#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:53:30 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179027 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/25/4122543.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_4122543
loop_
_publ_author_name
'Guo, Xingwei'
'Mayr, Herbert'
_publ_section_title
;
 Quantification of the ambident electrophilicities of halogen-substituted
 quinones.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11499
_journal_page_last               11512
_journal_paper_doi               10.1021/ja505613b
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C10 H6 Cl4 O4'
_chemical_formula_sum            'C10 H6 Cl4 O4'
_chemical_formula_weight         331.963
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_block_code                C10H6Cl4O4_sq021_mayr
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             03-Feb-14
_cell_angle_alpha                90.00
_cell_angle_beta                 101.491(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0384(7)
_cell_length_b                   6.1634(4)
_cell_length_c                   16.5271(9)
_cell_measurement_reflns_used    118
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.7494
_cell_measurement_theta_min      4.0482
_cell_volume                     1201.69(12)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Quest'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11649
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.52
_diffrn_source_current           1
_diffrn_source_power             50
_diffrn_source_type              'Bruker I\mS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_correction_T_min  0.8863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.83490(18)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0524
_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)+(0.0307P)²+1.7135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1872
_reflns_number_total             2387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja505613b_si_002.cif
_cod_data_source_block           sq021
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4122543
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
C1 C 0.1595(3) -0.0810(5) 0.52491(19) 0.0227(7) Uani 1 1 d .
C2 C 0.1311(3) -0.0127(6) 0.5990(2) 0.0266(8) Uani 1 1 d .
C3 C 0.1786(3) 0.1766(6) 0.63581(19) 0.0283(8) Uani 1 1 d .
C4 C 0.2574(3) 0.2916(5) 0.60180(19) 0.0252(7) Uani 1 1 d .
C5 C 0.2891(3) 0.2191(5) 0.52956(18) 0.0209(7) Uani 1 1 d .
C6 C 0.2359(3) 0.0366(5) 0.49039(18) 0.0199(7) Uani 1 1 d .
C7 C 0.3339(3) -0.1800(5) 0.40550(18) 0.0211(7) Uani 1 1 d .
H7 H 0.3581 -0.2585 0.4591 0.025 Uiso 1 1 calc R
C8 C 0.4347(3) -0.0778(6) 0.37753(19) 0.0244(7) Uani 1 1 d .
C9 C 0.3974(3) -0.3968(6) 0.3071(2) 0.0315(8) Uani 1 1 d .
H9A H 0.4347 -0.5227 0.3386 0.038 Uiso 1 1 calc R
H9B H 0.3809 -0.4337 0.2476 0.038 Uiso 1 1 calc R
C10 C 0.2896(3) -0.3366(6) 0.3360(2) 0.0282(8) Uani 1 1 d .
H10A H 0.2343 -0.2658 0.2915 0.034 Uiso 1 1 calc R
H10B H 0.2540 -0.4652 0.3562 0.034 Uiso 1 1 calc R
O1 O 0.3684(2) 0.3326(4) 0.49950(15) 0.0274(6) Uani 1 1 d .
H1 H 0.390(3) 0.263(6) 0.470(2) 0.021(11) Uiso 1 1 d .
O2 O 0.25457(18) -0.0116(4) 0.41264(12) 0.0215(5) Uani 1 1 d .
O3 O 0.4699(2) -0.2040(4) 0.32247(13) 0.0288(6) Uani 1 1 d .
O4 O 0.4783(2) 0.0948(4) 0.39935(15) 0.0313(6) Uani 1 1 d .
Cl1 Cl 0.09958(7) -0.31018(14) 0.47491(5) 0.0315(2) Uani 1 1 d .
Cl2 Cl 0.03724(8) -0.16117(17) 0.64235(6) 0.0420(3) Uani 1 1 d .
Cl3 Cl 0.13994(10) 0.27409(17) 0.72388(5) 0.0468(3) Uani 1 1 d .
Cl4 Cl 0.31721(8) 0.52830(15) 0.64584(5) 0.0367(3) Uani 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
C6 C1 C2 120.2(3)
C6 C1 Cl1 118.8(2)
C2 C1 Cl1 121.0(3)
C3 C2 C1 119.1(3)
C3 C2 Cl2 120.9(3)
C1 C2 Cl2 120.0(3)
C2 C3 C4 120.5(3)
C2 C3 Cl3 120.5(3)
C4 C3 Cl3 119.0(3)
C3 C4 C5 120.4(3)
C3 C4 Cl4 121.5(3)
C5 C4 Cl4 118.0(3)
O1 C5 C6 122.7(3)
O1 C5 C4 118.7(3)
C6 C5 C4 118.6(3)
C1 C6 O2 121.2(3)
C1 C6 C5 121.1(3)
O2 C6 C5 117.5(3)
O2 C7 C10 112.7(3)
O2 C7 C8 108.1(3)
C10 C7 C8 102.4(2)
O2 C7 H7 111.1
C10 C7 H7 111.1
C8 C7 H7 111.1
O4 C8 O3 122.7(3)
O4 C8 C7 126.8(3)
O3 C8 C7 110.4(3)
O3 C9 C10 105.3(3)
O3 C9 H9A 110.7
C10 C9 H9A 110.7
O3 C9 H9B 110.7
C10 C9 H9B 110.7
H9A C9 H9B 108.8
C7 C10 C9 101.6(3)
C7 C10 H10A 111.5
C9 C10 H10A 111.5
C7 C10 H10B 111.5
C9 C10 H10B 111.5
H10A C10 H10B 109.3
C5 O1 H1 108(3)
C6 O2 C7 117.9(2)
C8 O3 C9 109.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.380(4)
C1 C2 1.400(4)
C1 Cl1 1.721(3)
C2 C3 1.385(5)
C2 Cl2 1.717(3)
C3 C4 1.391(5)
C3 Cl3 1.722(3)
C4 C5 1.397(4)
C4 Cl4 1.722(3)
C5 O1 1.355(4)
C5 C6 1.389(4)
C6 O2 1.380(3)
C7 O2 1.431(4)
C7 C10 1.514(4)
C7 C8 1.519(4)
C7 H7 1.0000
C8 O4 1.209(4)
C8 O3 1.328(4)
C9 O3 1.466(4)
C9 C10 1.515(5)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
O1 H1 0.73(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O4 0.73(4) 2.02(4) 2.741(4) 169(4)
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 1.6(5)
Cl1 C1 C2 C3 -177.9(2)
C6 C1 C2 Cl2 -179.3(2)
Cl1 C1 C2 Cl2 1.2(4)
C1 C2 C3 C4 -3.1(5)
Cl2 C2 C3 C4 177.8(3)
C1 C2 C3 Cl3 176.4(2)
Cl2 C2 C3 Cl3 -2.7(4)
C2 C3 C4 C5 0.7(5)
Cl3 C3 C4 C5 -178.8(2)
C2 C3 C4 Cl4 179.6(2)
Cl3 C3 C4 Cl4 0.1(4)
C3 C4 C5 O1 -178.3(3)
Cl4 C4 C5 O1 2.7(4)
C3 C4 C5 C6 3.3(4)
Cl4 C4 C5 C6 -175.7(2)
C2 C1 C6 O2 -171.9(3)
Cl1 C1 C6 O2 7.6(4)
C2 C1 C6 C5 2.4(4)
Cl1 C1 C6 C5 -178.1(2)
O1 C5 C6 C1 176.8(3)
C4 C5 C6 C1 -4.8(4)
O1 C5 C6 O2 -8.7(4)
C4 C5 C6 O2 169.7(3)
O2 C7 C8 O4 38.8(4)
C10 C7 C8 O4 158.0(3)
O2 C7 C8 O3 -139.9(2)
C10 C7 C8 O3 -20.7(3)
O2 C7 C10 C9 146.5(3)
C8 C7 C10 C9 30.5(3)
O3 C9 C10 C7 -31.1(3)
C1 C6 O2 C7 -84.0(3)
C5 C6 O2 C7 101.5(3)
C10 C7 O2 C6 133.9(3)
C8 C7 O2 C6 -113.6(3)
O4 C8 O3 C9 -177.9(3)
C7 C8 O3 C9 0.8(3)
C10 C9 O3 C8 19.6(3)
