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_1518771
_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         'C18 H26 Cl2 N2'
_chemical_formula_sum            'C18 H26 Cl2 N2'
_chemical_formula_weight         341.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2014-07-08
_audit_creation_method
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Olex2 1.2-beta
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
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_cell_angle_alpha                66.695(7)
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_cell_angle_gamma                62.115(7)
_cell_formula_units_Z            2
_cell_length_a                   9.3474(7)
_cell_length_b                   9.8657(7)
_cell_length_c                   12.3923(9)
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.7410
_cell_measurement_theta_min      3.5010
_cell_volume                     908.59(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -23.00   90.00   1.0000    2.5700
omega____ theta____ kappa____ phi______ frames
    -       10.8579   77.0000 -150.0000 113

  2 omega  -62.00   22.00   1.0000    2.5700
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -57.0000   90.0000 84

  3 omega   52.00   79.00   1.0000    2.5700
omega____ theta____ kappa____ phi______ frames
    -       10.8579 -178.0000   90.0000 27

  4 omega  -75.00   18.00   1.0000    2.5700
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -57.0000  -60.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0690451000
_diffrn_orient_matrix_UB_12      0.0025442000
_diffrn_orient_matrix_UB_13      0.0483552000
_diffrn_orient_matrix_UB_21      -0.0390672000
_diffrn_orient_matrix_UB_22      0.0832505000
_diffrn_orient_matrix_UB_23      -0.0257349000
_diffrn_orient_matrix_UB_31      -0.0372814000
_diffrn_orient_matrix_UB_32      -0.0156358000
_diffrn_orient_matrix_UB_33      -0.0323809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.397
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.569
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+0.6860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2611
_reflns_number_total             3578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00136_si_002.cif
_cod_data_source_block           14jun08c
_cod_original_cell_volume        908.60(14)
_cod_database_code               1518771
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C18 N2 H26 Cl2'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              20624
_shelx_hkl_checksum              53255
_olex2_submission_special_instructions 'No special instructions were received'