Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation.
Hardegger, Leo A.; Habegger, Jacqueline; Donohoe, Timothy J.; Organic letters 17 (2015) 3222–3225; doi:10.1021/acs.orglett.5b01312

data_1520573
_publ_section_title
;
 Modular Synthesis of Highly Substituted Pyridines via Enolate
 \a-Alkenylation.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3222
_journal_page_last               3225
_journal_paper_doi               10.1021/acs.orglett.5b01312
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 N1 S1'
_chemical_formula_sum            'C17 H15 N S'
_chemical_formula_weight         265.38
_chemical_melting_point          379.5(15)
_chemical_name_systematic        3,5-dimethyl-2-phenyl-4-(thiophen-2-yl)pyridine
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             15-03-27
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1669(2)
_cell_length_b                   12.1820(3)
_cell_length_c                   17.8605(6)
_cell_measurement_reflns_used    4943
_cell_measurement_temperature    150
_cell_measurement_theta_max      75
_cell_measurement_theta_min      5
_cell_volume                     1341.77(7)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11812
_diffrn_reflns_theta_full        74.580
_diffrn_reflns_theta_max         76.102
_diffrn_reflns_theta_min         4.393
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details 'Flack (1983), 1147 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.43(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9323
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.0002961
_refine_ls_shift/su_mean         0.0000405
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.49P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0880
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0880
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2604
_reflns_number_total             2783
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.67
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0368
_oxford_refine_ls_scale          7.8(2)
_oxford_reflns_number_all        2772
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 055tjd15
_cod_data_source_file            ol5b01312_si_002.cif
_cod_data_source_block           4o
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '378-381' was changed to '379.5(15)'
- the average value was taken and precision was estimated.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520573--1520574.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H15 N1 S1'
_cod_database_code               1520573
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S U'S 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE  S(16,U'S) C(119,U'S) 
RIDE  C(17,U'S) C(118,U'S) 
RIDE  C(18,U'S) C(117,U'S) 
RIDE  C(19,U'S) S(116,U'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   ( 117,X'S) H   (1171,X'S) 
RIDE C   ( 118,X'S) H   (1181,X'S) 
RIDE C   ( 119,X'S) H   (1191,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
SAME  C(4)  C(15)  S(16)   C(17)   C(18)   C(19)  AND 
CONT  C(4)  C(15)  S(116)  C(117)  C(118)  C(119) 
DIST  0, 0.01 = MEAN 
CONT  C(15)  TO  C(19)  C(15)  TO  C(119) 
CONT  C(17)  TO  C(18)  C(117) TO  C(118) 
PLANAR  C(4)  C(15)  S(16)   C(17)   C(18)   C(19) 
PLANAR  C(4)  C(15)  S(116)  C(117)  C(118)  C(119) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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