[4 + 3] Cycloaddition of Phthalazinium Dicyanomethanides with Azoalkenes Formed in Situ: Synthesis of Triazepine Derivatives.
Yang, Wenjun; Yuan, Chunhao; Liu, Yang; Mao, Biming; Sun, Zhanhu; Guo, Hongchao; The Journal of organic chemistry 81 (2016) 7597–7603; doi:10.1021/acs.joc.6b01296

data_4037025
_publ_section_title
;
 [4 + 3] Cycloaddition of Phthalazinium Dicyanomethanides with Azoalkenes
 Formed in Situ: Synthesis of Triazepine Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7597
_journal_page_last               7603
_journal_paper_doi               10.1021/acs.joc.6b01296
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H21 N5 O2'
_chemical_formula_sum            'C23 H21 N5 O2'
_chemical_formula_weight         399.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.070(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.458(2)
_cell_length_b                   17.775(7)
_cell_length_c                   20.714(8)
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4769
_cell_measurement_theta_min      2.2802
_cell_volume                     2004.5(13)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.1295
	          2theta: -20.9953
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.1295
	          2theta: -20.9953
;
_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      -0.0434
_diffrn_orient_matrix_UB_12      -0.0715
_diffrn_orient_matrix_UB_13      -0.1635
_diffrn_orient_matrix_UB_21      0.0106
_diffrn_orient_matrix_UB_22      -0.0516
_diffrn_orient_matrix_UB_23      0.0198
_diffrn_orient_matrix_UB_31      -0.0468
_diffrn_orient_matrix_UB_32      -0.0054
_diffrn_orient_matrix_UB_33      0.0110
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15519
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         1.511
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       rod
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0837
_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^)+(0.0192P)^2^+2.1803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3755
_reflns_number_total             4554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01296_si_002.cif
_cod_data_source_block           sa4360
_cod_original_cell_volume        2004.6(14)
_cod_database_code               4037025
_shelxl_version_number           2013-4
_diffrn_number_total             4726
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              49443
_shelx_hkl_checksum              73601
_olex2_submission_special_instructions 'No special instructions were received'