#------------------------------------------------------------------------------
#$Date: 2019-06-18 16:07:51 +0300 (Tue, 18 Jun 2019) $
#$Revision: 216071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/16/2021675.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_2021675
loop_
_publ_author_name
'Eugenia D. Voronova'
'Alexander A. Golovanov'
'Ivan S. Odin'
'Maksim A. Anisimov'
'Pavel V. Dorovatovskii'
'Yan V. Zubavichus'
'Anna V. Vologzhanina'
_publ_section_title
;
 Peculiarities of supramolecular organization of cyclic ketones with
 vinylacetylene fragments
;
_journal_coeditor_code           JX3023
_journal_issue                   12
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              1674
_journal_page_last               1683
_journal_paper_doi               10.1107/S2053229618015838
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C24 H18 O'
_chemical_formula_moiety         'C24 H18 O'
_chemical_formula_sum            'C24 H18 O'
_chemical_formula_weight         322.38
_chemical_name_systematic
;
2,6-Bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                90
_cell_angle_beta                 124.09(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.498(4)
_cell_length_b                   27.52(2)
_cell_length_c                   13.885(9)
_cell_measurement_reflns_used    160
_cell_measurement_temperature    120
_cell_measurement_theta_max      19.85
_cell_measurement_theta_min      3.54
_cell_volume                     1740(2)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2495
_diffrn_reflns_av_unetI/netI     0.1773
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31410
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.804
_diffrn_reflns_theta_min         1.919
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.293
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.2024
_refine_ls_R_factor_gt           0.0853
_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)+(0.0100P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                2379
_reflns_number_total             5336
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3c.cif
_cod_data_source_block           3c
_cod_database_code               2021675
_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   0.964
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2215(3) 0.38803(5) 0.43170(12) 0.0283(4) Uani d 1 . .
C C1 -0.0203(5) 0.49168(8) 0.69236(19) 0.0253(5) Uani d 1 . .
C C2 0.0487(5) 0.46686(8) 0.64072(19) 0.0255(5) Uani d 1 . .
C C3 0.1269(5) 0.43898(8) 0.57618(19) 0.0246(5) Uani d 1 . .
H H3 0.0025 0.4413 0.4938 0.030 Uiso calc 1 . .
C C4 0.3596(5) 0.40976(7) 0.62070(18) 0.0215(5) Uani d 1 . .
C C5 0.3993(5) 0.38318(7) 0.53697(18) 0.0213(5) Uani d 1 . .
C C6 0.6545(4) 0.35037(7) 0.58313(18) 0.0208(5) Uani d 1 . .
C C7 0.6980(5) 0.32912(8) 0.50745(18) 0.0242(5) Uani d 1 . .
H H7 0.5634 0.3365 0.4274 0.029 Uiso calc 1 . .
C C8 0.9293(5) 0.29653(8) 0.53765(18) 0.0256(5) Uani d 1 . .
C C9 1.1210(5) 0.26811(8) 0.56295(18) 0.0260(5) Uani d 1 . .
C C10 -0.0992(5) 0.52097(8) 0.75603(19) 0.0245(5) Uani d 1 . .
C C11 -0.3717(5) 0.54333(8) 0.7005(2) 0.0289(6) Uani d 1 . .
H H11 -0.5068 0.5396 0.6189 0.035 Uiso calc 1 . .
C C12 -0.4488(5) 0.57078(8) 0.7620(2) 0.0350(6) Uani d 1 . .
H H12 -0.6372 0.5856 0.7230 0.042 Uiso calc 1 . .
C C13 -0.2541(6) 0.57689(9) 0.8797(2) 0.0408(7) Uani d 1 . .
H H13 -0.3068 0.5963 0.9219 0.049 Uiso calc 1 . .
C C14 0.0170(6) 0.55503(10) 0.9364(2) 0.0468(7) Uani d 1 . .
H H14 0.1506 0.5591 1.0180 0.056 Uiso calc 1 . .
C C15 0.0961(6) 0.52717(9) 0.8753(2) 0.0387(7) Uani d 1 . .
H H15 0.2842 0.5122 0.9149 0.046 Uiso calc 1 . .
C C16 1.3528(5) 0.23453(7) 0.59615(19) 0.0233(5) Uani d 1 . .
C C17 1.3961(5) 0.21501(8) 0.5141(2) 0.0287(6) Uani d 1 . .
H H17 1.2690 0.2239 0.4346 0.034 Uiso calc 1 . .
C C18 1.6227(5) 0.18283(8) 0.5479(2) 0.0346(6) Uani d 1 . .
H H18 1.6492 0.1694 0.4913 0.042 Uiso calc 1 . .
C C19 1.8114(5) 0.16999(8) 0.6633(2) 0.0349(6) Uani d 1 . .
H H19 1.9683 0.1480 0.6863 0.042 Uiso calc 1 . .
C C20 1.7708(5) 0.18927(8) 0.7450(2) 0.0334(6) Uani d 1 . .
H H20 1.9007 0.1805 0.8244 0.040 Uiso calc 1 . .
C C21 1.5450(5) 0.22091(8) 0.71255(19) 0.0296(6) Uani d 1 . .
H H21 1.5187 0.2337 0.7697 0.036 Uiso calc 1 . .
C C22 0.8584(5) 0.34230(9) 0.71298(17) 0.0278(5) Uani d 1 . .
H H22A 1.0310 0.3639 0.7447 0.033 Uiso calc 1 . .
H H22B 0.9296 0.3083 0.7276 0.033 Uiso calc 1 . .
C C23 0.7109(5) 0.35207(8) 0.77629(18) 0.0284(6) Uani d 1 . .
H H23A 0.5543 0.3277 0.7524 0.034 Uiso calc 1 . .
H H23B 0.8569 0.3488 0.8611 0.034 Uiso calc 1 . .
C C24 0.5798(5) 0.40236(8) 0.74956(17) 0.0255(5) Uani d 1 . .
H H24A 0.7387 0.4267 0.7786 0.031 Uiso calc 1 . .
H H24B 0.4819 0.4076 0.7907 0.031 Uiso calc 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 C10 . . 179.0(3)
C1 C2 C3 . . 177.7(2)
C2 C3 H3 . . 117.1
C4 C3 C2 . . 125.8(2)
C4 C3 H3 . . 117.1
C3 C4 C5 . . 117.1(2)
C3 C4 C24 . . 123.6(2)
C5 C4 C24 . . 119.21(19)
O1 C5 C4 . . 120.6(2)
O1 C5 C6 . . 120.7(2)
C6 C5 C4 . . 118.68(19)
C5 C6 C22 . . 119.67(19)
C7 C6 C5 . . 118.09(19)
C7 C6 C22 . . 122.2(2)
C6 C7 H7 . . 117.6
C6 C7 C8 . . 124.9(2)
C8 C7 H7 . . 117.6
C9 C8 C7 . . 178.5(2)
C8 C9 C16 . . 178.5(2)
C11 C10 C1 . . 120.9(2)
C11 C10 C15 . . 118.7(2)
C15 C10 C1 . . 120.4(2)
C10 C11 H11 . . 119.6
C12 C11 C10 . . 120.8(2)
C12 C11 H11 . . 119.6
C11 C12 H12 . . 120.0
C13 C12 C11 . . 120.1(2)
C13 C12 H12 . . 120.0
C12 C13 H13 . . 120.0
C12 C13 C14 . . 120.1(2)
C14 C13 H13 . . 120.0
C13 C14 H14 . . 119.9
C13 C14 C15 . . 120.2(2)
C15 C14 H14 . . 119.9
C10 C15 H15 . . 120.0
C14 C15 C10 . . 120.1(2)
C14 C15 H15 . . 120.0
C17 C16 C9 . . 121.1(2)
C17 C16 C21 . . 118.5(2)
C21 C16 C9 . . 120.5(2)
C16 C17 H17 . . 119.9
C18 C17 C16 . . 120.3(2)
C18 C17 H17 . . 119.9
C17 C18 H18 . . 119.7
C17 C18 C19 . . 120.5(2)
C19 C18 H18 . . 119.7
C18 C19 H19 . . 120.2
C20 C19 C18 . . 119.6(2)
C20 C19 H19 . . 120.2
C19 C20 H20 . . 119.7
C21 C20 C19 . . 120.6(2)
C21 C20 H20 . . 119.7
C16 C21 H21 . . 119.7
C20 C21 C16 . . 120.6(2)
C20 C21 H21 . . 119.7
C6 C22 H22A . . 109.1
C6 C22 H22B . . 109.1
C6 C22 C23 . . 112.64(19)
H22A C22 H22B . . 107.8
C23 C22 H22A . . 109.1
C23 C22 H22B . . 109.1
C22 C23 H23A . . 109.5
C22 C23 H23B . . 109.5
H23A C23 H23B . . 108.0
C24 C23 C22 . . 110.91(19)
C24 C23 H23A . . 109.5
C24 C23 H23B . . 109.5
C4 C24 H24A . . 109.3
C4 C24 H24B . . 109.3
C23 C24 C4 . . 111.74(18)
C23 C24 H24A . . 109.3
C23 C24 H24B . . 109.3
H24A C24 H24B . . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C5 . 1.228(2)
C1 C2 . 1.195(3)
C1 C10 . 1.432(3)
C2 C3 . 1.417(3)
C3 H3 . 0.9500
C3 C4 . 1.334(3)
C4 C5 . 1.489(3)
C4 C24 . 1.510(3)
C5 C6 . 1.479(3)
C6 C7 . 1.336(3)
C6 C22 . 1.514(3)
C7 H7 . 0.9500
C7 C8 . 1.414(3)
C8 C9 . 1.196(3)
C9 C16 . 1.425(3)
C10 C11 . 1.387(3)
C10 C15 . 1.390(3)
C11 H11 . 0.9500
C11 C12 . 1.373(3)
C12 H12 . 0.9500
C12 C13 . 1.372(3)
C13 H13 . 0.9500
C13 C14 . 1.374(4)
C14 H14 . 0.9500
C14 C15 . 1.383(3)
C15 H15 . 0.9500
C16 C17 . 1.396(3)
C16 C21 . 1.398(3)
C17 H17 . 0.9500
C17 C18 . 1.379(3)
C18 H18 . 0.9500
C18 C19 . 1.380(3)
C19 H19 . 0.9500
C19 C20 . 1.379(3)
C20 H20 . 0.9500
C20 C21 . 1.370(3)
C21 H21 . 0.9500
C22 H22A . 0.9900
C22 H22B . 0.9900
C22 C23 . 1.517(3)
C23 H23A . 0.9900
C23 H23B . 0.9900
C23 C24 . 1.508(3)
C24 H24A . 0.9900
C24 H24B . 0.9900

_cod_database_fobs_code 2021675
