#------------------------------------------------------------------------------
#$Date: 2019-11-04 10:36:43 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/39/4033928.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_4033928
loop_
_publ_author_name
'Ebule, Rene'
'Mudshinge, Sagar'
'Nantz, Michael H.'
'Mashuta, Mark S.'
'Hammond, Gerald B.'
'Xu, Bo'
_publ_section_title
;
 A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of
 4-Chloropiperidines from Homoallylic Amines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3249
_journal_page_last               3259
_journal_paper_doi               10.1021/acs.joc.8b03162
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C11 H13 Cl N2 O2'
_chemical_formula_sum            'C11 H13 Cl N2 O2'
_chemical_formula_weight         240.68
_chemical_name_common
; 
 1-(4-nitrophenyl)-4-chloro-piperidine
;
_chemical_name_systematic
; 
 1-(4-nitrophenyl)-4-chloro-piperidine
;
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.33.66 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2486(2)
_cell_length_b                   10.17867(17)
_cell_length_c                   6.17147(11)
_cell_measurement_reflns_used    12554
_cell_measurement_temperature    101.95(10)
_cell_measurement_theta_max      33.7450
_cell_measurement_theta_min      3.8430
_cell_volume                     1083.51(3)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      101.95(10)
_diffrn_detector_area_resol_mean 10.2836
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759  -57.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -55.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759  -57.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   95.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   57.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446  -77.0000  150.0000 111

#__ type_ start__ end____ width___ exp.time_
  5 omega   65.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   57.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   -5.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   57.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega  -52.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759   57.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega  -52.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759   57.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
  9 omega  -10.00  102.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 10 omega  -55.00   14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446  -77.0000  -90.0000 69

;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26127
_diffrn_reflns_theta_full        33.12
_diffrn_reflns_theta_max         33.12
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0320
_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)+(0.0214P)²+0.5871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                1941
_reflns_number_total             2160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b03162_si_002.cif
_cod_data_source_block           2n
_cod_original_sg_symbol_Hall     '-P 2ac 2n  '
_cod_database_code               4033928
_exptl_absorpt_correction_details
;
(CrysAlisPro SCALE3 ABSPACK, Oxford Diffraction Ltd., 2010) 
;
_shelx_res_file_2n
;
TITL gbh49ltb in Pnma
CELL 0.71073  17.248603  10.178669   6.171469  90.0000  90.0000  90.0000
ZERR    4.00   0.000240   0.000173   0.000109   0.0000   0.0000   0.0000
LATT 1
SYMM -x+1/2,-y, z+1/2
SYMM -x, y+1/2,-z
SYMM  x+1/2,-y+1/2,-z+1/2
SFAC C  H  N  O  Cl 
UNIT 44  52  8  8  4  
L.S. 14
ACTA 
bond $H
FMAP 2
PLAN 4
conf
mpla
htab
WGHT   0.021400   0.587100 
FVAR 5.794310 
MOLE 1
Cl1    5   0.316682   0.250000   0.684439  10.500000   0.022470 = 
           0.050510   0.024630   0.000000  -0.008100   0.000000
O1     4  -0.046633   0.143663  -0.548402  11.000000   0.028220 = 
           0.022530   0.024060  -0.006680  -0.006340   0.000500
N1     3   0.138264   0.250000   0.315139  10.500000   0.017510 = 
           0.019850   0.016950   0.000000  -0.002090   0.000000
N2     3  -0.027239   0.250000  -0.468847  10.500000   0.016940 = 
           0.020270   0.015810   0.000000   0.000260   0.000000
C1     1   0.304009   0.250000   0.390284  10.500000   0.016610 = 
           0.037010   0.020860   0.000000   0.003290   0.000000
H1     2   0.356384   0.250000   0.332104  10.500000  -1.200000
C2     1   0.260382   0.126469   0.324450  11.000000   0.023150 = 
           0.026780   0.021240   0.000640   0.000800   0.006700
H2A    2   0.284584   0.050761   0.380143  11.000000  -1.200000
H2B    2   0.261886   0.121811   0.166392  11.000000  -1.200000
C3     1   0.176058   0.131834   0.399252  11.000000   0.020510 = 
           0.023000   0.019250   0.005350  -0.002910  -0.001140
H3A    2   0.148479   0.054093   0.359414  11.000000  -1.200000
H3B    2   0.174204   0.135424   0.560739  11.000000  -1.200000
C4     1   0.101914   0.250000   0.116799  10.500000   0.013230 = 
           0.016820   0.014710   0.000000   0.001400   0.000000
C5     1   0.080968   0.131328   0.012549  11.000000   0.018700 = 
           0.014430   0.018190   0.001140   0.000060   0.000720
H5     2   0.094067   0.049932   0.072727  11.000000  -1.200000
C6     1   0.039406   0.131324  -0.178976  11.000000   0.018230 = 
           0.014580   0.017110  -0.000870   0.000900  -0.000600
H6     2   0.026209   0.051603  -0.244431  11.000000  -1.200000
C7     1   0.018171   0.250000  -0.272729  10.500000   0.014790 = 
           0.016300   0.014200   0.000000   0.000480   0.000000
HKLF 4
END 
HKLF 4
REM  gbh49ltb in Pnma
REM R1=  0.0320 for   1941 Fo > 4sig(Fo)  and  0.0364 for all   2160 data
REM    102 parameters refined using      0 restraints

REM XShell GPWARNING : The following atoms were created either by GROW or PACK.

O1A   4  -0.046633   0.356337  -0.548402  11.000000   0.028220
C2A   1   0.260382   0.373531   0.324450  11.000000   0.023150
H2AA   2   0.284584   0.449239   0.380143  11.000000  -1.200000
H2BA   2   0.261886   0.378189   0.166392  11.000000  -1.200000
C3A   1   0.176058   0.368166   0.399252  11.000000   0.020510
H3AA   2   0.148479   0.445907   0.359414  11.000000  -1.200000
H3BA   2   0.174204   0.364576   0.560739  11.000000  -1.200000
C5A   1   0.080968   0.368672   0.012549  11.000000   0.018700
H5A   2   0.094067   0.450068   0.072727  11.000000  -1.200000
C6A   1   0.039406   0.368676  -0.178976  11.000000   0.018230
H6A   2   0.026209   0.448397  -0.244431  11.000000  -1.200000
MOLE 
HKLF 4
END 
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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
Cl1 Cl 0.31668(2) 0.2500 0.68444(6) 0.03254(10) Uani 1 2 d S
O1 O -0.04663(4) 0.14366(7) -0.54840(11) 0.02493(14) Uani 1 1 d .
N1 N 0.13826(6) 0.2500 0.31514(17) 0.01810(18) Uani 1 2 d S
N2 N -0.02724(6) 0.2500 -0.46885(17) 0.01767(18) Uani 1 2 d S
C1 C 0.30401(7) 0.2500 0.3903(2) 0.0248(3) Uani 1 2 d S
H1 H 0.3564(11) 0.2500 0.332(3) 0.030 Uiso 1 2 d S
C2 C 0.26038(5) 0.12647(10) 0.32445(16) 0.02372(17) Uani 1 1 d .
H2A H 0.2846(7) 0.0508(13) 0.380(2) 0.028 Uiso 1 1 d .
H2B H 0.2619(8) 0.1218(13) 0.166(2) 0.028 Uiso 1 1 d .
C3 C 0.17606(5) 0.13183(9) 0.39925(15) 0.02092(16) Uani 1 1 d .
H3A H 0.1485(7) 0.0541(13) 0.359(2) 0.025 Uiso 1 1 d .
H3B H 0.1742(7) 0.1354(13) 0.561(2) 0.025 Uiso 1 1 d .
C4 C 0.10191(6) 0.2500 0.11680(18) 0.01492(19) Uani 1 2 d S
C5 C 0.08097(5) 0.13133(8) 0.01255(14) 0.01710(14) Uani 1 1 d .
H5 H 0.0941(7) 0.0499(12) 0.0727(19) 0.021 Uiso 1 1 d .
C6 C 0.03941(5) 0.13132(8) -0.17898(13) 0.01664(14) Uani 1 1 d .
H6 H 0.0262(7) 0.0516(12) -0.244(2) 0.020 Uiso 1 1 d .
C7 C 0.01817(6) 0.2500 -0.27273(18) 0.01510(19) Uani 1 2 d S
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 C3 121.26(5) . 7_565
C4 N1 C3 121.26(5) . .
C3 N1 C3 110.57(10) 7_565 .
O1 N2 O1 122.48(10) . 7_565
O1 N2 C7 118.75(5) . .
O1 N2 C7 118.75(5) 7_565 .
C2 C1 C2 111.56(11) 7_565 .
C2 C1 Cl1 108.93(7) 7_565 .
C2 C1 Cl1 108.93(7) . .
C2 C1 H1 111.2(5) 7_565 .
C2 C1 H1 111.2(5) . .
Cl1 C1 H1 104.8(11) . .
C1 C2 C3 111.16(8) . .
C1 C2 H2A 111.1(8) . .
C3 C2 H2A 110.0(8) . .
C1 C2 H2B 107.1(8) . .
C3 C2 H2B 109.2(8) . .
H2A C2 H2B 108.2(11) . .
N1 C3 C2 110.27(8) . .
N1 C3 H3A 111.6(8) . .
C2 C3 H3A 111.5(8) . .
N1 C3 H3B 108.1(8) . .
C2 C3 H3B 109.5(7) . .
H3A C3 H3B 105.7(10) . .
N1 C4 C5 121.39(5) . .
N1 C4 C5 121.39(5) . 7_565
C5 C4 C5 117.16(10) . 7_565
C6 C5 C4 121.40(8) . .
C6 C5 H5 117.7(7) . .
C4 C5 H5 120.9(7) . .
C5 C6 C7 119.54(8) . .
C5 C6 H6 119.7(7) . .
C7 C6 H6 120.7(7) . .
C6 C7 C6 120.90(10) 7_565 .
C6 C7 N2 119.55(5) 7_565 .
C6 C7 N2 119.55(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.8285(14) .
O1 N2 1.2347(8) .
N1 C4 1.3753(15) .
N1 C3 1.4632(11) 7_565
N1 C3 1.4632(11) .
N2 O1 1.2347(8) 7_565
N2 C7 1.4417(15) .
C1 C2 1.5206(13) 7_565
C1 C2 1.5206(13) .
C1 H1 0.972(19) .
C2 C3 1.5270(13) .
C2 H2A 0.941(13) .
C2 H2B 0.977(13) .
C3 H3A 0.955(13) .
C3 H3B 0.998(13) .
C4 C5 1.4155(10) .
C4 C5 1.4155(10) 7_565
C5 C6 1.3824(11) .
C5 H5 0.936(12) .
C6 C7 1.3886(10) .
C6 H6 0.935(12) .
C7 C6 1.3885(10) 7_565
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 -50.40(13) 7_565 .
Cl1 C1 C2 C3 69.88(9) . .
C4 N1 C3 C2 88.96(11) . .
C3 N1 C3 C2 -62.21(12) 7_565 .
C1 C2 C3 N1 55.97(11) . .
C3 N1 C4 C5 165.40(9) 7_565 .
C3 N1 C4 C5 17.28(15) . .
C3 N1 C4 C5 -17.28(15) 7_565 7_565
C3 N1 C4 C5 -165.40(9) . 7_565
N1 C4 C5 C6 175.18(9) . .
C5 C4 C5 C6 -2.25(15) 7_565 .
C4 C5 C6 C7 0.55(13) . .
C5 C6 C7 C6 1.26(16) . 7_565
C5 C6 C7 N2 -178.08(9) . .
O1 N2 C7 C6 -178.93(9) . 7_565
O1 N2 C7 C6 -0.42(15) 7_565 7_565
O1 N2 C7 C6 0.42(15) . .
O1 N2 C7 C6 178.93(9) 7_565 .
