Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship.
Miloserdov, Fedor M.; Kirillova, Mariia S.; Muratore, Michael E.; Echavarren, Antonio M.; Journal of the American Chemical Society 140 (2018) 5393–5400; doi:10.1021/jacs.7b13484

data_4131946
_publ_section_title
;
 Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on
 Their Biosynthetic Relationship.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5393
_journal_page_last               5400
_journal_paper_doi               10.1021/jacs.7b13484
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C20 H16 Br3 N4 Ru'
_chemical_formula_weight         653.17
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.686(4)
_cell_angle_beta                 83.158(3)
_cell_angle_gamma                69.733(4)
_cell_formula_units_Z            1
_cell_length_a                   7.2777(3)
_cell_length_b                   8.2938(4)
_cell_length_c                   9.0157(3)
_cell_measurement_reflns_used    10035
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.737
_cell_measurement_theta_min      2.315
_cell_volume                     498.14(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.39f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.39f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.39f (Rigaku OD, 2015)'
_computing_molecular_graphics
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'XCIF, SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT V2014/4 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
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_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10035
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.737
_diffrn_reflns_theta_min         2.315
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    6.817
_exptl_absorpt_correction_T_max  0.727
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 CrysAlisPro 1.171.38.39f (Rigaku Oxford Diffraction, 2015)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    2.177
_exptl_crystal_description       block
_exptl_crystal_F_000             313
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         4.464
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.310
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         10035
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_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1672P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.2071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8029
_reflns_number_total             10035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b13484_si_002.cif
_cod_data_source_block           FM22_twin1_hklf5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4131946
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.727
_shelx_res_checksum              62390
_shelx_hkl_checksum              57553