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_4037921
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                81.053(12)
_cell_angle_beta                 83.731(16)
_cell_angle_gamma                79.026(18)
_cell_formula_units_Z            2
_cell_length_a                   3.8928(10)
_cell_length_b                   9.3628(16)
_cell_length_c                   10.7006(14)
_cell_measurement_reflns_used    865
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      4.8750
_cell_volume                     376.94(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.973
_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      7.00  63.00   1.00    4.00    --   37.32 -99.00   0.00   56
  2  \w     14.00  57.00   1.00    4.00    --   37.32 -99.00-150.00   43
  3  \w     18.00  75.00   1.00    4.00    --   37.32  19.00   0.00   57
  4  \w     22.00 108.00   1.00    4.00    --   37.32  19.00  60.00   86
  5  \w     42.00  75.00   1.00    4.00    --   37.32 -99.00  60.00   33
  6  \w    -18.00  31.00   1.00    4.00    --   37.32 -77.00  60.00   49
  7  \w    -28.00  49.00   1.00    4.00    --   37.32 -57.00 120.00   77
  8  \w     41.00  70.00   1.00    4.00    --   37.32 -99.00-120.00   29
  9  \w    -21.00  15.00   1.00    4.00    --   37.32 -57.00-120.00   36
 10  \w    106.00 154.00   1.00   18.00    --  111.00 111.00 -90.00   48
 11  \w    106.00 135.00   1.00   18.00    --  111.00 111.00  60.00   29
 12  \w     93.00 155.00   1.00   18.00    --  111.00  38.00 150.00   62
 13  \w     41.00  68.00   1.00   18.00    --  111.00 -12.00 -30.00   27
 14  \w     49.00 127.00   1.00   18.00    --  111.00 -50.00 -90.00   78
 15  \w     50.00  94.00   1.00   18.00    --  111.00 -92.00-180.00   44
 16  \w     62.00 145.00   1.00   18.00    --  111.00 178.00 150.00   83
 17  \w     63.00 109.00   1.00   18.00    --  111.00-111.00  90.00   46
 18  \w     44.00  69.00   1.00   18.00    --  111.00 -92.00 150.00   25
 19  \w     78.00 106.00   1.00   18.00    --  111.00-111.00 -90.00   28
 20  \w     77.00 134.00   1.00   18.00    --  111.00 -25.00  60.00   57
 21  \w     43.00 104.00   1.00   18.00    --  111.00 -92.00 -90.00   61
 22  \w     41.00  68.00   1.00   18.00    --  111.00-111.00 -90.00   27
 23  \w    108.00 163.00   1.00   18.00    --  111.00  50.00   0.00   55
 24  \w     97.00 132.00   1.00   18.00    --  111.00 -77.00   0.00   35
 25  \w     44.00 101.00   1.00   18.00    --  111.00 -64.00-180.00   57
 26  \w     75.00 104.00   1.00   18.00    --  111.00 -92.00 -30.00   29
 27  \w     58.00  99.00   1.00   18.00    --  111.00-111.00 120.00   41
 28  \w     76.00 108.00   1.00   18.00    --  111.00-111.00 -30.00   32
 29  \w    108.00 135.00   1.00   18.00    --  111.00 -12.00 -30.00   27
 30  \w     78.00 105.00   1.00   18.00    --  111.00-111.00-180.00   27
 31  \w    121.00 150.00   1.00   18.00    --  111.00 111.00-150.00   29
 32  \w    139.00 174.00   1.00   18.00    --  111.00  50.00  30.00   35
 33  \w    105.00 167.00   1.00   18.00    --  111.00  77.00-120.00   62
 34  \w     44.00 104.00   1.00   18.00    --  111.00 -50.00 120.00   60
 35  \w     43.00 108.00   1.00   18.00    --  111.00 -27.00-134.77   65
;
_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      -0.3387274000
_diffrn_orient_matrix_UB_12      0.0548646000
_diffrn_orient_matrix_UB_13      0.0803259000
_diffrn_orient_matrix_UB_21      -0.1314794000
_diffrn_orient_matrix_UB_22      0.1090186000
_diffrn_orient_matrix_UB_23      -0.1152988000
_diffrn_orient_matrix_UB_31      -0.1777077000
_diffrn_orient_matrix_UB_32      -0.1172265000
_diffrn_orient_matrix_UB_33      -0.0404848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2786
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.652
_diffrn_reflns_theta_min         4.197
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (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    1.473
_exptl_crystal_description       needle
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0649
_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^)+(0.1093P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1760
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1141
_reflns_number_total             1486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-27e3scaled
_cod_database_code               4037921
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C8H9N1O3
_reflns_odcompleteness_completeness 96.57
_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:
 N1(H1), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              9132
_shelx_hkl_checksum              44786
_ins_header
;
TITL MN-27e3scaled in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184   3.892835   9.362845  10.700594  81.0530  83.7309  79.0262
ZERR    2.00   0.001013   0.001579   0.001374   0.0124   0.0164   0.0182
LATT  1
SFAC C H N O
UNIT 16.00 18.00 2.00 6.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-16
_olex2_date_sample_submission    2019-05-13
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_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 2.083
_oxdiff_exptl_absorpt_empirical_full_min 0.735