#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/64/4306412.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_4306412
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 H31 N O8'
_chemical_formula_sum            'C25 H31 N O8'
_chemical_formula_weight         473.51
_chemical_name_common            AQHNH(CH2CH3)CO.H2O-(5)
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.912(4)
_cell_length_b                   13.222(6)
_cell_length_c                   22.398(11)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      1.0
_cell_volume                     2343(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      100(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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23063
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0261
_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)+(0.0367P)²+0.3745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0675
_reflns_number_gt                4019
_reflns_number_total             4158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801238a_si_003_03.cif
_cod_data_source_block           07039
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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               4306412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O6 O 0.03961(11) 0.67496(7) 0.17247(4) 0.0217(2) Uani 1 1 d . . .
O2 O 0.58341(12) 0.67447(7) 0.07508(4) 0.0198(2) Uani 1 1 d . . .
O5 O -0.00419(12) 0.46529(7) 0.15467(4) 0.0254(2) Uani 1 1 d . . .
O3 O 0.53538(12) 0.46736(7) 0.03708(4) 0.0246(2) Uani 1 1 d . . .
O7 O 0.43314(13) 0.87772(7) 0.23045(4) 0.0249(2) Uani 1 1 d . . .
O1 O 0.28551(13) 1.08309(7) 0.10590(5) 0.0309(2) Uani 1 1 d . . .
O4 O 0.27481(13) 0.36248(7) 0.09589(4) 0.0276(2) Uani 1 1 d . . .
N1 N 0.39397(13) 0.72848(9) 0.18297(5) 0.0169(2) Uani 1 1 d . . .
C12 C 0.15613(16) 0.82839(10) 0.14045(5) 0.0171(3) Uani 1 1 d . . .
C1 C 0.57676(17) 0.77593(10) 0.06335(5) 0.0180(3) Uani 1 1 d . . .
C5 C 0.43164(17) 0.93282(10) 0.08160(6) 0.0185(3) Uani 1 1 d . . .
C14 C 0.44466(16) 0.82872(9) 0.09111(5) 0.0165(3) Uani 1 1 d . . .
C13 C 0.31758(16) 0.77029(9) 0.12828(5) 0.0167(3) Uani 1 1 d . . .
H13 H 0.2838 0.7107 0.1035 0.020 Uiso 1 1 calc R . .
C10 C -0.13803(17) 0.82512(11) 0.17100(6) 0.0222(3) Uani 1 1 d . . .
H10 H -0.2330 0.7888 0.1855 0.027 Uiso 1 1 calc R . .
C15 C 0.70441(18) 0.61670(10) 0.04167(6) 0.0234(3) Uani 1 1 d . . .
H15A H 0.8200 0.6413 0.0503 0.028 Uiso 1 1 calc R . .
H15B H 0.6831 0.6248 -0.0016 0.028 Uiso 1 1 calc R . .
C2 C 0.69031(17) 0.82619(11) 0.02601(6) 0.0213(3) Uani 1 1 d . . .
H2 H 0.7781 0.7896 0.0067 0.026 Uiso 1 1 calc R . .
C8 C -0.01450(18) 0.98116(10) 0.13789(6) 0.0232(3) Uani 1 1 d . . .
H8 H -0.0246 1.0513 0.1295 0.028 Uiso 1 1 calc R . .
C24 C 0.50382(17) 0.72322(11) 0.28305(6) 0.0237(3) Uani 1 1 d . . .
H24B H 0.5719 0.6654 0.2686 0.028 Uiso 1 1 calc R . .
H24A H 0.5777 0.7662 0.3081 0.028 Uiso 1 1 calc R . .
C3 C 0.67475(18) 0.92992(11) 0.01710(6) 0.0244(3) Uani 1 1 d . . .
H3 H 0.7521 0.9641 -0.0083 0.029 Uiso 1 1 calc R . .
C7 C 0.14020(17) 0.93184(10) 0.12934(6) 0.0187(3) Uani 1 1 d . . .
C4 C 0.54770(17) 0.98312(10) 0.04494(6) 0.0218(3) Uani 1 1 d . . .
H4 H 0.5387 1.0541 0.0393 0.026 Uiso 1 1 calc R . .
C6 C 0.28689(17) 0.99031(10) 0.10659(6) 0.0212(3) Uani 1 1 d . . .
C11 C 0.01509(17) 0.77576(10) 0.16218(6) 0.0191(3) Uani 1 1 d . . .
C18 C 0.3537(2) 0.32389(11) 0.04380(7) 0.0289(3) Uani 1 1 d . . .
H18B H 0.2932 0.3478 0.0078 0.035 Uiso 1 1 calc R . .
H18A H 0.3511 0.2490 0.0442 0.035 Uiso 1 1 calc R . .
C23 C 0.44156(16) 0.78437(10) 0.22990(6) 0.0182(3) Uani 1 1 d . . .
C22 C -0.09598(18) 0.61909(11) 0.19921(6) 0.0230(3) Uani 1 1 d . . .
H22B H -0.1951 0.6181 0.1722 0.028 Uiso 1 1 calc R . .
H22A H -0.1300 0.6510 0.2373 0.028 Uiso 1 1 calc R . .
C21 C -0.03514(18) 0.51400(11) 0.21012(6) 0.0256(3) Uani 1 1 d . . .
H21B H 0.0701 0.5158 0.2340 0.031 Uiso 1 1 calc R . .
H21A H -0.1213 0.4758 0.2329 0.031 Uiso 1 1 calc R . .
C9 C -0.15190(17) 0.92771(11) 0.15851(6) 0.0235(3) Uani 1 1 d . . .
H9 H -0.2569 0.9612 0.1642 0.028 Uiso 1 1 calc R . .
C19 C 0.11184(19) 0.32091(11) 0.10606(7) 0.0311(3) Uani 1 1 d . . .
H19A H 0.1189 0.2463 0.1087 0.037 Uiso 1 1 calc R . .
H19B H 0.0351 0.3387 0.0728 0.037 Uiso 1 1 calc R . .
C25 C 0.3585(2) 0.68401(13) 0.32055(7) 0.0360(4) Uani 1 1 d . . .
H25C H 0.2863 0.6404 0.2960 0.054 Uiso 1 1 calc R . .
H25B H 0.2921 0.7412 0.3356 0.054 Uiso 1 1 calc R . .
H25A H 0.4032 0.6451 0.3543 0.054 Uiso 1 1 calc R . .
C16 C 0.68970(17) 0.50764(10) 0.05856(6) 0.0233(3) Uani 1 1 d . . .
H16B H 0.7856 0.4693 0.0414 0.028 Uiso 1 1 calc R . .
H16A H 0.6944 0.5009 0.1025 0.028 Uiso 1 1 calc R . .
C20 C 0.0461(2) 0.36367(10) 0.16358(8) 0.0324(3) Uani 1 1 d . . .
H20B H -0.0515 0.3232 0.1775 0.039 Uiso 1 1 calc R . .
H20A H 0.1353 0.3606 0.1945 0.039 Uiso 1 1 calc R . .
C17 C 0.5323(2) 0.36053(10) 0.04298(7) 0.0303(3) Uani 1 1 d . . .
H17A H 0.5897 0.3405 0.0804 0.036 Uiso 1 1 calc R . .
H17B H 0.5935 0.3292 0.0092 0.036 Uiso 1 1 calc R . .
O8 O 0.57106(16) 1.01068(8) 0.31418(5) 0.0341(3) Uani 1 1 d . . .
H8A H 0.528(2) 0.9659(14) 0.2888(9) 0.044(5) Uiso 1 1 d . . .
H8B H 0.619(3) 0.9784(15) 0.3426(10) 0.048(6) Uiso 1 1 d . . .
H98 H 0.405(2) 0.6637(13) 0.1852(7) 0.026(4) 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'
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
C11 O6 C22 117.84(10) . . ?
C1 O2 C15 116.58(10) . . ?
C20 O5 C21 110.83(11) . . ?
C16 O3 C17 110.95(10) . . ?
C18 O4 C19 113.09(11) . . ?
C23 N1 C13 124.11(11) . . ?
C23 N1 H98 118.4(10) . . ?
C13 N1 H98 117.4(10) . . ?
C7 C12 C11 118.44(12) . . ?
C7 C12 C13 122.74(12) . . ?
C11 C12 C13 118.79(12) . . ?
O2 C1 C2 123.86(12) . . ?
O2 C1 C14 115.57(11) . . ?
C2 C1 C14 120.56(12) . . ?
C14 C5 C4 120.62(12) . . ?
C14 C5 C6 120.27(12) . . ?
C4 C5 C6 118.95(12) . . ?
C5 C14 C1 118.55(12) . . ?
C5 C14 C13 122.46(12) . . ?
C1 C14 C13 118.94(11) . . ?
N1 C13 C12 112.73(10) . . ?
N1 C13 C14 112.05(10) . . ?
C12 C13 C14 113.53(11) . . ?
N1 C13 H13 105.9 . . ?
C12 C13 H13 105.9 . . ?
C14 C13 H13 105.9 . . ?
C9 C10 C11 119.91(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O2 C15 C16 109.23(11) . . ?
O2 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O2 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C3 C2 C1 119.88(13) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C9 C8 C7 119.82(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C25 C24 C23 111.72(12) . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
H24B C24 H24A 107.9 . . ?
C4 C3 C2 120.24(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C12 C7 C8 120.73(12) . . ?
C12 C7 C6 120.05(12) . . ?
C8 C7 C6 119.20(12) . . ?
C3 C4 C5 120.13(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O1 C6 C5 120.95(13) . . ?
O1 C6 C7 121.20(13) . . ?
C5 C6 C7 117.77(11) . . ?
O6 C11 C10 123.89(12) . . ?
O6 C11 C12 115.45(11) . . ?
C10 C11 C12 120.65(12) . . ?
O4 C18 C17 108.04(12) . . ?
O4 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
O4 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
H18B C18 H18A 108.4 . . ?
O7 C23 N1 122.94(12) . . ?
O7 C23 C24 122.72(12) . . ?
N1 C23 C24 114.34(12) . . ?
O6 C22 C21 107.89(11) . . ?
O6 C22 H22B 110.1 . . ?
C21 C22 H22B 110.1 . . ?
O6 C22 H22A 110.1 . . ?
C21 C22 H22A 110.1 . . ?
H22B C22 H22A 108.4 . . ?
O5 C21 C22 109.57(11) . . ?
O5 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
O5 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
H21B C21 H21A 108.2 . . ?
C8 C9 C10 120.43(13) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
O4 C19 C20 107.86(12) . . ?
O4 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O4 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C24 C25 H25C 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25C C25 H25B 109.5 . . ?
C24 C25 H25A 109.5 . . ?
H25C C25 H25A 109.5 . . ?
H25B C25 H25A 109.5 . . ?
O3 C16 C15 110.11(11) . . ?
O3 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
O3 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
H16B C16 H16A 108.2 . . ?
O5 C20 C19 109.52(13) . . ?
O5 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
O5 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
H20B C20 H20A 108.2 . . ?
O3 C17 C18 109.89(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 . . ?
H8A O8 H8B 108.2(17) . . ?
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
O6 C11 1.3664(17) . ?
O6 C22 1.4336(17) . ?
O2 C1 1.3680(16) . ?
O2 C15 1.4353(16) . ?
O5 C20 1.4154(18) . ?
O5 C21 1.4204(18) . ?
O3 C16 1.4162(18) . ?
O3 C17 1.4189(17) . ?
O7 C23 1.2361(17) . ?
O1 C6 1.2269(17) . ?
O4 C18 1.4182(18) . ?
O4 C19 1.4200(19) . ?
N1 C23 1.3390(18) . ?
N1 C13 1.4737(17) . ?
N1 H98 0.862(17) . ?
C12 C7 1.3960(19) . ?
C12 C11 1.4022(19) . ?
C12 C13 1.5152(18) . ?
C1 C2 1.3959(19) . ?
C1 C14 1.4021(19) . ?
C5 C14 1.3966(19) . ?
C5 C4 1.3999(19) . ?
C5 C6 1.484(2) . ?
C14 C13 1.5168(18) . ?
C13 H13 1.0000 . ?
C10 C9 1.389(2) . ?
C10 C11 1.3902(19) . ?
C10 H10 0.9500 . ?
C15 C16 1.495(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C2 C3 1.391(2) . ?
C2 H2 0.9500 . ?
C8 C9 1.376(2) . ?
C8 C7 1.400(2) . ?
C8 H8 0.9500 . ?
C24 C25 1.515(2) . ?
C24 C23 1.5210(19) . ?
C24 H24B 0.9900 . ?
C24 H24A 0.9900 . ?
C3 C4 1.376(2) . ?
C3 H3 0.9500 . ?
C7 C6 1.485(2) . ?
C4 H4 0.9500 . ?
C18 C17 1.494(2) . ?
C18 H18B 0.9900 . ?
C18 H18A 0.9900 . ?
C22 C21 1.491(2) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21A 0.9900 . ?
C9 H9 0.9500 . ?
C19 C20 1.500(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C25 H25C 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25A 0.9800 . ?
C16 H16B 0.9900 . ?
C16 H16A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 H20A 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O8 H8A 0.89(2) . ?
O8 H8B 0.85(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660817
