#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015209.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_2015209
loop_
_publ_author_name
'Linden, Anthony'
'Şimşek, Rahime'
'Gündz̈, Miyase'
'Şafak, Cihat'
_publ_section_title
;(+-)-Methyl and (+-)-ethyl
 4-(2,3-difluorophenyl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
;
_journal_coeditor_code           SK1884
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o731
_journal_page_last               o734
_journal_paper_doi               10.1107/S0108270105037066
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H21 F2 N O3'
_chemical_formula_moiety         'C20 H21 F2 N O3'
_chemical_formula_sum            'C20 H21 F2 N O3'
_chemical_formula_weight         361.39
_chemical_name_systematic
;
(+-)-methyl 4-(2,3-difluorophenyl)-2,6,6-trimethyl-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.9639(19)
_cell_angle_beta                 92.624(2)
_cell_angle_gamma                107.904(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2055(2)
_cell_length_b                   9.6702(4)
_cell_length_c                   12.9606(6)
_cell_measurement_reflns_used    4905
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     855.15(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans with κ  offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21670
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0583P)²+0.1694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3409
_reflns_number_total             4980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk1884.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P -1         '
_cod_database_code               2015209
_cod_database_fobs_code          2015209
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
F1 0.55963(12) 0.41606(10) 0.29982(7) 0.0313(2) Uani d . 1 . . F
F2 0.55884(13) 0.30670(10) 0.48190(7) 0.0348(2) Uani d . 1 . . F
O5 0.60328(14) 0.73105(11) 0.24549(8) 0.0258(2) Uani d . 1 . . O
O10 -0.09097(16) 0.21379(12) 0.02186(9) 0.0356(3) Uani d . 1 . . O
O11 0.22881(14) 0.27902(11) 0.06998(8) 0.0273(3) Uani d . 1 . . O
N1 -0.07918(17) 0.60996(13) 0.19709(10) 0.0228(3) Uani d . 1 . . N
H1 -0.187(3) 0.641(2) 0.2032(14) 0.043(5) Uiso d . 1 . . H
C2 -0.0968(2) 0.47989(15) 0.13909(11) 0.0208(3) Uani d . 1 . . C
C3 0.05715(19) 0.42745(15) 0.13928(11) 0.0201(3) Uani d . 1 . . C
C4 0.24052(19) 0.50149(15) 0.21054(11) 0.0193(3) Uani d . 1 . . C
H4 0.3569 0.4945 0.1739 0.023 Uiso calc R 1 . . H
C4a 0.2606(2) 0.66214(15) 0.23426(11) 0.0197(3) Uani d . 1 . . C
C5 0.4540(2) 0.76767(15) 0.25426(11) 0.0195(3) Uani d . 1 . . C
C6 0.4723(2) 0.92792(15) 0.28174(12) 0.0229(3) Uani d . 1 . . C
C7 0.2881(2) 0.93810(17) 0.33260(13) 0.0271(3) Uani d . 1 . . C
H71 0.2822 0.8962 0.4004 0.033 Uiso calc R 1 . . H
H72 0.2964 1.0420 0.3454 0.033 Uiso calc R 1 . . H
C8 0.1023(2) 0.85787(16) 0.26556(13) 0.0274(3) Uani d . 1 . . C
H81 -0.0131 0.8554 0.3050 0.033 Uiso calc R 1 . . H
H82 0.0957 0.9104 0.2033 0.033 Uiso calc R 1 . . H
C8a 0.0982(2) 0.70525(15) 0.23318(11) 0.0214(3) Uani d . 1 . . C
C9 -0.2905(2) 0.41411(17) 0.07901(12) 0.0259(3) Uani d . 1 . . C
H91 -0.2700 0.3808 0.0086 0.039 Uiso calc R 1 . . H
H92 -0.3585 0.4875 0.0758 0.039 Uiso calc R 1 . . H
H93 -0.3698 0.3311 0.1134 0.039 Uiso calc R 1 . . H
C10 0.0510(2) 0.29734(15) 0.07182(11) 0.0222(3) Uani d . 1 . . C
C12 0.2413(2) 0.16022(17) 0.00046(13) 0.0309(4) Uani d . 1 . . C
H121 0.1659 0.0675 0.0254 0.046 Uiso calc R 1 . . H
H122 0.3784 0.1638 -0.0024 0.046 Uiso calc R 1 . . H
H123 0.1881 0.1684 -0.0690 0.046 Uiso calc R 1 . . H
C13 0.2361(2) 0.42794(15) 0.31152(11) 0.0198(3) Uani d . 1 . . C
C14 0.3958(2) 0.39328(15) 0.35196(11) 0.0220(3) Uani d . 1 . . C
C15 0.3952(2) 0.33561(16) 0.44632(12) 0.0248(3) Uani d . 1 . . C
C16 0.2364(2) 0.30959(17) 0.50472(12) 0.0285(4) Uani d . 1 . . C
H16 0.2385 0.2720 0.5704 0.034 Uiso calc R 1 . . H
C17 0.0721(2) 0.33991(18) 0.46493(13) 0.0297(4) Uani d . 1 . . C
H17 -0.0412 0.3208 0.5031 0.036 Uiso calc R 1 . . H
C18 0.0724(2) 0.39750(17) 0.37044(12) 0.0259(3) Uani d . 1 . . C
H18 -0.0417 0.4171 0.3446 0.031 Uiso calc R 1 . . H
C19 0.6511(2) 1.00115(18) 0.35628(14) 0.0357(4) Uani d . 1 . . C
H191 0.7688 0.9937 0.3244 0.054 Uiso calc R 1 . . H
H192 0.6372 0.9526 0.4207 0.054 Uiso calc R 1 . . H
H193 0.6623 1.1042 0.3717 0.054 Uiso calc R 1 . . H
C20 0.4957(3) 1.00363(18) 0.18072(14) 0.0343(4) Uani d . 1 . . C
H201 0.4846 1.1017 0.1937 0.051 Uiso calc R 1 . . H
H202 0.3932 0.9468 0.1284 0.051 Uiso calc R 1 . . H
H203 0.6242 1.0107 0.1556 0.051 Uiso calc R 1 . . H
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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
F F 0.0171 0.0103
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
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
C10 O11 C12 115.61(11) ?
C8a N1 C2 122.11(12) yes
C8a N1 H1 117.6(12) ?
C2 N1 H1 119.6(12) ?
N1 C2 C3 119.21(13) yes
N1 C2 C9 113.94(12) yes
C3 C2 C9 126.83(13) yes
C2 C3 C10 120.94(13) ?
C2 C3 C4 120.62(12) yes
C10 C3 C4 118.44(11) ?
C3 C4 C4a 109.74(11) yes
C4a C4 C13 109.92(11) ?
C3 C4 C13 111.54(11) ?
C4a C4 H4 108.5 ?
C3 C4 H4 108.5 ?
C13 C4 H4 108.5 ?
C8a C4a C5 120.92(13) ?
C4 C4a C8a 119.69(12) yes
C5 C4a C4 119.36(11) ?
O5 C5 C4a 121.20(12) ?
O5 C5 C6 119.80(12) ?
C4a C5 C6 118.94(12) ?
C19 C6 C5 110.60(12) ?
C19 C6 C20 109.23(13) ?
C5 C6 C20 107.55(12) ?
C19 C6 C7 109.27(13) ?
C5 C6 C7 109.55(12) ?
C20 C6 C7 110.63(12) ?
C8 C7 C6 112.17(13) ?
C8 C7 H71 109.2 ?
C6 C7 H71 109.2 ?
C8 C7 H72 109.2 ?
C6 C7 H72 109.2 ?
H71 C7 H72 107.9 ?
C8a C8 C7 110.47(12) ?
C8a C8 H81 109.6 ?
C7 C8 H81 109.6 ?
C8a C8 H82 109.6 ?
C7 C8 H82 109.6 ?
H81 C8 H82 108.1 ?
C4a C8a N1 120.38(13) yes
C4a C8a C8 123.26(13) ?
N1 C8a C8 116.30(12) ?
C2 C9 H91 109.5 ?
C2 C9 H92 109.5 ?
H91 C9 H92 109.5 ?
C2 C9 H93 109.5 ?
H91 C9 H93 109.5 ?
H92 C9 H93 109.5 ?
O10 C10 O11 121.76(13) yes
O10 C10 C3 126.97(13) yes
O11 C10 C3 111.28(12) yes
O11 C12 H121 109.5 ?
O11 C12 H122 109.5 ?
H121 C12 H122 109.5 ?
O11 C12 H123 109.5 ?
H121 C12 H123 109.5 ?
H122 C12 H123 109.5 ?
C14 C13 C18 116.31(13) ?
C14 C13 C4 122.08(12) ?
C18 C13 C4 121.57(12) ?
F1 C14 C15 117.50(12) ?
F1 C14 C13 120.73(13) ?
C15 C14 C13 121.77(13) ?
F2 C15 C16 119.98(13) ?
F2 C15 C14 118.42(13) ?
C16 C15 C14 121.59(13) ?
C15 C16 C17 117.95(14) ?
C15 C16 H16 121.0 ?
C17 C16 H16 121.0 ?
C18 C17 C16 120.50(14) ?
C18 C17 H17 119.8 ?
C16 C17 H17 119.8 ?
C17 C18 C13 121.85(13) ?
C17 C18 H18 119.1 ?
C13 C18 H18 119.1 ?
C6 C19 H191 109.5 ?
C6 C19 H192 109.5 ?
H191 C19 H192 109.5 ?
C6 C19 H193 109.5 ?
H191 C19 H193 109.5 ?
H192 C19 H193 109.5 ?
C6 C20 H201 109.5 ?
C6 C20 H202 109.5 ?
H201 C20 H202 109.5 ?
C6 C20 H203 109.5 ?
H201 C20 H203 109.5 ?
H202 C20 H203 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
F1 C14 . 1.3540(16) ?
F2 C15 . 1.3607(16) ?
O5 C5 . 1.2388(16) ?
O10 C10 . 1.2155(17) yes
O11 C10 . 1.3474(16) yes
O11 C12 . 1.4379(18) ?
N1 C8a . 1.3651(18) yes
N1 C2 . 1.3878(18) yes
N1 H1 . 0.915(19) ?
C2 C3 . 1.3537(19) yes
C2 C9 . 1.499(2) ?
C3 C10 . 1.470(2) yes
C3 C4 . 1.5253(19) yes
C4 C4a . 1.5234(19) yes
C4 C13 . 1.5292(19) ?
C4 H4 . 1.0000 ?
C4a C8a . 1.3570(19) yes
C4a C5 . 1.452(2) ?
C5 C6 . 1.5296(19) ?
C6 C19 . 1.525(2) ?
C6 C20 . 1.535(2) ?
C6 C7 . 1.535(2) ?
C7 C8 . 1.520(2) ?
C7 H71 . 0.9900 ?
C7 H72 . 0.9900 ?
C8 C8a . 1.497(2) ?
C8 H81 . 0.9900 ?
C8 H82 . 0.9900 ?
C9 H91 . 0.9800 ?
C9 H92 . 0.9800 ?
C9 H93 . 0.9800 ?
C12 H121 . 0.9800 ?
C12 H122 . 0.9800 ?
C12 H123 . 0.9800 ?
C13 C14 . 1.3842(19) ?
C13 C18 . 1.401(2) ?
C14 C15 . 1.378(2) ?
C15 C16 . 1.369(2) ?
C16 C17 . 1.390(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.380(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H191 . 0.9800 ?
C19 H192 . 0.9800 ?
C19 H193 . 0.9800 ?
C20 H201 . 0.9800 ?
C20 H202 . 0.9800 ?
C20 H203 . 0.9800 ?
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
N1 H1 O5 1_455 0.915(19) 2.04(2) 2.9456(15) 168.0(17) 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
C8a N1 C2 C3 16.7(2)
C8a N1 C2 C9 -161.59(13)
N1 C2 C3 C10 -174.48(12)
C9 C2 C3 C10 3.6(2)
N1 C2 C3 C4 6.1(2)
C9 C2 C3 C4 -175.77(13)
C2 C3 C4 C4a -26.57(17)
C10 C3 C4 C4a 154.03(12)
C2 C3 C4 C13 95.50(15)
C10 C3 C4 C13 -83.90(15)
C3 C4 C4a C8a 28.03(18)
C13 C4 C4a C8a -95.00(15)
C3 C4 C4a C5 -149.88(12)
C13 C4 C4a C5 87.09(15)
C8a C4a C5 O5 -172.93(13)
C4 C4a C5 O5 5.0(2)
C8a C4a C5 C6 4.2(2)
C4 C4a C5 C6 -177.88(12)
O5 C5 C6 C19 -35.44(19)
C4a C5 C6 C19 147.35(14)
O5 C5 C6 C20 83.75(16)
C4a C5 C6 C20 -93.45(15)
O5 C5 C6 C7 -155.95(13)
C4a C5 C6 C7 26.84(18)
C19 C6 C7 C8 -176.00(13)
C5 C6 C7 C8 -54.69(16)
C20 C6 C7 C8 63.71(16)
C6 C7 C8 C8a 51.46(17)
C5 C4a C8a N1 168.68(13)
C4 C4a C8a N1 -9.2(2)
C5 C4a C8a C8 -8.3(2)
C4 C4a C8a C8 173.82(13)
C2 N1 C8a C4a -15.2(2)
C2 N1 C8a C8 162.02(13)
C7 C8 C8a C4a -19.8(2)
C7 C8 C8a N1 163.05(13)
C12 O11 C10 O10 3.7(2)
C12 O11 C10 C3 -175.85(12)
C2 C3 C10 O10 -10.6(2)
C4 C3 C10 O10 168.80(14)
C2 C3 C10 O11 168.94(13)
C4 C3 C10 O11 -11.67(18)
C4a C4 C13 C14 -104.31(15)
C3 C4 C13 C14 133.73(13)
C4a C4 C13 C18 72.98(16)
C3 C4 C13 C18 -48.98(17)
C18 C13 C14 F1 178.76(13)
C4 C13 C14 F1 -3.8(2)
C18 C13 C14 C15 -1.7(2)
C4 C13 C14 C15 175.76(13)
F1 C14 C15 F2 0.7(2)
C13 C14 C15 F2 -178.85(12)
F1 C14 C15 C16 179.66(13)
C13 C14 C15 C16 0.1(2)
F2 C15 C16 C17 -179.59(13)
C14 C15 C16 C17 1.5(2)
C15 C16 C17 C18 -1.4(2)
C16 C17 C18 C13 -0.2(2)
C14 C13 C18 C17 1.7(2)
C4 C13 C18 C17 -175.70(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10020748
