#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227842.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_2227842
loop_
_publ_author_name
'Shi, Yao-Cheng'
'Zhu, Bei-Bei'
'Zhang, Su-Hua'
_publ_section_title
;
 (Z)-1-Phenyl-3-(3-pyridylmethylamino)but-2-en-1-one
;
_journal_coeditor_code           NG5038
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2854
_journal_paper_doi               10.1107/S1600536810041127
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H16 N2 O'
_chemical_formula_moiety         'C16 H16 N2 O'
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_formula_weight         252.31
_chemical_name_systematic
;
(Z)-1-Phenyl-3-(3-pyridylmethylamino)but-2-en-1-one
;
_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                 99.111(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.256(2)
_cell_length_b                   10.5851(13)
_cell_length_c                   12.7122(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      15
_cell_measurement_theta_min      9
_cell_volume                     1362.6(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    'PLATON (Spek, 2009)'
_computing_publication_material  'WinGx (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2821
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.145
_refine_ls_extinction_coef       0.109(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0503
_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)+(0.0680P)²+0.2036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                1833
_reflns_number_total             2668
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ng5038.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227842
_cod_database_fobs_code          2227842
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_disorder_assembly
_atom_site_disorder_group
O O1 0.73670(14) 0.56511(13) 0.69319(11) 0.0534(4) Uani d . 1 . .
N N1 0.59836(16) 0.37872(14) 0.58418(13) 0.0458(4) Uani d . 1 . .
H H1N 0.6149 0.4207 0.6427 0.055 Uiso calc R 1 . .
N N2 0.5078(2) -0.05640(17) 0.67650(16) 0.0637(5) Uani d . 1 . .
C C3 1.0847(2) 0.8702(2) 0.6330(2) 0.0707(7) Uani d . 1 . .
H H3 1.1485 0.9334 0.6384 0.085 Uiso calc R 1 . .
C C2 1.0519(2) 0.8161(2) 0.7229(2) 0.0695(7) Uani d . 1 . .
H H2 1.0933 0.8426 0.7897 0.083 Uiso calc R 1 . .
C C1 0.9572(2) 0.7219(2) 0.71505(18) 0.0578(6) Uani d . 1 . .
H H1 0.9345 0.6868 0.7767 0.069 Uiso calc R 1 . .
C C6 0.89565(18) 0.67926(17) 0.61661(15) 0.0438(5) Uani d . 1 . .
C C5 0.9296(2) 0.7356(2) 0.52626(18) 0.0589(6) Uani d . 1 . .
H H5 0.8889 0.7090 0.4593 0.071 Uiso calc R 1 . .
C C4 1.0232(3) 0.8308(2) 0.5344(2) 0.0722(7) Uani d . 1 . .
H H4 1.0445 0.8682 0.4732 0.087 Uiso calc R 1 . .
C C7 0.79188(18) 0.57881(16) 0.61283(15) 0.0418(5) Uani d . 1 . .
C C8 0.7605(2) 0.50372(17) 0.52032(15) 0.0460(5) Uani d . 1 . .
H H8 0.8073 0.5183 0.4646 0.055 Uiso calc R 1 . .
C C9 0.6656(2) 0.41061(16) 0.50683(15) 0.0438(5) Uani d . 1 . .
C C10 0.6336(2) 0.3439(2) 0.40183(17) 0.0612(6) Uani d . 1 . .
H H10A 0.6344 0.2543 0.4134 0.092 Uiso calc R 1 . .
H H10B 0.6982 0.3654 0.3578 0.092 Uiso calc R 1 . .
H H10C 0.5476 0.3693 0.3670 0.092 Uiso calc R 1 . .
C C11 0.49955(19) 0.27955(18) 0.57884(17) 0.0493(5) Uani d . 1 . .
H H11A 0.4534 0.2741 0.5062 0.059 Uiso calc R 1 . .
H H11B 0.4354 0.3033 0.6238 0.059 Uiso calc R 1 . .
C C12 0.55373(18) 0.14986(16) 0.61276(14) 0.0400(5) Uani d . 1 . .
C C13 0.6826(2) 0.11570(19) 0.61395(18) 0.0547(6) Uani d . 1 . .
H H13 0.7427 0.1733 0.5941 0.066 Uiso calc R 1 . .
C C14 0.7228(2) -0.0054(2) 0.64491(18) 0.0612(6) Uani d . 1 . .
H H14 0.8097 -0.0308 0.6454 0.073 Uiso calc R 1 . .
C C15 0.6321(3) -0.0869(2) 0.67473(18) 0.0606(6) Uani d . 1 . .
H H15 0.6595 -0.1683 0.6949 0.073 Uiso calc R 1 . .
C C16 0.4712(2) 0.06032(19) 0.64491(16) 0.0509(5) Uani d . 1 . .
H H16 0.3834 0.0827 0.6446 0.061 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 H1N . . 117.0 ?
C11 N1 H1N . . 117.0 ?
C15 N2 C16 . . 116.63(18) ?
C2 C3 C4 . . 119.8(2) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C2 C1 . . 120.3(2) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C1 C6 . . 120.9(2) ?
C2 C1 H1 . . 119.5 ?
C6 C1 H1 . . 119.5 ?
C1 C6 C5 . . 118.07(19) ?
C1 C6 C7 . . 118.65(18) ?
C5 C6 C7 . . 123.23(18) ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C3 C4 C5 . . 120.1(2) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
O1 C7 C6 . . 117.78(17) ?
O1 C7 C8 . . 122.73(18) ?
C6 C7 C8 . . 119.49(17) ?
C7 C8 C9 . . 124.71(18) ?
C9 C8 H8 . . 117.6 ?
C7 C8 H8 . . 117.6 ?
N1 C9 C8 . . 121.90(17) ?
N1 C9 C10 . . 118.18(18) ?
C8 C9 C10 . . 119.91(18) ?
C9 N1 C11 . . 126.01(17) ?
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 ?
N1 C11 C12 . . 114.76(16) ?
N1 C11 H11A . . 108.6 ?
C12 C11 H11A . . 108.6 ?
N1 C11 H11B . . 108.6 ?
C12 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
C13 C12 C16 . . 116.98(18) ?
C13 C12 C11 . . 123.50(17) ?
C16 C12 C11 . . 119.53(17) ?
C12 C13 C14 . . 119.4(2) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C15 C14 C13 . . 118.6(2) ?
C15 C14 H14 . . 120.7 ?
C13 C14 H14 . . 120.7 ?
N2 C15 C14 . . 123.6(2) ?
N2 C15 H15 . . 118.2 ?
C14 C15 H15 . . 118.2 ?
N2 C16 C12 . . 124.7(2) ?
N2 C16 H16 . . 117.6 ?
C12 C16 H16 . . 117.6 ?
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
O1 C7 . 1.252(2) ?
N1 C9 . 1.331(2) ?
N1 C11 . 1.453(2) ?
N1 H1N . 0.8600 ?
N2 C15 . 1.319(3) ?
N2 C16 . 1.335(3) ?
C3 C2 . 1.368(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C2 C1 . 1.384(3) ?
C2 H2 . 0.9300 ?
C1 C6 . 1.385(3) ?
C1 H1 . 0.9300 ?
C6 C5 . 1.386(3) ?
C6 C7 . 1.500(3) ?
C5 C4 . 1.385(3) ?
C5 H5 . 0.9300 ?
C4 H4 . 0.9300 ?
C7 C8 . 1.414(3) ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.500(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.518(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.368(3) ?
C12 C16 . 1.375(3) ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.365(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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 H1N O1 . 0.86 2.01 2.684(2) 134 y
C14 H14 Cg2 1_545 0.93 2.80 3.632(2) 149 y
C16 H16 O1 2_646 0.93 2.57 3.190(3) 124 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4595679
