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#$Date: 2024-08-05 22:58:40 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159980.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159980
loop_
_publ_author_name
'Lin, Bohong'
'Ruan, Yaoping'
'Hou, Qi'
'Yuan, Zhijun'
'Liang, Yunshi'
'Zhang, Jing'
_publ_section_title
;
 Regioselective 5-exo-dig (halo)cyclization of
 N-propargyloxycarbonyl guanidine derivatives under mild
 conditions.
;
_journal_issue                   27
_journal_name_full               'Organic & 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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0972P)²+2.0667P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.15169(3) 0.11913(4) 0.60994(2) 0.02021(19) Uani 1 1 d . . . . .
O3 O 1.0353(3) 0.6957(6) 0.6989(3) 0.0249(8) Uani 1 1 d . U . . .
O1 O 0.3610(3) 0.1392(5) 0.2801(3) 0.0215(8) Uani 1 1 d . U . . .
O2 O 0.8692(4) 0.8326(6) 0.6550(3) 0.0310(9) Uani 1 1 d . U . . .
N3 N 0.8997(3) 0.5457(6) 0.5977(3) 0.0152(7) Uani 1 1 d . U . . .
N1 N 0.7812(4) 0.3689(5) 0.4890(3) 0.0166(8) Uani 1 1 d . U . . .
N2 N 0.7084(4) 0.6148(6) 0.5575(3) 0.0232(10) Uani 1 1 d . U . . .
H2A H 0.643872 0.581129 0.521060 0.028 Uiso 1 1 d R U . . .
H2B H 0.706689 0.600900 0.613637 0.028 Uiso 1 1 d R U . . .
C5 C 0.7908(4) 0.5061(6) 0.5420(3) 0.0133(8) Uani 1 1 d . U . . .
C9 C 0.4631(4) 0.2061(7) 0.3293(3) 0.0157(8) Uani 1 1 d . U . . .
C1 C 1.0009(4) 0.2644(7) 0.5743(3) 0.0169(9) Uani 1 1 d . U . . .
H1 H 0.937616 0.213724 0.531887 0.020 Uiso 1 1 calc R U . . .
C2 C 0.9941(4) 0.4281(7) 0.6114(3) 0.0144(8) Uani 1 1 d . U . . .
C10 C 0.5061(5) 0.3757(6) 0.3140(4) 0.0180(10) Uani 1 1 d . U . . .
H10 H 0.464635 0.453445 0.267135 0.022 Uiso 1 1 calc R U . . .
C4 C 0.9284(5) 0.7041(7) 0.6506(4) 0.0208(9) Uani 1 1 d . U . . .
C8 C 0.5256(5) 0.0907(7) 0.3967(4) 0.0193(10) Uani 1 1 d . U . . .
H8 H 0.497528 -0.027231 0.406303 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6723(4) 0.3195(7) 0.4358(3) 0.0157(8) Uani 1 1 d . U . . .
C7 C 0.6291(4) 0.1485(7) 0.4498(4) 0.0175(9) Uani 1 1 d . U . . .
H7 H 0.670920 0.070228 0.496290 0.021 Uiso 1 1 calc R U . . .
C3 C 1.0864(4) 0.5278(7) 0.6779(3) 0.0190(9) Uani 1 1 d . U . . .
H3A H 1.116062 0.452243 0.732679 0.023 Uiso 1 1 calc R U . . .
H3B H 1.148102 0.556832 0.651369 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6096(4) 0.4317(8) 0.3671(4) 0.0190(9) Uani 1 1 d . U . . .
H11 H 0.638217 0.548498 0.356586 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2914(4) 0.2614(7) 0.2169(3) 0.0189(10) Uani 1 1 d . U . . .
H12A H 0.327210 0.291407 0.169673 0.028 Uiso 1 1 calc R U . . .
H12B H 0.279804 0.375009 0.247534 0.028 Uiso 1 1 calc R U . . .
H12C H 0.219337 0.201998 0.189931 0.028 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C3 110.2(4) . . ?
C9 O1 C12 117.1(4) . . ?
C2 N3 C5 125.7(4) . . ?
C4 N3 C5 124.6(4) . . ?
C4 N3 C2 109.7(4) . . ?
C5 N1 C6 118.2(4) . . ?
H2A N2 H2B 109.4 . . ?
C5 N2 H2A 109.1 . . ?
C5 N2 H2B 109.4 . . ?
N1 C5 N3 116.9(4) . . ?
N1 C5 N2 128.4(5) . . ?
N2 C5 N3 114.6(4) . . ?
O1 C9 C10 124.0(5) . . ?
O1 C9 C8 116.3(4) . . ?
C10 C9 C8 119.7(5) . . ?
I1 C1 H1 120.2 . . ?
C2 C1 I1 119.7(4) . . ?
C2 C1 H1 120.2 . . ?
N3 C2 C3 105.2(4) . . ?
C1 C2 N3 128.2(5) . . ?
C1 C2 C3 126.6(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
O3 C4 N3 110.2(4) . . ?
O2 C4 O3 122.5(5) . . ?
O2 C4 N3 127.3(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C7 C6 N1 118.8(5) . . ?
C7 C6 C11 118.5(5) . . ?
C11 C6 N1 122.6(5) . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O3 C3 C2 104.8(4) . . ?
O3 C3 H3A 110.8 . . ?
O3 C3 H3B 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C10 C11 C6 121.1(5) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.092(5) . ?
O3 C4 1.338(7) . ?
O3 C3 1.450(7) . ?
O1 C9 1.378(6) . ?
O1 C12 1.423(6) . ?
O2 C4 1.202(7) . ?
N3 C5 1.422(6) . ?
N3 C2 1.420(6) . ?
N3 C4 1.397(7) . ?
N1 C5 1.272(6) . ?
N1 C6 1.425(7) . ?
N2 H2A 0.8802 . ?
N2 H2B 0.8803 . ?
N2 C5 1.368(6) . ?
C9 C10 1.386(7) . ?
C9 C8 1.395(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.330(7) . ?
C2 C3 1.501(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(8) . ?
C8 H8 0.9500 . ?
C8 C7 1.389(8) . ?
C6 C7 1.391(7) . ?
C6 C11 1.394(8) . ?
C7 H7 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 N3 -178.7(4) . . . . ?
I1 C1 C2 C3 1.1(7) . . . . ?
O1 C9 C10 C11 179.8(5) . . . . ?
O1 C9 C8 C7 -179.5(5) . . . . ?
N3 C2 C3 O3 1.5(5) . . . . ?
N1 C6 C7 C8 -176.9(5) . . . . ?
N1 C6 C11 C10 177.0(5) . . . . ?
C5 N3 C2 C1 2.2(8) . . . . ?
C5 N3 C2 C3 -177.7(4) . . . . ?
C5 N3 C4 O3 176.5(4) . . . . ?
C5 N3 C4 O2 -3.3(9) . . . . ?
C5 N1 C6 C7 -116.0(5) . . . . ?
C5 N1 C6 C11 67.4(7) . . . . ?
C9 C10 C11 C6 0.5(8) . . . . ?
C9 C8 C7 C6 -1.0(8) . . . . ?
C1 C2 C3 O3 -178.4(5) . . . . ?
C2 N3 C5 N1 -12.2(7) . . . . ?
C2 N3 C5 N2 163.4(4) . . . . ?
C2 N3 C4 O3 -0.8(6) . . . . ?
C2 N3 C4 O2 179.4(5) . . . . ?
C10 C9 C8 C7 1.8(8) . . . . ?
C4 O3 C3 C2 -2.1(5) . . . . ?
C4 N3 C5 N1 171.0(5) . . . . ?
C4 N3 C5 N2 -13.4(7) . . . . ?
C4 N3 C2 C1 179.4(5) . . . . ?
C4 N3 C2 C3 -0.5(5) . . . . ?
C8 C9 C10 C11 -1.6(7) . . . . ?
C6 N1 C5 N3 176.7(4) . . . . ?
C6 N1 C5 N2 1.8(8) . . . . ?
C7 C6 C11 C10 0.4(8) . . . . ?
C3 O3 C4 O2 -178.4(5) . . . . ?
C3 O3 C4 N3 1.8(6) . . . . ?
C11 C6 C7 C8 -0.1(7) . . . . ?
C12 O1 C9 C10 -7.2(7) . . . . ?
C12 O1 C9 C8 174.2(4) . . . . ?
