Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to prepare pentacyclic chromeno[4,3-b]indolines
Nie, Chang-Rui; Zhao, Hong-Ping; Liang, Wang-Fu; Zhong, Xin-Xian; Liang, Cui; Su, Gui-Fa; Mo, Dong-Liang; Green Chemistry 24 (2022) 6854–6859; doi:10.1039/D2GC02225G

data_7245456
_publ_section_title
;
 Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to
 prepare pentacyclic chromeno[4,3-b]indolines
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              6854
_journal_page_last               6859
_journal_paper_doi               10.1039/D2GC02225G
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C30 H25 N O2'
_chemical_formula_sum            'C30 H25 N O2'
_chemical_formula_weight         431.53
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-09 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                99.033(4)
_cell_angle_beta                 97.884(4)
_cell_angle_gamma                107.657(4)
_cell_formula_units_Z            2
_cell_length_a                   9.206(3)
_cell_length_b                   10.087(3)
_cell_length_c                   13.161(4)
_cell_measurement_reflns_used    5487
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.37
_cell_volume                     1127.7(6)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14151
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.783
_diffrn_reflns_theta_min         1.598
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0659P)^2^+0.2182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3807
_reflns_number_total             4768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02225g2.cif
_cod_data_source_block           aaaa
_cod_depositor_comments
;
          Adding full bibliography for 7245456.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.61 H2.17 N0.09 O0.17'
_cod_original_formula_weight         37.52
_cod_original_formula_moiety         '0.09(C30 H25 N O2)'
_cod_original_formula_units_Z            23
_cod_original_cell_volume        1127.8(5)
_cod_database_code               7245456
_shelx_shelxl_version_number     2014/7
_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.a Riding coordinates:
 N003(H003)
2.b Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
2.c Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00C), C00K(H00I,H00K)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
;
_shelx_res_checksum              3626
_olex2_submission_special_instructions 'No special instructions were received'