#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202543.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202543
loop_
_publ_author_name
'H\"okelek, Tuncer'
'Bilge, Selen'
'K\?il\?i\,c, Zeynel'
_publ_section_title
;
 1,15-Diaza-3,4:12,13-dibenzo-5,8,11-trioxacycloheptadecane hemihydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1607
_journal_page_last               o1609
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C20 H26 N2 O3, 0.5H2 O'
_chemical_formula_moiety         'C20 H26 N2 O3, 0.5H2 O'
_chemical_formula_sum            'C20 H27 N2 O3.5'
_chemical_formula_weight         351.44
_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                 116.768(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.457(2)
_cell_length_b                   7.5165(12)
_cell_length_c                   23.865(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      10
_cell_volume                     3917.0(8)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadle, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled \w'
_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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3856
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rod shaped'
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.242
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0516
_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/[\s^2^(Fo^2^)+(0.0951P)^2^+0.1096P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1686
_reflns_number_gt                1752
_reflns_number_total             3786
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    cm6055.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_database_code               2202543
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O26 0.0000 0.8760(6) 0.2500 0.130 Uani d S 1 O
H8 0.1216(14) 0.075(4) 0.3627(13) 0.071(9) Uiso d . 1 H
H26 0.0316(12) 0.916(4) 0.2405(12) 0.075 Uiso d . 1 H
H11 0.1465(13) 0.321(3) 0.3299(14) 0.075 Uiso d D 1 H
H2 0.2605(15) 0.027(4) 0.5687(13) 0.072(9) Uiso d . 1 H
O19 0.17834(8) 0.2592(2) 0.24813(8) 0.0699(5) Uani d . 1 O
O22 0.22177(9) 0.0241(2) 0.35207(9) 0.0690(6) Uani d . 1 O
O25 0.20186(8) -0.0789(2) 0.45371(9) 0.0676(5) Uani d . 1 O
N11 0.13632(13) 0.4231(4) 0.33408(12) 0.0792(8) Uani d D 1 N
N8 0.08400(13) 0.0684(4) 0.35653(11) 0.0755(8) Uani d . 1 N
C6 0.11695(14) -0.0064(4) 0.46899(13) 0.0679(8) Uani d . 1 C
C1 0.18040(14) -0.0154(3) 0.49357(12) 0.0599(7) Uani d . 1 C
C13 0.11233(13) 0.5043(4) 0.22189(13) 0.0635(7) Uani d . 1 C
C2 0.21807(18) 0.0393(4) 0.55449(14) 0.0701(8) Uani d . 1 C
C18 0.13043(12) 0.3531(4) 0.20192(13) 0.0624(7) Uani d . 1 C
C23 0.26748(15) -0.0654(4) 0.40503(16) 0.0800(9) Uani d . 1 C
H23A 0.3078 -0.0298 0.4107 0.096 Uiso calc R 1 H
H23B 0.2636 -0.1928 0.3980 0.096 Uiso calc R 1 H
C17 0.10319(15) 0.3043(5) 0.13910(14) 0.0806(9) Uani d . 1 C
H17 0.1157 0.2020 0.1262 0.097 Uiso calc R 1 H
C3 0.1928(2) 0.1020(4) 0.59099(15) 0.0855(10) Uani d . 1 C
H3 0.2182 0.1385 0.6318 0.103 Uiso calc R 1 H
C12 0.14166(15) 0.5542(4) 0.29084(14) 0.0731(8) Uani d . 1 C
H12A 0.1848 0.5764 0.3042 0.088 Uiso calc R 1 H
H12B 0.1236 0.6650 0.2951 0.088 Uiso calc R 1 H
C24 0.26073(14) -0.0211(4) 0.46244(14) 0.0720(8) Uani d . 1 C
H24A 0.2925 -0.0800 0.4986 0.086 Uiso calc R 1 H
H24B 0.2648 0.1063 0.4697 0.086 Uiso calc R 1 H
C20 0.17801(17) 0.0706(4) 0.24199(15) 0.0825(9) Uani d . 1 C
H20A 0.1818 0.0386 0.2045 0.099 Uiso calc R 1 H
H20B 0.1398 0.0222 0.2385 0.099 Uiso calc R 1 H
C21 0.23002(17) -0.0026(4) 0.29805(16) 0.0828(10) Uani d . 1 C
H21A 0.2338 -0.1289 0.2922 0.099 Uiso calc R 1 H
H21B 0.2676 0.0549 0.3035 0.099 Uiso calc R 1 H
C4 0.1304(2) 0.1123(4) 0.56853(18) 0.0923(11) Uani d . 1 C
H4 0.1135 0.1550 0.5939 0.111 Uiso calc R 1 H
C14 0.06591(15) 0.6064(4) 0.17652(15) 0.0784(9) Uani d . 1 C
H14 0.0530 0.7094 0.1886 0.094 Uiso calc R 1 H
C15 0.03892(17) 0.5581(5) 0.11436(16) 0.0892(10) Uani d . 1 C
H15 0.0080 0.6280 0.0848 0.107 Uiso calc R 1 H
C7 0.07780(15) -0.0545(5) 0.40125(14) 0.0838(10) Uani d . 1 C
H7A 0.0886 -0.1734 0.3939 0.101 Uiso calc R 1 H
H7B 0.0353 -0.0569 0.3933 0.101 Uiso calc R 1 H
C9 0.06774(14) 0.2495(5) 0.36249(13) 0.0789(9) Uani d . 1 C
H9A 0.0936 0.2905 0.4049 0.095 Uiso calc R 1 H
H9B 0.0257 0.2521 0.3561 0.095 Uiso calc R 1 H
C10 0.07427(15) 0.3773(5) 0.31624(14) 0.0877(10) Uani d . 1 C
H10A 0.0569 0.3227 0.2750 0.105 Uiso calc R 1 H
H10B 0.0512 0.4847 0.3134 0.105 Uiso calc R 1 H
C5 0.09277(17) 0.0578(5) 0.50723(16) 0.0892(10) Uani d . 1 C
H5 0.0505 0.0649 0.4918 0.107 Uiso calc R 1 H
C16 0.05732(17) 0.4094(6) 0.09617(15) 0.0928(11) Uani d . 1 C
H16 0.0388 0.3773 0.0540 0.111 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O26 0.160 0.106 0.108 0.000 0.045 0.000
O19 0.0786(12) 0.0583(12) 0.0750(12) -0.0008(10) 0.0367(10) -0.0041(10)
O22 0.0841(13) 0.0540(11) 0.0787(13) 0.0185(10) 0.0453(11) 0.0129(9)
O25 0.0740(12) 0.0548(11) 0.0687(11) -0.0085(9) 0.0275(10) 0.0004(9)
N11 0.0848(19) 0.0798(19) 0.0669(14) -0.0089(15) 0.0289(13) -0.0060(15)
N8 0.0636(17) 0.098(2) 0.0574(14) -0.0029(15) 0.0209(13) 0.0058(13)
C6 0.076(2) 0.0645(19) 0.0623(17) -0.0058(14) 0.0298(16) 0.0166(14)
C1 0.079(2) 0.0407(15) 0.0523(15) -0.0069(13) 0.0231(15) 0.0073(12)
C13 0.0657(17) 0.0566(18) 0.0700(18) -0.0097(14) 0.0322(15) 0.0017(15)
C2 0.088(2) 0.0511(17) 0.0590(19) -0.0050(16) 0.0217(18) 0.0131(14)
C18 0.0663(17) 0.0618(18) 0.0652(17) -0.0063(14) 0.0350(15) 0.0024(14)
C23 0.087(2) 0.0565(18) 0.104(2) 0.0207(16) 0.0496(19) 0.0217(17)
C17 0.096(2) 0.086(2) 0.0712(19) -0.0100(19) 0.0477(18) -0.0094(18)
C3 0.134(3) 0.0565(19) 0.0612(19) -0.0072(19) 0.040(2) 0.0084(14)
C12 0.0817(19) 0.0604(18) 0.0755(19) -0.0158(15) 0.0340(16) -0.0066(15)
C24 0.073(2) 0.0533(17) 0.0777(19) 0.0032(14) 0.0238(16) 0.0147(15)
C20 0.116(3) 0.059(2) 0.083(2) 0.0009(18) 0.054(2) -0.0085(16)
C21 0.115(3) 0.0593(19) 0.099(2) 0.0166(18) 0.071(2) 0.0047(17)
C4 0.140(4) 0.075(2) 0.083(3) 0.016(2) 0.068(3) 0.0194(18)
C14 0.088(2) 0.070(2) 0.079(2) -0.0028(17) 0.0394(18) 0.0085(17)
C15 0.090(2) 0.094(3) 0.075(2) 0.001(2) 0.0309(19) 0.019(2)
C7 0.076(2) 0.091(2) 0.071(2) -0.0205(17) 0.0210(17) 0.0056(17)
C9 0.0732(18) 0.100(3) 0.0660(17) 0.0006(18) 0.0338(15) 0.0096(17)
C10 0.077(2) 0.119(3) 0.0607(17) -0.005(2) 0.0257(16) 0.0112(18)
C5 0.091(2) 0.099(3) 0.084(2) 0.0061(19) 0.045(2) 0.032(2)
C16 0.099(3) 0.115(3) 0.0592(18) -0.013(2) 0.0314(19) 0.006(2)
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_publ_flag
C18 O19 C20 117.5(2) yes
C21 O22 C23 111.6(2) yes
C1 O25 C24 118.2(2) yes
C10 N11 C12 111.8(2) yes
C10 N11 H11 94(2) ?
C12 N11 H11 114(2) ?
C9 N8 C7 113.5(3) yes
C9 N8 H8 104(2) ?
C7 N8 H8 111.3(19) ?
C5 C6 C1 117.8(3) ?
C5 C6 C7 122.7(3) ?
C1 C6 C7 119.3(3) yes
O25 C1 C2 123.5(3) ?
O25 C1 C6 115.4(2) yes
C2 C1 C6 121.0(3) ?
C18 C13 C14 117.4(3) ?
C18 C13 C12 120.7(3) yes
C14 C13 C12 121.9(3) ?
C3 C2 C1 119.7(4) ?
C3 C2 H2 123.2(17) ?
C1 C2 H2 117.0(17) ?
C13 C18 O19 115.6(2) yes
C13 C18 C17 121.2(3) ?
O19 C18 C17 123.1(3) ?
O22 C23 C24 110.1(2) yes
O22 C23 H23A 109.6 ?
C24 C23 H23A 109.6 ?
O22 C23 H23B 109.6 ?
C24 C23 H23B 109.6 ?
H23A C23 H23B 108.2 ?
C16 C17 C18 119.0(3) ?
C16 C17 H17 120.5 ?
C18 C17 H17 120.5 ?
C2 C3 C4 121.0(3) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
N11 C12 C13 116.5(2) yes
N11 C12 H12A 108.2 ?
C13 C12 H12A 108.2 ?
N11 C12 H12B 108.2 ?
C13 C12 H12B 108.2 ?
H12A C12 H12B 107.3 ?
O25 C24 C23 108.7(2) yes
O25 C24 H24A 110.0 ?
C23 C24 H24A 110.0 ?
O25 C24 H24B 110.0 ?
C23 C24 H24B 110.0 ?
H24A C24 H24B 108.3 ?
O19 C20 C21 108.4(3) yes
O19 C20 H20A 110.0 ?
C21 C20 H20A 110.0 ?
O19 C20 H20B 110.0 ?
C21 C20 H20B 110.0 ?
H20A C20 H20B 108.4 ?
O22 C21 C20 110.9(2) yes
O22 C21 H21A 109.5 ?
C20 C21 H21A 109.5 ?
O22 C21 H21B 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 108.0 ?
C3 C4 C5 119.1(3) ?
C3 C4 H4 120.5 ?
C5 C4 H4 120.5 ?
C15 C14 C13 121.4(3) ?
C15 C14 H14 119.3 ?
C13 C14 H14 119.3 ?
C16 C15 C14 120.0(3) ?
C16 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
N8 C7 C6 113.9(2) yes
N8 C7 H7A 108.8 ?
C6 C7 H7A 108.8 ?
N8 C7 H7B 108.8 ?
C6 C7 H7B 108.8 ?
H7A C7 H7B 107.7 ?
N8 C9 C10 113.5(3) yes
N8 C9 H9A 108.9 ?
C10 C9 H9A 108.9 ?
N8 C9 H9B 108.9 ?
C10 C9 H9B 108.9 ?
H9A C9 H9B 107.7 ?
N11 C10 C9 112.4(3) yes
N11 C10 H10A 109.1 ?
C9 C10 H10A 109.1 ?
N11 C10 H10B 109.1 ?
C9 C10 H10B 109.1 ?
H10A C10 H10B 107.8 ?
C6 C5 C4 121.3(3) ?
C6 C5 H5 119.3 ?
C4 C5 H5 119.3 ?
C15 C16 C17 121.0(3) ?
C15 C16 H16 119.5 ?
C17 C16 H16 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O26 H26 0.95(3) ?
O19 C18 1.387(3) yes
O19 C20 1.425(3) yes
O22 C21 1.406(3) yes
O22 C23 1.424(4) yes
O25 C1 1.363(3) yes
O25 C24 1.427(4) yes
N11 C10 1.422(4) yes
N11 C12 1.475(4) yes
N11 H11 0.829(17) ?
N8 C9 1.443(4) yes
N8 C7 1.470(4) yes
N8 H8 0.86(3) ?
C6 C5 1.379(4) ?
C6 C1 1.392(4) yes
C6 C7 1.506(4) yes
C1 C2 1.387(4) ?
C13 C18 1.380(4) yes
C13 C14 1.394(4) ?
C13 C12 1.516(4) yes
C2 C3 1.359(5) ?
C2 H2 0.94(3) ?
C18 C17 1.388(4) ?
C23 C24 1.490(4) yes
C23 H23A 0.9700 ?
C23 H23B 0.9700 ?
C17 C16 1.377(5) ?
C17 H17 0.9300 ?
C3 C4 1.374(5) ?
C3 H3 0.9300 ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C24 H24A 0.9700 ?
C24 H24B 0.9700 ?
C20 C21 1.475(5) yes
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C4 C5 1.393(5) ?
C4 H4 0.9300 ?
C14 C15 1.373(5) ?
C14 H14 0.9300 ?
C15 C16 1.348(5) ?
C15 H15 0.9300 ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C9 C10 1.525(4) yes
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C5 H5 0.9300 ?
C16 H16 0.9300 ?
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_publ_flag
C24 O25 C1 C2 -27.1(3) yes
C24 O25 C1 C6 152.2(2) yes
C5 C6 C1 O25 -179.7(2) yes
C7 C6 C1 O25 -3.7(4) yes
C5 C6 C1 C2 -0.3(4) ?
C7 C6 C1 C2 175.6(3) ?
O25 C1 C2 C3 179.6(2) ?
C6 C1 C2 C3 0.3(4) ?
C14 C13 C18 O19 177.5(2) ?
C12 C13 C18 O19 -3.3(4) yes
C14 C13 C18 C17 -0.4(4) ?
C12 C13 C18 C17 178.8(2) ?
C20 O19 C18 C13 146.5(3) yes
C20 O19 C18 C17 -35.6(4) yes
C21 O22 C23 C24 174.9(2) yes
C13 C18 C17 C16 0.1(4) ?
O19 C18 C17 C16 -177.7(3) ?
C1 C2 C3 C4 0.0(4) ?
C10 N11 C12 C13 -55.5(4) yes
C18 C13 C12 N11 -59.3(4) yes
C14 C13 C12 N11 119.8(3) yes
C1 O25 C24 C23 -164.8(2) yes
O22 C23 C24 O25 60.9(3) yes
C18 O19 C20 C21 -175.8(2) yes
C23 O22 C21 C20 172.5(3) yes
O19 C20 C21 O22 66.6(3) yes
C2 C3 C4 C5 -0.2(5) ?
C18 C13 C14 C15 0.4(4) ?
C12 C13 C14 C15 -178.8(3) ?
C13 C14 C15 C16 -0.1(5) ?
C9 N8 C7 C6 -59.7(4) yes
C5 C6 C7 N8 109.5(3) yes
C1 C6 C7 N8 -66.2(4) yes
C7 N8 C9 C10 179.9(2) yes
C12 N11 C10 C9 -176.9(3) yes
N8 C9 C10 N11 -76.5(4) yes
C1 C6 C5 C4 0.1(5) ?
C7 C6 C5 C4 -175.7(3) ?
C3 C4 C5 C6 0.2(5) ?
C14 C15 C16 C17 -0.2(5) ?
C18 C17 C16 C15 0.2(5) ?