#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:13:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180066 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051248.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_7051248
loop_
_publ_author_name
'Laxmi Madhavi, N. N.'
'Bilton, Clair'
'Howard, Judith A. K.'
'Allen, Frank H.'
'Nangia, Ashwini'
'Desiraju, Gautam R.'
_publ_section_title
;
 Seeking structural repetitivity in systems with interaction
 interference: crystal engineering in the gem-alkynol family
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1
_journal_paper_doi               10.1039/a908233f
_journal_volume                  24
_journal_year                    2000
_chemical_formula_moiety         'C18 H12 O2'
_chemical_formula_sum            'C18 H12 O2'
_chemical_formula_weight         260.28
_chemical_melting_point          479.5(5)
_chemical_name_common
; 
 trans-9,10-Diethynyl-9,10-dihydroxy-9,10-dihydroanthracene
;
_chemical_name_systematic
; 
 trans-9,10-Diethynyl-9,10-dihydroxy-9,10-dihydroanthracene
;
_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_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.78(3)
_cell_angle_beta                 102.06(3)
_cell_angle_gamma                102.59(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7684(18)
_cell_length_b                   8.9558(18)
_cell_length_c                   10.315(2)
_cell_measurement_reflns_used    440
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      5.78
_cell_volume                     682.3(4)
_computing_cell_refinement       'Brucker SMART'
_computing_data_collection       'Brucker SMART'
_computing_data_reduction        'Brucker SAINT'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_device_type  'Brucker SMART CCD'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6577
_diffrn_reflns_theta_full        30.38
_diffrn_reflns_theta_max         30.38
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         'not relevant'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.4119
_exptl_absorpt_correction_T_min  0.3520
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'empirical correction using psi-scans'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0540
_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)+(0.0368P)²+0.5022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                2404
_reflns_number_total             3623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a908233f.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '479-480 K' was changed to '479.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        682.2(2)
_cod_database_code               7051248
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2626(3) -0.2681(3) 0.0455(3) 0.0338(5) Uani 1 1 d . . .
H1 H 0.290(3) -0.363(3) 0.046(3) 0.048(7) Uiso 1 1 d . . .
C2 C 0.3852(3) -0.1105(3) 0.0951(2) 0.0304(5) Uani 1 1 d . . .
H2 H 0.500(3) -0.100(3) 0.127(3) 0.035(6) Uiso 1 1 d . . .
C3 C 0.3410(2) 0.0283(3) 0.0941(2) 0.0256(4) Uani 1 1 d . . .
H3 H 0.427(3) 0.140(3) 0.130(3) 0.034(6) Uiso 1 1 d . . .
C4 C 0.1736(2) 0.0129(2) 0.04628(19) 0.0186(4) Uani 1 1 d . . .
C5 C 0.1330(2) 0.1706(2) 0.0485(2) 0.0190(4) Uani 1 1 d . . .
O1 O 0.21482(17) 0.31803(17) 0.19720(15) 0.0275(3) Uani 1 1 d . . .
HA H 0.194(4) 0.276(4) 0.269(4) 0.087(11) Uiso 1 1 d . . .
C6 C 0.2069(2) 0.2237(2) -0.0505(2) 0.0249(4) Uani 1 1 d . . .
C7 C 0.2679(3) 0.2669(3) -0.1283(3) 0.0334(5) Uani 1 1 d . . .
H7 H 0.317(3) 0.304(3) -0.195(3) 0.053(8) Uiso 1 1 d . . .
C8 C -0.0513(2) 0.1439(2) 0.0007(2) 0.0197(4) Uani 1 1 d . . .
C9 C -0.0974(3) 0.2856(3) 0.0023(2) 0.0282(4) Uani 1 1 d . . .
H9 H -0.006(3) 0.396(3) 0.043(3) 0.035(6) Uiso 1 1 d . . .
C21 C 0.8055(3) 0.2958(3) 0.3612(3) 0.0363(5) Uani 1 1 d . . .
H21 H 0.889(3) 0.274(3) 0.314(3) 0.048(7) Uiso 1 1 d . . .
C22 C 0.7475(3) 0.4286(3) 0.3655(2) 0.0301(4) Uani 1 1 d . . .
H22 H 0.791(3) 0.500(3) 0.320(3) 0.034(6) Uiso 1 1 d . . .
C23 C 0.6262(2) 0.4628(2) 0.4319(2) 0.0206(4) Uani 1 1 d . . .
C24 C 0.5697(2) 0.6133(2) 0.4337(2) 0.0205(4) Uani 1 1 d . . .
O2 O 0.51293(18) 0.59111(18) 0.28344(15) 0.0262(3) Uani 1 1 d . . .
HB H 0.418(4) 0.502(4) 0.234(3) 0.058(8) Uiso 1 1 d . . .
C25 C 0.7171(2) 0.7758(2) 0.5189(2) 0.0246(4) Uani 1 1 d . . .
C26 C 0.8354(3) 0.9037(3) 0.5925(2) 0.0332(5) Uani 1 1 d . . .
H26 H 0.931(3) 1.003(3) 0.652(3) 0.044(7) Uiso 1 1 d . . .
C27 C 0.4359(2) 0.6393(2) 0.5062(2) 0.0206(4) Uani 1 1 d . . .
C28 C 0.3738(3) 0.7721(3) 0.5092(2) 0.0292(4) Uani 1 1 d . . .
H28 H 0.416(3) 0.840(3) 0.462(3) 0.039(6) Uiso 1 1 d . . .
C29 C 0.2540(3) 0.8040(3) 0.5739(3) 0.0357(5) Uani 1 1 d . . .
H29 H 0.210(3) 0.896(3) 0.575(3) 0.043(7) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 120.27(19) 2 . yes
C9 C1 H1 118.9(16) 2 . yes
C2 C1 H1 120.8(16) . . yes
C3 C2 C1 119.74(19) . . yes
C3 C2 H2 120.5(14) . . yes
C1 C2 H2 119.7(14) . . yes
C2 C3 C4 120.72(19) . . yes
C2 C3 H3 120.0(13) . . yes
C4 C3 H3 119.3(13) . . yes
C8 C4 C3 119.44(17) 2 . yes
C8 C4 C5 122.36(15) 2 . yes
C3 C4 C5 118.20(16) . . yes
O1 C5 C6 104.47(14) . . yes
O1 C5 C8 109.21(15) . . yes
C6 C5 C8 108.97(15) . . yes
O1 C5 C4 109.89(14) . . yes
C6 C5 C4 109.36(15) . . yes
C8 C5 C4 114.46(14) . . yes
C5 O1 HA 107(2) . . yes
C7 C6 C5 179.2(2) . . yes
C6 C7 H7 178.8(15) . . yes
C4 C8 C9 119.44(17) 2 . yes
C4 C8 C5 123.15(15) 2 . yes
C9 C8 C5 117.40(16) . . yes
C1 C9 C8 120.37(19) 2 . yes
C1 C9 H9 123.3(13) 2 . yes
C8 C9 H9 116.3(13) . . yes
C22 C21 C29 120.0(2) . 2_666 yes
C22 C21 H21 119.6(15) . . yes
C29 C21 H21 120.4(15) 2_666 . yes
C21 C22 C23 120.87(19) . . yes
C21 C22 H22 119.5(13) . . yes
C23 C22 H22 119.7(13) . . yes
C27 C23 C22 119.18(17) 2_666 . yes
C27 C23 C24 123.08(16) 2_666 . yes
C22 C23 C24 117.73(16) . . yes
O2 C24 C25 105.98(14) . . yes
O2 C24 C27 109.72(14) . . yes
C25 C24 C27 108.40(15) . . yes
O2 C24 C23 110.19(15) . . yes
C25 C24 C23 108.16(15) . . yes
C27 C24 C23 114.05(14) . . yes
C24 O2 HB 107.2(18) . . yes
C26 C25 C24 176.9(2) . . yes
C25 C26 H26 178.0(16) . . yes
C23 C27 C28 119.31(17) 2_666 . yes
C23 C27 C24 122.85(16) 2_666 . yes
C28 C27 C24 117.84(16) . . yes
C29 C28 C27 121.03(19) . . yes
C29 C28 H28 120.8(14) . . yes
C27 C28 H28 118.2(14) . . yes
C28 C29 C21 119.6(2) . 2_666 yes
C28 C29 H29 121.0(14) . . yes
C21 C29 H29 119.4(14) 2_666 . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.381(3) 2 yes
C1 C2 1.391(3) . yes
C1 H1 0.94(3) . yes
C2 C3 1.383(3) . yes
C2 H2 0.96(2) . yes
C3 C4 1.404(3) . yes
C3 H3 0.98(2) . yes
C4 C8 1.391(2) 2 yes
C4 C5 1.523(2) . yes
C5 O1 1.450(2) . yes
C5 C6 1.491(3) . yes
C5 C8 1.522(2) . yes
O1 HA 0.99(3) . yes
C6 C7 1.191(3) . yes
C7 H7 1.01(3) . yes
C8 C4 1.391(2) 2 yes
C8 C9 1.408(3) . yes
C9 C1 1.381(3) 2 yes
C9 H9 0.99(2) . yes
C21 C22 1.380(3) . yes
C21 C29 1.394(3) 2_666 yes
C21 H21 0.97(3) . yes
C22 C23 1.404(3) . yes
C22 H22 0.99(2) . yes
C23 C27 1.393(2) 2_666 yes
C23 C24 1.529(3) . yes
C24 O2 1.440(2) . yes
C24 C25 1.494(3) . yes
C24 C27 1.529(3) . yes
O2 HB 0.89(3) . yes
C25 C26 1.190(3) . yes
C26 H26 0.94(3) . yes
C27 C23 1.393(2) 2_666 yes
C27 C28 1.403(3) . yes
C28 C29 1.379(3) . yes
C28 H28 0.98(2) . yes
C29 C21 1.394(3) 2_666 yes
C29 H29 0.98(2) . yes
