Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids
Lindsay, Vincent; Murphy, Rebecca; Sarpong, Richmond; Chem. Commun.  (2017) –; doi:10.1039/C7CC06367A

data_7120605
_publ_section_title
;
 Effect of protic additives in Cu-catalysed asymmetric Diels-Alder
 cycloadditions of doubly activated dienophiles: towards the synthesis of
 magellanine-type Lycopodium alkaloids
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06367A
_journal_year                    2017
_chemical_formula_sum            'C22 H33 N O3 Si'
_chemical_formula_weight         387.58
_chemical_name_common            RMXII-193
_chemical_name_systematic
; 
 sarpong59 
;
_space_group.centring_type       P
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-08-14 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.906(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6138(8)
_cell_length_b                   11.1045(5)
_cell_length_c                   11.1829(5)
_cell_measurement_reflns_used    9656
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.51
_cell_volume                     2182.21(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2013
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32201
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         2.514
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.110
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+2.2930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3468
_reflns_number_total             3982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06367a2.cif
_cod_data_source_block           sarpong59
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               7120605
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2013-4
_shelx_res_checksum              97560