#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:06:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180287 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/01/7150160.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_7150160
loop_
_publ_author_name
'Feuillet, Fred J. P.'
'Cheeseman, Matt'
'Mahon, Mary F.'
'Bull, Steven D.'
_publ_section_title
;
 Stereoselective synthesis of (E)-trisubstituted alpha,beta-unsaturated
 amides and acids.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2976
_journal_page_last               2989
_journal_paper_doi               10.1039/b503633j
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C14 H25 N O2'
_chemical_formula_weight         239.35
_chemical_name_systematic
;
?
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1530(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.3540(2)
_cell_length_b                   9.79700(10)
_cell_length_c                   17.7370(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     2924.06(6)
_computing_data_reduction
'Denzo and Scalepack (otwinowski & Minor, 1997'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       KappaCCD
_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  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43295
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9651
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0085(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc
[1.00000+0.00000exp(0.00(sinθ/λ)²)]/
[σ²(Fo²)+0.0000+0.4117*P+(0.0558P)²+0.0000sinθ/λ]
where P = 0.00000Fo² + 1.00000Fc²
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                4436
_reflns_number_total             6676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503633j.txt
_cod_data_source_block           k02sdb1
_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 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7150160
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37040(6) 0.23652(9) -0.04306(6) 0.0391(3) Uani 1 1 d . . .
O2 O 0.46882(6) 0.09071(10) 0.20573(5) 0.0337(2) Uani 1 1 d . . .
H2 H 0.4874 0.1703 0.2110 0.040 Uiso 1 1 calc R . .
O1A O 0.47390(6) -0.14451(10) 0.29538(5) 0.0335(2) Uani 1 1 d . . .
H1A H 0.4814 -0.0753 0.2701 0.040 Uiso 1 1 calc R . .
O2A O 0.36282(6) -0.23541(9) 0.48687(6) 0.0391(3) Uani 1 1 d . . .
N1 N 0.38350(7) 0.01792(12) -0.00347(6) 0.0294(3) Uani 1 1 d . . .
N1A N 0.37893(7) -0.02080(12) 0.44907(6) 0.0277(3) Uani 1 1 d . . .
C1 C 0.17077(9) -0.08817(16) -0.17769(8) 0.0393(4) Uani 1 1 d . . .
H1E H 0.1680 -0.0422 -0.2286 0.047 Uiso 1 1 calc R . .
C2 C 0.18458(10) -0.2408(2) -0.18626(12) 0.0605(5) Uani 1 1 d . . .
H2E H 0.1928 -0.2853 -0.1348 0.073 Uiso 1 1 calc R . .
H2B H 0.2334 -0.2542 -0.2049 0.073 Uiso 1 1 calc R . .
C3 C 0.11443(11) -0.3085(2) -0.24327(14) 0.0773(7) Uani 1 1 d . . .
H3A H 0.1108 -0.2729 -0.2962 0.093 Uiso 1 1 calc R . .
H3B H 0.1238 -0.4082 -0.2440 0.093 Uiso 1 1 calc R . .
C4 C 0.03739(10) -0.28249(18) -0.22160(13) 0.0616(5) Uani 1 1 d . . .
H4A H -0.0068 -0.3218 -0.2619 0.074 Uiso 1 1 calc R . .
H4B H 0.0383 -0.3285 -0.1717 0.074 Uiso 1 1 calc R . .
C5 C 0.02308(9) -0.13280(17) -0.21386(10) 0.0464(4) Uani 1 1 d . . .
H5A H -0.0265 -0.1194 -0.1965 0.056 Uiso 1 1 calc R . .
H5B H 0.0164 -0.0880 -0.2651 0.056 Uiso 1 1 calc R . .
C6 C 0.09214(9) -0.06795(17) -0.15560(9) 0.0421(4) Uani 1 1 d . . .
H6A H 0.0959 -0.1083 -0.1037 0.051 Uiso 1 1 calc R . .
H6B H 0.0819 0.0310 -0.1522 0.051 Uiso 1 1 calc R . .
C7 C 0.23773(9) -0.02697(15) -0.11709(8) 0.0371(3) Uani 1 1 d . . .
H7 H 0.2441 -0.0618 -0.0660 0.045 Uiso 1 1 calc R . .
C8 C 0.28949(8) 0.06910(14) -0.12480(7) 0.0297(3) Uani 1 1 d . . .
C9 C 0.35088(8) 0.11563(13) -0.05384(7) 0.0281(3) Uani 1 1 d . . .
C10 C 0.44438(8) 0.04575(14) 0.06735(7) 0.0300(3) Uani 1 1 d . . .
H10A H 0.4780 0.1223 0.0579 0.036 Uiso 1 1 calc R . .
H10B H 0.4788 -0.0356 0.0811 0.036 Uiso 1 1 calc R . .
C11 C 0.40895(8) 0.08157(16) 0.13473(8) 0.0346(3) Uani 1 1 d . . .
H11A H 0.3807 0.1700 0.1242 0.042 Uiso 1 1 calc R . .
H11B H 0.3697 0.0110 0.1398 0.042 Uiso 1 1 calc R . .
C12 C 0.28982(8) 0.13865(14) -0.20142(8) 0.0323(3) Uani 1 1 d . . .
H12 H 0.2609 0.0771 -0.2440 0.039 Uiso 1 1 calc R . .
C13 C 0.37366(10) 0.15665(17) -0.21227(9) 0.0442(4) Uani 1 1 d . . .
H13A H 0.4022 0.0696 -0.2024 0.066 Uiso 1 1 calc R . .
H13B H 0.4018 0.2257 -0.1758 0.066 Uiso 1 1 calc R . .
H13C H 0.3709 0.1862 -0.2657 0.066 Uiso 1 1 calc R . .
C14 C 0.24542(11) 0.27433(17) -0.21126(9) 0.0509(4) Uani 1 1 d . . .
H14A H 0.2450 0.3132 -0.2623 0.076 Uiso 1 1 calc R . .
H14B H 0.2720 0.3376 -0.1703 0.076 Uiso 1 1 calc R . .
H14C H 0.1906 0.2594 -0.2075 0.076 Uiso 1 1 calc R . .
C1A C 0.16358(8) 0.10062(15) 0.51321(8) 0.0363(3) Uani 1 1 d . . .
H1A1 H 0.1417 0.0339 0.5453 0.044 Uiso 1 1 calc R A 1
C2A C 0.0976(4) 0.1444(6) 0.4444(4) 0.0492(13) Uani 0.55 1 d P B 1
H2A1 H 0.0753 0.0630 0.4136 0.059 Uiso 0.55 1 calc PR B 1
H2A2 H 0.1197 0.2056 0.4105 0.059 Uiso 0.55 1 calc PR B 1
C3A C 0.0311(4) 0.2192(8) 0.4716(4) 0.0582(18) Uani 0.55 1 d P B 1
H3A1 H -0.0099 0.2502 0.4256 0.070 Uiso 0.55 1 calc PR B 1
H3A2 H 0.0056 0.1551 0.5012 0.070 Uiso 0.55 1 calc PR B 1
C4A C 0.0630(5) 0.3416(9) 0.5224(4) 0.059(2) Uani 0.55 1 d P B 1
H4A1 H 0.0197 0.3830 0.5422 0.071 Uiso 0.55 1 calc PR B 1
H4A2 H 0.0826 0.4112 0.4912 0.071 Uiso 0.55 1 calc PR B 1
C5A C 0.1305(5) 0.2979(10) 0.5907(4) 0.0511(14) Uani 0.55 1 d P B 1
H5A1 H 0.1531 0.3795 0.6211 0.061 Uiso 0.55 1 calc PR B 1
H5A2 H 0.1093 0.2368 0.6252 0.061 Uiso 0.55 1 calc PR B 1
C6A C 0.1957(5) 0.2243(9) 0.5631(3) 0.0416(12) Uani 0.55 1 d P B 1
H6A1 H 0.2374 0.1944 0.6088 0.050 Uiso 0.55 1 calc PR B 1
H6A2 H 0.2203 0.2882 0.5326 0.050 Uiso 0.55 1 calc PR B 1
C7A C 0.23037(8) 0.03413(14) 0.48655(8) 0.0328(3) Uani 1 1 d . B .
H7A H 0.2381 0.0653 0.4382 0.039 Uiso 1 1 calc R . .
C8A C 0.28005(8) -0.06262(13) 0.52174(7) 0.0285(3) Uani 1 1 d . . .
C9A C 0.34371(8) -0.11351(13) 0.48458(7) 0.0273(3) Uani 1 1 d . B .
C10A C 0.44232(8) -0.05540(13) 0.41164(7) 0.0286(3) Uani 1 1 d . . .
H10C H 0.4792 -0.1205 0.4449 0.034 Uiso 1 1 calc R . .
H10D H 0.4727 0.0282 0.4064 0.034 Uiso 1 1 calc R . .
C11A C 0.41055(8) -0.11827(15) 0.33199(8) 0.0322(3) Uani 1 1 d . . .
H11C H 0.3828 -0.2047 0.3372 0.039 Uiso 1 1 calc R . .
H11D H 0.3717 -0.0554 0.2992 0.039 Uiso 1 1 calc R . .
C12A C 0.27580(9) -0.12908(14) 0.59817(8) 0.0339(3) Uani 1 1 d . B .
H12A H 0.2440 -0.0669 0.6236 0.041 Uiso 1 1 calc R . .
C13A C 0.35788(10) -0.14307(19) 0.65387(9) 0.0495(4) Uani 1 1 d . . .
H13D H 0.3520 -0.1715 0.7051 0.074 Uiso 1 1 calc R B .
H13E H 0.3854 -0.0550 0.6584 0.074 Uiso 1 1 calc R . .
H13F H 0.3888 -0.2116 0.6338 0.074 Uiso 1 1 calc R . .
C14A C 0.23226(11) -0.26635(17) 0.58556(9) 0.0485(4) Uani 1 1 d . . .
H14D H 0.1786 -0.2531 0.5525 0.073 Uiso 1 1 calc R B .
H14E H 0.2288 -0.3037 0.6359 0.073 Uiso 1 1 calc R . .
H14F H 0.2615 -0.3300 0.5603 0.073 Uiso 1 1 calc R . .
C2C C 0.0845(5) 0.0899(7) 0.4495(5) 0.0499(17) Uani 0.45 1 d P B 2
H2C1 H 0.0915 0.1335 0.4012 0.060 Uiso 0.45 1 calc PR B 2
H2C2 H 0.0719 -0.0076 0.4380 0.060 Uiso 0.45 1 calc PR B 2
C3C C 0.0151(5) 0.1577(8) 0.4738(6) 0.060(2) Uani 0.45 1 d P B 2
H3C1 H -0.0328 0.1554 0.4300 0.072 Uiso 0.45 1 calc PR B 2
H3C2 H 0.0033 0.1072 0.5180 0.072 Uiso 0.45 1 calc PR B 2
C4C C 0.0360(7) 0.3047(10) 0.4975(7) 0.064(3) Uani 0.45 1 d P B 2
H4C1 H 0.0425 0.3566 0.4516 0.077 Uiso 0.45 1 calc PR B 2
H4C2 H -0.0084 0.3462 0.5154 0.077 Uiso 0.45 1 calc PR B 2
C5C C 0.1090(5) 0.3164(10) 0.5595(6) 0.075(3) Uani 0.45 1 d P B 2
H5C1 H 0.1014 0.2716 0.6071 0.091 Uiso 0.45 1 calc PR B 2
H5C2 H 0.1209 0.4140 0.5714 0.091 Uiso 0.45 1 calc PR B 2
C6C C 0.1805(6) 0.2485(11) 0.5348(5) 0.067(2) Uani 0.45 1 d P B 2
H6C1 H 0.1910 0.2983 0.4898 0.080 Uiso 0.45 1 calc PR B 2
H6C2 H 0.2286 0.2549 0.5782 0.080 Uiso 0.45 1 calc PR B 2
H1 H 0.3674(8) 0.0628(16) 0.4527(8) 0.027(4) Uiso 1 1 d . . .
H2A H 0.3716(9) -0.0662(17) -0.0148(8) 0.036(4) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C10 122.81(12) . . ?
C9A N1A C10A 122.70(11) . . ?
C7 C1 C6 110.46(12) . . ?
C7 C1 C2 110.45(13) . . ?
C6 C1 C2 108.99(13) . . ?
C1 C2 C3 111.78(15) . . ?
C4 C3 C2 111.82(16) . . ?
C5 C4 C3 111.57(16) . . ?
C4 C5 C6 110.55(14) . . ?
C5 C6 C1 112.27(12) . . ?
C8 C7 C1 129.24(13) . . ?
C7 C8 C9 119.02(12) . . ?
C7 C8 C12 123.95(13) . . ?
C9 C8 C12 117.01(11) . . ?
O1 C9 N1 121.90(13) . . ?
O1 C9 C8 122.07(12) . . ?
N1 C9 C8 116.03(11) . . ?
N1 C10 C11 112.06(11) . . ?
O2 C11 C10 111.29(11) . . ?
C8 C12 C13 112.14(12) . . ?
C8 C12 C14 112.35(11) . . ?
C13 C12 C14 110.86(12) . . ?
C6C C1A C7A 112.3(4) . . ?
C6C C1A C2A 89.7(4) . . ?
C7A C1A C2A 110.9(3) . . ?
C6C C1A C6A 21.3(3) . . ?
C7A C1A C6A 109.1(3) . . ?
C2A C1A C6A 109.8(3) . . ?
C6C C1A C2C 109.4(4) . . ?
C7A C1A C2C 110.7(4) . . ?
C2A C1A C2C 22.3(3) . . ?
C6A C1A C2C 127.5(4) . . ?
C1A C2A C3A 111.0(5) . . ?
C4A C3A C2A 111.7(6) . . ?
C3A C4A C5A 110.3(8) . . ?
C6A C5A C4A 111.4(6) . . ?
C5A C6A C1A 111.6(6) . . ?
C8A C7A C1A 128.50(12) . . ?
C7A C8A C9A 119.49(11) . . ?
C7A C8A C12A 123.78(12) . . ?
C9A C8A C12A 116.72(11) . . ?
O2A C9A N1A 121.45(12) . . ?
O2A C9A C8A 121.71(12) . . ?
N1A C9A C8A 116.83(11) . . ?
N1A C10A C11A 112.08(11) . . ?
O1A C11A C10A 110.57(11) . . ?
C8A C12A C13A 111.95(12) . . ?
C8A C12A C14A 112.03(12) . . ?
C13A C12A C14A 111.35(13) . . ?
C3C C2C C1A 112.5(7) . . ?
C4C C3C C2C 109.8(7) . . ?
C5C C4C C3C 112.7(9) . . ?
C4C C5C C6C 110.9(8) . . ?
C1A C6C C5C 111.2(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2338(15) . ?
O2 C11 1.4260(16) . ?
O1A C11A 1.4302(15) . ?
O2A C9A 1.2374(15) . ?
N1 C9 1.3370(17) . ?
N1 C10 1.4558(17) . ?
N1A C9A 1.3356(17) . ?
N1A C10A 1.4571(16) . ?
C1 C7 1.501(2) . ?
C1 C6 1.522(2) . ?
C1 C2 1.528(2) . ?
C2 C3 1.530(2) . ?
C3 C4 1.501(3) . ?
C4 C5 1.499(2) . ?
C5 C6 1.517(2) . ?
C7 C8 1.3310(19) . ?
C8 C9 1.5071(19) . ?
C8 C12 1.5216(18) . ?
C10 C11 1.5130(19) . ?
C12 C13 1.524(2) . ?
C12 C14 1.525(2) . ?
C1A C6C 1.509(11) . ?
C1A C7A 1.5032(19) . ?
C1A C2A 1.517(7) . ?
C1A C6A 1.524(9) . ?
C1A C2C 1.553(10) . ?
C2A C3A 1.541(10) . ?
C3A C4A 1.521(9) . ?
C4A C5A 1.526(7) . ?
C5A C6A 1.520(12) . ?
C7A C8A 1.3297(19) . ?
C8A C9A 1.5032(18) . ?
C8A C12A 1.5218(18) . ?
C10A C11A 1.5159(18) . ?
C12A C13A 1.528(2) . ?
C12A C14A 1.532(2) . ?
C2C C3C 1.527(13) . ?
C3C C4C 1.519(10) . ?
C4C C5C 1.464(11) . ?
C5C C6C 1.561(13) . ?
