#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/43/2004319.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_2004319
loop_
_publ_author_name
'Klei, H. E.'
'Callegari, E.'
'Edwards, J. M.'
'Kelly, J. A.'
_publ_section_title
8,16-Methano-16H-dinaphtho[2,1-d:1',2'-g][1,3]dioxocine-2,14-diol
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2621
_journal_page_last               2624
_journal_paper_doi               10.1107/S0108270195003520
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C23 H16 O4'
_chemical_formula_sum            'C23 H16 O4'
_chemical_formula_weight         356.40
_chemical_melting_point          510
_chemical_name_systematic
;
8,16-Methano-16H-dinaphtho[2,1-d:1',2'-g][1,3]dioxocin-2,14-diol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.93(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.458(2)
_cell_length_b                   16.969(3)
_cell_length_c                   9.739(2)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      4.2
_cell_volume                     1670.0(6)
_computing_cell_refinement       'Siemens SHELXTL-Plus (VMS)'
_computing_data_collection       'Siemens SHELXTL-Plus (VMS)'
_computing_data_reduction        'Siemens SHELXTL-Plus (VMS)'
_computing_molecular_graphics    'Biosym Insight II/Discover'
_computing_publication_material  'Microsoft Word for Windows 6.0'
_computing_structure_refinement  'Siemens SHELXTL-Plus (VMS)'
_computing_structure_solution    'Siemens SHELXTL-Plus (VMS)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Siemens R3m/V diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1708
_diffrn_reflns_theta_max         50
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       '\c = 0.017(2)'
_refine_ls_extinction_method     'F^*^ = F[1 + 0.002\cF²/sin(2θ)]^-1/4^'
_refine_ls_goodness_of_fit_obs   1.25
_refine_ls_hydrogen_treatment
'noref except for the positions of H18 and H27'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         1283
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_obs          0.0561
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(σ²(F)+0.0021F²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0796
_refine_ls_wR_factor_obs         0.0730
_reflns_number_observed          1283
_reflns_number_total             1708
_reflns_observed_criterion       '[F > 3\s(F)]'
_cod_data_source_file            sz1012.cif
_cod_data_source_block           h001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/(\s^2^(F)+0.0021F^2^)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/(\s^2^(F)+0.0021F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2004319
loop_
_symmetry_equiv_pos_as_xyz
' x,     y,     z'
'-x, 1/2+y, 1/2-z'
'-x,    -y,    -z'
' x, 1/2-y, 1/2+z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_type_symbol
O1 .2782(3) .9247(2) .1933(4) .0580(10) Uij O
C2 .3249(4) .8495(3) .2383(5) .039(2) Uij C
C3 .2684(4) .7816(2) .1741(4) .031(2) Uij C
C4 .1421(4) .7891(2) .0543(4) .034(2) Uij C
C5 .1519(5) .8648(2) -.0273(5) .043(2) Uij C
C6 .1662(5) .9316(3) .0745(5) .047(2) Uij C
O7 .0521(3) .9398(2) .1291(3) .0490(10) Uij O
C8 -.0145(5) .8713(3) .1500(5) .038(2) Uij C
C9 .0209(4) .7972(2) .1151(4) .031(2) Uij C
C10 -.0600(4) .7334(2) .1387(4) .035(2) Uij C
C11 -0.1632(4) .7472(3) .2062(5) .040(2) Uij C
C12 -0.1923(5) .8252(3) .2393(5) .048(2) Uij C
C13 -0.1209(5) .8864(3) .2088(5) .046(2) Uij C
C14 -.0405(5) .6542(3) .0988(5) .045(2) Uij C
C15 -0.1176(5) .5947(3) .1280(6) .060(2) Uij C
C16 -0.2167(5) .6077(3) .1982(6) .069(3) Uij C
C17 -0.2385(5) .6830(3) .2361(6) .063(2) Uij C
O18 -0.1003(4) .5172(2) .0880(5) .083(2) Uij O
C19 .4340(5) .8502(3) .3582(6) .054(2) Uij C
C20 .4882(5) .7811(3) .4135(5) .053(2) Uij C
C21 .4412(4) .7088(3) .3490(5) .043(2) Uij C
C22 .3336(4) .7081(3) .2229(5) .034(2) Uij C
C23 .5019(5) .6356(3) .4017(5) .054(2) Uij C
C24 .4630(5) .5661(3) .3315(6) .057(2) Uij C
C25 .3623(5) .5667(3) .2054(5) .045(2) Uij C
C26 .2987(4) .6349(2) .1528(5) .035(2) Uij C
O27 .3329(4) .4956(2) .1386(4) .065(2) Uij O
H4 .1326 .7432 -0.0051 .080 Uiso H
H5A .0732 .8715 -0.1031 .080 Uiso H
H5B .2275 .8625 -0.0659 .080 Uiso H
H6 .1770 .9770 .0198 .080 Uiso H
H12 -0.2629 .8349 .2835 .080 Uiso H
H13 -0.1429 .9395 .2274 .080 Uiso H
H16 -0.2681 .5646 .2194 .080 Uiso H
H17 -0.3065 .6927 .2840 .080 Uiso H
H19 .4696 .8992 .4004 .080 Uiso H
H20 .5598 .7813 .4981 .080 Uiso H
H23 .5714 .6351 .4881 .080 Uiso H
H24 .5045 .5174 .3687 .080 Uiso H
H14 .0271 .6426 .0512 .080 Uiso H
H26 .2290 .6332 .0667 .080 Uiso H
H18 -.072(6) .508(4) .021(7) .080 Uiso H
H27 .256(6) .496(3) .063(6) .080 Uiso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 SHELXTL-Plus_(Sheldrick,_1990)
H 0 0 SHELXTL-Plus_(Sheldrick,_1990)
O 0.047 0.032 SHELXTL-Plus_(Sheldrick,_1990)
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 -2
2 0 0
1 2 2
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
C4 C3 C22 124.5(3) yes
O1 C2 C19 113.4(4) yes
C3 C4 C9 110.5(3) yes
C4 C9 C10 125.2(4) yes
O7 C8 C13 112.7(4) yes
O1 C6 O7 107.3(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.395(5) no
O1 C6 1.423(5) no
C2 C3 1.371(6) no
C2 C19 1.406(6) no
C3 C4 1.526(5) no
C3 C22 1.441(6) no
C4 C5 1.528(6) no
C4 C9 1.537(6) no
C5 C6 1.488(6) no
C6 O7 1.432(6) no
O7 C8 1.398(5) no
C8 C9 1.377(6) no
C8 C13 1.400(7) no
C9 C10 1.427(6) no
C10 C11 1.421(7) no
C10 C14 1.429(6) no
C11 C12 1.414(7) no
C11 C17 1.418(7) no
C12 C13 1.356(7) no
C14 C15 1.366(7) no
C15 C16 1.398(9) no
C15 O18 1.397(6) no
C16 C17 1.365(8) no
C19 C20 1.352(7) no
C20 C21 1.408(7) no
C21 C22 1.436(5) no
C21 C23 1.428(7) no
C22 C26 1.420(6) no
C23 C24 1.372(7) no
C24 C25 1.396(6) no
C25 C26 1.366(6) no
C25 O27 1.368(6) no
O18 H18 0.800(7) no
O27 H27 0.943(5) no
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
C22 C3 C4 C9 98.8(5) yes
O1 C2 C3 C22 174.4(5) yes
C6 O1 C2 C19 -178.7(5) yes
C2 O1 C6 C5 -28.1(6) yes
O1 C2 C3 C4 -4.7(7) yes
C6 O1 C2 C3 0.1(7) yes
C3 C4 C9 C10 -93.3(4) yes
O7 C8 C9 C10 -177.9(3) yes
C6 O7 C8 C13 177.6(3) yes
C5 C6 O7 C8 34.0(5) yes
O7 C8 C9 C4 1.8(6) yes
C6 O7 C8 C9 -2.8(5) yes
C2 C3 C22 C26 -169.9(5) yes
C4 C3 C22 C26 9.1(7) yes
C20 C21 C22 C26 173.4(5) yes
C23 C21 C22 C3 177.0(5) yes
C8 C9 C10 C14 175.7(4) yes
C4 C9 C10 C14 -4.1(6) yes
C14 C10 C11 C12 -175.9(4) yes
C9 C10 C11 C17 -176.6(4) yes
C19 C2 C3 C22 -7.0(8) yes
C3 C2 C19 C20 0.7(9) yes
C2 C19 C20 C21 3.1(9) yes
C19 C20 C21 C23 176.7(5) yes
C20 C21 C23 C24 -174.4(5) yes
C21 C23 C24 C25 0.3(9) yes
C23 C24 C25 C26 -2.2(9) yes
C24 C25 C26 C22 1.0(8) yes
C3 C22 C26 C25 -178.7(5) yes
C13 C8 C9 C10 1.6(6) yes
C9 C8 C13 C12 2.5(6) yes
C11 C12 C13 C8 -2.8(6) yes
C17 C11 C12 C13 -179.2(4) yes
C12 C11 C17 C16 176.5(4) yes
C15 C16 C17 C11 -0.1(7) yes
C14 C15 C16 C17 1.3(8) yes
C10 C14 C15 C16 -0.6(7) yes
C9 C10 C14 C15 177.7(4) yes
C21 C22 C26 H26 -178.0(3) yes
C24 C25 C26 H26 -179.0(4) yes
C11 C10 C14 H14 178.7(2) yes
H14 C14 C15 C16 179.4(4) yes
