#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/28/2212851.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_2212851
loop_
_publ_author_name
'B. Thimme Gowda'
'Jozef Kožíšek'
'Miroslav Tokarčík'
'Hartmut Fuess '
_publ_section_title
;
 N-(2-Methylphenyl)acetamide
;
_journal_coeditor_code           DN2139
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1977
_journal_page_last               o1978
_journal_paper_doi               10.1107/S1600536807012998
_journal_volume                  63
_journal_year                    2007
_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_systematic
;
N-(2-Methylphenyl)acetamide
;
_space_group_IT_number           61
_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                   8.9608(10)
_cell_length_b                   12.4784(17)
_cell_length_c                   15.012(2)
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.3
_cell_volume                     1678.6(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX
(Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.4012
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10081
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         4.2
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+1.0901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.177
_reflns_number_gt                895
_reflns_number_total             1639
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2139.cif
_cod_data_source_block           I
_cod_database_code               2212851
_cod_database_fobs_code          2212851
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_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
C C1 0.0254(4) 0.9605(3) 0.1188(2) 0.0745(11) Uani d . 1
H H1A -0.0774 0.9533 0.1358 0.089 Uiso calc R 1
H H1B 0.0430 0.9211 0.0649 0.089 Uiso calc R 1
H H1C 0.0480 1.0348 0.1092 0.089 Uiso calc R 1
C C2 0.1220(3) 0.9178(2) 0.1908(2) 0.0507(8) Uani d . 1
O O3 0.2570(2) 0.91709(19) 0.18313(13) 0.0617(7) Uani d . 1
N N4 0.0523(3) 0.8809(2) 0.26354(16) 0.0561(7) Uani d . 1
H H4N -0.0436 0.8820 0.2637 0.067 Uiso calc R 1
C C5 0.1248(3) 0.8402(3) 0.3404(2) 0.0515(8) Uani d . 1
C C6 0.2072(4) 0.7471(3) 0.3372(2) 0.0626(9) Uani d . 1
C C7 0.2717(5) 0.7132(3) 0.4163(3) 0.0850(12) Uani d . 1
H H7 0.3276 0.6505 0.4162 0.102 Uiso calc R 1
C C8 0.2564(4) 0.7683(4) 0.4942(3) 0.0851(12) Uani d . 1
H H8 0.3023 0.7433 0.5458 0.102 Uiso calc R 1
C C9 0.1743(4) 0.8595(3) 0.4963(2) 0.0754(11) Uani d . 1
H H9 0.1630 0.8974 0.5492 0.090 Uiso calc R 1
C C10 0.1079(3) 0.8953(3) 0.4196(2) 0.0606(9) Uani d . 1
H H10 0.0508 0.9575 0.4209 0.073 Uiso calc R 1
C C11 0.2227(5) 0.6830(3) 0.2542(3) 0.0935(13) Uani d . 1
H H11A 0.2584 0.6126 0.2687 0.112 Uiso calc R 1
H H11B 0.2922 0.7175 0.2150 0.112 Uiso calc R 1
H H11C 0.1273 0.6775 0.2254 0.112 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
C1 0.058(2) 0.100(3) 0.065(2) 0.000(2) -0.0088(18) 0.016(2)
C2 0.0426(17) 0.0572(19) 0.0531(18) 0.0006(15) -0.0022(15) -0.0036(15)
O3 0.0395(11) 0.0856(16) 0.0602(13) 0.0003(11) 0.0000(10) 0.0052(11)
N4 0.0376(12) 0.0725(17) 0.0581(16) 0.0014(14) -0.0007(13) 0.0058(14)
C5 0.0420(15) 0.0588(19) 0.0539(18) -0.0031(15) 0.0029(14) 0.0072(15)
C6 0.070(2) 0.0537(19) 0.064(2) 0.0051(18) 0.0044(18) 0.0038(17)
C7 0.098(3) 0.068(2) 0.091(3) 0.026(2) 0.006(3) 0.019(2)
C8 0.085(3) 0.105(3) 0.065(2) 0.016(3) -0.002(2) 0.022(3)
C9 0.071(2) 0.098(3) 0.055(2) 0.001(2) 0.0064(19) -0.003(2)
C10 0.0528(19) 0.071(2) 0.057(2) 0.0048(17) 0.0071(17) 0.0006(18)
C11 0.122(3) 0.066(2) 0.092(3) 0.011(2) 0.007(3) -0.015(2)
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 0 '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 0.006 '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
_geom_angle_publ_flag
C2 C1 H1A 109.5 no
C2 C1 H1B 109.5 no
H1A C1 H1B 109.5 no
C2 C1 H1C 109.5 no
H1A C1 H1C 109.5 no
H1B C1 H1C 109.5 no
O3 C2 N4 122.6(3) ?
O3 C2 C1 121.0(3) ?
N4 C2 C1 116.4(3) ?
C2 N4 C5 125.0(2) ?
C2 N4 H4N 117.5 no
C5 N4 H4N 117.5 no
C6 C5 C10 120.6(3) ?
C6 C5 N4 121.1(3) ?
C10 C5 N4 118.3(3) ?
C5 C6 C7 116.6(3) ?
C5 C6 C11 122.2(3) ?
C7 C6 C11 121.1(3) no
C6 C7 C8 122.8(4) no
C6 C7 H7 118.7 no
C8 C7 H7 118.7 no
C9 C8 C7 119.8(4) no
C9 C8 H8 120.1 no
C7 C8 H8 120.1 no
C8 C9 C10 119.3(4) no
C9 C10 C5 120.9(4) no
C8 C9 H9 120.3 no
C10 C9 H9 120.3 no
C9 C10 H10 119.5 no
C5 C10 H10 119.5 no
C6 C11 H11A 109.5 no
C6 C11 H11B 109.5 no
H11A C11 H11B 109.5 no
C6 C11 H11C 109.5 no
H11A C11 H11C 109.5 no
H11B C11 H11C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.483(4) ?
C1 H1A 0.96 no
C1 H1B 0.96 no
C1 H1C 0.96 no
C2 O3 1.215(3) ?
C2 N4 1.341(4) ?
N4 C5 1.417(4) ?
N4 H4N 0.86 no
C5 C6 1.377(4) ?
C5 C10 1.387(4) ?
C6 C7 1.389(5) ?
C6 C11 1.486(5) ?
C7 C8 1.360(6) ?
C7 H7 0.93 no
C8 C9 1.358(5) ?
C8 H8 0.93 no
C9 C10 1.369(5) ?
C9 H9 0.93 no
C10 H10 0.93 no
C11 H11A 0.96 no
C11 H11B 0.96 no
C11 H11C 0.96 no
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
O3 C2 N4 C5 2.4(5) ?
C1 C2 N4 C5 -177.7(3) ?
C2 N4 C5 C6 -66.3(4) ?
C2 N4 C5 C10 115.2(3) ?
C10 C5 C6 C7 -0.5(5) no
N4 C5 C6 C7 -178.9(3) no
C10 C5 C6 C11 177.4(3) no
N4 C5 C6 C11 -1.1(5) no
C5 C6 C7 C8 -0.3(6) no
C11 C6 C7 C8 -178.1(4) no
C6 C7 C8 C9 0.7(7) no
C7 C8 C9 C10 -0.4(6) no
C8 C9 C10 C5 -0.3(5) no
C6 C5 C10 C9 0.8(5) no
N4 C5 C10 C9 179.3(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10298354
