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_7134875
_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         'C20 H17 Cl3 N2 O2'
_chemical_formula_sum            'C20 H17 Cl3 N2 O2'
_chemical_formula_weight         423.70
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-21
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0344(2)
_cell_length_b                   10.3333(2)
_cell_length_c                   21.6961(6)
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    300
_cell_measurement_theta_max      65.70
_cell_measurement_theta_min      4.08
_cell_volume                     2025.44(8)
_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      300
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0760
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24640
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.438
_diffrn_reflns_theta_min         4.075
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.243
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0757 after correction.
The Ratio of minimum to maximum transmission is 0.7963.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0592P)^2^+0.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2910
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03254g2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7134874--7134876.cif.'
_cod_database_code               7134875
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.758
_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:
 C00E(H00B,H00D), C00M(H00E,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00A(H00A), C00C(H00C), C00F(H00F), C00G(H00G), C00L(H00L),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00N(H00I,H00J,H00K)
;
_shelx_res_checksum              71524
_shelx_hkl_checksum              68167
_olex2_submission_special_instructions 'No special instructions were received'