#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:40:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178476 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/97/4029779.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_4029779
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            'C21 H24 N4'
_chemical_formula_weight         332.44
_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                 94.6725(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.80020(10)
_cell_length_b                   7.24450(10)
_cell_length_c                   26.1183(4)
_cell_measurement_reflns_used    4585
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1848.17(4)
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8154
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block cut from rod'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         .255
_refine_diff_density_min         -.273
_refine_diff_density_rms         .047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0460
_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)+(0.0727P)²+0.2958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                3010
_reflns_number_total             4245
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            7b_Ci.cif
_cod_data_source_block           k05296
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4029779
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 0.46773(11) 0.52461(16) 0.41922(4) 0.0192(3) Uani 1 1 d .
C2 C 0.49426(14) 0.6753(2) 0.44978(5) 0.0198(3) Uani 1 1 d .
N3 N 0.62193(12) 0.67304(17) 0.47000(4) 0.0213(3) Uani 1 1 d .
C4 C 0.68055(14) 0.5141(2) 0.45137(5) 0.0208(3) Uani 1 1 d .
C5 C 0.58757(14) 0.4190(2) 0.42049(5) 0.0211(3) Uani 1 1 d .
C6 C 0.33571(14) 0.4755(2) 0.39469(5) 0.0198(3) Uani 1 1 d .
N7 N 0.27716(12) 0.55734(17) 0.35572(4) 0.0226(3) Uani 1 1 d .
N8 N 0.28019(12) 0.33277(17) 0.42007(4) 0.0206(3) Uani 1 1 d .
H8 H 0.3261 0.2991 0.4489 0.025 Uiso 1 1 calc R
C9 C 0.38982(15) 0.8193(2) 0.45727(6) 0.0234(3) Uani 1 1 d .
H9A H 0.4117 0.8812 0.4903 0.035 Uiso 1 1 calc R
H9B H 0.2993 0.7618 0.4570 0.035 Uiso 1 1 calc R
H9C H 0.3896 0.9101 0.4294 0.035 Uiso 1 1 calc R
C10 C 0.82855(14) 0.4681(2) 0.46522(6) 0.0273(4) Uani 1 1 d .
H10A H 0.8491 0.3465 0.4513 0.041 Uiso 1 1 calc R
H10B H 0.8464 0.4664 0.5027 0.041 Uiso 1 1 calc R
H10C H 0.8866 0.5614 0.4507 0.041 Uiso 1 1 calc R
C11 C 0.59663(15) 0.2434(2) 0.39130(6) 0.0281(4) Uani 1 1 d .
H11A H 0.6930 0.2132 0.3880 0.042 Uiso 1 1 calc R
H11B H 0.5492 0.2577 0.3570 0.042 Uiso 1 1 calc R
H11C H 0.5537 0.1437 0.4096 0.042 Uiso 1 1 calc R
C12 C 0.34556(15) 0.6958(2) 0.32924(5) 0.0229(3) Uani 1 1 d .
C13 C 0.28017(16) 0.8651(2) 0.32058(6) 0.0265(4) Uani 1 1 d .
H13 H 0.1943 0.8869 0.3340 0.032 Uiso 1 1 calc R
C14 C 0.33923(17) 1.0022(2) 0.29263(6) 0.0299(4) Uani 1 1 d .
H14 H 0.2935 1.1171 0.2875 0.036 Uiso 1 1 calc R
C15 C 0.46399(17) 0.9748(2) 0.27202(6) 0.0303(4) Uani 1 1 d .
C16 C 0.52740(16) 0.8050(2) 0.28058(5) 0.0291(4) Uani 1 1 d .
H16 H 0.6127 0.7830 0.2668 0.035 Uiso 1 1 calc R
C17 C 0.47014(16) 0.6667(2) 0.30849(5) 0.0260(3) Uani 1 1 d .
H17 H 0.5160 0.5518 0.3135 0.031 Uiso 1 1 calc R
C18 C 0.52709(19) 1.1243(3) 0.24123(6) 0.0413(5) Uani 1 1 d .
H18A H 0.6268 1.1098 0.2440 0.062 Uiso 1 1 calc R
H18B H 0.5034 1.2455 0.2546 0.062 Uiso 1 1 calc R
H18C H 0.4919 1.1145 0.2051 0.062 Uiso 1 1 calc R
C19 C 0.15997(14) 0.2319(2) 0.40658(5) 0.0198(3) Uani 1 1 d .
C20 C 0.12293(14) 0.1012(2) 0.44211(5) 0.0209(3) Uani 1 1 d .
H20 H 0.1740 0.0924 0.4745 0.025 Uiso 1 1 calc R
C21 C 0.01348(15) -0.0152(2) 0.43095(5) 0.0221(3) Uani 1 1 d .
H21 H -0.0088 -0.1042 0.4557 0.027 Uiso 1 1 calc R
C22 C -0.06556(14) -0.0052(2) 0.38396(6) 0.0219(3) Uani 1 1 d .
C23 C -0.02951(15) 0.1297(2) 0.34960(6) 0.0246(3) Uani 1 1 d .
H23 H -0.0827 0.1413 0.3177 0.030 Uiso 1 1 calc R
C24 C 0.08091(14) 0.2483(2) 0.35985(5) 0.0233(3) Uani 1 1 d .
H24 H 0.1022 0.3389 0.3355 0.028 Uiso 1 1 calc R
C25 C -0.18133(15) -0.1370(2) 0.37077(6) 0.0278(4) Uani 1 1 d .
H25A H -0.2378 -0.0908 0.3408 0.042 Uiso 1 1 calc R
H25B H -0.2375 -0.1476 0.4000 0.042 Uiso 1 1 calc R
H25C H -0.1443 -0.2584 0.3629 0.042 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 107.69(11)
C2 N1 C6 125.37(12)
C5 N1 C6 126.65(12)
N3 C2 N1 110.72(12)
N3 C2 C9 126.70(13)
N1 C2 C9 122.57(12)
C2 N3 C4 106.00(12)
C5 C4 N3 110.61(12)
C5 C4 C10 128.26(14)
N3 C4 C10 121.13(13)
C4 C5 N1 104.97(13)
C4 C5 C11 132.36(13)
N1 C5 C11 122.66(12)
N7 C6 N8 124.71(13)
N7 C6 N1 124.77(13)
N8 C6 N1 110.49(11)
C6 N7 C12 121.28(13)
C6 N8 C19 129.09(12)
C6 N8 H8 115.5
C19 N8 H8 115.5
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
C4 C10 H10A 109.5
C4 C10 H10B 109.5
H10A C10 H10B 109.5
C4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C5 C11 H11A 109.5
C5 C11 H11B 109.5
H11A C11 H11B 109.5
C5 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C17 C12 C13 118.45(14)
C17 C12 N7 123.20(14)
C13 C12 N7 118.20(13)
C14 C13 C12 120.63(15)
C14 C13 H13 119.7
C12 C13 H13 119.7
C13 C14 C15 121.33(16)
C13 C14 H14 119.3
C15 C14 H14 119.3
C16 C15 C14 117.42(15)
C16 C15 C18 121.58(15)
C14 C15 C18 121.00(16)
C17 C16 C15 122.05(15)
C17 C16 H16 119.0
C15 C16 H16 119.0
C16 C17 C12 120.11(15)
C16 C17 H17 119.9
C12 C17 H17 119.9
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C20 C19 C24 118.90(13)
C20 C19 N8 116.37(12)
C24 C19 N8 124.66(13)
C21 C20 C19 121.05(13)
C21 C20 H20 119.5
C19 C20 H20 119.5
C20 C21 C22 121.32(14)
C20 C21 H21 119.3
C22 C21 H21 119.3
C23 C22 C21 116.80(13)
C23 C22 C25 121.70(13)
C21 C22 C25 121.48(13)
C24 C23 C22 122.97(13)
C24 C23 H23 118.5
C22 C23 H23 118.5
C23 C24 C19 118.92(14)
C23 C24 H24 120.5
C19 C24 H24 120.5
C22 C25 H25A 109.5
C22 C25 H25B 109.5
H25A C25 H25B 109.5
C22 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3647(18)
N1 C5 1.3998(18)
N1 C6 1.4409(17)
C2 N3 1.3179(18)
C2 C9 1.4858(19)
N3 C4 1.3920(18)
C4 C5 1.355(2)
C4 C10 1.503(2)
C5 C11 1.489(2)
C6 N7 1.2733(18)
C6 N8 1.3651(18)
N7 C12 1.4177(18)
N8 C19 1.4066(18)
N8 H8 0.8800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C17 1.392(2)
C12 C13 1.394(2)
C13 C14 1.387(2)
C13 H13 0.9500
C14 C15 1.390(2)
C14 H14 0.9500
C15 C16 1.388(2)
C15 C18 1.511(2)
C16 C17 1.384(2)
C16 H16 0.9500
C17 H17 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 C20 1.394(2)
C19 C24 1.3963(19)
C20 C21 1.377(2)
C20 H20 0.9500
C21 C22 1.399(2)
C21 H21 0.9500
C22 C23 1.391(2)
C22 C25 1.501(2)
C23 C24 1.391(2)
C23 H23 0.9500
C24 H24 0.9500
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 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 2.15 2.9523(16) 151.9 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 0.29(16)
C6 N1 C2 N3 174.46(12)
C5 N1 C2 C9 179.56(12)
C6 N1 C2 C9 -6.3(2)
N1 C2 N3 C4 0.37(15)
C9 C2 N3 C4 -178.87(13)
C2 N3 C4 C5 -0.92(16)
C2 N3 C4 C10 178.20(13)
N3 C4 C5 N1 1.07(16)
C10 C4 C5 N1 -177.97(14)
N3 C4 C5 C11 179.99(15)
C10 C4 C5 C11 0.9(3)
C2 N1 C5 C4 -0.83(15)
C6 N1 C5 C4 -174.91(13)
C2 N1 C5 C11 -179.88(13)
C6 N1 C5 C11 6.0(2)
C2 N1 C6 N7 74.1(2)
C5 N1 C6 N7 -112.80(17)
C2 N1 C6 N8 -103.93(15)
C5 N1 C6 N8 69.15(17)
N8 C6 N7 C12 -175.43(13)
N1 C6 N7 C12 6.8(2)
N7 C6 N8 C19 8.4(2)
N1 C6 N8 C19 -173.57(12)
C6 N7 C12 C17 56.4(2)
C6 N7 C12 C13 -128.15(15)
C17 C12 C13 C14 -1.0(2)
N7 C12 C13 C14 -176.72(13)
C12 C13 C14 C15 0.7(2)
C13 C14 C15 C16 -0.1(2)
C13 C14 C15 C18 179.49(14)
C14 C15 C16 C17 0.0(2)
C18 C15 C16 C17 -179.65(14)
C15 C16 C17 C12 -0.3(2)
C13 C12 C17 C16 0.9(2)
N7 C12 C17 C16 176.32(13)
C6 N8 C19 C20 -175.43(13)
C6 N8 C19 C24 7.7(2)
C24 C19 C20 C21 2.4(2)
N8 C19 C20 C21 -174.68(13)
C19 C20 C21 C22 -0.9(2)
C20 C21 C22 C23 -1.0(2)
C20 C21 C22 C25 177.44(14)
C21 C22 C23 C24 1.3(2)
C25 C22 C23 C24 -177.09(14)
C22 C23 C24 C19 0.2(2)
C20 C19 C24 C23 -2.1(2)
N8 C19 C24 C23 174.77(13)
