#------------------------------------------------------------------------------
#$Date: 2019-06-18 16:09:15 +0300 (Tue, 18 Jun 2019) $
#$Revision: 216076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/16/2021680.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_2021680
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          'C18 H20 O2'
_chemical_formula_moiety         'C18 H20 O2'
_chemical_formula_sum            'C18 H20 O2'
_chemical_formula_weight         268.34
_chemical_name_systematic
;
6-(3-Butylprop-2-yn-1-ylidene)-2-(furan-2-ylmethylene)cyclohexanone
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.218(3)
_cell_angle_beta                 70.882(3)
_cell_angle_gamma                66.632(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2801(14)
_cell_length_b                   9.5498(14)
_cell_length_c                   9.6407(14)
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.66
_cell_measurement_theta_min      2.32
_cell_volume                     740.63(19)
_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_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13735
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.053
_diffrn_reflns_theta_min         2.325
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.324
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                4496
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            5b.cif
_cod_data_source_block           5b
_cod_database_code               2021680
_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   0.970
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.23655(10) 0.69376(8) 0.12731(9) 0.02436(17) Uani d 1 . .
O O2 0.06610(10) 0.31249(8) 0.04610(9) 0.02500(17) Uani d 1 . .
C C1 0.33819(12) 0.58373(11) 0.16766(11) 0.01795(18) Uani d 1 . .
C C2 0.46380(12) 0.60414(11) 0.21891(11) 0.01820(18) Uani d 1 . .
C C3 0.60114(13) 0.46600(12) 0.24468(13) 0.0239(2) Uani d 1 . .
H H3A 0.6485 0.4939 0.3108 0.029 Uiso calc 1 . .
H H3B 0.6898 0.4268 0.1502 0.029 Uiso calc 1 . .
C C4 0.53785(15) 0.34239(12) 0.31322(13) 0.0248(2) Uani d 1 . .
H H4A 0.4514 0.3808 0.4090 0.030 Uiso calc 1 . .
H H4B 0.6297 0.2524 0.3310 0.030 Uiso calc 1 . .
C C5 0.46633(13) 0.29535(11) 0.21279(12) 0.0210(2) Uani d 1 . .
H H5A 0.5576 0.2404 0.1247 0.025 Uiso calc 1 . .
H H5B 0.4148 0.2239 0.2649 0.025 Uiso calc 1 . .
C C6 0.33968(12) 0.42801(11) 0.16475(11) 0.01714(18) Uani d 1 . .
C C7 0.22526(12) 0.41645(11) 0.11416(11) 0.01856(18) Uani d 1 . .
H H7 0.1503 0.5099 0.0905 0.022 Uiso calc 1 . .
C C8 0.20164(12) 0.28237(11) 0.09137(11) 0.01880(18) Uani d 1 . .
C C9 0.27716(13) 0.12861(11) 0.10131(12) 0.0217(2) Uani d 1 . .
H H9 0.3737 0.0765 0.1294 0.026 Uiso calc 1 . .
C C10 0.18437(14) 0.06108(12) 0.06178(13) 0.0259(2) Uani d 1 . .
H H10 0.2061 -0.0447 0.0588 0.031 Uiso calc 1 . .
C C11 0.05936(15) 0.17637(13) 0.02933(14) 0.0282(2) Uani d 1 . .
H H11 -0.0225 0.1639 -0.0012 0.034 Uiso calc 1 . .
C C12 0.44379(13) 0.74814(12) 0.24116(12) 0.0217(2) Uani d 1 . .
H H12 0.3501 0.8275 0.2242 0.026 Uiso calc 1 . .
C C13 0.55011(14) 0.79231(12) 0.28780(12) 0.0232(2) Uani d 1 . .
C C14 0.63463(14) 0.83827(13) 0.32581(13) 0.0250(2) Uani d 1 . .
C C15 0.73884(15) 0.88956(13) 0.37614(14) 0.0270(2) Uani d 1 . .
H H15A 0.6674 0.9664 0.4573 0.032 Uiso calc 1 . .
H H15B 0.7952 0.9402 0.2946 0.032 Uiso calc 1 . .
C C16 0.86873(14) 0.76120(13) 0.42901(13) 0.0250(2) Uani d 1 . .
H H16A 0.8134 0.7083 0.5088 0.030 Uiso calc 1 . .
H H16B 0.9435 0.6861 0.3471 0.030 Uiso calc 1 . .
C C17 0.96963(16) 0.82046(16) 0.48471(15) 0.0330(3) Uani d 1 . .
H H17A 0.8937 0.9013 0.5613 0.040 Uiso calc 1 . .
H H17B 1.0308 0.8670 0.4027 0.040 Uiso calc 1 . .
C C18 1.09177(17) 0.69700(19) 0.54821(16) 0.0439(4) Uani d 1 . .
H H18A 1.1686 0.6173 0.4726 0.066 Uiso calc 1 . .
H H18B 1.0318 0.6525 0.6314 0.066 Uiso calc 1 . .
H H18C 1.1539 0.7414 0.5817 0.066 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
C11 O2 C8 . . 106.96(8)
O1 C1 C2 . . 120.48(9)
O1 C1 C6 . . 120.95(9)
C6 C1 C2 . . 118.56(8)
C1 C2 C3 . . 119.03(9)
C12 C2 C1 . . 116.87(9)
C12 C2 C3 . . 124.09(9)
C2 C3 H3A . . 109.6
C2 C3 H3B . . 109.6
C2 C3 C4 . . 110.44(9)
H3A C3 H3B . . 108.1
C4 C3 H3A . . 109.6
C4 C3 H3B . . 109.6
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
C3 C4 C5 . . 110.80(9)
H4A C4 H4B . . 108.1
C5 C4 H4A . . 109.5
C5 C4 H4B . . 109.5
C4 C5 H5A . . 108.9
C4 C5 H5B . . 108.9
H5A C5 H5B . . 107.7
C6 C5 C4 . . 113.29(8)
C6 C5 H5A . . 108.9
C6 C5 H5B . . 108.9
C1 C6 C5 . . 119.92(9)
C7 C6 C1 . . 115.73(8)
C7 C6 C5 . . 124.33(9)
C6 C7 H7 . . 115.7
C6 C7 C8 . . 128.70(9)
C8 C7 H7 . . 115.7
O2 C8 C7 . . 113.56(8)
C9 C8 O2 . . 108.80(9)
C9 C8 C7 . . 137.64(10)
C8 C9 H9 . . 126.5
C8 C9 C10 . . 107.02(9)
C10 C9 H9 . . 126.5
C9 C10 H10 . . 126.8
C11 C10 C9 . . 106.45(9)
C11 C10 H10 . . 126.8
O2 C11 H11 . . 124.6
C10 C11 O2 . . 110.78(10)
C10 C11 H11 . . 124.6
C2 C12 H12 . . 117.1
C2 C12 C13 . . 125.79(10)
C13 C12 H12 . . 117.1
C14 C13 C12 . . 176.18(12)
C13 C14 C15 . . 177.80(12)
C14 C15 H15A . . 108.8
C14 C15 H15B . . 108.8
C14 C15 C16 . . 113.67(9)
H15A C15 H15B . . 107.7
C16 C15 H15A . . 108.8
C16 C15 H15B . . 108.8
C15 C16 H16A . . 109.3
C15 C16 H16B . . 109.3
H16A C16 H16B . . 107.9
C17 C16 C15 . . 111.74(10)
C17 C16 H16A . . 109.3
C17 C16 H16B . . 109.3
C16 C17 H17A . . 109.0
C16 C17 H17B . . 109.0
C16 C17 C18 . . 113.00(12)
H17A C17 H17B . . 107.8
C18 C17 H17A . . 109.0
C18 C17 H17B . . 109.0
C17 C18 H18A . . 109.5
C17 C18 H18B . . 109.5
C17 C18 H18C . . 109.5
H18A C18 H18B . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2317(12)
O2 C8 . 1.3793(12)
O2 C11 . 1.3540(13)
C1 C2 . 1.4892(14)
C1 C6 . 1.4847(13)
C2 C3 . 1.4947(14)
C2 C12 . 1.3424(14)
C3 H3A . 0.9900
C3 H3B . 0.9900
C3 C4 . 1.5211(15)
C4 H4A . 0.9900
C4 H4B . 0.9900
C4 C5 . 1.5248(15)
C5 H5A . 0.9900
C5 H5B . 0.9900
C5 C6 . 1.5026(13)
C6 C7 . 1.3494(14)
C7 H7 . 0.9500
C7 C8 . 1.4306(14)
C8 C9 . 1.3623(14)
C9 H9 . 0.9500
C9 C10 . 1.4169(15)
C10 H10 . 0.9500
C10 C11 . 1.3457(15)
C11 H11 . 0.9500
C12 H12 . 0.9500
C12 C13 . 1.4187(15)
C13 C14 . 1.1982(15)
C14 C15 . 1.4635(15)
C15 H15A . 0.9900
C15 H15B . 0.9900
C15 C16 . 1.5231(16)
C16 H16A . 0.9900
C16 H16B . 0.9900
C16 C17 . 1.5154(16)
C17 H17A . 0.9900
C17 H17B . 0.9900
C17 C18 . 1.5161(19)
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800

_cod_database_fobs_code 2021680
