Electronic halocyclization and radical haloazidation of benzene-linked 1,7-dienes for the synthesis of functionalized 3,1-benzoxazines.
Sun, Yuan-Ming; Yu, Liu-Zhu; Zhu, Zi-Zhong; Hu, Xu-Bo; Gao, Yu-Ning; Shi, Min; Organic & biomolecular chemistry 15 (2017) 634–639; doi:10.1039/c6ob02566h

data_7155415
_publ_section_title
;
 Electronic halocyclization and radical haloazidation of benzene-linked
 1,7-dienes for the synthesis of functionalized 3,1-benzoxazines.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              634
_journal_page_last               639
_journal_paper_doi               10.1039/c6ob02566h
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C20 H18 Br2 N4 O'
_chemical_formula_sum            'C20 H18 Br2 N4 O'
_chemical_formula_weight         490.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2016-03-04 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.893(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.968(2)
_cell_length_b                   9.5866(12)
_cell_length_c                   26.313(3)
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    130
_cell_measurement_theta_max      26.335
_cell_measurement_theta_min      2.501
_cell_volume                     3892.7(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.891
_diffrn_reflns_theta_min         1.602
_exptl_absorpt_coefficient_mu    4.183
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0433 after correction.
The Ratio of minimum to maximum transmission is 0.7079.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+3.6333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4085
_reflns_number_total             5583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02566h2.cif
_cod_data_source_block           mo_dm16094_0m
_cod_depositor_comments          'Adding full bibliography for 7155415.cif.'
_cod_original_cell_volume        3892.5(8)
_cod_database_code               7155415
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.680
_shelx_estimated_absorpt_t_min   0.488
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              95348
_olex2_submission_special_instructions 'No special instructions were received'