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_7226214
_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         'C25 H20 N3 O2, C25 H21 N3 O2'
_chemical_formula_sum            'C50 H41 N6 O4'
_chemical_formula_weight         789.89
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-02-24 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.14(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.156(3)
_cell_length_b                   10.118(2)
_cell_length_c                   25.816(5)
_cell_measurement_reflns_used    12022
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4843
_cell_measurement_theta_min      1.3057
_cell_volume                     4073.6(15)
_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., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0136
_diffrn_orient_matrix_UB_12      0.0118
_diffrn_orient_matrix_UB_13      -0.0616
_diffrn_orient_matrix_UB_21      -0.0660
_diffrn_orient_matrix_UB_22      0.0736
_diffrn_orient_matrix_UB_23      -0.0005
_diffrn_orient_matrix_UB_31      0.0299
_diffrn_orient_matrix_UB_32      0.0268
_diffrn_orient_matrix_UB_33      0.0008
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28360
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.306
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7639
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             1660
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         9274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0704
_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^)+(0.0475P)^2^+1.8113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7997
_reflns_number_total             9274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra13643e2.cif
_cod_data_source_block           mx3423
_cod_original_cell_volume        4073.8(15)
_cod_database_code               7226214
_shelxl_version_number           2013-4
_diffrn_number_total             9808
_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. Others
 Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C9)=Sof(H9)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C34(H34), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C35(H35A,H35B), C42(H42A,H42B), C44(H44A,H44B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32), C46(H46),
  C47(H47), C48(H48), C49(H49), C50(H50)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              54798