Organocatalytic regio- and enantioselective C1-arylation of β,γ-alkynyl-α-imino esters with pyrrolo[2,1-<i>a</i>]isoquinolines.
Zhang, Xuan; Song, Xiaoxiao; Ni, Qijian; Chemical communications (Cambridge, England) 60 (2024) 831–834; doi:10.1039/d3cc04946a

data_7132487
_publ_section_title
;
 Organocatalytic regio- and enantioselective C1-arylation of
 &#x3b2;,&#x3b3;-alkynyl-&#x3b1;-imino esters with
 pyrrolo[2,1-<i>a</i>]isoquinolines.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              831
_journal_page_last               834
_journal_paper_doi               10.1039/d3cc04946a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H30 N2 O6'
_chemical_formula_sum            'C31 H30 N2 O6'
_chemical_formula_weight         526.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-09 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                105.430(3)
_cell_angle_beta                 99.759(3)
_cell_angle_gamma                108.874(4)
_cell_formula_units_Z            2
_cell_length_a                   10.1018(8)
_cell_length_b                   11.4504(7)
_cell_length_c                   13.7104(12)
_cell_measurement_reflns_used    3536
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      29.684
_cell_measurement_theta_min      3.083
_cell_volume                     1388.58(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.735
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.735
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12577
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.134
_diffrn_reflns_theta_min         2.802
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0511 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9223.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0607P)^2^+0.1134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4171
_reflns_number_total             7152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04946a2.cif
_cod_data_source_block           20220530c
_cod_depositor_comments
'Adding full bibliography for 7132486--7132487.cif.'
_cod_database_code               7132487
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_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. Uiso/Uaniso restraints and constraints
O6A \\sim O6 \\sim C30 \\sim C30A \\sim C31 \\sim C31A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C29, O6, C30, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C29, O6A, C30A, C31A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(O6A)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=1-FVAR(1)
 Sof(O6)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C30A(H30C,H30D)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C31(H31A,H31B,H31C), C31A(H31D,H31E,H31F)
;
_shelx_res_checksum              19330
_shelx_hkl_checksum              6644
_olex2_submission_special_instructions 'No special instructions were received'