Extension of hydrogen borrowing alkylation reactions for the total synthesis of (−)-γ-lycorane
Hall, Christopher J. J.; Marriott, Indi S.; Christensen, Kirsten E.; Day, Aaron J.; Goundry, William R. F.; Donohoe, Timothy J.; Chemical Communications  (2022) –; doi:10.1039/D2CC01248K

data_7129901
_publ_section_title
;
 Extension of hydrogen borrowing alkylation reactions for the total
 synthesis of (&#x2212;)-\g-lycorane
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01248K
_journal_year                    2022
_chemical_formula_moiety         'C16 H19 N O2'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.33
_chemical_melting_point          ?
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2022-02-01
_audit_creation_method           'CRYSTALS_ver_14.61_build_7932 '
_audit_update_record
;
2022-02-09 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                101.237(6)
_cell_angle_beta                 99.446(5)
_cell_angle_gamma                110.609(7)
_cell_formula_units_Z            4
_cell_length_a                   9.5572(6)
_cell_length_b                   12.2819(10)
_cell_length_c                   12.4294(6)
_cell_measurement_reflns_used    5384
_cell_measurement_temperature    150
_cell_measurement_theta_max      75.45
_cell_measurement_theta_min      3.75
_cell_volume                     1295.68(17)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_av_unetI/netI     0.076
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21905
_diffrn_reflns_theta_full        75.275
_diffrn_reflns_theta_max         76.811
_diffrn_reflns_theta_min         3.748
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             551.996
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.0001002
_refine_ls_shift/su_mean         0.0000092
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.12P)^2^ + 0.42P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2172
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2172
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4112
_reflns_number_total             5401
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.13
_oxford_diffrn_Wilson_scale      0.05
_oxford_refine_ls_scale          4.83(17)
_oxford_structure_analysis_title 7144
_cod_data_source_file            d2cc01248k2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

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

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7129901
_oxford_refine_reflns_threshold_expression I>-10.0\s(I)
_refine_ls_r_factor_ref          0.0839
_reflns_number_all               5401