Haber-independent, diversity-oriented synthesis of nitrogen compounds from biorenewable chitin
Pham, Thuy Trang; Chen, Xi; Söhnel, Tilo; Yan, Ning; Sperry, Jonathan; Green Chemistry 22 (2020) 1978–1984; doi:10.1039/D0GC00208A

data_7239985
_publ_section_title
;
 Haber-independent, diversity-oriented synthesis of nitrogen compounds
 from biorenewable chitin
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1978
_journal_page_last               1984
_journal_paper_doi               10.1039/D0GC00208A
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 N O5'
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.25
_chemical_name_systematic        TR205
_chemical_temperature_decomposition_gt 473.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-06 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.19640(10)
_cell_length_b                   11.9878(3)
_cell_length_c                   14.7510(3)
_cell_measurement_reflns_used    5724
_cell_measurement_temperature    107(5)
_cell_measurement_theta_max      74.0910
_cell_measurement_theta_min      6.0290
_cell_volume                     1272.55(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_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     29.00  76.00   0.50    0.50    --   47.48  38.00 -82.00   94
  2  \w     30.00  69.00   0.50    2.00    --  101.53 -30.00  30.00   78
  3  \w     91.00 122.00   0.50    2.00    --  101.53 -30.00  30.00   62
  4  \w     84.00 119.00   0.50    2.00    --  101.53 -38.00 122.00   70
  5  \w     82.00 176.00   0.50    2.00    --  101.53  45.00   0.00  188
  6  \w    153.00 178.00   0.50    2.00    --  101.53 111.00 120.00   50
  7  \w    111.00 137.00   0.50    2.00    --  101.53 111.00 120.00   52
  8  \w     29.00  68.00   0.50    2.00    --  101.53 -38.00 122.00   78
  9  \w     32.00 110.00   0.50    2.00    --  101.53 -94.00 120.00  156
 10  \w     24.00 100.00   0.50    2.00    --  101.53 -94.00  60.00  152
 11  \w    -42.00 -14.00   0.50    2.00    --  -90.25 128.00 -27.00   56
 12  \w    -66.00 -11.00   0.50    2.00    --  -90.25 111.00 -60.00  110
 13  \w    -72.00 -47.00   0.50    2.00    --  -90.25 128.00 -27.00   50
 14  \w    -81.00 -56.00   0.50    2.00    --  -90.25 111.00  30.00   50
 15  \w    -90.00  -9.00   0.50    0.50    --  -47.48 125.00  90.00  162
 16  \w   -108.00 -35.00   0.50    0.50    --  -47.48 -57.00  90.00  146
 17  \w    -86.00 -61.00   0.50    2.00    --  -90.25 -83.00 -33.00   50
 18  \w   -105.00 -80.00   0.50    0.50    --  -47.48-142.00  86.00   50
 19  \w   -169.00-119.00   0.50    2.00    --  -90.25 -38.00 122.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0972551000
_diffrn_orient_matrix_UB_12      0.0547404000
_diffrn_orient_matrix_UB_13      -0.0817060000
_diffrn_orient_matrix_UB_21      -0.0356750000
_diffrn_orient_matrix_UB_22      -0.1160720000
_diffrn_orient_matrix_UB_23      -0.0412946000
_diffrn_orient_matrix_UB_31      -0.1873983000
_diffrn_orient_matrix_UB_32      -0.0062714000
_diffrn_orient_matrix_UB_33      0.0502514000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7454
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.738
_diffrn_reflns_theta_min         6.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate + light petroleum'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0416P)^2^+0.2116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0728
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2230
_reflns_number_total             2314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00208a2.cif
_cod_data_source_block           tr205_0
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified as 'more than' ('>') a certain temperature. The value '>200
oC (decomposed)' was changed to '473.15' -- it was converted from
degrees Celsius (C) to kelvins (K).

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7239983--7239986.cif.

 Adding full bibliography for 7239983--7239986.cif.
;
_cod_database_code               7239985
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C14H13NO5
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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), C4(H4), C11(H11), C12(H12), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.798