Alcohol Mediated Isocyanide Domino Reactions Toward 2-Aminofuronaphthoquinones
Martin-Acosta, Pedro; Bratukhin, Maksim; Estévez-Braun, Ana; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB02014J

data_7161101
_publ_section_title
;
 Alcohol-mediated isocyanide domino reactions toward the synthesis of
 2-aminofuronaphthoquinones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3709
_journal_page_last               3720
_journal_paper_doi               10.1039/d5ob02014j
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-30 deposited with the CCDC.	2026-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   35.7051(19)
_cell_length_b                   35.7051(19)
_cell_length_c                   6.9742(5)
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      61.8800
_cell_measurement_theta_min      8.5790
_cell_volume                     7699.9(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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     20.00  74.00   1.00   30.00    --    0.00  19.00-180.00   54
  2  \w      9.00  78.00   1.00  150.00    --   83.48 -30.00 -90.00   69
  3  \w      2.00  84.00   1.00  150.00    --   83.48   0.00-180.00   82
  4  \w    119.00 163.00   1.00  150.00    --   83.48   0.00-180.00   44
  5  \w    108.00 153.00   1.00  150.00    --   83.48 125.00  30.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0176332000
_diffrn_orient_matrix_UB_12      0.0326472000
_diffrn_orient_matrix_UB_13      -0.1669111000
_diffrn_orient_matrix_UB_21      0.0407205000
_diffrn_orient_matrix_UB_22      -0.0044746000
_diffrn_orient_matrix_UB_23      -0.0082515000
_diffrn_orient_matrix_UB_31      -0.0226470000
_diffrn_orient_matrix_UB_32      -0.0373715000
_diffrn_orient_matrix_UB_33      -0.1443330000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4797
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        62.043
_diffrn_reflns_theta_max         62.043
_diffrn_reflns_theta_min         4.289
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             2988
_exptl_crystal_size_max          0.072
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0669P)^2^+4.0399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2117
_reflns_number_total             2628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob02014j2.cif
_cod_data_source_block           pma_compa
_cod_depositor_comments          'Adding full bibliography for 7161101.cif.'
_cod_original_cell_volume        7699.9(10)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7161101
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H19 O4 N1'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4809
_shelx_fab_checksum              90924
_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.736