#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:40:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178476 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/97/4029784.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_4029784
loop_
_publ_author_name
'Long, Sihui'
'Muthusamy, Venkatraj'
'Willis, Peter G.'
'Parkin, Sean'
'Cammers, Arthur'
_publ_section_title
;
 Inversion symmetry and local vs. dispersive interactions in the
 nucleation of hydrogen bonded cyclic n-mer and tape of
 imidazolecarboxamidines.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              23
_journal_paper_doi               10.3762/bjoc.4.23
_journal_volume                  4
_journal_year                    2008
_chemical_formula_sum            'C23 H22 N4'
_chemical_formula_weight         354.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 94.6029(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.22820(10)
_cell_length_b                   14.5797(3)
_cell_length_c                   18.0219(4)
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1893.11(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1994)'
_computing_publication_material
; 
SHELX97-2 (Sheldrick, 1997) and local procedures 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8482
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block cut from rod'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         .267
_refine_diff_density_min         -.279
_refine_diff_density_rms         .061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0483
_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)+(0.0803P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                2950
_reflns_number_total             4332
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            11b_Ci.cif
_cod_data_source_block           k05286
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4029784
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.48325(16) 0.37928(8) 0.44766(7) 0.0172(3) Uani 1 1 d .
C2 C 0.32678(19) 0.41405(9) 0.47685(8) 0.0173(3) Uani 1 1 d .
N3 N 0.34145(16) 0.41443(8) 0.55012(7) 0.0195(3) Uani 1 1 d .
C4 C 0.5149(2) 0.37512(10) 0.57073(8) 0.0188(3) Uani 1 1 d .
C5 C 0.6060(2) 0.35342(9) 0.50762(8) 0.0181(3) Uani 1 1 d .
C6 C 0.51314(19) 0.36602(10) 0.37014(8) 0.0174(3) Uani 1 1 d .
N7 N 0.42234(16) 0.30926(8) 0.32744(7) 0.0196(3) Uani 1 1 d .
N8 N 0.64965(16) 0.42241(8) 0.34971(6) 0.0181(3) Uani 1 1 d .
H8 H 0.6860 0.4651 0.3822 0.022 Uiso 1 1 calc R
C9 C 0.16575(19) 0.44737(11) 0.42826(8) 0.0215(3) Uani 1 1 d .
H9A H 0.0765 0.3973 0.4189 0.032 Uiso 1 1 calc R
H9B H 0.2081 0.4687 0.3809 0.032 Uiso 1 1 calc R
H9C H 0.1061 0.4981 0.4529 0.032 Uiso 1 1 calc R
C10 C 0.6006(2) 0.35753(10) 0.64139(9) 0.0235(4) Uani 1 1 d .
H10 H 0.5415 0.3724 0.6850 0.028 Uiso 1 1 calc R
C11 C 0.7748(2) 0.31770(11) 0.64561(9) 0.0256(4) Uani 1 1 d .
H11 H 0.8360 0.3048 0.6931 0.031 Uiso 1 1 calc R
C12 C 0.8627(2) 0.29599(10) 0.58185(9) 0.0241(4) Uani 1 1 d .
H12 H 0.9826 0.2689 0.5870 0.029 Uiso 1 1 calc R
C13 C 0.78009(19) 0.31285(10) 0.51117(8) 0.0211(4) Uani 1 1 d .
H13 H 0.8392 0.2975 0.4676 0.025 Uiso 1 1 calc R
C14 C 0.28790(19) 0.25073(10) 0.35587(8) 0.0181(3) Uani 1 1 d .
C15 C 0.11243(19) 0.24833(10) 0.31770(8) 0.0204(3) Uani 1 1 d .
H15 H 0.0872 0.2851 0.2746 0.024 Uiso 1 1 calc R
C16 C -0.0252(2) 0.19270(10) 0.34231(8) 0.0215(3) Uani 1 1 d .
H16 H -0.1441 0.1921 0.3157 0.026 Uiso 1 1 calc R
C17 C 0.0064(2) 0.13777(10) 0.40501(8) 0.0202(3) Uani 1 1 d .
C18 C 0.1832(2) 0.13994(10) 0.44214(9) 0.0222(4) Uani 1 1 d .
H18 H 0.2086 0.1029 0.4851 0.027 Uiso 1 1 calc R
C19 C 0.3224(2) 0.19487(10) 0.41787(8) 0.0218(3) Uani 1 1 d .
H19 H 0.4422 0.1944 0.4438 0.026 Uiso 1 1 calc R
C20 C -0.1433(2) 0.07705(11) 0.43127(9) 0.0291(4) Uani 1 1 d .
H20A H -0.2652 0.1015 0.4134 0.044 Uiso 1 1 calc R
H20B H -0.1330 0.0752 0.4858 0.044 Uiso 1 1 calc R
H20C H -0.1294 0.0149 0.4117 0.044 Uiso 1 1 calc R
C21 C 0.74126(19) 0.42171(10) 0.28331(8) 0.0182(3) Uani 1 1 d .
C22 C 0.87550(19) 0.48970(10) 0.27676(8) 0.0205(3) Uani 1 1 d .
H22 H 0.8920 0.5364 0.3134 0.025 Uiso 1 1 calc R
C23 C 0.9843(2) 0.48916(10) 0.21704(8) 0.0225(4) Uani 1 1 d .
H23 H 1.0752 0.5357 0.2134 0.027 Uiso 1 1 calc R
C24 C 0.9636(2) 0.42194(10) 0.16209(8) 0.0210(3) Uani 1 1 d .
C25 C 0.8237(2) 0.35727(10) 0.16785(8) 0.0203(3) Uani 1 1 d .
H25 H 0.8041 0.3121 0.1300 0.024 Uiso 1 1 calc R
C26 C 0.7118(2) 0.35659(10) 0.22703(8) 0.0197(3) Uani 1 1 d .
H26 H 0.6163 0.3122 0.2291 0.024 Uiso 1 1 calc R
C27 C 1.0860(2) 0.41993(11) 0.09843(9) 0.0268(4) Uani 1 1 d .
H27A H 1.0439 0.4664 0.0616 0.040 Uiso 1 1 calc R
H27B H 1.0795 0.3592 0.0751 0.040 Uiso 1 1 calc R
H27C H 1.2144 0.4329 0.1171 0.040 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 '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 N1 C5 107.08(12)
C2 N1 C6 127.47(12)
C5 N1 C6 125.34(12)
N3 C2 N1 112.40(12)
N3 C2 C9 126.01(13)
N1 C2 C9 121.58(13)
C2 N3 C4 105.23(12)
C10 C4 C5 119.90(14)
C10 C4 N3 129.78(14)
C5 C4 N3 110.32(12)
C13 C5 N1 132.05(14)
C13 C5 C4 123.00(14)
N1 C5 C4 104.94(12)
N7 C6 N8 125.39(13)
N7 C6 N1 124.13(13)
N8 C6 N1 110.48(12)
C6 N7 C14 120.42(13)
C6 N8 C21 128.71(12)
C6 N8 H8 115.6
C21 N8 H8 115.6
C2 C9 H9A 109.5
C2 C9 H9B 109.5
H9A C9 H9B 109.5
C2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C4 117.59(14)
C11 C10 H10 121.2
C4 C10 H10 121.2
C10 C11 C12 121.56(14)
C10 C11 H11 119.2
C12 C11 H11 119.2
C13 C12 C11 121.79(14)
C13 C12 H12 119.1
C11 C12 H12 119.1
C12 C13 C5 116.16(14)
C12 C13 H13 121.9
C5 C13 H13 121.9
C19 C14 C15 118.67(13)
C19 C14 N7 123.98(12)
C15 C14 N7 117.33(13)
C16 C15 C14 120.38(14)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C17 121.54(14)
C15 C16 H16 119.2
C17 C16 H16 119.2
C16 C17 C18 117.50(13)
C16 C17 C20 121.34(13)
C18 C17 C20 121.15(14)
C19 C18 C17 121.54(14)
C19 C18 H18 119.2
C17 C18 H18 119.2
C18 C19 C14 120.34(14)
C18 C19 H19 119.8
C14 C19 H19 119.8
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C26 C21 C22 119.20(13)
C26 C21 N8 124.53(13)
C22 C21 N8 116.21(13)
C23 C22 C21 120.22(14)
C23 C22 H22 119.9
C21 C22 H22 119.9
C22 C23 C24 121.46(14)
C22 C23 H23 119.3
C24 C23 H23 119.3
C25 C24 C23 117.43(14)
C25 C24 C27 121.25(14)
C23 C24 C27 121.31(14)
C26 C25 C24 122.20(14)
C26 C25 H25 118.9
C24 C25 H25 118.9
C25 C26 C21 119.34(14)
C25 C26 H26 120.3
C21 C26 H26 120.3
C24 C27 H27A 109.5
C24 C27 H27B 109.5
H27A C27 H27B 109.5
C24 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3814(18)
N1 C5 1.3939(18)
N1 C6 1.4437(17)
C2 N3 1.3161(18)
C2 C9 1.4812(19)
N3 C4 1.4013(18)
C4 C10 1.394(2)
C4 C5 1.396(2)
C5 C13 1.387(2)
C6 N7 1.2755(18)
C6 N8 1.3578(17)
N7 C14 1.4195(18)
N8 C21 1.4133(17)
N8 H8 0.8800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.383(2)
C10 H10 0.9500
C11 C12 1.393(2)
C11 H11 0.9500
C12 C13 1.385(2)
C12 H12 0.9500
C13 H13 0.9500
C14 C19 1.389(2)
C14 C15 1.3939(19)
C15 C16 1.384(2)
C15 H15 0.9500
C16 C17 1.389(2)
C16 H16 0.9500
C17 C18 1.395(2)
C17 C20 1.503(2)
C18 C19 1.384(2)
C18 H18 0.9500
C19 H19 0.9500
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 C26 1.393(2)
C21 C22 1.399(2)
C22 C23 1.383(2)
C22 H22 0.9500
C23 C24 1.393(2)
C23 H23 0.9500
C24 C25 1.393(2)
C24 C27 1.504(2)
C25 C26 1.389(2)
C25 H25 0.9500
C26 H26 0.9500
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
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
N8 H8 N3 0.88 2.16 2.9839(17) 156.4 3_666
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
C5 N1 C2 N3 1.47(16)
C6 N1 C2 N3 177.87(12)
C5 N1 C2 C9 -179.32(12)
C6 N1 C2 C9 -2.9(2)
N1 C2 N3 C4 -1.87(15)
C9 C2 N3 C4 178.96(13)
C2 N3 C4 C10 -179.08(15)
C2 N3 C4 C5 1.60(16)
C2 N1 C5 C13 178.15(15)
C6 N1 C5 C13 1.7(2)
C2 N1 C5 C4 -0.38(15)
C6 N1 C5 C4 -176.88(12)
C10 C4 C5 C13 1.2(2)
N3 C4 C5 C13 -179.44(13)
C10 C4 C5 N1 179.87(12)
N3 C4 C5 N1 -0.73(15)
C2 N1 C6 N7 -65.7(2)
C5 N1 C6 N7 110.12(16)
C2 N1 C6 N8 114.08(15)
C5 N1 C6 N8 -70.14(16)
N8 C6 N7 C14 177.18(13)
N1 C6 N7 C14 -3.1(2)
N7 C6 N8 C21 -11.1(2)
N1 C6 N8 C21 169.22(12)
C5 C4 C10 C11 -0.6(2)
N3 C4 C10 C11 -179.90(14)
C4 C10 C11 C12 0.2(2)
C10 C11 C12 C13 -0.2(2)
C11 C12 C13 C5 0.7(2)
N1 C5 C13 C12 -179.45(14)
C4 C5 C13 C12 -1.1(2)
C6 N7 C14 C19 -52.2(2)
C6 N7 C14 C15 129.31(14)
C19 C14 C15 C16 1.4(2)
N7 C14 C15 C16 179.94(13)
C14 C15 C16 C17 -0.2(2)
C15 C16 C17 C18 -0.6(2)
C15 C16 C17 C20 -179.64(14)
C16 C17 C18 C19 0.2(2)
C20 C17 C18 C19 179.27(14)
C17 C18 C19 C14 1.0(2)
C15 C14 C19 C18 -1.7(2)
N7 C14 C19 C18 179.79(13)
C6 N8 C21 C26 -3.9(2)
C6 N8 C21 C22 178.91(13)
C26 C21 C22 C23 -3.4(2)
N8 C21 C22 C23 173.92(13)
C21 C22 C23 C24 0.2(2)
C22 C23 C24 C25 2.6(2)
C22 C23 C24 C27 -178.15(14)
C23 C24 C25 C26 -2.2(2)
C27 C24 C25 C26 178.50(14)
C24 C25 C26 C21 -0.9(2)
C22 C21 C26 C25 3.8(2)
N8 C21 C26 C25 -173.36(13)
