Dictating photoreactivity through restricted bond rotations: cross-photoaddition of atropisomeric acrylimide derivatives under UV/visible-light irradiation.
Iyer, Akila; Jockusch, Steffen; Sivaguru, J.; The journal of physical chemistry. A 118 (2014) 10596–10602; doi:10.1021/jp505678b

data_1517658
_publ_section_title
;
 Dictating photoreactivity through restricted bond rotations:
 cross-photoaddition of atropisomeric acrylimide derivatives under
 UV/visible-light irradiation.
;
_journal_issue                   45
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              10596
_journal_page_last               10602
_journal_paper_doi               10.1021/jp505678b
_journal_volume                  118
_journal_year                    2014
_chemical_formula_moiety         'C23 H25 N O2'
_chemical_formula_sum            'C23 H25 N O2'
_chemical_formula_weight         347.44
_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             2014-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.611(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9205(4)
_cell_length_b                   8.8195(3)
_cell_length_c                   11.1609(4)
_cell_measurement_reflns_used    8548
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.736
_cell_measurement_theta_min      4.112
_cell_volume                     940.49(6)
_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      100.01
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.997
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10630
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.731
_diffrn_reflns_theta_min         4.113
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0499 before and 0.0379 after correction.
The Ratio of minimum to maximum transmission is 0.8880.
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    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0355P)^2^+0.1438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3260
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jp505678b_si_002.cif
_cod_data_source_block           M-isomer_1a
_cod_depositor_comments
'Adding full bibliography for 1517657--1517659.cif.'
_cod_database_code               1517658
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.838
_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 Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C21(H21),
 C22(H22)
2.b X=CH2 refined with riding coordinates:
 C19(H19A,H19B), C23(H23A,H23B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              18101
_shelx_hkl_checksum              51669
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'