#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/40/7204042.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_7204042
loop_
_publ_author_name
'Easton, Christopher J.'
'Heath, Graham A.'
'Hughes, C. Merrîcc M.'
'Lee, Connie K. Y.'
'Savage, G. Paul'
'Simpson, Gregory W.'
'Tiekink, Edward R. T.'
'Vuckovic, George J.'
'Webster, Richard D.'
_publ_section_title
;
 Electrochemical and yeast-catalysed ring-opening of isoxazoles in the
 synthesis of analogues of the herbicide Grasp ®
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1168
_journal_paper_doi               10.1039/b008081k
_journal_year                    2001
_chemical_formula_moiety         'C12 H9 Cl2 N O3 '
_chemical_formula_sum            'C12 H9 Cl2 N O3'
_chemical_formula_weight         286.11
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.131(4)
_cell_length_b                   25.771(4)
_cell_length_c                   8.699(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      7.4
_cell_measurement_theta_min      3.8
_cell_volume                     2495.4(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan for Windows (MSC, 1997)'
_computing_publication_material  'teXsan for Windows (MSC, 1997)'
_computing_structure_refinement  'teXsan for Windows (MSC, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Rigaku AFC6R'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.00362
_diffrn_orient_matrix_UB_12      -0.02366
_diffrn_orient_matrix_UB_13      0.09100
_diffrn_orient_matrix_UB_21      -0.01501
_diffrn_orient_matrix_UB_22      -0.03047
_diffrn_orient_matrix_UB_23      -0.06855
_diffrn_orient_matrix_UB_31      0.08850
_diffrn_orient_matrix_UB_32      -0.00420
_diffrn_orient_matrix_UB_33      -0.01535
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2635
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        -2.94
_diffrn_standards_interval_count 400
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.950
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     163
_refine_ls_number_reflns         994
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00005|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0480
_reflns_number_gt                994
_reflns_number_total             2633
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            b008081k.txt
_cod_data_source_block           '[C12H9Cl2NO3]'
_cod_original_cell_volume        2495.4(10)
_cod_original_sg_symbol_H-M      'P b c a    '
_cod_original_formula_sum        'C12 H9 Cl2 N O3 '
_cod_database_code               7204042
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2+x,1/2-y,   -z'
'   -x,1/2+y,1/2-z'
'1/2-x,   -y,1/2+z'
'   -x,   -y,   -z'
'1/2-x,1/2+y,   +z'
'   +x,1/2-y,1/2+z'
'1/2+x,   +y,1/2-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_occupancy
_atom_site_refinement_flags
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
Cl(32) 0.03940(11) 0.09007(5) 0.20720(16) 0.0988(5) 1.000 . Uani d ?
Cl(36) 0.05187(11) 0.23163(4) -0.23986(16) 0.0902(5) 1.000 . Uani d ?
O(1) 0.35065(26) 0.16578(12) 0.0129(4) 0.0719(11) 1.000 . Uani d ?
O(6) 0.07599(24) 0.07610(11) -0.2521(4) 0.0849(11) 1.000 . Uani d ?
O(8) 0.1357(4) 0.00883(21) -0.4906(6) 0.1868(24) 1.000 . Uani d ?
N(2) 0.2334(3) 0.18203(13) 0.0504(4) 0.0650(13) 1.000 . Uani d ?
C(3) 0.1635(4) 0.15316(15) -0.0312(5) 0.0492(13) 1.000 . Uani d ?
C(4) 0.2287(4) 0.11815(15) -0.1243(5) 0.0434(13) 1.000 . Uani d ?
C(5) 0.3434(4) 0.12841(17) -0.0888(6) 0.0586(16) 1.000 . Uani d ?
C(6) 0.1824(4) 0.07992(15) -0.2298(5) 0.0528(14) 1.000 . Uani d ?
C(7) 0.2686(4) 0.04718(17) -0.3139(5) 0.0605(14) 1.000 . Uani d ?
C(8) 0.2153(6) 0.0036(3) -0.4004(9) 0.156(3) 1.000 . Uani d ?
C(31) 0.0332(4) 0.16104(16) -0.0134(6) 0.0513(14) 1.000 . Uani d ?
C(32) -0.0314(4) 0.13470(17) 0.0936(5) 0.0628(16) 1.000 . Uani d ?
C(33) -0.1525(5) 0.14295(20) 0.1116(6) 0.0777(19) 1.000 . Uani d ?
C(34) -0.2075(4) 0.17923(24) 0.0225(7) 0.0839(21) 1.000 . Uani d ?
C(35) -0.1466(5) 0.20597(19) -0.0871(6) 0.0751(19) 1.000 . Uani d ?
C(36) -0.0252(4) 0.19683(16) -0.1044(5) 0.0591(15) 1.000 . Uani d ?
H(5) 0.4121 0.1105 -0.1325 0.070 1.000 . Uiso c ?
H(7b) 0.3249 0.0329 -0.2399 0.073 1.000 . Uiso c ?
H(7a) 0.3114 0.0691 -0.3862 0.073 1.000 . Uiso c ?
H(8) 0.0789 0.0227 -0.4664 0.077 1.000 . Uiso c ?
H(8b) 0.2811 -0.0122 -0.4570 0.187 1.000 . Uiso c ?
H(8a) 0.1860 -0.0206 -0.3238 0.187 1.000 . Uiso c ?
H(33) -0.1981 0.1232 0.1865 0.093 1.000 . Uiso c ?
H(34) -0.2924 0.1862 0.0376 0.101 1.000 . Uiso c ?
H(35) -0.1876 0.2310 -0.1519 0.090 1.000 . Uiso c ?
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 96 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
H 0 72 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Cl 0 16 0.132 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0 8 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0 24 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
? ? ?
? ? ?
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
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N(2) O(1) C(5) 108.6(4) . . . ?
C(8) O(8) H(8) 119.5 . . . no
O(1) N(2) C(3) 105.1(4) . . . ?
N(2) C(3) C(4) 112.0(5) . . . ?
N(2) C(3) C(31) 117.2(5) . . . ?
C(4) C(3) C(31) 130.9(6) . . . ?
C(3) C(4) C(5) 103.4(5) . . . ?
C(3) C(4) C(6) 128.1(5) . . . ?
C(5) C(4) C(6) 128.5(6) . . . ?
O(1) C(5) C(4) 111.1(5) . . . ?
O(1) C(5) H(5) 124.5 . . . no
C(4) C(5) H(5) 124.5 . . . no
O(6) C(6) C(4) 120.7(5) . . . ?
O(6) C(6) C(7) 120.9(6) . . . ?
C(4) C(6) C(7) 118.3(5) . . . ?
C(6) C(7) C(8) 115.3(5) . . . ?
C(6) C(7) H(7b) 108.0 . . . no
C(6) C(7) H(7a) 108.0 . . . no
C(8) C(7) H(7b) 108.0 . . . no
C(8) C(7) H(7a) 108.0 . . . no
H(7b) C(7) H(7a) 109.5 . . . no
O(8) C(8) C(7) 123.2(9) . . . ?
O(8) C(8) H(8b) 105.9 . . . no
O(8) C(8) H(8a) 105.9 . . . no
C(7) C(8) H(8b) 105.9 . . . no
C(7) C(8) H(8a) 105.9 . . . no
H(8b) C(8) H(8a) 109.4 . . . no
C(3) C(31) C(32) 121.6(6) . . . ?
C(3) C(31) C(36) 119.8(6) . . . ?
C(32) C(31) C(36) 118.6(5) . . . ?
Cl(32) C(32) C(31) 119.3(5) . . . ?
Cl(32) C(32) C(33) 119.4(6) . . . ?
C(31) C(32) C(33) 121.3(6) . . . ?
C(32) C(33) C(34) 118.9(7) . . . ?
C(32) C(33) H(33) 120.5 . . . no
C(34) C(33) H(33) 120.6 . . . no
C(33) C(34) C(35) 121.6(7) . . . ?
C(33) C(34) H(34) 119.2 . . . no
C(35) C(34) H(34) 119.2 . . . no
C(34) C(35) C(36) 118.6(7) . . . ?
C(34) C(35) H(35) 120.7 . . . no
C(36) C(35) H(35) 120.7 . . . no
Cl(36) C(36) C(31) 120.7(5) . . . ?
Cl(36) C(36) C(35) 118.4(6) . . . ?
C(31) C(36) C(35) 120.9(7) . . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl(32) C(32) 1.709(6) . . ?
Cl(36) C(36) 1.711(6) . . ?
O(1) N(2) 1.409(5) . . ?
O(1) C(5) 1.310(6) . . ?
O(6) C(6) 1.204(5) . . ?
O(8) C(8) 1.191(8) . . ?
O(8) H(8) 0.76 . . no
N(2) C(3) 1.290(6) . . ?
C(3) C(4) 1.413(7) . . ?
C(3) C(31) 1.473(7) . . ?
C(4) C(5) 1.340(7) . . ?
C(4) C(6) 1.441(7) . . ?
C(5) H(5) 0.97 . . no
C(6) C(7) 1.472(7) . . ?
C(7) C(8) 1.476(10) . . ?
C(7) H(7b) 0.97 . . no
C(7) H(7a) 0.97 . . no
C(8) H(8b) 0.97 . . no
C(8) H(8a) 0.97 . . no
C(31) C(32) 1.358(7) . . ?
C(31) C(36) 1.378(7) . . ?
C(32) C(33) 1.375(8) . . ?
C(33) C(34) 1.360(9) . . ?
C(33) H(33) 0.97 . . no
C(34) C(35) 1.358(9) . . ?
C(34) H(34) 0.97 . . no
C(35) C(36) 1.381(8) . . ?
C(35) H(35) 0.97 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl(32) O(8) 3.527(9) . 1_556 no
Cl(36) N(2) 3.516(5) . 7_554 no
O(1) C(33) 3.320(8) . 8 no
O(1) C(35) 3.368(8) . 2 no
O(6) C(5) 3.230(7) . 8_454 no
O(6) C(7) 3.549(7) . 8_454 no
O(8) O(8) 3.059(12) . 5_554 no
O(8) C(7) 3.336(8) . 4_554 no
N(2) C(35) 3.196(8) . 2 no
N(2) C(33) 3.357(9) . 8 no
C(5) C(35) 3.458(9) . 8_554 no
C(5) C(36) 3.518(8) . 8_554 no
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
Cl(32) C(32) C(31) C(3) . . . . -1.7(8) no
Cl(32) C(32) C(31) C(36) . . . . 179.9(4) no
Cl(32) C(32) C(33) C(34) . . . . 178.8(5) no
Cl(36) C(36) C(31) C(3) . . . . 0.9(7) no
Cl(36) C(36) C(31) C(32) . . . . 179.3(4) no
Cl(36) C(36) C(35) C(34) . . . . -178.6(5) no
O(1) N(2) C(3) C(4) . . . . -0.6(6) no
O(1) N(2) C(3) C(31) . . . . 179.0(5) no
O(1) C(5) C(4) C(3) . . . . -0.8(7) no
O(1) C(5) C(4) C(6) . . . . -179.6(5) no
O(6) C(6) C(4) C(3) . . . . 3.0(10) no
O(6) C(6) C(4) C(5) . . . . -178.4(7) no
O(6) C(6) C(7) C(8) . . . . -11.7(10) no
O(8) C(8) C(7) C(6) . . . . 52.8(14) no
N(2) O(1) C(5) C(4) . . . . 0.4(7) no
N(2) C(3) C(4) C(5) . . . . 0.9(7) no
N(2) C(3) C(4) C(6) . . . . 179.7(6) no
N(2) C(3) C(31) C(32) . . . . -89.3(7) no
N(2) C(3) C(31) C(36) . . . . 89.1(7) no
C(3) N(2) O(1) C(5) . . . . 0.1(6) no
C(3) C(4) C(6) C(7) . . . . -179.4(6) no
C(3) C(31) C(32) C(33) . . . . 178.8(6) no
C(3) C(31) C(36) C(35) . . . . -178.2(6) no
C(4) C(3) C(31) C(32) . . . . 90.3(8) no
C(4) C(3) C(31) C(36) . . . . -91.3(8) no
C(4) C(6) C(7) C(8) . . . . 170.7(7) no
C(5) C(4) C(3) C(31) . . . . -178.7(7) no
C(5) C(4) C(6) C(7) . . . . -0.8(9) no
C(6) C(4) C(3) C(31) . . . . 0.1(10) no
C(31) C(32) C(33) C(34) . . . . -1.7(10) no
C(31) C(36) C(35) C(34) . . . . 0.5(9) no
C(32) C(31) C(36) C(35) . . . . 0.2(9) no
C(32) C(33) C(34) C(35) . . . . 2.4(11) no
C(33) C(32) C(31) C(36) . . . . 0.3(9) no
C(33) C(34) C(35) C(36) . . . . -1.9(11) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8692688
