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_1544521
_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         'C26 H32 N2 O4 Si'
_chemical_formula_sum            'C26 H32 N2 O4 Si'
_chemical_formula_weight         464.62
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-07-14
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.85(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.118(2)
_cell_length_b                   19.642(3)
_cell_length_c                   12.625(2)
_cell_measurement_reflns_used    2952
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      25.8030
_cell_measurement_theta_min      4.1920
_cell_volume                     2576.5(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -33.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6528  -19.0000   90.0000 84

  2 omega   74.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6528    0.0000 -120.0000 25

  3 omega   45.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6528  178.0000  -30.0000 46

  4 omega  -77.00    1.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6528    0.0000 -120.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0593205000
_diffrn_orient_matrix_UB_12      -0.0049395000
_diffrn_orient_matrix_UB_13      -0.0084761000
_diffrn_orient_matrix_UB_21      0.0159343000
_diffrn_orient_matrix_UB_22      -0.0265345000
_diffrn_orient_matrix_UB_23      0.0406630000
_diffrn_orient_matrix_UB_31      -0.0299774000
_diffrn_orient_matrix_UB_32      -0.0238651000
_diffrn_orient_matrix_UB_33      -0.0434369000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15075
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.454
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0093(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0524P)^2^+0.4466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3302
_reflns_number_total             5252
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02965_si_002.cif
_cod_data_source_block           g160704a
_cod_depositor_comments
;Adding full bibliography for 1544521--1544523.cif.

 Adding full bibliography for 1544521--1544523.cif.
;
_cod_original_cell_volume        2576.5(9)
_cod_database_code               1544521
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.941
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              9607
_shelx_hkl_checksum              65752
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'