#------------------------------------------------------------------------------
#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/67/4116757.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_4116757
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_sum            'C24 H30 I2 N6'
_chemical_formula_weight         656.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             'Fri Jan  9 14:44:05 1998'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 113.56(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.929(2)
_cell_length_b                   11.173(2)
_cell_length_c                   11.895(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      22.0
_cell_volume                     1331.4(4)
_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    SAPI91
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      -0.04407
_diffrn_orient_matrix_UB_12      -0.00071
_diffrn_orient_matrix_UB_13      -0.09161
_diffrn_orient_matrix_UB_21      -0.01537
_diffrn_orient_matrix_UB_22      -0.08811
_diffrn_orient_matrix_UB_23      0.00144
_diffrn_orient_matrix_UB_31      -0.08824
_diffrn_orient_matrix_UB_32      0.01570
_diffrn_orient_matrix_UB_33      0.00403
_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  0.079
_diffrn_reflns_av_sigmaI/netI    0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2226
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         0.00
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        -3.07
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    18.716
_exptl_absorpt_correction_T_max  1.033
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   '\DF (DIFABS; Walker & Stuart, 1983)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             644.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.910
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     205
_refine_ls_number_reflns         1555
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0410
_refine_ls_shift/esd_max         5.6260
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00001|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0440
_reflns_number_observed          1555
_reflns_number_total             2105
_reflns_observed_criterion       >3.0sigma(I)
_cod_data_source_file            ja9806534_11.cif
_cod_data_source_block           Compound_10b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00001|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) + 0.00001|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1331.3(5)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C24 H30 I2 N6 '
_cod_database_code               4116757
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
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
I(1) 0.37859(7) 0.31187(6) 0.51120(6) 0.0474(2) Uani d 1.00
N(2) 0.7263(7) 0.4360(7) 0.8860(6) 0.035(2) Uani d 1.00
N(3) 0.7503(8) 0.2863(7) 1.0302(7) 0.037(2) Uani d 1.00
N(4) 0.5734(8) 0.2779(8) 0.8369(7) 0.056(3) Uani d 1.00
C(5) 0.6819(10) 0.3327(9) 0.9159(9) 0.041(3) Uani d 1.00
C(7) 0.8010(10) 0.3624(9) 1.1336(8) 0.037(3) Uani d 1.00
C(8) 0.904(1) 0.5829(9) 0.9978(9) 0.036(3) Uani d 1.00
C(9) 0.967(1) 0.3869(9) 0.9470(9) 0.034(3) Uani d 1.00
C(10) 0.932(1) 0.352(1) 1.220(1) 0.051(4) Uani d 1.00
C(11) 0.637(1) 0.514(1) 0.790(1) 0.056(4) Uani d 1.00
C(12) 0.721(1) 0.452(1) 1.1490(9) 0.051(4) Uani d 1.00
C(13) 0.985(1) 0.425(1) 1.3206(9) 0.053(4) Uani d 1.00
C(14) 0.773(1) 0.530(1) 1.249(1) 0.065(5) Uani d 1.00
C(15) 0.906(1) 0.514(1) 1.334(1) 0.058(4) Uani d 1.00
C(16) 0.744(1) 0.157(1) 1.045(1) 0.058(5) Uani d 1.00
C(17) 0.8669(10) 0.4694(8) 0.9439(7) 0.034(3) Uani d 1.00
H(3) 0.604(9) 0.460(8) 1.068(8) 0.07(3) Uiso calc 1.00
H(4) 0.846(8) 0.626(7) 0.998(8) 0.03(2) Uiso calc 1.00
H(5) 0.70(2) 0.19(2) 1.07(2) 0.15(2) Uiso calc 1.00
H(6) 0.77(1) 0.12(1) 1.00(1) 0.09(2) Uiso calc 1.00
H(7) 0.956(8) 0.309(8) 0.912(7) 0.04(2) Uiso calc 1.00
H(12) 0.81(1) 0.139(9) 1.100(9) 0.05(2) Uiso calc 1.00
H(13) 0.988(9) 0.291(9) 1.209(9) 0.05(3) Uiso calc 1.00
H(14) 1.074(8) 0.414(8) 1.379(8) 0.04(2) Uiso calc 1.00
H(15) 0.720(10) 0.592(10) 1.259(9) 0.07(3) Uiso calc 1.00
H(16) 0.941(9) 0.566(8) 1.403(8) 0.05(2) Uiso calc 1.00
H(17) 0.69(1) 0.58(1) 0.78(1) 0.06(2) Uiso calc 1.00
H(18) 0.60(1) 0.47(1) 0.72(1) 0.09(3) Uiso calc 1.00
H(19) 0.57(1) 0.54(1) 0.81(1) 0.12(2) Uiso calc 1.00
H(20) 0.543(1) 0.2060(9) 0.8599(9) 0.0671 Uiso calc 1.00
H(21) 0.526(1) 0.3108(9) 0.7575(9) 0.0699 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 48 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)
;
I 0 4 -0.326 6.836
;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
-5 1 0
-4 0 -2
-3 4 -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(5) N(2) C(11) 121.2(9) 1_555 1_555 1_555 yes
C(5) N(2) C(17) 120.6(8) 1_555 1_555 1_555 yes
C(11) N(2) C(17) 118.1(8) 1_555 1_555 1_555 yes
C(5) N(3) C(7) 119.7(8) 1_555 1_555 1_555 yes
C(5) N(3) C(16) 118.1(9) 1_555 1_555 1_555 yes
C(5) N(3) H(5) 125(7) 1_555 1_555 1_555 no
C(7) N(3) C(16) 121.0(9) 1_555 1_555 1_555 yes
C(7) N(3) H(5) 100(7) 1_555 1_555 1_555 no
C(16) N(3) H(5) 31(6) 1_555 1_555 1_555 no
C(5) N(4) H(20) 118(7) 1_555 1_555 1_555 no
C(5) N(4) H(21) 124(5) 1_555 1_555 1_555 no
H(20) N(4) H(21) 114(9) 1_555 1_555 1_555 no
N(2) C(5) N(3) 119.6(9) 1_555 1_555 1_555 yes
N(2) C(5) N(4) 120.0(9) 1_555 1_555 1_555 yes
N(3) C(5) N(4) 120.4(10) 1_555 1_555 1_555 yes
N(3) C(7) C(10) 121(1) 1_555 1_555 1_555 yes
N(3) C(7) C(12) 120.3(9) 1_555 1_555 1_555 yes
C(10) C(7) C(12) 118(1) 1_555 1_555 1_555 yes
C(9) C(8) C(17) 121.1(10) 3_767 1_555 1_555 yes
C(9) C(8) H(4) 122(6) 3_767 1_555 1_555 no
C(17) C(8) H(4) 116(6) 1_555 1_555 1_555 no
C(8) C(9) C(17) 119.6(9) 3_767 1_555 1_555 yes
C(8) C(9) H(7) 111(5) 3_767 1_555 1_555 no
C(17) C(9) H(7) 128(5) 1_555 1_555 1_555 no
C(7) C(10) C(13) 123(1) 1_555 1_555 1_555 yes
C(7) C(10) H(13) 122(6) 1_555 1_555 1_555 no
C(13) C(10) H(13) 114(6) 1_555 1_555 1_555 no
N(2) C(11) H(17) 109(8) 1_555 1_555 1_555 no
N(2) C(11) H(18) 107(6) 1_555 1_555 1_555 no
N(2) C(11) H(19) 106(8) 1_555 1_555 1_555 no
H(17) C(11) H(18) 106(10) 1_555 1_555 1_555 no
H(17) C(11) H(19) 112(11) 1_555 1_555 1_555 no
H(18) C(11) H(19) 114(9) 1_555 1_555 1_555 no
C(7) C(12) C(14) 119(1) 1_555 1_555 1_555 yes
C(7) C(12) H(3) 117(4) 1_555 1_555 1_555 no
C(14) C(12) H(3) 122(4) 1_555 1_555 1_555 no
C(10) C(13) C(15) 117(1) 1_555 1_555 1_555 yes
C(10) C(13) H(14) 126(5) 1_555 1_555 1_555 no
C(15) C(13) H(14) 115(5) 1_555 1_555 1_555 no
C(12) C(14) C(15) 120(1) 1_555 1_555 1_555 yes
C(12) C(14) H(15) 109(6) 1_555 1_555 1_555 no
C(15) C(14) H(15) 130(6) 1_555 1_555 1_555 no
C(13) C(15) C(14) 121(1) 1_555 1_555 1_555 yes
C(13) C(15) H(16) 111(6) 1_555 1_555 1_555 no
C(14) C(15) H(16) 127(6) 1_555 1_555 1_555 no
N(3) C(16) H(5) 69(14) 1_555 1_555 1_555 no
N(3) C(16) H(6) 113(8) 1_555 1_555 1_555 no
N(3) C(16) H(12) 108(8) 1_555 1_555 1_555 no
H(5) C(16) H(6) 173(16) 1_555 1_555 1_555 no
H(5) C(16) H(12) 98(15) 1_555 1_555 1_555 no
H(6) C(16) H(12) 84(10) 1_555 1_555 1_555 no
N(2) C(17) C(8) 120.7(9) 1_555 1_555 1_555 yes
N(2) C(17) C(9) 120.0(8) 1_555 1_555 1_555 yes
C(8) C(17) C(9) 119.3(9) 1_555 1_555 1_555 yes
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(2) C(5) 1.34(1) 1_555 1_555 yes
N(2) C(11) 1.45(1) 1_555 1_555 yes
N(2) C(17) 1.46(1) 1_555 1_555 yes
N(3) C(5) 1.36(1) 1_555 1_555 yes
N(3) C(7) 1.42(1) 1_555 1_555 yes
N(3) C(16) 1.45(1) 1_555 1_555 yes
N(4) C(5) 1.31(1) 1_555 1_555 yes
C(7) C(10) 1.40(1) 1_555 1_555 yes
C(7) C(12) 1.38(1) 1_555 1_555 yes
C(8) C(9) 1.34(1) 1_555 3_767 yes
C(8) C(17) 1.40(1) 1_555 1_555 yes
C(9) C(17) 1.41(1) 1_555 1_555 yes
C(10) C(13) 1.36(2) 1_555 1_555 yes
C(12) C(14) 1.39(2) 1_555 1_555 yes
C(13) C(15) 1.36(2) 1_555 1_555 yes
C(14) C(15) 1.39(2) 1_555 1_555 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139120623
