#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/59/2235941.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_2235941
loop_
_publ_author_name
'Zhou, Yu'
'Ren, Lili'
'Lu, Yongyu'
'Zhang, Feng'
'Chen, Guoguang'
_publ_section_title
;
 N-[4-Chloro-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide
;
_journal_coeditor_code           PK2427
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2534
_journal_paper_doi               10.1107/S1600536812031650
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H13 Cl F3 N O'
_chemical_formula_moiety         'C12 H13 Cl F3 N O'
_chemical_formula_sum            'C12 H13 Cl F3 N O'
_chemical_formula_weight         279.68
_chemical_name_systematic
;
N-[4-Chloro-3-(trifluoromethyl)phenyl]-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                 104.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8850(12)
_cell_length_b                   21.955(4)
_cell_length_c                   10.307(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1289.3(5)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2599
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0613
_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)+(0.1000P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1919
_reflns_number_gt                1477
_reflns_number_total             2364
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2427.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235941
_cod_database_fobs_code          2235941
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
Cl Cl 0.8303(2) 0.49337(6) 0.12942(14) 0.0873(5) Uani d . 1 1
O O 0.1944(5) 0.25926(12) 0.2729(2) 0.0647(8) Uani d . 1 1
N N 0.2134(5) 0.27644(13) 0.0605(3) 0.0494(7) Uani d . 1 1
H H0A 0.1632 0.2645 -0.0211 0.059 Uiso calc R 1 1
F F1 0.7046(6) 0.47123(13) 0.3967(3) 0.1021(10) Uani d . 1 1
C C1 0.4957(8) 0.46500(17) 0.3095(4) 0.0639(11) Uani d . 1 1
F F2 0.3471(6) 0.44832(12) 0.3808(3) 0.1073(11) Uani d . 1 1
C C2 0.5006(6) 0.42126(16) 0.1992(3) 0.0483(9) Uani d . 1 1
F F3 0.4298(5) 0.52091(10) 0.2663(3) 0.0797(8) Uani d . 1 1
C C3 0.3567(6) 0.37039(15) 0.1826(3) 0.0474(9) Uani d . 1 1
H H3A 0.2576 0.3643 0.2389 0.057 Uiso calc R 1 1
C C4 0.3598(6) 0.32856(15) 0.0826(3) 0.0444(8) Uani d . 1 1
C C5 0.5033(7) 0.33915(17) -0.0024(3) 0.0540(9) Uani d . 1 1
H H5A 0.5024 0.3120 -0.0718 0.065 Uiso calc R 1 1
C C6 0.6482(7) 0.38958(19) 0.0147(4) 0.0623(11) Uani d . 1 1
H H6A 0.7468 0.3957 -0.0420 0.075 Uiso calc R 1 1
C C7 0.6471(6) 0.43065(17) 0.1149(4) 0.0542(9) Uani d . 1 1
C C8 0.1439(6) 0.24321(15) 0.1556(3) 0.0442(8) Uani d . 1 1
C C9 0.0085(6) 0.18476(15) 0.1083(3) 0.0463(8) Uani d . 1 1
C C10 0.1853(9) 0.1369(2) 0.0953(7) 0.107(2) Uani d . 1 1
H H10A 0.2984 0.1321 0.1798 0.161 Uiso calc R 1 1
H H10B 0.2638 0.1493 0.0284 0.161 Uiso calc R 1 1
H H10C 0.1063 0.0989 0.0694 0.161 Uiso calc R 1 1
C C11 -0.1150(11) 0.1652(3) 0.2130(5) 0.110(2) Uani d . 1 1
H H11A -0.0022 0.1605 0.2976 0.165 Uiso calc R 1 1
H H11B -0.1931 0.1270 0.1872 0.165 Uiso calc R 1 1
H H11C -0.2283 0.1955 0.2210 0.165 Uiso calc R 1 1
C C12 -0.1714(9) 0.1921(2) -0.0249(5) 0.0984(18) Uani d . 1 1
H H12A -0.0938 0.2042 -0.0923 0.148 Uiso calc R 1 1
H H12B -0.2838 0.2226 -0.0166 0.148 Uiso calc R 1 1
H H12C -0.2504 0.1540 -0.0500 0.148 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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 N C4 126.6(3)
C8 N H0A 116.7
C4 N H0A 116.7
F2 C1 F3 105.3(4)
F2 C1 F1 106.2(3)
F3 C1 F1 105.8(3)
F2 C1 C2 112.6(3)
F3 C1 C2 113.4(3)
F1 C1 C2 112.8(4)
C7 C2 C3 119.9(3)
C7 C2 C1 121.1(3)
C3 C2 C1 119.0(3)
C4 C3 C2 120.4(3)
C4 C3 H3A 119.8
C2 C3 H3A 119.8
C5 C4 C3 119.0(3)
C5 C4 N 118.6(3)
C3 C4 N 122.3(3)
C4 C5 C6 120.7(3)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C7 C6 C5 120.2(3)
C7 C6 H6A 119.9
C5 C6 H6A 119.9
C6 C7 C2 119.7(3)
C6 C7 Cl 117.8(3)
C2 C7 Cl 122.4(3)
O C8 N 120.9(3)
O C8 C9 122.5(3)
N C8 C9 116.6(3)
C11 C9 C10 109.4(4)
C11 C9 C12 109.0(4)
C10 C9 C12 109.5(4)
C11 C9 C8 108.6(3)
C10 C9 C8 107.3(3)
C12 C9 C8 113.0(3)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C7 1.732(4)
O C8 1.222(4)
N C8 1.364(4)
N C4 1.416(4)
N H0A 0.8600
F1 C1 1.336(5)
C1 F2 1.326(5)
C1 F3 1.330(4)
C1 C2 1.494(5)
C2 C7 1.385(5)
C2 C3 1.386(5)
C3 C4 1.384(4)
C3 H3A 0.9300
C4 C5 1.379(5)
C5 C6 1.382(5)
C5 H5A 0.9300
C6 C7 1.372(5)
C6 H6A 0.9300
C8 C9 1.525(5)
C9 C11 1.506(6)
C9 C10 1.508(6)
C9 C12 1.518(5)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 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 5_554 0.86 2.24 3.041(4) 155 yes
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
F2 C1 C2 C7 -179.3(4)
F3 C1 C2 C7 61.3(5)
F1 C1 C2 C7 -59.1(5)
F2 C1 C2 C3 0.2(5)
F3 C1 C2 C3 -119.2(4)
F1 C1 C2 C3 120.5(4)
C7 C2 C3 C4 0.5(5)
C1 C2 C3 C4 -179.0(3)
C2 C3 C4 C5 -1.8(5)
C2 C3 C4 N -179.0(3)
C8 N C4 C5 148.6(3)
C8 N C4 C3 -34.1(5)
C3 C4 C5 C6 2.3(5)
N C4 C5 C6 179.6(3)
C4 C5 C6 C7 -1.5(6)
C5 C6 C7 C2 0.2(6)
C5 C6 C7 Cl -179.2(3)
C3 C2 C7 C6 0.3(5)
C1 C2 C7 C6 179.8(4)
C3 C2 C7 Cl 179.7(3)
C1 C2 C7 Cl -0.8(5)
C4 N C8 O 4.8(5)
C4 N C8 C9 -173.3(3)
O C8 C9 C11 19.1(5)
N C8 C9 C11 -162.8(4)
O C8 C9 C10 -99.1(5)
N C8 C9 C10 79.0(4)
O C8 C9 C12 140.2(4)
N C8 C9 C12 -41.7(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 624481
