The base-catalysed Tamura cycloaddition reaction: calculation, mechanism, isolation of intermediates and asymmetric catalysis
Lockett-Walters, Bruce; Trujillo, Cristina; Twamley, Brendan; Connon, Stephen; Chemical Communications  (2019) –; doi:10.1039/C9CC05064G

data_7124109
_publ_section_title
;
 The base-catalysed Tamura cycloaddition reaction: calculation, mechanism,
 isolation of intermediates and asymmetric catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05064G
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 N3 O7'
_chemical_formula_sum            'C21 H17 N3 O7'
_chemical_formula_weight         423.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-03 deposited with the CCDC.    2019-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.905(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6218(12)
_cell_length_b                   11.9315(18)
_cell_length_c                   11.960(2)
_cell_measurement_reflns_used    1058
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      3.11
_cell_volume                     933.5(3)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19135
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.824
_diffrn_reflns_theta_min         3.114
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0607 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.9438. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4860
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0415P)^2^+0.0865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4233
_reflns_number_total             4860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05064g2.cif
_cod_data_source_block           tcd1201
_cod_original_cell_volume        933.6(3)
_cod_database_code               7124109
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N20-H20
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C24(H24), C25(H25), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              31748
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id BLEW515
_olex2_submission_special_instructions 'No special instructions were received'