#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:13:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180066 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051249.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_7051249
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         'C14 H10 O2'
_chemical_formula_sum            'C14 H10 O2'
_chemical_formula_weight         210.22
_chemical_melting_point          407
_chemical_name_common
; 
 trans-1,4-Diethynyl-1,4-dihydroxy-1,4-dihydronaphthalene
;
_chemical_name_systematic
; 
 trans-1,4-Diethynyl-1,4-dihydroxy-1,4-dihydronaphthalene
;
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.1850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.8247(3)
_cell_length_b                   22.6384(8)
_cell_length_c                   10.4783(3)
_cell_measurement_reflns_used    935
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      5.18
_cell_volume                     2263.28(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker 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_detector_area_resol_mean 'not relevant'
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Brucker SMART CCD'
_diffrn_measurement_method       '/w 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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17967
_diffrn_reflns_theta_full        30.33
_diffrn_reflns_theta_max         30.33
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.6141
_exptl_absorpt_correction_T_min  0.3984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'empirical correction using psi-scans'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0897P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1597
_reflns_number_gt                3713
_reflns_number_total             6159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a908233f.txt
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '407 K' was changed to '407' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_database_code               7051249
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_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 0.6057(2) 0.16584(9) 0.0655(2) 0.0358(5) Uani 1 1 d . . .
H1 H 0.703(2) 0.1669(8) 0.105(2) 0.028(5) Uiso 1 1 d . . .
C2 C 0.48196(19) 0.16350(8) 0.01449(19) 0.0278(4) Uani 1 1 d . . .
C3 C 0.32622(18) 0.16012(8) -0.05833(17) 0.0237(4) Uani 1 1 d . . .
O1 O 0.28541(14) 0.17313(6) 0.05084(13) 0.0305(3) Uani 1 1 d . . .
H1A H 0.192(2) 0.1761(8) 0.008(2) 0.031(5) Uiso 1 1 d . . .
C4 C 0.28267(17) 0.09749(8) -0.11667(17) 0.0229(4) Uani 1 1 d . . .
C5 C 0.3303(2) 0.05028(8) -0.0182(2) 0.0317(4) Uani 1 1 d . . .
H5 H 0.387(2) 0.0605(9) 0.086(2) 0.036(5) Uiso 1 1 d . . .
C6 C 0.2980(2) -0.00698(9) -0.0650(2) 0.0390(5) Uani 1 1 d . . .
H6 H 0.339(2) -0.0405(9) 0.004(3) 0.041(6) Uiso 1 1 d . . .
C7 C 0.2183(2) -0.01898(9) -0.2132(2) 0.0397(5) Uani 1 1 d . . .
H7 H 0.198(2) -0.0609(11) -0.241(3) 0.050(7) Uiso 1 1 d . . .
C8 C 0.1701(2) 0.02680(9) -0.3109(2) 0.0330(4) Uani 1 1 d . . .
H8 H 0.112(2) 0.0179(9) -0.413(3) 0.039(6) Uiso 1 1 d . . .
C9 C 0.19988(17) 0.08572(7) -0.26428(17) 0.0229(4) Uani 1 1 d . . .
C10 C 0.13988(18) 0.13488(8) -0.37732(17) 0.0249(4) Uani 1 1 d . . .
C11 C -0.01601(19) 0.13251(8) -0.44756(18) 0.0288(4) Uani 1 1 d . . .
C12 C -0.1393(2) 0.13167(9) -0.4965(2) 0.0365(5) Uani 1 1 d . . .
H12 H -0.238(3) 0.1306(10) -0.533(3) 0.047(7) Uiso 1 1 d . . .
O2 O 0.17743(15) 0.12550(6) -0.49066(13) 0.0327(3) Uani 1 1 d . . .
H1B H 0.276(3) 0.1259(10) -0.448(3) 0.054(7) Uiso 1 1 d . . .
C13 C 0.18568(19) 0.19571(8) -0.31458(19) 0.0281(4) Uani 1 1 d . . .
H13 H 0.149(2) 0.2288(10) -0.382(3) 0.048(6) Uiso 1 1 d . . .
C14 C 0.26793(19) 0.20682(8) -0.17528(19) 0.0275(4) Uani 1 1 d . . .
H14 H 0.2925(19) 0.2480(9) -0.146(2) 0.027(5) Uiso 1 1 d . . .
C21 C 0.0004(2) 0.15781(10) 0.1815(2) 0.0379(5) Uani 1 1 d . . .
H21 H 0.044(3) 0.1561(11) 0.293(3) 0.068(8) Uiso 1 1 d . . .
C22 C -0.05315(18) 0.16146(8) 0.05225(19) 0.0282(4) Uani 1 1 d . . .
C23 C -0.11749(17) 0.16598(8) -0.10767(18) 0.0248(4) Uani 1 1 d . . .
O21 O -0.00582(14) 0.18835(6) -0.13431(15) 0.0325(3) Uani 1 1 d . . .
H2A H -0.036(3) 0.1888(14) -0.230(4) 0.090(10) Uiso 1 1 d . . .
C24 C -0.16527(17) 0.10569(8) -0.17697(17) 0.0234(4) Uani 1 1 d . . .
C25 C -0.0664(2) 0.06005(9) -0.1399(2) 0.0312(4) Uani 1 1 d . . .
H25 H 0.032(2) 0.0682(9) -0.079(2) 0.036(6) Uiso 1 1 d . . .
C26 C -0.1044(2) 0.00488(9) -0.2001(2) 0.0384(5) Uani 1 1 d . . .
H26 H -0.039(3) -0.0254(10) -0.178(3) 0.045(6) Uiso 1 1 d . . .
C27 C -0.2444(2) -0.00721(10) -0.2976(2) 0.0413(5) Uani 1 1 d . . .
H27 H -0.267(2) -0.0479(10) -0.337(3) 0.045(6) Uiso 1 1 d . . .
C28 C -0.3427(2) 0.03720(9) -0.3345(2) 0.0360(5) Uani 1 1 d . . .
H28 H -0.442(3) 0.0287(10) -0.397(3) 0.052(7) Uiso 1 1 d . . .
C29 C -0.30452(18) 0.09391(8) -0.27648(18) 0.0251(4) Uani 1 1 d . . .
C30 C -0.41771(18) 0.14099(8) -0.32551(18) 0.0262(4) Uani 1 1 d . . .
C31 C -0.48351(19) 0.14777(9) -0.48569(19) 0.0300(4) Uani 1 1 d . . .
C32 C -0.5363(2) 0.15364(10) -0.6138(2) 0.0382(5) Uani 1 1 d . . .
H32 H -0.582(3) 0.1582(13) -0.720(4) 0.084(9) Uiso 1 1 d . . .
O22 O -0.53108(14) 0.12168(7) -0.29872(16) 0.0354(3) Uani 1 1 d . . .
H2B H -0.500(3) 0.1227(12) -0.214(3) 0.065(9) Uiso 1 1 d . . .
C33 C -0.3652(2) 0.20015(9) -0.25591(19) 0.0293(4) Uani 1 1 d . . .
H33 H -0.436(2) 0.2292(10) -0.285(2) 0.042(6) Uiso 1 1 d . . .
C34 C -0.2337(2) 0.21101(8) -0.15949(19) 0.0285(4) Uani 1 1 d . . .
H34 H -0.208(2) 0.2508(10) -0.123(3) 0.046(6) 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
C1 C2 C3 176.53(19) . . yes
O1 C3 C2 106.31(13) . . yes
O1 C3 C14 109.52(14) . . yes
C2 C3 C14 108.51(15) . . yes
O1 C3 C4 110.83(14) . . yes
C2 C3 C4 108.27(14) . . yes
C14 C3 C4 113.13(14) . . yes
C9 C4 C5 119.27(16) . . yes
C9 C4 C3 122.32(15) . . yes
C5 C4 C3 118.40(15) . . yes
C6 C5 C4 120.91(18) . . yes
C5 C6 C7 119.93(18) . . yes
C8 C7 C6 119.83(19) . . yes
C7 C8 C9 120.87(18) . . yes
C4 C9 C8 119.15(16) . . yes
C4 C9 C10 122.27(15) . . yes
C8 C9 C10 118.58(16) . . yes
O2 C10 C11 106.39(13) . . yes
O2 C10 C13 109.37(14) . . yes
C11 C10 C13 108.13(15) . . yes
O2 C10 C9 110.45(14) . . yes
C11 C10 C9 108.92(14) . . yes
C13 C10 C9 113.32(14) . . yes
C12 C11 C10 176.43(19) . . yes
C14 C13 C10 124.44(16) . . yes
C13 C14 C3 124.44(16) . . yes
C21 C22 C23 179.2(2) . . yes
O21 C23 C22 104.57(13) . . yes
O21 C23 C34 108.87(14) . . yes
C22 C23 C34 108.68(15) . . yes
O21 C23 C24 110.35(14) . . yes
C22 C23 C24 110.52(14) . . yes
C34 C23 C24 113.46(14) . . yes
C29 C24 C25 118.65(17) . . yes
C29 C24 C23 122.24(15) . . yes
C25 C24 C23 119.11(16) . . yes
C26 C25 C24 121.25(19) . . yes
C25 C26 C27 120.04(19) . . yes
C28 C27 C26 119.2(2) . . yes
C27 C28 C29 121.2(2) . . yes
C24 C29 C28 119.62(17) . . yes
C24 C29 C30 122.20(16) . . yes
C28 C29 C30 118.17(16) . . yes
O22 C30 C31 104.56(14) . . yes
O22 C30 C33 109.59(15) . . yes
C31 C30 C33 108.96(15) . . yes
O22 C30 C29 110.15(15) . . yes
C31 C30 C29 109.48(15) . . yes
C33 C30 C29 113.69(14) . . yes
C32 C31 C30 179.5(2) . . yes
C34 C33 C30 124.07(17) . . yes
C33 C34 C23 124.31(17) . . 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 C2 1.185(3) . yes
C2 C3 1.488(2) . yes
C3 O1 1.438(2) . yes
C3 C14 1.512(2) . yes
C3 C4 1.528(2) . yes
C4 C9 1.399(2) . yes
C4 C5 1.404(2) . yes
C5 C6 1.371(3) . yes
C6 C7 1.401(3) . yes
C7 C8 1.374(3) . yes
C8 C9 1.405(3) . yes
C9 C10 1.529(2) . yes
C10 O2 1.441(2) . yes
C10 C11 1.490(2) . yes
C10 C13 1.505(3) . yes
C11 C12 1.183(3) . yes
C13 C14 1.326(2) . yes
C21 C22 1.198(3) . yes
C22 C23 1.484(2) . yes
C23 O21 1.454(2) . yes
C23 C34 1.507(3) . yes
C23 C24 1.518(2) . yes
C24 C29 1.395(2) . yes
C24 C25 1.404(3) . yes
C25 C26 1.372(3) . yes
C26 C27 1.397(3) . yes
C27 C28 1.380(3) . yes
C28 C29 1.397(3) . yes
C29 C30 1.519(2) . yes
C30 O22 1.450(2) . yes
C30 C31 1.490(2) . yes
C30 C33 1.502(3) . yes
C31 C32 1.192(3) . yes
C33 C34 1.323(3) . yes
