data_2203183
loop_
_publ_author_name
'Zaisu Jin'
'Wenxi Wang'
'Weixiao Hu'
'Zhongyu Yang'
'Hongwei Chen'
'Richeng Xuan'
_publ_section_title
;
5-Chloro-2-benzofuran-1,3-dione
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o239
_journal_page_last             o240
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C8 H3 Cl1 O3'
_chemical_formula_moiety       'C8 H3 Cl1 O3'
_chemical_formula_sum          'C8 H3 Cl O3'
_chemical_formula_weight       182.55
_symmetry_cell_setting         triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         'WinGX routine CIF_UPDATE'
_cell_angle_alpha              77.690(10)
_cell_angle_beta               88.090(10)
_cell_angle_gamma              85.48(2)
_cell_formula_units_Z          4
_cell_length_a                 6.929(2)
_cell_length_b                 7.8540(10)
_cell_length_c                 14.262(2)
_cell_measurement_reflns_used  4173
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    27.17
_cell_measurement_theta_min    1.46
_cell_volume                   755.8(3)
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_collection     'CAD-4 EXPRESS (Enraf--Nonius, 1994_'
_computing_data_reduction      'Datared (Harms & Wocadlo, 1995)'
_computing_molecular_graphics  'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type 'Enraf--Nonius CAD-4'
_diffrn_measurement_method     \w/2\q
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0154
_diffrn_reflns_av_sigmaI/netI  0.0275
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_number          4173
_diffrn_reflns_theta_full      27.17
_diffrn_reflns_theta_max       27.17
_diffrn_reflns_theta_min       1.46
_diffrn_standards_decay_%      0.5
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time 3600
_diffrn_standards_number       3
_exptl_absorpt_coefficient_mu  0.46
_exptl_absorpt_correction_T_max 0.9554
_exptl_absorpt_correction_T_min 0.8374
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details 'North et al., 1968'
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.604
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           368
_exptl_crystal_size_max        0.4
_exptl_crystal_size_mid        0.2
_exptl_crystal_size_min        0.1
_refine_diff_density_max       0.246
_refine_diff_density_min       -0.241
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.075
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   217
_refine_ls_number_reflns       3336
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.075
_refine_ls_R_factor_all        0.0738
_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/[\s^2^(Fo^2^)+(0.0367P)^2^+0.2624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0887
_refine_ls_wR_factor_ref       0.1036
_reflns_number_gt              2184
_reflns_number_total           3336
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
C1 0.3212(3) 0.2193(3) 0.85605(15) 0.0462(5) Uani d . 1 . . C
C2 0.4936(3) 0.1266(3) 0.84215(14) 0.0469(5) Uani d . 1 . . C
C3 0.6503(3) 0.1204(3) 0.89992(16) 0.0528(5) Uani d . 1 . . C
H3 0.7670 0.0591 0.8902 0.063 Uiso calc R 1 . . H
C4 0.6240(3) 0.2103(3) 0.97325(16) 0.0533(5) Uani d . 1 . . C
C5 0.4491(3) 0.2986(3) 0.98969(16) 0.0553(5) Uani d . 1 . . C
H5 0.4357 0.3535 1.0415 0.066 Uiso calc R 1 . . H
C6 0.2959(3) 0.3059(3) 0.93035(16) 0.0530(5) Uani d . 1 . . C
H6 0.1791 0.3671 0.9399 0.064 Uiso calc R 1 . . H
C7 0.1873(4) 0.2005(3) 0.78186(16) 0.0562(5) Uani d . 1 . . C
C8 0.4676(4) 0.0412(3) 0.76166(16) 0.0597(6) Uani d . 1 . . C
C9 0.2340(3) 0.3788(2) 0.38328(14) 0.0422(4) Uani d . 1 . . C
C10 0.1032(3) 0.3352(3) 0.32357(14) 0.0441(4) Uani d . 1 . . C
C11 -0.0642(3) 0.2581(3) 0.35791(16) 0.0518(5) Uani d . 1 . . C
H11 -0.1524 0.2286 0.3174 0.062 Uiso calc R 1 . . H
C12 -0.0931(3) 0.2275(3) 0.45612(17) 0.0528(5) Uani d . 1 . . C
C13 0.0390(3) 0.2679(3) 0.51685(16) 0.0579(6) Uani d . 1 . . C
H13 0.0152 0.2427 0.5827 0.069 Uiso calc R 1 . . H
C14 0.2058(3) 0.3453(3) 0.48115(15) 0.0533(5) Uani d . 1 . . C
H14 0.2953 0.3736 0.5215 0.064 Uiso calc R 1 . . H
C15 0.3910(3) 0.4619(3) 0.32289(16) 0.0512(5) Uani d . 1 . . C
C16 0.1766(3) 0.3868(3) 0.22439(16) 0.0540(5) Uani d . 1 . . C
O1 0.0252(3) 0.2577(3) 0.76504(14) 0.0765(5) Uani d . 1 . . O
O2 0.2818(3) 0.0922(2) 0.72697(11) 0.0641(4) Uani d . 1 . . O
O3 0.5714(3) -0.0572(3) 0.72757(14) 0.0879(6) Uani d . 1 . . O
O4 0.5314(2) 0.5253(2) 0.34222(13) 0.0731(5) Uani d . 1 . . O
O5 0.3512(2) 0.4620(2) 0.22825(10) 0.0567(4) Uani d . 1 . . O
O6 0.1155(3) 0.3741(3) 0.15003(12) 0.0785(5) Uani d . 1 . . O
Cl1 -0.30224(10) 0.13513(10) 0.50506(6) 0.0845(3) Uani d . 1 . . Cl
Cl2 0.81385(10) 0.21374(10) 1.04831(5) 0.0795(2) Uani d . 1 . . Cl
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0473(11) 0.0417(10) 0.0475(11) -0.0075(9) 0.0040(9) -0.0042(9)
C2 0.0518(12) 0.0405(10) 0.0449(11) -0.0058(9) 0.0086(9) -0.0021(8)
C3 0.0446(11) 0.0497(12) 0.0578(13) -0.0057(9) 0.0070(9) 0.0026(10)
C4 0.0542(13) 0.0529(12) 0.0503(12) -0.0210(10) -0.0024(10) 0.0013(10)
C5 0.0653(15) 0.0520(12) 0.0511(12) -0.0184(11) 0.0076(10) -0.0122(10)
C6 0.0528(13) 0.0477(12) 0.0586(13) -0.0069(10) 0.0097(10) -0.0120(10)
C7 0.0587(14) 0.0532(13) 0.0541(13) -0.0092(11) 0.0000(11) -0.0042(10)
C8 0.0762(16) 0.0512(13) 0.0489(12) -0.0014(12) 0.0086(11) -0.0069(10)
C9 0.0400(10) 0.0396(10) 0.0460(11) 0.0013(8) -0.0027(8) -0.0080(8)
C10 0.0401(10) 0.0464(11) 0.0451(11) 0.0019(8) -0.0010(8) -0.0098(9)
C11 0.0408(11) 0.0557(13) 0.0608(13) -0.0037(9) -0.0013(9) -0.0162(10)
C12 0.0429(11) 0.0456(11) 0.0639(14) 0.0039(9) 0.0117(10) -0.0026(10)
C13 0.0614(14) 0.0592(13) 0.0460(12) 0.0116(11) 0.0070(10) -0.0026(10)
C14 0.0565(13) 0.0552(13) 0.0475(12) 0.0037(10) -0.0086(10) -0.0112(10)
C15 0.0454(11) 0.0486(12) 0.0566(13) -0.0031(9) -0.0060(9) -0.0035(9)
C16 0.0465(12) 0.0666(14) 0.0493(12) -0.0016(10) -0.0008(9) -0.0141(10)
O1 0.0567(11) 0.0894(13) 0.0811(12) -0.0020(9) -0.0135(9) -0.0121(10)
O2 0.0776(11) 0.0635(10) 0.0526(9) -0.0048(9) -0.0064(8) -0.0148(8)
O3 0.1097(16) 0.0810(13) 0.0739(12) 0.0203(12) 0.0118(11) -0.0300(10)
O4 0.0592(10) 0.0780(12) 0.0802(12) -0.0255(9) -0.0098(9) -0.0039(9)
O5 0.0487(8) 0.0681(10) 0.0497(9) -0.0089(7) 0.0043(6) -0.0031(7)
O6 0.0704(11) 0.1223(16) 0.0468(9) -0.0112(11) -0.0055(8) -0.0251(10)
Cl1 0.0555(4) 0.0787(5) 0.1069(6) -0.0068(3) 0.0290(4) 0.0040(4)
Cl2 0.0710(4) 0.0875(5) 0.0768(4) -0.0327(4) -0.0188(3) 0.0020(3)
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 . . 121.4(2) ?
C6 C1 C7 . . 130.8(2) ?
C2 C1 C7 . . 107.75(19) ?
C3 C2 C1 . . 121.8(2) ?
C3 C2 C8 . . 130.6(2) ?
C1 C2 C8 . . 107.5(2) ?
C2 C3 C4 . . 116.1(2) ?
C2 C3 H3 . . 121.9 ?
C4 C3 H3 . . 121.9 ?
C3 C4 C5 . . 122.3(2) ?
C3 C4 Cl2 . . 119.58(19) ?
C5 C4 Cl2 . . 118.08(18) ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 117.6(2) ?
C5 C6 H6 . . 121.2 ?
C1 C6 H6 . . 121.2 ?
O1 C7 O2 . . 120.5(2) ?
O1 C7 C1 . . 131.8(2) ?
O2 C7 C1 . . 107.7(2) ?
O3 C8 O2 . . 120.8(2) ?
O3 C8 C2 . . 131.6(3) ?
O2 C8 C2 . . 107.58(19) ?
C10 C9 C14 . . 121.56(19) ?
C10 C9 C15 . . 107.64(18) ?
C14 C9 C15 . . 130.80(19) ?
C9 C10 C11 . . 122.18(19) ?
C9 C10 C16 . . 107.88(18) ?
C11 C10 C16 . . 129.9(2) ?
C10 C11 C12 . . 115.9(2) ?
C10 C11 H11 . . 122.0 ?
C12 C11 H11 . . 122.0 ?
C13 C12 C11 . . 122.3(2) ?
C13 C12 Cl1 . . 118.71(18) ?
C11 C12 Cl1 . . 118.95(18) ?
C12 C13 C14 . . 120.9(2) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C9 C14 C13 . . 117.1(2) ?
C9 C14 H14 . . 121.5 ?
C13 C14 H14 . . 121.5 ?
O4 C15 O5 . . 120.5(2) ?
O4 C15 C9 . . 131.7(2) ?
O5 C15 C9 . . 107.71(17) ?
O6 C16 O5 . . 120.5(2) ?
O6 C16 C10 . . 132.2(2) ?
O5 C16 C10 . . 107.27(18) ?
C7 O2 C8 . . 109.44(18) ?
C15 O5 C16 . . 109.48(16) ?
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
C1 C6 . 1.376(3) ?
C1 C2 . 1.380(3) y
C1 C7 . 1.468(3) y
C2 C3 . 1.376(3) ?
C2 C8 . 1.470(3) y
C3 C4 . 1.382(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(3) ?
C4 Cl2 . 1.729(2) y
C5 C6 . 1.370(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.189(3) y
C7 O2 . 1.388(3) y
C8 O3 . 1.183(3) y
C8 O2 . 1.393(3) y
C9 C10 . 1.374(3) y
C9 C14 . 1.374(3) ?
C9 C15 . 1.470(3) y
C10 C11 . 1.378(3) ?
C10 C16 . 1.471(3) y
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.380(3) ?
C12 Cl1 . 1.731(2) y
C13 C14 . 1.380(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 O4 . 1.193(3) y
C15 O5 . 1.386(3) y
C16 O6 . 1.181(3) y
C16 O5 . 1.395(3) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 O1 1_655 0.93 2.80 3.292(3) 114
C6 H6 O6 1_556 0.93 3.03 3.466(3) 111
C6 H6 O6 2_566 0.93 2.89 3.690(3) 145
C11 H11 O2 2_556 0.93 2.94 3.675(3) 137
C13 H13 O1 . 0.93 2.63 3.522(3) 161
C13 H13 O2 . 0.93 2.81 3.453(3) 127
C14 H14 O4 2_666 0.93 2.61 3.519(3) 166
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.9(3) ?
C7 C1 C2 C3 . . . . 179.21(18) ?
C6 C1 C2 C8 . . . . 176.22(19) ?
C7 C1 C2 C8 . . . . -2.6(2) ?
C1 C2 C3 C4 . . . . 0.8(3) ?
C8 C2 C3 C4 . . . . -176.9(2) ?
C2 C3 C4 C5 . . . . 1.5(3) ?
C2 C3 C4 Cl2 . . . . -178.79(15) ?
C3 C4 C5 C6 . . . . -2.7(3) ?
Cl2 C4 C5 C6 . . . . 177.56(16) ?
C4 C5 C6 C1 . . . . 1.5(3) ?
C2 C1 C6 C5 . . . . 0.7(3) ?
C7 C1 C6 C5 . . . . 179.3(2) ?
C6 C1 C7 O1 . . . . 2.0(4) y
C2 C1 C7 O1 . . . . -179.3(2) ?
C6 C1 C7 O2 . . . . -176.9(2) ?
C2 C1 C7 O2 . . . . 1.8(2) ?
C3 C2 C8 O3 . . . . 2.1(4) ?
C1 C2 C8 O3 . . . . -175.8(3) ?
C3 C2 C8 O2 . . . . -179.4(2) ?
C1 C2 C8 O2 . . . . 2.6(2) ?
C14 C9 C10 C11 . . . . 1.0(3) ?
C15 C9 C10 C11 . . . . -178.46(19) ?
C14 C9 C10 C16 . . . . -179.56(19) ?
C15 C9 C10 C16 . . . . 1.0(2) ?
C9 C10 C11 C12 . . . . 0.1(3) ?
C16 C10 C11 C12 . . . . -179.3(2) ?
C10 C11 C12 C13 . . . . -1.3(3) ?
C10 C11 C12 Cl1 . . . . 178.70(15) ?
C11 C12 C13 C14 . . . . 1.4(3) ?
Cl1 C12 C13 C14 . . . . -178.54(17) ?
C10 C9 C14 C13 . . . . -0.8(3) ?
C15 C9 C14 C13 . . . . 178.4(2) ?
C12 C13 C14 C9 . . . . -0.3(3) ?
C10 C9 C15 O4 . . . . 177.3(2) ?
C14 C9 C15 O4 . . . . -2.0(4) ?
C10 C9 C15 O5 . . . . -1.3(2) ?
C14 C9 C15 O5 . . . . 179.3(2) ?
C9 C10 C16 O6 . . . . 179.2(3) ?
C11 C10 C16 O6 . . . . -1.4(4) ?
C9 C10 C16 O5 . . . . -0.4(2) ?
C11 C10 C16 O5 . . . . 179.0(2) ?
O1 C7 O2 C8 . . . . -179.2(2) ?
C1 C7 O2 C8 . . . . -0.1(2) ?
O3 C8 O2 C7 . . . . 177.1(2) ?
C2 C8 O2 C7 . . . . -1.5(2) ?
O4 C15 O5 C16 . . . . -177.8(2) ?
C9 C15 O5 C16 . . . . 1.1(2) ?
O6 C16 O5 C15 . . . . 179.9(2) ?
C10 C16 O5 C15 . . . . -0.4(2) ?