Iron-Catalyzed Triazole-Enabled C‒H Activation with Bicyclopropylidenes
Mo, Jiayu; Messinis, Antonis M.; Oliveira, João C. A.; Demeshko, Serhiy; Meyer, Franc; Ackermann, Lutz; ACS Catalysis  (2021) 1053–1064; doi:10.1021/acscatal.0c04748

data_4518461
_publ_section_title
;
 Iron-Catalyzed Triazole-Enabled C--H Activation with Bicyclopropylidenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1053
_journal_page_last               1064
_journal_paper_doi               10.1021/acscatal.0c04748
_journal_year                    2021
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-07
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9071(8)
_cell_length_b                   9.5864(5)
_cell_length_c                   16.9660(10)
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.115
_cell_measurement_theta_min      2.450
_cell_volume                     2226.2(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture AgMo Dual Source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            67587
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.134
_diffrn_reflns_theta_min         2.084
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.8878
_exptl_absorpt_correction_T_min  0.7786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0776 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0774
_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^)+(0.1075P)^2^+2.4007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2080
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4122
_reflns_number_total             4911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04748_si_001.cif
_cod_data_source_block           mo_0913_cg_0m
_cod_database_code               4518461
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C13(H13), C14(H14), N2(H2), C25(H25), C26(H26),
 C27(H27), C28(H28)
;
_shelx_res_checksum              39329
_shelx_hkl_checksum              98519
_olex2_submission_special_instructions 'No special instructions were received'