Synthesis of Hydrazide-Containing Chroman-2-ones and Dihydroquinolin-2-ones via Photocatalytic Radical Cascade Reaction of Aroylhydrozones.
Zhao, Yu; Chen, Jia-Rong; Xiao, Wen-Jing; Organic letters 18 (2016) 6304–6307; doi:10.1021/acs.orglett.6b03174

data_1555953
_publ_section_title
;
 Synthesis of Hydrazide-Containing Chroman-2-ones and
 Dihydroquinolin-2-ones via Photocatalytic Radical Cascade Reaction of
 Aroylhydrozones.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6304
_journal_page_last               6307
_journal_paper_doi               10.1021/acs.orglett.6b03174
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H27 N3 O3'
_chemical_formula_sum            'C30 H27 N3 O3'
_chemical_formula_weight         477.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 119.294(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.279(2)
_cell_length_b                   20.305(4)
_cell_length_c                   9.8589(17)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      2.35
_cell_volume                     2492.9(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12287
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.840
_diffrn_reflns_theta_min         1.918
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0940 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.9134.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2083 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6272
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0650P)^2^+0.1402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                5432
_reflns_number_total             6272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03174_si_002.cif
_cod_data_source_block           zy201
_cod_database_code               1555953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Riding coordinates:
 N1(H1)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), N2(H2)
;
_shelx_res_checksum              38933
_shelx_hkl_checksum              54636
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'