#------------------------------------------------------------------------------
#$Date: 2015-08-28 16:15:16 +0300 (Fri, 28 Aug 2015) $
#$Revision: 153772 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/76/7117679.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_7117679
loop_
_publ_author_name
'Santosh J. Gharpure'
'V. Prasath'
'Vinod Kumar'
_publ_section_title
;
 Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and
 cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium
 ion cyclization of vinylogous carbamates: switch of regioselectivity
 using an internal hydroxy group as a nucleophile
;
_journal_name_full               Chem.Commun.
_journal_page_first              13623
_journal_paper_doi               10.1039/C5cc05292K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C28 H26 F3 N O7 S2'
_chemical_formula_sum            'C28 H26 F3 N O7 S2'
_chemical_formula_weight         609.63
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_update_record
;
2015-06-25 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.962(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.689(5)
_cell_length_b                   16.049(6)
_cell_length_c                   16.697(7)
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      6.70
_cell_volume                     2780(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54190
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21788
_diffrn_reflns_theta_full        68.51
_diffrn_reflns_theta_max         68.51
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.342
_exptl_absorpt_correction_T_max  0.656
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264.00
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.360
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0584P)²+0.2984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                4440
_reflns_number_total             4989
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c5cc05292k2.cif
_cod_data_source_block           SJG-VPS-OTF-CYS-1
_cod_database_code               7117679
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31823(4) 0.30607(3) 0.18752(3) 0.02054(13) Uani 1.0 4 d . . .
S2 S -0.12063(4) 0.35885(3) 0.28577(3) 0.02041(13) Uani 1.0 4 d . . .
F1 F 0.54592(10) 0.25095(7) 0.19227(7) 0.0331(3) Uani 1.0 4 d . . .
F2 F 0.43108(11) 0.27416(8) 0.06903(7) 0.0347(3) Uani 1.0 4 d . . .
F3 F 0.51388(11) 0.37690(7) 0.14694(8) 0.0357(3) Uani 1.0 4 d . . .
O1 O 0.34583(14) 0.35783(9) 0.25831(8) 0.0335(4) Uani 1.0 4 d . . .
O2 O 0.27810(13) 0.22232(8) 0.19018(9) 0.0342(4) Uani 1.0 4 d . . .
O3 O 0.21979(11) 0.34946(7) 0.11352(7) 0.0187(3) Uani 1.0 4 d . . .
O4 O -0.24012(13) 0.38486(8) 0.30216(8) 0.0280(3) Uani 1.0 4 d . . .
O5 O -0.08396(12) 0.27257(7) 0.29229(8) 0.0251(3) Uani 1.0 4 d . . .
O6 O -0.28010(13) 0.23263(8) 0.06823(9) 0.0328(4) Uani 1.0 4 d . . .
O7 O -0.08632(12) 0.17197(7) 0.11341(8) 0.0238(3) Uani 1.0 4 d . . .
N1 N -0.12801(14) 0.38559(8) 0.18819(9) 0.0183(3) Uani 1.0 4 d . . .
C1 C 0.27049(17) 0.56808(11) 0.16615(11) 0.0217(4) Uani 1.0 4 d . . .
C2 C 0.34607(17) 0.63504(11) 0.15336(11) 0.0233(4) Uani 1.0 4 d . . .
C3 C 0.40137(17) 0.63599(11) 0.08644(11) 0.0233(4) Uani 1.0 4 d . . .
C4 C 0.38272(17) 0.56878(11) 0.03224(11) 0.0228(4) Uani 1.0 4 d . . .
C5 C 0.30830(16) 0.50156(10) 0.04455(10) 0.0196(4) Uani 1.0 4 d . . .
C6 C 0.25021(15) 0.50099(10) 0.11130(10) 0.0175(4) Uani 1.0 4 d . . .
C7 C 0.16806(16) 0.43136(10) 0.12346(10) 0.0170(4) Uani 1.0 4 d . . .
C8 C 0.04950(16) 0.43131(10) 0.13681(10) 0.0169(4) Uani 1.0 4 d . . .
C9 C -0.03732(16) 0.50197(10) 0.13897(10) 0.0168(4) Uani 1.0 4 d . . .
C10 C -0.03497(17) 0.58505(10) 0.11529(10) 0.0183(4) Uani 1.0 4 d . . .
C11 C -0.13280(17) 0.63922(10) 0.12409(10) 0.0193(4) Uani 1.0 4 d . . .
C12 C -0.13048(19) 0.72903(10) 0.09833(11) 0.0240(4) Uani 1.0 4 d . . .
C13 C -0.23434(17) 0.60845(10) 0.15537(10) 0.0198(4) Uani 1.0 4 d . . .
C14 C -0.24055(16) 0.52507(11) 0.17711(10) 0.0196(4) Uani 1.0 4 d . . .
C15 C -0.14084(16) 0.47317(10) 0.16893(10) 0.0171(4) Uani 1.0 4 d . . .
C16 C -0.02335(16) 0.35350(10) 0.15082(10) 0.0175(4) Uani 1.0 4 d . . .
C17 C -0.08660(17) 0.31055(10) 0.06876(11) 0.0202(4) Uani 1.0 4 d . . .
C18 C -0.16475(17) 0.23545(11) 0.08225(11) 0.0211(4) Uani 1.0 4 d . . .
C19 C -0.15101(19) 0.09787(11) 0.13344(12) 0.0262(4) Uani 1.0 4 d . . .
C20 C -0.0497(3) 0.03358(12) 0.16518(14) 0.0375(5) Uani 1.0 4 d . . .
C21 C 0.00314(18) 0.41962(11) 0.34657(10) 0.0214(4) Uani 1.0 4 d . . .
C22 C -0.0264(2) 0.49781(12) 0.37344(11) 0.0320(5) Uani 1.0 4 d . . .
C23 C 0.0722(3) 0.54833(12) 0.41614(12) 0.0363(5) Uani 1.0 4 d . . .
C24 C 0.2002(3) 0.52346(12) 0.43201(11) 0.0311(5) Uani 1.0 4 d . . .
C25 C 0.3056(3) 0.57995(13) 0.47733(13) 0.0430(6) Uani 1.0 4 d . . .
C26 C 0.2279(2) 0.44477(12) 0.40544(11) 0.0289(5) Uani 1.0 4 d . . .
C27 C 0.13045(18) 0.39276(11) 0.36302(11) 0.0250(4) Uani 1.0 4 d . . .
C28 C 0.46257(17) 0.30192(11) 0.14595(11) 0.0235(4) Uani 1.0 4 d . . .
H1 H 0.2327 0.5680 0.2122 0.0260 Uiso 1.0 4 calc R . .
H2 H 0.3599 0.6805 0.1909 0.0280 Uiso 1.0 4 calc R . .
H3 H 0.4518 0.6823 0.0776 0.0279 Uiso 1.0 4 calc R . .
H4 H 0.4212 0.5690 -0.0134 0.0274 Uiso 1.0 4 calc R . .
H5 H 0.2966 0.4557 0.0076 0.0235 Uiso 1.0 4 calc R . .
H10 H 0.0334 0.6049 0.0931 0.0220 Uiso 1.0 4 calc R . .
H12A H -0.0410 0.7481 0.1082 0.0288 Uiso 1.0 4 calc R . .
H12B H -0.1766 0.7632 0.1306 0.0288 Uiso 1.0 4 calc R . .
H12C H -0.1724 0.7343 0.0395 0.0288 Uiso 1.0 4 calc R . .
H13 H -0.3005 0.6454 0.1619 0.0237 Uiso 1.0 4 calc R . .
H14 H -0.3108 0.5045 0.1969 0.0235 Uiso 1.0 4 calc R . .
H16 H 0.0344 0.3141 0.1892 0.0210 Uiso 1.0 4 calc R . .
H17A H -0.1435 0.3507 0.0321 0.0242 Uiso 1.0 4 calc R . .
H17B H -0.0189 0.2928 0.0411 0.0242 Uiso 1.0 4 calc R . .
H19A H -0.2133 0.0769 0.0837 0.0314 Uiso 1.0 4 calc R . .
H19B H -0.1985 0.1110 0.1760 0.0314 Uiso 1.0 4 calc R . .
H20A H -0.0009 0.0228 0.1235 0.0450 Uiso 1.0 4 calc R . .
H20B H -0.0908 -0.0181 0.1769 0.0450 Uiso 1.0 4 calc R . .
H20C H 0.0089 0.0539 0.2159 0.0450 Uiso 1.0 4 calc R . .
H22 H -0.1133 0.5162 0.3625 0.0384 Uiso 1.0 4 calc R . .
H23 H 0.0518 0.6013 0.4350 0.0436 Uiso 1.0 4 calc R . .
H25A H 0.2839 0.6008 0.5275 0.0516 Uiso 1.0 4 calc R . .
H25B H 0.3149 0.6270 0.4418 0.0516 Uiso 1.0 4 calc R . .
H25C H 0.3869 0.5489 0.4923 0.0516 Uiso 1.0 4 calc R . .
H26 H 0.3148 0.4264 0.4165 0.0347 Uiso 1.0 4 calc R . .
H27 H 0.1506 0.3392 0.3454 0.0300 Uiso 1.0 4 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 0.0181 0.0091
;
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, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 S1 O2 122.32(10) yes . . .
O1 S1 O3 111.09(8) yes . . .
O1 S1 C28 108.14(9) yes . . .
O2 S1 O3 107.09(8) yes . . .
O2 S1 C28 105.41(9) yes . . .
O3 S1 C28 100.49(8) yes . . .
O4 S2 O5 120.43(9) yes . . .
O4 S2 N1 106.12(8) yes . . .
O4 S2 C21 108.06(9) yes . . .
O5 S2 N1 105.65(8) yes . . .
O5 S2 C21 109.75(8) yes . . .
N1 S2 C21 105.86(9) yes . . .
S1 O3 C7 120.70(10) yes . . .
C18 O7 C19 115.00(15) yes . . .
S2 N1 C15 116.64(12) yes . . .
S2 N1 C16 117.03(11) yes . . .
C15 N1 C16 106.43(14) yes . . .
C2 C1 C6 119.93(18) yes . . .
C1 C2 C3 120.60(17) yes . . .
C2 C3 C4 119.63(18) yes . . .
C3 C4 C5 120.32(19) yes . . .
C4 C5 C6 120.27(16) yes . . .
C1 C6 C5 119.24(16) yes . . .
C1 C6 C7 120.04(17) yes . . .
C5 C6 C7 120.72(15) yes . . .
O3 C7 C6 114.67(15) yes . . .
O3 C7 C8 114.88(15) yes . . .
C6 C7 C8 130.28(16) yes . . .
C7 C8 C9 129.17(16) yes . . .
C7 C8 C16 124.55(16) yes . . .
C9 C8 C16 106.26(15) yes . . .
C8 C9 C10 132.55(18) yes . . .
C8 C9 C15 108.19(15) yes . . .
C10 C9 C15 119.21(16) yes . . .
C9 C10 C11 120.10(18) yes . . .
C10 C11 C12 120.14(18) yes . . .
C10 C11 C13 119.14(16) yes . . .
C12 C11 C13 120.71(17) yes . . .
C11 C13 C14 121.68(17) yes . . .
C13 C14 C15 117.78(17) yes . . .
N1 C15 C9 111.18(15) yes . . .
N1 C15 C14 126.77(17) yes . . .
C9 C15 C14 122.05(16) yes . . .
N1 C16 C8 104.10(14) yes . . .
N1 C16 C17 108.27(14) yes . . .
C8 C16 C17 111.28(15) yes . . .
C16 C17 C18 111.36(16) yes . . .
O6 C18 O7 124.32(17) yes . . .
O6 C18 C17 125.40(16) yes . . .
O7 C18 C17 110.28(15) yes . . .
O7 C19 C20 107.55(17) yes . . .
S2 C21 C22 119.25(15) yes . . .
S2 C21 C27 120.46(14) yes . . .
C22 C21 C27 120.14(17) yes . . .
C21 C22 C23 119.4(2) yes . . .
C22 C23 C24 121.52(19) yes . . .
C23 C24 C25 120.55(19) yes . . .
C23 C24 C26 118.35(18) yes . . .
C25 C24 C26 121.1(2) yes . . .
C24 C26 C27 121.1(2) yes . . .
C21 C27 C26 119.49(18) yes . . .
S1 C28 F1 108.16(14) yes . . .
S1 C28 F2 109.77(12) yes . . .
S1 C28 F3 110.23(13) yes . . .
F1 C28 F2 109.81(16) yes . . .
F1 C28 F3 109.82(14) yes . . .
F2 C28 F3 109.05(16) yes . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 O1 1.4163(15) yes . .
S1 O2 1.4148(15) yes . .
S1 O3 1.5784(12) yes . .
S1 C28 1.839(3) yes . .
S2 O4 1.4315(17) yes . .
S2 O5 1.4361(14) yes . .
S2 N1 1.6682(18) yes . .
S2 C21 1.7561(18) yes . .
F1 C28 1.315(2) yes . .
F2 C28 1.324(3) yes . .
F3 C28 1.321(3) yes . .
O3 C7 1.451(2) yes . .
O6 C18 1.199(3) yes . .
O7 C18 1.342(2) yes . .
O7 C19 1.455(3) yes . .
N1 C15 1.441(3) yes . .
N1 C16 1.498(3) yes . .
C1 C2 1.392(3) yes . .
C1 C6 1.396(3) yes . .
C2 C3 1.385(3) yes . .
C3 C4 1.391(3) yes . .
C4 C5 1.385(3) yes . .
C5 C6 1.401(3) yes . .
C6 C7 1.465(3) yes . .
C7 C8 1.339(3) yes . .
C8 C9 1.471(3) yes . .
C8 C16 1.519(3) yes . .
C9 C10 1.393(3) yes . .
C9 C15 1.398(3) yes . .
C10 C11 1.395(3) yes . .
C11 C12 1.506(3) yes . .
C11 C13 1.403(3) yes . .
C13 C14 1.392(3) yes . .
C14 C15 1.385(3) yes . .
C16 C17 1.537(3) yes . .
C17 C18 1.514(3) yes . .
C19 C20 1.497(3) yes . .
C21 C22 1.394(3) yes . .
C21 C27 1.390(3) yes . .
C22 C23 1.383(3) yes . .
C23 C24 1.388(4) yes . .
C24 C25 1.501(3) yes . .
C24 C26 1.394(3) yes . .
C26 C27 1.388(3) yes . .
