#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/26/2222613.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_2222613
loop_
_publ_author_name
'Kavitha, T.'
'Thenmozhi, M.'
'Ponnuswamy, S.'
'Sakthivel, P.'
'Ponnuswamy, M. N.'
_publ_section_title
t-3-Ethyl-r-2,c-6-bis(4-methoxyphenyl)-1-nitrosopiperidin-4-one
_journal_coeditor_code           CI2810
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1765
_journal_paper_doi               10.1107/S1600536809024878
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H24 N2 O4'
_chemical_formula_moiety         'C21 H24 N2 O4'
_chemical_formula_sum            'C21 H24 N2 O4'
_chemical_formula_weight         368.42
_chemical_name_systematic
;
t-3-Ethyl-r-2,c-6-bis(4-methoxyphenyl)-1-nitrosopiperidin-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.2742(4)
_cell_length_b                   15.8459(7)
_cell_length_c                   16.4800(7)
_cell_measurement_reflns_used    3334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      2.5
_cell_volume                     1899.59(16)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.76
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0398
_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)+(0.0555P)²+0.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                2550
_reflns_number_total             3334
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2810.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               2222613
_cod_database_fobs_code          2222613
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-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
O O1 1.2631(2) 0.06968(12) 0.09708(10) 0.0722(5) Uani d . 1 . .
O O2 0.56881(19) 0.08201(12) 0.27581(11) 0.0648(4) Uani d . 1 . .
O O3 1.2829(2) -0.26039(11) 0.42094(11) 0.0677(5) Uani d . 1 . .
O O4 0.96286(19) 0.17870(9) 0.59490(8) 0.0480(3) Uani d . 1 . .
N N1 0.82220(18) 0.02169(10) 0.24151(9) 0.0379(3) Uani d . 1 . .
C C2 0.9060(2) -0.04979(11) 0.19832(11) 0.0394(4) Uani d . 1 . .
H H2 0.8044 -0.0852 0.1792 0.047 Uiso calc R 1 . .
C C3 1.0038(3) -0.01651(12) 0.12220(12) 0.0431(4) Uani d . 1 . .
H H3 1.0693 -0.0633 0.0962 0.052 Uiso calc R 1 . .
C C4 1.1403(3) 0.05176(12) 0.14271(12) 0.0439(4) Uani d . 1 . .
C C5 1.1176(2) 0.09628(12) 0.22290(12) 0.0406(4) Uani d . 1 . .
H H5A 1.1624 0.1536 0.2166 0.049 Uiso calc R 1 . .
H H5B 1.1967 0.0686 0.2621 0.049 Uiso calc R 1 . .
C C6 0.9234(2) 0.10068(11) 0.25901(11) 0.0361(4) Uani d . 1 . .
H H6 0.8583 0.1469 0.2319 0.043 Uiso calc R 1 . .
N N7 0.6402(2) 0.01792(13) 0.24877(11) 0.0523(4) Uani d . 1 . .
C C8 1.0192(2) -0.10403(10) 0.25549(12) 0.0383(4) Uani d . 1 . .
C C9 1.2088(3) -0.11160(12) 0.25259(13) 0.0452(4) Uani d . 1 . .
H H9 1.2747 -0.0822 0.2134 0.054 Uiso calc R 1 . .
C C10 1.3015(3) -0.16248(13) 0.30744(13) 0.0496(5) Uani d . 1 . .
H H10 1.4290 -0.1664 0.3051 0.060 Uiso calc R 1 . .
C C11 1.2061(3) -0.20718(12) 0.36542(13) 0.0484(5) Uani d . 1 . .
C C12 1.0155(3) -0.20026(13) 0.36894(14) 0.0516(5) Uani d . 1 . .
H H12 0.9496 -0.2303 0.4077 0.062 Uiso calc R 1 . .
C C13 0.9252(3) -0.14900(12) 0.31510(13) 0.0473(5) Uani d . 1 . .
H H13 0.7980 -0.1441 0.3184 0.057 Uiso calc R 1 . .
C C16 0.9304(2) 0.12116(10) 0.34877(11) 0.0351(4) Uani d . 1 . .
C C17 1.0182(2) 0.06863(11) 0.40442(12) 0.0407(4) Uani d . 1 . .
H H17 1.0712 0.0186 0.3865 0.049 Uiso calc R 1 . .
C C18 1.0279(2) 0.08954(12) 0.48551(11) 0.0411(4) Uani d . 1 . .
H H18 1.0871 0.0537 0.5218 0.049 Uiso calc R 1 . .
C C19 0.9491(2) 0.16428(11) 0.51316(11) 0.0373(4) Uani d . 1 . .
C C20 0.8647(3) 0.21793(12) 0.45857(11) 0.0415(4) Uani d . 1 . .
H H20 0.8142 0.2686 0.4762 0.050 Uiso calc R 1 . .
C C21 0.8557(2) 0.19574(11) 0.37750(12) 0.0402(4) Uani d . 1 . .
H H21 0.7977 0.2320 0.3412 0.048 Uiso calc R 1 . .
C C22 1.4718(4) -0.28172(19) 0.41023(18) 0.0810(8) Uani d . 1 . .
H H22A 1.5095 -0.3196 0.4525 0.122 Uiso calc R 1 . .
H H22B 1.5451 -0.2314 0.4125 0.122 Uiso calc R 1 . .
H H22C 1.4881 -0.3085 0.3585 0.122 Uiso calc R 1 . .
C C23 0.8815(3) 0.25378(15) 0.62544(14) 0.0602(6) Uani d . 1 . .
H H23A 0.8998 0.2567 0.6831 0.090 Uiso calc R 1 . .
H H23B 0.7521 0.2535 0.6139 0.090 Uiso calc R 1 . .
H H23C 0.9375 0.3019 0.6000 0.090 Uiso calc R 1 . .
C C14 0.8639(4) 0.02004(17) 0.06142(14) 0.0644(6) Uani d . 1 . .
H H14A 0.7562 -0.0160 0.0604 0.077 Uiso calc R 1 . .
H H14B 0.8255 0.0753 0.0802 0.077 Uiso calc R 1 . .
C C15 0.9381(5) 0.0281(2) -0.02394(16) 0.0977(10) Uani d . 1 . .
H H15A 0.8446 0.0512 -0.0586 0.147 Uiso calc R 1 . .
H H15B 0.9737 -0.0265 -0.0436 0.147 Uiso calc R 1 . .
H H15C 1.0430 0.0649 -0.0238 0.147 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C11 O3 C22 . . 117.3(2) ?
C19 O4 C23 . . 117.23(16) ?
N7 N1 C2 . . 114.93(15) ?
N7 N1 C6 . . 121.01(16) ?
C2 N1 C6 . . 122.65(13) ?
N1 C2 C8 . . 111.15(14) ?
N1 C2 C3 . . 108.85(14) ?
C8 C2 C3 . . 116.74(15) ?
N1 C2 H2 . . 106.5 ?
C8 C2 H2 . . 106.5 ?
C3 C2 H2 . . 106.5 ?
C4 C3 C2 . . 111.62(15) ?
C4 C3 C14 . . 108.13(17) ?
C2 C3 C14 . . 110.74(17) ?
C4 C3 H3 . . 108.8 ?
C2 C3 H3 . . 108.8 ?
C14 C3 H3 . . 108.8 ?
O1 C4 C3 . . 121.27(18) ?
O1 C4 C5 . . 121.28(17) ?
C3 C4 C5 . . 117.44(16) ?
C4 C5 C6 . . 117.51(15) ?
C4 C5 H5A . . 107.9 ?
C6 C5 H5A . . 107.9 ?
C4 C5 H5B . . 107.9 ?
C6 C5 H5B . . 107.9 ?
H5A C5 H5B . . 107.2 ?
N1 C6 C16 . . 112.83(15) ?
N1 C6 C5 . . 110.11(14) ?
C16 C6 C5 . . 110.94(14) ?
N1 C6 H6 . . 107.6 ?
C16 C6 H6 . . 107.6 ?
C5 C6 H6 . . 107.6 ?
O2 N7 N1 . . 114.66(17) ?
C9 C8 C13 . . 117.96(18) ?
C9 C8 C2 . . 124.60(17) ?
C13 C8 C2 . . 117.44(16) ?
C8 C9 C10 . . 120.83(19) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C11 C10 C9 . . 120.40(18) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
O3 C11 C10 . . 125.24(18) ?
O3 C11 C12 . . 115.4(2) ?
C10 C11 C12 . . 119.37(19) ?
C13 C12 C11 . . 119.8(2) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C8 . . 121.65(18) ?
C12 C13 H13 . . 119.2 ?
C8 C13 H13 . . 119.2 ?
C21 C16 C17 . . 117.70(17) ?
C21 C16 C6 . . 120.23(15) ?
C17 C16 C6 . . 122.00(15) ?
C18 C17 C16 . . 121.19(16) ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C17 C18 C19 . . 120.04(17) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
O4 C19 C20 . . 124.75(17) ?
O4 C19 C18 . . 115.70(16) ?
C20 C19 C18 . . 119.55(17) ?
C19 C20 C21 . . 119.58(16) ?
C19 C20 H20 . . 120.2 ?
C21 C20 H20 . . 120.2 ?
C20 C21 C16 . . 121.92(17) ?
C20 C21 H21 . . 119.0 ?
C16 C21 H21 . . 119.0 ?
O3 C22 H22A . . 109.5 ?
O3 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O3 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O4 C23 H23A . . 109.5 ?
O4 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
O4 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C15 C14 C3 . . 113.7(2) ?
C15 C14 H14A . . 108.8 ?
C3 C14 H14A . . 108.8 ?
C15 C14 H14B . . 108.8 ?
C3 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
O1 C4 . 1.202(2) ?
O2 N7 . 1.225(2) ?
O3 C11 . 1.364(3) ?
O3 C22 . 1.426(3) ?
O4 C19 . 1.370(2) ?
O4 C23 . 1.421(2) ?
N1 N7 . 1.331(2) ?
N1 C2 . 1.470(2) ?
N1 C6 . 1.481(2) ?
C2 C8 . 1.518(3) ?
C2 C3 . 1.536(3) ?
C2 H2 . 0.98 ?
C3 C4 . 1.506(3) ?
C3 C14 . 1.541(3) ?
C3 H3 . 0.98 ?
C4 C5 . 1.507(3) ?
C5 C6 . 1.535(2) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 C16 . 1.515(3) ?
C6 H6 . 0.98 ?
C8 C9 . 1.385(3) ?
C8 C13 . 1.393(3) ?
C9 C10 . 1.386(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.392(3) ?
C12 C13 . 1.370(3) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C16 C21 . 1.384(2) ?
C16 C17 . 1.394(2) ?
C17 C18 . 1.379(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.392(3) ?
C18 H18 . 0.93 ?
C19 C20 . 1.382(3) ?
C20 C21 . 1.383(3) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
C14 C15 . 1.512(4) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C15 H15C O1 1 0.96 2.56 3.163(4) 121
C18 H18 O1 2_755 0.93 2.56 3.472(3) 167
C23 H23B Cg1 3_456 0.96 2.89 3.718(2) 144
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
N7 N1 C2 C8 . . . . -111.25(18) ?
C6 N1 C2 C8 . . . . 82.2(2) ?
N7 N1 C2 C3 . . . . 118.82(18) ?
C6 N1 C2 C3 . . . . -47.7(2) ?
N1 C2 C3 C4 . . . . 54.76(19) ?
C8 C2 C3 C4 . . . . -72.04(19) ?
N1 C2 C3 C14 . . . . -65.78(19) ?
C8 C2 C3 C14 . . . . 167.43(16) ?
C2 C3 C4 O1 . . . . 159.7(2) ?
C14 C3 C4 O1 . . . . -78.2(3) ?
C2 C3 C4 C5 . . . . -19.8(2) ?
C14 C3 C4 C5 . . . . 102.2(2) ?
O1 C4 C5 C6 . . . . 153.2(2) ?
C3 C4 C5 C6 . . . . -27.2(2) ?
N7 N1 C6 C16 . . . . 72.0(2) ?
C2 N1 C6 C16 . . . . -122.28(17) ?
N7 N1 C6 C5 . . . . -163.49(17) ?
C2 N1 C6 C5 . . . . 2.3(2) ?
C4 C5 C6 N1 . . . . 36.3(2) ?
C4 C5 C6 C16 . . . . 161.94(15) ?
C2 N1 N7 O2 . . . . -171.53(17) ?
C6 N1 N7 O2 . . . . -4.7(3) ?
N1 C2 C8 C9 . . . . -112.31(19) ?
C3 C2 C8 C9 . . . . 13.3(3) ?
N1 C2 C8 C13 . . . . 67.46(19) ?
C3 C2 C8 C13 . . . . -166.89(16) ?
C13 C8 C9 C10 . . . . 0.0(3) ?
C2 C8 C9 C10 . . . . 179.80(17) ?
C8 C9 C10 C11 . . . . 0.7(3) ?
C22 O3 C11 C10 . . . . -10.4(3) ?
C22 O3 C11 C12 . . . . 168.6(2) ?
C9 C10 C11 O3 . . . . 178.42(19) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
O3 C11 C12 C13 . . . . -179.33(18) ?
C10 C11 C12 C13 . . . . -0.2(3) ?
C11 C12 C13 C8 . . . . 1.0(3) ?
C9 C8 C13 C12 . . . . -0.9(3) ?
C2 C8 C13 C12 . . . . 179.36(17) ?
N1 C6 C16 C21 . . . . -119.97(17) ?
C5 C6 C16 C21 . . . . 115.94(18) ?
N1 C6 C16 C17 . . . . 63.0(2) ?
C5 C6 C16 C17 . . . . -61.1(2) ?
C21 C16 C17 C18 . . . . 1.0(3) ?
C6 C16 C17 C18 . . . . 178.05(17) ?
C16 C17 C18 C19 . . . . 0.0(3) ?
C23 O4 C19 C20 . . . . 1.0(3) ?
C23 O4 C19 C18 . . . . -179.06(16) ?
C17 C18 C19 O4 . . . . 178.80(17) ?
C17 C18 C19 C20 . . . . -1.3(3) ?
O4 C19 C20 C21 . . . . -178.57(18) ?
C18 C19 C20 C21 . . . . 1.5(3) ?
C19 C20 C21 C16 . . . . -0.5(3) ?
C17 C16 C21 C20 . . . . -0.7(3) ?
C6 C16 C21 C20 . . . . -177.86(17) ?
C4 C3 C14 C15 . . . . 75.9(3) ?
C2 C3 C14 C15 . . . . -161.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655826
