#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/05/2220536.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_2220536
loop_
_publ_author_name
'Maliha, Bushra'
'Tariq, Muhammad Ilyas'
'Tahir, M. Nawaz'
'Hussain, Ishtiaq'
'Ali, Muhammad'
_publ_section_title
;
 1,3-Dimethoxy-2,3-dihydro-1H-isoindole-2-carbothioamide
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o41
_journal_paper_doi               10.1107/S1600536808040075
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H14 N2 O2 S'
_chemical_formula_moiety         'C11 H14 N2 O2 S'
_chemical_formula_sum            'C11 H14 N2 O2 S'
_chemical_formula_weight         238.30
_chemical_name_systematic
;
(1R,3S)-1,3-dimethoxy-2,3-dihydro-1H-isoindole-2-carbothioamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 107.322(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4577(8)
_cell_length_b                   8.6455(5)
_cell_length_c                   18.2184(10)
_cell_measurement_reflns_used    1295
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.34
_cell_volume                     2324.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'Ortep3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
;
'WinGx publication routines (Farrugia, 1999) and PLATON'
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD diffractometer'
_diffrn_measurement_method       'ω 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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18083
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.368
_refine_ls_abs_structure_details ' '
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0799P)²+0.6600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2471
_reflns_number_total             2894
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2586.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220536
_cod_database_fobs_code          2220536
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 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
S S1 0.11517(2) 0.49877(3) 0.21266(2) 0.02040(10) Uani . . 1.000
O O1 0.14785(6) -0.02891(10) 0.15401(5) 0.0138(2) Uani . . 1.000
O O2 -0.01835(6) 0.30468(10) 0.05803(5) 0.0171(2) Uani . . 1.000
N N1 0.07220(7) 0.20405(11) 0.17484(6) 0.0120(3) Uani . . 1.000
N N2 0.21825(7) 0.25081(12) 0.24928(6) 0.0148(3) Uani . . 1.000
C C1 0.08273(8) 0.03577(13) 0.18556(7) 0.0110(3) Uani . . 1.000
C C2 -0.01336(8) -0.02006(14) 0.15260(7) 0.0117(3) Uani . . 1.000
C C3 -0.04573(8) -0.17035(14) 0.15157(7) 0.0154(3) Uani . . 1.000
C C4 -0.13922(9) -0.19328(15) 0.12533(8) 0.0174(3) Uani . . 1.000
C C5 -0.19841(9) -0.06902(15) 0.10138(7) 0.0167(3) Uani . . 1.000
C C6 -0.16516(8) 0.08113(14) 0.10175(7) 0.0141(3) Uani . . 1.000
C C7 -0.07174(8) 0.10380(13) 0.12693(7) 0.0119(3) Uani . . 1.000
C C8 -0.01925(8) 0.25238(13) 0.13215(7) 0.0128(3) Uani . . 1.000
C C9 0.12812(10) -0.01421(17) 0.07232(8) 0.0221(4) Uani . . 1.000
C C10 -0.08727(10) 0.41497(17) 0.02569(9) 0.0275(4) Uani . . 1.000
C C11 0.13705(8) 0.30768(14) 0.21217(7) 0.0125(3) Uani . . 1.000
H H1 0.1091(11) 0.0123(16) 0.2398(10) 0.0132 Uiso . . 1.000
H H1N 0.2602(11) 0.318(2) 0.2748(9) 0.0178 Uiso . . 1.000
H H2N 0.2325(11) 0.160(2) 0.2447(9) 0.0178 Uiso . . 1.000
H H3 -0.00537 -0.25487 0.16825 0.0184 Uiso . . 1.000
H H4 -0.16291 -0.29503 0.12374 0.0208 Uiso . . 1.000
H H5 -0.26194 -0.08673 0.08467 0.0201 Uiso . . 1.000
H H6 -0.20533 0.16594 0.08519 0.0169 Uiso . . 1.000
H H8 -0.0393(10) 0.3344(18) 0.1604(9) 0.0153 Uiso . . 1.000
H H9A 0.07524 -0.07779 0.04676 0.0265 Uiso . . 1.000
H H9B 0.18042 -0.04909 0.05681 0.0265 Uiso . . 1.000
H H9C 0.11520 0.09429 0.05753 0.0265 Uiso . . 1.000
H H10A -0.14679 0.36807 0.01925 0.0330 Uiso . . 1.000
H H10B -0.08290 0.44837 -0.02449 0.0330 Uiso . . 1.000
H H10C -0.07967 0.50456 0.05998 0.0330 Uiso . . 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C9 . . . 115.45(10) no
C8 O2 C10 . . . 112.80(10) no
C1 N1 C8 . . . 113.96(10) no
C1 N1 C11 . . . 123.18(10) no
C8 N1 C11 . . . 121.97(10) no
H1N N2 H2N . . . 119.8(16) no
C11 N2 H1N . . . 117.0(11) no
C11 N2 H2N . . . 122.7(12) no
O1 C1 N1 . . . 113.65(10) no
O1 C1 C2 . . . 116.61(10) no
N1 C1 C2 . . . 101.95(10) no
C1 C2 C3 . . . 127.81(11) no
C3 C2 C7 . . . 121.39(12) no
C1 C2 C7 . . . 110.61(10) no
C2 C3 C4 . . . 118.00(12) no
C3 C4 C5 . . . 120.95(12) no
C4 C5 C6 . . . 120.59(13) no
C5 C6 C7 . . . 118.48(11) no
C2 C7 C6 . . . 120.56(11) no
C2 C7 C8 . . . 110.63(11) no
C6 C7 C8 . . . 128.80(11) no
N1 C8 C7 . . . 101.99(9) no
O2 C8 N1 . . . 108.33(10) no
O2 C8 C7 . . . 111.52(10) no
S1 C11 N1 . . . 121.78(10) no
S1 C11 N2 . . . 121.31(10) no
N1 C11 N2 . . . 116.90(11) no
O1 C1 H1 . . . 101.4(10) no
N1 C1 H1 . . . 109.8(8) no
C2 C1 H1 . . . 113.8(10) no
C2 C3 H3 . . . 121.00 no
C4 C3 H3 . . . 121.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 121.00 no
C7 C6 H6 . . . 121.00 no
O2 C8 H8 . . . 111.2(9) no
N1 C8 H8 . . . 109.6(9) no
C7 C8 H8 . . . 113.7(9) no
O1 C9 H9A . . . 109.00 no
O1 C9 H9B . . . 109.00 no
O1 C9 H9C . . . 109.00 no
H9A C9 H9B . . . 109.00 no
H9A C9 H9C . . . 109.00 no
H9B C9 H9C . . . 109.00 no
O2 C10 H10A . . . 109.00 no
O2 C10 H10B . . . 109.00 no
O2 C10 H10C . . . 109.00 no
H10A C10 H10B . . . 109.00 no
H10A C10 H10C . . . 109.00 no
H10B C10 H10C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . . 1.6869(12) no
O1 C1 . . 1.4145(16) no
O1 C9 . . 1.4331(16) no
O2 C8 . . 1.4280(15) no
O2 C10 . . 1.4204(18) no
N1 C1 . . 1.4705(15) no
N1 C8 . . 1.4571(17) no
N1 C11 . . 1.3653(16) no
N2 C11 . . 1.3300(17) no
N2 H1N . . 0.891(17) no
N2 H2N . . 0.826(17) no
C1 C2 . . 1.5062(18) no
C2 C7 . . 1.3887(17) no
C2 C3 . . 1.3905(17) no
C3 C4 . . 1.3946(19) no
C4 C5 . . 1.3942(19) no
C5 C6 . . 1.3954(18) no
C6 C7 . . 1.3927(18) no
C7 C8 . . 1.5072(17) no
C1 H1 . . 0.972(17) no
C3 H3 . . 0.9500 no
C4 H4 . . 0.9500 no
C5 H5 . . 0.9500 no
C6 H6 . . 0.9500 no
C8 H8 . . 0.979(16) no
C9 H9A . . 0.9800 no
C9 H9B . . 0.9800 no
C9 H9C . . 0.9800 no
C10 H10A . . 0.9800 no
C10 H10B . . 0.9800 no
C10 H10C . . 0.9800 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 O2 3.3984(10) . . no
S1 N2 3.2857(11) . 6_555 no
S1 H3 2.7900 . 1_565 no
S1 H8 2.697(16) . . no
S1 H2N 2.646(17) . 6_555 no
O1 N2 2.9867(14) . . no
O1 N2 2.9738(14) . 6_545 no
O2 S1 3.3984(10) . . no
O1 H1N 2.087(17) . 6_545 no
O1 H2N 2.413(17) . . no
O2 H9C 2.7500 . . no
O2 H9A 2.7000 . 3_555 no
O2 H10B 2.8200 . 3_565 no
N2 C6 3.3938(16) . 2_555 no
N2 O1 2.9867(14) . . no
N2 O1 2.9738(14) . 6_555 no
N2 S1 3.2857(11) . 6_545 no
N1 H9C 2.6000 . . no
N2 H1 2.637(16) . . no
C1 C2 3.4582(18) . 2_555 no
C1 C7 3.5200(17) . 2_555 no
C2 C2 3.4486(17) . 2_555 no
C2 C1 3.4582(18) . 2_555 no
C3 C3 3.4413(17) . 2_555 no
C6 N2 3.3938(16) . 2_555 no
C6 C9 3.4352(19) . 3_555 no
C6 C10 3.563(2) . . no
C7 C1 3.5200(17) . 2_555 no
C7 C9 3.5571(19) . 3_555 no
C9 C7 3.5571(19) . 3_555 no
C9 C6 3.4352(19) . 3_555 no
C10 C10 3.438(2) . 3_565 no
C10 C6 3.563(2) . . no
C1 H1N 2.986(17) . 6_545 no
C1 H2N 2.488(17) . . no
C2 H9A 2.7200 . . no
C2 H1 2.800(18) . 2_555 no
C3 H1 2.920(17) . 2_555 no
C4 H1 2.955(16) . 2_555 no
C5 H1 2.897(17) . 2_555 no
C6 H10A 2.9600 . . no
C6 H1 2.819(17) . 2_555 no
C6 H9B 2.8400 . 3_555 no
C7 H1 2.773(17) . 2_555 no
C7 H10A 3.0100 . . no
C10 H10B 2.8900 . 3_565 no
C10 H5 2.9800 . 7_455 no
H1 N2 2.637(16) . . no
H1 H2N 2.28(2) . . no
H1 C2 2.800(18) . 2_555 no
H1 C3 2.920(17) . 2_555 no
H1 C4 2.955(16) . 2_555 no
H1 C5 2.897(17) . 2_555 no
H1 C6 2.819(17) . 2_555 no
H1 C7 2.773(17) . 2_555 no
H1N O1 2.087(17) . 6_555 no
H1N C1 2.986(17) . 6_555 no
H2N O1 2.413(17) . . no
H2N C1 2.488(17) . . no
H2N H1 2.28(2) . . no
H2N S1 2.646(17) . 6_545 no
H3 S1 2.7900 . 1_545 no
H5 C10 2.9800 . 7_455 no
H6 H10A 2.4400 . . no
H6 H10A 2.5200 . 7_455 no
H8 S1 2.697(16) . . no
H8 H10C 2.2800 . . no
H9A C2 2.7200 . . no
H9A O2 2.7000 . 3_555 no
H9B C6 2.8400 . 3_555 no
H9C O2 2.7500 . . no
H9C N1 2.6000 . . no
H10A C6 2.9600 . . no
H10A C7 3.0100 . . no
H10A H6 2.4400 . . no
H10A H6 2.5200 . 7_455 no
H10B O2 2.8200 . 3_565 no
H10B C10 2.8900 . 3_565 no
H10C H8 2.2800 . . 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
N2 H1N O1 6_555 0.891(17) 2.087(17) 2.9738(14) 172.9(15) yes
N2 H2N O1 . 0.826(17) 2.413(17) 2.9867(14) 127.3(14) yes
N2 H2N S1 6_545 0.826(17) 2.646(17) 3.2857(11) 135.4(15) yes
C3 H3 S1 1_545 0.9500 2.7900 3.7362(13) 178.00 yes
C8 H8 S1 . 0.979(16) 2.697(16) 3.0318(12) 100.5(11) yes
C9 H9C N1 . 0.9800 2.6000 2.9593(18) 102.00 yes
C1 H1 CgB 2_555 0.9800 2.500(17) 3.4059(13) 155.10(10) yes
C9 H9C CgA . 0.9800 2.74 2.9052(16) 90 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 O1 C1 N1 . . . . -62.73(14) no
C9 O1 C1 C2 . . . . 55.45(14) no
C10 O2 C8 N1 . . . . -153.14(10) no
C10 O2 C8 C7 . . . . 95.39(12) no
C8 N1 C1 O1 . . . . 120.77(11) no
C8 N1 C1 C2 . . . . -5.57(13) no
C11 N1 C1 O1 . . . . -69.90(15) no
C11 N1 C1 C2 . . . . 163.77(11) no
C1 N1 C8 O2 . . . . -108.78(11) no
C1 N1 C8 C7 . . . . 8.96(13) no
C11 N1 C8 O2 . . . . 81.74(13) no
C11 N1 C8 C7 . . . . -160.52(11) no
C1 N1 C11 S1 . . . . -167.45(9) no
C1 N1 C11 N2 . . . . 11.57(18) no
C8 N1 C11 S1 . . . . 1.05(17) no
C8 N1 C11 N2 . . . . -179.93(11) no
O1 C1 C2 C3 . . . . 60.04(17) no
O1 C1 C2 C7 . . . . -125.00(11) no
N1 C1 C2 C3 . . . . -175.58(12) no
N1 C1 C2 C7 . . . . -0.62(13) no
C1 C2 C3 C4 . . . . 173.19(12) no
C7 C2 C3 C4 . . . . -1.28(19) no
C1 C2 C7 C6 . . . . -173.11(11) no
C1 C2 C7 C8 . . . . 6.27(14) no
C3 C2 C7 C6 . . . . 2.22(19) no
C3 C2 C7 C8 . . . . -178.40(11) no
C2 C3 C4 C5 . . . . -0.45(19) no
C3 C4 C5 C6 . . . . 1.3(2) no
C4 C5 C6 C7 . . . . -0.33(19) no
C5 C6 C7 C2 . . . . -1.37(18) no
C5 C6 C7 C8 . . . . 179.37(12) no
C2 C7 C8 O2 . . . . 106.35(12) no
C2 C7 C8 N1 . . . . -9.08(13) no
C6 C7 C8 O2 . . . . -74.34(16) no
C6 C7 C8 N1 . . . . 170.24(12) no
