Regioselective 5-<i>exo-dig</i> (halo)cyclization of <i>N</i>-propargyloxycarbonyl guanidine derivatives under mild conditions.
Lin, Bohong; Ruan, Yaoping; Hou, Qi; Yuan, Zhijun; Liang, Yunshi; Zhang, Jing; Organic & biomolecular chemistry 22 (2024) 5585–5590; doi:10.1039/d4ob00579a

data_7159981
_publ_section_title
;
 Regioselective 5-<i>exo-dig</i> (halo)cyclization of
 <i>N</i>-propargyloxycarbonyl guanidine derivatives under mild
 conditions.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5585
_journal_page_last               5590
_journal_paper_doi               10.1039/d4ob00579a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C11 H9 Br F N3 O2'
_chemical_formula_sum            'C11 H9 Br F N3 O2'
_chemical_formula_weight         314.12
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.264(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3126(16)
_cell_length_b                   6.7487(10)
_cell_length_c                   16.077(2)
_cell_measurement_reflns_used    7737
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.548
_cell_measurement_theta_min      5.162
_cell_volume                     1158.7(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9147
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.684
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1450 before and 0.0866 after correction.
The Ratio of minimum to maximum transmission is 0.6784.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0388
_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
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.6187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2143
_reflns_number_total             2340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00579a2.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7159978--7159982.cif.'
_cod_database_code               7159981
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C10(H10), C11(H11)
;
_shelx_res_checksum              38027
_shelx_hkl_checksum              37671
_olex2_submission_special_instructions 'No special instructions were received'