#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/19/2101921.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_2101921
loop_
_publ_author_name
'Steiner, T.'
'Mason, S. A.'
'Tamm, M.'
_publ_section_title
;
 Neutron Diffraction Study of Aromatic Hydrogen Bonds:
 5-Ethynyl-5H-dibenzo[a,d]cyclohepten-5-ol at 20K
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              843
_journal_page_last               848
_journal_paper_doi               10.1107/S0108768197006174
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C17 H12 O'
_chemical_formula_sum            'C17 H12 O'
_chemical_formula_weight         232.28
_chemical_name_systematic
;
 5-ethynyl-5H-dibenzo[a,d]cyclohepten-5-ol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 94.951(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8097(9)
_cell_length_b                   8.2776(7)
_cell_length_c                   12.0030(10)
_cell_measurement_reflns_used    757
_cell_measurement_temperature    20
_cell_measurement_theta_max      50.4
_cell_measurement_theta_min      6.9
_cell_volume                     1168.99(17)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'D19 of the ILL'
_diffrn_measurement_method       ω
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'thermal neutron'
_diffrn_radiation_wavelength     1.31350
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2952
_diffrn_reflns_theta_max         50.30
_diffrn_reflns_theta_min         5.54
_diffrn_standards_interval_count '12 and 6 h'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       prisma
_exptl_crystal_F_000             356
_exptl_crystal_size_max          1.48
_exptl_crystal_size_mid          1.28
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.832
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.065
_refine_ls_goodness_of_fit_obs   1.113
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_restrained_S_obs      1.113
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_obs          0.0483
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0524P)²+6.2121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1207
_refine_ls_wR_factor_obs         0.1038
_reflns_number_observed          1551
_reflns_number_total             1939
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ka0035.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+6.2121P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+6.2121P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1169.0(2)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2101921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O 0.7162(2) 0.0610(3) 0.3086(2) 0.0089(5) Uani d 1 O
C1 0.9991(2) 0.3650(2) 0.1280(2) 0.0096(4) Uani d 1 C
C2 0.9471(2) 0.5058(2) 0.1624(2) 0.0096(4) Uani d 1 C
C3 0.8579(2) 0.4954(3) 0.2301(2) 0.0110(4) Uani d 1 C
C4 0.8181(2) 0.3446(2) 0.2604(2) 0.0094(4) Uani d 1 C
C5 0.8157(2) 0.0381(2) 0.2531(2) 0.0068(4) Uani d 1 C
C6 0.8676(2) -0.1133(2) 0.4345(2) 0.0097(4) Uani d 1 C
C7 0.9370(2) -0.2189(2) 0.5006(2) 0.0112(4) Uani d 1 C
C8 1.0377(2) -0.2752(2) 0.4634(2) 0.0107(4) Uani d 1 C
C9 1.0699(2) -0.2226(2) 0.3605(2) 0.0092(4) Uani d 1 C
C10 1.0475(2) -0.0672(2) 0.1881(2) 0.0084(4) Uani d 1 C
C11 1.0291(2) 0.0717(2) 0.1310(2) 0.0086(4) Uani d 1 C
C12 0.9625(2) 0.2110(2) 0.1625(2) 0.0069(4) Uani d 1 C
C13 0.86790(15) 0.2029(2) 0.2258(2) 0.0061(4) Uani d 1 C
C14 0.8988(2) -0.0631(2) 0.3300(2) 0.0077(4) Uani d 1 C
C15 1.0026(2) -0.1151(2) 0.2933(2) 0.0078(4) Uani d 1 C
C16 0.7844(2) -0.0520(2) 0.1478(2) 0.0081(4) Uani d 1 C
C17 0.7493(2) -0.1238(2) 0.0645(2) 0.0087(5) Uani d 1 C
H(O) 0.6533(5) 0.0744(7) 0.2567(5) 0.0315(10) Uani d 1 H
H1 1.0687(4) 0.3726(6) 0.0740(4) 0.0268(10) Uani d 1 H
H2 0.9776(4) 0.6225(5) 0.1357(4) 0.0266(10) Uani d 1 H
H3 0.8186(4) 0.6054(5) 0.2585(4) 0.0256(9) Uani d 1 H
H4 0.7461(4) 0.3370(5) 0.3104(4) 0.0224(9) Uani d 1 H
H6 0.7874(4) -0.0714(6) 0.4624(4) 0.0254(9) Uani d 1 H
H7 0.9091(4) -0.2579(6) 0.5811(4) 0.0294(10) Uani d 1 H
H8 1.0913(4) -0.3596(6) 0.5138(4) 0.0293(10) Uani d 1 H
H9 1.1496(4) -0.2673(6) 0.3316(4) 0.0280(10) Uani d 1 H
H10 1.1091(4) -0.1510(5) 0.1572(4) 0.0236(9) Uani d 1 H
H11 1.0768(4) 0.0916(5) 0.0586(4) 0.0241(9) Uani d 1 H
H17 0.7179(5) -0.1845(7) -0.0100(4) 0.0358(12) Uani d 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 '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
C5 O H(O) 110.3(4)
C2 C1 C12 120.7(2)
C2 C1 H1 120.1(3)
C12 C1 H1 119.2(3)
C3 C2 C1 119.8(2)
C3 C2 H2 121.0(3)
C1 C2 H2 119.2(3)
C2 C3 C4 120.0(2)
C2 C3 H3 119.8(3)
C4 C3 H3 120.2(3)
C13 C4 C3 121.0(2)
C13 C4 H4 119.3(3)
C3 C4 H4 119.7(3)
O C5 C16 108.2(2)
O C5 C14 107.7(2)
C16 C5 C14 109.66(15)
O C5 C13 110.2(2)
C16 C5 C13 109.7(2)
C14 C5 C13 111.27(15)
C7 C6 C14 120.5(2)
C7 C6 H6 120.5(3)
C14 C6 H6 119.0(3)
C8 C7 C6 120.3(2)
C8 C7 H7 121.0(3)
C6 C7 H7 118.7(3)
C7 C8 C9 119.2(2)
C7 C8 H8 120.6(3)
C9 C8 H8 120.2(3)
C8 C9 C15 121.7(2)
C8 C9 H9 118.9(3)
C15 C9 H9 119.4(3)
C11 C10 C15 127.9(2)
C11 C10 H10 117.0(3)
C15 C10 H10 114.9(3)
C10 C11 C12 127.5(2)
C10 C11 H11 117.6(3)
C12 C11 H11 114.4(3)
C13 C12 C1 118.5(2)
C13 C12 C11 124.9(2)
C1 C12 C11 116.6(2)
C4 C13 C12 119.8(2)
C4 C13 C5 119.6(2)
C12 C13 C5 120.5(2)
C6 C14 C15 119.6(2)
C6 C14 C5 119.7(2)
C15 C14 C5 120.6(2)
C9 C15 C14 118.7(2)
C9 C15 C10 116.0(2)
C14 C15 C10 125.2(2)
C17 C16 C5 174.3(2)
C16 C17 H17 178.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C5 1.412(3)
O H(O) 0.934(8)
C1 C2 1.397(3)
C1 C12 1.419(3)
C1 H1 1.092(5)
C2 C3 1.387(3)
C2 H2 1.088(4)
C3 C4 1.393(3)
C3 H3 1.091(4)
C4 C13 1.392(3)
C4 H4 1.084(4)
C5 C16 1.486(3)
C5 C14 1.536(2)
C5 C13 1.545(2)
C6 C7 1.397(3)
C6 C14 1.400(3)
C6 H6 1.088(5)
C7 C8 1.388(3)
C7 H7 1.096(5)
C8 C9 1.392(3)
C8 H8 1.090(4)
C9 C15 1.401(3)
C9 H9 1.096(4)
C10 C11 1.346(3)
C10 C15 1.466(3)
C10 H10 1.093(4)
C11 C12 1.464(3)
C11 H11 1.088(4)
C12 C13 1.405(3)
C14 C15 1.406(3)
C16 C17 1.206(3)
C17 H17 1.064(5)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C12 C1 C2 C3 -0.6(3)
C1 C2 C3 C4 -2.2(3)
C2 C3 C4 C13 1.4(3)
C14 C6 C7 C8 0.0(3)
C6 C7 C8 C9 1.3(3)
C7 C8 C9 C15 -0.5(3)
C15 C10 C11 C12 2.1(3)
C2 C1 C12 C13 4.2(3)
C2 C1 C12 C11 -174.3(2)
C10 C11 C12 C13 -30.2(3)
C10 C11 C12 C1 148.2(2)
C3 C4 C13 C12 2.3(3)
C3 C4 C13 C5 -175.2(2)
C1 C12 C13 C4 -5.0(3)
C11 C12 C13 C4 173.4(2)
C1 C12 C13 C5 172.5(2)
C11 C12 C13 C5 -9.1(3)
O C5 C13 C4 2.6(2)
C16 C5 C13 C4 121.7(2)
C14 C5 C13 C4 -116.8(2)
O C5 C13 C12 -174.8(2)
C16 C5 C13 C12 -55.8(2)
C14 C5 C13 C12 65.7(2)
C7 C6 C14 C15 -2.2(3)
C7 C6 C14 C5 173.4(2)
O C5 C14 C6 -0.2(2)
C16 C5 C14 C6 -117.7(2)
C13 C5 C14 C6 120.7(2)
O C5 C14 C15 175.4(2)
C16 C5 C14 C15 57.8(2)
C13 C5 C14 C15 -63.7(2)
C8 C9 C15 C14 -1.7(3)
C8 C9 C15 C10 178.9(2)
C6 C14 C15 C9 3.0(3)
C5 C14 C15 C9 -172.6(2)
C6 C14 C15 C10 -177.6(2)
C5 C14 C15 C10 6.8(3)
C11 C10 C15 C9 -151.7(2)
C11 C10 C15 C14 28.9(3)
O C5 C16 C17 6.(2)
C14 C5 C16 C17 123.1(19)
C13 C5 C16 C17 -114.4(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8736938
