#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225230.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_2225230
loop_
_publ_author_name
'Susindran, V.'
'Athimoolam, S.'
'Bahadur, S. Asath'
'Sridhar, B.'
'Manikannan, R.'
'Muthusubramanian, S.'
_publ_section_title
;
 (E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazolyl)-2-propenal
;
_journal_coeditor_code           FJ2268
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o577
_journal_paper_doi               10.1107/S1600536810004332
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H14 N2 O'
_chemical_formula_moiety         'C18 H14 N2 O'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_chemical_name_common
;
(E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazolyl)-2-propenal
;
_chemical_name_systematic
;
(E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazolyl)-2-propenal
;
_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           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 113.091(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6157(7)
_cell_length_b                   18.0969(12)
_cell_length_c                   10.0861(6)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      1.7
_cell_volume                     1446.61(19)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            13719
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.8627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                2262
_reflns_number_total             2547
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2268.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2225230
_cod_database_fobs_code          2225230
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
N N1 0.61426(14) 0.02209(6) 0.24676(12) 0.0463(3) Uani d . 1 . .
N N2 0.74924(13) -0.01152(6) 0.23393(12) 0.0447(3) Uani d . 1 . .
C C3 0.81474(17) -0.05400(8) 0.34980(14) 0.0467(3) Uani d . 1 . .
C C4 0.7236(2) -0.04724(11) 0.43775(17) 0.0663(5) Uani d . 1 . .
H H4 0.7448 -0.0712 0.5247 0.080 Uiso calc R 1 . .
C C5 0.5990(2) 0.00119(10) 0.37010(17) 0.0649(5) Uani d . 1 . .
H H5 0.5172 0.0174 0.4022 0.078 Uiso calc R 1 . .
C C11 0.52083(16) 0.07517(7) 0.14569(14) 0.0432(3) Uani d . 1 . .
C C12 0.36253(17) 0.10037(7) 0.15681(14) 0.0442(3) Uani d . 1 . .
C C13 0.3380(2) 0.17479(9) 0.17313(18) 0.0573(4) Uani d . 1 . .
H H13 0.4230 0.2085 0.1821 0.069 Uiso calc R 1 . .
C C14 0.1874(2) 0.19915(10) 0.17617(19) 0.0690(5) Uani d . 1 . .
H H14 0.1716 0.2493 0.1871 0.083 Uiso calc R 1 . .
C C15 0.0613(2) 0.14992(10) 0.16317(18) 0.0653(5) Uani d . 1 . .
H H15 -0.0406 0.1667 0.1633 0.078 Uiso calc R 1 . .
C C16 0.08564(19) 0.07612(10) 0.14998(17) 0.0595(4) Uani d . 1 . .
H H16 0.0008 0.0427 0.1428 0.071 Uiso calc R 1 . .
C C17 0.23541(18) 0.05101(8) 0.14726(15) 0.0510(4) Uani d . 1 . .
H H17 0.2513 0.0007 0.1390 0.061 Uiso calc R 1 . .
C C31 0.96351(17) -0.09984(7) 0.37111(16) 0.0478(4) Uani d . 1 . .
C C32 1.0553(2) -0.13183(9) 0.50393(17) 0.0626(4) Uani d . 1 . .
H H32 1.0215 -0.1250 0.5801 0.075 Uiso calc R 1 . .
C C33 1.1966(2) -0.17376(10) 0.5237(2) 0.0757(5) Uani d . 1 . .
H H33 1.2567 -0.1955 0.6128 0.091 Uiso calc R 1 . .
C C34 1.2482(2) -0.18350(11) 0.4134(3) 0.0815(6) Uani d . 1 . .
H H34 1.3454 -0.2106 0.4281 0.098 Uiso calc R 1 . .
C C35 1.1569(2) -0.15340(10) 0.2805(2) 0.0772(5) Uani d . 1 . .
H H35 1.1913 -0.1608 0.2048 0.093 Uiso calc R 1 . .
C C36 1.0147(2) -0.11233(9) 0.25925(19) 0.0598(4) Uani d . 1 . .
H H36 0.9524 -0.0928 0.1686 0.072 Uiso calc R 1 . .
C C1A 0.57622(17) 0.10007(8) 0.04689(15) 0.0483(3) Uani d . 1 . .
H H1A 0.6831 0.0854 0.0552 0.058 Uiso calc R 1 . .
C C2A 0.48155(19) 0.14796(8) -0.07132(16) 0.0524(4) Uani d . 1 . .
H H2A 0.3733 0.1617 -0.0819 0.063 Uiso calc R 1 . .
O O1 0.53501(16) 0.17125(7) -0.15736(13) 0.0747(4) Uani d . 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
C5 N1 N2 . . 110.89(11) ?
C5 N1 C11 . . 128.59(12) ?
N2 N1 C11 . . 120.31(11) ?
C3 N2 N1 . . 105.02(11) ?
N2 C3 C4 . . 110.90(13) ?
N2 C3 C31 . . 120.10(13) ?
C4 C3 C31 . . 129.01(13) ?
C5 C4 C3 . . 105.64(14) ?
C5 C4 H4 . . 127.2 ?
C3 C4 H4 . . 127.2 ?
C4 C5 N1 . . 107.55(14) ?
C4 C5 H5 . . 126.2 ?
N1 C5 H5 . . 126.2 ?
C1A C11 N1 . . 120.03(12) ?
C1A C11 C12 . . 123.97(13) ?
N1 C11 C12 . . 116.00(12) ?
C13 C12 C17 . . 118.80(13) ?
C13 C12 C11 . . 119.78(13) ?
C17 C12 C11 . . 121.40(12) ?
C14 C13 C12 . . 120.15(15) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.42(16) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C16 C15 C14 . . 119.87(15) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.33(16) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C16 C17 C12 . . 120.40(14) ?
C16 C17 H17 . . 119.8 ?
C12 C17 H17 . . 119.8 ?
C36 C31 C32 . . 118.46(14) ?
C36 C31 C3 . . 120.81(13) ?
C32 C31 C3 . . 120.73(14) ?
C33 C32 C31 . . 120.37(17) ?
C33 C32 H32 . . 119.8 ?
C31 C32 H32 . . 119.8 ?
C34 C33 C32 . . 120.31(17) ?
C34 C33 H33 . . 119.8 ?
C32 C33 H33 . . 119.8 ?
C33 C34 C35 . . 120.04(17) ?
C33 C34 H34 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C34 C35 C36 . . 120.04(18) ?
C34 C35 H35 . . 120.0 ?
C36 C35 H35 . . 120.0 ?
C35 C36 C31 . . 120.73(16) ?
C35 C36 H36 . . 119.6 ?
C31 C36 H36 . . 119.6 ?
C11 C1A C2A . . 124.51(13) ?
C11 C1A H1A . . 117.7 ?
C2A C1A H1A . . 117.7 ?
O1 C2A C1A . . 123.61(14) ?
O1 C2A H2A . . 118.2 ?
C1A C2A H2A . . 118.2 ?
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
N1 C5 . 1.3552(19) ?
N1 N2 . 1.3627(15) ?
N1 C11 . 1.4023(18) ?
N2 C3 . 1.3259(17) ?
C3 C4 . 1.402(2) ?
C3 C31 . 1.470(2) ?
C4 C5 . 1.346(2) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C11 C1A . 1.340(2) ?
C11 C12 . 1.4835(18) ?
C12 C13 . 1.383(2) ?
C12 C17 . 1.387(2) ?
C13 C14 . 1.381(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.371(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.366(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.378(2) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C31 C36 . 1.382(2) ?
C31 C32 . 1.387(2) ?
C32 C33 . 1.380(2) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.363(3) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.373(3) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.376(2) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C1A C2A . 1.440(2) ?
C1A H1A . 0.9300 ?
C2A O1 . 1.2068(18) ?
C2A H2A . 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
C35 H35 O1 3_755 0.93 2.59 3.358(2) 140
C13 H13 O1 4_566 0.93 2.66 3.360(2) 133
C14 H14 Cg 2_655 0.93 2.95 3.703(2) 139
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
C5 N1 N2 C3 . . . . 0.88(16) ?
C11 N1 N2 C3 . . . . 175.96(12) ?
N1 N2 C3 C4 . . . . -0.64(16) ?
N1 N2 C3 C31 . . . . 179.26(12) ?
N2 C3 C4 C5 . . . . 0.2(2) ?
C31 C3 C4 C5 . . . . -179.71(15) ?
C3 C4 C5 N1 . . . . 0.4(2) ?
N2 N1 C5 C4 . . . . -0.8(2) ?
C11 N1 C5 C4 . . . . -175.36(15) ?
C5 N1 C11 C1A . . . . 165.51(15) ?
N2 N1 C11 C1A . . . . -8.60(19) ?
C5 N1 C11 C12 . . . . -14.5(2) ?
N2 N1 C11 C12 . . . . 171.43(11) ?
C1A C11 C12 C13 . . . . -56.2(2) ?
N1 C11 C12 C13 . . . . 123.79(15) ?
C1A C11 C12 C17 . . . . 122.03(16) ?
N1 C11 C12 C17 . . . . -58.00(17) ?
C17 C12 C13 C14 . . . . -1.6(2) ?
C11 C12 C13 C14 . . . . 176.68(14) ?
C12 C13 C14 C15 . . . . 0.0(3) ?
C13 C14 C15 C16 . . . . 1.3(3) ?
C14 C15 C16 C17 . . . . -1.1(3) ?
C15 C16 C17 C12 . . . . -0.5(2) ?
C13 C12 C17 C16 . . . . 1.8(2) ?
C11 C12 C17 C16 . . . . -176.44(13) ?
N2 C3 C31 C36 . . . . -14.4(2) ?
C4 C3 C31 C36 . . . . 165.51(16) ?
N2 C3 C31 C32 . . . . 165.91(14) ?
C4 C3 C31 C32 . . . . -14.2(2) ?
C36 C31 C32 C33 . . . . 1.4(2) ?
C3 C31 C32 C33 . . . . -178.88(15) ?
C31 C32 C33 C34 . . . . 0.7(3) ?
C32 C33 C34 C35 . . . . -1.9(3) ?
C33 C34 C35 C36 . . . . 1.1(3) ?
C34 C35 C36 C31 . . . . 1.1(3) ?
C32 C31 C36 C35 . . . . -2.3(2) ?
C3 C31 C36 C35 . . . . 178.02(15) ?
N1 C11 C1A C2A . . . . 172.66(13) ?
C12 C11 C1A C2A . . . . -7.4(2) ?
C11 C1A C2A O1 . . . . 178.19(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744446
