Organocatalytic Enantioselective Synthesis of 2,3-Dyhidropyridazines
Maitane Fernandez; Jose L. Vicario; Efraim Reyes; Luisa Carrillo; Dolores Badia; Chem.Commun. 48 (2012) 2092–; doi:10.1039/c2cc17370k

data_7107365
_publ_section_title
;
 Organocatalytic Enantioselective Synthesis of 2,3-Dyhidropyridazines
;
_journal_name_full               Chem.Commun.
_journal_page_first              2092
_journal_paper_doi               10.1039/c2cc17370k
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H19 N3 O5 S1'
_chemical_formula_sum            'C19 H19 N3 O5 S'
_chemical_formula_weight         401.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-21T15:06:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 107.716(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0573(2)
_cell_length_b                   10.8477(2)
_cell_length_c                   11.3405(2)
_cell_measurement_reflns_used    6172
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9792
_cell_measurement_theta_min      4.0719
_cell_measurement_wavelength     1.54184
_cell_volume                     944.19(4)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4023
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -58.00 35.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.6693 38.0000 -180.0000 93

2 omega -97.00 -13.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.6693 125.0000 -180.0000 84

3 omega 71.00 116.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.6693 77.0000 90.0000 45

4 omega 27.00 57.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.6693 77.0000 120.0000 30

5 omega 16.00 117.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.6693 38.0000 60.0000 101

6 omega 9.00 45.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.6693 77.0000 90.0000 36

7 omega -75.00 -49.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 30.0000 26

8 omega -80.00 -53.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -65.0000 113.0000 27

9 omega -75.00 -49.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 120.0000 26

10 omega -74.00 -49.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 60.0000 25

11 omega -74.00 -49.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 90.0000 25

12 omega -79.00 -52.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -70.0000 32.0000 27

13 omega -74.00 -49.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 150.0000 25

14 omega -78.00 -52.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -70.0000 0.0000 26

15 omega -77.00 -51.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -71.0000 91.0000 26

16 omega 132.00 158.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 150.0000 26

17 omega 79.00 111.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 150.0000 32

18 omega 43.00 74.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 60.0000 31

19 omega 110.00 158.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 45.0000 -180.0000 48

20 omega 39.00 71.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 120.0000 32

21 omega 128.00 157.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 45.0000 -120.0000 29

22 omega 38.00 76.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 30.0000 38

23 omega 90.00 133.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 0.0000 43

24 omega 79.00 143.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 60.0000 64

25 omega 41.00 73.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -180.0000 32

26 omega 107.00 154.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 90.0000 47

27 omega 46.00 73.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 150.0000 27

28 omega 60.00 115.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -112.0000 34.0000 55

29 omega 79.00 106.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 90.0000 27

30 omega 80.00 145.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 30.0000 65

31 omega 40.00 66.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -120.0000 26

32 omega 44.00 77.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -90.0000 33

33 omega 79.00 154.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 120.0000 75

34 omega 55.00 132.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 30.0000 77

35 omega 40.00 65.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 0.0000 25

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.184322
_diffrn_orient_matrix_UB_12      0.0042798
_diffrn_orient_matrix_UB_13      -0.0934746
_diffrn_orient_matrix_UB_21      -0.0767561
_diffrn_orient_matrix_UB_22      0.0272192
_diffrn_orient_matrix_UB_23      0.1061639
_diffrn_orient_matrix_UB_31      0.0206275
_diffrn_orient_matrix_UB_32      0.1393605
_diffrn_orient_matrix_UB_33      -0.0178338
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8056
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         4.09
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.85289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (94%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
The results indicated that the absolute structure had been correctly
assigned. The method calculated that the probability that the structure
is inverted is smaller than 10-99. The absolute structure parameter y
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.028(5), which together with Flack parameter
value, indicate that the absolute structure has surely been determined
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915;
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands;
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717
;
_refine_ls_abs_structure_Flack   -0.008(11)
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.025
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.066
_reflns_number_gt                3585
_reflns_number_total             3637
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c2cc17370k.txt
_cod_data_source_block           mf464
_cod_original_cell_volume        944.19(3)
_cod_database_code               7107365