#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/87/4508767.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4508767
loop_
_publ_author_name
'Said, Farouq F.'
'Ong, Tiow-Gan'
'Bazinet, Patrick'
'Yap, Glenn P. A.'
'Richeson, Darrin S.'
_publ_section_title
;
 Linking Hydrogen Dicarboxylate Synthons with Substituted Guanidinium
 Cations:  Transforming Rings and Chains into Two- and
 Three-Dimensional Structures
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1848
_journal_paper_doi               10.1021/cg060167p
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C14 H29 N3 O4'
_chemical_formula_weight         303.40
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8833(13)
_cell_length_b                   11.4815(16)
_cell_length_c                   15.678(2)
_cell_measurement_reflns_used    54
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      1.47
_cell_volume                     1779.1(4)
_computing_cell_refinement       'SMART, Bruker (2000)'
_computing_data_collection       'SMART, Bruker (2000)'
_computing_data_reduction        'XPREP, Bruker (2000)'
_computing_molecular_graphics    'SHELXTL, Bruker (2000)'
_computing_publication_material  'SHELXTL, Bruker (2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1797
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_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     190
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1355P)²+1.4763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2148
_reflns_number_gt                1585
_reflns_number_total             1797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060167psup4.cif
_cod_data_source_block           2094
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4508767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.5325(7) 0.8119(6) 0.2502(4) 0.0608(18) Uani 1 1 d .
H1A H 0.6314 0.8217 0.2571 0.073 Uiso 1 1 calc R
C2 C 0.4990(17) 0.8570(9) 0.1671(4) 0.143(6) Uani 1 1 d .
H2A H 0.5213 0.9392 0.1647 0.214 Uiso 1 1 calc R
H2B H 0.4029 0.8468 0.1568 0.214 Uiso 1 1 calc R
H2C H 0.5501 0.8153 0.1240 0.214 Uiso 1 1 calc R
C3 C 0.5043(12) 0.6841(7) 0.2577(6) 0.096(3) Uani 1 1 d .
H3A H 0.5292 0.6574 0.3142 0.144 Uiso 1 1 calc R
H3B H 0.5567 0.6422 0.2153 0.144 Uiso 1 1 calc R
H3C H 0.4087 0.6700 0.2483 0.144 Uiso 1 1 calc R
C4 C 0.3128(5) 0.9401(5) 0.4671(3) 0.0434(13) Uani 1 1 d .
H4A H 0.2798 0.8742 0.4321 0.052 Uiso 1 1 calc R
C5 C 0.2489(7) 1.0504(6) 0.4310(5) 0.073(2) Uani 1 1 d .
H5A H 0.2781 1.0611 0.3725 0.110 Uiso 1 1 calc R
H5B H 0.2769 1.1169 0.4649 0.110 Uiso 1 1 calc R
H5C H 0.1512 1.0434 0.4328 0.110 Uiso 1 1 calc R
C6 C 0.2694(7) 0.9174(7) 0.5569(4) 0.069(2) Uani 1 1 d .
H6A H 0.3122 0.8467 0.5774 0.103 Uiso 1 1 calc R
H6B H 0.1719 0.9083 0.5589 0.103 Uiso 1 1 calc R
H6C H 0.2961 0.9823 0.5927 0.103 Uiso 1 1 calc R
C7 C 0.7465(5) 0.9740(6) 0.4606(4) 0.0490(15) Uani 1 1 d .
H7A H 0.7032 0.9527 0.5154 0.059 Uiso 1 1 calc R
C8 C 0.7484(9) 1.1031(7) 0.4571(5) 0.076(2) Uani 1 1 d .
H8A H 0.6563 1.1323 0.4568 0.114 Uiso 1 1 calc R
H8B H 0.7945 1.1282 0.4056 0.114 Uiso 1 1 calc R
H8C H 0.7957 1.1333 0.5066 0.114 Uiso 1 1 calc R
C9 C 0.8866(7) 0.9204(8) 0.4620(4) 0.071(2) Uani 1 1 d .
H9A H 0.8790 0.8363 0.4642 0.106 Uiso 1 1 calc R
H9B H 0.9354 0.9479 0.5118 0.106 Uiso 1 1 calc R
H9C H 0.9353 0.9429 0.4108 0.106 Uiso 1 1 calc R
C10 C 0.5322(4) 0.9135(4) 0.3919(3) 0.0274(9) Uani 1 1 d .
C11 C -0.0844(4) 0.9201(4) 0.1852(3) 0.0274(9) Uani 1 1 d .
C12 C -0.0289(5) 0.8009(4) 0.1611(3) 0.0350(11) Uani 1 1 d .
H12A H 0.0538 0.8117 0.1275 0.042 Uiso 1 1 calc R
H12B H -0.0951 0.7613 0.1247 0.042 Uiso 1 1 calc R
C13 C 0.0034(5) 0.7226(4) 0.2370(3) 0.0350(11) Uani 1 1 d .
H13A H -0.0755 0.7196 0.2748 0.042 Uiso 1 1 calc R
H13B H 0.0209 0.6434 0.2164 0.042 Uiso 1 1 calc R
C14 C 0.1247(5) 0.7646(4) 0.2873(3) 0.0359(11) Uani 1 1 d .
N1 N 0.4696(5) 0.8722(5) 0.3210(3) 0.0507(12) Uani 1 1 d .
H1B H 0.3826 0.8830 0.3178 0.061 Uiso 1 1 calc R
N2 N 0.4594(5) 0.9417(4) 0.4597(3) 0.0457(12) Uani 1 1 d .
H2D H 0.5041 0.9635 0.5047 0.055 Uiso 1 1 calc R
N3 N 0.6692(4) 0.9167(4) 0.3942(3) 0.0429(11) Uani 1 1 d .
H3D H 0.7134 0.8823 0.3533 0.051 Uiso 1 1 calc R
O1 O -0.1492(4) 0.9344(3) 0.2513(2) 0.0462(10) Uani 1 1 d .
O2 O -0.0626(3) 1.0017(3) 0.13101(19) 0.0336(8) Uani 1 1 d .
O3 O 0.1809(4) 0.8563(3) 0.2731(3) 0.0509(11) Uani 1 1 d .
O4 O 0.1676(4) 0.6971(3) 0.3485(2) 0.0509(11) Uani 1 1 d .
H4 H 0.1249 0.6349 0.3477 0.061 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 N1 115.0(7)
C2 C1 C3 112.3(7)
N1 C1 C3 109.2(6)
N2 C4 C6 111.3(5)
N2 C4 C5 111.9(5)
C6 C4 C5 112.1(6)
N3 C7 C8 115.7(6)
N3 C7 C9 107.9(5)
C8 C7 C9 113.2(6)
N2 C10 N3 121.0(4)
N2 C10 N1 119.6(4)
N3 C10 N1 119.1(4)
O1 C11 O2 123.2(4)
O1 C11 C12 121.2(4)
O2 C11 C12 115.6(4)
C11 C12 C13 114.3(4)
C14 C13 C12 112.6(4)
O3 C14 O4 120.2(5)
O3 C14 C13 123.0(5)
O4 C14 C13 116.8(4)
C10 N1 C1 126.8(5)
C10 N2 C4 127.1(5)
C10 N3 C7 123.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.440(10)
C1 N1 1.448(8)
C1 C3 1.499(11)
C4 N2 1.453(7)
C4 C6 1.495(8)
C4 C5 1.524(8)
C7 N3 1.449(7)
C7 C8 1.484(10)
C7 C9 1.515(9)
C10 N2 1.324(7)
C10 N3 1.355(6)
C10 N1 1.358(6)
C11 O1 1.229(6)
C11 O2 1.283(5)
C11 C12 1.522(6)
C12 C13 1.525(7)
C13 C14 1.514(7)
C14 O3 1.211(6)
C14 O4 1.305(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O3 0.87 2.14 2.956(6) 157.1 .
N2 H2D O2 0.87 2.10 2.946(6) 163.6 2_575
N3 H3D O1 0.87 2.18 2.877(5) 136.7 1_655
O4 H4 O2 0.83 1.68 2.493(5) 164.9 3_545
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
O1 C11 C12 C13 -28.8(6)
O2 C11 C12 C13 153.3(4)
C11 C12 C13 C14 -70.0(6)
C12 C13 C14 O3 6.7(8)
C12 C13 C14 O4 -173.7(4)
N2 C10 N1 C1 -164.1(6)
N3 C10 N1 C1 10.9(9)
C2 C1 N1 C10 -130.0(9)
C3 C1 N1 C10 102.7(8)
N3 C10 N2 C4 -178.7(5)
N1 C10 N2 C4 -3.8(9)
C6 C4 N2 C10 151.0(6)
C5 C4 N2 C10 -82.7(8)
N2 C10 N3 C7 -14.3(8)
N1 C10 N3 C7 170.7(5)
C8 C7 N3 C10 -74.2(8)
C9 C7 N3 C10 157.8(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146756
