#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/64/4306413.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_4306413
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         'C29 H29 N O7'
_chemical_formula_sum            'C29 H29 N O7'
_chemical_formula_weight         503.53
_chemical_name_common            AQHNHC(O)phenyl-(7)
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.9390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0944(7)
_cell_length_b                   13.4476(7)
_cell_length_c                   14.3000(8)
_cell_measurement_reflns_used    8139
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.19
_cell_volume                     2472.3(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      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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23904
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0404
_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)+(0.0478P)²+0.7022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                3285
_reflns_number_total             4360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801238a_si_003_04.cif
_cod_data_source_block           08078
_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/c'
_cod_database_code               4306413
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
H98 H 0.2865(16) 0.2123(14) -0.0276(13) 0.033(6) Uiso 1 1 d . . .
C1 C 0.39563(13) 0.13460(12) -0.21967(13) 0.0219(4) Uani 1 1 d . . .
C2 C 0.43258(14) 0.13763(13) -0.30444(13) 0.0252(4) Uani 1 1 d . . .
H2 H 0.3851 0.1356 -0.3635 0.030 Uiso 1 1 calc R . .
C3 C 0.53831(15) 0.14358(13) -0.30326(13) 0.0270(4) Uani 1 1 d . . .
H3 H 0.5630 0.1449 -0.3616 0.032 Uiso 1 1 calc R . .
C4 C 0.60780(15) 0.14755(13) -0.21840(13) 0.0261(4) Uani 1 1 d . . .
H4 H 0.6804 0.1510 -0.2180 0.031 Uiso 1 1 calc R . .
C5 C 0.57120(13) 0.14641(12) -0.13224(13) 0.0221(4) Uani 1 1 d . . .
C6 C 0.64757(14) 0.15340(13) -0.04183(13) 0.0247(4) Uani 1 1 d . . .
C7 C 0.60989(13) 0.13893(13) 0.04882(13) 0.0223(4) Uani 1 1 d . . .
C8 C 0.68200(14) 0.13422(13) 0.13459(14) 0.0266(4) Uani 1 1 d . . .
H8 H 0.7543 0.1402 0.1345 0.032 Uiso 1 1 calc R . .
C9 C 0.64803(15) 0.12098(13) 0.21893(14) 0.0280(4) Uani 1 1 d . . .
H9 H 0.6972 0.1185 0.2770 0.034 Uiso 1 1 calc R . .
C10 C 0.54269(14) 0.11111(13) 0.22055(13) 0.0252(4) Uani 1 1 d . . .
H10 H 0.5198 0.1027 0.2793 0.030 Uiso 1 1 calc R . .
C11 C 0.47141(13) 0.11361(12) 0.13549(13) 0.0210(4) Uani 1 1 d . . .
C12 C 0.50413(13) 0.12973(12) 0.04850(12) 0.0201(4) Uani 1 1 d . . .
C13 C 0.42206(13) 0.13760(12) -0.04133(12) 0.0201(4) Uani 1 1 d . . .
H13 H 0.3780 0.0765 -0.0442 0.024 Uiso 1 1 calc R . .
C14 C 0.46538(13) 0.13995(12) -0.13207(12) 0.0207(4) Uani 1 1 d . . .
C15 C 0.22053(14) 0.11618(14) -0.30271(13) 0.0281(4) Uani 1 1 d . . .
H15A H 0.2431 0.0621 -0.3412 0.034 Uiso 1 1 calc R . .
H15B H 0.2176 0.1788 -0.3395 0.034 Uiso 1 1 calc R . .
C16 C 0.11621(15) 0.09304(14) -0.28142(14) 0.0329(5) Uani 1 1 d . . .
H16A H 0.0682 0.0745 -0.3410 0.039 Uiso 1 1 calc R . .
H16B H 0.1218 0.0357 -0.2373 0.039 Uiso 1 1 calc R . .
C17 C -0.02856(15) 0.16144(17) -0.22742(15) 0.0380(5) Uani 1 1 d . . .
H17A H -0.0425 0.0895 -0.2223 0.046 Uiso 1 1 calc R . .
H17B H -0.0773 0.1880 -0.2833 0.046 Uiso 1 1 calc R . .
C18 C -0.04528(15) 0.21315(16) -0.13982(14) 0.0354(5) Uani 1 1 d . . .
H18A H -0.0230 0.2834 -0.1407 0.043 Uiso 1 1 calc R . .
H18B H -0.1199 0.2115 -0.1356 0.043 Uiso 1 1 calc R . .
C19 C -0.00313(15) 0.19625(15) 0.02887(14) 0.0335(5) Uani 1 1 d . . .
H19A H -0.0788 0.1980 0.0286 0.040 Uiso 1 1 calc R . .
H19B H 0.0249 0.2643 0.0416 0.040 Uiso 1 1 calc R . .
C20 C 0.04909(14) 0.12730(15) 0.10404(14) 0.0312(5) Uani 1 1 d . . .
H20A H 0.0235 0.1395 0.1639 0.037 Uiso 1 1 calc R . .
H20B H 0.0325 0.0577 0.0842 0.037 Uiso 1 1 calc R . .
C21 C 0.21203(14) 0.06951(14) 0.18267(13) 0.0266(4) Uani 1 1 d . . .
H21A H 0.2072 0.0039 0.1507 0.032 Uiso 1 1 calc R . .
H21B H 0.1797 0.0639 0.2396 0.032 Uiso 1 1 calc R . .
C22 C 0.32331(14) 0.09864(13) 0.21191(12) 0.0248(4) Uani 1 1 d . . .
H22A H 0.3289 0.1649 0.2427 0.030 Uiso 1 1 calc R . .
H22B H 0.3609 0.0497 0.2576 0.030 Uiso 1 1 calc R . .
C23 C 0.38230(13) 0.31808(13) -0.04524(11) 0.0186(4) Uani 1 1 d . . .
C24 C 0.30017(13) 0.39674(13) -0.04382(12) 0.0209(4) Uani 1 1 d . . .
C25 C 0.19398(13) 0.37594(14) -0.06117(13) 0.0242(4) Uani 1 1 d . . .
H25 H 0.1699 0.3102 -0.0763 0.029 Uiso 1 1 calc R . .
C26 C 0.12368(15) 0.45213(14) -0.05612(14) 0.0297(5) Uani 1 1 d . . .
H26 H 0.0512 0.4384 -0.0682 0.036 Uiso 1 1 calc R . .
C27 C 0.15840(15) 0.54814(14) -0.03360(14) 0.0299(5) Uani 1 1 d . . .
H27 H 0.1099 0.5997 -0.0293 0.036 Uiso 1 1 calc R . .
C28 C 0.26343(15) 0.56885(14) -0.01738(14) 0.0286(4) Uani 1 1 d . . .
H28 H 0.2872 0.6347 -0.0025 0.034 Uiso 1 1 calc R . .
C29 C 0.33443(14) 0.49332(13) -0.02285(13) 0.0241(4) Uani 1 1 d . . .
H29 H 0.4067 0.5078 -0.0122 0.029 Uiso 1 1 calc R . .
N1 N 0.35285(12) 0.22335(10) -0.03661(10) 0.0196(3) Uani 1 1 d . . .
O1 O 0.73942(10) 0.16991(11) -0.04200(10) 0.0377(4) Uani 1 1 d . . .
O2 O 0.29279(9) 0.12615(9) -0.21438(8) 0.0255(3) Uani 1 1 d . . .
O3 O 0.07583(10) 0.17590(10) -0.23977(9) 0.0331(3) Uani 1 1 d . . .
O4 O 0.01492(10) 0.16265(11) -0.06084(10) 0.0384(4) Uani 1 1 d . . .
O5 O 0.15841(9) 0.14207(9) 0.11958(9) 0.0271(3) Uani 1 1 d . . .
O6 O 0.36664(9) 0.10107(9) 0.12705(8) 0.0239(3) Uani 1 1 d . . .
O7 O 0.47137(9) 0.34117(9) -0.05286(8) 0.0240(3) Uani 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
O2 C1 C2 124.10(16) . . ?
O2 C1 C14 115.80(15) . . ?
C2 C1 C14 120.11(16) . . ?
C3 C2 C1 120.31(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.46(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.73(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C14 C5 C4 120.59(17) . . ?
C14 C5 C6 120.76(16) . . ?
C4 C5 C6 118.64(16) . . ?
O1 C6 C5 120.76(17) . . ?
O1 C6 C7 121.01(17) . . ?
C5 C6 C7 118.23(15) . . ?
C12 C7 C8 120.33(16) . . ?
C12 C7 C6 120.33(16) . . ?
C8 C7 C6 119.35(16) . . ?
C9 C8 C7 119.86(17) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.97(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.21(17) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O6 C11 C10 124.95(16) . . ?
O6 C11 C12 114.23(15) . . ?
C10 C11 C12 120.81(16) . . ?
C7 C12 C11 118.76(16) . . ?
C7 C12 C13 122.89(15) . . ?
C11 C12 C13 118.34(15) . . ?
N1 C13 C14 110.88(14) . . ?
N1 C13 C12 111.04(13) . . ?
C14 C13 C12 114.09(14) . . ?
N1 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C12 C13 H13 106.8 . . ?
C5 C14 C1 118.79(16) . . ?
C5 C14 C13 122.67(16) . . ?
C1 C14 C13 118.54(15) . . ?
O2 C15 C16 108.51(15) . . ?
O2 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O2 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
O3 C16 C15 110.67(15) . . ?
O3 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
O3 C17 C18 109.83(16) . . ?
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 107.36(17) . . ?
O4 C18 H18A 110.2 . . ?
C17 C18 H18A 110.2 . . ?
O4 C18 H18B 110.2 . . ?
C17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
O4 C19 C20 108.80(16) . . ?
O4 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
O4 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O5 C20 C19 109.76(15) . . ?
O5 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
O5 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
O5 C21 C22 109.68(14) . . ?
O5 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
O5 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O6 C22 C21 106.94(14) . . ?
O6 C22 H22A 110.3 . . ?
C21 C22 H22A 110.3 . . ?
O6 C22 H22B 110.3 . . ?
C21 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?
O7 C23 N1 122.71(16) . . ?
O7 C23 C24 120.86(15) . . ?
N1 C23 C24 116.43(15) . . ?
C29 C24 C25 119.80(16) . . ?
C29 C24 C23 117.14(15) . . ?
C25 C24 C23 123.06(16) . . ?
C26 C25 C24 119.45(17) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C25 120.52(18) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 119.98(17) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.98(18) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 120.26(17) . . ?
C24 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C23 N1 C13 123.17(15) . . ?
C23 N1 H98 117.7(12) . . ?
C13 N1 H98 119.2(12) . . ?
C1 O2 C15 116.82(14) . . ?
C16 O3 C17 112.92(15) . . ?
C18 O4 C19 113.77(15) . . ?
C20 O5 C21 111.43(13) . . ?
C11 O6 C22 118.72(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 1.368(2) . ?
C1 C2 1.388(2) . ?
C1 C14 1.405(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(2) . ?
C4 H4 0.9500 . ?
C5 C14 1.389(2) . ?
C5 C6 1.480(3) . ?
C6 O1 1.224(2) . ?
C6 C7 1.485(3) . ?
C7 C12 1.390(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 O6 1.365(2) . ?
C11 C12 1.407(2) . ?
C12 C13 1.514(2) . ?
C13 N1 1.476(2) . ?
C13 C14 1.512(2) . ?
C13 H13 1.0000 . ?
C15 O2 1.433(2) . ?
C15 C16 1.488(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O3 1.413(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O3 1.424(2) . ?
C17 C18 1.485(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O4 1.421(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O4 1.422(2) . ?
C19 C20 1.485(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O5 1.420(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O5 1.421(2) . ?
C21 C22 1.490(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O6 1.434(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O7 1.2316(19) . ?
C23 N1 1.343(2) . ?
C23 C24 1.511(2) . ?
C24 C29 1.388(2) . ?
C24 C25 1.394(2) . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.379(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
N1 H98 0.91(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660818
