#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/64/4306415.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_4306415
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 O12'
_chemical_formula_sum            'C25 H30 Cl N O12'
_chemical_formula_weight         571.95
_chemical_name_common            '[AQHNH(CHO)CH=CH2(H2O)]ClO4-(7)'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4132(6)
_cell_length_b                   17.8022(9)
_cell_length_c                   13.2483(7)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.29
_cell_volume                     2566.3(2)
_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      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25444
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_correction_T_min  0.8285
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0407P)²+1.0905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                4358
_reflns_number_total             4716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801238a_si_003_06.cif
_cod_data_source_block           07082a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4306415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12947(11) -0.14378(7) 0.10232(10) 0.0187(3) Uani 1 1 d . . .
C2 C 0.09576(12) -0.16325(7) -0.00431(10) 0.0222(3) Uani 1 1 d . . .
H2 H 0.1476 -0.1942 -0.0308 0.027 Uiso 1 1 calc R . .
C3 C -0.01558(12) -0.13662(7) -0.07180(10) 0.0233(3) Uani 1 1 d . . .
H3 H -0.0394 -0.1499 -0.1446 0.028 Uiso 1 1 calc R . .
C4 C -0.09143(12) -0.09139(7) -0.03458(10) 0.0215(3) Uani 1 1 d . . .
H4 H -0.1666 -0.0736 -0.0816 0.026 Uiso 1 1 calc R . .
C5 C -0.05733(11) -0.07169(7) 0.07281(10) 0.0182(3) Uani 1 1 d . . .
C6 C -0.13795(11) -0.02095(7) 0.11203(10) 0.0192(3) Uani 1 1 d . . .
C7 C -0.08638(11) 0.01191(7) 0.21963(10) 0.0179(3) Uani 1 1 d . . .
C8 C -0.14737(12) 0.07097(7) 0.25137(10) 0.0214(3) Uani 1 1 d . . .
H8 H -0.2232 0.0889 0.2055 0.026 Uiso 1 1 calc R . .
C9 C -0.09737(12) 0.10346(7) 0.34973(10) 0.0229(3) Uani 1 1 d . . .
H9 H -0.1390 0.1439 0.3708 0.028 Uiso 1 1 calc R . .
C10 C 0.01348(12) 0.07764(7) 0.41853(10) 0.0214(3) Uani 1 1 d . . .
H10 H 0.0471 0.1001 0.4861 0.026 Uiso 1 1 calc R . .
C11 C 0.07396(11) 0.01871(7) 0.38705(9) 0.0176(3) Uani 1 1 d . . .
C12 C 0.02517(11) -0.01427(7) 0.28715(9) 0.0163(2) Uani 1 1 d . . .
C13 C 0.09496(11) -0.07819(6) 0.25770(9) 0.0158(2) Uani 1 1 d . . .
H13 H 0.1837 -0.0639 0.2776 0.019 Uiso 1 1 calc R . .
C14 C 0.05320(11) -0.09793(7) 0.14158(9) 0.0170(2) Uani 1 1 d . . .
C15 C 0.33475(12) -0.19798(7) 0.14711(10) 0.0223(3) Uani 1 1 d . . .
H15A H 0.3031 -0.2374 0.0930 0.027 Uiso 1 1 calc R . .
H15B H 0.3934 -0.2220 0.2095 0.027 Uiso 1 1 calc R . .
C16 C 0.40190(12) -0.14011(8) 0.10329(10) 0.0236(3) Uani 1 1 d . . .
H16A H 0.4696 -0.1642 0.0828 0.028 Uiso 1 1 calc R . .
H16B H 0.3450 -0.1165 0.0395 0.028 Uiso 1 1 calc R . .
C17 C 0.53518(14) -0.03357(8) 0.15804(12) 0.0307(3) Uani 1 1 d . . .
H17A H 0.5411 -0.0443 0.0864 0.037 Uiso 1 1 calc R . .
H17B H 0.6177 -0.0402 0.2096 0.037 Uiso 1 1 calc R . .
C18 C 0.49248(13) 0.04547(8) 0.16267(11) 0.0269(3) Uani 1 1 d . . .
H18A H 0.5490 0.0809 0.1432 0.032 Uiso 1 1 calc R . .
H18B H 0.4092 0.0521 0.1122 0.032 Uiso 1 1 calc R . .
C19 C 0.42971(13) 0.12822(8) 0.27593(11) 0.0267(3) Uani 1 1 d . . .
H19A H 0.3444 0.1269 0.2278 0.032 Uiso 1 1 calc R . .
H19B H 0.4730 0.1709 0.2550 0.032 Uiso 1 1 calc R . .
C20 C 0.42836(13) 0.13846(7) 0.38772(12) 0.0278(3) Uani 1 1 d . . .
H20A H 0.5137 0.1400 0.4358 0.033 Uiso 1 1 calc R . .
H20B H 0.3879 0.1866 0.3944 0.033 Uiso 1 1 calc R . .
C21 C 0.31124(12) 0.09743(7) 0.49869(10) 0.0240(3) Uani 1 1 d . . .
H21A H 0.2449 0.1348 0.4718 0.029 Uiso 1 1 calc R . .
H21B H 0.3752 0.1201 0.5589 0.029 Uiso 1 1 calc R . .
C22 C 0.26040(12) 0.02815(7) 0.53488(10) 0.0217(3) Uani 1 1 d . . .
H22A H 0.3293 -0.0044 0.5744 0.026 Uiso 1 1 calc R . .
H22B H 0.2137 0.0428 0.5838 0.026 Uiso 1 1 calc R . .
C23 C 0.17137(11) -0.18119(7) 0.39117(9) 0.0173(2) Uani 1 1 d . . .
C24 C 0.13396(12) -0.24443(7) 0.44619(10) 0.0203(3) Uani 1 1 d . . .
H24 H 0.0493 -0.2569 0.4297 0.024 Uiso 1 1 calc R . .
C25 C 0.21610(13) -0.28412(7) 0.51822(10) 0.0240(3) Uani 1 1 d . . .
H25A H 0.3009 -0.2720 0.5353 0.029 Uiso 1 1 calc R . .
H25B H 0.1903 -0.3247 0.5529 0.029 Uiso 1 1 calc R . .
N1 N 0.08323(10) -0.14501(6) 0.32063(8) 0.0164(2) Uani 1 1 d . . .
O1 O -0.24164(8) -0.00534(5) 0.05640(7) 0.0265(2) Uani 1 1 d . . .
O2 O 0.23376(8) -0.16744(5) 0.17792(7) 0.0208(2) Uani 1 1 d . . .
O3 O 0.45009(10) -0.08463(6) 0.18209(8) 0.0329(2) Uani 1 1 d . . .
O4 O 0.49040(8) 0.06006(5) 0.26786(7) 0.0245(2) Uani 1 1 d . . .
O5 O 0.36315(9) 0.07751(5) 0.41651(7) 0.0264(2) Uani 1 1 d . . .
O6 O 0.18097(8) -0.01362(5) 0.44768(7) 0.01929(19) Uani 1 1 d . . .
O7 O 0.28536(8) -0.16615(5) 0.41498(7) 0.0212(2) Uani 1 1 d . . .
O12 O 0.39991(8) -0.06644(6) 0.36498(8) 0.0218(2) Uani 1 1 d . . .
O9 O -0.17957(10) -0.15073(6) 0.28965(10) 0.0376(3) Uani 1 1 d . . .
O10 O -0.17455(10) -0.27788(6) 0.24897(9) 0.0343(2) Uani 1 1 d . . .
O11 O -0.35483(9) -0.22504(6) 0.27008(9) 0.0357(3) Uani 1 1 d . . .
O8 O -0.18025(11) -0.24136(8) 0.41669(8) 0.0450(3) Uani 1 1 d . . .
Cl1 Cl -0.22382(3) -0.224407(17) 0.30576(2) 0.01962(9) Uani 1 1 d . . .
H12A H 0.4142(17) -0.0692(10) 0.3063(16) 0.045(5) Uiso 1 1 d . . .
H12B H 0.3930(17) -0.0214(12) 0.3796(15) 0.044(5) Uiso 1 1 d . . .
H98 H 0.0108(15) -0.1588(8) 0.3128(11) 0.018(4) Uiso 1 1 d . . .
H99 H 0.325(2) -0.1200(14) 0.3831(19) 0.078(7) 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'
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
O2 C1 C2 125.35(12) . . ?
O2 C1 C14 114.03(11) . . ?
C2 C1 C14 120.60(12) . . ?
C1 C2 C3 118.98(12) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.16(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.84(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C14 C5 C4 119.90(12) . . ?
C14 C5 C6 120.46(11) . . ?
C4 C5 C6 119.61(11) . . ?
O1 C6 C7 121.28(12) . . ?
O1 C6 C5 120.98(11) . . ?
C7 C6 C5 117.71(10) . . ?
C8 C7 C12 120.01(11) . . ?
C8 C7 C6 119.75(11) . . ?
C12 C7 C6 120.19(11) . . ?
C9 C8 C7 119.89(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.89(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.21(12) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O6 C11 C10 125.31(11) . . ?
O6 C11 C12 114.07(11) . . ?
C10 C11 C12 120.60(11) . . ?
C7 C12 C11 119.40(11) . . ?
C7 C12 C13 122.49(11) . . ?
C11 C12 C13 118.10(10) . . ?
N1 C13 C12 108.42(9) . . ?
N1 C13 C14 109.42(9) . . ?
C12 C13 C14 114.28(10) . . ?
N1 C13 H13 108.2 . . ?
C12 C13 H13 108.2 . . ?
C14 C13 H13 108.2 . . ?
C5 C14 C1 119.52(11) . . ?
C5 C14 C13 122.23(11) . . ?
C1 C14 C13 118.25(11) . . ?
O2 C15 C16 113.33(10) . . ?
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 . . ?
O3 C16 C15 108.80(10) . . ?
O3 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O3 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O3 C17 C18 109.64(11) . . ?
O3 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O3 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O4 C18 C17 108.26(11) . . ?
O4 C18 H18A 110.0 . . ?
C17 C18 H18A 110.0 . . ?
O4 C18 H18B 110.0 . . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
O4 C19 C20 109.28(11) . . ?
O4 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
O4 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
O5 C20 C19 109.44(11) . . ?
O5 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
O5 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
O5 C21 C22 109.12(10) . . ?
O5 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O5 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O6 C22 C21 112.21(10) . . ?
O6 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
O6 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O7 C23 N1 125.36(11) . . ?
O7 C23 C24 117.78(11) . . ?
N1 C23 C24 116.86(11) . . ?
C25 C24 C23 121.15(12) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
C23 N1 C13 127.79(11) . . ?
C23 N1 H98 117.3(10) . . ?
C13 N1 H98 114.7(10) . . ?
C1 O2 C15 120.13(10) . . ?
C16 O3 C17 114.51(10) . . ?
C19 O4 C18 112.50(10) . . ?
C20 O5 C21 112.49(10) . . ?
C11 O6 C22 119.15(9) . . ?
C23 O7 H99 125.6(13) . . ?
H12A O12 H12B 109.2(18) . . ?
H12A O12 H99 115.5(16) . . ?
H12B O12 H99 122.1(17) . . ?
O11 Cl1 O10 111.10(6) . . ?
O11 Cl1 O8 110.04(7) . . ?
O10 Cl1 O8 109.23(7) . . ?
O11 Cl1 O9 109.68(6) . . ?
O10 Cl1 O9 108.44(7) . . ?
O8 Cl1 O9 108.30(8) . . ?
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 1.3703(15) . ?
C1 C2 1.3915(18) . ?
C1 C14 1.4028(18) . ?
C2 C3 1.3977(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3778(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4016(17) . ?
C4 H4 0.9500 . ?
C5 C14 1.3951(17) . ?
C5 C6 1.4903(18) . ?
C6 O1 1.2225(15) . ?
C6 C7 1.4881(17) . ?
C7 C8 1.3941(18) . ?
C7 C12 1.3968(17) . ?
C8 C9 1.3818(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3953(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3873(18) . ?
C10 H10 0.9500 . ?
C11 O6 1.3697(14) . ?
C11 C12 1.4006(17) . ?
C12 C13 1.5063(16) . ?
C13 N1 1.4817(15) . ?
C13 C14 1.5082(16) . ?
C13 H13 1.0000 . ?
C15 O2 1.4403(15) . ?
C15 C16 1.5015(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O3 1.4217(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O3 1.4345(16) . ?
C17 C18 1.496(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O4 1.4248(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O4 1.4170(17) . ?
C19 C20 1.497(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O5 1.4311(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O5 1.4323(16) . ?
C21 C22 1.5019(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O6 1.4413(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O7 1.2713(15) . ?
C23 N1 1.3164(16) . ?
C23 C24 1.4728(17) . ?
C24 C25 1.3224(19) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9500 . ?
C25 H25B 0.9500 . ?
N1 H98 0.838(16) . ?
O7 H99 1.09(3) . ?
O12 H12A 0.84(2) . ?
O12 H12B 0.83(2) . ?
O12 H99 1.35(3) . ?
O9 Cl1 1.4444(10) . ?
O10 Cl1 1.4297(10) . ?
O11 Cl1 1.4257(10) . ?
O8 Cl1 1.4343(11) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660819
