#------------------------------------------------------------------------------
#$Date: 2017-03-21 08:23:39 +0200 (Tue, 21 Mar 2017) $
#$Revision: 194383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/78/7227885.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_7227885
loop_
_publ_author_name
'Sathiyashivan, Shankar Deval'
'Kumar, Chakka Kiran'
'Shankar, Bhaskaran'
'Sathiyendiran, Malaichamy'
'Masram, Dhanraj T.'
_publ_section_title
;
 Perfect symmetrical cyclic aromatic trimer motif in tripodal molecule
;
_journal_issue                   28
_journal_name_full               'RSC Adv.'
_journal_page_first              17297
_journal_paper_doi               10.1039/C7RA01682D
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C121 H132 Cl6 N12 O15'
_chemical_formula_sum            'C121 H132 Cl6 N12 O15'
_chemical_formula_weight         2207.08
_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_Hall           '-P 3 2"c'
_space_group_name_H-M_alt        'P -3 c 1'
_symmetry_space_group_name_Hall  '-P 3 2"c'
_symmetry_space_group_name_H-M   'P -3 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-08 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   18.620(3)
_cell_length_b                   18.620(3)
_cell_length_c                   18.075(3)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.19
_cell_volume                     5427.1(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1389
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            97883
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         2.526
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0071(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4173
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1132P)²+3.4630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2281
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2761
_reflns_number_total             4173
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ra01682d2.cif
_cod_data_source_block           Compound6
_cod_original_cell_volume        5427(2)
_cod_database_code               7227885
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.10384(19) 0.82644(16) 0.86344(17) 0.0872(9) Uani 1 1 d . . .
O2 O 0.06195(17) 0.84997(14) 0.99341(17) 0.0789(8) Uani 1 1 d . . .
N1 N -0.12369(12) 0.47769(12) 1.04413(10) 0.0297(5) Uani 1 1 d . . .
N2 N -0.04748(14) 0.57221(15) 1.13017(12) 0.0434(6) Uani 1 1 d . . .
C1 C -0.20818(17) 0.35824(17) 1.13436(14) 0.0397(6) Uani 1 1 d . . .
H1 H -0.2410 0.3182 1.0998 0.048 Uiso 1 1 calc R U .
C2 C -0.21624(19) 0.34080(19) 1.20906(15) 0.0477(7) Uani 1 1 d . . .
H2 H -0.2553 0.2880 1.2251 0.057 Uiso 1 1 calc R U .
C3 C -0.1670(2) 0.4007(2) 1.26116(15) 0.0539(8) Uani 1 1 d . . .
H3 H -0.1736 0.3868 1.3111 0.065 Uiso 1 1 calc R U .
C4 C -0.10957(19) 0.4790(2) 1.24019(15) 0.0514(8) Uani 1 1 d . . .
H4 H -0.0771 0.5186 1.2752 0.062 Uiso 1 1 calc R U .
C5 C -0.10060(16) 0.49836(17) 1.16476(14) 0.0389(6) Uani 1 1 d . . .
C6 C -0.14905(15) 0.43811(16) 1.11263(12) 0.0318(6) Uani 1 1 d . . .
C7 C -0.06261(15) 0.55854(16) 1.05900(14) 0.0345(6) Uani 1 1 d . . .
C8 C -0.02100(15) 0.62440(16) 1.00305(15) 0.0363(6) Uani 1 1 d . . .
C9 C -0.00238(17) 0.70395(17) 1.02368(17) 0.0458(7) Uani 1 1 d . . .
H9 H -0.0189 0.7123 1.0699 0.055 Uiso 1 1 calc R U .
C10 C 0.03997(19) 0.77041(18) 0.97684(19) 0.0535(8) Uani 1 1 d . . .
C11 C 0.06322(19) 0.7580(2) 0.90643(19) 0.0559(8) Uani 1 1 d . . .
C12 C 0.04467(18) 0.67890(19) 0.88516(17) 0.0496(8) Uani 1 1 d . . .
H12 H 0.0599 0.6703 0.8384 0.060 Uiso 1 1 calc R U .
C13 C 0.00343(16) 0.61255(17) 0.93346(15) 0.0401(6) Uani 1 1 d . . .
H13 H -0.0079 0.5599 0.9192 0.048 Uiso 1 1 calc R U .
C14 C 0.1342(4) 0.8171(3) 0.7927(3) 0.126(2) Uani 1 1 d . . .
H14A H 0.1685 0.8708 0.7710 0.189 Uiso 1 1 calc R U .
H14B H 0.0881 0.7843 0.7606 0.189 Uiso 1 1 calc R U .
H14C H 0.1661 0.7901 0.7994 0.189 Uiso 1 1 calc R U .
C15 C 0.0475(3) 0.8677(2) 1.0668(3) 0.0857(13) Uani 1 1 d . . .
H15A H 0.0683 0.9262 1.0717 0.128 Uiso 1 1 calc R U .
H15B H 0.0756 0.8509 1.1013 0.128 Uiso 1 1 calc R U .
H15C H -0.0109 0.8380 1.0769 0.128 Uiso 1 1 calc R U .
C16 C -0.15458(14) 0.44221(15) 0.97017(12) 0.0289(5) Uani 1 1 d . . .
H16A H -0.1275 0.4117 0.9547 0.035 Uiso 1 1 calc R U .
H16B H -0.1393 0.4871 0.9353 0.035 Uiso 1 1 calc R U .
C17 C -0.24724(14) 0.38513(14) 0.96720(11) 0.0244(5) Uani 1 1 d . . .
C18 C -0.29888(14) 0.42012(13) 0.96660(11) 0.0247(5) Uani 1 1 d . . .
C19 C -0.26087(15) 0.51416(15) 0.96767(13) 0.0323(6) Uani 1 1 d . . .
H19A H -0.2982 0.5277 0.9935 0.039 Uiso 1 1 calc R U .
H19B H -0.2093 0.5384 0.9952 0.039 Uiso 1 1 calc R U .
C20 C -0.2437(2) 0.55296(19) 0.89104(17) 0.0531(8) Uani 1 1 d . . .
H20A H -0.2195 0.6120 0.8956 0.080 Uiso 1 1 calc R U .
H20B H -0.2948 0.5308 0.8639 0.080 Uiso 1 1 calc R U .
H20C H -0.2061 0.5406 0.8653 0.080 Uiso 1 1 calc R U .
Cl1 Cl 0.9405(5) 0.9046(6) 0.2195(5) 0.516(5) Uani 1 1 d D . .
O3 O 0.0126(6) 0.7082(5) 0.2395(5) 0.096(2) Uiso 0.5 1 d D . P
C23 C 1.0000 1.0000 0.2500 0.279(17) Uiso 1 6 d DS . P
H25 H 0.047(2) 0.742(2) 0.2016(19) 0.096(2) Uiso 1 1 d D . .
H27 H -0.011(3) 0.667(2) 0.2006(19) 0.096(2) Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 O1 C14 117.6(3) . .
C10 O2 C15 118.0(3) . .
C7 N1 C6 106.17(19) . .
C7 N1 C16 125.95(19) . .
C6 N1 C16 127.9(2) . .
C7 N2 C5 105.9(2) . .
C2 C1 C6 117.5(2) . .
C2 C1 H1 121.2 . .
C6 C1 H1 121.2 . .
C1 C2 C3 121.5(3) . .
C1 C2 H2 119.3 . .
C3 C2 H2 119.3 . .
C4 C3 C2 121.2(3) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C3 C4 C5 118.4(3) . .
C3 C4 H4 120.8 . .
C5 C4 H4 120.8 . .
N2 C5 C6 110.4(2) . .
N2 C5 C4 129.3(2) . .
C6 C5 C4 120.3(3) . .
C1 C6 C5 121.1(2) . .
C1 C6 N1 133.7(2) . .
C5 C6 N1 105.2(2) . .
N2 C7 N1 112.4(2) . .
N2 C7 C8 122.5(2) . .
N1 C7 C8 125.1(2) . .
C13 C8 C9 118.9(3) . .
C13 C8 C7 124.4(2) . .
C9 C8 C7 116.6(2) . .
C10 C9 C8 121.2(3) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
O2 C10 C9 124.7(3) . .
O2 C10 C11 115.5(3) . .
C9 C10 C11 119.8(3) . .
O1 C11 C12 124.4(3) . .
O1 C11 C10 116.1(3) . .
C12 C11 C10 119.5(3) . .
C11 C12 C13 120.2(3) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C12 C13 C8 120.4(3) . .
C12 C13 H13 119.8 . .
C8 C13 H13 119.8 . .
O1 C14 H14A 109.5 . .
O1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O2 C15 H15A 109.5 . .
O2 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O2 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N1 C16 C17 113.61(18) . .
N1 C16 H16A 108.8 . .
C17 C16 H16A 108.8 . .
N1 C16 H16B 108.8 . .
C17 C16 H16B 108.8 . .
H16A C16 H16B 107.7 . .
C18 C17 C18 120.8(2) 3_455 .
C18 C17 C16 120.5(2) 3_455 .
C18 C17 C16 118.7(2) . .
C17 C18 C17 119.2(2) 2_565 .
C17 C18 C19 120.8(2) 2_565 .
C17 C18 C19 120.0(2) . .
C20 C19 C18 113.6(2) . .
C20 C19 H19A 108.8 . .
C18 C19 H19A 108.8 . .
C20 C19 H19B 108.8 . .
C18 C19 H19B 108.8 . .
H19A C19 H19B 107.7 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Cl1 Cl1 C23 61.0(2) 4 .
Cl1 Cl1 Cl1 88.3(8) 4 5_765
C23 Cl1 Cl1 47.9(4) . 5_765
O3 O3 H25 160(3) 5 .
O3 O3 H27 102(3) 5 .
H25 O3 H27 84(4) . .
Cl1 C23 Cl1 84.3(8) 6_675 2_765
Cl1 C23 Cl1 109.4(4) 6_675 4
Cl1 C23 Cl1 164.7(6) 2_765 4
Cl1 C23 Cl1 164.7(6) 6_675 .
Cl1 C23 Cl1 109.4(4) 2_765 .
Cl1 C23 Cl1 58.0(5) 4 .
Cl1 C23 Cl1 109.4(4) 6_675 5_765
Cl1 C23 Cl1 58.0(5) 2_765 5_765
Cl1 C23 Cl1 109.4(4) 4 5_765
Cl1 C23 Cl1 84.3(8) . 5_765
Cl1 C23 Cl1 58.0(5) 6_675 3_675
Cl1 C23 Cl1 109.4(4) 2_765 3_675
Cl1 C23 Cl1 84.3(8) 4 3_675
Cl1 C23 Cl1 109.4(4) . 3_675
Cl1 C23 Cl1 164.7(6) 5_765 3_675
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.354(4) .
O1 C14 1.442(5) .
O2 C10 1.359(4) .
O2 C15 1.425(5) .
N1 C7 1.386(3) .
N1 C6 1.397(3) .
N1 C16 1.474(3) .
N2 C7 1.314(3) .
N2 C5 1.378(4) .
C1 C2 1.379(4) .
C1 C6 1.393(4) .
C1 H1 0.9300 .
C2 C3 1.396(4) .
C2 H2 0.9300 .
C3 C4 1.362(5) .
C3 H3 0.9300 .
C4 C5 1.399(4) .
C4 H4 0.9300 .
C5 C6 1.396(4) .
C7 C8 1.475(4) .
C8 C13 1.392(4) .
C8 C9 1.393(4) .
C9 C10 1.376(4) .
C9 H9 0.9300 .
C10 C11 1.400(5) .
C11 C12 1.389(5) .
C12 C13 1.389(4) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C17 1.508(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.402(3) 3_455
C17 C18 1.406(3) .
C18 C17 1.402(3) 2_565
C18 C19 1.526(3) .
C19 C20 1.520(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
Cl1 Cl1 1.599(12) 4
Cl1 C23 1.648(7) .
Cl1 Cl1 2.212(18) 5_765
O3 O3 0.555(16) 5
O3 H25 0.937(19) .
O3 H27 0.973(19) .
C23 Cl1 1.648(7) 6_675
C23 Cl1 1.648(7) 2_765
C23 Cl1 1.648(7) 4
C23 Cl1 1.648(7) 5_765
C23 Cl1 1.648(7) 3_675
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.1(5) . .
C1 C2 C3 C4 0.6(5) . .
C2 C3 C4 C5 -0.1(5) . .
C7 N2 C5 C6 0.3(3) . .
C7 N2 C5 C4 179.6(3) . .
C3 C4 C5 N2 -180.0(3) . .
C3 C4 C5 C6 -0.7(4) . .
C2 C1 C6 C5 -0.8(4) . .
C2 C1 C6 N1 179.9(3) . .
N2 C5 C6 C1 -179.4(2) . .
C4 C5 C6 C1 1.2(4) . .
N2 C5 C6 N1 0.0(3) . .
C4 C5 C6 N1 -179.3(2) . .
C7 N1 C6 C1 179.0(3) . .
C16 N1 C6 C1 -0.9(4) . .
C7 N1 C6 C5 -0.4(3) . .
C16 N1 C6 C5 179.7(2) . .
C5 N2 C7 N1 -0.5(3) . .
C5 N2 C7 C8 176.7(2) . .
C6 N1 C7 N2 0.6(3) . .
C16 N1 C7 N2 -179.5(2) . .
C6 N1 C7 C8 -176.5(2) . .
C16 N1 C7 C8 3.4(4) . .
N2 C7 C8 C13 143.0(3) . .
N1 C7 C8 C13 -40.1(4) . .
N2 C7 C8 C9 -34.1(4) . .
N1 C7 C8 C9 142.8(3) . .
C13 C8 C9 C10 -0.5(4) . .
C7 C8 C9 C10 176.8(3) . .
C15 O2 C10 C9 6.4(5) . .
C15 O2 C10 C11 -173.7(3) . .
C8 C9 C10 O2 -178.6(3) . .
C8 C9 C10 C11 1.6(5) . .
C14 O1 C11 C12 -3.9(6) . .
C14 O1 C11 C10 175.5(4) . .
O2 C10 C11 O1 -0.6(4) . .
C9 C10 C11 O1 179.3(3) . .
O2 C10 C11 C12 178.8(3) . .
C9 C10 C11 C12 -1.3(5) . .
O1 C11 C12 C13 179.3(3) . .
C10 C11 C12 C13 -0.1(5) . .
C11 C12 C13 C8 1.2(4) . .
C9 C8 C13 C12 -0.9(4) . .
C7 C8 C13 C12 -177.9(2) . .
C7 N1 C16 C17 -139.7(2) . .
C6 N1 C16 C17 40.2(3) . .
N1 C16 C17 C18 -102.3(2) . 3_455
N1 C16 C17 C18 76.4(2) . .
C18 C17 C18 C17 1.5(4) 3_455 2_565
C16 C17 C18 C17 -177.16(13) . 2_565
C18 C17 C18 C19 179.69(14) 3_455 .
C16 C17 C18 C19 1.0(3) . .
C17 C18 C19 C20 -92.1(3) 2_565 .
C17 C18 C19 C20 89.8(3) . .
Cl1 Cl1 C23 Cl1 -37.1(7) 4 6_675
Cl1 Cl1 C23 Cl1 -154.2(4) 5_765 6_675
Cl1 Cl1 C23 Cl1 170.3(5) 4 2_765
Cl1 Cl1 C23 Cl1 53.2(7) 5_765 2_765
Cl1 Cl1 C23 Cl1 -117.1(10) 5_765 4
Cl1 Cl1 C23 Cl1 117.1(10) 4 5_765
Cl1 Cl1 C23 Cl1 -69.9(12) 4 3_675
Cl1 Cl1 C23 Cl1 173.0(3) 5_765 3_675
