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_1555575
_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_formula_moiety         'C16 H15 F3 N2'
_chemical_formula_sum            'C16 H15 F3 N2'
_chemical_formula_weight         292.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-30
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Olex2 1.2
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_cell_measurement_reflns_used    12418
_cell_measurement_temperature    180.00(10)
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_cell_measurement_theta_min      5.0260
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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;
  1 omega  -93.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -49.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993   38.0000    0.0000 53

  3 omega  101.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6993  178.0000 -180.0000 25

  4 omega   41.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000 -120.0000 58

  5 omega   30.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000   60.0000 61

  6 omega  119.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000   90.0000 59

  7 omega   30.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  120.0000 56

  8 omega   64.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000 -180.0000 27

  9 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993  -57.0000    0.0000 104

 10 omega -131.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000 -180.0000 101

 12 omega   23.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000   60.0000 86

 13 omega   80.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000 -120.0000 98

 14 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000   90.0000 101

 15 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993  -57.0000  120.0000 104

 16 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993   38.0000  -90.0000 85

 17 omega   46.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   15.0000   30.0000 132

 18 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  -90.0000 104

 19 omega   33.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   33.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000  -90.0000 65

 21 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993  -77.0000  -60.0000 112

 22 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993   38.0000   60.0000 85

 23 omega   80.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000  120.0000 98

 24 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  150.0000 104

 26 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000 -180.0000 104

 27 omega -119.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6993  -77.0000   60.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      -0.0422848000
_diffrn_orient_matrix_UB_13      0.0503915000
_diffrn_orient_matrix_UB_21      -0.2159610000
_diffrn_orient_matrix_UB_22      0.0020668000
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_diffrn_orient_matrix_UB_33      -0.0112357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_Laue_measured_fraction_full 0.972
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_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17421
_diffrn_reflns_point_group_measured_fraction_full 0.972
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.491
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_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
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;
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description
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_exptl_crystal_F_000             608
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_refine_diff_density_min         -0.148
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_refine_ls_abs_structure_details
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
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_refine_ls_restrained_S_all      1.175
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.2227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
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_cod_data_source_file            ol6b01186_si_001.cif
_cod_data_source_block           exp_5785
_cod_original_cell_volume        1381.97(4)
_cod_database_code               1555575
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C16 H24 N2 F3'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.911
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Uiso/Uaniso restraints and constraints
Uanis(F3B) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.01
Uanis(F2B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.008
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C13(H13), C14(H14)
4.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c)
;
_shelx_res_checksum              29641
_shelx_hkl_checksum              38738
_olex2_submission_special_instructions 'No special instructions were received'