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_7159980
_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         'C12 H12 I N3 O3'
_chemical_formula_sum            'C12 H12 I N3 O3'
_chemical_formula_weight         373.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4737(4)
_cell_length_b                   7.2411(2)
_cell_length_c                   15.4718(5)
_cell_measurement_reflns_used    7561
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.594
_cell_measurement_theta_min      3.520
_cell_volume                     1343.03(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.952
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9658
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.864
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.392
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.3393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1554 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.4513.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.425
_refine_diff_density_min         -2.416
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     253
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0972P)^2^+2.0667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2469
_reflns_number_total             2930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00579a2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7159978--7159982.cif.'
_cod_database_code               7159980
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Rotating group:
 N2(H2A,H2B)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C8(H8), C7(H7), C11(H11)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              31666
_shelx_hkl_checksum              53536
_olex2_submission_special_instructions 'No special instructions were received'