#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229033.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_2229033
loop_
_publ_author_name
'Jayarajan, R.'
'Sharmila, P.'
'Jagadeesan, G.'
'Vasuki, G.'
'Aravindhan, S.'
_publ_section_title
;
 (Z)-4-{1-[(2-Hydroxyethyl)amino]ethylidene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           DS2072
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o444
_journal_paper_doi               10.1107/S1600536810054127
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H17 N3 O2'
_chemical_formula_moiety         'C14 H17 N3 O2'
_chemical_formula_sum            'C14 H17 N3 O2'
_chemical_formula_weight         259.31
_chemical_name_systematic
;
(Z)-4-{1-[(2-Hydroxyethyl)amino]ethylidene}-3-methyl-1-phenyl-1H-\
pyrazol-5(4H)-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                 110.926(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.4703(13)
_cell_length_b                   7.0902(4)
_cell_length_c                   18.0565(11)
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.2679
_cell_measurement_theta_min      2.7207
_cell_volume                     2687.0(3)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4492
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0549
_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)+(0.1157P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1730
_reflns_number_gt                1544
_reflns_number_total             2353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ds2072.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229033
_cod_database_fobs_code          2229033
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_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
O O1 -0.05676(8) 0.3364(3) 0.35564(9) 0.0534(5) Uani d . 1 . .
N N1 -0.11378(9) 0.2982(3) 0.44012(10) 0.0384(5) Uani d . 1 . .
N N2 -0.10103(10) 0.2539(3) 0.51998(10) 0.0439(5) Uani d . 1 . .
C C11 -0.19444(10) 0.4030(3) 0.31598(12) 0.0432(6) Uani d . 1 . .
H H11 -0.1628 0.4457 0.2982 0.052 Uiso calc R 1 . .
C C10 -0.25819(11) 0.4237(4) 0.26886(14) 0.0523(7) Uani d . 1 . .
H H10 -0.2690 0.4794 0.2192 0.063 Uiso calc R 1 . .
N N3 0.06883(10) 0.2770(3) 0.43754(13) 0.0500(6) Uani d . 1 . .
C C6 -0.17841(10) 0.3190(3) 0.38911(12) 0.0378(6) Uani d . 1 . .
C C4 -0.00882(11) 0.2571(3) 0.49473(13) 0.0382(6) Uani d . 1 . .
C C9 -0.30523(12) 0.3635(4) 0.29449(15) 0.0586(8) Uani d . 1 . .
H H9 -0.3478 0.3793 0.2628 0.070 Uiso calc R 1 . .
C C13 0.05492(11) 0.2441(3) 0.50051(13) 0.0397(6) Uani d . 1 . .
C C14 0.10798(12) 0.1939(4) 0.57534(14) 0.0539(7) Uani d . 1 . .
H H14A 0.1475 0.1930 0.5661 0.081 Uiso calc R 1 . .
H H14B 0.1004 0.0711 0.5926 0.081 Uiso calc R 1 . .
H H14C 0.1103 0.2852 0.6155 0.081 Uiso calc R 1 . .
C C8 -0.28911(13) 0.2791(4) 0.36768(16) 0.0627(8) Uani d . 1 . .
H H8 -0.3210 0.2374 0.3852 0.075 Uiso calc R 1 . .
C C3 -0.03936(12) 0.2315(3) 0.55172(13) 0.0413(6) Uani d . 1 . .
C C7 -0.22638(12) 0.2558(4) 0.41503(14) 0.0510(7) Uani d . 1 . .
H H7 -0.2159 0.1980 0.4643 0.061 Uiso calc R 1 . .
C C5 -0.05950(11) 0.3010(3) 0.42224(12) 0.0379(6) Uani d . 1 . .
C C12 -0.01114(13) 0.1893(4) 0.63896(13) 0.0569(7) Uani d . 1 . .
H H12A -0.0446 0.1807 0.6602 0.085 Uiso calc R 1 . .
H H12B 0.0177 0.2884 0.6654 0.085 Uiso calc R 1 . .
H H12C 0.0115 0.0718 0.6470 0.085 Uiso calc R 1 . .
C C16 0.12548(15) 0.2950(5) 0.34639(18) 0.0694(9) Uani d . 1 . .
C C15 0.13080(13) 0.2678(5) 0.42954(18) 0.0677(8) Uani d . 1 A .
H H15A 0.1501 0.1461 0.4481 0.081 Uiso calc R 1 . .
H H15B 0.1583 0.3644 0.4624 0.081 Uiso calc R 1 . .
O O2A 0.08008(17) 0.1945(5) 0.2936(2) 0.0683(13) Uiso d P 0.567(5) A 1
O O2B 0.0870(2) 0.4236(7) 0.3041(3) 0.0637(16) Uiso d P 0.433(5) A 2
H H 0.0343(14) 0.315(4) 0.3970(16) 0.063(8) Uiso 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 . . 111.97(17) ?
C5 N1 C6 . . 129.44(18) ?
N2 N1 C6 . . 118.40(18) ?
C3 N2 N1 . . 105.88(18) ?
C6 C11 C10 . . 119.6(2) ?
C6 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C9 C10 C11 . . 120.9(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C13 N3 C15 . . 128.0(2) ?
C13 N3 H . . 111.0(18) ?
C15 N3 H . . 120.9(18) ?
C11 C6 C7 . . 119.6(2) ?
C11 C6 N1 . . 121.6(2) ?
C7 C6 N1 . . 118.8(2) ?
C13 C4 C3 . . 132.4(2) ?
C13 C4 C5 . . 122.8(2) ?
C3 C4 C5 . . 104.8(2) ?
C10 C9 C8 . . 119.4(2) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
N3 C13 C4 . . 118.7(2) ?
N3 C13 C14 . . 118.0(2) ?
C4 C13 C14 . . 123.3(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C7 C8 C9 . . 120.7(3) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
N2 C3 C4 . . 111.9(2) ?
N2 C3 C12 . . 117.9(2) ?
C4 C3 C12 . . 130.1(2) ?
C8 C7 C6 . . 119.8(2) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
O1 C5 N1 . . 125.7(2) ?
O1 C5 C4 . . 128.8(2) ?
N1 C5 C4 . . 105.45(19) ?
C3 C12 H12A . . 109.5 ?
C3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O2B C16 O2A . . 77.0(3) ?
O2B C16 C15 . . 119.0(3) ?
O2A C16 C15 . . 114.9(3) ?
N3 C15 C16 . . 111.3(2) ?
N3 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
N3 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
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
O1 C5 . 1.251(3) ?
N1 C5 . 1.369(3) ?
N1 N2 . 1.402(2) ?
N1 C6 . 1.423(3) ?
N2 C3 . 1.306(3) ?
C11 C6 . 1.374(3) ?
C11 C10 . 1.388(3) ?
C11 H11 . 0.9300 ?
C10 C9 . 1.365(4) ?
C10 H10 . 0.9300 ?
N3 C13 . 1.303(3) ?
N3 C15 . 1.452(4) ?
N3 H . 0.90(3) ?
C6 C7 . 1.394(4) ?
C4 C13 . 1.401(4) ?
C4 C3 . 1.438(3) ?
C4 C5 . 1.429(3) ?
C9 C8 . 1.376(4) ?
C9 H9 . 0.9300 ?
C13 C14 . 1.491(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C8 C7 . 1.373(3) ?
C8 H8 . 0.9300 ?
C3 C12 . 1.503(3) ?
C7 H7 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C16 O2B . 1.300(5) ?
C16 O2A . 1.328(4) ?
C16 C15 . 1.476(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
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
N3 H O1 . 0.90(3) 1.92(3) 2.711(3) 146(3)
