#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/09/2230950.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_2230950
loop_
_publ_author_name
'Alliouche, Hayette'
'Bouacida, Sofiane'
'Roisnel, Thierry'
'Belfaitah, Ali'
_publ_section_title
;
 Ethyl
 3-(2-chloro-5,8-dimethoxyquinolin-3-yl)-2-cyanooxirane-2-carboxylate
;
_journal_coeditor_code           ZJ2015
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1754
_journal_page_last               o1755
_journal_paper_doi               10.1107/S1600536811023336
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H15 Cl N2 O5'
_chemical_formula_moiety         'C17 H15 Cl N2 O5'
_chemical_formula_sum            'C17 H15 Cl N2 O5'
_chemical_formula_weight         362.76
_chemical_name_systematic
;
Ethyl 3-(2-chloro-5,8-dimethoxyquinolin-3-yl)-2-cyanooxirane-2-carboxylate
;
_space_group_IT_number           2
_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
_cell_angle_alpha                102.489(2)
_cell_angle_beta                 103.977(2)
_cell_angle_gamma                96.026(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3784(3)
_cell_length_b                   10.1071(4)
_cell_length_c                   10.7027(4)
_cell_measurement_reflns_used    7904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.52
_cell_volume                     846.77(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12867
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0775P)²+0.5515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                3369
_reflns_number_total             3803
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zj2015.cif
_cod_data_source_block           I
_cod_database_code               2230950
_cod_database_fobs_code          2230950
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.21857(5) -0.03042(5) 1.03331(5) 0.03620(16) Uani d . 1 1 . .
C C1 0.3363(2) 0.09251(17) 0.98421(17) 0.0277(4) Uani d . 1 1 . .
N N2 0.45074(18) 0.18016(15) 1.07892(14) 0.0279(3) Uani d . 1 1 . .
C C3 0.5441(2) 0.27800(17) 1.04347(17) 0.0274(4) Uani d . 1 1 . .
C C4 0.6751(2) 0.37174(18) 1.14484(18) 0.0312(4) Uani d . 1 1 . .
O O5 0.69369(17) 0.35382(14) 1.27008(13) 0.0379(3) Uani d . 1 1 . .
C C6 0.8178(3) 0.4523(3) 1.3736(2) 0.0508(6) Uani d . 1 1 . .
H H6A 0.9272 0.448 1.3567 0.076 Uiso calc R 1 1 . .
H H6B 0.8202 0.4318 1.4593 0.076 Uiso calc R 1 1 . .
H H6C 0.7909 0.5447 1.3756 0.076 Uiso calc R 1 1 . .
C C7 0.7706(2) 0.4691(2) 1.1101(2) 0.0371(4) Uani d . 1 1 . .
H H7 0.8587 0.5309 1.177 0.045 Uiso calc R 1 1 . .
C C8 0.7410(3) 0.4798(2) 0.9768(2) 0.0387(4) Uani d . 1 1 . .
H H8 0.8091 0.5483 0.9558 0.046 Uiso calc R 1 1 . .
C C9 0.6153(2) 0.3923(2) 0.8783(2) 0.0349(4) Uani d . 1 1 . .
O O10 0.5731(2) 0.39496(16) 0.74704(15) 0.0439(4) Uani d . 1 1 . .
C C11 0.6705(3) 0.4986(2) 0.7119(2) 0.0502(6) Uani d . 1 1 . .
H H11A 0.6632 0.5894 0.7635 0.075 Uiso calc R 1 1 . .
H H11B 0.628 0.4926 0.6168 0.075 Uiso calc R 1 1 . .
H H11C 0.7871 0.4848 0.7313 0.075 Uiso calc R 1 1 . .
C C12 0.5154(2) 0.28768(18) 0.90951(18) 0.0307(4) Uani d . 1 1 . .
C C13 0.3894(2) 0.18913(19) 0.81199(18) 0.0326(4) Uani d . 1 1 . .
H H13 0.3669 0.1923 0.7214 0.039 Uiso calc R 1 1 . .
C C14 0.2996(2) 0.08919(18) 0.84700(17) 0.0309(4) Uani d . 1 1 . .
C C15 0.1747(3) -0.0235(2) 0.74667(18) 0.0367(4) Uani d . 1 1 . .
H H15 0.1828 -0.1184 0.7581 0.044 Uiso calc R 1 1 . .
O O16 0.13334(18) -0.01119(16) 0.61244(13) 0.0421(4) Uani d . 1 1 . .
C C17 0.0041(2) -0.00089(19) 0.67835(18) 0.0347(4) Uani d . 1 1 . .
C C18 -0.0392(2) 0.1364(2) 0.7104(2) 0.0379(4) Uani d . 1 1 . .
N N19 -0.0698(2) 0.2443(2) 0.7373(3) 0.0590(6) Uani d . 1 1 . .
C C20 -0.1344(3) -0.1243(2) 0.6298(2) 0.0429(5) Uani d . 1 1 . .
O O21 -0.1073(3) -0.23961(17) 0.6035(2) 0.0796(7) Uani d . 1 1 . .
O O22 -0.27917(19) -0.08591(15) 0.62274(14) 0.0423(4) Uani d . 1 1 . .
C C23 -0.4215(3) -0.1992(3) 0.5871(3) 0.0537(6) Uani d . 1 1 . .
H H23A -0.4089 -0.275 0.516 0.064 Uiso calc R 1 1 . .
H H23B -0.4248 -0.2353 0.6655 0.064 Uiso calc R 1 1 . .
C C24 -0.5687(4) -0.1501(3) 0.5431(4) 0.0786(10) Uani d . 1 1 . .
H H24A -0.5758 -0.07 0.6108 0.118 Uiso calc R 1 1 . .
H H24B -0.6643 -0.2222 0.5272 0.118 Uiso calc R 1 1 . .
H H24C -0.5697 -0.1233 0.4602 0.118 Uiso calc R 1 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 0 '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 0.006 '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
N2 C1 C14 . . 125.66(17) ?
N2 C1 Cl1 . . 116.16(14) ?
C14 C1 Cl1 . . 118.18(13) ?
C1 N2 C3 . . 117.43(15) ?
N2 C3 C12 . . 122.01(15) ?
N2 C3 C4 . . 118.49(16) ?
C12 C3 C4 . . 119.50(17) ?
O5 C4 C7 . . 125.88(16) ?
O5 C4 C3 . . 115.19(16) ?
C7 C4 C3 . . 118.92(17) ?
C4 O5 C6 . . 115.66(16) ?
O5 C6 H6A . . 109.5 ?
O5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
O5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C4 C7 C8 . . 121.65(18) ?
C4 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C9 C8 C7 . . 120.54(19) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 O10 . . 125.59(18) ?
C8 C9 C12 . . 119.68(18) ?
O10 C9 C12 . . 114.73(17) ?
C9 O10 C11 . . 116.36(18) ?
O10 C11 H11A . . 109.5 ?
O10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C3 . . 117.46(17) ?
C13 C12 C9 . . 122.83(17) ?
C3 C12 C9 . . 119.69(17) ?
C14 C13 C12 . . 120.43(17) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C1 . . 116.95(16) ?
C13 C14 C15 . . 122.41(17) ?
C1 C14 C15 . . 120.56(17) ?
O16 C15 C14 . . 116.67(17) ?
O16 C15 C17 . . 58.19(12) ?
C14 C15 C17 . . 122.08(16) ?
O16 C15 H15 . . 115.8 ?
C14 C15 H15 . . 115.8 ?
C17 C15 H15 . . 115.8 ?
C17 O16 C15 . . 63.54(12) ?
O16 C17 C18 . . 114.72(17) ?
O16 C17 C15 . . 58.27(12) ?
C18 C17 C15 . . 118.78(16) ?
O16 C17 C20 . . 114.39(16) ?
C18 C17 C20 . . 118.84(17) ?
C15 C17 C20 . . 117.05(17) ?
N19 C18 C17 . . 178.6(2) ?
O21 C20 O22 . . 127.0(2) ?
O21 C20 C17 . . 122.2(2) ?
O22 C20 C17 . . 110.79(17) ?
C20 O22 C23 . . 115.01(18) ?
C24 C23 O22 . . 109.0(2) ?
C24 C23 H23A . . 109.9 ?
O22 C23 H23A . . 109.9 ?
C24 C23 H23B . . 109.9 ?
O22 C23 H23B . . 109.9 ?
H23A C23 H23B . . 108.3 ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
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
Cl1 C1 . 1.7514(19) ?
C1 N2 . 1.302(2) ?
C1 C14 . 1.418(2) ?
N2 C3 . 1.370(2) ?
C3 C12 . 1.422(2) ?
C3 C4 . 1.429(2) ?
C4 O5 . 1.365(2) ?
C4 C7 . 1.372(3) ?
O5 C6 . 1.431(2) ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C8 . 1.417(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.367(3) ?
C8 H8 . 0.95 ?
C9 O10 . 1.371(2) ?
C9 C12 . 1.425(3) ?
O10 C11 . 1.430(3) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.412(3) ?
C13 C14 . 1.366(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.492(2) ?
C15 O16 . 1.430(2) ?
C15 C17 . 1.505(3) ?
C15 H15 . 1 ?
O16 C17 . 1.429(3) ?
C17 C18 . 1.461(3) ?
C17 C20 . 1.516(3) ?
C18 N19 . 1.139(3) ?
C20 O21 . 1.197(3) ?
C20 O22 . 1.302(3) ?
O22 C23 . 1.478(3) ?
C23 C24 . 1.393(4) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
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
_geom_hbond_publ_flag
C7 H7 N19 2_667 0.95 2.57 3.434(3) 151 yes
C24 H24A O16 1_455 0.98 2.57 3.152(4) 118 yes
C13 H13 O16 . 0.95 2.54 2.875(2) 101 ?
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
C14 C1 N2 C3 . . . . 0.1(3) ?
Cl1 C1 N2 C3 . . . . -179.64(12) ?
C1 N2 C3 C12 . . . . 1.9(2) ?
C1 N2 C3 C4 . . . . -177.41(15) ?
N2 C3 C4 O5 . . . . -0.2(2) ?
C12 C3 C4 O5 . . . . -179.61(15) ?
N2 C3 C4 C7 . . . . 179.25(16) ?
C12 C3 C4 C7 . . . . -0.1(3) ?
C7 C4 O5 C6 . . . . 4.2(3) ?
C3 C4 O5 C6 . . . . -176.33(17) ?
O5 C4 C7 C8 . . . . -179.77(17) ?
C3 C4 C7 C8 . . . . 0.8(3) ?
C4 C7 C8 C9 . . . . -0.1(3) ?
C7 C8 C9 O10 . . . . 178.50(18) ?
C7 C8 C9 C12 . . . . -1.3(3) ?
C8 C9 O10 C11 . . . . 0.2(3) ?
C12 C9 O10 C11 . . . . 179.96(17) ?
N2 C3 C12 C13 . . . . -2.0(2) ?
C4 C3 C12 C13 . . . . 177.30(15) ?
N2 C3 C12 C9 . . . . 179.44(15) ?
C4 C3 C12 C9 . . . . -1.2(3) ?
C8 C9 C12 C13 . . . . -176.53(17) ?
O10 C9 C12 C13 . . . . 3.7(3) ?
C8 C9 C12 C3 . . . . 1.9(3) ?
O10 C9 C12 C3 . . . . -177.88(15) ?
C3 C12 C13 C14 . . . . 0.1(3) ?
C9 C12 C13 C14 . . . . 178.57(16) ?
C12 C13 C14 C1 . . . . 1.7(3) ?
C12 C13 C14 C15 . . . . -175.11(16) ?
N2 C1 C14 C13 . . . . -1.9(3) ?
Cl1 C1 C14 C13 . . . . 177.79(13) ?
N2 C1 C14 C15 . . . . 174.96(17) ?
Cl1 C1 C14 C15 . . . . -5.3(2) ?
C13 C14 C15 O16 . . . . -9.4(3) ?
C1 C14 C15 O16 . . . . 173.87(16) ?
C13 C14 C15 C17 . . . . -77.0(3) ?
C1 C14 C15 C17 . . . . 106.3(2) ?
C14 C15 O16 C17 . . . . -112.82(19) ?
C15 O16 C17 C18 . . . . 109.79(18) ?
C15 O16 C17 C20 . . . . -107.86(18) ?
C14 C15 C17 O16 . . . . 103.6(2) ?
O16 C15 C17 C18 . . . . -102.8(2) ?
C14 C15 C17 C18 . . . . 0.8(3) ?
O16 C15 C17 C20 . . . . 103.26(19) ?
C14 C15 C17 C20 . . . . -153.18(19) ?
O16 C17 C20 O21 . . . . 40.3(3) ?
C18 C17 C20 O21 . . . . -179.0(2) ?
C15 C17 C20 O21 . . . . -25.1(3) ?
O16 C17 C20 O22 . . . . -140.08(17) ?
C18 C17 C20 O22 . . . . 0.6(3) ?
C15 C17 C20 O22 . . . . 154.55(18) ?
O21 C20 O22 C23 . . . . 4.5(4) ?
C17 C20 O22 C23 . . . . -175.12(17) ?
C20 O22 C23 C24 . . . . -161.8(2) ?
