Synthesis of tetrahydro-β-carbolines from 2-indolylmethyl azides and propargylic alcohols
Yin, Haiting; Ma, Qin; Wang, Yushan; Gu, Xiaoxia; Feng, Zhijun; Wu, Yunjun; Wang, Ming; Wang, Shaoyin; RSC Advances 11 (2021) 19639–19646; doi:10.1039/D1RA03022A

data_7242947
_publ_section_title
;
 Synthesis of tetrahydro-\b-carbolines from 2-indolylmethyl azides and
 propargylic alcohols
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              19639
_journal_page_last               19646
_journal_paper_doi               10.1039/D1RA03022A
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C30 H22 N4, [+ solvents]'
_chemical_formula_sum            'C30 H22 N4'
_chemical_formula_weight         438.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-24 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.9730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3091(8)
_cell_length_b                   14.2045(9)
_cell_length_c                   16.5877(11)
_cell_measurement_reflns_used    8019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.799
_cell_measurement_theta_min      2.217
_cell_volume                     2837.2(3)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23952
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_min         1.885
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6452
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0745P)^2^+0.0612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4408
_reflns_number_total             6452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra03022a2.cif
_cod_data_source_block           140902b_0m
_cod_database_code               7242947
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C26, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C24(H24), C14(H14), C20(H20), C23(H23), C22(H22), C15(H15),
 C21(H21), C4(H4), C3(H3), C2(H2), C30(H30), C18(H18), C16(H16), C26(H26),
 C28(H28), C29(H29), C17(H17), C27(H27)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              23676
_shelx_fab_checksum              12242
_olex2_submission_special_instructions 'No special instructions were received'