#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/07/7150760.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_7150760
loop_
_publ_author_name
'Bollans, Lee'
'Bacsa, John'
'Iggo, Jonathan A.'
'Morris, Gareth A.'
'Stachulski, Andrew V.'
_publ_section_title
;
 The acyl nitroso Diels--Alder (ANDA) reaction of sorbate derivatives:
 an X-ray and 15N NMR study with an application to amino-acid synthesis
;
_journal_issue                   21
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4531
_journal_page_last               4538
_journal_paper_doi               10.1039/b912963d
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C18 H22 N2 O7'
_chemical_formula_sum            'C18 H22 N2 O7'
_chemical_formula_weight         378.38
_chemical_name_common
;
tert-butyl 3-methyl-6-((((4-nitrophenyl)carbonyl)oxy)methyl)-
1,2-oxazinane-2-carboxylate
;
_chemical_name_systematic
;
tert-butyl
3-methyl-6-
({[(4-nitrophenyl)carbonyl]oxy}methyl)-1,2-oxazinane-
2-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.694(4)
_cell_angle_beta                 88.672(4)
_cell_angle_gamma                85.198(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8725(14)
_cell_length_b                   10.826(3)
_cell_length_c                   14.459(3)
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.73
_cell_volume                     883.5(4)
_computing_cell_refinement       'SAINT v6.45a (Bruker, 2005)'
_computing_data_collection       'SMART v.5.632 (Bruker, 2005)'
_computing_data_reduction        'SAINT v6.45a (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX detector'
_diffrn_measurement_method       'ω scans with a narrow frame width'
_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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5215
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008-1 (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0386
_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)+(0.0590P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                3168
_reflns_number_total             3709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b912963d.txt
_cod_data_source_block           stac205m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150760
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.05280(15) 0.75888(8) 0.57661(6) 1.000 0.0160(3) . .
O2 O Uani 0.26712(16) 0.75442(8) 0.39251(6) 1.000 0.0180(3) . .
O3 O Uani 0.61876(17) 0.65679(8) 0.38129(6) 1.000 0.0216(3) . .
O4 O Uani -0.06615(15) 0.61858(8) 0.73560(6) 1.000 0.0171(3) . .
O5 O Uani 0.08058(16) 0.74111(8) 0.82260(6) 1.000 0.0210(3) . .
O6 O Uani 0.4746(2) 1.23414(10) -0.01057(7) 1.000 0.0332(3) . .
O7 O Uani 0.82112(19) 1.15150(10) -0.01509(7) 1.000 0.0334(3) . .
N1 N Uani 0.07834(18) 0.80390(9) 0.65928(7) 1.000 0.0153(3) . .
N2 N Uani 0.6300(2) 1.15293(10) 0.02099(8) 1.000 0.0223(3) . .
C1 C Uani 0.2784(2) 0.87903(11) 0.65061(9) 1.000 0.0166(4) . .
C2 C Uani 0.4829(2) 0.80352(12) 0.62296(8) 1.000 0.0184(4) . .
C3 C Uani 0.4631(2) 0.70508(12) 0.58625(8) 1.000 0.0182(4) . .
C4 C Uani 0.2350(2) 0.66393(11) 0.56820(8) 1.000 0.0168(4) . .
C5 C Uani 0.0361(2) 0.71807(11) 0.74764(9) 1.000 0.0161(3) . .
C6 C Uani -0.1354(2) 0.51560(12) 0.81937(8) 1.000 0.0176(4) . .
C7 C Uani -0.3130(2) 0.57075(13) 0.87798(9) 1.000 0.0235(4) . .
C8 C Uani 0.0751(2) 0.45069(13) 0.87666(10) 1.000 0.0242(4) . .
C9 C Uani -0.2384(2) 0.42582(12) 0.77053(9) 1.000 0.0227(4) . .
C10 C Uani 0.2336(2) 1.00933(12) 0.57872(9) 1.000 0.0200(4) . .
C11 C Uani 0.2060(2) 0.64498(12) 0.46893(8) 1.000 0.0184(4) . .
C12 C Uani 0.4748(2) 0.74444(11) 0.35274(8) 1.000 0.0166(4) . .
C13 C Uani 0.5069(2) 0.85435(11) 0.26671(8) 1.000 0.0163(4) . .
C14 C Uani 0.3371(2) 0.95352(12) 0.23341(9) 1.000 0.0181(4) . .
C15 C Uani 0.3755(2) 1.05228(12) 0.15216(9) 1.000 0.0193(4) . .
C16 C Uani 0.5856(2) 1.04859(12) 0.10704(9) 1.000 0.0186(4) . .
C17 C Uani 0.7568(2) 0.95206(12) 0.13838(9) 1.000 0.0206(4) . .
C18 C Uani 0.7160(2) 0.85416(12) 0.21926(9) 1.000 0.0201(4) . .
H1 H Uiso 0.20960 0.58150 0.61690 1.000 0.0200 calc R
H2 H Uiso 0.59760 0.65930 0.57090 1.000 0.0220 calc R
H3 H Uiso 0.63130 0.82720 0.63210 1.000 0.0220 calc R
H4 H Uiso 0.30840 0.89340 0.71460 1.000 0.0200 calc R
H6A H Uiso 0.30240 0.56760 0.46370 1.000 0.0220 calc R
H6B H Uiso 0.04480 0.62960 0.46060 1.000 0.0220 calc R
H7A H Uiso 0.19450 0.99700 0.51640 1.000 0.0300 calc R
H7B H Uiso 0.37090 1.05650 0.57210 1.000 0.0300 calc R
H7C H Uiso 0.10640 1.05830 0.60140 1.000 0.0300 calc R
H10 H Uiso 0.83130 0.78670 0.24240 1.000 0.0240 calc R
H11 H Uiso 0.89880 0.95260 0.10550 1.000 0.0250 calc R
H13 H Uiso 0.26110 1.12010 0.12840 1.000 0.0230 calc R
H14 H Uiso 0.19510 0.95360 0.26620 1.000 0.0220 calc R
H18A H Uiso 0.18810 0.42250 0.83400 1.000 0.0360 calc R
H18B H Uiso 0.03240 0.37610 0.92700 1.000 0.0360 calc R
H18C H Uiso 0.14080 0.51150 0.90600 1.000 0.0360 calc R
H19A H Uiso -0.37200 0.47050 0.73310 1.000 0.0340 calc R
H19B H Uiso -0.28520 0.35040 0.81910 1.000 0.0340 calc R
H19C H Uiso -0.12470 0.39830 0.72780 1.000 0.0340 calc R
H20A H Uiso -0.24240 0.62810 0.90910 1.000 0.0350 calc R
H20B H Uiso -0.37520 0.50070 0.92690 1.000 0.0350 calc R
H20C H Uiso -0.43660 0.61920 0.83590 1.000 0.0350 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 0.0000 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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C4 111.89(8) . . . yes
C11 O2 C12 116.69(9) . . . yes
C5 O4 C6 121.02(9) . . . yes
O1 N1 C1 111.18(9) . . . yes
O1 N1 C5 116.44(9) . . . yes
C1 N1 C5 118.35(10) . . . yes
O6 N2 O7 123.96(12) . . . yes
O6 N2 C16 118.30(11) . . . yes
O7 N2 C16 117.73(11) . . . yes
N1 C1 C2 109.17(10) . . . yes
N1 C1 C10 110.75(10) . . . yes
C2 C1 C10 111.69(10) . . . no
C1 C2 C3 122.13(11) . . . no
C2 C3 C4 121.87(11) . . . no
O1 C4 C3 111.29(10) . . . yes
O1 C4 C11 104.79(9) . . . yes
C3 C4 C11 114.79(10) . . . no
O4 C5 O5 127.74(12) . . . yes
O4 C5 N1 110.80(10) . . . yes
O5 C5 N1 121.35(11) . . . yes
O4 C6 C7 109.91(10) . . . yes
O4 C6 C8 109.42(10) . . . yes
O4 C6 C9 101.54(9) . . . yes
C7 C6 C8 113.27(10) . . . no
C7 C6 C9 110.93(10) . . . no
C8 C6 C9 111.14(11) . . . no
O2 C11 C4 112.99(10) . . . yes
O2 C12 O3 124.67(11) . . . yes
O2 C12 C13 111.97(10) . . . yes
O3 C12 C13 123.35(11) . . . yes
C12 C13 C14 122.67(11) . . . no
C12 C13 C18 117.13(11) . . . no
C14 C13 C18 120.19(11) . . . no
C13 C14 C15 120.12(11) . . . no
C14 C15 C16 117.92(12) . . . no
N2 C16 C15 118.71(11) . . . yes
N2 C16 C17 118.02(11) . . . yes
C15 C16 C17 123.27(12) . . . no
C16 C17 C18 118.19(11) . . . no
C13 C18 C17 120.31(11) . . . no
N1 C1 H4 108.00 . . . no
C2 C1 H4 108.00 . . . no
C10 C1 H4 108.00 . . . no
C1 C2 H3 119.00 . . . no
C3 C2 H3 119.00 . . . no
C2 C3 H2 119.00 . . . no
C4 C3 H2 119.00 . . . no
O1 C4 H1 109.00 . . . no
C3 C4 H1 109.00 . . . no
C11 C4 H1 109.00 . . . no
C6 C7 H20A 109.00 . . . no
C6 C7 H20B 109.00 . . . no
C6 C7 H20C 109.00 . . . no
H20A C7 H20B 110.00 . . . no
H20A C7 H20C 109.00 . . . no
H20B C7 H20C 109.00 . . . no
C6 C8 H18A 109.00 . . . no
C6 C8 H18B 109.00 . . . no
C6 C8 H18C 109.00 . . . no
H18A C8 H18B 109.00 . . . no
H18A C8 H18C 109.00 . . . no
H18B C8 H18C 109.00 . . . no
C6 C9 H19A 110.00 . . . no
C6 C9 H19B 109.00 . . . no
C6 C9 H19C 109.00 . . . no
H19A C9 H19B 109.00 . . . no
H19A C9 H19C 109.00 . . . no
H19B C9 H19C 109.00 . . . no
C1 C10 H7A 109.00 . . . no
C1 C10 H7B 109.00 . . . no
C1 C10 H7C 109.00 . . . no
H7A C10 H7B 109.00 . . . no
H7A C10 H7C 109.00 . . . no
H7B C10 H7C 109.00 . . . no
O2 C11 H6A 109.00 . . . no
O2 C11 H6B 109.00 . . . no
C4 C11 H6A 109.00 . . . no
C4 C11 H6B 109.00 . . . no
H6A C11 H6B 108.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C14 C15 H13 121.00 . . . no
C16 C15 H13 121.00 . . . no
C16 C17 H11 121.00 . . . no
C18 C17 H11 121.00 . . . no
C13 C18 H10 120.00 . . . no
C17 C18 H10 120.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4202(14) . . yes
O1 C4 1.4464(15) . . yes
O2 C11 1.4544(15) . . yes
O2 C12 1.3446(15) . . yes
O3 C12 1.2086(16) . . yes
O4 C5 1.3278(16) . . yes
O4 C6 1.4885(15) . . yes
O5 C5 1.2132(15) . . yes
O6 N2 1.2195(16) . . yes
O7 N2 1.2273(16) . . yes
N1 C1 1.4686(16) . . yes
N1 C5 1.3980(16) . . yes
N2 C16 1.4779(17) . . yes
C1 C2 1.5021(18) . . no
C1 C10 1.5218(18) . . no
C2 C3 1.3241(19) . . no
C3 C4 1.4961(17) . . no
C4 C11 1.5179(17) . . no
C6 C7 1.5114(18) . . no
C6 C8 1.5175(18) . . no
C6 C9 1.5132(18) . . no
C12 C13 1.4980(17) . . no
C13 C14 1.3960(18) . . no
C13 C18 1.3928(17) . . no
C14 C15 1.3925(18) . . no
C15 C16 1.3848(17) . . no
C16 C17 1.3796(18) . . no
C17 C18 1.3869(18) . . no
C1 H4 1.0000 . . no
C2 H3 0.9500 . . no
C3 H2 0.9500 . . no
C4 H1 1.0000 . . no
C7 H20A 0.9800 . . no
C7 H20B 0.9800 . . no
C7 H20C 0.9800 . . no
C8 H18A 0.9800 . . no
C8 H18B 0.9800 . . no
C8 H18C 0.9800 . . no
C9 H19A 0.9800 . . no
C9 H19B 0.9800 . . no
C9 H19C 0.9800 . . no
C10 H7A 0.9800 . . no
C10 H7B 0.9800 . . no
C10 H7C 0.9800 . . no
C11 H6A 0.9900 . . no
C11 H6B 0.9900 . . no
C14 H14 0.9500 . . no
C15 H13 0.9500 . . no
C17 H11 0.9500 . . no
C18 H10 0.9500 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H1 O4 1.0000 2.4200 2.9235(16) 110.00 . yes
C1 H4 O5 1.0000 2.4200 2.8212(17) 103.00 . yes
C11 H6A O3 0.9900 2.3200 2.7058(17) 102.00 . yes
C17 H11 O7 0.9500 2.4600 3.3111(19) 149.00 2_775 yes
C8 H18C O5 0.9800 2.4600 3.0357(19) 117.00 . yes
C7 H20A O5 0.9800 2.4800 3.0386(18) 116.00 . yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 N1 C1 67.76(11) . . . . no
C4 O1 N1 C5 -71.84(12) . . . . no
N1 O1 C4 C3 -45.39(12) . . . . no
N1 O1 C4 C11 -170.02(9) . . . . no
C12 O2 C11 C4 100.16(12) . . . . no
C11 O2 C12 O3 -6.56(17) . . . . no
C11 O2 C12 C13 172.34(9) . . . . no
C6 O4 C5 O5 -1.98(19) . . . . no
C6 O4 C5 N1 -178.15(10) . . . . no
C5 O4 C6 C7 63.22(13) . . . . no
C5 O4 C6 C8 -61.75(14) . . . . no
C5 O4 C6 C9 -179.29(10) . . . . no
O1 N1 C1 C2 -50.78(12) . . . . no
O1 N1 C1 C10 72.60(12) . . . . no
C5 N1 C1 C2 87.96(13) . . . . no
C5 N1 C1 C10 -148.67(11) . . . . no
O1 N1 C5 O4 -12.88(14) . . . . no
O1 N1 C5 O5 170.66(11) . . . . no
C1 N1 C5 O4 -149.51(10) . . . . no
C1 N1 C5 O5 34.04(17) . . . . no
O6 N2 C16 C15 -4.53(18) . . . . no
O6 N2 C16 C17 175.48(12) . . . . no
O7 N2 C16 C15 176.35(12) . . . . no
O7 N2 C16 C17 -3.64(18) . . . . no
N1 C1 C2 C3 17.67(16) . . . . no
C10 C1 C2 C3 -105.15(13) . . . . no
C1 C2 C3 C4 1.12(18) . . . . no
C2 C3 C4 O1 11.93(15) . . . . no
C2 C3 C4 C11 130.73(12) . . . . no
O1 C4 C11 O2 71.29(12) . . . . no
C3 C4 C11 O2 -51.09(14) . . . . no
O2 C12 C13 C14 -0.31(17) . . . . no
O2 C12 C13 C18 -179.83(11) . . . . no
O3 C12 C13 C14 178.60(12) . . . . no
O3 C12 C13 C18 -0.91(18) . . . . no
C12 C13 C14 C15 -179.05(11) . . . . no
C18 C13 C14 C15 0.45(19) . . . . no
C12 C13 C18 C17 179.23(11) . . . . no
C14 C13 C18 C17 -0.30(19) . . . . no
C13 C14 C15 C16 -0.44(19) . . . . no
C14 C15 C16 N2 -179.68(11) . . . . no
C14 C15 C16 C17 0.3(2) . . . . no
N2 C16 C17 C18 179.83(11) . . . . no
C15 C16 C17 C18 -0.2(2) . . . . no
C16 C17 C18 C13 0.15(19) . . . . no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25944570
