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_4037923
_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         'C2 F3 O2, C5 H6 N O'
_chemical_formula_sum            'C7 H6 F3 N O3'
_chemical_formula_weight         209.13
_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             2019-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                103.85(2)
_cell_angle_beta                 94.753(18)
_cell_angle_gamma                95.55(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2250(14)
_cell_length_b                   7.862(3)
_cell_length_c                   8.7433(18)
_cell_measurement_reflns_used    393
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      69.9910
_cell_measurement_theta_min      7.1820
_cell_volume                     411.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_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  33.00   1.00    7.50    --  -36.03  38.00   0.00   85
  2  \w    -96.00  33.00   1.00    7.50    --  -36.03   0.00 -30.00  129
  3  \w     30.00  81.00   1.00    7.50    --   36.03-125.00 -90.00   51
  4  \w      8.00  57.00   1.00    7.50    --   36.03 -99.00 150.00   49
  5  \w     32.00  76.00   1.00    7.50    --   36.03-125.00  60.00   44
  6  \w     40.00 120.00   1.00   31.00    --  105.15 -61.00-150.00   80
  7  \w     37.00 101.00   1.00   31.00    --  105.15 -30.00 120.00   64
  8  \w     89.00 171.00   1.00   31.00    --  105.15  30.00  60.00   82
  9  \w     87.00 162.00   1.00   31.00    --  105.15  61.00 150.00   75
 10  \w     37.00 123.00   1.00   31.00    --  105.15 -45.00 -30.00   86
 11  \w     62.00 110.00   1.00   31.00    --  105.15 178.00-150.00   48
 12  \w     60.00 100.00   1.00   31.00    --  105.15 -95.00  60.00   40
 13  \w     73.00 105.00   1.00   31.00    --  105.15 -95.00-180.00   32
 14  \w     37.00 108.00   1.00   31.00    --  105.15-111.00   0.00   71
 15  \w     90.00 162.00   1.00   31.00    --  105.15  45.00 -60.00   72
 16  \w     67.00 124.00   1.00   31.00    --  105.15 -77.00  90.00   57
;
_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      -0.1524450000
_diffrn_orient_matrix_UB_12      -0.1107867000
_diffrn_orient_matrix_UB_13      -0.1446949000
_diffrn_orient_matrix_UB_21      0.0074372000
_diffrn_orient_matrix_UB_22      0.1594268000
_diffrn_orient_matrix_UB_23      -0.0739554000
_diffrn_orient_matrix_UB_31      0.1981963000
_diffrn_orient_matrix_UB_32      -0.0602955000
_diffrn_orient_matrix_UB_33      -0.0832401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1947
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         5.242
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (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    1.690
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0856
_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^)+(0.0795P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                788
_reflns_number_total             1393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-24h2scaledfiltered
_cod_original_cell_volume        411.04(19)
_cod_database_code               4037923
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C7H6F3N1O3
_reflns_odcompleteness_completeness 95.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C3(H3), C4(H4), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              72193
_shelx_hkl_checksum              45812
_ins_header
;
TITL MN-24h2scaledfiltered in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184   6.225034   7.862445   8.743328 103.8524  94.7529  95.5484
ZERR    2.00   0.001405   0.002539   0.001835   0.0234   0.0180   0.0223
LATT  1
SFAC C H N O F
UNIT 14.00 12.00 2.00 6.00 6.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-30
_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 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.646