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_4121981
_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_formula_moiety         '0.5(H2 O), C15 H15 N O3'
_chemical_formula_sum            'C15 H16 N O3.5'
_chemical_formula_weight         266.29
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9133(2)
_cell_length_b                   17.4560(4)
_cell_length_c                   6.68560(10)
_cell_measurement_reflns_used    6988
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.55
_cell_measurement_theta_min      4.78
_cell_volume                     1273.62(4)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 1.000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9437
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.571
_diffrn_reflns_theta_min         4.779
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6698
_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 0.0364 after correction.
The Ratio of minimum to maximum transmission is 0.8897.
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    1.389
_exptl_crystal_description       rod
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0636P)^2^+0.3352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2202
_reflns_number_total             2245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5034638_si_002.cif
_cod_data_source_block           1S5R7R-3a
_cod_depositor_comments
'Adding full bibliography for 4121977--4121989.cif.'
_cod_original_formula_sum        'C15 H16 N O3.50'
_cod_database_code               4121981
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.826
_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, All O(H,H) groups
2. Others
 Fixed Sof: H1SA(0.5) H1SB(0.5)
3.a Free rotating group:
 O1S(H1SA,H1SB)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C5(H5)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C6(H6A,H6B)
3.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C11(H11)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              91932
_shelx_hkl_checksum              1228