#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224869.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_2224869
loop_
_publ_author_name
'Khan, F. Nawaz'
'Manivel, P.'
'Kone, Sriramakrishnaswamy'
'Hathwar, Venkatesha R.'
'Ng, Seik Weng'
_publ_section_title
;
 3-Methyl-5-phenyl-1-(3-phenylisoquinolin-1-yl)-1H-pyrazole
;
_journal_coeditor_code           BT5159
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o368
_journal_paper_doi               10.1107/S160053680905572X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C25 H19 N3'
_chemical_formula_moiety         'C25 H19 N3'
_chemical_formula_sum            'C25 H19 N3'
_chemical_formula_weight         361.43
_chemical_name_systematic
;
3-Methyl-5-phenyl-1-(3-phenylisoquinolin-1-yl)-1H-pyrazole
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.9610(9)
_cell_length_b                   16.8078(13)
_cell_length_c                   21.3118(17)
_cell_measurement_reflns_used    1667
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      19.5
_cell_measurement_theta_min      2.4
_cell_volume                     3926.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      290(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 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  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26302
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0586
_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)+(0.0822P)²+0.3609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                2031
_reflns_number_total             3452
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5159.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224869
_cod_database_fobs_code          2224869
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.42399(17) 0.56804(11) 0.65341(8) 0.0632(5) Uani d . 1 . .
N N2 0.58627(17) 0.61748(12) 0.59624(9) 0.0707(6) Uani d . 1 . .
N N3 0.70861(18) 0.60123(14) 0.60212(10) 0.0846(7) Uani d . 1 . .
C C1 0.5164(2) 0.61722(15) 0.65309(11) 0.0634(6) Uani d . 1 . .
C C2 0.5528(2) 0.66672(14) 0.70362(11) 0.0633(6) Uani d . 1 . .
C C3 0.6493(2) 0.72259(17) 0.70207(14) 0.0799(8) Uani d . 1 . .
H H3 0.6940 0.7293 0.6654 0.096 Uiso calc R 1 . .
C C4 0.6771(3) 0.76627(17) 0.75330(18) 0.0925(9) Uani d . 1 . .
H H4 0.7414 0.8023 0.7517 0.111 Uiso calc R 1 . .
C C5 0.6101(3) 0.75780(18) 0.80879(16) 0.0963(9) Uani d . 1 . .
H H5 0.6304 0.7881 0.8438 0.116 Uiso calc R 1 . .
C C6 0.5156(3) 0.70560(18) 0.81196(14) 0.0876(8) Uani d . 1 . .
H H6 0.4713 0.7006 0.8490 0.105 Uiso calc R 1 . .
C C7 0.4844(2) 0.65902(14) 0.75938(11) 0.0681(6) Uani d . 1 . .
C C8 0.3851(2) 0.60570(14) 0.75944(11) 0.0691(7) Uani d . 1 . .
H H8 0.3392 0.5993 0.7958 0.083 Uiso calc R 1 . .
C C9 0.3554(2) 0.56334(14) 0.70713(11) 0.0617(6) Uani d . 1 . .
C C10 0.2482(2) 0.50980(14) 0.70392(11) 0.0635(6) Uani d . 1 . .
C C11 0.1918(2) 0.48178(15) 0.75749(12) 0.0745(7) Uani d . 1 . .
H H11 0.2226 0.4958 0.7966 0.089 Uiso calc R 1 . .
C C12 0.0904(3) 0.43317(16) 0.75384(15) 0.0858(8) Uani d . 1 . .
H H12 0.0538 0.4149 0.7905 0.103 Uiso calc R 1 . .
C C13 0.0441(3) 0.4121(2) 0.69771(17) 0.0999(10) Uani d . 1 . .
H H13 -0.0241 0.3793 0.6955 0.120 Uiso calc R 1 . .
C C14 0.0978(3) 0.4392(2) 0.64406(16) 0.1194(12) Uani d . 1 . .
H H14 0.0660 0.4248 0.6052 0.143 Uiso calc R 1 . .
C C15 0.1993(3) 0.4880(2) 0.64698(13) 0.0944(9) Uani d . 1 . .
H H15 0.2350 0.5062 0.6101 0.113 Uiso calc R 1 . .
C C16 0.8797(3) 0.5726(3) 0.53211(16) 0.1305(13) Uani d . 1 . .
H H16A 0.9202 0.5639 0.5715 0.196 Uiso calc R 1 . .
H H16B 0.9171 0.6166 0.5108 0.196 Uiso calc R 1 . .
H H16C 0.8864 0.5257 0.5067 0.196 Uiso calc R 1 . .
C C17 0.7463(2) 0.59087(19) 0.54383(14) 0.0888(8) Uani d . 1 . .
C C18 0.6524(3) 0.59926(17) 0.50078(13) 0.0849(8) Uani d . 1 . .
H H18 0.6579 0.5946 0.4574 0.102 Uiso calc R 1 . .
C C19 0.5500(2) 0.61580(14) 0.53516(12) 0.0688(7) Uani d . 1 . .
C C20 0.4262(2) 0.63444(15) 0.51195(12) 0.0700(7) Uani d . 1 . .
C C21 0.3472(3) 0.68436(17) 0.54353(13) 0.0869(8) Uani d . 1 . .
H H21 0.3704 0.7068 0.5816 0.104 Uiso calc R 1 . .
C C22 0.2326(3) 0.7011(2) 0.51841(16) 0.1031(10) Uani d . 1 . .
H H22 0.1792 0.7335 0.5407 0.124 Uiso calc R 1 . .
C C23 0.1976(3) 0.6712(2) 0.46237(18) 0.1081(10) Uani d . 1 . .
H H23 0.1214 0.6835 0.4458 0.130 Uiso calc R 1 . .
C C24 0.2752(3) 0.6231(2) 0.43068(16) 0.1117(11) Uani d . 1 . .
H H24 0.2522 0.6027 0.3919 0.134 Uiso calc R 1 . .
C C25 0.3885(3) 0.60395(18) 0.45521(13) 0.0887(8) Uani d . 1 . .
H H25 0.4398 0.5700 0.4330 0.106 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'
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
C1 N1 C9 . . 117.7(2) ?
C19 N2 N3 . . 111.61(19) ?
C19 N2 C1 . . 130.7(2) ?
N3 N2 C1 . . 116.34(19) ?
C17 N3 N2 . . 104.2(2) ?
N1 C1 C2 . . 125.8(2) ?
N1 C1 N2 . . 114.9(2) ?
C2 C1 N2 . . 119.3(2) ?
C7 C2 C3 . . 118.5(2) ?
C7 C2 C1 . . 115.9(2) ?
C3 C2 C1 . . 125.6(2) ?
C4 C3 C2 . . 120.7(3) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.6(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.5(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.3(3) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C2 . . 118.0(2) ?
C8 C7 C6 . . 122.7(2) ?
C2 C7 C6 . . 119.3(2) ?
C9 C8 C7 . . 121.1(2) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 N1 . . 121.5(2) ?
C8 C9 C10 . . 123.0(2) ?
N1 C9 C10 . . 115.5(2) ?
C15 C10 C11 . . 117.6(2) ?
C15 C10 C9 . . 120.8(2) ?
C11 C10 C9 . . 121.6(2) ?
C12 C11 C10 . . 121.0(2) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C13 C12 C11 . . 120.6(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 119.6(3) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C15 . . 120.5(3) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.8 ?
C10 C15 C14 . . 120.7(3) ?
C10 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C17 C16 H16A . . 109.5 ?
C17 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C17 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N3 C17 C18 . . 112.2(2) ?
N3 C17 C16 . . 118.9(3) ?
C18 C17 C16 . . 128.9(3) ?
C19 C18 C17 . . 106.0(2) ?
C19 C18 H18 . . 127.0 ?
C17 C18 H18 . . 127.0 ?
N2 C19 C18 . . 106.0(2) ?
N2 C19 C20 . . 125.7(2) ?
C18 C19 C20 . . 128.1(2) ?
C25 C20 C21 . . 117.8(3) ?
C25 C20 C19 . . 119.4(2) ?
C21 C20 C19 . . 122.8(2) ?
C20 C21 C22 . . 120.0(3) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C23 C22 C21 . . 121.4(3) ?
C23 C22 H22 . . 119.3 ?
C21 C22 H22 . . 119.3 ?
C22 C23 C24 . . 118.9(3) ?
C22 C23 H23 . . 120.5 ?
C24 C23 H23 . . 120.5 ?
C23 C24 C25 . . 120.9(3) ?
C23 C24 H24 . . 119.5 ?
C25 C24 H24 . . 119.5 ?
C20 C25 C24 . . 120.9(3) ?
C20 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
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
N1 C1 . 1.308(3) ?
N1 C9 . 1.372(3) ?
N2 C19 . 1.362(3) ?
N2 N3 . 1.374(3) ?
N2 C1 . 1.433(3) ?
N3 C17 . 1.321(3) ?
C1 C2 . 1.418(3) ?
C2 C7 . 1.411(3) ?
C2 C3 . 1.414(3) ?
C3 C4 . 1.351(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.359(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.409(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.410(3) ?
C8 C9 . 1.362(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.481(3) ?
C10 C15 . 1.376(3) ?
C10 C11 . 1.381(3) ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.347(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.365(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.515(4) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.385(4) ?
C18 C19 . 1.370(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.478(3) ?
C20 C25 . 1.377(3) ?
C20 C21 . 1.381(4) ?
C21 C22 . 1.394(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.351(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.355(5) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.385(4) ?
C24 H24 . 0.9300 ?
C25 H25 . 0.9300 ?
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
C19 N2 N3 C17 . . . . 0.9(3) ?
C1 N2 N3 C17 . . . . 169.0(2) ?
C9 N1 C1 C2 . . . . 0.0(3) ?
C9 N1 C1 N2 . . . . 178.25(18) ?
C19 N2 C1 N1 . . . . 42.3(3) ?
N3 N2 C1 N1 . . . . -123.0(2) ?
C19 N2 C1 C2 . . . . -139.3(2) ?
N3 N2 C1 C2 . . . . 55.3(3) ?
N1 C1 C2 C7 . . . . 2.4(3) ?
N2 C1 C2 C7 . . . . -175.80(18) ?
N1 C1 C2 C3 . . . . -176.8(2) ?
N2 C1 C2 C3 . . . . 5.1(3) ?
C7 C2 C3 C4 . . . . 1.6(3) ?
C1 C2 C3 C4 . . . . -179.3(2) ?
C2 C3 C4 C5 . . . . -0.8(4) ?
C3 C4 C5 C6 . . . . -0.2(4) ?
C4 C5 C6 C7 . . . . 0.4(4) ?
C3 C2 C7 C8 . . . . 177.2(2) ?
C1 C2 C7 C8 . . . . -2.0(3) ?
C3 C2 C7 C6 . . . . -1.4(3) ?
C1 C2 C7 C6 . . . . 179.4(2) ?
C5 C6 C7 C8 . . . . -178.1(2) ?
C5 C6 C7 C2 . . . . 0.4(4) ?
C2 C7 C8 C9 . . . . -0.5(3) ?
C6 C7 C8 C9 . . . . 178.0(2) ?
C7 C8 C9 N1 . . . . 3.1(3) ?
C7 C8 C9 C10 . . . . -176.8(2) ?
C1 N1 C9 C8 . . . . -2.8(3) ?
C1 N1 C9 C10 . . . . 177.05(19) ?
C8 C9 C10 C15 . . . . 159.6(2) ?
N1 C9 C10 C15 . . . . -20.2(3) ?
C8 C9 C10 C11 . . . . -18.6(3) ?
N1 C9 C10 C11 . . . . 161.5(2) ?
C15 C10 C11 C12 . . . . 0.4(4) ?
C9 C10 C11 C12 . . . . 178.7(2) ?
C10 C11 C12 C13 . . . . -0.1(4) ?
C11 C12 C13 C14 . . . . -0.1(5) ?
C12 C13 C14 C15 . . . . 0.1(5) ?
C11 C10 C15 C14 . . . . -0.4(4) ?
C9 C10 C15 C14 . . . . -178.7(3) ?
C13 C14 C15 C10 . . . . 0.2(5) ?
N2 N3 C17 C18 . . . . -0.5(3) ?
N2 N3 C17 C16 . . . . 179.2(3) ?
N3 C17 C18 C19 . . . . -0.1(3) ?
C16 C17 C18 C19 . . . . -179.8(3) ?
N3 N2 C19 C18 . . . . -1.0(3) ?
C1 N2 C19 C18 . . . . -166.9(2) ?
N3 N2 C19 C20 . . . . -176.8(2) ?
C1 N2 C19 C20 . . . . 17.3(4) ?
C17 C18 C19 N2 . . . . 0.6(3) ?
C17 C18 C19 C20 . . . . 176.3(3) ?
N2 C19 C20 C25 . . . . -156.5(2) ?
C18 C19 C20 C25 . . . . 28.6(4) ?
N2 C19 C20 C21 . . . . 26.4(4) ?
C18 C19 C20 C21 . . . . -148.5(3) ?
C25 C20 C21 C22 . . . . 1.3(4) ?
C19 C20 C21 C22 . . . . 178.5(2) ?
C20 C21 C22 C23 . . . . -2.0(5) ?
C21 C22 C23 C24 . . . . 1.0(5) ?
C22 C23 C24 C25 . . . . 0.6(6) ?
C21 C20 C25 C24 . . . . 0.3(4) ?
C19 C20 C25 C24 . . . . -177.0(3) ?
C23 C24 C25 C20 . . . . -1.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744222
