#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229919.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_2229919
loop_
_publ_author_name
'Luo, Xun'
'Huang, Yun-Chuang'
'Gao, Chao'
'Yu, Luo-Ting'
_publ_section_title
;
 (2-Chloro-3,5-dinitrophenyl)(piperidin-1-yl)methanone
;
_journal_coeditor_code           BT5492
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1066
_journal_paper_doi               10.1107/S1600536811011469
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H12 Cl N3 O5'
_chemical_formula_moiety         'C12 H12 Cl N3 O5'
_chemical_formula_sum            'C12 H12 Cl N3 O5'
_chemical_formula_weight         313.70
_chemical_name_systematic
;
(2-Chloro-3,5-dinitrophenyl)(piperidin-1-yl)methanone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   10.7864(3)
_cell_length_b                   11.1264(3)
_cell_length_c                   21.9775(5)
_cell_measurement_reflns_used    3316
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.0546
_cell_measurement_theta_min      3.2116
_cell_volume                     2637.60(12)
_computing_cell_refinement
;
CrysAlisPro
;
_computing_data_collection
;
CrysAlisPro (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlisPro  (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6722
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.97869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0331
_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)+(0.0283P)²+0.9862P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2240
_reflns_number_total             2696
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5492.cif
_cod_data_source_block           I
_cod_original_cell_volume        2637.60(11)
_cod_database_code               2229919
_cod_database_fobs_code          2229919
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 '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
Cl Cl1 0.14710(4) 0.51437(4) 0.126198(18) 0.02618(12) Uani d . 1 . .
O O1 0.28382(11) 0.39665(10) 0.03083(6) 0.0308(3) Uani d . 1 . .
O O2 0.37259(10) 0.52238(11) -0.03080(6) 0.0297(3) Uani d . 1 . .
O O3 0.06436(13) 0.74355(12) -0.14870(6) 0.0376(3) Uani d . 1 . .
O O4 -0.09872(13) 0.81129(12) -0.10265(6) 0.0409(4) Uani d . 1 . .
O O5 -0.18116(11) 0.60708(11) 0.10878(6) 0.0331(3) Uani d . 1 . .
N N1 0.28706(12) 0.49108(12) 0.00224(6) 0.0219(3) Uani d . 1 . .
N N2 -0.00012(14) 0.75653(13) -0.10356(7) 0.0269(3) Uani d . 1 . .
N N3 -0.05433(13) 0.73621(12) 0.15851(6) 0.0238(3) Uani d . 1 . .
C C1 0.10865(14) 0.58412(14) 0.05898(7) 0.0179(3) Uani d . 1 . .
C C2 0.17880(14) 0.57192(13) 0.00600(7) 0.0178(3) Uani d . 1 . .
C C3 0.14762(15) 0.63140(14) -0.04708(7) 0.0188(3) Uani d . 1 . .
H H3 0.1955(17) 0.6182(15) -0.0830(8) 0.028(5) Uiso d . 1 . .
C C4 0.04113(15) 0.69969(13) -0.04645(7) 0.0191(3) Uani d . 1 . .
C C5 -0.03125(16) 0.71333(14) 0.00470(7) 0.0204(4) Uani d . 1 . .
H H5 -0.1055(16) 0.7566(15) 0.0036(7) 0.018(4) Uiso d . 1 . .
C C6 0.00352(14) 0.65690(13) 0.05846(7) 0.0177(3) Uani d . 1 . .
C C7 -0.08451(15) 0.66492(14) 0.11200(7) 0.0207(3) Uani d . 1 . .
C C8 0.05941(16) 0.80784(16) 0.16249(9) 0.0274(4) Uani d . 1 . .
H H8A 0.1068(18) 0.7963(17) 0.1263(9) 0.034(5) Uiso d . 1 . .
H H8B 0.1111(17) 0.7754(16) 0.1984(9) 0.032(5) Uiso d . 1 . .
C C9 0.02738(18) 0.93938(16) 0.17196(8) 0.0274(4) Uani d . 1 . .
H H9A -0.0143(18) 0.9693(16) 0.1353(9) 0.031(5) Uiso d . 1 . .
H H9B 0.1038(18) 0.9841(16) 0.1769(8) 0.029(5) Uiso d . 1 . .
C C10 -0.05450(17) 0.95620(17) 0.22745(8) 0.0274(4) Uani d . 1 . .
H H10A -0.0069(16) 0.9325(15) 0.2639(8) 0.025(5) Uiso d . 1 . .
H H10B -0.0785(17) 1.0388(17) 0.2320(8) 0.033(5) Uiso d . 1 . .
C C11 -0.16990(17) 0.87786(17) 0.22253(9) 0.0306(4) Uani d . 1 . .
H H11A -0.2230(19) 0.9067(18) 0.1888(9) 0.040(6) Uiso d . 1 . .
H H11B -0.2193(18) 0.8836(16) 0.2593(10) 0.041(6) Uiso d . 1 . .
C C12 -0.13634(17) 0.74677(16) 0.21155(8) 0.0269(4) Uani d . 1 . .
H H12A -0.2103(16) 0.7001(15) 0.2041(8) 0.022(4) Uiso d . 1 . .
H H12B -0.0908(17) 0.7123(15) 0.2473(9) 0.028(5) Uiso d . 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'
Cl Cl 0.1484 0.1585 '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 N1 C2 . . 118.12(13) ?
O2 N1 O1 . . 124.73(14) ?
O2 N1 C2 . . 117.11(13) ?
O3 N2 O4 . . 124.53(15) ?
O3 N2 C4 . . 118.00(14) ?
O4 N2 C4 . . 117.45(15) ?
O5 C7 N3 . . 124.28(15) ?
O5 C7 C6 . . 117.18(14) ?
N3 C7 C6 . . 118.51(13) ?
N3 C8 H8A . . 109.0(11) ?
N3 C8 H8B . . 107.9(10) ?
N3 C8 C9 . . 109.99(15) ?
N3 C12 C11 . . 110.24(15) ?
N3 C12 H12A . . 108.7(10) ?
N3 C12 H12B . . 107.2(10) ?
C1 C2 N1 . . 122.34(14) ?
C1 C6 C7 . . 122.55(14) ?
C2 C1 Cl1 . . 122.84(12) ?
C2 C3 H3 . . 119.5(11) ?
C3 C2 N1 . . 115.90(14) ?
C3 C2 C1 . . 121.70(14) ?
C3 C4 N2 . . 118.68(14) ?
C4 C3 C2 . . 117.30(15) ?
C4 C3 H3 . . 122.9(11) ?
C4 C5 H5 . . 121.5(10) ?
C4 C5 C6 . . 119.43(15) ?
C5 C4 N2 . . 118.47(14) ?
C5 C4 C3 . . 122.80(15) ?
C5 C6 C1 . . 119.29(14) ?
C5 C6 C7 . . 117.69(14) ?
C6 C1 Cl1 . . 117.75(12) ?
C6 C1 C2 . . 119.41(14) ?
C6 C5 H5 . . 119.0(10) ?
C7 N3 C8 . . 124.97(14) ?
C7 N3 C12 . . 120.59(13) ?
C8 N3 C12 . . 114.43(13) ?
C8 C9 H9A . . 108.6(11) ?
C8 C9 H9B . . 108.5(10) ?
H8A C8 H8B . . 107.6(15) ?
C9 C8 H8A . . 111.5(12) ?
C9 C8 H8B . . 110.8(10) ?
C9 C10 H10A . . 108.5(10) ?
C9 C10 H10B . . 111.1(11) ?
C9 C10 C11 . . 110.37(15) ?
H9A C9 H9B . . 107.9(15) ?
C10 C9 C8 . . 111.20(15) ?
C10 C9 H9A . . 110.6(11) ?
C10 C9 H9B . . 110.0(11) ?
C10 C11 H11A . . 109.9(12) ?
C10 C11 H11B . . 110.6(11) ?
H10A C10 H10B . . 108.1(15) ?
C11 C10 H10A . . 109.2(10) ?
C11 C10 H10B . . 109.5(11) ?
C11 C12 H12A . . 110.2(10) ?
C11 C12 H12B . . 111.0(10) ?
H11A C11 H11B . . 106.6(16) ?
C12 C11 C10 . . 111.42(15) ?
C12 C11 H11A . . 109.2(12) ?
C12 C11 H11B . . 109.0(11) ?
H12A C12 H12B . . 109.3(14) ?
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
Cl1 C1 . 1.7196(16) ?
O1 N1 . 1.2247(17) ?
O2 N1 . 1.2246(17) ?
O3 N2 . 1.2200(19) ?
O4 N2 . 1.2260(19) ?
O5 C7 . 1.2273(19) ?
N1 C2 . 1.476(2) ?
N2 C4 . 1.474(2) ?
N3 C7 . 1.334(2) ?
N3 C8 . 1.466(2) ?
N3 C12 . 1.468(2) ?
C1 C2 . 1.395(2) ?
C1 C6 . 1.394(2) ?
C2 C3 . 1.383(2) ?
C3 H3 . 0.954(18) ?
C3 C4 . 1.377(2) ?
C4 C5 . 1.377(2) ?
C5 H5 . 0.935(17) ?
C5 C6 . 1.389(2) ?
C6 C7 . 1.515(2) ?
C8 H8A . 0.95(2) ?
C8 H8B . 1.032(19) ?
C8 C9 . 1.518(3) ?
C9 H9A . 0.98(2) ?
C9 H9B . 0.97(2) ?
C9 C10 . 1.517(2) ?
C10 H10A . 0.987(18) ?
C10 H10B . 0.960(19) ?
C10 C11 . 1.523(2) ?
C11 H11A . 0.99(2) ?
C11 H11B . 0.97(2) ?
C11 C12 . 1.522(3) ?
C12 H12A . 0.966(17) ?
C12 H12B . 1.004(19) ?
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
Cl1 C1 C2 N1 . . . . 4.4(2) ?
Cl1 C1 C2 C3 . . . . -178.34(12) ?
Cl1 C1 C6 C5 . . . . -179.12(12) ?
Cl1 C1 C6 C7 . . . . -7.17(19) ?
O1 N1 C2 C1 . . . . 34.7(2) ?
O1 N1 C2 C3 . . . . -142.65(15) ?
O2 N1 C2 C1 . . . . -147.16(15) ?
O2 N1 C2 C3 . . . . 35.45(19) ?
O3 N2 C4 C3 . . . . -2.2(2) ?
O3 N2 C4 C5 . . . . -179.72(14) ?
O4 N2 C4 C3 . . . . 176.04(14) ?
O4 N2 C4 C5 . . . . -1.4(2) ?
N1 C2 C3 C4 . . . . 174.76(13) ?
N2 C4 C5 C6 . . . . 177.67(14) ?
N3 C8 C9 C10 . . . . 55.5(2) ?
C1 C2 C3 C4 . . . . -2.6(2) ?
C1 C6 C7 O5 . . . . -100.86(19) ?
C1 C6 C7 N3 . . . . 81.0(2) ?
C2 C1 C6 C5 . . . . 1.7(2) ?
C2 C1 C6 C7 . . . . 173.67(14) ?
C2 C3 C4 N2 . . . . -175.24(14) ?
C2 C3 C4 C5 . . . . 2.1(2) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
C4 C5 C6 C1 . . . . -2.2(2) ?
C4 C5 C6 C7 . . . . -174.59(14) ?
C5 C6 C7 O5 . . . . 71.21(19) ?
C5 C6 C7 N3 . . . . -106.95(18) ?
C6 C1 C2 N1 . . . . -176.46(13) ?
C6 C1 C2 C3 . . . . 0.8(2) ?
C7 N3 C8 C9 . . . . 123.65(18) ?
C7 N3 C12 C11 . . . . -124.47(17) ?
C8 N3 C7 O5 . . . . -178.63(17) ?
C8 N3 C7 C6 . . . . -0.6(2) ?
C8 N3 C12 C11 . . . . 56.3(2) ?
C8 C9 C10 C11 . . . . -55.0(2) ?
C9 C10 C11 C12 . . . . 54.1(2) ?
C10 C11 C12 N3 . . . . -53.7(2) ?
C12 N3 C7 O5 . . . . 2.2(3) ?
C12 N3 C7 C6 . . . . -179.80(15) ?
C12 N3 C8 C9 . . . . -57.1(2) ?
