#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/42/2224289.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_2224289
loop_
_publ_author_name
'Ferreira de Lima, Marcelle'
'de Souza, Marcus V. N.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 N-(2,6-Dimethylphenyl)-2-(2-thienyl)acetamide
;
_journal_coeditor_code           HG2603
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3203
_journal_paper_doi               10.1107/S1600536809049782
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H15 N O S'
_chemical_formula_moiety         'C14 H15 N O S'
_chemical_formula_sum            'C14 H15 N O S'
_chemical_formula_weight         245.34
_chemical_name_systematic
;
N-(2,6-Dimethylphenyl)-2-(2-thienyl)acetamide
;
_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                100.981(2)
_cell_angle_beta                 95.427(2)
_cell_angle_gamma                101.104(2)
_cell_formula_units_Z            2
_cell_length_a                   4.7489(2)
_cell_length_b                   11.7309(5)
_cell_length_c                   11.8117(4)
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     627.96(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11243
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.6
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            pale-brown
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.4276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                2388
_reflns_number_total             2840
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2603.cif
_cod_data_source_block           I
_cod_database_code               2224289
_cod_database_fobs_code          2224289
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5541(2) 0.54877(11) 0.35576(11) 0.0269(3) Uani d . 1 . .
N N1 0.1431(3) 0.61274(11) 0.31337(12) 0.0198(3) Uani d . 1 . .
H H1 -0.0473 0.5949 0.3056 0.024 Uiso calc R 1 . .
C C1 0.0819(3) 0.31943(14) 0.26257(15) 0.0227(3) Uani d P 0.569(3) A 1
S S1 0.2856(3) 0.21398(11) 0.27132(12) 0.0304(3) Uani d P 0.569(3) A 1
C C2 0.1372(5) 0.14166(18) 0.13388(18) 0.0401(5) Uani d P 0.569(3) A 1
H H2 0.1810 0.0680 0.1000 0.048 Uiso calc PR 0.569(3) A 1
C C3 -0.0428(5) 0.19078(19) 0.0743(2) 0.0431(5) Uani d P 0.569(3) A 1
H H3 -0.1283 0.1653 -0.0048 0.052 Uiso calc PR 0.569(3) A 1
C C4 -0.0767(15) 0.2938(6) 0.1609(6) 0.0469(15) Uani d P 0.569(3) A 1
H H4 -0.2108 0.3405 0.1432 0.056 Uiso calc PR 0.569(3) A 1
C C1' 0.0819(3) 0.31943(14) 0.26257(15) 0.0227(3) Uani d P 0.431(3) A 2
S S1' -0.1147(5) 0.32153(18) 0.13045(17) 0.0394(5) Uani d P 0.431(3) A 2
C C2' -0.0428(5) 0.19078(19) 0.0743(2) 0.0431(5) Uani d P 0.431(3) A 2
H H2' -0.1318 0.1500 -0.0018 0.052 Uiso calc PR 0.431(3) A 2
C C3' 0.1372(5) 0.14166(18) 0.13388(18) 0.0401(5) Uani d P 0.431(3) A 2
H H3' 0.2157 0.0741 0.1085 0.048 Uiso calc PR 0.431(3) A 2
C C4' 0.1802(19) 0.2208(7) 0.2491(7) 0.0390(18) Uani d P 0.431(3) A 2
H H4' 0.2787 0.2009 0.3140 0.047 Uiso calc PR 0.431(3) A 2
C C5 0.1040(3) 0.42001(14) 0.36525(14) 0.0216(3) Uani d . 1 . .
H H5A 0.1911 0.3995 0.4362 0.026 Uiso calc R 1 A 1
H H5B -0.0922 0.4326 0.3774 0.026 Uiso calc R 1 A 1
C C6 0.2889(3) 0.53354(14) 0.34521(13) 0.0199(3) Uani d . 1 A .
C C7 0.2832(3) 0.72479(14) 0.29151(14) 0.0203(3) Uani d . 1 . .
C C8 0.2477(3) 0.82854(14) 0.36467(14) 0.0220(3) Uani d . 1 . .
C C9 0.3851(4) 0.93774(15) 0.34462(16) 0.0279(4) Uani d . 1 . .
H H9 0.3609 1.0093 0.3922 0.033 Uiso calc R 1 . .
C C10 0.5560(4) 0.94333(16) 0.25656(17) 0.0313(4) Uani d . 1 . .
H H10 0.6530 1.0183 0.2453 0.038 Uiso calc R 1 . .
C C11 0.5854(4) 0.83976(17) 0.18487(16) 0.0308(4) Uani d . 1 . .
H H11 0.7023 0.8446 0.1243 0.037 Uiso calc R 1 . .
C C12 0.4471(4) 0.72805(16) 0.19947(14) 0.0254(4) Uani d . 1 . .
C C13 0.0684(4) 0.82262(15) 0.46287(15) 0.0261(4) Uani d . 1 . .
H H13A -0.1323 0.7830 0.4311 0.039 Uiso calc R 1 . .
H H13B 0.0740 0.9034 0.5059 0.039 Uiso calc R 1 . .
H H13C 0.1469 0.7776 0.5155 0.039 Uiso calc R 1 . .
C C14 0.4706(4) 0.61673(17) 0.11603(16) 0.0339(4) Uani d . 1 . .
H H14A 0.5533 0.6381 0.0481 0.051 Uiso calc R 1 . .
H H14B 0.2776 0.5652 0.0909 0.051 Uiso calc R 1 . .
H H14C 0.5962 0.5745 0.1549 0.051 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C6 N1 C7 . . 123.24(13) ?
C6 N1 H1 . . 118.4 ?
C7 N1 H1 . . 118.4 ?
C4 C1 C5 . . 130.6(3) ?
C4 C1 S1 . . 109.9(3) ?
C5 C1 S1 . . 119.57(13) ?
C2 S1 C1 . . 89.60(12) ?
C3 C2 S1 . . 118.43(17) ?
C3 C2 H2 . . 120.8 ?
S1 C2 H2 . . 120.8 ?
C2 C3 C4 . . 103.3(3) ?
C2 C3 H3 . . 128.3 ?
C4 C3 H3 . . 128.3 ?
C1 C4 C3 . . 118.4(5) ?
C1 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
C4' C1' C5 . . 132.7(4) ?
C4' C1' S1' . . 108.1(4) ?
C5 C1' S1' . . 119.22(13) ?
C2' S1' C1' . . 88.81(14) ?
C3' C2' S1' . . 121.55(19) ?
C3' C2' H2' . . 119.2 ?
S1' C2' H2' . . 119.2 ?
C2' C3' C4' . . 100.8(4) ?
C2' C3' H3' . . 129.6 ?
C4' C3' H3' . . 129.6 ?
C1' C4' C3' . . 119.9(6) ?
C1' C4' H4' . . 120.1 ?
C3' C4' H4' . . 120.1 ?
C1' C5 C6 . . 110.43(13) ?
C1 C5 C6 . . 110.43(13) ?
C1' C5 H5A . . 109.6 ?
C1 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
C1' C5 H5B . . 109.6 ?
C1 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
O1 C6 N1 . . 123.38(15) ?
O1 C6 C5 . . 120.78(14) ?
N1 C6 C5 . . 115.82(13) ?
C12 C7 C8 . . 122.10(14) ?
C12 C7 N1 . . 120.16(14) ?
C8 C7 N1 . . 117.74(13) ?
C9 C8 C7 . . 118.09(15) ?
C9 C8 C13 . . 120.84(15) ?
C7 C8 C13 . . 121.07(14) ?
C10 C9 C8 . . 120.92(16) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 C9 . . 119.88(16) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 121.52(16) ?
C10 C11 H11 . . 119.2 ?
C12 C11 H11 . . 119.2 ?
C11 C12 C7 . . 117.44(16) ?
C11 C12 C14 . . 120.33(15) ?
C7 C12 C14 . . 122.21(15) ?
C8 C13 H13A . . 109.5 ?
C8 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C8 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
O1 C6 . 1.2285(19) ?
N1 C6 . 1.347(2) ?
N1 C7 . 1.4360(19) ?
N1 H1 . 0.8800 ?
C1 C4 . 1.305(7) ?
C1 C5 . 1.502(2) ?
C1 S1 . 1.723(2) ?
S1 C2 . 1.697(2) ?
C2 C3 . 1.337(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.472(7) ?
C3 H3 . 0.9500 ?
C4 H4 . 0.9500 ?
C1' C4' . 1.317(9) ?
C1' C5 . 1.502(2) ?
C1' S1' . 1.748(3) ?
S1' C2' . 1.663(3) ?
C2' C3' . 1.337(3) ?
C2' H2' . 0.9500 ?
C3' C4' . 1.466(8) ?
C3' H3' . 0.9500 ?
C4' H4' . 0.9500 ?
C5 C6 . 1.520(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C7 C12 . 1.398(2) ?
C7 C8 . 1.401(2) ?
C8 C9 . 1.395(2) ?
C8 C13 . 1.507(2) ?
C9 C10 . 1.382(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.398(2) ?
C11 H11 . 0.9500 ?
C12 C14 . 1.509(2) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
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
N1 H1 O1 1_455 0.88 2.04 2.8701(18) 157
C5 H5b O1 1_455 0.99 2.38 3.2622(19) 148
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
C4 C1 S1 C2 . . . . -0.1(4) ?
C5 C1 S1 C2 . . . . 179.05(14) ?
C1 S1 C2 C3 . . . . 4.17(19) ?
S1 C2 C3 C4 . . . . -6.2(4) ?
C5 C1 C4 C3 . . . . 177.3(3) ?
S1 C1 C4 C3 . . . . -3.7(6) ?
C2 C3 C4 C1 . . . . 6.3(6) ?
C4' C1' S1' C2' . . . . 0.3(4) ?
C5 C1' S1' C2' . . . . -178.34(14) ?
C1' S1' C2' C3' . . . . -6.5(2) ?
S1' C2' C3' C4' . . . . 9.5(4) ?
C5 C1' C4' C3' . . . . -176.3(3) ?
S1' C1' C4' C3' . . . . 5.4(7) ?
C2' C3' C4' C1' . . . . -9.1(7) ?
C4' C1' C5 C6 . . . . 112.7(5) ?
S1' C1' C5 C6 . . . . -69.07(18) ?
C4 C1 C5 C6 . . . . -78.1(5) ?
S1 C1 C5 C6 . . . . 102.98(15) ?
C7 N1 C6 O1 . . . . -1.8(2) ?
C7 N1 C6 C5 . . . . 179.66(13) ?
C1 C5 C6 O1 . . . . -76.75(19) ?
C1 C5 C6 N1 . . . . 101.88(16) ?
C6 N1 C7 C12 . . . . 64.1(2) ?
C6 N1 C7 C8 . . . . -116.27(17) ?
C12 C7 C8 C9 . . . . -0.9(2) ?
N1 C7 C8 C9 . . . . 179.47(14) ?
C12 C7 C8 C13 . . . . 179.62(15) ?
N1 C7 C8 C13 . . . . 0.0(2) ?
C7 C8 C9 C10 . . . . -1.3(3) ?
C13 C8 C9 C10 . . . . 178.25(16) ?
C8 C9 C10 C11 . . . . 1.9(3) ?
C9 C10 C11 C12 . . . . -0.4(3) ?
C10 C11 C12 C7 . . . . -1.6(3) ?
C10 C11 C12 C14 . . . . 176.81(17) ?
C8 C7 C12 C11 . . . . 2.3(2) ?
N1 C7 C12 C11 . . . . -178.09(15) ?
C8 C7 C12 C14 . . . . -176.12(16) ?
N1 C7 C12 C14 . . . . 3.5(2) ?
