Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with <i>o</i>-quinones.
Tsou, Yun-Jie; Guan, Ren-You; Han, Jeng-Liang; Organic & biomolecular chemistry 19 (2021) 5836–5843; doi:10.1039/d1ob00888a

data_7158109
_publ_section_title
;
 Enantioselective organocatalytic vinylogous aldol-cyclization cascade
 reaction of 3-alkylidene oxindoles with <i>o</i>-quinones.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5836
_journal_page_last               5843
_journal_paper_doi               10.1039/d1ob00888a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C28 H24 Br N O5'
_chemical_formula_sum            'C28 H24 Br N O5'
_chemical_formula_weight         534.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-09-28
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2020-09-29 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2170(7)
_cell_length_b                   15.0680(14)
_cell_length_c                   23.762(2)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.95
_cell_volume                     2584.0(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            40741
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         2.905
_exptl_absorpt_coefficient_mu    1.628
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1096
_exptl_transmission_factor_max   0.987
_exptl_transmission_factor_min   0.253
_platon_squeeze_details
;
TITL g129qn_5br2_2_0m_a.res in P1 New:P212121
CELL    7.2170   15.0680   23.7620     90.00     90.00     90.00
SPGR P212121
Q101 0.288 0.858 0.711 !       1.15 eA-3
Q102 0.945 0.362 0.892 !       0.90 eA-3
Q103 0.056 0.095 0.917 !       0.83 eA-3
C104 0.147 0.302 0.936 !       0.78 eA-3
Q105 0.663 0.812 0.572 !       0.65 eA-3
Q106 0.184 0.419 0.944 !       0.58 eA-3
Q107 0.265 0.684 0.494 !       0.58 eA-3
Q108 0.213 0.623 0.463 !       0.51 eA-3
;
_refine_diff_density_max         1.101
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.047(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0646P)^2^+4.6172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4934
_reflns_number_total             5270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00888a2.cif
_cod_data_source_block           g129qn_5br2_2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158108--7158109.cif.
;
_cod_database_code               7158109
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.953(16)
 0.047(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H03H,H03I,H03J} of C03L, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  {H03E,H03F,H03G} of C03H, {H03K,H03L,H03M} of C03W, {H03A,H03B,H03C} of C039
3.a Riding coordinates:
 N00V(H00V), C03L(H03H,H03I,H03J)
3.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B)
3.c Aromatic/amide H refined with riding coordinates:
 C013(H013), C014(H014), C01W(H01W), C027(H027), C02D(H02D), C02R(H02R),
 C035(H035), C038(H038), C03B(H03D)
3.d Idealised Me refined as rotating group:
 C039(H03A,H03B,H03C), C03H(H03E,H03F,H03G), C03W(H03K,H03L,H03M)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'