#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228447.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228447
loop_
_publ_author_name
'Zhou, Feng-yan'
'Huang, Jian-ying'
_publ_section_title
;
 rac-2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide
;
_journal_coeditor_code           KP2271
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3168
_journal_paper_doi               10.1107/S1600536810046271
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H24 F N O3'
_chemical_formula_moiety         'C26 H24 F N O3'
_chemical_formula_sum            'C26 H24 F N O3'
_chemical_formula_weight         417.46
_chemical_name_systematic
;
rac-2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-
N-phenylpentanamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.651(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1694(14)
_cell_length_b                   9.8307(9)
_cell_length_c                   16.6367(16)
_cell_measurement_reflns_used    2549
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.78
_cell_measurement_theta_min      2.42
_cell_volume                     2284.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10555
_diffrn_reflns_theta_full        24.49
_diffrn_reflns_theta_max         24.49
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.677
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0667
_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)+(0.1129P)²+1.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2265
_reflns_number_gt                2493
_reflns_number_total             3792
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2271.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228447
_cod_database_fobs_code          2228447
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.0713(3) 0.2839(5) 0.9806(3) 0.0948(13) Uani d . 1 . .
H H1A 0.0361 0.2691 1.0236 0.114 Uiso calc R 1 . .
C C2 0.0430(3) 0.3814(5) 0.9239(3) 0.0996(14) Uani d . 1 . .
H H2A -0.0107 0.4368 0.9286 0.120 Uiso calc R 1 . .
C C3 0.0911(2) 0.4006(4) 0.8599(2) 0.0769(10) Uani d . 1 . .
H H3A 0.0698 0.4674 0.8196 0.092 Uiso calc R 1 . .
C C4 0.1710(2) 0.3222(3) 0.85420(17) 0.0521(7) Uani d . 1 . .
C C5 0.2012(3) 0.2269(3) 0.9127(2) 0.0763(10) Uani d . 1 . .
H H5A 0.2569 0.1745 0.9100 0.092 Uiso calc R 1 . .
C C6 0.1503(4) 0.2071(4) 0.9758(2) 0.0958(14) Uani d . 1 . .
H H6A 0.1705 0.1398 1.0159 0.115 Uiso calc R 1 . .
C C7 0.2586(2) 0.2567(3) 0.74381(17) 0.0499(7) Uani d . 1 . .
C C8 0.2898(2) 0.3116(3) 0.66692(17) 0.0546(7) Uani d . 1 . .
H H8A 0.2728 0.4103 0.6617 0.066 Uiso calc R 1 . .
C C9 0.2357(2) 0.2362(3) 0.59207(18) 0.0617(8) Uani d . 1 . .
H H9A 0.2563 0.1388 0.5948 0.074 Uiso calc R 1 . .
C C10 0.1280(3) 0.2419(4) 0.5882(2) 0.0743(10) Uani d . 1 . .
C C11 0.0794(4) 0.3651(5) 0.5882(3) 0.1127(15) Uani d . 1 . .
H H11A 0.1140 0.4482 0.5908 0.135 Uiso calc R 1 . .
C C12 -0.0191(4) 0.3675(8) 0.5845(4) 0.142(2) Uani d . 1 . .
H H12A -0.0511 0.4524 0.5845 0.170 Uiso calc R 1 . .
C C13 -0.0706(5) 0.2506(10) 0.5810(4) 0.146(2) Uani d . 1 . .
H H13A -0.1381 0.2531 0.5782 0.175 Uiso calc R 1 . .
C C14 -0.0231(5) 0.1283(8) 0.5815(3) 0.131(2) Uani d . 1 . .
H H14A -0.0580 0.0456 0.5793 0.158 Uiso calc R 1 . .
C C15 0.0746(3) 0.1249(5) 0.5851(2) 0.0931(12) Uani d . 1 . .
H H15A 0.1059 0.0394 0.5855 0.112 Uiso calc R 1 . .
C C16 0.3973(2) 0.2978(3) 0.6729(2) 0.0695(9) Uani d . 1 . .
C C17 0.4603(3) 0.3732(5) 0.7404(3) 0.1074(10) Uani d U 1 . .
H H17A 0.4183 0.4299 0.7697 0.129 Uiso calc R 1 . .
C C18 0.5129(5) 0.2730(6) 0.8006(4) 0.168(3) Uani d U 1 . .
H H18A 0.5533 0.3225 0.8447 0.253 Uiso calc R 1 . .
H H18B 0.5531 0.2142 0.7728 0.253 Uiso calc R 1 . .
H H18C 0.4665 0.2173 0.8234 0.253 Uiso calc R 1 . .
C C19 0.5271(3) 0.4666(5) 0.7060(3) 0.1074(10) Uani d . 1 . .
H H19A 0.5669 0.5158 0.7505 0.161 Uiso calc R 1 . .
H H19B 0.4898 0.5319 0.6690 0.161 Uiso calc R 1 . .
H H19C 0.5681 0.4133 0.6759 0.161 Uiso calc R 1 . .
C C20 0.2594(3) 0.2989(3) 0.5144(2) 0.0752(10) Uani d . 1 . .
C C21 0.2747(2) 0.2140(3) 0.44349(17) 0.0595(8) Uani d . 1 . .
C C22 0.2713(2) 0.0741(3) 0.44226(19) 0.0632(8) Uani d . 1 . .
H H22A 0.2592 0.0261 0.4890 0.076 Uiso calc R 1 . .
C C23 0.2853(3) 0.0031(4) 0.3737(2) 0.0784(10) Uani d . 1 . .
H H23A 0.2820 -0.0934 0.3725 0.094 Uiso calc R 1 . .
C C24 0.3038(3) 0.0743(4) 0.3080(2) 0.0821(11) Uani d . 1 . .
C C25 0.3089(3) 0.2124(4) 0.3068(2) 0.0882(11) Uani d . 1 . .
H H25A 0.3221 0.2593 0.2600 0.106 Uiso calc R 1 . .
C C26 0.2945(3) 0.2819(4) 0.3749(2) 0.0776(10) Uani d . 1 . .
H H26A 0.2980 0.3784 0.3754 0.093 Uiso calc R 1 . .
N N1 0.21798(16) 0.3485(2) 0.78690(14) 0.0535(6) Uani d . 1 . .
H H1 0.2207 0.4340 0.7719 0.066(9) Uiso calc R 1 . .
O O1 0.26887(16) 0.13615(19) 0.76232(13) 0.0648(6) Uani d . 1 . .
O O2 0.2615(3) 0.4226(3) 0.50929(17) 0.1281(13) Uani d . 1 . .
O O3 0.4304(2) 0.2291(3) 0.62480(19) 0.1088(11) Uani d . 1 . .
F F1 0.3192(2) 0.0052(3) 0.24109(15) 0.1311(11) Uani d . 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'
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
C2 C1 C6 . . 120.0(3) ?
C2 C1 H1A . . 120.0 ?
C6 C1 H1A . . 120.0 ?
C1 C2 C3 . . 120.7(4) ?
C1 C2 H2A . . 119.7 ?
C3 C2 H2A . . 119.7 ?
C2 C3 C4 . . 119.7(4) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C5 C4 C3 . . 119.6(3) ?
C5 C4 N1 . . 123.7(3) ?
C3 C4 N1 . . 116.7(3) ?
C4 C5 C6 . . 119.8(3) ?
C4 C5 H5A . . 120.1 ?
C6 C5 H5A . . 120.1 ?
C1 C6 C5 . . 120.3(4) ?
C1 C6 H6A . . 119.9 ?
C5 C6 H6A . . 119.9 ?
O1 C7 N1 . . 124.0(2) ?
O1 C7 C8 . . 121.0(2) ?
N1 C7 C8 . . 115.0(2) ?
C16 C8 C7 . . 110.1(3) ?
C16 C8 C9 . . 111.7(2) ?
C7 C8 C9 . . 109.5(2) ?
C16 C8 H8A . . 108.5 ?
C7 C8 H8A . . 108.5 ?
C9 C8 H8A . . 108.5 ?
C10 C9 C20 . . 108.3(3) ?
C10 C9 C8 . . 112.2(3) ?
C20 C9 C8 . . 110.0(2) ?
C10 C9 H9A . . 108.8 ?
C20 C9 H9A . . 108.8 ?
C8 C9 H9A . . 108.8 ?
C15 C10 C11 . . 117.3(4) ?
C15 C10 C9 . . 121.0(4) ?
C11 C10 C9 . . 121.7(3) ?
C12 C11 C10 . . 120.5(5) ?
C12 C11 H11A . . 119.7 ?
C10 C11 H11A . . 119.7 ?
C13 C12 C11 . . 121.2(6) ?
C13 C12 H12A . . 119.4 ?
C11 C12 H12A . . 119.4 ?
C12 C13 C14 . . 118.7(6) ?
C12 C13 H13A . . 120.7 ?
C14 C13 H13A . . 120.7 ?
C15 C14 C13 . . 120.6(6) ?
C15 C14 H14A . . 119.7 ?
C13 C14 H14A . . 119.7 ?
C10 C15 C14 . . 121.7(5) ?
C10 C15 H15A . . 119.2 ?
C14 C15 H15A . . 119.2 ?
O3 C16 C17 . . 121.6(4) ?
O3 C16 C8 . . 120.4(3) ?
C17 C16 C8 . . 118.0(3) ?
C19 C17 C16 . . 110.4(4) ?
C19 C17 C18 . . 112.4(5) ?
C16 C17 C18 . . 109.8(4) ?
C19 C17 H17A . . 108.0 ?
C16 C17 H17A . . 108.0 ?
C18 C17 H17A . . 108.0 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O2 C20 C21 . . 119.7(3) ?
O2 C20 C9 . . 118.3(3) ?
C21 C20 C9 . . 121.9(3) ?
C22 C21 C26 . . 118.6(3) ?
C22 C21 C20 . . 124.2(3) ?
C26 C21 C20 . . 117.2(3) ?
C21 C22 C23 . . 120.6(3) ?
C21 C22 H22A . . 119.7 ?
C23 C22 H22A . . 119.7 ?
C24 C23 C22 . . 118.5(3) ?
C24 C23 H23A . . 120.7 ?
C22 C23 H23A . . 120.7 ?
F1 C24 C25 . . 118.3(3) ?
F1 C24 C23 . . 118.8(4) ?
C25 C24 C23 . . 122.9(3) ?
C24 C25 C26 . . 118.1(3) ?
C24 C25 H25A . . 121.0 ?
C26 C25 H25A . . 121.0 ?
C25 C26 C21 . . 121.3(3) ?
C25 C26 H26A . . 119.4 ?
C21 C26 H26A . . 119.4 ?
C7 N1 C4 . . 126.8(2) ?
C7 N1 H1 . . 116.6 ?
C4 N1 H1 . . 116.6 ?
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
C1 C2 . 1.357(6) ?
C1 C6 . 1.363(6) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.370(5) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.387(4) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.366(4) ?
C4 N1 . 1.419(3) ?
C5 C6 . 1.383(5) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 O1 . 1.227(3) ?
C7 N1 . 1.341(3) ?
C7 C8 . 1.521(4) ?
C8 C16 . 1.516(5) ?
C8 C9 . 1.539(4) ?
C8 H8A . 1.0000 ?
C9 C10 . 1.517(5) ?
C9 C20 . 1.520(4) ?
C9 H9A . 1.0000 ?
C10 C15 . 1.372(5) ?
C10 C11 . 1.394(6) ?
C11 C12 . 1.387(7) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.357(8) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.377(8) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.376(7) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
C16 O3 . 1.201(4) ?
C16 C17 . 1.507(6) ?
C17 C19 . 1.499(6) ?
C17 C18 . 1.509(7) ?
C17 H17A . 1.0000 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 O2 . 1.220(4) ?
C20 C21 . 1.490(4) ?
C21 C22 . 1.375(4) ?
C21 C26 . 1.390(4) ?
C22 C23 . 1.379(4) ?
C22 H22A . 0.9500 ?
C23 C24 . 1.361(5) ?
C23 H23A . 0.9500 ?
C24 F1 . 1.352(4) ?
C24 C25 . 1.360(6) ?
C25 C26 . 1.368(5) ?
C25 H25A . 0.9500 ?
C26 H26A . 0.9500 ?
N1 H1 . 0.8800 ?
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
N1 H1 O1 2_556 0.88 2.10 2.959(2) 178(4) y
C1 H1A O3 4_566 0.95 2.43 3.371(5) 169 y
C5 H5A O1 1_555 0.95 2.52 2.963(4) 109 n
C26 H26A O2 1_555 0.95 2.41 2.735(4) 100 n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8085523
