Syntheses of Tetrahydropyridazine and Tetrahydro-1,2-diazepine Scaffolds through Cycloaddition Reactions of Azoalkenes with Enol Diazoacetates.
Deng, Yongming; Pei, Chao; Arman, Hadi; Dong, Kuiyong; Xu, Xinfang; Doyle, Michael P.; Organic letters 18 (2016) 5884–5887; doi:10.1021/acs.orglett.6b02965

data_1544522
_publ_section_title
;
 Syntheses of Tetrahydropyridazine and Tetrahydro-1,2-diazepine Scaffolds
 through Cycloaddition Reactions of Azoalkenes with Enol Diazoacetates.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5884
_journal_page_last               5887
_journal_paper_doi               10.1021/acs.orglett.6b02965
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         352.38
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 124.417(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.35(4)
_cell_length_b                   5.606(5)
_cell_length_c                   21.40(2)
_cell_measurement_reflns_used    6850
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.3
_cell_volume                     3498(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
    Number of images: 246
               Slice: -68.0000 - 55.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 180.0000
                 XTD: 34.5407
              2theta: -34.4110
scan:
    Number of images: 176
               Slice: -52.0000 - 36.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 0.0000
                 XTD: 34.5407
              2theta: -34.4110
scan:
    Number of images: 122
               Slice: -81.0000 - -20.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 34.5407
              2theta: -34.4110
scan:
    Number of images: 94
               Slice: -65.0000 - -18.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 270.0000
                 XTD: 34.5407
              2theta: -34.4110
scan:
    Number of images: 60
               Slice: -115.0000 - -85.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 270.0000
                 XTD: 34.5407
              2theta: -34.4110
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.009726
_diffrn_orient_matrix_UB_12      -0.009529
_diffrn_orient_matrix_UB_13      0.031468
_diffrn_orient_matrix_UB_21      0.169004
_diffrn_orient_matrix_UB_22      0.040860
_diffrn_orient_matrix_UB_23      -0.039860
_diffrn_orient_matrix_UB_31      0.002159
_diffrn_orient_matrix_UB_32      0.034692
_diffrn_orient_matrix_UB_33      0.044718
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11965
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         2.417
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       plank
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0300P)^2^+3.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2892
_reflns_number_total             3703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02965_si_003.cif
_cod_data_source_block           cd1453
_cod_depositor_comments
;Adding full bibliography for 1544521--1544523.cif.

 Adding full bibliography for 1544521--1544523.cif.
;
_cod_original_cell_volume        3499(6)
_cod_database_code               1544522
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H,H,H,H,H,H,H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'