#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/72/4027289.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_4027289
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         'C6 Cl4 O2, C9 H10 O '
_chemical_formula_sum            'C15 H10 Cl4 O3'
_chemical_formula_weight         380.03
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0317(15)
_cell_length_b                   14.8962(15)
_cell_length_c                   6.9832(7)
_cell_measurement_reflns_used    3822
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.71
_cell_volume                     1563.6(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17179
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_description       rock
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0485
_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)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2740
_reflns_number_total             4614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300614k_si_003.cif
_cod_data_source_block           vas1
_cod_database_code               4027289
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags
Cl3 Cl 0.19417(7) 0.81470(6) 0.60829(16) 0.0588(3) Uani 1 1 d .
Cl4 Cl 0.39051(7) 0.79865(7) 0.45578(15) 0.0588(3) Uani 1 1 d .
Cl5 Cl 0.48337(5) 0.61542(8) 0.43822(17) 0.0625(3) Uani 1 1 d .
Cl6 Cl 0.38008(7) 0.43791(7) 0.53163(17) 0.0629(3) Uani 1 1 d .
O1 O 0.19580(17) 0.47440(16) 0.6394(4) 0.0537(7) Uani 1 1 d .
O2 O 0.11912(15) 0.63875(19) 0.6970(4) 0.0521(7) Uani 1 1 d .
O11 O 0.06409(17) 0.59679(19) 0.2334(4) 0.0546(7) Uani 1 1 d .
C1 C 0.2382(2) 0.5419(2) 0.6118(5) 0.0356(7) Uani 1 1 d .
C2 C 0.19461(19) 0.6340(2) 0.6398(5) 0.0354(7) Uani 1 1 d .
C3 C 0.2464(2) 0.7140(2) 0.5876(5) 0.0348(7) Uani 1 1 d .
C4 C 0.3316(2) 0.7063(2) 0.5250(5) 0.0362(7) Uani 1 1 d .
C5 C 0.37530(18) 0.6182(2) 0.5102(5) 0.0360(7) Uani 1 1 d .
C6 C 0.3320(2) 0.5406(2) 0.5530(5) 0.0367(7) Uani 1 1 d .
C11 C 0.3204(2) 0.6561(3) 0.0269(5) 0.0458(8) Uani 1 1 d .
C12 C 0.2937(3) 0.5667(2) 0.0561(5) 0.0498(9) Uani 1 1 d .
H12A H 0.3345 0.5198 0.0276 0.060 Uiso 1 1 calc R
C13 C 0.2108(2) 0.5445(2) 0.1243(6) 0.0467(9) Uani 1 1 d .
H13A H 0.1955 0.4832 0.1430 0.056 Uiso 1 1 calc R
C14 C 0.1497(2) 0.6111(2) 0.1657(5) 0.0420(8) Uani 1 1 d .
C15 C 0.1752(2) 0.7013(2) 0.1384(5) 0.0460(8) Uani 1 1 d .
H15A H 0.1340 0.7478 0.1664 0.055 Uiso 1 1 calc R
C16 C 0.2580(2) 0.7232(3) 0.0724(5) 0.0461(8) Uani 1 1 d .
H16A H 0.2737 0.7846 0.0572 0.055 Uiso 1 1 calc R
C17 C 0.40939(19) 0.6749(2) -0.0472(6) 0.0418(8) Uani 1 1 d .
H17A H 0.4454 0.6254 -0.0840 0.050 Uiso 1 1 calc R
C18 C 0.4427(2) 0.7562(3) -0.0660(6) 0.0667(12) Uani 1 1 d .
H18A H 0.4083 0.8070 -0.0304 0.080 Uiso 1 1 calc R
H18B H 0.5011 0.7640 -0.1151 0.080 Uiso 1 1 calc R
C19 C 0.0356(2) 0.5080(3) 0.2665(6) 0.0538(10) Uani 1 1 d .
H19A H -0.0259 0.5085 0.3129 0.081 Uiso 1 1 calc R
H19B H 0.0740 0.4799 0.3628 0.081 Uiso 1 1 calc R
H19C H 0.0389 0.4737 0.1469 0.081 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
C14 O11 C19 118.8(3)
O1 C1 C6 122.8(3)
O1 C1 C2 120.0(3)
C6 C1 C2 117.3(2)
O2 C2 C3 122.2(3)
O2 C2 C1 119.9(3)
C3 C2 C1 117.9(3)
C4 C3 C2 120.7(3)
C4 C3 Cl3 122.5(2)
C2 C3 Cl3 116.8(2)
C3 C4 C5 121.3(3)
C3 C4 Cl4 120.9(3)
C5 C4 Cl4 117.9(2)
C6 C5 C4 122.0(3)
C6 C5 Cl5 120.0(3)
C4 C5 Cl5 118.0(2)
C5 C6 C1 120.6(3)
C5 C6 Cl6 122.9(2)
C1 C6 Cl6 116.4(2)
C12 C11 C16 116.8(3)
C12 C11 C17 119.6(3)
C16 C11 C17 123.6(3)
C13 C12 C11 122.5(3)
C13 C12 H12A 118.8
C11 C12 H12A 118.8
C12 C13 C14 120.1(3)
C12 C13 H13A 119.9
C14 C13 H13A 119.9
C13 C14 O11 125.3(3)
C13 C14 C15 118.4(3)
O11 C14 C15 116.4(3)
C16 C15 C14 121.4(3)
C16 C15 H15A 119.3
C14 C15 H15A 119.3
C15 C16 C11 120.8(3)
C15 C16 H16A 119.6
C11 C16 H16A 119.6
C18 C17 C11 124.0(4)
C18 C17 H17A 118.0
C11 C17 H17A 118.0
C17 C18 H18A 120.0
C17 C18 H18B 120.0
H18A C18 H18B 120.0
O11 C19 H19A 109.5
O11 C19 H19B 109.5
H19A C19 H19B 109.5
O11 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl3 C3 1.699(3)
Cl4 C4 1.706(3)
Cl5 C5 1.701(3)
Cl6 C6 1.698(3)
O1 C1 1.206(4)
O2 C2 1.205(4)
O11 C14 1.388(4)
O11 C19 1.410(5)
C1 C6 1.469(4)
C1 C2 1.532(4)
C2 C3 1.470(4)
C3 C4 1.358(4)
C4 C5 1.471(5)
C5 C6 1.360(5)
C11 C12 1.406(5)
C11 C16 1.407(5)
C11 C17 1.462(5)
C12 C13 1.374(5)
C12 H12A 0.9500
C13 C14 1.383(5)
C13 H13A 0.9500
C14 C15 1.411(5)
C15 C16 1.367(5)
C15 H15A 0.9500
C16 H16A 0.9500
C17 C18 1.317(5)
C17 H17A 0.9500
C18 H18A 0.9500
C18 H18B 0.9500
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 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
O1 C1 C2 O2 3.1(5)
C6 C1 C2 O2 -176.4(3)
O1 C1 C2 C3 -174.6(3)
C6 C1 C2 C3 6.0(4)
O2 C2 C3 C4 179.5(3)
C1 C2 C3 C4 -2.9(5)
O2 C2 C3 Cl3 -1.0(5)
C1 C2 C3 Cl3 176.6(2)
C2 C3 C4 C5 -1.1(5)
Cl3 C3 C4 C5 179.5(2)
C2 C3 C4 Cl4 177.5(2)
Cl3 C3 C4 Cl4 -2.0(4)
C3 C4 C5 C6 2.0(5)
Cl4 C4 C5 C6 -176.6(3)
C3 C4 C5 Cl5 -177.8(3)
Cl4 C4 C5 Cl5 3.6(4)
C4 C5 C6 C1 1.5(5)
Cl5 C5 C6 C1 -178.8(3)
C4 C5 C6 Cl6 178.4(3)
Cl5 C5 C6 Cl6 -1.9(4)
O1 C1 C6 C5 175.3(3)
C2 C1 C6 C5 -5.3(5)
O1 C1 C6 Cl6 -1.8(5)
C2 C1 C6 Cl6 177.6(2)
C16 C11 C12 C13 0.5(5)
C17 C11 C12 C13 -179.6(3)
C11 C12 C13 C14 0.5(6)
C12 C13 C14 O11 179.4(3)
C12 C13 C14 C15 -0.8(5)
C19 O11 C14 C13 0.9(5)
C19 O11 C14 C15 -178.9(3)
C13 C14 C15 C16 0.1(5)
O11 C14 C15 C16 179.9(3)
C14 C15 C16 C11 0.9(6)
C12 C11 C16 C15 -1.2(5)
C17 C11 C16 C15 179.0(4)
C12 C11 C17 C18 -174.8(4)
C16 C11 C17 C18 5.0(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659503
