#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/25/1502547.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_1502547
loop_
_publ_author_name
'Zhou, Ling'
'Chen, Jie'
'Zhou, Jing'
'Yeung, Ying-Yeung'
_publ_section_title
;
 N-Bromosuccinimide promoted one-pot synthesis of guanidine: scope and
 mechanism.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5804
_journal_page_last               5807
_journal_paper_doi               10.1021/ol202402y
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C18 H18 N4 O4 S'
_chemical_formula_weight         386.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.5580(10)
_cell_angle_beta                 105.0690(10)
_cell_angle_gamma                95.0010(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9534(5)
_cell_length_b                   9.0801(6)
_cell_length_c                   12.9399(8)
_cell_measurement_reflns_used    6839
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.31
_cell_volume                     874.43(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11348
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9371
_exptl_absorpt_correction_T_min  0.8797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.2900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                3673
_reflns_number_total             4006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202402y_si_005.cif
_cod_data_source_block           a010
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502547
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.27263(4) 0.52679(4) 0.21817(3) 0.02912(11) Uani 1 1 d .
O1 O 0.21432(15) 0.37345(12) 0.21745(8) 0.0397(3) Uani 1 1 d .
O2 O 0.42145(14) 0.55999(13) 0.17993(8) 0.0390(2) Uani 1 1 d .
O3 O -0.47213(18) 0.7614(2) -0.00744(13) 0.0701(4) Uani 1 1 d .
O4 O -0.2883(2) 0.92175(17) -0.04182(12) 0.0647(4) Uani 1 1 d .
N1 N 0.31555(14) 0.62491(12) 0.34848(8) 0.0263(2) Uani 1 1 d .
N2 N 0.19943(15) 0.84230(13) 0.40676(9) 0.0292(2) Uani 1 1 d .
N3 N 0.42912(15) 0.86761(14) 0.32549(10) 0.0330(3) Uani 1 1 d .
N4 N -0.3236(2) 0.81319(17) -0.00474(11) 0.0467(3) Uani 1 1 d .
C1 C 0.31499(17) 0.78825(14) 0.36337(10) 0.0265(3) Uani 1 1 d .
C2 C 0.19821(17) 0.57919(15) 0.41327(10) 0.0275(3) Uani 1 1 d .
H2 H 0.1167 0.4845 0.3728 0.033 Uiso 1 1 calc R
C3 C 0.09773(17) 0.71726(15) 0.43151(10) 0.0275(3) Uani 1 1 d .
H3 H -0.0259 0.6951 0.3849 0.033 Uiso 1 1 calc R
C4 C 0.11084(16) 0.74954(15) 0.55269(11) 0.0269(3) Uani 1 1 d .
C5 C 0.23064(17) 0.66802(15) 0.60714(11) 0.0281(3) Uani 1 1 d .
C6 C 0.3053(2) 0.56665(17) 0.52852(11) 0.0338(3) Uani 1 1 d .
H6A H 0.2906 0.4615 0.5362 0.041 Uiso 1 1 calc R
H6B H 0.4308 0.6016 0.5417 0.041 Uiso 1 1 calc R
C7 C 0.03137(18) 0.85403(16) 0.61063(12) 0.0330(3) Uani 1 1 d .
H7 H -0.0511 0.9078 0.5737 0.040 Uiso 1 1 calc R
C8 C 0.0765(2) 0.87738(17) 0.72455(12) 0.0378(3) Uani 1 1 d .
H8 H 0.0233 0.9473 0.7649 0.045 Uiso 1 1 calc R
C9 C 0.1988(2) 0.79909(18) 0.77931(12) 0.0372(3) Uani 1 1 d .
H9 H 0.2297 0.8180 0.8565 0.045 Uiso 1 1 calc R
C10 C 0.27616(18) 0.69283(17) 0.72113(11) 0.0337(3) Uani 1 1 d .
H10 H 0.3579 0.6386 0.7582 0.040 Uiso 1 1 calc R
C11 C 0.09574(17) 0.60493(15) 0.14448(10) 0.0282(3) Uani 1 1 d .
C12 C 0.12990(19) 0.71969(16) 0.09304(11) 0.0329(3) Uani 1 1 d .
H12 H 0.2452 0.7511 0.0921 0.039 Uiso 1 1 calc R
C13 C -0.0093(2) 0.78721(17) 0.04296(11) 0.0365(3) Uani 1 1 d .
H13 H 0.0098 0.8648 0.0071 0.044 Uiso 1 1 calc R
C14 C -0.1762(2) 0.73836(17) 0.04684(11) 0.0349(3) Uani 1 1 d .
C15 C -0.21336(19) 0.62262(18) 0.09561(12) 0.0374(3) Uani 1 1 d .
H15 H -0.3292 0.5905 0.0951 0.045 Uiso 1 1 calc R
C16 C -0.07415(19) 0.55510(17) 0.14555(11) 0.0341(3) Uani 1 1 d .
H16 H -0.0945 0.4761 0.1799 0.041 Uiso 1 1 calc R
C17 C 0.61147(19) 0.8375(2) 0.34257(14) 0.0440(4) Uani 1 1 d .
H17A H 0.6866 0.9085 0.4080 0.066 Uiso 1 1 calc R
H17B H 0.6506 0.8497 0.2793 0.066 Uiso 1 1 calc R
H17C H 0.6177 0.7344 0.3516 0.066 Uiso 1 1 calc R
C18 C 0.4060(2) 1.02502(18) 0.32627(14) 0.0457(4) Uani 1 1 d .
H18A H 0.2818 1.0312 0.2987 0.069 Uiso 1 1 calc R
H18B H 0.4694 1.0624 0.2798 0.069 Uiso 1 1 calc R
H18C H 0.4514 1.0863 0.4009 0.069 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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
O1 S1 O2 119.49(7)
O1 S1 N1 106.08(6)
O2 S1 N1 108.32(6)
O1 S1 C11 109.70(7)
O2 S1 C11 107.85(6)
N1 S1 C11 104.37(6)
C1 N1 C2 103.70(9)
C1 N1 S1 115.52(8)
C2 N1 S1 117.06(8)
C1 N2 C3 108.60(11)
C1 N3 C18 116.12(12)
C1 N3 C17 120.65(12)
C18 N3 C17 114.82(13)
O4 N4 O3 124.65(15)
O4 N4 C14 117.82(15)
O3 N4 C14 117.53(15)
N2 C1 N3 125.94(12)
N2 C1 N1 116.09(11)
N3 C1 N1 117.87(11)
N1 C2 C6 111.47(11)
N1 C2 C3 103.37(10)
C6 C2 C3 106.54(10)
N2 C3 C4 110.41(11)
N2 C3 C2 105.26(10)
C4 C3 C2 104.16(10)
C7 C4 C5 120.79(12)
C7 C4 C3 127.98(12)
C5 C4 C3 111.01(11)
C10 C5 C4 120.36(12)
C10 C5 C6 128.01(12)
C4 C5 C6 111.48(11)
C5 C6 C2 104.57(10)
C4 C7 C8 118.51(13)
C9 C8 C7 120.89(13)
C8 C9 C10 120.55(13)
C9 C10 C5 118.88(13)
C12 C11 C16 121.62(13)
C12 C11 S1 119.76(11)
C16 C11 S1 118.50(10)
C11 C12 C13 118.76(13)
C14 C13 C12 118.74(14)
C15 C14 C13 123.39(13)
C15 C14 N4 118.16(14)
C13 C14 N4 118.44(14)
C14 C15 C16 117.81(14)
C15 C16 C11 119.65(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4261(11)
S1 O2 1.4279(11)
S1 N1 1.6731(11)
S1 C11 1.7719(13)
O3 N4 1.222(2)
O4 N4 1.221(2)
N1 C1 1.4574(16)
N1 C2 1.4916(16)
N2 C1 1.2796(17)
N2 C3 1.4718(17)
N3 C1 1.3573(17)
N3 C18 1.455(2)
N3 C17 1.4675(19)
N4 C14 1.4819(19)
C2 C6 1.5450(18)
C2 C3 1.5558(17)
C3 C4 1.5104(17)
C4 C7 1.3884(18)
C4 C5 1.3911(18)
C5 C10 1.3901(19)
C5 C6 1.5064(18)
C7 C8 1.390(2)
C8 C9 1.385(2)
C9 C10 1.389(2)
C11 C12 1.3876(19)
C11 C16 1.3915(19)
C12 C13 1.388(2)
C13 C14 1.379(2)
C14 C15 1.378(2)
C15 C16 1.387(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037507
