#------------------------------------------------------------------------------
#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/67/4116750.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_4116750
loop_
_publ_author_name
'Aya Tanatani'
'Kentaro Yamaguchi'
'Isao Azumaya'
'Ryuuta Fukutomi'
'Koichi Shudo'
'Hiroyuki Kagechika'
_publ_section_title
;
 N-Methylated Diphenylguanidines: Conformations, Propeller-Type Molecular
 Chirality, and Construction of Water-Soluble Oligomers with Multilayered
 Aromatic Structures
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6433
_journal_page_last               6442
_journal_paper_doi               10.1021/ja9806534
_journal_volume                  120
_journal_year                    1998
_chemical_formula_moiety         'C14 H15 N3 '
_chemical_formula_sum            'C14 H15 N3'
_chemical_formula_weight         225.29
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_audit_creation_date             'Fri Jan  9 14:32:42 1998'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 112.21(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.212(2)
_cell_length_b                   12.757(2)
_cell_length_c                   9.281(1)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      24.5
_cell_volume                     1229.0(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.07558
_diffrn_orient_matrix_UB_12      -0.04843
_diffrn_orient_matrix_UB_13      0.04040
_diffrn_orient_matrix_UB_21      -0.01315
_diffrn_orient_matrix_UB_22      -0.00675
_diffrn_orient_matrix_UB_23      0.10032
_diffrn_orient_matrix_UB_31      -0.05828
_diffrn_orient_matrix_UB_32      -0.06126
_diffrn_orient_matrix_UB_33      -0.04297
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.110
_diffrn_reflns_av_sigmaI/netI    0.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1197
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         0.00
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        -0.02
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  1.120
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   '\DF (DIFABS; Walker & Stuart, 1983)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   6.690
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1004
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0620
_refine_ls_shift/esd_max         5.1370
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00000|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0640
_reflns_number_observed          1004
_reflns_number_total             1135
_reflns_observed_criterion       >3.0sigma(I)
_cod_data_source_file            ja9806534_04.cif
_cod_data_source_block           Compound_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00000|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1229.1(4)
_cod_original_sg_symbol_H-M      'C c '
_cod_original_formula_sum        'C14 H15 N3 '
_cod_database_code               4116750
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_refinement_flags
N(1) 0.6496 0.0787(5) 0.0378 0.052(2) Uani d 1.00 S
N(2) 0.7015(8) 0.0523(5) -0.1857(9) 0.058(2) Uani d 1.00 .
N(3) 0.5635(9) -0.0579(5) -0.1323(10) 0.060(2) Uani d 1.00 .
C(1) 0.6399(9) 0.0301(5) -0.0856(9) 0.047(2) Uani d 1.00 .
C(2) 0.6918(9) 0.1837(5) 0.0648(10) 0.048(2) Uani d 1.00 .
C(3) 0.7756(10) 0.2127(7) 0.209(1) 0.058(2) Uani d 1.00 .
C(4) 0.8125(10) 0.3143(7) 0.246(1) 0.067(3) Uani d 1.00 .
C(5) 0.765(1) 0.3928(8) 0.134(1) 0.074(3) Uani d 1.00 .
C(6) 0.680(1) 0.3640(7) -0.008(1) 0.070(3) Uani d 1.00 .
C(7) 0.6436(10) 0.2610(6) -0.047(1) 0.056(2) Uani d 1.00 .
C(8) 0.8273(9) 0.0924(5) -0.1460(10) 0.051(2) Uani d 1.00 .
C(9) 0.9197(10) 0.0872(6) 0.003(1) 0.059(2) Uani d 1.00 .
C(10) 1.0445(10) 0.1229(7) 0.032(1) 0.067(3) Uani d 1.00 .
C(11) 1.074(1) 0.1615(8) -0.085(1) 0.077(3) Uani d 1.00 .
C(12) 0.986(1) 0.1639(7) -0.231(1) 0.081(4) Uani d 1.00 .
C(13) 0.861(1) 0.1342(7) -0.263(1) 0.068(3) Uani d 1.00 .
C(14) 0.471(1) -0.0839(8) -0.062(1) 0.068(3) Uani d 1.00 .
H(2) 0.657(7) 0.034(6) -0.292(9) 0.08(3) Uiso calc 1.00 .
H(3) 0.812(8) 0.163(6) 0.281(10) 0.08(3) Uiso calc 1.00 .
H(4) 0.872(8) 0.322(6) 0.350(10) 0.08(3) Uiso calc 1.00 .
H(5) 0.797(9) 0.471(7) 0.16(1) 0.10(3) Uiso calc 1.00 .
H(6) 0.660(8) 0.412(6) -0.082(10) 0.08(3) Uiso calc 1.00 .
H(7) 0.586(7) 0.248(6) -0.153(9) 0.07(2) Uiso calc 1.00 .
H(8) 0.884(7) 0.051(6) 0.080(9) 0.09(3) Uiso calc 1.00 .
H(9) 1.111(9) 0.119(5) 0.144(10) 0.07(3) Uiso calc 1.00 .
H(10) 1.15(1) 0.190(7) -0.06(1) 0.12(3) Uiso calc 1.00 .
H(11) 1.003(8) 0.188(7) -0.31(1) 0.11(3) Uiso calc 1.00 .
H(12) 0.805(8) 0.134(6) -0.362(10) 0.07(3) Uiso calc 1.00 .
H(13) 0.422(8) -0.027(7) -0.058(10) 0.09(3) Uiso calc 1.00 .
H(14) 0.426(8) -0.128(7) -0.129(10) 0.08(3) Uiso calc 1.00 .
H(15) 0.520(8) -0.125(6) 0.03(1) 0.08(3) Uiso calc 1.00 .
H(16) 0.571(8) -0.100(6) -0.218(9) 0.08(3) Uiso calc 1.00 .
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 56 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 60 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 12 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -7 0
1 -7 0
4 -6 -1
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) N(1) C(2) 122.2(6) 1_555 1_555 1_555 yes
C(1) N(2) C(8) 127.1(7) 1_555 1_555 1_555 yes
C(1) N(2) H(2) 116(5) 1_555 1_555 1_555 no
C(8) N(2) H(2) 116(5) 1_555 1_555 1_555 no
C(1) N(3) C(14) 120.5(8) 1_555 1_555 1_555 yes
C(1) N(3) H(16) 117(5) 1_555 1_555 1_555 no
C(14) N(3) H(16) 121(5) 1_555 1_555 1_555 no
N(1) C(1) N(2) 127.8(7) 1_555 1_555 1_555 yes
N(1) C(1) N(3) 120.8(7) 1_555 1_555 1_555 yes
N(2) C(1) N(3) 111.4(7) 1_555 1_555 1_555 yes
N(1) C(2) C(3) 119.4(8) 1_555 1_555 1_555 yes
N(1) C(2) C(7) 122.2(7) 1_555 1_555 1_555 yes
C(3) C(2) C(7) 118.2(8) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 122.1(10) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 118(5) 1_555 1_555 1_555 no
C(4) C(3) H(3) 118(5) 1_555 1_555 1_555 no
C(3) C(4) C(5) 120.2(10) 1_555 1_555 1_555 yes
C(3) C(4) H(4) 112(5) 1_555 1_555 1_555 no
C(5) C(4) H(4) 127(5) 1_555 1_555 1_555 no
C(4) C(5) C(6) 117(1) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 121(6) 1_555 1_555 1_555 no
C(6) C(5) H(5) 120(6) 1_555 1_555 1_555 no
C(5) C(6) C(7) 122(1) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 116(6) 1_555 1_555 1_555 no
C(7) C(6) H(6) 119(6) 1_555 1_555 1_555 no
C(2) C(7) C(6) 119.2(9) 1_555 1_555 1_555 yes
C(2) C(7) H(7) 123(5) 1_555 1_555 1_555 no
C(6) C(7) H(7) 116(5) 1_555 1_555 1_555 no
N(2) C(8) C(9) 122.8(7) 1_555 1_555 1_555 yes
N(2) C(8) C(13) 118.6(8) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 118.5(8) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 119.7(8) 1_555 1_555 1_555 yes
C(8) C(9) H(8) 111(4) 1_555 1_555 1_555 no
C(10) C(9) H(8) 128(4) 1_555 1_555 1_555 no
C(9) C(10) C(11) 119(1) 1_555 1_555 1_555 yes
C(9) C(10) H(9) 118(5) 1_555 1_555 1_555 no
C(11) C(10) H(9) 122(5) 1_555 1_555 1_555 no
C(10) C(11) C(12) 120(1) 1_555 1_555 1_555 yes
C(10) C(11) H(10) 119(7) 1_555 1_555 1_555 no
C(12) C(11) H(10) 119(7) 1_555 1_555 1_555 no
C(11) C(12) C(13) 121.3(10) 1_555 1_555 1_555 yes
C(11) C(12) H(11) 122(7) 1_555 1_555 1_555 no
C(13) C(12) H(11) 116(7) 1_555 1_555 1_555 no
C(8) C(13) C(12) 119.7(10) 1_555 1_555 1_555 yes
C(8) C(13) H(12) 120(5) 1_555 1_555 1_555 no
C(12) C(13) H(12) 119(5) 1_555 1_555 1_555 no
N(3) C(14) H(13) 111(6) 1_555 1_555 1_555 no
N(3) C(14) H(14) 98(6) 1_555 1_555 1_555 no
N(3) C(14) H(15) 104(5) 1_555 1_555 1_555 no
H(13) C(14) H(14) 111(9) 1_555 1_555 1_555 no
H(13) C(14) H(15) 122(8) 1_555 1_555 1_555 no
H(14) C(14) H(15) 105(8) 1_555 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N(1) C(1) 1.270(9) 1_555 1_555 yes
N(1) C(2) 1.411(9) 1_555 1_555 yes
N(2) C(1) 1.380(9) 1_555 1_555 yes
N(2) C(8) 1.412(9) 1_555 1_555 yes
N(3) C(1) 1.379(10) 1_555 1_555 yes
N(3) C(14) 1.46(1) 1_555 1_555 yes
C(2) C(3) 1.37(1) 1_555 1_555 yes
C(2) C(7) 1.38(1) 1_555 1_555 yes
C(3) C(4) 1.36(1) 1_555 1_555 yes
C(4) C(5) 1.39(1) 1_555 1_555 yes
C(5) C(6) 1.35(1) 1_555 1_555 yes
C(6) C(7) 1.38(1) 1_555 1_555 yes
C(8) C(9) 1.38(1) 1_555 1_555 yes
C(8) C(13) 1.39(1) 1_555 1_555 yes
C(9) C(10) 1.40(1) 1_555 1_555 yes
C(10) C(11) 1.34(1) 1_555 1_555 yes
C(11) C(12) 1.34(2) 1_555 1_555 yes
C(12) C(13) 1.36(1) 1_555 1_555 yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N(1) N(2) 2.931(9) 1_555 2_555
N(1) N(3) 3.552(9) 1_555 2_555
N(1) C(8) 3.60(1) 1_555 2_555
N(2) C(14) 3.50(2) 1_555 2_554
C(4) C(11) 3.59(1) 1_555 4_455
C(5) C(14) 3.45(1) 1_555 3_555
C(6) C(14) 3.54(1) 1_555 3_555
C(11) C(14) 3.48(2) 1_555 3_555
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13443960
