#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227513.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_2227513
loop_
_publ_author_name
'Asad, Mohammad'
'Oo, Chuan-Wei'
'Osman, Hasnah'
'Quah, Ching Kheng'
'Fun, Hoong-Kun'
_publ_section_title
;
 4-[(E)-(4-Hydroxy-2-oxo-2H-chromen-3-yl)methylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
 monohydrate
;
_journal_coeditor_code           HB5618
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2491
_journal_page_last               o2492
_journal_paper_doi               10.1107/S160053681003480X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H17 N3 O4, H2 O'
_chemical_formula_moiety         'C21 H17 N3 O4, H2 O'
_chemical_formula_sum            'C21 H19 N3 O5'
_chemical_formula_weight         393.39
_chemical_name_systematic
;
4-{[(E)-(4-Hydroxy-2-oxo-2H-chromen-3-yl)methylidene]amino}-1,5-
dimethyl-2-phenyl-1H-pyrazol-3(2H)-one monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 108.008(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.225(4)
_cell_length_b                   6.4269(7)
_cell_length_c                   17.6163(18)
_cell_measurement_reflns_used    6036
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.92
_cell_measurement_theta_min      2.43
_cell_volume                     3792.7(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35398
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.660
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0911P)²+2.8654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                3412
_reflns_number_total             5044
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5618.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227513
_cod_database_fobs_code          2227513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.00970(3) 0.25568(17) 0.35782(6) 0.0201(3) Uani d . 1 . .
O O2 0.07480(4) 0.2578(2) 0.41212(7) 0.0269(3) Uani d . 1 . .
O O3 -0.00816(3) 0.24563(17) 0.57775(6) 0.0212(3) Uani d . 1 . .
O O4 0.15875(3) 0.2277(2) 0.65776(7) 0.0275(3) Uani d . 1 . .
N N1 0.06937(4) 0.24627(19) 0.64206(7) 0.0160(3) Uani d . 1 . .
N N2 0.13874(4) 0.2275(2) 0.83849(8) 0.0246(3) Uani d . 1 . .
N N3 0.16474(4) 0.2441(2) 0.79281(8) 0.0258(3) Uani d . 1 . .
C C1 0.04266(5) 0.2552(2) 0.42474(9) 0.0183(3) Uani d . 1 . .
C C2 -0.02838(5) 0.2533(2) 0.36347(9) 0.0173(3) Uani d . 1 . .
C C3 -0.05929(5) 0.2540(2) 0.29108(9) 0.0210(3) Uani d . 1 . .
H H3A -0.0537 0.2560 0.2428 0.025 Uiso calc R 1 . .
C C4 -0.09821(5) 0.2515(2) 0.29271(10) 0.0239(3) Uani d . 1 . .
H H4A -0.1191 0.2517 0.2450 0.029 Uiso calc R 1 . .
C C5 -0.10675(5) 0.2486(3) 0.36506(10) 0.0245(3) Uani d . 1 . .
H H5A -0.1331 0.2471 0.3654 0.029 Uiso calc R 1 . .
C C6 -0.07578(5) 0.2482(2) 0.43627(10) 0.0207(3) Uani d . 1 . .
H H6A -0.0815 0.2462 0.4844 0.025 Uiso calc R 1 . .
C C7 -0.03600(4) 0.2507(2) 0.43656(9) 0.0170(3) Uani d . 1 . .
C C8 -0.00234(5) 0.2493(2) 0.51080(9) 0.0160(3) Uani d . 1 . .
C C9 0.03653(4) 0.2519(2) 0.50194(8) 0.0155(3) Uani d . 1 . .
C C10 0.07103(5) 0.2515(2) 0.56840(9) 0.0170(3) Uani d . 1 . .
H H10A 0.0959 0.2551 0.5602 0.020 Uiso calc R 1 . .
C C11 0.10243(4) 0.2456(2) 0.71053(8) 0.0169(3) Uani d . 1 . .
C C12 0.10082(5) 0.2418(2) 0.78734(9) 0.0188(3) Uani d . 1 . .
C C13 0.14344(5) 0.2403(3) 0.71201(9) 0.0202(3) Uani d . 1 . .
C C14 0.20606(5) 0.1917(3) 0.82639(10) 0.0273(4) Uani d . 1 . .
C C15 0.21734(6) 0.0144(4) 0.87239(12) 0.0404(5) Uani d . 1 . .
H H15A 0.1982 -0.0713 0.8826 0.048 Uiso calc R 1 . .
C C16 0.25772(6) -0.0340(4) 0.90322(13) 0.0462(5) Uani d . 1 . .
H H16A 0.2657 -0.1526 0.9343 0.055 Uiso calc R 1 . .
C C17 0.28592(5) 0.0944(4) 0.88758(11) 0.0376(5) Uani d . 1 . .
H H17A 0.3129 0.0606 0.9074 0.045 Uiso calc R 1 . .
C C18 0.27429(6) 0.2720(4) 0.84276(12) 0.0389(5) Uani d . 1 . .
H H18A 0.2935 0.3589 0.8334 0.047 Uiso calc R 1 . .
C C19 0.23402(5) 0.3225(3) 0.81140(11) 0.0348(4) Uani d . 1 . .
H H19A 0.2261 0.4422 0.7809 0.042 Uiso calc R 1 . .
C C20 0.06538(5) 0.2483(3) 0.81601(10) 0.0260(4) Uani d . 1 . .
H H20A 0.0660 0.1315 0.8504 0.039 Uiso calc R 1 . .
H H20B 0.0415 0.2427 0.7712 0.039 Uiso calc R 1 . .
H H20C 0.0657 0.3751 0.8450 0.039 Uiso calc R 1 . .
C C21 0.15162(6) 0.3240(4) 0.91767(10) 0.0374(5) Uani d . 1 . .
H H21A 0.1323 0.2962 0.9446 0.056 Uiso calc R 1 . .
H H21B 0.1541 0.4716 0.9122 0.056 Uiso calc R 1 . .
H H21C 0.1770 0.2674 0.9482 0.056 Uiso calc R 1 . .
O O1W 0.15736(5) 0.1509(3) 0.49339(10) 0.0663(6) Uani d . 1 . .
H H1OW 0.1580 0.1624 0.5429 0.099 Uiso d R 1 . .
H H2OW 0.1317 0.1766 0.4741 0.099 Uiso d R 1 . .
H H1N1 0.0428(7) 0.242(3) 0.6406(15) 0.042(7) Uiso 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 0.0000 0.0000 '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 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 . . 121.45(12) ?
C10 N1 C11 . . 124.94(14) ?
C10 N1 H1N1 . . 109.0(16) ?
C11 N1 H1N1 . . 126.1(16) ?
C12 N2 N3 . . 107.25(12) ?
C12 N2 C21 . . 123.53(15) ?
N3 N2 C21 . . 116.80(14) ?
C13 N3 N2 . . 110.25(13) ?
C13 N3 C14 . . 125.28(14) ?
N2 N3 C14 . . 120.50(13) ?
O2 C1 O1 . . 115.41(13) ?
O2 C1 C9 . . 126.19(14) ?
O1 C1 C9 . . 118.40(13) ?
O1 C2 C7 . . 122.50(13) ?
O1 C2 C3 . . 115.85(14) ?
C7 C2 C3 . . 121.64(15) ?
C4 C3 C2 . . 118.66(15) ?
C4 C3 H3A . . 120.7 ?
C2 C3 H3A . . 120.7 ?
C3 C4 C5 . . 120.96(14) ?
C3 C4 H4A . . 119.5 ?
C5 C4 H4A . . 119.5 ?
C6 C5 C4 . . 119.67(15) ?
C6 C5 H5A . . 120.2 ?
C4 C5 H5A . . 120.2 ?
C5 C6 C7 . . 120.71(15) ?
C5 C6 H6A . . 119.6 ?
C7 C6 H6A . . 119.6 ?
C2 C7 C6 . . 118.36(14) ?
C2 C7 C8 . . 119.30(14) ?
C6 C7 C8 . . 122.34(14) ?
O3 C8 C9 . . 122.90(14) ?
O3 C8 C7 . . 120.93(14) ?
C9 C8 C7 . . 116.16(13) ?
C10 C9 C8 . . 121.49(13) ?
C10 C9 C1 . . 116.33(13) ?
C8 C9 C1 . . 122.18(13) ?
N1 C10 C9 . . 122.09(14) ?
N1 C10 H10A . . 119.0 ?
C9 C10 H10A . . 119.0 ?
C12 C11 N1 . . 125.13(14) ?
C12 C11 C13 . . 109.24(13) ?
N1 C11 C13 . . 125.59(13) ?
N2 C12 C11 . . 108.80(14) ?
N2 C12 C20 . . 122.12(14) ?
C11 C12 C20 . . 129.07(14) ?
O4 C13 N3 . . 124.51(15) ?
O4 C13 C11 . . 131.58(14) ?
N3 C13 C11 . . 103.87(13) ?
C19 C14 C15 . . 121.39(17) ?
C19 C14 N3 . . 118.14(17) ?
C15 C14 N3 . . 120.47(17) ?
C14 C15 C16 . . 119.12(19) ?
C14 C15 H15A . . 120.4 ?
C16 C15 H15A . . 120.4 ?
C17 C16 C15 . . 119.9(2) ?
C17 C16 H16A . . 120.0 ?
C15 C16 H16A . . 120.0 ?
C18 C17 C16 . . 120.30(18) ?
C18 C17 H17A . . 119.9 ?
C16 C17 H17A . . 119.9 ?
C17 C18 C19 . . 120.48(19) ?
C17 C18 H18A . . 119.8 ?
C19 C18 H18A . . 119.8 ?
C14 C19 C18 . . 118.77(19) ?
C14 C19 H19A . . 120.6 ?
C18 C19 H19A . . 120.6 ?
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 ?
N2 C21 H21A . . 109.5 ?
N2 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N2 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
H1OW O1W H2OW . . 94.6 ?
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
O1 C1 . 1.3753(18) ?
O1 C2 . 1.3755(19) ?
O2 C1 . 1.219(2) ?
O3 C8 . 1.2583(17) ?
O4 C13 . 1.2367(19) ?
N1 C10 . 1.3175(19) ?
N1 C11 . 1.3937(18) ?
N1 H1N1 . 0.93(2) ?
N2 C12 . 1.364(2) ?
N2 N3 . 1.3977(19) ?
N2 C21 . 1.465(2) ?
N3 C13 . 1.3890(19) ?
N3 C14 . 1.432(2) ?
C1 C9 . 1.4416(19) ?
C2 C7 . 1.394(2) ?
C2 C3 . 1.398(2) ?
C3 C4 . 1.380(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.397(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.385(2) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.400(2) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.469(2) ?
C8 C9 . 1.425(2) ?
C9 C10 . 1.403(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.3718(19) ?
C11 C13 . 1.437(2) ?
C12 C20 . 1.485(2) ?
C14 C19 . 1.381(3) ?
C14 C15 . 1.383(3) ?
C15 C16 . 1.392(3) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.383(3) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.376(3) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.392(3) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
O1W H1OW . 0.8673 ?
O1W H2OW . 0.8763 ?
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
O1W H1OW O4 . 0.87 2.06 2.923(2) 173 yes
O1W H2OW O2 . 0.88 2.03 2.899(2) 170 yes
N1 H1N1 O3 . 0.93(3) 1.79(3) 2.6132(18) 146(2) yes
C3 H3A O2 2_555 0.93 2.60 3.450(2) 153 yes
C10 H10A O4 . 0.93 2.35 3.007(2) 127 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N2 N3 C13 . . . . -8.12(18) ?
C21 N2 N3 C13 . . . . -151.71(16) ?
C12 N2 N3 C14 . . . . -166.83(15) ?
C21 N2 N3 C14 . . . . 49.6(2) ?
C2 O1 C1 O2 . . . . -179.86(13) ?
C2 O1 C1 C9 . . . . 0.1(2) ?
C1 O1 C2 C7 . . . . 0.1(2) ?
C1 O1 C2 C3 . . . . -179.95(13) ?
O1 C2 C3 C4 . . . . 179.93(13) ?
C7 C2 C3 C4 . . . . -0.1(2) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C4 C5 C6 C7 . . . . 0.1(2) ?
O1 C2 C7 C6 . . . . -179.92(13) ?
C3 C2 C7 C6 . . . . 0.1(2) ?
O1 C2 C7 C8 . . . . -0.3(2) ?
C3 C2 C7 C8 . . . . 179.73(14) ?
C5 C6 C7 C2 . . . . -0.1(2) ?
C5 C6 C7 C8 . . . . -179.68(15) ?
C2 C7 C8 O3 . . . . -179.56(14) ?
C6 C7 C8 O3 . . . . 0.0(2) ?
C2 C7 C8 C9 . . . . 0.3(2) ?
C6 C7 C8 C9 . . . . 179.91(14) ?
O3 C8 C9 C10 . . . . -0.3(2) ?
C7 C8 C9 C10 . . . . 179.79(13) ?
O3 C8 C9 C1 . . . . 179.74(14) ?
C7 C8 C9 C1 . . . . -0.2(2) ?
O2 C1 C9 C10 . . . . -0.1(2) ?
O1 C1 C9 C10 . . . . 180.00(13) ?
O2 C1 C9 C8 . . . . 179.89(15) ?
O1 C1 C9 C8 . . . . 0.0(2) ?
C11 N1 C10 C9 . . . . 180.00(14) ?
C8 C9 C10 N1 . . . . 0.8(2) ?
C1 C9 C10 N1 . . . . -179.23(14) ?
C10 N1 C11 C12 . . . . 179.45(15) ?
C10 N1 C11 C13 . . . . -3.2(2) ?
N3 N2 C12 C11 . . . . 6.06(18) ?
C21 N2 C12 C11 . . . . 146.60(17) ?
N3 N2 C12 C20 . . . . -174.70(15) ?
C21 N2 C12 C20 . . . . -34.2(3) ?
N1 C11 C12 N2 . . . . 175.77(14) ?
C13 C11 C12 N2 . . . . -1.98(18) ?
N1 C11 C12 C20 . . . . -3.4(3) ?
C13 C11 C12 C20 . . . . 178.85(16) ?
N2 N3 C13 O4 . . . . -171.06(16) ?
C14 N3 C13 O4 . . . . -13.6(3) ?
N2 N3 C13 C11 . . . . 6.66(17) ?
C14 N3 C13 C11 . . . . 164.13(16) ?
C12 C11 C13 O4 . . . . 174.61(18) ?
N1 C11 C13 O4 . . . . -3.1(3) ?
C12 C11 C13 N3 . . . . -2.89(17) ?
N1 C11 C13 N3 . . . . 179.38(14) ?
C13 N3 C14 C19 . . . . 68.3(2) ?
N2 N3 C14 C19 . . . . -136.40(18) ?
C13 N3 C14 C15 . . . . -111.6(2) ?
N2 N3 C14 C15 . . . . 43.7(2) ?
C19 C14 C15 C16 . . . . -0.9(3) ?
N3 C14 C15 C16 . . . . 179.04(19) ?
C14 C15 C16 C17 . . . . -0.1(3) ?
C15 C16 C17 C18 . . . . 1.1(3) ?
C16 C17 C18 C19 . . . . -1.2(3) ?
C15 C14 C19 C18 . . . . 0.8(3) ?
N3 C14 C19 C18 . . . . -179.13(17) ?
C17 C18 C19 C14 . . . . 0.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656233
