#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/21/2102179.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_2102179
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         'C15 H10 Cl2 O'
_chemical_formula_sum            'C15 H10 Cl2 O'
_chemical_formula_weight         277.13
_chemical_melting_point          72.5(5)
_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                117.268(1)
_cell_angle_beta                 99.257(1)
_cell_angle_gamma                96.726(1)
_cell_formula_units_Z            2
_cell_length_a                   5.7082(1)
_cell_length_b                   11.3645(2)
_cell_length_c                   11.5167(1)
_cell_measurement_reflns_used    500
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.17
_cell_measurement_theta_min      5.44
_cell_volume                     639.735(19)
_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 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4371
_diffrn_reflns_theta_full        27.31
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  0.332
_exptl_absorpt_correction_T_min  0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0378
_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)+(0.0467P)²+0.3533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                2617
_reflns_number_total             2826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0034.cif
_cod_data_source_block           3X
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '72-73' was changed to '72.5(5)' -
the average value was taken and precision was estimated.

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

The following automatic conversions were performed:

'_chemical_melting_point' value '72-73' was changed to '72.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        639.734(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2102179
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
H1 H 1.044(5) -0.109(3) 0.266(3) 0.051(7) Uiso 1 1 d
C1 C 1.0066(3) -0.02664(17) 0.30273(19) 0.0305(4) Uani 1 1 d
C2 C 0.9579(3) 0.08150(16) 0.35028(16) 0.0235(3) Uani 1 1 d
C3 C 0.9001(3) 0.21751(15) 0.40912(16) 0.0214(3) Uani 1 1 d
O1 O 1.1132(2) 0.31881(11) 0.44629(13) 0.0267(3) Uani 1 1 d
HA H 1.163(5) 0.298(2) 0.383(3) 0.040(6) Uiso 1 1 d
C4 C 0.8200(3) 0.24719(14) 0.53893(15) 0.0201(3) Uani 1 1 d
C5 C 0.9651(3) 0.34161(15) 0.66530(16) 0.0243(3) Uani 1 1 d
H5 H 1.126(4) 0.391(2) 0.673(2) 0.035(5) Uiso 1 1 d
C6 C 0.8855(3) 0.36662(16) 0.78075(17) 0.0270(3) Uani 1 1 d
H6 H 0.986(4) 0.430(2) 0.867(2) 0.029(5) Uiso 1 1 d
C7 C 0.6591(3) 0.29600(16) 0.76799(16) 0.0249(3) Uani 1 1 d
Cl1 Cl 0.04963(8) 0.26483(5) 0.05839(5) 0.03706(14) Uani 1 1 d
C8 C 0.5132(3) 0.20033(17) 0.64306(17) 0.0272(3) Uani 1 1 d
H8 H 0.357(4) 0.147(2) 0.632(2) 0.040(6) Uiso 1 1 d
C9 C 0.5949(3) 0.17631(17) 0.52931(16) 0.0252(3) Uani 1 1 d
H9 H 0.494(4) 0.110(2) 0.444(2) 0.036(6) Uiso 1 1 d
C10 C 0.6949(3) 0.22598(15) 0.31106(15) 0.0214(3) Uani 1 1 d
C11 C 0.6523(3) 0.35366(15) 0.33946(17) 0.0253(3) Uani 1 1 d
H11 H 0.751(4) 0.432(2) 0.414(2) 0.026(5) Uiso 1 1 d
C12 C 0.4577(3) 0.36638(17) 0.26036(17) 0.0276(3) Uani 1 1 d
H12 H 0.435(4) 0.455(2) 0.279(2) 0.036(6) Uiso 1 1 d
C13 C 0.3042(3) 0.25021(17) 0.15251(16) 0.0271(3) Uani 1 1 d
Cl2 Cl 0.55431(8) 0.32701(5) 0.91110(4) 0.03824(15) Uani 1 1 d
C14 C 0.3448(3) 0.12307(17) 0.12157(17) 0.0291(3) Uani 1 1 d
H14 H 0.247(4) 0.048(2) 0.050(2) 0.036(6) Uiso 1 1 d
C15 C 0.5417(3) 0.11124(16) 0.20127(17) 0.0264(3) Uani 1 1 d
H15 H 0.566(4) 0.025(2) 0.179(2) 0.029(5) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0236(7) 0.0274(8) 0.0405(9) 0.0149(7) 0.0108(7) 0.0084(6)
C2 0.0164(6) 0.0271(7) 0.0270(8) 0.0134(6) 0.0064(5) 0.0029(5)
C3 0.0176(6) 0.0196(6) 0.0249(7) 0.0097(6) 0.0058(5) 0.0004(5)
O1 0.0208(5) 0.0248(5) 0.0316(6) 0.0119(5) 0.0099(5) -0.0018(4)
C4 0.0175(6) 0.0192(6) 0.0254(7) 0.0118(6) 0.0062(5) 0.0048(5)
C5 0.0210(7) 0.0214(7) 0.0271(8) 0.0103(6) 0.0041(6) 0.0016(5)
C6 0.0289(8) 0.0225(7) 0.0246(8) 0.0083(6) 0.0040(6) 0.0046(6)
C7 0.0259(7) 0.0293(7) 0.0255(7) 0.0153(6) 0.0103(6) 0.0139(6)
Cl1 0.0344(2) 0.0452(3) 0.0350(2) 0.0229(2) 0.00330(18) 0.01327(19)
C8 0.0186(7) 0.0352(8) 0.0312(9) 0.0185(7) 0.0075(6) 0.0057(6)
C9 0.0175(7) 0.0299(8) 0.0253(8) 0.0124(6) 0.0035(6) 0.0006(6)
C10 0.0208(7) 0.0216(7) 0.0230(7) 0.0111(6) 0.0082(5) 0.0034(5)
C11 0.0268(7) 0.0205(7) 0.0280(8) 0.0115(6) 0.0074(6) 0.0027(6)
C12 0.0301(8) 0.0252(7) 0.0330(8) 0.0176(7) 0.0103(7) 0.0078(6)
C13 0.0259(7) 0.0359(8) 0.0252(8) 0.0184(7) 0.0086(6) 0.0090(6)
Cl2 0.0370(2) 0.0542(3) 0.0297(2) 0.0204(2) 0.01751(18) 0.0189(2)
C14 0.0290(8) 0.0283(8) 0.0237(8) 0.0087(7) 0.0034(6) 0.0047(6)
C15 0.0275(8) 0.0222(7) 0.0265(8) 0.0095(6) 0.0060(6) 0.0054(6)
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 H1 179.0(17)
C1 C2 C3 179.12(17)
O1 C3 C2 109.98(12)
O1 C3 C4 106.71(12)
C2 C3 C4 109.22(12)
O1 C3 C10 110.68(12)
C2 C3 C10 111.25(12)
C4 C3 C10 108.87(12)
C3 O1 HA 106.2(19)
C5 C4 C9 119.18(14)
C5 C4 C3 122.08(13)
C9 C4 C3 118.74(13)
C4 C5 C6 120.45(14)
C4 C5 H5 119.4(13)
C6 C5 H5 120.2(13)
C7 C6 C5 119.10(15)
C7 C6 H6 120.6(12)
C5 C6 H6 120.3(13)
C8 C7 C6 121.27(15)
C8 C7 Cl2 118.85(12)
C6 C7 Cl2 119.88(13)
C9 C8 C7 119.00(15)
C9 C8 H8 118.4(14)
C7 C8 H8 122.6(14)
C8 C9 C4 120.99(15)
C8 C9 H9 118.5(14)
C4 C9 H9 120.5(13)
C15 C10 C11 119.32(15)
C15 C10 C3 122.36(13)
C11 C10 C3 118.18(13)
C12 C11 C10 120.56(15)
C12 C11 H11 118.5(12)
C10 C11 H11 121.0(12)
C11 C12 C13 119.19(15)
C11 C12 H12 119.5(14)
C13 C12 H12 121.3(14)
C14 C13 C12 121.21(15)
C14 C13 Cl1 119.30(13)
C12 C13 Cl1 119.45(13)
C13 C14 C15 119.21(15)
C13 C14 H14 120.6(14)
C15 C14 H14 120.1(14)
C10 C15 C14 120.50(15)
C10 C15 H15 121.5(13)
C14 C15 H15 118.0(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.183(2)
C1 H1 0.90(3)
C2 C3 1.479(2)
C3 O1 1.4287(17)
C3 C4 1.534(2)
C3 C10 1.535(2)
O1 HA 0.77(3)
C4 C5 1.389(2)
C4 C9 1.394(2)
C5 C6 1.391(2)
C5 H5 0.99(2)
C6 C7 1.387(2)
C6 H6 0.95(2)
C7 C8 1.384(2)
C7 Cl2 1.7415(16)
Cl1 C13 1.7404(17)
C8 C9 1.381(2)
C8 H8 0.97(2)
C9 H9 0.95(2)
C10 C15 1.389(2)
C10 C11 1.395(2)
C11 C12 1.385(2)
C11 H11 0.93(2)
C12 C13 1.389(2)
C12 H12 0.95(2)
C13 C14 1.379(2)
C14 C15 1.393(2)
C14 H14 0.90(2)
C15 H15 0.93(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 195714
