Tertiary Amine Synthesis via Reductive Coupling of Amides with Grignard Reagents
Dixon, Darren; Xie, Lan-Gui; Chem. Sci.  (2017) –; doi:10.1039/C7SC03613B

data_1546995
_publ_section_title
;
 Tertiary Amine Synthesis via Reductive Coupling of Amides with Grignard
 Reagents
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03613B
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17.67 H21.28 Cl1.30 N0.89 O1.78'
_chemical_formula_sum            'C17.67 H21.28 Cl1.3 N0.89 O1.78'
_chemical_formula_weight         320.75
_chemical_melting_point          ?
_chemical_name_systematic        'Compound 24'
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2017-05-26
_audit_creation_method           CRYSTALS_ver_14.61_build_6156
_audit_update_record
;
2017-06-30 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.376(14)
_cell_angle_gamma                90
_cell_formula_units_Z            9
_cell_length_a                   18.548(4)
_cell_length_b                   11.9461(13)
_cell_length_c                   18.0773(18)
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    150
_cell_measurement_theta_max      73
_cell_measurement_theta_min      4
_cell_volume                     3980.7(10)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.088
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20977
_diffrn_reflns_theta_full        74.871
_diffrn_reflns_theta_max         78.811
_diffrn_reflns_theta_min         4.410
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.29
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528.965
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.64
_refine_diff_density_min         -0.68
_refine_ls_abs_structure_details 'Flack (1983), 3811 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0347
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         8132
_refine_ls_number_restraints     558
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0893
_refine_ls_shift/su_max          0.0111264
_refine_ls_shift/su_mean         0.0007827
_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: 
 0.402E+04 0.659E+04 0.404E+04 0.167E+04 314. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2966
_refine_ls_wR_factor_gt          0.2241
_refine_ls_wR_factor_ref         0.2959
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                5403
_reflns_number_total             8167
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.37
_oxford_diffrn_Wilson_scale      0.13
_oxford_refine_ls_r_factor_ref   0.1184
_oxford_refine_ls_scale          3.01(6)
_oxford_reflns_number_all        8133
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 016djd17
_cod_data_source_file            c7sc03613b2.cif
_cod_data_source_block           24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2 '
_cod_original_formula_sum        'C17.67 H21.28 Cl1.30 N0.89 O1.78'
_cod_database_code               1546995