#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/66/1506637.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_1506637
loop_
_publ_author_name
'Katz, Jeffrey L.'
'Selby, Kevin J.'
'Conry, Rebecca R.'
_publ_section_title
;
 Single-step synthesis of D3h-symmetric bicyclooxacalixarenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3505
_journal_page_last               3507
_journal_paper_doi               10.1021/ol051180q
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C36 H24 N6 O20'
_chemical_formula_weight         860.61
_chemical_melting_point_gt       533
_chemical_name_common            'compound 4 acetone solvate'
_chemical_name_systematic
;
     4,6,16,18,31,33-hexanitro-2,8,14,20,29,35-
hexaoxabicyclocalix[4]arene
;
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3865(8)
_cell_length_b                   21.2279(17)
_cell_length_c                   18.8177(15)
_cell_measurement_reflns_used    8158
_cell_measurement_temperature    167(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.17
_cell_volume                     3748.4(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      167(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1268
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16695
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0559
_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)+(0.0913P)²+1.3214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1712
_reflns_number_gt                3752
_reflns_number_total             4489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051180qsi20050519_042848.cif
_cod_data_source_block           cif_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>533K' was changed to
'533' - it should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1506637
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 -0.31473(15) 0.31847(6) 0.42048(8) 0.0301(3) Uani 1 1 d .
C2 C -0.23107(16) 0.33120(7) 0.48012(8) 0.0317(3) Uani 1 1 d .
H2 H -0.2724 0.3471 0.5221 0.038 Uiso 1 1 calc R
C3 C -0.08706(16) 0.32044(6) 0.47761(7) 0.0299(3) Uani 1 1 d .
C4 C -0.02531(15) 0.29387(7) 0.41812(7) 0.0294(3) Uani 1 1 d .
C5 C 0.17431(14) 0.24947(7) 0.36450(7) 0.0291(3) Uani 1 1 d .
C6 C 0.17139(15) 0.18419(7) 0.36735(8) 0.0318(3) Uani 1 1 d .
H6 H 0.1315 0.1626 0.4063 0.038 Uiso 1 1 calc R
C7 C 0.22874(15) 0.15207(7) 0.31128(8) 0.0319(3) Uani 1 1 d .
C8 C 0.28807(15) 0.18170(7) 0.25369(8) 0.0318(3) Uani 1 1 d .
H8 H 0.3274 0.1584 0.2157 0.038 Uiso 1 1 calc R
C9 C 0.28746(14) 0.24713(7) 0.25398(7) 0.0289(3) Uani 1 1 d .
C10 C 0.23187(14) 0.28198(7) 0.30863(7) 0.0292(3) Uani 1 1 d .
H10 H 0.2332 0.3267 0.3078 0.035 Uiso 1 1 calc R
C11 C 0.11140(16) 0.05740(7) 0.28259(8) 0.0346(3) Uani 1 1 d .
C12 C 0.10903(18) -0.00828(7) 0.28284(8) 0.0373(4) Uani 1 1 d .
C13 C 0.0000 -0.04117(10) 0.2500 0.0397(5) Uani 1 2 d S
H13 H 0.0000 -0.0859 0.2500 0.048 Uiso 1 2 calc SR
C14 C 0.0000 0.08975(10) 0.2500 0.0366(5) Uani 1 2 d S
H11 H 0.0000 0.1345 0.2500 0.044 Uiso 1 2 calc SR
C15 C 0.25722(15) 0.29173(6) 0.14013(8) 0.0289(3) Uani 1 1 d .
C16 C 0.11243(15) 0.27823(7) 0.13990(8) 0.0310(3) Uani 1 1 d .
H16 H 0.0726 0.2581 0.1799 0.037 Uiso 1 1 calc R
O1 O 0.11740(11) 0.28380(5) 0.42059(6) 0.0340(3) Uani 1 1 d .
O2 O 0.22692(12) 0.08615(5) 0.31325(6) 0.0401(3) Uani 1 1 d .
O3 O 0.34594(10) 0.27890(5) 0.19639(5) 0.0334(3) Uani 1 1 d .
O4 O -0.52017(12) 0.35922(6) 0.36987(6) 0.0417(3) Uani 1 1 d .
O5 O -0.52627(15) 0.32683(9) 0.47810(8) 0.0652(5) Uani 1 1 d .
O6 O 0.10045(15) 0.37403(7) 0.52986(7) 0.0540(4) Uani 1 1 d .
O7 O -0.02912(16) 0.31681(8) 0.59690(7) 0.0642(5) Uani 1 1 d .
O8 O 0.2513(2) -0.03135(7) 0.37982(8) 0.0680(5) Uani 1 1 d .
O9 O 0.28256(17) -0.08425(6) 0.28401(9) 0.0624(4) Uani 1 1 d .
N1 N -0.46459(13) 0.33561(6) 0.42271(7) 0.0346(3) Uani 1 1 d .
N2 N 0.00172(14) 0.33843(6) 0.53960(7) 0.0349(3) Uani 1 1 d .
N3 N 0.22393(17) -0.04349(6) 0.31831(8) 0.0452(4) Uani 1 1 d .
C17 C 0.4001(8) -0.0046(4) 0.1283(5) 0.226(4) Uani 1 1 d .
H17A H 0.4713 -0.0013 0.0912 0.339 Uiso 1 1 calc R
H17B H 0.3822 -0.0491 0.1386 0.339 Uiso 1 1 calc R
H17C H 0.4357 0.0166 0.1715 0.339 Uiso 1 1 calc R
C18 C 0.2687(4) 0.02514(12) 0.10392(16) 0.0871(9) Uani 1 1 d .
C19 C 0.1841(9) -0.0110(3) 0.0546(3) 0.183(3) Uani 1 1 d .
H19A H 0.0902 0.0087 0.0483 0.274 Uiso 1 1 calc R
H19B H 0.1727 -0.0539 0.0729 0.274 Uiso 1 1 calc R
H19C H 0.2314 -0.0126 0.0088 0.274 Uiso 1 1 calc R
O10 O 0.2348(3) 0.07744(10) 0.11919(11) 0.1043(8) 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 0.0033 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
C2 C1 C15 121.38(13) . 2
C2 C1 N1 117.32(13) . .
C15 C1 N1 121.28(13) 2 .
C3 C2 C1 118.72(14) . .
C2 C3 C4 121.64(13) . .
C2 C3 N2 118.03(13) . .
C4 C3 N2 120.33(13) . .
O1 C4 C16 123.47(13) . 2
O1 C4 C3 117.81(12) . .
C16 C4 C3 118.71(13) 2 .
C10 C5 C6 122.55(13) . .
C10 C5 O1 118.58(13) . .
C6 C5 O1 118.87(13) . .
C7 C6 C5 117.18(13) . .
C6 C7 C8 123.23(13) . .
C6 C7 O2 118.01(13) . .
C8 C7 O2 118.76(13) . .
C7 C8 C9 116.77(13) . .
C10 C9 C8 122.73(13) . .
C10 C9 O3 118.77(12) . .
C8 C9 O3 118.50(13) . .
C5 C10 C9 117.54(13) . .
O2 C11 C14 123.50(14) . .
O2 C11 C12 117.37(13) . .
C14 C11 C12 119.11(15) . .
C13 C12 C11 121.23(15) . .
C13 C12 N3 118.65(14) . .
C11 C12 N3 120.11(14) . .
C12 C13 C12 118.9(2) . 2
C11 C14 C11 120.40(19) 2 .
O3 C15 C16 122.84(13) . .
O3 C15 C1 118.48(12) . 2
C16 C15 C1 118.66(13) . 2
C4 C16 C15 120.71(13) 2 .
C4 O1 C5 116.82(10) . .
C11 O2 C7 116.57(11) . .
C15 O3 C9 117.09(10) . .
O5 N1 O4 123.89(14) . .
O5 N1 C1 117.79(13) . .
O4 N1 C1 118.30(12) . .
O6 N2 O7 124.71(14) . .
O6 N2 C3 117.59(13) . .
O7 N2 C3 117.70(13) . .
O8 N3 O9 124.81(16) . .
O8 N3 C12 117.82(15) . .
O9 N3 C12 117.34(15) . .
O10 C18 C19 120.5(5) . .
O10 C18 C17 124.0(5) . .
C19 C18 C17 115.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.381(2) .
C1 C15 1.394(2) 2
C1 N1 1.4546(19) .
C2 C3 1.373(2) .
C3 C4 1.392(2) .
C3 N2 1.4675(18) .
C4 O1 1.3562(17) .
C4 C16 1.3885(19) 2
C5 C10 1.379(2) .
C5 C6 1.387(2) .
C5 O1 1.3993(17) .
C6 C7 1.377(2) .
C7 C8 1.382(2) .
C7 O2 1.3998(18) .
C8 C9 1.389(2) .
C9 C10 1.380(2) .
C9 O3 1.3999(16) .
C11 O2 1.3605(19) .
C11 C14 1.3820(18) .
C11 C12 1.394(2) .
C12 C13 1.373(2) .
C12 N3 1.460(2) .
C13 C12 1.373(2) 2
C14 C11 1.3820(18) 2
C15 O3 1.3585(17) .
C15 C16 1.389(2) .
C15 C1 1.394(2) 2
C16 C4 1.3885(19) 2
O4 N1 1.2194(17) .
O5 N1 1.2188(18) .
O6 N2 1.2133(18) .
O7 N2 1.2133(18) .
O8 N3 1.207(2) .
O9 N3 1.219(2) .
C17 C18 1.450(7) .
C18 O10 1.192(3) .
C18 C19 1.430(7) .
