Tandem Construction of Indole-Fused Phthalazines from (2-Alkynylbenzylidene)hydrazines under Metal-Free Conditions.
Shi, Zhaojiang; Wang, Lianhui; Yang, Zi; Jie, Lianghua; Liu, Xiao; Cui, Xiuling; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02937

data_4037956
_publ_section_title
;
 Tandem Construction of Indole-Fused Phthalazines from
 (2-Alkynylbenzylidene)hydrazines under Metal-Free Conditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02937
_journal_year                    2020
_chemical_formula_moiety         'C21 H14 N2'
_chemical_formula_sum            'C21 H14 N2'
_chemical_formula_weight         294.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.458(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7095(10)
_cell_length_b                   9.6147(4)
_cell_length_c                   18.3936(10)
_cell_measurement_reflns_used    3374
_cell_measurement_temperature    293.01(10)
_cell_measurement_theta_max      28.5020
_cell_measurement_theta_min      4.0300
_cell_volume                     3032.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.864
_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     -1.00  83.00   1.00    5.00    --   15.65  57.00  60.00   84
  2  \w     25.00  56.00   1.00    5.00    --   15.65  57.00 120.00   31
  3  \w     35.00  72.00   1.00    5.00    --   15.65 178.00 -60.00   37
  4  \w    -33.00  44.00   1.00    5.00    --  -16.43  77.00 150.00   77
  5  \w    -52.00  42.00   1.00    5.00    --   15.65 -77.00 -60.00   94
  6  \w    -23.00  22.00   1.00    5.00    --  -16.43 -99.00-150.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0222569000
_diffrn_orient_matrix_UB_12      0.0578978000
_diffrn_orient_matrix_UB_13      0.0171709000
_diffrn_orient_matrix_UB_21      -0.0348453000
_diffrn_orient_matrix_UB_22      0.0383174000
_diffrn_orient_matrix_UB_23      -0.0027013000
_diffrn_orient_matrix_UB_31      -0.0018221000
_diffrn_orient_matrix_UB_32      -0.0248421000
_diffrn_orient_matrix_UB_33      0.0358200000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11902
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         29.399
_diffrn_reflns_theta_min         3.535
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0549P)^2^+1.8545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2540
_reflns_number_total             3623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02937_si_002.cif
_cod_data_source_block           exp_6031
_cod_database_code               4037956
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C1 \\sim C5: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C3 \\sim C18: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              66716
_shelx_hkl_checksum              7880
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.743