A photo-auxiliary approach - enabling excited state classical phototransformations with metal free visible light irradiation.
Iyer, Akila; Jockusch, Steffen; Sivaguru, Jayaraman; Chemical communications (Cambridge, England) 53 (2017) 1692–1695; doi:10.1039/c6cc09261f

data_7119270
_publ_section_title
;
 A photo-auxiliary approach - enabling excited state classical
 phototransformations with metal free visible light irradiation.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1692
_journal_page_last               1695
_journal_paper_doi               10.1039/c6cc09261f
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C12 H10 N2 O3'
_chemical_formula_sum            'C12 H10 N2 O3'
_chemical_formula_weight         230.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-15 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.098(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   8.5484(3)
_cell_length_b                   34.4488(11)
_cell_length_c                   15.2307(5)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.634
_cell_measurement_theta_min      3.916
_cell_volume                     4401.3(3)
_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)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29898
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.713
_diffrn_reflns_theta_max         66.713
_diffrn_reflns_theta_min         2.565
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.9121.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .06
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         7716
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0457P)^2^+1.9956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6847
_reflns_number_total             7716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09261f2.cif
_cod_data_source_block           compd_15
_cod_depositor_comments
'Adding full bibliography for 7119269--7119271.cif.'
_cod_database_code               7119270
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H4A,H4B} of C4, {H9A,H9B} of C9, {H1A,H1B} of C1, All
  N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H7A,H7B} of C7
2. Restrained distances
 C7-H7B
 0.86 with sigma of 0.01
 C7-H7A
 0.86 with sigma of 0.01
 H7B-H7A
 1.404623 with sigma of 0.03
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N11(H11), C6(H6), C2AA(H2AA), C4AA(H4AA), C10(H10), C12(H12),
 C13(H13), N16(H16), C21(H21), C22(H22), N26(H26), C29(H29), C30(H30), C33(H33),
  C34(H34), C40(H40), C41(H41), C43(H43), C44(H44)
3.b X=CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C1(H1A,H1B)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C19(H19A,H19B,H19C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              48767
_shelx_hkl_checksum              85758
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'