#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/64/4306410.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_4306410
loop_
_publ_author_name
'Mariappan Kadarkaraisamy'
'Gerald Caple'
'Andrea R. Gorden'
'Marie A. Squire'
'Andrew G. Sykes'
_publ_contact_author_address     'University of South Dakota'
_publ_contact_author_email       asykes@usd.edu
_publ_contact_author_name        'Andrew G. Sykes'
_publ_section_title
;
Large Amplitude, Proton- and Cation-Activated Latch-Type Mechanical
Switches: O-Protonated Amides Stabilized by Intramolecular, Low-Barrier
Hydrogen Bonds within Macrocycles
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11644
_journal_page_last               11655
_journal_paper_doi               10.1021/ic801238a
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C24 H28 Cl N O11'
_chemical_formula_sum            'C24 H28 Cl N O11'
_chemical_formula_weight         541.92
_chemical_name_common            '[AQHNH(CH3)COH]ClO4-(3)'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                96.6500(10)
_cell_angle_beta                 91.4210(10)
_cell_angle_gamma                107.3660(10)
_cell_formula_units_Z            2
_cell_length_a                   8.91580(10)
_cell_length_b                   11.8831(2)
_cell_length_c                   11.9370(2)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      1.0
_cell_volume                     1196.57(3)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2006)'
_computing_data_collection       'Bruker APEXII (Bruker, 2006)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3(Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997a)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14685
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0354
_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)+(0.0390P)²+0.5844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                3349
_reflns_number_total             4232
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801238a_si_003_01.cif
_cod_data_source_block           06035
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               4306410
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2267(2) 0.54533(15) 1.00548(16) 0.0169(4) Uani 1 1 d . . .
C2 C 0.1598(2) 0.48082(16) 1.09070(16) 0.0198(4) Uani 1 1 d . . .
H2 H 0.1017 0.5124 1.1448 0.024 Uiso 1 1 calc R . .
C3 C 0.1783(2) 0.36931(17) 1.09653(17) 0.0223(4) Uani 1 1 d . . .
H3 H 0.1320 0.3248 1.1547 0.027 Uiso 1 1 calc R . .
C4 C 0.2630(2) 0.32278(16) 1.01906(17) 0.0211(4) Uani 1 1 d . . .
H4 H 0.2769 0.2475 1.0251 0.025 Uiso 1 1 calc R . .
C5 C 0.3282(2) 0.38634(16) 0.93183(17) 0.0190(4) Uani 1 1 d . . .
C6 C 0.4204(2) 0.33514(16) 0.84938(17) 0.0202(4) Uani 1 1 d . . .
C7 C 0.4948(2) 0.40640(16) 0.76007(17) 0.0191(4) Uani 1 1 d . . .
C8 C 0.5889(2) 0.36262(17) 0.68527(17) 0.0226(5) Uani 1 1 d . . .
H8 H 0.5981 0.2854 0.6881 0.027 Uiso 1 1 calc R . .
C9 C 0.6679(2) 0.43180(18) 0.60773(17) 0.0248(5) Uani 1 1 d . . .
H9 H 0.7314 0.4015 0.5572 0.030 Uiso 1 1 calc R . .
C10 C 0.6568(2) 0.54526(17) 0.60178(17) 0.0225(4) Uani 1 1 d . . .
H10 H 0.7121 0.5922 0.5479 0.027 Uiso 1 1 calc R . .
C11 C 0.5637(2) 0.58871(16) 0.67580(16) 0.0187(4) Uani 1 1 d . . .
C12 C 0.4803(2) 0.51927(15) 0.75458(16) 0.0169(4) Uani 1 1 d . . .
C13 C 0.3771(2) 0.56953(15) 0.83061(16) 0.0160(4) Uani 1 1 d . . .
H13 H 0.4409 0.6507 0.8662 0.019 Uiso 1 1 calc R . .
C14 C 0.3094(2) 0.49786(15) 0.92352(16) 0.0161(4) Uani 1 1 d . . .
C15 C 0.1610(2) 0.71922(16) 1.08354(16) 0.0198(4) Uani 1 1 d . . .
H15A H 0.2028 0.7074 1.1574 0.024 Uiso 1 1 calc R . .
H15B H 0.0447 0.6886 1.0807 0.024 Uiso 1 1 calc R . .
C16 C 0.2125(2) 0.84852(17) 1.06994(17) 0.0228(5) Uani 1 1 d . . .
H16A H 0.1859 0.8944 1.1370 0.027 Uiso 1 1 calc R . .
H16B H 0.3282 0.8762 1.0652 0.027 Uiso 1 1 calc R . .
C17 C 0.1882(2) 0.99284(16) 0.95632(18) 0.0252(5) Uani 1 1 d . . .
H17A H 0.3034 1.0264 0.9731 0.030 Uiso 1 1 calc R . .
H17B H 0.1356 1.0371 1.0091 0.030 Uiso 1 1 calc R . .
C18 C 0.1475(2) 1.00582(17) 0.83749(18) 0.0261(5) Uani 1 1 d . . .
H18A H 0.0375 0.9574 0.8146 0.031 Uiso 1 1 calc R . .
H18B H 0.1580 1.0900 0.8305 0.031 Uiso 1 1 calc R . .
C19 C 0.2911(3) 1.01559(18) 0.66382(18) 0.0292(5) Uani 1 1 d . . .
H19A H 0.2773 1.0956 0.6694 0.035 Uiso 1 1 calc R . .
H19B H 0.2213 0.9642 0.6001 0.035 Uiso 1 1 calc R . .
C20 C 0.4588(3) 1.02300(17) 0.64592(18) 0.0274(5) Uani 1 1 d . . .
H20A H 0.4955 1.0682 0.5820 0.033 Uiso 1 1 calc R . .
H20B H 0.5260 1.0650 0.7145 0.033 Uiso 1 1 calc R . .
C21 C 0.6261(2) 0.90161(17) 0.64614(18) 0.0255(5) Uani 1 1 d . . .
H21A H 0.6535 0.9230 0.7283 0.031 Uiso 1 1 calc R . .
H21B H 0.7014 0.9606 0.6064 0.031 Uiso 1 1 calc R . .
C22 C 0.6393(2) 0.78025(17) 0.60943(17) 0.0230(4) Uani 1 1 d . . .
H22A H 0.6005 0.7543 0.5294 0.028 Uiso 1 1 calc R . .
H22B H 0.7507 0.7816 0.6167 0.028 Uiso 1 1 calc R . .
C23 C 0.2281(2) 0.68378(17) 0.74350(16) 0.0193(4) Uani 1 1 d . . .
C24 C 0.1079(2) 0.68900(19) 0.65805(18) 0.0275(5) Uani 1 1 d . . .
H03G H 0.0407 0.7333 0.6930 0.041 Uiso 1 1 calc R . .
H03H H 0.0433 0.6081 0.6286 0.041 Uiso 1 1 calc R . .
H03I H 0.1602 0.7291 0.5959 0.041 Uiso 1 1 calc R . .
O1 O 0.43898(16) 0.23828(11) 0.85789(12) 0.0267(3) Uani 1 1 d . . .
O2 O 0.22034(15) 0.65655(11) 0.99296(11) 0.0191(3) Uani 1 1 d . . .
O3 O 0.13859(15) 0.87011(11) 0.97118(11) 0.0221(3) Uani 1 1 d . . .
O4 O 0.2543(2) 0.96581(13) 0.76738(13) 0.0379(4) Uani 1 1 d . . .
O5 O 0.47090(16) 0.90509(11) 0.62208(11) 0.0234(3) Uani 1 1 d . . .
O6 O 0.54642(15) 0.69955(11) 0.68000(11) 0.0215(3) Uani 1 1 d . . .
O7 O 0.31710(16) 0.77840(12) 0.80257(12) 0.0224(3) Uani 1 1 d . . .
O8 O 0.08853(18) 0.25011(13) 0.73068(12) 0.0342(4) Uani 1 1 d . . .
O9 O 0.05126(19) 0.38223(13) 0.60861(14) 0.0437(5) Uani 1 1 d . . .
O10 O 0.0696(2) 0.19641(16) 0.53458(13) 0.0448(4) Uani 1 1 d . . .
O11 O -0.15283(16) 0.20947(13) 0.62593(13) 0.0324(4) Uani 1 1 d . . .
Cl1 Cl 0.01372(5) 0.25818(4) 0.62559(4) 0.02011(13) Uani 1 1 d . . .
N1 N 0.24753(18) 0.58211(14) 0.75802(14) 0.0163(3) Uani 1 1 d . . .
H98 H 0.191(2) 0.5188(18) 0.7168(17) 0.019(5) Uiso 1 1 d . . .
H99 H 0.292(3) 0.845(3) 0.789(2) 0.064(9) Uiso 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'
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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
O2 C1 C2 124.81(17) . . ?
O2 C1 C14 114.66(16) . . ?
C2 C1 C14 120.53(17) . . ?
C1 C2 C3 119.49(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.87(19) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.91(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C14 120.19(18) . . ?
C4 C5 C6 119.19(16) . . ?
C14 C5 C6 120.61(18) . . ?
O1 C6 C7 120.97(18) . . ?
O1 C6 C5 120.54(18) . . ?
C7 C6 C5 118.43(16) . . ?
C12 C7 C8 119.80(19) . . ?
C12 C7 C6 120.71(17) . . ?
C8 C7 C6 119.36(17) . . ?
C9 C8 C7 119.81(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.35(18) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 118.90(19) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
O6 C11 C10 124.34(18) . . ?
O6 C11 C12 114.85(16) . . ?
C10 C11 C12 120.81(17) . . ?
C7 C12 C11 119.31(17) . . ?
C7 C12 C13 122.12(17) . . ?
C11 C12 C13 118.57(16) . . ?
N1 C13 C14 109.49(15) . . ?
N1 C13 C12 107.29(15) . . ?
C14 C13 C12 115.57(15) . . ?
N1 C13 H13 108.1 . . ?
C14 C13 H13 108.1 . . ?
C12 C13 H13 108.1 . . ?
C5 C14 C1 118.97(18) . . ?
C5 C14 C13 122.09(17) . . ?
C1 C14 C13 118.93(16) . . ?
O2 C15 C16 108.20(16) . . ?
O2 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O2 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
O3 C16 C15 111.38(15) . . ?
O3 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
O3 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O3 C17 C18 109.50(16) . . ?
O3 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O3 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O4 C18 C17 107.29(16) . . ?
O4 C18 H18A 110.3 . . ?
C17 C18 H18A 110.3 . . ?
O4 C18 H18B 110.3 . . ?
C17 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
O4 C19 C20 106.51(17) . . ?
O4 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
O4 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O5 C20 C19 109.09(16) . . ?
O5 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
O5 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
O5 C21 C22 110.75(15) . . ?
O5 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
O6 C22 C21 108.28(16) . . ?
O6 C22 H22A 110.0 . . ?
C21 C22 H22A 110.0 . . ?
O6 C22 H22B 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
O7 C23 N1 118.67(18) . . ?
O7 C23 C24 121.35(17) . . ?
N1 C23 C24 119.97(17) . . ?
C23 C24 H03G 109.5 . . ?
C23 C24 H03H 109.5 . . ?
H03G C24 H03H 109.5 . . ?
C23 C24 H03I 109.5 . . ?
H03G C24 H03I 109.5 . . ?
H03H C24 H03I 109.5 . . ?
C1 O2 C15 117.90(15) . . ?
C16 O3 C17 111.98(14) . . ?
C18 O4 C19 118.15(15) . . ?
C21 O5 C20 111.90(14) . . ?
C11 O6 C22 118.32(15) . . ?
C23 O7 H99 112.2(18) . . ?
O10 Cl1 O11 109.33(10) . . ?
O10 Cl1 O8 110.15(9) . . ?
O11 Cl1 O8 110.87(9) . . ?
O10 Cl1 O9 108.67(11) . . ?
O11 Cl1 O9 108.68(9) . . ?
O8 Cl1 O9 109.09(9) . . ?
C23 N1 C13 123.80(16) . . ?
C23 N1 H98 119.0(13) . . ?
C13 N1 H98 116.6(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.365(2) . ?
C1 C2 1.384(3) . ?
C1 C14 1.405(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C14 1.399(2) . ?
C5 C6 1.488(3) . ?
C6 O1 1.226(2) . ?
C6 C7 1.484(3) . ?
C7 C12 1.394(2) . ?
C7 C8 1.401(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 O6 1.366(2) . ?
C11 C12 1.402(3) . ?
C12 C13 1.507(3) . ?
C13 N1 1.480(2) . ?
C13 C14 1.505(3) . ?
C13 H13 1.0000 . ?
C15 O2 1.442(2) . ?
C15 C16 1.496(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O3 1.422(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O3 1.426(2) . ?
C17 C18 1.492(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O4 1.432(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O4 1.435(3) . ?
C19 C20 1.494(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O5 1.434(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O5 1.420(2) . ?
C21 C22 1.498(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O6 1.436(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O7 1.283(2) . ?
C23 N1 1.301(2) . ?
C23 C24 1.481(3) . ?
C24 H03G 0.9800 . ?
C24 H03H 0.9800 . ?
C24 H03I 0.9800 . ?
O7 H99 0.91(3) . ?
O8 Cl1 1.4326(14) . ?
O9 Cl1 1.4506(15) . ?
O10 Cl1 1.4240(15) . ?
O11 Cl1 1.4240(14) . ?
N1 H98 0.86(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660815
