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_1520574
_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_formula_moiety         'C19 H17 N1 O1'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.35
_chemical_melting_point          381.0(10)
_chemical_name_systematic        4-(4-methoxyphenyl)-3-methyl-2-phenylpyridine
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2015-04-21
_audit_creation_method           CRYSTALS_ver_14.61
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4565(1)
_cell_length_b                   18.3137(2)
_cell_length_c                   20.6855(3)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2824.73(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            66732
_diffrn_reflns_theta_full        26.935
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         5.232
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9741
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.0004486
_refine_ls_shift/su_mean         0.0000582
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 18.0 28.0 14.1 3.74 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1211
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1211
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2443
_reflns_number_total             3216
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.33
_oxford_diffrn_Wilson_scale      9.78
_oxford_refine_ls_r_factor_ref   0.0604
_oxford_refine_ls_scale          0.3124(5)
_oxford_reflns_number_all        3216
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 049tjd15
_cod_data_source_file            ol5b01312_si_002.cif
_cod_data_source_block           4s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '380-382' was changed to '381.0(10)'
- 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.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

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 b c a '
_cod_original_formula_sum        'C19 H17 N1 O1'
_cod_database_code               1520574