Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C-N bonds.
Millward, Makenzie J.; Ellis, Emily; Ward, John W.; Clayden, Jonathan; Chemical science 12 (2020) 2091–2096; doi:10.1039/d0sc06188c

data_1559763
_publ_section_title
;
 Hydantoin-bridged medium ring scaffolds by migratory insertion of
 urea-tethered nitrile anions into aromatic C-N bonds.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2091
_journal_page_last               2096
_journal_paper_doi               10.1039/d0sc06188c
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C17 H21 N3 O'
_chemical_formula_sum            'C17 H21 N3 O'
_chemical_formula_weight         283.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                88.989(2)
_cell_angle_beta                 74.751(2)
_cell_angle_gamma                77.777(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0488(2)
_cell_length_b                   8.6329(3)
_cell_length_c                   12.6463(5)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.42
_cell_volume                     725.03(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13480
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.115
_diffrn_reflns_theta_min         1.670
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0487 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.9181. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.322
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0422P)^2^+0.3184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3130
_reflns_number_total             3531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06188c2.cif
_cod_data_source_block           testt1_CCDC1
_cod_depositor_comments
;Adding full bibliography for 1559758--1559767.cif.

 Adding full bibliography for 1559758--1559767.cif.
;
_cod_database_code               1559763
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              65439
_olex2_submission_special_instructions 'No special instructions were received'