#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/98/2209849.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_2209849
loop_
_publ_author_name
'Whiteaker, Laura R.'
'Pal Chaudhuri, Urmila'
'Powell, Douglas R.'
'Houser, Robert P.'
_publ_section_title
;
 2-Phenyl-N-(2-pyridylmethyl)acetamide
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3337
_journal_page_last               o3338
_journal_paper_doi               10.1107/S1600536806026092
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H14 N2 O'
_chemical_formula_moiety         'C14 H14 N2 O'
_chemical_formula_sum            'C14 H14 N2 O'
_chemical_formula_weight         226.27
_chemical_name_systematic
;
2-phenyl-N-(2-pyridylmethyl)acetamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.106(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.414(2)
_cell_length_b                   9.2478(14)
_cell_length_c                   19.280(3)
_cell_measurement_reflns_used    7260
_cell_measurement_temperature    97(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.43
_cell_volume                     2361.5(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2002)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      97(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24749
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0334
_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)+(0.0470P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                4394
_reflns_number_total             4628
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2100.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209849
_cod_database_fobs_code          2209849
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
O O1A 0.41046(5) 0.19066(8) 0.49858(4) 0.02455(17) Uani d . 1
N N1A 0.09065(7) 0.33296(10) 0.40327(5) 0.0247(2) Uani d . 1
N N2A 0.35481(6) 0.25774(9) 0.38664(4) 0.01997(18) Uani d . 1
H H2A 0.3648(9) 0.2579(13) 0.3419(7) 0.024 Uiso d . 1
C C1A 0.00369(8) 0.26396(13) 0.40589(6) 0.0292(2) Uani d . 1
H H1A -0.0556 0.3206 0.4050 0.035 Uiso calc R 1
C C2A -0.00522(9) 0.11539(14) 0.40986(6) 0.0338(3) Uani d . 1
H H2A1 -0.0687 0.0712 0.4116 0.041 Uiso calc R 1
C C3A 0.08101(9) 0.03299(13) 0.41116(7) 0.0341(3) Uani d . 1
H H3A 0.0779 -0.0694 0.4138 0.041 Uiso calc R 1
C C4A 0.17199(8) 0.10205(12) 0.40855(6) 0.0267(2) Uani d . 1
H H4A 0.2322 0.0476 0.4094 0.032 Uiso calc R 1
C C5A 0.17388(7) 0.25170(11) 0.40471(5) 0.0202(2) Uani d . 1
C C6A 0.26974(7) 0.33835(11) 0.40475(5) 0.0211(2) Uani d . 1
H H6A1 0.2548 0.4194 0.3711 0.025 Uiso calc R 1
H H6A2 0.2897 0.3808 0.4521 0.025 Uiso calc R 1
C C7A 0.42158(7) 0.19393(10) 0.43619(5) 0.0191(2) Uani d . 1
C C8A 0.51323(7) 0.12599(11) 0.41186(5) 0.0205(2) Uani d . 1
H H8A1 0.5209 0.0250 0.4288 0.025 Uiso calc R 1
H H8A2 0.5035 0.1244 0.3599 0.025 Uiso calc R 1
C C9A 0.60759(7) 0.21078(10) 0.43959(5) 0.0196(2) Uani d . 1
C C10A 0.65429(8) 0.19666(12) 0.50905(6) 0.0243(2) Uani d . 1
H H10A 0.6275 0.1314 0.5394 0.029 Uiso calc R 1
C C11A 0.73967(8) 0.27696(12) 0.53436(6) 0.0276(2) Uani d . 1
H H11A 0.7711 0.2663 0.5818 0.033 Uiso calc R 1
C C12A 0.77918(8) 0.37277(12) 0.49047(6) 0.0282(2) Uani d . 1
H H12A 0.8376 0.4280 0.5077 0.034 Uiso calc R 1
C C13A 0.73305(8) 0.38747(12) 0.42146(6) 0.0298(2) Uani d . 1
H H13A 0.7599 0.4531 0.3913 0.036 Uiso calc R 1
C C14A 0.64779(8) 0.30693(12) 0.39598(6) 0.0251(2) Uani d . 1
H H14A 0.6167 0.3176 0.3484 0.030 Uiso calc R 1
O O1B 0.40684(6) 0.23413(9) 0.24750(4) 0.02860(18) Uani d . 1
N N1B 0.71458(6) 0.11980(9) 0.21749(4) 0.02299(19) Uani d . 1
N N2B 0.45353(6) 0.21462(10) 0.14074(5) 0.02155(19) Uani d . 1
H H2B 0.4425(10) 0.2386(14) 0.0956(7) 0.026 Uiso d . 1
C C1B 0.80120(8) 0.18496(12) 0.24404(6) 0.0263(2) Uani d . 1
H H1B 0.8582 0.1258 0.2597 0.032 Uiso calc R 1
C C2B 0.81281(8) 0.33329(12) 0.25005(6) 0.0274(2) Uani d . 1
H H2B1 0.8764 0.3748 0.2681 0.033 Uiso calc R 1
C C3B 0.72921(8) 0.41951(12) 0.22896(5) 0.0258(2) Uani d . 1
H H3B 0.7339 0.5217 0.2330 0.031 Uiso calc R 1
C C4B 0.63845(8) 0.35400(11) 0.20188(5) 0.0229(2) Uani d . 1
H H4B 0.5798 0.4108 0.1874 0.027 Uiso calc R 1
C C5B 0.63425(7) 0.20438(11) 0.19615(5) 0.0199(2) Uani d . 1
C C6B 0.53961(7) 0.12282(11) 0.16506(5) 0.0234(2) Uani d . 1
H H6B1 0.5546 0.0639 0.1251 0.028 Uiso calc R 1
H H6B2 0.5213 0.0556 0.2010 0.028 Uiso calc R 1
C C7B 0.39365(7) 0.26525(11) 0.18448(5) 0.0207(2) Uani d . 1
C C8B 0.30853(7) 0.36495(11) 0.15184(5) 0.0226(2) Uani d . 1
H H8B1 0.3124 0.4570 0.1784 0.027 Uiso calc R 1
H H8B2 0.3166 0.3873 0.1028 0.027 Uiso calc R 1
C C9B 0.20639(7) 0.29570(10) 0.15253(5) 0.0200(2) Uani d . 1
C C10B 0.15460(8) 0.23117(12) 0.09212(5) 0.0247(2) Uani d . 1
H H10B 0.1818 0.2356 0.0496 0.030 Uiso calc R 1
C C11B 0.06378(8) 0.16053(12) 0.09346(6) 0.0278(2) Uani d . 1
H H11B 0.0293 0.1167 0.0519 0.033 Uiso calc R 1
C C12B 0.02290(8) 0.15338(12) 0.15501(6) 0.0270(2) Uani d . 1
H H12B -0.0387 0.1034 0.1561 0.032 Uiso calc R 1
C C13B 0.07293(8) 0.22003(12) 0.21520(6) 0.0263(2) Uani d . 1
H H13B 0.0449 0.2170 0.2574 0.032 Uiso calc R 1
C C14B 0.16385(8) 0.29112(11) 0.21380(5) 0.0231(2) Uani d . 1
H H14B 0.1973 0.3371 0.2551 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'
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
C1A N1A C5A 117.36(10) ?
C7A N2A C6A 121.16(9) ?
C7A N2A H2A 120.3(8) ?
C6A N2A H2A 118.4(8) ?
N1A C1A C2A 124.04(11) ?
N1A C1A H1A 118.0 ?
C2A C1A H1A 118.0 ?
C3A C2A C1A 118.01(11) ?
C3A C2A H2A1 121.0 ?
C1A C2A H2A1 121.0 ?
C2A C3A C4A 119.00(11) ?
C2A C3A H3A 120.5 ?
C4A C3A H3A 120.5 ?
C3A C4A C5A 119.07(10) ?
C3A C4A H4A 120.5 ?
C5A C4A H4A 120.5 ?
N1A C5A C4A 122.52(10) ?
N1A C5A C6A 114.01(9) ?
C4A C5A C6A 123.42(9) ?
N2A C6A C5A 115.33(8) ?
N2A C6A H6A1 108.4 ?
C5A C6A H6A1 108.4 ?
N2A C6A H6A2 108.4 ?
C5A C6A H6A2 108.4 ?
H6A1 C6A H6A2 107.5 ?
O1A C7A N2A 122.36(9) n
O1A C7A C8A 121.24(9) n
N2A C7A C8A 116.40(9) n
C9A C8A C7A 110.44(8) ?
C9A C8A H8A1 109.6 ?
C7A C8A H8A1 109.6 ?
C9A C8A H8A2 109.6 ?
C7A C8A H8A2 109.6 ?
H8A1 C8A H8A2 108.1 ?
C14A C9A C10A 118.91(9) ?
C14A C9A C8A 120.05(9) ?
C10A C9A C8A 121.03(9) ?
C11A C10A C9A 120.60(10) ?
C11A C10A H10A 119.7 ?
C9A C10A H10A 119.7 ?
C12A C11A C10A 120.08(10) ?
C12A C11A H11A 120.0 ?
C10A C11A H11A 120.0 ?
C13A C12A C11A 119.60(10) ?
C13A C12A H12A 120.2 ?
C11A C12A H12A 120.2 ?
C12A C13A C14A 120.40(10) ?
C12A C13A H13A 119.8 ?
C14A C13A H13A 119.8 ?
C13A C14A C9A 120.41(10) ?
C13A C14A H14A 119.8 ?
C9A C14A H14A 119.8 ?
C1B N1B C5B 117.49(9) ?
C7B N2B C6B 121.86(9) ?
C7B N2B H2B 120.5(8) ?
C6B N2B H2B 117.6(8) ?
N1B C1B C2B 123.96(10) ?
N1B C1B H1B 118.0 ?
C2B C1B H1B 118.0 ?
C1B C2B C3B 118.13(10) ?
C1B C2B H2B1 120.9 ?
C3B C2B H2B1 120.9 ?
C2B C3B C4B 118.79(10) ?
C2B C3B H3B 120.6 ?
C4B C3B H3B 120.6 ?
C3B C4B C5B 119.19(10) ?
C3B C4B H4B 120.4 ?
C5B C4B H4B 120.4 ?
N1B C5B C4B 122.39(9) ?
N1B C5B C6B 114.37(9) ?
C4B C5B C6B 123.24(9) ?
N2B C6B C5B 114.24(9) ?
N2B C6B H6B1 108.7 ?
C5B C6B H6B1 108.7 ?
N2B C6B H6B2 108.7 ?
C5B C6B H6B2 108.7 ?
H6B1 C6B H6B2 107.6 ?
O1B C7B N2B 122.16(10) n
O1B C7B C8B 121.95(9) n
N2B C7B C8B 115.89(9) n
C9B C8B C7B 111.11(8) ?
C9B C8B H8B1 109.4 ?
C7B C8B H8B1 109.4 ?
C9B C8B H8B2 109.4 ?
C7B C8B H8B2 109.4 ?
H8B1 C8B H8B2 108.0 ?
C14B C9B C10B 118.67(10) ?
C14B C9B C8B 120.90(9) ?
C10B C9B C8B 120.40(9) ?
C11B C10B C9B 120.66(10) ?
C11B C10B H10B 119.7 ?
C9B C10B H10B 119.7 ?
C12B C11B C10B 120.44(10) ?
C12B C11B H11B 119.8 ?
C10B C11B H11B 119.8 ?
C11B C12B C13B 119.33(10) ?
C11B C12B H12B 120.3 ?
C13B C12B H12B 120.3 ?
C14B C13B C12B 120.20(10) ?
C14B C13B H13B 119.9 ?
C12B C13B H13B 119.9 ?
C13B C14B C9B 120.67(10) ?
C13B C14B H14B 119.7 ?
C9B C14B H14B 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C7A 1.2357(12) n
N1A C1A 1.3376(15) ?
N1A C5A 1.3424(13) ?
N2A C7A 1.3387(13) n
N2A C6A 1.4512(13) n
N2A H2A 0.893(13) ?
C1A C2A 1.3823(18) ?
C1A H1A 0.9500 ?
C2A C3A 1.3820(17) ?
C2A H2A1 0.9500 ?
C3A C4A 1.3852(15) ?
C3A H3A 0.9500 ?
C4A C5A 1.3864(15) ?
C4A H4A 0.9500 ?
C5A C6A 1.5150(14) ?
C6A H6A1 0.9900 ?
C6A H6A2 0.9900 ?
C7A C8A 1.5194(14) n
C8A C9A 1.5129(13) ?
C8A H8A1 0.9900 ?
C8A H8A2 0.9900 ?
C9A C14A 1.3899(15) ?
C9A C10A 1.3919(15) ?
C10A C11A 1.3873(15) ?
C10A H10A 0.9500 ?
C11A C12A 1.3871(17) ?
C11A H11A 0.9500 ?
C12A C13A 1.3825(17) ?
C12A H12A 0.9500 ?
C13A C14A 1.3878(15) ?
C13A H13A 0.9500 ?
C14A H14A 0.9500 ?
O1B C7B 1.2339(13) n
N1B C1B 1.3367(14) ?
N1B C5B 1.3424(13) ?
N2B C7B 1.3379(13) n
N2B C6B 1.4500(13) n
N2B H2B 0.888(14) ?
C1B C2B 1.3833(16) ?
C1B H1B 0.9500 ?
C2B C3B 1.3836(16) ?
C2B H2B1 0.9500 ?
C3B C4B 1.3858(15) ?
C3B H3B 0.9500 ?
C4B C5B 1.3886(15) ?
C4B H4B 0.9500 ?
C5B C6B 1.5162(14) ?
C6B H6B1 0.9900 ?
C6B H6B2 0.9900 ?
C7B C8B 1.5240(14) n
C8B C9B 1.5144(14) ?
C8B H8B1 0.9900 ?
C8B H8B2 0.9900 ?
C9B C14B 1.3915(15) ?
C9B C10B 1.3925(15) ?
C10B C11B 1.3862(16) ?
C10B H10B 0.9500 ?
C11B C12B 1.3855(16) ?
C11B H11B 0.9500 ?
C12B C13B 1.3894(16) ?
C12B H12B 0.9500 ?
C13B C14B 1.3894(15) ?
C13B H13B 0.9500 ?
C14B H14B 0.9500 ?
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
N2A H2A O1B . 0.893(13) 2.001(14) 2.8850(12) 170.0(11)
N2B H2B O1A 4_565 0.888(14) 1.964(14) 2.8483(12) 174.0(12)
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
C5A N1A C1A C2A -0.08(16) ?
N1A C1A C2A C3A -0.03(18) ?
C1A C2A C3A C4A 0.07(18) ?
C2A C3A C4A C5A 0.00(17) ?
C1A N1A C5A C4A 0.16(15) ?
C1A N1A C5A C6A -177.48(9) ?
C3A C4A C5A N1A -0.12(16) ?
C3A C4A C5A C6A 177.29(10) ?
C7A N2A C6A C5A -91.32(11) n
N1A C5A C6A N2A -163.48(8) n
C4A C5A C6A N2A 18.90(14) ?
C6A N2A C7A O1A 5.63(14) ?
C6A N2A C7A C8A -173.87(8) ?
O1A C7A C8A C9A -68.83(12) n
N2A C7A C8A C9A 110.68(10) n
C7A C8A C9A C14A -101.21(11) n
C7A C8A C9A C10A 77.39(12) ?
C14A C9A C10A C11A -0.13(15) ?
C8A C9A C10A C11A -178.74(9) ?
C9A C10A C11A C12A 0.20(16) ?
C10A C11A C12A C13A -0.09(16) ?
C11A C12A C13A C14A -0.09(17) ?
C12A C13A C14A C9A 0.16(17) ?
C10A C9A C14A C13A -0.05(15) ?
C8A C9A C14A C13A 178.58(10) ?
C5B N1B C1B C2B -0.66(16) ?
N1B C1B C2B C3B 1.68(17) ?
C1B C2B C3B C4B -1.01(15) ?
C2B C3B C4B C5B -0.53(15) ?
C1B N1B C5B C4B -1.02(14) ?
C1B N1B C5B C6B 178.57(9) ?
C3B C4B C5B N1B 1.62(15) ?
C3B C4B C5B C6B -177.94(9) ?
C7B N2B C6B C5B -83.22(12) n
N1B C5B C6B N2B -178.80(8) n
C4B C5B C6B N2B 0.79(14) ?
C6B N2B C7B O1B -1.69(15) ?
C6B N2B C7B C8B 177.80(9) ?
O1B C7B C8B C9B -67.02(13) n
N2B C7B C8B C9B 113.49(10) n
C7B C8B C9B C14B 77.53(12) n
C7B C8B C9B C10B -100.44(11) ?
C14B C9B C10B C11B -1.66(15) ?
C8B C9B C10B C11B 176.35(9) ?
C9B C10B C11B C12B 0.18(16) ?
C10B C11B C12B C13B 1.16(16) ?
C11B C12B C13B C14B -1.01(16) ?
C12B C13B C14B C9B -0.49(16) ?
C10B C9B C14B C13B 1.81(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 719434
