Combining photochemistry and catalysis: rapid access to sp3– rich polyheterocycles from simple pyrroles
Blackham, Emma E.; Knowles, Jonathan P.; Burgess, Jonathan; Booker-Milburn, Kevin I.; Chem. Sci. 7 (2016) 2302–; doi:10.1039/C5SC04062K

data_1542276
_publ_section_title
;
 Combining photochemistry and catalysis: rapid access to sp3-- rich
 polyheterocycles from simple pyrroles
;
_journal_issue                   3
_journal_name_full               'Chem. Sci.'
_journal_page_first              2302
_journal_paper_doi               10.1039/C5SC04062K
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C25 H28 N4 O5 S'
_chemical_formula_sum            'C25 H28 N4 O5 S'
_chemical_formula_weight         496.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-09 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.776(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4546(4)
_cell_length_b                   18.7124(10)
_cell_length_c                   34.4314(19)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.02
_cell_measurement_theta_min      2.26
_cell_volume                     4800.6(4)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_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  0.0971
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            113630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.088
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.8710.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 6474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1269
_refine_ls_number_reflns         19637
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0293P)^2^+6.7524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                15856
_reflns_number_total             19637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc04062k3.cif
_cod_data_source_block           20a
_cod_depositor_comments
'Adding full bibliography for 1542275--1542277.cif.'
_cod_database_code               1542276
_shelxl_version_number           2013-4
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C13(H13), C58(H58), C60(H60), C63(H63), C33(H33), C35(H35),
 C38(H38), C83(H83), C85(H85), C88(H88)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C24(H24A,H24B), C61(H61A,
 H61B), C62(H62A,H62B), C64(H64A,H64B), C74(H74A,H74B), C36(H36A,H36B),
 C37(H37A,H37B), C39(H39A,H39B), C49(H49A,H49B), C86(H86A,H86B), C87(H87A,H87B),
  C89(H89A,H89B), C99(H99A,H99B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C3(H3), C5(H5), C6(H6), C15(H15), C16(H16), C18(H18),
 C19(H19), C21(H21), C22(H22), N12(H12), C52(H52), C53(H53), C55(H55), C56(H56),
  C65(H65), C66(H66), C68(H68), C69(H69), C71(H71), C72(H72), N8(H8A), C27(H27),
  C28(H28), C30(H30), C31(H31), C40(H40), C41(H41), C43(H43), C44(H44),
 C46(H46), C47(H47), N16(H16A), C77(H77), C78(H78), C80(H80), C81(H81),
 C90(H90), C91(H91), C93(H93), C94(H94), C96(H96), C97(H97)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C25(H25A,H25B,H25C), C57(H57A,H57B,H57C), C75(H75A,H75B,
 H75C), C32(H32A,H32B,H32C), C50(H50A,H50B,H50C), C82(H82A,H82B,H82C),
 C100(H10A,H10B,H10C)
;
_shelx_res_checksum              75698
_olex2_submission_special_instructions 'No special instructions were received'