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#$Date: 2016-11-06 05:42:49 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187990 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/05/2020589.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_2020589
loop_
_publ_author_name
'Bosch, Eric'
_publ_section_title
;
 Cocrystals of 1,4-diethynylbenzene with 1,3-diacetylbenzene and
 benzene-1,4-dicarbaldehyde exhibiting strong nonconventional
 alkyne--carbonyl C---H···O hydrogen bonds between
 the components
;
_journal_coeditor_code           FN3222
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              748
_journal_page_last               752
_journal_paper_doi               10.1107/S2053229616014972
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C10 H6, C10 H10 O2'
_chemical_formula_moiety         'C10 H6, C10 H10 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.33
_chemical_name_common
;
1,3-Diacetylbenzene--1,4-diethynylbenzene (1/1)
;
_chemical_name_systematic
;
1-(3-Acetylphenyl)ethan-1-one--1,4-diethynylbenzene (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 125.890(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.749(10)
_cell_length_b                   7.284(3)
_cell_length_c                   13.374(7)
_cell_measurement_reflns_used    2546
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.55
_cell_volume                     1558.6(13)
_computing_cell_refinement
;
SMART (Bruker, 2012)
;
_computing_data_collection
;
SMART (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2001)
;
_computing_publication_material
;
X-SEED (Barbour, 2001)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0788
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9573
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.242
_diffrn_reflns_theta_min         2.546
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       irregular
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1007P)²+0.1951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1588
_reflns_number_gt                1356
_reflns_number_total             1741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fn3222sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2020589--2020590.cif.'
_cod_database_code               2020589
_cod_database_fobs_code          2020589
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_occupancy
O O1 0.39785(6) 0.49943(17) 0.42438(9) 0.0420(4) Uani d 1
C C1 0.5000 0.7982(3) 0.7500 0.0418(5) Uani d 1
H H1 0.5000 0.9286 0.7500 0.050 Uiso calc 1
C C2 0.46566(9) 0.7038(2) 0.64051(14) 0.0367(4) Uani d 1
H H2 0.4423 0.7697 0.5657 0.044 Uiso calc 1
C C3 0.46517(8) 0.5125(2) 0.63941(12) 0.0292(4) Uani d 1
C C4 0.5000 0.4185(3) 0.7500 0.0290(5) Uani d 1
H H4 0.5000 0.2881 0.7500 0.035 Uiso calc 1
C C5 0.42691(9) 0.4141(2) 0.51946(13) 0.0314(4) Uani d 1
C C6 0.42518(11) 0.2082(2) 0.51840(14) 0.0445(4) Uani d 1
H H6A 0.3975 0.1640 0.4337 0.067 Uiso calc 1
H H6B 0.3944 0.1650 0.5506 0.067 Uiso calc 1
H H6C 0.4825 0.1611 0.5703 0.067 Uiso calc 1
C C7 0.25624(9) 1.4300(2) 0.03752(13) 0.0351(4) Uani d 1
H H7 0.2606 1.5537 0.0632 0.042 Uiso calc 1
C C8 0.28409(9) 1.2900(2) 0.12288(13) 0.0343(4) Uani d 1
H H8 0.3072 1.3177 0.2066 0.041 Uiso calc 1
C C9 0.27822(9) 1.1082(2) 0.08614(13) 0.0326(4) Uani d 1
C C10 0.30741(10) 0.9613(2) 0.17345(14) 0.0380(4) Uani d 1
C C11 0.33131(11) 0.8371(3) 0.24456(16) 0.0472(5) Uani d 1
H H11 0.3485(11) 0.740(3) 0.3019(16) 0.059(6) Uiso d 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'
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
C2 C1 C2 . 2_656 120.4(2)
C1 C2 C3 . . 120.29(15)
C4 C3 C2 . . 118.99(14)
C4 C3 C5 . . 121.89(14)
C2 C3 C5 . . 119.12(13)
C3 C4 C3 2_656 . 121.06(19)
O1 C5 C3 . . 120.58(14)
O1 C5 C6 . . 120.49(13)
C3 C5 C6 . . 118.92(12)
C8 C7 C9 . 7_575 120.83(14)
C7 C8 C9 . . 119.97(14)
C8 C9 C7 . 7_575 119.20(13)
C8 C9 C10 . . 120.80(14)
C7 C9 C10 7_575 . 120.00(14)
C11 C10 C9 . . 178.91(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C5 . 1.2154(17)
C1 C2 . 1.383(2)
C1 C2 2_656 1.383(2)
C2 C3 . 1.394(2)
C3 C4 . 1.3915(17)
C3 C5 . 1.496(2)
C4 C3 2_656 1.3915(17)
C5 C6 . 1.500(2)
C7 C8 . 1.382(2)
C7 C9 7_575 1.398(2)
C8 C9 . 1.394(2)
C9 C7 7_575 1.398(2)
C9 C10 . 1.432(2)
C10 C11 . 1.192(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11 O1 . 0.946(19) 2.200(19) 3.139(2) 171.8(16)
C8 H8 O1 1_565 0.95 2.71 3.607(3) 158.4
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_4
_geom_torsion
C2 C1 C2 C3 2_656 . 0.14(9)
C1 C2 C3 C4 . . -0.27(19)
C1 C2 C3 C5 . . 179.45(10)
C2 C3 C4 C3 . 2_656 0.14(9)
C5 C3 C4 C3 . 2_656 -179.58(13)
C4 C3 C5 O1 . . -179.06(11)
C2 C3 C5 O1 . . 1.2(2)
C4 C3 C5 C6 . . 0.77(18)
C2 C3 C5 C6 . . -178.94(14)
C9 C7 C8 C9 7_575 . 0.2(2)
C7 C8 C9 C7 . 7_575 -0.2(2)
C7 C8 C9 C10 . . 179.46(13)
