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_7059873
_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 H16 Cl N O2'
_chemical_formula_sum            'C18 H16 Cl N O2'
_chemical_formula_weight         313.77
_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             2020-04-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.04.02 svn.r1fbe7b6f for OlexSys, GUI svn.r6076)
;
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                100.487(8)
_cell_angle_beta                 104.790(7)
_cell_angle_gamma                106.520(8)
_cell_formula_units_Z            2
_cell_length_a                   7.3932(6)
_cell_length_b                   10.0477(10)
_cell_length_c                   11.2604(10)
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0750
_cell_measurement_theta_min      3.0230
_cell_volume                     745.56(13)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -60.00  40.00   1.00    1.00    --   11.74 -57.00 150.00  100
  2  \w    -21.00  88.00   1.00    1.00    --   11.74  77.00  60.00  109
  3  \w    -16.00  85.00   1.00    1.00    --   11.74  57.00 -60.00  101
  4  \w     34.00  99.00   1.00    1.00    --   11.74-178.00 150.00   65
  5  \w    -16.00  23.00   1.00    1.00    --   11.74  57.00-180.00   39
  6  \w    -20.00  53.00   1.00    1.00    --   11.74 -99.00 -30.00   73
;
_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      -0.0982811000
_diffrn_orient_matrix_UB_12      -0.0506208000
_diffrn_orient_matrix_UB_13      -0.0302614000
_diffrn_orient_matrix_UB_21      -0.0390454000
_diffrn_orient_matrix_UB_22      0.0526527000
_diffrn_orient_matrix_UB_23      0.0225581000
_diffrn_orient_matrix_UB_31      -0.0043050000
_diffrn_orient_matrix_UB_32      0.0230069000
_diffrn_orient_matrix_UB_33      -0.0562680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45234
_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    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0382P)^2^+0.2861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2354
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01981j2.cif
_cod_data_source_block           33-2
_cod_depositor_comments
;Adding full bibliography for 7059872--7059873.cif.

 Adding full bibliography for 7059872--7059873.cif.
;
_cod_original_cell_volume        745.55(12)
_cod_database_code               7059873
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C14(H14), C5(H5), C3(H3), C11(H11), C13(H13), C2(H2), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              28538
_olex2_date_sample_data_collection 2019-03-22
_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 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.638