Exploiting Chitin as a Source of Biologically Fixed Nitrogen: Formation and Full Characterization of Small-Molecule Hetero- and Carbocyclic Pyrolysis Products.
Nikahd, Maryam; Mikusek, Jiri; Yu, Li-Juan; Coote, Michelle L.; Banwell, Martin G.; Ma, Chenxi; Gardiner, Michael G.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03438

data_4037916
_publ_section_title
;
 Exploiting Chitin as a Source of Biologically Fixed Nitrogen: Formation
 and Full Characterization of Small-Molecule Hetero- and Carbocyclic
 Pyrolysis Products.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03438
_journal_year                    2020
_chemical_formula_moiety         'C8 H9 N O3'
_chemical_formula_sum            'C8 H9 N O3'
_chemical_formula_weight         167.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                89.422(18)
_cell_angle_beta                 86.974(13)
_cell_angle_gamma                80.489(18)
_cell_formula_units_Z            2
_cell_length_a                   4.6446(8)
_cell_length_b                   8.456(2)
_cell_length_c                   10.7100(16)
_cell_measurement_reflns_used    896
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.1900
_cell_measurement_theta_min      5.2410
_cell_volume                     414.27(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -69.00 -21.00   1.00    1.00    --  -37.35 -57.00  30.00   48
  2  \w     22.00 106.00   1.00    1.00    --   37.35  38.00 -60.00   84
  3  \w     56.00  81.00   1.00    1.00    --   37.35  57.00 -60.00   25
  4  \w     57.00  89.00   1.00    1.00    --   37.35-125.00  60.00   32
  5  \w     60.00 105.00   1.00    1.00    --   37.35  57.00  30.00   45
  6  \w     32.00  91.00   1.00    1.00    --   37.35-125.00-180.00   59
  7  \w     16.00  59.00   1.00    1.00    --   37.35 -99.00 -60.00   43
  8  \w    -17.00  14.00   1.00    1.00    --   37.35 -38.00 -60.00   31
  9  \w     28.00 102.00   1.00    1.00    --   37.35  57.00 150.00   74
 10  \w     44.00  86.00   1.00    1.00    --   37.35  57.00-150.00   42
 11  \w      6.00  54.00   1.00    1.00    --   37.35 -99.00   0.00   48
 12  \w     68.00  95.00   1.00    2.20    --  111.00 -12.00 -90.00   27
 13  \w     56.00 113.00   1.00    2.20    --  111.00-111.00  90.00   57
 14  \w     44.00 103.00   1.00    2.20    --  111.00 -50.00 -30.00   59
 15  \w     52.00  94.00   1.00    2.20    --  111.00 -64.00 120.00   42
 16  \w     90.00 153.00   1.00    2.20    --  111.00  77.00-120.00   63
 17  \w     75.00 107.00   1.00    2.20    --  111.00-111.00-120.00   32
 18  \w     42.00  69.00   1.00    2.20    --  111.00-111.00 -90.00   27
 19  \w    139.00 169.00   1.00    2.20    --  111.00  64.00-180.00   30
 20  \w    131.00 173.00   1.00    2.20    --  111.00  50.00   0.00   42
 21  \w     93.00 126.00   1.00    2.20    --  111.00  64.00-180.00   33
 22  \w     93.00 172.00   1.00    2.20    --  111.00  25.00 150.00   79
 23  \w     82.00 109.00   1.00    2.20    --  111.00 -92.00 -30.00   27
 24  \w     46.00 123.00   1.00    2.20    --  111.00 -64.00-180.00   77
 25  \w     78.00 110.00   1.00    2.20    --  111.00-111.00-180.00   32
 26  \w     54.00 105.00   1.00    2.20    --  111.00-111.00   0.00   51
 27  \w     45.00  70.00   1.00    2.20    --  111.00-111.00-180.00   25
 28  \w    119.00 144.00   1.00    2.20    --  111.00 -12.00 -90.00   25
 29  \w     77.00 119.00   1.00    2.20    --  111.00 -50.00   0.00   42
 30  \w     54.00 126.00   1.00    2.20    --  111.00 -25.00-150.00   72
 31  \w     88.00 113.00   1.00    2.20    --  111.00-111.00 -90.00   25
 32  \w     58.00 115.00   1.00    2.20    --  111.00 -64.00 -90.00   57
 33  \w     68.00 120.00   1.00    2.20    --  111.00 -59.00  67.56   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1352111000
_diffrn_orient_matrix_UB_12      0.0883073000
_diffrn_orient_matrix_UB_13      0.1196452000
_diffrn_orient_matrix_UB_21      -0.3001060000
_diffrn_orient_matrix_UB_22      0.0321191000
_diffrn_orient_matrix_UB_23      -0.0585309000
_diffrn_orient_matrix_UB_31      -0.0711638000
_diffrn_orient_matrix_UB_32      -0.1590430000
_diffrn_orient_matrix_UB_33      0.0548440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2846
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.483
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0872
_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/[\s^2^(Fo^2^)+(0.1717P)^2^+0.0267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2302
_refine_ls_wR_factor_ref         0.2656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1222
_reflns_number_total             1635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           MN115A3_scale
_cod_database_code               4037916
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C8H9N1O3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.773
_reflns_odcompleteness_completeness 96.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), N1(H1)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              64447
_shelx_hkl_checksum              10519
_ins_header
;
TITL KMA_MN114A3_scale in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184   4.644612   8.455864  10.710020  89.4218  86.9737  80.4889
ZERR    2.00   0.000787   0.002129   0.001632   0.0180   0.0133   0.0182
LATT  1
SFAC C H N O
UNIT 16.00 18.00 2.00 6.00
TREF
HKLF 4
END
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.603