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_4037917
_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 H9 N O2'
_chemical_formula_sum            'C7 H9 N O2'
_chemical_formula_weight         139.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.918(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5157(10)
_cell_length_b                   9.4421(5)
_cell_length_c                   7.9012(4)
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2550
_cell_measurement_theta_min      4.3930
_cell_volume                     1351.57(13)
_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 0.993
_diffrn_measured_fraction_theta_max 0.826
_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    -49.00  30.00   1.00   10.00    --   15.42 -57.00-120.00   79
  2  \w     28.00  54.00   1.00   10.00    --   15.42 -99.00  30.00   26
  3  \w      0.00  76.00   1.00   10.00    --   15.42  38.00  60.00   76
;
_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      -0.0100585000
_diffrn_orient_matrix_UB_12      -0.0712997000
_diffrn_orient_matrix_UB_13      0.0112440000
_diffrn_orient_matrix_UB_21      0.0097800000
_diffrn_orient_matrix_UB_22      0.0085874000
_diffrn_orient_matrix_UB_23      0.0910876000
_diffrn_orient_matrix_UB_31      -0.0365367000
_diffrn_orient_matrix_UB_32      0.0220170000
_diffrn_orient_matrix_UB_33      0.0010129000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2572
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.223
_diffrn_reflns_theta_min         3.754
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70256
_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    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0435P)^2^+1.2810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1263
_reflns_number_total             1519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-j5ascalednofilter
_cod_database_code               4037917
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C7H9N1O2
_reflns_odcompleteness_completeness 98.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7B,H7C,H7A)
;
_shelx_res_checksum              51269
_shelx_hkl_checksum              79301
_ins_header
;
TITL MN-J5ascalednofilter in C2/c 
REM C2/c (#15 in standard setting)
CELL 0.71073  18.515720   9.442068   7.901247  90.0000 101.9176  90.0000
ZERR    8.00   0.000964   0.000544   0.000424   0.0000   0.0055   0.0000
LATT  7
SYMM -x, y,-z+1/2 
SFAC C H N O
UNIT 56.00 72.00 8.00 16.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-02-12
_olex2_date_sample_submission    2019-02-12
_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 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.684