#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007334.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_2007334
loop_
_publ_author_name
'Linden, Anthony'
'Şafak, Cihat'
'Şimşek, Rahime'
_publ_section_title
;Racemic Ethyl
 4-(2-Fluorophenyl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              879
_journal_page_last               882
_journal_paper_doi               10.1107/S0108270198000195
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C21 H24 F N O3'
_chemical_formula_sum            'C21 H24 F N O3'
_chemical_formula_weight         357.41
_chemical_melting_point          487
_chemical_name_systematic
;
2,6,6-trimethyl-3-carbethoxy-4-(fluorophenyl)-5-oxo-
1,4,5,6,7,8-hexahydroquinoline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                90.242(7)
_cell_angle_beta                 106.042(7)
_cell_angle_gamma                85.257(8)
_cell_formula_units_Z            2
_cell_length_a                   10.9500(12)
_cell_length_b                   12.2333(9)
_cell_length_c                   7.1453(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      19.5
_cell_volume                     916.55(15)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1991)
;
_computing_data_reduction
;
TEXSAN PROCESS (Molecular Structure Corporation, 1989)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5585
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.96
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment
'H atoms treated by a mixture of independent and constrained refinement'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.052
_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)+(0.0875P)²+0.2634P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.160
_reflns_number_gt                4309
_reflns_number_total             5326
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1427.cif
_cod_data_source_block           I
_cod_original_cell_volume        916.55(14)
_cod_database_code               2007334
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 .77451(11) .71201(11) .07651(17) .0565(3) Uani d . 1 . . F
O1 .76058(13) .40618(9) .6011(2) .0454(3) Uani d . 1 . . O
O2 .79170(10) .49734(8) .34898(15) .0309(2) Uani d . 1 . . O
O5 .47629(10) .78894(9) .01715(14) .0344(2) Uani d . 1 . . O
N1 .52488(11) .69412(11) .66912(16) .0291(3) Uani d . 1 . . N
C2 .60289(12) .59994(11) .66184(18) .0246(2) Uani d . 1 . . C
C3 .65542(11) .58697(10) .51053(17) .0213(2) Uani d . 1 . . C
C4 .63685(11) .67791(10) .35712(17) .0202(2) Uani d . 1 . . C
C4a .51850(11) .75359(10) .35175(17) .0205(2) Uani d . 1 . . C
C5 .44811(11) .80937(10) .16997(18) .0221(2) Uani d . 1 . . C
C6 .33226(12) .89041(10) .16546(19) .0241(2) Uani d . 1 . . C
C7 .33611(14) .93080(12) .3702(2) .0308(3) Uani d . 1 . . C
C8 .36098(14) .83874(14) .5209(2) .0329(3) Uani d . 1 . . C
C8a .47318(12) .76234(11) .51101(18) .0242(2) Uani d . 1 . . C
C9 .61549(16) .52081(14) .8279(2) .0333(3) Uani d . 1 . . C
C10 .73777(12) .48735(10) .49674(19) .0253(2) Uani d . 1 . . C
C11 .88221(18) .40655(13) .3302(3) .0397(4) Uani d . 1 . . C
C12 .94707(18) .44011(17) .1833(3) .0447(4) Uani d . 1 . . C
C13 .75488(12) .74179(10) .3933(2) .0261(3) Uani d . 1 . . C
C14 .81847(14) .75433(13) .2520(3) .0386(4) Uani d . 1 . . C
C15 .92802(17) .80936(17) .2846(4) .0584(6) Uani d . 1 . . C
C16 .97668(16) .85484(14) .4646(4) .0633(7) Uani d . 1 . . C
C17 .91591(16) .84543(14) .6085(4) .0550(6) Uani d . 1 . . C
C18 .80590(14) .78910(12) .5735(3) .0379(4) Uani d . 1 . . C
H18 .765(2) .7899(17) .684(3) .045 Uiso d . 1 . . H
C19 .33078(18) .98959(14) .0346(3) .0423(4) Uani d . 1 . . C
C20 .21304(14) .82946(15) .0800(3) .0372(3) Uani d . 1 . . C
H1 .507(2) .7103(17) .776(3) .048(6) Uiso d . 1 . . H
H4 .6263(15) .6439(13) .231(2) .022(4) Uiso d . 1 . . H
H15 .959(3) .814(3) .179(5) .089(9) Uiso d . 1 . . H
H16 1.051(3) .893(2) .494(4) .085(9) Uiso d . 1 . . H
H17 .949(2) .8780(19) .736(3) .055(6) Uiso d . 1 . . H
H71 .404(2) .9821(17) .409(3) .040(5) Uiso d . 1 . . H
H72 .2535(19) .9744(16) .366(3) .041(5) Uiso d . 1 . . H
H81 .285(2) .7942(17) .498(3) .046(5) Uiso d . 1 . . H
H82 .380(2) .8672(18) .653(3) .048(5) Uiso d . 1 . . H
H91 .673(4) .539(3) .935(5) .106(11) Uiso d . 1 . . H
H92 .628(3) .444(3) .803(5) .112(12) Uiso d . 1 . . H
H93 .533(4) .533(3) .870(6) .131(13) Uiso d . 1 . . H
H111 .832(2) .3495(18) .285(3) .045(5) Uiso d . 1 . . H
H112 .948(2) .391(2) .464(4) .067(7) Uiso d . 1 . . H
H121 1.010(2) .379(2) .172(4) .065(7) Uiso d . 1 . . H
H122 .988(3) .509(2) .225(4) .073(8) Uiso d . 1 . . H
H123 .890(3) .454(2) .055(4) .081(8) Uiso d . 1 . . H
H191 .255(2) 1.0438(19) .035(3) .052(6) Uiso d . 1 . . H
H192 .323(2) .965(2) -.100(4) .064(7) Uiso d . 1 . . H
H193 .410(2) 1.030(2) .095(3) .060(7) Uiso d . 1 . . H
H201 .211(2) .809(2) -.047(4) .062(7) Uiso d . 1 . . H
H202 .213(2) .7628(19) .161(3) .054(6) Uiso d . 1 . . H
H203 .137(2) .886(2) .066(3) .061(7) Uiso d . 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -2 -1
2 2 -1
2 1 -1
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 O2 C11 115.59(11) yes
C8a N1 C2 122.57(11) yes
C8a N1 H1 118.0(14) ?
C2 N1 H1 119.4(14) ?
C3 C2 N1 119.28(11) yes
C3 C2 C9 127.60(12) yes
N1 C2 C9 113.09(11) yes
C2 C3 C10 120.83(11) yes
C2 C3 C4 120.84(11) yes
C4 C3 C10 118.24(10) yes
C4a C4 C13 111.24(10) ?
C3 C4 C4a 110.44(9) yes
C13 C4 C3 111.07(10) ?
C4a C4 H4 109.1(9) ?
C13 C4 H4 106.6(10) ?
C3 C4 H4 108.2(9) ?
C4 C4a C8a 120.36(11) yes
C5 C4a C8a 120.19(11) yes
C5 C4a C4 119.24(10) ?
O5 C5 C4a 120.98(11) ?
O5 C5 C6 119.31(11) ?
C4a C5 C6 119.62(10) yes
C19 C6 C7 108.73(12) ?
C19 C6 C20 109.48(13) ?
C7 C6 C20 110.73(11) ?
C19 C6 C5 109.90(11) ?
C5 C6 C7 111.10(10) yes
C20 C6 C5 106.89(11) ?
C6 C7 C8 113.32(11) yes
C8 C7 H71 109.5(12) ?
C6 C7 H71 108.3(11) ?
C8 C7 H72 109.6(11) ?
C6 C7 H72 109.4(11) ?
H71 C7 H72 106.5(16) ?
C7 C8 C8a 111.12(11) yes
C8a C8 H81 107.5(12) ?
C7 C8 H81 110.6(12) ?
C8a C8 H82 106.9(13) ?
C7 C8 H82 111.4(13) ?
H81 C8 H82 109.2(17) ?
C4a C8a N1 120.14(11) yes
C4a C8a C8 123.71(11) yes
N1 C8a C8 116.01(11) ?
C2 C9 H91 112(2) ?
C2 C9 H92 117(2) ?
H91 C9 H92 111(3) ?
C2 C9 H93 107(2) ?
H91 C9 H93 101(3) ?
H92 C9 H93 108(3) ?
O1 C10 O2 121.65(12) yes
O1 C10 C3 127.48(12) yes
O2 C10 C3 110.85(10) yes
O2 C11 C12 107.79(13) ?
O2 C11 H111 104.2(13) ?
C12 C11 H111 110.9(13) ?
O2 C11 H112 109.0(14) ?
C12 C11 H112 110.4(14) ?
H111 C11 H112 114.3(19) ?
C11 C12 H121 108.0(15) ?
C11 C12 H122 109.2(16) ?
H121 C12 H122 112(2) ?
C11 C12 H123 113.5(17) ?
H121 C12 H123 107(2) ?
H122 C12 H123 107(2) ?
C14 C13 C18 116.65(14) ?
C14 C13 C4 122.30(13) ?
C18 C13 C4 121.03(13) ?
F1 C14 C15 117.25(17) ?
F1 C14 C13 119.80(14) ?
C15 C14 C13 122.95(19) ?
C16 C15 C14 119.1(2) ?
C16 C15 H15 126(2) ?
C14 C15 H15 114(2) ?
C17 C16 C15 119.90(16) ?
C17 C16 H16 117.6(19) ?
C15 C16 H16 122.5(19) ?
C16 C17 C18 120.2(2) ?
C16 C17 H17 120.7(14) ?
C18 C17 H17 119.0(14) ?
C13 C18 C17 121.12(18) ?
C13 C18 H18 123.8(12) ?
C17 C18 H18 115.0(12) ?
C6 C19 H191 109.5(13) ?
C6 C19 H192 109.6(15) ?
H191 C19 H192 109(2) ?
C6 C19 H193 108.4(14) ?
H191 C19 H193 105.4(18) ?
H192 C19 H193 115(2) ?
C6 C20 H201 108.9(15) ?
C6 C20 H202 111.0(13) ?
H201 C20 H202 110(2) ?
C6 C20 H203 106.5(14) ?
H201 C20 H203 105(2) ?
H202 C20 H203 115.0(19) ?
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 . 1.332(2) yes
O1 C10 . 1.2113(16) yes
O2 C10 . 1.3549(16) yes
O2 C11 . 1.4572(17) yes
O5 C5 . 1.2334(15) yes
N1 C8a . 1.3673(16) yes
N1 C2 . 1.3860(17) yes
N1 H1 . .86(2) ?
C2 C3 . 1.3610(17) yes
C2 C9 . 1.5037(18) ?
C3 C10 . 1.4745(17) yes
C3 C4 . 1.5265(16) yes
C4 C4a . 1.5207(16) yes
C4 C13 . 1.5260(17) yes
C4 H4 . .974(16) ?
C4a C8a . 1.3619(16) yes
C4a C5 . 1.4540(17) yes
C5 C6 . 1.5372(17) yes
C6 C19 . 1.531(2) ?
C6 C7 . 1.5326(19) yes
C6 C20 . 1.533(2) ?
C7 C8 . 1.517(2) yes
C7 H71 . .99(2) ?
C7 H72 . 1.00(2) ?
C8 C8a . 1.4986(18) yes
C8 H81 . 1.01(2) ?
C8 H82 . .98(2) ?
C9 H91 . .89(4) ?
C9 H92 . .96(4) ?
C9 H93 . 1.03(4) ?
C11 C12 . 1.497(2) ?
C11 H111 . .93(2) ?
C11 H112 . 1.03(3) ?
C12 H121 . .99(3) ?
C12 H122 . .99(3) ?
C12 H123 . .96(3) ?
C13 C14 . 1.391(2) ?
C13 C18 . 1.398(2) ?
C14 C15 . 1.387(2) ?
C15 C16 . 1.383(4) ?
C15 H15 . .91(3) ?
C16 C17 . 1.380(4) ?
C16 H16 . .94(3) ?
C17 C18 . 1.399(2) ?
C17 H17 . .98(2) ?
C18 H18 . 1.01(2) ?
C19 H191 . 1.02(2) ?
C19 H192 . .98(3) ?
C19 H193 . 1.02(3) ?
C20 H201 . .93(3) ?
C20 H202 . 1.00(2) ?
C20 H203 . 1.02(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
_geom_hbond_publ_flag
N1 H1 O5 1_556 0.86(2) 2.06(2) 2.9012(15) 165(2) 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
C8a N1 C2 C3 16.1(2) yes
C8a N1 C2 C9 -162.20(13) ?
N1 C2 C3 C10 -179.34(11) ?
C9 C2 C3 C10 -1.3(2) ?
N1 C2 C3 C4 4.19(18) yes
C9 C2 C3 C4 -177.74(12) ?
C2 C3 C4 C4a -22.60(16) yes
C10 C3 C4 C4a 160.84(10) ?
C2 C3 C4 C13 101.31(13) ?
C10 C3 C4 C13 -75.25(14) ?
C13 C4 C4a C8a -99.59(14) ?
C3 C4 C4a C8a 24.22(16) yes
C4 C4a C8a N1 -7.44(19) yes
C2 N1 C8a C4a -14.5(2) yes
C13 C4 C4a C5 85.55(14) ?
C3 C4 C4a C5 -150.63(11) ?
C8a C4a C5 O5 -168.48(13) ?
C4 C4a C5 O5 6.39(18) ?
C8a C4a C5 C6 8.15(18) yes
C4 C4a C5 C6 -176.98(10) ?
O5 C5 C6 C19 -42.69(18) ?
C4a C5 C6 C19 140.62(14) ?
O5 C5 C6 C7 -163.07(13) ?
C4a C5 C6 C7 20.24(16) yes
O5 C5 C6 C20 76.03(15) ?
C4a C5 C6 C20 -100.66(13) ?
C19 C6 C7 C8 -169.97(13) ?
C20 C6 C7 C8 69.72(15) ?
C5 C6 C7 C8 -48.90(15) yes
C6 C7 C8 C8a 49.25(17) yes
C7 C8 C8a C4a -20.8(2) yes
C5 C4a C8a N1 167.37(12) ?
C5 C4a C8a C8 -8.1(2) yes
C4 C4a C8a C8 177.05(12) ?
C2 N1 C8a C8 161.34(13) ?
C7 C8 C8a N1 163.55(12) ?
C11 O2 C10 O1 -2.5(2) ?
C11 O2 C10 C3 175.90(12) ?
C2 C3 C10 O1 5.7(2) yes
C4 C3 C10 O1 -177.78(14) yes
C2 C3 C10 O2 -172.64(11) yes
C4 C3 C10 O2 3.92(16) yes
C10 O2 C11 C12 -170.76(14) ?
C4a C4 C13 C14 -112.04(13) ?
C3 C4 C13 C14 124.51(13) ?
C4a C4 C13 C18 69.21(15) ?
C3 C4 C13 C18 -54.24(15) ?
C18 C13 C14 F1 -179.51(13) ?
C4 C13 C14 F1 1.7(2) ?
C18 C13 C14 C15 0.8(2) ?
C4 C13 C14 C15 -178.03(14) ?
F1 C14 C15 C16 179.81(15) ?
C13 C14 C15 C16 -0.5(3) ?
C14 C15 C16 C17 -0.3(3) ?
C15 C16 C17 C18 0.6(3) ?
C14 C13 C18 C17 -0.4(2) ?
C4 C13 C18 C17 178.43(13) ?
C16 C17 C18 C13 -0.3(2) ?
