#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/28/4502815.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_4502815
loop_
_publ_author_name
'Bhattacharya, Suman'
'Saha, Binoy K.'
_publ_section_title
;
 Isostructurality in the Guest Free Forms and in the Clathrates of
 1,3,5-Triethyl-2,4,6-tris(4-halophenoxy)methylbenzenes
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              169
_journal_paper_doi               10.1021/cg2009144
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C33 H33 Cl3 O3, C7 H7'
_chemical_formula_sum            'C40 H40 Cl3 O3'
_chemical_formula_weight         675.08
_chemical_name_common            '1Cl, toluene'
_chemical_name_systematic
;
1,3,5-triethyl-2,4,6-tris(4-chlorophenoxy)methylbenzene, tolene
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-21
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.08.18 svn.r1932, GUI svn.r3819)
;
_cell_angle_alpha                106.41(3)
_cell_angle_beta                 108.55(4)
_cell_angle_gamma                99.14(4)
_cell_formula_units_Z            2
_cell_length_a                   10.472(6)
_cell_length_b                   14.437(5)
_cell_length_c                   15.721(6)
_cell_measurement_reflns_used    1590
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.7729
_cell_measurement_theta_min      2.8741
_cell_volume                     2079.1(18)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13580
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.009(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         7328
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.1037
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2934
_refine_ls_wR_factor_ref         0.3471
_reflns_number_gt                3706
_reflns_number_total             7328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg2009144_si_001.cif
_cod_data_source_block           1Cl.toluene-sqz
_cod_original_cell_volume        2079.0(17)
_cod_database_code               4502815
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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
Cl1 Cl 0.17928(15) 0.21786(16) 0.08661(11) 0.1193(9) Uani 1 1 d .
Cl3 Cl 1.5462(2) 0.28930(13) 0.97709(13) 0.1086(7) Uani 1 1 d .
Cl2 Cl 1.53368(19) 1.17004(12) 0.64178(16) 0.1119(7) Uani 1 1 d .
C3 C 1.0233(4) 0.7014(3) 0.6506(3) 0.0402(9) Uani 1 1 d .
O3 O 1.2170(3) 0.4967(2) 0.7657(2) 0.0571(8) Uani 1 1 d .
C4 C 1.0856(4) 0.6679(3) 0.7236(3) 0.0416(10) Uani 1 1 d .
O1 O 0.6417(3) 0.4622(2) 0.4460(2) 0.0591(9) Uani 1 1 d .
C5 C 1.0384(4) 0.5668(3) 0.7112(3) 0.0420(10) Uani 1 1 d .
O2 O 1.1881(3) 0.8063(2) 0.6262(2) 0.0584(9) Uani 1 1 d .
C6 C 0.9368(4) 0.4998(3) 0.6239(3) 0.0424(10) Uani 1 1 d .
C1 C 0.8786(4) 0.5348(3) 0.5515(3) 0.0424(10) Uani 1 1 d .
C2 C 0.9212(4) 0.6355(3) 0.5636(3) 0.0431(10) Uani 1 1 d .
C8 C 1.0798(4) 0.8078(3) 0.6618(3) 0.0513(11) Uani 1 1 d .
H8A H 1.0074 0.8316 0.6251 0.062 Uiso 1 1 calc R
H8B H 1.1164 0.8511 0.7287 0.062 Uiso 1 1 calc R
C16 C 0.5378(4) 0.4024(3) 0.3603(3) 0.0489(11) Uani 1 1 d .
C7 C 0.7782(4) 0.4625(3) 0.4559(3) 0.0524(11) Uani 1 1 d .
H7A H 0.7979 0.4810 0.4057 0.063 Uiso 1 1 calc R
H7B H 0.7894 0.3956 0.4490 0.063 Uiso 1 1 calc R
C9 C 1.1089(5) 0.5305(3) 0.7877(3) 0.0506(11) Uani 1 1 d .
H9A H 1.1467 0.5843 0.8498 0.061 Uiso 1 1 calc R
H9B H 1.0433 0.4762 0.7895 0.061 Uiso 1 1 calc R
C17 C 0.5585(5) 0.3425(4) 0.2856(3) 0.0669(15) Uani 1 1 d .
H17 H 0.6486 0.3393 0.2909 0.080 Uiso 1 1 calc R
C18 C 0.4466(5) 0.2866(4) 0.2018(3) 0.0677(15) Uani 1 1 d .
H18 H 0.4614 0.2467 0.1499 0.081 Uiso 1 1 calc R
C22 C 1.2640(4) 0.8950(3) 0.6323(3) 0.0504(11) Uani 1 1 d .
C12 C 1.2008(4) 0.7381(3) 0.8157(3) 0.0505(11) Uani 1 1 d .
H12A H 1.2642 0.7011 0.8401 0.061 Uiso 1 1 calc R
H12B H 1.2533 0.7899 0.8022 0.061 Uiso 1 1 calc R
C28 C 1.2914(5) 0.4506(3) 0.8203(3) 0.0510(11) Uani 1 1 d .
C21 C 0.4072(5) 0.4068(4) 0.3510(4) 0.0749(17) Uani 1 1 d .
H21 H 0.3922 0.4487 0.4018 0.090 Uiso 1 1 calc R
C26 C 1.4551(6) 0.9725(4) 0.6063(4) 0.0785(16) Uani 1 1 d .
H26 H 1.5294 0.9686 0.5864 0.094 Uiso 1 1 calc R
C33 C 1.2755(5) 0.4387(3) 0.8991(3) 0.0603(12) Uani 1 1 d .
H33 H 1.2105 0.4643 0.9204 0.072 Uiso 1 1 calc R
C19 C 0.3179(5) 0.2888(4) 0.1942(4) 0.0759(17) Uani 1 1 d .
C23 C 1.2377(5) 0.9846(3) 0.6619(3) 0.0561(12) Uani 1 1 d .
H23 H 1.1615 0.9884 0.6797 0.067 Uiso 1 1 calc R
C13 C 1.1525(6) 0.7869(4) 0.8915(3) 0.0690(15) Uani 1 1 d .
H13A H 1.0998 0.8310 0.8716 0.104 Uiso 1 1 calc R
H13B H 1.2321 0.8249 0.9499 0.104 Uiso 1 1 calc R
H13C H 1.0943 0.7365 0.9022 0.104 Uiso 1 1 calc R
C10 C 0.8560(5) 0.6739(4) 0.4854(3) 0.0615(13) Uani 1 1 d .
H10A H 0.9257 0.7292 0.4886 0.074 Uiso 1 1 calc R
H10B H 0.8285 0.6209 0.4237 0.074 Uiso 1 1 calc R
C20 C 0.2960(5) 0.3503(4) 0.2675(4) 0.0813(18) Uani 1 1 d .
H20 H 0.2058 0.3541 0.2611 0.098 Uiso 1 1 calc R
C31 C 1.4461(6) 0.3529(4) 0.9172(4) 0.0688(15) Uani 1 1 d .
C24 C 1.3224(6) 1.0705(3) 0.6661(4) 0.0678(14) Uani 1 1 d .
H24 H 1.3044 1.1322 0.6872 0.081 Uiso 1 1 calc R
C30 C 1.4661(6) 0.3660(4) 0.8400(4) 0.0768(16) Uani 1 1 d .
H30 H 1.5330 0.3415 0.8205 0.092 Uiso 1 1 calc R
C29 C 1.3879(5) 0.4152(4) 0.7910(3) 0.0628(13) Uani 1 1 d .
H29 H 1.4010 0.4243 0.7378 0.075 Uiso 1 1 calc R
C27 C 1.3706(5) 0.8882(4) 0.6027(4) 0.0721(15) Uani 1 1 d .
H27 H 1.3865 0.8261 0.5797 0.087 Uiso 1 1 calc R
C32 C 1.3543(6) 0.3895(4) 0.9474(4) 0.0722(15) Uani 1 1 d .
H32 H 1.3434 0.3817 1.0016 0.087 Uiso 1 1 calc R
C14 C 0.8919(5) 0.3915(3) 0.6110(4) 0.0585(13) Uani 1 1 d .
H14A H 0.8764 0.3506 0.5460 0.070 Uiso 1 1 calc R
H14B H 0.9665 0.3755 0.6547 0.070 Uiso 1 1 calc R
C15 C 0.7623(6) 0.3657(5) 0.6288(5) 0.091(2) Uani 1 1 d .
H15A H 0.6866 0.3774 0.5832 0.137 Uiso 1 1 calc R
H15B H 0.7764 0.4067 0.6926 0.137 Uiso 1 1 calc R
H15C H 0.7400 0.2962 0.6220 0.137 Uiso 1 1 calc R
C25 C 1.4290(6) 1.0641(4) 0.6400(4) 0.0713(15) Uani 1 1 d .
C11 C 0.7328(7) 0.7084(5) 0.4908(5) 0.094(2) Uani 1 1 d .
H11A H 0.7072 0.7432 0.4469 0.141 Uiso 1 1 calc R
H11B H 0.7548 0.7528 0.5549 0.141 Uiso 1 1 calc R
H11C H 0.6561 0.6516 0.4740 0.141 Uiso 1 1 calc R
C1G C 0.9362(13) 0.4094(9) 0.9500(9) 0.150(3) Uiso 1 1 d .
C1H C 1.4507(12) 1.0087(7) 1.0692(8) 0.146(3) Uiso 1 1 d D
C1F C 1.4322(12) 1.0286(8) 0.9260(8) 0.154(3) Uiso 1 1 d .
H1F H 1.3878 1.0475 0.8748 0.185 Uiso 1 1 calc R
C1I C 1.3910(11) 1.0354(7) 0.9902(8) 0.143(3) Uiso 1 1 d .
H1I H 1.3136 1.0603 0.9868 0.171 Uiso 1 1 calc R
C1M C 1.1169(16) 0.5086(12) 1.0741(11) 0.198(5) Uiso 1 1 d .
H1M H 1.1996 0.5186 1.1250 0.237 Uiso 1 1 calc R
C1N C 1.0451(15) 0.4324(10) 1.0234(10) 0.169(4) Uiso 1 1 d .
H1N H 1.0706 0.3783 1.0383 0.203 Uiso 1 1 calc R
C1O C 1.428(2) 1.0071(16) 1.1469(14) 0.162(7) Uiso 0.50 1 d PD
H1OA H 1.4695 0.9599 1.1700 0.243 Uiso 0.50 1 calc PR
H1OB H 1.3286 0.9874 1.1313 0.243 Uiso 0.50 1 calc PR
H1OC H 1.4680 1.0728 1.1957 0.243 Uiso 0.50 1 calc PR
C1P C 0.855(3) 0.3335(18) 0.8856(17) 0.177(8) Uiso 0.50 1 d P
H1PA H 0.7751 0.3138 0.9002 0.265 Uiso 0.50 1 calc PR
H1PB H 0.9010 0.2808 0.8793 0.265 Uiso 0.50 1 calc PR
H1PC H 0.8258 0.3460 0.8265 0.265 Uiso 0.50 1 calc PR
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'
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
_geom_angle_site_symmetry_3
C4 C3 C2 121.2(3) .
C4 C3 C8 118.8(3) .
C2 C3 C8 119.6(4) .
C28 O3 C9 118.9(4) .
C3 C4 C5 119.0(3) .
C3 C4 C12 121.1(4) .
C5 C4 C12 119.8(4) .
C16 O1 C7 117.3(3) .
C4 C5 C9 118.9(3) .
C6 C5 C4 120.2(4) .
C6 C5 C9 120.6(4) .
C22 O2 C8 118.0(3) .
C5 C6 C14 119.3(4) .
C1 C6 C5 119.5(4) .
C1 C6 C14 121.2(4) .
C6 C1 C2 121.1(3) .
C6 C1 C7 119.6(4) .
C2 C1 C7 119.1(4) .
C3 C2 C1 118.9(4) .
C3 C2 C10 120.0(4) .
C1 C2 C10 121.1(4) .
O2 C8 C3 105.1(3) .
C17 C16 O1 124.6(4) .
C21 C16 O1 116.1(4) .
C21 C16 C17 119.2(4) .
O1 C7 C1 110.4(3) .
O3 C9 C5 106.5(4) .
C16 C17 C18 119.9(4) .
C19 C18 C17 120.5(4) .
C23 C22 O2 125.6(4) .
C27 C22 O2 114.5(4) .
C27 C22 C23 119.9(4) .
C13 C12 C4 114.5(4) .
C33 C28 O3 125.3(4) .
C29 C28 O3 115.2(4) .
C29 C28 C33 119.6(5) .
C16 C21 C20 120.5(5) .
C27 C26 C25 119.1(5) .
C28 C33 C32 120.2(5) .
C18 C19 Cl1 119.1(4) .
C18 C19 C20 120.2(4) .
C20 C19 Cl1 120.6(4) .
C22 C23 C24 120.8(5) .
C11 C10 C2 113.8(5) .
C19 C20 C21 119.6(5) .
C30 C31 Cl3 118.6(5) .
C32 C31 Cl3 120.6(5) .
C32 C31 C30 120.8(5) .
C25 C24 C23 119.1(5) .
C31 C30 C29 119.9(5) .
C28 C29 C30 119.5(5) .
C22 C27 C26 119.9(5) .
C31 C32 C33 120.0(5) .
C15 C14 C6 112.7(4) .
C26 C25 Cl2 118.9(4) .
C24 C25 Cl2 119.9(4) .
C24 C25 C26 121.1(4) .
C1N C1G C1M 118.2(12) 2_767
C1P C1G C1M 104.2(18) 2_767
C1P C1G C1N 137.6(18) .
C1I C1H C1F 117.2(11) 2_877
C1O C1H C1F 105.4(15) 2_877
C1O C1H C1I 137.4(16) .
C1I C1F C1H 118.0(12) 2_877
C1F C1I C1H 124.8(12) .
C1N C1M C1G 111.9(15) 2_767
C1M C1N C1G 129.8(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C19 1.733(5) .
Cl3 C31 1.731(5) .
Cl2 C25 1.722(5) .
C3 C4 1.385(6) .
C3 C2 1.389(5) .
C3 C8 1.495(6) .
O3 C9 1.403(5) .
O3 C28 1.359(5) .
C4 C5 1.399(5) .
C4 C12 1.500(5) .
O1 C16 1.362(5) .
O1 C7 1.387(5) .
C5 C6 1.395(5) .
C5 C9 1.477(6) .
O2 C8 1.416(5) .
O2 C22 1.355(5) .
C6 C1 1.380(6) .
C6 C14 1.495(6) .
C1 C2 1.390(6) .
C1 C7 1.488(5) .
C2 C10 1.502(6) .
C16 C17 1.350(6) .
C16 C21 1.343(6) .
C17 C18 1.369(6) .
C18 C19 1.321(7) .
C22 C23 1.349(6) .
C22 C27 1.347(7) .
C12 C13 1.481(6) .
C28 C33 1.355(7) .
C28 C29 1.350(6) .
C21 C20 1.366(7) .
C26 C27 1.361(7) .
C26 C25 1.384(8) .
C33 C32 1.361(7) .
C19 C20 1.349(7) .
C23 C24 1.377(6) .
C10 C11 1.472(8) .
C31 C30 1.353(8) .
C31 C32 1.318(8) .
C24 C25 1.314(7) .
C30 C29 1.364(7) .
C14 C15 1.482(7) .
C1G C1M 1.477(16) 2_767
C1G C1N 1.252(13) .
C1G C1P 1.21(2) .
C1H C1F 1.404(14) 2_877
C1H C1I 1.390(13) .
C1H C1O 1.324(15) .
C1F C1H 1.404(14) 2_877
C1F C1I 1.204(12) .
C1M C1G 1.477(16) 2_767
C1M C1N 1.128(14) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.003 430 54 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145055
