#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017475.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_2017475
loop_
_publ_author_name
'Bakowicz, Julia'
'Turowska-Tyrk, Ilona'
_publ_section_title
;
 Monitoring structural transformations in crystals. 13. On
 photocyclization in 2,3,4,5,6-pentamethylbenzophenone,
 1,3-diphenylbutan-1-one and 2,4,6-triisopropyl-4'-methoxybenzophenone
;
_journal_coeditor_code           GZ3170
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o29
_journal_page_last               o32
_journal_paper_doi               10.1107/S0108270109052858
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H20 O'
_chemical_formula_moiety         'C18 H20 O'
_chemical_formula_sum            'C18 H20 O'
_chemical_formula_weight         252.34
_chemical_name_systematic
;
2,3,4,5,6-pentamethylbenzophenone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.28(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3784(15)
_cell_length_b                   12.793(2)
_cell_length_c                   18.014(5)
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.68
_cell_measurement_theta_min      2.80
_cell_volume                     1458.1(6)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Kuma KM-4 CCD diffractometer'
_diffrn_measurement_method       'ω 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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7742
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1124P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                1751
_reflns_number_total             2553
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gz3170.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017475
_cod_database_fobs_code          2017475
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1217(3) 0.48343(12) 0.23147(10) 0.0904(6) Uani d . 1 . .
C C1 0.2385(3) 0.47419(14) 0.18363(11) 0.0530(5) Uani d . 1 . .
C C2 0.2922(3) 0.36765(14) 0.15748(10) 0.0444(5) Uani d . 1 . .
C C3 0.4785(3) 0.31976(14) 0.19035(10) 0.0468(5) Uani d . 1 . .
C C4 0.5255(3) 0.21971(14) 0.16754(11) 0.0509(5) Uani d . 1 . .
C C5 0.3858(3) 0.16787(15) 0.11418(10) 0.0536(5) Uani d . 1 . .
C C6 0.2003(3) 0.21668(15) 0.08186(10) 0.0549(5) Uani d . 1 . .
C C7 0.1537(3) 0.31763(15) 0.10326(11) 0.0502(5) Uani d . 1 . .
C C8 0.6199(3) 0.37545(19) 0.25120(13) 0.0691(6) Uani d . 1 . .
H H8A 0.6419 0.3319 0.2949 0.104 Uiso calc R 1 . .
H H8B 0.5544 0.4397 0.2634 0.104 Uiso calc R 1 . .
H H8C 0.7533 0.3903 0.2341 0.104 Uiso calc R 1 . .
C C9 0.7268(3) 0.16752(19) 0.20307(14) 0.0751(7) Uani d . 1 . .
H H9A 0.8384 0.2182 0.2102 0.113 Uiso calc R 1 . .
H H9B 0.7649 0.1127 0.1710 0.113 Uiso calc R 1 . .
H H9C 0.7044 0.1386 0.2506 0.113 Uiso calc R 1 . .
C C10 0.4354(5) 0.05735(19) 0.09262(15) 0.0874(8) Uani d . 1 . .
H H10A 0.5479 0.0582 0.0619 0.131 Uiso calc R 1 . .
H H10B 0.3119 0.0264 0.0652 0.131 Uiso calc R 1 . .
H H10C 0.4777 0.0172 0.1370 0.131 Uiso calc R 1 . .
C C11 0.0473(4) 0.1600(2) 0.02402(14) 0.0895(8) Uani d . 1 . .
H H11A -0.0805 0.2000 0.0138 0.134 Uiso calc R 1 . .
H H11B 0.0153 0.0925 0.0429 0.134 Uiso calc R 1 . .
H H11C 0.1104 0.1518 -0.0213 0.134 Uiso calc R 1 . .
C C12 -0.0445(3) 0.3729(2) 0.06800(14) 0.0760(7) Uani d . 1 . .
H H12A -0.0510 0.4413 0.0894 0.114 Uiso calc R 1 . .
H H12B -0.1665 0.3333 0.0772 0.114 Uiso calc R 1 . .
H H12C -0.0415 0.3789 0.0150 0.114 Uiso calc R 1 . .
C C13 0.3258(3) 0.56766(14) 0.14940(10) 0.0454(5) Uani d . 1 . .
C C14 0.4642(3) 0.55909(16) 0.09658(10) 0.0535(5) Uani d . 1 . .
H H14 0.5038 0.4934 0.0812 0.064 Uiso calc R 1 . .
C C15 0.5438(3) 0.64792(18) 0.06656(12) 0.0658(6) Uani d . 1 . .
H H15 0.6359 0.6421 0.0307 0.079 Uiso calc R 1 . .
C C16 0.4867(3) 0.74431(17) 0.08979(12) 0.0664(6) Uani d . 1 . .
H H16 0.5409 0.8040 0.0697 0.080 Uiso calc R 1 . .
C C17 0.3507(3) 0.75374(16) 0.14225(12) 0.0674(6) Uani d . 1 . .
H H17 0.3121 0.8197 0.1575 0.081 Uiso calc R 1 . .
C C18 0.2710(3) 0.66603(15) 0.17239(11) 0.0577(5) Uani d . 1 . .
H H18 0.1797 0.6727 0.2085 0.069 Uiso calc R 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
_geom_angle_publ_flag
O1 C1 C13 . . 120.82(17) ?
O1 C1 C2 . . 119.85(17) ?
C13 C1 C2 . . 119.32(15) ?
C7 C2 C3 . . 121.77(17) ?
C7 C2 C1 . . 119.42(16) ?
C3 C2 C1 . . 118.78(16) ?
C4 C3 C2 . . 118.78(16) ?
C4 C3 C8 . . 121.31(17) ?
C2 C3 C8 . . 119.88(17) ?
C3 C4 C5 . . 120.01(17) ?
C3 C4 C9 . . 118.95(18) ?
C5 C4 C9 . . 121.02(19) ?
C4 C5 C6 . . 120.55(18) ?
C4 C5 C10 . . 119.14(19) ?
C6 C5 C10 . . 120.31(19) ?
C7 C6 C5 . . 119.91(17) ?
C7 C6 C11 . . 119.5(2) ?
C5 C6 C11 . . 120.6(2) ?
C2 C7 C6 . . 118.95(17) ?
C2 C7 C12 . . 120.18(19) ?
C6 C7 C12 . . 120.86(19) ?
C3 C8 H8A . . 109.5 ?
C3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C4 C9 H9A . . 109.5 ?
C4 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C4 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C5 C10 H10A . . 109.5 ?
C5 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C5 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C6 C11 H11A . . 109.5 ?
C6 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C6 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 119.08(17) ?
C14 C13 C1 . . 121.86(17) ?
C18 C13 C1 . . 119.05(16) ?
C13 C14 C15 . . 120.17(19) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C16 C15 C14 . . 119.8(2) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.6(2) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C16 C17 C18 . . 120.1(2) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C17 C18 C13 . . 120.34(19) ?
C17 C18 H18 . . 119.8 ?
C13 C18 H18 . . 119.8 ?
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 C1 . 1.214(2) ?
C1 C13 . 1.486(2) ?
C1 C2 . 1.496(2) ?
C2 C7 . 1.387(3) ?
C2 C3 . 1.400(2) ?
C3 C4 . 1.389(3) ?
C3 C8 . 1.507(3) ?
C4 C5 . 1.393(3) ?
C4 C9 . 1.515(3) ?
C5 C6 . 1.398(3) ?
C5 C10 . 1.510(3) ?
C6 C7 . 1.391(3) ?
C6 C11 . 1.518(3) ?
C7 C12 . 1.516(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.382(3) ?
C13 C18 . 1.384(3) ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.366(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.367(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.372(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 453381
