#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010194.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_2010194
loop_
_publ_author_name
'Lindeman, Sergey V.'
'Struchkov, Yuri T.'
'Guryshev, Vyacheslav N.'
_publ_contact_author
;
Dr. Sergey V. Lindeman
Institute of Organoelement Compounds
28 Vavilov St.,
Moscow 117813
Russia
;
_publ_section_title
;
 5-Acetyl[2.2]paracyclophane
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1747
_journal_page_last               1749
_journal_paper_doi               10.1107/S0108270194003264
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C18 H18 O1'
_chemical_formula_sum            'C18 H18 O'
_chemical_formula_weight         250.32
_chemical_name_common            monoacetylparacyclophane
_chemical_name_systematic        ' 4-acetyl(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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.17(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.724(3)
_cell_length_b                   7.621(2)
_cell_length_c                   11.844(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      11
_cell_volume                     1323.6(5)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL-Plus (PC Version) (Sheldrick, 1989)'
_diffrn_ambient_temperature      153(2)
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3892
_diffrn_reflns_theta_max         33.04
_diffrn_reflns_theta_min         2.78
_diffrn_standards_decay_%        2.5
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       'well-formed prisms'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.057
_refine_ls_goodness_of_fit_obs   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_restrained_S_obs      1.056
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_obs          0.0512
_refine_ls_shift/esd_max         0.147
_refine_ls_shift/esd_mean        0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fₒ²) + (0.0969P)² + 0.2841P] where P=(Fₒ² + 2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1668
_refine_ls_wR_factor_obs         0.1461
_reflns_number_observed          3343
_reflns_number_total             3771
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            hu1077.cif
_cod_data_source_block           z5sva
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' calc
w=1/[\s^2^(F~o~^2^) + (0.0969P)^2^ + 0.2841P] where P=(F~o~^2^ +
2F~c~^2^)/3' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w=1/[\s^2^(F~o~^2^) + (0.0969P)^2^ + 0.2841P] where
P=(F~o~^2^ + 2F~c~^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C18 H18 O1'
_cod_database_code               2010194
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
C1 0.68273(8) 0.15250(14) 0.65165(10) 0.0274(2) Uani d . 1 . C
C2 0.65981(7) 0.05648(14) 0.74675(9) 0.0259(2) Uani d . 1 . C
C3 0.72487(8) 0.03463(15) 0.83931(9) 0.0267(2) Uani d . 1 . C
C4 0.81175(7) 0.1071(2) 0.84020(9) 0.0280(2) Uani d . 1 . C
C5 0.82361(8) 0.2367(2) 0.75984(11) 0.0310(2) Uani d . 1 . C
C6 0.76004(8) 0.25912(14) 0.66755(10) 0.0304(2) Uani d . 1 . C
C7 0.63974(10) 0.1257(2) 0.53202(11) 0.0379(3) Uani d . 1 . C
C8 0.67785(13) -0.0432(2) 0.47417(13) 0.0496(4) Uani d . 1 . C
C9 0.76203(10) -0.1165(2) 0.53935(11) 0.0370(3) Uani d . 1 . C
C10 0.75468(10) -0.2424(2) 0.62424(12) 0.0370(3) Uani d . 1 . C
C11 0.82170(10) -0.2579(2) 0.71410(11) 0.0361(3) Uani d . 1 . C
C12 0.89799(9) -0.1487(2) 0.72201(11) 0.0349(3) Uani d . 1 . C
C13 0.91427(10) -0.0547(2) 0.62481(12) 0.0376(3) Uani d . 1 . C
C14 0.84738(11) -0.0386(2) 0.53487(11) 0.0390(3) Uani d . 1 . C
C15 0.94745(11) -0.1035(3) 0.83575(14) 0.0484(4) Uani d . 1 . C
C16 0.89244(9) 0.0251(2) 0.90810(12) 0.0378(3) Uani d . 1 . C
C17 0.57123(9) -0.0395(2) 0.74588(12) 0.0356(3) Uani d . 1 . C
C18 0.52467(11) -0.0402(2) 0.8536(2) 0.0460(4) Uani d . 1 . C
O1 0.53722(9) -0.1125(2) 0.66124(10) 0.0608(4) Uani d . 1 . O
H3 0.7121(11) -0.046(2) 0.9016(13) 0.030(4) Uiso d . 1 . H
H5 0.8802(11) 0.299(2) 0.7631(14) 0.042(4) Uiso d . 1 . H
H6 0.7744(12) 0.336(2) 0.6054(14) 0.043(4) Uiso d . 1 . H
H7A 0.5722(13) 0.105(3) 0.5306(14) 0.044(5) Uiso d . 1 . H
H7B 0.6542(13) 0.225(3) 0.4847(16) 0.056(5) Uiso d . 1 . H
H8A 0.6897(16) -0.005(3) 0.396(2) 0.072(7) Uiso d . 1 . H
H8B 0.6273(16) -0.129(3) 0.4742(18) 0.070(7) Uiso d . 1 . H
H10 0.6978(13) -0.306(3) 0.6242(14) 0.050(5) Uiso d . 1 . H
H11 0.8123(13) -0.329(3) 0.7810(15) 0.051(5) Uiso d . 1 . H
H13 0.9720(13) 0.022(2) 0.6268(15) 0.046(5) Uiso d . 1 . H
H14 0.8563(14) 0.041(3) 0.4704(16) 0.048(5) Uiso d . 1 . H
H15A 1.0102(17) -0.046(3) 0.8245(18) 0.069(6) Uiso d . 1 . H
H15B 0.9572(17) -0.212(4) 0.881(2) 0.083(7) Uiso d . 1 . H
H16A 0.9360(14) 0.122(3) 0.9369(16) 0.054(5) Uiso d . 1 . H
H16B 0.8721(13) -0.044(3) 0.9734(16) 0.048(5) Uiso d . 1 . H
H18A 0.5649(18) -0.086(4) 0.919(2) 0.083(7) Uiso d . 1 . H
H18B 0.4736(19) -0.103(4) 0.843(2) 0.086(8) Uiso d . 1 . H
H18C 0.514(2) 0.084(4) 0.878(2) 0.097(9) 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
_geom_angle_publ_flag
C6 C1 C2 116.42(11) yes
C6 C1 C7 118.14(11) yes
C2 C1 C7 124.64(11) yes
C3 C2 C1 119.45(10) yes
C3 C2 C17 118.84(10) yes
C1 C2 C17 121.35(11) yes
C4 C3 C2 121.48(10) yes
C3 C4 C5 116.59(11) yes
C3 C4 C16 121.22(12) yes
C5 C4 C16 121.09(11) yes
C6 C5 C4 120.62(10) yes
C5 C6 C1 121.29(11) yes
C1 C7 C8 112.33(11) yes
C9 C8 C7 112.73(12) yes
C14 C9 C10 116.54(13) yes
C14 C9 C8 121.66(14) yes
C10 C9 C8 120.54(14) yes
C11 C10 C9 120.82(13) yes
C10 C11 C12 120.85(12) yes
C11 C12 C13 116.65(13) yes
C11 C12 C15 121.06(13) yes
C13 C12 C15 120.90(14) yes
C14 C13 C12 121.01(13) yes
C13 C14 C9 120.81(12) yes
C12 C15 C16 113.37(11) yes
C4 C16 C15 112.77(11) yes
O1 C17 C2 121.64(13) yes
O1 C17 C18 120.93(13) yes
C2 C17 C18 117.43(12) 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
C1 C6 . 1.397(2) yes
C1 C2 . 1.409(2) yes
C1 C7 . 1.513(2) yes
C2 C3 . 1.399(2) yes
C2 C17 . 1.495(2) yes
C3 C4 . 1.393(2) yes
C4 C5 . 1.393(2) yes
C4 C16 . 1.509(2) yes
C5 C6 . 1.384(2) yes
C7 C8 . 1.585(2) yes
C9 C10 . 1.401(2) yes
C10 C11 . 1.390(2) yes
C11 C12 . 1.395(2) yes
C12 C13 . 1.395(2) yes
C12 C15 . 1.512(2) yes
C13 C14 . 1.389(2) yes
C15 C16 . 1.574(2) yes
C17 O1 . 1.214(2) 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
_geom_torsion_publ_flag
C3 C4 C16 C15 94.8(2) yes
C4 C16 C15 C12 -12.3(2) yes
C16 C15 C12 C11 -71.7(2) yes
C15 C12 C11 C10 152.12(12) ?
C11 C10 C9 C8 -152.80(13) ?
C10 C9 C8 C7 89.8(2) yes
C9 C8 C7 C1 -12.8(2) yes
C8 C7 C1 C2 -76.9(2) yes
C7 C1 C2 C3 152.85(11) ?
C5 C4 C16 C15 -72.9(2) yes
C16 C15 C12 C13 94.4(2) yes
C14 C9 C8 C7 -77.0(2) yes
C8 C7 C1 C6 92.50(15) yes
C9 C10 C11 C12 -0.1(2) yes
C10 C11 C12 C13 -14.6(2) yes
C11 C12 C13 C14 14.7(2) yes
C12 C13 C14 C9 -0.1(2) yes
C1 C2 C3 C4 0.6(2) yes
C2 C3 C4 C5 15.7(2) yes
C3 C4 C5 C6 -15.8(2) yes
C4 C5 C6 C1 -0.4(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2746441
