Synthesis of <sup>13</sup>C/<sup>19</sup>F/<sup>2</sup>H labeled indoles for use as tryptophan precursors for protein NMR spectroscopy.
Maleckis, Ansis; Herath, Iresha D.; Otting, Gottfried; Organic & biomolecular chemistry 19 (2021) 5133–5147; doi:10.1039/d1ob00611h

data_7158087
_publ_section_title
;
 Synthesis of <sup>13</sup>C/<sup>19</sup>F/<sup>2</sup>H labeled indoles
 for use as tryptophan precursors for protein NMR spectroscopy.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5133
_journal_page_last               5147
_journal_paper_doi               10.1039/d1ob00611h
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H21 Br N O3 P'
_chemical_formula_sum            'C13 H21 Br N O3 P'
_chemical_formula_weight         350.18
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_symmetry_Int_Tables_number      146
_audit_block_doi                 10.5517/ccdc.csd.cc27m311
_audit_creation_date             2020-05-12
_audit_update_record
;
2021-03-29 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   26.9719(7)
_cell_length_b                   26.9719(7)
_cell_length_c                   11.6599(3)
_cell_measurement_reflns_used    5132
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.0
_cell_measurement_theta_min      0.9
_cell_volume                     7346.0(3)
_diffrn_ambient_temperature      150.0(2)
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9863
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9863
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27194
_diffrn_reflns_point_group_measured_fraction_full 0.9915
_diffrn_reflns_point_group_measured_fraction_max 0.9672
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         77.93
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.399
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_correction_T_min  0.419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       'Block '
_exptl_crystal_F_000             3240
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.7449
_refine_diff_density_min         -0.6910
_refine_diff_density_rms         0.0854
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_d_res_high            0.7883
_refine_ls_d_res_low             13.4860
_refine_ls_goodness_of_fit_ref   1.0281
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     359
_refine_ls_number_reflns         6772
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0281
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.0060
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+24.8302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.948
_reflns_limit_h_max              28
_reflns_limit_h_min              -28
_reflns_limit_k_max              29
_reflns_limit_k_min              -29
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                6605
_reflns_number_total             6772
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob00611h2.cif
_cod_data_source_block           OSM6AMf279
_cod_depositor_comments          'Adding full bibliography for 7158087.cif.'
_cod_original_cell_volume        7345.9(3)
_cod_original_sg_symbol_Hall     ' R 3'
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               7158087
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C24(H24), C5(H5), C25(H25), C4(H4)
2.b Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C12(H12a,H12b,H12c), C35(H35a,H35b,H35c), C32(H32a,H32b,
 H32c), C11(H11a,H11b,H11c), C36(H36a,H36b,H36c), C31(H31a,H31b,H31c), C16(H16a,
 H16b,H16c), C34(H34a,H34b,H34c), C17(H17a,H17b,H17c), C15(H15a,H15b,H15c),
 C30(H30a,H30b,H30c)
;