#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013227.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_2013227
loop_
_publ_author_name
'Andrau, Laura'
'White, Jonathan'
_publ_section_title
;
 Conformation of N-methyl-4-piperidyl 2,4-dinitrobenzoate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o60
_journal_page_last               o61
_journal_paper_doi               10.1107/S0108270102022254
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C13 H15 N3 O6'
_chemical_formula_sum            'C13 H15 N3 O6'
_chemical_formula_weight         309.28
_chemical_melting_point          .341E-305
_chemical_name_systematic
;
N-methyl-4-piperidyl 2,4-dinitrobenzoate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 94.096(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.040(3)
_cell_length_b                   13.303(5)
_cell_length_c                   17.699(7)
_cell_measurement_reflns_used    1163
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.31
_cell_volume                     1418.5(10)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Make Model CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.046
_diffrn_reflns_av_sigmaI/netI    0.066
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7269
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0423P)²+0.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.118
_reflns_number_gt                1840
_reflns_number_total             2486
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ta1405.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1418.4(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013227
_cod_database_fobs_code          2013227
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_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
_atom_site_type_symbol
C1 0.5166(4) 0.58042(16) 0.37429(14) 0.0246(6) Uani d . 1 . . C
C2 0.7151(4) 0.59858(18) 0.42946(16) 0.0288(6) Uani d . 1 . . C
C3 0.7719(4) 0.71038(18) 0.42932(16) 0.0281(6) Uani d . 1 . . C
C4 0.3909(4) 0.75462(18) 0.39534(15) 0.0266(6) Uani d . 1 . . C
C5 0.3232(4) 0.64419(18) 0.39445(15) 0.0257(6) Uani d . 1 . . C
C6 0.6440(5) 0.87898(19) 0.44762(17) 0.0328(6) Uani d . 1 . . C
C7 0.5287(4) 0.41043(17) 0.33026(13) 0.0259(6) Uani d . 1 . . C
C8 0.4029(4) 0.31227(17) 0.33187(13) 0.0241(5) Uani d . 1 . . C
C9 0.4847(4) 0.22388(17) 0.36624(13) 0.0238(5) Uani d . 1 . . C
C10 0.3691(4) 0.13469(18) 0.36076(13) 0.0251(6) Uani d . 1 . . C
C11 0.1634(4) 0.13496(16) 0.32174(12) 0.0234(5) Uani d . 1 . . C
C12 0.0744(4) 0.22087(18) 0.28761(13) 0.0267(6) Uani d . 1 . . C
C13 0.1948(4) 0.30890(18) 0.29322(14) 0.0274(6) Uani d . 1 . . C
N1 0.5832(3) 0.77231(14) 0.44892(11) 0.0253(5) Uani d . 1 . . N
N2 0.6986(3) 0.22487(16) 0.41149(11) 0.0290(5) Uani d . 1 . . N
N3 0.0317(3) 0.04132(15) 0.31820(11) 0.0291(5) Uani d . 1 . . N
O1 0.4419(2) 0.47566(11) 0.37704(9) 0.0272(4) Uani d . 1 . . O
O2 0.6703(3) 0.42739(12) 0.28798(9) 0.0351(5) Uani d . 1 . . O
O3 0.7879(3) 0.30659(13) 0.42425(10) 0.0367(5) Uani d . 1 . . O
O4 0.7777(3) 0.14396(13) 0.43376(9) 0.0366(5) Uani d . 1 . . O
O5 0.1025(3) -0.03040(12) 0.35554(10) 0.0362(5) Uani d . 1 . . O
O6 -0.1423(3) 0.04116(13) 0.27776(10) 0.0391(5) Uani d . 1 . . O
H1 0.558(4) 0.5948(17) 0.3217(13) 0.028(6) Uiso d . 1 . . H
H2A 0.842(4) 0.5577(17) 0.4169(12) 0.024(6) Uiso d . 1 . . H
H2B 0.682(4) 0.5762(19) 0.4790(16) 0.041(8) Uiso d . 1 . . H
H3A 0.889(4) 0.7261(16) 0.4664(13) 0.025(6) Uiso d . 1 . . H
H3B 0.818(4) 0.7298(19) 0.3766(16) 0.045(8) Uiso d . 1 . . H
H4A 0.420(4) 0.7760(18) 0.3414(16) 0.039(7) Uiso d . 1 . . H
H4B 0.269(4) 0.7947(17) 0.4102(13) 0.026(6) Uiso d . 1 . . H
H5A 0.286(3) 0.6235(15) 0.4466(12) 0.017(6) Uiso d . 1 . . H
H5B 0.196(4) 0.6338(16) 0.3589(13) 0.024(6) Uiso d . 1 . . H
H6A 0.678(4) 0.8990(18) 0.3949(15) 0.039(7) Uiso d . 1 . . H
H6B 0.771(4) 0.8896(18) 0.4832(14) 0.035(7) Uiso d . 1 . . H
H6C 0.516(4) 0.9206(19) 0.4643(14) 0.042(7) Uiso d . 1 . . H
H10 0.423(3) 0.0770(17) 0.3838(12) 0.019(6) Uiso d . 1 . . H
H12 -0.069(4) 0.2177(18) 0.2611(14) 0.038(7) Uiso d . 1 . . H
H13 0.135(4) 0.3702(17) 0.2696(12) 0.024(6) Uiso d . 1 . . H
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
_geom_angle_publ_flag
O1 C1 C5 106.35(18) y
O1 C1 C2 111.25(19) y
C5 C1 C2 110.5(2) y
O1 C1 H1 108.1(13) ?
C5 C1 H1 111.2(13) ?
C2 C1 H1 109.4(13) ?
C1 C2 C3 108.8(2) y
C1 C2 H2A 111.3(13) ?
C3 C2 H2A 111.1(13) ?
C1 C2 H2B 109.5(15) ?
C3 C2 H2B 111.3(15) ?
H2A C2 H2B 105(2) ?
N1 C3 C2 111.6(2) y
N1 C3 H3A 105.3(14) ?
C2 C3 H3A 111.6(13) ?
N1 C3 H3B 109.9(14) ?
C2 C3 H3B 108.8(14) ?
H3A C3 H3B 110(2) ?
N1 C4 C5 111.16(19) y
N1 C4 H4A 112.3(14) ?
C5 C4 H4A 108.8(14) ?
N1 C4 H4B 108.7(13) ?
C5 C4 H4B 109.1(14) ?
H4A C4 H4B 106.7(19) ?
C1 C5 C4 109.4(2) y
C1 C5 H5A 107.1(12) ?
C4 C5 H5A 109.4(12) ?
C1 C5 H5B 110.9(13) ?
C4 C5 H5B 110.1(13) ?
H5A C5 H5B 109.8(18) ?
N1 C6 H6A 109.8(14) ?
N1 C6 H6B 108.6(14) ?
H6A C6 H6B 111(2) ?
N1 C6 H6C 109.2(14) ?
H6A C6 H6C 110(2) ?
H6B C6 H6C 108(2) ?
O2 C7 O1 126.6(2) ?
O2 C7 C8 123.8(2) ?
O1 C7 C8 109.26(19) ?
C13 C8 C9 117.8(2) ?
C13 C8 C7 117.2(2) ?
C9 C8 C7 124.9(2) ?
C10 C9 C8 122.2(2) ?
C10 C9 N2 117.9(2) ?
C8 C9 N2 119.9(2) ?
C9 C10 C11 117.9(2) ?
C9 C10 H10 121.8(13) ?
C11 C10 H10 120.3(14) ?
C10 C11 C12 122.0(2) ?
C10 C11 N3 118.9(2) ?
C12 C11 N3 119.1(2) ?
C13 C12 C11 118.9(2) ?
C13 C12 H12 121.9(15) ?
C11 C12 H12 119.2(15) ?
C12 C13 C8 121.2(2) ?
C12 C13 H13 120.3(13) ?
C8 C13 H13 118.6(13) ?
C3 N1 C4 110.49(19) ?
C3 N1 C6 109.9(2) ?
C4 N1 C6 109.45(19) ?
O3 N2 O4 124.1(2) ?
O3 N2 C9 117.73(19) ?
O4 N2 C9 118.2(2) ?
O5 N3 O6 124.5(2) ?
O5 N3 C11 118.0(2) ?
O6 N3 C11 117.51(19) ?
C7 O1 C1 117.54(18) ?
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
C1 O1 . 1.467(3) y
C1 C5 . 1.507(3) y
C1 C2 . 1.511(3) y
C1 H1 . 1.00(2) ?
C2 C3 . 1.526(3) y
C2 H2A . 0.98(2) ?
C2 H2B . 0.96(3) ?
C3 N1 . 1.468(3) y
C3 H3A . 0.95(2) ?
C3 H3B . 1.03(3) ?
C4 N1 . 1.465(3) y
C4 C5 . 1.525(3) y
C4 H4A . 1.02(3) ?
C4 H4B . 0.96(2) ?
C5 H5A . 1.01(2) ?
C5 H5B . 0.96(2) ?
C6 N1 . 1.466(3) y
C6 H6A . 1.01(3) ?
C6 H6B . 0.97(3) ?
C6 H6C . 1.01(3) ?
C7 O2 . 1.197(3) ?
C7 O1 . 1.333(3) ?
C7 C8 . 1.512(3) ?
C8 C13 . 1.389(3) ?
C8 C9 . 1.398(3) ?
C9 C10 . 1.376(3) ?
C9 N2 . 1.471(3) ?
C10 C11 . 1.378(3) ?
C10 H10 . 0.92(2) ?
C11 C12 . 1.383(3) ?
C11 N3 . 1.477(3) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.96(2) ?
C13 H13 . 0.97(2) ?
N2 O3 . 1.227(2) ?
N2 O4 . 1.231(2) ?
N3 O5 . 1.221(2) ?
N3 O6 . 1.228(2) ?
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
O1 C1 C2 C3 -174.9(2) y
C5 C1 C2 C3 -57.0(3) y
C1 C2 C3 N1 57.7(3) y
O1 C1 C5 C4 178.15(19) y
C2 C1 C5 C4 57.3(3) y
N1 C4 C5 C1 -57.8(3) y
O2 C7 C8 C13 -98.2(3) y
O1 C7 C8 C13 75.8(3) y
O2 C7 C8 C9 78.7(3) y
O1 C7 C8 C9 -107.4(2) ?
C13 C8 C9 C10 2.1(3) ?
C7 C8 C9 C10 -174.8(2) ?
C13 C8 C9 N2 -176.5(2) ?
C7 C8 C9 N2 6.6(3) ?
C8 C9 C10 C11 -2.0(3) ?
N2 C9 C10 C11 176.65(19) ?
C9 C10 C11 C12 1.1(3) ?
C9 C10 C11 N3 -177.1(2) ?
C10 C11 C12 C13 -0.4(4) ?
N3 C11 C12 C13 177.8(2) ?
C11 C12 C13 C8 0.4(4) ?
C9 C8 C13 C12 -1.3(3) ?
C7 C8 C13 C12 175.8(2) ?
C2 C3 N1 C4 -58.7(3) ?
C2 C3 N1 C6 -179.6(2) ?
C5 C4 N1 C3 58.4(3) ?
C5 C4 N1 C6 179.5(2) ?
C10 C9 N2 O3 -171.0(2) ?
C8 C9 N2 O3 7.6(3) ?
C10 C9 N2 O4 9.4(3) ?
C8 C9 N2 O4 -171.9(2) ?
C10 C11 N3 O5 6.2(3) ?
C12 C11 N3 O5 -172.1(2) ?
C10 C11 N3 O6 -173.9(2) ?
C12 C11 N3 O6 7.8(3) ?
O2 C7 O1 C1 3.6(3) ?
C8 C7 O1 C1 -170.20(17) ?
C5 C1 O1 C7 149.1(2) ?
C2 C1 O1 C7 -90.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107463
