#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503814.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_1503814
loop_
_publ_author_name
'Van Rossom, Wim'
'Ovaere, Margriet'
'Van Meervelt, Luc'
'Dehaen, Wim'
'Maes, Wouter'
_publ_section_title
;
 Efficient fragment coupling approaches toward large oxacalix[n]arenes (n
 = 6, 8).
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1681
_journal_page_last               1684
_journal_paper_doi               10.1021/ol900116h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C68 H48 N8 O8'
_chemical_formula_sum            'C68 H48 N8 O8'
_chemical_formula_weight         1105.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.919(7)
_cell_angle_beta                 104.689(7)
_cell_angle_gamma                91.598(8)
_cell_formula_units_Z            1
_cell_length_a                   10.2187(11)
_cell_length_b                   10.7224(12)
_cell_length_c                   12.9364(13)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.30
_cell_measurement_theta_min      3.56
_cell_volume                     1358.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Pluton
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'crossed Goebel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_sigmaI/netI    0.1061
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23684
_diffrn_reflns_theta_full        71.30
_diffrn_reflns_theta_max         71.30
_diffrn_reflns_theta_min         3.56
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0514
_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)+(0.0000P)²+0.3014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                4046
_reflns_number_total             5186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900116h_si_002.cif
_cod_data_source_block           wim57
_cod_database_code               1503814
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.2210(2) 0.40460(17) 0.52878(16) 0.0262(4) Uani 1 1 d .
H1 H 0.2767 0.3776 0.4828 0.031 Uiso 1 1 calc R
C2 C 0.1532(2) 0.31619(18) 0.56999(17) 0.0296(4) Uani 1 1 d .
H2 H 0.1641 0.2291 0.5529 0.036 Uiso 1 1 calc R
C3 C 0.0700(2) 0.35444(19) 0.63572(17) 0.0306(5) Uani 1 1 d .
H3 H 0.0238 0.2938 0.6637 0.037 Uiso 1 1 calc R
C4 C 0.0543(2) 0.48165(19) 0.66059(16) 0.0277(4) Uani 1 1 d .
H4 H -0.0043 0.5079 0.7044 0.033 Uiso 1 1 calc R
C5 C 0.12365(19) 0.57097(17) 0.62193(15) 0.0234(4) Uani 1 1 d .
H5 H 0.1143 0.6580 0.6410 0.028 Uiso 1 1 calc R
C6 C 0.20720(19) 0.53301(17) 0.55488(14) 0.0212(4) Uani 1 1 d .
C7 C 0.27884(18) 0.62867(16) 0.51191(14) 0.0200(4) Uani 1 1 d .
N8 N 0.27932(15) 0.74863(14) 0.55521(12) 0.0203(3) Uani 1 1 d .
C9 C 0.34923(18) 0.83210(16) 0.51855(14) 0.0195(4) Uani 1 1 d .
C10 C 0.41761(19) 0.80214(17) 0.44088(15) 0.0219(4) Uani 1 1 d .
H10 H 0.4685 0.8632 0.4173 0.026 Uiso 1 1 calc R
C11 C 0.40622(18) 0.67558(17) 0.39980(14) 0.0202(4) Uani 1 1 d .
N12 N 0.33849(16) 0.58811(14) 0.43371(12) 0.0217(3) Uani 1 1 d .
O13 O 0.46746(14) 0.64780(12) 0.31894(11) 0.0247(3) Uani 1 1 d .
O14 O 0.35696(13) 0.95587(11) 0.56079(10) 0.0225(3) Uani 1 1 d .
C15 C 0.2876(2) 0.99278(16) 0.63851(15) 0.0213(4) Uani 1 1 d .
C16 C 0.1471(2) 0.97637(16) 0.61485(15) 0.0218(4) Uani 1 1 d .
H16 H 0.0956 0.9334 0.5476 0.026 Uiso 1 1 calc R
C17 C 0.0857(2) 1.02488(16) 0.69282(16) 0.0238(4) Uani 1 1 d .
C18 C 0.1583(2) 1.08947(17) 0.79149(15) 0.0259(4) Uani 1 1 d .
H18 H 0.1124 1.1240 0.8426 0.031 Uiso 1 1 calc R
C19 C 0.2989(2) 1.10286(17) 0.81435(16) 0.0267(4) Uani 1 1 d .
C20 C 0.3625(2) 1.05457(17) 0.73666(16) 0.0248(4) Uani 1 1 d .
H20 H 0.4584 1.0640 0.7510 0.030 Uiso 1 1 calc R
C21 C 0.3808(2) 1.1635(2) 0.92394(17) 0.0352(5) Uani 1 1 d .
H21A H 0.4065 1.0986 0.9713 0.053 Uiso 1 1 calc R
H21B H 0.3265 1.2239 0.9550 0.053 Uiso 1 1 calc R
H21C H 0.4628 1.2074 0.9166 0.053 Uiso 1 1 calc R
O22 O -0.05716(14) 1.00977(12) 0.66642(11) 0.0263(3) Uani 1 1 d .
C23 C -0.1135(2) 0.93848(16) 0.72552(15) 0.0228(4) Uani 1 1 d .
C24 C -0.2534(2) 0.91283(17) 0.69271(15) 0.0238(4) Uani 1 1 d .
H24 H -0.3097 0.9444 0.6323 0.029 Uiso 1 1 calc R
C25 C -0.30353(19) 0.83767(16) 0.75535(15) 0.0211(4) Uani 1 1 d .
N26 N -0.22777(16) 0.79463(14) 0.84204(12) 0.0223(3) Uani 1 1 d .
C27 C -0.09498(19) 0.82682(16) 0.86574(15) 0.0208(4) Uani 1 1 d .
N28 N -0.03397(16) 0.89630(14) 0.81035(13) 0.0235(3) Uani 1 1 d .
C29 C -0.0084(2) 0.78354(17) 0.96373(15) 0.0236(4) Uani 1 1 d .
C30 C -0.0516(2) 0.67998(19) 1.00454(16) 0.0285(4) Uani 1 1 d .
H30 H -0.1363 0.6364 0.9690 0.034 Uiso 1 1 calc R
C31 C 0.0288(2) 0.6400(2) 1.09715(17) 0.0351(5) Uani 1 1 d .
H31 H -0.0001 0.5685 1.1243 0.042 Uiso 1 1 calc R
C32 C 0.1513(2) 0.7050(2) 1.14952(17) 0.0383(5) Uani 1 1 d .
H32 H 0.2057 0.6786 1.2133 0.046 Uiso 1 1 calc R
C33 C 0.1946(2) 0.8075(2) 1.10991(18) 0.0350(5) Uani 1 1 d .
H33 H 0.2785 0.8516 1.1469 0.042 Uiso 1 1 calc R
C34 C 0.1168(2) 0.84727(19) 1.01625(17) 0.0287(4) Uani 1 1 d .
H34 H 0.1482 0.9169 0.9882 0.034 Uiso 1 1 calc R
O35 O -0.43971(13) 0.80974(12) 0.72947(11) 0.0243(3) Uani 1 1 d .
C36 C -0.48135(18) 0.69401(17) 0.75613(15) 0.0221(4) Uani 1 1 d .
C37 C -0.44157(19) 0.58544(17) 0.70557(15) 0.0226(4) Uani 1 1 d .
H37 H -0.3836 0.5890 0.6589 0.027 Uiso 1 1 calc R
C38 C -0.49032(19) 0.47167(17) 0.72623(15) 0.0216(4) Uani 1 1 d .
C39 C -0.57267(19) 0.46754(18) 0.79653(15) 0.0244(4) Uani 1 1 d .
H39 H -0.6034 0.3884 0.8106 0.029 Uiso 1 1 calc R
C40 C -0.6105(2) 0.57747(18) 0.84631(15) 0.0256(4) Uani 1 1 d .
C41 C -0.56443(19) 0.69322(18) 0.82423(15) 0.0246(4) Uani 1 1 d .
H41 H -0.5904 0.7700 0.8560 0.030 Uiso 1 1 calc R
C42 C -0.6999(2) 0.5718(2) 0.92228(18) 0.0347(5) Uani 1 1 d .
H42A H -0.7422 0.4866 0.9128 0.052 Uiso 1 1 calc R
H42B H -0.7704 0.6320 0.9067 0.052 Uiso 1 1 calc R
H42C H -0.6451 0.5931 0.9968 0.052 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C2 C1 C6 120.2(2) .
C2 C1 H1 119.9 .
C6 C1 H1 119.9 .
C3 C2 C1 120.38(19) .
C3 C2 H2 119.8 .
C1 C2 H2 119.8 .
C2 C3 C4 119.71(18) .
C2 C3 H3 120.1 .
C4 C3 H3 120.1 .
C3 C4 C5 120.5(2) .
C3 C4 H4 119.8 .
C5 C4 H4 119.8 .
C4 C5 C6 120.10(18) .
C4 C5 H5 119.9 .
C6 C5 H5 119.9 .
C1 C6 C5 119.13(17) .
C1 C6 C7 120.94(18) .
C5 C6 C7 119.93(16) .
N8 C7 N12 125.47(16) .
N8 C7 C6 116.92(17) .
N12 C7 C6 117.61(16) .
C9 N8 C7 115.77(16) .
N8 C9 O14 119.09(17) .
N8 C9 C10 124.32(16) .
O14 C9 C10 116.58(16) .
C9 C10 C11 114.59(17) .
C9 C10 H10 122.7 .
C11 C10 H10 122.7 .
N12 C11 O13 122.05(16) .
N12 C11 C10 123.66(18) .
O13 C11 C10 114.26(16) .
C11 N12 C7 116.13(15) .
C11 O13 C38 126.89(14) 2_566
C9 O14 C15 119.37(14) .
C20 C15 C16 121.34(18) .
C20 C15 O14 117.54(17) .
C16 C15 O14 120.95(16) .
C17 C16 C15 117.26(17) .
C17 C16 H16 121.4 .
C15 C16 H16 121.4 .
C16 C17 C18 122.65(18) .
C16 C17 O22 116.44(16) .
C18 C17 O22 120.88(18) .
C19 C18 C17 119.20(19) .
C19 C18 H18 120.4 .
C17 C18 H18 120.4 .
C20 C19 C18 118.94(17) .
C20 C19 C21 120.68(19) .
C18 C19 C21 120.31(19) .
C15 C20 C19 120.59(18) .
C15 C20 H20 119.7 .
C19 C20 H20 119.7 .
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 .
C23 O22 C17 117.57(14) .
N28 C23 O22 119.00(17) .
N28 C23 C24 123.40(18) .
O22 C23 C24 117.59(16) .
C25 C24 C23 114.47(17) .
C25 C24 H24 122.8 .
C23 C24 H24 122.8 .
N26 C25 O35 117.68(17) .
N26 C25 C24 124.18(17) .
O35 C25 C24 118.08(16) .
C25 N26 C27 115.57(16) .
N28 C27 N26 125.92(17) .
N28 C27 C29 117.19(16) .
N26 C27 C29 116.88(17) .
C23 N28 C27 116.44(16) .
C30 C29 C34 119.64(18) .
C30 C29 C27 120.16(17) .
C34 C29 C27 120.20(18) .
C29 C30 C31 120.3(2) .
C29 C30 H30 119.9 .
C31 C30 H30 119.9 .
C32 C31 C30 119.6(2) .
C32 C31 H31 120.2 .
C30 C31 H31 120.2 .
C33 C32 C31 120.48(19) .
C33 C32 H32 119.8 .
C31 C32 H32 119.8 .
C32 C33 C34 120.7(2) .
C32 C33 H33 119.7 .
C34 C33 H33 119.7 .
C33 C34 C29 119.3(2) .
C33 C34 H34 120.4 .
C29 C34 H34 120.4 .
C25 O35 C36 116.09(14) .
C41 C36 C37 123.43(18) .
C41 C36 O35 119.37(17) .
C37 C36 O35 117.08(18) .
C38 C37 C36 116.96(18) .
C38 C37 H37 121.5 .
C36 C37 H37 121.5 .
C37 C38 C39 121.06(17) .
C37 C38 O13 126.41(18) 2_566
C39 C38 O13 112.52(16) 2_566
C40 C39 C38 120.79(17) .
C40 C39 H39 119.6 .
C38 C39 H39 119.6 .
C39 C40 C41 118.74(19) .
C39 C40 C42 120.31(18) .
C41 C40 C42 120.95(18) .
C36 C41 C40 118.99(18) .
C36 C41 H41 120.5 .
C40 C41 H41 120.5 .
C40 C42 H42A 109.5 .
C40 C42 H42B 109.5 .
H42A C42 H42B 109.5 .
C40 C42 H42C 109.5 .
H42A C42 H42C 109.5 .
H42B C42 H42C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.391(3) .
C1 C6 1.397(3) .
C1 H1 0.9500 .
C2 C3 1.385(3) .
C2 H2 0.9500 .
C3 C4 1.386(3) .
C3 H3 0.9500 .
C4 C5 1.388(3) .
C4 H4 0.9500 .
C5 C6 1.399(3) .
C5 H5 0.9500 .
C6 C7 1.483(3) .
C7 N8 1.339(2) .
C7 N12 1.344(3) .
N8 C9 1.332(2) .
C9 O14 1.365(2) .
C9 C10 1.375(3) .
C10 C11 1.387(3) .
C10 H10 0.9500 .
C11 N12 1.330(2) .
C11 O13 1.357(2) .
O13 C38 1.394(2) 2_566
O14 C15 1.397(2) .
C15 C20 1.383(3) .
C15 C16 1.392(3) .
C16 C17 1.376(3) .
C16 H16 0.9500 .
C17 C18 1.392(3) .
C17 O22 1.413(2) .
C18 C19 1.391(3) .
C18 H18 0.9500 .
C19 C20 1.388(3) .
C19 C21 1.510(3) .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
O22 C23 1.356(2) .
C23 N28 1.326(2) .
C23 C24 1.393(3) .
C24 C25 1.383(3) .
C24 H24 0.9500 .
C25 N26 1.332(2) .
C25 O35 1.362(2) .
N26 C27 1.339(3) .
C27 N28 1.337(3) .
C27 C29 1.484(3) .
C29 C30 1.392(3) .
C29 C34 1.401(3) .
C30 C31 1.392(3) .
C30 H30 0.9500 .
C31 C32 1.385(4) .
C31 H31 0.9500 .
C32 C33 1.374(4) .
C32 H32 0.9500 .
C33 C34 1.392(3) .
C33 H33 0.9500 .
C34 H34 0.9500 .
O35 C36 1.410(2) .
C36 C41 1.370(3) .
C36 C37 1.388(3) .
C37 C38 1.386(3) .
C37 H37 0.9500 .
C38 C39 1.390(3) .
C38 O13 1.394(2) 2_566
C39 C40 1.386(3) .
C39 H39 0.9500 .
C40 C41 1.402(3) .
C40 C42 1.507(3) .
C41 H41 0.9500 .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
