Synthesis of α,α,α',α'-Tetrachloro-Δ(1)-bipyrrolines and 4,8-Dichloro-2,6-diazasemibuvallenes.
Zhan, Ming; Zhang, Shaoguang; Huang, Zhe; Xi, Zhenfeng; Organic letters 17 (2015) 1026–1029; doi:10.1021/acs.orglett.5b00136

data_1518770
_publ_section_title
;
 Synthesis of \a,\a,\a',\a'-Tetrachloro-\D(1)-bipyrrolines and
 4,8-Dichloro-2,6-diazasemibuvallenes.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1026
_journal_page_last               1029
_journal_paper_doi               10.1021/acs.orglett.5b00136
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H16 Cl4 N2'
_chemical_formula_sum            'C20 H16 Cl4 N2'
_chemical_formula_weight         426.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2813(6)
_cell_length_b                   14.1148(7)
_cell_length_c                   24.5832(14)
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      28.4950
_cell_measurement_theta_min      3.3070
_cell_volume                     3914.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.8409
_diffrn_measurement_details
;
  1 omega  -60.00   34.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  -60.0000 94

  2 omega  -99.00  -71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  178.0000    0.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0359071000
_diffrn_orient_matrix_UB_12      0.0402174000
_diffrn_orient_matrix_UB_13      0.0052469000
_diffrn_orient_matrix_UB_21      0.0158142000
_diffrn_orient_matrix_UB_22      -0.0191550000
_diffrn_orient_matrix_UB_23      0.0256763000
_diffrn_orient_matrix_UB_31      0.0491020000
_diffrn_orient_matrix_UB_32      -0.0232713000
_diffrn_orient_matrix_UB_33      -0.0120860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10680
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic ? colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.9168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2916
_reflns_number_total             3848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00136_si_002.cif
_cod_data_source_block           13dec30b
_cod_original_cell_volume        3914.4(4)
_cod_database_code               1518770
_chemical_oxdiff_formula         'C10 H10 N2 Cl4'
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
;