#------------------------------------------------------------------------------
#$Date: 2022-03-30 05:02:56 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566718.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_1566718
loop_
_publ_author_name
'Meenatchi, C. Selva'
'Athimoolam, S.'
'Suresh, J.'
'Priya, R. Vishnu'
'Rubina, S. Raja'
'Bhandari, S. R.'
_publ_section_title
;
 (E)-5-(4-Methylbenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one
;
_journal_coeditor_code           TK4075
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x220283
_journal_paper_doi               10.1107/S2414314622002838
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C21 H18 N2 O'
_chemical_formula_moiety         'C21 H18 N2 O'
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_chemical_name_systematic
(E)-5-(4-Methylbenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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
_cell_angle_beta                 115.367(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.3989(15)
_cell_length_b                   8.7177(5)
_cell_length_c                   14.0581(7)
_cell_measurement_reflns_used    3243
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      1.8
_cell_measurement_theta_min      28.7
_cell_volume                     3366.3(3)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al.,
2020) and
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ 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  0.0482
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22457
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         2.900
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.175
_refine_ls_extinction_coef       0.075(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+1.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                2557
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tk4075sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1566718
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.67927(8) 0.0162(3) 1.06046(15) 0.0789(6) Uani d 1 . .
H H1 0.6816 -0.0935 1.0667 0.118 Uiso calc 1 . .
H H9 0.6614 0.0543 1.0977 0.118 Uiso calc 1 . .
H H10 0.7114 0.0599 1.0900 0.118 Uiso calc 1 . .
C C2 0.65323(6) 0.0598(2) 0.94602(13) 0.0543(4) Uani d 1 . .
C C3 0.66930(6) 0.1813(2) 0.90557(14) 0.0586(5) Uani d 1 . .
H H11 0.6970 0.2352 0.9496 0.070 Uiso calc 1 . .
C C4 0.64503(6) 0.2237(2) 0.80118(14) 0.0550(4) Uani d 1 . .
H H6 0.6572 0.3038 0.7758 0.066 Uiso calc 1 . .
C C5 0.60276(5) 0.14887(18) 0.73320(12) 0.0450(4) Uani d 1 . .
C C6 0.57687(6) 0.20157(19) 0.62334(12) 0.0487(4) Uani d 1 . .
H H12 0.5965 0.2260 0.5899 0.058 Uiso calc 1 . .
C C7 0.52919(6) 0.21900(18) 0.56538(11) 0.0445(4) Uani d 1 . .
C C8 0.48996(6) 0.1884(2) 0.60232(12) 0.0516(4) Uani d 1 . .
H H13 0.5052 0.1753 0.6781 0.062 Uiso calc 1 . .
H H14 0.4736 0.0931 0.5713 0.062 Uiso calc 1 . .
C C9 0.45177(5) 0.3169(2) 0.57388(11) 0.0462(4) Uani d 1 . .
H H15 0.4246 0.2838 0.5876 0.055 Uiso calc 1 . .
H H16 0.4660 0.4074 0.6160 0.055 Uiso calc 1 . .
C C10 0.43483(5) 0.35272(17) 0.45978(11) 0.0416(4) Uani d 1 . .
C C11 0.34983(5) 0.45572(19) 0.40541(12) 0.0487(4) Uani d 1 . .
C C12 0.35632(6) 0.5344(2) 0.49555(13) 0.0541(4) Uani d 1 . .
H H4 0.3875 0.5536 0.5471 0.065 Uiso calc 1 . .
C C13 0.31616(7) 0.5847(2) 0.50901(16) 0.0657(5) Uani d 1 . .
H H3 0.3205 0.6369 0.5701 0.079 Uiso calc 1 . .
C C14 0.27001(7) 0.5582(3) 0.43271(17) 0.0761(6) Uani d 1 . .
H H2 0.2431 0.5928 0.4417 0.091 Uiso calc 1 . .
C C15 0.51236(6) 0.27563(18) 0.45440(11) 0.0449(4) Uani d 1 . .
C C16 0.46258(6) 0.32941(18) 0.40502(11) 0.0440(4) Uani d 1 . .
C C17 0.43202(6) 0.3710(2) 0.30018(12) 0.0518(4) Uani d 1 . .
H H5 0.4413 0.3674 0.2453 0.062 Uiso calc 1 . .
C C18 0.61226(6) -0.01863(19) 0.87812(13) 0.0545(4) Uani d 1 . .
H H8 0.6013 -0.1025 0.9029 0.065 Uiso calc 1 . .
C C19 0.58722(6) 0.02523(18) 0.77400(13) 0.0509(4) Uani d 1 . .
H H7 0.5595 -0.0287 0.7304 0.061 Uiso calc 1 . .
C C20 0.30333(6) 0.4275(3) 0.32794(14) 0.0679(5) Uani d 1 . .
H H18 0.2989 0.3743 0.2671 0.081 Uiso calc 1 . .
C C21 0.26374(7) 0.4799(3) 0.34264(17) 0.0825(7) Uani d 1 . .
H H17 0.2324 0.4620 0.2910 0.099 Uiso calc 1 . .
N N1 0.39101(4) 0.40554(15) 0.38972(9) 0.0463(3) Uani d 1 . .
N N2 0.38894(5) 0.41551(17) 0.28944(10) 0.0550(4) Uani d 1 . .
O O1 0.53899(4) 0.27719(16) 0.40893(9) 0.0624(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
C2 C1 H1 . . 109.5 ?
C2 C1 H9 . . 109.5 ?
H1 C1 H9 . . 109.5 ?
C2 C1 H10 . . 109.5 ?
H1 C1 H10 . . 109.5 ?
H9 C1 H10 . . 109.5 ?
C18 C2 C3 . . 117.79(15) ?
C18 C2 C1 . . 121.21(17) ?
C3 C2 C1 . . 120.99(17) ?
C4 C3 C2 . . 121.26(16) ?
C4 C3 H11 . . 119.4 ?
C2 C3 H11 . . 119.4 ?
C3 C4 C5 . . 121.32(16) ?
C3 C4 H6 . . 119.3 ?
C5 C4 H6 . . 119.3 ?
C4 C5 C19 . . 117.09(14) ?
C4 C5 C6 . . 119.64(14) ?
C19 C5 C6 . . 123.27(14) ?
C7 C6 C5 . . 128.94(14) ?
C7 C6 H12 . . 115.5 ?
C5 C6 H12 . . 115.5 ?
C6 C7 C15 . . 118.02(14) ?
C6 C7 C8 . . 125.46(13) ?
C15 C7 C8 . . 116.51(13) ?
C7 C8 C9 . . 113.58(13) ?
C7 C8 H13 . . 108.8 ?
C9 C8 H13 . . 108.8 ?
C7 C8 H14 . . 108.8 ?
C9 C8 H14 . . 108.8 ?
H13 C8 H14 . . 107.7 ?
C10 C9 C8 . . 107.83(12) ?
C10 C9 H15 . . 110.1 ?
C8 C9 H15 . . 110.1 ?
C10 C9 H16 . . 110.1 ?
C8 C9 H16 . . 110.1 ?
H15 C9 H16 . . 108.5 ?
N1 C10 C16 . . 106.89(12) ?
N1 C10 C9 . . 129.20(13) ?
C16 C10 C9 . . 123.85(13) ?
C12 C11 C20 . . 120.41(16) ?
C12 C11 N1 . . 120.27(13) ?
C20 C11 N1 . . 119.30(15) ?
C11 C12 C13 . . 119.73(16) ?
C11 C12 H4 . . 120.1 ?
C13 C12 H4 . . 120.1 ?
C14 C13 C12 . . 120.38(19) ?
C14 C13 H3 . . 119.8 ?
C12 C13 H3 . . 119.8 ?
C13 C14 C21 . . 119.64(18) ?
C13 C14 H2 . . 120.2 ?
C21 C14 H2 . . 120.2 ?
O1 C15 C16 . . 122.29(13) ?
O1 C15 C7 . . 122.50(14) ?
C16 C15 C7 . . 115.20(12) ?
C10 C16 C17 . . 104.99(13) ?
C10 C16 C15 . . 122.98(13) ?
C17 C16 C15 . . 132.02(14) ?
N2 C17 C16 . . 111.97(14) ?
N2 C17 H5 . . 124.0 ?
C16 C17 H5 . . 124.0 ?
C2 C18 C19 . . 121.22(16) ?
C2 C18 H8 . . 119.4 ?
C19 C18 H8 . . 119.4 ?
C18 C19 C5 . . 121.25(15) ?
C18 C19 H7 . . 119.4 ?
C5 C19 H7 . . 119.4 ?
C21 C20 C11 . . 118.89(19) ?
C21 C20 H18 . . 120.6 ?
C11 C20 H18 . . 120.6 ?
C14 C21 C20 . . 120.94(18) ?
C14 C21 H17 . . 119.5 ?
C20 C21 H17 . . 119.5 ?
C10 N1 N2 . . 111.28(12) ?
C10 N1 C11 . . 130.21(12) ?
N2 N1 C11 . . 118.44(12) ?
C17 N2 N1 . . 104.86(12) ?
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
C1 C2 . 1.506(2) ?
C1 H1 . 0.9600 ?
C1 H9 . 0.9600 ?
C1 H10 . 0.9600 ?
C2 C18 . 1.382(2) ?
C2 C3 . 1.386(3) ?
C3 C4 . 1.381(2) ?
C3 H11 . 0.9300 ?
C4 C5 . 1.392(2) ?
C4 H6 . 0.9300 ?
C5 C19 . 1.395(2) ?
C5 C6 . 1.474(2) ?
C6 C7 . 1.333(2) ?
C6 H12 . 0.9300 ?
C7 C15 . 1.502(2) ?
C7 C8 . 1.514(2) ?
C8 C9 . 1.538(2) ?
C8 H13 . 0.9700 ?
C8 H14 . 0.9700 ?
C9 C10 . 1.4925(19) ?
C9 H15 . 0.9700 ?
C9 H16 . 0.9700 ?
C10 N1 . 1.3535(18) ?
C10 C16 . 1.379(2) ?
C11 C12 . 1.379(2) ?
C11 C20 . 1.388(2) ?
C11 N1 . 1.430(2) ?
C12 C13 . 1.384(2) ?
C12 H4 . 0.9300 ?
C13 C14 . 1.372(3) ?
C13 H3 . 0.9300 ?
C14 C21 . 1.378(3) ?
C14 H2 . 0.9300 ?
C15 O1 . 1.2279(18) ?
C15 C16 . 1.446(2) ?
C16 C17 . 1.412(2) ?
C17 N2 . 1.311(2) ?
C17 H5 . 0.9300 ?
C18 C19 . 1.383(2) ?
C18 H8 . 0.9300 ?
C19 H7 . 0.9300 ?
C20 C21 . 1.383(3) ?
C20 H18 . 0.9300 ?
C21 H17 . 0.9300 ?
N1 N2 . 1.3867(17) ?
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
C6 H12 O1 . 0.93 2.43 2.806(2) 104
C12 H4 O1 5_666 0.93 2.52 3.312(2) 143
C17 H5 O1 2_655 0.93 2.60 3.5081(19) 164
C18 H8 O1 6_556 0.93 2.46 3.325(2) 155
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
C18 C2 C3 C4 . . . . 0.6(3) ?
C1 C2 C3 C4 . . . . -178.75(18) ?
C2 C3 C4 C5 . . . . 1.8(3) ?
C3 C4 C5 C19 . . . . -2.7(2) ?
C3 C4 C5 C6 . . . . 177.62(15) ?
C4 C5 C6 C7 . . . . -137.43(18) ?
C19 C5 C6 C7 . . . . 42.9(3) ?
C5 C6 C7 C15 . . . . 179.80(15) ?
C5 C6 C7 C8 . . . . 0.7(3) ?
C6 C7 C8 C9 . . . . 133.31(17) ?
C15 C7 C8 C9 . . . . -45.8(2) ?
C7 C8 C9 C10 . . . . 49.38(18) ?
C8 C9 C10 N1 . . . . 150.39(16) ?
C8 C9 C10 C16 . . . . -26.6(2) ?
C20 C11 C12 C13 . . . . 0.4(3) ?
N1 C11 C12 C13 . . . . 178.88(16) ?
C11 C12 C13 C14 . . . . -0.7(3) ?
C12 C13 C14 C21 . . . . 0.5(3) ?
C6 C7 C15 O1 . . . . 14.8(2) ?
C8 C7 C15 O1 . . . . -166.01(16) ?
C6 C7 C15 C16 . . . . -164.78(15) ?
C8 C7 C15 C16 . . . . 14.4(2) ?
N1 C10 C16 C17 . . . . -0.32(17) ?
C9 C10 C16 C17 . . . . 177.24(15) ?
N1 C10 C16 C15 . . . . 178.78(14) ?
C9 C10 C16 C15 . . . . -3.7(2) ?
O1 C15 C16 C10 . . . . -168.78(15) ?
C7 C15 C16 C10 . . . . 10.8(2) ?
O1 C15 C16 C17 . . . . 10.0(3) ?
C7 C15 C16 C17 . . . . -170.40(16) ?
C10 C16 C17 N2 . . . . -0.38(19) ?
C15 C16 C17 N2 . . . . -179.36(16) ?
C3 C2 C18 C19 . . . . -1.9(3) ?
C1 C2 C18 C19 . . . . 177.42(17) ?
C2 C18 C19 C5 . . . . 0.9(3) ?
C4 C5 C19 C18 . . . . 1.3(2) ?
C6 C5 C19 C18 . . . . -178.96(15) ?
C12 C11 C20 C21 . . . . 0.1(3) ?
N1 C11 C20 C21 . . . . -178.39(18) ?
C13 C14 C21 C20 . . . . 0.0(4) ?
C11 C20 C21 C14 . . . . -0.3(3) ?
C16 C10 N1 N2 . . . . 0.89(17) ?
C9 C10 N1 N2 . . . . -176.49(15) ?
C16 C10 N1 C11 . . . . -176.18(15) ?
C9 C10 N1 C11 . . . . 6.4(3) ?
C12 C11 N1 C10 . . . . 36.0(2) ?
C20 C11 N1 C10 . . . . -145.48(17) ?
C12 C11 N1 N2 . . . . -140.90(16) ?
C20 C11 N1 N2 . . . . 37.6(2) ?
C16 C17 N2 N1 . . . . 0.89(19) ?
C10 N1 N2 C17 . . . . -1.10(18) ?
C11 N1 N2 C17 . . . . 176.35(14) ?

_cod_database_fobs_code 1566718
