#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:46:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180215 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/01/7110197.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_7110197
loop_
_publ_author_name
'Dinesh Pratapsinh Chauhan'
'Sreejith Jayasree Varma'
'Arjun Vijeta'
'Pallavi Banerjee'
'Pinaki Talukdar'
_publ_section_title
;
 A 1,3-amino group migration route to form acrylamidines
;
_journal_name_full               Chem.Commun.
_journal_page_first              323
_journal_paper_doi               10.1039/c3cc47182a
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C21 H26 N2 O3 S'
_chemical_formula_sum            'C21 H26 N2 O3 S'
_chemical_formula_weight         386.51
_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           SHELXL-97
_cell_angle_alpha                76.805(2)
_cell_angle_beta                 86.796(2)
_cell_angle_gamma                74.132(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0234(13)
_cell_length_b                   9.3284(13)
_cell_length_c                   12.4285(18)
_cell_measurement_reflns_used    9597
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.33
_cell_volume                     979.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18623
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0346
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                4400
_reflns_number_total             4933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47182a.txt
_cod_data_source_block           dinesh
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7110197
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
S1 S 1.01770(3) 0.12680(3) 0.27068(2) 0.02449(12) Uani 1 1 d .
O1 O 0.37532(10) 0.33144(10) -0.22648(7) 0.0331(2) Uani 1 1 d .
O2 O 1.02840(10) 0.20543(9) 0.15721(7) 0.0320(2) Uani 1 1 d .
O3 O 0.87625(10) 0.18058(10) 0.32747(8) 0.0345(2) Uani 1 1 d .
N2 N 1.09692(11) -0.28413(10) 0.24171(8) 0.0246(2) Uani 1 1 d .
N1 N 1.06241(11) -0.05640(10) 0.28983(8) 0.0262(2) Uani 1 1 d .
C5 C 1.16871(12) 0.14982(11) 0.34459(9) 0.0234(2) Uani 1 1 d .
C11 C 0.67284(12) 0.10777(12) 0.04157(9) 0.0237(2) Uani 1 1 d .
C8 C 1.02511(12) -0.13397(12) 0.22376(9) 0.0228(2) Uani 1 1 d .
C10 C 0.78167(13) 0.03650(12) 0.13303(10) 0.0254(2) Uani 1 1 d .
H10 H 0.7573 0.0690 0.1988 0.031 Uiso 1 1 calc R
C12 C 0.67322(13) 0.04694(12) -0.05223(10) 0.0257(2) Uani 1 1 d .
H12 H 0.7430 -0.0459 -0.0560 0.031 Uiso 1 1 calc R
C13 C 0.57239(13) 0.12232(13) -0.13810(9) 0.0267(2) Uani 1 1 d .
H13 H 0.5729 0.0792 -0.1986 0.032 Uiso 1 1 calc R
C16 C 0.56465(13) 0.24670(13) 0.04402(10) 0.0265(2) Uani 1 1 d .
H16 H 0.5599 0.2872 0.1063 0.032 Uiso 1 1 calc R
C6 C 1.16025(14) 0.13069(13) 0.45912(10) 0.0284(2) Uani 1 1 d .
H6 H 1.0772 0.1028 0.4973 0.034 Uiso 1 1 calc R
C7 C 1.27711(15) 0.15374(14) 0.51540(10) 0.0315(3) Uani 1 1 d .
H7 H 1.2710 0.1417 0.5917 0.038 Uiso 1 1 calc R
C14 C 0.46833(12) 0.26403(12) -0.13546(9) 0.0248(2) Uani 1 1 d .
C3 C 1.41080(14) 0.21006(13) 0.34607(10) 0.0294(3) Uani 1 1 d .
H3 H 1.4954 0.2348 0.3081 0.035 Uiso 1 1 calc R
C2 C 1.40348(14) 0.19455(13) 0.46045(10) 0.0288(3) Uani 1 1 d .
C9 C 0.91427(12) -0.07217(12) 0.13069(9) 0.0251(2) Uani 1 1 d .
H9 H 0.9374 -0.1104 0.0671 0.030 Uiso 1 1 calc R
C15 C 0.46396(13) 0.32620(13) -0.04345(10) 0.0276(2) Uani 1 1 d .
H15 H 0.3947 0.4196 -0.0405 0.033 Uiso 1 1 calc R
C4 C 1.29393(14) 0.18928(12) 0.28788(9) 0.0272(2) Uani 1 1 d .
H4 H 1.2996 0.2017 0.2115 0.033 Uiso 1 1 calc R
C1 C 1.52769(16) 0.22200(16) 0.52182(12) 0.0388(3) Uani 1 1 d .
H1A H 1.4873 0.3129 0.5496 0.058 Uiso 1 1 calc R
H1B H 1.6116 0.2343 0.4728 0.058 Uiso 1 1 calc R
H1C H 1.5638 0.1364 0.5824 0.058 Uiso 1 1 calc R
C17 C 0.30233(14) 0.49168(14) -0.24164(11) 0.0343(3) Uani 1 1 d .
H17A H 0.2339 0.5094 -0.1812 0.051 Uiso 1 1 calc R
H17B H 0.2448 0.5272 -0.3097 0.051 Uiso 1 1 calc R
H17C H 0.3793 0.5459 -0.2442 0.051 Uiso 1 1 calc R
C18 C 1.22371(13) -0.35354(13) 0.32217(10) 0.0268(2) Uani 1 1 d .
H18A H 1.2768 -0.2775 0.3264 0.032 Uiso 1 1 calc R
H18B H 1.2968 -0.4360 0.2964 0.032 Uiso 1 1 calc R
C19 C 1.17027(17) -0.41554(16) 0.43627(11) 0.0400(3) Uani 1 1 d .
H19A H 1.1045 -0.3331 0.4649 0.060 Uiso 1 1 calc R
H19B H 1.2580 -0.4648 0.4842 0.060 Uiso 1 1 calc R
H19C H 1.1143 -0.4882 0.4323 0.060 Uiso 1 1 calc R
C20 C 1.04560(13) -0.39043(13) 0.19116(10) 0.0288(3) Uani 1 1 d .
H20A H 0.9401 -0.3437 0.1656 0.035 Uiso 1 1 calc R
H20B H 1.0468 -0.4823 0.2470 0.035 Uiso 1 1 calc R
C21 C 1.14456(16) -0.43439(15) 0.09484(11) 0.0362(3) Uani 1 1 d .
H21A H 1.1280 -0.3479 0.0334 0.054 Uiso 1 1 calc R
H21B H 1.1171 -0.5167 0.0738 0.054 Uiso 1 1 calc R
H21C H 1.2512 -0.4664 0.1164 0.054 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
O2 S1 O3 116.52(5)
O2 S1 N1 114.26(5)
O3 S1 N1 110.16(5)
O2 S1 C5 106.93(5)
O3 S1 C5 106.87(5)
N1 S1 C5 100.50(5)
C14 O1 C17 116.92(9)
C8 N2 C18 120.97(9)
C8 N2 C20 122.85(9)
C18 N2 C20 115.94(9)
C8 N1 S1 125.71(8)
C4 C5 C6 120.30(11)
C4 C5 S1 119.78(9)
C6 C5 S1 119.91(9)
C16 C11 C12 117.42(10)
C16 C11 C10 119.04(10)
C12 C11 C10 123.50(10)
N1 C8 N2 116.93(10)
N1 C8 C9 126.65(10)
N2 C8 C9 116.42(10)
C9 C10 C11 125.69(10)
C13 C12 C11 121.02(10)
C12 C13 C14 120.55(10)
C15 C16 C11 122.22(10)
C7 C6 C5 119.21(11)
C6 C7 C2 121.68(11)
O1 C14 C15 124.34(10)
O1 C14 C13 115.90(9)
C15 C14 C13 119.76(10)
C4 C3 C2 121.21(11)
C7 C2 C3 118.02(11)
C7 C2 C1 121.25(11)
C3 C2 C1 120.73(12)
C10 C9 C8 123.44(10)
C16 C15 C14 118.97(10)
C5 C4 C3 119.56(11)
N2 C18 C19 113.04(10)
N2 C20 C21 113.36(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4447(9)
S1 O3 1.4457(9)
S1 N1 1.6087(10)
S1 C5 1.7711(12)
O1 C14 1.3683(14)
O1 C17 1.4320(14)
N2 C8 1.3450(13)
N2 C18 1.4681(14)
N2 C20 1.4699(14)
N1 C8 1.3216(15)
C5 C4 1.3889(16)
C5 C6 1.3939(16)
C11 C16 1.3987(14)
C11 C12 1.4077(15)
C11 C10 1.4565(15)
C8 C9 1.4766(15)
C10 C9 1.3440(15)
C12 C13 1.3702(16)
C13 C14 1.4028(14)
C16 C15 1.3897(16)
C6 C7 1.3865(17)
C7 C2 1.3940(19)
C14 C15 1.3895(15)
C3 C4 1.3907(16)
C3 C2 1.3953(17)
C2 C1 1.4983(17)
C18 C19 1.5099(18)
C20 C21 1.5175(17)
