#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/61/1506188.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_1506188
loop_
_publ_author_name
'Maes, Wouter'
'Van Rossom, Wim'
'Van Hecke, Kristof'
'Van Meervelt, Luc'
'Dehaen, Wim'
_publ_section_title
;
 Selective synthesis of functionalized thia- and
 oxacalix[2]arene[2]pyrimidines.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4161
_journal_page_last               4164
_journal_paper_doi               10.1021/ol0617446
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C34 H24 N4 O4'
_chemical_formula_sum            'C34 H24 N4 O4'
_chemical_formula_weight         552.57
_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                 129.9540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   33.2904(6)
_cell_length_b                   4.64990(10)
_cell_length_c                   21.8825(3)
_cell_measurement_temperature    100(2)
_cell_volume                     2596.60(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'omega and phi 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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11670
_diffrn_reflns_theta_full        70.86
_diffrn_reflns_theta_max         70.86
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.069
_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     191
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0410
_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)+(0.0637P)²+2.0491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2214
_reflns_number_total             2447
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0617446si20060717_031001.cif
_cod_data_source_block           wdb06
_cod_original_cell_volume        2596.61(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1506188
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
C1 C 0.17963(5) -0.3066(3) 0.31415(8) 0.0202(3) Uani 1 1 d .
C2 C 0.21949(6) -0.4020(3) 0.39167(8) 0.0263(3) Uani 1 1 d .
H2 H 0.2216 -0.3307 0.4343 0.032 Uiso 1 1 calc R
C3 C 0.25615(6) -0.6001(3) 0.40701(9) 0.0300(3) Uani 1 1 d .
H3 H 0.2832 -0.6642 0.4600 0.036 Uiso 1 1 calc R
C4 C 0.25325(6) -0.7043(3) 0.34497(9) 0.0283(3) Uani 1 1 d .
H4 H 0.2785 -0.8391 0.3555 0.034 Uiso 1 1 calc R
C5 C 0.21372(6) -0.6124(3) 0.26776(9) 0.0267(3) Uani 1 1 d .
H5 H 0.2118 -0.6853 0.2253 0.032 Uiso 1 1 calc R
C6 C 0.17680(5) -0.4137(3) 0.25194(8) 0.0234(3) Uani 1 1 d .
H6 H 0.1497 -0.3510 0.1988 0.028 Uiso 1 1 calc R
C7 C 0.14151(5) -0.0895(3) 0.29916(8) 0.0192(3) Uani 1 1 d .
C8 C 0.07206(5) 0.2007(3) 0.21342(8) 0.0194(3) Uani 1 1 d .
C9 C 0.07521(5) 0.3191(3) 0.27470(8) 0.0199(3) Uani 1 1 d .
H9 H 0.0520 0.4642 0.2661 0.024 Uiso 1 1 calc R
C10 C 0.11518(5) 0.2069(3) 0.34936(8) 0.0197(3) Uani 1 1 d .
C11 C 0.09049(5) 0.4295(3) 0.42057(7) 0.0196(3) Uani 1 1 d .
C12 C 0.10896(5) 0.6467(3) 0.47637(7) 0.0203(3) Uani 1 1 d .
H12 H 0.1431 0.7232 0.5038 0.024 Uiso 1 1 calc R
C13 C 0.07712(5) 0.7522(3) 0.49201(7) 0.0195(3) Uani 1 1 d .
C14 C -0.02645(5) 0.6421(3) 0.05107(8) 0.0197(3) Uani 1 1 d .
H14 H -0.0038 0.7163 0.0426 0.024 Uiso 1 1 calc R
C15 C -0.00944(5) 0.4245(3) 0.10601(7) 0.0192(3) Uani 1 1 d .
C16 C 0.04097(5) 0.3121(3) 0.37884(7) 0.0198(3) Uani 1 1 d .
H16 H 0.0290 0.1611 0.3415 0.024 Uiso 1 1 calc R
C17 C 0.09794(6) 0.9711(3) 0.55668(8) 0.0236(3) Uani 1 1 d .
H17A H 0.1062 0.8769 0.6036 0.035 Uiso 1 1 calc R
H17B H 0.0715 1.1204 0.5376 0.035 Uiso 1 1 calc R
H17C H 0.1298 1.0587 0.5710 0.035 Uiso 1 1 calc R
N1 N 0.10394(4) -0.0025(2) 0.22391(6) 0.0200(3) Uani 1 1 d .
N2 N 0.14803(4) 0.0046(2) 0.36302(6) 0.0206(3) Uani 1 1 d .
O1 O 0.03791(4) 0.2951(2) 0.13661(5) 0.0237(2) Uani 1 1 d .
O2 O 0.12759(4) 0.3078(2) 0.41819(5) 0.0249(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 0.0181 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_1
_geom_angle_site_symmetry_3
C2 C1 C6 119.29(13) . .
C2 C1 C7 119.72(12) . .
C6 C1 C7 120.98(12) . .
C3 C2 C1 120.51(14) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C4 C3 C2 119.88(14) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 120.14(13) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 120.29(14) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 119.91(13) . .
C5 C6 H6 120.0 . .
C1 C6 H6 120.0 . .
N1 C7 N2 125.49(12) . .
N1 C7 C1 117.89(12) . .
N2 C7 C1 116.62(11) . .
N1 C8 O1 112.60(11) . .
N1 C8 C9 123.99(12) . .
O1 C8 C9 123.27(12) . .
C10 C9 C8 114.13(12) . .
C10 C9 H9 122.9 . .
C8 C9 H9 122.9 . .
N2 C10 O2 112.01(11) . .
N2 C10 C9 124.23(12) . .
O2 C10 C9 123.59(12) . .
C16 C11 C12 122.31(12) . .
C16 C11 O2 121.70(12) . .
C12 C11 O2 115.29(11) . .
C11 C12 C13 119.64(12) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C12 C13 C14 118.93(12) . 2
C12 C13 C17 120.34(12) . .
C14 C13 C17 120.67(12) 2 .
C15 C14 C13 119.80(12) . 2
C15 C14 H14 120.1 . .
C13 C14 H14 120.1 2 .
C14 C15 C16 122.12(12) . 2
C14 C15 O1 116.04(11) . .
C16 C15 O1 121.18(12) 2 .
C11 C16 C15 117.15(12) . 2
C11 C16 H16 121.4 . .
C15 C16 H16 121.4 2 .
C13 C17 H17A 109.5 . .
C13 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C13 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C8 N1 C7 116.07(11) . .
C10 N2 C7 116.04(11) . .
C8 O1 C15 121.51(10) . .
C10 O2 C11 122.36(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3942(19) .
C1 C6 1.395(2) .
C1 C7 1.4843(18) .
C2 C3 1.387(2) .
C2 H2 0.9500 .
C3 C4 1.385(2) .
C3 H3 0.9500 .
C4 C5 1.383(2) .
C4 H4 0.9500 .
C5 C6 1.392(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 N1 1.3395(17) .
C7 N2 1.3423(17) .
C8 N1 1.3262(17) .
C8 O1 1.3624(16) .
C8 C9 1.3900(19) .
C9 C10 1.3856(19) .
C9 H9 0.9500 .
C10 N2 1.3230(17) .
C10 O2 1.3639(16) .
C11 C16 1.3843(19) .
C11 C12 1.3875(19) .
C11 O2 1.3895(16) .
C12 C13 1.3954(19) .
C12 H12 0.9500 .
C13 C14 1.3979(19) 2
C13 C17 1.5032(18) .
C14 C15 1.3838(19) .
C14 C13 1.3979(19) 2
C14 H14 0.9500 .
C15 C16 1.3899(19) 2
C15 O1 1.3927(16) .
C16 C15 1.3902(19) 2
C16 H16 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
