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_7239984
_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_formula_moiety         '0.5(C20 H22 N2 O4)'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-07 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.515(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1931(3)
_cell_length_b                   7.0581(4)
_cell_length_c                   8.4454(4)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    107(4)
_cell_measurement_theta_max      73.6120
_cell_measurement_theta_min      5.2710
_cell_volume                     428.36(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    -35.00  -5.00   0.50    0.10    --  -47.48 101.00  34.00   60
  2  \w     27.00  53.00   0.50    0.10    --   47.48-101.00 -70.00   52
  3  \w   -134.00 -83.00   0.50    0.37    --  -90.25-101.00 -70.00  102
  4  \w    -78.00 -48.00   0.50    0.37    --  -90.25 101.00  34.00   60
  5  \w     45.00 101.00   0.50    0.37    --  101.53-101.00 -70.00  112
  6  \w   -103.00 -27.00   0.50    0.10    --  -47.48 -57.00  60.00  152
  7  \w   -124.00 -70.00   0.50    0.10    --  -47.48-125.00 -30.00  108
  8  \w   -124.00 -74.00   0.50    0.10    --  -47.48-125.00  30.00  100
  9  \w    -26.00  67.00   0.50    0.10    --   47.48 -57.00 -90.00  186
 10  \w   -159.00 -85.00   0.50    0.37    --  -90.25 -94.00 -90.00  148
 11  \w   -169.00 -94.00   0.50    0.37    --  -90.25 -30.00-180.00  150
 12  \w   -119.00 -85.00   0.50    0.37    --  -90.25  15.00  60.00   68
 13  \w   -169.00-103.00   0.50    0.37    --  -90.25-111.00  60.00  132
 14  \w    -50.00 -17.00   0.50    0.37    --  -90.25  15.00  60.00   66
 15  \w     26.00  66.00   0.50    0.37    --  101.53 -45.00 -90.00   80
 16  \w     23.00  58.00   0.50    0.37    --  101.53 -94.00 -60.00   70
 17  \w     70.00 110.00   0.50    0.37    --  101.53 -94.00 150.00   80
 18  \w     65.00 103.00   0.50    0.37    --  101.53 -94.00 -60.00   76
 19  \w     76.00 109.00   0.50    0.37    --  101.53 -61.00 150.00   66
 20  \w     61.00 116.00   0.50    0.37    --  101.53 178.00-180.00  110
 21  \w     32.00  63.00   0.50    0.37    --  101.53 -94.00 150.00   62
 22  \w     76.00 143.00   0.50    0.37    --  101.53  77.00   0.00  134
 23  \w     36.00  67.00   0.50    0.37    --  101.53 -61.00 150.00   62
 24  \w    141.00 170.00   0.50    0.37    --  101.53  45.00 -60.00   58
 25  \w     92.00 124.00   0.50    0.37    --  101.53  45.00 -60.00   64
 26  \w     79.00 119.00   0.50    0.37    --  101.53 -45.00 -90.00   80
 27  \w    120.00 145.00   0.50    0.37    --  101.53 178.00-180.00   50
 28  \w     29.00  55.00   0.50    0.37    --  101.53 -94.00-120.00   52
 29  \w     63.00  88.00   0.50    0.37    --  101.53 -94.00-120.00   50
 30  \w     49.00 109.00   0.50    0.37    --  101.53 -94.00 -30.00  120
 31  \w    140.00 165.00   0.50    0.37    --  101.53 111.00-180.00   50
 32  \w     83.00 173.00   0.50    0.37    --  101.53  61.00 120.00  180
;
_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      -0.0781987000
_diffrn_orient_matrix_UB_12      -0.1977921000
_diffrn_orient_matrix_UB_13      0.0358423000
_diffrn_orient_matrix_UB_21      -0.0381642000
_diffrn_orient_matrix_UB_22      0.0644061000
_diffrn_orient_matrix_UB_23      0.1699893000
_diffrn_orient_matrix_UB_31      -0.1959077000
_diffrn_orient_matrix_UB_32      0.0661388000
_diffrn_orient_matrix_UB_33      -0.0562361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.867
_diffrn_reflns_theta_min         5.242
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       irregular
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.011(3)
_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   1.057
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         928
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0466P)^2^+0.1017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                826
_reflns_number_total             928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00208a2.cif
_cod_data_source_block           tr_199_0
_cod_depositor_comments
;Adding full bibliography for 7239983--7239986.cif.

 Adding full bibliography for 7239983--7239986.cif.
;
_cod_original_cell_volume        428.35(3)
_cod_database_code               7239984
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C10H11NO2
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.858
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.89 with sigma of 0.01
 C2-H2 = C9-H9
 0.92 with sigma of 0.01
 C5-H5A = C5-H5B = C5-H5C = C6-H6B = C6-H6A = C7-H7A = C7-H7B
 0.93 with sigma of 0.01
3. Others
 Fixed Sof: O1(0.5) N1(0.5) H1A(0.5) H1B(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5)
 C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5) C6(0.5) H6B(0.5) H6A(0.5) C7(0.5) H7A(0.5)
 H7B(0.5) C8(0.5) C10(0.5)
;
_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 1.935
_oxdiff_exptl_absorpt_empirical_full_min 0.789