# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010
data_global
_journal_coden_Cambridge 177
loop_
_publ_author_name
'Mihaela Gulea'
'Annie-Claude Gaumont'
'Mihaela Gulea'
'Remi Legay'
'Jocelyne Levillain'
'Jean-Fran\,cois Lohier'
'Guillaume Mercey'
'Sopkova-de Oliveira Santos, Jana'
_publ_contact_author_name 'Mihaela Gulea'
_publ_contact_author_email MIHAELA.GULEA@ENSICAEN.FR
_publ_section_title
;
Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines,
via an unprecedented intramolecular electrophilic aromatic substitution
;
# Attachment 'CIF-gulea__R_-3a1'
data_(R)-3a
_database_code_depnum_ccdc_archive 'CCDC 766389'
#TrackingRef 'CIF-gulea__R_-3a1'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(R)-3-Aminothiochromane hydrochloride
;
_chemical_name_common ?
_chemical_melting_point 487
_chemical_formula_moiety 'C9 H12 N S, Cl'
_chemical_formula_sum 'C9 H12 Cl N S'
_chemical_formula_weight 201.71
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_chemical_absolute_configuration ad
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 5.3436(12)
_cell_length_b 6.2291(19)
_cell_length_c 29.214(8)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 972.4(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 291(2)
_cell_measurement_reflns_used 9953
_cell_measurement_theta_min 2.79
_cell_measurement_theta_max 34.91
_exptl_crystal_description polyhedron
_exptl_crystal_colour 'pale purple'
_exptl_crystal_size_max 0.56
_exptl_crystal_size_mid 0.31
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.378
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 424
_exptl_absorpt_coefficient_mu 0.551
_exptl_absorpt_correction_type numerical
_exptl_absorpt_correction_T_min 0.7343
_exptl_absorpt_correction_T_max 0.9288
_exptl_absorpt_process_details (SAINT)
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 291(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 39910
_diffrn_reflns_av_R_equivalents 0.0214
_diffrn_reflns_av_sigmaI/netI 0.0142
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -47
_diffrn_reflns_limit_l_max 47
_diffrn_reflns_theta_min 2.79
_diffrn_reflns_theta_max 35.66
_reflns_number_total 4476
_reflns_number_gt 3896
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 software (Bruker, 2007)'
_computing_cell_refinement 'APEX2 software'
_computing_data_reduction 'SAINT (Bruker, 2007)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.1184P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), 1862 Friedel pairs'
_refine_ls_abs_structure_Flack 0.02(5)
_refine_ls_number_reflns 4476
_refine_ls_number_parameters 110
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0413
_refine_ls_R_factor_gt 0.0337
_refine_ls_wR_factor_ref 0.0847
_refine_ls_wR_factor_gt 0.0809
_refine_ls_goodness_of_fit_ref 1.115
_refine_ls_restrained_S_all 1.115
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Cl1 Cl 0.32834(6) 0.55814(5) 0.223623(10) 0.03729(7) Uani 1 1 d . . .
S1 S 0.02320(8) 0.78196(6) 0.413624(12) 0.04380(9) Uani 1 1 d . . .
C8 C -0.0013(2) 0.59576(17) 0.32991(3) 0.02927(19) Uani 1 1 d . . .
H8 H 0.1337 0.6975 0.3232 0.035 Uiso 1 1 calc R . .
C2 C 0.2561(2) 0.39727(18) 0.38948(4) 0.02901(19) Uani 1 1 d . . .
C1 C 0.2262(2) 0.5622(2) 0.42133(4) 0.0312(2) Uani 1 1 d . . .
C7 C 0.1132(3) 0.38466(19) 0.34499(4) 0.0351(2) Uani 1 1 d . . .
H7A H -0.0192 0.2792 0.3482 0.042 Uiso 1 1 calc R . .
H7B H 0.2255 0.3345 0.3212 0.042 Uiso 1 1 calc R . .
C3 C 0.4281(3) 0.2354(2) 0.39938(5) 0.0382(3) Uani 1 1 d . . .
H3 H 0.4494 0.1238 0.3786 0.046 Uiso 1 1 calc R . .
C9 C -0.1672(3) 0.6901(2) 0.36692(4) 0.0363(2) Uani 1 1 d . . .
H9A H -0.2838 0.5819 0.3777 0.044 Uiso 1 1 calc R . .
H9B H -0.2629 0.8090 0.3545 0.044 Uiso 1 1 calc R . .
C4 C 0.5681(3) 0.2363(3) 0.43930(5) 0.0467(3) Uani 1 1 d . . .
H4 H 0.6812 0.1263 0.4452 0.056 Uiso 1 1 calc R . .
C6 C 0.3686(3) 0.5627(3) 0.46155(4) 0.0423(3) Uani 1 1 d . . .
H6 H 0.3479 0.6733 0.4826 0.051 Uiso 1 1 calc R . .
C5 C 0.5380(3) 0.4030(3) 0.47040(5) 0.0489(3) Uani 1 1 d . . .
H5 H 0.6325 0.4061 0.4971 0.059 Uiso 1 1 calc R . .
N1 N -0.1499(2) 0.55877(17) 0.28697(3) 0.0355(2) Uani 1 1 d . . .
H1A H -0.2401 0.4394 0.2899 0.053 Uiso 1 1 calc R . .
H1B H -0.0462 0.5452 0.2633 0.053 Uiso 1 1 calc R . .
H1C H -0.2516 0.6697 0.2822 0.053 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.04250(14) 0.02962(12) 0.03975(13) 0.00087(10) -0.00659(12) -0.00063(11)
S1 0.0537(2) 0.03654(15) 0.04118(15) -0.01290(12) -0.00053(14) 0.01006(14)
C8 0.0297(5) 0.0278(4) 0.0303(4) -0.0017(3) -0.0009(4) -0.0013(4)
C2 0.0285(4) 0.0287(5) 0.0299(4) -0.0030(4) 0.0012(4) -0.0005(4)
C1 0.0303(5) 0.0331(5) 0.0301(4) -0.0031(4) 0.0034(4) -0.0025(4)
C7 0.0399(6) 0.0296(5) 0.0358(5) -0.0080(4) -0.0088(4) 0.0061(4)
C3 0.0402(6) 0.0359(6) 0.0384(5) -0.0023(5) -0.0022(5) 0.0071(5)
C9 0.0342(5) 0.0373(6) 0.0374(5) -0.0003(4) 0.0022(5) 0.0060(5)
C4 0.0444(7) 0.0529(8) 0.0428(6) 0.0038(6) -0.0076(6) 0.0112(6)
C6 0.0460(7) 0.0501(7) 0.0308(5) -0.0081(5) -0.0014(5) -0.0023(6)
C5 0.0473(7) 0.0657(9) 0.0337(5) 0.0013(6) -0.0075(5) 0.0035(7)
N1 0.0390(5) 0.0324(4) 0.0351(4) 0.0005(4) -0.0078(4) 0.0016(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7613(13) . ?
S1 C9 1.7957(14) . ?
C8 N1 1.5026(14) . ?
C8 C7 1.5157(16) . ?
C8 C9 1.5166(16) . ?
C8 H8 0.9800 . ?
C2 C3 1.3945(17) . ?
C2 C1 1.3951(15) . ?
C2 C7 1.5095(16) . ?
C1 C6 1.3998(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9300 . ?
C6 C5 1.370(2) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C9 101.44(6) . . ?
N1 C8 C7 108.84(9) . . ?
N1 C8 C9 110.21(10) . . ?
C7 C8 C9 111.40(10) . . ?
N1 C8 H8 108.8 . . ?
C7 C8 H8 108.8 . . ?
C9 C8 H8 108.8 . . ?
C3 C2 C1 117.99(11) . . ?
C3 C2 C7 118.31(10) . . ?
C1 C2 C7 123.69(10) . . ?
C2 C1 C6 119.97(12) . . ?
C2 C1 S1 123.88(9) . . ?
C6 C1 S1 116.11(10) . . ?
C2 C7 C8 114.16(9) . . ?
C2 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C2 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C4 C3 C2 121.84(12) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C8 C9 S1 109.50(9) . . ?
C8 C9 H9A 109.8 . . ?
S1 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
S1 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C3 C4 C5 119.42(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C5 C6 C1 121.05(13) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C6 C5 C4 119.72(13) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 35.66
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.387
_refine_diff_density_min -0.169
_refine_diff_density_rms 0.051
# Attachment 'CIF-gulea__S_-3a1'
data_(S)-3a
_database_code_depnum_ccdc_archive 'CCDC 766390'
#TrackingRef 'CIF-gulea__S_-3a1'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(S)-3-Aminothiochromane hydrochloride
;
_chemical_name_common ?
_chemical_melting_point 487
_chemical_formula_moiety 'C9 H12 N S, Cl'
_chemical_formula_sum 'C9 H12 Cl N S'
_chemical_formula_weight 201.71
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_chemical_absolute_configuration ad
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 5.3668(11)
_cell_length_b 6.2152(12)
_cell_length_c 29.035(6)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 968.5(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 291(2)
_cell_measurement_reflns_used 5571
_cell_measurement_theta_min 2.80
_cell_measurement_theta_max 28.50
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.58
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.383
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 424
_exptl_absorpt_coefficient_mu 0.554
_exptl_absorpt_correction_type numerical
_exptl_absorpt_correction_T_min 0.7235
_exptl_absorpt_correction_T_max 0.9718
_exptl_absorpt_process_details (SAINT)
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 291(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 15838
_diffrn_reflns_av_R_equivalents 0.0690
_diffrn_reflns_av_sigmaI/netI 0.0471
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -41
_diffrn_reflns_limit_l_max 37
_diffrn_reflns_theta_min 2.81
_diffrn_reflns_theta_max 30.34
_reflns_number_total 2871
_reflns_number_gt 2343
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 software (Bruker, 2007)'
_computing_cell_refinement 'APEX2 software'
_computing_data_reduction 'SAINT (Bruker, 2007)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.5533P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), 1157 Friedel pairs'
_refine_ls_abs_structure_Flack 0.11(14)
_refine_ls_number_reflns 2871
_refine_ls_number_parameters 110
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0774
_refine_ls_R_factor_gt 0.0590
_refine_ls_wR_factor_ref 0.1406
_refine_ls_wR_factor_gt 0.1336
_refine_ls_goodness_of_fit_ref 1.124
_refine_ls_restrained_S_all 1.124
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Cl1 Cl 0.82820(17) 0.05843(13) 0.77637(3) 0.0379(2) Uani 1 1 d . . .
S1 S 0.4770(2) 0.78170(14) 0.91356(3) 0.0456(3) Uani 1 1 d . . .
C8 C 0.5007(6) 0.5953(5) 0.82982(10) 0.0290(6) Uani 1 1 d . . .
H8 H 0.3671 0.6981 0.8230 0.035 Uiso 1 1 calc R . .
C1 C 0.2735(6) 0.5610(5) 0.92137(10) 0.0322(6) Uani 1 1 d . . .
C3 C 0.0720(7) 0.2363(6) 0.89948(12) 0.0394(8) Uani 1 1 d . . .
H3 H 0.0508 0.1245 0.8785 0.047 Uiso 1 1 calc R . .
C9 C 0.6665(7) 0.6897(5) 0.86679(11) 0.0374(7) Uani 1 1 d . . .
H9A H 0.7616 0.8089 0.8543 0.045 Uiso 1 1 calc R . .
H9B H 0.7826 0.5814 0.8777 0.045 Uiso 1 1 calc R . .
C7 C 0.3854(7) 0.3865(5) 0.84494(11) 0.0362(7) Uani 1 1 d . . .
H7A H 0.2731 0.3373 0.8210 0.043 Uiso 1 1 calc R . .
H7B H 0.5163 0.2799 0.8480 0.043 Uiso 1 1 calc R . .
C2 C 0.2440(6) 0.3976(5) 0.88946(11) 0.0311(6) Uani 1 1 d . . .
C6 C 0.1324(7) 0.5620(7) 0.96143(12) 0.0418(8) Uani 1 1 d . . .
H6 H 0.1535 0.6727 0.9826 0.050 Uiso 1 1 calc R . .
C4 C -0.0673(7) 0.2363(7) 0.93915(14) 0.0484(9) Uani 1 1 d . . .
H4 H -0.1800 0.1260 0.9450 0.058 Uiso 1 1 calc R . .
C5 C -0.0375(8) 0.4026(7) 0.97025(12) 0.0474(9) Uani 1 1 d . . .
H5 H -0.1324 0.4064 0.9971 0.057 Uiso 1 1 calc R . .
N1 N 0.6498(6) 0.5593(5) 0.78685(9) 0.0374(6) Uani 1 1 d . . .
H1A H 0.7439 0.4425 0.7902 0.056 Uiso 1 1 calc R . .
H1B H 0.7470 0.6729 0.7817 0.056 Uiso 1 1 calc R . .
H1C H 0.5472 0.5413 0.7631 0.056 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0437(4) 0.0257(3) 0.0443(4) -0.0008(3) 0.0069(4) -0.0005(3)
S1 0.0570(6) 0.0326(4) 0.0471(5) -0.0136(4) 0.0017(4) -0.0106(4)
C8 0.0251(13) 0.0262(14) 0.0356(14) -0.0020(11) 0.0004(12) 0.0006(12)
C1 0.0316(15) 0.0305(14) 0.0346(15) -0.0011(13) -0.0035(11) 0.0053(13)
C3 0.0448(19) 0.0321(16) 0.0414(17) -0.0034(13) 0.0030(14) -0.0075(14)
C9 0.0363(16) 0.0319(15) 0.0439(18) 0.0007(13) 0.0010(15) -0.0064(14)
C7 0.0431(18) 0.0254(14) 0.0402(16) -0.0075(13) 0.0062(14) -0.0057(12)
C2 0.0321(15) 0.0253(14) 0.0358(15) -0.0023(12) -0.0016(12) -0.0008(11)
C6 0.0400(19) 0.0467(19) 0.0386(16) -0.0092(16) -0.0021(14) 0.0001(17)
C4 0.044(2) 0.049(2) 0.052(2) 0.0045(17) 0.0047(16) -0.0085(18)
C5 0.042(2) 0.062(2) 0.0382(17) -0.0007(16) 0.0079(15) -0.0034(19)
N1 0.0435(15) 0.0298(13) 0.0390(13) 0.0010(11) 0.0071(12) -0.0017(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.768(4) . ?
S1 C9 1.790(4) . ?
C8 N1 1.499(4) . ?
C8 C7 1.503(4) . ?
C8 C9 1.513(4) . ?
C8 H8 0.9800 . ?
C1 C2 1.384(4) . ?
C1 C6 1.388(5) . ?
C3 C4 1.373(5) . ?
C3 C2 1.394(4) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C2 1.500(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C5 1.370(6) . ?
C6 H6 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C9 101.56(15) . . ?
N1 C8 C7 109.5(2) . . ?
N1 C8 C9 109.5(3) . . ?
C7 C8 C9 111.7(3) . . ?
N1 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 S1 123.7(2) . . ?
C6 C1 S1 116.2(3) . . ?
C4 C3 C2 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C8 C9 S1 109.1(2) . . ?
C8 C9 H9A 109.9 . . ?
S1 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
S1 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C2 C7 C8 114.8(3) . . ?
C2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C1 C2 C3 117.7(3) . . ?
C1 C2 C7 123.5(3) . . ?
C3 C2 C7 118.8(3) . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 30.34
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 0.449
_refine_diff_density_min -0.589
_refine_diff_density_rms 0.078