#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240739.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_2240739
loop_
_publ_author_name
'Pradeep, P. S.'
'Naveen, S.'
'Kumara, M. N.'
'Mahadevan, K. M.'
'Lokanath, N. K.'
_publ_section_title
;
 Crystal structure of
 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
;
_journal_coeditor_code           SU2767
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              153
_journal_page_last               156
_journal_paper_doi               10.1107/S1600536814019254
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C14 H17 F N2 O'
_chemical_formula_sum            'C14 H17 F N2 O'
_chemical_formula_weight         248.30
_chemical_name_systematic
1-[(2S,4R)-6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'PLATON <TABLE ACC> option'
_cell_angle_alpha                90
_cell_angle_beta                 111.569(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3414(3)
_cell_length_b                   9.1909(3)
_cell_length_c                   12.6799(4)
_cell_measurement_reflns_used    2009
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.40
_cell_measurement_theta_min      4.48
_cell_volume                     1229.17(7)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and
publCIF
(Westrip, 2010)'
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios multilayer optics'
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8574
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        64.40
_diffrn_reflns_theta_max         64.40
_diffrn_reflns_theta_min         4.48
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0682P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                1488
_reflns_number_total             2009
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2767sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2240739
_cod_database_fobs_code          2240739
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F1 0.84526(11) 0.14151(14) 0.28243(11) 0.0311(4) Uani d . 1.000
O O1 1.19100(13) 0.59593(18) 0.49292(13) 0.0316(5) Uani d . 1.000
N N1 1.15416(15) 0.3610(2) 0.07073(15) 0.0220(6) Uani d . 1.000
N N12 1.06638(14) 0.62374(18) 0.30482(14) 0.0181(5) Uani d . 1.000
C C2 1.23865(17) 0.4842(2) 0.11812(18) 0.0208(6) Uani d . 1.000
C C3 1.16936(17) 0.5931(2) 0.16463(18) 0.0217(6) Uani d . 1.000
C C4 1.13482(16) 0.5243(2) 0.25882(17) 0.0191(6) Uani d . 1.000
C C5 0.98300(17) 0.3254(2) 0.26777(18) 0.0201(7) Uani d . 1.000
C C6 0.92150(17) 0.1966(2) 0.22961(19) 0.0226(7) Uani d . 1.000
C C7 0.93354(18) 0.1203(2) 0.14035(19) 0.0236(7) Uani d . 1.000
C C8 1.01288(18) 0.1756(2) 0.09018(19) 0.0224(7) Uani d . 1.000
C C9 1.07908(16) 0.3066(2) 0.12729(17) 0.0188(6) Uani d . 1.000
C C10 1.06312(16) 0.3830(2) 0.21747(17) 0.0177(6) Uani d . 1.000
C C11 1.27895(19) 0.5500(3) 0.02753(19) 0.0280(7) Uani d . 1.000
C C13 1.09465(18) 0.6419(2) 0.41705(18) 0.0217(7) Uani d . 1.000
C C14 0.98829(18) 0.7274(2) 0.4329(2) 0.0252(7) Uani d . 1.000
C C15 0.92345(18) 0.7996(2) 0.31843(19) 0.0246(7) Uani d . 1.000
C C16 0.94501(18) 0.6917(2) 0.23558(19) 0.0242(7) Uani d . 1.000
H H1N 1.182(2) 0.296(3) 0.039(2) 0.033(7) Uiso d . 1.000
H H2 1.31410 0.44940 0.18040 0.0250 Uiso c R 1.000
H H3A 1.09290 0.62550 0.10410 0.0260 Uiso c R 1.000
H H3B 1.22290 0.67730 0.19400 0.0260 Uiso c R 1.000
H H4 1.21440 0.49960 0.32060 0.0230 Uiso c R 1.000
H H5 0.97130 0.37440 0.32730 0.0240 Uiso c R 1.000
H H7 0.88930 0.03410 0.11480 0.0280 Uiso c R 1.000
H H8 1.02290 0.12520 0.03040 0.0270 Uiso c R 1.000
H H11A 1.31770 0.47640 -0.00270 0.0420 Uiso c R 1.000
H H11B 1.33870 0.62680 0.05990 0.0420 Uiso c R 1.000
H H11C 1.20600 0.58850 -0.03210 0.0420 Uiso c R 1.000
H H14A 1.02120 0.79930 0.49250 0.0300 Uiso c R 1.000
H H14B 0.93040 0.66350 0.45110 0.0300 Uiso c R 1.000
H H15A 0.96160 0.89310 0.31530 0.0300 Uiso c R 1.000
H H15B 0.83370 0.81320 0.30230 0.0300 Uiso c R 1.000
H H16A 0.87740 0.62030 0.21000 0.0290 Uiso c R 1.000
H H16B 0.95120 0.74120 0.17030 0.0290 Uiso c R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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'
F F 0.0727 0.0534 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' 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
C2 N1 C9 119.93(17) no
C4 N12 C13 123.12(17) no
C4 N12 C16 123.22(16) no
C13 N12 C16 112.59(17) no
C2 N1 H1N 116.2(17) no
C9 N1 H1N 113.5(18) no
C3 C2 C11 112.08(17) no
N1 C2 C3 108.38(17) no
N1 C2 C11 109.48(18) no
C2 C3 C4 110.45(15) no
N12 C4 C10 112.27(16) no
C3 C4 C10 110.07(16) no
N12 C4 C3 112.50(15) no
C6 C5 C10 120.03(19) no
F1 C6 C7 118.91(17) no
F1 C6 C5 118.54(18) no
C5 C6 C7 122.6(2) no
C6 C7 C8 118.04(18) no
C7 C8 C9 121.42(19) no
N1 C9 C10 121.63(17) no
N1 C9 C8 119.20(18) no
C8 C9 C10 119.11(18) no
C4 C10 C9 119.59(17) no
C4 C10 C5 121.56(17) no
C5 C10 C9 118.84(17) no
O1 C13 C14 126.5(2) no
N12 C13 C14 108.20(18) no
O1 C13 N12 125.3(2) no
C13 C14 C15 103.28(18) no
C14 C15 C16 103.30(16) no
N12 C16 C15 102.49(17) no
N1 C2 H2 109.00 no
C3 C2 H2 109.00 no
C11 C2 H2 109.00 no
C2 C3 H3A 110.00 no
C2 C3 H3B 110.00 no
C4 C3 H3A 110.00 no
C4 C3 H3B 110.00 no
H3A C3 H3B 108.00 no
N12 C4 H4 107.00 no
C3 C4 H4 107.00 no
C10 C4 H4 107.00 no
C6 C5 H5 120.00 no
C10 C5 H5 120.00 no
C6 C7 H7 121.00 no
C8 C7 H7 121.00 no
C7 C8 H8 119.00 no
C9 C8 H8 119.00 no
C2 C11 H11A 109.00 no
C2 C11 H11B 109.00 no
C2 C11 H11C 109.00 no
H11A C11 H11B 110.00 no
H11A C11 H11C 109.00 no
H11B C11 H11C 110.00 no
C13 C14 H14A 111.00 no
C13 C14 H14B 111.00 no
C15 C14 H14A 111.00 no
C15 C14 H14B 111.00 no
H14A C14 H14B 109.00 no
C14 C15 H15A 111.00 no
C14 C15 H15B 111.00 no
C16 C15 H15A 111.00 no
C16 C15 H15B 111.00 no
H15A C15 H15B 109.00 no
N12 C16 H16A 111.00 no
N12 C16 H16B 111.00 no
C15 C16 H16A 111.00 no
C15 C16 H16B 111.00 no
H16A C16 H16B 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C6 1.371(2) no
O1 C13 1.235(3) no
N1 C2 1.462(3) no
N1 C9 1.392(3) no
N12 C4 1.453(3) no
N12 C13 1.349(3) no
N12 C16 1.472(3) no
N1 H1N 0.84(3) no
C2 C11 1.510(3) no
C2 C3 1.519(3) no
C3 C4 1.524(3) no
C4 C10 1.520(3) no
C5 C6 1.369(3) no
C5 C10 1.392(3) no
C6 C7 1.380(3) no
C7 C8 1.376(3) no
C8 C9 1.405(3) no
C9 C10 1.409(3) no
C13 C14 1.514(3) no
C14 C15 1.518(3) no
C15 C16 1.528(3) no
C2 H2 0.9800 no
C3 H3A 0.9700 no
C3 H3B 0.9700 no
C4 H4 0.9800 no
C5 H5 0.9300 no
C7 H7 0.9300 no
C8 H8 0.9300 no
C11 H11A 0.9600 no
C11 H11B 0.9600 no
C11 H11C 0.9600 no
C14 H14A 0.9700 no
C14 H14B 0.9700 no
C15 H15A 0.9700 no
C15 H15B 0.9700 no
C16 H16A 0.9700 no
C16 H16B 0.9700 no
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 H1N O1 2_745 0.84(3) 2.46(3) 3.273(2) 162(2) yes
C7 H7 O1 4_454 0.93 2.51 3.351(3) 150 yes
C15 H15B F1 2_655 0.97 2.48 3.189(3) 130 yes
C11 H11C Cg1 3_765 0.97 2.80 3.748(3) 168 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
C9 N1 C2 C3 -40.8(2) no
C9 N1 C2 C11 -163.35(18) no
C2 N1 C9 C8 -170.60(18) no
C2 N1 C9 C10 12.4(3) no
C13 N12 C4 C3 -133.86(19) no
C13 N12 C4 C10 101.3(2) no
C16 N12 C4 C3 58.9(2) no
C16 N12 C4 C10 -66.0(2) no
C4 N12 C13 O1 11.8(3) no
C4 N12 C13 C14 -168.15(17) no
C16 N12 C13 O1 -179.74(19) no
C16 N12 C13 C14 0.4(2) no
C4 N12 C16 C15 -172.51(17) no
C13 N12 C16 C15 19.0(2) no
N1 C2 C3 C4 61.2(2) no
C11 C2 C3 C4 -177.83(17) no
C2 C3 C4 N12 -179.05(16) no
C2 C3 C4 C10 -53.0(2) no
N12 C4 C10 C5 -30.7(3) no
N12 C4 C10 C9 150.31(18) no
C3 C4 C10 C5 -156.85(18) no
C3 C4 C10 C9 24.2(2) no
C10 C5 C6 F1 178.75(18) no
C10 C5 C6 C7 -1.1(3) no
C6 C5 C10 C4 -178.91(19) no
C6 C5 C10 C9 0.1(3) no
F1 C6 C7 C8 -178.47(19) no
C5 C6 C7 C8 1.4(3) no
C6 C7 C8 C9 -0.7(3) no
C7 C8 C9 N1 -177.40(19) no
C7 C8 C9 C10 -0.3(3) no
N1 C9 C10 C4 -3.4(3) no
N1 C9 C10 C5 177.61(19) no
C8 C9 C10 C4 179.63(18) no
C8 C9 C10 C5 0.6(3) no
O1 C13 C14 C15 160.3(2) no
N12 C13 C14 C15 -19.8(2) no
C13 C14 C15 C16 30.3(2) no
C14 C15 C16 N12 -29.9(2) no
