
H3A C3 H3B 108.4 ?
C16 C2 C24 121.5(5) ?
C16 C2 H2A 119.2 ?
C24 C2 H2A 119.2 ?
C21 C1 C7 104.1(3) ?
C21 C1 H1A 110.9 ?
C7 C1 H1A 110.9 ?
C21 C1 H1B 110.9 ?
C7 C1 H1B 110.9 ?
H1A C1 H1B 109 ?
C21 O31 C13 111.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O30 C8 1.360(5) ?
O30 C3 1.450(5) ?
N29 C19 1.370(5) n
N29 C17 1.371(6) n
N29 C21 1.462(5) n
O28 C12 1.352(5) ?
O28 C7 1.451(4) ?
O27 C8 1.220(5) ?
C26 C14 1.394(6) ?
C26 C24 1.395(6) ?
C26 C12 1.480(5) ?
C25 C17 1.360(6) n
C25 N23 1.379(6) n
C25 H25A 0.95 ?
C24 C2 1.393(6) ?
C24 H24A 0.95 ?
N23 C19 1.315(6) n
C22 C4 1.381(6) ?
C22 C10 1.393(6) ?
C22 H22A 0.95 ?
C21 O31 1.432(5) n
C21 C1 1.523(6) n
C21 H21A 1 ?
C20 C15 1.396(6) ?
C20 C4 1.404(5) ?
C20 C8 1.473(6) ?
C19 H19A 0.95 ?
O18 C12 1.205(5) ?
C17 H17A 0.95 ?
C16 C2 1.382(6) ?
C16 C5 1.393(7) ?
C16 C11 1.516(6) ?
C15 C9 1.377(6) ?
C15 H15A 0.95 ?
C14 C5 1.400(6) ?
C14 H14A 0.95 ?
C13 O31 1.445(5) n
C13 C3 1.509(5) ?
C13 C7 1.525(6) n
C13 H13A 1 ?
C11 H11A 0.98 ?
C11 H11B 0.98 ?
C11 H11C 0.98 ?
C10 C9 1.400(6) ?
C10 C6 1.506(6) ?
C9 H9A 0.95 ?
C7 C1 1.530(6) n
C7 H7A 1 ?
C6 H6A 0.98 ?
C6 H6B 0.98 ?
C6 H6C 0.98 ?
C5 H5A 0.95 ?
C4 H4A 0.95 ?
C3 H3A 0.99 ?
C3 H3B 0.99 ?
C2 H2A 0.95 ?
C1 H1A 0.99 ?
C1 H1B 0.99 ?
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_publ_flag
C12 O28 C7 C1 75.4(5) ?
C12 O28 C7 C13 -171.7(3) ?
C7 O28 C12 O18 -7.0(6) ?
C7 O28 C12 C26 171.5(3) ?
C8 O30 C3 C13 153.6(4) ?
C3 O30 C8 O27 -1.7(6) ?
C3 O30 C8 C20 180.0(4) ?
C21 O31 C13 C3 139.0(4) ?
C21 O31 C13 C7 13.4(4) n
C13 O31 C21 N29 -117.7(3) ?
C13 O31 C21 C1 5.6(4) n
C19 N23 C25 C17 1.3(5) ?
C25 N23 C19 N29 -1.3(5) ?
C19 N29 C17 C25 0.0(5) ?
C19 N29 C21 O31 -104.2(4) n
C19 N29 C21 C1 137.4(4) ?
C21 N29 C19 N23 177.9(4) ?
C21 N29 C17 C25 -176.9(4) ?
C17 N29 C19 N23 0.9(5) ?
C17 N29 C21 O31 72.1(5) ?
C17 N29 C21 C1 -46.3(6) ?
C21 C1 C7 C13 29.4(4) n
C7 C1 C21 O31 -22.1(4) n
C21 C1 C7 O28 143.8(4) ?
C7 C1 C21 N29 97.1(4) ?
C16 C2 C24 C26 0.2(7) ?
C24 C2 C16 C11 179.7(4) ?
C24 C2 C16 C5 -1.1(7) ?
O30 C3 C13 O31 -67.2(4) ?
O30 C3 C13 C7 52.4(5) n
C22 C4 C20 C8 -178.2(4) ?
C22 C4 C20 C15 2.7(7) ?
C20 C4 C22 C10 -2.3(7) ?
C14 C5 C16 C2 1.0(7) ?
C14 C5 C16 C11 -179.8(4) ?
C16 C5 C14 C26 0.0(7) ?
O28 C7 C13 O31 -146.7(3) ?
O28 C7 C13 C3 92.0(4) ?
C1 C7 C13 O31 -26.5(4) n
C1 C7 C13 C3 -147.8(4) ?
O30 C8 C20 C15 -17.9(6) ?
O27 C8 C20 C15 163.9(5) ?
O30 C8 C20 C4 163.0(4) ?
O27 C8 C20 C4 -15.2(7) ?
C15 C9 C10 C6 -180.0(4) ?
C10 C9 C15 C20 0.5(7) ?
C15 C9 C10 C22 0.0(7) ?
C6 C10 C22 C4 -179.1(4) ?
C9 C10 C22 C4 1.0(7) ?
O18 C12 C26 C24 -179.6(4) ?
O28 C12 C26 C14 -179.6(4) ?
O18 C12 C26 C14 -1.1(7) ?
O28 C12 C26 C24 1.9(6) ?
C5 C14 C26 C12 -179.5(4) ?
C5 C14 C26 C24 -0.9(7) ?
C9 C15 C20 C8 179.1(4) ?
C9 C15 C20 C4 -1.8(7) ?
N29 C17 C25 N23 -0.8(5) ?
C2 C24 C26 C14 0.8(7) ?
C2 C24 C26 C12 179.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196330
2 PubChem 139073754
