#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223102.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223102
loop_
_publ_author_name
'Hu, Jun'
'Chen, Guo-song'
'Guo, Li-hua'
'Wang, Ji-kui'
'Xu, Yan-hua'
_publ_section_title
;
 (S)-Ethyl 2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2082
_journal_paper_doi               10.1107/S1600536809030074
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H17 Cl N2 O4'
_chemical_formula_moiety         'C19 H17 Cl N2 O4'
_chemical_formula_sum            'C19 H17 Cl N2 O4'
_chemical_formula_weight         372.80
_chemical_melting_point          350
_chemical_name_common            Quizalofop-P
_chemical_name_systematic
;
(S)-Ethyl 2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.970(2)
_cell_length_b                   4.4760(9)
_cell_length_c                   20.450(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     909.7(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3762
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.9324
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.195
_refine_ls_abs_structure_details 'Flack (1983), 932 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0500
_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)+(0.085P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                1254
_reflns_number_total             1898
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2712.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2223102
_cod_database_fobs_code          2223102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_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
Cl Cl 0.50826(14) 0.9066(5) 0.08796(7) 0.0921(6) Uani d . 1 . .
O O1 1.8615(3) 0.4503(12) 0.3878(2) 0.0925(14) Uani d . 1 . .
O O2 1.7523(4) 0.0871(12) 0.3367(2) 0.0956(14) Uani d . 1 . .
O O3 1.5198(3) 0.2389(10) 0.38949(16) 0.0730(11) Uani d . 1 . .
O O4 1.2147(3) 0.1148(12) 0.15458(16) 0.0838(13) Uani d . 1 . .
N N1 0.9132(4) 0.2496(12) 0.05649(17) 0.0616(11) Uani d . 1 . .
N N2 1.0378(4) 0.4196(12) 0.18081(17) 0.0563(10) Uani d . 1 . .
C C1 2.0926(5) 0.474(2) 0.4119(4) 0.131(3) Uani d . 1 . .
H H1B 2.1793 0.4138 0.3993 0.196 Uiso calc R 1 . .
H H1C 2.0803 0.3998 0.4551 0.196 Uiso calc R 1 . .
H H1D 2.0871 0.6882 0.4120 0.196 Uiso calc R 1 . .
C C2 1.9882(5) 0.353(2) 0.3656(3) 0.095(2) Uani d . 1 . .
H H2B 1.9988 0.4282 0.3218 0.115 Uiso calc R 1 . .
H H2C 1.9928 0.1370 0.3648 0.115 Uiso calc R 1 . .
C C3 1.7536(5) 0.3000(15) 0.3698(3) 0.0657(15) Uani d . 1 . .
C C4 1.6313(4) 0.4380(16) 0.3988(2) 0.0710(15) Uani d . 1 . .
H H4A 1.6092 0.6308 0.3779 0.085 Uiso calc R 1 . .
C C5 1.6551(6) 0.476(2) 0.4726(3) 0.107(3) Uani d . 1 . .
H H5A 1.5771 0.5645 0.4893 0.161 Uiso calc R 1 . .
H H5B 1.7316 0.6029 0.4824 0.161 Uiso calc R 1 . .
H H5C 1.6716 0.2841 0.4927 0.161 Uiso calc R 1 . .
C C6 1.4468(4) 0.2317(14) 0.3298(2) 0.0582(13) Uani d . 1 . .
C C7 1.3386(5) 0.0408(14) 0.3263(2) 0.0656(14) Uani d . 1 . .
H H7A 1.3203 -0.0682 0.3633 0.079 Uiso calc R 1 . .
C C8 1.2570(5) 0.0074(15) 0.2696(2) 0.0715(17) Uani d . 1 . .
H H8A 1.1837 -0.1217 0.2677 0.086 Uiso calc R 1 . .
C C9 1.2861(5) 0.1681(15) 0.2160(2) 0.0637(15) Uani d . 1 . .
C C10 1.3937(5) 0.3564(15) 0.2181(3) 0.0720(15) Uani d . 1 . .
H H10A 1.4119 0.4639 0.1808 0.086 Uiso calc R 1 . .
C C11 1.4758(5) 0.3883(16) 0.2752(3) 0.0718(15) Uani d . 1 . .
H H11A 1.5500 0.5147 0.2765 0.086 Uiso calc R 1 . .
C C12 1.0919(5) 0.2395(14) 0.1409(2) 0.0612(13) Uani d . 1 . .
C C13 0.9127(4) 0.5295(12) 0.1580(2) 0.0517(12) Uani d . 1 . .
C C14 0.8466(5) 0.7268(13) 0.1979(2) 0.0586(13) Uani d . 1 . .
H H14A 0.8859 0.7811 0.2389 0.070 Uiso calc R 1 . .
C C15 0.7228(5) 0.8395(14) 0.1757(2) 0.0658(15) Uani d . 1 . .
H H15A 0.6783 0.9715 0.2017 0.079 Uiso calc R 1 . .
C C16 0.6646(5) 0.7562(14) 0.1148(2) 0.0626(14) Uani d . 1 . .
C C17 0.7261(5) 0.5646(14) 0.0749(2) 0.0614(14) Uani d . 1 . .
H H17A 0.6852 0.5136 0.0340 0.074 Uiso calc R 1 . .
C C18 0.8516(4) 0.4457(12) 0.0964(2) 0.0509(12) Uani d . 1 . .
C C19 1.0293(5) 0.1538(15) 0.0790(2) 0.0646(15) Uani d . 1 . .
H H19A 1.0746 0.0216 0.0534 0.078 Uiso calc R 1 . .
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 118.8(5) ?
C6 O3 C4 . . 119.1(4) ?
C12 O4 C9 . . 119.8(4) ?
C19 N1 C18 . . 115.6(4) ?
C12 N2 C13 . . 114.7(4) ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1C . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
O1 C2 C1 . . 106.4(6) ?
O1 C2 H2B . . 110.4 ?
C1 C2 H2B . . 110.4 ?
O1 C2 H2C . . 110.4 ?
C1 C2 H2C . . 110.4 ?
H2B C2 H2C . . 108.6 ?
O2 C3 O1 . . 124.0(6) ?
O2 C3 C4 . . 125.6(6) ?
O1 C3 C4 . . 110.4(5) ?
O3 C4 C5 . . 105.1(5) ?
O3 C4 C3 . . 109.5(5) ?
C5 C4 C3 . . 111.4(4) ?
O3 C4 H4A . . 110.3 ?
C5 C4 H4A . . 110.3 ?
C3 C4 H4A . . 110.3 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C11 C6 O3 . . 125.7(5) ?
C11 C6 C7 . . 119.5(5) ?
O3 C6 C7 . . 114.9(5) ?
C8 C7 C6 . . 121.5(5) ?
C8 C7 H7A . . 119.2 ?
C6 C7 H7A . . 119.2 ?
C9 C8 C7 . . 118.3(5) ?
C9 C8 H8A . . 120.9 ?
C7 C8 H8A . . 120.9 ?
C8 C9 C10 . . 121.3(5) ?
C8 C9 O4 . . 120.1(5) ?
C10 C9 O4 . . 118.1(5) ?
C9 C10 C11 . . 120.2(5) ?
C9 C10 H10A . . 119.9 ?
C11 C10 H10A . . 119.9 ?
C6 C11 C10 . . 119.2(5) ?
C6 C11 H11A . . 120.4 ?
C10 C11 H11A . . 120.4 ?
N2 C12 O4 . . 122.8(4) ?
N2 C12 C19 . . 123.7(5) ?
O4 C12 C19 . . 113.5(5) ?
N2 C13 C14 . . 118.7(4) ?
N2 C13 C18 . . 121.4(4) ?
C14 C13 C18 . . 119.9(4) ?
C15 C14 C13 . . 119.4(4) ?
C15 C14 H14A . . 120.3 ?
C13 C14 H14A . . 120.3 ?
C14 C15 C16 . . 119.9(5) ?
C14 C15 H15A . . 120.1 ?
C16 C15 H15A . . 120.1 ?
C17 C16 C15 . . 122.2(5) ?
C17 C16 Cl . . 119.2(4) ?
C15 C16 Cl . . 118.6(5) ?
C16 C17 C18 . . 119.1(4) ?
C16 C17 H17A . . 120.4 ?
C18 C17 H17A . . 120.4 ?
N1 C18 C17 . . 119.2(4) ?
N1 C18 C13 . . 121.3(4) ?
C17 C18 C13 . . 119.5(5) ?
N1 C19 C12 . . 123.3(5) ?
N1 C19 H19A . . 118.3 ?
C12 C19 H19A . . 118.3 ?
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
Cl C16 . 1.746(5) ?
O1 C2 . 1.443(6) ?
O1 C3 . 1.298(7) ?
O2 C3 . 1.168(7) ?
O3 C4 . 1.426(6) ?
O3 C6 . 1.371(5) ?
O4 C9 . 1.414(6) ?
O4 C12 . 1.355(6) ?
N1 C18 . 1.375(6) ?
N1 C19 . 1.285(6) ?
N2 C12 . 1.294(7) ?
N2 C13 . 1.386(6) ?
C1 C2 . 1.455(9) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 C4 . 1.528(8) ?
C4 C5 . 1.519(7) ?
C4 H4A . 0.9800 ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C11 . 1.370(7) ?
C6 C7 . 1.373(7) ?
C7 C8 . 1.372(6) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.361(8) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.363(8) ?
C10 C11 . 1.379(7) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
C12 C19 . 1.420(6) ?
C13 C14 . 1.401(7) ?
C13 C18 . 1.407(6) ?
C14 C15 . 1.376(7) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.383(7) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.362(7) ?
C17 C18 . 1.398(6) ?
C17 H17A . 0.9300 ?
C19 H19A . 0.9300 ?
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
C19 H19A N1 2_745 0.93 2.57 3.396(7) 149
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
C3 O1 C2 C1 . . . . -157.4(6) ?
C2 O1 C3 O2 . . . . 0.7(9) ?
C2 O1 C3 C4 . . . . 179.7(5) ?
C6 O3 C4 C5 . . . . 159.6(5) ?
C6 O3 C4 C3 . . . . -80.7(6) ?
O2 C3 C4 O3 . . . . 10.5(8) ?
O1 C3 C4 O3 . . . . -168.5(4) ?
O2 C3 C4 C5 . . . . 126.3(7) ?
O1 C3 C4 C5 . . . . -52.7(8) ?
C4 O3 C6 C11 . . . . 4.3(8) ?
C4 O3 C6 C7 . . . . -177.8(5) ?
C11 C6 C7 C8 . . . . -1.3(9) ?
O3 C6 C7 C8 . . . . -179.3(5) ?
C6 C7 C8 C9 . . . . 0.3(8) ?
C7 C8 C9 C10 . . . . 0.4(8) ?
C7 C8 C9 O4 . . . . 172.5(5) ?
C12 O4 C9 C8 . . . . 81.4(7) ?
C12 O4 C9 C10 . . . . -106.3(6) ?
C8 C9 C10 C11 . . . . -0.1(9) ?
O4 C9 C10 C11 . . . . -172.4(6) ?
O3 C6 C11 C10 . . . . 179.3(5) ?
C7 C6 C11 C10 . . . . 1.5(9) ?
C9 C10 C11 C6 . . . . -0.9(9) ?
C13 N2 C12 O4 . . . . 178.9(5) ?
C13 N2 C12 C19 . . . . -1.0(8) ?
C9 O4 C12 N2 . . . . 3.3(9) ?
C9 O4 C12 C19 . . . . -176.8(5) ?
C12 N2 C13 C14 . . . . -179.9(5) ?
C12 N2 C13 C18 . . . . 0.4(7) ?
N2 C13 C14 C15 . . . . 179.5(5) ?
C18 C13 C14 C15 . . . . -0.8(7) ?
C13 C14 C15 C16 . . . . 0.4(8) ?
C14 C15 C16 C17 . . . . -0.3(8) ?
C14 C15 C16 Cl . . . . -179.3(4) ?
C15 C16 C17 C18 . . . . 0.6(8) ?
Cl C16 C17 C18 . . . . 179.7(4) ?
C19 N1 C18 C17 . . . . 178.8(5) ?
C19 N1 C18 C13 . . . . -0.9(7) ?
C16 C17 C18 N1 . . . . 179.3(5) ?
C16 C17 C18 C13 . . . . -1.0(7) ?
N2 C13 C18 N1 . . . . 0.5(7) ?
C14 C13 C18 N1 . . . . -179.2(5) ?
N2 C13 C18 C17 . . . . -179.2(5) ?
C14 C13 C18 C17 . . . . 1.1(7) ?
C18 N1 C19 C12 . . . . 0.4(8) ?
N2 C12 C19 N1 . . . . 0.6(9) ?
O4 C12 C19 N1 . . . . -179.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 83441
