Bis(heterocumulenes) Derived from the 1,4-Diphenyl-1,3-butadiyne Framework. Synthesis of Three New Classes of Axially Chiral Biheteroaryls
Mateo Alajarín; Baltasar Bonillo; Ángel Vidal; Delia Bautista; Journal of Organic Chemistry 73 (2008) 291–294; doi:10.1021/jo7021058

data_4023180
_publ_section_title
;
 Bis(heterocumulenes) Derived from the 1,4-Diphenyl-1,3-butadiyne
 Framework. Synthesis of Three New Classes of Axially
 Chiral Biheteroaryls
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              291
_journal_page_last               294
_journal_paper_doi               10.1021/jo7021058
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C47 H34 Cl2 N4 O'
_chemical_formula_weight         741.68
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.963(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9537(5)
_cell_length_b                   23.4956(14)
_cell_length_c                   19.4769(11)
_cell_measurement_reflns_used    6317
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.27
_cell_volume                     3620.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40684
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.224
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    'NH free,methyls rigid, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         7918
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0763
_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^)+(0.0598P)^2^+6.7448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1838
_refine_ls_wR_factor_ref         0.1898
_reflns_number_gt                6546
_reflns_number_total             7918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7021058-File006.cif
_cod_data_source_block           ibbf109m
_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 21/c'
_cod_database_code               4023180