#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:13:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180417 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/86/7208645.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_7208645
loop_
_publ_author_name
'Li, Xiao-Yan'
'Yu, Ke-Ying'
'Zhao, Xiao-Li'
'Ma, Ming-Liang'
'Guo, Fang'
'Mi, Xian-Qiang'
'Jiang, Biao'
'Wen, Ke'
_publ_section_title
;
 Carboxylic acid-derived oxacalix[2]arene[2]pyrazine self-assembles into
 unprecedented diamondoid networks
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              7869
_journal_paper_doi               10.1039/c2ce25315a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C22 H12 N4 O8, (H2 O)'
_chemical_formula_sum            'C22 H14 N4 O9'
_chemical_formula_weight         478.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           34
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 -2n'
_symmetry_space_group_name_H-M   'P n n 2'
_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                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.7028(17)
_cell_length_b                   13.9075(14)
_cell_length_c                   5.0090(5)
_cell_measurement_reflns_used    7007
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1233.2(2)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13525
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.73
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
;
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0469
_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)+(0.1081P)²+0.1972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2037
_reflns_number_total             2121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25315a.txt
_cod_data_source_block           z3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pnn2
_cod_database_code               7208645
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z+1/2'
'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
O1 O 0.31405(10) -0.01455(16) 0.2797(5) 0.0488(6) Uani 1 1 d .
O2 O 0.50326(13) -0.23880(13) 0.1526(6) 0.0611(8) Uani 1 1 d .
O3 O 0.29982(11) 0.29774(15) -0.5279(5) 0.0469(6) Uani 1 1 d .
O4 O 0.21678(10) 0.17868(13) -0.4689(4) 0.0370(5) Uani 1 1 d .
H4A H 0.1932 0.2074 -0.5906 0.055 Uiso 1 1 calc R
N1 N 0.41439(12) -0.11944(15) 0.2156(4) 0.0324(5) Uani 1 1 d .
N2 N 0.35514(12) -0.22821(14) 0.6312(5) 0.0327(5) Uani 1 1 d .
C1 C 0.28050(13) 0.22462(17) -0.4185(5) 0.0276(5) Uani 1 1 d .
C2 C 0.32617(14) 0.17820(17) -0.2040(5) 0.0274(5) Uani 1 1 d .
C3 C 0.30288(13) 0.09514(19) -0.0740(5) 0.0320(6) Uani 1 1 d .
H3A H 0.2578 0.0633 -0.1267 0.038 Uiso 1 1 calc R
C4 C 0.34618(14) 0.05931(18) 0.1331(5) 0.0326(6) Uani 1 1 d .
C5 C 0.41262(14) 0.10172(19) 0.2132(5) 0.0331(6) Uani 1 1 d .
H5A H 0.4418 0.0760 0.3554 0.040 Uiso 1 1 calc R
C6 C 0.43519(15) 0.18408(18) 0.0765(6) 0.0364(7) Uani 1 1 d .
C7 C 0.39396(14) 0.22280(17) -0.1298(6) 0.0318(6) Uani 1 1 d .
H7A H 0.4111 0.2787 -0.2203 0.038 Uiso 1 1 calc R
C8 C 0.35272(13) -0.09443(19) 0.3472(6) 0.0308(6) Uani 1 1 d .
C9 C 0.32297(14) -0.14754(19) 0.5544(5) 0.0313(6) Uani 1 1 d .
H9A H 0.2787 -0.1256 0.6428 0.038 Uiso 1 1 calc R
C10 C 0.41718(16) -0.25686(19) 0.5027(7) 0.0389(7) Uani 1 1 d .
H10A H 0.4422 -0.3145 0.5533 0.047 Uiso 1 1 calc R
C11 C 0.44455(15) -0.20158(19) 0.2949(6) 0.0372(7) Uani 1 1 d .
O1W O 0.5000 0.0000 -0.2628(16) 0.130(2) Uani 1 2 d S
H1WA H 0.5006 -0.0493 -0.1624 0.156 Uiso 0.50 1 d PR
H1WB H 0.4994 0.0493 -0.1624 0.156 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
C8 O1 C4 122.4(2) . .
C11 O2 C6 122.4(2) . 2_655
C1 O4 H4A 109.5 . .
C8 N1 C11 114.3(2) . .
C9 N2 C10 118.0(2) . .
O3 C1 O4 124.3(2) . .
O3 C1 C2 122.6(2) . .
O4 C1 C2 113.0(2) . .
C3 C2 C7 119.9(2) . .
C3 C2 C1 122.5(2) . .
C7 C2 C1 117.6(2) . .
C4 C3 C2 119.1(2) . .
C4 C3 H3A 120.4 . .
C2 C3 H3A 120.4 . .
C5 C4 C3 122.6(2) . .
C5 C4 O1 121.0(2) . .
C3 C4 O1 115.9(2) . .
C4 C5 C6 117.0(2) . .
C4 C5 H5A 121.5 . .
C6 C5 H5A 121.5 . .
C7 C6 O2 114.2(2) . 2_655
C7 C6 C5 122.6(2) . .
O2 C6 C5 122.9(3) 2_655 .
C6 C7 C2 118.7(2) . .
C6 C7 H7A 120.6 . .
C2 C7 H7A 120.6 . .
N1 C8 O1 120.7(2) . .
N1 C8 C9 123.4(2) . .
O1 C8 C9 115.9(2) . .
N2 C9 C8 120.8(2) . .
N2 C9 H9A 119.6 . .
C8 C9 H9A 119.6 . .
N2 C10 C11 119.1(2) . .
N2 C10 H10A 120.5 . .
C11 C10 H10A 120.5 . .
N1 C11 O2 118.6(3) . .
N1 C11 C10 124.4(2) . .
O2 C11 C10 116.8(2) . .
H1WA O1W H1WB 107.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.348(3) .
O1 C4 1.385(3) .
O2 C11 1.363(3) .
O2 C6 1.383(3) 2_655
O3 C1 1.205(3) .
O4 C1 1.321(3) .
O4 H4A 0.8400 .
N1 C8 1.322(3) .
N1 C11 1.322(4) .
N2 C9 1.316(3) .
N2 C10 1.334(3) .
C1 C2 1.492(3) .
C2 C3 1.389(3) .
C2 C7 1.401(3) .
C3 C4 1.383(4) .
C3 H3A 0.9500 .
C4 C5 1.375(4) .
C5 C6 1.393(4) .
C5 H5A 0.9500 .
C6 C7 1.375(4) .
C6 O2 1.383(3) 2_655
C7 H7A 0.9500 .
C8 C9 1.378(4) .
C9 H9A 0.9500 .
C10 C11 1.382(4) .
C10 H10A 0.9500 .
O1W H1WA 0.8500 .
O1W H1WB 0.8500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O3 C1 C2 C3 178.5(3) . .
O4 C1 C2 C3 0.1(3) . .
O3 C1 C2 C7 0.1(4) . .
O4 C1 C2 C7 -178.3(2) . .
C7 C2 C3 C4 1.9(4) . .
C1 C2 C3 C4 -176.4(2) . .
C2 C3 C4 C5 -1.3(4) . .
C2 C3 C4 O1 170.5(2) . .
C8 O1 C4 C5 -53.6(4) . .
C8 O1 C4 C3 134.5(3) . .
C3 C4 C5 C6 0.3(4) . .
O1 C4 C5 C6 -171.1(2) . .
C4 C5 C6 C7 0.1(4) . .
C4 C5 C6 O2 173.7(3) . 2_655
O2 C6 C7 C2 -173.5(3) 2_655 .
C5 C6 C7 C2 0.6(4) . .
C3 C2 C7 C6 -1.6(4) . .
C1 C2 C7 C6 176.8(2) . .
C11 N1 C8 O1 -177.0(3) . .
C11 N1 C8 C9 1.6(4) . .
C4 O1 C8 N1 -20.0(4) . .
C4 O1 C8 C9 161.3(3) . .
C10 N2 C9 C8 0.0(4) . .
N1 C8 C9 N2 -0.6(4) . .
O1 C8 C9 N2 178.1(2) . .
C9 N2 C10 C11 -0.5(4) . .
C8 N1 C11 O2 172.9(2) . .
C8 N1 C11 C10 -2.2(4) . .
C6 O2 C11 N1 47.9(5) 2_655 .
C6 O2 C11 C10 -136.7(3) 2_655 .
N2 C10 C11 N1 1.7(5) . .
N2 C10 C11 O2 -173.4(3) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.067 149 46 ' '
2 0.500 0.500 -0.038 149 46 ' '
