#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024461.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_4024461
loop_
_publ_author_name
'Elise Claveau'
'Isabelle Gillaizeau'
'Justyna Kalinowska-Tluscik'
'Pascal Bouyssou'
'Gérard Coudert'
_publ_section_title
;
Nucleophilic Addition onto Methyl-4H-1,4-oxazine-3-carboxylate Moiety:
Short Access to 1,4-Diazine Privileged Substructures
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2911
_journal_page_last               2914
_journal_paper_doi               10.1021/jo900291f
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H15 N1 O5'
_chemical_formula_sum            'C11 H15 N O5'
_chemical_formula_weight         241.24
_chemical_name_common            'Compound ec616'
_chemical_name_systematic
;
?
;
_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_date             2008-07-17T01:19:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                77.0301(11)
_cell_angle_beta                 76.9064(10)
_cell_angle_gamma                81.5540(13)
_cell_formula_units_Z            2
_cell_length_a                   6.2233(2)
_cell_length_b                   7.3164(2)
_cell_length_c                   13.5519(4)
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.508
_cell_measurement_theta_min      0.998
_cell_volume                     582.67(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines (Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.1288353
_diffrn_orient_matrix_UB_12      0.0628353
_diffrn_orient_matrix_UB_13      0.0833765
_diffrn_orient_matrix_UB_21      0.0382395
_diffrn_orient_matrix_UB_22      -0.0918167
_diffrn_orient_matrix_UB_23      0.0999152
_diffrn_orient_matrix_UB_31      0.0529756
_diffrn_orient_matrix_UB_32      0.0555438
_diffrn_orient_matrix_UB_33      0.009126
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5652
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.1262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2713
_reflns_number_total             3540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900291f_si_001.cif
_cod_data_source_block           ec616
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43256(13) 0.17543(12) 0.58438(6) 0.02019(19) Uani 1 1 d . . .
O4 O 0.61138(12) 0.19015(11) 0.23981(6) 0.01586(18) Uani 1 1 d . . .
O3 O 0.48014(13) 0.57399(11) 0.25835(6) 0.01998(19) Uani 1 1 d . . .
O5 O 0.95556(13) 0.09901(12) 0.27789(6) 0.01896(18) Uani 1 1 d . . .
O2 O 0.14684(12) 0.47974(11) 0.34388(6) 0.01787(18) Uani 1 1 d . . .
N1 N 0.68143(15) 0.24802(13) 0.38334(7) 0.0156(2) Uani 1 1 d . . .
C2 C 0.34518(19) 0.28871(16) 0.50471(9) 0.0176(2) Uani 1 1 d . . .
C1 C 0.45749(17) 0.32652(15) 0.40801(8) 0.0144(2) Uani 1 1 d . . .
C6 C 0.0440(2) 0.61808(17) 0.26922(10) 0.0203(2) Uani 1 1 d . . .
C7 C 0.76651(18) 0.17112(15) 0.29634(9) 0.0152(2) Uani 1 1 d . . .
C5 C 0.36885(18) 0.47328(15) 0.32781(9) 0.0148(2) Uani 1 1 d . . .
C3 C 0.66443(19) 0.14831(16) 0.56412(9) 0.0180(2) Uani 1 1 d . . .
C8 C 0.67233(18) 0.17662(16) 0.12958(8) 0.0161(2) Uani 1 1 d . . .
C9 C 0.7649(2) -0.02356(17) 0.11859(10) 0.0217(2) Uani 1 1 d . . .
C10 C 0.4499(2) 0.2274(2) 0.09629(10) 0.0231(3) Uani 1 1 d . . .
C4 C 0.78560(19) 0.18414(16) 0.46990(9) 0.0168(2) Uani 1 1 d . . .
C11 C 0.8325(2) 0.32139(18) 0.07258(10) 0.0217(2) Uani 1 1 d . . .
H2 H 0.198(3) 0.342(2) 0.5277(12) 0.026 Uiso 1 1 d . . .
H4 H 0.943(3) 0.169(2) 0.4559(12) 0.026 Uiso 1 1 d . . .
H6A H 0.058(3) 0.741(2) 0.2771(13) 0.033 Uiso 1 1 d . . .
H3 H 0.722(2) 0.105(2) 0.6274(12) 0.026 Uiso 1 1 d . . .
H10A H 0.343(3) 0.136(2) 0.1350(13) 0.033 Uiso 1 1 d . . .
H10B H 0.389(3) 0.358(2) 0.1077(12) 0.033 Uiso 1 1 d . . .
H9A H 0.912(3) -0.055(2) 0.1329(12) 0.033 Uiso 1 1 d . . .
H6B H -0.110(3) 0.593(2) 0.2840(13) 0.033 Uiso 1 1 d . . .
H10C H 0.472(3) 0.224(2) 0.0223(13) 0.033 Uiso 1 1 d . . .
H11A H 0.770(3) 0.447(2) 0.0828(13) 0.033 Uiso 1 1 d . . .
H11B H 0.976(3) 0.292(2) 0.0940(12) 0.033 Uiso 1 1 d . . .
H11C H 0.859(3) 0.323(2) -0.0037(13) 0.033 Uiso 1 1 d . . .
H6C H 0.113(3) 0.596(2) 0.1981(13) 0.033 Uiso 1 1 d . . .
H9B H 0.662(3) -0.116(2) 0.1640(13) 0.033 Uiso 1 1 d . . .
H9C H 0.776(3) -0.039(2) 0.0464(13) 0.033 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 0 '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'
N N 0.0061 0.0033 '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
C2 O1 C3 114.10(9) . . ?
C7 O4 C8 121.01(8) . . ?
C5 O2 C6 115.07(9) . . ?
C7 N1 C1 123.18(9) . . ?
C7 N1 C4 117.98(9) . . ?
C1 N1 C4 114.35(9) . . ?
C1 C2 O1 123.58(10) . . ?
C1 C2 H2 124.3(9) . . ?
O1 C2 H2 112.1(9) . . ?
C2 C1 N1 119.60(10) . . ?
C2 C1 C5 121.52(10) . . ?
N1 C1 C5 118.13(9) . . ?
O2 C6 H6A 109.5(10) . . ?
O2 C6 H6B 105.6(10) . . ?
H6A C6 H6B 111.7(13) . . ?
O2 C6 H6C 109.0(9) . . ?
H6A C6 H6C 112.6(13) . . ?
H6B C6 H6C 108.2(13) . . ?
O5 C7 O4 127.47(10) . . ?
O5 C7 N1 122.60(10) . . ?
O4 C7 N1 109.93(9) . . ?
O3 C5 O2 124.47(10) . . ?
O3 C5 C1 124.78(10) . . ?
O2 C5 C1 110.75(9) . . ?
C4 C3 O1 122.69(10) . . ?
C4 C3 H3 125.6(9) . . ?
O1 C3 H3 111.7(9) . . ?
O4 C8 C11 108.98(9) . . ?
O4 C8 C9 110.39(9) . . ?
C11 C8 C9 113.03(10) . . ?
O4 C8 C10 102.02(9) . . ?
C11 C8 C10 111.05(10) . . ?
C9 C8 C10 110.81(10) . . ?
C8 C9 H9A 112.2(10) . . ?
C8 C9 H9B 110.4(9) . . ?
H9A C9 H9B 110.8(13) . . ?
C8 C9 H9C 110.2(9) . . ?
H9A C9 H9C 106.5(13) . . ?
H9B C9 H9C 106.5(13) . . ?
C8 C10 H10A 111.3(9) . . ?
C8 C10 H10B 109.1(9) . . ?
H10A C10 H10B 110.1(13) . . ?
C8 C10 H10C 108.8(9) . . ?
H10A C10 H10C 107.7(13) . . ?
H10B C10 H10C 109.8(13) . . ?
C3 C4 N1 120.15(10) . . ?
C3 C4 H4 123.0(9) . . ?
N1 C4 H4 116.8(9) . . ?
C8 C11 H11A 111.0(10) . . ?
C8 C11 H11B 112.3(10) . . ?
H11A C11 H11B 109.1(13) . . ?
C8 C11 H11C 109.0(9) . . ?
H11A C11 H11C 107.3(13) . . ?
H11B C11 H11C 108.0(13) . . ?
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 C2 1.3712(13) . ?
O1 C3 1.3993(14) . ?
O4 C7 1.3365(13) . ?
O4 C8 1.4777(13) . ?
O3 C5 1.2050(13) . ?
O5 C7 1.2119(13) . ?
O2 C5 1.3445(13) . ?
O2 C6 1.4496(13) . ?
N1 C7 1.3836(14) . ?
N1 C1 1.4226(13) . ?
N1 C4 1.4228(14) . ?
C2 C1 1.3272(16) . ?
C2 H2 0.952(15) . ?
C1 C5 1.4874(15) . ?
C6 H6A 0.947(17) . ?
C6 H6B 0.967(17) . ?
C6 H6C 1.001(17) . ?
C3 C4 1.3188(17) . ?
C3 H3 0.973(16) . ?
C8 C11 1.5185(16) . ?
C8 C9 1.5199(16) . ?
C8 C10 1.5213(16) . ?
C9 H9A 0.965(16) . ?
C9 H9B 1.004(17) . ?
C9 H9C 0.995(17) . ?
C10 H10A 0.989(17) . ?
C10 H10B 1.009(17) . ?
C10 H10C 0.986(17) . ?
C4 H4 0.952(15) . ?
C11 H11A 0.973(17) . ?
C11 H11B 0.979(16) . ?
C11 H11C 1.007(17) . ?
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
C3 O1 C2 C1 18.33(16) . . . . ?
O1 C2 C1 N1 -0.31(17) . . . . ?
O1 C2 C1 C5 -170.16(10) . . . . ?
C7 N1 C1 C2 136.87(12) . . . . ?
C4 N1 C1 C2 -18.81(14) . . . . ?
C7 N1 C1 C5 -52.94(14) . . . . ?
C4 N1 C1 C5 151.38(10) . . . . ?
C8 O4 C7 O5 -19.29(17) . . . . ?
C8 O4 C7 N1 160.61(9) . . . . ?
C1 N1 C7 O5 -177.49(10) . . . . ?
C4 N1 C7 O5 -22.63(16) . . . . ?
C1 N1 C7 O4 2.61(14) . . . . ?
C4 N1 C7 O4 157.47(9) . . . . ?
C6 O2 C5 O3 0.95(16) . . . . ?
C6 O2 C5 C1 -179.65(9) . . . . ?
C2 C1 C5 O3 145.12(12) . . . . ?
N1 C1 C5 O3 -24.87(16) . . . . ?
C2 C1 C5 O2 -34.28(14) . . . . ?
N1 C1 C5 O2 155.73(9) . . . . ?
C2 O1 C3 C4 -17.20(16) . . . . ?
C7 O4 C8 C11 -56.69(12) . . . . ?
C7 O4 C8 C9 68.01(12) . . . . ?
C7 O4 C8 C10 -174.18(10) . . . . ?
O1 C3 C4 N1 -1.86(17) . . . . ?
C7 N1 C4 C3 -137.21(11) . . . . ?
C1 N1 C4 C3 19.82(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20565014
