#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222541.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_2222541
loop_
_publ_author_name
'Xu, Jing'
'Sheng, Hui'
'He, Mei'
'He, Ping'
_publ_section_title
;Ethyl
 5-cyano-4-[2-(2,4-dichlorophenoxy)acetamido]-1-phenyl-1H-pyrrole-3-carboxylate
;
_journal_coeditor_code           AT2840
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1950
_journal_paper_doi               10.1107/S1600536809027809
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H17 Cl2 N3 O4'
_chemical_formula_moiety         'C22 H17 Cl2 N3 O4'
_chemical_formula_sum            'C22 H17 Cl2 N3 O4'
_chemical_formula_weight         458.29
_chemical_name_systematic
;Ethyl
 5-cyano-4-[2-(2,4-dichlorophenoxy)acetamido]-1-phenyl-1H-pyrrole-
3-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 90.00
_cell_angle_gamma                89.7730(10)
_cell_formula_units_Z            8
_cell_length_a                   32.8846(18)
_cell_length_b                   7.6224(4)
_cell_length_c                   17.2834(9)
_cell_measurement_reflns_used    4400
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.47
_cell_volume                     4332.2(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0807
_diffrn_reflns_av_sigmaI/netI    0.088
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16521
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.307
_refine_ls_extinction_coef       0.0042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0658
_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/[σ²(Fo²)+(0.055P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                3034
_reflns_number_total             4279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2840.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222541
_cod_database_fobs_code          2222541
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'
'-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_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
C C1 1.06329(6) 0.1879(3) 0.05715(13) 0.0426(6) Uani d . 1 . .
C C2 1.09068(7) 0.1312(3) 0.11185(14) 0.0466(6) Uani d . 1 . .
H H2 1.0813 0.0801 0.1573 0.056 Uiso calc R 1 . .
C C3 1.13204(7) 0.1495(3) 0.09995(14) 0.0472(6) Uani d . 1 . .
H H3 1.1505 0.1107 0.1369 0.057 Uiso calc R 1 . .
C C4 1.14550(7) 0.2257(3) 0.03284(15) 0.0463(6) Uani d . 1 . .
C C5 1.11863(7) 0.2840(3) -0.02255(14) 0.0470(6) Uani d . 1 . .
H H5 1.1282 0.3351 -0.0679 0.056 Uiso calc R 1 . .
C C6 1.07783(7) 0.2659(3) -0.01021(14) 0.0469(6) Uani d . 1 . .
C C7 1.00695(6) 0.1112(4) 0.13490(13) 0.0558(7) Uani d . 1 . .
H H7A 1.0184 0.1792 0.1770 0.067 Uiso calc R 1 . .
H H7B 1.0147 -0.0103 0.1420 0.067 Uiso calc R 1 . .
C C8 0.96114(7) 0.1270(4) 0.13558(14) 0.0511(7) Uani d . 1 . .
C C9 0.90125(6) 0.1809(3) 0.05703(13) 0.0368(5) Uani d . 1 . .
C C10 0.88509(6) 0.2629(3) -0.00962(13) 0.0399(6) Uani d . 1 . .
C C11 0.84392(7) 0.2760(3) 0.00079(14) 0.0440(6) Uani d . 1 . .
H H11 0.8259 0.3266 -0.0340 0.053 Uiso calc R 1 . .
C C12 0.86902(6) 0.1425(3) 0.10524(12) 0.0387(5) Uani d . 1 . .
C C13 0.86531(6) 0.0454(3) 0.17456(14) 0.0446(6) Uani d . 1 . .
C C14 0.90849(7) 0.3115(3) -0.07786(13) 0.0431(6) Uani d . 1 . .
C C15 0.90645(8) 0.4263(4) -0.20453(14) 0.0589(7) Uani d . 1 . .
H H15A 0.9189 0.3226 -0.2267 0.071 Uiso calc R 1 . .
H H15B 0.9277 0.5115 -0.1943 0.071 Uiso calc R 1 . .
C C16 0.87619(9) 0.5007(4) -0.25914(15) 0.0693(8) Uani d . 1 . .
H H16A 0.8568 0.4119 -0.2729 0.104 Uiso calc R 1 . .
H H16B 0.8898 0.5412 -0.3048 0.104 Uiso calc R 1 . .
H H16C 0.8624 0.5970 -0.2350 0.104 Uiso calc R 1 . .
C C17 0.79429(7) 0.2161(4) 0.10469(13) 0.0448(6) Uani d . 1 . .
C C18 0.77391(8) 0.0684(4) 0.12715(16) 0.0647(8) Uani d . 1 . .
H H18 0.7852 -0.0419 0.1193 0.078 Uiso calc R 1 . .
C C19 0.73596(8) 0.0858(5) 0.16203(18) 0.0770(10) Uani d . 1 . .
H H19 0.7217 -0.0133 0.1775 0.092 Uiso calc R 1 . .
C C20 0.71982(8) 0.2485(5) 0.17348(18) 0.0729(10) Uani d . 1 . .
H H20 0.6945 0.2596 0.1968 0.088 Uiso calc R 1 . .
C C21 0.74032(9) 0.3942(5) 0.15128(18) 0.0774(10) Uani d . 1 . .
H H21 0.7291 0.5045 0.1596 0.093 Uiso calc R 1 . .
C C22 0.77795(8) 0.3792(4) 0.11624(16) 0.0650(8) Uani d . 1 . .
H H22 0.7920 0.4789 0.1007 0.078 Uiso calc R 1 . .
Cl Cl1 1.197500(19) 0.25261(10) 0.01853(5) 0.0708(3) Uani d . 1 . .
Cl Cl2 1.04355(2) 0.33930(11) -0.07912(4) 0.0718(3) Uani d . 1 . .
N N1 0.94269(5) 0.1515(3) 0.06772(11) 0.0413(5) Uani d . 1 . .
H H1 0.9550(7) 0.163(3) 0.0265(14) 0.050 Uiso d . 1 . .
N N2 0.83373(5) 0.2042(3) 0.06907(11) 0.0428(5) Uani d . 1 . .
N N3 0.85896(7) -0.0374(3) 0.22814(13) 0.0672(7) Uani d . 1 . .
O O1 1.02216(4) 0.1736(3) 0.06353(9) 0.0548(5) Uani d . 1 . .
O O2 0.94335(5) 0.1152(3) 0.19676(10) 0.0876(8) Uani d . 1 . .
O O3 0.94465(5) 0.2865(3) -0.08352(10) 0.0602(5) Uani d . 1 . .
O O4 0.88571(5) 0.3817(2) -0.13360(9) 0.0512(5) Uani d . 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
O1 C1 C2 . . 124.7(2) ?
O1 C1 C6 . . 116.3(2) ?
C2 C1 C6 . . 119.0(2) ?
C1 C2 C3 . . 120.7(2) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.1(2) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 121.2(2) ?
C3 C4 Cl1 . . 119.2(2) ?
C5 C4 Cl1 . . 119.60(19) ?
C6 C5 C4 . . 119.3(2) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 120.7(2) ?
C5 C6 Cl2 . . 119.96(19) ?
C1 C6 Cl2 . . 119.30(18) ?
O1 C7 C8 . . 109.44(19) ?
O1 C7 H7A . . 109.8 ?
C8 C7 H7A . . 109.8 ?
O1 C7 H7B . . 109.8 ?
C8 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.2 ?
O2 C8 N1 . . 123.9(2) ?
O2 C8 C7 . . 118.8(2) ?
N1 C8 C7 . . 117.25(19) ?
C12 C9 N1 . . 129.6(2) ?
C12 C9 C10 . . 107.26(19) ?
N1 C9 C10 . . 123.14(18) ?
C11 C10 C9 . . 107.27(19) ?
C11 C10 C14 . . 127.6(2) ?
C9 C10 C14 . . 124.99(19) ?
N2 C11 C10 . . 109.4(2) ?
N2 C11 H11 . . 125.3 ?
C10 C11 H11 . . 125.3 ?
C9 C12 N2 . . 107.22(19) ?
C9 C12 C13 . . 133.6(2) ?
N2 C12 C13 . . 118.87(18) ?
N3 C13 C12 . . 173.9(2) ?
O3 C14 O4 . . 123.9(2) ?
O3 C14 C10 . . 123.1(2) ?
O4 C14 C10 . . 112.99(19) ?
O4 C15 C16 . . 108.3(2) ?
O4 C15 H15A . . 110.0 ?
C16 C15 H15A . . 110.0 ?
O4 C15 H15B . . 110.0 ?
C16 C15 H15B . . 110.0 ?
H15A C15 H15B . . 108.4 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 C22 . . 120.9(2) ?
C18 C17 N2 . . 120.8(2) ?
C22 C17 N2 . . 118.3(2) ?
C17 C18 C19 . . 118.9(3) ?
C17 C18 H18 . . 120.5 ?
C19 C18 H18 . . 120.5 ?
C20 C19 C18 . . 119.9(3) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C21 C20 C19 . . 120.7(3) ?
C21 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
C20 C21 C22 . . 120.1(3) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C17 C22 C21 . . 119.4(3) ?
C17 C22 H22 . . 120.3 ?
C21 C22 H22 . . 120.3 ?
C8 N1 C9 . . 125.75(19) ?
C8 N1 H1 . . 123.4(17) ?
C9 N1 H1 . . 110.5(18) ?
C11 N2 C12 . . 108.81(17) ?
C11 N2 C17 . . 125.1(2) ?
C12 N2 C17 . . 125.30(19) ?
C1 O1 C7 . . 116.70(18) ?
C14 O4 C15 . . 116.29(18) ?
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 O1 . 1.363(2) ?
C1 C2 . 1.377(3) ?
C1 C6 . 1.393(3) ?
C2 C3 . 1.384(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(4) ?
C4 Cl1 . 1.742(2) ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.9300 ?
C6 Cl2 . 1.734(3) ?
C7 O1 . 1.415(2) ?
C7 C8 . 1.513(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O2 . 1.213(3) ?
C8 N1 . 1.335(3) ?
C9 C12 . 1.381(3) ?
C9 N1 . 1.395(3) ?
C9 C10 . 1.416(3) ?
C10 C11 . 1.371(3) ?
C10 C14 . 1.458(3) ?
C11 N2 . 1.345(3) ?
C11 H11 . 0.9300 ?
C12 N2 . 1.401(3) ?
C12 C13 . 1.415(3) ?
C13 N3 . 1.141(3) ?
C14 O3 . 1.210(3) ?
C14 O4 . 1.334(3) ?
C15 O4 . 1.445(3) ?
C15 C16 . 1.486(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.368(4) ?
C17 C22 . 1.370(3) ?
C17 N2 . 1.440(3) ?
C18 C19 . 1.394(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.365(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.356(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.384(3) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
N1 H1 . 0.82(2) ?
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
N1 H1 O3 . 0.82(2) 2.15(3) 2.813(3) 137(2)
C7 H7A O2 2_755 0.97 2.57 3.341(3) 136.7
C3 H3 N3 2_755 0.93 2.61 3.312(3) 132.5
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
O1 C1 C2 C3 . . . . 179.2(2) ?
C6 C1 C2 C3 . . . . -0.7(4) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C2 C3 C4 Cl1 . . . . 178.79(19) ?
C3 C4 C5 C6 . . . . 0.2(4) ?
Cl1 C4 C5 C6 . . . . -178.57(18) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
C4 C5 C6 Cl2 . . . . 179.78(19) ?
O1 C1 C6 C5 . . . . -179.0(2) ?
C2 C1 C6 C5 . . . . 0.9(4) ?
O1 C1 C6 Cl2 . . . . 0.6(3) ?
C2 C1 C6 Cl2 . . . . -179.51(19) ?
O1 C7 C8 O2 . . . . -164.7(3) ?
O1 C7 C8 N1 . . . . 15.9(3) ?
C12 C9 C10 C11 . . . . 1.5(3) ?
N1 C9 C10 C11 . . . . -177.7(2) ?
C12 C9 C10 C14 . . . . -174.7(2) ?
N1 C9 C10 C14 . . . . 6.1(4) ?
C9 C10 C11 N2 . . . . -1.1(3) ?
C14 C10 C11 N2 . . . . 174.9(2) ?
N1 C9 C12 N2 . . . . 177.8(2) ?
C10 C9 C12 N2 . . . . -1.3(2) ?
N1 C9 C12 C13 . . . . -9.1(4) ?
C10 C9 C12 C13 . . . . 171.7(3) ?
C11 C10 C14 O3 . . . . -175.9(2) ?
C9 C10 C14 O3 . . . . -0.5(4) ?
C11 C10 C14 O4 . . . . 2.5(4) ?
C9 C10 C14 O4 . . . . 177.9(2) ?
C22 C17 C18 C19 . . . . 0.2(4) ?
N2 C17 C18 C19 . . . . 179.4(2) ?
C17 C18 C19 C20 . . . . -0.2(5) ?
C18 C19 C20 C21 . . . . 0.0(5) ?
C19 C20 C21 C22 . . . . 0.3(5) ?
C18 C17 C22 C21 . . . . 0.1(4) ?
N2 C17 C22 C21 . . . . -179.2(3) ?
C20 C21 C22 C17 . . . . -0.4(5) ?
O2 C8 N1 C9 . . . . 5.3(4) ?
C7 C8 N1 C9 . . . . -175.4(2) ?
C12 C9 N1 C8 . . . . -21.0(4) ?
C10 C9 N1 C8 . . . . 158.0(2) ?
C10 C11 N2 C12 . . . . 0.3(3) ?
C10 C11 N2 C17 . . . . 170.5(2) ?
C9 C12 N2 C11 . . . . 0.7(3) ?
C13 C12 N2 C11 . . . . -173.6(2) ?
C9 C12 N2 C17 . . . . -169.5(2) ?
C13 C12 N2 C17 . . . . 16.2(3) ?
C18 C17 N2 C11 . . . . 126.0(3) ?
C22 C17 N2 C11 . . . . -54.7(3) ?
C18 C17 N2 C12 . . . . -65.4(3) ?
C22 C17 N2 C12 . . . . 113.9(3) ?
C2 C1 O1 C7 . . . . 6.4(3) ?
C6 C1 O1 C7 . . . . -173.7(2) ?
C8 C7 O1 C1 . . . . 172.4(2) ?
O3 C14 O4 C15 . . . . 0.9(4) ?
C10 C14 O4 C15 . . . . -177.4(2) ?
C16 C15 O4 C14 . . . . 179.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742881
