#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/06/4500681.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_4500681
loop_
_publ_author_name
'Guan, Yang-Fan'
'Li, Zheng-Yi'
'Ni, Meng-Fei'
'Lin, Chen'
'Jiang, Juli'
'Li, Yi-Zhi'
'Wang, Leyong'
_publ_section_title
;
 Chiral Moieties-Oriented Single-Stranded Helical Assembly of
 Calix[4]azacrown Derivatives
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2684
_journal_paper_doi               10.1021/cg2000975
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C51 H64 N O7, C H4 O, H2 O'
_chemical_formula_sum            'C52 H70 N O9'
_chemical_formula_weight         853.09
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           152
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31 2"'
_symmetry_space_group_name_H-M   'P 31 2 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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   12.6602(9)
_cell_length_b                   12.6602(9)
_cell_length_c                   28.733(4)
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      20.17
_cell_measurement_theta_min      2.33
_cell_volume                     3988.3(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart Apex CCD '
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            21817
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1383
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0606
_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)+(0.05P)²+1.55P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                4042
_reflns_number_total             5230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg2000975_si_001.cif
_cod_data_source_block           S-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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_sg_symbol_Hall     'P 31 2" '
_cod_original_sg_symbol_H-M      'P3(1)21 '
_cod_database_code               4500681
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'-x, -x+y, -z+1/3'
'x-y, -y, -z+2/3'
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
C1 C 0.0876(3) 0.0173(3) 0.73791(10) 0.0415(7) Uani 1 1 d .
C2 C 0.1943(3) 0.1311(3) 0.73307(10) 0.0401(7) Uani 1 1 d .
C3 C 0.2955(3) 0.1302(3) 0.71263(11) 0.0464(8) Uani 1 1 d .
H3 H 0.3667 0.2043 0.7080 0.056 Uiso 1 1 calc R
C4 C 0.2936(3) 0.0249(3) 0.69923(10) 0.0459(8) Uani 1 1 d .
C5 C 0.1881(3) -0.0854(3) 0.70769(11) 0.0459(8) Uani 1 1 d .
H5 H 0.1865 -0.1578 0.7004 0.055 Uiso 1 1 calc R
C6 C 0.0822(3) -0.0903(3) 0.72724(10) 0.0472(7) Uani 1 1 d .
C7 C 0.2142(3) 0.2566(3) 0.74588(11) 0.0417(7) Uani 1 1 d .
H7A H 0.1381 0.2576 0.7446 0.050 Uiso 1 1 calc R
H7B H 0.2724 0.3186 0.7250 0.050 Uiso 1 1 calc R
C8 C 0.2663(3) 0.2790(3) 0.79804(11) 0.0451(7) Uani 1 1 d .
C9 C 0.2023(3) 0.2354(3) 0.83993(11) 0.0432(7) Uani 1 1 d .
C10 C 0.2584(3) 0.2613(3) 0.88246(10) 0.0417(7) Uani 1 1 d .
C11 C 0.3842(4) 0.3293(3) 0.88379(12) 0.0529(8) Uani 1 1 d .
H11 H 0.4237 0.3427 0.9123 0.063 Uiso 1 1 calc R
C12 C 0.4536(4) 0.3782(3) 0.84381(12) 0.0608(10) Uani 1 1 d .
C13 C 0.3941(4) 0.3524(3) 0.80095(12) 0.0585(10) Uani 1 1 d .
H13 H 0.4394 0.3842 0.7739 0.070 Uiso 1 1 calc R
C14 C 0.1843(3) 0.2091(3) 0.92709(12) 0.0536(8) Uani 1 1 d .
H14A H 0.2239 0.2662 0.9524 0.064 Uiso 1 1 calc R
H14B H 0.1037 0.1990 0.9229 0.064 Uiso 1 1 calc R
C15 C 0.4083(3) 0.0345(3) 0.67783(11) 0.0451(7) Uani 1 1 d .
C16 C 0.4272(3) 0.0977(3) 0.63103(11) 0.0484(8) Uani 1 1 d .
H16A H 0.4071 0.0393 0.6065 0.073 Uiso 1 1 calc R
H16B H 0.5109 0.1608 0.6281 0.073 Uiso 1 1 calc R
H16C H 0.3755 0.1328 0.6290 0.073 Uiso 1 1 calc R
C17 C 0.3844(3) -0.0943(3) 0.66835(12) 0.0515(8) Uani 1 1 d .
H17A H 0.3416 -0.1460 0.6942 0.077 Uiso 1 1 calc R
H17B H 0.4607 -0.0922 0.6642 0.077 Uiso 1 1 calc R
H17C H 0.3360 -0.1256 0.6407 0.077 Uiso 1 1 calc R
C18 C 0.5198(3) 0.1276(3) 0.70404(12) 0.0508(9) Uani 1 1 d .
H18A H 0.5374 0.2082 0.6956 0.076 Uiso 1 1 calc R
H18B H 0.5881 0.1178 0.6963 0.076 Uiso 1 1 calc R
H18C H 0.5046 0.1161 0.7369 0.076 Uiso 1 1 calc R
C19 C 0.5925(4) 0.4513(3) 0.84654(12) 0.0557(9) Uani 1 1 d .
C20 C 0.6554(3) 0.4404(3) 0.80257(11) 0.0522(9) Uani 1 1 d .
H20A H 0.7410 0.4987 0.8040 0.078 Uiso 1 1 calc R
H20B H 0.6207 0.4563 0.7756 0.078 Uiso 1 1 calc R
H20C H 0.6438 0.3596 0.8006 0.078 Uiso 1 1 calc R
C21 C 0.6422(3) 0.4303(3) 0.89149(11) 0.0440(7) Uani 1 1 d .
H21A H 0.5971 0.4358 0.9174 0.066 Uiso 1 1 calc R
H21B H 0.7267 0.4910 0.8946 0.066 Uiso 1 1 calc R
H21C H 0.6341 0.3507 0.8909 0.066 Uiso 1 1 calc R
C22 C 0.6200(4) 0.5799(3) 0.84665(12) 0.0532(9) Uani 1 1 d .
H22A H 0.5931 0.5970 0.8755 0.080 Uiso 1 1 calc R
H22B H 0.5784 0.5925 0.8212 0.080 Uiso 1 1 calc R
H22C H 0.7063 0.6334 0.8434 0.080 Uiso 1 1 calc R
C23 C -0.0954(3) 0.0170(3) 0.72110(11) 0.0432(7) Uani 1 1 d .
H23A H -0.1181 -0.0500 0.6995 0.052 Uiso 1 1 calc R
H23B H -0.0534 0.0928 0.7038 0.052 Uiso 1 1 calc R
C24 C -0.2077(3) 0.0058(3) 0.74349(11) 0.0469(8) Uani 1 1 d .
C25 C -0.3354(3) -0.0519(3) 0.81504(12) 0.0506(8) Uani 1 1 d .
H25 H -0.3964 -0.0472 0.7955 0.061 Uiso 1 1 d R
C26 C -0.3900(8) -0.1686(7) 0.8403(2) 0.0565(19) Uani 0.50 1 d P
H26A H -0.4639 -0.2268 0.8250 0.085 Uiso 0.50 1 calc PR
H26B H -0.4080 -0.1565 0.8717 0.085 Uiso 0.50 1 calc PR
H26C H -0.3337 -0.1985 0.8407 0.085 Uiso 0.50 1 calc PR
C27 C 0.3513(6) -0.0729(6) 0.8273(2) 0.0488(15) Uani 0.50 1 d P
H27A H 0.4378 -0.0321 0.8324 0.073 Uiso 0.50 1 calc PR
H27B H 0.3338 -0.1033 0.7960 0.073 Uiso 0.50 1 calc PR
H27C H 0.3111 -0.1396 0.8487 0.073 Uiso 0.50 1 calc PR
N1 N -0.2251(2) -0.0281(2) 0.78623(8) 0.0429(5) Uani 0.50 1 d P
H1A H -0.1603 0.0297 0.8019 0.052 Uiso 0.50 1 d PR
O1 O -0.0160(2) 0.01485(19) 0.75640(7) 0.0449(5) Uani 1 1 d .
O2 O 0.0752(2) 0.16051(19) 0.83821(7) 0.0421(5) Uani 1 1 d .
H2B H 0.0492 0.1609 0.8069 0.063 Uiso 1 1 d R
O3 O -0.2797(2) 0.0171(2) 0.72088(8) 0.0493(5) Uani 1 1 d .
O4 O -0.2251(2) -0.0281(2) 0.78623(8) 0.0429(5) Uani 0.50 1 d P
O5 O 0.3142(2) 0.0000 0.8333 0.0443(7) Uani 1 2 d S
H5B H 0.2817 0.0065 0.8084 0.066 Uiso 0.25 1 d PR
H5C H 0.2616 -0.0261 0.8551 0.066 Uiso 0.25 1 d PR
O6 O 0.8714(4) 0.3174(4) 0.68655(15) 0.0551(13) Uani 0.50 1 d P
H6A H 0.8861 0.2591 0.6837 0.083 Uiso 0.50 1 d PR
H6B H 0.8917 0.3594 0.6617 0.083 Uiso 0.50 1 d PR
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
C6 C1 O1 119.0(3) . .
C6 C1 C2 122.9(3) . .
O1 C1 C2 118.1(3) . .
C1 C2 C3 116.3(3) . .
C1 C2 C7 128.1(3) . .
C3 C2 C7 115.5(3) . .
C4 C3 C2 123.1(3) . .
C4 C3 H3 118.4 . .
C2 C3 H3 118.4 . .
C3 C4 C5 117.9(3) . .
C3 C4 C15 118.7(3) . .
C5 C4 C15 123.3(3) . .
C4 C5 C6 121.5(3) . .
C4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C1 C6 C5 118.0(3) . .
C1 C6 C14 121.6(3) . 6_556
C5 C6 C14 120.1(3) . 6_556
C2 C7 C8 104.4(2) . .
C2 C7 H7A 110.9 . .
C8 C7 H7A 110.9 . .
C2 C7 H7B 110.9 . .
C8 C7 H7B 110.9 . .
H7A C7 H7B 108.9 . .
C9 C8 C13 117.1(3) . .
C9 C8 C7 128.8(3) . .
C13 C8 C7 114.0(3) . .
C10 C9 C8 123.0(3) . .
C10 C9 O2 118.4(3) . .
C8 C9 O2 118.6(3) . .
C9 C10 C11 118.2(3) . .
C9 C10 C14 120.8(3) . .
C11 C10 C14 120.8(3) . .
C10 C11 C12 122.0(3) . .
C10 C11 H11 119.0 . .
C12 C11 H11 119.0 . .
C11 C12 C13 118.6(4) . .
C11 C12 C19 120.5(3) . .
C13 C12 C19 120.8(4) . .
C12 C13 C8 121.0(4) . .
C12 C13 H13 119.5 . .
C8 C13 H13 119.5 . .
C6 C14 C10 111.6(3) 6_556 .
C6 C14 H14A 109.3 6_556 .
C10 C14 H14A 109.3 . .
C6 C14 H14B 109.3 6_556 .
C10 C14 H14B 109.3 . .
H14A C14 H14B 108.0 . .
C18 C15 C16 101.0(3) . .
C18 C15 C4 110.0(3) . .
C16 C15 C4 106.9(3) . .
C18 C15 C17 122.1(3) . .
C16 C15 C17 107.4(3) . .
C4 C15 C17 108.3(3) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C15 C18 H18A 109.5 . .
C15 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C15 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C22 C19 C21 107.5(3) . .
C22 C19 C12 103.4(3) . .
C21 C19 C12 113.0(3) . .
C22 C19 C20 104.6(3) . .
C21 C19 C20 114.0(3) . .
C12 C19 C20 113.3(3) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C19 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
O1 C23 C24 109.5(3) . .
O1 C23 H23A 109.8 . .
C24 C23 H23A 109.8 . .
O1 C23 H23B 109.8 . .
C24 C23 H23B 109.8 . .
H23A C23 H23B 108.2 . .
O3 C24 N1 123.5(3) . .
O3 C24 C23 120.2(3) . .
N1 C24 C23 115.9(3) . .
C26 C25 N1 113.1(4) . .
C26 C25 C25 107.7(4) . 6_556
N1 C25 C25 104.1(2) . 6_556
C26 C25 H25 110.7 . .
N1 C25 H25 110.6 . .
C25 C25 H25 110.4 6_556 .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
O5 C27 C27 48.7(3) . 6_556
O5 C27 H27A 109.5 . .
C27 C27 H27A 60.8 6_556 .
O5 C27 H27B 109.5 . .
C27 C27 H27B 122.7 6_556 .
H27A C27 H27B 109.5 . .
O5 C27 H27C 109.5 . .
C27 C27 H27C 127.4 6_556 .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C24 N1 C25 125.1(3) . .
C24 N1 H1A 105.8 . .
C25 N1 H1A 105.2 . .
C1 O1 C23 112.8(2) . .
C9 O2 H2B 108.1 . .
C27 O5 C27 82.6(7) . 6_556
C27 O5 H5B 109.6 . .
C27 O5 H5B 117.7 6_556 .
C27 O5 H5C 109.2 . .
C27 O5 H5C 123.8 6_556 .
H5B O5 H5C 109.5 . .
H6A O6 H6B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.365(4) .
C1 O1 1.400(4) .
C1 C2 1.405(4) .
C2 C3 1.415(4) .
C2 C7 1.525(4) .
C3 C4 1.376(4) .
C3 H3 0.9300 .
C4 C5 1.388(5) .
C4 C15 1.525(5) .
C5 C6 1.426(5) .
C5 H5 0.9300 .
C6 C14 1.479(5) 6_556
C7 C8 1.605(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.401(4) .
C8 C13 1.408(6) .
C9 C10 1.368(4) .
C9 O2 1.402(4) .
C10 C11 1.381(5) .
C10 C14 1.530(5) .
C11 C12 1.390(5) .
C11 H11 0.9300 .
C12 C13 1.395(5) .
C12 C19 1.526(6) .
C13 H13 0.9300 .
C14 C6 1.479(5) 6_556
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C18 1.512(4) .
C15 C16 1.521(4) .
C15 C17 1.526(4) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 C22 1.486(4) .
C19 C21 1.517(5) .
C19 C20 1.536(5) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 O1 1.438(4) .
C23 C24 1.502(4) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 O3 1.185(4) .
C24 N1 1.283(4) .
C25 C26 1.471(8) .
C25 N1 1.518(4) .
C25 C25 1.550(6) 6_556
C25 H25 0.9800 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 O5 1.239(7) .
C27 C27 1.635(13) 6_556
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
N1 H1A 0.9000 .
O2 H2B 0.9600 .
O5 C27 1.239(7) 6_556
O5 H5B 0.8500 .
O5 H5C 0.8500 .
O6 H6A 0.8500 .
O6 H6B 0.8501 .
