#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:56:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178451 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/72/4027290.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_4027290
loop_
_publ_author_name
'Sergiy V. Rosokha'
'Vasiliy Korotchenko'
'Charlotte L. Stern'
'Vladimir Zaitsev'
'Jeremy T. Ritzert'
_publ_section_title
;
 Substituent-Induced Switch of the Role of Charge-Transfer Complexes in
 the Diels-Alder Reactions of o-Chloranil and Styrenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5971
_journal_page_last               5981
_journal_paper_doi               10.1021/jo300614k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C15 H10 Cl4 O2'
_chemical_formula_sum            'C15 H10 Cl4 O2'
_chemical_formula_weight         364.03
_chemical_name_systematic
; 
 ? 
;
_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'
_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                 110.531(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7205(7)
_cell_length_b                   10.0860(6)
_cell_length_c                   13.4468(8)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.59
_cell_volume                     1488.62(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4558
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  0.8012
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2008/4 (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0066P)²+6.1365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                4117
_reflns_number_total             4558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300614k_si_004.cif
_cod_data_source_block           n0699t
_cod_original_cell_volume        1488.62(15)
_cod_database_code               4027290
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_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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.0879(9) 0.5517(9) 0.1691(10) 0.028(2) Uani 0.41(8) 1 d P A 1
Cl2A Cl 0.0791(12) 0.8386(11) 0.2541(10) 0.026(4) Uani 0.31(8) 1 d P A 1
Cl1B Cl 0.107(2) 0.5429(15) 0.1608(12) 0.054(2) Uani 0.59(8) 1 d P A 2
Cl2B Cl 0.0713(9) 0.8258(15) 0.2456(10) 0.056(2) Uani 0.69(8) 1 d P A 2
Cl3 Cl 0.31842(14) 1.00459(10) 0.34643(10) 0.0510(3) Uani 1 1 d . A .
Cl4 Cl 0.56577(10) 0.86798(16) 0.37436(9) 0.0590(4) Uani 1 1 d . . .
O1 O 0.4793(3) 0.7788(4) 0.1492(3) 0.0459(8) Uani 1 1 d . A .
O2 O 0.2625(4) 0.6295(3) 0.0550(2) 0.0455(8) Uani 1 1 d . . .
C1 C 0.2335(3) 0.6347(3) 0.2265(3) 0.0248(6) Uani 1 1 d . . .
C2 C 0.2159(3) 0.7715(4) 0.2658(3) 0.0242(6) Uani 1 1 d . A .
C3 C 0.3159(3) 0.8440(3) 0.3070(3) 0.0257(7) Uani 1 1 d . . .
C4 C 0.4336(3) 0.7735(4) 0.3139(3) 0.0295(7) Uani 1 1 d . A .
C5 C 0.4155(3) 0.7441(4) 0.1983(3) 0.0308(8) Uani 1 1 d . . .
C6 C 0.2961(4) 0.6635(4) 0.1452(3) 0.0292(7) Uani 1 1 d . A .
C7 C 0.4399(3) 0.6410(4) 0.3746(3) 0.0297(8) Uani 1 1 d . . .
H7A H 0.4431 0.6601 0.4478 0.036 Uiso 1 1 calc R A .
H7B H 0.5152 0.5928 0.3793 0.036 Uiso 1 1 calc R . .
C8 C 0.3272(3) 0.5525(3) 0.3175(3) 0.0251(6) Uani 1 1 d . A .
H8 H 0.3560 0.4782 0.2830 0.030 Uiso 1 1 calc R . .
C9 C 0.2706(3) 0.4905(3) 0.3917(3) 0.0237(6) Uani 1 1 d . . .
C10 C 0.2334(4) 0.5664(4) 0.4607(3) 0.0310(8) Uani 1 1 d . A .
H10 H 0.2462 0.6595 0.4639 0.037 Uiso 1 1 calc R . .
C11 C 0.1773(4) 0.5071(4) 0.5257(3) 0.0339(8) Uani 1 1 d . . .
H11 H 0.1516 0.5608 0.5719 0.041 Uiso 1 1 calc R A .
C12 C 0.1586(3) 0.3710(4) 0.5236(3) 0.0310(8) Uani 1 1 d . A .
C13 C 0.1968(3) 0.2949(4) 0.4544(3) 0.0290(7) Uani 1 1 d . . .
H13 H 0.1850 0.2016 0.4517 0.035 Uiso 1 1 calc R A .
C14 C 0.2519(3) 0.3541(4) 0.3895(3) 0.0262(7) Uani 1 1 d . A .
H14 H 0.2772 0.3005 0.3429 0.031 Uiso 1 1 calc R . .
C15 C 0.0988(4) 0.3062(5) 0.5938(4) 0.0425(10) Uani 1 1 d . . .
H15A H 0.1588 0.2518 0.6475 0.064 Uiso 1 1 calc R A .
H15B H 0.0316 0.2499 0.5505 0.064 Uiso 1 1 calc R . .
H15C H 0.0672 0.3747 0.6289 0.064 Uiso 1 1 calc R . .
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
C2 C1 C6 103.4(3)
C2 C1 C8 110.7(3)
C6 C1 C8 106.0(3)
C2 C1 Cl1B 118.3(11)
C6 C1 Cl1B 106.1(10)
C8 C1 Cl1B 111.1(5)
C2 C1 Cl1A 110.2(4)
C6 C1 Cl1A 113.3(5)
C8 C1 Cl1A 112.7(4)
Cl1B C1 Cl1A 9.0(11)
C3 C2 C1 116.0(3)
C3 C2 Cl2A 119.1(6)
C1 C2 Cl2A 124.8(6)
C3 C2 Cl2B 124.8(7)
C1 C2 Cl2B 119.0(7)
Cl2A C2 Cl2B 5.9(6)
C2 C3 C4 114.6(3)
C2 C3 Cl3 124.8(3)
C4 C3 Cl3 120.5(3)
C5 C4 C3 103.3(3)
C5 C4 C7 109.4(3)
C3 C4 C7 107.9(3)
C5 C4 Cl4 111.3(2)
C3 C4 Cl4 114.1(3)
C7 C4 Cl4 110.6(2)
O1 C5 C4 127.5(4)
O1 C5 C6 121.9(4)
C4 C5 C6 110.5(3)
O2 C6 C1 126.8(4)
O2 C6 C5 122.8(4)
C1 C6 C5 110.3(3)
C4 C7 C8 111.0(3)
C4 C7 H7A 109.4
C8 C7 H7A 109.4
C4 C7 H7B 109.4
C8 C7 H7B 109.4
H7A C7 H7B 108.0
C9 C8 C7 113.8(3)
C9 C8 C1 112.6(3)
C7 C8 C1 108.8(3)
C9 C8 H8 107.1
C7 C8 H8 107.1
C1 C8 H8 107.1
C10 C9 C14 118.4(3)
C10 C9 C8 121.8(3)
C14 C9 C8 119.8(3)
C9 C10 C11 120.6(4)
C9 C10 H10 119.7
C11 C10 H10 119.7
C12 C11 C10 121.1(4)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 118.1(3)
C11 C12 C15 121.4(4)
C13 C12 C15 120.5(4)
C14 C13 C12 120.8(4)
C14 C13 H13 119.6
C12 C13 H13 119.6
C13 C14 C9 121.0(3)
C13 C14 H14 119.5
C9 C14 H14 119.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1A C1 1.813(12)
Cl2A C2 1.696(11)
Cl1B C1 1.708(13)
Cl2B C2 1.710(7)
Cl3 C3 1.701(4)
Cl4 C4 1.757(4)
O1 C5 1.211(4)
O2 C6 1.187(5)
C1 C2 1.517(5)
C1 C6 1.542(5)
C1 C8 1.565(5)
C2 C3 1.326(5)
C3 C4 1.525(5)
C4 C5 1.523(5)
C4 C7 1.554(5)
C5 C6 1.558(6)
C7 C8 1.555(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.514(5)
C8 H8 1.0000
C9 C10 1.387(5)
C9 C14 1.392(5)
C10 C11 1.398(5)
C10 H10 0.9500
C11 C12 1.389(6)
C11 H11 0.9500
C12 C13 1.395(5)
C12 C15 1.508(5)
C13 C14 1.390(5)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
C6 C1 C2 C3 -56.8(4)
C8 C1 C2 C3 56.4(4)
Cl1B C1 C2 C3 -173.7(7)
Cl1A C1 C2 C3 -178.2(5)
C6 C1 C2 Cl2A 119.7(5)
C8 C1 C2 Cl2A -127.1(5)
Cl1B C1 C2 Cl2A 2.8(9)
Cl1A C1 C2 Cl2A -1.8(7)
C6 C1 C2 Cl2B 118.5(4)
C8 C1 C2 Cl2B -128.3(4)
Cl1B C1 C2 Cl2B 1.6(8)
Cl1A C1 C2 Cl2B -2.9(6)
C1 C2 C3 C4 -3.5(4)
Cl2A C2 C3 C4 179.8(5)
Cl2B C2 C3 C4 -178.4(4)
C1 C2 C3 Cl3 174.4(3)
Cl2A C2 C3 Cl3 -2.3(6)
Cl2B C2 C3 Cl3 -0.6(6)
C2 C3 C4 C5 61.9(4)
Cl3 C3 C4 C5 -116.1(3)
C2 C3 C4 C7 -53.9(4)
Cl3 C3 C4 C7 128.2(3)
C2 C3 C4 Cl4 -177.2(3)
Cl3 C3 C4 Cl4 4.8(4)
C3 C4 C5 O1 122.2(4)
C7 C4 C5 O1 -123.1(4)
Cl4 C4 C5 O1 -0.6(5)
C3 C4 C5 C6 -55.7(4)
C7 C4 C5 C6 59.0(4)
Cl4 C4 C5 C6 -178.5(3)
C2 C1 C6 O2 -124.7(4)
C8 C1 C6 O2 118.8(4)
Cl1B C1 C6 O2 0.5(10)
Cl1A C1 C6 O2 -5.3(6)
C2 C1 C6 C5 56.4(3)
C8 C1 C6 C5 -60.1(4)
Cl1B C1 C6 C5 -178.4(9)
Cl1A C1 C6 C5 175.8(4)
O1 C5 C6 O2 1.6(6)
C4 C5 C6 O2 179.6(4)
O1 C5 C6 C1 -179.4(4)
C4 C5 C6 C1 -1.4(4)
C5 C4 C7 C8 -53.3(4)
C3 C4 C7 C8 58.4(4)
Cl4 C4 C7 C8 -176.2(3)
C4 C7 C8 C9 -135.2(3)
C4 C7 C8 C1 -8.6(4)
C2 C1 C8 C9 81.0(4)
C6 C1 C8 C9 -167.4(3)
Cl1B C1 C8 C9 -52.5(13)
Cl1A C1 C8 C9 -42.9(5)
C2 C1 C8 C7 -46.2(4)
C6 C1 C8 C7 65.3(3)
Cl1B C1 C8 C7 -179.8(13)
Cl1A C1 C8 C7 -170.1(5)
C7 C8 C9 C10 54.7(5)
C1 C8 C9 C10 -69.8(4)
C7 C8 C9 C14 -127.0(4)
C1 C8 C9 C14 108.5(4)
C14 C9 C10 C11 -0.7(6)
C8 C9 C10 C11 177.7(4)
C9 C10 C11 C12 0.7(6)
C10 C11 C12 C13 -0.3(6)
C10 C11 C12 C15 179.7(4)
C11 C12 C13 C14 0.0(6)
C15 C12 C13 C14 180.0(4)
C12 C13 C14 C9 0.0(6)
C10 C9 C14 C13 0.3(5)
C8 C9 C14 C13 -178.0(3)
