Construction of Fused Polyheterocycles through Sequential [4 + 2] and [3 + 2] Cycloadditions.
Feng, Yadong; Tian, Nian; Li, Yudong; Jia, Chunqi; Li, Xuening; Wang, Lianhui; Cui, Xiuling; Organic letters 19 (2017) 1658–1661; doi:10.1021/acs.orglett.7b00452

data_1556024
_publ_section_title
;
 Construction of Fused Polyheterocycles through Sequential [4 + 2] and [3
 + 2] Cycloadditions.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1658
_journal_page_last               1661
_journal_paper_doi               10.1021/acs.orglett.7b00452
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C43 H30 N2 O2'
_chemical_formula_sum            'C43 H30 N2 O2'
_chemical_formula_weight         606.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                92.552(7)
_cell_angle_beta                 94.697(7)
_cell_angle_gamma                98.319(7)
_cell_formula_units_Z            2
_cell_length_a                   10.4789(9)
_cell_length_b                   12.0740(11)
_cell_length_c                   12.5011(11)
_cell_measurement_reflns_used    2522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2480
_cell_measurement_theta_min      3.6920
_cell_volume                     1557.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -31.00  53.00   1.00    9.00    --  -14.59  57.00  30.00   84
  2  \w    -25.00  19.00   1.00    9.00    --  -14.59 -99.00  60.00   44
  3  \w    -81.00   5.00   1.00    9.00    --  -14.59 -37.00-120.00   86
  4  \w     35.00  65.00   1.00    9.00    --   17.71 178.00-180.00   30
  5  \w      2.00  49.00   1.00    9.00    --   17.71  57.00 -60.00   47
  6  \w    -47.00  28.00   1.00    9.00    --   17.71 -77.00-180.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302478000
_diffrn_orient_matrix_UB_12      0.0428838000
_diffrn_orient_matrix_UB_13      0.0383253000
_diffrn_orient_matrix_UB_21      0.0242163000
_diffrn_orient_matrix_UB_22      -0.0409010000
_diffrn_orient_matrix_UB_23      0.0318232000
_diffrn_orient_matrix_UB_31      0.0567569000
_diffrn_orient_matrix_UB_32      0.0053425000
_diffrn_orient_matrix_UB_33      -0.0278317000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12467
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.637
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0732P)^2^+0.0381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3968
_reflns_number_total             6359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00452_si_003.cif
_cod_data_source_block           201512175
_cod_database_code               1556024
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 96.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C34(H34), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39), C41(H41), C42(H42)
2.b Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C)
;
_shelx_res_checksum              87950
_shelx_hkl_checksum              91905
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.162
_oxdiff_exptl_absorpt_empirical_full_min 0.877