#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/75/2007536.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_2007536
loop_
_publ_author_name
'Krieger, Claus'
'Wartini, Alexander R.'
'Neugebauer, Franz A.'
_publ_section_title
;9,10-Dihydro-1,4-dimethoxy-5,8-dimethyl-cis-9,10-diphenyl-9,10-anthracenediol,
 a Crowded Planar 9,10-Dihydroanthracene
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1125
_journal_page_last               1127
_journal_paper_doi               10.1107/S0108270198003187
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C30 H28 O4'
_chemical_formula_sum            'C30 H28 O4'
_chemical_formula_weight         452.55
_chemical_name_systematic
;
9,10-dihydro-1,4-dimethoxy-5,8-dimethyl-cis-9,10-diphenyl-
9,10-anthracenediol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           'Waasmaier & Kirfel (1995)'
_cell_angle_alpha                66.33(2)
_cell_angle_beta                 79.23(2)
_cell_angle_gamma                70.08(2)
_cell_formula_units_Z            2
_cell_length_a                   8.229(3)
_cell_length_b                   11.522(3)
_cell_length_c                   14.430(4)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    298
_cell_measurement_theta_max      16
_cell_measurement_theta_min      12
_cell_volume                     1176.1(7)
_computing_cell_refinement       'CAD-4 Operations Manual'
_computing_data_collection
'CAD-4 Operations Manual (Enraf-Nonius, 1977)'
_computing_data_reduction        'maXus (Mackay et al., 1998)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  maXus
_computing_structure_refinement  maXus
_computing_structure_solution    'SIR (Burla et al., 1989)'
_diffrn_ambient_temperature      294
_diffrn_measurement_device       'Enraf Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4782
_diffrn_reflns_theta_max         25.03
_diffrn_standards_decay_%        2.9
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      1.300
_exptl_crystal_density_method    'flotation in heptane/tetrachloromethane'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.022
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3366
_refine_ls_R_factor_obs          .068
_refine_ls_shift/esd_max         0.0235
_refine_ls_shift/esd_mean        0.0021
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fₒ) + 0.0021Fₒ²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .056
_reflns_number_observed          3366
_reflns_number_total             4611
_reflns_observed_criterion       I>0.5\s(I)
_cod_data_source_file            jz1274.cif
_cod_data_source_block           jz1274
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (18 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 34 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F~o~) +
0.0021F~o~^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~o~) + 0.0021F~o~^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1176.0(7)
_cod_database_code               2007536
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-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_occupancy
C1 .1991(2) .06810(10) .43770(10) .0517(8) Uani 1.00
C2 .2537(2) .0073(2) .53400(10) .0611(9) Uani 1.00
C3 .3710(2) -.1177(2) .56290(10) .0605(9) Uani 1.00
C4 .4316(2) -.17930(10) .49400(10) .0544(8) Uani 1.00
C4a .3847(2) -.11590(10) .39240(10) .0463(8) Uani 1.00
C5 .4386(2) -.1873(2) .14650(10) .0700(10) Uani 1.00
C6 .3663(3) -.1267(2) .05360(10) .0910(10) Uani 1.00
C7 .2448(3) -.0049(2) .02700(10) .0860(10) Uani 1.00
C8 .1896(2) .0642(2) .09120(10) .0690(10) Uani 1.00
C8a .2611(2) .00590(10) .18710(10) .0528(8) Uani 1.00
C9 .1949(2) .08290(10) .25870(10) .0498(8) Uani 1.00
C9a .2656(2) .01000(10) .36368(9) .0452(7) Uani 1.00
C10 .4573(2) -.19200(10) .32090(10) .0495(8) Uani 1.00
C10a .3838(2) -.12020(10) .21560(10) .0537(8) Uani 1.00
O1' .07150(10) .18810(10) .40659(8) .0695(6) Uani 1.00
O4' .53640(10) -.30910(10) .52040(8) .0702(6) Uani 1.00
C1" -.0109(3) .2459(2) .48130(10) .0850(10) Uani 1.00
C4" .5941(3) -.3760(2) .62080(10) .0870(10) Uani 1.00
C5' .5722(3) -.3224(2) .1670(2) .1010(10) Uani 1.00
C8' .0525(3) .1965(2) .0523(2) .0970(10) Uani 1.00
O9' .01020(10) .10150(10) .27134(7) .0637(6) Uani 1.00
O10' .40250(10) -.31097(9) .36410(8) .0600(6) Uani 1.00
C11 .6567(2) -.22680(10) .31150(10) .0520(8) Uani 1.00
C12 .7355(2) -.1294(2) .25930(10) .0580(9) Uani 1.00
C13 .9152(2) -.1581(2) .24640(10) .0710(10) Uani 1.00
C14 1.0177(2) -.2848(2) .28560(10) .0770(10) Uani 1.00
C15 .9425(2) -.3839(2) .3390(2) .0870(10) Uani 1.00
C16 .7644(2) -.3555(2) .35270(10) .0780(10) Uani 1.00
C91 .2346(2) .21800(10) .20930(10) .0577(9) Uani 1.00
C92 .4026(2) .2205(2) .18080(10) .0740(10) Uani 1.00
C93 .4442(3) .3399(2) .13510(10) .0950(10) Uani 1.00
C94 .3156(4) .4570(2) .11910(10) .103(2) Uani 1.00
C95 .1470(4) .4571(2) .1484(2) .104(2) Uani 1.00
C96 .1070(3) .3383(2) .19290(10) .0820(10) Uani 1.00
H9' -.0215 .1390 .3223 .061(6) Uiso 1.00
H10' .4353 -.3506 .4302 .046(6) Uiso 1.00
H2 .2102 .0515 .5815 .019(4) Uiso 1.00
H3 .4100 -.1611 .6305 .025(4) Uiso 1.00
H7 .1969 .0332 -.0381 .056(6) Uiso 1.00
H6 .4023 -.1713 .0062 .039(5) Uiso 1.00
H92 .5033 .1384 .1934 .034(5) Uiso 1.00
H93 .5718 .3374 .1197 .064(6) Uiso 1.00
H94 .3786 .5281 .0937 .086(7) Uiso 1.00
H95 .0851 .5460 .1354 .130(10) Uiso 1.00
H96 -.0112 .3393 .2131 .040(5) Uiso 1.00
H12 .6622 -.0391 .2295 .027(4) Uiso 1.00
H13 .9597 -.0841 .2133 .049(5) Uiso 1.00
H14 1.1395 -.3071 .2788 .033(4) Uiso 1.00
H15 1.0034 -.4743 .3702 .075(7) Uiso 1.00
H16 .7044 -.4242 .3859 .046(5) Uiso 1.00
H4A .6577 -.4651 .6211 .066(6) Uiso 1.00
H4B .4867 -.3814 .6670 .074(7) Uiso 1.00
H4C .6596 -.3302 .6364 .067(7) Uiso 1.00
H1A -.0830 .3235 .4407 .080(8) Uiso 1.00
H1B .0899 .2677 .5019 .081(7) Uiso 1.00
H1C -.0543 .1850 .5359 .053(6) Uiso 1.00
H8A -.0337 .2124 .1008 .100(10) Uiso 1.00
H8B .0251 .2060 -.0124 .060(6) Uiso 1.00
H8C .1070 .2690 .0382 .089(8) Uiso 1.00
H5A .5407 -.3896 .2282 .099(9) Uiso 1.00
H5B .6930 -.3184 .1632 .087(8) Uiso 1.00
H5C .5611 -.3480 .1119 .066(6) Uiso 1.00
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 2 0
4 -3 0
0 3 6
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 C9a 122.1(2) ?
C2 C1 O1' 122.6(2) ?
C9a C1 O1' 115.3(2) ?
C1 C2 C3 119.8(2) ?
C2 C3 C4 119.3(2) ?
C3 C4 C4a 122.0(2) ?
C3 C4 O4' 122.3(2) ?
C4a C4 O4' 115.6(2) ?
C4 C4a C10 118.6(2) ?
C4 C4a C9a 118.3(2) ?
C10 C4a C9a 122.9(2) y
C6 C5 C10a 118.3(2) ?
C9 C8a C10a 122.1(2) y
C8a C9 C9a 114.9(2) y
C8a C9 O9' 104.3(2) y
C8a C9 C91 109.8(2) y
C9a C9 O9' 107.2(2) y
C91 C9 C9a 109.3(2) y
C91 C9 O9' 111.1(2) y
C6 C5 C5' 116.9(2) y
C10a C5 C5' 124.8(2) y
C5 C6 C7 121.9(2) ?
C6 C7 C8 121.6(2) ?
C8 C8a C9 117.5(2) ?
C8 C8a C10a 120.3(2) ?
C1 C9a C9 118.8(2) ?
C1 C9a C4a 118.2(2) ?
C10 C10a C8a 122.7(2) y
C9 C9a C4a 122.9(2) y
C10a C10 C4a 114.4(2) y
C4a C10 O10' 107.1(2) y
C11 C10 C4a 109.4(2) y
C10a C10 O10' 104.4(2) y
C11 C10 C10a 110.4(2) y
C11 C10 O10' 111.0(2) y
C7 C8 C8' 115.8(2) y
C7 C8 C8a 118.3(2) ?
C8' C8 C8a 125.9(2) y
C5 C10a C10 117.8(2) ?
C5 C10a C8a 119.5(2) ?
C10 C11 C12 120.3(2) ?
C10 C11 C16 122.8(2) ?
C12 C11 C16 116.9(2) ?
C11 C12 C13 121.7(2) ?
C12 C13 C14 120.3(2) ?
C13 C14 C15 119.2(2) ?
C14 C15 C16 120.6(2) ?
C11 C16 C15 121.3(2) ?
C9 C91 C92 119.6(2) ?
C9 C91 C96 122.7(2) ?
C92 C91 C96 117.7(2) ?
C91 C92 C93 121.5(2) ?
C92 C93 C94 119.5(3) ?
C93 C94 C95 120.0(2) ?
C94 C95 C96 120.0(2) ?
C91 C96 C95 121.2(2) ?
C1 O1' C1" 117.5(2) ?
C4 O4' C4" 118.0(2) ?
C9 O9' H9' 100.8(2) ?
C10 O10' H10' 105.3(2) ?
C1 C2 H2 120.0(2) ?
C3 C2 H2 120.2(2) ?
C2 C3 H3 120.4(2) ?
C4 C3 H3 120.3(2) ?
C5 C6 H6 119.1(2) ?
C7 C6 H6 119.0(2) ?
C6 C7 H7 119.2(2) ?
C11 C12 H12 118.0(2) ?
C13 C12 H12 120.3(2) ?
C12 C13 H13 116.4(2) ?
C14 C13 H13 123.1(2) ?
C13 C14 H14 122.2(2) ?
C15 C14 H14 118.5(2) ?
C14 C15 H15 125.0(2) ?
C16 C15 H15 114.4(2) ?
C11 C16 H16 115.1(2) ?
C15 C16 H16 123.3(2) ?
C8 C7 H7 119.2(2) ?
O1' C1" H1A 99.2(2) ?
O1' C1" H1B 104.3(2) ?
O1' C1" H1C 109.3(2) ?
H1A C1" H1B 108.8(2) ?
H1A C1" H1C 121.4(2) ?
H1B C1" H1C 111.9(2) ?
O4' C4" H4A 101.8(2) ?
O4' C4" H4B 105.8(2) ?
O4' C4" H4C 112.0(2) ?
H4A C4" H4B 108.2(2) ?
H4A C4" H4C 116.2(2) ?
H4B C4" H4C 111.9(2) ?
C5 C5' H5A 112.0(2) ?
C5 C5' H5B 112.3(2) ?
C5 C5' H5C 103.8(2) ?
H5A C5' H5B 114.7(2) ?
H5A C5' H5C 104.1(2) ?
H5B C5' H5C 108.9(2) ?
C8 C8' H8A 113.7(2) ?
C8 C8' H8B 106.5(2) ?
C8 C8' H8C 108.1(2) ?
H8A C8' H8B 121.2(2) ?
H8A C8' H8C 100.8(2) ?
H8B C8' H8C 105.6(2) ?
C91 C92 H92 123.0(2) ?
C93 C92 H92 115.4(3) ?
C92 C93 H93 119.1(3) ?
C94 C93 H93 121.2(3) ?
C93 C94 H94 104.9(3) ?
C95 C94 H94 134.5(3) ?
C94 C95 H95 104.7(3) ?
C96 C95 H95 135.1(3) ?
C91 C96 H96 119.4(2) ?
C95 C96 H96 119.4(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.364(2) ?
C1 C9a . . 1.413(2) y
C1 O1' . . 1.380(2) y
C2 C3 . . 1.379(3) ?
C3 C4 . . 1.372(2) ?
C4 C4a . . 1.411(2) y
C4 O4' . . 1.383(2) y
C4a C9a . . 1.392(2) y
C4a C10 . . 1.526(2) y
C5 C6 . . 1.379(3) ?
C5 C10a . . 1.417(3) y
C5 C5' . . 1.518(3) y
C6 C7 . . 1.368(4) ?
C7 C8 . . 1.374(3) ?
C8 C8a . . 1.415(2) y
C8 C8' . . 1.513(3) y
C8a C9 . . 1.531(2) y
C8a C10a . . 1.405(3) y
C9 C91 . . 1.551(2) y
C9 C9a . . 1.522(2) y
C9 O9' . . 1.448(2) y
C10 C11 . . 1.544(2) y
C10 C10a . . 1.534(2) y
C10 O10' . . 1.449(2) y
C1" O1' . . 1.436(3) ?
C4" O4' . . 1.425(3) ?
C11 C12 . . 1.372(3) ?
C11 C16 . . 1.390(3) ?
C12 C13 . . 1.394(3) ?
C13 C14 . . 1.356(3) ?
C14 C15 . . 1.369(3) ?
C15 C16 . . 1.382(3) ?
C91 C92 . . 1.373(3) ?
C91 C96 . . 1.385(3) ?
C92 C93 . . 1.397(3) ?
C93 C94 . . 1.365(4) ?
C94 C95 . . 1.373(5) ?
C95 C96 . . 1.384(3) ?
C2 H2 . . .959(2) ?
C3 H3 . . .959(2) ?
C6 H6 . . .960(2) ?
C7 H7 . . .960(2) ?
C12 H12 . . .970(2) ?
C13 H13 . . .954(2) ?
C14 H14 . . .942(2) ?
C15 H15 . . .944(2) ?
C16 H16 . . .988(2) ?
C1" H1A . . .928(2) ?
C1" H1B . . 1.056(2) ?
C1" H1C . . .928(2) ?
C4" H4A . . .979(3) ?
C4" H4B . . 1.005(3) ?
C4" H4C . . .978(2) ?
C5' H5A . . .973(3) ?
C5' H5B . . 1.010(3) ?
C5' H5C . . .981(2) ?
C8' H8A . . .925(3) ?
C8' H8B . . .956(2) ?
C8' H8C . . 1.013(3) ?
C92 H92 . . .999(2) ?
C93 H93 . . 1.025(2) ?
C94 H94 . . 1.025(2) ?
C95 H95 . . .933(3) ?
C96 H96 . . .959(3) ?
O9' H9' . . .950(2) ?
O10' H10' . . .924(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O9' H9' O1' 0.950(2) 1.892(2) 2.709(2) 142.5(2) y
O10' H10' O4' 0.924(2) 1.946(2) 2.699(2) 137.3(2) y
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
C4 C4a C9a C1 0.5(2) y
C10 C4a C9a C9 0.7(2) y
C9a C4a C10 C10a -1.9(2) y
C4 C4a C10 C10a 174.1(2) y
C4a C10 C10a C5 -177.0(2) y
C4a C10 C10a C8a 0.7(2) y
C4 C4a C10 O10' 58.7(2) y
C4 C4a C10 C11 -61.7(2) y
C8 C8a C10a C5 1.5(2) y
C9 C8a C10a C10 1.7(2) y
C10a C8a C9 C9a -2.7(2) y
C8 C8a C9 C9a 175.1(2) y
C8a C9 C9a C1 -174.0(2) y
C8a C9 C9a C4a 1.6(2) y
C8 C8a C9 O9' 58.0(2) y
C8 C8a C9 C91 -61.1(2) y
C9a C1 C2 C3 -3.3(2) ?
O1' C1 C2 C3 174.5(2) ?
C2 C1 C9a C4a 2.9(2) ?
C2 C1 C9a C9 178.7(2) ?
O1' C1 C9a C4a -175.0(2) ?
O1' C1 C9a C9 0.7(2) ?
C2 C1 O1' C1" -3.1(2) ?
C1 C2 C3 C4 0.1(2) ?
C2 C3 C4 C4a 3.5(2) ?
C2 C3 C4 O4' -174.3(2) ?
C3 C4 C4a C9a -3.5(4) ?
C3 C4 C4a C10 -179.6(2) ?
O4' C4 C4a C9a 174.1(2) ?
O4' C4 C4a C10 -2.0(3) ?
C3 C4 O4' C4" -5.4(2) ?
C4 C4a C9a C9 -175.0(2) ?
C10 C4a C9a C1 176.3(2) ?
C9a C4a C10 O10' -117.0(2) ?
C9a C4a C10 C11 122.6(2) ?
C10a C5 C6 C7 0.1(2) ?
C5' C5 C6 C7 -180.0(3) ?
C6 C5 C10a C8a -1.2(2) ?
C6 C5 C10a C10 176.6(2) ?
C5' C5 C10a C8a 178.9(2) ?
C5' C5 C10a C10 -3.8(2) ?
C5 C6 C7 C8 0.7(2) ?
C6 C7 C8 C8a -0.4(2) ?
C6 C7 C8 C8' -179.0(3) ?
C7 C8 C8a C9 -178.6(2) ?
C7 C8 C8a C10a -0.7(2) ?
C8' C8 C8a C9 -0.2(2) ?
C8' C8 C8a C10a 178.0(2) ?
C10a C8a C9 O9' -119.8(2) ?
C10a C8a C9 C91 121.0(2) ?
C8 C8a C10a C10 -176.1(2) ?
C9 C8a C10a C5 179.3(2) ?
O9' C9 C9a C1 -58.5(2) ?
O9' C9 C9a C4a 117.0(2) ?
C91 C9 C9a C1 62.0(2) ?
C91 C9 C9a C4a -122.4(2) ?
C9a C9 O9' H9' 50.4(2) ?
C8a C9 C91 C92 -57.9(2) ?
C9a C9 C91 C92 69.1(2) ?
O9' C9 C91 C96 7.8(2) ?
O10' C10 C10a C5 -60.3(2) ?
C11 C10 C10a C5 58.7(2) ?
C11 C10 C10a C8a -123.3(2) ?
C4a C10 O10' H10' -52.1(2) ?
C4a C10 C11 C12 -71.4(2) ?
C10a C10 C11 C12 55.4(2) ?
