Photoredox Catalysis: Construction of Polyheterocycles via Alkoxycarbonylation/Addition/Cyclization Sequence.
Li, Xuanxuan; Fang, Xinxin; Zhuang, Shengyi; Liu, Ping; Sun, Peipei; Organic letters 19 (2017) 3580–3583; doi:10.1021/acs.orglett.7b01553

data_1547096
_publ_section_title
;
 Photoredox Catalysis: Construction of Polyheterocycles via
 Alkoxycarbonylation/Addition/Cyclization Sequence.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3580
_journal_page_last               3583
_journal_paper_doi               10.1021/acs.orglett.7b01553
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C21 H17 N3 O3'
_chemical_formula_sum            'C21 H17 N3 O3'
_chemical_formula_weight         359.38
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.109
_cell_length_b                   20.109
_cell_length_c                   9.5683(6)
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.198
_cell_measurement_theta_min      3.110
_cell_volume                     3869.2(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17129
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         3.108
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1560 before and 0.0438 after correction. The Ratio of minimum to maximum transmission is 0.6538. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0800P)^2^+1.0350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2955
_reflns_number_total             3457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01553_si_002.cif
_cod_data_source_block           cu_pzxxxl1_0m_sq
_cod_original_cell_volume        3869.0(2)
_cod_database_code               1547096
_shelx_shelxl_version_number     2014/7
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C17(H17), C18(H18), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
;
_shelx_fab_checksum              30684
_olex2_submission_special_instructions 'No special instructions were received'