#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/68/2016820.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_2016820
loop_
_publ_author_name
'Śmiszek-Lindert, Wioleta'
'Lindert, Olaf'
'Nowak, Maria'
'Kusz, Joachim'
_publ_section_title
;
 3'-Methylacetanilide and N-benzylthioacetamide at low
 temperature
;
_journal_coeditor_code           AV3158
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o599
_journal_page_last               o603
_journal_paper_doi               10.1107/S0108270108033374
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H11 N O'
_chemical_formula_moiety         'C9 H11 N O'
_chemical_formula_sum            'C9 H11 N O'
_chemical_formula_weight         149.19
_chemical_name_common            3'-Methylacetanilide
_chemical_name_systematic
;
3'-Methylacetanilide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.280(3)
_cell_length_b                   9.4471(19)
_cell_length_c                   7.3028(15)
_cell_measurement_reflns_used    4166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.7327
_cell_measurement_theta_min      3.3607
_cell_volume                     834.4(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.0328
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Oxford Diffraction KM-4-CCD Sapphire3'
_diffrn_measurement_method       ω
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7872
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.80
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0420
_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/[σ²(Fo²)+(0.0879P)²+0.0298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                1965
_reflns_number_total             2807
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av3158.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O O1 -0.02585(6) 0.73920(8) 0.14590(10) 0.02283(19) Uani d . 1
N N1 0.05229(7) 0.95381(9) 0.22691(12) 0.01784(19) Uani d . 1
H H1 0.0399(10) 1.0377(14) 0.2722(18) 0.021 Uiso d . 1
C C1 0.15971(8) 0.93353(10) 0.18758(13) 0.0171(2) Uani d . 1
C C2 0.23887(9) 1.03419(11) 0.26142(14) 0.0198(2) Uani d . 1
H H2 0.2186 1.1085 0.3366 0.024 Uiso calc R 1
C C3 0.34665(9) 1.02751(11) 0.22684(15) 0.0218(2) Uani d . 1
C C4 0.37505(9) 0.91664(12) 0.11781(15) 0.0223(2) Uani d . 1
H H4 0.4484 0.9100 0.0933 0.027 Uiso calc R 1
C C5 0.29710(9) 0.81616(11) 0.04498(14) 0.0216(2) Uani d . 1
H H5 0.3179 0.7413 -0.0287 0.026 Uiso calc R 1
C C6 0.18906(9) 0.82308(11) 0.07795(14) 0.0194(2) Uani d . 1
H H6 0.1361 0.7541 0.0270 0.023 Uiso calc R 1
C C7 0.42999(10) 1.13762(14) 0.30661(19) 0.0320(3) Uani d . 1
H H7A 0.3971 1.2320 0.2850 0.048 Uiso calc R 1
H H7B 0.4951 1.1307 0.2463 0.048 Uiso calc R 1
H H7C 0.4520 1.1219 0.4406 0.048 Uiso calc R 1
C C8 -0.03272(8) 0.86013(11) 0.20571(13) 0.0176(2) Uani d . 1
C C9 -0.13768(9) 0.91364(12) 0.26136(14) 0.0216(2) Uani d . 1
H H9A -0.1970 0.9140 0.1526 0.032 Uiso calc R 1
H H9B -0.1261 1.0101 0.3103 0.032 Uiso calc R 1
H H9C -0.1584 0.8517 0.3574 0.032 Uiso calc R 1
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
O1 0.0271(4) 0.0175(4) 0.0245(4) -0.0038(3) 0.0063(3) -0.0021(3)
N1 0.0199(4) 0.0150(4) 0.0191(4) -0.0002(3) 0.0049(3) -0.0019(3)
C1 0.0195(5) 0.0167(4) 0.0152(4) 0.0003(3) 0.0036(3) 0.0024(3)
C2 0.0235(5) 0.0179(5) 0.0181(5) -0.0013(4) 0.0044(4) -0.0015(4)
C3 0.0220(5) 0.0208(5) 0.0224(5) -0.0028(4) 0.0031(4) 0.0021(4)
C4 0.0206(5) 0.0246(5) 0.0227(5) 0.0018(4) 0.0060(4) 0.0026(4)
C5 0.0242(5) 0.0210(5) 0.0202(5) 0.0039(4) 0.0056(4) 0.0001(4)
C6 0.0224(5) 0.0172(5) 0.0183(4) -0.0002(4) 0.0027(4) -0.0006(3)
C7 0.0256(6) 0.0312(6) 0.0389(7) -0.0088(5) 0.0045(5) -0.0052(5)
C8 0.0211(5) 0.0178(5) 0.0137(4) 0.0000(4) 0.0024(3) 0.0027(3)
C9 0.0217(5) 0.0219(5) 0.0213(5) -0.0006(4) 0.0039(4) 0.0025(4)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C1 128.04(9)
C8 N1 H1 116.8(8)
C1 N1 H1 115.2(8)
C2 C1 C6 119.76(9)
C2 C1 N1 116.16(9)
C6 C1 N1 124.06(9)
C3 C2 C1 121.23(9)
C3 C2 H2 119.4
C1 C2 H2 119.4
C2 C3 C4 118.50(10)
C2 C3 C7 120.21(10)
C4 C3 C7 121.29(10)
C5 C4 C3 120.54(10)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 121.15(10)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C1 118.82(9)
C5 C6 H6 120.6
C1 C6 H6 120.6
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O1 C8 N1 123.17(9)
O1 C8 C9 121.48(9)
N1 C8 C9 115.35(9)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 1.2312(13) y
N1 C8 1.3568(13) y
N1 C1 1.4109(14) y
N1 H1 0.882(13) y
C1 C2 1.3995(14) y
C1 C6 1.3999(14) y
C2 C3 1.3912(15) y
C2 H2 0.9500 ?
C3 C4 1.3960(15) y
C3 C7 1.5041(16) ?
C4 C5 1.3870(16) y
C4 H4 0.9500 ?
C5 C6 1.3904(15) y
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 H7A 0.9800 ?
C7 H7B 0.9800 ?
C7 H7C 0.9800 ?
C8 C9 1.5046(15) y
C9 H9A 0.9800 ?
C9 H9B 0.9800 ?
C9 H9C 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 2 0.882(13) 2.011(14) 2.8882(12) 172.3(12)
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
_geom_torsion_publ_flag
C8 N1 C1 C2 -165.66(9) y
C8 N1 C1 C6 15.95(16) y
C6 C1 C2 C3 0.51(15) ?
N1 C1 C2 C3 -177.95(9) ?
C1 C2 C3 C4 -0.71(15) ?
C1 C2 C3 C7 179.54(10) ?
C2 C3 C4 C5 0.39(15) ?
C7 C3 C4 C5 -179.86(10) ?
C3 C4 C5 C6 0.13(16) ?
C4 C5 C6 C1 -0.33(15) ?
C2 C1 C6 C5 0.02(15) ?
N1 C1 C6 C5 178.35(9) ?
C1 N1 C8 O1 -0.09(16) ?
C1 N1 C8 C9 179.68(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11332993
