Tailoring atropisomeric maleimides for stereospecific [2 + 2] photocycloaddition-photochemical and photophysical investigations leading to visible-light photocatalysis.
Kumarasamy, Elango; Raghunathan, Ramya; Jockusch, Steffen; Ugrinov, Angel; Sivaguru, J.; Journal of the American Chemical Society 136 (2014) 8729–8737; doi:10.1021/ja5034638

data_4121978
_publ_section_title
;
 Tailoring atropisomeric maleimides for stereospecific [2 + 2]
 photocycloaddition-photochemical and photophysical investigations leading
 to visible-light photocatalysis.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8729
_journal_page_last               8737
_journal_paper_doi               10.1021/ja5034638
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            'C15 H15 N O3'
_chemical_formula_weight         257.28
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2839 for OlexSys, GUI svn.r4715)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5256(3)
_cell_length_b                   6.9706(2)
_cell_length_c                   24.6411(6)
_cell_measurement_reflns_used    9043
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.61
_cell_measurement_theta_min      3.04
_cell_volume                     2493.31(11)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35878
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.654
_diffrn_reflns_theta_min         3.044
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0598 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.9118.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       rod
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         8708
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0357P)^2^+0.5856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                8348
_reflns_number_total             8708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5034638_si_002.cif
_cod_data_source_block           1R5S6R-2a
_cod_depositor_comments
'Adding full bibliography for 4121977--4121989.cif.'
_cod_database_code               4121978
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C6D(H6D), C5D(H5D), C6C(H6C), C5C(H5C), C6A(H6A), C5A(H5A), C6B(H6B), C5B(H5B)
2.b Secondary CH2 refined with riding coordinates:
 C8D(H8DA,H8DB), C7D(H7DA,H7DB), C8C(H8CA,H8CB), C7C(H7CA,H7CB), C7A(H7AA,
 H7AB), C8A(H8AA,H8AB), C7B(H7BA,H7BB), C8B(H8BA,H8BB)
2.c Aromatic/amide H refined with riding coordinates:
 C12D(H12D), C11D(H11D), C13D(H13D), C12C(H12C), C11C(H11C), C13C(H13C),
 C13A(H13A), C12A(H12A), C11A(H11A), C13B(H13B), C12B(H12B), C11B(H11B)
2.d Idealised Me refined as rotating group:
 C19D(H19A,H19B,H19C), C16D(H16A,H16B,H16C), C19C(H19D,H19E,H19F), C16C(H16D,
 H16E,H16F), C19A(H19G,H19H,H19I), C16A(H16G,H16H,H16I), C19B(H19J,H19K,H19L),
 C16B(H16J,H16K,H16L)
;
_shelx_res_checksum              98434
_shelx_hkl_checksum              65188