Ruthenium-Catalyzed Enantioselective Hydrogenation of 1,8-Naphthyridine Derivatives.
Ma, Wenpeng; Chen, Fei; Liu, Youran; He, Yan-Mei; Fan, Qing-Hua; Organic letters 18 (2016) 2730–2733; doi:10.1021/acs.orglett.6b01186

data_1555576
_publ_section_title
;
 Ruthenium-Catalyzed Enantioselective Hydrogenation of 1,8-Naphthyridine
 Derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2730
_journal_page_last               2733
_journal_paper_doi               10.1021/acs.orglett.6b01186
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H24 N2 O2 S'
_chemical_formula_sum            'C27 H24 N2 O2 S'
_chemical_formula_weight         440.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.577(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.581(3)
_cell_length_b                   9.532(3)
_cell_length_c                   11.106(3)
_cell_measurement_reflns_used    3728
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4786
_cell_measurement_theta_min      1.8339
_cell_volume                     1120.1(6)
_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 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0729
	          2theta: -19.9826
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0729
	          2theta: -19.9826
scan:
	Number of images: 312
	           Slice: -110.0000 - 46.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0729
	          2theta: -19.9826
;
_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      -0.0037
_diffrn_orient_matrix_UB_12      0.0536
_diffrn_orient_matrix_UB_13      -0.0778
_diffrn_orient_matrix_UB_21      0.0906
_diffrn_orient_matrix_UB_22      -0.0415
_diffrn_orient_matrix_UB_23      -0.0329
_diffrn_orient_matrix_UB_31      -0.0453
_diffrn_orient_matrix_UB_32      -0.0646
_diffrn_orient_matrix_UB_33      -0.0434
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12116
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.646
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.1982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                4971
_reflns_number_total             5021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01186_si_002.cif
_cod_data_source_block           sa4399
_cod_original_cell_volume        1120.0(5)
_cod_database_code               1555576
_diffrn_number_total             2717
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              21245
_shelx_hkl_checksum              78132
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'