#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/23/1502307.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_1502307
loop_
_publ_author_name
'Niu, Zhenbin'
'Slebodnick, Carla'
'Schoonover, Daniel'
'Azurmendi, Hugo'
'Harich, Kim'
'Gibson, Harry W.'
_publ_section_title
;
 Pseudocryptand-type [2]pseudorotaxanes based on
 bis(meta-phenylene)-32-crown-10 derivatives and paraquats with remarkably
 improved association constants.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3992
_journal_page_last               3995
_journal_paper_doi               10.1021/ol201502r
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C42 H50 N2 O14'
_chemical_formula_sum            'C42 H50 N2 O14'
_chemical_formula_weight         806.84
_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                 93.7759(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.03389(14)
_cell_length_b                   8.73956(18)
_cell_length_c                   32.8330(7)
_cell_measurement_reflns_used    13224
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3183
_cell_measurement_theta_min      4.0447
_cell_volume                     2013.97(7)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_publication_material
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_solution
'SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3174
_diffrn_detector_type            'Oxford Diffraction Onyx CCD'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Nova'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.1277003000
_diffrn_orient_matrix_UB_12      0.0915429000
_diffrn_orient_matrix_UB_13      0.0312207000
_diffrn_orient_matrix_UB_21      -0.0239086000
_diffrn_orient_matrix_UB_22      -0.1257756000
_diffrn_orient_matrix_UB_23      0.0321642000
_diffrn_orient_matrix_UB_31      0.1769023000
_diffrn_orient_matrix_UB_32      -0.0828870000
_diffrn_orient_matrix_UB_33      -0.0142441000
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            24093
_diffrn_reflns_theta_full        76.51
_diffrn_reflns_theta_max         76.51
_diffrn_reflns_theta_min         5.24
_diffrn_source                   'Nova Micro-focus X-ray Source (Cu)'
_diffrn_source_current           0.95
_diffrn_source_voltage           49.5
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro, Oxford Diffraction Ltd., V1.171.34.36 (release 02-08-2010
 CrysAlis171 .NET) (compiled Aug  2 2010,13:00:58). Numerical absorption
 correction based on gaussian integration over a multifaceted crystal model.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0410
_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)+(0.0549P)²+1.0130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                3761
_reflns_number_total             4172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201502r_si_002.cif
_cod_data_source_block           cs1613
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2013.96(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1502307
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
O1 O 0.09315(14) 0.57649(12) 0.59822(3) 0.0272(2) Uani 1 1 d .
O2 O -0.15356(13) 0.65253(12) 0.52889(3) 0.0256(2) Uani 1 1 d .
O3 O -0.20581(14) 0.86209(11) 0.46059(3) 0.0256(2) Uani 1 1 d .
O4 O 0.11954(14) 0.93262(11) 0.41997(3) 0.0250(2) Uani 1 1 d .
O5 O 0.33196(13) 0.71977(11) 0.37022(3) 0.0249(2) Uani 1 1 d .
O6 O 0.49081(14) 0.91220(11) 0.68632(3) 0.0266(2) Uani 1 1 d .
O7 O 0.69896(15) 1.02940(12) 0.73076(3) 0.0310(2) Uani 1 1 d .
N1 N 0.24614(17) 1.14200(14) 0.68611(4) 0.0250(3) Uani 1 1 d .
C1 C 0.27207(19) 0.55368(16) 0.61623(4) 0.0227(3) Uani 1 1 d .
C2 C 0.37556(19) 0.41969(15) 0.61123(4) 0.0214(3) Uani 1 1 d .
H2 H 0.3257 0.3394 0.5942 0.026 Uiso 1 1 calc R
C3 C 0.55448(19) 0.40675(15) 0.63199(4) 0.0218(3) Uani 1 1 d .
C4 C 0.62989(19) 0.52452(16) 0.65643(4) 0.0239(3) Uani 1 1 d .
H4 H 0.7529 0.5147 0.6699 0.029 Uiso 1 1 calc R
C5 C 0.5240(2) 0.65685(16) 0.66097(4) 0.0237(3) Uani 1 1 d .
C6 C 0.3443(2) 0.67234(16) 0.64100(4) 0.0242(3) Uani 1 1 d .
H6 H 0.2717 0.7627 0.6442 0.029 Uiso 1 1 calc R
C7 C 0.0246(2) 0.46529(16) 0.56860(4) 0.0263(3) Uani 1 1 d .
H7B H 0.0163 0.3636 0.5816 0.032 Uiso 1 1 calc R
H7A H 0.1135 0.4577 0.5465 0.032 Uiso 1 1 calc R
C8 C -0.1685(2) 0.51397(18) 0.55124(5) 0.0294(3) Uani 1 1 d .
H8A H -0.2238 0.4329 0.5330 0.035 Uiso 1 1 calc R
H8B H -0.2542 0.5294 0.5736 0.035 Uiso 1 1 calc R
C9 C -0.33331(19) 0.69819(18) 0.51101(4) 0.0269(3) Uani 1 1 d .
H9B H -0.4294 0.6945 0.5317 0.032 Uiso 1 1 calc R
H9A H -0.3739 0.6271 0.4886 0.032 Uiso 1 1 calc R
C10 C -0.3204(2) 0.85767(17) 0.49460(4) 0.0273(3) Uani 1 1 d .
H10A H -0.4499 0.8954 0.4862 0.033 Uiso 1 1 calc R
H10B H -0.2651 0.9261 0.5163 0.033 Uiso 1 1 calc R
C11 C -0.1646(2) 1.01592(16) 0.44993(4) 0.0275(3) Uani 1 1 d .
H11B H -0.0913 1.0662 0.4730 0.033 Uiso 1 1 calc R
H11A H -0.2851 1.0731 0.4445 0.033 Uiso 1 1 calc R
C12 C -0.0515(2) 1.01965(16) 0.41275(4) 0.0270(3) Uani 1 1 d .
H12A H -0.1284 0.9765 0.3891 0.032 Uiso 1 1 calc R
H12B H -0.0194 1.1268 0.4062 0.032 Uiso 1 1 calc R
C13 C 0.2554(2) 0.97012(16) 0.39156(4) 0.0250(3) Uani 1 1 d .
H13B H 0.3134 1.0708 0.3985 0.030 Uiso 1 1 calc R
H13A H 0.1926 0.9763 0.3637 0.030 Uiso 1 1 calc R
C14 C 0.40728(19) 0.84842(16) 0.39300(4) 0.0236(3) Uani 1 1 d .
H14A H 0.5231 0.8873 0.3809 0.028 Uiso 1 1 calc R
H14B H 0.4416 0.8183 0.4216 0.028 Uiso 1 1 calc R
C15 C 0.6081(2) 0.77663(15) 0.68970(4) 0.0269(3) Uani 1 1 d .
H15B H 0.6135 0.7378 0.7181 0.032 Uiso 1 1 calc R
H15A H 0.7394 0.8013 0.6827 0.032 Uiso 1 1 calc R
C16 C 0.5510(2) 1.02950(16) 0.70991(4) 0.0232(3) Uani 1 1 d .
C17 C 0.41246(19) 1.16020(16) 0.70818(4) 0.0219(3) Uani 1 1 d .
C18 C 0.4626(2) 1.29131(17) 0.72986(4) 0.0272(3) Uani 1 1 d .
H18 H 0.5827 1.2989 0.7447 0.033 Uiso 1 1 calc R
C19 C 0.3339(2) 1.41140(18) 0.72939(5) 0.0314(3) Uani 1 1 d .
H19 H 0.3640 1.5034 0.7438 0.038 Uiso 1 1 calc R
C20 C 0.1606(2) 1.39439(18) 0.70740(4) 0.0295(3) Uani 1 1 d .
H20 H 0.0682 1.4738 0.7068 0.035 Uiso 1 1 calc R
C21 C 0.1241(2) 1.25914(17) 0.68617(4) 0.0277(3) Uani 1 1 d .
H21 H 0.0055 1.2493 0.6708 0.033 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0354 -0.0006 0.0005 -1.0004 -0.0312 -0.0322 0.0142
0 0 1 0.0354 0.0006 -0.0005 1.0004 0.0312 0.0322 -0.0142
0 1 1 0.0464 -0.0002 0.9992 1.0116 0.1228 -0.0936 -0.0971
0 -1 -1 0.0464 0.0002 -0.9992 -1.0116 -0.1228 0.0936 0.0971
1 0 0 0.1950 0.9998 -0.0003 -0.0073 0.1277 -0.0239 0.1769
-1 0 0 0.1751 -0.9998 0.0003 0.0073 -0.1277 0.0239 -0.1769
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
C1 O1 C7 116.87(11) .
C9 O2 C8 111.05(11) .
C10 O3 C11 110.76(11) .
C13 O4 C12 111.38(10) .
C3 O5 C14 117.69(10) 3_666
C16 O6 C15 115.28(10) .
C21 N1 C17 116.41(12) .
O1 C1 C6 115.66(12) .
O1 C1 C2 122.93(12) .
C6 C1 C2 121.39(12) .
C1 C2 C3 118.13(12) .
O5 C3 C4 115.30(11) 3_666
O5 C3 C2 123.37(12) 3_666
C4 C3 C2 121.32(12) .
C3 C4 C5 119.48(12) .
C4 C5 C6 120.48(13) .
C4 C5 C15 117.08(12) .
C6 C5 C15 122.37(12) .
C5 C6 C1 119.18(12) .
O1 C7 C8 108.71(12) .
O2 C8 C7 109.97(12) .
O2 C9 C10 109.74(12) .
O3 C10 C9 111.02(11) .
O3 C11 C12 110.37(11) .
O4 C12 C11 109.81(11) .
O4 C13 C14 108.90(11) .
O5 C14 C13 107.51(10) .
O6 C15 C5 108.89(11) .
O7 C16 O6 123.80(13) .
O7 C16 C17 123.75(12) .
O6 C16 C17 112.44(11) .
N1 C17 C18 124.00(13) .
N1 C17 C16 118.06(12) .
C18 C17 C16 117.93(12) .
C17 C18 C19 118.53(13) .
C20 C19 C18 118.50(14) .
C19 C20 C21 118.76(13) .
N1 C21 C20 123.78(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3693(16) .
O1 C7 1.4357(17) .
O2 C9 1.4158(15) .
O2 C8 1.4234(18) .
O3 C10 1.4202(18) .
O3 C11 1.4240(18) .
O4 C13 1.4173(18) .
O4 C12 1.4300(16) .
O5 C3 1.3688(16) 3_666
O5 C14 1.4325(16) .
O6 C16 1.3369(16) .
O6 C15 1.4438(16) .
O7 C16 1.2072(17) .
N1 C21 1.3362(19) .
N1 C17 1.3445(17) .
C1 C6 1.3930(19) .
C1 C2 1.3942(19) .
C2 C3 1.3958(18) .
C3 O5 1.3688(16) 3_666
C3 C4 1.3886(19) .
C4 C5 1.3890(19) .
C5 C6 1.3917(19) .
C5 C15 1.5041(19) .
C7 C8 1.4997(19) .
C9 C10 1.499(2) .
C11 C12 1.500(2) .
C13 C14 1.5057(18) .
C16 C17 1.5003(18) .
C17 C18 1.3824(19) .
C18 C19 1.386(2) .
C19 C20 1.383(2) .
C20 C21 1.387(2) .
