#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017177.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_2017177
loop_
_publ_author_name
'Telzhensky, Marina'
'Kaftory, Menahem'
_publ_section_title
;
 Structural effects on the solid-state photodimerization of 2-pyridone
 derivatives in inclusion compounds
;
_journal_coeditor_code           FG3097
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o314
_journal_page_last               o320
_journal_paper_doi               10.1107/S010827010901751X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C30 H22 O2, 2C6 H7 N O'
_chemical_formula_moiety         'C30 H22 O2, 2(C6 H7 N O)'
_chemical_formula_sum            'C42 H36 N2 O4'
_chemical_formula_weight         632.73
_chemical_name_systematic
;1,1,6,6-tetraphenyl-2,4-hexdiyne-1,6-diol--4-methyl-2-(1H)-pyridone
 (1/2)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.71(3)
_cell_angle_beta                 111.54(2)
_cell_angle_gamma                95.87(2)
_cell_formula_units_Z            1
_cell_length_a                   8.640(2)
_cell_length_b                   10.203(2)
_cell_length_c                   11.403(3)
_cell_measurement_reflns_used    8509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.05
_cell_volume                     870.8(4)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-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  0.034
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8509
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             334.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.086(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0429
_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)+(0.0731P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                1947
_reflns_number_total             3215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fg3097.cif
_cod_data_source_block           II-c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2017177
_cod_database_fobs_code          2017177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.62987(16) 0.15238(11) 0.24833(12) 0.0502(4) Uani d . 1 . .
H H1O1 0.6312 0.1551 0.3213 0.060 Uiso calc R 1 . .
O O2 0.62699(18) 0.13777(15) 0.48594(15) 0.0700(4) Uani d . 1 . .
N N1 0.7118(2) -0.02291(18) 0.58322(17) 0.0632(5) Uani d . 1 . .
H H1N1 0.6061 -0.0638 0.5547 0.076 Uiso calc R 1 . .
C C1 0.9242(2) 0.45897(18) 0.44718(17) 0.0457(5) Uani d . 1 . .
C C2 0.7922(2) 0.38783(18) 0.35623(18) 0.0438(4) Uani d . 1 . .
C C3 0.63810(19) 0.29019(16) 0.24071(16) 0.0377(4) Uani d . 1 . .
C C4 0.65921(18) 0.28371(17) 0.11167(16) 0.0378(4) Uani d . 1 . .
C C5 0.6658(2) 0.16042(19) 0.02543(18) 0.0488(5) Uani d . 1 . .
H H5 0.6560 0.0780 0.0444 0.059 Uiso calc R 1 . .
C C6 0.6869(3) 0.1591(2) -0.0900(2) 0.0619(6) Uani d . 1 . .
H H6 0.6904 0.0753 -0.1482 0.074 Uiso calc R 1 . .
C C7 0.7026(3) 0.2794(2) -0.1192(2) 0.0643(6) Uani d . 1 . .
H H7 0.7187 0.2780 -0.1958 0.077 Uiso calc R 1 . .
C C8 0.6944(3) 0.4029(2) -0.0340(2) 0.0660(6) Uani d . 1 . .
H H8 0.7039 0.4850 -0.0536 0.079 Uiso calc R 1 . .
C C9 0.6723(2) 0.4046(2) 0.0800(2) 0.0553(5) Uani d . 1 . .
H H9 0.6660 0.4881 0.1366 0.066 Uiso calc R 1 . .
C C10 0.4727(2) 0.33443(18) 0.23599(17) 0.0415(4) Uani d . 1 . .
C C11 0.4676(3) 0.4546(2) 0.3267(2) 0.0573(5) Uani d . 1 . .
H H11 0.5691 0.5146 0.3951 0.069 Uiso calc R 1 . .
C C12 0.3115(3) 0.4873(3) 0.3172(3) 0.0781(7) Uani d . 1 . .
H H12 0.3091 0.5685 0.3792 0.094 Uiso calc R 1 . .
C C13 0.1615(3) 0.3993(3) 0.2161(3) 0.0877(9) Uani d . 1 . .
H H13 0.0575 0.4209 0.2099 0.105 Uiso calc R 1 . .
C C14 0.1646(3) 0.2806(3) 0.1246(3) 0.0817(8) Uani d . 1 . .
H H14 0.0626 0.2217 0.0560 0.098 Uiso calc R 1 . .
C C15 0.3185(2) 0.2475(2) 0.1335(2) 0.0595(6) Uani d . 1 . .
H H15 0.3194 0.1665 0.0704 0.071 Uiso calc R 1 . .
C C16 0.8338(3) -0.0784(3) 0.6539(2) 0.0758(7) Uani d . 1 . .
H H16 0.8017 -0.1597 0.6691 0.091 Uiso calc R 1 . .
C C17 1.0003(3) -0.0172(3) 0.7020(2) 0.0769(7) Uani d . 1 . .
H H17 1.0832 -0.0560 0.7500 0.092 Uiso calc R 1 . .
C C18 1.0489(3) 0.1056(2) 0.6797(2) 0.0676(6) Uani d . 1 . .
C C19 0.9245(3) 0.1592(2) 0.6076(2) 0.0647(6) Uani d . 1 . .
H H19 0.9561 0.2406 0.5925 0.078 Uiso calc R 1 . .
C C20 0.7493(3) 0.0947(2) 0.5554(2) 0.0584(5) Uani d . 1 . .
C C21 1.2355(3) 0.1750(3) 0.7349(3) 0.0949(8) Uani d . 1 . .
H H21A 1.2989 0.1044 0.7211 0.142 Uiso calc R 1 . .
H H22B 1.2770 0.2270 0.8294 0.142 Uiso calc R 1 . .
H H21C 1.2499 0.2379 0.6892 0.142 Uiso calc R 1 . .
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 H1O1 . . 109.5 ?
C16 N1 C20 . . 123.0(2) ?
C16 N1 H1N1 . . 118.5 ?
C20 N1 H1N1 . . 118.5 ?
C2 C1 C1 . 2_766 179.5(2) ?
C1 C2 C3 . . 174.69(19) ?
O1 C3 C2 . . 108.84(15) ?
O1 C3 C10 . . 109.47(12) ?
C2 C3 C10 . . 112.85(15) ?
O1 C3 C4 . . 107.53(14) ?
C2 C3 C4 . . 107.83(15) ?
C10 C3 C4 . . 110.17(13) ?
C5 C4 C9 . . 118.68(18) ?
C5 C4 C3 . . 121.74(16) ?
C9 C4 C3 . . 119.58(16) ?
C4 C5 C6 . . 120.04(19) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 120.82(19) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 119.5(2) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C9 C8 C7 . . 120.0(2) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C4 . . 121.03(19) ?
C8 C9 H9 . . 119.5 ?
C4 C9 H9 . . 119.5 ?
C11 C10 C15 . . 118.40(19) ?
C11 C10 C3 . . 123.75(16) ?
C15 C10 C3 . . 117.85(17) ?
C10 C11 C12 . . 120.5(2) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.9(2) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C14 C13 C12 . . 120.2(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.2(2) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C10 . . 120.7(2) ?
C14 C15 H15 . . 119.7 ?
C10 C15 H15 . . 119.7 ?
C17 C16 N1 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
N1 C16 H16 . . 119.7 ?
C16 C17 C18 . . 119.8(2) ?
C16 C17 H17 . . 120.1 ?
C18 C17 H17 . . 120.1 ?
C19 C18 C17 . . 118.7(2) ?
C19 C18 C21 . . 121.6(2) ?
C17 C18 C21 . . 119.7(2) ?
C18 C19 C20 . . 121.9(2) ?
C18 C19 H19 . . 119.1 ?
C20 C19 H19 . . 119.1 ?
O2 C20 N1 . . 118.82(19) ?
O2 C20 C19 . . 125.17(19) ?
N1 C20 C19 . . 116.01(19) ?
C18 C21 H21A . . 109.5 ?
C18 C21 H22B . . 109.5 ?
H21A C21 H22B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H22B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.430(2) ?
O1 H1O1 . 0.8200 ?
O2 C20 . 1.272(3) ?
N1 C16 . 1.357(3) ?
N1 C20 . 1.364(3) ?
N1 H1N1 . 0.8600 ?
C1 C2 . 1.197(2) ?
C1 C1 2_766 1.380(4) ?
C2 C3 . 1.479(3) ?
C3 C10 . 1.529(3) ?
C3 C4 . 1.532(3) ?
C4 C5 . 1.377(3) ?
C4 C9 . 1.386(3) ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.367(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.378(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.378(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.375(3) ?
C10 C15 . 1.395(3) ?
C11 C12 . 1.395(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.373(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.362(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.342(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.402(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.364(3) ?
C18 C21 . 1.504(3) ?
C19 C20 . 1.410(3) ?
C19 H19 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H22B . 0.9600 ?
C21 H21C . 0.9600 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C1 C2 C3 2_766 . . . -12E1(3) ?
C1 C2 C3 O1 . . . . 48.3(19) ?
C1 C2 C3 C10 . . . . 170.1(18) ?
C1 C2 C3 C4 . . . . -68.0(19) ?
O1 C3 C4 C5 . . . . 0.6(2) ?
C2 C3 C4 C5 . . . . 117.78(17) ?
C10 C3 C4 C5 . . . . -118.67(17) ?
O1 C3 C4 C9 . . . . -179.40(14) ?
C2 C3 C4 C9 . . . . -62.2(2) ?
C10 C3 C4 C9 . . . . 61.36(19) ?
C9 C4 C5 C6 . . . . 0.7(3) ?
C3 C4 C5 C6 . . . . -179.30(15) ?
C4 C5 C6 C7 . . . . 0.5(3) ?
C5 C6 C7 C8 . . . . -1.1(3) ?
C6 C7 C8 C9 . . . . 0.7(3) ?
C7 C8 C9 C4 . . . . 0.5(3) ?
C5 C4 C9 C8 . . . . -1.1(3) ?
C3 C4 C9 C8 . . . . 178.83(17) ?
O1 C3 C10 C11 . . . . 123.40(19) ?
C2 C3 C10 C11 . . . . 2.0(2) ?
C4 C3 C10 C11 . . . . -118.6(2) ?
O1 C3 C10 C15 . . . . -56.7(2) ?
C2 C3 C10 C15 . . . . -178.04(14) ?
C4 C3 C10 C15 . . . . 61.4(2) ?
C15 C10 C11 C12 . . . . 0.9(3) ?
C3 C10 C11 C12 . . . . -179.13(17) ?
C10 C11 C12 C13 . . . . -0.4(3) ?
C11 C12 C13 C14 . . . . -0.3(3) ?
C12 C13 C14 C15 . . . . 0.4(4) ?
C13 C14 C15 C10 . . . . 0.2(3) ?
C11 C10 C15 C14 . . . . -0.9(3) ?
C3 C10 C15 C14 . . . . 179.18(17) ?
C20 N1 C16 C17 . . . . 0.9(4) ?
N1 C16 C17 C18 . . . . 0.3(4) ?
C16 C17 C18 C19 . . . . -0.7(4) ?
C16 C17 C18 C21 . . . . 179.4(2) ?
C17 C18 C19 C20 . . . . 0.0(3) ?
C21 C18 C19 C20 . . . . 179.9(2) ?
C16 N1 C20 O2 . . . . 178.4(2) ?
C16 N1 C20 C19 . . . . -1.5(3) ?
C18 C19 C20 O2 . . . . -178.9(2) ?
C18 C19 C20 N1 . . . . 1.0(3) ?
