#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210473.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_2210473
loop_
_publ_author_name
'Diao, Chun-Hua'
'Chen, Xin'
_publ_section_title
(E)-1,5-Dimethyl-4-{2-[2-(2-nitrophenoxy)ethoxy]benzylideneamino}-2-phenyl-1H-pyrazol-3(2H)-one
_journal_coeditor_code           AT2106
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4422
_journal_page_last               o4424
_journal_paper_doi               10.1107/S1600536806036269
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C26 H24 N4 O5'
_chemical_formula_moiety         'C26 H24 N4 O5'
_chemical_formula_sum            'C26 H24 N4 O5'
_chemical_formula_weight         472.49
_chemical_name_systematic
;
(E)-1,5-Dimethyl-4-{2-[2-(2-nitrophenoxy)ethoxy]benzylideneamino}-2-phenyl-
1H-pyrazol-3(2H)-one
;
_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                 103.140(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.255(4)
_cell_length_b                   18.369(5)
_cell_length_c                   10.040(3)
_cell_measurement_reflns_used    2344
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.72
_cell_volume                     2380.5(12)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_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      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1018
_diffrn_reflns_av_sigmaI/netI    0.1285
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11202
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.3376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                1986
_reflns_number_total             4173
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2106.cif
_cod_data_source_block           I
_cod_original_cell_volume        2380.6(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210473
_cod_database_fobs_code          2210473
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_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 O1 0.3954(2) 0.18062(14) 1.0379(3) 0.0832(8) Uani d . 1
O O2 0.3156(2) 0.19113(14) 0.8264(3) 0.0776(8) Uani d . 1
O O3 0.41896(18) 0.09153(12) 0.7040(2) 0.0662(7) Uani d . 1
O O4 0.54619(15) 0.12133(10) 0.51040(19) 0.0483(6) Uani d . 1
O O5 0.75766(16) -0.03508(11) 0.7282(2) 0.0535(6) Uani d . 1
N N1 0.3581(2) 0.15495(17) 0.9246(4) 0.0572(8) Uani d . 1
N N2 0.8552(2) 0.09536(13) 0.5989(2) 0.0429(6) Uani d . 1
N N3 1.02532(18) -0.04255(15) 0.7749(2) 0.0482(7) Uani d . 1
N N4 0.92898(19) -0.07322(14) 0.7819(2) 0.0461(7) Uani d . 1
C C1 0.3643(2) 0.07581(18) 0.9094(3) 0.0473(8) Uani d . 1
C C2 0.3423(3) 0.0340(2) 1.0123(4) 0.0647(10) Uani d . 1
H H2 0.3256 0.0558 1.0881 0.078 Uiso calc R 1
C C3 0.3452(3) -0.0404(2) 1.0019(4) 0.0761(12) Uani d . 1
H H3 0.3296 -0.0696 1.0702 0.091 Uiso calc R 1
C C4 0.3713(3) -0.0716(2) 0.8900(5) 0.0749(11) Uani d . 1
H H4 0.3738 -0.1221 0.8833 0.090 Uiso calc R 1
C C5 0.3937(3) -0.0292(2) 0.7878(4) 0.0658(10) Uani d . 1
H H5 0.4111 -0.0512 0.7126 0.079 Uiso calc R 1
C C6 0.3906(2) 0.04590(19) 0.7959(3) 0.0506(9) Uani d . 1
C C7 0.3986(3) 0.06975(18) 0.5655(3) 0.0597(10) Uani d . 1
H H7A 0.3248 0.0624 0.5313 0.072 Uiso calc R 1
H H7B 0.4337 0.0242 0.5573 0.072 Uiso calc R 1
C C8 0.4362(2) 0.12742(18) 0.4843(3) 0.0544(9) Uani d . 1
H H8A 0.4060 0.1208 0.3875 0.065 Uiso calc R 1
H H8B 0.4166 0.1751 0.5113 0.065 Uiso calc R 1
C C9 0.6004(2) 0.17281(16) 0.4563(3) 0.0392(8) Uani d . 1
C C10 0.5538(3) 0.22674(18) 0.3679(3) 0.0528(9) Uani d . 1
H H10 0.4820 0.2294 0.3409 0.063 Uiso calc R 1
C C11 0.6148(3) 0.27705(18) 0.3196(3) 0.0636(10) Uani d . 1
H H11 0.5837 0.3138 0.2607 0.076 Uiso calc R 1
C C12 0.7209(3) 0.27294(19) 0.3580(4) 0.0664(11) Uani d . 1
H H12 0.7614 0.3073 0.3263 0.080 Uiso calc R 1
C C13 0.7668(3) 0.21848(17) 0.4425(3) 0.0539(9) Uani d . 1
H H13 0.8387 0.2159 0.4675 0.065 Uiso calc R 1
C C14 0.7081(2) 0.16638(16) 0.4924(3) 0.0381(8) Uani d . 1
C C15 0.7570(2) 0.10536(16) 0.5752(3) 0.0407(8) Uani d . 1
H H15 0.7163 0.0731 0.6116 0.049 Uiso calc R 1
C C16 0.8991(2) 0.03392(16) 0.6707(3) 0.0386(8) Uani d . 1
C C17 1.0022(2) 0.02004(18) 0.6993(3) 0.0446(8) Uani d . 1
C C18 0.8493(2) -0.02573(16) 0.7257(3) 0.0394(8) Uani d . 1
C C19 1.0869(2) 0.06350(18) 0.6607(3) 0.0662(10) Uani d . 1
H H19A 1.1168 0.0359 0.5981 0.099 Uiso calc R 1
H H19B 1.1393 0.0743 0.7413 0.099 Uiso calc R 1
H H19C 1.0588 0.1081 0.6178 0.099 Uiso calc R 1
C C20 1.1003(3) -0.09503(19) 0.7445(4) 0.0724(11) Uani d . 1
H H20A 1.0735 -0.1162 0.6562 0.109 Uiso calc R 1
H H20B 1.1121 -0.1326 0.8127 0.109 Uiso calc R 1
H H20C 1.1644 -0.0706 0.7448 0.109 Uiso calc R 1
C C21 0.9250(3) -0.12698(17) 0.8830(3) 0.0432(8) Uani d . 1
C C22 0.8468(3) -0.17782(18) 0.8560(3) 0.0532(9) Uani d . 1
H H22 0.7968 -0.1762 0.7743 0.064 Uiso calc R 1
C C23 0.8436(3) -0.23127(19) 0.9518(4) 0.0661(10) Uani d . 1
H H23 0.7907 -0.2656 0.9350 0.079 Uiso calc R 1
C C24 0.9182(4) -0.2339(2) 1.0717(4) 0.0759(12) Uani d . 1
H H24 0.9169 -0.2707 1.1349 0.091 Uiso calc R 1
C C25 0.9946(3) -0.1821(2) 1.0980(4) 0.0696(11) Uani d . 1
H H25 1.0443 -0.1836 1.1799 0.084 Uiso calc R 1
C C26 0.9987(3) -0.12811(18) 1.0049(3) 0.0568(9) Uani d . 1
H H26 1.0503 -0.0928 1.0236 0.068 Uiso calc R 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
_geom_angle_publ_flag
C6 O3 C7 118.2(2) ?
C9 O4 C8 118.6(2) ?
O2 N1 O1 123.8(3) ?
O2 N1 C1 118.9(3) ?
O1 N1 C1 117.2(3) ?
C15 N2 C16 119.9(3) yes
C17 N3 N4 105.7(2) yes
C17 N3 C20 120.8(3) ?
N4 N3 C20 114.3(3) ?
C18 N4 N3 110.0(2) yes
C18 N4 C21 125.2(2) ?
N3 N4 C21 119.5(2) ?
C2 C1 C6 122.5(3) ?
C2 C1 N1 116.7(3) ?
C6 C1 N1 120.8(3) ?
C1 C2 C3 119.1(4) ?
C1 C2 H2 120.5 ?
C3 C2 H2 120.5 ?
C2 C3 C4 119.6(4) ?
C2 C3 H3 120.2 ?
C4 C3 H3 120.2 ?
C5 C4 C3 120.8(4) ?
C5 C4 H4 119.6 ?
C3 C4 H4 119.6 ?
C4 C5 C6 120.5(4) ?
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
O3 C6 C1 118.4(3) ?
O3 C6 C5 123.9(3) ?
C1 C6 C5 117.6(3) ?
O3 C7 C8 108.9(3) ?
O3 C7 H7A 109.9 ?
C8 C7 H7A 109.9 ?
O3 C7 H7B 109.9 ?
C8 C7 H7B 109.9 ?
H7A C7 H7B 108.3 ?
O4 C8 C7 107.4(3) ?
O4 C8 H8A 110.2 ?
C7 C8 H8A 110.2 ?
O4 C8 H8B 110.2 ?
C7 C8 H8B 110.2 ?
H8A C8 H8B 108.5 ?
O4 C9 C10 123.5(3) ?
O4 C9 C14 115.8(3) ?
C10 C9 C14 120.7(3) ?
C9 C10 C11 119.5(3) ?
C9 C10 H10 120.3 ?
C11 C10 H10 120.3 ?
C12 C11 C10 120.5(3) ?
C12 C11 H11 119.8 ?
C10 C11 H11 119.8 ?
C13 C12 C11 119.9(3) ?
C13 C12 H12 120.0 ?
C11 C12 H12 120.0 ?
C12 C13 C14 121.3(3) ?
C12 C13 H13 119.3 ?
C14 C13 H13 119.3 ?
C9 C14 C13 118.0(3) ?
C9 C14 C15 120.6(3) ?
C13 C14 C15 121.3(3) ?
N2 C15 C14 121.2(3) yes
N2 C15 H15 119.4 ?
C14 C15 H15 119.4 ?
C17 C16 N2 123.0(3) yes
C17 C16 C18 107.5(3) ?
N2 C16 C18 129.5(3) yes
C16 C17 N3 111.2(3) ?
C16 C17 C19 128.6(3) ?
N3 C17 C19 120.2(3) ?
O5 C18 N4 124.5(3) ?
O5 C18 C16 130.4(3) ?
N4 C18 C16 105.1(3) ?
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 ?
N3 C20 H20A 109.5 ?
N3 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
N3 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C22 C21 C26 121.0(3) ?
C22 C21 N4 118.5(3) ?
C26 C21 N4 120.5(3) ?
C21 C22 C23 119.1(3) ?
C21 C22 H22 120.5 ?
C23 C22 H22 120.5 ?
C24 C23 C22 120.3(4) ?
C24 C23 H23 119.9 ?
C22 C23 H23 119.9 ?
C25 C24 C23 119.8(4) ?
C25 C24 H24 120.1 ?
C23 C24 H24 120.1 ?
C24 C25 C26 120.8(4) ?
C24 C25 H25 119.6 ?
C26 C25 H25 119.6 ?
C25 C26 C21 119.0(3) ?
C25 C26 H26 120.5 ?
C21 C26 H26 120.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.227(3) ?
O2 N1 1.216(3) ?
O3 C6 1.362(4) ?
O3 C7 1.412(3) ?
O4 C9 1.372(3) ?
O4 C8 1.426(3) ?
O5 C18 1.233(3) ?
N1 C1 1.466(4) ?
N2 C15 1.282(3) yes
N2 C16 1.393(3) yes
N3 C17 1.373(4) ?
N3 N4 1.412(3) yes
N3 C20 1.465(4) ?
N4 C18 1.387(3) ?
N4 C21 1.426(4) ?
C1 C2 1.371(4) ?
C1 C6 1.379(4) ?
C2 C3 1.373(5) ?
C2 H2 0.9300 ?
C3 C4 1.374(5) ?
C3 H3 0.9300 ?
C4 C5 1.373(5) ?
C4 H4 0.9300 ?
C5 C6 1.383(4) ?
C5 H5 0.9300 ?
C7 C8 1.490(4) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.379(4) ?
C9 C14 1.395(4) ?
C10 C11 1.387(4) ?
C10 H10 0.9300 ?
C11 C12 1.373(4) ?
C11 H11 0.9300 ?
C12 C13 1.363(4) ?
C12 H12 0.9300 ?
C13 C14 1.397(4) ?
C13 H13 0.9300 ?
C14 C15 1.457(4) ?
C15 H15 0.9300 ?
C16 C17 1.356(4) ?
C16 C18 1.451(4) ?
C17 C19 1.498(4) ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C21 C22 1.375(4) ?
C21 C26 1.381(4) ?
C22 C23 1.382(4) ?
C22 H22 0.9300 ?
C23 C24 1.375(5) ?
C23 H23 0.9300 ?
C24 C25 1.370(5) ?
C24 H24 0.9300 ?
C25 C26 1.373(4) ?
C25 H25 0.9300 ?
C26 H26 0.9300 ?
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
C2 H2 O5 3_657 0.93 2.39 3.180(4) 143 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
C17 N3 N4 C18 -7.0(3)
C20 N3 N4 C18 -142.3(3)
C17 N3 N4 C21 -162.7(2)
C20 N3 N4 C21 62.0(3)
O2 N1 C1 C2 -135.9(3)
O1 N1 C1 C2 43.1(4)
O2 N1 C1 C6 43.8(4)
O1 N1 C1 C6 -137.2(3)
C6 C1 C2 C3 -0.8(5)
N1 C1 C2 C3 178.9(3)
C1 C2 C3 C4 0.8(6)
C2 C3 C4 C5 -0.5(6)
C3 C4 C5 C6 0.1(6)
C7 O3 C6 C1 -150.3(3)
C7 O3 C6 C5 34.6(5)
C2 C1 C6 O3 -175.0(3)
N1 C1 C6 O3 5.3(5)
C2 C1 C6 C5 0.4(5)
N1 C1 C6 C5 -179.3(3)
C4 C5 C6 O3 175.1(3)
C4 C5 C6 C1 -0.1(5)
C6 O3 C7 C8 -179.8(3)
C9 O4 C8 C7 -174.4(2)
O3 C7 C8 O4 76.3(3)
C8 O4 C9 C10 -5.9(4)
C8 O4 C9 C14 176.2(2)
O4 C9 C10 C11 179.2(3)
C14 C9 C10 C11 -3.0(4)
C9 C10 C11 C12 0.7(5)
C10 C11 C12 C13 1.0(5)
C11 C12 C13 C14 -0.4(5)
O4 C9 C14 C13 -178.5(2)
C10 C9 C14 C13 3.5(4)
O4 C9 C14 C15 3.8(4)
C10 C9 C14 C15 -174.1(3)
C12 C13 C14 C9 -1.8(4)
C12 C13 C14 C15 175.8(3)
C16 N2 C15 C14 -175.7(2)
C9 C14 C15 N2 173.8(3)
C13 C14 C15 N2 -3.8(4)
C15 N2 C16 C17 -180.0(3)
C15 N2 C16 C18 1.1(4)
N2 C16 C17 N3 178.0(2)
C18 C16 C17 N3 -2.9(3)
N2 C16 C17 C19 -1.4(5)
C18 C16 C17 C19 177.8(3)
N4 N3 C17 C16 6.1(3)
C20 N3 C17 C16 137.8(3)
N4 N3 C17 C19 -174.5(3)
C20 N3 C17 C19 -42.8(4)
N3 N4 C18 O5 -173.5(3)
C21 N4 C18 O5 -19.5(5)
N3 N4 C18 C16 5.3(3)
C21 N4 C18 C16 159.2(3)
C17 C16 C18 O5 177.1(3)
N2 C16 C18 O5 -3.8(5)
C17 C16 C18 N4 -1.5(3)
N2 C16 C18 N4 177.5(3)
C18 N4 C21 C22 56.2(4)
N3 N4 C21 C22 -152.0(3)
C18 N4 C21 C26 -124.3(3)
N3 N4 C21 C26 27.4(4)
C26 C21 C22 C23 -1.0(4)
N4 C21 C22 C23 178.4(3)
C21 C22 C23 C24 -0.7(5)
C22 C23 C24 C25 1.7(5)
C23 C24 C25 C26 -1.0(5)
C24 C25 C26 C21 -0.7(5)
C22 C21 C26 C25 1.7(4)
N4 C21 C26 C25 -177.7(3)
