#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:19:32 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311625.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_2311625
loop_
_publ_author_name
'Manjula, M.'
'Jayaroopa, P.'
'Manjunath, B. C.'
'Ajay Kumar, K.'
'Lokanath, N. K.'
_publ_section_title
;
 3-Methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole.
;
_journal_coeditor_code           HB7053
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o602
_journal_paper_doi               10.1107/S1600536813007575
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H16 N2'
_chemical_formula_moiety         'C16 H16 N2'
_chemical_formula_structural     'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_formula_weight         236.31
_chemical_melting_point_gt       363
_chemical_melting_point_lt       365
_chemical_name_systematic
;
3-Methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole
;
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 132.207(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1224(17)
_cell_length_b                   7.8055(6)
_cell_length_c                   12.5057(13)
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    301
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1310.3(3)
_computing_cell_refinement       'CrysAlisPRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'Mercury (Macrae et al., 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      301
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       '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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_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            11856
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2362
_reflns_number_total             2973
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7053sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2311625
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x,-y,1/2+z
3 1/2+x,1/2+y,z
4 1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.57189(12) 0.5350(3) 0.53221(17) 0.0583(6) Uani d . 1.000
N N2 0.63012(12) 0.5538(2) 0.49747(18) 0.0528(5) Uani d . 1.000
C C1 0.43700(15) 0.4218(3) 0.2954(2) 0.0539(6) Uani d . 1.000
C C2 0.34060(17) 0.3632(3) 0.1948(2) 0.0683(7) Uani d . 1.000
C C3 0.27852(16) 0.3631(3) 0.2214(3) 0.0694(7) Uani d . 1.000
C C4 0.31410(16) 0.4245(3) 0.3516(3) 0.0617(7) Uani d . 1.000
C C5 0.41076(14) 0.4857(2) 0.4546(2) 0.0529(6) Uani d . 1.000
C C6 0.47391(13) 0.4829(2) 0.42818(19) 0.0439(5) Uani d . 1.000
C C7 0.62148(15) 0.5986(2) 0.6767(2) 0.0487(5) Uani d . 1.000
C C8 0.58591(12) 0.7740(2) 0.67789(18) 0.0425(5) Uani d . 1.000
C C9 0.53469(16) 0.8844(3) 0.5615(2) 0.0558(6) Uani d . 1.000
C C10 0.50989(18) 1.0475(3) 0.5715(3) 0.0710(8) Uani d . 1.000
C C11 0.53636(18) 1.1018(3) 0.6979(3) 0.0725(9) Uani d . 1.000
C C12 0.58650(17) 0.9929(3) 0.8138(3) 0.0644(8) Uani d . 1.000
C C13 0.61057(14) 0.8294(3) 0.80360(19) 0.0502(6) Uani d . 1.000
C C14 0.73007(16) 0.6028(3) 0.7433(2) 0.0618(6) Uani d . 1.000
C C15 0.71843(15) 0.5947(2) 0.6134(2) 0.0563(6) Uani d . 1.000
C C16 0.8000(2) 0.6260(4) 0.6152(4) 0.0878(11) Uani d . 1.000
H H1 0.47760 0.42050 0.27480 0.0650 Uiso c R 1.000
H H2 0.31700 0.32270 0.10660 0.0820 Uiso c R 1.000
H H3 0.21360 0.32240 0.15260 0.0830 Uiso c R 1.000
H H4 0.27280 0.42500 0.37110 0.0740 Uiso c R 1.000
H H5 0.43330 0.52860 0.54160 0.0640 Uiso c R 1.000
H H7 0.61430 0.51580 0.72810 0.0580 Uiso c R 1.000
H H9 0.51670 0.84890 0.47570 0.0670 Uiso c R 1.000
H H10 0.47520 1.12070 0.49240 0.0850 Uiso c R 1.000
H H11 0.52030 1.21200 0.70480 0.0870 Uiso c R 1.000
H H12 0.60430 1.02910 0.89940 0.0770 Uiso c R 1.000
H H13 0.64380 0.75570 0.88220 0.0600 Uiso c R 1.000
H H14A 0.76320 0.70760 0.79730 0.0740 Uiso c R 1.000
H H14B 0.76730 0.50530 0.80630 0.0740 Uiso c R 1.000
H H16A 0.77370 0.62300 0.51830 0.1320 Uiso c R 1.000
H H16B 0.85000 0.53900 0.67170 0.1320 Uiso c R 1.000
H H16C 0.82900 0.73640 0.65690 0.1320 Uiso c R 1.000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C6 120.09(17) n
N2 N1 C7 112.6(2) n
C6 N1 C7 126.7(2) n
N1 N2 C15 107.8(2) n
C2 C1 C6 120.1(3) no
C1 C2 C3 121.6(2) no
C2 C3 C4 118.6(3) no
C3 C4 C5 121.0(3) no
C4 C5 C6 120.2(2) no
N1 C6 C1 120.5(3) n
N1 C6 C5 121.00(18) n
C1 C6 C5 118.5(2) no
N1 C7 C8 113.95(16) n
N1 C7 C14 100.2(2) n
C8 C7 C14 111.89(18) no
C7 C8 C9 122.80(19) no
C7 C8 C13 118.56(16) no
C9 C8 C13 118.55(19) no
C8 C9 C10 120.5(2) no
C9 C10 C11 120.3(2) no
C10 C11 C12 119.7(2) no
C11 C12 C13 120.1(3) no
C8 C13 C12 120.8(2) no
C7 C14 C15 102.47(18) no
N2 C15 C14 113.4(3) n
N2 C15 C16 122.1(2) n
C14 C15 C16 124.5(2) no
C2 C1 H1 120.00 no
C6 C1 H1 120.00 no
C1 C2 H2 119.00 no
C3 C2 H2 119.00 no
C2 C3 H3 121.00 no
C4 C3 H3 121.00 no
C3 C4 H4 120.00 no
C5 C4 H4 119.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
N1 C7 H7 110.00 no
C8 C7 H7 110.00 no
C14 C7 H7 110.00 no
C8 C9 H9 120.00 no
C10 C9 H9 120.00 no
C9 C10 H10 120.00 no
C11 C10 H10 120.00 no
C10 C11 H11 120.00 no
C12 C11 H11 120.00 no
C11 C12 H12 120.00 no
C13 C12 H12 120.00 no
C8 C13 H13 120.00 no
C12 C13 H13 120.00 no
C7 C14 H14A 111.00 no
C7 C14 H14B 111.00 no
C15 C14 H14A 111.00 no
C15 C14 H14B 111.00 no
H14A C14 H14B 109.00 no
C15 C16 H16A 109.00 no
C15 C16 H16B 109.00 no
C15 C16 H16C 109.00 no
H16A C16 H16B 110.00 no
H16A C16 H16C 110.00 no
H16B C16 H16C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.393(4) n
N1 C6 1.381(3) n
N1 C7 1.462(3) n
N2 C15 1.284(3) n
C1 C2 1.375(4) no
C1 C6 1.393(3) no
C2 C3 1.371(5) no
C3 C4 1.373(4) no
C4 C5 1.387(4) no
C5 C6 1.388(4) no
C7 C8 1.518(3) no
C7 C14 1.538(4) no
C8 C9 1.381(3) no
C8 C13 1.384(3) no
C9 C10 1.383(4) no
C10 C11 1.375(4) no
C11 C12 1.371(4) no
C12 C13 1.382(4) no
C14 C15 1.492(3) no
C15 C16 1.484(6) no
C1 H1 0.9300 no
C2 H2 0.9300 no
C3 H3 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C7 H7 0.9800 no
C9 H9 0.9300 no
C10 H10 0.9300 no
C11 H11 0.9300 no
C12 H12 0.9300 no
C13 H13 0.9300 no
C14 H14A 0.9700 no
C14 H14B 0.9700 no
C16 H16A 0.9600 no
C16 H16B 0.9600 no
C16 H16C 0.9600 no
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
_geom_torsion_publ_flag
C6 N1 N2 C15 -176.91(18) no
C7 N1 N2 C15 11.2(2) no
N2 N1 C6 C1 10.6(3) no
N2 N1 C6 C5 -171.14(17) no
C7 N1 C6 C1 -178.8(2) no
C7 N1 C6 C5 -0.5(3) no
N2 N1 C7 C8 101.5(3) no
N2 N1 C7 C14 -18.2(2) no
C6 N1 C7 C8 -69.7(3) no
C6 N1 C7 C14 170.6(2) no
N1 N2 C15 C14 1.8(2) no
N1 N2 C15 C16 -179.6(2) no
C6 C1 C2 C3 0.1(3) no
C2 C1 C6 N1 177.2(2) no
C2 C1 C6 C5 -1.1(3) no
C1 C2 C3 C4 0.5(4) no
C2 C3 C4 C5 0.1(4) no
C3 C4 C5 C6 -1.1(3) no
C4 C5 C6 N1 -176.63(19) no
C4 C5 C6 C1 1.7(3) no
N1 C7 C8 C9 -18.0(4) no
N1 C7 C8 C13 165.6(2) no
C14 C7 C8 C9 94.8(3) no
C14 C7 C8 C13 -81.6(3) no
N1 C7 C14 C15 17.20(19) no
C8 C7 C14 C15 -103.93(19) no
C7 C8 C9 C10 -175.5(3) no
C13 C8 C9 C10 0.8(4) no
C7 C8 C13 C12 175.1(3) no
C9 C8 C13 C12 -1.4(4) no
C8 C9 C10 C11 0.3(5) no
C9 C10 C11 C12 -0.8(6) no
C10 C11 C12 C13 0.2(6) no
C11 C12 C13 C8 0.9(5) no
C7 C14 C15 N2 -12.9(2) no
C7 C14 C15 C16 168.6(2) no
