#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/98/2219814.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_2219814
loop_
_publ_author_name
'Saeed, Aamer'
'Khera, Rasheed Ahmad'
'Abbas, Naeem'
'Flörke, Ulrich'
_publ_section_title
;
 N-Cyclohexyl-3-fluorobenzamide
;
_journal_coeditor_code           CI2689
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2209
_journal_paper_doi               10.1107/S1600536808034478
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H16 F N O'
_chemical_formula_moiety         'C13 H16 F N O'
_chemical_formula_sum            'C13 H16 F N O'
_chemical_formula_weight         221.27
_chemical_name_systematic
;
N-Cyclohexyl-3-fluorobenzamide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.090(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.267(3)
_cell_length_b                   6.599(4)
_cell_length_c                   16.755(9)
_cell_measurement_reflns_used    796
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.43
_cell_volume                     582.4(6)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5071
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         2387
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0354
_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)+(0.0686P)²+0.0394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1420
_reflns_number_total             1492
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2689.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2219814
_cod_database_fobs_code          2219814
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
F F1 0.9633(3) 0.6562(2) 0.49344(8) 0.0376(4) Uani d P 0.873(3) A 1
F F2 0.249(2) 0.9837(17) 0.3846(6) 0.043(3) Uiso d P 0.127(3) A 2
O O1 0.2561(2) 0.2922(2) 0.25636(8) 0.0316(3) Uani d . 1 . .
N N1 0.6841(3) 0.2208(2) 0.25218(8) 0.0206(3) Uani d . 1 . .
H H1A 0.8356 0.2505 0.2710 0.025 Uiso calc R 1 . .
C C1 0.4794(3) 0.3278(2) 0.27778(10) 0.0208(3) Uani d . 1 . .
C C2 0.5341(3) 0.5002(2) 0.33504(9) 0.0198(3) Uani d . 1 . .
C C3 0.7409(3) 0.4971(3) 0.38818(10) 0.0229(3) Uani d . 1 A .
H H3A 0.8556 0.3860 0.3894 0.027 Uiso calc R 1 . .
C C4 0.7720(3) 0.6615(3) 0.43877(10) 0.0269(4) Uani d . 1 . .
H H4A 0.9080 0.6591 0.4760 0.032 Uiso calc PR 0.127(3) A 2
C C5 0.6128(4) 0.8300(3) 0.43745(10) 0.0288(4) Uani d . 1 A .
H H5A 0.6419 0.9416 0.4721 0.035 Uiso calc R 1 . .
C C6 0.4084(4) 0.8306(3) 0.38366(11) 0.0295(4) Uani d . 1 . .
H H6A 0.2973 0.9439 0.3817 0.035 Uiso calc PR 0.873(3) A 1
C C7 0.3671(3) 0.6659(3) 0.33314(10) 0.0253(4) Uani d . 1 A .
H H7A 0.2265 0.6658 0.2976 0.030 Uiso calc R 1 . .
C C8 0.6571(3) 0.0567(2) 0.19365(9) 0.0195(3) Uani d . 1 . .
H H8A 0.4853 -0.0054 0.2003 0.023 Uiso calc R 1 . .
C C9 0.6786(4) 0.1391(3) 0.10784(10) 0.0275(4) Uani d . 1 . .
H H9A 0.5431 0.2403 0.0984 0.033 Uiso calc R 1 . .
H H9B 0.8445 0.2074 0.1011 0.033 Uiso calc R 1 . .
C C10 0.6542(4) -0.0336(3) 0.04667(10) 0.0299(4) Uani d . 1 . .
H H10A 0.4813 -0.0920 0.0497 0.036 Uiso calc R 1 . .
H H10B 0.6781 0.0216 -0.0078 0.036 Uiso calc R 1 . .
C C11 0.8501(4) -0.2007(3) 0.06182(11) 0.0291(4) Uani d . 1 . .
H H11A 1.0228 -0.1466 0.0524 0.035 Uiso calc R 1 . .
H H11B 0.8212 -0.3136 0.0240 0.035 Uiso calc R 1 . .
C C12 0.8313(4) -0.2802(3) 0.14799(11) 0.0272(4) Uani d . 1 . .
H H12A 0.6653 -0.3480 0.1555 0.033 Uiso calc R 1 . .
H H12B 0.9664 -0.3818 0.1573 0.033 Uiso calc R 1 . .
C C13 0.8582(3) -0.1078(3) 0.20882(11) 0.0232(3) Uani d . 1 . .
H H13A 1.0299 -0.0476 0.2047 0.028 Uiso calc R 1 . .
H H13B 0.8379 -0.1624 0.2635 0.028 Uiso calc R 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
C1 N1 C8 121.23(14)
C1 N1 H1A 119.4
C8 N1 H1A 119.4
O1 C1 N1 123.89(15)
O1 C1 C2 120.02(14)
N1 C1 C2 116.09(14)
C7 C2 C3 120.72(15)
C7 C2 C1 116.85(14)
C3 C2 C1 122.42(15)
C4 C3 C2 117.78(16)
C4 C3 H3A 121.1
C2 C3 H3A 121.1
F1 C4 C3 118.55(17)
F1 C4 C5 118.43(16)
C3 C4 C5 123.00(16)
C3 C4 H4A 118.5
C5 C4 H4A 118.5
C4 C5 C6 118.30(16)
C4 C5 H5A 120.9
C6 C5 H5A 120.9
F2 C6 C7 120.5(5)
F2 C6 C5 119.0(5)
C7 C6 C5 120.42(16)
C7 C6 H6A 119.8
C5 C6 H6A 119.8
C6 C7 C2 119.75(15)
C6 C7 H7A 120.1
C2 C7 H7A 120.1
N1 C8 C13 110.16(13)
N1 C8 C9 110.86(13)
C13 C8 C9 110.58(13)
N1 C8 H8A 108.4
C13 C8 H8A 108.4
C9 C8 H8A 108.4
C10 C9 C8 110.76(15)
C10 C9 H9A 109.5
C8 C9 H9A 109.5
C10 C9 H9B 109.5
C8 C9 H9B 109.5
H9A C9 H9B 108.1
C11 C10 C9 111.55(14)
C11 C10 H10A 109.3
C9 C10 H10A 109.3
C11 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 108.0
C10 C11 C12 110.90(15)
C10 C11 H11A 109.5
C12 C11 H11A 109.5
C10 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108.0
C13 C12 C11 111.33(15)
C13 C12 H12A 109.4
C11 C12 H12A 109.4
C13 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108.0
C12 C13 C8 110.55(13)
C12 C13 H13A 109.5
C8 C13 H13A 109.5
C12 C13 H13B 109.5
C8 C13 H13B 109.5
H13A C13 H13B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.361(2)
F2 C6 1.315(11)
O1 C1 1.252(2)
N1 C1 1.359(2)
N1 C8 1.468(2)
N1 H1A 0.88
C1 C2 1.515(2)
C2 C7 1.404(2)
C2 C3 1.406(2)
C3 C4 1.386(3)
C3 H3A 0.95
C4 C5 1.393(3)
C4 H4A 0.95
C5 C6 1.403(3)
C5 H5A 0.95
C6 C7 1.394(3)
C6 H6A 0.95
C7 H7A 0.95
C8 C13 1.538(2)
C8 C9 1.541(2)
C8 H8A 1.00
C9 C10 1.538(2)
C9 H9A 0.99
C9 H9B 0.99
C10 C11 1.531(3)
C10 H10A 0.99
C10 H10B 0.99
C11 C12 1.540(3)
C11 H11A 0.99
C11 H11B 0.99
C12 C13 1.534(2)
C12 H12A 0.99
C12 H12B 0.99
C13 H13A 0.99
C13 H13B 0.99
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 H1A O1 1_655 0.88 2.25 3.050(2) 152
C5 H5A F1 2_756 0.95 2.58 3.310(3) 134
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
C8 N1 C1 O1 2.5(2)
C8 N1 C1 C2 -177.01(13)
O1 C1 C2 C7 -29.1(2)
N1 C1 C2 C7 150.37(15)
O1 C1 C2 C3 150.71(16)
N1 C1 C2 C3 -29.8(2)
C7 C2 C3 C4 0.6(2)
C1 C2 C3 C4 -179.20(14)
C2 C3 C4 F1 176.62(15)
C2 C3 C4 C5 -1.9(3)
F1 C4 C5 C6 -176.95(16)
C3 C4 C5 C6 1.6(3)
C4 C5 C6 F2 176.4(6)
C4 C5 C6 C7 0.1(3)
F2 C6 C7 C2 -177.6(5)
C5 C6 C7 C2 -1.2(3)
C3 C2 C7 C6 0.9(2)
C1 C2 C7 C6 -179.27(15)
C1 N1 C8 C13 -148.28(15)
C1 N1 C8 C9 89.00(18)
N1 C8 C9 C10 179.17(14)
C13 C8 C9 C10 56.69(18)
C8 C9 C10 C11 -55.8(2)
C9 C10 C11 C12 55.0(2)
C10 C11 C12 C13 -55.56(19)
C11 C12 C13 C8 56.76(19)
N1 C8 C13 C12 179.90(13)
C9 C8 C13 C12 -57.21(18)
