The first stereoselective syntheses of 2,2'-biindoline
Steven Wales; Anthony Willis; Paul Keller; Chem.Commun. 46 (2010) 9226–; doi:10.1039/c0cc04045b

data_7105736
_publ_section_title
;
 The first stereoselective syntheses of 2,2'-biindoline
;
_journal_name_full               Chem.Commun.
_journal_page_first              9226
_journal_paper_doi               10.1039/c0cc04045b
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_formula_weight         236.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-03-05
_audit_creation_method           CRYSTALS_ver_12.85
_audit_update_record
;
2009-03-05 - Report on C16 H16 N2
by Anthony C. Willis
for Paul Keller

2009-03-05 - passes checkcif tests with minor warnings

2010-09-28 - combine wol0902a and wol0903 for manuscript to Chem Comm
Manuscript ID: CC-COM-09-2010-004045
;
_cell_angle_alpha                90
_cell_angle_beta                 109.257(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6395(4)
_cell_length_b                   7.8596(3)
_cell_length_c                   14.2979(6)
_cell_measurement_reflns_used    53015
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1234.81(8)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25324
_diffrn_reflns_theta_full        27.482
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.749
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8712
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.005551
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.00P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0945
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0945
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2134
_reflns_number_total             3033
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.04
_oxford_diffrn_Wilson_scale      0.87
_oxford_refine_ls_r_factor_ref   0.0597
_oxford_refine_ls_scale          1.110(5)
_oxford_reflns_number_all        3033
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '3051226 wol0902'
_cod_data_source_file            C0CC04045B.TXT
_cod_data_source_block           wol0902a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7105736