Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines: Congruence Between Computation and Experiment.
Li, Yifei; Jackson, Kelvin E.; Charlton, Andrew; Le Neve-Foster, Ben; Khurshid, Asma; Rudy, Heinrich-K A; Thompson, Amber L.; Paton, Robert S.; Hodgson, David M.; The Journal of organic chemistry 82 (2017) 10479–10488; doi:10.1021/acs.joc.7b01954

data_4032906
_publ_section_title
;
 Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines:
 Congruence Between Computation and Experiment.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10479
_journal_page_last               10488
_journal_paper_doi               10.1021/acs.joc.7b01954
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H25 N2 O, C2 F3 O2'
_chemical_formula_sum            'C19 H25 F3 N2 O3'
_chemical_formula_weight         386.41
_chemical_melting_point          ?
_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             2016-06-13
_audit_creation_method           CRYSTALS_ver_14.61_build_5555
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7402(2)
_cell_length_b                   11.5964(2)
_cell_length_c                   24.9844(6)
_cell_measurement_reflns_used    8972
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1952.83(8)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.045
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20916
_diffrn_reflns_theta_full        76.223
_diffrn_reflns_theta_max         76.223
_diffrn_reflns_theta_min         4.203
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  0.98
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_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.21
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_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details 'Flack (1983), 1719 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     484
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.0004129
_refine_ls_shift/su_mean         0.0000536
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 0.41P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1275
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                3820
_reflns_number_total             4085
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.20
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0488
_oxford_refine_ls_scale          6.8(2)
_oxford_reflns_number_all        4069
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6560
_cod_data_source_file            jo7b01954_si_003.cif
_cod_data_source_block           M-S1R5S-5-TFA
_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/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032906.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4032906