#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:44:41 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179024 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/22/4122268.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4122268
loop_
_publ_author_name
'Hwang, Heejun'
'Kim, Jinwoo'
'Jeong, Jisu'
'Chang, Sukbok'
_publ_section_title
;
 Regioselective introduction of heteroatoms at the C-8 position of
 quinoline N-oxides: remote C-h activation using N-oxide as a stepping
 stone.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10770
_journal_page_last               10776
_journal_paper_doi               10.1021/ja5053768
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C20 H16 N2 O3 S'
_chemical_formula_sum            'C20 H16 N2 O3 S'
_chemical_formula_weight         364.41
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXTL
_cell_angle_alpha                85.534(2)
_cell_angle_beta                 82.6980(10)
_cell_angle_gamma                73.5320(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9399(5)
_cell_length_b                   7.6809(5)
_cell_length_c                   16.4129(11)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.50
_cell_volume                     831.39(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      199(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5225
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0607
_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)+(0.1229P)²+0.3178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.2406
_reflns_number_gt                2105
_reflns_number_total             3254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5053768_si_003.cif
_cod_data_source_block           No2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4122266--4122269.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4122268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1728(6) 0.1320(5) 0.1965(2) 0.0331(9) Uani 1 1 d .
C2 C 0.1918(6) -0.0196(5) 0.2483(3) 0.0375(10) Uani 1 1 d .
H2 H 0.1722 -0.0068 0.3062 0.045 Uiso 1 1 calc R
C3 C 0.2389(7) -0.1907(6) 0.2173(3) 0.0431(11) Uani 1 1 d .
H3 H 0.2527 -0.2939 0.2543 0.052 Uiso 1 1 calc R
C4 C 0.2663(6) -0.2143(5) 0.1343(3) 0.0395(10) Uani 1 1 d .
H4 H 0.2974 -0.3330 0.1143 0.047 Uiso 1 1 calc R
C5 C 0.2482(5) -0.0621(5) 0.0782(2) 0.0308(8) Uani 1 1 d .
C6 C 0.2714(5) -0.0830(5) -0.0104(2) 0.0306(9) Uani 1 1 d .
C7 C 0.3162(6) -0.2503(5) -0.0475(3) 0.0389(10) Uani 1 1 d .
H7 H 0.3341 -0.3597 -0.0144 0.047 Uiso 1 1 calc R
C8 C 0.3342(6) -0.2562(6) -0.1318(3) 0.0447(11) Uani 1 1 d .
H8 H 0.3612 -0.3701 -0.1561 0.054 Uiso 1 1 calc R
C9 C 0.3138(6) -0.0997(6) -0.1820(3) 0.0407(10) Uani 1 1 d .
H9 H 0.3312 -0.1074 -0.2401 0.049 Uiso 1 1 calc R
C10 C 0.2686(6) 0.0658(6) -0.1477(3) 0.0365(9) Uani 1 1 d .
H10 H 0.2505 0.1737 -0.1818 0.044 Uiso 1 1 calc R
C11 C 0.2492(5) 0.0755(5) -0.0616(2) 0.0312(9) Uani 1 1 d .
C12 C 0.2045(6) 0.2452(5) -0.0255(2) 0.0328(9) Uani 1 1 d .
H12 H 0.1880 0.3515 -0.0606 0.039 Uiso 1 1 calc R
N1 N 0.1845(5) 0.2636(4) 0.0542(2) 0.0320(7) Uani 1 1 d .
O1 O 0.1466(5) 0.4305(3) 0.08131(18) 0.0430(8) Uani 1 1 d .
C13 C 0.2014(5) 0.1112(5) 0.1110(2) 0.0269(8) Uani 1 1 d .
N2 N 0.1262(5) 0.3077(4) 0.2274(2) 0.0369(8) Uani 1 1 d .
H2A H 0.1833 0.3856 0.1992 0.044 Uiso 1 1 calc R
S1 S -0.02213(15) 0.37947(15) 0.30951(6) 0.0409(4) Uani 1 1 d .
O2 O -0.1795(4) 0.2904(5) 0.32550(19) 0.0543(9) Uani 1 1 d .
O3 O -0.0755(5) 0.5736(4) 0.29752(19) 0.0512(8) Uani 1 1 d .
C14 C 0.1278(6) 0.3164(5) 0.3921(2) 0.0358(9) Uani 1 1 d .
C15 C 0.0540(6) 0.2402(6) 0.4636(3) 0.0437(10) Uani 1 1 d .
H15 H -0.0731 0.2146 0.4677 0.052 Uiso 1 1 calc R
C16 C 0.1693(7) 0.2009(6) 0.5303(3) 0.0469(11) Uani 1 1 d .
H16 H 0.1180 0.1501 0.5800 0.056 Uiso 1 1 calc R
C17 C 0.3551(6) 0.2342(6) 0.5253(3) 0.0397(10) Uani 1 1 d .
C18 C 0.4236(6) 0.3104(6) 0.4525(3) 0.0449(11) Uani 1 1 d .
H18 H 0.5506 0.3363 0.4482 0.054 Uiso 1 1 calc R
C19 C 0.3143(6) 0.3502(6) 0.3859(3) 0.0431(10) Uani 1 1 d .
H19 H 0.3666 0.4005 0.3361 0.052 Uiso 1 1 calc R
C20 C 0.4783(7) 0.1890(6) 0.5971(3) 0.0534(12) Uani 1 1 d .
H20A H 0.4363 0.2903 0.6341 0.080 Uiso 1 1 calc R
H20B H 0.6218 0.1680 0.5771 0.080 Uiso 1 1 calc R
H20C H 0.4569 0.0791 0.6268 0.080 Uiso 1 1 calc R
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C2 C1 C13 119.1(4)
C2 C1 N2 121.3(4)
C13 C1 N2 119.6(3)
C1 C2 C3 120.7(4)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 121.3(4)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 120.2(4)
C3 C4 H4 119.9
C5 C4 H4 119.9
C13 C5 C4 117.7(4)
C13 C5 C6 121.0(3)
C4 C5 C6 121.3(4)
C7 C6 C11 118.2(4)
C7 C6 C5 124.3(3)
C11 C6 C5 117.5(3)
C8 C7 C6 120.0(4)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 121.5(4)
C7 C8 H8 119.2
C9 C8 H8 119.2
C10 C9 C8 119.9(4)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 119.7(4)
C9 C10 H10 120.2
C11 C10 H10 120.2
C6 C11 C10 120.7(4)
C6 C11 C12 119.1(4)
C10 C11 C12 120.2(3)
N1 C12 C11 123.3(3)
N1 C12 H12 118.4
C11 C12 H12 118.4
C12 N1 O1 118.1(3)
C12 N1 C13 121.7(3)
O1 N1 C13 120.2(3)
C1 C13 C5 121.1(3)
C1 C13 N1 121.6(3)
C5 C13 N1 117.3(3)
C1 N2 S1 126.4(3)
C1 N2 H2A 116.8
S1 N2 H2A 116.8
O2 S1 O3 119.2(2)
O2 S1 N2 111.42(18)
O3 S1 N2 103.83(18)
O2 S1 C14 106.92(19)
O3 S1 C14 108.59(18)
N2 S1 C14 106.27(17)
C15 C14 C19 120.3(4)
C15 C14 S1 119.5(3)
C19 C14 S1 120.1(3)
C14 C15 C16 118.9(4)
C14 C15 H15 120.5
C16 C15 H15 120.5
C17 C16 C15 121.6(4)
C17 C16 H16 119.2
C15 C16 H16 119.2
C16 C17 C18 117.6(4)
C16 C17 C20 120.9(4)
C18 C17 C20 121.4(4)
C19 C18 C17 122.2(4)
C19 C18 H18 118.9
C17 C18 H18 118.9
C18 C19 C14 119.3(4)
C18 C19 H19 120.4
C14 C19 H19 120.4
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.373(5)
C1 C13 1.407(5)
C1 N2 1.414(5)
C2 C3 1.382(6)
C2 H2 0.9500
C3 C4 1.371(6)
C3 H3 0.9500
C4 C5 1.417(5)
C4 H4 0.9500
C5 C13 1.411(5)
C5 C6 1.458(5)
C6 C7 1.402(5)
C6 C11 1.407(5)
C7 C8 1.376(6)
C7 H7 0.9500
C8 C9 1.386(6)
C8 H8 0.9500
C9 C10 1.369(5)
C9 H9 0.9500
C10 C11 1.408(5)
C10 H10 0.9500
C11 C12 1.411(5)
C12 N1 1.311(5)
C12 H12 0.9500
N1 O1 1.334(4)
N1 C13 1.427(5)
N2 S1 1.620(3)
N2 H2A 0.8800
S1 O2 1.433(3)
S1 O3 1.435(3)
S1 C14 1.768(4)
C14 C15 1.376(6)
C14 C19 1.380(6)
C15 C16 1.401(6)
C15 H15 0.9500
C16 C17 1.375(6)
C16 H16 0.9500
C17 C18 1.378(6)
C17 C20 1.504(6)
C18 C19 1.376(6)
C18 H18 0.9500
C19 H19 0.9500
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
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
C13 C1 C2 C3 0.2(6)
N2 C1 C2 C3 -179.5(3)
C1 C2 C3 C4 -0.6(6)
C2 C3 C4 C5 0.6(6)
C3 C4 C5 C13 -0.1(6)
C3 C4 C5 C6 -178.4(4)
C13 C5 C6 C7 -179.5(3)
C4 C5 C6 C7 -1.3(6)
C13 C5 C6 C11 1.2(5)
C4 C5 C6 C11 179.4(3)
C11 C6 C7 C8 -1.0(6)
C5 C6 C7 C8 179.7(4)
C6 C7 C8 C9 1.6(6)
C7 C8 C9 C10 -2.0(6)
C8 C9 C10 C11 1.9(6)
C7 C6 C11 C10 0.9(5)
C5 C6 C11 C10 -179.7(3)
C7 C6 C11 C12 -179.9(3)
C5 C6 C11 C12 -0.5(5)
C9 C10 C11 C6 -1.4(5)
C9 C10 C11 C12 179.4(3)
C6 C11 C12 N1 0.8(5)
C10 C11 C12 N1 -180.0(4)
C11 C12 N1 O1 178.5(3)
C11 C12 N1 C13 -1.7(6)
C2 C1 C13 C5 0.2(5)
N2 C1 C13 C5 180.0(3)
C2 C1 C13 N1 -179.7(3)
N2 C1 C13 N1 0.0(5)
C4 C5 C13 C1 -0.3(5)
C6 C5 C13 C1 178.0(3)
C4 C5 C13 N1 179.7(3)
C6 C5 C13 N1 -2.0(5)
C12 N1 C13 C1 -177.7(3)
O1 N1 C13 C1 2.0(5)
C12 N1 C13 C5 2.3(5)
O1 N1 C13 C5 -178.0(3)
C2 C1 N2 S1 -35.8(5)
C13 C1 N2 S1 144.5(3)
C1 N2 S1 O2 -30.3(4)
C1 N2 S1 O3 -159.8(3)
C1 N2 S1 C14 85.8(3)
O2 S1 C14 C15 -16.0(4)
O3 S1 C14 C15 113.8(4)
N2 S1 C14 C15 -135.1(3)
O2 S1 C14 C19 166.6(3)
O3 S1 C14 C19 -63.7(4)
N2 S1 C14 C19 47.5(4)
C19 C14 C15 C16 1.2(6)
S1 C14 C15 C16 -176.2(3)
C14 C15 C16 C17 -1.0(7)
C15 C16 C17 C18 0.9(7)
C15 C16 C17 C20 -179.2(4)
C16 C17 C18 C19 -1.0(7)
C20 C17 C18 C19 179.0(4)
C17 C18 C19 C14 1.3(7)
C15 C14 C19 C18 -1.3(6)
S1 C14 C19 C18 176.1(3)
