#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222515.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_2222515
loop_
_publ_author_name
'Tailor, Dishant'
'Edler, Kate L.'
'Casper, David M.'
'Hitchcock, Shawn R.'
'Ferrence, Gregory M.'
_publ_section_title
(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one
_journal_coeditor_code           ZL2203
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1685
_journal_page_last               o1686
_journal_paper_doi               10.1107/S1600536809022363
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H22 N2 O3'
_chemical_formula_moiety         'C16 H22 N2 O3'
_chemical_formula_sum            'C16 H22 N2 O3'
_chemical_formula_weight         290.36
_chemical_name_systematic
;
(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-
1,3,4-oxadiazinan-2-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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8644(3)
_cell_length_b                   10.8370(5)
_cell_length_c                   21.2348(10)
_cell_measurement_reflns_used    7989
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.437
_cell_measurement_theta_min      2.6855
_cell_volume                     1579.65(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and publCIF (Westrip, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16184
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.8781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0392
_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)+(0.0467P)²+0.4577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2231
_reflns_number_total             2263
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            zl2203.cif
_cod_data_source_block           I
_cod_database_code               2222515
_cod_database_fobs_code          2222515
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 0.75439(18) 0.26491(11) 0.44189(6) 0.0196(3) Uani d . 1 . .
C C2 0.8863(3) 0.34214(16) 0.41773(8) 0.0188(3) Uani d . 1 . .
N N3 0.8136(2) 0.44240(13) 0.38381(7) 0.0178(3) Uani d . 1 . .
N N4 0.6120(2) 0.47290(13) 0.39003(6) 0.0166(3) Uani d . 1 . .
C C5 0.5006(2) 0.36039(15) 0.37440(7) 0.0165(3) Uani d . 1 . .
H H5 0.3593 0.3803 0.3796 0.020 Uiso calc R 1 . .
C C6 0.5509(2) 0.25838(16) 0.42207(8) 0.0163(3) Uani d . 1 . .
H H6 0.4683 0.2717 0.4602 0.020 Uiso calc R 1 . .
C C7 0.5138(3) 0.12801(16) 0.39890(8) 0.0187(3) Uani d . 1 . .
C C8 0.6638(3) 0.05224(17) 0.37881(9) 0.0262(4) Uani d . 1 . .
H H8 0.7946 0.0806 0.3807 0.031 Uiso calc R 1 . .
C C9 0.6234(4) -0.06520(19) 0.35596(10) 0.0326(5) Uani d . 1 . .
H H9 0.7270 -0.1166 0.3421 0.039 Uiso calc R 1 . .
C C10 0.4342(4) -0.10773(17) 0.35327(9) 0.0320(5) Uani d . 1 . .
H H10 0.4073 -0.1883 0.3380 0.038 Uiso calc R 1 . .
C C11 0.2841(3) -0.03214(19) 0.37300(10) 0.0315(4) Uani d . 1 . .
H H11 0.1535 -0.0608 0.3710 0.038 Uiso calc R 1 . .
C C12 0.3230(3) 0.08577(17) 0.39586(9) 0.0251(4) Uani d . 1 . .
H H12 0.2191 0.1373 0.4094 0.030 Uiso calc R 1 . .
C C13 0.5331(3) 0.32666(16) 0.30550(8) 0.0208(3) Uani d . 1 . .
H H13A 0.4971 0.3968 0.2788 0.031 Uiso calc R 1 . .
H H13B 0.4523 0.2552 0.2946 0.031 Uiso calc R 1 . .
H H13C 0.6706 0.3063 0.2988 0.031 Uiso calc R 1 . .
C C14 0.5736(3) 0.52506(17) 0.45405(8) 0.0225(4) Uani d . 1 . .
H H14 0.6017 0.4607 0.4865 0.027 Uiso calc R 1 . .
C C15 0.7025(3) 0.63686(18) 0.46590(10) 0.0310(4) Uani d . 1 . .
H H15A 0.8396 0.6123 0.4632 0.046 Uiso calc R 1 . .
H H15B 0.6756 0.6700 0.5079 0.046 Uiso calc R 1 . .
H H15C 0.6752 0.7002 0.4342 0.046 Uiso calc R 1 . .
C C16 0.3600(3) 0.5623(2) 0.45843(11) 0.0344(5) Uani d . 1 . .
H H16B 0.2776 0.4899 0.4511 0.052 Uiso calc R 1 . .
H H16A 0.3318 0.6253 0.4266 0.052 Uiso calc R 1 . .
H H16C 0.3334 0.5958 0.5004 0.052 Uiso calc R 1 . .
C C17 0.9228(2) 0.50008(16) 0.33572(8) 0.0195(3) Uani d . 1 . .
C C18 0.8239(3) 0.60532(17) 0.30136(9) 0.0245(4) Uani d . 1 . .
H H18A 0.7224 0.5718 0.2730 0.029 Uiso calc R 1 . .
H H18B 0.7594 0.6601 0.3323 0.029 Uiso calc R 1 . .
C C19 0.9691(3) 0.6793(2) 0.26320(11) 0.0344(5) Uani d . 1 . .
H H19C 0.9013 0.7465 0.2414 0.052 Uiso calc R 1 . .
H H19B 1.0317 0.6254 0.2322 0.052 Uiso calc R 1 . .
H H19A 1.0682 0.7139 0.2913 0.052 Uiso calc R 1 . .
O O20 1.08450(19) 0.46487(14) 0.32269(7) 0.0296(3) Uani d . 1 . .
O O21 1.05596(18) 0.32428(13) 0.42830(6) 0.0266(3) Uani d . 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 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
C2 O1 C6 . . 124.62(13) ?
O21 C2 O1 . . 118.98(16) ?
O21 C2 N3 . . 124.62(16) ?
O1 C2 N3 . . 116.34(15) ?
C2 N3 C17 . . 121.86(14) ?
C2 N3 N4 . . 118.59(14) ?
C17 N3 N4 . . 118.58(14) ?
N3 N4 C5 . . 106.83(12) ?
N3 N4 C14 . . 110.01(13) ?
C5 N4 C14 . . 115.14(13) ?
N4 C5 C13 . . 109.75(13) ?
N4 C5 C6 . . 109.23(13) ?
C13 C5 C6 . . 115.24(14) ?
N4 C5 H5 . . 107.4 ?
C13 C5 H5 . . 107.4 ?
C6 C5 H5 . . 107.4 ?
O1 C6 C7 . . 107.41(14) ?
O1 C6 C5 . . 111.69(13) ?
C7 C6 C5 . . 114.71(13) ?
O1 C6 H6 . . 107.6 ?
C7 C6 H6 . . 107.6 ?
C5 C6 H6 . . 107.6 ?
C8 C7 C12 . . 119.44(17) ?
C8 C7 C6 . . 121.81(16) ?
C12 C7 C6 . . 118.71(15) ?
C7 C8 C9 . . 120.16(19) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C10 C9 C8 . . 120.54(19) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 119.44(18) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C10 C11 C12 . . 120.46(19) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C7 C12 C11 . . 119.96(18) ?
C7 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C5 C13 H13A . . 109.5 ?
C5 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C5 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N4 C14 C15 . . 110.40(15) ?
N4 C14 C16 . . 108.99(15) ?
C15 C14 C16 . . 109.78(16) ?
N4 C14 H14 . . 109.2 ?
C15 C14 H14 . . 109.2 ?
C16 C14 H14 . . 109.2 ?
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 ?
C14 C16 H16B . . 109.5 ?
C14 C16 H16A . . 109.5 ?
H16B C16 H16A . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
O20 C17 N3 . . 120.94(16) ?
O20 C17 C18 . . 122.72(16) ?
N3 C17 C18 . . 116.33(15) ?
C19 C18 C17 . . 111.18(16) ?
C19 C18 H18A . . 109.4 ?
C17 C18 H18A . . 109.4 ?
C19 C18 H18B . . 109.4 ?
C17 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
C18 C19 H19C . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19C C19 H19B . . 109.5 ?
C18 C19 H19A . . 109.5 ?
H19C C19 H19A . . 109.5 ?
H19B C19 H19A . . 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 C2 . 1.336(2) ?
O1 C6 . 1.460(2) ?
C2 O21 . 1.202(2) ?
C2 N3 . 1.396(2) ?
N3 C17 . 1.413(2) ?
N3 N4 . 1.4291(19) ?
N4 C5 . 1.477(2) ?
N4 C14 . 1.496(2) ?
C5 C13 . 1.524(2) ?
C5 C6 . 1.538(2) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.518(2) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.384(3) ?
C7 C12 . 1.389(3) ?
C8 C9 . 1.390(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.379(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.393(3) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 C15 . 1.521(3) ?
C14 C16 . 1.523(3) ?
C14 H14 . 1.0000 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16C . 0.9800 ?
C17 O20 . 1.206(2) ?
C17 C18 . 1.515(2) ?
C18 C19 . 1.514(3) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 H19C . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19A . 0.9800 ?
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
C8 H8 O1 . 0.95 2.40 2.737(2) 100.5
C14 H14 O1 . 1.00 2.55 3.091(2) 113.8
C15 H15A N3 . 0.98 2.50 2.839(2) 99.8
C5 H5 O20 1_455 1.00 2.42 3.263(2) 141.5
C16 H16B O21 1_455 0.98 2.40 3.380(3) 174.9
C12 H12 O21 1_455 0.95 2.35 3.243(2) 156.4
C5 H5 O21 1_455 1.00 2.40 3.283(2) 146.5
C6 H6 O1 3_456 1.00 2.58 3.543(2) 162.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 O1 C2 O21 . . . . -165.68(17) ?
C6 O1 C2 N3 . . . . 17.1(2) ?
O21 C2 N3 C17 . . . . 29.6(3) ?
O1 C2 N3 C17 . . . . -153.40(15) ?
O21 C2 N3 N4 . . . . -161.87(17) ?
O1 C2 N3 N4 . . . . 15.2(2) ?
C2 N3 N4 C5 . . . . -55.15(18) ?
C17 N3 N4 C5 . . . . 113.79(15) ?
C2 N3 N4 C14 . . . . 70.48(18) ?
C17 N3 N4 C14 . . . . -120.58(16) ?
N3 N4 C5 C13 . . . . -64.81(16) ?
C14 N4 C5 C13 . . . . 172.72(14) ?
N3 N4 C5 C6 . . . . 62.43(16) ?
C14 N4 C5 C6 . . . . -60.04(17) ?
C2 O1 C6 C7 . . . . 120.86(16) ?
C2 O1 C6 C5 . . . . -5.7(2) ?
N4 C5 C6 O1 . . . . -34.68(18) ?
C13 C5 C6 O1 . . . . 89.39(17) ?
N4 C5 C6 C7 . . . . -157.20(14) ?
C13 C5 C6 C7 . . . . -33.1(2) ?
O1 C6 C7 C8 . . . . -22.1(2) ?
C5 C6 C7 C8 . . . . 102.74(19) ?
O1 C6 C7 C12 . . . . 160.20(15) ?
C5 C6 C7 C12 . . . . -75.0(2) ?
C12 C7 C8 C9 . . . . -0.2(3) ?
C6 C7 C8 C9 . . . . -177.88(17) ?
C7 C8 C9 C10 . . . . -0.3(3) ?
C8 C9 C10 C11 . . . . 0.6(3) ?
C9 C10 C11 C12 . . . . -0.4(3) ?
C8 C7 C12 C11 . . . . 0.3(3) ?
C6 C7 C12 C11 . . . . 178.08(16) ?
C10 C11 C12 C7 . . . . 0.0(3) ?
N3 N4 C14 C15 . . . . 56.73(18) ?
C5 N4 C14 C15 . . . . 177.48(15) ?
N3 N4 C14 C16 . . . . 177.38(15) ?
C5 N4 C14 C16 . . . . -61.87(18) ?
C2 N3 C17 O20 . . . . -0.7(3) ?
N4 N3 C17 O20 . . . . -169.21(16) ?
C2 N3 C17 C18 . . . . 178.17(16) ?
N4 N3 C17 C18 . . . . 9.6(2) ?
O20 C17 C18 C19 . . . . -15.4(3) ?
N3 C17 C18 C19 . . . . 165.80(17) ?
O21 C2 C17 O20 . . . . 23.67(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742614
