Development of synthetic equivalent of α,α-dicationic acetic acid leading to unnatural amino acid derivatives via tetrafunctionalized methanes
Asahara, Haruyasu; Bonkohara, Atsushi; Takagi, Masaya; Iwai, Kento; Ito, Akitaka; Yoshioka, Kotaro; Tani, Shinki; Umezu, Kazuto; Nishiwaki, Nagatoshi; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D1OB02482E

data_7158539
_publ_section_title
;
 Development of synthetic equivalent of \a,\a-dicationic acetic acid
 leading to unnatural amino acid derivatives via tetrafunctionalized
 methanes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02482E
_journal_year                    2022
_chemical_formula_moiety         'C21 H28 N2 O6'
_chemical_formula_sum            'C21 H28 N2 O6'
_chemical_formula_weight         404.45
_chemical_melting_point          401.5(3)
_chemical_name_systematic
'1,3-Diethyl 2-(tert-butylcarboxyamino)-2-(1-methylindol-3-yl)propanedioate'
_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_cell_setting           monoclinic
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.526(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3357(3)
_cell_length_b                   7.9301(2)
_cell_length_c                   13.6175(4)
_cell_measurement_reflns_used    10093
_cell_measurement_temperature    103(1)
_cell_measurement_theta_max      29.3740
_cell_measurement_theta_min      2.1810
_cell_volume                     1064.32(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      103(1)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13103
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plate
_exptl_crystal_F_000             430
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/Dichloromethane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0614P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3615
_reflns_number_total             3961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02482e2.cif
_cod_data_source_block           ki_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '401.1-401.8' was changed
to '401.5(3)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158539
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              76883