2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade: access to tetracyclic indoles.
Han, Tian-Jiao; Wang, Min-Can; Mei, Guang-Jian; Chemical communications (Cambridge, England) 57 (2021) 8921–8924; doi:10.1039/d1cc03653j

data_7128746
_publ_section_title
;
 2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade:
 access to tetracyclic indoles.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8921
_journal_page_last               8924
_journal_paper_doi               10.1039/d1cc03653j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 Br N O3'
_chemical_formula_sum            'C22 H18 Br N O3'
_chemical_formula_weight         424.28
_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     direct
_audit_creation_date             2021-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.200(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1529(6)
_cell_length_b                   30.7743(11)
_cell_length_c                   8.7822(4)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9910
_cell_measurement_theta_min      5.4260
_cell_volume                     2194.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -102.00 -11.00   1.00    1.75    --  -33.50 -77.00-180.00   91
  2  \w    -44.00 -16.00   1.00    1.75    --  -33.50 -57.00-150.00   28
  3  \w    -91.00 -65.00   1.00    1.75    --  -33.50 -57.00 120.00   26
  4  \w   -107.00 -81.00   1.00    1.75    --  -33.50 178.00   0.00   26
  5  \w     39.00  98.00   1.00    1.75    --   36.47  57.00  30.00   59
  6  \w     -3.00  74.00   1.00    1.75    --   36.47 -99.00  60.00   77
  7  \w     59.00 104.00   1.00    1.75    --   36.47  57.00  90.00   45
  8  \w     70.00  97.00   1.00   10.50    --  108.00 -94.00-150.00   27
  9  \w     79.00 177.00   1.00   10.50    --  108.00  77.00 -90.00   98
 10  \w    101.00 155.00   1.00   10.50    --  108.00 111.00 150.00   54
 11  \w    133.00 174.00   1.00   10.50    --  108.00  61.00-180.00   41
 12  \w     89.00 130.00   1.00   10.50    --  108.00  61.00-180.00   41
 13  \w    116.00 142.00   1.00   10.50    --  108.00  61.00-120.00   26
 14  \w     41.00 112.00   1.00   10.50    --  108.00-111.00 -30.00   71
 15  \w     38.00 110.00   1.00   10.50    --  108.00 -94.00-180.00   72
 16  \w    139.00 167.00   1.00   10.50    --  108.00  61.00 -60.00   28
 17  \w     41.00  67.00   1.00   10.50    --  108.00 -94.00   0.00   26
 18  \w     66.00 129.00   1.00   10.50    --  108.00 178.00   0.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1864409000
_diffrn_orient_matrix_UB_12      -0.0009990000
_diffrn_orient_matrix_UB_13      -0.0479855000
_diffrn_orient_matrix_UB_21      0.0042915000
_diffrn_orient_matrix_UB_22      -0.0500479000
_diffrn_orient_matrix_UB_23      -0.0023492000
_diffrn_orient_matrix_UB_31      -0.0346879000
_diffrn_orient_matrix_UB_32      -0.0009694000
_diffrn_orient_matrix_UB_33      0.1695000000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.258
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0810P)^2^+0.2436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2805
_reflns_number_total             3918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03653j2.cif
_cod_data_source_block           202104106
_cod_depositor_comments
'Adding full bibliography for 7128745--7128746.cif.'
_cod_original_cell_volume        2194.41(19)
_cod_database_code               7128746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2Br1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.703
_reflns_odcompleteness_completeness 99.85
_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. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br1A)
3. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C18(H18), C19(H19), C21(H21), C22(H22), N1(H1A)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.807