#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/95/2229554.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_2229554
loop_
_publ_author_name
'Abdel-Aziz, Hatem A.'
'Bari, Ahmed'
'Ng, Seik Weng'
_publ_section_title
;
 3-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-5-phenyl-1H-pyrazole-4-carbonitrile
;
_journal_coeditor_code           XU5162
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o694
_journal_paper_doi               10.1107/S1600536811005770
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C27 H21 N3 O2'
_chemical_formula_sum            'C27 H21 N3 O2'
_chemical_formula_weight         419.47
_chemical_name_systematic
;
3-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-5-
phenyl-1H-pyrazole-4-carbonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.113(6)
_cell_angle_beta                 111.582(6)
_cell_angle_gamma                118.219(7)
_cell_formula_units_Z            2
_cell_length_a                   10.9995(7)
_cell_length_b                   11.0531(8)
_cell_length_c                   11.4381(8)
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      2.2
_cell_volume                     1079.13(18)
_computing_cell_refinement       'CrysAlis PRO  (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO  (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO  (Agilent, 2010)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8250
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0530
_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)+(0.0431P)²+0.3112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                3346
_reflns_number_total             4779
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5162.cif
_cod_data_source_block           I
_cod_database_code               2229554
_cod_database_fobs_code          2229554
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.38684(16) 0.57825(15) 0.44798(13) 0.0300(3) Uani d . 1 . .
O O2 0.12051(18) 0.40793(16) 1.05036(14) 0.0367(4) Uani d . 1 . .
N N1 0.23698(18) 0.80105(17) 0.43686(15) 0.0234(4) Uani d . 1 . .
N N2 0.24257(18) 0.88927(17) 0.36089(15) 0.0224(4) Uani d . 1 . .
N N3 0.5147(2) 0.73362(19) 0.22677(18) 0.0346(4) Uani d . 1 . .
C C1 0.3312(2) 0.9656(2) 0.19190(18) 0.0240(4) Uani d . 1 . .
C C2 0.4740(2) 1.0450(2) 0.1918(2) 0.0279(4) Uani d . 1 . .
H H2 0.5633 1.0516 0.2562 0.033 Uiso calc R 1 . .
C C3 0.4859(3) 1.1146(2) 0.0974(2) 0.0333(5) Uani d . 1 . .
H H3 0.5835 1.1689 0.0975 0.040 Uiso calc R 1 . .
C C4 0.3566(3) 1.1051(2) 0.0037(2) 0.0345(5) Uani d . 1 . .
H H4 0.3654 1.1535 -0.0602 0.041 Uiso calc R 1 . .
C C5 0.2142(3) 1.0253(2) 0.0027(2) 0.0351(5) Uani d . 1 . .
H H5 0.1252 1.0183 -0.0626 0.042 Uiso calc R 1 . .
C C6 0.2004(2) 0.9555(2) 0.09631(19) 0.0296(5) Uani d . 1 . .
H H6 0.1024 0.9011 0.0954 0.036 Uiso calc R 1 . .
C C7 0.3174(2) 0.8880(2) 0.28932(18) 0.0232(4) Uani d . 1 . .
C C8 0.3647(2) 0.7940(2) 0.32243(18) 0.0231(4) Uani d . 1 . .
C C9 0.3105(2) 0.7419(2) 0.41342(18) 0.0230(4) Uani d . 1 . .
C C10 0.4468(2) 0.7579(2) 0.26995(19) 0.0253(4) Uani d . 1 . .
C C11 0.1709(2) 0.9692(2) 0.36361(17) 0.0219(4) Uani d . 1 . .
C C12 0.2558(2) 1.1174(2) 0.39088(18) 0.0242(4) Uani d . 1 . .
H H12 0.3621 1.1678 0.4095 0.029 Uiso calc R 1 . .
C C13 0.1838(2) 1.1919(2) 0.39070(18) 0.0258(4) Uani d . 1 . .
H H13 0.2418 1.2942 0.4103 0.031 Uiso calc R 1 . .
C C14 0.0275(2) 1.1190(2) 0.36219(18) 0.0237(4) Uani d . 1 . .
C C15 -0.0541(2) 0.9696(2) 0.33824(18) 0.0254(4) Uani d . 1 . .
H H15 -0.1599 0.9188 0.3211 0.031 Uiso calc R 1 . .
C C16 0.0174(2) 0.8946(2) 0.33918(17) 0.0235(4) Uani d . 1 . .
H H16 -0.0386 0.7929 0.3232 0.028 Uiso calc R 1 . .
C C17 -0.0532(3) 1.1984(2) 0.3558(2) 0.0328(5) Uani d . 1 . .
H H17A 0.0250 1.3027 0.3984 0.049 Uiso calc R 1 . .
H H17B -0.1163 1.1647 0.4020 0.049 Uiso calc R 1 . .
H H17C -0.1209 1.1796 0.2627 0.049 Uiso calc R 1 . .
C C18 0.3238(2) 0.6344(2) 0.47637(18) 0.0238(4) Uani d . 1 . .
C C19 0.2638(2) 0.6043(2) 0.57209(19) 0.0258(4) Uani d . 1 . .
H H19 0.1994 0.6368 0.5774 0.031 Uiso calc R 1 . .
C C20 0.2979(2) 0.5315(2) 0.65250(18) 0.0250(4) Uani d . 1 . .
H H20 0.3597 0.4983 0.6416 0.030 Uiso calc R 1 . .
C C21 0.2506(2) 0.4980(2) 0.75476(18) 0.0235(4) Uani d . 1 . .
C C22 0.3173(2) 0.4435(2) 0.84454(19) 0.0259(4) Uani d . 1 . .
H H22 0.3919 0.4272 0.8368 0.031 Uiso calc R 1 . .
C C23 0.2780(2) 0.4123(2) 0.94527(19) 0.0274(4) Uani d . 1 . .
H H23 0.3254 0.3755 1.0058 0.033 Uiso calc R 1 . .
C C24 0.1695(2) 0.4353(2) 0.95637(19) 0.0285(5) Uani d . 1 . .
C C25 0.0980(2) 0.4876(2) 0.8662(2) 0.0309(5) Uani d . 1 . .
H H25 0.0217 0.5016 0.8729 0.037 Uiso calc R 1 . .
C C26 0.1392(2) 0.5187(2) 0.7676(2) 0.0280(4) Uani d . 1 . .
H H26 0.0911 0.5550 0.7069 0.034 Uiso calc R 1 . .
C C27 0.1885(3) 0.3532(3) 1.1453(2) 0.0384(5) Uani d . 1 . .
H H27A 0.1401 0.3340 1.2040 0.058 Uiso calc R 1 . .
H H27B 0.3008 0.4251 1.1981 0.058 Uiso calc R 1 . .
H H27C 0.1710 0.2632 1.0988 0.058 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C24 O2 C27 . . 117.63(16) ?
C9 N1 N2 . . 105.08(14) ?
N1 N2 C7 . . 112.95(14) ?
N1 N2 C11 . . 118.61(14) ?
C7 N2 C11 . . 128.44(15) ?
C2 C1 C6 . . 119.62(18) ?
C2 C1 C7 . . 119.97(17) ?
C6 C1 C7 . . 120.36(18) ?
C3 C2 C1 . . 119.9(2) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 120.02(19) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.7(2) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N2 C7 C8 . . 105.58(16) ?
N2 C7 C1 . . 124.52(16) ?
C8 C7 C1 . . 129.79(17) ?
C7 C8 C9 . . 105.63(16) ?
C7 C8 C10 . . 125.37(17) ?
C9 C8 C10 . . 128.98(17) ?
N1 C9 C8 . . 110.75(16) ?
N1 C9 C18 . . 120.93(16) ?
C8 C9 C18 . . 128.29(17) ?
N3 C10 C8 . . 177.4(2) ?
C12 C11 C16 . . 121.29(17) ?
C12 C11 N2 . . 119.98(17) ?
C16 C11 N2 . . 118.73(17) ?
C11 C12 C13 . . 119.05(18) ?
C11 C12 H12 . . 120.5 ?
C13 C12 H12 . . 120.5 ?
C12 C13 C14 . . 120.95(18) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C13 C14 C15 . . 118.65(17) ?
C13 C14 C17 . . 121.14(18) ?
C15 C14 C17 . . 120.21(18) ?
C16 C15 C14 . . 120.69(18) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C11 C16 C15 . . 119.32(18) ?
C11 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O1 C18 C19 . . 123.83(18) ?
O1 C18 C9 . . 118.84(17) ?
C19 C18 C9 . . 117.31(16) ?
C20 C19 C18 . . 121.14(18) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C19 C20 C21 . . 127.01(18) ?
C19 C20 H20 . . 116.5 ?
C21 C20 H20 . . 116.5 ?
C22 C21 C26 . . 117.69(18) ?
C22 C21 C20 . . 119.60(17) ?
C26 C21 C20 . . 122.71(17) ?
C21 C22 C23 . . 121.73(18) ?
C21 C22 H22 . . 119.1 ?
C23 C22 H22 . . 119.1 ?
C24 C23 C22 . . 119.28(18) ?
C24 C23 H23 . . 120.4 ?
C22 C23 H23 . . 120.4 ?
O2 C24 C23 . . 124.75(18) ?
O2 C24 C25 . . 114.80(18) ?
C23 C24 C25 . . 120.44(18) ?
C26 C25 C24 . . 119.41(19) ?
C26 C25 H25 . . 120.3 ?
C24 C25 H25 . . 120.3 ?
C25 C26 C21 . . 121.43(18) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
O2 C27 H27A . . 109.5 ?
O2 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O2 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 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
O1 C18 . 1.228(2) ?
O2 C24 . 1.367(2) ?
O2 C27 . 1.432(2) ?
N1 C9 . 1.335(2) ?
N1 N2 . 1.358(2) ?
N2 C7 . 1.361(2) ?
N2 C11 . 1.440(2) ?
N3 C10 . 1.146(2) ?
C1 C2 . 1.391(3) ?
C1 C6 . 1.396(3) ?
C1 C7 . 1.474(3) ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.389(3) ?
C8 C9 . 1.417(3) ?
C8 C10 . 1.425(3) ?
C9 C18 . 1.481(3) ?
C11 C12 . 1.379(3) ?
C11 C16 . 1.380(3) ?
C12 C13 . 1.387(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.393(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.394(3) ?
C14 C17 . 1.505(3) ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.461(3) ?
C19 C20 . 1.340(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.456(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.390(3) ?
C21 C26 . 1.402(3) ?
C22 C23 . 1.389(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.378(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.399(3) ?
C25 C26 . 1.376(3) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
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
C12 H12 O1 2_676 0.95 2.59 3.350(3) 137 y
C22 H22 N3 2_666 0.95 2.61 3.487(3) 154 y
C25 H25 O2 2_567 0.95 2.56 3.484(3) 164 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656562
