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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/7/15/99/7159978.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_7159978
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         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                99.818(4)
_cell_angle_beta                 98.950(4)
_cell_angle_gamma                101.433(4)
_cell_formula_units_Z            4
_cell_length_a                   8.7766(8)
_cell_length_b                   9.6982(9)
_cell_length_c                   13.2431(13)
_cell_measurement_reflns_used    7696
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.596
_cell_measurement_theta_min      5.600
_cell_volume                     1067.53(18)
_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 0.981
_diffrn_measured_fraction_theta_max 0.967
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14132
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.190
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1148 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.7564.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0528P)²+0.2928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3797
_reflns_number_total             4746
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00579a2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7159978--7159982.cif.'
_cod_database_code               7159978
_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) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C11(H11), C18(H18), C7(H7), C22(H22), C21(H21), C8(H8),
 C9(H9), C20(H20), C19(H19), C10(H10)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N2(H2A,H2B)
2.d :
 C1(H1A), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O2 O 0.87106(11) 0.14248(10) 0.34839(7) 0.0221(2) Uani 1 1 d . . . . .
O4 O 0.36914(12) 0.33233(10) 0.34279(7) 0.0245(2) Uani 1 1 d . . . . .
O3 O 0.31822(12) 0.11593(10) 0.38721(8) 0.0267(2) Uani 1 1 d . . . . .
O1 O 0.81569(12) 0.35925(10) 0.39275(8) 0.0263(2) Uani 1 1 d . . . . .
N3 N 0.74367(13) 0.17181(11) 0.47953(8) 0.0203(2) Uani 1 1 d . . . . .
N1 N 0.62145(14) 0.17413(12) 0.61836(9) 0.0212(2) Uani 1 1 d . . . . .
H1 H 0.609840 0.080245 0.602937 0.025 Uiso 1 1 calc R U . . .
N6 N 0.24928(13) 0.31775(11) 0.47672(8) 0.0212(2) Uani 1 1 d . . . . .
N5 N 0.18312(14) 0.11786(12) 0.55630(9) 0.0238(3) Uani 1 1 d . . . . .
H5A H 0.222702 0.062292 0.512742 0.029 Uiso 1 1 calc R U . . .
H5B H 0.140379 0.083850 0.605501 0.029 Uiso 1 1 calc R U . . .
N4 N 0.12895(14) 0.33882(12) 0.61551(9) 0.0239(3) Uani 1 1 d . . . . .
H4 H 0.119416 0.421195 0.598891 0.029 Uiso 1 1 calc R U . . .
N2 N 0.66231(15) 0.38081(12) 0.55197(9) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.696548 0.428631 0.505977 0.032 Uiso 1 1 calc R U . . .
H2B H 0.617571 0.421783 0.600261 0.032 Uiso 1 1 calc R U . . .
C15 C 0.31025(16) 0.24275(14) 0.40453(10) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.80770(15) 0.23740(13) 0.40925(10) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.18786(15) 0.25236(14) 0.54782(10) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.67812(16) 0.24726(14) 0.54852(10) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.57851(15) 0.22983(14) 0.71313(10) 0.0194(3) Uani 1 1 d . . . . .
C17 C 0.08065(16) 0.31471(14) 0.70935(10) 0.0204(3) Uani 1 1 d . . . . .
C3 C 0.94395(17) 0.19684(15) 0.26827(11) 0.0239(3) Uani 1 1 d . . . . .
H3A H 1.023564 0.142070 0.250698 0.029 Uiso 1 1 calc R U . . .
H3B H 0.999740 0.298915 0.295256 0.029 Uiso 1 1 calc R U . . .
C11 C 0.46780(17) 0.13845(15) 0.75061(11) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.421181 0.043766 0.711418 0.030 Uiso 1 1 calc R U . . .
C14 C 0.44331(17) 0.27018(16) 0.26236(11) 0.0260(3) Uani 1 1 d . . . . .
H14A H 0.494554 0.196426 0.286824 0.031 Uiso 1 1 calc R U . . .
H14B H 0.526837 0.345971 0.249005 0.031 Uiso 1 1 calc R U . . .
C18 C 0.12804(17) 0.42873(15) 0.79532(11) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.191221 0.517509 0.789367 0.032 Uiso 1 1 calc R U . . .
C7 C 0.64924(17) 0.36720(15) 0.77250(11) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.727954 0.429193 0.748929 0.030 Uiso 1 1 calc R U . . .
C2 C 0.82685(18) 0.18527(15) 0.17367(11) 0.0270(3) Uani 1 1 d . . . . .
C13 C 0.32900(18) 0.20419(15) 0.16505(11) 0.0276(3) Uani 1 1 d . . . . .
C22 C -0.01471(16) 0.18589(15) 0.71793(11) 0.0240(3) Uani 1 1 d . . . . .
H22 H -0.050416 0.108294 0.659081 0.029 Uiso 1 1 calc R U . . .
C21 C -0.05736(18) 0.17132(16) 0.81277(12) 0.0301(3) Uani 1 1 d . . . . .
H21 H -0.121226 0.082917 0.818815 0.036 Uiso 1 1 calc R U . . .
C8 C 0.60435(19) 0.41317(16) 0.86613(11) 0.0295(3) Uani 1 1 d . . . . .
H8 H 0.651323 0.507475 0.905896 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4920(2) 0.32311(17) 0.90212(12) 0.0323(3) Uani 1 1 d . . . . .
H9 H 0.460700 0.355756 0.965799 0.039 Uiso 1 1 calc R U . . .
C20 C -0.0080(2) 0.28396(18) 0.89850(12) 0.0340(4) Uani 1 1 d . . . . .
H20 H -0.036640 0.272716 0.963404 0.041 Uiso 1 1 calc R U . . .
C19 C 0.08397(19) 0.41398(17) 0.88937(12) 0.0321(3) Uani 1 1 d . . . . .
H19 H 0.116422 0.492506 0.947685 0.038 Uiso 1 1 calc R U . . .
C1 C 0.7335(2) 0.17456(18) 0.09597(13) 0.0392(4) Uani 1 1 d . . . . .
H1A H 0.658796 0.165987 0.033766 0.047 Uiso 1 1 calc R U . . .
C10 C 0.42520(19) 0.18478(17) 0.84472(12) 0.0316(3) Uani 1 1 d . . . . .
H10 H 0.349973 0.121627 0.870071 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2399(2) 0.15222(19) 0.08463(13) 0.0403(4) Uani 1 1 d . . . . .
H12 H 0.168367 0.110512 0.020090 0.048 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'
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 O2 C3 115.73(10) . . ?
C15 O4 C14 116.28(10) . . ?
C5 N3 C4 118.55(11) . . ?
C5 N1 H1 115.9 . . ?
C5 N1 C6 128.11(11) . . ?
C6 N1 H1 115.9 . . ?
C16 N6 C15 119.28(11) . . ?
H5A N5 H5B 120.0 . . ?
C16 N5 H5A 120.0 . . ?
C16 N5 H5B 120.0 . . ?
C16 N4 H4 115.6 . . ?
C16 N4 C17 128.80(11) . . ?
C17 N4 H4 115.6 . . ?
H2A N2 H2B 120.0 . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
O3 C15 O4 119.86(12) . . ?
O3 C15 N6 131.36(12) . . ?
N6 C15 O4 108.77(11) . . ?
O1 C4 O2 119.55(12) . . ?
O1 C4 N3 131.48(13) . . ?
N3 C4 O2 108.97(11) . . ?
N6 C16 N4 113.62(11) . . ?
N5 C16 N6 126.17(13) . . ?
N5 C16 N4 120.21(12) . . ?
N3 C5 N1 114.43(11) . . ?
N2 C5 N3 126.35(12) . . ?
N2 C5 N1 119.21(12) . . ?
C11 C6 N1 117.55(12) . . ?
C11 C6 C7 119.39(13) . . ?
C7 C6 N1 122.93(12) . . ?
C18 C17 N4 117.15(12) . . ?
C18 C17 C22 119.45(13) . . ?
C22 C17 N4 123.36(12) . . ?
O2 C3 H3A 109.3 . . ?
O2 C3 H3B 109.3 . . ?
O2 C3 C2 111.71(11) . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.33(13) . . ?
C10 C11 H11 119.8 . . ?
O4 C14 H14A 109.2 . . ?
O4 C14 H14B 109.2 . . ?
O4 C14 C13 111.84(12) . . ?
H14A C14 H14B 107.9 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.54(14) . . ?
C19 C18 H18 119.7 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.79(13) . . ?
C8 C7 H7 120.1 . . ?
C1 C2 C3 178.80(17) . . ?
C12 C13 C14 177.99(16) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.72(13) . . ?
C21 C22 H22 120.1 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.69(14) . . ?
C20 C21 H21 119.7 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.64(14) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.61(14) . . ?
C10 C9 H9 120.2 . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.68(14) . . ?
C19 C20 H20 120.2 . . ?
C18 C19 C20 119.89(14) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C2 C1 H1A 180.0 . . ?
C11 C10 C9 120.19(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C13 C12 H12 180.0 . . ?
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
O2 C4 1.3769(16) . ?
O2 C3 1.4426(16) . ?
O4 C15 1.3734(16) . ?
O4 C14 1.4401(16) . ?
O3 C15 1.2301(16) . ?
O1 C4 1.2285(16) . ?
N3 C4 1.3451(17) . ?
N3 C5 1.3430(17) . ?
N1 H1 0.8800 . ?
N1 C5 1.3538(17) . ?
N1 C6 1.4163(17) . ?
N6 C15 1.3438(17) . ?
N6 C16 1.3436(17) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C16 1.3213(17) . ?
N4 H4 0.8800 . ?
N4 C16 1.3542(17) . ?
N4 C17 1.4150(17) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C5 1.3236(17) . ?
C6 C11 1.3909(19) . ?
C6 C7 1.3933(19) . ?
C17 C18 1.390(2) . ?
C17 C22 1.3920(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.464(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.462(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C2 C1 1.187(2) . ?
C13 C12 1.184(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.391(2) . ?
C19 H19 0.9500 . ?
C1 H1A 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
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
N1 C6 C11 C10 177.65(13) . . . . ?
N1 C6 C7 C8 -178.16(13) . . . . ?
N4 C17 C18 C19 179.25(13) . . . . ?
N4 C17 C22 C21 -179.68(13) . . . . ?
C15 O4 C14 C13 88.78(14) . . . . ?
C15 N6 C16 N5 1.4(2) . . . . ?
C15 N6 C16 N4 -179.40(11) . . . . ?
C4 O2 C3 C2 -83.54(14) . . . . ?
C4 N3 C5 N1 -177.91(11) . . . . ?
C4 N3 C5 N2 3.6(2) . . . . ?
C16 N6 C15 O4 -178.43(11) . . . . ?
C16 N6 C15 O3 2.4(2) . . . . ?
C16 N4 C17 C18 136.08(14) . . . . ?
C16 N4 C17 C22 -46.1(2) . . . . ?
C5 N3 C4 O2 178.55(10) . . . . ?
C5 N3 C4 O1 -2.1(2) . . . . ?
C5 N1 C6 C11 154.68(13) . . . . ?
C5 N1 C6 C7 -29.5(2) . . . . ?
C6 N1 C5 N3 164.77(12) . . . . ?
C6 N1 C5 N2 -16.6(2) . . . . ?
C6 C11 C10 C9 0.4(2) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C17 N4 C16 N6 -168.33(12) . . . . ?
C17 N4 C16 N5 10.9(2) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C17 C22 C21 C20 0.9(2) . . . . ?
C3 O2 C4 O1 0.19(17) . . . . ?
C3 O2 C4 N3 179.67(10) . . . . ?
C11 C6 C7 C8 -2.4(2) . . . . ?
C14 O4 C15 O3 -2.28(18) . . . . ?
C14 O4 C15 N6 178.40(10) . . . . ?
C18 C17 C22 C21 -1.9(2) . . . . ?
C7 C6 C11 C10 1.7(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C22 C17 C18 C19 1.4(2) . . . . ?
C22 C21 C20 C19 0.8(2) . . . . ?
C21 C20 C19 C18 -1.3(2) . . . . ?
C8 C9 C10 C11 -1.7(2) . . . . ?
