#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013749.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_2013749
loop_
_publ_author_name
'Soylu, Serkan'
'Tas̨, Murat'
'Saraçoĝlu, Hanife'
'Batı, Hümeyra'
'Çalıs̨kan, Nezihe'
'Büyükgüngör, Orhan'
_publ_section_title
N¹-(2,6-Dimethylphenyl)-N²-hydroxy-α-oxo-α-phenylacetamidine
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o115
_journal_page_last               o117
_journal_paper_doi               10.1107/S0108270103028178
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H16 N2 O2'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic
;
N¹-(2,6-Dimethylphenyl)-N²-hydroxy-α-oxo-α-phenylacetamidine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90.828(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1002(10)
_cell_length_b                   7.8837(10)
_cell_length_c                   23.108(3)
_cell_measurement_reflns_used    8969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      1.76
_cell_volume                     1475.5(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996; Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       φ
_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  0.060
_diffrn_reflns_av_sigmaI/netI    0.056
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10735
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.042
_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)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.116
_reflns_number_gt                1316
_reflns_number_total             2566
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1035.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2013749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
C11 -0.2014(3) 0.4467(3) 0.31533(12) 0.0913(7) Uani d . 1 . . C
H11 -0.3086 0.4148 0.3242 0.110 Uiso calc R 1 . . H
C16 0.2019(4) -0.0671(4) 0.37992(16) 0.1328(11) Uani d . 1 . . C
H16A 0.1397 -0.0411 0.4138 0.199 Uiso calc R 1 . . H
H16B 0.1851 -0.1839 0.3696 0.199 Uiso calc R 1 . . H
H16C 0.1659 0.0042 0.3485 0.199 Uiso calc R 1 . . H
C12 -0.1729(4) 0.5500(4) 0.26919(12) 0.1054(9) Uani d . 1 . . C
H12 -0.2612 0.5893 0.2468 0.126 Uiso calc R 1 . . H
C10 -0.0703(3) 0.3900(3) 0.34865(10) 0.0791(6) Uani d . 1 . . C
H10 -0.0903 0.3199 0.3801 0.095 Uiso calc R 1 . . H
O2 0.1117(2) 0.34282(19) 0.51940(6) 0.0839(5) Uani d . 1 . . O
H2 0.0446 0.3965 0.5383 0.126 Uiso calc R 1 . . H
C6 0.3817(3) -0.0369(3) 0.39211(11) 0.0897(7) Uani d . 1 . . C
N2 0.1069(2) 0.3994(2) 0.46136(7) 0.0718(5) Uani d . 1 . . N
C13 -0.0158(4) 0.5961(4) 0.25567(12) 0.1062(9) Uani d . 1 . . C
H13 0.0021 0.6669 0.2242 0.127 Uiso calc R 1 . . H
C5 0.5015(5) -0.1436(3) 0.36988(12) 0.1077(9) Uani d . 1 . . C
H5 0.4697 -0.2333 0.3461 0.129 Uiso calc R 1 . . H
C9 0.0907(3) 0.4351(2) 0.33628(9) 0.0679(6) Uani d . 1 . . C
C7 0.2158(3) 0.3189(2) 0.43162(9) 0.0657(6) Uani d . 1 . . C
N1 0.3167(2) 0.2002(2) 0.45496(8) 0.0794(5) Uani d . 1 . . N
H1 0.3085 0.1851 0.4917 0.095 Uiso calc R 1 . . H
C1 0.4345(3) 0.0970(3) 0.42672(9) 0.0717(6) Uani d . 1 . . C
C14 0.1165(3) 0.5384(3) 0.28824(10) 0.0858(7) Uani d . 1 . . C
H14 0.2233 0.5685 0.2782 0.103 Uiso calc R 1 . . H
C8 0.2352(3) 0.3777(2) 0.37040(9) 0.0689(6) Uani d . 1 . . C
C4 0.6643(5) -0.1196(4) 0.38224(13) 0.1096(10) Uani d . 1 . . C
H4 0.7422 -0.1937 0.3673 0.132 Uiso calc R 1 . . H
C2 0.6001(3) 0.1248(3) 0.43946(10) 0.0769(6) Uani d . 1 . . C
O1 0.3731(2) 0.3817(2) 0.35085(7) 0.0971(5) Uani d . 1 . . O
C3 0.7146(3) 0.0128(4) 0.41663(12) 0.0983(8) Uani d . 1 . . C
H3 0.8264 0.0280 0.4248 0.118 Uiso calc R 1 . . H
C15 0.6534(3) 0.2719(3) 0.47589(12) 0.1080(9) Uani d . 1 . . C
H15A 0.6311 0.3756 0.4555 0.162 Uiso calc R 1 . . H
H15B 0.7697 0.2636 0.4841 0.162 Uiso calc R 1 . . H
H15C 0.5939 0.2711 0.5115 0.162 Uiso calc R 1 . . H
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_publ_flag
C12 C11 C10 119.5(3) ?
C12 C11 H11 120.2 ?
C10 C11 H11 120.2 ?
C6 C16 H16A 109.5 ?
C6 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C6 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C13 C12 C11 120.5(3) ?
C13 C12 H12 119.8 ?
C11 C12 H12 119.8 ?
C11 C10 C9 121.5(2) ?
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
N2 O2 H2 109.5 ?
C1 C6 C5 117.5(3) ?
C1 C6 C16 121.3(2) ?
C5 C6 C16 121.1(3) ?
C7 N2 O2 109.89(15) y
C12 C13 C14 120.5(3) ?
C12 C13 H13 119.7 ?
C14 C13 H13 119.7 ?
C4 C5 C6 121.3(3) ?
C4 C5 H5 119.3 ?
C6 C5 H5 119.3 ?
C10 C9 C14 117.8(2) ?
C10 C9 C8 123.6(2) y
C14 C9 C8 118.6(2) y
N2 C7 N1 122.81(19) y
N2 C7 C8 115.55(18) ?
N1 C7 C8 121.37(19) y
C7 N1 C1 128.37(18) y
C7 N1 H1 115.8 ?
C1 N1 H1 115.8 ?
C2 C1 C6 122.1(2) ?
C2 C1 N1 117.8(2) y
C6 C1 N1 119.8(2) y
C13 C14 C9 120.2(3) ?
C13 C14 H14 119.9 ?
C9 C14 H14 119.9 ?
O1 C8 C9 121.5(2) y
O1 C8 C7 118.0(2) y
C9 C8 C7 120.5(2) y
C5 C4 C3 120.5(2) ?
C5 C4 H4 119.7 ?
C3 C4 H4 119.7 ?
C1 C2 C3 117.9(2) ?
C1 C2 C15 120.9(2) ?
C3 C2 C15 121.2(2) ?
C4 C3 C2 120.6(3) ?
C4 C3 H3 119.7 ?
C2 C3 H3 119.7 ?
C2 C15 H15A 109.5 ?
C2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
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
C11 C12 . 1.364(4) ?
C11 C10 . 1.377(3) ?
C11 H11 . 0.9300 ?
C16 C6 . 1.498(3) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C12 C13 . 1.364(4) ?
C12 H12 . 0.9300 ?
C10 C9 . 1.386(3) ?
C10 H10 . 0.9300 ?
O2 N2 . 1.413(2) y
O2 H2 . 0.8200 ?
C6 C1 . 1.388(3) ?
C6 C5 . 1.389(4) ?
N2 C7 . 1.292(2) y
C13 C14 . 1.378(3) ?
C13 H13 . 0.9300 ?
C5 C4 . 1.358(4) ?
C5 H5 . 0.9300 ?
C9 C14 . 1.395(3) ?
C9 C8 . 1.473(3) y
C7 N1 . 1.349(2) y
C7 C8 . 1.499(3) y
N1 C1 . 1.420(2) y
N1 H1 . 0.8600 ?
C1 C2 . 1.386(3) ?
C14 H14 . 0.9300 ?
C8 O1 . 1.212(2) y
C4 C3 . 1.371(4) ?
C4 H4 . 0.9300 ?
C2 C3 . 1.390(3) ?
C2 C15 . 1.494(3) ?
C3 H3 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
O2 H2 N2 3_566 0.82 2.02 2.737(2) 145
N1 H1 O2 . 0.86 2.13 2.512(2) 107
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
O2 N2 C7 C8 -174.53(17) y
N2 C7 N1 C1 176.4(2) y
C7 N1 C1 C8 5.08(18) y
C7 N1 C1 C2 112.4(2) y
C10 C9 C8 O1 160.7(2) y
C9 C14 C8 O1 164.5(2) y
N2 C7 C8 O1 141.4(2) y
C7 N1 C8 O1 151.4(3) y
N2 C9 C7 C8 -147.8(2) y
C9 C7 N1 C8 25.47(18) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21134337
