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_7239986
_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         '4(C15 H21 N O6)'
_chemical_formula_sum            'C60 H84 N4 O24'
_chemical_formula_weight         1245.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-11-13
_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                 115.7230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.7484(3)
_cell_length_b                   10.70600(10)
_cell_length_c                   26.2577(3)
_cell_measurement_reflns_used    38480
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      74.1160
_cell_measurement_theta_min      3.2790
_cell_volume                     6267.71(13)
_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      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     23.00  51.00   0.50    2.00    --   47.48  75.00  -8.00   56
  2  \w     55.00  99.00   0.50    2.00    --   47.48  75.00  -8.00   88
  3  \w     76.00 177.00   0.50   15.00    --  101.53  75.00  -8.00  202
  4  \w    143.00 176.00   0.50   15.00    --  101.53  30.00  90.00   66
  5  \w    138.00 173.00   0.50   15.00    --  101.53  61.00  90.00   70
  6  \w    110.00 155.00   0.50   15.00    --  101.53  77.00 -30.00   90
  7  \w    114.00 175.00   0.50   15.00    --  101.53 111.00  30.00  122
  8  \w     94.00 165.00   0.50   15.00    --  101.53  45.00 150.00  142
  9  \w     95.00 174.00   0.50   15.00    --  101.53  45.00 120.00  158
 10  \w     85.00 131.00   0.50   15.00    --  101.53  61.00  90.00   92
 11  \w     80.00 177.00   0.50   15.00    --  101.53  77.00  30.00  194
 12  \w     83.00 175.00   0.50   15.00    --  101.53  61.00-120.00  184
 13  \w     81.00 133.00   0.50   15.00    --  101.53  61.00 -90.00  104
 14  \w     75.00 178.00   0.50   15.00    --  101.53  77.00 -60.00  206
 15  \w     82.00 137.00   0.50   15.00    --  101.53  30.00  90.00  110
 16  \w     73.00 128.00   0.50   15.00    --  101.53 -77.00 120.00  110
 17  \w     75.00 110.00   0.50   15.00    --  101.53 -94.00  60.00   70
 18  \w     52.00  89.00   0.50   15.00    --  101.53 -94.00 -60.00   74
 19  \w     48.00  74.00   0.50   15.00    --  101.53 -75.00-136.00   52
 20  \w     92.00 121.00   0.50   15.00    --  101.53 -75.00-136.00   58
 21  \w     31.00  73.00   0.50    2.00    --   47.48 -75.00-136.00   84
 22  \w     27.00  87.00   0.50    2.00    --   47.48  57.00  90.00  120
 23  \w     65.00 149.00   0.50   15.00    --  101.53 178.00 150.00  168
 24  \w    -23.00   3.00   0.50    2.00    --  -47.48  75.00  -8.00   52
 25  \w    -62.00 -35.00   0.50    2.00    --  -47.48  75.00  -8.00   54
 26  \w    -89.00 -64.00   0.50   15.00    --  -90.25  75.00  -8.00   50
 27  \w    -87.00 -24.00   0.50   15.00    --  -90.25 111.00-120.00  126
 28  \w   -122.00 -27.00   0.50    2.00    --  -47.48 -57.00-180.00  190
 29  \w    -96.00 -71.00   0.50    2.00    --  -47.48 -75.00-136.00   50
 30  \w   -123.00 -71.00   0.50    2.00    --  -47.48-125.00 -90.00  104
 31  \w   -123.00 -78.00   0.50    2.00    --  -47.48-125.00-180.00   90
 32  \w   -139.00-114.00   0.50   15.00    --  -90.25 -75.00-136.00   50
 33  \w    -28.00  25.00   0.50    2.00    --   47.48 -75.00-136.00  106
 34  \w     31.00  96.00   0.50    2.00    --   47.48-125.00-150.00  130
 35  \w     36.00  96.00   0.50   15.00    --  101.53 -94.00 -30.00  120
 36  \w     44.00  93.00   0.50    2.00    --   47.48-125.00  60.00   98
 37  \w     32.00 102.00   0.50   15.00    --  101.53 -94.00 150.00  140
 38  \w     26.00  52.00   0.50   15.00    --  101.53 -77.00 120.00   52
;
_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      0.0493459000
_diffrn_orient_matrix_UB_12      -0.0357538000
_diffrn_orient_matrix_UB_13      0.0585710000
_diffrn_orient_matrix_UB_21      0.0374603000
_diffrn_orient_matrix_UB_22      0.1132969000
_diffrn_orient_matrix_UB_23      -0.0018790000
_diffrn_orient_matrix_UB_31      -0.0305351000
_diffrn_orient_matrix_UB_32      0.0812181000
_diffrn_orient_matrix_UB_33      0.0284324000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            80297
_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         5.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78823
_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_density_diffrn    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         11351
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+2.8171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10012
_reflns_number_total             11351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00208a2.cif
_cod_data_source_block           tr235_0
_cod_depositor_comments
;Adding full bibliography for 7239983--7239986.cif.

 Adding full bibliography for 7239983--7239986.cif.
;
_cod_database_code               7239986
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C15H21NO6
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.97
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C53A-O21A \\sim C53-O21
 with sigma of 0.005
 C52-O21A \\sim C52-O21
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C53A) = Uanis(C53)
Uanis(O21A) = Uanis(O21)
4. Others
 Sof(O21)=Sof(C53)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(1)
 Sof(O21A)=Sof(C53A)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C18(H18), C33(H33), C48(H48)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C49(H49A,H49B),
  C50(H50A,H50B), C51(H51A,H51B)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C25(H25), C45(H45), C60(H60)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,
 H43B,H43C), C46(H46A,H46B,H46C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C),
 C53A(H53A,H53B,H53C), C53(H53D,H53E,H53F)
5.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O12(H12), O18(H18A), O23(H23)
;
_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.796