Phosphine-Catalyzed [3+2] Cycloaddition of Phthalazinium Dicyanomethanides with Allenoates: Highly Efficient Synthesis of 1,2,3,10b-Tetrahydropyrrolo[2,1-a]phthalazine Derivatives
Guo, Hongchao; Zhou, Leijie; Sun, Zhanhu; Yuan, Chunhao; RSC Adv.  (2016) –; doi:10.1039/C6RA13643E

data_7226215
_publ_section_title
;
 Phosphine-Catalyzed [3+2] Cycloaddition of Phthalazinium
 Dicyanomethanides with Allenoates: Highly Efficient Synthesis of
 1,2,3,10b-Tetrahydropyrrolo[2,1-a]phthalazine Derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA13643E
_journal_year                    2016
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-02-24 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                83.90(3)
_cell_angle_beta                 89.32(3)
_cell_angle_gamma                71.399(19)
_cell_formula_units_Z            2
_cell_length_a                   8.427(5)
_cell_length_b                   8.87(5)
_cell_length_c                   11.531(7)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4667
_cell_measurement_theta_min      1.7766
_cell_volume                     812(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.1167
              2theta: -20.2741
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.1167
              2theta: -20.2741
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0163
_diffrn_orient_matrix_UB_12      -0.1132
_diffrn_orient_matrix_UB_13      0.0510
_diffrn_orient_matrix_UB_21      -0.0207
_diffrn_orient_matrix_UB_22      -0.0077
_diffrn_orient_matrix_UB_23      -0.1177
_diffrn_orient_matrix_UB_31      0.0856
_diffrn_orient_matrix_UB_32      -0.0165
_diffrn_orient_matrix_UB_33      -0.0043
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6873
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.452
_diffrn_reflns_theta_min         2.858
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0943
_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^)+(0.1504P)^2^+0.3504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.2690
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3003
_reflns_number_total             3614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra13643e2.cif
_cod_data_source_block           sa4018a
_cod_database_code               7226215
_diffrn_number_total             3616
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              26281
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'