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_4037922
_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         'C7 H7 N O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_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             2019-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                63.995(8)
_cell_angle_beta                 84.352(7)
_cell_angle_gamma                80.203(7)
_cell_formula_units_Z            2
_cell_length_a                   3.7878(3)
_cell_length_b                   9.6277(8)
_cell_length_c                   10.3407(8)
_cell_measurement_reflns_used    1162
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2850
_cell_measurement_theta_min      5.1470
_cell_volume                     333.86(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.992
_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    -43.00  -6.00   1.00    1.04    --  -37.23  38.00 -90.00   37
  2  \w     -2.00  29.00   1.00    1.04    --  -37.23  38.00 -90.00   31
  3  \w     18.00  74.00   1.00    1.04    --   37.23  38.00  60.00   56
  4  \w     50.00  89.00   1.00    1.04    --   37.23-125.00 -30.00   39
  5  \w    -30.00  52.00   1.00    1.04    --   37.23 -57.00 -90.00   82
  6  \w     27.00 105.00   1.00    1.04    --   37.23  38.00  90.00   78
  7  \w     36.00  87.00   1.00    1.04    --   37.23-125.00-180.00   51
  8  \w     53.00  78.00   1.00    1.04    --   37.23-125.00 150.00   25
  9  \w     17.00  47.00   1.00    1.04    --   37.23 -38.00 120.00   30
 10  \w    -31.00  16.00   1.00    1.04    --   37.23 -38.00 120.00   47
 11  \w     44.00 102.00   1.00    4.15    --  111.00 -50.00 -60.00   58
 12  \w     94.00 133.00   1.00    4.15    --  111.00  50.00 -90.00   39
 13  \w     44.00  94.00   1.00    4.15    --  111.00 -64.00  30.00   50
 14  \w     69.00  97.00   1.00    4.15    --  111.00 -92.00   0.00   28
 15  \w     89.00 132.00   1.00    4.15    --  111.00 178.00 -60.00   43
 16  \w     45.00  89.00   1.00    4.15    --  111.00 -77.00 -60.00   44
 17  \w     68.00 109.00   1.00    4.15    --  111.00-111.00-180.00   41
 18  \w     47.00  96.00   1.00    4.15    --  111.00-111.00 -60.00   49
 19  \w     87.00 124.00   1.00    4.15    --  111.00  25.00  30.00   37
 20  \w    114.00 151.00   1.00    4.15    --  111.00 -12.00  90.00   37
 21  \w     46.00 106.00   1.00    4.15    --  111.00 -12.00  90.00   60
 22  \w     42.00  93.00   1.00    4.15    --  111.00 -25.00 -30.00   51
 23  \w     75.00 109.00   1.00    4.15    --  111.00-111.00  90.00   34
 24  \w     82.00 114.00   1.00    4.15    --  111.00 -38.00  60.00   32
 25  \w     84.00 109.00   1.00    4.15    --  111.00-111.00-120.00   25
 26  \w    105.00 167.00   1.00    4.15    --  111.00 111.00  90.00   62
 27  \w     82.00 108.00   1.00    4.15    --  111.00-111.00  30.00   26
 28  \w     96.00 129.00   1.00    4.15    --  111.00 -64.00  30.00   33
 29  \w     43.00  77.00   1.00    4.15    --  111.00 -38.00  60.00   34
 30  \w     80.00 105.00   1.00    4.15    --  111.00 178.00  30.00   25
 31  \w    108.00 160.00   1.00    4.15    --  111.00 111.00   0.00   52
 32  \w     86.00 113.00   1.00    4.15    --  111.00 178.00-180.00   27
 33  \w     86.00 178.00   1.00    4.15    --  111.00  25.00 120.00   92
;
_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      -0.2203111000
_diffrn_orient_matrix_UB_12      0.1062657000
_diffrn_orient_matrix_UB_13      0.0638946000
_diffrn_orient_matrix_UB_21      -0.1783459000
_diffrn_orient_matrix_UB_22      -0.1394901000
_diffrn_orient_matrix_UB_23      0.1101640000
_diffrn_orient_matrix_UB_31      0.3002133000
_diffrn_orient_matrix_UB_32      -0.0400100000
_diffrn_orient_matrix_UB_33      0.1062023000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2350
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.496
_diffrn_reflns_theta_min         4.760
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95400
_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    1.523
_exptl_crystal_description       prism
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_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     101
_refine_ls_number_reflns         1337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0534P)^2^+0.0588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1192
_reflns_number_total             1337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-27g1scaled
_cod_database_code               4037922
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         c7h7n1o3
_reflns_odcompleteness_completeness 98.17
_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 C(H,H,H,H,H,H) groups, All N(H) groups
2. Others
 Sof(H4D)=Sof(H4E)=Sof(H4F)=1-FVAR(1)
 Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7)
3.b Disordered Me refined with riding coordinates:
 C4(H4A,H4B,H4C,H4D,H4E,H4F)
;
_shelx_res_checksum              32823
_shelx_hkl_checksum              82050
_ins_header
;
TITL MN-27g1scaled in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184   3.787821   9.627664  10.340677  63.9946  84.3520  80.2030
ZERR    2.00   0.000311   0.000778   0.000842   0.0080   0.0067   0.0068
LATT  1
SFAC C H N O
UNIT 14.00 14.00 2.00 6.00
TREF
HKLF 4
END
;
_olex2_date_sample_submission    2019-05-22
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.800