data_2203232
loop_
_publ_author_name
'Vande Velde, Christophe M. L.'
'Geise, Herman J.'
'Blockhuys, Frank'
_publ_section_title
;
O-(3,5-Dimethoxyphenyl)-N,N-dimethylthiocarbamate
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o199
_journal_page_last             o200
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C11 H15 N O3 S'
_chemical_formula_moiety       'C11 H15 N O3 S'
_chemical_formula_sum          'C11 H15 N O3 S'
_chemical_formula_weight       241.30
_chemical_melting_point        .349E-305
_chemical_name_common          dimethoxyphenylthiocarbamate
_chemical_name_systematic
;
O-(3,5-dimethoxyphenyl)-N,N-dimethylthiocarbamate
;
_symmetry_cell_setting         orthorhombic
_symmetry_space_group_name_Hall '-p 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              90
_cell_angle_beta               90
_cell_angle_gamma              90
_cell_formula_units_Z          8
_cell_length_a                 13.113(3)
_cell_length_b                 9.999(3)
_cell_length_c                 18.474(3)
_cell_measurement_reflns_used  25
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    18
_cell_measurement_theta_min    6
_cell_volume                   2422.2(10)
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_collection     'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction      'XCAD4 (Harms, 1996)'
_computing_molecular_graphics  'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material 'PLATON (Spek, 2003)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Enraf-Nonius MACH3'
_diffrn_measurement_method     \w/2\q
_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 0.059
_diffrn_reflns_av_sigmaI/netI  0.083
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_l_max     22
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_number          4457
_diffrn_reflns_theta_full      25.5
_diffrn_reflns_theta_max       25.5
_diffrn_reflns_theta_min       2.2
_diffrn_standards_decay_%      1
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_number       3
_exptl_absorpt_coefficient_mu  0.259
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.323
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           1024
_exptl_crystal_size_max        0.4
_exptl_crystal_size_mid        0.2
_exptl_crystal_size_min        0.2
_refine_diff_density_max       0.20
_refine_diff_density_min       -0.21
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 0.95
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   185
_refine_ls_number_reflns       2241
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    0.95
_refine_ls_R_factor_all        0.118
_refine_ls_R_factor_gt         0.034
_refine_ls_shift/su_max        0.001
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0445P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.078
_refine_ls_wR_factor_ref       0.097
_reflns_number_gt              1159
_reflns_number_total           2241
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.03899(6) 0.03280(7) 0.63759(4) 0.0547(2) Uani d . 1 . . S
O5 0.23043(14) 0.42672(18) 0.77810(9) 0.0578(5) Uani d . 1 . . O
O3 -0.02344(14) 0.57373(17) 0.61201(9) 0.0573(5) Uani d . 1 . . O
C5 0.18068(19) 0.4051(2) 0.71422(13) 0.0440(6) Uani d . 1 . . C
C1 0.14130(19) 0.2892(2) 0.60666(12) 0.0430(6) Uani d . 1 . . C
O1 0.16281(13) 0.18447(17) 0.55796(9) 0.0498(5) Uani d . 1 . . O
N1 0.14936(16) -0.0247(2) 0.52075(10) 0.0460(5) Uani d . 1 . . N
C4 0.10547(19) 0.4986(3) 0.69767(15) 0.0451(6) Uani d . 1 . . C
C6 0.1985(2) 0.2984(3) 0.66914(13) 0.0458(6) Uani d . 1 . . C
C7 0.11917(19) 0.0619(2) 0.57030(12) 0.0408(6) Uani d . 1 . . C
C8 0.2209(2) 0.0079(3) 0.46337(15) 0.0650(9) Uani d . 1 . . C
H8A 0.1873(6) 0.014(2) 0.4209(8) 0.098 Uiso calc R 1 . . H
H8B 0.2687(12) -0.0565(15) 0.4604(7) 0.098 Uiso calc R 1 . . H
H8C 0.2510(13) 0.0869(17) 0.4732(6) 0.098 Uiso calc R 1 . . H
C11 0.3139(2) 0.3408(4) 0.79478(18) 0.0622(8) Uani d . 1 . . C
C3 0.05107(18) 0.4872(2) 0.63404(13) 0.0442(6) Uani d . 1 . . C
C2 0.0696(2) 0.3813(3) 0.58678(14) 0.0463(6) Uani d . 1 . . C
C9 0.1089(2) -0.1610(2) 0.52162(16) 0.0620(8) Uani d . 1 . . C
H9A 0.1424(11) -0.2112(10) 0.5582(9) 0.093 Uiso calc R 1 . . H
H9B 0.1203(12) -0.2018(9) 0.4759(8) 0.093 Uiso calc R 1 . . H
H9C 0.0378(12) -0.1585(3) 0.5313(10) 0.093 Uiso calc R 1 . . H
C10 -0.0568(3) 0.6730(3) 0.6621(2) 0.0671(8) Uani d . 1 . . C
H6 0.2472(18) 0.238(3) 0.6808(11) 0.046(7) Uiso d . 1 . . H
H3A -0.083(2) 0.629(3) 0.7078(17) 0.081(10) Uiso d . 1 . . H
H3B -0.002(2) 0.730(3) 0.6761(15) 0.074(10) Uiso d . 1 . . H
H3C -0.110(2) 0.722(3) 0.6358(15) 0.083(10) Uiso d . 1 . . H
H4 0.0943(17) 0.561(2) 0.7263(12) 0.044(7) Uiso d . 1 . . H
H5A 0.3665(19) 0.348(2) 0.7531(14) 0.059(8) Uiso d . 1 . . H
H5B 0.289(2) 0.242(3) 0.8017(16) 0.088(10) Uiso d . 1 . . H
H5C 0.345(2) 0.375(3) 0.8371(15) 0.071(9) Uiso d . 1 . . H
H2 0.0308(17) 0.377(2) 0.5428(11) 0.042(6) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0651(4) 0.0491(4) 0.0499(4) -0.0062(3) 0.0105(4) -0.0024(3)
O5 0.0589(12) 0.0665(13) 0.0479(10) 0.0047(10) -0.0069(9) -0.0152(9)
O3 0.0652(12) 0.0483(11) 0.0583(11) 0.0088(9) -0.0042(10) -0.0007(8)
C5 0.0434(14) 0.0468(15) 0.0418(14) -0.0070(12) 0.0082(11) -0.0054(12)
C1 0.0498(14) 0.0399(14) 0.0394(13) -0.0100(12) 0.0110(12) -0.0085(11)
O1 0.0606(11) 0.0414(10) 0.0475(10) -0.0092(9) 0.0130(9) -0.0115(8)
N1 0.0537(12) 0.0435(11) 0.0409(11) 0.0007(10) 0.0001(10) -0.0105(10)
C4 0.0548(16) 0.0371(15) 0.0434(15) -0.0056(13) 0.0080(12) -0.0106(12)
C6 0.0464(15) 0.0425(15) 0.0486(15) 0.0005(13) 0.0041(14) -0.0052(13)
C7 0.0428(14) 0.0399(14) 0.0395(13) 0.0001(12) -0.0065(11) -0.0032(11)
C8 0.0685(19) 0.071(2) 0.0553(16) 0.0046(16) 0.0084(14) -0.0205(15)
C11 0.0500(18) 0.085(3) 0.0517(17) 0.0001(18) -0.0053(16) -0.0091(17)
C3 0.0450(14) 0.0384(13) 0.0492(14) -0.0038(12) 0.0084(13) 0.0018(12)
C2 0.0502(16) 0.0466(15) 0.0419(14) -0.0093(13) 0.0017(13) -0.0014(12)
C9 0.076(2) 0.0430(16) 0.0675(18) 0.0041(15) -0.0147(15) -0.0140(14)
C10 0.073(2) 0.0533(19) 0.075(2) 0.0122(18) 0.004(2) -0.0028(18)
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'
S S 0.1246 0.1234 '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'
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_3
_geom_angle
_geom_angle_publ_flag
C5 O5 C11 . . 117.3(2) ?
C3 O3 C10 . . 117.8(2) ?
O5 C5 C6 . . 124.4(2) ?
O5 C5 C4 . . 115.0(2) ?
C6 C5 C4 . . 120.6(2) ?
C2 C1 C6 . . 123.7(2) ?
C2 C1 O1 . . 117.8(2) ?
C6 C1 O1 . . 118.3(2) ?
C7 O1 C1 . . 118.32(18) ?
C7 N1 C8 . . 123.5(2) ?
C7 N1 C9 . . 119.6(2) ?
C8 N1 C9 . . 116.8(2) ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 H4 . . 120.9(16) ?
C5 C4 H4 . . 119.2(16) ?
C5 C6 C1 . . 117.8(3) ?
C5 C6 H6 . . 119.6(15) ?
C1 C6 H6 . . 122.6(14) ?
N1 C7 O1 . . 110.2(2) ?
N1 C7 S1 . . 126.6(2) ?
O1 C7 S1 . . 123.16(17) ?
N1 C8 H8A . . 109.5 ?
N1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O5 C11 H5A . . 108.0(14) ?
O5 C11 H5B . . 110.9(17) ?
H5A C11 H5B . . 111(2) ?
O5 C11 H5C . . 107.0(18) ?
H5A C11 H5C . . 108(2) ?
H5B C11 H5C . . 112(2) ?
O3 C3 C4 . . 124.8(2) ?
O3 C3 C2 . . 114.8(2) ?
C4 C3 C2 . . 120.4(2) ?
C1 C2 C3 . . 117.6(2) ?
C1 C2 H2 . . 124.3(14) ?
C3 C2 H2 . . 118.1(14) ?
N1 C9 H9A . . 109.5 ?
N1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O3 C10 H3A . . 110.0(17) ?
O3 C10 H3B . . 111.4(18) ?
H3A C10 H3B . . 107(2) ?
O3 C10 H3C . . 104.3(18) ?
H3A C10 H3C . . 113(2) ?
H3B C10 H3C . . 111(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.654(3) ?
O5 C5 . 1.365(3) ?
O5 C11 . 1.425(3) ?
O3 C3 . 1.367(3) ?
O3 C10 . 1.426(4) ?
C5 C6 . 1.374(3) ?
C5 C4 . 1.392(3) ?
C1 C2 . 1.366(4) ?
C1 C6 . 1.380(3) ?
C1 O1 . 1.409(3) ?
O1 C7 . 1.372(3) ?
N1 C7 . 1.320(3) ?
N1 C8 . 1.452(3) ?
N1 C9 . 1.462(3) ?
C4 C3 . 1.380(4) ?
C4 H4 . 0.83(2) ?
C6 H6 . 0.90(2) ?
C8 H8A . 0.9010 ?
C8 H8B . 0.9010 ?
C8 H8C . 0.9010 ?
C11 H5A . 1.04(3) ?
C11 H5B . 1.05(3) ?
C11 H5C . 0.95(3) ?
C3 C2 . 1.394(3) ?
C2 H2 . 0.96(2) ?
C9 H9A . 0.9498 ?
C9 H9B . 0.9498 ?
C9 H9C . 0.9498 ?
C10 H3A . 1.01(3) ?
C10 H3B . 0.95(3) ?
C10 H3C . 0.98(3) ?