A visible-light Paternò–Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles
Mateos, Javier; Vega-Peñaloza, Alberto; Franceschi, Pietro; Rigodanza, Francesco; Andreetta, Philip; Companyó, Xavier; Pelosi, Giorgio; Bonchio, Marcella; Dell’Amico, Luca; Chemical Science 11 (2020) 6532–6538; doi:10.1039/D0SC01569E

data_1557811
_publ_section_title
;
 A visible-light Patern\`o--B\"uchi dearomatisation process towards the
 construction of oxeto-indolinic polycycles
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              6532
_journal_page_last               6538
_journal_paper_doi               10.1039/D0SC01569E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C35 H33 N O4'
_chemical_formula_sum            'C35 H33 N O4'
_chemical_formula_weight         531.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F -2d 2'
_space_group_name_H-M_alt        'F 2 d d'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-17 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   8.4764(13)
_cell_length_b                   33.008(5)
_cell_length_c                   40.934(6)
_cell_measurement_reflns_used    3730
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.305
_cell_measurement_theta_min      2.341
_cell_volume                     11453(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS CCD diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            34654
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.464
_diffrn_reflns_theta_min         1.585
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1759 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.8842.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prim
_exptl_crystal_F_000             4512
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5881
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0366P)^2^+2.5070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3900
_reflns_number_total             5881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01569e2.cif
_cod_data_source_block           luc2_0m
_cod_depositor_comments
;

 Adding full bibliography for 1557811.cif.

2022-09-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C560 H528 N16 O64'
_cod_original_formula_weight         8505.95
_cod_original_formula_moiety         '16(C35 H33 N O4)'
_cod_original_formula_units_Z            1
_cod_database_code               1557811
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H0AA,H0AB,H0AC} of C0AA, All C(H,H) groups
 At 1.5 times of:
  {H5CA,H5CB,H5CC} of C5CA, {H2DA,H2DB,H2DC} of C2DA, {H4DA,H4DB,H4DC} of C4DA
2.a Secondary CH2 refined with riding coordinates:
 C6BA(H6BA,H6BB)
2.b Aromatic/amide H refined with riding coordinates:
 C0BA(H0BA), C1BA(H1BA), C3BA(H3BA), C4BA(H4BA), C5BA(H5BA), C7BA(H7BA),
 C8BA(H8BA), C9BA(H9BA), C0CA(H0CA), C1CA(H1CA), C2CA(H2CA), C3CA(H3CA),
 C4CA(H4CA), C7CA(H7CA), C8CA(H8CA), C9CA(H9CA), C0DA(H0DA), C1DA(H1DA),
 C3DA(H3DA)
2.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C5CA(H5CA,H5CB,H5CC), C2DA(H2DA,H2DB,H2DC), C4DA(H4DA,
 H4DB,H4DC)
;