#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/55/2005560.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_2005560
loop_
_publ_author_name
'Blake, A. J.'
'McNab, H.'
'Monahan, L. C.'
'Parsons, S.'
'Stevenson, E.'
_publ_section_title
;
 Two C-Unsubstituted Enaminals
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2814
_journal_page_last               2818
_journal_paper_doi               10.1107/S0108270196007020
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C9 H17 N O'
_chemical_formula_sum            'C9 H17 N O'
_chemical_formula_weight         155.24
_chemical_melting_point          348.5(5)
_chemical_name_systematic
;
 3-(di-isopropylamino)prop-2-enal
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                102.08(3)
_cell_angle_beta                 98.93(3)
_cell_angle_gamma                109.48(2)
_cell_formula_units_Z            4
_cell_length_a                   8.304(3)
_cell_length_b                   11.163(5)
_cell_length_c                   11.802(6)
_cell_measurement_reflns_used    53
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      17
_cell_measurement_theta_min      14
_cell_volume                     978.0(8)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992b)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1995)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_measurement_device       'Stoe Stadi-4 four-circle diffractometer'
_diffrn_measurement_method       'ω-2θ 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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4905
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Cube
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.49
_refine_ls_extinction_coef       0.025(6)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   0.984
_refine_ls_goodness_of_fit_obs   1.021
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_restrained_S_obs      1.021
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_obs          0.0638
_refine_ls_shift/esd_max         -0.61
_refine_ls_shift/esd_mean        0.05
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.082P)² + 0.667P] where P = (Fo² + 2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1844
_refine_ls_wR_factor_obs         0.1598
_reflns_number_observed          3392
_reflns_number_total             4642
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab1382.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_chemical_melting_point' value '348-349K' was changed to '348.5(5)'
- the average value was taken and precision was
estimated.

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

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.082P)^2^ + 0.667P] where P = (Fo^2^ + 2Fc^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.082P)^2^ + 0.667P] where P = (Fo^2^ + 2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        978.1(8)
_cod_database_code               2005560
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_type_symbol
O1 1 0.5775(2) 0.3431(2) 1.09554(12) 0.0474(4) Uani d . . O
C1 1 0.5514(2) 0.2971(2) 0.9867(2) 0.0328(4) Uani d . . C
H1A 1 0.5988(2) 0.2323(2) 0.9615(2) 0.039 Uiso calc R . H
C2 1 0.4585(2) 0.3307(2) 0.8957(2) 0.0289(4) Uani d . . C
H2A 1 0.4076(2) 0.3947(2) 0.9145(2) 0.035 Uiso calc R . H
C3 1 0.4444(2) 0.2684(2) 0.7801(2) 0.0265(4) Uani d . . C
H3A 1 0.4975(2) 0.2048(2) 0.7699(2) 0.032 Uiso calc R . H
N4 1 0.3671(2) 0.28362(15) 0.67909(13) 0.0303(3) Uani d . . N
C5 1 0.3626(3) 0.1989(2) 0.5630(2) 0.0336(4) Uani d . . C
H5A 1 0.2928(3) 0.2205(2) 0.4988(2) 0.040 Uiso calc R . H
C51 1 0.2704(3) 0.0526(2) 0.5516(2) 0.0418(5) Uani d . . C
H51A 1 0.1524(3) 0.0361(2) 0.5651(2) 0.063 Uiso calc R . H
H51B 1 0.3387(3) 0.0274(2) 0.6112(2) 0.063 Uiso calc R . H
H51C 1 0.2609(3) 0.0001(2) 0.4714(2) 0.063 Uiso calc R . H
C52 1 0.5465(3) 0.2292(2) 0.5428(2) 0.0449(5) Uani d . . C
H52A 1 0.6025(3) 0.3239(2) 0.5507(2) 0.067 Uiso calc R . H
H52B 1 0.5389(3) 0.1781(2) 0.4624(2) 0.067 Uiso calc R . H
H52C 1 0.6168(3) 0.2052(2) 0.6022(2) 0.067 Uiso calc R . H
C6 1 0.2746(3) 0.3758(2) 0.6801(2) 0.0367(4) Uani d . . C
H6A 1 0.3046(3) 0.4319(2) 0.7643(2) 0.044 Uiso calc R . H
C61 1 0.0755(3) 0.2994(3) 0.6431(2) 0.0553(6) Uani d . . C
H61A 1 0.0419(3) 0.2413(3) 0.6944(2) 0.083 Uiso calc R . H
H61B 1 0.0411(3) 0.2459(3) 0.5597(2) 0.083 Uiso calc R . H
H61C 1 0.0157(3) 0.3619(3) 0.6515(2) 0.083 Uiso calc R . H
C62 1 0.3355(4) 0.4677(2) 0.6040(2) 0.0533(6) Uani d . . C
H62A 1 0.4636(4) 0.5146(2) 0.6306(2) 0.080 Uiso calc R . H
H62B 1 0.2785(4) 0.5320(2) 0.6120(2) 0.080 Uiso calc R . H
H62C 1 0.3037(4) 0.4160(2) 0.5202(2) 0.080 Uiso calc R . H
O1' 1 0.3753(3) -0.0389(2) 0.2489(2) 0.0723(6) Uani d . . O
C1' 1 0.3465(3) 0.0531(2) 0.2199(2) 0.0468(5) Uani d . . C
H1'A 1 0.4351(3) 0.1103(2) 0.1924(2) 0.056 Uiso d R . H
C2' 1 0.1938(3) 0.0821(2) 0.2231(2) 0.0367(4) Uani d . . C
H2'A 1 0.1018(3) 0.0311(2) 0.2525(2) 0.044 Uiso d R . H
C3' 1 0.1834(2) 0.1854(2) 0.1830(2) 0.0332(4) Uani d . . C
H3'A 1 0.2817(2) 0.2317(2) 0.1561(2) 0.040 Uiso d R . H
N4' 1 0.0530(2) 0.2299(2) 0.1760(2) 0.0557(6) Uani d . . N
C5' 0.647(4) 0.0324(4) 0.3235(3) 0.1229(3) 0.0345(7) Uani d P 1 C
H5' 0.647(4) -0.0835(4) 0.3294(3) 0.1294(3) 0.041 Uiso calc PR 1 H
C51' 1 0.0354(4) 0.2938(4) -0.0131(3) 0.0838(10) Uani d . 1 C
H51D 1 -0.0587(4) 0.2085(4) -0.0577(3) 0.126 Uiso calc R 1 H
H51E 1 0.1495(4) 0.2905(4) -0.0213(3) 0.126 Uiso calc R 1 H
H51F 1 0.0171(4) 0.3639(4) -0.0448(3) 0.126 Uiso calc R 1 H
C52' 0.647(4) 0.1772(5) 0.4568(4) 0.1921(5) 0.0685(14) Uani d P 1 C
H52D 0.647(4) 0.1747(5) 0.4756(4) 0.2765(5) 0.103 Uiso calc PR 1 H
H52E 0.647(4) 0.1581(5) 0.5263(4) 0.1597(5) 0.103 Uiso calc PR 1 H
H52F 0.647(4) 0.2919(5) 0.4542(4) 0.1845(5) 0.103 Uiso calc PR 1 H
C5" 0.353(4) 0.1316(8) 0.3619(6) 0.1067(5) 0.0357(14) Uiso d P 2 C
C52" 0.353(4) 0.1075(11) 0.4819(8) 0.1801(7) 0.055(2) Uiso d P 2 C
C6' 0.647(4) -0.1097(3) 0.1545(3) 0.2274(3) 0.0304(7) Uani d P 3 C
H6' 0.647(4) -0.0686(3) 0.1052(3) 0.2796(3) 0.036 Uiso calc PR 3 H
C61' 1 -0.2454(4) 0.0540(2) 0.1184(3) 0.0652(8) Uani d . 3 C
H61D 1 -0.1925(4) -0.0026(2) 0.0764(3) 0.098 Uiso calc R 3 H
H61E 1 -0.2861(4) 0.1000(2) 0.0651(3) 0.098 Uiso calc R 3 H
H61F 1 -0.3455(4) -0.0006(2) 0.1432(3) 0.098 Uiso calc R 3 H
C62' 0.647(4) -0.1704(4) 0.2515(3) 0.3033(3) 0.0387(8) Uani d P 3 C
H62D 0.647(4) -0.0725(4) 0.3121(3) 0.3709(3) 0.058 Uiso calc PR 3 H
H62E 0.647(4) -0.2684(4) 0.2025(3) 0.3333(3) 0.058 Uiso calc PR 3 H
H62F 0.647(4) -0.2093(4) 0.3024(3) 0.2545(3) 0.058 Uiso calc PR 3 H
C6" 0.353(4) -0.0993(6) 0.2017(5) 0.1744(5) 0.0278(12) Uiso d P 4 C
C62" 0.353(4) -0.0973(8) 0.2236(6) 0.3071(5) 0.0380(14) Uiso d P 4 C
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 C2 126.8(2) n
C3 C2 C1 117.8(2) n
N4 C3 C2 129.6(2) n
C3 N4 C6 121.64(15) n
C3 N4 C5 119.30(14) n
C6 N4 C5 118.91(14) n
N4 C5 C52 111.1(2) n
N4 C5 C51 111.8(2) n
C52 C5 C51 111.3(2) n
N4 C6 C62 111.8(2) n
N4 C6 C61 110.4(2) n
C62 C6 C61 112.2(2) n
O1' C1' C2' 126.4(2) n
C3' C2' C1' 117.7(2) n
N4' C3' C2' 128.4(2) n
C3' N4' C5' 128.6(2) ?
C3' N4' C6' 115.4(2) ?
C5' N4' C6' 115.8(2) ?
C3' N4' C5" 101.9(2) ?
C3' N4' C6" 144.1(3) ?
C5" N4' C6" 111.4(2) ?
N4' C5' C52' 108.4(3) ?
N4' C5' C51' 114.5(3) ?
C52' C5' C51' 109.5(3) ?
C52" C5" N4' 106.5(5) ?
C61' C6' C62' 116.4(2) ?
C61' C6' N4' 104.6(2) ?
C62' C6' N4' 111.8(2) ?
N4' C6" C62" 102.3(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.235(2) n
C1 C2 1.412(2) n
C2 C3 1.363(3) n
C3 N4 1.334(2) n
N4 C6 1.475(2) n
N4 C5 1.480(2) n
C5 C52 1.518(3) n
C5 C51 1.521(3) n
C6 C62 1.515(3) n
C6 C61 1.527(3) n
O1' C1' 1.231(3) n
C1' C2' 1.413(3) n
C2' C3' 1.358(3) n
C3' N4' 1.332(2) n
N4' C6" 1.193(5) ?
N4' C5' 1.369(3) ?
N4' C6' 1.616(4) ?
N4' C5" 1.816(7) ?
C5' C52' 1.523(5) ?
C5' C51' 1.575(4) ?
C5" C52" 1.527(10) ?
C6' C61' 1.512(4) ?
C6' C62' 1.525(4) ?
C6" C62" 1.530(8) ?
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 179.9(2) n
C1 C2 C3 N4 -178.8(2) n
C2 C3 N4 C5 -177.3(2) n
C2 C3 N4 C6 -1.8(3) n
C3 N4 C5 C52 -66.5(2) n
C6 N4 C5 C52 117.9(2) n
C3 N4 C5 C51 58.5(2) n
C6 N4 C5 C51 -117.1(2) n
C3 N4 C6 C62 129.1(2) n
C5 N4 C6 C62 -55.4(2) n
C3 N4 C6 C61 -105.3(2) n
C5 N4 C6 C61 70.2(2) n
O1' C1' C2' C3' -177.4(2) n
C1' C2' C3' N4' 179.1(2) n
C2' C3' N4' C6" -18.9(6) n
C2' C3' N4' C5' -171.4(2) ?
C2' C3' N4' C6' 2.9(3) ?
C2' C3' N4' C5" -176.9(3) ?
C6" N4' C5' C52' 129.2(4) ?
C3' N4' C5' C52' -66.6(4) ?
C6' N4' C5' C52' 119.1(3) ?
C5" N4' C5' C52' -54.8(5) ?
C6" N4' C5' C51' -108.2(3) ?
C3' N4' C5' C51' 56.0(3) ?
C6' N4' C5' C51' -118.4(2) ?
C5" N4' C5' C51' 67.8(5) ?
C6" N4' C5" C52" 61.3(6) ?
C3' N4' C5" C52" -132.3(4) ?
C5' N4' C5" C52" 57.1(6) ?
C6' N4' C5" C52" 47.9(7) ?
C6" N4' C6' C61' 59.4(5) ?
C3' N4' C6' C61' -97.0(2) ?
C5' N4' C6' C61' 78.1(3) ?
C5" N4' C6' C61' 82.7(4) ?
C6" N4' C6' C62' -67.4(5) ?
C3' N4' C6' C62' 136.2(2) ?
C5' N4' C6' C62' -48.7(3) ?
C5" N4' C6' C62' -44.0(5) ?
C3' N4' C6" C62" 80.8(6) ?
C5' N4' C6" C62" -120.5(4) ?
C6' N4' C6" C62" 42.7(4) ?
C5" N4' C6" C62" -122.4(4) ?
