#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101766.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101766
loop_
_publ_author_name
'X.-L. Zhang'
'Z.-X. Li'
_publ_section_title
;
Crystal structure of 4-{[1-(4-dimethylaminophenyl)-methylidene]amino}-
1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one, C₂₀H₂₂N₄O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              263
_journal_page_last               264
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C20 H22 N4 O'
_chemical_formula_weight         334.42
_chemical_name_systematic
; 
4-{[1-(4-dimethylaminophenyl)methylidene]amino}-1,5-dimethyl-2-phenyl-1,2-
dihydropyrazol-3-one 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   '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                90.00
_cell_angle_beta                 101.010(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.875(4)
_cell_length_b                   6.8775(16)
_cell_length_c                   29.747(7)
_cell_measurement_reflns_used    785
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.201
_cell_measurement_theta_min      2.37
_cell_volume                     3589.6(14)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       omega
_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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7218
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+2.2071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                1911
_reflns_number_total             3169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1515.cff
_cod_data_source_block           50122d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        3589.6(15)
_cod_database_code               8101766
loop_
_symmetry_equiv_pos_as_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55503(14) 0.3614(3) 0.37538(8) 0.0598(7) Uani 1 8 f d . . .
N1 N 0.58460(14) 0.0998(4) 0.33309(9) 0.0442(7) Uani 1 8 f d . . .
N2 N 0.54710(15) -0.0727(3) 0.31590(9) 0.0454(7) Uani 1 8 f d . . .
N3 N 0.41412(15) 0.0933(4) 0.38221(9) 0.0516(7) Uani 1 8 f d . . .
N4 N 0.12227(19) 0.4057(6) 0.45740(11) 0.0826(11) Uani 1 8 f d . . .
C1 C 0.54022(18) 0.1959(5) 0.35984(10) 0.0445(8) Uani 1 8 f d . . .
C2 C 0.47813(17) 0.0654(5) 0.36250(10) 0.0432(8) Uani 1 8 f d . . .
C3 C 0.48717(18) -0.0940(4) 0.33748(11) 0.0427(8) Uani 1 8 f d . . .
C4 C 0.4388(2) -0.2723(5) 0.33074(13) 0.0627(10) Uani 1 8 f d . . .
H4A H 0.4690 -0.3832 0.3424 0.094 Uiso 1 8 f calc R . .
H4B H 0.4189 -0.2901 0.2987 0.094 Uiso 1 8 f calc R . .
H4C H 0.3974 -0.2585 0.3468 0.094 Uiso 1 8 f calc R . .
C5 C 0.5989(2) -0.2336(5) 0.31035(12) 0.0586(10) Uani 1 8 f d . . .
H5A H 0.6260 -0.2741 0.3399 0.088 Uiso 1 8 f calc R . .
H5B H 0.6346 -0.1908 0.2921 0.088 Uiso 1 8 f calc R . .
H5C H 0.5699 -0.3408 0.2954 0.088 Uiso 1 8 f calc R . .
C6 C 0.4020(2) 0.2552(5) 0.40101(11) 0.0554(9) Uani 1 8 f d . . .
H6 H 0.4391 0.3518 0.4044 0.067 Uiso 1 8 f calc R . .
C7 C 0.3309(2) 0.2907(6) 0.41729(11) 0.0548(9) Uani 1 8 f d . . .
C8 C 0.3146(2) 0.4752(6) 0.43193(12) 0.0660(11) Uani 1 8 f d . . .
H8 H 0.3502 0.5743 0.4325 0.079 Uiso 1 8 f calc R . .
C9 C 0.2462(2) 0.5144(6) 0.44567(13) 0.0726(12) Uani 1 8 f d . . .
H9 H 0.2366 0.6395 0.4550 0.087 Uiso 1 8 f calc R . .
C10 C 0.1913(2) 0.3684(6) 0.44573(11) 0.0634(10) Uani 1 8 f d . . .
C11 C 0.2095(2) 0.1811(6) 0.43127(12) 0.0644(10) Uani 1 8 f d . . .
H11 H 0.1748 0.0800 0.4307 0.077 Uiso 1 8 f calc R . .
C12 C 0.2775(2) 0.1473(6) 0.41816(12) 0.0593(10) Uani 1 8 f d . . .
H12 H 0.2882 0.0220 0.4094 0.071 Uiso 1 8 f calc R . .
C13 C 0.1081(3) 0.5914(7) 0.47811(15) 0.0988(16) Uani 1 8 f d . . .
H13A H 0.1404 0.6024 0.5077 0.148 Uiso 1 8 f calc R . .
H13B H 0.0557 0.5979 0.4813 0.148 Uiso 1 8 f calc R . .
H13C H 0.1188 0.6960 0.4589 0.148 Uiso 1 8 f calc R . .
C14 C 0.0669(2) 0.2517(7) 0.45777(14) 0.0913(14) Uani 1 8 f d . . .
H14A H 0.0606 0.1803 0.4296 0.137 Uiso 1 8 f calc R . .
H14B H 0.0190 0.3072 0.4610 0.137 Uiso 1 8 f calc R . .
H14C H 0.0846 0.1655 0.4830 0.137 Uiso 1 8 f calc R . .
C15 C 0.62924(17) 0.1997(4) 0.30559(10) 0.0388(7) Uani 1 8 f d . . .
C16 C 0.60923(17) 0.1996(4) 0.25850(11) 0.0447(8) Uani 1 8 f d . . .
H16 H 0.5673 0.1284 0.2440 0.054 Uiso 1 8 f calc R . .
C17 C 0.65172(19) 0.3057(5) 0.23282(11) 0.0482(8) Uani 1 8 f d . . .
H17 H 0.6385 0.3049 0.2010 0.058 Uiso 1 8 f calc R . .
C18 C 0.71364(19) 0.4128(5) 0.25424(12) 0.0506(9) Uani 1 8 f d . . .
H18 H 0.7418 0.4856 0.2370 0.061 Uiso 1 8 f calc R . .
C19 C 0.73325(19) 0.4111(5) 0.30092(12) 0.0543(9) Uani 1 8 f d . . .
H19 H 0.7751 0.4830 0.3154 0.065 Uiso 1 8 f calc R . .
C20 C 0.69191(19) 0.3042(5) 0.32698(11) 0.0501(9) Uani 1 8 f d . . .
H20 H 0.7062 0.3027 0.3587 0.060 Uiso 1 8 f calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 108.9(2) . . ?
C1 N1 C15 122.8(2) . . ?
N2 N1 C15 118.5(2) . . ?
C3 N2 N1 106.4(2) . . ?
C3 N2 C5 122.8(3) . . ?
N1 N2 C5 114.1(2) . . ?
C6 N3 C2 121.5(3) . . ?
C10 N4 C14 120.9(4) . . ?
C10 N4 C13 120.6(4) . . ?
C14 N4 C13 117.5(3) . . ?
O1 C1 N1 123.0(3) . . ?
O1 C1 C2 131.6(3) . . ?
N1 C1 C2 105.3(3) . . ?
C3 C2 N3 122.5(3) . . ?
C3 C2 C1 107.5(3) . . ?
N3 C2 C1 129.8(3) . . ?
C2 C3 N2 111.1(3) . . ?
C2 C3 C4 127.9(3) . . ?
N2 C3 C4 121.0(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 121.2(3) . . ?
N3 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C12 C7 C8 117.5(3) . . ?
C12 C7 C6 122.3(3) . . ?
C8 C7 C6 120.2(4) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
N4 C10 C9 122.0(4) . . ?
N4 C10 C11 121.3(4) . . ?
C9 C10 C11 116.6(3) . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 122.8(4) . . ?
C11 C12 H12 118.6 . . ?
C7 C12 H12 118.6 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.9(3) . . ?
C16 C15 N1 121.3(3) . . ?
C20 C15 N1 118.8(3) . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 119.5(3) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.238(4) . ?
N1 C1 1.393(4) . ?
N1 N2 1.410(3) . ?
N1 C15 1.424(4) . ?
N2 C3 1.358(4) . ?
N2 C5 1.472(4) . ?
N3 C6 1.283(4) . ?
N3 C2 1.395(4) . ?
N4 C10 1.368(5) . ?
N4 C14 1.451(5) . ?
N4 C13 1.461(5) . ?
C1 C2 1.441(4) . ?
C2 C3 1.352(4) . ?
C3 C4 1.491(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.465(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.376(5) . ?
C7 C8 1.390(5) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.415(5) . ?
C11 C12 1.366(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.378(4) . ?
C15 C20 1.380(4) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 474433
