Synthesis of dibromo- and tetrabromo-bipyrrolines and their corresponding 2,6-diazasemibullvalene derivatives
Huang, Zhe; Zhan, Ming; Zhang, Shaoguang; Luo, Qian; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic Chemistry Frontiers 4 (2017) 1785–; doi:10.1039/C7QO00287D

data_1553784
_publ_section_title
;
 Synthesis of dibromo- and tetrabromo-bipyrrolines and their corresponding
 2,6-diazasemibullvalene derivatives
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1785
_journal_paper_doi               10.1039/C7QO00287D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C18 H26 Br2 N2'
_chemical_formula_sum            'C18 H26 Br2 N2'
_chemical_formula_weight         430.23
_chemical_name_systematic        tBu-2Br-NSBV-re
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2015-03-27 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.924(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6642(4)
_cell_length_b                   19.8278(16)
_cell_length_c                   14.8224(10)
_cell_measurement_reflns_used    3290
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.5220
_cell_measurement_theta_min      3.3180
_cell_volume                     1916.3(2)
_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    '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      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -67.00   18.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -77.0000   30.0000 85

  2 omega   34.00   81.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579 -178.0000  -90.0000 47

  3 omega  -75.00    4.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -77.0000   90.0000 79

  4 omega  -14.00   27.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -99.0000  -90.0000 41
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0598411000
_diffrn_orient_matrix_UB_12      0.0077067000
_diffrn_orient_matrix_UB_13      0.0330590000
_diffrn_orient_matrix_UB_21      -0.0839397000
_diffrn_orient_matrix_UB_22      0.0085576000
_diffrn_orient_matrix_UB_23      -0.0360270000
_diffrn_orient_matrix_UB_31      -0.0347636000
_diffrn_orient_matrix_UB_32      -0.0338578000
_diffrn_orient_matrix_UB_33      -0.0016091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.809
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74189
_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            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0594P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2465
_reflns_number_total             3773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00287d2.cif
_cod_data_source_block           14apr15f
_cod_database_code               1553784
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C15 H15 Br1 N2'
_reflns_odcompleteness_completeness 99.82
_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              31111
_shelx_hkl_checksum              71447
_olex2_submission_special_instructions 'No special instructions were received'