#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1516179
loop_
_publ_author_name
'Rosokha, S. V.'
'Dibrov, S. M.'
'Rosokha, T. Y.'
'Kochi, J. K.'
_publ_section_title
;
 Electronic structures of intermolecular charge-transfer states in fast
 electron transfers with tetrathiafulvalene donor. Thermal and
 photoactivation of [2 + 4] cycloaddition to o-chloranil acceptor.
;
_journal_issue                   10
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              914
_journal_page_last               924
_journal_paper_doi               10.1039/b607431f
_journal_volume                  5
_journal_year                    2006
_chemical_formula_moiety         'c10 H14, C6 Cl4 O2'
_chemical_formula_sum            'C16 H14 Cl4 O2'
_chemical_formula_weight         380.07
_chemical_name_systematic
;
durene tetrachloro-o-benzoquinnone
;
_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                 100.2020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1022(5)
_cell_length_b                   13.8161(8)
_cell_length_c                   13.3595(8)
_cell_measurement_reflns_used    5137
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.84
_cell_measurement_theta_min      2.71
_cell_volume                     1653.49(17)
_computing_cell_refinement       'SAINT V6.28 (BrukerAXS, 1997-2001)'
_computing_data_collection       'SMART V5.630 (BrukerAXS, 1997-2001)'
_computing_data_reduction        'SAINT & SADABS V2.06 (Sheldrick, 2000)'
_computing_molecular_graphics    'XP V5.06 (BrukerAXS, 1997-99)'
_computing_publication_material  'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)'
_computing_structure_refinement  'SHELXTL v. 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL v. 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5361
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         31.96
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Semi-empirical (SADABS procedure)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.5673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                4919
_reflns_number_total             5361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607431f.txt
_cod_data_source_block           ros-psx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1653.49(16)
_cod_original_sg_symbol_H-M      'P2(1)/n '
_cod_database_code               1516179
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl 0.16968(3) 0.08699(3) 0.22050(3) 0.04179(10) Uani 1 1 d
Cl2 Cl 0.44505(4) 0.22336(2) 0.25103(3) 0.03743(9) Uani 1 1 d
Cl3 Cl 0.76310(3) 0.14428(2) 0.27537(2) 0.03332(8) Uani 1 1 d
Cl4 Cl 0.82359(4) -0.08047(3) 0.28300(3) 0.04184(10) Uani 1 1 d
O1 O 0.54195(12) -0.19052(7) 0.25545(8) 0.0375(2) Uani 1 1 d
O2 O 0.25997(11) -0.11812(8) 0.22260(8) 0.0374(2) Uani 1 1 d
C1 C 0.52458(13) -0.10373(8) 0.25315(9) 0.0273(2) Uani 1 1 d
C2 C 0.36426(13) -0.06276(8) 0.23558(9) 0.0277(2) Uani 1 1 d
C3 C 0.34712(12) 0.04303(9) 0.23625(9) 0.0269(2) Uani 1 1 d
C4 C 0.46782(12) 0.10119(8) 0.24940(9) 0.0244(2) Uani 1 1 d
C5 C 0.62086(12) 0.06244(8) 0.26342(9) 0.0242(2) Uani 1 1 d
C6 C 0.64793(12) -0.03360(8) 0.26589(9) 0.0266(2) Uani 1 1 d
C1A C 0.39684(13) 0.07285(9) -0.01519(10) 0.0295(2) Uani 1 1 d
C2A C 0.54750(14) 0.09699(9) -0.00455(9) 0.0288(2) Uani 1 1 d
C3A C 0.65350(12) 0.02209(10) 0.01126(9) 0.0292(2) Uani 1 1 d
C4A C 0.5949(2) 0.20099(11) -0.00849(12) 0.0416(3) Uani 1 1 d
C5A C 0.81784(14) 0.04329(14) 0.02492(12) 0.0427(3) Uani 1 1 d
C1B C 0.39475(13) 0.07171(8) 0.49298(9) 0.0272(2) Uani 1 1 d
C2B C 0.54541(13) 0.09742(8) 0.51476(9) 0.0268(2) Uani 1 1 d
C3B C 0.65342(12) 0.02389(9) 0.52230(9) 0.0267(2) Uani 1 1 d
C4B C 0.59034(18) 0.20187(10) 0.52890(12) 0.0366(3) Uani 1 1 d
C5B C 0.81721(14) 0.04698(12) 0.54459(12) 0.0373(3) Uani 1 1 d
H1A H 0.326(2) 0.1233(15) -0.0278(14) 0.044(5) Uiso 1 1 d
H4AA H 0.510(3) 0.2435(18) -0.0208(17) 0.068(7) Uiso 1 1 d
H4AB H 0.657(2) 0.2206(15) 0.0537(16) 0.053(6) Uiso 1 1 d
H4AC H 0.649(2) 0.2130(15) -0.0644(15) 0.051(5) Uiso 1 1 d
H5AA H 0.871(3) -0.0198(19) 0.0368(18) 0.067(7) Uiso 1 1 d
H5AB H 0.851(2) 0.0878(15) 0.0817(16) 0.055(6) Uiso 1 1 d
H5AC H 0.843(2) 0.0736(15) -0.0349(15) 0.050(5) Uiso 1 1 d
H1B H 0.322(2) 0.1233(15) 0.4897(14) 0.043(5) Uiso 1 1 d
H4BA H 0.650(2) 0.2234(16) 0.4806(16) 0.057(6) Uiso 1 1 d
H4BB H 0.503(2) 0.2434(16) 0.5208(15) 0.054(6) Uiso 1 1 d
H4BC H 0.645(2) 0.2135(15) 0.5929(15) 0.049(5) Uiso 1 1 d
H5BA H 0.844(2) 0.0819(14) 0.6071(15) 0.047(5) Uiso 1 1 d
H5BB H 0.874(3) -0.0147(18) 0.5497(17) 0.059(6) Uiso 1 1 d
H5BC H 0.848(2) 0.0864(16) 0.4927(16) 0.055(6) Uiso 1 1 d
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
O1 C1 C6 123.85(11) .
O1 C1 C2 118.90(11) .
C6 C1 C2 117.25(9) .
O2 C2 C3 123.30(12) .
O2 C2 C1 119.17(11) .
C3 C2 C1 117.52(10) .
C4 C3 C2 120.58(10) .
C4 C3 Cl1 122.48(9) .
C2 C3 Cl1 116.94(9) .
C3 C4 C5 122.06(10) .
C3 C4 Cl2 119.67(9) .
C5 C4 Cl2 118.27(8) .
C6 C5 C4 121.68(10) .
C6 C5 Cl3 121.17(9) .
C4 C5 Cl3 117.14(8) .
C5 C6 C1 120.87(10) .
C5 C6 Cl4 122.72(9) .
C1 C6 Cl4 116.41(8) .
C3A C1A C2A 123.06(11) 3_655
C3A C1A H1A 119.0(12) 3_655
C2A C1A H1A 117.9(12) .
C1A C2A C3A 118.43(11) .
C1A C2A C4A 120.55(12) .
C3A C2A C4A 121.02(12) .
C1A C3A C2A 118.51(10) 3_655
C1A C3A C5A 120.37(12) 3_655
C2A C3A C5A 121.11(13) .
C2A C4A H4AA 111.2(14) .
C2A C4A H4AB 111.6(13) .
H4AA C4A H4AB 107.9(19) .
C2A C4A H4AC 112.0(12) .
H4AA C4A H4AC 105.5(18) .
H4AB C4A H4AC 108.3(17) .
C3A C5A H5AA 106.9(14) .
C3A C5A H5AB 112.4(13) .
H5AA C5A H5AB 110.5(19) .
C3A C5A H5AC 111.3(12) .
H5AA C5A H5AC 109.4(18) .
H5AB C5A H5AC 106.3(17) .
C3B C1B C2B 122.88(10) 3_656
C3B C1B H1B 119.7(12) 3_656
C2B C1B H1B 117.4(12) .
C1B C2B C3B 118.68(10) .
C1B C2B C4B 120.39(11) .
C3B C2B C4B 120.93(11) .
C1B C3B C2B 118.44(10) 3_656
C1B C3B C5B 120.35(11) 3_656
C2B C3B C5B 121.20(11) .
C2B C4B H4BA 112.7(13) .
C2B C4B H4BB 110.7(13) .
H4BA C4B H4BB 107.1(17) .
C2B C4B H4BC 111.9(13) .
H4BA C4B H4BC 107.1(18) .
H4BB C4B H4BC 107.1(17) .
C3B C5B H5BA 111.9(12) .
C3B C5B H5BB 108.7(13) .
H5BA C5B H5BB 108.7(17) .
C3B C5B H5BC 112.6(13) .
H5BA C5B H5BC 106.3(17) .
H5BB C5B H5BC 108.6(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.7032(11) .
Cl2 C4 1.7012(11) .
Cl3 C5 1.7050(11) .
Cl4 C6 1.7025(11) .
O1 C1 1.2091(14) .
O2 C2 1.2074(14) .
C1 C6 1.4700(16) .
C1 C2 1.5439(17) .
C2 C3 1.4702(16) .
C3 C4 1.3473(16) .
C4 C5 1.4729(15) .
C5 C6 1.3490(15) .
C1A C3A 1.3934(18) 3_655
C1A C2A 1.3939(17) .
C1A H1A 0.94(2) .
C2A C3A 1.4051(17) .
C2A C4A 1.5038(18) .
C3A C1A 1.3934(18) 3_655
C3A C5A 1.5034(17) .
C4A H4AA 0.96(3) .
C4A H4AB 0.96(2) .
C4A H4AC 0.98(2) .
C5A H5AA 1.00(3) .
C5A H5AB 0.98(2) .
C5A H5AC 0.97(2) .
C1B C3B 1.3953(16) 3_656
C1B C2B 1.3964(16) .
C1B H1B 0.97(2) .
C2B C3B 1.4049(16) .
C2B C4B 1.5027(17) .
C3B C1B 1.3953(16) 3_656
C3B C5B 1.5020(16) .
C4B H4BA 0.96(2) .
C4B H4BB 0.97(2) .
C4B H4BC 0.92(2) .
C5B H5BA 0.96(2) .
C5B H5BB 0.99(2) .
C5B H5BC 0.96(2) .
