Synthesis and characterization of isomerically pure anti- and syn-anthradiindole derivatives.
Balandier, Jean-Yves; Henry, Nicolas; Arlin, Jean-Baptiste; Sanguinet, Lionel; Lemaur, Vincent; Niebel, Claude; Chattopadhyay, Basab; Kennedy, Alan Robert; Leriche, Philippe; Blanchard, Philippe; Cornil, Jérôme; Geerts, Yves Henri; Organic letters 15 (2013) 302–305; doi:10.1021/ol303214j

data_1556133
_publ_section_title
;
 Synthesis and characterization of isomerically pure anti- and
 syn-anthradiindole derivatives.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              302
_journal_page_last               305
_journal_paper_doi               10.1021/ol303214j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C42 H46 N2 O2'
_chemical_formula_sum            'C42 H46 N2 O2'
_chemical_formula_weight         610.81
_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_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-10-25 # Formatted by publCIF
;
_cell_angle_alpha                101.869(10)
_cell_angle_beta                 94.696(5)
_cell_angle_gamma                114.24(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2943(10)
_cell_length_b                   8.331(9)
_cell_length_c                   13.551(14)
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     820.9(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8234
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.3431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                2921
_reflns_number_total             3574
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol303214j_si_002.cif
_cod_data_source_block           2012ncs0733
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1556133