#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:13:38 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/95/7039583.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_7039583
loop_
_publ_author_name
'Guchhait, Tapas'
'Mani, Ganesan'
'Schulzke, Carola'
_publ_section_title
;
 Synthesis and structural characterization of anion complexes with
 azacalix[2]dipyrrolylmethane: effect of anion charge on the conformation
 of the macrocycle.
;
_journal_issue                   29
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11781
_journal_page_last               11790
_journal_paper_doi               10.1039/c6dt01396a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C33 H52 Cl2 N6 O'
_chemical_formula_weight         619.70
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-06-13 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                101.215(4)
_cell_angle_beta                 109.626(4)
_cell_angle_gamma                96.150(4)
_cell_formula_units_Z            2
_cell_length_a                   11.4134(14)
_cell_length_b                   11.7294(14)
_cell_length_c                   14.5809(17)
_cell_measurement_reflns_used    19156
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.171
_cell_measurement_theta_min      1.530
_cell_volume                     1771.8(4)
_computing_data_collection       APEX2
_computing_molecular_graphics    Diamond3.2
_computing_publication_material  'CIFTAB (Sheldrick 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    sir92
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Brucker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.895
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19156
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.171
_diffrn_reflns_theta_min         1.530
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       Prism
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5590
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0700
_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)+(0.1571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2357
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2891
_reflns_number_total             5590
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01396a2.cif
_cod_data_source_block           2c
_cod_depositor_comments
'Adding full bibliography for 7039581--7039589.cif.'
_cod_database_code               7039583
_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   0.899
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.33090(12) 0.52877(11) 0.48077(10) 0.0797(5) Uani 1 1 d . .
Cl2 Cl 0.81757(12) 0.02954(10) 0.53642(10) 0.0758(4) Uani 1 1 d . .
N1 N 0.9805(3) 0.2695(3) 0.5861(3) 0.0531(9) Uani 1 1 d . .
H1N H 0.910(4) 0.186(4) 0.565(3) 0.079(11) Uiso 1 1 d . U
N2 N 1.1303(4) -0.1630(3) 0.6587(3) 0.0584(10) Uani 1 1 d . .
H2N H 1.192(5) -0.108(4) 0.652(3) 0.078(8) Uiso 1 1 d . U
N3 N 1.1207(4) 0.0966(3) 0.7015(3) 0.0558(10) Uani 1 1 d . .
H3N H 1.053(5) 0.043(4) 0.655(4) 0.078(8) Uiso 1 1 d . U
N4 N 0.5666(4) 0.4013(4) 0.7151(3) 0.0574(10) Uani 1 1 d . .
H4N H 0.516(5) 0.444(4) 0.713(4) 0.078(8) Uiso 1 1 d . U
N5 N 0.3080(3) 0.3529(3) 0.2736(3) 0.0565(10) Uani 1 1 d . .
H5N H 0.291(4) 0.412(4) 0.318(4) 0.078(8) Uiso 1 1 d . U
N6 N 0.4513(3) 0.2508(3) 0.4750(3) 0.0571(11) Uani 1 1 d . .
H6N H 0.478(5) 0.315(4) 0.478(4) 0.079(11) Uiso 1 1 d . U
C1 C 1.2821(9) -0.1560(7) 0.9462(6) 0.161(4) Uani 1 1 d . U
H1A H 1.2512 -0.1313 0.9991 0.242 Uiso 1 1 calc R U
H1B H 1.3642 -0.1757 0.9739 0.242 Uiso 1 1 calc R U
H1C H 1.2248 -0.2241 0.8980 0.242 Uiso 1 1 calc R U
C2 C 1.2918(6) -0.0580(5) 0.8960(4) 0.100(2) Uani 1 1 d . U
H2A H 1.3425 -0.0766 0.8554 0.120 Uiso 1 1 calc R U
H2B H 1.3380 0.0133 0.9478 0.120 Uiso 1 1 calc R U
C3 C 0.9607(6) 0.0435(6) 0.8376(5) 0.0985(19) Uani 1 1 d . .
H3A H 0.9824 0.1172 0.8224 0.148 Uiso 1 1 calc R U
H3B H 0.9132 0.0546 0.8808 0.148 Uiso 1 1 calc R U
H3C H 0.9106 -0.0143 0.7764 0.148 Uiso 1 1 calc R U
C4 C 1.0795(7) 0.0014(5) 0.8893(4) 0.0935(18) Uani 1 1 d . .
H4A H 1.0559 -0.0684 0.9102 0.112 Uiso 1 1 calc R U
H4B H 1.1299 0.0621 0.9496 0.112 Uiso 1 1 calc R U
C5 C 1.1649(5) -0.0295(4) 0.8274(4) 0.0689(13) Uani 1 1 d . .
C6 C 1.0955(4) -0.1365(4) 0.7412(3) 0.0585(12) Uani 1 1 d . .
C7 C 1.0035(4) -0.2274(4) 0.7296(4) 0.0614(12) Uani 1 1 d . .
H7 H 0.9630 -0.2339 0.7746 0.074 Uiso 1 1 calc R U
C8 C 0.9793(4) -0.3101(4) 0.6385(4) 0.0598(12) Uani 1 1 d . .
H8 H 0.9205 -0.3805 0.6127 0.072 Uiso 1 1 calc R U
C9 C 0.9431(4) 0.2690(4) 0.4048(3) 0.0537(11) Uani 1 1 d . .
C10 C 0.4291(4) 0.2406(4) 0.5710(3) 0.0652(13) Uani 1 1 d . .
H10A H 0.3637 0.2844 0.5776 0.078 Uiso 1 1 calc R U
H10B H 0.3991 0.1582 0.5661 0.078 Uiso 1 1 calc R U
C11 C 0.5401(5) 0.1754(5) 0.4533(4) 0.0815(16) Uani 1 1 d . .
H11A H 0.5590 0.1922 0.3973 0.122 Uiso 1 1 calc R U
H11B H 0.5018 0.0936 0.4372 0.122 Uiso 1 1 calc R U
H11C H 0.6169 0.1918 0.5112 0.122 Uiso 1 1 calc R U
C12 C 0.3262(4) 0.2218(4) 0.3884(3) 0.0619(12) Uani 1 1 d . .
H12A H 0.2917 0.1384 0.3751 0.074 Uiso 1 1 calc R U
H12B H 0.2681 0.2662 0.4084 0.074 Uiso 1 1 calc R U
C13 C 0.3313(4) 0.2470(4) 0.2949(4) 0.0605(12) Uani 1 1 d . .
C14 C 0.3484(5) 0.1798(5) 0.2139(4) 0.0758(15) Uani 1 1 d . .
H14 H 0.3645 0.1031 0.2069 0.091 Uiso 1 1 calc R U
C15 C 0.3371(5) 0.2482(4) 0.1441(4) 0.0733(14) Uani 1 1 d . .
H15 H 0.3459 0.2248 0.0824 0.088 Uiso 1 1 calc R U
C16 C 0.6886(4) 0.6455(4) 0.8195(3) 0.0607(12) Uani 1 1 d . .
C17 C 0.7259(5) 0.5459(4) 0.8676(3) 0.0687(14) Uani 1 1 d . .
C18 C 0.8773(7) 0.5679(5) 0.9105(5) 0.137(3) Uani 1 1 d . U
H18A H 0.9022 0.5064 0.9448 0.164 Uiso 1 1 calc R U
H18B H 0.9034 0.5552 0.8531 0.164 Uiso 1 1 calc R U
C19 C 0.9494(8) 0.6767(7) 0.9761(7) 0.162(4) Uani 1 1 d . U
H19A H 0.9308 0.7395 0.9432 0.243 Uiso 1 1 calc R U
H19B H 1.0379 0.6739 0.9945 0.243 Uiso 1 1 calc R U
H19C H 0.9287 0.6907 1.0354 0.243 Uiso 1 1 calc R U
C20 C 0.6619(10) 0.5428(6) 0.9467(5) 0.152(4) Uani 1 1 d . U
H20A H 0.6901 0.6190 0.9951 0.182 Uiso 1 1 calc R U
H20B H 0.5712 0.5335 0.9124 0.182 Uiso 1 1 calc R U
C21 C 0.6855(14) 0.4495(9) 1.0030(7) 0.232(6) Uani 1 1 d . U
H21A H 0.7156 0.3883 0.9679 0.348 Uiso 1 1 calc R U
H21B H 0.6083 0.4164 1.0085 0.348 Uiso 1 1 calc R U
H21C H 0.7480 0.4834 1.0690 0.348 Uiso 1 1 calc R U
C22 C 0.6798(4) 0.4275(4) 0.7932(3) 0.0566(11) Uani 1 1 d . .
C23 C 0.7293(5) 0.3263(5) 0.7879(4) 0.0754(14) Uani 1 1 d . .
H23 H 0.8067 0.3171 0.8315 0.090 Uiso 1 1 calc R U
C24 C 0.6449(6) 0.2398(4) 0.7067(4) 0.0821(16) Uani 1 1 d . .
H24 H 0.6555 0.1625 0.6869 0.099 Uiso 1 1 calc R U
C25 C 0.5451(4) 0.2863(4) 0.6613(3) 0.0592(12) Uani 1 1 d . .
C26 C 0.9284(4) 0.3253(4) 0.4988(4) 0.0612(12) Uani 1 1 d . .
H26A H 0.8389 0.3239 0.4853 0.073 Uiso 1 1 calc R U
H26B H 0.9700 0.4076 0.5192 0.073 Uiso 1 1 calc R U
C27 C 0.9744(5) 0.3436(4) 0.6779(4) 0.0787(15) Uani 1 1 d . .
H27A H 0.8897 0.3574 0.6653 0.118 Uiso 1 1 calc R U
H27B H 1.0314 0.4179 0.6971 0.118 Uiso 1 1 calc R U
H27C H 0.9983 0.3038 0.7312 0.118 Uiso 1 1 calc R U
C28 C 1.1106(4) 0.2449(4) 0.5990(3) 0.0568(12) Uani 1 1 d . .
H28A H 1.1058 0.1863 0.5402 0.068 Uiso 1 1 calc R U
H28B H 1.1646 0.3168 0.6030 0.068 Uiso 1 1 calc R U
C29 C 1.1689(4) 0.2017(4) 0.6895(3) 0.0516(11) Uani 1 1 d . .
C30 C 1.2775(5) 0.2499(4) 0.7702(4) 0.0671(13) Uani 1 1 d . .
H30 H 1.3300 0.3216 0.7817 0.081 Uiso 1 1 calc R U
C31 C 1.2956(5) 0.1712(4) 0.8330(4) 0.0704(14) Uani 1 1 d . .
H31 H 1.3629 0.1815 0.8934 0.084 Uiso 1 1 calc R U
C32 C 1.1970(4) 0.0767(4) 0.7900(4) 0.0606(12) Uani 1 1 d . .
O1 O 0.3336(5) 0.5067(4) 0.6808(4) 0.1323(17) Uani 1 1 d . .
H1 H 0.2819 0.4941 0.6234 0.198 Uiso 1 1 calc R U
C33 C 0.3168(7) 0.6067(7) 0.7401(5) 0.114(2) Uani 1 1 d . .
H33A H 0.3294 0.5951 0.8058 0.171 Uiso 1 1 calc R U
H33B H 0.2325 0.6205 0.7100 0.171 Uiso 1 1 calc R U
H33C H 0.3770 0.6738 0.7453 0.171 Uiso 1 1 calc R U
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
C27 N1 C28 113.0(4) . .
C27 N1 C26 109.6(3) . .
C28 N1 C26 112.2(3) . .
C6 N2 C9 109.3(4) . 2_756
C29 N3 C32 109.9(4) . .
C22 N4 C25 110.4(4) . .
C13 N5 C16 109.9(4) . 2_666
C11 N6 C12 111.1(4) . .
C11 N6 C10 112.7(4) . .
C12 N6 C10 109.4(4) . .
C1 C2 C5 117.6(6) . .
C3 C4 C5 116.8(5) . .
C32 C5 C6 111.3(4) . .
C32 C5 C4 108.6(4) . .
C6 C5 C4 109.3(4) . .
C32 C5 C2 108.4(4) . .
C6 C5 C2 109.1(4) . .
C4 C5 C2 110.1(5) . .
C7 C6 N2 106.6(4) . .
C7 C6 C5 131.5(5) . .
N2 C6 C5 121.6(4) . .
C6 C7 C8 108.8(4) . .
C9 C8 C7 107.6(4) 2_756 .
C8 C9 N2 107.6(4) 2_756 2_756
C8 C9 C26 128.6(4) 2_756 .
N2 C9 C26 123.7(4) 2_756 .
C25 C10 N6 112.1(4) . .
C13 C12 N6 115.1(4) . .
N5 C13 C14 107.4(4) . .
N5 C13 C12 120.0(4) . .
C14 C13 C12 132.4(5) . .
C13 C14 C15 107.0(4) . .
C16 C15 C14 109.3(4) 2_666 .
C15 C16 N5 106.4(4) 2_666 2_666
C15 C16 C17 131.7(4) 2_666 .
N5 C16 C17 121.4(4) 2_666 .
C22 C17 C16 112.3(4) . .
C22 C17 C20 107.0(5) . .
C16 C17 C20 108.0(4) . .
C22 C17 C18 107.2(4) . .
C16 C17 C18 106.6(4) . .
C20 C17 C18 115.9(6) . .
C19 C18 C17 120.9(7) . .
C21 C20 C17 117.0(7) . .
N4 C22 C23 105.8(4) . .
N4 C22 C17 122.2(4) . .
C23 C22 C17 131.9(4) . .
C22 C23 C24 108.5(5) . .
C25 C24 C23 108.5(5) . .
C24 C25 N4 106.8(4) . .
C24 C25 C10 133.9(5) . .
N4 C25 C10 119.3(4) . .
C9 C26 N1 115.6(3) . .
C29 C28 N1 113.3(3) . .
C30 C29 N3 107.9(4) . .
C30 C29 C28 129.4(4) . .
N3 C29 C28 122.6(4) . .
C29 C30 C31 107.3(4) . .
C32 C31 C30 108.3(4) . .
C31 C32 N3 106.6(4) . .
C31 C32 C5 130.7(4) . .
N3 C32 C5 122.6(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C27 1.475(5) .
N1 C28 1.499(5) .
N1 C26 1.517(5) .
N2 C6 1.379(6) .
N2 C9 1.382(5) 2_756
N3 C29 1.363(5) .
N3 C32 1.372(6) .
N4 C22 1.360(6) .
N4 C25 1.372(6) .
N5 C13 1.370(6) .
N5 C16 1.376(6) 2_666
N6 C11 1.486(6) .
N6 C12 1.506(6) .
N6 C10 1.528(6) .
C1 C2 1.491(9) .
C2 C5 1.572(7) .
C3 C4 1.501(8) .
C4 C5 1.560(8) .
C5 C32 1.512(7) .
C5 C6 1.513(6) .
C6 C7 1.356(6) .
C7 C8 1.407(6) .
C8 C9 1.348(6) 2_756
C9 C8 1.348(6) 2_756
C9 N2 1.382(5) 2_756
C9 C26 1.474(6) .
C10 C25 1.475(6) .
C12 C13 1.469(6) .
C13 C14 1.370(6) .
C14 C15 1.397(7) .
C15 C16 1.359(6) 2_666
C16 C15 1.359(6) 2_666
C16 N5 1.376(6) 2_666
C16 C17 1.504(6) .
C17 C22 1.502(6) .
C17 C20 1.562(8) .
C17 C18 1.600(8) .
C18 C19 1.411(9) .
C20 C21 1.486(10) .
C22 C23 1.369(6) .
C23 C24 1.384(7) .
C24 C25 1.341(7) .
C28 C29 1.478(6) .
C29 C30 1.360(6) .
C30 C31 1.405(7) .
C31 C32 1.369(6) .
O1 C33 1.387(7) .
