#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102180.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_2102180
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                117.240(1)
_cell_angle_beta                 99.250(1)
_cell_angle_gamma                96.860(1)
_cell_formula_units_Z            2
_cell_length_a                   5.7280(1)
_cell_length_b                   11.3620(2)
_cell_length_c                   11.5210(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150
_cell_volume                     641.866(19)
_computing_cell_refinement       'SXD (Keen & Wilson, 1996)'
_computing_data_collection       'SXD (Keen & Wilson, 1996)'
_computing_data_reduction        'SXD (Keen & Wilson, 1996)'
_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_measured_fraction_theta_full 0.197
_diffrn_measured_fraction_theta_max 0.197
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.5-5.0
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10674
_diffrn_reflns_theta_full        16.16
_diffrn_reflns_theta_max         16.16
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    '1.450 at 1 angstrom'
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
The linear absorption coefficient is wavelength dependent
 and it is calculated as:
          mu = 0.64 + 0.81 * lambda  [cm^-1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          1.5
_exptl_crystal_size_min          1.0
_refine_ls_extinction_coef       0.296
_refine_ls_extinction_method     'Becker-Coppens Lorentzian model'
_refine_ls_goodness_of_fit_ref   5.444
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      5.444
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0668
_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)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                2928
_reflns_number_total             2929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0034.cif
_cod_data_source_block           3N
_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        641.865(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2102180
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
C1 C 1.0047(4) -0.02661(18) 0.3033(2) 0.0333(5) Uani 1 1 d
C2 C 0.9559(3) 0.08311(16) 0.35113(19) 0.0223(4) Uani 1 1 d
C3 C 0.8984(3) 0.21786(15) 0.40894(17) 0.0187(3) Uani 1 1 d
O1 O 1.1102(4) 0.3181(2) 0.4452(3) 0.0268(5) Uani 1 1 d
C4 C 0.8194(3) 0.24703(14) 0.53838(16) 0.0171(3) Uani 1 1 d
C5 C 0.9649(3) 0.34106(16) 0.66423(18) 0.0236(4) Uani 1 1 d
C6 C 0.8860(4) 0.36646(17) 0.78000(19) 0.0269(4) Uani 1 1 d
C7 C 0.6603(3) 0.29618(17) 0.76792(18) 0.0236(4) Uani 1 1 d
Cl1 Cl 0.0542(3) 0.26511(16) 0.05897(17) 0.0421(4) Uani 1 1 d
C8 C 0.5148(4) 0.2012(2) 0.6435(2) 0.0278(4) Uani 1 1 d
C9 C 0.5950(3) 0.17659(18) 0.52866(19) 0.0247(4) Uani 1 1 d
C10 C 0.6940(3) 0.22635(15) 0.31199(17) 0.0193(3) Uani 1 1 d
C11 C 0.6513(4) 0.35329(16) 0.34004(19) 0.0248(4) Uani 1 1 d
C12 C 0.4579(4) 0.36662(18) 0.2611(2) 0.0282(4) Uani 1 1 d
C13 C 0.3053(4) 0.25032(18) 0.15295(19) 0.0266(4) Uani 1 1 d
Cl2 Cl 0.5579(3) 0.32699(17) 0.91032(17) 0.0434(4) Uani 1 1 d
C14 C 0.3467(4) 0.12323(18) 0.1226(2) 0.0299(4) Uani 1 1 d
C15 C 0.5422(4) 0.11157(17) 0.20187(19) 0.0265(4) Uani 1 1 d
H11 H 0.7679(9) 0.4433(4) 0.4257(5) 0.0482(12) Uani 1 1 d
H15 H 0.5713(10) 0.0116(4) 0.1802(5) 0.0514(13) Uani 1 1 d
H5 H 1.1370(10) 0.3966(5) 0.6715(5) 0.0532(12) Uani 1 1 d
H9 H 0.4800(9) 0.1024(5) 0.4320(5) 0.0549(12) Uani 1 1 d
H6 H 0.9997(11) 0.4397(5) 0.8769(5) 0.0602(14) Uani 1 1 d
H8 H 0.3403(10) 0.1454(6) 0.6355(6) 0.0570(13) Uani 1 1 d
H14 H 0.2271(10) 0.0345(5) 0.0377(5) 0.0556(13) Uani 1 1 d
H12 H 0.4225(10) 0.4649(4) 0.2825(5) 0.0560(14) Uani 1 1 d
HA H 1.1791(10) 0.2951(5) 0.3698(6) 0.0572(13) Uani 1 1 d
H1 H 1.0485(11) -0.1217(5) 0.2613(7) 0.0671(17) Uani 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 6.646 'International Tables Vol C Tables 4.4.4.1'
H H -3.739 'International Tables Vol C Tables 4.4.4.1'
O O 5.803 'International Tables Vol C Tables 4.4.4.1'
Cl Cl 9.577 'International Tables Vol C Tables 4.4.4.1'
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 179.4(5) .
C1 C2 C3 179.3(2) .
O1 C3 C2 109.59(16) .
O1 C3 C10 110.84(15) .
C2 C3 C10 111.64(14) .
O1 C3 C4 107.04(16) .
C2 C3 C4 108.89(13) .
C10 C3 C4 108.70(14) .
C3 O1 HA 109.4(4) .
C5 C4 C9 119.38(17) .
C5 C4 C3 121.94(16) .
C9 C4 C3 118.69(15) .
C4 C5 C6 120.45(18) .
C4 C5 H5 119.3(3) .
C6 C5 H5 120.2(3) .
C7 C6 C5 119.22(17) .
C7 C6 H6 120.9(4) .
C5 C6 H6 119.9(4) .
C8 C7 C6 120.99(19) .
C8 C7 Cl2 119.03(17) .
C6 C7 Cl2 119.98(15) .
C7 C8 C9 119.38(19) .
C7 C8 H8 120.3(4) .
C9 C8 H8 120.3(4) .
C8 C9 C4 120.58(17) .
C8 C9 H9 118.8(3) .
C4 C9 H9 120.6(3) .
C15 C10 C11 119.24(15) .
C15 C10 C3 122.25(13) .
C11 C10 C3 118.41(14) .
C12 C11 C10 120.99(16) .
C12 C11 H11 119.1(3) .
C10 C11 H11 119.9(3) .
C11 C12 C13 118.87(15) .
C11 C12 H12 121.6(3) .
C13 C12 H12 119.6(3) .
C14 C13 C12 120.92(16) .
C14 C13 Cl1 119.74(15) .
C12 C13 Cl1 119.29(13) .
C7 Cl2 Cl1 93.85(9) 1_656
C13 C14 C15 119.54(17) .
C13 C14 H14 119.7(3) .
C15 C14 H14 120.8(3) .
C14 C15 C10 120.42(14) .
C14 C15 H15 119.6(3) .
C10 C15 H15 119.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.200(2) .
C1 H1 1.044(4) .
C2 C3 1.467(2) .
C3 O1 1.420(3) .
C3 C10 1.528(2) .
C3 C4 1.529(3) .
O1 HA 0.951(7) .
C4 C5 1.385(2) .
C4 C9 1.390(3) .
C5 C6 1.393(3) .
C5 H5 1.074(6) .
C6 C7 1.386(3) .
C6 H6 1.072(5) .
C7 C8 1.378(3) .
C7 Cl2 1.729(3) .
Cl1 C13 1.730(2) .
C8 C9 1.389(3) .
C8 H8 1.084(6) .
C9 H9 1.075(5) .
C10 C15 1.388(2) .
C10 C11 1.388(2) .
C11 C12 1.385(3) .
C11 H11 1.080(5) .
C12 C13 1.389(3) .
C12 H12 1.080(4) .
C13 C14 1.382(2) .
Cl2 Cl1 3.394(2) 1_656
C14 C15 1.387(3) .
C14 H14 1.077(5) .
C15 H15 1.086(4) .
