#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/67/4116751.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_4116751
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            'C16.5 H21.5 N3 O0.5'
_chemical_formula_weight         269.87
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Fri Jan  9 15:42:12 1998'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                97.21(7)
_cell_angle_beta                 90.73(3)
_cell_angle_gamma                77.50(7)
_cell_formula_units_Z            4
_cell_length_a                   11.590(5)
_cell_length_b                   16.44(2)
_cell_length_c                   8.320(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    288.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     1535(2)
_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      288.2
_diffrn_measurement_device       'Rigaku RAXISII'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4425
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         0.00
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       prism
_exptl_crystal_F_000             582.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   3.870
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     517
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0970
_refine_ls_shift/esd_max         4.0290
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.1270
_reflns_number_observed          2320
_reflns_number_total             4425
_reflns_observed_criterion       >4.5sigma(I)
_cod_data_source_file            ja9806534_05.cif
_cod_data_source_block           Compound_4a
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C16.50 H21.50 N3 O0.50 '
_cod_database_code               4116751
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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
O(1) 0.9398(6) 0.4988(5) 0.2470(9) 0.044(2) Uani d 1.00
N(1) 0.7797(8) 0.6899(5) 0.798(1) 0.041(3) Uani d 1.00
N(2) 0.7440(8) 0.7167(6) 1.076(1) 0.041(3) Uani d 1.00
N(3) 0.8665(9) 0.5894(6) 0.962(1) 0.050(3) Uani d 1.00
N(4) 1.1114(8) 0.6852(5) 0.302(1) 0.043(3) Uani d 1.00
N(5) 1.1520(8) 0.7094(6) 0.576(1) 0.043(3) Uani d 1.00
N(6) 1.0813(9) 0.5888(6) 0.474(1) 0.051(3) Uani d 1.00
C(1) 1.1135(10) 0.6557(8) 0.453(1) 0.040(4) Uani d 1.00
C(2) 1.126(1) 0.6969(9) 0.742(1) 0.052(4) Uani d 1.00
C(3) 1.147(1) 0.6233(9) 0.159(2) 0.053(5) Uani d 1.00
C(4) 1.235(1) 0.7578(8) 0.550(1) 0.044(4) Uani d 1.00
C(5) 1.332(1) 0.7236(9) 0.450(2) 0.055(5) Uani d 1.00
C(6) 1.411(1) 0.775(1) 0.417(2) 0.077(6) Uani d 1.00
C(7) 1.394(2) 0.858(1) 0.491(2) 0.083(7) Uani d 1.00
C(8) 1.295(2) 0.889(1) 0.593(2) 0.082(6) Uani d 1.00
C(9) 1.215(1) 0.8401(8) 0.624(2) 0.052(4) Uani d 1.00
C(10) 1.074(1) 0.7702(7) 0.282(1) 0.038(3) Uani d 1.00
C(11) 1.125(1) 0.8041(8) 0.159(1) 0.044(4) Uani d 1.00
C(12) 1.088(1) 0.8874(8) 0.139(2) 0.049(4) Uani d 1.00
C(13) 1.000(1) 0.9386(9) 0.237(2) 0.052(4) Uani d 1.00
C(14) 0.950(1) 0.9065(8) 0.360(2) 0.050(4) Uani d 1.00
C(15) 0.987(1) 0.8215(8) 0.382(1) 0.045(4) Uani d 1.00
C(16) 0.801(1) 0.6606(8) 0.949(1) 0.042(4) Uani d 1.00
C(17) 0.780(1) 0.6987(9) 1.242(1) 0.048(4) Uani d 1.00
C(18) 0.633(1) 0.7726(8) 1.060(1) 0.045(4) Uani d 1.00
C(19) 0.619(1) 0.8557(8) 1.134(2) 0.051(4) Uani d 1.00
C(20) 0.510(1) 0.9110(10) 1.116(2) 0.071(5) Uani d 1.00
C(21) 0.420(2) 0.884(1) 1.021(2) 0.080(6) Uani d 1.00
C(22) 0.439(1) 0.800(1) 0.946(2) 0.070(5) Uani d 1.00
C(23) 0.547(1) 0.7434(9) 0.968(2) 0.051(4) Uani d 1.00
C(24) 0.7741(9) 0.7748(7) 0.777(1) 0.037(3) Uani d 1.00
C(25) 0.8427(10) 0.8221(7) 0.872(1) 0.042(4) Uani d 1.00
C(26) 0.835(1) 0.9052(8) 0.846(2) 0.050(4) Uani d 1.00
C(27) 0.764(1) 0.9417(8) 0.728(1) 0.048(4) Uani d 1.00
C(28) 0.695(1) 0.8934(8) 0.635(1) 0.048(4) Uani d 1.00
C(29) 0.698(1) 0.8116(8) 0.660(1) 0.043(4) Uani d 1.00
C(30) 0.778(1) 0.6291(9) 0.654(2) 0.053(4) Uani d 1.00
C(31) 0.618(2) 0.503(1) 0.348(3) 0.091(8) Uani d 1.00
C(32) 0.553(2) 0.471(1) 0.209(3) 0.123(9) Uani d 1.00
C(33) 0.533(2) 0.517(1) 0.071(2) 0.103(7) Uani d 1.00
H(1) 1.14(1) 0.743(9) 0.82(2) 0.09(3) Uiso calc 1.00
H(2) 1.05(1) 0.693(8) 0.75(2) 0.09(3) Uiso calc 1.00
H(3) 1.18(1) 0.646(10) 0.77(2) 0.10(3) Uiso calc 1.00
H(4) 1.11(1) 0.58(1) 0.16(2) 0.12(3) Uiso calc 1.00
H(5) 1.13(1) 0.65(1) 0.06(2) 0.12(3) Uiso calc 1.00
H(6) 1.23(2) 0.60(1) 0.16(2) 0.14(3) Uiso calc 1.00
H(7) 1.345(10) 0.666(7) 0.40(1) 0.05(3) Uiso calc 1.00
H(8) 1.48(1) 0.753(8) 0.34(2) 0.08(3) Uiso calc 1.00
H(10) 1.28(1) 0.946(10) 0.64(2) 0.10(3) Uiso calc 1.00
H(11) 1.15(1) 0.862(8) 0.69(2) 0.09(3) Uiso calc 1.00
H(12) 1.186(10) 0.769(7) 0.09(1) 0.05(3) Uiso calc 1.00
H(13) 1.123(9) 0.910(6) 0.06(1) 0.04(3) Uiso calc 1.00
H(14) 0.97(1) 0.996(8) 0.22(1) 0.07(3) Uiso calc 1.00
H(15) 0.89(1) 0.942(8) 0.43(1) 0.08(3) Uiso calc 1.00
H(16) 0.952(10) 0.800(7) 0.47(1) 0.06(3) Uiso calc 1.00
H(17) 0.76(1) 0.650(8) 1.26(1) 0.06(3) Uiso calc 1.00
H(18) 0.86(1) 0.690(8) 1.25(2) 0.08(3) Uiso calc 1.00
H(19) 0.74(1) 0.745(7) 1.32(1) 0.05(3) Uiso calc 1.00
H(20) 0.68(1) 0.874(8) 1.19(2) 0.08(3) Uiso calc 1.00
H(21) 0.50(1) 0.97(1) 1.17(2) 0.12(3) Uiso calc 1.00
H(23) 0.38(2) 0.78(1) 0.88(2) 0.14(3) Uiso calc 1.00
H(24) 0.56(1) 0.686(8) 0.92(1) 0.06(3) Uiso calc 1.00
H(25) 0.893(9) 0.798(7) 0.95(1) 0.05(3) Uiso calc 1.00
H(26) 0.88(1) 0.938(9) 0.91(2) 0.10(3) Uiso calc 1.00
H(27) 0.76(1) 0.998(8) 0.71(1) 0.07(3) Uiso calc 1.00
H(28) 0.64(1) 0.918(8) 0.55(1) 0.07(3) Uiso calc 1.00
H(29) 0.65(1) 0.780(7) 0.60(1) 0.06(3) Uiso calc 1.00
H(30) 0.72(1) 0.601(10) 0.66(2) 0.10(3) Uiso calc 1.00
H(31) 0.77(1) 0.658(9) 0.56(2) 0.11(3) Uiso calc 1.00
H(32) 0.85(1) 0.59(1) 0.64(2) 0.13(3) Uiso calc 1.00
H(33) 0.63(2) 0.46(1) 0.43(3) 0.17(3) Uiso calc 1.00
H(34) 0.69(2) 0.51(1) 0.31(2) 0.13(3) Uiso calc 1.00
H(35) 0.57(1) 0.555(9) 0.40(2) 0.09(3) Uiso calc 1.00
H(36) 1.45(1) 0.89(1) 0.47(2) 0.08(3) Uiso calc 1.00
H(37) 0.35(1) 0.92(1) 1.01(2) 0.11(3) Uiso calc 1.00
H(38) 0.60(1) 0.42(1) 0.17(2) 0.15(3) Uiso calc 1.00
H(39) 0.48(1) 0.47(1) 0.25(2) 0.15(3) Uiso calc 1.00
H(40) 0.61(1) 0.52(1) 0.03(2) 0.12(3) Uiso calc 1.00
H(42) 0.4892 0.5722 0.1041 0.1238 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 66 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 86 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 12 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 2 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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(16) 1.40(1) 1_555 1_555 yes
N(1) C(24) 1.41(1) 1_555 1_555 yes
N(1) C(30) 1.46(2) 1_555 1_555 yes
N(2) C(16) 1.39(1) 1_555 1_555 yes
N(2) C(17) 1.48(1) 1_555 1_555 yes
N(2) C(18) 1.43(1) 1_555 1_555 yes
N(3) C(16) 1.26(1) 1_555 1_555 yes
N(4) C(1) 1.40(1) 1_555 1_555 yes
N(4) C(3) 1.47(2) 1_555 1_555 yes
N(4) C(10) 1.40(1) 1_555 1_555 yes
N(5) C(1) 1.40(1) 1_555 1_555 yes
N(5) C(2) 1.47(1) 1_555 1_555 yes
N(5) C(4) 1.41(1) 1_555 1_555 yes
N(6) C(1) 1.27(1) 1_555 1_555 yes
C(4) C(5) 1.38(2) 1_555 1_555 yes
C(4) C(9) 1.39(2) 1_555 1_555 yes
C(5) C(6) 1.43(2) 1_555 1_555 yes
C(6) C(7) 1.40(2) 1_555 1_555 yes
C(7) C(8) 1.41(2) 1_555 1_555 yes
C(8) C(9) 1.41(2) 1_555 1_555 yes
C(10) C(11) 1.42(2) 1_555 1_555 yes
C(10) C(15) 1.38(2) 1_555 1_555 yes
C(11) C(12) 1.38(2) 1_555 1_555 yes
C(12) C(13) 1.38(2) 1_555 1_555 yes
C(13) C(14) 1.40(2) 1_555 1_555 yes
C(14) C(15) 1.41(2) 1_555 1_555 yes
C(18) C(19) 1.40(2) 1_555 1_555 yes
C(18) C(23) 1.38(2) 1_555 1_555 yes
C(19) C(20) 1.40(2) 1_555 1_555 yes
C(20) C(21) 1.41(2) 1_555 1_555 yes
C(21) C(22) 1.42(2) 1_555 1_555 yes
C(22) C(23) 1.41(2) 1_555 1_555 yes
C(24) C(25) 1.40(2) 1_555 1_555 yes
C(24) C(29) 1.42(2) 1_555 1_555 yes
C(25) C(26) 1.39(2) 1_555 1_555 yes
C(26) C(27) 1.38(2) 1_555 1_555 yes
C(27) C(28) 1.41(2) 1_555 1_555 yes
C(28) C(29) 1.38(2) 1_555 1_555 yes
C(31) C(32) 1.48(3) 1_555 1_555 yes
C(32) C(33) 1.45(3) 1_555 1_555 yes
C(33) C(33) 1.51(3) 1_555 2_665 yes
