#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/81/2208108.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_2208108
loop_
_publ_author_name
'Yan-Ping Luo'
'Hong-Bin Zhou'
_publ_section_title
;
 1,3,5-Tris(4-chlorophenyl)-1,3,5-triazinane-2,4,6-trione acetone
 solvate
;
_journal_coeditor_code           KP6070
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o538
_journal_page_last               o539
_journal_paper_doi               10.1107/S1600536806000365
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H12 Cl3 N3 O3, C4 H9 O'
_chemical_formula_moiety         'C21 H12 Cl3 N3 O3, C4 H9 O'
_chemical_formula_sum            'C25 H21 Cl3 N3 O4'
_chemical_formula_weight         533.80
_chemical_name_systematic
;
1,3,5-Tris(4-chlorophenyl)-1,3,5-triazinane-2,4,6-trione acetone solvate
;
_space_group_IT_number           161
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   12.7911(9)
_cell_length_b                   12.7911(9)
_cell_length_c                   26.403(4)
_cell_measurement_reflns_used    2224
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.46
_cell_measurement_theta_min      2.31
_cell_volume                     3741.1(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4820
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_correction_T_min  0.8882
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1650
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.156
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.08(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1261
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0491
_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)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                966
_reflns_number_total             1261
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp6070.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
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:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
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 
;
_cod_original_cell_volume        3741.1(6)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               2208108
_cod_database_fobs_code          2208108
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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
C1 0.9859(3) 1.1031(3) 0.98324(12) 0.0472(6) Uani d . 1 . . C
C2 0.7677(3) 0.9712(3) 0.97957(12) 0.0479(7) Uani d . 1 . . C
C3 0.7272(3) 0.9857(3) 0.93385(12) 0.0552(8) Uani d . 1 . . C
H3 0.7768 1.0062 0.9055 0.062(9) Uiso calc R 1 . . H
C4 0.6126(4) 0.9700(4) 0.92961(13) 0.0651(9) Uani d . 1 . . C
H4 0.5854 0.9828 0.8988 0.055(9) Uiso calc R 1 . . H
C5 0.5404(3) 0.9356(4) 0.97124(16) 0.0666(10) Uani d . 1 . . C
C6 0.5808(4) 0.9210(5) 1.01771(13) 0.0728(11) Uani d . 1 . . C
H6 0.5304 0.8986 1.0459 0.089(13) Uiso calc R 1 . . H
C7 0.6962(3) 0.9401(4) 1.02202(12) 0.0604(9) Uani d . 1 . . C
H7 0.7253 0.9320 1.0532 0.053(9) Uiso calc R 1 . . H
C8 0.740(2) 0.294(3) 0.9989(6) 0.197(10) Uiso d PD 0.70(4) A 1 C
H8A 0.7718 0.2553 0.9779 0.295 Uiso calc PR 0.70(4) A 1 H
H8B 0.6890 0.2393 1.0245 0.295 Uiso calc PR 0.70(4) A 1 H
H8C 0.8055 0.3641 1.0146 0.295 Uiso calc PR 0.70(4) A 1 H
C8' 0.634(6) 0.221(3) 0.9966(16) 0.21(2) Uiso d PD 0.30(4) A 2 C
H8E 0.6926 0.1962 0.9907 0.308 Uiso calc PR 0.30(4) A 2 H
H8F 0.5556 0.1570 0.9864 0.308 Uiso calc PR 0.30(4) A 2 H
H8D 0.6323 0.2370 1.0320 0.308 Uiso calc PR 0.30(4) A 2 H
C9 0.6667 0.3333 0.9663(4) 0.118(4) Uani d SD 1 . . C
Cl1 0.39437(12) 0.9114(2) 0.96640(5) 0.1199(7) Uani d . 1 . . Cl
N1 0.8886(2) 0.9865(2) 0.98283(9) 0.0466(6) Uani d . 1 . . N
O1 0.9734(2) 1.1898(2) 0.98321(9) 0.0641(7) Uani d . 1 . . O
O2 0.6667 0.3333 0.9215(3) 0.230(6) Uani d S 1 A . O
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
C1 0.0438(18) 0.0450(17) 0.0569(16) 0.0253(15) 0.0028(13) 0.0027(13)
C2 0.0385(16) 0.0457(17) 0.0592(18) 0.0209(14) 0.0019(12) 0.0035(13)
C3 0.0535(19) 0.064(2) 0.0508(17) 0.0311(18) 0.0080(14) 0.0080(14)
C4 0.058(2) 0.087(3) 0.0571(19) 0.042(2) -0.0070(16) 0.0078(17)
C5 0.051(2) 0.099(3) 0.0634(19) 0.048(2) 0.0035(16) 0.0112(18)
C6 0.055(2) 0.111(3) 0.060(2) 0.047(2) 0.0126(16) 0.016(2)
C7 0.058(2) 0.084(3) 0.0492(17) 0.043(2) -0.0008(14) 0.0057(15)
C9 0.140(6) 0.140(6) 0.072(5) 0.070(3) 0.000 0.000
Cl1 0.0724(8) 0.227(2) 0.0895(8) 0.0965(10) 0.0048(5) 0.0206(8)
N1 0.0365(13) 0.0384(15) 0.0625(14) 0.0168(12) 0.0023(11) 0.0030(11)
O1 0.0538(15) 0.0472(14) 0.095(2) 0.0281(11) 0.0056(12) 0.0014(11)
O2 0.309(11) 0.309(11) 0.071(6) 0.155(5) 0.000 0.000
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 N1 . 3_675 122.8(3)
O1 C1 N1 . . 122.2(3)
N1 C1 N1 3_675 . 115.0(3)
C3 C2 C7 . . 121.3(3)
C3 C2 N1 . . 118.9(3)
C7 C2 N1 . . 119.8(3)
C2 C3 C4 . . 120.0(3)
C2 C3 H3 . . 120.0
C4 C3 H3 . . 120.0
C5 C4 C3 . . 118.8(3)
C5 C4 H4 . . 120.6
C3 C4 H4 . . 120.6
C4 C5 C6 . . 121.6(3)
C4 C5 Cl1 . . 119.6(3)
C6 C5 Cl1 . . 118.9(3)
C7 C6 C5 . . 119.4(3)
C7 C6 H6 . . 120.3
C5 C6 H6 . . 120.3
C2 C7 C6 . . 118.9(3)
C2 C7 H7 . . 120.5
C6 C7 H7 . . 120.5
C9 C8 H8A . . 109.5
C9 C8 H8B . . 109.5
C9 C8 H8C . . 109.5
C9 C8' H8E . . 109.5
C9 C8' H8F . . 109.5
H8E C8' H8F . . 109.5
C9 C8' H8D . . 109.5
H8E C8' H8D . . 109.5
H8F C8' H8D . . 109.5
O2 C9 C8' . 2_655 122(2)
O2 C9 C8' . 3_665 122.0(19)
C8' C9 C8' 2_655 3_665 95(3)
O2 C9 C8' . . 122.0(19)
C8' C9 C8' 2_655 . 95(3)
C8' C9 C8' 3_665 . 95(3)
O2 C9 C8 . 3_665 124.2(8)
C8' C9 C8 2_655 3_665 114(2)
C8' C9 C8 3_665 3_665 46.8(19)
C8' C9 C8 . 3_665 52.3(18)
O2 C9 C8 . 2_655 124.2(8)
C8' C9 C8 2_655 2_655 46.8(19)
C8' C9 C8 3_665 2_655 52.3(18)
C8' C9 C8 . 2_655 114(2)
C8 C9 C8 3_665 2_655 91.4(11)
O2 C9 C8 . . 124.2(8)
C8' C9 C8 2_655 . 52.3(18)
C8' C9 C8 3_665 . 114(2)
C8' C9 C8 . . 46.8(19)
C8 C9 C8 3_665 . 91.4(11)
C8 C9 C8 2_655 . 91.4(11)
C1 N1 C1 2_765 . 125.0(3)
C1 N1 C2 2_765 . 117.1(2)
C1 N1 C2 . . 117.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O1 . 1.198(4)
C1 N1 3_675 1.383(4)
C1 N1 . 1.385(4)
C2 C3 . 1.362(4)
C2 C7 . 1.374(5)
C2 N1 . 1.461(4)
C3 C4 . 1.381(5)
C3 H3 . 0.9300
C4 C5 . 1.360(6)
C4 H4 . 0.9300
C5 C6 . 1.379(6)
C5 Cl1 . 1.739(3)
C6 C7 . 1.375(5)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 C9 . 1.529(9)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C8' C9 . 1.515(9)
C8' H8E . 0.9600
C8' H8F . 0.9600
C8' H8D . 0.9600
C9 O2 . 1.181(13)
C9 C8' 2_655 1.514(9)
C9 C8' 3_665 1.514(9)
C9 C8 3_665 1.529(9)
C9 C8 2_655 1.529(9)
N1 C1 2_765 1.383(4)
