#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/41/2234145.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_2234145
loop_
_publ_author_name
'Wang, Hai-Wen'
_publ_section_title
;
 4-[(Z)-(n-Butylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           CV5252
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o969
_journal_paper_doi               10.1107/S1600536812009166
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C21 H23 N3 O'
_chemical_formula_moiety         'C21 H23 N3 O'
_chemical_formula_sum            'C21 H23 N3 O'
_chemical_formula_weight         333.42
_chemical_name_systematic
;
4-[(Z)-(n-Butylamino)(phenyl)methylidene]-3-methyl-
1-phenyl-1H-pyrazol-5(4H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.645(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5215(9)
_cell_length_b                   14.7867(14)
_cell_length_c                   12.8055(12)
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.57
_cell_volume                     1771.9(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16506
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712.0
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0400
_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/[σ²(Fo²)+(0.0499P)²+0.4177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                3362
_reflns_number_total             4368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv5252.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234145
_cod_database_fobs_code          2234145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
C C1 0.21783(12) 0.26068(9) 0.88837(9) 0.0167(2) Uani d . 1 1
C C2 0.10538(13) 0.21696(9) 0.92399(9) 0.0204(3) Uani d . 1 1
H H2 0.1013 0.1541 0.9255 0.024 Uiso calc R 1 1
C C3 -0.00037(13) 0.26856(9) 0.95714(10) 0.0218(3) Uani d . 1 1
H H3 -0.0742 0.2397 0.9824 0.026 Uiso calc R 1 1
C C4 0.00239(13) 0.36198(9) 0.95320(9) 0.0218(3) Uani d . 1 1
H H4 -0.0699 0.3957 0.9744 0.026 Uiso calc R 1 1
C C5 0.11413(13) 0.40483(9) 0.91726(10) 0.0220(3) Uani d . 1 1
H H5 0.1166 0.4676 0.9144 0.026 Uiso calc R 1 1
C C6 0.22209(13) 0.35488(9) 0.88561(9) 0.0193(3) Uani d . 1 1
H H6 0.2973 0.3842 0.8626 0.023 Uiso calc R 1 1
C C7 0.35303(12) 0.11883(8) 0.85902(9) 0.0158(2) Uani d . 1 1
C C8 0.48777(12) 0.10785(8) 0.82441(9) 0.0159(2) Uani d . 1 1
C C9 0.53156(12) 0.19778(8) 0.80232(9) 0.0168(2) Uani d . 1 1
C C10 0.66208(13) 0.22991(9) 0.76371(10) 0.0217(3) Uani d . 1 1
H H10A 0.6553 0.2136 0.6904 0.033 Uiso calc R 1 1
H H10B 0.7453 0.2023 0.8052 0.033 Uiso calc R 1 1
H H10C 0.6693 0.2945 0.7708 0.033 Uiso calc R 1 1
C C11 0.55372(12) 0.02287(8) 0.82705(9) 0.0152(2) Uani d . 1 1
C C12 0.69661(12) 0.00963(8) 0.79819(9) 0.0153(2) Uani d . 1 1
C C13 0.81099(13) -0.01709(9) 0.87666(9) 0.0185(3) Uani d . 1 1
H H13 0.7970 -0.0279 0.9456 0.022 Uiso calc R 1 1
C C14 0.94570(13) -0.02752(9) 0.85151(10) 0.0221(3) Uani d . 1 1
H H14 1.0223 -0.0446 0.9038 0.027 Uiso calc R 1 1
C C15 0.96628(13) -0.01252(9) 0.74855(10) 0.0228(3) Uani d . 1 1
H H15 1.0567 -0.0195 0.7319 0.027 Uiso calc R 1 1
C C16 0.85241(14) 0.01285(9) 0.67051(10) 0.0212(3) Uani d . 1 1
H H16 0.8663 0.0221 0.6013 0.025 Uiso calc R 1 1
C C17 0.71793(13) 0.02451(8) 0.69496(9) 0.0179(2) Uani d . 1 1
H H17 0.6419 0.0423 0.6425 0.021 Uiso calc R 1 1
C C18 0.53117(13) -0.14295(8) 0.85933(9) 0.0177(2) Uani d . 1 1
H H18A 0.6204 -0.1519 0.9088 0.021 Uiso calc R 1 1
H H18B 0.5456 -0.1600 0.7889 0.021 Uiso calc R 1 1
C C19 0.41494(13) -0.20109(8) 0.89147(9) 0.0172(2) Uani d . 1 1
H H19A 0.4043 -0.1852 0.9631 0.021 Uiso calc R 1 1
H H19B 0.3250 -0.1886 0.8444 0.021 Uiso calc R 1 1
C C20 0.44787(13) -0.30125(9) 0.88723(10) 0.0197(3) Uani d . 1 1
H H20A 0.5401 -0.3132 0.9316 0.024 Uiso calc R 1 1
H H20B 0.4540 -0.3177 0.8149 0.024 Uiso calc R 1 1
C C21 0.33508(15) -0.35963(9) 0.92449(11) 0.0262(3) Uani d . 1 1
H H21A 0.3317 -0.3456 0.9972 0.039 Uiso calc R 1 1
H H21B 0.3589 -0.4223 0.9188 0.039 Uiso calc R 1 1
H H21C 0.2435 -0.3478 0.8810 0.039 Uiso calc R 1 1
H H3A 0.4031(17) -0.0341(11) 0.8798(12) 0.030(4) Uiso d . 1 1
N N1 0.32840(10) 0.21097(7) 0.85512(8) 0.0172(2) Uani d . 1 1
N N2 0.43854(10) 0.25859(7) 0.82022(8) 0.0182(2) Uani d . 1 1
N N3 0.48854(11) -0.04789(7) 0.85966(8) 0.0172(2) Uani d . 1 1
O O1 0.27412(9) 0.06007(6) 0.88848(7) 0.0195(2) Uani d . 1 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
C6 C1 C2 119.87(11)
C6 C1 N1 119.04(11)
C2 C1 N1 121.09(11)
C3 C2 C1 119.18(13)
C3 C2 H2 120.4
C1 C2 H2 120.4
C4 C3 C2 121.15(12)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 119.28(12)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 120.60(13)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 119.90(12)
C5 C6 H6 120.0
C1 C6 H6 120.0
O1 C7 N1 126.02(11)
O1 C7 C8 129.22(12)
N1 C7 C8 104.75(10)
C11 C8 C9 133.54(11)
C11 C8 C7 120.89(11)
C9 C8 C7 105.26(10)
N2 C9 C8 111.72(11)
N2 C9 C10 117.95(11)
C8 C9 C10 130.33(11)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 C8 118.83(11)
N3 C11 C12 118.58(11)
C8 C11 C12 122.56(11)
C17 C12 C13 119.83(11)
C17 C12 C11 121.06(10)
C13 C12 C11 119.10(10)
C14 C13 C12 119.75(11)
C14 C13 H13 120.1
C12 C13 H13 120.1
C15 C14 C13 120.14(11)
C15 C14 H14 119.9
C13 C14 H14 119.9
C16 C15 C14 120.05(11)
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C17 120.31(11)
C15 C16 H16 119.8
C17 C16 H16 119.8
C16 C17 C12 119.91(11)
C16 C17 H17 120.0
C12 C17 H17 120.0
N3 C18 C19 109.09(10)
N3 C18 H18A 109.9
C19 C18 H18A 109.9
N3 C18 H18B 109.9
C19 C18 H18B 109.9
H18A C18 H18B 108.3
C20 C19 C18 112.19(10)
C20 C19 H19A 109.2
C18 C19 H19A 109.2
C20 C19 H19B 109.2
C18 C19 H19B 109.2
H19A C19 H19B 107.9
C19 C20 C21 112.34(11)
C19 C20 H20A 109.1
C21 C20 H20A 109.1
C19 C20 H20B 109.1
C21 C20 H20B 109.1
H20A C20 H20B 107.9
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C7 N1 N2 111.99(9)
C7 N1 C1 129.28(10)
N2 N1 C1 118.52(10)
C9 N2 N1 106.27(10)
C11 N3 C18 127.75(10)
C11 N3 H3A 113.8(10)
C18 N3 H3A 118.3(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3942(18)
C1 C2 1.3975(17)
C1 N1 1.4125(15)
C2 C3 1.3906(18)
C2 H2 0.9300
C3 C4 1.3827(19)
C3 H3 0.9300
C4 C5 1.3879(19)
C4 H4 0.9300
C5 C6 1.3858(18)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.2516(15)
C7 N1 1.3819(16)
C7 C8 1.4418(16)
C8 C11 1.4023(17)
C8 C9 1.4373(17)
C9 N2 1.3117(16)
C9 C10 1.4971(16)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 N3 1.3230(15)
C11 C12 1.4872(16)
C12 C17 1.3914(16)
C12 C13 1.3956(16)
C13 C14 1.3876(17)
C13 H13 0.9300
C14 C15 1.3861(18)
C14 H14 0.9300
C15 C16 1.3838(18)
C15 H15 0.9300
C16 C17 1.3840(17)
C16 H16 0.9300
C17 H17 0.9300
C18 N3 1.4633(16)
C18 C19 1.5171(16)
C18 H18A 0.9700
C18 H18B 0.9700
C19 C20 1.5169(17)
C19 H19A 0.9700
C19 H19B 0.9700
C20 C21 1.5218(18)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
N1 N2 1.4030(14)
N3 H3A 0.921(16)
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
N3 H3A O1 . 0.921(16) 1.873(16) 2.6704(14) 143.5(14)
C13 H13 O1 3_657 0.93 2.39 3.3175(15) 172
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
C6 C1 C2 C3 -0.55(16)
N1 C1 C2 C3 179.27(10)
C1 C2 C3 C4 1.43(17)
C2 C3 C4 C5 -1.14(18)
C3 C4 C5 C6 -0.03(18)
C4 C5 C6 C1 0.89(17)
C2 C1 C6 C5 -0.60(17)
N1 C1 C6 C5 179.59(10)
O1 C7 C8 C11 -4.43(18)
N1 C7 C8 C11 174.38(10)
O1 C7 C8 C9 -178.92(11)
N1 C7 C8 C9 -0.11(11)
C11 C8 C9 N2 -173.37(12)
C7 C8 C9 N2 0.10(13)
C11 C8 C9 C10 6.6(2)
C7 C8 C9 C10 -179.93(11)
C9 C8 C11 N3 174.20(12)
C7 C8 C11 N3 1.54(16)
C9 C8 C11 C12 -3.62(19)
C7 C8 C11 C12 -176.27(10)
N3 C11 C12 C17 116.65(13)
C8 C11 C12 C17 -65.53(16)
N3 C11 C12 C13 -64.14(15)
C8 C11 C12 C13 113.67(13)
C17 C12 C13 C14 0.82(18)
C11 C12 C13 C14 -178.40(11)
C12 C13 C14 C15 -0.77(19)
C13 C14 C15 C16 0.0(2)
C14 C15 C16 C17 0.8(2)
C15 C16 C17 C12 -0.76(19)
C13 C12 C17 C16 -0.06(18)
C11 C12 C17 C16 179.14(11)
N3 C18 C19 C20 176.92(9)
C18 C19 C20 C21 177.25(10)
O1 C7 N1 N2 178.95(10)
C8 C7 N1 N2 0.09(12)
O1 C7 N1 C1 4.41(19)
C8 C7 N1 C1 -174.45(10)
C6 C1 N1 C7 174.10(11)
C2 C1 N1 C7 -5.72(17)
C6 C1 N1 N2 -0.14(15)
C2 C1 N1 N2 -179.96(10)
C8 C9 N2 N1 -0.04(12)
C10 C9 N2 N1 179.98(9)
C7 N1 N2 C9 -0.03(12)
C1 N1 N2 C9 175.16(9)
C8 C11 N3 C18 173.83(11)
C12 C11 N3 C18 -8.27(17)
C19 C18 N3 C11 -173.20(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657580
