#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2205181.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_2205181
loop_
_publ_author_name
'Li, Zong-Xiao'
'Zhang, Xin-Li'
_publ_section_title
;
1,5-Dimethyl-2-phenyl-4-[(E,E)-3-phenylprop-2-enylideneamino]-
1H-pyrazol-3(2H)-one
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o375
_journal_page_last               o377
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H19 N3 O'
_chemical_formula_moiety         'C20 H19 N3 O'
_chemical_formula_sum            'C20 H19 N3 O'
_chemical_formula_weight         317.38
_chemical_name_systematic
;
1,5-Dimethyl-2-phenyl-4-[(E,E)-3-phenylprop-2-enylideneamino]-
1H-pyrazol-3(2H)-one
;
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_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                 97.556(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.480(3)
_cell_length_b                   9.796(2)
_cell_length_c                   13.757(3)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.615
_cell_measurement_theta_min      2.56
_cell_volume                     1800.8(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9060
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.199
_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     219
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0492
_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/[\s^2^(Fo^2^)+(0.0583P)^2^+0.4155P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1740
_reflns_number_total             3172
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    wn6320.cif
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_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_
_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_type_symbol
N1 1.05042(13) 0.2801(2) 1.00112(14) 0.0488(5) Uani d . 1 N
N2 1.06534(13) 0.1906(2) 1.08125(13) 0.0469(5) Uani d . 1 N
N3 0.81671(14) 0.0959(2) 0.98788(15) 0.0503(5) Uani d . 1 N
O1 0.92753(12) 0.3089(2) 0.86907(13) 0.0688(6) Uani d . 1 O
C1 0.95631(16) 0.2551(3) 0.94844(18) 0.0477(6) Uani d . 1 C
C2 0.91046(16) 0.1572(2) 1.00619(17) 0.0426(6) Uani d . 1 C
C3 0.97793(16) 0.1236(2) 1.08543(17) 0.0425(6) Uani d . 1 C
C4 0.96537(18) 0.0309(3) 1.16789(18) 0.0567(7) Uani d . 1 C
H4A 0.9635 0.0835 1.2265 0.085 Uiso calc R 1 H
H4B 1.0205 -0.0318 1.1775 0.085 Uiso calc R 1 H
H4C 0.9040 -0.0190 1.1532 0.085 Uiso calc R 1 H
C5 1.1330(2) 0.2339(3) 1.16722(19) 0.0739(9) Uani d . 1 C
H5A 1.1120 0.3212 1.1889 0.111 Uiso calc R 1 H
H5B 1.1997 0.2410 1.1506 0.111 Uiso calc R 1 H
H5C 1.1317 0.1682 1.2188 0.111 Uiso calc R 1 H
C6 1.13460(16) 0.3308(3) 0.95975(17) 0.0462(6) Uani d . 1 C
C7 1.21553(17) 0.2487(3) 0.95127(18) 0.0565(7) Uani d . 1 C
H7 1.2161 0.1586 0.9726 0.068 Uiso calc R 1 H
C8 1.29582(19) 0.3008(3) 0.9110(2) 0.0730(9) Uani d . 1 C
H8 1.3512 0.2459 0.9058 0.088 Uiso calc R 1 H
C9 1.2945(2) 0.4325(4) 0.8787(2) 0.0822(10) Uani d . 1 C
H9 1.3491 0.4675 0.8520 0.099 Uiso calc R 1 H
C10 1.2129(2) 0.5130(3) 0.8856(2) 0.0792(9) Uani d . 1 C
H10 1.2117 0.6024 0.8626 0.095 Uiso calc R 1 H
C11 1.13252(19) 0.4625(3) 0.9264(2) 0.0611(7) Uani d . 1 C
H11 1.0772 0.5175 0.9313 0.073 Uiso calc R 1 H
C12 0.75440(17) 0.1314(3) 0.91381(19) 0.0554(7) Uani d . 1 C
H12 0.7721 0.1987 0.8716 0.067 Uiso calc R 1 H
C13 0.65771(17) 0.0687(3) 0.89533(19) 0.0555(7) Uani d . 1 C
H13 0.6419 0.0013 0.9384 0.067 Uiso calc R 1 H
C14 0.58931(18) 0.1012(3) 0.8204(2) 0.0636(8) Uani d . 1 C
H14 0.6077 0.1691 0.7790 0.076 Uiso calc R 1 H
C15 0.48950(17) 0.0449(3) 0.7942(2) 0.0586(7) Uani d . 1 C
C16 0.44461(19) -0.0375(3) 0.8558(2) 0.0688(8) Uani d . 1 C
H16 0.4793 -0.0617 0.9163 0.083 Uiso calc R 1 H
C17 0.3479(2) -0.0854(3) 0.8291(3) 0.0848(10) Uani d . 1 C
H17 0.3175 -0.1397 0.8722 0.102 Uiso calc R 1 H
C18 0.2973(2) -0.0527(4) 0.7393(3) 0.0867(11) Uani d . 1 C
H18 0.2324 -0.0842 0.7214 0.104 Uiso calc R 1 H
C19 0.3418(2) 0.0252(4) 0.6766(3) 0.0915(11) Uani d . 1 C
H19 0.3082 0.0445 0.6147 0.110 Uiso calc R 1 H
C20 0.4365(2) 0.0764(3) 0.7035(2) 0.0788(9) Uani d . 1 C
H20 0.4653 0.1327 0.6605 0.095 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0401(11) 0.0558(13) 0.0488(13) -0.0047(9) -0.0009(9) 0.0079(10)
N2 0.0412(11) 0.0588(14) 0.0385(12) -0.0048(10) -0.0032(9) 0.0015(10)
N3 0.0396(11) 0.0605(14) 0.0501(13) -0.0041(10) 0.0030(10) 0.0024(11)
O1 0.0507(10) 0.0890(15) 0.0625(13) -0.0065(10) -0.0075(9) 0.0299(11)
C1 0.0374(13) 0.0591(17) 0.0455(15) 0.0002(11) 0.0012(11) 0.0028(13)
C2 0.0359(12) 0.0486(15) 0.0428(14) -0.0007(11) 0.0027(11) -0.0019(12)
C3 0.0417(13) 0.0449(15) 0.0409(14) -0.0001(11) 0.0051(11) -0.0066(11)
C4 0.0593(15) 0.0666(18) 0.0440(16) -0.0076(13) 0.0059(12) 0.0023(13)
C5 0.0712(19) 0.094(2) 0.0500(17) -0.0244(17) -0.0154(14) -0.0018(16)
C6 0.0400(13) 0.0506(16) 0.0466(15) -0.0067(11) 0.0006(11) -0.0015(12)
C7 0.0474(15) 0.0594(17) 0.0617(18) -0.0022(13) 0.0030(13) 0.0019(14)
C8 0.0478(16) 0.090(2) 0.082(2) -0.0044(16) 0.0131(15) -0.0007(19)
C9 0.064(2) 0.102(3) 0.083(2) -0.0258(19) 0.0206(17) 0.008(2)
C10 0.082(2) 0.063(2) 0.094(2) -0.0197(18) 0.0167(19) 0.0144(17)
C11 0.0609(17) 0.0507(18) 0.072(2) -0.0023(13) 0.0104(15) 0.0002(14)
C12 0.0438(14) 0.0634(18) 0.0573(17) -0.0044(13) -0.0004(13) 0.0098(14)
C13 0.0405(14) 0.0660(18) 0.0584(17) -0.0051(12) 0.0007(13) 0.0043(13)
C14 0.0461(15) 0.077(2) 0.0652(19) -0.0028(14) -0.0010(14) 0.0075(16)
C15 0.0397(14) 0.0700(19) 0.0636(19) 0.0028(13) -0.0025(14) -0.0093(15)
C16 0.0529(16) 0.088(2) 0.065(2) -0.0157(15) 0.0057(14) -0.0182(17)
C17 0.0595(19) 0.102(3) 0.096(3) -0.0218(17) 0.0195(19) -0.037(2)
C18 0.0409(17) 0.100(3) 0.116(3) -0.0012(17) -0.001(2) -0.056(2)
C19 0.053(2) 0.112(3) 0.100(3) 0.0184(19) -0.0235(19) -0.023(2)
C20 0.0528(17) 0.094(2) 0.083(2) 0.0110(16) -0.0169(16) 0.0004(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.397(3)
N1 N2 1.403(2)
N1 C6 1.424(3)
N2 C3 1.356(3)
N2 C5 1.458(3)
N3 C12 1.281(3)
N3 C2 1.392(3)
O1 C1 1.229(3)
C1 C2 1.436(3)
C2 C3 1.365(3)
C3 C4 1.480(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C11 1.367(3)
C6 C7 1.373(3)
C7 C8 1.377(4)
C7 H7 0.9300
C8 C9 1.364(4)
C8 H8 0.9300
C9 C10 1.366(4)
C9 H9 0.9300
C10 C11 1.377(4)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.433(3)
C12 H12 0.9300
C13 C14 1.329(3)
C13 H13 0.9300
C14 C15 1.455(3)
C14 H14 0.9300
C15 C16 1.367(4)
C15 C20 1.389(4)
C16 C17 1.389(4)
C16 H16 0.9300
C17 C18 1.368(5)
C17 H17 0.9300
C18 C19 1.350(5)
C18 H18 0.9300
C19 C20 1.375(4)
C19 H19 0.9300
C20 H20 0.9300
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 108.93(18)
C1 N1 C6 124.79(19)
N2 N1 C6 119.53(18)
C3 N2 N1 107.47(17)
C3 N2 C5 124.1(2)
N1 N2 C5 117.7(2)
C12 N3 C2 120.7(2)
O1 C1 N1 123.0(2)
O1 C1 C2 132.0(2)
N1 C1 C2 104.9(2)
C3 C2 N3 122.3(2)
C3 C2 C1 108.2(2)
N3 C2 C1 129.4(2)
N2 C3 C2 109.9(2)
N2 C3 C4 121.1(2)
C2 C3 C4 129.0(2)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N2 C5 H5A 109.5
N2 C5 H5B 109.5
H5A C5 H5B 109.5
N2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C11 C6 C7 120.4(2)
C11 C6 N1 118.7(2)
C7 C6 N1 120.9(2)
C6 C7 C8 119.5(3)
C6 C7 H7 120.2
C8 C7 H7 120.2
C9 C8 C7 120.3(3)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 120.0(3)
C8 C9 H9 120.0
C10 C9 H9 120.0
C9 C10 C11 120.3(3)
C9 C10 H10 119.9
C11 C10 H10 119.9
C6 C11 C10 119.6(3)
C6 C11 H11 120.2
C10 C11 H11 120.2
N3 C12 C13 120.7(2)
N3 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 123.9(3)
C14 C13 H13 118.1
C12 C13 H13 118.1
C13 C14 C15 128.7(3)
C13 C14 H14 115.6
C15 C14 H14 115.6
C16 C15 C20 118.1(3)
C16 C15 C14 122.7(3)
C20 C15 C14 119.2(3)
C15 C16 C17 120.8(3)
C15 C16 H16 119.6
C17 C16 H16 119.6
C18 C17 C16 119.9(3)
C18 C17 H17 120.0
C16 C17 H17 120.0
C19 C18 C17 119.9(3)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C20 120.6(3)
C18 C19 H19 119.7
C20 C19 H19 119.7
C19 C20 C15 120.7(3)
C19 C20 H20 119.7
C15 C20 H20 119.7
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
C4 H4A O1 4_566 0.96 2.33 3.279(3) 168
C12 H12 O1 ? 0.93 2.36 3.038(3) 129