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_4037925
_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         'C6 H7 N O2'
_chemical_formula_sum            'C6 H7 N O2'
_chemical_formula_weight         125.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6520(4)
_cell_length_b                   9.3307(5)
_cell_length_c                   13.2182(6)
_cell_measurement_reflns_used    1835
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5030
_cell_measurement_theta_min      7.3710
_cell_volume                     1190.43(10)
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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   -103.00 -24.00   1.00    1.80    --  -36.95 -57.00-150.00   79
  2  \w     56.00  83.00   1.00    1.80    --   36.95-125.00-150.00   27
  3  \w     16.00  50.00   1.00    1.80    --   36.95 -38.00   0.00   34
  4  \w     11.00  36.00   1.00    1.80    --   36.95  19.00   0.00   25
  5  \w     83.00 108.00   1.00    1.80    --   36.95  19.00   0.00   25
  6  \w    -31.00  -5.00   1.00    1.80    --   36.95 -38.00   0.00   26
  7  \w     44.00  71.00   1.00    1.80    --   36.95 -99.00 -30.00   27
  8  \w     51.00  80.00   1.00    7.20    --  111.00 -92.00  60.00   29
  9  \w     47.00  95.00   1.00    7.20    --  111.00 -92.00  30.00   48
 10  \w     68.00 106.00   1.00    7.20    --  111.00 -92.00-180.00   38
 11  \w    144.00 173.00   1.00    7.20    --  111.00  77.00  60.00   29
 12  \w     42.00  67.00   1.00    7.20    --  111.00-111.00  30.00   25
 13  \w    109.00 137.00   1.00    7.20    --  111.00  77.00  60.00   28
 14  \w     55.00 106.00   1.00    7.20    --  111.00 -92.00 -90.00   51
 15  \w     92.00 118.00   1.00    7.20    --  111.00 -38.00 150.00   26
 16  \w     52.00 122.00   1.00    7.20    --  111.00 -25.00-150.00   70
 17  \w     43.00  69.00   1.00    7.20    --  111.00 -92.00-150.00   26
 18  \w     76.00 101.00   1.00    7.20    --  111.00 -92.00-150.00   25
 19  \w    141.00 166.00   1.00    7.20    --  111.00   0.00-120.00   25
 20  \w     69.00  98.00   1.00    7.20    --  111.00   0.00-120.00   29
;
_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      -0.0053671000
_diffrn_orient_matrix_UB_12      0.1634923000
_diffrn_orient_matrix_UB_13      -0.0158932000
_diffrn_orient_matrix_UB_21      -0.1586525000
_diffrn_orient_matrix_UB_22      -0.0078776000
_diffrn_orient_matrix_UB_23      -0.0100953000
_diffrn_orient_matrix_UB_31      -0.0146530000
_diffrn_orient_matrix_UB_32      0.0218542000
_diffrn_orient_matrix_UB_33      0.1151415000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.748
_diffrn_reflns_theta_min         6.699
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97317
_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    1.396
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0806P)^2^+0.3034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1073
_reflns_number_total             1199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-13a1scaled
_cod_database_code               4037925
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C6H7N1O2
_reflns_odcompleteness_completeness 98.47
_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), C1(H1A), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              5709
_shelx_hkl_checksum              48884
_ins_header
;
TITL MN-13a1scaled in Pbca 
REM Pbca (#61, found as Pcab in ba-c setting)
CELL 1.54184   9.651998   9.330658  13.218171  90.0000  90.0000  90.0000
ZERR    7.00   0.000444   0.000530   0.000583   0.0000   0.0000   0.0000
LATT  1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H N O
UNIT 42.00 49.00 7.00 14.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-03-06
_olex2_date_sample_submission    2019-02-25
_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 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.772