Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds.
Biswas, Soumen; Empel, Claire; Sanchez-Palestino, Luis Mario; Arman, Hadi; Koenigs, Rene M.; Doyle, Michael P.; Chemical science 15 (2024) 11065–11071; doi:10.1039/d4sc01578a

data_1571927
_publ_section_title
;
 Denitrogenative dismantling of heteroaromatics by nucleophilic
 substitution reactions with diazomethyl compounds.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              11065
_journal_page_last               11071
_journal_paper_doi               10.1039/d4sc01578a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C20 H17 N5 O4'
_chemical_formula_sum            'C20 H17 N5 O4'
_chemical_formula_weight         391.39
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-29 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.256(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4348(2)
_cell_length_b                   9.9373(2)
_cell_length_c                   18.8362(3)
_cell_measurement_reflns_used    8976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4380
_cell_measurement_theta_min      4.5540
_cell_volume                     1927.76(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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     33.00  71.00   0.50    1.45    --  106.29 -61.00  60.00   76
  2  \w     33.00  71.00   0.50    1.45    --  106.29 -61.00 150.00   76
  3  \w     92.00 178.00   0.50    1.45    --  106.29  45.00  90.00  172
  4  \w     90.00 178.00   0.50    1.45    --  106.29  59.00 172.00  176
  5  \w     30.00 120.00   0.50    0.36    --   46.90  59.00 172.00  180
  6  \w     33.00  68.00   0.50    1.45    --  106.29 -59.00  32.00   70
  7  \w     33.00  65.00   0.50    1.45    --  106.29 -61.00   0.00   64
  8  \w    -25.00  64.00   0.50    0.36    --   46.90 -59.00  32.00  178
  9  \w     35.00  61.00   0.50    1.45    --  106.29 -61.00-180.00   52
 10  \w     33.00 105.00   0.50    1.45    --  106.29 -94.00 -30.00  144
 11  \w    -63.00  26.00   0.50    0.36    --  -46.90  59.00 172.00  178
 12  \w    -68.00 -19.00   0.50    1.45    --  -91.75  59.00 172.00   98
 13  \w    -71.00 -19.00   0.50    1.45    --  -91.75  61.00 120.00  104
 14  \w    -71.00 -19.00   0.50    1.45    --  -91.75  61.00  30.00  104
 15  \w    -51.00 -19.00   0.50    1.45    --  -91.75  45.00  30.00   64
 16  \w    -51.00 -19.00   0.50    1.45    --  -91.75  45.00   0.00   64
 17  \w    -51.00 -19.00   0.50    1.45    --  -91.75  45.00 -60.00   64
 18  \w    -51.00 -19.00   0.50    1.45    --  -91.75  45.00 -90.00   64
 19  \w    -51.00 -19.00   0.50    1.45    --  -91.75  45.00 150.00   64
 20  \w   -164.00 -91.00   0.50    1.45    --  -91.75 -61.00 120.00  146
 21  \w   -164.00-100.00   0.50    1.45    --  -91.75 -94.00 150.00  128
 22  \w   -164.00 -75.00   0.50    1.45    --  -91.75 -59.00  32.00  178
 23  \w   -119.00 -30.00   0.50    0.36    --  -46.90 -59.00  32.00  178
 24  \w   -119.00 -87.00   0.50    0.36    --  -46.90-125.00-150.00   64
 25  \w   -119.00 -87.00   0.50    0.36    --  -46.90-125.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0856504000
_diffrn_orient_matrix_UB_12      -0.0240940000
_diffrn_orient_matrix_UB_13      -0.0734819000
_diffrn_orient_matrix_UB_21      0.0793563000
_diffrn_orient_matrix_UB_22      0.1052097000
_diffrn_orient_matrix_UB_23      -0.0344811000
_diffrn_orient_matrix_UB_31      0.0935328000
_diffrn_orient_matrix_UB_32      -0.1112539000
_diffrn_orient_matrix_UB_33      -0.0166933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.362
_diffrn_reflns_theta_min         4.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0519P)^2^+0.7248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3170
_reflns_number_total             3713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01578a2.cif
_cod_data_source_block           hpd630b2
_cod_depositor_comments
'Adding full bibliography for 1571926--1571927.cif.'
_cod_database_code               1571927
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'SB2-104B try 2'
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.834
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 N5-O1B
 1.2 with sigma of 0.02
3. Others
 Fixed Sof: O1A(0.85) O1B(0.15)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C9(H9), C13(H13), C16(H16), C12(H12), C11(H11), C10(H10), C19(H19),
 C18(H18), C17(H17)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              64862
_shelx_hkl_checksum              85308
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 3.461
_oxdiff_exptl_absorpt_empirical_full_min 0.380