C(sp<sup>3</sup>)-H functionalization of <i>N</i>-protected dialkylpyrrole derivatives with azodicarboxylates.
Guo, Jing; Yan, Maying; Xiao, Lei; Li, Jiajie; Qu, Zheng-Wang; Grimme, Stefan; Stephan, Douglas W.; Chemical communications (Cambridge, England) 61 (2025) 13659–13662; doi:10.1039/d5cc03254g

data_7134876
_publ_section_title
;
 C(sp<sup>3</sup>)-H functionalization of <i>N</i>-protected
 dialkylpyrrole derivatives with azodicarboxylates.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13659
_journal_page_last               13662
_journal_paper_doi               10.1039/d5cc03254g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C32 H35 N3 O4'
_chemical_formula_sum            'C32 H35 N3 O4'
_chemical_formula_weight         525.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-27 deposited with the CCDC.	2025-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.8400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0792(4)
_cell_length_b                   20.6051(6)
_cell_length_c                   9.7661(3)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.06
_cell_measurement_theta_min      3.83
_cell_volume                     2799.52(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            73567
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.118
_diffrn_reflns_theta_min         3.834
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1467 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.7968.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0549P)^2^+0.5985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4831
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03254g2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7134874--7134876.cif.'
_cod_database_code               7134876
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C25(H25A,H25B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C31(H31), C6(H6), C12(H12), C30(H30), C8(H8), C7(H7),
 C13(H13), C27(H27), C29(H29), C24(H24), C28(H28), C20(H20), C23(H23), C22(H22),
  C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              84914
_shelx_hkl_checksum              96858
_olex2_submission_special_instructions 'No special instructions were received'