#------------------------------------------------------------------------------
#$Date: 2019-11-25 23:06:11 +0200 (Mon, 25 Nov 2019) $
#$Revision: 242016 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/19/4131946.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4131946
loop_
_publ_author_name
'Miloserdov, Fedor M.'
'Kirillova, Mariia S.'
'Muratore, Michael E.'
'Echavarren, Antonio M.'
_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'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_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
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_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
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         10035
_refine_ls_number_restraints     0
_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/[σ²(Fo²)+(0.1672P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.727
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ru1 Ru 0.0000 1.0000 0.5000 0.01303(17) Uani 1 2 d S . P
Br1 Br 0.28850(8) 1.03761(7) 0.34474(6) 0.01720(18) Uani 1 1 d . . .
N1 N 0.1312(7) 0.7305(6) 0.5259(5) 0.0146(9) Uani 1 1 d . . .
N2 N -0.0929(7) 0.9426(6) 0.3146(5) 0.0143(8) Uani 1 1 d . . .
C1 C 0.2097(8) 0.6186(7) 0.6517(6) 0.0175(10) Uani 1 1 d . . .
H1 H 0.1943 0.6610 0.7416 0.021 Uiso 1 1 calc R U .
C2 C 0.3123(8) 0.4433(8) 0.6532(7) 0.0193(11) Uani 1 1 d . . .
H2 H 0.3663 0.3700 0.7418 0.023 Uiso 1 1 calc R U .
C3 C 0.3328(8) 0.3793(8) 0.5209(7) 0.0203(11) Uani 1 1 d . . .
H3 H 0.4041 0.2626 0.5184 0.024 Uiso 1 1 calc R U .
C4 C 0.2458(8) 0.4909(7) 0.3909(7) 0.0182(11) Uani 1 1 d . . .
H4 H 0.2558 0.4495 0.3012 0.022 Uiso 1 1 calc R U .
C5 C 0.1440(8) 0.6649(7) 0.3976(6) 0.0151(10) Uani 1 1 d . . .
C6 C 0.0228(8) 0.7856(7) 0.2766(6) 0.0149(10) Uani 1 1 d . . .
C7 C 0.0022(9) 0.7418(8) 0.1399(6) 0.0184(11) Uani 1 1 d . . .
H7 H 0.0863 0.6377 0.1132 0.022 Uiso 1 1 calc R U .
C8 C -0.1420(9) 0.8519(8) 0.0447(7) 0.0219(12) Uani 1 1 d . . .
H8 H -0.1556 0.8242 -0.0472 0.026 Uiso 1 1 calc R U .
C9 C -0.2678(9) 1.0064(8) 0.0887(7) 0.0195(11) Uani 1 1 d . . .
H9 H -0.3702 1.0807 0.0286 0.023 Uiso 1 1 calc R U .
C10 C -0.2381(8) 1.0469(7) 0.2224(6) 0.0174(10) Uani 1 1 d . . .
H10 H -0.3215 1.1505 0.2504 0.021 Uiso 1 1 calc R U .
Br2 Br 0.5000 0.5000 0.0000 0.0269(2) Uani 1 2 d S . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Ru1 N2 180.0 . 2_576
N2 Ru1 N1 102.82(17) . 2_576
N2 Ru1 N1 77.18(17) 2_576 2_576
N2 Ru1 N1 77.18(17) . .
N2 Ru1 N1 102.82(17) 2_576 .
N1 Ru1 N1 180.0 2_576 .
N2 Ru1 Br1 90.88(13) . 2_576
N2 Ru1 Br1 89.12(13) 2_576 2_576
N1 Ru1 Br1 89.55(13) 2_576 2_576
N1 Ru1 Br1 90.45(13) . 2_576
N2 Ru1 Br1 89.12(13) . .
N2 Ru1 Br1 90.88(13) 2_576 .
N1 Ru1 Br1 90.45(13) 2_576 .
N1 Ru1 Br1 89.55(13) . .
Br1 Ru1 Br1 180.0 2_576 .
C1 N1 C5 118.0(5) . .
C1 N1 Ru1 127.3(4) . .
C5 N1 Ru1 114.6(4) . .
C10 N2 C6 118.2(5) . .
C10 N2 Ru1 127.8(4) . .
C6 N2 Ru1 113.8(3) . .
N1 C1 C2 122.9(5) . .
C3 C2 C1 118.8(5) . .
C2 C3 C4 119.4(5) . .
C5 C4 C3 118.8(5) . .
N1 C5 C4 121.9(5) . .
N1 C5 C6 114.6(5) . .
C4 C5 C6 123.0(5) . .
N2 C6 C7 120.9(5) . .
N2 C6 C5 114.4(5) . .
C7 C6 C5 124.2(5) . .
C8 C7 C6 120.2(5) . .
C7 C8 C9 118.7(5) . .
C10 C9 C8 119.1(5) . .
N2 C10 C9 122.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 N2 2.076(5) .
Ru1 N2 2.076(5) 2_576
Ru1 N1 2.077(5) 2_576
Ru1 N1 2.077(5) .
Ru1 Br1 2.4561(5) 2_576
Ru1 Br1 2.4561(5) .
N1 C1 1.346(7) .
N1 C5 1.360(7) .
N2 C10 1.351(7) .
N2 C6 1.373(7) .
C1 C2 1.383(8) .
C2 C3 1.379(9) .
C3 C4 1.392(8) .
C4 C5 1.386(7) .
C5 C6 1.457(8) .
C6 C7 1.395(8) .
C7 C8 1.375(9) .
C8 C9 1.398(8) .
C9 C10 1.378(8) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 C2 4.1(8)
Ru1 N1 C1 C2 -173.0(4)
N1 C1 C2 C3 -1.0(9)
C1 C2 C3 C4 -1.7(8)
C2 C3 C4 C5 1.3(8)
C1 N1 C5 C4 -4.5(8)
Ru1 N1 C5 C4 173.0(4)
C1 N1 C5 C6 168.2(5)
Ru1 N1 C5 C6 -14.4(6)
C3 C4 C5 N1 1.8(8)
C3 C4 C5 C6 -170.2(5)
C10 N2 C6 C7 5.5(7)
Ru1 N2 C6 C7 -168.5(4)
C10 N2 C6 C5 -166.5(5)
Ru1 N2 C6 C5 19.5(6)
N1 C5 C6 N2 -3.4(7)
C4 C5 C6 N2 169.1(5)
N1 C5 C6 C7 -175.1(5)
C4 C5 C6 C7 -2.6(9)
N2 C6 C7 C8 -3.5(8)
C5 C6 C7 C8 167.7(5)
C6 C7 C8 C9 -0.8(8)
C7 C8 C9 C10 2.8(8)
C6 N2 C10 C9 -3.5(8)
Ru1 N2 C10 C9 169.6(4)
C8 C9 C10 N2 -0.7(8)
