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_4037920
_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, H2 O'
_chemical_formula_sum            'C8 H11 N O4'
_chemical_formula_weight         185.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.768(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8160(4)
_cell_length_b                   11.4782(5)
_cell_length_c                   11.3108(5)
_cell_measurement_reflns_used    1487
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.4630
_cell_measurement_theta_min      3.9870
_cell_volume                     863.02(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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 0.998
_diffrn_measured_fraction_theta_max 0.884
_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    -52.00  32.00   1.00    1.37    --   15.42 -57.00-180.00   84
  2  \w     34.00  88.00   1.00    1.37    --   15.42-178.00  30.00   54
  3  \w    -56.00  45.00   1.00    1.37    --   15.42 -19.00 -90.00  101
  4  \w     35.00  88.00   1.00    1.37    --   15.42 178.00-180.00   53
  5  \w     -1.00  26.00   1.00    1.37    --   15.42  57.00  90.00   27
  6  \w    -11.00  83.00   1.00    1.37    --   15.42  77.00 -60.00   94
;
_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      0.0210516000
_diffrn_orient_matrix_UB_12      0.0266436000
_diffrn_orient_matrix_UB_13      0.0579866000
_diffrn_orient_matrix_UB_21      -0.0455087000
_diffrn_orient_matrix_UB_22      -0.0476334000
_diffrn_orient_matrix_UB_23      0.0236548000
_diffrn_orient_matrix_UB_31      0.0941825000
_diffrn_orient_matrix_UB_32      -0.0289908000
_diffrn_orient_matrix_UB_33      0.0145791000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7228
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.158
_diffrn_reflns_theta_min         3.542
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (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    1.425
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1389
_reflns_number_total             2066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-13b1-hplcscaled
_cod_database_code               4037920
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C8H11NO3
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              36287
_shelx_hkl_checksum              16248
_ins_header
;
TITL MN-13b1-hplcscaled in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 0.71073   6.815954  11.478156  11.310765  90.0000 102.7683  90.0000
ZERR    4.00   0.000376   0.000506   0.000544   0.0000   0.0054   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 32.00 44.00 4.00 12.00
TREF
HKLF 4
END
;
_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 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.867