#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:53:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180403 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/72/7207201.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7207201
loop_
_publ_author_name
'Dai, Fangna'
'Sun, Di'
'Sun, Wenming'
'Liu, Yun-Qi'
'Sun, Daofeng'
_publ_section_title
;
 Conformation variation of tris(2-carboxyethyl)isocyanuric acid induced by
 cocrystallized N-heterocyclic organic molecules
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1376
_journal_paper_doi               10.1039/c1ce06209c
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C12 H15 N3 O9'
_chemical_formula_weight         345.27
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.0660(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6775(7)
_cell_length_b                   15.7719(12)
_cell_length_c                   10.9612(8)
_cell_measurement_reflns_used    3492
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      54.608
_cell_measurement_theta_min      4.543
_cell_volume                     1491.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7268
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0393
_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)+(0.0540P)²+0.5636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                2262
_reflns_number_total             2621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06209c.txt
_cod_data_source_block           p1
_cod_original_sg_symbol_H-M      p2(1)/n
_cod_database_code               7207201
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.73077(18) 0.01817(10) 0.69296(14) 0.0339(4) Uani 1 1 d .
C2 C 0.76322(19) 0.17234(10) 0.70736(15) 0.0345(4) Uani 1 1 d .
C3 C 0.80761(19) 0.08478(11) 0.88970(14) 0.0358(4) Uani 1 1 d .
C4 C 0.7845(2) -0.06869(11) 0.87921(16) 0.0410(4) Uani 1 1 d .
H4A H 0.8776 -0.0708 0.9365 0.049 Uiso 1 1 calc R
H4B H 0.7924 -0.1127 0.8183 0.049 Uiso 1 1 calc R
C5 C 0.6447(2) -0.08657(12) 0.94788(16) 0.0434(4) Uani 1 1 d .
H5A H 0.5797 -0.0364 0.9440 0.052 Uiso 1 1 calc R
H5B H 0.5849 -0.1319 0.9061 0.052 Uiso 1 1 calc R
C6 C 0.68223(19) -0.11070(11) 1.07861(15) 0.0392(4) Uani 1 1 d .
C7 C 0.6795(2) 0.10592(11) 0.50972(14) 0.0371(4) Uani 1 1 d .
H7A H 0.6411 0.1627 0.4907 0.044 Uiso 1 1 calc R
H7B H 0.5968 0.0661 0.4851 0.044 Uiso 1 1 calc R
C8 C 0.8145(2) 0.08817(16) 0.43990(16) 0.0581(6) Uani 1 1 d .
H8A H 0.8989 0.1258 0.4690 0.070 Uiso 1 1 calc R
H8B H 0.8492 0.0304 0.4566 0.070 Uiso 1 1 calc R
C9 C 0.7795(2) 0.09910(17) 0.30502(17) 0.0596(6) Uani 1 1 d .
C10 C 0.8466(2) 0.23711(12) 0.90838(16) 0.0436(4) Uani 1 1 d .
H10A H 0.8834 0.2818 0.8580 0.052 Uiso 1 1 calc R
H10B H 0.9293 0.2230 0.9717 0.052 Uiso 1 1 calc R
C11 C 0.7066(2) 0.26855(12) 0.96774(17) 0.0456(4) Uani 1 1 d .
H11A H 0.6484 0.3072 0.9115 0.055 Uiso 1 1 calc R
H11B H 0.6401 0.2205 0.9801 0.055 Uiso 1 1 calc R
C12 C 0.7444(2) 0.31250(11) 1.08758(16) 0.0416(4) Uani 1 1 d .
O1 O 0.69904(17) -0.04416(8) 0.63164(11) 0.0533(4) Uani 1 1 d .
O2 O 0.75848(18) 0.24076(8) 0.65907(12) 0.0548(4) Uani 1 1 d .
O3 O 0.83623(16) 0.07838(9) 1.00058(10) 0.0526(4) Uani 1 1 d .
O4 O 0.81440(15) -0.12289(11) 1.12639(12) 0.0622(4) Uani 1 1 d .
O5 O 0.56036(15) -0.11847(11) 1.13747(12) 0.0634(4) Uani 1 1 d .
H5C H 0.5861 -0.1373 1.2063 0.095 Uiso 1 1 calc R
O6' O 0.8984(9) 0.0870(5) 0.2470(6) 0.109(3) Uani 0.70 1 d P
H6B H 0.8889 0.1131 0.1820 0.164 Uiso 0.70 1 calc PR
O6 O 0.8709(19) 0.0560(9) 0.2405(16) 0.083(5) Uani 0.30 1 d P
H6A H 0.8299 0.0520 0.1698 0.124 Uiso 0.30 1 calc PR
O7 O 0.6704(4) 0.1404(3) 0.2572(3) 0.0881(11) Uani 0.70 1 d P
O7' O 0.6542(8) 0.0750(7) 0.2543(6) 0.102(3) Uani 0.30 1 d P
O8 O 0.87693(16) 0.32091(11) 1.13651(13) 0.0638(4) Uani 1 1 d .
O9 O 0.62381(16) 0.34022(11) 1.13572(13) 0.0683(5) Uani 1 1 d .
H9A H 0.6476 0.3508 1.2085 0.102 Uiso 1 1 calc R
N1 N 0.77530(16) 0.01462(8) 0.81774(11) 0.0345(3) Uani 1 1 d .
N2 N 0.72404(15) 0.09854(8) 0.64291(11) 0.0323(3) Uani 1 1 d .
N3 N 0.80690(16) 0.16161(8) 0.83165(12) 0.0357(3) Uani 1 1 d .
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
O1 C1 N2 121.97(14)
O1 C1 N1 122.80(14)
N2 C1 N1 115.23(13)
O2 C2 N2 122.36(15)
O2 C2 N3 122.43(15)
N2 C2 N3 115.20(14)
O3 C3 N3 121.83(15)
O3 C3 N1 120.99(16)
N3 C3 N1 117.18(13)
N1 C4 C5 112.60(13)
N1 C4 H4A 109.1
C5 C4 H4A 109.1
N1 C4 H4B 109.1
C5 C4 H4B 109.1
H4A C4 H4B 107.8
C6 C5 C4 114.86(14)
C6 C5 H5A 108.6
C4 C5 H5A 108.6
C6 C5 H5B 108.6
C4 C5 H5B 108.6
H5A C5 H5B 107.5
O4 C6 O5 123.13(15)
O4 C6 C5 123.56(15)
O5 C6 C5 113.31(15)
N2 C7 C8 110.81(14)
N2 C7 H7A 109.5
C8 C7 H7A 109.5
N2 C7 H7B 109.5
C8 C7 H7B 109.5
H7A C7 H7B 108.1
C9 C8 C7 113.50(16)
C9 C8 H8A 108.9
C7 C8 H8A 108.9
C9 C8 H8B 108.9
C7 C8 H8B 108.9
H8A C8 H8B 107.7
O7 C9 O7' 50.3(5)
O7 C9 O6' 119.7(4)
O7' C9 O6' 116.7(5)
O7 C9 O6 122.1(7)
O7' C9 O6 98.8(9)
O7 C9 C8 123.8(2)
O7' C9 C8 119.5(4)
O6' C9 C8 112.6(4)
O6 C9 C8 113.9(7)
N3 C10 C11 110.97(14)
N3 C10 H10A 109.4
C11 C10 H10A 109.4
N3 C10 H10B 109.4
C11 C10 H10B 109.4
H10A C10 H10B 108.0
C12 C11 C10 114.68(15)
C12 C11 H11A 108.6
C10 C11 H11A 108.6
C12 C11 H11B 108.6
C10 C11 H11B 108.6
H11A C11 H11B 107.6
O8 C12 O9 123.14(16)
O8 C12 C11 123.08(16)
O9 C12 C11 113.78(15)
C6 O5 H5C 109.5
O6 O6' C9 81(2)
O6 O6' H6B 109.5
C9 O6' H6B 110.1
O6' O6 C9 75(2)
O6' O6 H6A 109.5
C9 O6 H6A 108.8
O7' O7 C9 65.2(4)
O7 O7' C9 64.5(5)
C12 O9 H9A 109.5
C3 N1 C1 123.74(13)
C3 N1 C4 117.29(13)
C1 N1 C4 118.95(13)
C1 N2 C2 124.84(13)
C1 N2 C7 117.50(13)
C2 N2 C7 117.58(13)
C3 N3 C2 123.56(13)
C3 N3 C10 117.37(14)
C2 N3 C10 118.98(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2063(19)
C1 N2 1.380(2)
C1 N1 1.383(2)
C2 O2 1.201(2)
C2 N2 1.385(2)
C2 N3 1.385(2)
C3 O3 1.219(2)
C3 N3 1.368(2)
C3 N1 1.371(2)
C4 N1 1.475(2)
C4 C5 1.520(2)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.485(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 O4 1.225(2)
C6 O5 1.301(2)
C7 N2 1.4748(19)
C7 C8 1.492(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.488(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 O7 1.220(4)
C9 O7' 1.228(7)
C9 O6' 1.283(7)
C9 O6 1.308(15)
C10 N3 1.477(2)
C10 C11 1.520(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.491(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O8 1.223(2)
C12 O9 1.297(2)
O5 H5C 0.8200
O6' O6 0.55(2)
O6' H6B 0.8200
O6 H6A 0.8200
O7 O7' 1.041(10)
O9 H9A 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5C O8 0.82 1.84 2.6577(18) 174.2 2_647
O6 H6A O3 0.82 1.91 2.639(17) 148.0 1_554
O9 H9A O4 0.82 1.85 2.6701(18) 175.6 2_657
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
N1 C4 C5 C6 -126.93(17)
N2 C7 C8 C9 -176.90(18)
N3 C10 C11 C12 151.17(16)
