Chloride-incorporating cascade dearomatization of isoquinolines with chloroformate and DMAD achieving 100% atom economy.
Mao, Zhuo-Ya; Yan, De-Xiang; Zhou, Su-Fan; Liu, Meng-En; Li, You-Zherui; Liang, Tai-Gang; Wei, Bang-Guo; Chemical communications (Cambridge, England) 62 (2026) 1860–1863; doi:10.1039/d5cc06083d

data_7135507
_publ_section_title
;
 Chloride-incorporating cascade dearomatization of isoquinolines with
 chloroformate and DMAD achieving 100% atom economy.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1860
_journal_page_last               1863
_journal_paper_doi               10.1039/d5cc06083d
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C21 H24 Cl N O6'
_chemical_formula_sum            'C21 H24 Cl N O6'
_chemical_formula_weight         421.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-12 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.366(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5201(5)
_cell_length_b                   8.6569(2)
_cell_length_c                   22.7664(6)
_cell_measurement_reflns_used    9410
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      29.1860
_cell_measurement_theta_min      1.8010
_cell_volume                     4044.15(17)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_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 0.823
_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    -74.00 -36.00   0.50    0.13    --   10.52 -19.00-150.00   76
  2  \w    -12.00  23.00   0.50    0.13    --   10.52 -19.00-150.00   70
  3  \w     28.00  78.00   0.50    0.13    --   10.52  57.00   0.00  100
  4  \w     -8.00  86.00   0.50    0.13    --   10.52  57.00  90.00  188
  5  \w    -53.00   9.00   0.50    0.13    --  -11.30  98.00 160.00  124
  6  \w      2.00  28.00   0.50    0.13    --   10.52 -99.00 120.00   52
  7  \w    -86.00 -46.50   0.50    0.13    --  -11.30 -77.00 -30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0278775000
_diffrn_orient_matrix_UB_12      0.0228580000
_diffrn_orient_matrix_UB_13      -0.0163978000
_diffrn_orient_matrix_UB_21      -0.0140931000
_diffrn_orient_matrix_UB_22      -0.0738520000
_diffrn_orient_matrix_UB_23      0.0045536000
_diffrn_orient_matrix_UB_31      -0.0148000000
_diffrn_orient_matrix_UB_32      0.0271902000
_diffrn_orient_matrix_UB_33      0.0260910000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16369
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.476
_diffrn_reflns_theta_min         1.789
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0383P)^2^+3.0256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3882
_reflns_number_total             4621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06083d2.cif
_cod_data_source_block           6813-a027-100k_auto
_cod_database_code               7135507
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.889
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B), C20(H20A,H20B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C7(H7), C4(H4), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              93630
_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 1.140
_oxdiff_exptl_absorpt_empirical_full_min 0.890