#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503014.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_1503014
loop_
_publ_author_name
'Zhang, Zibin'
'Xia, Binyuan'
'Han, Chengyou'
'Yu, Yihua'
'Huang, Feihe'
_publ_section_title
;
 Syntheses of copillar[5]arenes by co-oligomerization of different
 monomers.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3285
_journal_page_last               3287
_journal_paper_doi               10.1021/ol100883k
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C51 H62 O10, 2(C H2 Cl2)'
_chemical_formula_sum            'C53 H66 Cl4 O10'
_chemical_formula_weight         1004.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.311(2)
_cell_length_b                   21.467(4)
_cell_length_c                   21.439(4)
_cell_measurement_reflns_used    20668
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     5056.1(17)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    XP
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19677
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count image
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0574
_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)+(0.0760P)²+15.9211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1610
_reflns_number_gt                4089
_reflns_number_total             4457
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol100883k_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        5055.8(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1503014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cl1 Cl 0.31267(8) 0.37882(5) 0.21702(4) 0.0545(3) Uani 1 1 d .
Cl2 Cl 0.05459(8) 0.34845(4) 0.17554(4) 0.0420(2) Uani 1 1 d .
O1 O 0.61306(16) 0.48106(9) 0.14084(9) 0.0250(4) Uani 1 1 d .
O2 O 1.09417(16) 0.54081(9) 0.15132(9) 0.0237(4) Uani 1 1 d .
O3 O 0.62532(16) 0.24243(8) 0.15592(8) 0.0209(4) Uani 1 1 d .
O4 O 0.88889(16) 0.36698(8) 0.00669(8) 0.0194(4) Uani 1 1 d .
O5 O 1.06651(16) 0.18202(9) 0.13361(8) 0.0210(4) Uani 1 1 d .
C1 C 1.0000 0.58717(16) 0.2500 0.0192(7) Uani 1 2 d S
H1A H 1.0488 0.6144 0.2317 0.023 Uiso 1 1 d .
C2 C 0.9235(2) 0.54817(11) 0.19612(11) 0.0166(5) Uani 1 1 d .
C3 C 0.8022(2) 0.53360(11) 0.19453(12) 0.0183(5) Uani 1 1 d .
H3A H 0.7674 0.5482 0.2269 0.022 Uiso 1 1 calc R
C4 C 0.7329(2) 0.49744(11) 0.14508(12) 0.0183(5) Uani 1 1 d .
C5 C 0.7827(2) 0.47544(11) 0.09557(11) 0.0167(5) Uani 1 1 d .
C6 C 0.9036(2) 0.49012(11) 0.09714(11) 0.0174(5) Uani 1 1 d .
H6A H 0.9380 0.4760 0.0644 0.021 Uiso 1 1 calc R
C7 C 0.9735(2) 0.52552(11) 0.14671(12) 0.0175(5) Uani 1 1 d .
C8 C 0.7078(2) 0.43478(11) 0.04271(11) 0.0181(5) Uani 1 1 d .
H8A H 0.7303 0.4432 0.0026 0.022 Uiso 1 1 calc R
H8B H 0.6220 0.4444 0.0369 0.022 Uiso 1 1 calc R
C9 C 0.7300(2) 0.36648(11) 0.06039(11) 0.0166(5) Uani 1 1 d .
C10 C 0.6613(2) 0.33591(12) 0.09710(11) 0.0170(5) Uani 1 1 d .
H10A H 0.5964 0.3565 0.1077 0.020 Uiso 1 1 calc R
C11 C 0.6884(2) 0.27486(12) 0.11822(11) 0.0163(5) Uani 1 1 d .
C12 C 0.7852(2) 0.24282(11) 0.10229(11) 0.0156(5) Uani 1 1 d .
C13 C 0.8523(2) 0.27328(11) 0.06453(11) 0.0156(5) Uani 1 1 d .
H13A H 0.9159 0.2525 0.0529 0.019 Uiso 1 1 calc R
C14 C 0.8254(2) 0.33432(11) 0.04395(11) 0.0157(5) Uani 1 1 d .
C15 C 0.8186(2) 0.17747(11) 0.12690(11) 0.0169(5) Uani 1 1 d .
H15A H 0.8511 0.1546 0.0957 0.020 Uiso 1 1 calc R
H15B H 0.7461 0.1560 0.1322 0.020 Uiso 1 1 calc R
C16 C 0.8770(2) 0.17996(11) 0.24859(12) 0.0170(5) Uani 1 1 d .
H16A H 0.7946 0.1801 0.2480 0.020 Uiso 1 1 calc R
C17 C 0.9126(2) 0.17888(10) 0.19083(11) 0.0152(5) Uani 1 1 d .
C18 C 1.0374(2) 0.18078(11) 0.19278(11) 0.0169(5) Uani 1 1 d .
C19 C 1.1914(2) 0.18676(13) 0.13201(12) 0.0216(5) Uani 1 1 d .
H19A H 1.2382 0.1539 0.1577 0.026 Uiso 1 1 calc R
H19B H 1.2242 0.2266 0.1493 0.026 Uiso 1 1 calc R
C20 C 1.1989(2) 0.18066(13) 0.06240(13) 0.0246(6) Uani 1 1 d .
H20A H 1.2838 0.1787 0.0608 0.030 Uiso 1 1 calc R
H20B H 1.1638 0.2175 0.0390 0.030 Uiso 1 1 calc R
C21 C 1.1331(3) 0.12321(14) 0.02921(13) 0.0305(6) Uani 1 1 d .
H21A H 1.0461 0.1307 0.0194 0.037 Uiso 1 1 calc R
H21B H 1.1502 0.0882 0.0586 0.037 Uiso 1 1 calc R
C22 C 1.1700(3) 0.10605(15) -0.03274(13) 0.0303(6) Uani 1 1 d .
H22A H 1.1261 0.0696 -0.0512 0.045 Uiso 1 1 calc R
H22B H 1.2558 0.0977 -0.0233 0.045 Uiso 1 1 calc R
H22C H 1.1513 0.1400 -0.0626 0.045 Uiso 1 1 calc R
C23 C 0.5503(3) 0.51293(17) 0.18005(19) 0.0447(9) Uani 1 1 d .
H23A H 0.4686 0.4973 0.1725 0.067 Uiso 1 1 calc R
H23B H 0.5484 0.5566 0.1702 0.067 Uiso 1 1 calc R
H23C H 0.5910 0.5067 0.2243 0.067 Uiso 1 1 calc R
C24 C 1.1519(2) 0.51330(13) 0.10598(12) 0.0228(6) Uani 1 1 d .
H24A H 1.2347 0.5273 0.1141 0.034 Uiso 1 1 calc R
H24B H 1.1095 0.5253 0.0634 0.034 Uiso 1 1 calc R
H24C H 1.1503 0.4688 0.1099 0.034 Uiso 1 1 calc R
C25 C 0.5104(2) 0.26696(13) 0.16039(14) 0.0278(6) Uani 1 1 d .
H25A H 0.4759 0.2407 0.1877 0.042 Uiso 1 1 calc R
H25B H 0.4567 0.2685 0.1184 0.042 Uiso 1 1 calc R
H25C H 0.5214 0.3082 0.1782 0.042 Uiso 1 1 calc R
C26 C 0.9917(2) 0.33753(13) -0.00804(12) 0.0212(5) Uani 1 1 d .
H26A H 1.0271 0.3649 -0.0340 0.032 Uiso 1 1 calc R
H26B H 0.9665 0.2996 -0.0311 0.032 Uiso 1 1 calc R
H26C H 1.0507 0.3283 0.0311 0.032 Uiso 1 1 calc R
C27 C 0.1736(3) 0.3691(2) 0.24044(17) 0.0503(9) Uani 1 1 d .
H27A H 0.1836 0.3370 0.2731 0.060 Uiso 1 1 calc R
H27B H 0.1532 0.4077 0.2590 0.060 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 0.0033 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'
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
C4 O1 C23 117.7(2) . .
C7 O2 C24 117.25(19) . .
C11 O3 C25 117.2(2) . .
C14 O4 C26 117.80(19) . .
C18 O5 C19 118.47(19) . .
C2 C1 C2 113.1(3) . 2_755
C2 C1 H1A 107.9 . .
C2 C1 H1A 111.8 2_755 .
C3 C2 C7 118.2(2) . .
C3 C2 C1 121.27(19) . .
C7 C2 C1 120.5(2) . .
C4 C3 C2 120.9(2) . .
C4 C3 H3A 119.6 . .
C2 C3 H3A 119.6 . .
O1 C4 C3 123.8(2) . .
O1 C4 C5 115.5(2) . .
C3 C4 C5 120.7(2) . .
C6 C5 C4 118.4(2) . .
C6 C5 C8 121.1(2) . .
C4 C5 C8 120.5(2) . .
C7 C6 C5 121.2(2) . .
C7 C6 H6A 119.4 . .
C5 C6 H6A 119.4 . .
O2 C7 C6 123.8(2) . .
O2 C7 C2 115.6(2) . .
C6 C7 C2 120.6(2) . .
C5 C8 C9 109.78(19) . .
C5 C8 H8A 109.7 . .
C9 C8 H8A 109.7 . .
C5 C8 H8B 109.7 . .
C9 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C10 C9 C14 118.5(2) . .
C10 C9 C8 120.9(2) . .
C14 C9 C8 120.4(2) . .
C9 C10 C11 121.0(2) . .
C9 C10 H10A 119.5 . .
C11 C10 H10A 119.5 . .
O3 C11 C10 123.8(2) . .
O3 C11 C12 115.8(2) . .
C10 C11 C12 120.4(2) . .
C13 C12 C11 118.4(2) . .
C13 C12 C15 120.7(2) . .
C11 C12 C15 120.9(2) . .
C14 C13 C12 121.1(2) . .
C14 C13 H13A 119.5 . .
C12 C13 H13A 119.5 . .
O4 C14 C13 123.7(2) . .
O4 C14 C9 115.7(2) . .
C13 C14 C9 120.6(2) . .
C12 C15 C17 111.00(19) . .
C12 C15 H15A 109.4 . .
C17 C15 H15A 109.4 . .
C12 C15 H15B 109.4 . .
C17 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C17 C16 C18 121.2(2) . 2_755
C17 C16 H16A 119.4 . .
C18 C16 H16A 119.4 2_755 .
C16 C17 C18 118.4(2) . .
C16 C17 C15 120.9(2) . .
C18 C17 C15 120.7(2) . .
O5 C18 C16 124.2(2) . 2_755
O5 C18 C17 115.5(2) . .
C16 C18 C17 120.3(2) 2_755 .
O5 C19 C20 107.7(2) . .
O5 C19 H19A 110.2 . .
C20 C19 H19A 110.2 . .
O5 C19 H19B 110.2 . .
C20 C19 H19B 110.2 . .
H19A C19 H19B 108.5 . .
C19 C20 C21 113.1(2) . .
C19 C20 H20A 109.0 . .
C21 C20 H20A 109.0 . .
C19 C20 H20B 109.0 . .
C21 C20 H20B 109.0 . .
H20A C20 H20B 107.8 . .
C20 C21 C22 113.3(2) . .
C20 C21 H21A 108.9 . .
C22 C21 H21A 108.9 . .
C20 C21 H21B 108.9 . .
C22 C21 H21B 108.9 . .
H21A C21 H21B 107.7 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
O1 C23 H23A 109.5 . .
O1 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
O1 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O2 C24 H24A 109.5 . .
O2 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O2 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
O3 C25 H25A 109.5 . .
O3 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
O3 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
O4 C26 H26A 109.5 . .
O4 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
O4 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
Cl2 C27 Cl1 111.8(2) . .
Cl2 C27 H27A 109.3 . .
Cl1 C27 H27A 109.3 . .
Cl2 C27 H27B 109.3 . .
Cl1 C27 H27B 109.3 . .
H27A C27 H27B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C27 1.773(4) .
Cl2 C27 1.747(3) .
O1 C4 1.383(3) .
O1 C23 1.401(3) .
O2 C7 1.384(3) .
O2 C24 1.422(3) .
O3 C11 1.386(3) .
O3 C25 1.427(3) .
O4 C14 1.385(3) .
O4 C26 1.423(3) .
O5 C18 1.385(3) .
O5 C19 1.425(3) .
C1 C2 1.519(3) .
C1 C2 1.519(3) 2_755
C1 H1A 0.9504 .
C2 C3 1.400(3) .
C2 C7 1.401(3) .
C3 C4 1.395(4) .
C3 H3A 0.9300 .
C4 C5 1.397(3) .
C5 C6 1.396(3) .
C5 C8 1.519(3) .
C6 C7 1.390(4) .
C6 H6A 0.9300 .
C8 C9 1.520(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.395(4) .
C9 C14 1.395(3) .
C10 C11 1.396(4) .
C10 H10A 0.9300 .
C11 C12 1.402(3) .
C12 C13 1.397(3) .
C12 C15 1.515(3) .
C13 C14 1.393(3) .
C13 H13A 0.9300 .
C15 C17 1.522(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.391(3) .
C16 C18 1.392(4) 2_755
C16 H16A 0.9300 .
C17 C18 1.402(3) .
C18 C16 1.392(4) 2_755
C19 C20 1.520(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.526(4) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.529(4) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
