#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006551.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_2006551
loop_
_publ_author_name
'Muneer, M.'
'Rath, Nigam P.'
'George, M. V.'
_publ_section_title
;
 Photoproducts Derived from 9-Substituted Dibenzobarrelenes
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1475
_journal_page_last               1478
_journal_paper_doi               10.1107/S0108270197006343
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C31 H22 O3'
_chemical_formula_weight         442.49
_chemical_name_systematic
;
 ?
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.8270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.81440(10)
_cell_length_b                   9.14810(10)
_cell_length_c                   27.8748(3)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.0
_cell_measurement_theta_min      2.0
_cell_volume                     2226.74(4)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1995)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Siemens SMART'
_diffrn_measurement_method       'ω 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  0.045
_diffrn_reflns_av_sigmaI/netI    0.040
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15746
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.01
_refine_ls_goodness_of_fit_obs   1.07
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_restrained_S_obs      1.07
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_obs          .048
_refine_ls_shift/esd_max         0.0
_refine_ls_shift/esd_mean        0.0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0495P)²+0.7533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.128
_refine_ls_wR_factor_obs         .104
_reflns_number_observed          2896
_reflns_number_total             4380
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            bk1278.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.7533P] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0495P)^2^+0.7533P] where P=(Fo^2^+2Fc^2^)/3'.

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               2006551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .4328(2) .0169(2) .17353(5) .0567(4) Uani d . 1 . O
O2 .1492(2) .0873(2) .06819(6) .0847(6) Uani d . 1 . O
O3 .4766(2) .3222(2) .24558(6) .0636(5) Uani d . 1 . O
H3 .503(4) .370(3) .2710(10) .103(11) Uiso d . 1 . H
C1 .1968(2) .5130(2) .04391(8) .0494(5) Uani d . 1 . C
H1a .1756 .4688 .01368 .059 Uiso calc R 1 . H
C2 .1523(3) .6557(3) .05088(10) .0596(6) Uani d . 1 . C
H2a .0996 .7074 .02509 .072 Uiso calc R 1 . H
C3 .1847(3) .7223(2) .09534(10) .0602(6) Uani d . 1 . C
H3b .1523 .8177 .09942 .072 Uiso calc R 1 . H
C4 .2650(2) .6486(2) .13399(9) .0518(6) Uani d . 1 . C
H4a .2898 .6949 .16374 .062 Uiso calc R 1 . H
C4a .3082(2) .5053(2) .12793(7) .0385(4) Uani d . 1 . C
C4b .4100(2) .4061(2) .16323(7) .0372(4) Uani d . 1 . C
C4c .5714(2) .4448(2) .15257(7) .0396(5) Uani d . 1 . C
C5 .6675(2) .5561(2) .17167(8) .0514(5) Uani d . 1 . C
H5a .6428 .6131 .19713 .062 Uiso calc R 1 . H
C6 .8014(3) .5808(3) .15198(10) .0625(7) Uani d . 1 . C
H6a .8692 .6526 .16525 .075 Uiso calc R 1 . H
C7 .8356(3) .5006(3) .11311(9) .0612(6) Uani d . 1 . C
H7a .9244 .5214 .0998 .073 Uiso calc R 1 . H
C8 .7403(2) .3897(3) .09355(8) .0529(6) Uani d . 1 . C
H8a .7632 .3362 .06710 .064 Uiso calc R 1 . H
C8a .6090(2) .3604(2) .11451(7) .0420(5) Uani d . 1 . C
C8b .4951(2) .2428(2) .10339(7) .0399(5) Uani d . 1 . C
H8ba .5320 .1462 .09510 .048 Uiso calc R 1 . H
C8c .3822(2) .2505(2) .13937(6) .0348(4) Uani d . 1 . C
C8d .3243(2) .2812(2) .08629(6) .0362(4) Uani d . 1 . C
C8e .2738(2) .4370(2) .08305(7) .0389(5) Uani d . 1 . C
C9 .3849(3) .4233(2) .21587(7) .0498(5) Uani d . 1 . C
H9a .410 .5221 .22663 .060 Uiso calc R 1 . H
H9b .2777 .4069 .21875 .060 Uiso calc R 1 . H
C10 .3403(2) .1167(2) .16630(6) .0387(4) Uani d . 1 . C
C11 .1868(2) .1061(2) .18250(6) .0390(5) Uani d . 1 . C
C12 .1496(3) -.0169(2) .20770(8) .0554(6) Uani d . 1 . C
H12a .2229 -.0889 .2160 .067 Uiso calc R 1 . H
C13 .0050(3) -.0328(3) .22033(9) .0710(7) Uani d . 1 . C
H13a -.0196 -.1168 .23639 .085 Uiso calc R 1 . H
C14 -.1033(3) .0745(3) .20939(9) .0647(7) Uani d . 1 . C
H14a -.2005 .0636 .21832 .078 Uiso calc R 1 . H
C15 -.0675(2) .1975(3) .18531(8) .0533(6) Uani d . 1 . C
H15a -.1399 .2711 .17846 .064 Uiso calc R 1 . H
C16 .0757(2) .2125(2) .17116(7) .0439(5) Uani d . 1 . C
H16a .097 .2948 .15384 .053 Uiso calc R 1 . H
C17 .2411(2) .1687(2) .05334(7) .0450(5) Uani d . 1 . C
C18 .2762(2) .1576(2) .00286(7) .0422(5) Uani d . 1 . C
C19 .3926(3) .2384(3) -.01354(8) .0545(6) Uani d . 1 . C
H19a .4495 .304 .00709 .065 Uiso calc R 1 . H
C20 .4238(3) .2211(3) -.06039(9) .0656(7) Uani d . 1 . C
H20a .5028 .2740 -.07109 .079 Uiso calc R 1 . H
C21 .3383(3) .1260(3) -.09127(8) .0658(7) Uani d . 1 . C
H21a .3599 .1146 -.12280 .079 Uiso calc R 1 . H
C22 .2219(3) .0483(3) -.07587(8) .0650(7) Uani d . 1 . C
H22a .1633 -.0146 -.09710 .078 Uiso calc R 1 . H
C23 .1909(3) .0627(3) -.02906(8) .0542(6) Uani d . 1 . C
H23a .1122 .0085 -.01870 .065 Uiso calc R 1 . H
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'
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
C2 C1 C8e 118.6(2) ?
C3 C2 C1 121.1(2) ?
C2 C3 C4 120.5(2) ?
C3 C4 C4a 119.2(2) ?
C4 C4a C8e 120.3(2) ?
C4 C4a C4b 129.0(2) ?
C8e C4a C4b 110.3(2) yes
C9 C4b C4c 115.1(2) ?
C9 C4b C4a 114.1(2) ?
C4c C4b C4a 102.48(15) yes
C9 C4b C8c 117.7(2) ?
C4c C4b C8c 102.81(15) yes
C4a C4b C8c 102.69(14) yes
C5 C4c C8a 120.4(2) ?
C5 C4c C4b 129.1(2) ?
C8a C4c C4b 110.1(2) yes
C4c C5 C6 118.5(2) ?
C7 C6 C5 121.0(2) ?
C6 C7 C8 121.0(2) ?
C7 C8 C8a 118.2(2) ?
C4c C8a C8 120.8(2) ?
C4c C8a C8b 109.9(2) yes
C8 C8a C8b 129.3(2) yes
C8a C8b C8c 108.6(2) yes
C8a C8b C8d 120.1(2) yes
C8c C8b C8d 59.62(12) yes
C10 C8c C8b 121.4(2) ?
C10 C8c C8d 124.1(2) ?
C8b C8c C8d 61.77(12) yes
C10 C8c C4b 123.88(15) ?
C8b C8c C4b 104.13(15) yes
C8d C8c C4b 104.82(14) yes
C8e C8d C17 120.0(2) ?
C8e C8d C8c 106.99(15) yes
C17 C8d C8c 122.6(2) ?
C8e C8d C8b 120.1(2) yes
C17 C8d C8b 113.8(2) ?
C8c C8d C8b 58.61(12) yes
C1 C8e C4a 120.2(2) ?
C1 C8e C8d 129.4(2) ?
C4a C8e C8d 110.3(2) yes
O3 C9 C4b 110.5(2) ?
O1 C10 C11 121.0(2) ?
O1 C10 C8c 119.1(2) ?
C11 C10 C8c 119.9(2) ?
C16 C11 C12 118.4(2) ?
C16 C11 C10 121.9(2) ?
C12 C11 C10 119.6(2) ?
C13 C12 C11 120.4(2) ?
C14 C13 C12 120.5(2) ?
C15 C14 C13 119.8(2) ?
C14 C15 C16 120.2(2) ?
C15 C16 C11 120.7(2) ?
O2 C17 C18 121.1(2) ?
O2 C17 C8d 120.3(2) ?
C18 C17 C8d 118.6(2) ?
C23 C18 C19 118.7(2) ?
C23 C18 C17 119.0(2) ?
C19 C18 C17 122.2(2) ?
C20 C19 C18 120.0(2) ?
C21 C20 C19 120.2(2) ?
C22 C21 C20 120.3(2) ?
C21 C22 C23 120.2(2) ?
C22 C23 C18 120.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.222(2) ?
O2 C17 . 1.214(2) ?
O3 C9 . 1.418(3) ?
C1 C2 . 1.385(3) ?
C1 C8e . 1.390(3) ?
C2 C3 . 1.376(3) ?
C3 C4 . 1.381(3) ?
C4 C4a . 1.382(3) ?
C4a C8e . 1.394(3) yes
C4a C4b . 1.535(3) yes
C4b C9 . 1.522(3) ?
C4b C4c . 1.534(3) yes
C4b C8c . 1.576(3) yes
C4C C5 . 1.384(3) ?
C4c C8a . 1.388(3) yes
C5 C6 . 1.386(3) ?
C6 C7 . 1.375(3) ?
C7 C8 . 1.381(3) ?
C8 C8a . 1.391(3) ?
C8a C8b . 1.475(3) yes
C8b C8c . 1.508(3) yes
C8b C8d . 1.556(3) yes
C8c C10 . 1.508(3) ?
C8c C8d . 1.524(2) yes
C8d C8e . 1.492(3) yes
C8d C17 . 1.502(3) ?
C10 C11 . 1.487(3) ?
C11 C16 . 1.386(3) ?
C11 C12 . 1.389(3) ?
C12 C13 . 1.375(3) ?
C13 C14 . 1.375(4) ?
C14 C15 . 1.369(3) ?
C15 C16 . 1.379(3) ?
C17 C18 . 1.485(3) ?
C18 C23 . 1.389(3) ?
C18 C19 . 1.391(3) ?
C19 C20 . 1.379(3) ?
C20 C21 . 1.374(3) ?
C21 C22 . 1.365(3) ?
C22 C23 . 1.375(3) ?
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
C8e C1 C2 C3 0.7(3)
C1 C2 C3 C4 1.1(3)
C2 C3 C4 C4a -2.1(3)
C3 C4 C4a C8e 1.3(3)
C3 C4 C4a C4b 173.5(2)
C4 C4a C4b C9 39.0(3)
C8e C4a C4b C9 -148.2(2)
C4 C4a C4b C4c -86.0(2)
C8e C4a C4b C4c 86.8(2)
C4 C4a C4b C8c 167.6(2)
C8e C4a C4b C8c -19.6(2)
C9 C4b C4c C5 -38.3(3)
C4a C4b C4c C5 86.1(2)
C8c C4b C4c C5 -167.6(2)
C9 C4b C4c C8a 149.1(2)
C4a C4b C4c C8a -86.5(2)
C8c C4b C4c C8a 19.8(2)
C8a C4c C5 C6 -0.1(3)
C4b C4c C5 C6 -172.1(2)
C4c C5 C6 C7 2.5(3)
C5 C6 C7 C8 -2.2(4)
C6 C7 C8 C8a -0.5(3)
C5 C4c C8a C8 -2.7(3)
C4b C4c C8a C8 170.7(2)
C5 C4c C8a C8b 175.6(2)
C4b C4c C8a C8b -11.0(2)
C7 C8 C8a C4c 3.0(3)
C7 C8 C8a C8b -175.0(2)
C4c C8a C8b C8c -3.2(2)
C8 C8a C8b C8c 174.9(2)
C4c C8a C8b C8d 61.9(2)
C8 C8a C8b C8d -120.0(2)
C8a C8b C8c C10 -130.6(2)
C8d C8b C8c C10 114.7(2)
C8a C8b C8c C8d 114.7(2)
C8d C8b C8c C8d 0.0
C8a C8b C8c C4b 15.2(2)
C8d C8b C8c C4b -99.45(15)
C9 C4b C8c C10 -3.3(3)
C4c C4b C8c C10 124.3(2)
C4a C4b C8c C10 -129.5(2)
C9 C4b C8c C8b -148.1(2)
C4c C4b C8c C8b -20.5(2)
C4a C4b C8c C8b 85.7(2)
C9 C4b C8c C8d 147.9(2)
C4c C4b C8c C8d -84.5(2)
C4a C4b C8c C8d 21.7(2)
C10 C8c C8d C8e 134.1(2)
C8b C8c C8d C8e -115.4(2)
C4b C8c C8d C8e -17.1(2)
C10 C8c C8d C17 -10.7(3)
C8b C8c C8d C17 99.9(2)
C4b C8c C8d C17 -161.8(2)
C10 C8c C8d C8b -110.6(2)
C8b C8c C8d C8b 0.0
C4b C8c C8d C8b 98.3(2)
C8a C8b C8d C8e -2.6(3)
C8c C8b C8d C8e 92.4(2)
C8a C8b C8d C17 150.2(2)
C8c C8b C8d C17 -114.8(2)
C8a C8b C8d C8c -95.0(2)
C8c C8b C8d C8c 0.0
C2 C1 C8e C4a -1.5(3)
C2 C1 C8e C8d 175.3(2)
C4 C4a C8e C1 0.5(3)
C4b C4a C8e C1 -173.0(2)
C4 C4a C8e C8d -176.9(2)
C4b C4a C8e C8d 9.6(2)
C17 C8d C8e C1 -26.1(3)
C8c C8d C8e C1 -171.9(2)
C8b C8d C8e C1 125.0(2)
C17 C8d C8e C4a 151.0(2)
C8c C8d C8e C4a 5.2(2)
C8b C8d C8e C4a -57.9(2)
C4c C4b C9 O3 -65.3(2)
C4a C4b C9 O3 176.6(2)
C8c C4b C9 O3 56.2(2)
C8b C8c C10 O1 27.0(3)
C8d C8c C10 O1 102.2(2)
C4b C8c C10 O1 -112.0(2)
C8b C8c C10 C11 -151.4(2)
C8d C8c C10 C11 -76.2(2)
C4b C8c C10 C11 69.6(2)
O1 C10 C11 C16 -174.5(2)
C8c C10 C11 C16 3.9(3)
O1 C10 C11 C12 2.2(3)
C8c C10 C11 C12 -179.4(2)
C16 C11 C12 C13 0.9(3)
C10 C11 C12 C13 -175.9(2)
C11 C12 C13 C14 -1.8(4)
C12 C13 C14 C15 0.7(4)
C13 C14 C15 C16 1.3(4)
C14 C15 C16 C11 -2.2(3)
C12 C11 C16 C15 1.1(3)
C10 C11 C16 C15 177.9(2)
C8e C8d C17 O2 -101.4(2)
C8c C8d C17 O2 39.0(3)
C8b C8d C17 O2 105.8(2)
C8e C8d C17 C18 80.0(2)
C8c C8d C17 C18 -139.7(2)
C8b C8d C17 C18 -72.9(2)
O2 C17 C18 C23 6.7(3)
C8d C17 C18 C23 -174.6(2)
O2 C17 C18 C19 -172.9(2)
C8d C17 C18 C19 5.8(3)
C23 C18 C19 C20 -1.5(3)
C17 C18 C19 C20 178.1(2)
C18 C19 C20 C21 1.2(4)
C19 C20 C21 C22 0.1(4)
C20 C21 C22 C23 -1.1(4)
C21 C22 C23 C18 0.8(4)
C19 C18 C23 C22 0.5(3)
C17 C18 C23 C22 -179.1(2)
