#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/51/2235196.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_2235196
loop_
_publ_author_name
'Fang, Zheng'
'Zhang, Feng'
'Zou, Bao-hua'
'Guo, Kai'
_publ_section_title
;
 N-(4-Fluorophenyl)-2,2-dimethylpropanamide
;
_journal_coeditor_code           PV2534
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1757
_journal_paper_doi               10.1107/S1600536812020570
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H14 F N O'
_chemical_formula_moiety         'C11 H14 F N O'
_chemical_formula_sum            'C11 H14 F N O'
_chemical_formula_weight         195.23
_chemical_name_systematic
;
N-(4-Fluorophenyl)-2,2-dimethylpropanamide
;
_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                 92.07(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5750(19)
_cell_length_b                   13.027(3)
_cell_length_c                   8.8340(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1101.2(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0819
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4219
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.202
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                1091
_reflns_number_total             2025
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2534.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235196
_cod_database_fobs_code          2235196
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
_atom_site_symmetry_multiplicity
O O 0.55665(18) 0.65320(14) 0.18951(19) 0.0619(6) Uani d . 1 1
F F 0.01604(17) 0.92797(16) 0.1759(2) 0.1032(7) Uani d . 1 1
N N 0.4924(2) 0.74067(17) -0.0211(2) 0.0588(7) Uani d . 1 1
H H0A 0.5136 0.7547 -0.1126 0.071 Uiso calc R 1 1
C C1 0.2795(3) 0.7359(2) 0.1236(3) 0.0638(8) Uani d . 1 1
H H1A 0.2982 0.6683 0.1514 0.077 Uiso calc R 1 1
C C2 0.1603(3) 0.7837(3) 0.1726(4) 0.0728(9) Uani d . 1 1
H H2A 0.0995 0.7493 0.2349 0.087 Uiso calc R 1 1
C C3 0.1340(3) 0.8806(3) 0.1284(3) 0.0693(9) Uani d . 1 1
C C4 0.2195(3) 0.9346(2) 0.0395(3) 0.0731(9) Uani d . 1 1
H H4A 0.1981 1.0016 0.0110 0.088 Uiso calc R 1 1
C C5 0.3409(3) 0.8869(2) -0.0081(3) 0.0640(8) Uani d . 1 1
H H5A 0.4019 0.9225 -0.0687 0.077 Uiso calc R 1 1
C C6 0.3705(3) 0.7878(2) 0.0339(3) 0.0507(7) Uani d . 1 1
C C7 0.5775(3) 0.6763(2) 0.0568(3) 0.0496(7) Uani d . 1 1
C C8 0.7023(3) 0.6356(2) -0.0266(3) 0.0560(7) Uani d . 1 1
C C9 0.8029(3) 0.7255(3) -0.0500(4) 0.0864(11) Uani d . 1 1
H H9A 0.8316 0.7537 0.0465 0.130 Uiso calc R 1 1
H H9B 0.7565 0.7775 -0.1102 0.130 Uiso calc R 1 1
H H9C 0.8834 0.7014 -0.1011 0.130 Uiso calc R 1 1
C C10 0.7752(4) 0.5529(3) 0.0688(4) 0.1008(13) Uani d . 1 1
H H10A 0.7121 0.4967 0.0829 0.151 Uiso calc R 1 1
H H10B 0.8036 0.5809 0.1657 0.151 Uiso calc R 1 1
H H10C 0.8560 0.5289 0.0181 0.151 Uiso calc R 1 1
C C11 0.6568(3) 0.5904(2) -0.1808(3) 0.0759(10) Uani d . 1 1
H H11A 0.5945 0.5338 -0.1662 0.114 Uiso calc R 1 1
H H11B 0.7375 0.5669 -0.2321 0.114 Uiso calc R 1 1
H H11C 0.6097 0.6422 -0.2408 0.114 Uiso calc R 1 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
O 0.0662(12) 0.0774(14) 0.0430(11) 0.0127(10) 0.0146(9) 0.0049(10)
F 0.0656(12) 0.1364(17) 0.1092(15) 0.0362(11) 0.0246(11) -0.0114(13)
N 0.0603(14) 0.0756(15) 0.0418(12) 0.0164(13) 0.0204(11) 0.0052(12)
C1 0.0579(17) 0.071(2) 0.0637(18) 0.0048(15) 0.0160(15) 0.0065(15)
C2 0.0509(17) 0.099(3) 0.070(2) 0.0022(18) 0.0194(15) 0.0051(19)
C3 0.0507(17) 0.095(2) 0.0631(18) 0.0197(18) 0.0119(15) -0.0072(18)
C4 0.073(2) 0.073(2) 0.073(2) 0.0218(18) 0.0069(17) 0.0059(17)
C5 0.0660(19) 0.071(2) 0.0564(17) 0.0073(16) 0.0177(14) 0.0078(15)
C6 0.0519(15) 0.0640(18) 0.0370(13) 0.0053(14) 0.0113(12) -0.0002(13)
C7 0.0537(16) 0.0574(17) 0.0384(14) 0.0016(13) 0.0114(12) -0.0005(13)
C8 0.0548(16) 0.0679(19) 0.0461(15) 0.0087(14) 0.0119(12) -0.0050(14)
C9 0.0548(18) 0.112(3) 0.093(3) -0.0102(18) 0.0193(18) -0.023(2)
C10 0.097(2) 0.125(3) 0.082(2) 0.059(2) 0.022(2) 0.014(2)
C11 0.080(2) 0.082(2) 0.067(2) 0.0074(18) 0.0224(16) -0.0181(17)
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'
F F 0.0171 0.0103 '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
C7 N C6 125.9(2)
C7 N H0A 117.1
C6 N H0A 117.1
C6 C1 C2 120.4(3)
C6 C1 H1A 119.8
C2 C1 H1A 119.8
C3 C2 C1 118.7(3)
C3 C2 H2A 120.6
C1 C2 H2A 120.6
C2 C3 C4 123.1(3)
C2 C3 F 118.9(3)
C4 C3 F 117.9(3)
C3 C4 C5 118.2(3)
C3 C4 H4A 120.9
C5 C4 H4A 120.9
C6 C5 C4 120.2(3)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C5 C6 C1 119.3(2)
C5 C6 N 118.6(2)
C1 C6 N 122.0(3)
O C7 N 121.6(2)
O C7 C8 122.1(2)
N C7 C8 116.3(2)
C7 C8 C10 109.3(2)
C7 C8 C11 111.2(2)
C10 C8 C11 109.3(2)
C7 C8 C9 107.9(2)
C10 C8 C9 109.7(3)
C11 C8 C9 109.4(2)
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
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C7 1.233(3)
F C3 1.366(3)
N C7 1.342(3)
N C6 1.420(3)
N H0A 0.8600
C1 C6 1.376(4)
C1 C2 1.383(4)
C1 H1A 0.9300
C2 C3 1.343(4)
C2 H2A 0.9300
C3 C4 1.352(4)
C4 C5 1.397(4)
C4 H4A 0.9300
C5 C6 1.371(4)
C5 H5A 0.9300
C7 C8 1.522(3)
C8 C10 1.522(4)
C8 C11 1.533(4)
C8 C9 1.535(4)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
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
_geom_hbond_publ_flag
N H0A O 4_575 0.86 2.17 2.990(3) 159 y
C1 H1A O . 0.93 2.49 2.904(3) 107 n
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
C6 C1 C2 C3 1.4(5)
C1 C2 C3 C4 -0.9(5)
C1 C2 C3 F 179.7(3)
C2 C3 C4 C5 0.0(5)
F C3 C4 C5 179.4(2)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C1 0.0(4)
C4 C5 C6 N 177.8(2)
C2 C1 C6 C5 -0.9(4)
C2 C1 C6 N -178.7(2)
C7 N C6 C5 142.3(3)
C7 N C6 C1 -39.9(4)
C6 N C7 O -1.2(4)
C6 N C7 C8 -179.9(2)
O C7 C8 C10 9.3(4)
N C7 C8 C10 -172.0(3)
O C7 C8 C11 130.1(3)
N C7 C8 C11 -51.3(3)
O C7 C8 C9 -110.0(3)
N C7 C8 C9 68.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 274227
