Structural Diversification of Hapalindole and Fischerindole Natural Products via Cascade Biocatalysis
Hohlman, Robert M.; Newmister, Sean A.; Sanders, Jacob N.; Khatri, Yogan; Li, Shasha; Keramati, Nikki R.; Lowell, Andrew N.; Houk, K. N.; Sherman, David H.; ACS Catalysis 11 (2021) 4670–4681; doi:10.1021/acscatal.0c05656

data_4518602
_publ_section_title
;
 Structural Diversification of Hapalindole and Fischerindole Natural
 Products via Cascade Biocatalysis
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              4670
_journal_page_last               4681
_journal_paper_doi               10.1021/acscatal.0c05656
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C20 H23 N3), C4 H10 O'
_chemical_formula_sum            'C44 H56 N6 O'
_chemical_formula_weight         684.94
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3688(9)
_cell_length_b                   15.8213(4)
_cell_length_c                   22.0726(9)
_cell_measurement_reflns_used    8462
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.5720
_cell_measurement_theta_min      4.0440
_cell_volume                     3970.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            61153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.917
_diffrn_reflns_theta_min         3.437
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       plate
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 1830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7384
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0874
_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^)+(0.1469P)^2^+1.9902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2539
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5502
_reflns_number_total             7384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c05656_si_002.cif
_cod_data_source_block           rh7a2a
_cod_depositor_comments          'Adding full bibliography for 4518602.cif.'
_cod_database_code               4518602
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              74106
_shelx_hkl_checksum              74856