#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226538.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_2226538
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
'Asiri, Abdullah M.'
'Khan, Salman A.'
_publ_section_title
;
 4-{(E)-[2-(4-Iodobutoxy)benzylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           IS2554
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1588
_journal_page_last               o1589
_journal_paper_doi               10.1107/S1600536810020374
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H24 I N3 O2'
_chemical_formula_moiety         'C22 H24 I N3 O2'
_chemical_formula_sum            'C22 H24 I N3 O2'
_chemical_formula_weight         489.34
_chemical_name_systematic
;
4-{(E)-[2-(4-Iodobutoxy)benzylidene]amino}-
1,5-dimethyl-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                 94.010(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5235(10)
_cell_length_b                   16.4156(14)
_cell_length_c                   11.2828(9)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.43
_cell_measurement_theta_min      2.74
_cell_volume                     2129.1(3)
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type
;
Bruker APEXII DUO 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36214
_diffrn_reflns_theta_full        35.59
_diffrn_reflns_theta_max         35.59
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  0.6625
_exptl_absorpt_correction_T_min  0.5714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blcok
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         1.262
_refine_diff_density_min         -1.679
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         9632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1027P)²+1.5532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1585
_reflns_number_gt                7935
_reflns_number_total             9632
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2554.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226538
_cod_database_fobs_code          2226538
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.290561(14) 0.362436(10) 0.802978(17) 0.03475(7) Uani d . 1 . .
O O1 0.68399(13) 0.05872(8) 0.94462(12) 0.0192(2) Uani d . 1 . .
O O2 0.71122(14) 0.22745(9) 0.66181(13) 0.0206(2) Uani d . 1 . .
N N1 0.76696(14) -0.05557(10) 1.03829(14) 0.0182(3) Uani d . 1 . .
N N2 0.87138(14) -0.09878(10) 1.03161(15) 0.0200(3) Uani d . 1 . .
N N3 0.89080(14) 0.03071(9) 0.78003(13) 0.0163(2) Uani d . 1 . .
C C1 0.78638(19) -0.05051(15) 1.25448(18) 0.0266(4) Uani d . 1 . .
H H1A 0.8669 -0.0531 1.2531 0.032 Uiso calc R 1 . .
C C2 0.7339(2) -0.04626(17) 1.36239(19) 0.0315(5) Uani d . 1 . .
H H2A 0.7798 -0.0461 1.4336 0.038 Uiso calc R 1 . .
C C3 0.6135(2) -0.04230(14) 1.3637(2) 0.0275(4) Uani d . 1 . .
H H3A 0.5791 -0.0395 1.4357 0.033 Uiso calc R 1 . .
C C4 0.54450(18) -0.04253(12) 1.25739(19) 0.0232(3) Uani d . 1 . .
H H4A 0.4640 -0.0392 1.2586 0.028 Uiso calc R 1 . .
C C5 0.59526(17) -0.04769(11) 1.14967(18) 0.0199(3) Uani d . 1 . .
H H5A 0.5492 -0.0490 1.0786 0.024 Uiso calc R 1 . .
C C6 0.71592(17) -0.05082(11) 1.14923(16) 0.0186(3) Uani d . 1 . .
C C7 0.92082(16) -0.07340(11) 0.93152(15) 0.0172(3) Uani d . 1 . .
C C8 0.85924(15) -0.00877(10) 0.88180(15) 0.0156(3) Uani d . 1 . .
C C9 0.75980(16) 0.00540(10) 0.95158(15) 0.0161(3) Uani d . 1 . .
C C10 0.82737(16) 0.09014(10) 0.73798(15) 0.0166(3) Uani d . 1 . .
H H10A 0.7665 0.1092 0.7803 0.020 Uiso calc R 1 . .
C C11 0.85006(16) 0.12799(10) 0.62451(15) 0.0160(3) Uani d . 1 . .
C C12 0.93106(16) 0.09552(11) 0.55089(16) 0.0184(3) Uani d . 1 . .
H H12A 0.9768 0.0516 0.5775 0.022 Uiso calc R 1 . .
C C13 0.94457(18) 0.12744(12) 0.43891(17) 0.0209(3) Uani d . 1 . .
H H13A 0.9995 0.1057 0.3912 0.025 Uiso calc R 1 . .
C C14 0.87488(18) 0.19228(12) 0.39885(16) 0.0210(3) Uani d . 1 . .
H H14A 0.8814 0.2124 0.3226 0.025 Uiso calc R 1 . .
C C15 0.79573(17) 0.22751(11) 0.47051(16) 0.0195(3) Uani d . 1 . .
H H15A 0.7510 0.2717 0.4432 0.023 Uiso calc R 1 . .
C C16 0.78371(16) 0.19599(10) 0.58414(15) 0.0167(3) Uani d . 1 . .
C C17 0.64112(18) 0.29607(12) 0.62471(18) 0.0224(3) Uani d . 1 . .
H H17A 0.5886 0.2813 0.5572 0.027 Uiso calc R 1 . .
H H17B 0.6902 0.3403 0.6010 0.027 Uiso calc R 1 . .
C C18 0.57265(18) 0.32256(11) 0.72692(19) 0.0229(3) Uani d . 1 . .
H H18A 0.5220 0.3673 0.7010 0.027 Uiso calc R 1 . .
H H18B 0.6262 0.3426 0.7905 0.027 Uiso calc R 1 . .
C C19 0.49946(19) 0.25498(12) 0.7752(2) 0.0244(3) Uani d . 1 . .
H H19A 0.4505 0.2319 0.7103 0.029 Uiso calc R 1 . .
H H19B 0.5506 0.2122 0.8072 0.029 Uiso calc R 1 . .
C C20 0.4233(2) 0.28321(15) 0.8710(2) 0.0301(4) Uani d . 1 . .
H H20A 0.4709 0.3111 0.9327 0.036 Uiso calc R 1 . .
H H20B 0.3884 0.2362 0.9066 0.036 Uiso calc R 1 . .
C C21 0.8675(2) -0.18482(14) 1.0635(2) 0.0313(5) Uani d . 1 . .
H H21A 0.9438 -0.2080 1.0613 0.047 Uiso calc R 1 . .
H H21B 0.8147 -0.2129 1.0080 0.047 Uiso calc R 1 . .
H H21C 0.8414 -0.1902 1.1421 0.047 Uiso calc R 1 . .
C C22 1.02298(18) -0.11555(13) 0.88815(18) 0.0223(3) Uani d . 1 . .
H H22A 1.0828 -0.1196 0.9515 0.033 Uiso calc R 1 . .
H H22B 1.0517 -0.0852 0.8236 0.033 Uiso calc R 1 . .
H H22C 1.0008 -0.1692 0.8612 0.033 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'
I I -0.4742 1.8119 '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
C16 O2 C17 . . 118.14(15) ?
C9 N1 N2 . . 109.46(14) ?
C9 N1 C6 . . 124.67(15) ?
N2 N1 C6 . . 118.95(15) ?
C7 N2 N1 . . 107.41(14) ?
C7 N2 C21 . . 121.40(17) ?
N1 N2 C21 . . 115.78(16) ?
C10 N3 C8 . . 118.86(15) ?
C6 C1 C2 . . 118.8(2) ?
C6 C1 H1A . . 120.6 ?
C2 C1 H1A . . 120.6 ?
C3 C2 C1 . . 120.3(2) ?
C3 C2 H2A . . 119.9 ?
C1 C2 H2A . . 119.9 ?
C2 C3 C4 . . 120.08(19) ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C5 C4 C3 . . 120.3(2) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
C4 C5 C6 . . 119.19(18) ?
C4 C5 H5A . . 120.4 ?
C6 C5 H5A . . 120.4 ?
C1 C6 C5 . . 121.36(18) ?
C1 C6 N1 . . 119.94(18) ?
C5 C6 N1 . . 118.69(17) ?
N2 C7 C8 . . 109.87(15) ?
N2 C7 C22 . . 121.27(16) ?
C8 C7 C22 . . 128.82(16) ?
C7 C8 N3 . . 122.69(16) ?
C7 C8 C9 . . 107.86(15) ?
N3 C8 C9 . . 129.42(15) ?
O1 C9 N1 . . 123.96(16) ?
O1 C9 C8 . . 131.28(16) ?
N1 C9 C8 . . 104.73(14) ?
N3 C10 C11 . . 120.79(16) ?
N3 C10 H10A . . 119.6 ?
C11 C10 H10A . . 119.6 ?
C12 C11 C16 . . 118.64(16) ?
C12 C11 C10 . . 121.71(16) ?
C16 C11 C10 . . 119.52(16) ?
C13 C12 C11 . . 121.30(17) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C12 C13 C14 . . 119.12(18) ?
C12 C13 H13A . . 120.4 ?
C14 C13 H13A . . 120.4 ?
C15 C14 C13 . . 121.23(17) ?
C15 C14 H14A . . 119.4 ?
C13 C14 H14A . . 119.4 ?
C14 C15 C16 . . 119.45(17) ?
C14 C15 H15A . . 120.3 ?
C16 C15 H15A . . 120.3 ?
O2 C16 C15 . . 123.87(16) ?
O2 C16 C11 . . 115.96(15) ?
C15 C16 C11 . . 120.17(17) ?
O2 C17 C18 . . 108.56(15) ?
O2 C17 H17A . . 110.0 ?
C18 C17 H17A . . 110.0 ?
O2 C17 H17B . . 110.0 ?
C18 C17 H17B . . 110.0 ?
H17A C17 H17B . . 108.4 ?
C17 C18 C19 . . 113.44(16) ?
C17 C18 H18A . . 108.9 ?
C19 C18 H18A . . 108.9 ?
C17 C18 H18B . . 108.9 ?
C19 C18 H18B . . 108.9 ?
H18A C18 H18B . . 107.7 ?
C20 C19 C18 . . 113.41(18) ?
C20 C19 H19A . . 108.9 ?
C18 C19 H19A . . 108.9 ?
C20 C19 H19B . . 108.9 ?
C18 C19 H19B . . 108.9 ?
H19A C19 H19B . . 107.7 ?
C19 C20 I1 . . 111.76(15) ?
C19 C20 H20A . . 109.3 ?
I1 C20 H20A . . 109.3 ?
C19 C20 H20B . . 109.3 ?
I1 C20 H20B . . 109.3 ?
H20A C20 H20B . . 107.9 ?
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 ?
C7 C22 H22A . . 109.5 ?
C7 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C7 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
I1 C20 . 2.111(2) ?
O1 C9 . 1.235(2) ?
O2 C16 . 1.355(2) ?
O2 C17 . 1.432(2) ?
N1 C9 . 1.398(2) ?
N1 N2 . 1.403(2) ?
N1 C6 . 1.422(2) ?
N2 C7 . 1.365(2) ?
N2 C21 . 1.459(3) ?
N3 C10 . 1.289(2) ?
N3 C8 . 1.389(2) ?
C1 C6 . 1.391(3) ?
C1 C2 . 1.398(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.390(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.392(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.388(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.392(3) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.374(2) ?
C7 C22 . 1.478(3) ?
C8 C9 . 1.454(2) ?
C10 C11 . 1.463(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.398(3) ?
C11 C16 . 1.410(2) ?
C12 C13 . 1.387(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.390(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.387(3) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.398(2) ?
C15 H15A . 0.9300 ?
C17 C18 . 1.506(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.518(3) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.512(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
C10 H10A O1 . 0.93 2.30 2.995(2) 132 yes
C17 H17B O1 4_565 0.97 2.42 3.193(2) 137 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
C9 N1 N2 C7 . . . . -8.6(2) ?
C6 N1 N2 C7 . . . . -160.89(17) ?
C9 N1 N2 C21 . . . . -147.91(19) ?
C6 N1 N2 C21 . . . . 59.8(2) ?
C6 C1 C2 C3 . . . . -0.1(4) ?
C1 C2 C3 C4 . . . . 0.0(4) ?
C2 C3 C4 C5 . . . . 0.8(3) ?
C3 C4 C5 C6 . . . . -1.4(3) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
C2 C1 C6 N1 . . . . -179.6(2) ?
C4 C5 C6 C1 . . . . 1.3(3) ?
C4 C5 C6 N1 . . . . -179.60(17) ?
C9 N1 C6 C1 . . . . -116.1(2) ?
N2 N1 C6 C1 . . . . 31.7(3) ?
C9 N1 C6 C5 . . . . 64.8(3) ?
N2 N1 C6 C5 . . . . -147.45(18) ?
N1 N2 C7 C8 . . . . 7.2(2) ?
C21 N2 C7 C8 . . . . 143.72(19) ?
N1 N2 C7 C22 . . . . -170.71(17) ?
C21 N2 C7 C22 . . . . -34.2(3) ?
N2 C7 C8 N3 . . . . 178.79(16) ?
C22 C7 C8 N3 . . . . -3.5(3) ?
N2 C7 C8 C9 . . . . -3.2(2) ?
C22 C7 C8 C9 . . . . 174.55(19) ?
C10 N3 C8 C7 . . . . 178.99(17) ?
C10 N3 C8 C9 . . . . 1.4(3) ?
N2 N1 C9 O1 . . . . -171.71(17) ?
C6 N1 C9 O1 . . . . -21.4(3) ?
N2 N1 C9 C8 . . . . 6.5(2) ?
C6 N1 C9 C8 . . . . 156.82(17) ?
C7 C8 C9 O1 . . . . 175.93(19) ?
N3 C8 C9 O1 . . . . -6.2(3) ?
C7 C8 C9 N1 . . . . -2.11(19) ?
N3 C8 C9 N1 . . . . 175.74(17) ?
C8 N3 C10 C11 . . . . -173.62(16) ?
N3 C10 C11 C12 . . . . 7.8(3) ?
N3 C10 C11 C16 . . . . -176.25(17) ?
C16 C11 C12 C13 . . . . -1.8(3) ?
C10 C11 C12 C13 . . . . 174.17(18) ?
C11 C12 C13 C14 . . . . -0.9(3) ?
C12 C13 C14 C15 . . . . 2.6(3) ?
C13 C14 C15 C16 . . . . -1.6(3) ?
C17 O2 C16 C15 . . . . 1.2(3) ?
C17 O2 C16 C11 . . . . -179.42(17) ?
C14 C15 C16 O2 . . . . 178.16(18) ?
C14 C15 C16 C11 . . . . -1.2(3) ?
C12 C11 C16 O2 . . . . -176.58(16) ?
C10 C11 C16 O2 . . . . 7.4(2) ?
C12 C11 C16 C15 . . . . 2.8(3) ?
C10 C11 C16 C15 . . . . -173.23(17) ?
C16 O2 C17 C18 . . . . -177.32(16) ?
O2 C17 C18 C19 . . . . -55.7(2) ?
C17 C18 C19 C20 . . . . -175.30(18) ?
C18 C19 C20 I1 . . . . 67.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745203
