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_7226213
_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         'C24 H20 N4 O2'
_chemical_formula_sum            'C24 H20 N4 O2'
_chemical_formula_weight         396.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2014-11-20
_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                 112.20(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.285(2)
_cell_length_b                   14.466(3)
_cell_length_c                   13.528(3)
_cell_measurement_reflns_used    7622
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4813
_cell_measurement_theta_min      1.4076
_cell_volume                     2044.7(8)
_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 0.998
_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      0.0646
_diffrn_orient_matrix_UB_12      -0.0687
_diffrn_orient_matrix_UB_13      -0.0167
_diffrn_orient_matrix_UB_21      0.0027
_diffrn_orient_matrix_UB_22      -0.0139
_diffrn_orient_matrix_UB_23      0.0677
_diffrn_orient_matrix_UB_31      -0.0341
_diffrn_orient_matrix_UB_32      -0.0710
_diffrn_orient_matrix_UB_33      -0.0132
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24275
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.012
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       rod
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8978
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0380P)^2^+0.5320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                8603
_reflns_number_total             8978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra13643e2.cif
_cod_data_source_block           mx3405
_cod_original_cell_volume        2044.9(8)
_cod_database_code               7226213
_shelxl_version_number           2013-4
_diffrn_number_total             4884
_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:
 C7(H7), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B), C18(H18A,H18B), C33(H33A,H33B), C40(H40A,H40B),
 C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C44(H44),
  C45(H45), C46(H46), C47(H47), C48(H48)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              66138