Asymmetric construction of pyrido[1,2-<i>a</i>]-1<i>H</i>-indole derivatives <i>via</i> a gold-catalyzed cycloisomerization.
Jiang, Feng; Fu, Chunling; Ma, Shengming; Chemical science 12 (2020) 696–701; doi:10.1039/d0sc05619g

data_1560133
_publ_section_title
;
 Asymmetric construction of pyrido[1,2-<i>a</i>]-1<i>H</i>-indole
 derivatives <i>via</i> a gold-catalyzed cycloisomerization.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              696
_journal_page_last               701
_journal_paper_doi               10.1039/d0sc05619g
_journal_volume                  12
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H16 Br N'
_chemical_formula_sum            'C19 H16 Br N'
_chemical_formula_weight         338.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-26 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.922(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.077(4)
_cell_length_b                   5.678(3)
_cell_length_c                   13.478(6)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.91
_cell_measurement_theta_min      2.39
_cell_volume                     765.6(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17069
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.014
_diffrn_reflns_theta_min         2.391
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.677
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1466 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.6670.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0251P)^2^+0.0365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4253
_reflns_number_total             4827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05619g2.cif
_cod_data_source_block           190329_jf_3_020_0m
_cod_depositor_comments
'Adding full bibliography for 1560133--1560134.cif.'
_cod_database_code               1560133
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.368
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              30316
_olex2_submission_special_instructions 'No special instructions were received'