#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/35/2013591.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_2013591
loop_
_publ_author_name
'Odabas̨oǧlu, Mustafa'
'Albayrak, Çiǧdem'
'Büyükgüngör, Orhan'
'Lönnecke, Peter'
_publ_section_title
;2-{[Tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one
 and its 6-hydroxy and 6-methoxy derivatives
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o616
_journal_page_last               o619
_journal_paper_doi               10.1107/S0108270103020997
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C11 H15 N O4'
_chemical_formula_moiety         'C11 H15 N O4'
_chemical_formula_sum            'C11 H15 N O4'
_chemical_formula_weight         225.24
_chemical_melting_point          422.5(5)
_chemical_name_systematic
;
2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.801(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4437(9)
_cell_length_b                   8.7029(7)
_cell_length_c                   12.6147(11)
_cell_measurement_reflns_used    986
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.78
_cell_volume                     1122.32(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.039
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12824
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.044
_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)+(0.0531P)²+0.3161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.111
_reflns_number_gt                2226
_reflns_number_total             2701
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1432.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '422-423' was changed to '422.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '422-423' was changed to '422.5(5)' -
the average value was taken and precision was
estimated.

'_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_values 1715 2011-07-08 13:25:40Z adriana 

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/c'
_cod_database_code               2013591
_cod_database_fobs_code          2013591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 0.27644(10) 0.47289(11) 0.65317(7) 0.0278(2) Uani d . 1 . . O
O2 0.53462(11) 0.28376(13) 0.57069(8) 0.0325(3) Uani d . 1 . . O
O3 0.39387(11) 0.00670(11) 0.35914(8) 0.0304(3) Uani d . 1 . . O
O4 0.23193(12) 0.31687(14) 0.21920(8) 0.0363(3) Uani d . 1 . . O
N1 0.29931(11) 0.37796(12) 0.46098(9) 0.0221(2) Uani d . 1 . . N
C1 0.15370(13) 0.57931(15) 0.48991(10) 0.0223(3) Uani d . 1 . . C
C2 0.19332(13) 0.57507(15) 0.60510(11) 0.0236(3) Uani d . 1 . . C
C3 0.13955(16) 0.68809(19) 0.66395(12) 0.0343(4) Uani d . 1 . . C
C4 0.05145(17) 0.79386(19) 0.61230(13) 0.0369(4) Uani d . 1 . . C
C5 0.00882(15) 0.79419(17) 0.49954(13) 0.0307(3) Uani d . 1 . . C
C6 0.06057(14) 0.68829(16) 0.43998(11) 0.0258(3) Uani d . 1 . . C
C7 0.21039(13) 0.47852(15) 0.42278(11) 0.0232(3) Uani d . 1 . . C
C8 0.37286(13) 0.27869(14) 0.39986(10) 0.0215(3) Uani d . 1 . . C
C9 0.51718(14) 0.29251(17) 0.45650(11) 0.0271(3) Uani d . 1 . . C
C10 0.32288(14) 0.11389(15) 0.40903(11) 0.0258(3) Uani d . 1 . . C
C11 0.36008(15) 0.33264(17) 0.28286(11) 0.0276(3) Uani d . 1 . . C
H1N 0.3223(16) 0.375(2) 0.5350(14) 0.030(4) Uiso d . 1 . . H
H2O 0.554(2) 0.193(3) 0.5903(17) 0.051(6) Uiso d . 1 . . H
H3O 0.355(2) 0.005(2) 0.2878(18) 0.049(6) Uiso d . 1 . . H
H4O 0.228(2) 0.227(3) 0.1896(18) 0.056(6) Uiso d . 1 . . H
H3 0.1679(18) 0.690(2) 0.7424(15) 0.041(5) Uiso d . 1 . . H
H4 0.017(2) 0.869(3) 0.6519(16) 0.054(6) Uiso d . 1 . . H
H5 -0.0549(18) 0.864(2) 0.4654(14) 0.039(5) Uiso d . 1 . . H
H6 0.0318(16) 0.6853(19) 0.3639(13) 0.027(4) Uiso d . 1 . . H
H7 0.1814(15) 0.4834(18) 0.3459(13) 0.022(4) Uiso d . 1 . . H
H9A 0.5507(16) 0.397(2) 0.4396(13) 0.031(4) Uiso d . 1 . . H
H9B 0.5666(17) 0.216(2) 0.4289(14) 0.032(4) Uiso d . 1 . . H
H10A 0.2263(17) 0.1103(19) 0.3756(13) 0.027(4) Uiso d . 1 . . H
H10B 0.3356(15) 0.0895(19) 0.4868(14) 0.028(4) Uiso d . 1 . . H
H11A 0.3831(15) 0.445(2) 0.2857(13) 0.026(4) Uiso d . 1 . . H
H11B 0.4242(15) 0.2736(18) 0.2503(12) 0.023(4) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
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
C9 O2 H2O 108.8(14) ?
C10 O3 H3O 106.7(13) ?
C11 O4 H4O 106.8(15) ?
C7 N1 C8 127.74(11) ?
C7 N1 H1N 114.8(11) ?
C8 N1 H1N 117.3(11) ?
C6 C1 C2 120.10(12) ?
C6 C1 C7 118.64(12) y
C2 C1 C7 121.22(12) y
O1 C2 C3 121.89(12) y
O1 C2 C1 121.22(12) y
C3 C2 C1 116.89(12) ?
C4 C3 C2 121.18(14) ?
C4 C3 H3 120.4(11) ?
C2 C3 H3 118.4(11) ?
C3 C4 C5 121.86(14) ?
C3 C4 H4 120.6(12) ?
C5 C4 H4 117.5(12) ?
C6 C5 C4 118.49(14) ?
C6 C5 H5 120.5(11) ?
C4 C5 H5 121.0(11) ?
C5 C6 C1 121.41(13) ?
C5 C6 H6 119.8(10) ?
C1 C6 H6 118.8(10) ?
N1 C7 C1 123.15(12) y
N1 C7 H7 117.5(9) ?
C1 C7 H7 119.3(9) ?
N1 C8 C11 111.91(11) ?
N1 C8 C9 106.12(10) ?
C11 C8 C9 108.00(11) ?
N1 C8 C10 106.61(10) ?
C11 C8 C10 113.27(11) ?
C9 C8 C10 110.72(11) ?
O2 C9 C8 112.27(11) ?
O2 C9 H9A 106.6(9) ?
C8 C9 H9A 108.8(9) ?
O2 C9 H9B 111.6(10) ?
C8 C9 H9B 109.2(10) ?
H9A C9 H9B 108.2(14) ?
O3 C10 C8 111.35(11) ?
O3 C10 H10A 111.2(9) ?
C8 C10 H10A 108.8(9) ?
O3 C10 H10B 108.9(9) ?
C8 C10 H10B 107.3(10) ?
H10A C10 H10B 109.2(13) ?
O4 C11 C8 113.74(12) ?
O4 C11 H11A 107.7(9) ?
C8 C11 H11A 106.9(9) ?
O4 C11 H11B 110.6(9) ?
C8 C11 H11B 107.8(9) ?
H11A C11 H11B 109.9(13) ?
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 C2 . 1.3025(16) y
O2 C9 . 1.4166(17) ?
O2 H2O . 0.84(2) ?
O3 C10 . 1.4166(16) ?
O3 H3O . 0.91(2) ?
O4 C11 . 1.4196(19) ?
O4 H4O . 0.86(2) ?
N1 C7 . 1.2952(18) y
N1 C8 . 1.4741(16) y
N1 H1N . 0.915(17) ?
C1 C6 . 1.4113(19) y
C1 C2 . 1.4276(18) y
C1 C7 . 1.4290(18) y
C2 C3 . 1.4158(19) y
C3 C4 . 1.369(2) y
C3 H3 . 0.973(19) ?
C4 C5 . 1.401(2) y
C4 H4 . 0.94(2) ?
C5 C6 . 1.368(2) y
C5 H5 . 0.938(19) ?
C6 H6 . 0.945(16) ?
C7 H7 . 0.957(16) ?
C8 C11 . 1.5283(18) ?
C8 C9 . 1.535(2) ?
C8 C10 . 1.5387(19) ?
C9 H9A . 1.009(17) ?
C9 H9B . 0.951(18) ?
C10 H10A . 1.011(17) ?
C10 H10B . 0.986(17) ?
C11 H11A . 1.009(17) ?
C11 H11B . 0.997(16) ?
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
N1 H1N O1 . 0.915(17) 1.865(17) 2.6181(14) 138.1(15)
O2 H2O O3 3_656 0.84(2) 1.89(2) 2.7314(15) 177(2)
O3 H3O O1 4_565 0.91(2) 1.74(2) 2.6426(14) 172(2)
O4 H4O O1 4_565 0.86(2) 1.90(2) 2.7254(15) 161(2)
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 C1 C2 O1 178.12(12) y
C7 C1 C2 O1 -4.3(2) ?
C6 C1 C2 C3 -2.8(2) ?
C7 C1 C2 C3 174.79(13) ?
O1 C2 C3 C4 -179.43(15) ?
C1 C2 C3 C4 1.5(2) ?
C2 C3 C4 C5 1.0(3) ?
C3 C4 C5 C6 -2.1(3) ?
C4 C5 C6 C1 0.7(2) ?
C2 C1 C6 C5 1.7(2) ?
C7 C1 C6 C5 -175.90(13) ?
C8 N1 C7 C1 -173.88(12) ?
C6 C1 C7 N1 177.91(13) ?
C2 C1 C7 N1 0.3(2) y
C7 N1 C8 C11 14.74(19) ?
C7 N1 C8 C9 132.31(14) ?
C7 N1 C8 C10 -109.61(15) ?
N1 C8 C9 O2 44.58(14) ?
C11 C8 C9 O2 164.73(11) ?
C10 C8 C9 O2 -70.73(14) ?
N1 C8 C10 O3 -175.90(10) ?
C11 C8 C10 O3 60.59(15) ?
C9 C8 C10 O3 -60.90(14) ?
N1 C8 C11 O4 -67.18(15) ?
C9 C8 C11 O4 176.38(11) ?
C10 C8 C11 O4 53.38(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12945477
