#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/64/4306411.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_4306411
loop_
_publ_author_name
'Mariappan Kadarkaraisamy'
'Gerald Caple'
'Andrea R. Gorden'
'Marie A. Squire'
'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         'C25 H30 Cl N O11'
_chemical_formula_sum            'C25 H30 Cl N O11'
_chemical_formula_weight         555.95
_chemical_name_common            '[AQHNHC(CH2CH3)OH]ClO4-(4)'
_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                107.619(2)
_cell_angle_beta                 92.281(2)
_cell_angle_gamma                98.963(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3525(11)
_cell_length_b                   10.9335(14)
_cell_length_c                   15.163(2)
_cell_measurement_reflns_used    7490
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      1.0
_cell_volume                     1298.1(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12013
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.9079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0854P)²+1.5945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1647
_reflns_number_gt                3357
_reflns_number_total             4560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801238a_si_003_02.cif
_cod_data_source_block           07038
_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               4306411
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
O9 O 0.8432(3) 0.8101(3) 0.2365(2) 0.0519(8) Uani 1 1 d . . .
H98 H 0.187(4) 0.596(3) -0.304(2) 0.011(8) Uiso 1 1 d . . .
H99 H 0.570(5) 0.666(4) -0.178(3) 0.034(12) Uiso 1 1 d . . .
Cl1 Cl 0.99030(9) 0.87144(8) 0.21418(6) 0.0298(2) Uani 1 1 d . . .
O1 O 0.0591(3) 0.4866(2) -0.65447(15) 0.0286(5) Uani 1 1 d . . .
O2 O 0.4729(3) 0.3950(2) -0.34649(14) 0.0239(5) Uani 1 1 d . . .
O6 O 0.4181(3) 0.8440(2) -0.30447(14) 0.0235(5) Uani 1 1 d . . .
O3 O 0.5927(3) 0.4534(2) -0.14813(15) 0.0257(5) Uani 1 1 d . . .
O7 O 0.5307(3) 0.6563(2) -0.22513(16) 0.0217(5) Uani 1 1 d . . .
O5 O 0.5686(3) 0.9270(2) -0.11412(14) 0.0258(5) Uani 1 1 d . . .
O11 O 1.0463(3) 0.7913(2) 0.12566(16) 0.0361(6) Uani 1 1 d . . .
O4 O 0.6902(3) 0.7196(2) -0.05877(15) 0.0290(5) Uani 1 1 d . . .
O10 O 1.1210(3) 0.8916(2) 0.28751(15) 0.0338(6) Uani 1 1 d . . .
N1 N 0.2813(3) 0.6081(2) -0.30461(17) 0.0189(6) Uani 1 1 d . . .
C5 C 0.2142(3) 0.4178(3) -0.5448(2) 0.0215(7) Uani 1 1 d . . .
C12 C 0.2831(3) 0.6873(3) -0.4371(2) 0.0198(6) Uani 1 1 d . . .
C6 C 0.1476(3) 0.5170(3) -0.5799(2) 0.0225(7) Uani 1 1 d . . .
C14 C 0.3114(3) 0.4525(3) -0.4585(2) 0.0199(7) Uani 1 1 d . . .
C11 C 0.3172(4) 0.8177(3) -0.3855(2) 0.0221(7) Uani 1 1 d . . .
C7 C 0.1867(3) 0.6524(3) -0.5234(2) 0.0214(7) Uani 1 1 d . . .
C8 C 0.1274(4) 0.7465(3) -0.5572(2) 0.0249(7) Uani 1 1 d . . .
H8 H 0.0663 0.7206 -0.6160 0.030 Uiso 1 1 calc R . .
C9 C 0.1591(4) 0.8726(3) -0.5048(2) 0.0265(7) Uani 1 1 d . . .
H9 H 0.1191 0.9363 -0.5262 0.032 Uiso 1 1 calc R . .
C3 C 0.2360(4) 0.1960(3) -0.5675(2) 0.0286(8) Uani 1 1 d . . .
H3 H 0.2091 0.1072 -0.6048 0.034 Uiso 1 1 calc R . .
C1 C 0.3720(4) 0.3547(3) -0.4285(2) 0.0224(7) Uani 1 1 d . . .
C16 C 0.6540(4) 0.3600(3) -0.2269(2) 0.0267(7) Uani 1 1 d . . .
H16A H 0.6905 0.2902 -0.2064 0.032 Uiso 1 1 calc R . .
H16B H 0.7479 0.4056 -0.2493 0.032 Uiso 1 1 calc R . .
C13 C 0.3501(3) 0.5895(3) -0.3970(2) 0.0193(6) Uani 1 1 d . . .
H13 H 0.4711 0.6156 -0.3856 0.023 Uiso 1 1 calc R . .
C21 C 0.6173(4) 0.9782(3) -0.1849(2) 0.0266(7) Uani 1 1 d . . .
H21A H 0.6958 0.9276 -0.2200 0.032 Uiso 1 1 calc R . .
H21B H 0.6737 1.0695 -0.1568 0.032 Uiso 1 1 calc R . .
C4 C 0.1790(4) 0.2896(3) -0.5993(2) 0.0253(7) Uani 1 1 d . . .
H4 H 0.1168 0.2652 -0.6577 0.030 Uiso 1 1 calc R . .
C10 C 0.2518(4) 0.9101(3) -0.4180(2) 0.0256(7) Uani 1 1 d . . .
H10 H 0.2709 0.9990 -0.3807 0.031 Uiso 1 1 calc R . .
C2 C 0.3322(4) 0.2273(3) -0.4823(2) 0.0259(7) Uani 1 1 d . . .
H2 H 0.3686 0.1607 -0.4628 0.031 Uiso 1 1 calc R . .
C23 C 0.3703(4) 0.6413(3) -0.2244(2) 0.0204(7) Uani 1 1 d . . .
C15 C 0.5184(4) 0.3016(3) -0.3042(2) 0.0249(7) Uani 1 1 d . . .
H15A H 0.5531 0.2297 -0.3526 0.030 Uiso 1 1 calc R . .
H15B H 0.4219 0.2641 -0.2791 0.030 Uiso 1 1 calc R . .
C20 C 0.7055(4) 0.9389(3) -0.0466(2) 0.0310(8) Uani 1 1 d . . .
H20A H 0.8041 0.9247 -0.0798 0.037 Uiso 1 1 calc R . .
H20B H 0.7271 1.0285 -0.0024 0.037 Uiso 1 1 calc R . .
C17 C 0.7226(4) 0.5030(3) -0.0743(2) 0.0313(8) Uani 1 1 d . . .
H17A H 0.8278 0.5213 -0.0998 0.038 Uiso 1 1 calc R . .
H17B H 0.7305 0.4382 -0.0414 0.038 Uiso 1 1 calc R . .
O8 O 0.9512(3) 0.9928(3) 0.20622(19) 0.0425(7) Uani 1 1 d . . .
C22 C 0.4717(4) 0.9745(3) -0.2530(2) 0.0256(7) Uani 1 1 d . . .
H22A H 0.3832 1.0111 -0.2182 0.031 Uiso 1 1 calc R . .
H22B H 0.5064 1.0261 -0.2946 0.031 Uiso 1 1 calc R . .
C24 C 0.2872(4) 0.6604(4) -0.1349(2) 0.0309(8) Uani 1 1 d . . .
H24A H 0.3617 0.7257 -0.0842 0.037 Uiso 1 1 calc R . .
H24B H 0.2738 0.5771 -0.1205 0.037 Uiso 1 1 calc R . .
C25 C 0.1124(3) 0.7059(3) -0.13223(18) 0.0600(13) Uani 1 1 d . . .
H25A H 0.1199 0.7839 -0.1519 0.090 Uiso 1 1 calc R . .
H25B H 0.0795 0.7257 -0.0688 0.090 Uiso 1 1 calc R . .
H25C H 0.0314 0.6357 -0.1743 0.090 Uiso 1 1 calc R . .
C18 C 0.6841(3) 0.6258(3) -0.00891(17) 0.0409(9) Uani 1 1 d R . .
H18A H 0.5744 0.6091 0.0121 0.049 Uiso 1 1 calc R . .
H18B H 0.7646 0.6590 0.0463 0.049 Uiso 1 1 calc R . .
C19 C 0.6752(3) 0.8462(2) 0.0050(2) 0.0415(9) Uani 1 1 d R . .
H19A H 0.7557 0.8708 0.0599 0.050 Uiso 1 1 calc R . .
H19B H 0.5647 0.8440 0.0265 0.050 Uiso 1 1 calc R . .
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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O9 Cl1 O8 103.30(16) . . ?
O9 Cl1 O10 110.14(17) . . ?
O8 Cl1 O10 112.95(15) . . ?
O9 Cl1 O11 112.68(16) . . ?
O8 Cl1 O11 111.59(15) . . ?
O10 Cl1 O11 106.32(14) . . ?
C1 O2 C15 121.1(2) . . ?
C11 O6 C22 117.4(2) . . ?
C17 O3 C16 107.2(2) . . ?
C23 O7 H99 110(3) . . ?
C21 O5 C20 112.0(2) . . ?
C18 O4 C19 109.5(2) . . ?
C23 N1 C13 124.3(3) . . ?
C23 N1 H98 118(2) . . ?
C13 N1 H98 118(2) . . ?
C4 C5 C14 119.5(3) . . ?
C4 C5 C6 117.8(3) . . ?
C14 C5 C6 122.7(3) . . ?
C11 C12 C7 117.5(3) . . ?
C11 C12 C13 118.0(3) . . ?
C7 C12 C13 124.5(3) . . ?
O1 C6 C7 119.1(3) . . ?
O1 C6 C5 122.9(3) . . ?
C7 C6 C5 118.0(3) . . ?
C5 C14 C1 120.5(3) . . ?
C5 C14 C13 121.2(3) . . ?
C1 C14 C13 118.4(3) . . ?
C12 C11 O6 113.8(3) . . ?
C12 C11 C10 119.7(3) . . ?
O6 C11 C10 126.5(3) . . ?
C8 C7 C12 122.3(3) . . ?
C8 C7 C6 118.2(3) . . ?
C12 C7 C6 119.5(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C4 C3 C2 122.9(3) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C2 C1 O2 122.8(3) . . ?
C2 C1 C14 119.3(3) . . ?
O2 C1 C14 117.9(3) . . ?
O3 C16 C15 108.7(2) . . ?
O3 C16 H16A 110.0 . . ?
C15 C16 H16A 110.0 . . ?
O3 C16 H16B 110.0 . . ?
C15 C16 H16B 110.0 . . ?
H16A C16 H16B 108.3 . . ?
C14 C13 N1 112.7(2) . . ?
C14 C13 C12 114.1(2) . . ?
N1 C13 C12 105.0(2) . . ?
C14 C13 H13 108.3 . . ?
N1 C13 H13 108.3 . . ?
C12 C13 H13 108.3 . . ?
O5 C21 C22 112.4(2) . . ?
O5 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
O5 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C23 O7 118.1(3) . . ?
N1 C23 C24 119.6(3) . . ?
O7 C23 C24 122.2(3) . . ?
O2 C15 C16 113.3(2) . . ?
O2 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
O2 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C19 C20 O5 112.7(2) . . ?
C19 C20 H20A 109.1 . . ?
O5 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
O5 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
O3 C17 C18 107.3(3) . . ?
O3 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
O6 C22 C21 106.7(3) . . ?
O6 C22 H22A 110.4 . . ?
C21 C22 H22A 110.4 . . ?
O6 C22 H22B 110.4 . . ?
C21 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
C23 C24 C25 117.8(3) . . ?
C23 C24 H24A 107.8 . . ?
C25 C24 H24A 107.8 . . ?
C23 C24 H24B 107.8 . . ?
C25 C24 H24B 107.8 . . ?
H24A C24 H24B 107.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C18 C17 107.2(2) . . ?
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 106.3(3) . . ?
O4 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
O4 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
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
O9 Cl1 1.410(3) . ?
Cl1 O8 1.453(3) . ?
Cl1 O10 1.468(2) . ?
Cl1 O11 1.501(2) . ?
O1 C6 1.251(4) . ?
O2 C1 1.386(4) . ?
O2 C15 1.448(4) . ?
O6 C11 1.389(4) . ?
O6 C22 1.394(4) . ?
O3 C17 1.442(4) . ?
O3 C16 1.485(4) . ?
O7 C23 1.325(4) . ?
O7 H99 0.75(4) . ?
O5 C21 1.399(4) . ?
O5 C20 1.467(4) . ?
O4 C18 1.444(3) . ?
O4 C19 1.456(3) . ?
N1 C23 1.319(4) . ?
N1 C13 1.503(4) . ?
N1 H98 0.78(3) . ?
C5 C4 1.373(4) . ?
C5 C14 1.426(4) . ?
C5 C6 1.511(4) . ?
C12 C11 1.380(4) . ?
C12 C7 1.423(4) . ?
C12 C13 1.543(4) . ?
C6 C7 1.446(4) . ?
C14 C1 1.431(4) . ?
C14 C13 1.483(4) . ?
C11 C10 1.420(4) . ?
C7 C8 1.422(4) . ?
C8 C9 1.344(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(5) . ?
C9 H9 0.9500 . ?
C3 C4 1.393(5) . ?
C3 C2 1.412(5) . ?
C3 H3 0.9500 . ?
C1 C2 1.365(4) . ?
C16 C15 1.509(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C13 H13 1.0000 . ?
C21 C22 1.552(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C2 H2 0.9500 . ?
C23 C24 1.523(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C20 C19 1.457(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C17 C18 1.497(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 C25 1.612(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660816
