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_7119622
_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         'C14 H12 Br N O2'
_chemical_formula_sum            'C14 H12 Br N O2'
_chemical_formula_weight         306.16
_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
_audit_creation_date             2014-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.4870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1984(5)
_cell_length_b                   7.3629(2)
_cell_length_c                   19.2858(5)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.502
_cell_measurement_theta_min      2.910
_cell_volume                     2450.81(11)
_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  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.96
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.993
_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  0.0475
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34112
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.851
_diffrn_reflns_theta_min         2.910
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.534
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0904 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.7792.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       plate
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0315P)^2^+4.2277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3735
_reflns_number_total             4323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc02962k2.cif
_cod_data_source_block           2c
_cod_depositor_comments
;

2017-10-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H12 Br N O2)'
_cod_original_formula_sum        'C27 H24 Br2 N3 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     614.31
_cod_database_code               7119622
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.773
_shelx_estimated_absorpt_t_min   0.409
_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:
 C10(H10), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C13(H13), C20(H20), C21(H21), C23(H23), C25(H25)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              33599
_shelx_hkl_checksum              50290
_olex2_submission_special_instructions 'No special instructions were received'