Phosphine-Catalyzed [3 + 3]-Domino Cycloaddition of Ynones and Azomethine Imines To Construct Functionalized Hydropyridazine Derivatives.
Liang, Ling; Huang, You; Organic letters 18 (2016) 2604–2607; doi:10.1021/acs.orglett.6b00988

data_1555561
_publ_section_title
;
 Phosphine-Catalyzed [3 + 3]-Domino Cycloaddition of Ynones and Azomethine
 Imines To Construct Functionalized Hydropyridazine Derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2604
_journal_page_last               2607
_journal_paper_doi               10.1021/acs.orglett.6b00988
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H17 Br N2 O2'
_chemical_formula_sum            'C20 H17 Br N2 O2'
_chemical_formula_weight         397.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                107.480(3)
_cell_angle_beta                 90.474(3)
_cell_angle_gamma                97.723(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7454(2)
_cell_length_b                   10.3627(3)
_cell_length_c                   11.1019(4)
_cell_measurement_reflns_used    8216
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.9700
_cell_measurement_theta_min      1.9300
_cell_volume                     841.10(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_temperature      113.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -105.00  75.00   0.50    5.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50    5.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50    5.00    --  -15.00  45.00 180.00  360
;
_diffrn_measurement_device       'Rigaku Xtalab P200'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0705844000
_diffrn_orient_matrix_UB_12      0.0541089000
_diffrn_orient_matrix_UB_13      0.0197299000
_diffrn_orient_matrix_UB_21      0.0180705000
_diffrn_orient_matrix_UB_22      -0.0075382000
_diffrn_orient_matrix_UB_23      -0.0640873000
_diffrn_orient_matrix_UB_31      -0.0570494000
_diffrn_orient_matrix_UB_32      0.0476803000
_diffrn_orient_matrix_UB_33      -0.0014867000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11170
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.030
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.0272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4137
_reflns_number_total             4537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00988_si_001.cif
_cod_data_source_block           m20160111a
_cod_original_cell_volume        841.09(5)
_cod_database_code               1555561
_chemical_oxdiff_formula         'C20 H17 Br N2 O2'
_shelx_estimated_absorpt_t_max   0.757
_shelx_estimated_absorpt_t_min   0.639
_reflns_odcompleteness_completeness 84.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.96
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Riding coordinates:
 C8(H8A,H8B)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              701
_shelx_hkl_checksum              69263
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.575