#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102182.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_2102182
loop_
_publ_author_name
'Bilton, Clair'
'Howard, Judith A. K.'
'Madhavi, N. N. L.'
'Nangia, Ashwini'
'Desiraju, Gautam R.'
'Allen, Frank H.'
'Wilson, Chick C.'
_publ_section_title
;
 Crystal engineering in the gem-alkynol family; synthon
 repetitivity and topological similarity in diphenylethynylmethanols:
 structures that lack O---H···O hydrogen bonds
;
_journal_coeditor_code           BM0034
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1071
_journal_page_last               1079
_journal_paper_doi               10.1107/S010876810001154X
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C27 H20 O'
_chemical_formula_sum            'C27 H20 O'
_chemical_formula_weight         360.43
_chemical_melting_point          157
_chemical_name_systematic
; 
 ? 
;
_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                100.450(2)
_cell_angle_beta                 97.790(2)
_cell_angle_gamma                95.477(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6413(3)
_cell_length_b                   10.2599(5)
_cell_length_c                   17.3238(9)
_cell_measurement_reflns_used    927
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      10.15
_cell_volume                     969.51(9)
_computing_cell_refinement       'Bruker SMART (Bruker Systems Inc., 1999a)'
_computing_data_collection       'Bruker SMART (Bruker Systems Inc., 1999a)'
_computing_data_reduction        'Bruker SAINT (Bruker Systems Inc., 1999b)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 'not relevant'
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12424
_diffrn_reflns_theta_full        30.45
_diffrn_reflns_theta_max         30.45
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(XPREP in SHELX97; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0759
_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)+(0.1193P)²+0.5780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2336
_reflns_number_gt                3419
_reflns_number_total             5270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0034.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2102182
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 0.0423(4) -0.0743(3) 0.29797(15) 0.0354(5) Uani 1 1 d . . .
H1 H -0.037(6) -0.155(3) 0.2918(18) 0.049(8) Uiso 1 1 d . . .
C2 C 0.1443(4) 0.0348(2) 0.30668(13) 0.0297(5) Uani 1 1 d . . .
C3 C 0.2633(4) 0.1735(2) 0.31647(13) 0.0277(4) Uani 1 1 d . . .
O1 O 0.0883(3) 0.26591(16) 0.32794(10) 0.0326(4) Uani 1 1 d . . .
H1A H -0.003(8) 0.238(4) 0.360(3) 0.096(14) Uiso 1 1 d . . .
C4 C 0.3638(4) 0.1901(2) 0.24024(13) 0.0275(4) Uani 1 1 d . . .
C5 C 0.2812(6) 0.2778(3) 0.19456(17) 0.0510(8) Uani 1 1 d . . .
H5 H 0.149(7) 0.331(4) 0.211(2) 0.085(12) Uiso 1 1 d . . .
C6 C 0.3804(7) 0.2913(4) 0.12649(19) 0.0662(10) Uani 1 1 d . . .
H6 H 0.294(8) 0.355(4) 0.093(3) 0.098(14) Uiso 1 1 d . . .
C7 C 0.5632(4) 0.2191(2) 0.10295(15) 0.0387(5) Uiso 1 1 d . A .
C8 C 0.6933(12) 0.2569(7) 0.0337(4) 0.0444(16) Uiso 0.50 1 d P . .
C9 C 0.7488(13) 0.1532(8) -0.0184(4) 0.0479(17) Uiso 0.50 1 d P A 1
C11 C 0.8695(17) 0.1854(10) -0.0857(6) 0.070(2) Uiso 0.50 1 d P A 1
C10 C 0.9392(17) 0.3032(10) -0.0909(6) 0.079(2) Uiso 0.50 1 d P A 1
C12 C 0.9046(16) 0.4169(8) -0.0341(5) 0.076(2) Uiso 0.50 1 d P . 1
C13 C 0.7765(13) 0.3910(7) 0.0277(4) 0.0614(16) Uiso 0.50 1 d P A 1
C8A C 0.6508(10) 0.2181(6) 0.0279(3) 0.0345(13) Uiso 0.50 1 d P . .
C9A C 0.8893(16) 0.1860(9) 0.0183(5) 0.0309(18) Uiso 0.25 1 d P A 2
C10A C 0.984(2) 0.1971(11) -0.0516(7) 0.045(2) Uiso 0.25 1 d P A 2
C11A C 0.776(3) 0.2539(14) -0.1172(8) 0.051(4) Uiso 0.25 1 d P A 2
C12A C 0.595(2) 0.2654(12) -0.1054(7) 0.051(3) Uiso 0.25 1 d P A 2
C13A C 0.5090(19) 0.2510(11) -0.0363(7) 0.042(2) Uiso 0.25 1 d P A 2
C9B C 0.755(2) 0.1131(15) -0.0142(9) 0.047(3) Uiso 0.25 1 d P A 3
C10B C 0.8428(18) 0.1373(12) -0.0838(6) 0.032(2) Uiso 0.25 1 d P A 3
C11B C 0.857(2) 0.2489(10) -0.1105(6) 0.0241(19) Uiso 0.25 1 d P A 3
C12B C 0.758(2) 0.3675(13) -0.0672(8) 0.054(3) Uiso 0.25 1 d P A 3
C13B C 0.654(2) 0.3512(11) -0.0001(7) 0.044(2) Uiso 0.25 1 d P A 3
C14 C 0.6400(5) 0.1299(3) 0.14867(16) 0.0410(6) Uani 1 1 d . . .
H14 H 0.770(6) 0.076(3) 0.134(2) 0.064(10) Uiso 1 1 d . . .
C15 C 0.5424(5) 0.1155(3) 0.21671(17) 0.0418(6) Uani 1 1 d . A .
H15 H 0.594(5) 0.052(3) 0.2491(19) 0.051(8) Uiso 1 1 d . . .
C16 C 0.4697(4) 0.2080(2) 0.38763(13) 0.0265(4) Uani 1 1 d . . .
C17 C 0.5842(4) 0.1103(2) 0.41913(14) 0.0302(5) Uani 1 1 d . . .
H17 H 0.528(5) 0.014(3) 0.3960(16) 0.034(7) Uiso 1 1 d . . .
C18 C 0.7747(4) 0.1467(2) 0.48245(14) 0.0291(5) Uani 1 1 d . . .
H18 H 0.844(5) 0.079(3) 0.5071(16) 0.033(6) Uiso 1 1 d . . .
C19 C 0.8535(3) 0.2812(2) 0.51612(12) 0.0248(4) Uani 1 1 d . . .
C20 C 1.0514(3) 0.3190(2) 0.58493(12) 0.0247(4) Uani 1 1 d . . .
C21 C 1.2571(4) 0.2522(2) 0.58795(14) 0.0287(5) Uani 1 1 d . . .
H21 H 1.280(4) 0.184(3) 0.5441(16) 0.030(6) Uiso 1 1 d . . .
C22 C 1.4380(4) 0.2851(2) 0.65346(15) 0.0342(5) Uani 1 1 d . . .
H22 H 1.568(5) 0.238(3) 0.6546(18) 0.047(8) Uiso 1 1 d . . .
C23 C 1.4181(5) 0.3860(3) 0.71682(16) 0.0414(6) Uani 1 1 d . . .
H23 H 1.546(6) 0.409(3) 0.761(2) 0.063(10) Uiso 1 1 d . . .
C24 C 1.2180(4) 0.4552(3) 0.71411(15) 0.0385(6) Uani 1 1 d . . .
H24 H 1.204(5) 0.529(3) 0.7583(19) 0.049(8) Uiso 1 1 d . . .
C25 C 1.0358(4) 0.4217(2) 0.64876(14) 0.0299(5) Uani 1 1 d . . .
H25 H 0.895(5) 0.470(2) 0.6447(15) 0.032(6) Uiso 1 1 d . . .
C26 C 0.7358(4) 0.3784(2) 0.48418(13) 0.0262(4) Uani 1 1 d . . .
H26 H 0.789(5) 0.472(3) 0.5058(16) 0.032(6) Uiso 1 1 d . . .
C27 C 0.5500(4) 0.3425(2) 0.42013(13) 0.0272(4) Uani 1 1 d . . .
H27 H 0.480(4) 0.413(2) 0.3993(15) 0.029(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_3
C2 C1 H1 179(2) .
C1 C2 C3 177.7(2) .
O1 C3 C2 109.60(17) .
O1 C3 C4 107.55(17) .
C2 C3 C4 109.28(18) .
O1 C3 C16 109.25(16) .
C2 C3 C16 111.68(18) .
C4 C3 C16 109.38(16) .
C3 O1 H1A 107(3) .
C5 C4 C15 118.8(2) .
C5 C4 C3 121.7(2) .
C15 C4 C3 119.5(2) .
C4 C5 C6 119.8(2) .
C4 C5 H5 119(2) .
C6 C5 H5 121(2) .
C7 C6 C5 122.1(3) .
C7 C6 H6 124(2) .
C5 C6 H6 114(2) .
C14 C7 C6 117.2(2) .
C14 C7 C8A 118.5(3) .
C6 C7 C8A 123.7(3) .
C14 C7 C8 123.6(3) .
C6 C7 C8 118.6(3) .
C8A C7 C8 15.8(3) .
C13B C8 C9 110.1(8) .
C13B C8 C9A 119.4(8) .
C9 C8 C9A 39.6(5) .
C13B C8 C13 34.3(6) .
C9 C8 C13 119.2(7) .
C9A C8 C13 103.8(6) .
C13B C8 C13A 54.5(7) .
C9 C8 C13A 78.1(6) .
C9A C8 C13A 114.7(7) .
C13 C8 C13A 88.5(6) .
C13B C8 C7 125.4(7) .
C9 C8 C7 116.0(6) .
C9A C8 C7 114.6(6) .
C13 C8 C7 124.5(6) .
C13A C8 C7 108.4(6) .
C13B C8 C9B 122.2(9) .
C9 C8 C9B 12.3(6) .
C9A C8 C9B 38.7(6) .
C13 C8 C9B 130.0(7) .
C13A C8 C9B 85.3(7) .
C7 C8 C9B 104.4(7) .
C8A C9 C8 18.0(4) .
C8A C9 C11 132.2(8) .
C8 C9 C11 117.4(7) .
C10 C11 C9 122.5(8) .
C11 C10 C12 122.7(9) .
C13 C12 C10 116.5(8) .
C13 C12 C12 92.8(7) 2_765
C10 C12 C12 139.5(9) 2_765
C12 C13 C8 121.3(7) .
C12 C13 C8A 119.6(6) .
C8 C13 C8A 4.8(4) .
C9 C8A C13A 87.6(7) .
C9 C8A C9B 16.4(7) .
C13A C8A C9B 98.4(8) .
C9 C8A C9A 40.5(5) .
C13A C8A C9A 118.1(7) .
C9B C8A C9A 42.7(7) .
C9 C8A C7 142.1(6) .
C13A C8A C7 121.0(6) .
C9B C8A C7 125.9(7) .
C9A C8A C7 120.9(5) .
C9 C8A C13B 102.8(7) .
C13A C8A C13B 50.9(6) .
C9B C8A C13B 119.2(9) .
C9A C8A C13B 100.9(7) .
C7 C8A C13B 114.5(6) .
C9 C8A C13 103.2(6) .
C13A C8A C13 76.2(6) .
C9B C8A C13 117.8(7) .
C9A C8A C13 84.9(5) .
C7 C8A C13 107.3(4) .
C13B C8A C13 25.7(4) .
C10A C9A C8 117.0(8) .
C10A C9A C8A 121.1(8) .
C8 C9A C8A 17.4(3) .
C9A C10A C11A 110.2(9) .
C12A C11A C10A 121.6(13) .
C11A C12A C13A 125.9(14) .
C12A C13A C8A 122.6(9) .
C12A C13A C8 115.8(9) .
C8A C13A C8 17.1(4) .
C8A C9B C10B 116.2(12) .
C8A C9B C8 13.6(4) .
C10B C9B C8 107.3(11) .
C11B C10B C9B 128.0(11) .
C10B C11B C12B 119.0(9) .
C13B C12B C11B 117.3(11) .
C8 C13B C12B 121.1(10) .
C8 C13B C8A 13.4(4) .
C12B C13B C8A 120.1(9) .
C7 C14 C15 121.3(2) .
C7 C14 H14 120(2) .
C15 C14 H14 119(2) .
C4 C15 C14 120.8(2) .
C4 C15 H15 117.1(19) .
C14 C15 H15 122.1(19) .
C17 C16 C27 118.86(19) .
C17 C16 C3 122.48(19) .
C27 C16 C3 118.63(18) .
C16 C17 C18 120.3(2) .
C16 C17 H17 119.2(15) .
C18 C17 H17 120.4(15) .
C17 C18 C19 121.09(19) .
C17 C18 H18 120.2(15) .
C19 C18 H18 118.5(15) .
C18 C19 C26 117.96(19) .
C18 C19 C20 120.75(18) .
C26 C19 C20 121.27(18) .
C25 C20 C21 118.40(19) .
C25 C20 C19 120.66(18) .
C21 C20 C19 120.94(19) .
C22 C21 C20 120.7(2) .
C22 C21 H21 117.7(15) .
C20 C21 H21 121.6(15) .
C21 C22 C23 120.2(2) .
C21 C22 H22 118.8(19) .
C23 C22 H22 121.0(19) .
C22 C23 C24 119.9(2) .
C22 C23 H23 119(2) .
C24 C23 H23 121(2) .
C25 C24 C23 120.0(2) .
C25 C24 H24 119.4(17) .
C23 C24 H24 120.7(17) .
C24 C25 C20 120.8(2) .
C24 C25 H25 121.6(15) .
C20 C25 H25 117.5(15) .
C27 C26 C19 121.04(19) .
C27 C26 H26 119.4(15) .
C19 C26 H26 119.5(15) .
C26 C27 C16 120.68(19) .
C26 C27 H27 117.4(15) .
C16 C27 H27 121.9(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.182(3) .
C1 H1 0.89(3) .
C2 C3 1.485(3) .
C3 O1 1.441(2) .
C3 C4 1.536(3) .
C3 C16 1.541(3) .
O1 H1A 0.87(5) .
C4 C5 1.375(3) .
C4 C15 1.383(3) .
C5 C6 1.395(4) .
C5 H5 1.01(4) .
C6 C7 1.388(4) .
C6 H6 1.06(4) .
C7 C14 1.378(4) .
C7 C8A 1.451(6) .
C7 C8 1.576(7) .
C8 C13B 1.240(13) .
C8 C9 1.356(10) .
C8 C9A 1.409(11) .
C8 C13 1.436(10) .
C8 C13A 1.474(12) .
C8 C9B 1.649(16) .
C9 C8A 1.179(9) .
C9 C11 1.498(12) .
C11 C10 1.257(14) .
C10 C12 1.431(12) .
C12 C13 1.419(11) .
C12 C12 2.009(18) 2_765
C13 C8A 1.847(10) .
C8A C13A 1.391(12) .
C8A C9B 1.410(16) .
C8A C9A 1.439(10) .
C8A C13B 1.529(13) .
C9A C10A 1.406(15) .
C10A C11A 1.74(2) .
C11A C12A 1.078(18) .
C12A C13A 1.380(16) .
C9B C10B 1.418(18) .
C10B C11B 1.309(15) .
C11B C12B 1.507(16) .
C12B C13B 1.399(17) .
C14 C15 1.392(4) .
C14 H14 0.99(3) .
C15 H15 0.97(3) .
C16 C17 1.396(3) .
C16 C27 1.398(3) .
C17 C18 1.397(3) .
C17 H17 1.00(3) .
C18 C19 1.401(3) .
C18 H18 0.96(3) .
C19 C26 1.403(3) .
C19 C20 1.485(3) .
C20 C25 1.401(3) .
C20 C21 1.403(3) .
C21 C22 1.387(3) .
C21 H21 0.97(3) .
C22 C23 1.390(4) .
C22 H22 0.92(3) .
C23 C24 1.390(3) .
C23 H23 0.96(3) .
C24 C25 1.390(3) .
C24 H24 0.99(3) .
C25 H25 0.98(3) .
C26 C27 1.389(3) .
C26 H26 0.97(3) .
C27 H27 0.96(2) .
