#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/39/2223939.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_2223939
loop_
_publ_author_name
'N'Gouan, A. J.'
'Mansilla-Koblavi, F.'
'Timotou, A.'
'Adjou, A.'
'Ebby, N.'
_publ_section_title
;
 5-Nitro-2-(piperidin-1-yl)benzaldehyde
;
_journal_coeditor_code           NG2664
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2880
_journal_paper_doi               10.1107/S1600536809043700
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H14 N2 O3'
_chemical_formula_moiety         'C12 H14 N2 O3'
_chemical_formula_sum            'C12 H14 N2 O3'
_chemical_formula_weight         234.25
_chemical_melting_point          388
_chemical_name_systematic
;
5-Nitro-2-(piperidin-1-yl)benzaldehyde
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                80.767(2)
_cell_angle_beta                 80.733(3)
_cell_angle_gamma                86.034(2)
_cell_formula_units_Z            2
_cell_length_a                   5.686(2)
_cell_length_b                   10.102(5)
_cell_length_c                   10.221(4)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    295
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     571.4(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  'nonius KappaCCCD area detector'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11460
_diffrn_reflns_theta_full        28.074
_diffrn_reflns_theta_max         30.188
_diffrn_reflns_theta_min         2.042
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000392
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick
 w=1/[σ²(F²) + ( 0.06P)² + 0.10P]
 ,where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1353
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2239
_reflns_number_total             3280
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            ng2664.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2223939
_cod_database_fobs_code          2223939
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.2540(2) -0.19297(12) 0.65442(13) 0.0538 Uani 1.0000 . .
N N2 0.1530(2) 0.26552(11) 0.75678(11) 0.0494 Uani 1.0000 . .
C C1 -0.1479(2) -0.07454(13) 0.68028(13) 0.0446 Uani 1.0000 . .
C C2 0.0235(2) -0.08957(12) 0.76296(12) 0.0437 Uani 1.0000 . .
C C3 0.1255(2) 0.02260(12) 0.78871(12) 0.0421 Uani 1.0000 . .
C C4 0.0534(2) 0.15293(12) 0.73040(12) 0.0428 Uani 1.0000 . .
C C5 -0.1174(3) 0.16295(13) 0.64329(14) 0.0514 Uani 1.0000 . .
C C6 -0.2181(3) 0.05102(14) 0.61906(14) 0.0516 Uani 1.0000 . .
C C7 0.3268(3) -0.00219(15) 0.86587(14) 0.0530 Uani 1.0000 . .
C C8 0.1313(3) 0.28678(15) 0.89744(13) 0.0539 Uani 1.0000 . .
C C9 0.3194(3) 0.37797(17) 0.91473(16) 0.0665 Uani 1.0000 . .
C C10 0.3053(4) 0.51042(17) 0.82255(17) 0.0676 Uani 1.0000 . .
C C11 0.3178(3) 0.48655(15) 0.67935(16) 0.0630 Uani 1.0000 . .
C C12 0.1293(3) 0.39255(14) 0.66607(15) 0.0573 Uani 1.0000 . .
O O1 -0.1742(2) -0.30357(10) 0.69841(14) 0.0772 Uani 1.0000 . .
O O2 -0.4183(2) -0.17831(12) 0.58925(14) 0.0796 Uani 1.0000 . .
O O3 0.3735(2) -0.10961(12) 0.92869(13) 0.0761 Uani 1.0000 . .
H H2 0.0775 -0.1770 0.8003 0.0524 Uiso 1.0000 . .
H H5 -0.1691 0.2482 0.6013 0.0617 Uiso 1.0000 . .
H H6 -0.3366 0.0604 0.5608 0.0619 Uiso 1.0000 . .
H H7 0.4264 0.0706 0.8620 0.0636 Uiso 1.0000 . .
H H81 0.1423 0.1992 0.9549 0.0647 Uiso 1.0000 . .
H H82 -0.0258 0.3295 0.9232 0.0647 Uiso 1.0000 . .
H H91 0.3019 0.3901 1.0089 0.0798 Uiso 1.0000 . .
H H92 0.4712 0.3336 0.8926 0.0798 Uiso 1.0000 . .
H H101 0.4289 0.5645 0.8298 0.0812 Uiso 1.0000 . .
H H102 0.1507 0.5572 0.8515 0.0812 Uiso 1.0000 . .
H H111 0.2952 0.5712 0.6206 0.0756 Uiso 1.0000 . .
H H112 0.4750 0.4465 0.6503 0.0756 Uiso 1.0000 . .
H H121 -0.0316 0.4328 0.6880 0.0688 Uiso 1.0000 . .
H H122 0.1462 0.3734 0.5738 0.0688 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C1 . . . 118.62(12) no
O1 N1 O2 . . . 122.42(13) no
C1 N1 O2 . . . 118.96(12) no
C4 C3 C2 . . . 120.29(12) no
C4 C3 C7 . . . 122.63(12) no
C2 C3 C7 . . . 116.75(12) no
C3 C4 N2 . . . 120.58(12) no
C3 C4 C5 . . . 117.61(12) no
N2 C4 C5 . . . 121.79(12) no
C4 N2 C8 . . . 118.01(11) no
C4 N2 C12 . . . 118.40(11) no
C8 N2 C12 . . . 111.78(11) no
C4 C5 C6 . . . 121.51(12) no
C4 C5 H51 . . . 120.3 no
C6 C5 H51 . . . 118.1 no
C3 C2 C1 . . . 119.98(12) no
C3 C2 H21 . . . 119.5 no
C1 C2 H21 . . . 120.4 no
C3 C7 O3 . . . 123.42(14) no
C3 C7 H71 . . . 117.1 no
O3 C7 H71 . . . 119.4 no
N1 C1 C2 . . . 119.43(12) no
N1 C1 C6 . . . 119.35(12) no
C2 C1 C6 . . . 121.20(12) no
C1 C6 C5 . . . 119.35(13) no
C1 C6 H61 . . . 120.6 no
C5 C6 H61 . . . 120.1 no
N2 C8 C9 . . . 110.88(12) no
N2 C8 H81 . . . 109.1 no
C9 C8 H81 . . . 111.4 no
N2 C8 H82 . . . 108.6 no
C9 C8 H82 . . . 108.4 no
H81 C8 H82 . . . 108.4 no
N2 C12 C11 . . . 109.92(13) no
N2 C12 H122 . . . 108.8 no
C11 C12 H122 . . . 110.7 no
N2 C12 H121 . . . 109.0 no
C11 C12 H121 . . . 110.9 no
H122 C12 H121 . . . 107.5 no
C8 C9 C10 . . . 110.77(14) no
C8 C9 H92 . . . 107.4 no
C10 C9 H92 . . . 109.5 no
C8 C9 H91 . . . 109.3 no
C10 C9 H91 . . . 112.0 no
H92 C9 H91 . . . 107.7 no
C12 C11 C10 . . . 111.64(13) no
C12 C11 H112 . . . 108.8 no
C10 C11 H112 . . . 108.6 no
C12 C11 H111 . . . 108.5 no
C10 C11 H111 . . . 110.5 no
H112 C11 H111 . . . 108.8 no
C9 C10 C11 . . . 110.19(14) no
C9 C10 H101 . . . 110.3 no
C11 C10 H101 . . . 110.4 no
C9 C10 H102 . . . 107.9 no
C11 C10 H102 . . . 109.6 no
H101 C10 H102 . . . 108.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O1 . . 1.2210(16) no
N1 C1 . . 1.4553(18) no
N1 O2 . . 1.2195(16) no
C3 C4 . . 1.4174(17) no
C3 C2 . . 1.3878(19) no
C3 C7 . . 1.4773(19) no
C4 N2 . . 1.3868(17) no
C4 C5 . . 1.4081(19) no
N2 C8 . . 1.4720(18) no
N2 C12 . . 1.4694(17) no
C5 C6 . . 1.376(2) no
C5 H51 . . 0.949 no
C2 C1 . . 1.3750(19) no
C2 H21 . . 0.955 no
C7 O3 . . 1.2049(18) no
C7 H71 . . 0.951 no
C1 C6 . . 1.3839(19) no
C6 H61 . . 0.959 no
C8 C9 . . 1.507(2) no
C8 H81 . . 0.984 no
C8 H82 . . 0.980 no
C12 C11 . . 1.516(2) no
C12 H122 . . 0.981 no
C12 H121 . . 0.982 no
C9 C10 . . 1.513(2) no
C9 H92 . . 0.956 no
C9 H91 . . 0.978 no
C11 C10 . . 1.511(2) no
C11 H112 . . 0.977 no
C11 H111 . . 0.977 no
C10 H101 . . 0.939 no
C10 H102 . . 0.993 no
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
C12 N2 C8 C9 -58.84(17) yes
C8 N2 C12 C11 58.21(16) yes
N2 C8 C9 C10 56.24(17) yes
C8 C9 C10 C11 -54.06(18) yes
C9 C10 C11 C12 54.45(18) yes
C10 C11 C12 N2 -56.22(17) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2018727
