#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/94/2009440.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_2009440
loop_
_publ_author_name
'Hornish, Michael J.'
'Watt, William'
_publ_contact_author
;
    Watt, William
    Research Laboratories,
    The Upjohn Company,
    Kalamazoo,
    MI 49007
    USA
;
_publ_section_title
;
 1,3,5-Triethyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione,
 C₉H₁₅N₃O₃
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              263
_journal_page_last               265
_journal_paper_doi               10.1107/S0108270193008212
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C9 H15 N3 O3'
_chemical_formula_weight         213.24
_chemical_name_systematic
1,3,5-Triethylperhydro-1,3,5-triazine-2,4,6-trione
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8450(10)
_cell_length_b                   8.1600(10)
_cell_length_c                   16.8400(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    123
_cell_measurement_theta_max      69
_cell_measurement_theta_min      60
_cell_volume                     1078.0(2)
_computing_cell_refinement       'Duchamp (1977)'
_computing_data_reduction        'CRYM (Duchamp, 1984)'
_computing_structure_refinement  'CRYM (Duchamp, 1984)'
_computing_structure_solution    'MULTAN (Main et al., 1980)'
_diffrn_ambient_temperature      123
_diffrn_measurement_device       'Siemens P1'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1183
_diffrn_reflns_theta_max         69
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 80
_diffrn_standards_number         9
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_density_meas      1.25
_exptl_crystal_density_method    XX?
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.220
_refine_ls_goodness_of_fit_all   1.57
_refine_ls_goodness_of_fit_obs   1.57
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1183
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_obs          0.035
_refine_ls_shift/esd_max         0.027
_refine_ls_shift/esd_mean        0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(F²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.081
_refine_ls_wR_factor_obs         0.078
_reflns_number_observed          942
_reflns_number_total             1183
_reflns_observed_criterion       I>3.0\s(I)
_cod_data_source_file            cd1063.cif
_cod_data_source_block           default
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Bij' was replaced with
'Bani' value 15 times.

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

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(F^2^)]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F^2^)]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1078.00(10)
_cod_database_code               2009440
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N(1) 0.0084(4) 0.0071(4) 0.00160(10) -0.0009(7) 0.0009(3) 0.0000(3)
C(1) 0.0129(6) 0.0083(5) 0.00240(10) -0.0027(10) 0.0013(5) 0.0007(4)
O(2) 0.0112(4) 0.0120(3) 0.00240(10) 0.0022(6) -0.0018(3) 0.0030(3)
C(2) 0.0086(5) 0.0105(5) 0.00150(10) 0.0022(9) 0.0007(3) 0.0006(3)
N(3) 0.0073(4) 0.0091(4) 0.00140(10) -0.0005(7) -0.0008(3) -0.0007(3)
C(3) 0.0085(5) 0.0133(5) 0.00170(10) -0.0017(9) -0.0007(4) -0.0016(4)
O(4) 0.0134(4) 0.0077(3) 0.00300(10) -0.0037(6) -0.0018(3) 0.0001(3)
C(4) 0.0089(5) 0.0093(5) 0.00160(10) 0.0010(8) 0.0009(4) -0.0007(3)
N(5) 0.0085(4) 0.0081(4) 0.00170(10) 0.0000(7) -0.0003(3) 0.0001(3)
C(5) 0.0095(5) 0.0095(5) 0.00210(10) 0.0040(8) -0.0013(4) 0.0007(4)
O(6) 0.0098(4) 0.0112(3) 0.00200(10) -0.0027(6) -0.0015(3) -0.0007(3)
C(6) 0.0081(5) 0.0100(4) 0.00140(10) 0.0008(8) 0.0009(4) -0.0006(3)
C(11) 0.0134(6) 0.0141(6) 0.00240(10) -0.0080(11) 0.0006(5) 0.0017(4)
C(33) 0.0091(5) 0.0178(8) 0.00290(10) -0.0036(12) -0.0007(5) -0.0039(5)
C(55) 0.0132(7) 0.0110(5) 0.00220(10) 0.0039(11) -0.0007(5) 0.0016(4)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
N(1) 0.1067(3) 0.1951(3) 0.61160(10) Bani ? ?
C(1) 0.0574(5) 0.0214(4) 0.6212(2) Bani ? ?
O(2) 0.3263(3) 0.1599(3) 0.69710(10) Bani ? ?
C(2) 0.2463(4) 0.2494(3) 0.65380(10) Bani ? ?
N(3) 0.2890(3) 0.4127(3) 0.64410(10) Bani ? ?
C(3) 0.4403(4) 0.4758(4) 0.6857(2) Bani ? ?
O(4) 0.2457(3) 0.6602(2) 0.58550(10) Bani ? ?
C(4) 0.2024(4) 0.5188(4) 0.59400(10) Bani ? ?
N(5) 0.0625(3) 0.4538(3) 0.55510(10) Bani ? ?
C(5) -0.0273(4) 0.5627(4) 0.4988(2) Bani ? ?
O(6) -0.1066(3) 0.2375(2) 0.52130(10) Bani ? ?
C(6) 0.0114(4) 0.2915(3) 0.55950(10) Bani ? ?
C(11) -0.0487(5) -0.0049(5) 0.6958(2) Bani ? ?
C(33) 0.5998(5) 0.4589(5) 0.6353(2) Bani ? ?
C(55) 0.0677(5) 0.5766(4) 0.4206(2) Bani ? ?
H(1A) 0.173(5) -0.048(4) 0.624(2) Biso ? ?
H(1B) -0.005(5) -0.003(4) 0.575(2) Biso ? ?
H(11A) -0.105(5) -0.123(4) 0.699(2) Biso ? ?
H(11B) -0.182(5) 0.070(5) 0.698(2) Biso ? ?
H(11C) 0.023(6) 0.017(5) 0.738(2) Biso ? ?
H(3A) 0.451(4) 0.416(4) 0.734(2) Biso ? ?
H(3B) 0.427(4) 0.593(4) 0.699(2) Biso ? ?
H(33A) 0.688(5) 0.498(5) 0.665(2) Biso ? ?
H(33B) 0.588(5) 0.530(5) 0.586(2) Biso ? ?
H(33C) 0.624(5) 0.346(5) 0.625(2) Biso ? ?
H(5A) -0.039(4) 0.663(4) 0.525(2) Biso ? ?
H(5B) -0.151(4) 0.512(4) 0.490(2) Biso ? ?
H(55A) -0.006(4) 0.645(4) 0.384(2) Biso ? ?
H(55B) 0.077(5) 0.471(4) 0.395(2) Biso ? ?
H(55C) 0.174(4) 0.626(4) 0.431(2) Biso ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 'Doyle \& Turner (1968)'
H 0 0 'Stewart, Davidson \& Simpson (1965)'
N 0.029 0.018 'Doyle \& Turner (1968)'
O 0.047 0.032 'Doyle \& Turner (1968)'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 4
-3 -1 3
0 -3 3
1 0 5
0 4 0
2 2 0
1 2 4
1 3 3
3 0 2
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
C(1) N(1) C(2) 117.4(2) yes
C(1) N(1) C(6) 118.0(2) yes
C(2) N(1) C(6) 124.6(2) yes
N(1) C(1) C(11) 111.7(3) ys
N(1) C(2) O(2) 122.0(3) yes
N(1) C(2) N(3) 116.2(2) yes
O(2) C(2) N(3) 121.9(3) yes
C(2) N(3) C(3) 118.4(2) yes
C(2) N(3) C(4) 123.7(2) yes
C(3) N(3) C(4) 117.8(2) yes
N(3) C(3) C(33) 111.5(2) yes
N(3) C(4) O(4) 121.9(3) yes
N(3) C(4) N(5) 116.0(2) yes
O(4) C(4) N(5) 122.1(3) yes
C(4) N(5) C(5) 116.8(2) yes
C(4) N(5) C(6) 124.8(2) yes
C(5) N(5) C(6) 118.1(2) yes
N(5) C(5) C(55) 111.5(3) yes
N(1) C(6) N(5) 114.6(2) yes
N(1) C(6) O(6) 122.6(3) yes
N(5) C(6) O(6) 122.8(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(1) . . 1.478(4) yes
N(1) C(2) . . 1.378(4) yes
N(1) C(6) . . 1.396(4) yes
C(1) C(11) . . 1.523(5) yes
O(2) C(2) . . 1.208(3) yes
C(2) N(3) . . 1.384(4) yes
N(3) C(3) . . 1.471(4) yes
N(3) C(4) . . 1.386(4) yes
C(3) C(33) . . 1.518(5) yes
O(4) C(4) . . 1.211(4) yes
C(4) N(5) . . 1.383(4) yes
N(5) C(5) . . 1.478(4) yes
N(5) C(6) . . 1.386(4) yes
C(5) C(55) . . 1.518(4) yes
O(6) C(6) . . 1.210(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10130566
