#------------------------------------------------------------------------------
#$Date: 2022-07-27 03:43:02 +0300 (Wed, 27 Jul 2022) $
#$Revision: 276954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158797.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_7158797
loop_
_publ_author_name
'Sperry, Jonathan'
'Lau, Michelle'
'Neville, Jessica'
'Söhnel, Tilo'
_publ_section_title
;
 Haber-independent, asymmetric synthesis of the marine alkaloid
 epi-leptosphaerin from a chitin-derived chiral pool synthon
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01251K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H11 N O5'
_chemical_formula_sum            'C8 H11 N O5'
_chemical_formula_weight         201.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-06-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-06 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0853(2)
_cell_length_b                   6.9127(2)
_cell_length_c                   21.3235(4)
_cell_measurement_reflns_used    4269
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      73.4970
_cell_measurement_theta_min      4.1440
_cell_volume                     896.99(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  53.00   0.50    0.40    --  100.91 -61.00 120.00   50
  2  ω     29.00  55.00   0.50    0.40    --  100.91 -61.00-150.00   52
  3  ω     28.00  68.00   0.50    0.40    --  100.91 -61.00-120.00   80
  4  ω     23.00  48.00   0.50    0.40    --  100.91 -45.00 120.00   50
  5  ω     24.00  49.00   0.50    0.40    --  100.91 -45.00  60.00   50
  6  ω     23.00  48.00   0.50    0.40    --  100.91 -45.00 -30.00   50
  7  ω     25.00  51.00   0.50    0.40    --  100.91 -45.00  30.00   52
  8  ω     24.00  50.00   0.50    0.40    --  100.91 -45.00-120.00   52
  9  ω     25.00  51.00   0.50    0.40    --  100.91 -45.00 -60.00   52
 10  ω    102.00 178.00   0.50    0.40    --  100.91 111.00 -18.00  152
 11  ω    -26.00   0.00   0.50    0.10    --   47.23 -19.00 150.00   52
 12  ω     97.00 135.00   0.50    0.40    --  100.91  17.00 177.00   76
 13  ω     91.00 117.00   0.50    0.40    --  100.91-147.00  -1.00   52
 14  ω     62.00 104.00   0.50    0.40    --  100.91 -95.00-120.00   84
 15  ω    -43.00  26.00   0.50    0.10    --  -47.23  38.00 -60.00  138
 16  ω     -2.00  28.00   0.50    0.10    --  -47.23  17.00 177.00   60
 17  ω   -101.00 -54.00   0.50    0.40    --  -90.25  77.00-150.00   94
 18  ω    -62.00 -23.00   0.50    0.40    --  -90.25  61.00   0.00   78
 19  ω    -71.00 -41.00   0.50    0.40    --  -90.25  61.00 -30.00   60
 20  ω    -39.00 -14.00   0.50    0.40    --  -90.25  45.00  60.00   50
 21  ω    -47.00 -20.00   0.50    0.40    --  -90.25  45.00  90.00   54
 22  ω   -146.00 -85.00   0.50    0.40    --  -90.25-125.00 164.00  122
 23  ω   -111.00 -86.00   0.50    0.10    --  -47.23-125.00 -90.00   50
 24  ω   -120.00 -76.00   0.50    0.10    --  -47.23-125.00  30.00   88
 25  ω    -99.00 -74.00   0.50    0.10    --  -47.23 -17.00   8.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1023832000
_diffrn_orient_matrix_UB_12      -0.2037362000
_diffrn_orient_matrix_UB_13      -0.0007891000
_diffrn_orient_matrix_UB_21      -0.2257340000
_diffrn_orient_matrix_UB_22      -0.0885994000
_diffrn_orient_matrix_UB_23      0.0158510000
_diffrn_orient_matrix_UB_31      -0.0518346000
_diffrn_orient_matrix_UB_32      -0.0176098000
_diffrn_orient_matrix_UB_33      -0.0704606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5090
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.733
_diffrn_reflns_theta_min         4.147
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_extinction_coef       0.0042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0356P)²+0.1955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1558
_reflns_number_total             1620
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01251k2.cif
_cod_data_source_block           jcn_npg11_4
_cod_database_code               7158797
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H11NO5
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.881
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), N(H)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.793
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1482(4) -0.0648(3) 0.71057(10) 0.0194(5) Uani 1 1 d . . . . .
H1A H -0.001971 -0.030043 0.700258 0.023 Uiso 1 1 calc R U . . .
H1B H 0.198061 -0.158802 0.679944 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2923(4) 0.1142(3) 0.70688(10) 0.0168(5) Uani 1 1 d . . . . .
H2 H 0.254549 0.196385 0.742748 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2493(4) 0.2328(3) 0.64727(9) 0.0175(5) Uani 1 1 d . . . . .
H3 H 0.093767 0.268659 0.644836 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4692(4) 0.2107(3) 0.56072(9) 0.0165(5) Uani 1 1 d . . . . .
C5 C 0.3896(4) 0.4091(3) 0.64302(10) 0.0177(5) Uani 1 1 d . . . . .
H5 H 0.384915 0.513917 0.670346 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5226(4) 0.3924(3) 0.59385(10) 0.0165(5) Uani 1 1 d . . . . .
C7 C 0.7335(4) 0.6907(3) 0.58995(9) 0.0178(5) Uani 1 1 d . . . . .
C8 C 0.9174(4) 0.7900(4) 0.55556(11) 0.0245(5) Uani 1 1 d . . . . .
H8A H 0.910828 0.926601 0.563386 0.037 Uiso 1 1 calc R U . . .
H8B H 0.902914 0.766458 0.511379 0.037 Uiso 1 1 calc R U . . .
H8C H 1.055722 0.740187 0.569952 0.037 Uiso 1 1 calc R U . . .
N N 0.6898(3) 0.5079(3) 0.57003(8) 0.0174(4) Uani 1 1 d . . . . .
H H 0.770914 0.460726 0.540775 0.021 Uiso 1 1 calc R U . . .
O1 O 0.1535(3) -0.1493(3) 0.77117(7) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.5195(3) 0.0668(2) 0.71231(7) 0.0168(4) Uani 1 1 d . . . . .
O3 O 0.3108(3) 0.1177(2) 0.59265(6) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.5461(3) 0.1488(2) 0.51253(7) 0.0213(4) Uani 1 1 d . . . . .
O5 O 0.6283(3) 0.7663(2) 0.63239(7) 0.0235(4) Uani 1 1 d . . . . .
H2A H 0.544(5) -0.021(5) 0.6854(14) 0.031(8) Uiso 1 1 d . . . . .
H1 H 0.273(7) -0.230(5) 0.7720(15) 0.046(9) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.70(18) . . ?
C1 C2 H2 107.3 . . ?
C1 C2 C3 112.33(18) . . ?
C3 C2 H2 107.3 . . ?
O2 C2 C1 111.64(18) . . ?
O2 C2 H2 107.3 . . ?
O2 C2 C3 110.79(17) . . ?
C2 C3 H3 110.1 . . ?
C5 C3 C2 112.93(18) . . ?
C5 C3 H3 110.1 . . ?
O3 C3 C2 109.02(17) . . ?
O3 C3 H3 110.1 . . ?
O3 C3 C5 104.51(17) . . ?
O3 C4 C6 108.80(18) . . ?
O4 C4 C6 128.5(2) . . ?
O4 C4 O3 122.7(2) . . ?
C3 C5 H5 125.5 . . ?
C6 C5 C3 109.0(2) . . ?
C6 C5 H5 125.5 . . ?
C5 C6 C4 108.5(2) . . ?
C5 C6 N 133.1(2) . . ?
N C6 C4 118.37(19) . . ?
N C7 C8 114.7(2) . . ?
O5 C7 C8 123.7(2) . . ?
O5 C7 N 121.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 N H 117.9 . . ?
C7 N C6 124.30(19) . . ?
C7 N H 117.9 . . ?
C1 O1 H1 107(2) . . ?
C2 O2 H2A 106(2) . . ?
C4 O3 C3 109.11(17) . . ?
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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.519(3) . ?
C1 O1 1.418(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.535(3) . ?
C2 O2 1.426(3) . ?
C3 H3 0.9800 . ?
C3 C5 1.491(3) . ?
C3 O3 1.459(3) . ?
C4 C6 1.477(3) . ?
C4 O3 1.344(3) . ?
C4 O4 1.208(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.329(3) . ?
C6 N 1.390(3) . ?
C7 C8 1.503(3) . ?
C7 N 1.359(3) . ?
C7 O5 1.225(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N H 0.8600 . ?
O1 H1 0.92(4) . ?
O2 H2A 0.85(3) . ?
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
C1 C2 C3 C5 179.97(18) . . . . ?
C1 C2 C3 O3 -64.3(2) . . . . ?
C2 C3 C5 C6 115.6(2) . . . . ?
C2 C3 O3 C4 -119.98(18) . . . . ?
C3 C5 C6 C4 3.3(3) . . . . ?
C3 C5 C6 N -176.9(2) . . . . ?
C4 C6 N C7 169.6(2) . . . . ?
C5 C3 O3 C4 1.0(2) . . . . ?
C5 C6 N C7 -10.1(4) . . . . ?
C6 C4 O3 C3 0.9(2) . . . . ?
C8 C7 N C6 -177.9(2) . . . . ?
O1 C1 C2 C3 -167.11(18) . . . . ?
O1 C1 C2 O2 67.7(2) . . . . ?
O2 C2 C3 C5 -54.4(2) . . . . ?
O2 C2 C3 O3 61.3(2) . . . . ?
O3 C3 C5 C6 -2.8(2) . . . . ?
O3 C4 C6 C5 -2.7(3) . . . . ?
O3 C4 C6 N 177.44(18) . . . . ?
O4 C4 C6 C5 176.3(2) . . . . ?
O4 C4 C6 N -3.6(4) . . . . ?
O4 C4 O3 C3 -178.2(2) . . . . ?
O5 C7 N C6 1.7(3) . . . . ?
