#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:33:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236513 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554058.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_1554058
loop_
_publ_author_name
'Jeeva, Mani'
'Prabhu, G. Venkatesa'
'Boobalan, Maria susai'
'Rajesh, Chinnaiyan Mahalingam'
_publ_section_title
;
 Interactions and Inhibition Effect of Urea-Derived Mannich Bases on a
 Mild Steel Surface in HCl
;
_journal_issue                   38
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              22025
_journal_paper_doi               10.1021/acs.jpcc.5b05788
_journal_volume                  119
_journal_year                    2015
_chemical_formula_moiety         'C12 H18 N4 O'
_chemical_formula_sum            'C12 H18 N4 O'
_chemical_formula_weight         234.30
_chemical_melting_point          432.3(2)
_chemical_name_systematic        1-(piperidin-1-yl(pyridin-4-yl)methyl)urea
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      43
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   12.6630(17)
_cell_length_b                   33.528(4)
_cell_length_c                   12.2027(12)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.94
_cell_volume                     5180.8(11)
_computing_cell_refinement       'Agilent CrysAlisPro'
_computing_data_collection       'Agilent CrysAlisPro'
_computing_data_reduction        'Agilent CrysAlisPro'
_computing_molecular_graphics    Wingx
_computing_publication_material  Wingx
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.2760
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3393
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0533
_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)+(0.0787P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1540
_reflns_number_total             2014
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jp5b05788_si_004.cif
_cod_data_source_block           mdj
_cod_database_code               1554058
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.08366(16) 0.39974(7) 0.99281(19) 0.0559(6) Uani 1 1 d .
N3 N 0.1725(2) 0.40254(7) 0.8314(2) 0.0496(7) Uani 1 1 d .
C12 C 0.1577(2) 0.38814(8) 0.9345(2) 0.0436(7) Uani 1 1 d .
N1 N -0.0093(2) 0.40861(9) 0.4591(2) 0.0601(8) Uani 1 1 d .
N2 N 0.1589(2) 0.47338(8) 0.7806(2) 0.0488(7) Uani 1 1 d .
C11 C 0.1087(2) 0.43381(8) 0.7845(3) 0.0430(7) Uani 1 1 d .
H4 H 0.0462 0.4364 0.8313 0.052 Uiso 1 1 calc R
C10 C 0.1709(3) 0.49084(11) 0.8899(3) 0.0659(10) Uani 1 1 d .
H5A H 0.2213 0.4753 0.9319 0.079 Uiso 1 1 calc R
H5B H 0.1037 0.4902 0.9279 0.079 Uiso 1 1 calc R
C4 C -0.0477(3) 0.43769(11) 0.5215(3) 0.0597(9) Uani 1 1 d .
H6 H -0.1027 0.4530 0.4936 0.072 Uiso 1 1 calc R
C2 C 0.1067(3) 0.39280(10) 0.6066(3) 0.0586(9) Uani 1 1 d .
H7 H 0.1594 0.3761 0.6334 0.070 Uiso 1 1 calc R
C3 C 0.0666(3) 0.38666(10) 0.5035(3) 0.0644(10) Uani 1 1 d .
H8 H 0.0943 0.3658 0.4622 0.077 Uiso 1 1 calc R
N4 N 0.2265(2) 0.36017(9) 0.9664(3) 0.0621(8) Uani 1 1 d .
H2A H 0.2204 0.3494 1.0300 0.075 Uiso 1 1 calc R
H2B H 0.2768 0.3530 0.9234 0.075 Uiso 1 1 calc R
C5 C -0.0107(2) 0.44647(9) 0.6252(3) 0.0493(8) Uani 1 1 d .
H9 H -0.0392 0.4677 0.6644 0.059 Uiso 1 1 calc R
C1 C 0.0692(2) 0.42344(8) 0.6706(3) 0.0403(6) Uani 1 1 d .
C6 C 0.2592(3) 0.47319(12) 0.7214(4) 0.0689(11) Uani 1 1 d .
H11A H 0.2492 0.4613 0.6497 0.083 Uiso 1 1 calc R
H11B H 0.3102 0.4571 0.7611 0.083 Uiso 1 1 calc R
C7 C 0.3017(4) 0.51558(14) 0.7084(4) 0.0887(15) Uani 1 1 d .
H12A H 0.3699 0.5147 0.6723 0.106 Uiso 1 1 calc R
H12B H 0.2540 0.5309 0.6626 0.106 Uiso 1 1 calc R
C9 C 0.2090(4) 0.53358(12) 0.8809(4) 0.0933(14) Uani 1 1 d .
H13A H 0.2187 0.5446 0.9538 0.112 Uiso 1 1 calc R
H13B H 0.1561 0.5495 0.8435 0.112 Uiso 1 1 calc R
C8 C 0.3130(4) 0.53581(15) 0.8181(5) 0.1030(18) Uani 1 1 d .
H55A H 0.3327 0.5635 0.8074 0.124 Uiso 1 1 calc R
H55B H 0.3684 0.5229 0.8600 0.124 Uiso 1 1 calc R
H50 H 0.225(2) 0.3928(10) 0.789(3) 0.056(10) Uiso 1 1 d .
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
C12 N3 C11 123.2(3)
C12 N3 H50 120(2)
C11 N3 H50 117(2)
O1 C12 N4 123.0(3)
O1 C12 N3 121.5(3)
N4 C12 N3 115.4(3)
C3 N1 C4 116.0(3)
C6 N2 C10 111.2(3)
C6 N2 C11 112.8(3)
C10 N2 C11 112.1(3)
N3 C11 N2 115.2(2)
N3 C11 C1 112.4(2)
N2 C11 C1 108.6(2)
N3 C11 H4 106.7
N2 C11 H4 106.7
C1 C11 H4 106.7
N2 C10 C9 110.2(3)
N2 C10 H5A 109.6
C9 C10 H5A 109.6
N2 C10 H5B 109.6
C9 C10 H5B 109.6
H5A C10 H5B 108.1
N1 C4 C5 123.9(3)
N1 C4 H6 118.1
C5 C4 H6 118.1
C3 C2 C1 120.4(3)
C3 C2 H7 119.8
C1 C2 H7 119.8
N1 C3 C2 124.0(3)
N1 C3 H8 118.0
C2 C3 H8 118.0
C12 N4 H2A 120.0
C12 N4 H2B 120.0
H2A N4 H2B 120.0
C4 C5 C1 119.6(3)
C4 C5 H9 120.2
C1 C5 H9 120.2
C2 C1 C5 116.1(3)
C2 C1 C11 125.3(3)
C5 C1 C11 118.6(3)
N2 C6 C7 110.7(4)
N2 C6 H11A 109.5
C7 C6 H11A 109.5
N2 C6 H11B 109.5
C7 C6 H11B 109.5
H11A C6 H11B 108.1
C8 C7 C6 111.1(4)
C8 C7 H12A 109.4
C6 C7 H12A 109.4
C8 C7 H12B 109.4
C6 C7 H12B 109.4
H12A C7 H12B 108.0
C10 C9 C8 110.9(4)
C10 C9 H13A 109.5
C8 C9 H13A 109.5
C10 C9 H13B 109.5
C8 C9 H13B 109.5
H13A C9 H13B 108.0
C7 C8 C9 110.0(4)
C7 C8 H55A 109.7
C9 C8 H55A 109.7
C7 C8 H55B 109.7
C9 C8 H55B 109.7
H55A C8 H55B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.240(4)
N3 C12 1.361(4)
N3 C11 1.442(4)
N3 H50 0.90(4)
C12 N4 1.338(4)
N1 C3 1.326(4)
N1 C4 1.329(5)
N2 C6 1.461(4)
N2 C10 1.464(4)
N2 C11 1.472(4)
C11 C1 1.518(4)
C11 H4 0.9800
C10 C9 1.516(5)
C10 H5A 0.9700
C10 H5B 0.9700
C4 C5 1.381(5)
C4 H6 0.9300
C2 C3 1.373(5)
C2 C1 1.374(4)
C2 H7 0.9300
C3 H8 0.9300
N4 H2A 0.8600
N4 H2B 0.8600
C5 C1 1.389(4)
C5 H9 0.9300
C6 C7 1.528(5)
C6 H11A 0.9700
C6 H11B 0.9700
C7 C8 1.507(6)
C7 H12A 0.9700
C7 H12B 0.9700
C9 C8 1.526(7)
C9 H13A 0.9700
C9 H13B 0.9700
C8 H55A 0.9700
C8 H55B 0.9700
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
C11 N3 C12 O1 4.1(5)
C11 N3 C12 N4 -177.6(3)
C12 N3 C11 N2 103.4(3)
C12 N3 C11 C1 -131.4(3)
C6 N2 C11 N3 56.6(4)
C10 N2 C11 N3 -69.9(3)
C6 N2 C11 C1 -70.6(3)
C10 N2 C11 C1 163.0(3)
C6 N2 C10 C9 60.3(4)
C11 N2 C10 C9 -172.4(3)
C3 N1 C4 C5 2.1(5)
C4 N1 C3 C2 -0.9(5)
C1 C2 C3 N1 -0.7(6)
N1 C4 C5 C1 -1.8(6)
C3 C2 C1 C5 1.0(5)
C3 C2 C1 C11 -178.5(3)
C4 C5 C1 C2 0.2(5)
C4 C5 C1 C11 179.8(3)
N3 C11 C1 C2 -14.2(4)
N2 C11 C1 C2 114.6(3)
N3 C11 C1 C5 166.3(3)
N2 C11 C1 C5 -65.0(3)
C10 N2 C6 C7 -59.6(4)
C11 N2 C6 C7 173.5(3)
N2 C6 C7 C8 56.2(5)
N2 C10 C9 C8 -57.4(5)
C6 C7 C8 C9 -53.2(5)
C10 C9 C8 C7 54.2(5)
