#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/19/2001916.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_2001916
loop_
_publ_author_name
'Kharitonov, V. G.'
'Antonov, D. Yu.'
'Rozenberg, V. I.'
'Nikanorov, V. A.'
'Yanovsky, A. I.'
'Struchkov, Yu. T.'
_publ_contact_author
;
Dr. Alexander I. Yanovsky
Institute of Organoelement Compounds
28 Vavilov Street,
Moscow 117813
Russia
;
_publ_section_title
;
 4-[2-Benzoyl-1-(benzoylmethyl)ethyl][2.2]paracyclophane
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              612
_journal_page_last               615
_journal_paper_doi               10.1107/S010827019201076X
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C33 H30 O2'
_chemical_formula_sum            'C33 H30 O2'
_chemical_formula_weight         458.57
_chemical_name_systematic
;
4-[2-benzoyl-1-(benzoylmethyl)ethyl][2.2]paracyclophane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.77(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.032(3)
_cell_length_b                   21.366(4)
_cell_length_c                   9.041(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      13
_cell_volume                     2473.0(9)
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1992)'
_computing_structure_solution    'SHELXTL-PLUS (Sheldrick, 1987)'
_diffrn_ambient_temperature      293.0(10)
_diffrn_measurement_device       'Siemens P3/PC'
_diffrn_measurement_method       θ/2θ
_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  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5007
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       cubes
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.022
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     436
_refine_ls_number_reflns         4766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_obs          0.0458
_refine_ls_shift/esd_max         -0.038
_refine_ls_shift/esd_mean        0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[\s^2^(F~o~^2^)+(0.0553P)^2^+0.1277P]
where P = (F~o~^2^+2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1432
_refine_ls_wR_factor_obs         0.0984
_reflns_number_observed          2872
_reflns_number_total             4797
_reflns_observed_criterion       I>2sigma(I)
_cod_data_source_file            na1020.cif
_cod_data_source_block           chalcon
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               2001916
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.71976(12) 0.08376(8) 0.2614(2) 0.0734(10) Uani d . 1 . O
O2 0.44027(12) 0.20677(8) 0.2657(2) 0.0794(9) Uani d . 1 . O
C1 0.7883(2) 0.23729(13) 0.6642(5) 0.090(2) Uani d . 1 . C
H1A 0.810(3) 0.2722(18) 0.738(4) 0.153(14) Uiso d . 1 . H
H1B 0.782(3) 0.2571(16) 0.568(4) 0.145(13) Uiso d . 1 . H
C2 0.6776(2) 0.21628(11) 0.6841(3) 0.070(2) Uani d . 1 . C
H2A 0.655(2) 0.2411(14) 0.767(3) 0.118(10) Uiso d . 1 . H
H2B 0.627(2) 0.2308(12) 0.598(3) 0.103(9) Uiso d . 1 . H
C3 0.67028(14) 0.14678(9) 0.7152(2) 0.0515(10) Uani d . 1 . C
C4 0.64383(13) 0.10138(9) 0.6004(2) 0.0441(9) Uani d . 1 . C
C5 0.68464(14) 0.04148(9) 0.6283(2) 0.0460(10) Uani d . 1 . C
H5 0.6773(13) 0.0116(8) 0.545(2) 0.047(5) Uiso d . 1 . H
C6 0.74747(14) 0.02443(9) 0.7655(2) 0.0502(11) Uani d . 1 . C
C7 0.7480(2) 0.06489(10) 0.8845(2) 0.0562(12) Uani d . 1 . C
H7 0.7839(15) 0.0535(9) 0.987(2) 0.063(6) Uiso d . 1 . H
C8 0.7107(2) 0.12497(11) 0.8586(2) 0.0576(13) Uani d . 1 . C
H8 0.7205(14) 0.1539(9) 0.938(2) 0.059(6) Uiso d . 1 . H
C9 0.8263(2) -0.02765(11) 0.7763(3) 0.068(2) Uani d . 1 . C
H9A 0.799(2) -0.0612(13) 0.699(3) 0.100(9) Uiso d . 1 . H
H9B 0.8341(19) -0.0477(12) 0.875(3) 0.098(8) Uiso d . 1 . H
C10 0.9367(2) -0.00632(14) 0.7530(6) 0.099(2) Uani d . 1 . C
H10A 0.960(3) -0.0336(18) 0.673(4) 0.162(15) Uiso d . 1 . H
H10B 0.989(3) -0.0189(19) 0.827(5) 0.169(16) Uiso d . 1 . H
C11 0.9418(2) 0.06235(11) 0.7187(3) 0.0713(11) Uani d . 1 . C
C12 0.9020(2) 0.08447(13) 0.5758(3) 0.0688(12) Uani d . 1 . C
H12 0.8893(16) 0.0563(10) 0.495(3) 0.070(7) Uiso d . 1 . H
C13 0.8646(2) 0.14484(12) 0.5537(3) 0.0631(12) Uani d . 1 . C
H13 0.8257(16) 0.1581(10) 0.453(3) 0.074(7) Uiso d . 1 . H
C14 0.8666(2) 0.18516(10) 0.6747(3) 0.0639(13) Uani d . 1 . C
C15 0.9268(2) 0.16727(13) 0.8110(3) 0.0720(15) Uani d . 1 . C
H15 0.9330(18) 0.1952(11) 0.898(3) 0.084(8) Uiso d . 1 . H
C16 0.9637(2) 0.10696(13) 0.8327(3) 0.0773(14) Uani d . 1 . C
H16 0.9923(19) 0.0947(11) 0.933(3) 0.087(8) Uiso d . 1 . H
C17 0.57489(14) 0.12030(10) 0.4513(2) 0.0493(10) Uani d . 1 . C
H17 0.6069(14) 0.1550(9) 0.406(2) 0.050(5) Uiso d . 1 . H
C18 0.5548(2) 0.06838(12) 0.3335(2) 0.0558(11) Uani d . 1 . C
H18A 0.5221(15) 0.0331(9) 0.375(2) 0.053(5) Uiso d . 1 . H
H18B 0.5015(16) 0.0826(9) 0.249(2) 0.063(6) Uiso d . 1 . H
C19 0.6474(2) 0.04798(11) 0.2665(2) 0.0546(11) Uani d . 1 . C
C20 0.64774(15) -0.01695(10) 0.2051(2) 0.0530(12) Uani d . 1 . C
C21 0.7428(2) -0.04473(13) 0.1921(3) 0.0650(14) Uani d . 1 . C
H21 0.8053(17) -0.0194(10) 0.224(2) 0.069(6) Uiso d . 1 . H
C22 0.7449(2) -0.10425(13) 0.1337(3) 0.077(2) Uani d . 1 . C
H22 0.8114(19) -0.1226(11) 0.130(3) 0.089(8) Uiso d . 1 . H
C23 0.6538(2) -0.13644(14) 0.0852(3) 0.078(2) Uani d . 1 . C
H23 0.656(2) -0.1767(13) 0.048(3) 0.102(9) Uiso d . 1 . H
C24 0.5597(2) -0.10971(12) 0.0961(3) 0.075(2) Uani d . 1 . C
H24 0.4921(19) -0.1322(11) 0.063(3) 0.086(8) Uiso d . 1 . H
C25 0.5562(2) -0.05063(11) 0.1578(2) 0.0612(13) Uani d . 1 . C
H25 0.4876(18) -0.0313(10) 0.165(2) 0.078(7) Uiso d . 1 . H
C26 0.4688(2) 0.14215(12) 0.4835(2) 0.0543(11) Uani d . 1 . C
H26A 0.4271(16) 0.1066(10) 0.507(2) 0.070(6) Uiso d . 1 . H
H26B 0.4799(16) 0.1685(10) 0.571(3) 0.070(7) Uiso d . 1 . H
C27 0.40255(15) 0.17988(9) 0.3614(2) 0.0514(11) Uani d . 1 . C
C28 0.28769(14) 0.18372(8) 0.3601(2) 0.0468(10) Uani d . 1 . C
C29 0.2219(2) 0.20791(10) 0.2345(3) 0.0608(13) Uani d . 1 . C
H29 0.2554(15) 0.2240(9) 0.156(2) 0.064(6) Uiso d . 1 . H
C30 0.1155(2) 0.20840(12) 0.2274(3) 0.0745(14) Uani d . 1 . C
H30 0.0733(19) 0.2241(11) 0.141(3) 0.093(8) Uiso d . 1 . H
C31 0.0735(2) 0.18544(11) 0.3449(3) 0.0705(13) Uani d . 1 . C
H31 -0.003(2) 0.1861(10) 0.343(3) 0.089(7) Uiso d . 1 . H
C32 0.1367(2) 0.16267(11) 0.4706(3) 0.0640(13) Uani d . 1 . C
H32 0.1088(18) 0.1458(11) 0.553(3) 0.088(8) Uiso d . 1 . H
C33 0.2437(2) 0.16120(10) 0.4790(2) 0.0551(12) Uani d . 1 . C
H33 0.2880(15) 0.1454(9) 0.568(2) 0.061(6) Uiso 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 0.0033 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
_geom_angle_publ_flag
C14 C1 C2 . . 114.4(2) yes
C3 C2 C1 . . 113.3(2) yes
C8 C3 C4 . . 117.0(2) yes
C8 C3 C2 . . 118.5(2) yes
C4 C3 C2 . . 123.3(2) yes
C5 C4 C3 . . 117.7(2) yes
C5 C4 C17 . . 123.0(2) yes
C3 C4 C17 . . 119.2(2) yes
C4 C5 C6 . . 122.7(2) yes
C7 C6 C5 . . 116.4(2) yes
C7 C6 C9 . . 120.6(2) yes
C5 C6 C9 . . 121.9(2) yes
C8 C7 C6 . . 120.1(2) yes
C7 C8 C3 . . 122.2(2) yes
C6 C9 C10 . . 114.3(2) yes
C11 C10 C9 . . 113.0(2) yes
C12 C11 C16 . . 116.5(2) yes
C12 C11 C10 . . 120.2(3) yes
C16 C11 C10 . . 121.7(3) yes
C13 C12 C11 . . 121.0(3) yes
C12 C13 C14 . . 120.8(2) yes
C15 C14 C13 . . 116.9(2) yes
C15 C14 C1 . . 121.8(3) yes
C13 C14 C1 . . 119.9(2) yes
C16 C15 C14 . . 120.7(3) yes
C15 C16 C11 . . 121.1(2) yes
C18 C17 C4 . . 114.80(10) yes
C18 C17 C26 . . 108.00(10) yes
C4 C17 C26 . . 108.30(10) yes
C19 C18 C17 . . 116.3(2) yes
O1 C19 C20 . . 120.8(2) yes
O1 C19 C18 . . 120.9(2) yes
C20 C19 C18 . . 118.3(2) yes
C25 C20 C21 . . 118.5(2) yes
C25 C20 C19 . . 122.2(2) yes
C21 C20 C19 . . 119.3(2) yes
C22 C21 C20 . . 120.4(2) yes
C23 C22 C21 . . 120.4(3) yes
C22 C23 C24 . . 120.0(3) yes
C23 C24 C25 . . 120.4(3) yes
C24 C25 C20 . . 120.3(2) yes
C27 C26 C17 . . 115.9(2) yes
O2 C27 C28 . . 120.3(2) yes
O2 C27 C26 . . 121.5(2) yes
C28 C27 C26 . . 118.1(2) yes
C29 C28 C33 . . 118.6(2) yes
C29 C28 C27 . . 119.4(2) yes
C33 C28 C27 . . 122.0(2) yes
C30 C29 C28 . . 120.2(2) yes
C31 C30 C29 . . 120.3(2) yes
C32 C31 C30 . . 120.4(2) yes
C31 C32 C33 . . 120.0(2) yes
C32 C33 C28 . . 120.4(2) yes
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 C19 . 1.221(2) yes
O2 C27 . 1.216(2) yes
C1 C2 . 1.554(4) yes
C1 C14 . 1.501(4) yes
C2 C3 . 1.518(3) yes
C3 C4 . 1.415(3) yes
C3 C8 . 1.386(3) yes
C4 C5 . 1.391(3) yes
C4 C17 . 1.528(3) yes
C5 C6 . 1.401(3) yes
C6 C7 . 1.379(3) yes
C6 C9 . 1.505(3) yes
C7 C8 . 1.377(3) yes
C9 C10 . 1.560(4) yes
C10 C11 . 1.504(4) yes
C11 C12 . 1.382(3) yes
C11 C16 . 1.394(4) yes
C12 C13 . 1.380(3) yes
C13 C14 . 1.389(3) yes
C14 C15 . 1.385(3) yes
C15 C16 . 1.376(4) yes
C17 C18 . 1.526(2) yes
C17 C26 . 1.538(2) yes
C18 C19 . 1.512(3) yes
C19 C20 . 1.494(3) yes
C20 C25 . 1.391(3) yes
C20 C21 . 1.398(3) yes
C21 C22 . 1.379(4) yes
C22 C23 . 1.371(4) yes
C23 C24 . 1.373(3) yes
C24 C25 . 1.384(3) yes
C26 C27 . 1.503(3) yes
C27 C28 . 1.497(3) yes
C28 C29 . 1.388(3) yes
C28 C33 . 1.395(3) yes
C29 C30 . 1.377(3) yes
C30 C31 . 1.374(3) yes
C31 C32 . 1.363(3) yes
C32 C33 . 1.382(3) yes
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
C4 C17 C18 C19 . . . . -69.1(2) ?
C17 C18 C19 C20 . . . . 154.4(2) ?
C18 C19 C20 C21 . . . . -157.6(2) ?
C4 C17 C18 C19 . . . . -69.1(2) ?
C17 C18 C19 O1 . . . . -26.2(3) ?
C4 C17 C26 C27 . . . . 162.67(15) ?
C17 C26 C27 C28 . . . . 159.3(2) ?
C26 C27 C28 C29 . . . . -168.0(2) ?
C4 C17 C26 C27 . . . . 162.67(15) ?
C17 C26 C27 O2 . . . . -20.7(3) ?
C6 C9 C10 C11 . . . . -2.0(5) ?
C3 C2 C1 C14 . . . . 1.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21139825
