Progress toward the Total Synthesis of Lymphostins: Preparation of a Functionalized Tetrahydropyrrolo[4,3,2-<i>de</i>]quinoline and Unusual Oxidative Dimerization.
Seiler, Grant S.; Hughes, Chambers C.; The Journal of organic chemistry 84 (2019) 9339–9343; doi:10.1021/acs.joc.9b01041

data_4034197
_publ_section_title
;
 Progress toward the Total Synthesis of Lymphostins: Preparation of a
 Functionalized Tetrahydropyrrolo[4,3,2-<i>de</i>]quinoline and Unusual
 Oxidative Dimerization.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9339
_journal_page_last               9343
_journal_paper_doi               10.1021/acs.joc.9b01041
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         '2(C24 H16 Br2 N4 O4), C7 H8'
_chemical_formula_sum            'C55 H40 Br4 N8 O8'
_chemical_formula_weight         1260.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8041(2)
_cell_length_b                   20.9989(7)
_cell_length_c                   15.3544(5)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      2.35
_cell_volume                     2515.88(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX Mo - Kappa'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43067
_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         25.680
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.265
_exptl_absorpt_correction_T_max  0.5622
_exptl_absorpt_correction_T_min  0.5064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0665 before and 0.0487 after correction. The Ratio of minimum to maximum transmission is 0.9007. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0281P)^2^+2.5492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3944
_reflns_number_total             4784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01041_si_002.cif
_cod_data_source_block           hughes_gs-vi-170
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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_database_code               4034197
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.705
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2S-C1S
 1.55 with sigma of 0.01
3. Rigid body (RIGU) restrains
 C1S, C2S, C3S, C4S, C5S, C6S, C7S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C2S(0.5) C7S(0.5) H7S(0.5)
 C6S(0.5) H6S(0.5) C5S(0.5) H5S(0.5) C4S(0.5) H4S(0.5) C3S(0.5) H3S(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C7(H7), C8(H8), C15(H15), C18(H18), C19(H19), C7S(H7S),
 C6S(H6S), C5S(H5S), C4S(H4S), C3S(H3S)
5.d Fitted hexagon refined as free rotating group:
 C2S(C7S,C6S,C5S,C4S,C3S)
5.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C1S(H1SA,H1SB,H1SC)
;
_shelx_res_checksum              81916
_shelx_hkl_checksum              68085
_olex2_submission_special_instructions 'No special instructions were received'