#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028911.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4028911
loop_
_publ_author_name
'Morgan, Ian R.'
'Yazici, Arife'
'Pyne, Stephen G.'
'Skelton, Brian W.'
_publ_section_title
;
 Diastereoselective Ritter Reactions of Chiral CyclicN-Acyliminium
 Ions:  Synthesis of Pyrido- and Pyrrolo[2,3-d]oxazoles and
 4-Hydroxy-5-N-acylaminopyrrolidines and
 5-Hydroxy-6-N-acylaminopiperidines
;
_journal_issue                   7
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              2943
_journal_page_last               2946
_journal_paper_doi               10.1021/jo800007g
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H20 N2 O4'
_chemical_formula_sum            'C15 H20 N2 O4'
_chemical_formula_weight         292.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-10-12T20:06:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.224(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2974(4)
_cell_length_b                   7.5545(2)
_cell_length_c                   10.7280(4)
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.4825
_cell_measurement_theta_min      2.6306
_cell_volume                     736.42(5)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
;

 Oxford Diffraction Xcalibur diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10276
_diffrn_reflns_theta_full        31
_diffrn_reflns_theta_max         31
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.95381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                1902
_reflns_number_total             2430
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo800007gsup2.cif
_cod_data_source_block           irm065
_cod_original_sg_symbol_Hall     p_2yb
_cod_database_code               4028911
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
N1 N 0.59305(16) 0.2849(2) 0.36032(14) 0.0146(3) Uani 1 1 d .
C1 C 0.75372(19) 0.2576(2) 0.38273(17) 0.0165(4) Uani 1 1 d .
H1A H 0.7748 0.1531 0.3338 0.02 Uiso 1 1 calc R
H1B H 0.7927 0.2337 0.4744 0.02 Uiso 1 1 calc R
C2 C 0.5310(2) 0.3413(2) 0.45638(17) 0.0165(4) Uani 1 1 d .
O2 O 0.60772(15) 0.37293(19) 0.56356(13) 0.0218(3) Uani 1 1 d .
C3 C 0.3668(2) 0.3716(3) 0.43030(18) 0.0189(4) Uani 1 1 d .
H3A H 0.3485 0.5008 0.4247 0.023 Uiso 1 1 calc R
H3B H 0.3292 0.3269 0.5041 0.023 Uiso 1 1 calc R
C4 C 0.2783(2) 0.2853(3) 0.30960(17) 0.0175(4) Uani 1 1 d .
H4A H 0.2696 0.1564 0.3229 0.021 Uiso 1 1 calc R
H4B H 0.1781 0.3365 0.2879 0.021 Uiso 1 1 calc R
C5 C 0.3579(2) 0.3193(2) 0.20308(18) 0.0172(4) Uani 1 1 d .
H5 H 0.3721 0.4499 0.1962 0.021 Uiso 1 1 calc R
O5 O 0.27464(15) 0.25699(19) 0.08531(12) 0.0219(3) Uani 1 1 d .
H5A H 0.2928 0.3194 0.0257 0.033 Uiso 1 1 calc R
C6 C 0.5093(2) 0.2308(2) 0.23384(17) 0.0144(4) Uani 1 1 d .
H6 H 0.5652 0.2697 0.1686 0.027 Uiso 1 1 calc R
N6 N 0.49991(18) 0.03895(18) 0.23012(15) 0.0166(3) Uani 1 1 d .
H6A H 0.4495 -0.0133 0.2805 0.03 Uiso 1 1 calc R
C61 C 0.5632(2) -0.0641(2) 0.15476(17) 0.0165(4) Uani 1 1 d .
O61 O 0.63191(15) -0.00389(19) 0.07726(13) 0.0213(3) Uani 1 1 d .
C62 C 0.5432(2) -0.2595(3) 0.17013(19) 0.0219(4) Uani 1 1 d .
H62A H 0.6386 -0.319 0.1804 0.033 Uiso 1 1 calc R
H62B H 0.4758 -0.3059 0.0944 0.033 Uiso 1 1 calc R
H62C H 0.502 -0.281 0.2457 0.033 Uiso 1 1 calc R
C11 C 0.8299(2) 0.4176(2) 0.34299(18) 0.0159(4) Uani 1 1 d .
C12 C 0.8554(2) 0.5656(3) 0.42247(18) 0.0184(4) Uani 1 1 d .
H12 H 0.8287 0.562 0.5032 0.022 Uiso 1 1 calc R
C13 C 0.9186(2) 0.7171(3) 0.38596(19) 0.0213(4) Uani 1 1 d .
H13 H 0.9335 0.8173 0.4407 0.026 Uiso 1 1 calc R
C14 C 0.9607(2) 0.7229(3) 0.2687(2) 0.0242(5) Uani 1 1 d .
O14 O 1.02293(18) 0.8780(2) 0.24180(14) 0.0371(4) Uani 1 1 d .
C141 C 1.0769(3) 0.8822(5) 0.1262(2) 0.0577(9) Uani 1 1 d .
H14A H 1.1537 0.7922 0.1301 0.087 Uiso 1 1 calc R
H14B H 1.118 0.9994 0.1159 0.087 Uiso 1 1 calc R
H14C H 0.9959 0.8577 0.0536 0.087 Uiso 1 1 calc R
C15 C 0.9373(2) 0.5767(3) 0.18860(19) 0.0250(5) Uani 1 1 d .
H15 H 0.9658 0.5796 0.1087 0.03 Uiso 1 1 calc R
C16 C 0.8715(2) 0.4253(3) 0.22615(18) 0.0210(4) Uani 1 1 d .
H16 H 0.855 0.3258 0.1708 0.025 Uiso 1 1 calc R
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
C2 N1 C6 124.21(15)
C2 N1 C1 120.01(15)
C6 N1 C1 115.52(14)
N1 C1 C11 111.20(15)
N1 C1 H1A 109.4
C11 C1 H1A 109.4
N1 C1 H1B 109.4
C11 C1 H1B 109.4
H1A C1 H1B 108
O2 C2 N1 120.85(17)
O2 C2 C3 120.16(16)
N1 C2 C3 118.96(16)
C2 C3 C4 115.78(16)
C2 C3 H3A 108.3
C4 C3 H3A 108.3
C2 C3 H3B 108.3
C4 C3 H3B 108.3
H3A C3 H3B 107.4
C5 C4 C3 107.89(15)
C5 C4 H4A 110.1
C3 C4 H4A 110.1
C5 C4 H4B 110.1
C3 C4 H4B 110.1
H4A C4 H4B 108.4
O5 C5 C4 110.87(15)
O5 C5 C6 110.58(15)
C4 C5 C6 109.81(15)
O5 C5 H5 108.5
C4 C5 H5 108.5
C6 C5 H5 108.5
C5 O5 H5A 109.5
N6 C6 N1 108.63(15)
N6 C6 C5 112.54(15)
N1 C6 C5 111.13(15)
N6 C6 H6 108.1
N1 C6 H6 108.1
C5 C6 H6 108.1
C61 N6 C6 124.29(16)
C61 N6 H6A 117.9
C6 N6 H6A 117.9
O61 C61 N6 123.02(17)
O61 C61 C62 121.93(17)
N6 C61 C62 115.04(17)
C61 C62 H62A 109.5
C61 C62 H62B 109.5
H62A C62 H62B 109.5
C61 C62 H62C 109.5
H62A C62 H62C 109.5
H62B C62 H62C 109.5
C16 C11 C12 118.28(18)
C16 C11 C1 121.77(17)
C12 C11 C1 119.92(16)
C13 C12 C11 121.21(18)
C13 C12 H12 119.4
C11 C12 H12 119.4
C12 C13 C14 119.96(19)
C12 C13 H13 120
C14 C13 H13 120
O14 C14 C15 124.83(19)
O14 C14 C13 115.46(19)
C15 C14 C13 119.72(18)
C14 O14 C141 116.3(2)
O14 C141 H14A 109.5
O14 C141 H14B 109.5
H14A C141 H14B 109.5
O14 C141 H14C 109.5
H14A C141 H14C 109.5
H14B C141 H14C 109.5
C14 C15 C16 119.64(18)
C14 C15 H15 120.2
C16 C15 H15 120.2
C11 C16 C15 121.19(19)
C11 C16 H16 119.4
C15 C16 H16 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.352(2)
N1 C6 1.472(2)
N1 C1 1.476(2)
C1 C11 1.507(3)
C1 H1A 0.99
C1 H1B 0.99
C2 O2 1.241(2)
C2 C3 1.510(3)
C3 C4 1.526(3)
C3 H3A 0.99
C3 H3B 0.99
C4 C5 1.509(3)
C4 H4A 0.99
C4 H4B 0.99
C5 O5 1.415(2)
C5 C6 1.530(3)
C5 H5 1
O5 H5A 0.84
C6 N6 1.452(2)
C6 H6 1
N6 C61 1.344(2)
N6 H6A 0.88
C61 O61 1.238(2)
C61 C62 1.501(3)
C62 H62A 0.98
C62 H62B 0.98
C62 H62C 0.98
C11 C16 1.389(3)
C11 C12 1.396(3)
C12 C13 1.381(3)
C12 H12 0.95
C13 C14 1.395(3)
C13 H13 0.95
C14 O14 1.364(3)
C14 C15 1.388(3)
O14 C141 1.433(3)
C141 H14A 0.98
C141 H14B 0.98
C141 H14C 0.98
C15 C16 1.395(3)
C15 H15 0.95
C16 H16 0.95
