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_4037924
_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 H7 N O2'
_chemical_formula_sum            'C8 H7 N O2'
_chemical_formula_weight         149.15
_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     direct
_audit_creation_date             2019-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                77.401(8)
_cell_angle_beta                 85.073(8)
_cell_angle_gamma                78.699(9)
_cell_formula_units_Z            2
_cell_length_a                   6.5474(7)
_cell_length_b                   7.2418(7)
_cell_length_c                   7.6043(7)
_cell_measurement_reflns_used    1089
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4400
_cell_measurement_theta_min      5.9530
_cell_volume                     344.70(6)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.990
_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   -104.00 -20.00   1.00    2.42    --  -37.08 -57.00   0.00   84
  2  \w    -21.00  64.00   1.00    2.42    --   37.08 -77.00  90.00   85
  3  \w     18.00 106.00   1.00    2.42    --   37.08  38.00 -60.00   88
  4  \w    -32.00 106.00   1.00    2.42    --   37.08   0.00  90.00  138
  5  \w     27.00  90.00   1.00    2.42    --   37.08-125.00  30.00   63
  6  \w     27.00  90.00   1.00    2.42    --   37.08-125.00-150.00   63
  7  \w     27.00  90.00   1.00    2.42    --   37.08-125.00-120.00   63
  8  \w     44.00 131.00   1.00    9.68    --  111.00 -64.00 150.00   87
  9  \w     41.00 136.00   1.00    9.68    --  111.00 -25.00 150.00   95
 10  \w     42.00 106.00   1.00    9.68    --  111.00 -92.00 120.00   64
 11  \w     41.00 109.00   1.00    9.68    --  111.00-111.00  60.00   68
 12  \w    138.00 164.00   1.00    9.68    --  111.00  38.00-150.00   26
 13  \w     42.00  68.00   1.00    9.68    --  111.00 -38.00  30.00   26
 14  \w     50.00  80.00   1.00    9.68    --  111.00-111.00-120.00   30
 15  \w     70.00 106.00   1.00    9.68    --  111.00 -92.00  60.00   36
 16  \w     95.00 120.00   1.00    9.68    --  111.00  38.00-150.00   25
 17  \w     98.00 177.00   1.00    9.68    --  111.00  50.00-180.00   79
 18  \w     63.00 102.00   1.00    9.68    --  111.00 178.00 150.00   39
 19  \w     84.00 109.00   1.00    9.68    --  111.00-111.00-120.00   25
 20  \w    110.00 170.00   1.00    9.68    --  111.00  77.00 120.00   60
 21  \w     45.00  71.00   1.00    9.68    --  111.00 -92.00  90.00   26
 22  \w     78.00 108.00   1.00    9.68    --  111.00-111.00 -60.00   30
 23  \w    101.00 165.00   1.00    9.68    --  111.00  64.00-120.00   64
 24  \w    133.00 176.00   1.00    9.68    --  111.00  77.00  90.00   43
 25  \w     62.00 124.00   1.00    9.68    --  111.00 -64.00 120.00   62
 26  \w     64.00  98.00   1.00    9.68    --  111.00 178.00-150.00   34
 27  \w    125.00 169.00   1.00    9.68    --  111.00  77.00 150.00   44
 28  \w     80.00 105.00   1.00    9.68    --  111.00 -92.00 150.00   25
 29  \w    106.00 132.00   1.00    9.68    --  111.00 178.00-150.00   26
 30  \w     92.00 146.00   1.00    9.68    --  111.00 178.00  90.00   54
 31  \w     73.00 129.00   1.00    9.68    --  111.00 -38.00  30.00   56
 32  \w     96.00 130.00   1.00    9.68    --  111.00 -64.00-120.00   34
 33  \w     43.00  69.00   1.00    9.68    --  111.00 -38.00  90.00   26
 34  \w     42.00  76.00   1.00    9.68    --  111.00-111.00 -30.00   34
;
_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      -0.0615159000
_diffrn_orient_matrix_UB_12      -0.1931251000
_diffrn_orient_matrix_UB_13      -0.0062115000
_diffrn_orient_matrix_UB_21      -0.2156005000
_diffrn_orient_matrix_UB_22      0.0653183000
_diffrn_orient_matrix_UB_23      0.0874875000
_diffrn_orient_matrix_UB_31      -0.0861567000
_diffrn_orient_matrix_UB_32      0.0870873000
_diffrn_orient_matrix_UB_33      -0.1883832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.827
_diffrn_reflns_theta_min         5.969
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96708
_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    1.437
_exptl_crystal_description       needle
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0572P)^2^+0.0903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1124
_reflns_number_total             1378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-27c4scaled
_cod_database_code               4037924
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         c8h7n1o2
_reflns_odcompleteness_completeness 98.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              9053
_shelx_hkl_checksum              39483
_ins_header
;
TITL MN-27c4scaled in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184   6.547420   7.241828   7.604319  77.4012  85.0734  78.6994
ZERR    2.00   0.000739   0.000668   0.000678   0.0077   0.0083   0.0088
LATT  1
SFAC C H N O
UNIT 16.00 14.00 2.00 4.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-29
_olex2_date_sample_submission    2019-05-29
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_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 3.344
_oxdiff_exptl_absorpt_empirical_full_min 0.761