#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/29/2212984.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_2212984
loop_
_publ_author_name
'Abdelmalek Bouraiou'
'Ali Belfaitah'
'Sofiane Bouacida'
'Patricia Benard-Rocherulle'
'Bertrand Carboni'
_publ_section_title
;Ethyl
 trans-3-(2-chloro-6,7-dimethylquinolin-3-yl)-1-cyclohexylaziridine-2-carboxylate
;
_journal_coeditor_code           RZ2120
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1626
_journal_page_last               o1628
_journal_paper_doi               10.1107/S1600536807009920
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H27 Cl N2 O2'
_chemical_formula_moiety         'C22 H27 Cl N2 O2'
_chemical_formula_structural     'C22 H27 Cl N2 O2'
_chemical_formula_sum            'C22 H27 Cl N2 O2'
_chemical_formula_weight         386.91
_chemical_name_systematic
;
Ethyl trans-3-(2-chloro-6,7-dimethylquinolin-3-yl)-1-
cyclohexylaziridine-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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                68.421(4)
_cell_angle_beta                 85.758(4)
_cell_angle_gamma                65.125(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8735(8)
_cell_length_b                   10.5870(2)
_cell_length_c                   11.5380(2)
_cell_measurement_reflns_used    9080
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      1.91
_cell_volume                     1012.83(10)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'SCALEPACK and DENZO  (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9080
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.445
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0489
_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)+(0.0293P)²+1.3984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1677
_reflns_number_gt                2618
_reflns_number_total             4083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2120.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2212984
_cod_database_fobs_code          2212984
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
Cl Cl1 0.12439(9) 0.87720(8) 0.43586(8) 0.0358(2) Uani d . 1
O O2 -0.2198(2) 0.7932(2) 0.64558(17) 0.0259(5) Uani d . 1
N N2 0.0953(2) 0.4584(3) 0.6415(2) 0.0189(5) Uani d . 1
N N1 0.3105(2) 0.7399(3) 0.3042(2) 0.0237(5) Uani d . 1
O O1 -0.0184(2) 0.6695(2) 0.78655(18) 0.0338(5) Uani d . 1
C C13 0.1618(3) 0.5650(3) 0.6017(2) 0.0209(6) Uani d . 1
H H13 0.2082 0.5718 0.6701 0.025 Uiso calc R 1
C C10 0.4004(3) 0.6155(3) 0.2781(2) 0.0200(6) Uani d . 1
C C15 0.1159(3) 0.3631(3) 0.7751(2) 0.0200(6) Uani d . 1
H H15 0.1337 0.4126 0.8255 0.024 Uiso calc R 1
C C5 0.4152(3) 0.4698(3) 0.3539(2) 0.0198(6) Uani d . 1
C C7 0.5964(3) 0.3656(3) 0.2204(3) 0.0229(6) Uani d . 1
C C3 0.2430(3) 0.5776(3) 0.4872(2) 0.0202(6) Uani d . 1
C C2 0.2388(3) 0.7175(3) 0.4037(3) 0.0236(6) Uani d . 1
C C9 0.4827(3) 0.6330(3) 0.1723(2) 0.0225(6) Uani d . 1
H H9 0.4710 0.7288 0.1206 0.027 Uiso calc R 1
C C16 -0.0232(3) 0.3355(3) 0.8126(2) 0.0240(6) Uani d . 1
H H16A -0.0461 0.2950 0.7576 0.029 Uiso calc R 1
H H16B -0.1080 0.4298 0.8035 0.029 Uiso calc R 1
C C12 0.6687(3) 0.5351(3) 0.0316(3) 0.0286(7) Uani d . 1
H H12A 0.6418 0.6402 -0.0121 0.043 Uiso calc R 1
H H12B 0.6473 0.4951 -0.0235 0.043 Uiso calc R 1
H H12C 0.7738 0.4839 0.0594 0.043 Uiso calc R 1
C C17 0.0015(3) 0.2262(3) 0.9477(3) 0.0280(7) Uani d . 1
H H17A -0.0865 0.2065 0.9687 0.034 Uiso calc R 1
H H17B 0.0150 0.2711 1.0031 0.034 Uiso calc R 1
C C14 -0.0054(3) 0.6208(3) 0.5977(2) 0.0205(6) Uani d . 1
H H14 -0.0598 0.6656 0.5146 0.025 Uiso calc R 1
C C18 0.1387(3) 0.0786(3) 0.9679(3) 0.0278(7) Uani d . 1
H H18A 0.1208 0.0283 0.9194 0.033 Uiso calc R 1
H H18B 0.1548 0.0138 1.0556 0.033 Uiso calc R 1
C C8 0.5790(3) 0.5131(3) 0.1438(2) 0.0235(6) Uani d . 1
C C22 -0.2986(4) 0.8731(3) 0.7270(3) 0.0349(8) Uani d . 1
H H22A -0.2344 0.9054 0.7571 0.042 Uiso calc R 1
H H22B -0.3261 0.8077 0.7988 0.042 Uiso calc R 1
C C4 0.3320(3) 0.4549(3) 0.4593(2) 0.0202(6) Uani d . 1
H H4 0.3378 0.3608 0.5100 0.024 Uiso calc R 1
C C20 0.2523(3) 0.2164(3) 0.7939(3) 0.0227(6) Uani d . 1
H H20A 0.3401 0.2364 0.7727 0.027 Uiso calc R 1
H H20B 0.2382 0.1725 0.7380 0.027 Uiso calc R 1
C C21 -0.0783(3) 0.6940(3) 0.6883(3) 0.0251(7) Uani d . 1
C C19 0.2787(3) 0.1051(3) 0.9289(3) 0.0282(7) Uani d . 1
H H19A 0.3039 0.1439 0.9842 0.034 Uiso calc R 1
H H19B 0.3624 0.0107 0.9363 0.034 Uiso calc R 1
C C11 0.7029(3) 0.2319(3) 0.1915(3) 0.0316(7) Uani d . 1
H H11A 0.7011 0.1423 0.2530 0.047 Uiso calc R 1
H H11B 0.8026 0.2258 0.1932 0.047 Uiso calc R 1
H H11C 0.6731 0.2424 0.1100 0.047 Uiso calc R 1
C C6 0.5132(3) 0.3476(3) 0.3221(2) 0.0230(6) Uani d . 1
H H6 0.5222 0.2518 0.3711 0.028 Uiso calc R 1
C C23 -0.4356(3) 1.0056(4) 0.6536(3) 0.0433(9) Uani d . 1
H H23A -0.4887 1.0603 0.7055 0.065 Uiso calc R 1
H H23B -0.4991 0.9725 0.6252 0.065 Uiso calc R 1
H H23C -0.4074 1.0694 0.5827 0.065 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
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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'
C C 0.0033 0.0016 '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
_geom_angle_publ_flag
C21 O2 C22 114.7(2) ?
C13 N2 C15 118.4(2) ?
C13 N2 C14 61.41(18) yes
C15 N2 C14 120.4(2) ?
C2 N1 C10 116.5(2) ?
N2 C13 C3 118.7(2) ?
N2 C13 C14 60.25(17) yes
C3 C13 C14 122.8(2) ?
N2 C13 H13 114.7 ?
C3 C13 H13 114.7 ?
C14 C13 H13 114.7 ?
N1 C10 C9 118.9(2) ?
N1 C10 C5 122.4(2) ?
C9 C10 C5 118.7(2) ?
N2 C15 C20 107.4(2) ?
N2 C15 C16 110.0(2) ?
C20 C15 C16 110.8(2) ?
N2 C15 H15 109.6 ?
C20 C15 H15 109.6 ?
C16 C15 H15 109.6 ?
C6 C5 C4 123.5(3) ?
C6 C5 C10 118.7(2) ?
C4 C5 C10 117.8(2) ?
C6 C7 C8 118.6(3) ?
C6 C7 C11 120.5(3) ?
C8 C7 C11 120.8(2) ?
C4 C3 C2 116.1(2) ?
C4 C3 C13 122.0(3) ?
C2 C3 C13 121.8(2) ?
N1 C2 C3 126.7(3) ?
N1 C2 Cl1 116.0(2) ?
C3 C2 Cl1 117.3(2) ?
C8 C9 C10 121.9(3) ?
C8 C9 H9 119.0 ?
C10 C9 H9 119.0 ?
C15 C16 C17 110.5(2) ?
C15 C16 H16A 109.5 ?
C17 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
C17 C16 H16B 109.5 ?
H16A C16 H16B 108.1 ?
C8 C12 H12A 109.5 ?
C8 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C8 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C16 C17 C18 111.4(2) ?
C16 C17 H17A 109.3 ?
C18 C17 H17A 109.3 ?
C16 C17 H17B 109.3 ?
C18 C17 H17B 109.3 ?
H17A C17 H17B 108.0 ?
N2 C14 C21 121.1(2) ?
N2 C14 C13 58.34(16) yes
C21 C14 C13 115.7(2) ?
N2 C14 H14 116.3 ?
C21 C14 H14 116.3 ?
C13 C14 H14 116.3 ?
C17 C18 C19 111.2(2) ?
C17 C18 H18A 109.4 ?
C19 C18 H18A 109.4 ?
C17 C18 H18B 109.4 ?
C19 C18 H18B 109.4 ?
H18A C18 H18B 108.0 ?
C9 C8 C7 119.9(2) ?
C9 C8 C12 120.7(3) ?
C7 C8 C12 119.4(3) ?
O2 C22 C23 108.2(3) ?
O2 C22 H22A 110.1 ?
C23 C22 H22A 110.1 ?
O2 C22 H22B 110.1 ?
C23 C22 H22B 110.1 ?
H22A C22 H22B 108.4 ?
C3 C4 C5 120.5(3) ?
C3 C4 H4 119.8 ?
C5 C4 H4 119.8 ?
C15 C20 C19 111.7(2) ?
C15 C20 H20A 109.3 ?
C19 C20 H20A 109.3 ?
C15 C20 H20B 109.3 ?
C19 C20 H20B 109.3 ?
H20A C20 H20B 107.9 ?
O1 C21 O2 123.8(2) ?
O1 C21 C14 125.2(3) ?
O2 C21 C14 111.0(2) ?
C20 C19 C18 110.6(2) ?
C20 C19 H19A 109.5 ?
C18 C19 H19A 109.5 ?
C20 C19 H19B 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 108.1 ?
C7 C11 H11A 109.5 ?
C7 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C7 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C7 C6 C5 122.1(3) ?
C7 C6 H6 119.0 ?
C5 C6 H6 119.0 ?
C22 C23 H23A 109.5 ?
C22 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C22 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 1.751(3) ?
O2 C21 1.336(3) yes
O2 C22 1.458(3) yes
N2 C13 1.453(3) yes
N2 C15 1.472(3) yes
N2 C14 1.482(3) yes
N1 C2 1.303(3) ?
N1 C10 1.372(3) ?
O1 C21 1.206(3) yes
C13 C3 1.487(4) ?
C13 C14 1.499(4) yes
C13 H13 0.9800 ?
C10 C9 1.413(4) ?
C10 C5 1.415(4) ?
C15 C20 1.519(4) ?
C15 C16 1.522(4) ?
C15 H15 0.9800 ?
C5 C6 1.411(4) ?
C5 C4 1.413(3) ?
C7 C6 1.383(4) ?
C7 C8 1.426(4) ?
C7 C11 1.504(4) ?
C3 C4 1.367(4) ?
C3 C2 1.424(4) ?
C9 C8 1.367(4) ?
C9 H9 0.9300 ?
C16 C17 1.524(4) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C12 C8 1.515(4) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C17 C18 1.526(4) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C14 C21 1.492(3) ?
C14 H14 0.9800 ?
C18 C19 1.528(4) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C22 C23 1.487(4) ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C4 H4 0.9300 ?
C20 C19 1.527(4) ?
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C6 H6 0.9300 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C13 H13 O1 0.98 2.55 2.908(4) 101 yes
C15 H15 O1 0.98 2.37 2.995(4) 121 yes
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
_geom_torsion_publ_flag
C15 N2 C13 C3 135.3(2) yes
C14 N2 C13 C3 -113.5(3) ?
C15 N2 C13 C14 -111.2(2) ?
C2 N1 C10 C9 -179.0(2) ?
C2 N1 C10 C5 0.3(4) ?
C13 N2 C15 C20 -93.9(3) ?
C14 N2 C15 C20 -165.7(2) ?
C13 N2 C15 C16 145.5(2) ?
C14 N2 C15 C16 73.7(3) ?
N1 C10 C5 C6 -178.3(2) ?
C9 C10 C5 C6 1.0(4) ?
N1 C10 C5 C4 0.7(4) ?
C9 C10 C5 C4 180.0(2) ?
N2 C13 C3 C4 -38.9(4) ?
C14 C13 C3 C4 -110.3(3) ?
N2 C13 C3 C2 144.5(3) ?
C14 C13 C3 C2 73.1(3) ?
C10 N1 C2 C3 -0.7(4) ?
C10 N1 C2 Cl1 -179.98(18) ?
C4 C3 C2 N1 0.1(4) ?
C13 C3 C2 N1 176.9(3) ?
C4 C3 C2 Cl1 179.38(19) ?
C13 C3 C2 Cl1 -3.8(4) ?
N1 C10 C9 C8 177.3(2) ?
C5 C10 C9 C8 -2.0(4) ?
N2 C15 C16 C17 175.1(2) ?
C20 C15 C16 C17 56.6(3) ?
C15 C16 C17 C18 -56.5(3) ?
C13 N2 C14 C21 -102.9(3) ?
C15 N2 C14 C21 5.1(4) yes
C15 N2 C14 C13 108.0(2) ?
C3 C13 C14 N2 106.9(3) ?
N2 C13 C14 C21 112.2(3) ?
C3 C13 C14 C21 -141.0(3) yes
C16 C17 C18 C19 55.8(3) ?
C10 C9 C8 C7 1.2(4) ?
C10 C9 C8 C12 -178.4(2) ?
C6 C7 C8 C9 0.6(4) ?
C11 C7 C8 C9 -179.3(2) ?
C6 C7 C8 C12 -179.7(2) ?
C11 C7 C8 C12 0.3(4) ?
C21 O2 C22 C23 164.7(2) ?
C2 C3 C4 C5 0.9(4) ?
C13 C3 C4 C5 -175.9(2) ?
C6 C5 C4 C3 177.7(2) ?
C10 C5 C4 C3 -1.3(4) ?
N2 C15 C20 C19 -176.8(2) ?
C16 C15 C20 C19 -56.7(3) ?
C22 O2 C21 O1 0.6(4) ?
C22 O2 C21 C14 -178.5(2) ?
N2 C14 C21 O1 41.0(4) ?
C13 C14 C21 O1 -26.1(4) ?
N2 C14 C21 O2 -139.9(2) ?
C13 C14 C21 O2 153.1(2) ?
C15 C20 C19 C18 55.5(3) ?
C17 C18 C19 C20 -54.7(3) ?
C8 C7 C6 C5 -1.7(4) ?
C11 C7 C6 C5 178.3(3) ?
C4 C5 C6 C7 -178.1(2) ?
C10 C5 C6 C7 0.9(4) ?
