#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/28/2202893.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_2202893
loop_
_publ_author_name
'Angela Celli'
'Donato Donati'
'Fabio Ponticelli'
_publ_section_title
1-[(2RS,3RS)-4-Acetyl-2-hydroxy-3-(5-methoxy-4-methyl-3-phenylpyrazol-1-ylamino)-2,5-dimethyl-2,3-dihydrofuran-3-yl]ethanone
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1170
_journal_page_last               o1172
_journal_paper_doi               10.1107/S1600536803015514
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C21 H25 N3 O5'
_chemical_formula_moiety         'C21 H25 N3 O5'
_chemical_formula_sum            'C21 H25 N3 O5'
_chemical_formula_weight         399.44
_chemical_melting_point          387
_chemical_name_systematic
;
1-[(2RS,3RS)-4-Acetyl-2-hydroxy-3-(5-methoxy-4-methyl-3-phenylpyrazol-1-
ylamino)-2,5-dimethyl-2,3-dihydro-furan-3-yl]ethanone
;
_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'
_cell_angle_alpha                90
_cell_angle_beta                 97.610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.339(3)
_cell_length_b                   7.444(2)
_cell_length_c                   24.546(4)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38
_cell_measurement_theta_min      4
_cell_volume                     2053.6(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4895
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_gt           0.056
_refine_ls_shift/su_max          0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.059P)²+0.0883P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                1988
_reflns_number_total             3612
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6034.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202893
_cod_database_fobs_code          2202893
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O4 0.95159(19) 0.0998(3) 0.67593(9) 0.0407(6) Uani d . 1 . . O
H4 0.8988 0.1048 0.6957 0.072(14) Uiso calc R 1 . . H
O1 0.94465(17) -0.2075(3) 0.68887(7) 0.0401(5) Uani d . 1 . . O
O5 0.47868(18) -0.0204(3) 0.62516(8) 0.0468(6) Uani d . 1 . . O
N2 0.6771(2) 0.0180(3) 0.66575(9) 0.0339(6) Uani d . 1 . . N
N1 0.7265(2) 0.0365(3) 0.61673(9) 0.0347(6) Uani d . 1 . . N
H1 0.7483 0.1629 0.6132 0.040(8) Uiso d R 1 . . H
O2 0.6968(2) -0.5574(3) 0.60277(11) 0.0742(8) Uani d . 1 . . O
O3 0.8716(2) -0.1866(4) 0.52146(9) 0.0673(8) Uani d . 1 . . O
N3 0.7434(2) 0.0313(3) 0.71573(9) 0.0361(6) Uani d . 1 . . N
C12 0.5472(3) 0.0030(4) 0.72479(12) 0.0356(7) Uani d . 1 . . C
C3 0.7924(3) -0.2816(4) 0.62245(11) 0.0334(7) Uani d . 1 . . C
C10 1.0562(3) -0.0852(5) 0.62198(13) 0.0497(9) Uani d . 1 . . C
H10C 1.0634 0.0129 0.5973 0.06 Uiso calc R 1 . . H
H10A 1.0519 -0.1962 0.6019 0.06 Uiso calc R 1 . . H
H10B 1.1241 -0.0871 0.6498 0.06 Uiso calc R 1 . . H
C14 0.7106(3) 0.0130(4) 0.81087(12) 0.0361(7) Uani d . 1 . . C
C13 0.6651(3) 0.0187(4) 0.75161(11) 0.0347(7) Uani d . 1 . . C
C18 0.8617(3) -0.0828(5) 0.88322(14) 0.0532(9) Uani d . 1 . . C
H18 0.9332 -0.1418 0.8943 0.056(10) Uiso calc R 1 . . H
C11 0.5601(3) 0.0020(4) 0.66994(12) 0.0354(7) Uani d . 1 . . C
C1 0.9451(3) -0.0619(4) 0.64851(11) 0.0355(7) Uani d . 1 . . C
C5 0.8627(3) -0.4933(4) 0.70387(13) 0.0499(9) Uani d . 1 . . C
H5A 0.7876 -0.5536 0.6959 0.06 Uiso calc R 1 . . H
H5B 0.8754 -0.4598 0.742 0.06 Uiso calc R 1 . . H
H5C 0.9253 -0.5723 0.6961 0.06 Uiso calc R 1 . . H
C2 0.8231(3) -0.0914(4) 0.60870(11) 0.0332(7) Uani d . 1 . . C
C8 0.8461(3) -0.0624(5) 0.54888(12) 0.0447(8) Uani d . 1 . . C
C4 0.8626(3) -0.3300(4) 0.66929(12) 0.0368(7) Uani d . 1 . . C
C20 0.4324(3) -0.0105(5) 0.74858(13) 0.0502(9) Uani d . 1 . . C
H20A 0.407 0.1075 0.7578 0.06 Uiso calc R 1 . . H
H20B 0.4438 -0.0834 0.7811 0.06 Uiso calc R 1 . . H
H20C 0.3728 -0.0641 0.7221 0.06 Uiso calc R 1 . . H
C16 0.6967(3) 0.0869(5) 0.90518(13) 0.0542(10) Uani d . 1 . . C
H16 0.6564 0.1428 0.9311 0.040(9) Uiso calc R 1 . . H
C19 0.8167(3) -0.0757(5) 0.82813(13) 0.0472(9) Uani d . 1 . . C
H23 0.8579 -0.1308 0.8024 0.070(12) Uiso calc R 1 . . H
C15 0.6509(3) 0.0950(4) 0.85003(12) 0.0453(9) Uani d . 1 . . C
H15 0.5799 0.1554 0.8392 0.053(10) Uiso calc R 1 . . H
C17 0.8009(3) -0.0025(5) 0.92185(14) 0.0547(9) Uani d . 1 . . C
H17 0.8304 -0.0091 0.959 0.049(9) Uiso calc R 1 . . H
C9 0.8402(4) 0.1253(5) 0.52642(14) 0.0733(13) Uani d . 1 . . C
H9A 0.8815 0.1306 0.4948 0.088 Uiso calc R 1 . . H
H9B 0.8767 0.2065 0.554 0.088 Uiso calc R 1 . . H
H9C 0.7585 0.1587 0.5161 0.088 Uiso calc R 1 . . H
C6 0.7027(3) -0.3966(4) 0.59270(13) 0.0447(8) Uani d . 1 . . C
C7 0.6170(3) -0.3197(5) 0.54709(13) 0.0583(10) Uani d . 1 . . C
H7A 0.5477 -0.3949 0.5409 0.07 Uiso calc R 1 . . H
H7B 0.6541 -0.3138 0.5142 0.07 Uiso calc R 1 . . H
H7C 0.5941 -0.2012 0.557 0.07 Uiso calc R 1 . . H
C21 0.4265(4) 0.1398(6) 0.60220(17) 0.0945(16) Uani d . 1 . . C
H21A 0.3877 0.2015 0.6292 0.113 Uiso calc R 1 . . H
H21B 0.3692 0.1111 0.571 0.113 Uiso calc R 1 . . H
H21C 0.4872 0.2155 0.5907 0.113 Uiso calc R 1 . . H
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
C1 O4 H4 109.5 ?
C4 O1 C1 108.9(2) yes
C11 O5 C21 115.2(3) ?
C11 N2 N3 111.8(2) ?
C11 N2 N1 125.7(2) ?
N3 N2 N1 122.2(2) yes
N2 N1 C2 116.0(2) yes
N2 N1 H1 107.7 ?
C2 N1 H1 114 ?
C13 N3 N2 104.8(2) yes
C11 C12 C13 103.9(2) ?
C11 C12 C20 126.3(3) ?
C13 C12 C20 129.8(3) ?
C4 C3 C6 124.3(3) ?
C4 C3 C2 108.1(3) yes
C6 C3 C2 127.6(3) ?
C1 C10 H10C 109.5 ?
C1 C10 H10A 109.5 ?
H10C C10 H10A 109.5 ?
C1 C10 H10B 109.5 ?
H10C C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C19 C14 C15 118.7(3) ?
C19 C14 C13 119.3(3) ?
C15 C14 C13 122.0(3) ?
N3 C13 C12 111.7(2) yes
N3 C13 C14 118.4(3) ?
C12 C13 C14 129.9(3) ?
C17 C18 C19 120.1(3) ?
C17 C18 H18 119.9 ?
C19 C18 H18 119.9 ?
O5 C11 N2 121.5(3) ?
O5 C11 C12 130.5(3) ?
N2 C11 C12 107.9(3) yes
O4 C1 O1 108.7(2) ?
O4 C1 C10 108.6(3) ?
O1 C1 C10 106.6(2) ?
O4 C1 C2 113.9(2) ?
O1 C1 C2 103.4(2) yes
C10 C1 C2 115.2(2) ?
C4 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C4 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
N1 C2 C3 112.1(2) ?
N1 C2 C8 104.9(2) ?
C3 C2 C8 114.7(2) ?
N1 C2 C1 115.1(2) ?
C3 C2 C1 101.5(2) yes
C8 C2 C1 108.8(2) ?
O3 C8 C9 120.9(3) ?
O3 C8 C2 120.7(3) ?
C9 C8 C2 118.4(3) ?
O1 C4 C3 115.0(3) ?
O1 C4 C5 113.7(3) ?
C3 C4 C5 131.2(3) ?
C12 C20 H20A 109.5 ?
C12 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C12 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C17 C16 C15 120.6(3) ?
C17 C16 H16 119.7 ?
C15 C16 H16 119.7 ?
C18 C19 C14 120.7(3) ?
C18 C19 H23 119.7 ?
C14 C19 H23 119.7 ?
C16 C15 C14 120.2(3) ?
C16 C15 H15 119.9 ?
C14 C15 H15 119.9 ?
C16 C17 C18 119.7(3) ?
C16 C17 H17 120.2 ?
C18 C17 H17 120.2 ?
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 ?
O2 C6 C3 121.9(3) ?
O2 C6 C7 118.5(3) ?
C3 C6 C7 119.6(3) ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
O5 C21 H21A 109.5 ?
O5 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O5 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O4 C1 . 1.376(3) ?
O4 H4 . 0.82 ?
O1 C4 . 1.345(3) yes
O1 C1 . 1.469(3) yes
O5 C11 . 1.349(3) yes
O5 C21 . 1.415(4) ?
N2 C11 . 1.349(4) yes
N2 N3 . 1.355(3) yes
N2 N1 . 1.400(3) yes
N1 C2 . 1.484(4) yes
N1 H1 . 0.9786 ?
O2 C6 . 1.226(4) ?
O3 C8 . 1.201(4) ?
N3 C13 . 1.334(3) yes
C12 C11 . 1.373(4) yes
C12 C13 . 1.415(4) yes
C12 C20 . 1.499(4) ?
C3 C4 . 1.357(4) yes
C3 C6 . 1.450(4) ?
C3 C2 . 1.508(4) yes
C10 C1 . 1.503(4) ?
C10 H10C . 0.96 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C14 C19 . 1.388(4) ?
C14 C15 . 1.388(4) ?
C14 C13 . 1.478(4) ?
C18 C17 . 1.380(5) ?
C18 C19 . 1.382(4) ?
C18 H18 . 0.93 ?
C1 C2 . 1.599(4) yes
C5 C4 . 1.483(4) ?
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?
C2 C8 . 1.540(4) ?
C8 C9 . 1.500(5) ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C16 C17 . 1.370(5) ?
C16 C15 . 1.386(4) ?
C16 H16 . 0.93 ?
C19 H23 . 0.93 ?
C15 H15 . 0.93 ?
C17 H17 . 0.93 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C6 C7 . 1.496(4) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 1_565 0.98 2.17 3.056(3) 150 yes
O4 H4 N2 . 0.82 2.61 3.149(3) 125 no
O4 H4 N3 . 0.82 1.97 2.720(3) 152 yes
C5 H5A O2 . 0.96 2.38 2.948(4) 117 no
C5 H5C O4 1_545 0.96 2.52 3.293(4) 138 yes
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
C11 N2 N1 C2 -127.9(3) ?
N3 N2 N1 C2 58.5(3) yes
C11 N2 N3 C13 1.5(3) ?
N1 N2 N3 C13 175.9(2) ?
N2 N3 C13 C12 -1.9(3) ?
N2 N3 C13 C14 174.9(2) ?
C11 C12 C13 N3 1.6(3) ?
C20 C12 C13 N3 -178.6(3) ?
C11 C12 C13 C14 -174.7(3) ?
C20 C12 C13 C14 5.1(5) ?
C19 C14 C13 N3 -35.7(4) ?
C15 C14 C13 N3 143.9(3) ?
C19 C14 C13 C12 140.5(3) ?
C15 C14 C13 C12 -40.0(5) ?
C21 O5 C11 N2 -92.7(4) yes
C21 O5 C11 C12 91.4(4) ?
N3 N2 C11 O5 -177.3(2) ?
N1 N2 C11 O5 8.5(4) ?
N3 N2 C11 C12 -0.5(3) ?
N1 N2 C11 C12 -174.7(3) ?
C13 C12 C11 O5 175.7(3) ?
C20 C12 C11 O5 -4.1(5) ?
C13 C12 C11 N2 -0.6(3) ?
C20 C12 C11 N2 179.5(3) ?
C4 O1 C1 O4 136.8(2) ?
C4 O1 C1 C10 -106.3(3) ?
C4 O1 C1 C2 15.5(3) ?
N2 N1 C2 C3 45.8(3) ?
N2 N1 C2 C8 171.0(2) ?
N2 N1 C2 C1 -69.5(3) yes
C4 C3 C2 N1 -110.0(3) ?
C6 C3 C2 N1 68.9(4) ?
C4 C3 C2 C8 130.5(3) ?
C6 C3 C2 C8 -50.6(4) ?
C4 C3 C2 C1 13.4(3) ?
C6 C3 C2 C1 -167.7(3) ?
O4 C1 C2 N1 -13.4(3) ?
O1 C1 C2 N1 104.3(3) ?
C10 C1 C2 N1 -139.9(3) ?
O4 C1 C2 C3 -134.7(2) ?
O1 C1 C2 C3 -17.0(3) ?
C10 C1 C2 C3 98.8(3) ?
O4 C1 C2 C8 103.9(3) ?
O1 C1 C2 C8 -138.3(2) ?
C10 C1 C2 C8 -22.5(3) ?
N1 C2 C8 O3 -144.1(3) ?
C3 C2 C8 O3 -20.7(4) ?
C1 C2 C8 O3 92.2(4) ?
N1 C2 C8 C9 38.0(4) ?
C3 C2 C8 C9 161.5(3) ?
C1 C2 C8 C9 -85.6(4) ?
C1 O1 C4 C3 -7.7(3) ?
C1 O1 C4 C5 173.9(2) ?
C6 C3 C4 O1 176.5(3) ?
C2 C3 C4 O1 -4.6(3) ?
C6 C3 C4 C5 -5.4(5) ?
C2 C3 C4 C5 173.5(3) ?
C17 C18 C19 C14 0.5(5) ?
C15 C14 C19 C18 0.2(5) ?
C13 C14 C19 C18 179.8(3) ?
C17 C16 C15 C14 -0.4(5) ?
C19 C14 C15 C16 -0.3(5) ?
C13 C14 C15 C16 -179.8(3) ?
C15 C16 C17 C18 1.1(5) ?
C19 C18 C17 C16 -1.2(5) ?
C4 C3 C6 O2 -12.2(5) ?
C2 C3 C6 O2 169.1(3) ?
C4 C3 C6 C7 169.8(3) ?
C2 C3 C6 C7 -8.9(5) ?
