Cu-catalyzed cyclization to construct indoles from N-(ortho-chloromethyl)aryl carbamates and terminal alkynes via a one-pot reaction
Shi, Yang; Wang, Gangqiang; Wang, Hang; Deng, Bin; Gao, Tao; Wang, Jian; Guo, Haibing; Wu, Minghu; Sun, Shaofa; New Journal of Chemistry 44 (2020) 14477–14480; doi:10.1039/D0NJ01981J

data_7059872
_publ_section_title
;
 Cu-catalyzed cyclization to construct indoles from
 N-(ortho-chloromethyl)aryl carbamates and terminal alkynes via a one-pot
 reaction
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14477
_journal_page_last               14480
_journal_paper_doi               10.1039/D0NJ01981J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.459(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7871(13)
_cell_length_b                   28.773(3)
_cell_length_c                   10.9288(12)
_cell_measurement_reflns_used    2881
_cell_measurement_temperature    293.02(10)
_cell_measurement_theta_max      73.2030
_cell_measurement_theta_min      4.4020
_cell_volume                     2966.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      293.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_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     20.00 113.00   1.00    1.00    --   40.98  57.00  90.00   93
  2  \w     96.00 124.00   1.00    1.80    --  107.58 123.00  -4.00   28
  3  \w    112.00 178.00   1.00    1.80    --  107.58  77.00 -30.00   66
  4  \w    144.00 178.00   1.00    1.80    --  107.58  30.00-180.00   34
  5  \w    115.00 140.00   1.00    1.80    --  107.58 -77.00 -90.00   25
  6  \w     80.00 122.00   1.00    1.80    --  107.58  30.00-180.00   42
  7  \w     32.00  68.00   1.00    1.80    --  107.58 -77.00 -90.00   36
  8  \w     37.00 108.00   1.00    1.80    --  107.58 -94.00-120.00   71
  9  \w     43.00 132.00   1.00    1.80    --  107.58 -45.00   0.00   89
 10  \w     29.00 109.00   1.00    1.80    --  107.58 -94.00 -30.00   80
 11  \w    -51.00 -17.00   1.00    1.00    --  -40.98 -37.00-120.00   34
 12  \w   -115.00 -59.00   1.00    1.00    --  -40.98 -37.00-120.00   56
 13  \w    -95.00 -36.00   1.00    1.00    --  -40.98 125.00  90.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0540168000
_diffrn_orient_matrix_UB_12      0.0385907000
_diffrn_orient_matrix_UB_13      -0.0986946000
_diffrn_orient_matrix_UB_21      -0.0369305000
_diffrn_orient_matrix_UB_22      -0.0368384000
_diffrn_orient_matrix_UB_23      -0.1061333000
_diffrn_orient_matrix_UB_31      -0.1496326000
_diffrn_orient_matrix_UB_32      -0.0047920000
_diffrn_orient_matrix_UB_33      0.0192428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.954
_diffrn_reflns_theta_min         4.470
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0941
_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^)+(0.1391P)^2^+8.9962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3152
_refine_ls_wR_factor_ref         0.3292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4334
_reflns_number_total             5845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01981j2.cif
_cod_data_source_block           fy-o-2
_cod_depositor_comments
;Adding full bibliography for 7059872--7059873.cif.

 Adding full bibliography for 7059872--7059873.cif.
;
_cod_database_code               7059872
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.76
_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 Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C9(H9A,H9B), C17(H17A,H17B), C010(H01A,H01B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N006(H006), C14(H14), C00G(H00G), C00I(H00I), C00K(H00K), C00P(H00P),
 C6(H6), C11(H11), C00T(H00T), C00U(H00U), C00V(H00V), C13(H13), C12(H12),
 C00Y(H00Y), C2(H2), C011(H011), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C015(H01C,H01D,H01E)
;
_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 2.561
_oxdiff_exptl_absorpt_empirical_full_min 0.477