Engaging electronic effects for atropselective [5+2]-photocycloaddition of maleimides
Ramya Raghunathan; Elango Kumarasamy; Steffen Jockusch; Angel Ugrinov; J. Sivaguru; Chem.Commun. 52 (2016) 8305–; doi:

data_7119619
_publ_section_title
;
 Engaging electronic effects for atropselective [5+2]-photocycloaddition
 of maleimides
;
_journal_name_full               Chem.Commun.
_journal_page_first              8305
_journal_volume                  52
_journal_year                    2016
_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           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.285(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9222(7)
_cell_length_b                   7.6509(3)
_cell_length_c                   20.5384(8)
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.548
_cell_measurement_theta_min      5.540
_cell_volume                     2509.90(18)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15458
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.763
_diffrn_reflns_theta_min         5.539
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.9033.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.1101
_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^+29.5786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2873
_refine_ls_wR_factor_ref         0.2902
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3820
_reflns_number_total             4309
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc02962k2.cif
_cod_data_source_block           2f
_cod_database_code               7119619
_shelxl_version_number           2014-3
_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:
 C5(H5), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C25(H25A,H25B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C15(H15), C18(H18), C22(H22), C23(H23), C29(H29)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              16985
_shelx_hkl_checksum              24843
_olex2_submission_special_instructions 'No special instructions were received'