#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017878.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_2017878
loop_
_publ_author_name
'Cuenú, Fernando'
'Abonía, Rodrigo'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 1-(2-Aminophenyl)-3-(4-pyridyl)prop-2-en-1-one: a three-dimensional
 framework structure built from N---H···N,
 C---H···O and
 C---H···π(arene) hydrogen bonds
;
_journal_coeditor_code           EG3062
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o589
_journal_page_last               o592
_journal_paper_doi               10.1107/S0108270110040825
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C14 H12 N2 O1'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_chemical_name_systematic
;
1-(2-Aminophenyl)-3-(4-pyridyl)prop-2-en-1-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 118.849(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.922(6)
_cell_length_b                   6.4261(8)
_cell_length_c                   14.668(3)
_cell_measurement_reflns_used    2653
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.17
_cell_volume                     2305.2(8)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17566
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Version 2.10, Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0458P)²+1.0151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1403
_reflns_number_total             2141
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3062.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C14 H12 N2 O1'
_cod_database_code               2017878
_cod_database_fobs_code          2017878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.54321(7) 0.5981(3) 0.44396(15) 0.0621(5) Uani d . 1 . .
O O1 0.56037(5) 0.7445(2) 0.50476(12) 0.0842(5) Uani d . 1 . .
C C2 0.48413(7) 0.5926(3) 0.37024(14) 0.0649(5) Uani d . 1 . .
H H2 0.4698 0.4822 0.3237 0.078 Uiso calc R 1 . .
C C3 0.45158(7) 0.7384(3) 0.36882(14) 0.0626(5) Uani d . 1 . .
H H3 0.4680 0.8470 0.4157 0.075 Uiso calc R 1 . .
C C11 0.57932(7) 0.4371(3) 0.44259(14) 0.0608(5) Uani d . 1 . .
C C12 0.63656(7) 0.4588(3) 0.50055(15) 0.0667(5) Uani d . 1 . .
C C13 0.66903(9) 0.2986(4) 0.49596(18) 0.0840(7) Uani d . 1 . .
H H13 0.7069 0.3115 0.5333 0.101 Uiso calc R 1 . .
C C14 0.64724(12) 0.1269(5) 0.4393(2) 0.0985(8) Uani d . 1 . .
H H14 0.6701 0.0231 0.4379 0.118 Uiso calc R 1 . .
C C15 0.59151(12) 0.1022(4) 0.3834(2) 0.0953(7) Uani d . 1 . .
H H15 0.5766 -0.0175 0.3442 0.114 Uiso calc R 1 . .
C C16 0.55856(9) 0.2545(3) 0.38591(16) 0.0745(6) Uani d . 1 . .
H H16 0.5209 0.2365 0.3486 0.089 Uiso calc R 1 . .
N N12 0.66033(6) 0.6265(3) 0.55805(15) 0.0893(6) Uani d . 1 . .
H H12A 0.6387 0.7218 0.5616 0.107 Uiso d R 1 . .
H H12B 0.6961 0.6417 0.5923 0.107 Uiso d R 1 . .
C C31 0.39277(7) 0.7529(3) 0.30313(13) 0.0601(5) Uani d . 1 . .
C C32 0.36174(7) 0.6042(4) 0.23288(16) 0.0791(6) Uani d . 1 . .
H H32 0.3779 0.4843 0.2247 0.095 Uiso calc R 1 . .
C C33 0.30680(9) 0.6335(4) 0.17490(19) 0.0964(8) Uani d . 1 . .
H H33 0.2866 0.5308 0.1271 0.116 Uiso calc R 1 . .
N N34 0.28030(7) 0.7964(4) 0.18169(15) 0.0911(6) Uani d . 1 . .
C C35 0.31025(8) 0.9374(4) 0.24939(18) 0.0933(8) Uani d . 1 . .
H H35 0.2928 1.0543 0.2568 0.112 Uiso calc R 1 . .
C C36 0.36590(7) 0.9231(4) 0.31018(16) 0.0819(7) Uani d . 1 . .
H H36 0.3852 1.0299 0.3562 0.098 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
O1 C1 C11 . . 121.84(16) ?
O1 C1 C2 . . 117.37(17) ?
C11 C1 C2 . . 120.78(18) ?
C3 C2 C1 . . 121.42(18) ?
C3 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
C2 C3 C31 . . 128.00(18) ?
C2 C3 H3 . . 116.0 ?
C31 C3 H3 . . 116.0 ?
C16 C11 C12 . . 117.90(19) ?
C16 C11 C1 . . 121.14(17) ?
C12 C11 C1 . . 120.95(18) ?
N12 C12 C13 . . 119.41(19) ?
N12 C12 C11 . . 122.41(18) ?
C13 C12 C11 . . 118.2(2) ?
C14 C13 C12 . . 121.8(2) ?
C14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
C13 C14 C15 . . 120.7(2) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C16 C15 C14 . . 119.2(2) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C11 . . 122.1(2) ?
C15 C16 H16 . . 118.9 ?
C11 C16 H16 . . 118.9 ?
C12 N12 H12A . . 117.0 ?
C12 N12 H12B . . 122.2 ?
H12A N12 H12B . . 120.8 ?
C36 C31 C32 . . 116.65(17) ?
C36 C31 C3 . . 119.38(18) ?
C32 C31 C3 . . 123.97(18) ?
C33 C32 C31 . . 119.2(2) ?
C33 C32 H32 . . 120.4 ?
C31 C32 H32 . . 120.4 ?
N34 C33 C32 . . 124.7(2) ?
N34 C33 H33 . . 117.6 ?
C32 C33 H33 . . 117.6 ?
C35 N34 C33 . . 115.67(18) ?
N34 C35 C36 . . 123.9(2) ?
N34 C35 H35 . . 118.1 ?
C36 C35 H35 . . 118.1 ?
C31 C36 C35 . . 119.9(2) ?
C31 C36 H36 . . 120.1 ?
C35 C36 H36 . . 120.1 ?
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
C11 C12 . 1.409(3) y
C12 C13 . 1.395(3) y
C13 C14 . 1.338(3) y
C14 C15 . 1.374(3) y
C15 C16 . 1.356(3) y
C16 C11 . 1.392(3) y
C12 N12 . 1.331(3) y
C1 C11 . 1.452(3) y
C1 O1 . 1.224(2) y
C1 C2 . 1.473(2) y
C2 C3 . 1.299(2) y
C2 H2 . 0.9300 ?
C3 C31 . 1.451(2) y
C3 H3 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
N12 H12A . 0.8799 ?
N12 H12B . 0.8801 ?
C31 C36 . 1.358(3) ?
C31 C32 . 1.365(3) ?
C32 C33 . 1.361(3) ?
C32 H32 . 0.9300 ?
C33 N34 . 1.313(3) ?
C33 H33 . 0.9300 ?
N34 C35 . 1.306(3) ?
C35 C36 . 1.371(3) ?
C35 H35 . 0.9300 ?
C36 H36 . 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
N12 H12A O1 . 0.88 1.93 2.621(3) 134 y
N12 H12B N34 8_566 0.88 2.10 2.982(3) 174 y
C36 H36 O1 5_676 0.93 2.36 3.283(3) 170 y
C32 H32 Cg1 2_655 0.93 2.87 3.611(3) 137 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 C11 C1 C2 . . . . 169.49(17) y
C11 C1 C2 C3 . . . . -178.21(18) y
O1 C1 C2 C3 . . . . 0.8(3) ?
C1 C2 C3 C31 . . . . -178.49(18) y
O1 C1 C11 C16 . . . . 169.07(18) ?
C2 C1 C11 C16 . . . . -11.9(3) ?
O1 C1 C11 C12 . . . . -9.5(3) ?
C16 C11 C12 N12 . . . . -179.29(19) ?
C1 C11 C12 N12 . . . . -0.7(3) ?
C16 C11 C12 C13 . . . . 1.4(3) ?
C1 C11 C12 C13 . . . . -179.99(18) ?
N12 C12 C13 C14 . . . . -180.0(2) ?
C11 C12 C13 C14 . . . . -0.6(3) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C13 C14 C15 C16 . . . . 0.1(4) ?
C14 C15 C16 C11 . . . . 0.8(3) ?
C12 C11 C16 C15 . . . . -1.5(3) ?
C1 C11 C16 C15 . . . . 179.88(19) ?
C2 C3 C31 C36 . . . . -177.3(2) ?
C2 C3 C31 C32 . . . . 2.6(3) y
C36 C31 C32 C33 . . . . 0.0(3) ?
C3 C31 C32 C33 . . . . -179.9(2) ?
C31 C32 C33 N34 . . . . -0.7(4) ?
C32 C33 N34 C35 . . . . 0.3(4) ?
C33 N34 C35 C36 . . . . 0.6(4) ?
C32 C31 C36 C35 . . . . 0.9(3) ?
C3 C31 C36 C35 . . . . -179.2(2) ?
N34 C35 C36 C31 . . . . -1.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654268
