#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/35/2013589.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_2013589
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 O5'
_chemical_formula_moiety         'C11 H15 N O5'
_chemical_formula_sum            'C11 H15 N O5'
_chemical_formula_weight         241.24
_chemical_melting_point          416.0(10)
_chemical_name_systematic
;
6-hydroxy-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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 106.110(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6807(17)
_cell_length_b                   11.793(2)
_cell_length_c                   9.8373(18)
_cell_measurement_reflns_used    560
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.32
_cell_measurement_theta_min      2.45
_cell_volume                     1079.0(3)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.029
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6019
_diffrn_reflns_theta_full        26.60
_diffrn_reflns_theta_max         26.60
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.040
_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)+(0.051P)²+0.326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.098
_refine_ls_wR_factor_ref         0.103
_reflns_number_gt                1972
_reflns_number_total             2258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1432.cif
_cod_data_source_block           II
_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 '415-417' was changed to '416.0(10)'
- 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 '415-417' was changed to '416.0(10)'
- 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_cell_volume        1078.9(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013589
_cod_database_fobs_code          2013589
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 0.82522(11) 0.59478(9) 0.55685(10) 0.0271(3) Uani d . 1 . . O
O2 0.95517(12) 0.32126(9) 0.15492(12) 0.0307(3) Uani d . 1 . . O
O3 1.03815(12) 0.59002(9) 0.31064(12) 0.0297(3) Uani d . 1 . . O
O4 0.63913(12) 0.57956(11) -0.01010(12) 0.0347(3) Uani d . 1 . . O
O5 0.74232(13) 0.67352(9) 0.77973(11) 0.0302(3) Uani d . 1 . . O
N1 0.75693(13) 0.53522(10) 0.29369(12) 0.0226(3) Uani d . 1 . . N
C1 0.58362(15) 0.60323(11) 0.40442(14) 0.0224(3) Uani d . 1 . . C
C2 0.69014(15) 0.61847(11) 0.53614(14) 0.0221(3) Uani d . 1 . . C
C3 0.64182(16) 0.66043(12) 0.65118(14) 0.0233(3) Uani d . 1 . . C
C4 0.50029(17) 0.68423(12) 0.63639(16) 0.0267(3) Uani d . 1 . . C
C5 0.39633(16) 0.66842(12) 0.50537(16) 0.0266(3) Uani d . 1 . . C
C6 0.43763(16) 0.62793(12) 0.39208(16) 0.0250(3) Uani d . 1 . . C
C7 0.62428(15) 0.55787(12) 0.28653(15) 0.0233(3) Uani d . 1 . . C
C8 0.81826(14) 0.48586(12) 0.18571(14) 0.0215(3) Uani d . 1 . . C
C9 0.87055(16) 0.36642(12) 0.24005(16) 0.0247(3) Uani d . 1 . . C
C10 0.94335(16) 0.56280(12) 0.17637(15) 0.0261(3) Uani d . 1 . . C
C11 0.70751(16) 0.47559(14) 0.04146(15) 0.0275(3) Uani d . 1 . . C
H1N 0.820(2) 0.5531(17) 0.376(2) 0.044(5) Uiso d . 1 . . H
H2O 0.949(2) 0.250(2) 0.158(2) 0.056(6) Uiso d . 1 . . H
H3O 1.090(2) 0.5297(19) 0.344(2) 0.052(6) Uiso d . 1 . . H
H4 0.4725(19) 0.7116(15) 0.7191(19) 0.032(4) Uiso d . 1 . . H
H4O 0.683(2) 0.6094(19) -0.063(2) 0.054(6) Uiso d . 1 . . H
H5 0.2955(19) 0.6846(14) 0.4974(18) 0.026(4) Uiso d . 1 . . H
H5O 0.829(3) 0.6636(19) 0.774(2) 0.057(7) Uiso d . 1 . . H
H6 0.364(2) 0.6157(15) 0.300(2) 0.037(5) Uiso d . 1 . . H
H7 0.553(2) 0.5427(16) 0.196(2) 0.041(5) Uiso d . 1 . . H
H9A 0.7856(19) 0.3186(14) 0.2350(18) 0.028(4) Uiso d . 1 . . H
H9B 0.9287(18) 0.3710(14) 0.3382(19) 0.027(4) Uiso d . 1 . . H
H10A 0.9051(18) 0.6359(14) 0.1348(18) 0.025(4) Uiso d . 1 . . H
H10B 0.9969(19) 0.5244(15) 0.1148(18) 0.033(4) Uiso d . 1 . . H
H11A 0.6312(18) 0.4235(14) 0.0471(17) 0.025(4) Uiso d . 1 . . H
H11B 0.760(2) 0.4438(16) -0.022(2) 0.035(5) 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 107.0(16) ?
C10 O3 H3O 108.7(14) ?
C11 O4 H4O 108.6(15) ?
C3 O5 H5O 112.1(16) ?
C7 N1 C8 129.40(12) ?
C7 N1 H1N 115.0(13) ?
C8 N1 H1N 115.6(13) ?
C6 C1 C2 120.36(13) ?
C6 C1 C7 120.08(13) y
C2 C1 C7 119.50(13) y
O1 C2 C1 124.00(13) y
O1 C2 C3 119.21(13) y
C1 C2 C3 116.78(13) ?
C4 C3 O5 120.54(13) ?
C4 C3 C2 121.76(13) ?
O5 C3 C2 117.68(13) ?
C3 C4 C5 120.69(14) ?
C3 C4 H4 118.5(11) ?
C5 C4 H4 120.8(11) ?
C6 C5 C4 119.61(14) ?
C6 C5 H5 120.9(10) ?
C4 C5 H5 119.4(10) ?
C5 C6 C1 120.79(14) ?
C5 C6 H6 119.6(11) ?
C1 C6 H6 119.6(11) ?
N1 C7 C1 121.74(13) y
N1 C7 H7 116.7(12) ?
C1 C7 H7 121.6(12) ?
N1 C8 C11 112.44(11) ?
N1 C8 C10 106.97(11) ?
C11 C8 C10 110.67(12) ?
N1 C8 C9 105.68(11) ?
C11 C8 C9 109.15(12) ?
C10 C8 C9 111.84(12) ?
O2 C9 C8 108.92(11) ?
O2 C9 H9A 111.3(10) ?
C8 C9 H9A 108.4(10) ?
O2 C9 H9B 109.5(10) ?
C8 C9 H9B 109.7(10) ?
H9A C9 H9B 109.0(14) ?
O3 C10 C8 113.23(12) ?
O3 C10 H10A 105.1(10) ?
C8 C10 H10A 109.3(10) ?
O3 C10 H10B 110.7(10) ?
C8 C10 H10B 108.4(10) ?
H10A C10 H10B 110.0(14) ?
O4 C11 C8 113.65(12) ?
O4 C11 H11A 106.2(10) ?
C8 C11 H11A 110.2(10) ?
O4 C11 H11B 112.0(11) ?
C8 C11 H11B 105.6(11) ?
H11A C11 H11B 109.2(15) ?
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 . 1.2968(17) y
O2 C9 . 1.4271(18) ?
O2 H2O . 0.84(2) ?
O3 C10 . 1.4203(18) ?
O3 H3O . 0.88(2) ?
O4 C11 . 1.4185(19) ?
O4 H4O . 0.84(2) ?
O5 C3 . 1.3737(18) y
O5 H5O . 0.87(3) ?
N1 C7 . 1.2943(19) y
N1 C8 . 1.4730(17) y
N1 H1N . 0.89(2) ?
C1 C6 . 1.415(2) y
C1 C2 . 1.4258(19) y
C1 C7 . 1.428(2) y
C2 C3 . 1.4277(19) y
C3 C4 . 1.366(2) y
C4 C5 . 1.410(2) y
C4 H4 . 0.979(19) ?
C5 C6 . 1.370(2) y
C5 H5 . 0.976(18) ?
C6 H6 . 1.000(19) ?
C7 H7 . 0.98(2) ?
C8 C11 . 1.5276(19) ?
C8 C10 . 1.536(2) ?
C8 C9 . 1.5414(19) ?
C9 H9A . 0.987(18) ?
C9 H9B . 0.975(17) ?
C10 H10A . 0.981(17) ?
C10 H10B . 1.007(18) ?
C11 H11A . 0.974(17) ?
C11 H11B . 0.980(19) ?
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 . 0.89(2) 1.84(2) 2.5851(16) 140.0(18)
O2 H2O O3 2_745 0.84(2) 1.91(3) 2.7465(16) 171(2)
O3 H3O O1 3_766 0.88(2) 1.83(2) 2.6910(15) 167(2)
O4 H4O O5 1_554 0.84(2) 1.95(3) 2.7652(17) 167(2)
O5 H5O O2 3_766 0.87(3) 2.02(3) 2.8193(17) 153(2)
O5 H5O O1 . 0.87(3) 2.27(2) 2.7000(15) 110.3(19)
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 178.02(13) ?
C7 C1 C2 O1 0.9(2) y
C6 C1 C2 C3 -0.75(19) ?
C7 C1 C2 C3 -177.88(12) ?
O1 C2 C3 C4 -178.41(13) ?
C1 C2 C3 C4 0.4(2) ?
O1 C2 C3 O5 -0.12(19) ?
C1 C2 C3 O5 178.71(12) ?
O5 C3 C4 C5 -178.54(13) ?
C2 C3 C4 C5 -0.3(2) ?
C3 C4 C5 C6 0.5(2) ?
C4 C5 C6 C1 -0.9(2) ?
C2 C1 C6 C5 1.0(2) ?
C7 C1 C6 C5 178.11(13) ?
C8 N1 C7 C1 178.20(13) ?
C6 C1 C7 N1 179.38(13) ?
C2 C1 C7 N1 -3.5(2) y
C7 N1 C8 C11 8.4(2) ?
C7 N1 C8 C10 130.12(15) ?
C7 N1 C8 C9 -110.56(16) ?
N1 C8 C9 O2 -169.27(11) ?
C11 C8 C9 O2 69.58(15) ?
C10 C8 C9 O2 -53.22(15) ?
N1 C8 C10 O3 47.88(15) ?
C11 C8 C10 O3 170.69(12) ?
C9 C8 C10 O3 -67.38(15) ?
N1 C8 C11 O4 55.60(17) ?
C10 C8 C11 O4 -63.97(16) ?
C9 C8 C11 O4 172.53(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652375
