Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence
Xie, Chao-Chao; Tan, Rui; Liu, Yan-Kai; Organic Chemistry Frontiers 6 (2019) 919–; doi:10.1039/C8QO01406J

data_1554585
_publ_section_title
;
 Asymmetric construction of polycyclic indole derivatives with different
 ring connectivities by an organocatalysis triggered two-step sequence
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              919
_journal_paper_doi               10.1039/C8QO01406J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C21 H24 N2 O7'
_chemical_formula_sum            'C21 H24 N2 O7'
_chemical_formula_weight         416.42
_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     dual
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-11-08 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.736(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6264(13)
_cell_length_b                   10.8580(14)
_cell_length_c                   11.2163(14)
_cell_measurement_reflns_used    1710
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      20.967
_cell_measurement_theta_min      2.311
_cell_volume                     1073.2(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      120.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6528
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_min         2.730
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0479 before and 0.0367 after correction. The Ratio of minimum to maximum transmission is 0.9139. The \l/2 correction factor is 0.00150.'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.9(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4646
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0501P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3074
_reflns_number_total             4646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01406j2.cif
_cod_data_source_block           180603xcc2_0m
_cod_database_code               1554585
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.9(18)
 -0.9(18)
2. 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
3. Rigid body (RIGU) restrains
 O6, C13, C14, O6A, C13A, C14A, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O6A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=1-FVAR(1)
 Sof(O6)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C13(H13A,H13B), C15(H15A,H15B), C13A(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C14A(H14D,H14E,
 H14F)
;
_shelx_res_checksum              99319
_shelx_hkl_checksum              88956
_olex2_submission_special_instructions 'No special instructions were received'