Synthesis of 3-Aminoindenes and cis-1-Aminoindanes by Zn(OTf)2-Catalyzed Cyclization of o-Alkynylbenzaldehydes with Tertiary Alkyl Primary Amines
Yao, Tuanli; Zhu, Rui; Liu, Tao; Chemical Communications  (2023) –; doi:10.1039/D3CC04180H

data_7132304
_publ_section_title
;
 Synthesis of 3-Aminoindenes and cis-1-Aminoindanes by Zn(OTf)2-Catalyzed
 Cyclization of o-Alkynylbenzaldehydes with Tertiary Alkyl Primary Amines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04180H
_journal_year                    2023
_chemical_formula_moiety         'C22 H24 Cl N O2'
_chemical_formula_sum            'C22 H24 Cl N O2'
_chemical_formula_weight         369.87
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-16 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                89.888(3)
_cell_angle_beta                 82.761(3)
_cell_angle_gamma                87.726(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4089(3)
_cell_length_b                   9.7814(3)
_cell_length_c                   10.8175(4)
_cell_measurement_reflns_used    6017
_cell_measurement_temperature    303.64(10)
_cell_measurement_theta_max      67.9080
_cell_measurement_theta_min      4.1160
_cell_volume                     986.84(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.64(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.963
_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     90.00 130.00   0.50    0.50    --   41.90  56.00  82.00   80
  2  \w     36.00  80.00   0.50    0.50    --   41.90  56.00  82.00   88
  3  \w     67.00 167.00   0.50    0.50    --   94.40  56.00  82.00  200
  4  \w     83.00 109.00   0.50    0.50    --   94.40 -56.00 -59.00   52
  5  \w     26.00  66.00   0.50    0.50    --   41.90 -82.00  90.00   80
  6  \w     29.00 106.00   0.50    0.50    --   41.90  54.00  30.00  154
  7  \w     20.00 113.00   0.50    0.50    --   41.90  65.00 -60.00  186
  8  \w    -28.00  -3.00   0.50    0.50    --   41.90 -82.00 120.00   50
  9  \w      6.00  34.00   0.50    0.50    --   41.90 -82.00 -30.00   56
 10  \w    -48.00  24.00   0.50    0.50    --   41.90 -82.00-150.00  144
 11  \w    -47.00 -22.00   0.50    0.50    --   41.90 -82.00 -60.00   50
 12  \w     43.00  96.00   0.50    0.50    --   41.90  65.00-150.00  106
 13  \w     38.00  69.00   0.50    0.50    --   41.90 -82.00 -30.00   62
 14  \w     24.00  67.00   0.50    0.50    --   41.90 -82.00 120.00   86
 15  \w     65.00 107.00   0.50    0.50    --   41.90  82.00 120.00   84
 16  \w     18.00  44.00   0.50    0.50    --   41.90  82.00 120.00   52
 17  \w     32.00  68.00   0.50    0.50    --   41.90 -82.00-150.00   72
 18  \w     12.00  37.00   0.50    0.50    --   41.90 -56.00 -59.00   50
 19  \w     31.00  67.00   0.50    0.50    --   41.90 -82.00  30.00   72
 20  \w     30.00  63.00   0.50    0.50    --   41.90 -82.00 -60.00   66
 21  \w     98.00 123.00   0.50    0.50    --   41.90  65.00-150.00   50
 22  \w     71.00 143.00   0.50    0.50    --   94.40  68.00-180.00  144
 23  \w     56.00 122.00   0.50    0.50    --   94.40 -59.00  30.00  132
 24  \w     33.00 119.00   0.50    0.50    --   94.40 -82.00   0.00  172
 25  \w     94.00 120.00   0.50    0.50    --   94.40 -77.00-150.00   52
 26  \w     31.00  87.00   0.50    0.50    --   94.40 -77.00-150.00  112
 27  \w    117.00 183.00   0.50    0.50    --   94.40  33.00 150.00  132
 28  \w     86.00 131.00   0.50    0.50    --   94.40 -33.00  90.00   90
 29  \w     16.00  69.00   0.50    0.50    --   94.40 -82.00-180.00  106
 30  \w     76.00 101.00   0.50    0.50    --   94.40 -82.00-180.00   50
 31  \w      6.00  46.00   0.50    0.50    --   94.40 -68.00-120.00   80
 32  \w    142.00 168.00   0.50    0.50    --   94.40  50.00 -30.00   52
 33  \w     11.00 102.00   0.50    0.50    --   94.40 -82.00  60.00  182
 34  \w     69.00  95.00   0.50    0.50    --   94.40 -82.00-150.00   52
 35  \w      6.00 108.00   0.50    0.50    --   94.40 -82.00 -90.00  204
 36  \w    139.00 184.00   0.50    0.50    --   94.40  50.00 120.00   90
 37  \w    101.00 182.00   0.50    0.50    --   94.40  42.00  60.00  162
 38  \w     82.00 108.00   0.50    0.50    --   94.40 -82.00 -30.00   52
 39  \w    107.00 134.00   0.50    0.50    --   94.40  50.00 120.00   54
 40  \w    101.00 126.00   0.50    0.50    --   94.40  68.00-150.00   50
 41  \w      9.00  65.00   0.50    0.50    --   94.40 -82.00 -30.00  112
 42  \w     68.00 102.00   0.50    0.50    --   94.40  50.00 120.00   68
 43  \w     65.00  92.00   0.50    0.50    --   94.40  42.00  60.00   54
 44  \w     40.00 111.00   0.50    0.50    --   94.40 -82.00 120.00  142
 45  \w     30.00  56.00   0.50    0.50    --   94.40 -82.00 -60.00   52
 46  \w     65.00  90.00   0.50    0.50    --   94.40 -82.00 -60.00   50
 47  \w      8.00  62.00   0.50    0.50    --   94.40 -33.00  90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1070874000
_diffrn_orient_matrix_UB_12      -0.0264041000
_diffrn_orient_matrix_UB_13      -0.0930898000
_diffrn_orient_matrix_UB_21      0.0633137000
_diffrn_orient_matrix_UB_22      -0.1470821000
_diffrn_orient_matrix_UB_23      -0.0203734000
_diffrn_orient_matrix_UB_31      -0.1086651000
_diffrn_orient_matrix_UB_32      -0.0501524000
_diffrn_orient_matrix_UB_33      0.1073703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8665
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.061
_diffrn_reflns_theta_min         4.120
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0625
_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^)+(0.1005P)^2^+0.4012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.1872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3088
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04180h2.cif
_cod_data_source_block           20230627c_autored
_cod_database_code               7132304
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     QINGXIANGYANG-2
_diffrn_oxdiff_digest_frames
;
018b0c197c60453c8e568cd801ac5ff18704394cf24
;
_diffrn_oxdiff_digest_hkl
;
0141b4e402289a62cfcd78ea9c44002c11f0f6
;
_reflns_odcompleteness_completeness 97.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C12(H12), C15(H15), C6(H6), C14(H14), C3(H3)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              73508
_shelx_hkl_checksum              28264
_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 1.804
_oxdiff_exptl_absorpt_empirical_full_min 0.506