#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/59/2015999.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_2015999
loop_
_publ_author_name
'Zeller, Matthias'
'Pett, Virginia B.'
'Haynes, LeRoy W.'
_publ_section_title
;
 Ring opening of pyridines: the pseudo-cis and
 pseudo-trans isomers of tetra-n-butylammonium
 4-nitro-5-oxo-2-pentenenitrilate
;
_journal_coeditor_code           LN3045
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o343
_journal_page_last               o346
_journal_paper_doi               10.1107/S0108270107019506
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H36 N +, C5 H3 N2 O3 -'
_chemical_formula_moiety         'C16 H36 N +, C5 H3 N2 O3 -'
_chemical_formula_sum            'C21 H39 N3 O3'
_chemical_formula_weight         381.55
_chemical_name_systematic
;
tetra-n-butylammonium 4-nitro-5-oxo-2-pentenenitrilate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 97.444(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2793(16)
_cell_length_b                   9.7588(12)
_cell_length_c                   18.422(2)
_cell_measurement_reflns_used    6428
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.67
_cell_volume                     2188.9(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21198
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0686
_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)+(0.0476P)²+2.9417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                4323
_reflns_number_total             5406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ln3045.cif
_cod_data_source_block           I_II
_cod_original_cell_volume        2189.0(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015999
_cod_database_fobs_code          2015999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C C1 0.66758(17) 0.4305(2) 0.51970(11) 0.0177(4) Uani d . 1 . .
H H1A 0.6227 0.4714 0.5550 0.021 Uiso calc R 1 . .
H H1B 0.6172 0.4070 0.4750 0.021 Uiso calc R 1 . .
C C2 0.71834(17) 0.2987(2) 0.55253(12) 0.0198(4) Uani d . 1 . .
H H2A 0.7618 0.3179 0.6006 0.024 Uiso calc R 1 . .
H H2B 0.7680 0.2591 0.5198 0.024 Uiso calc R 1 . .
C C3 0.62603(18) 0.1977(2) 0.56196(12) 0.0225(4) Uani d . 1 . .
H H3A 0.5743 0.2410 0.5920 0.027 Uiso calc R 1 . .
H H3B 0.5851 0.1767 0.5133 0.027 Uiso calc R 1 . .
C C4 0.6689(2) 0.0647(2) 0.59833(13) 0.0277(5) Uani d . 1 . .
H H4B 0.7051 0.0842 0.6478 0.042 Uiso calc R 1 . .
H H4C 0.7216 0.0226 0.5695 0.042 Uiso calc R 1 . .
H H4A 0.6074 0.0017 0.6011 0.042 Uiso calc R 1 . .
C C5 0.82398(17) 0.5857(2) 0.56707(11) 0.0180(4) Uani d . 1 . .
H H5A 0.8645 0.5051 0.5892 0.022 Uiso calc R 1 . .
H H5B 0.8786 0.6499 0.5511 0.022 Uiso calc R 1 . .
C C6 0.76742(18) 0.6557(2) 0.62561(12) 0.0220(4) Uani d . 1 . .
H H6A 0.7154 0.5910 0.6442 0.026 Uiso calc R 1 . .
H H6B 0.7250 0.7354 0.6041 0.026 Uiso calc R 1 . .
C C7 0.85114(18) 0.7034(2) 0.68867(12) 0.0244(5) Uani d . 1 . .
H H7B 0.9104 0.7548 0.6690 0.029 Uiso calc R 1 . .
H H7A 0.8845 0.6226 0.7154 0.029 Uiso calc R 1 . .
C C8 0.7982(2) 0.7949(2) 0.74164(12) 0.0259(5) Uani d . 1 . .
H H8B 0.7385 0.7449 0.7604 0.039 Uiso calc R 1 . .
H H8C 0.7687 0.8775 0.7160 0.039 Uiso calc R 1 . .
H H8A 0.8534 0.8210 0.7826 0.039 Uiso calc R 1 . .
C C9 0.67666(17) 0.6553(2) 0.46563(11) 0.0174(4) Uani d . 1 . .
H H9A 0.6309 0.6200 0.4214 0.021 Uiso calc R 1 . .
H H9B 0.6263 0.6836 0.5007 0.021 Uiso calc R 1 . .
C C10 0.73768(17) 0.7814(2) 0.44421(12) 0.0194(4) Uani d . 1 . .
H H10A 0.7813 0.7581 0.4043 0.023 Uiso calc R 1 . .
H H10B 0.7887 0.8141 0.4867 0.023 Uiso calc R 1 . .
C C11 0.65515(18) 0.8942(2) 0.41870(12) 0.0205(4) Uani d . 1 . .
H H11A 0.6056 0.8616 0.3755 0.025 Uiso calc R 1 . .
H H11B 0.6098 0.9141 0.4581 0.025 Uiso calc R 1 . .
C C12 0.7123(2) 1.0254(2) 0.39888(13) 0.0253(5) Uani d . 1 . .
H H12B 0.7546 1.0069 0.3584 0.038 Uiso calc R 1 . .
H H12C 0.7618 1.0575 0.4415 0.038 Uiso calc R 1 . .
H H12A 0.6570 1.0959 0.3840 0.038 Uiso calc R 1 . .
C C13 0.82321(17) 0.4830(2) 0.44702(11) 0.0185(4) Uani d . 1 . .
H H13A 0.8703 0.5588 0.4337 0.022 Uiso calc R 1 . .
H H13B 0.8720 0.4131 0.4731 0.022 Uiso calc R 1 . .
C C14 0.76606(18) 0.4194(2) 0.37688(11) 0.0201(4) Uani d . 1 . .
H H14A 0.7269 0.4912 0.3458 0.024 Uiso calc R 1 . .
H H14B 0.7116 0.3509 0.3887 0.024 Uiso calc R 1 . .
C C15 0.85185(19) 0.3506(2) 0.33596(13) 0.0257(5) Uani d . 1 . .
H H15A 0.9051 0.4205 0.3238 0.031 Uiso calc R 1 . .
H H15B 0.8926 0.2819 0.3684 0.031 Uiso calc R 1 . .
C C16 0.8011(2) 0.2806(2) 0.26595(12) 0.0278(5) Uani d . 1 . .
H H16B 0.7615 0.3484 0.2333 0.042 Uiso calc R 1 . .
H H16C 0.7499 0.2095 0.2778 0.042 Uiso calc R 1 . .
H H16A 0.8592 0.2388 0.2416 0.042 Uiso calc R 1 . .
N N1 0.74801(14) 0.53846(17) 0.49969(9) 0.0167(3) Uani d . 1 . .
C C17 0.50529(19) 0.8085(2) 0.77333(13) 0.0268(5) Uani d . 1 A .
H H17 0.5074 0.8763 0.7366 0.032 Uiso calc R 1 . .
C C18 0.50457(17) 0.6675(2) 0.75225(12) 0.0212(4) Uani d . 1 . .
N N2 0.50543(15) 0.6390(2) 0.67769(10) 0.0243(4) Uani d . 1 A .
O O1 0.50716(13) 0.51655(17) 0.65574(9) 0.0273(4) Uani d . 1 . .
O O2 0.50433(15) 0.7341(2) 0.63188(10) 0.0343(4) Uani d . 1 . .
O O3 0.50335(17) 0.84590(19) 0.83661(10) 0.0389(5) Uani d . 1 . .
C C19 0.50129(18) 0.5527(2) 0.79985(13) 0.0237(5) Uani d PD 0.917(3) A 1
H H19 0.4973 0.4675 0.7746 0.028 Uiso calc PR 0.917(3) A 1
C C20 0.5026(5) 0.5383(4) 0.87301(15) 0.0262(7) Uani d PD 0.917(3) A 1
H H20 0.4954 0.4462 0.8884 0.031 Uiso calc PR 0.917(3) A 1
C C21 0.51271(19) 0.6356(3) 0.93144(14) 0.0240(5) Uani d PD 0.917(3) A 1
N N3 0.51927(18) 0.6968(2) 0.98476(12) 0.0290(5) Uani d PD 0.917(3) A 1
C C19B 0.50129(18) 0.5527(2) 0.79985(13) 0.0237(5) Uani d P 0.083(3) A 2
H H19B 0.4882 0.4648 0.7783 0.028 Uiso calc PR 0.083(3) A 2
C C20B 0.516(7) 0.561(4) 0.8742(10) 0.0262(7) Uani d PD 0.083(3) A 2
H H20B 0.5323 0.6467 0.8975 0.031 Uiso calc PR 0.083(3) A 2
C C21B 0.506(2) 0.440(2) 0.9173(14) 0.0240(5) Uani d PD 0.083(3) A 2
N N3B 0.494(2) 0.341(2) 0.9503(13) 0.0290(5) Uani d PD 0.083(3) A 2
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
C2 C1 N1 115.89(17)
C2 C1 H1A 108.3
N1 C1 H1A 108.3
C2 C1 H1B 108.3
N1 C1 H1B 108.3
H1A C1 H1B 107.4
C1 C2 C3 108.59(17)
C1 C2 H2A 110.0
C3 C2 H2A 110.0
C1 C2 H2B 110.0
C3 C2 H2B 110.0
H2A C2 H2B 108.4
C4 C3 C2 112.38(19)
C4 C3 H3A 109.1
C2 C3 H3A 109.1
C4 C3 H3B 109.1
C2 C3 H3B 109.1
H3A C3 H3B 107.9
C3 C4 H4B 109.5
C3 C4 H4C 109.5
H4B C4 H4C 109.5
C3 C4 H4A 109.5
H4B C4 H4A 109.5
H4C C4 H4A 109.5
C6 C5 N1 115.24(17)
C6 C5 H5A 108.5
N1 C5 H5A 108.5
C6 C5 H5B 108.5
N1 C5 H5B 108.5
H5A C5 H5B 107.5
C5 C6 C7 110.73(18)
C5 C6 H6A 109.5
C7 C6 H6A 109.5
C5 C6 H6B 109.5
C7 C6 H6B 109.5
H6A C6 H6B 108.1
C6 C7 C8 111.41(19)
C6 C7 H7B 109.3
C8 C7 H7B 109.3
C6 C7 H7A 109.3
C8 C7 H7A 109.3
H7B C7 H7A 108.0
C7 C8 H8B 109.5
C7 C8 H8C 109.5
H8B C8 H8C 109.5
C7 C8 H8A 109.5
H8B C8 H8A 109.5
H8C C8 H8A 109.5
C10 C9 N1 115.90(17)
C10 C9 H9A 108.3
N1 C9 H9A 108.3
C10 C9 H9B 108.3
N1 C9 H9B 108.3
H9A C9 H9B 107.4
C9 C10 C11 109.49(17)
C9 C10 H10A 109.8
C11 C10 H10A 109.8
C9 C10 H10B 109.8
C11 C10 H10B 109.8
H10A C10 H10B 108.2
C12 C11 C10 111.75(18)
C12 C11 H11A 109.3
C10 C11 H11A 109.3
C12 C11 H11B 109.3
C10 C11 H11B 109.3
H11A C11 H11B 107.9
C11 C12 H12B 109.5
C11 C12 H12C 109.5
H12B C12 H12C 109.5
C11 C12 H12A 109.5
H12B C12 H12A 109.5
H12C C12 H12A 109.5
C14 C13 N1 115.80(17)
C14 C13 H13A 108.3
N1 C13 H13A 108.3
C14 C13 H13B 108.3
N1 C13 H13B 108.3
H13A C13 H13B 107.4
C13 C14 C15 109.07(18)
C13 C14 H14A 109.9
C15 C14 H14A 109.9
C13 C14 H14B 109.9
C15 C14 H14B 109.9
H14A C14 H14B 108.3
C16 C15 C14 112.53(19)
C16 C15 H15A 109.1
C14 C15 H15A 109.1
C16 C15 H15B 109.1
C14 C15 H15B 109.1
H15A C15 H15B 107.8
C15 C16 H16B 109.5
C15 C16 H16C 109.5
H16B C16 H16C 109.5
C15 C16 H16A 109.5
H16B C16 H16A 109.5
H16C C16 H16A 109.5
C1 N1 C9 105.15(15)
C1 N1 C13 111.98(15)
C9 N1 C13 111.56(15)
C1 N1 C5 111.12(15)
C9 N1 C5 111.58(15)
C13 N1 C5 105.59(15)
O3 C17 C18 123.1(2)
O3 C17 H17 118.5
C18 C17 H17 118.5
N2 C18 C19 116.78(19)
N2 C18 C17 117.1(2)
C19 C18 C17 126.1(2)
O2 N2 O1 118.96(19)
O2 N2 C18 120.8(2)
O1 N2 C18 120.24(19)
C20 C19 C18 134.1(2)
C20 C19 H19 113.0
C18 C19 H19 113.0
C19 C20 C21 132.1(3)
C19 C20 H20 113.9
C21 C20 H20 113.9
N3 C21 C20 169.7(3)
C21B C20B H20B 120.0
N3B C21B C20B 177(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.520(3)
C1 N1 1.522(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.529(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.523(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4B 0.9800
C4 H4C 0.9800
C4 H4A 0.9800
C5 C6 1.518(3)
C5 N1 1.524(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.521(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.529(3)
C7 H7B 0.9900
C7 H7A 0.9900
C8 H8B 0.9800
C8 H8C 0.9800
C8 H8A 0.9800
C9 C10 1.520(3)
C9 N1 1.522(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.528(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.527(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12B 0.9800
C12 H12C 0.9800
C12 H12A 0.9800
C13 C14 1.520(3)
C13 N1 1.523(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.528(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.520(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16B 0.9800
C16 H16C 0.9800
C16 H16A 0.9800
C17 O3 1.225(3)
C17 C18 1.429(3)
C17 H17 0.9500
C18 N2 1.403(3)
C18 C19 1.427(3)
N2 O2 1.253(3)
N2 O1 1.263(3)
C19 C20 1.353(4)
C19 H19 0.9500
C20 C21 1.428(4)
C20 H20 0.9500
C21 N3 1.143(3)
C20B C21B 1.44(2)
C20B H20B 0.9500
C21B N3B 1.163(18)
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
C20 H20 N3 3_667 0.95 2.75 3.519(4) 139
C20B H20B N3B 3_667 0.95 2.87 3.39(4) 116
C20B H20B O3 . 0.95 2.25 2.86(4) 122
