#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/41/2014142.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014142
loop_
_publ_author_name
'Gilles Gasser'
'Helen Stoeckli-Evans'
_publ_section_title
;2,6-Dibenzyl-1,2,3,5,6,7-hexahydro-2,4,6,8-tetraaza-s-indacene and
 2,6-bis(4-methoxybenzyl)-1,2,3,5,6,7-hexahydro-2,4,6,8-tetraaza-s-indacene
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o514
_journal_page_last               o516
_journal_paper_doi               10.1107/S0108270104009485
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H22 N4'
_chemical_formula_moiety         'C22 H22 N4'
_chemical_formula_sum            'C22 H22 N4'
_chemical_formula_weight         342.44
_chemical_name_common
;
2,6-Dibenzyl-1,2,3,5,6,7-hexahydro-2,4,6,8-tetraaza-s-indacene
;
_chemical_name_systematic
;
N,N'-di-N-benzylbispyrrolidino[3,4-5,6]pyrazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.205(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   36.228(3)
_cell_length_b                   5.5729(6)
_cell_length_c                   8.9677(7)
_cell_measurement_reflns_used    5182
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.26
_cell_volume                     1799.9(3)
_computing_cell_refinement       'CELL (Stoe & Cie, 2000)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Stoe image-plate'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12398
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0662P)²+1.3228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1812
_reflns_number_gt                1882
_reflns_number_total             3324
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1478.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014142
_cod_database_fobs_code          2014142
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.51743(7) 0.7941(4) 0.0756(3) 0.0331(6) Uani d . 1 . . N
N2 0.42069(7) 0.8561(5) 0.1259(3) 0.0337(6) Uani d . 1 . . N
C1 0.53399(8) 0.9340(5) -0.0185(3) 0.0293(7) Uani d . 1 . . C
C2 0.48283(8) 0.8674(5) 0.0922(3) 0.0297(7) Uani d . 1 . . C
C3 0.45659(9) 0.7575(6) 0.1901(4) 0.0344(7) Uani d . 1 . . C
H3A 0.4569 0.5802 0.1837 0.041 Uiso calc R 1 . . H
H3B 0.4625 0.8066 0.2961 0.041 Uiso calc R 1 . . H
C4 0.57247(9) 0.9067(5) -0.0620(4) 0.0336(7) Uani d . 1 . . C
H4A 0.5905 0.8718 0.0263 0.040 Uiso calc R 1 . . H
H4B 0.5737 0.7779 -0.1373 0.040 Uiso calc R 1 . . H
C5 0.39268(9) 0.8590(6) 0.2322(4) 0.0406(8) Uani d . 1 . . C
H5A 0.4000 0.9765 0.3128 0.049 Uiso calc R 1 . . H
H5B 0.3914 0.6987 0.2789 0.049 Uiso calc R 1 . . H
C6 0.35472(9) 0.9253(6) 0.1544(4) 0.0364(8) Uani d . 1 . . C
C7 0.33596(10) 1.1243(6) 0.1980(4) 0.0476(9) Uani d . 1 . . C
H7A 0.3467 1.2217 0.2781 0.057 Uiso calc R 1 . . H
C8 0.30114(11) 1.1832(7) 0.1246(5) 0.0570(11) Uani d . 1 . . C
H8A 0.2883 1.3210 0.1540 0.068 Uiso calc R 1 . . H
C9 0.28561(10) 1.0403(8) 0.0096(5) 0.0549(10) Uani d . 1 . . C
H9A 0.2618 1.0782 -0.0394 0.066 Uiso calc R 1 . . H
C10 0.30430(10) 0.8434(7) -0.0349(4) 0.0494(10) Uani d . 1 . . C
H10A 0.2937 0.7472 -0.1160 0.059 Uiso calc R 1 . . H
C11 0.33848(9) 0.7864(6) 0.0388(4) 0.0419(8) Uani d . 1 . . C
H11A 0.3511 0.6480 0.0090 0.050 Uiso calc R 1 . . H
N21 -0.01705(7) 0.2962(5) 0.0652(3) 0.0362(7) Uani d . 1 . . N
N22 0.08030(7) 0.3620(5) 0.1902(3) 0.0368(7) Uani d . 1 . . N
C21 -0.03425(9) 0.4333(5) -0.0443(4) 0.0340(7) Uani d . 1 . . C
C22 0.01775(9) 0.3711(5) 0.1066(4) 0.0334(7) Uani d . 1 . . C
C23 0.04457(9) 0.2660(6) 0.2267(4) 0.0375(8) Uani d . 1 . . C
H23A 0.0391 0.3189 0.3274 0.045 Uiso calc R 1 . . H
H23B 0.0443 0.0884 0.2227 0.045 Uiso calc R 1 . . H
C24 0.07269(9) 0.5967(6) 0.1174(4) 0.0370(8) Uani d . 1 . . C
H24A 0.0902 0.6298 0.0426 0.044 Uiso calc R 1 . . H
H24B 0.0742 0.7281 0.1921 0.044 Uiso calc R 1 . . H
C25 0.10884(10) 0.3692(7) 0.3173(4) 0.0440(9) Uani d . 1 . . C
H25A 0.1112 0.2088 0.3648 0.053 Uiso calc R 1 . . H
H25B 0.1015 0.4847 0.3927 0.053 Uiso calc R 1 . . H
C26 0.14594(9) 0.4430(6) 0.2682(4) 0.0404(8) Uani d . 1 . . C
C27 0.16199(9) 0.3038(7) 0.1647(4) 0.0449(9) Uani d . 1 . . C
H27A 0.1499 0.1611 0.1274 0.054 Uiso calc R 1 . . H
C28 0.19537(11) 0.3703(7) 0.1150(5) 0.0549(10) Uani d . 1 . . C
H28A 0.2061 0.2743 0.0433 0.066 Uiso calc R 1 . . H
C29 0.21316(10) 0.5770(8) 0.1698(5) 0.0542(10) Uani d . 1 . . C
H29A 0.2360 0.6237 0.1358 0.065 Uiso calc R 1 . . H
C30 0.19775(11) 0.7128(7) 0.2728(5) 0.0551(10) Uani d . 1 . . C
H30A 0.2101 0.8541 0.3108 0.066 Uiso calc R 1 . . H
C31 0.16432(11) 0.6476(7) 0.3228(4) 0.0492(9) Uani d . 1 . . C
H31A 0.1539 0.7440 0.3951 0.059 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 112.4(3) yes
C5 N2 C3 . . 113.2(3) yes
C5 N2 C4 . 3_675 113.6(3) yes
C3 N2 C4 . 3_675 108.0(2) yes
N1 C1 C2 . 3_675 124.0(3) ?
N1 C1 C4 . . 126.8(3) ?
C2 C1 C4 3_675 . 109.2(3) ?
N1 C2 C1 . 3_675 123.7(3) ?
N1 C2 C3 . . 127.0(3) ?
C1 C2 C3 3_675 . 109.3(3) ?
N2 C3 C2 . . 102.1(2) ?
N2 C3 H3A . . 111.4 ?
C2 C3 H3A . . 111.4 ?
N2 C3 H3B . . 111.4 ?
C2 C3 H3B . . 111.4 ?
H3A C3 H3B . . 109.2 ?
N2 C4 C1 3_675 . 102.2(2) ?
N2 C4 H4A 3_675 . 111.3 ?
C1 C4 H4A . . 111.3 ?
N2 C4 H4B 3_675 . 111.3 ?
C1 C4 H4B . . 111.3 ?
H4A C4 H4B . . 109.2 ?
N2 C5 C6 . . 111.1(3) ?
N2 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
N2 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C11 C6 C7 . . 118.9(3) ?
C11 C6 C5 . . 120.1(3) ?
C7 C6 C5 . . 121.0(3) ?
C6 C7 C8 . . 120.2(4) ?
C6 C7 H7A . . 119.9 ?
C8 C7 H7A . . 119.9 ?
C9 C8 C7 . . 119.5(4) ?
C9 C8 H8A . . 120.2 ?
C7 C8 H8A . . 120.2 ?
C10 C9 C8 . . 120.5(4) ?
C10 C9 H9A . . 119.8 ?
C8 C9 H9A . . 119.8 ?
C9 C10 C11 . . 119.5(4) ?
C9 C10 H10A . . 120.3 ?
C11 C10 H10A . . 120.3 ?
C6 C11 C10 . . 121.4(3) ?
C6 C11 H11A . . 119.3 ?
C10 C11 H11A . . 119.3 ?
C22 N21 C21 . . 111.9(3) yes
C25 N22 C23 . . 113.8(3) yes
C25 N22 C24 . . 113.9(3) yes
C23 N22 C24 . . 107.1(2) yes
N21 C22 C21 . 3_565 124.4(3) ?
N21 C22 C23 . . 126.7(3) ?
C21 C22 C23 3_565 . 108.9(3) ?
N22 C23 C22 . . 102.5(2) ?
N22 C23 H23A . . 111.3 ?
C22 C23 H23A . . 111.3 ?
N22 C23 H23B . . 111.3 ?
C22 C23 H23B . . 111.3 ?
H23A C23 H23B . . 109.2 ?
N21 C21 C22 . 3_565 123.7(3) ?
N21 C21 C24 . 3_565 126.8(3) ?
C22 C21 C24 3_565 3_565 109.6(3) ?
N22 C24 C21 . 3_565 102.6(2) ?
N22 C24 H24A . . 111.3 ?
C21 C24 H24A 3_565 . 111.3 ?
N22 C24 H24B . . 111.3 ?
C21 C24 H24B 3_565 . 111.3 ?
H24A C24 H24B . . 109.2 ?
N22 C25 C26 . . 111.0(3) ?
N22 C25 H25A . . 109.4 ?
C26 C25 H25A . . 109.4 ?
N22 C25 H25B . . 109.4 ?
C26 C25 H25B . . 109.4 ?
H25A C25 H25B . . 108.0 ?
C31 C26 C27 . . 118.6(3) ?
C31 C26 C25 . . 121.9(3) ?
C27 C26 C25 . . 119.5(3) ?
C28 C27 C26 . . 120.7(4) ?
C28 C27 H27A . . 119.6 ?
C26 C27 H27A . . 119.6 ?
C27 C28 C29 . . 119.9(4) ?
C27 C28 H28A . . 120.1 ?
C29 C28 H28A . . 120.1 ?
C30 C29 C28 . . 119.7(4) ?
C30 C29 H29A . . 120.2 ?
C28 C29 H29A . . 120.2 ?
C29 C30 C31 . . 120.8(4) ?
C29 C30 H30A . . 119.6 ?
C31 C30 H30A . . 119.6 ?
C26 C31 C30 . . 120.4(4) ?
C26 C31 H31A . . 119.8 ?
C30 C31 H31A . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.338(4) yes
N1 C2 . 1.342(4) yes
N2 C5 . 1.466(4) yes
N2 C3 . 1.471(4) yes
N2 C4 3_675 1.472(4) yes
C1 C2 3_675 1.395(4) yes
C1 C4 . 1.495(4) yes
C2 C1 3_675 1.395(4) ?
C2 C3 . 1.493(5) yes
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 N2 3_675 1.472(4) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.519(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C11 . 1.375(5) ?
C6 C7 . 1.379(5) ?
C7 C8 . 1.397(5) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.374(6) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.371(5) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.376(5) ?
C10 H10A . 0.9500 ?
C11 H11A . 0.9500 ?
N21 C21 . 1.343(4) yes
N21 C22 . 1.342(4) yes
N22 C25 . 1.454(4) yes
N22 C23 . 1.470(4) yes
N22 C24 . 1.475(4) yes
C21 C22 3_565 1.389(4) yes
C21 C24 3_565 1.483(5) yes
C22 C21 3_565 1.389(4) ?
C22 C23 . 1.491(5) yes
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C21 3_565 1.483(5) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 C26 . 1.516(5) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 C31 . 1.383(5) ?
C26 C27 . 1.385(5) ?
C27 C28 . 1.384(5) ?
C27 H27A . 0.9500 ?
C28 C29 . 1.384(6) ?
C28 H28A . 0.9500 ?
C29 C30 . 1.359(6) ?
C29 H29A . 0.9500 ?
C30 C31 . 1.385(6) ?
C30 H30A . 0.9500 ?
C31 H31A . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C2 N1 C1 C2 . 3_675 -0.5(5)
C2 N1 C1 C4 . . 179.5(3)
C1 N1 C2 C1 . 3_675 0.5(5)
C1 N1 C2 C3 . . -178.8(3)
C5 N2 C3 C2 . . -156.7(3)
C4 N2 C3 C2 3_675 . -29.9(3)
N1 C2 C3 N2 . . -161.8(3)
C1 C2 C3 N2 3_675 . 18.8(3)
N1 C1 C4 N2 . 3_675 -163.0(3)
C2 C1 C4 N2 3_675 3_675 17.0(3)
C3 N2 C5 C6 . . -171.2(3)
C4 N2 C5 C6 3_675 . 65.1(4)
N2 C5 C6 C11 . . 59.6(4)
N2 C5 C6 C7 . . -120.4(4)
C11 C6 C7 C8 . . -0.3(6)
C5 C6 C7 C8 . . 179.7(3)
C6 C7 C8 C9 . . 0.5(6)
C7 C8 C9 C10 . . -1.1(6)
C8 C9 C10 C11 . . 1.5(6)
C7 C6 C11 C10 . . 0.7(5)
C5 C6 C11 C10 . . -179.3(3)
C9 C10 C11 C6 . . -1.3(6)
C21 N21 C22 C21 . 3_565 0.0(5)
C21 N21 C22 C23 . . 178.5(3)
C25 N22 C23 C22 . . 156.8(3)
C24 N22 C23 C22 . . 29.9(3)
N21 C22 C23 N22 . . 162.3(3)
C21 C22 C23 N22 3_565 . -19.1(3)
C22 N21 C21 C22 . 3_565 0.0(5)
C22 N21 C21 C24 . 3_565 179.9(3)
C25 N22 C24 C21 . 3_565 -156.0(3)
C23 N22 C24 C21 . 3_565 -29.2(3)
C23 N22 C25 C26 . . 173.6(3)
C24 N22 C25 C26 . . -63.2(4)
N22 C25 C26 C31 . . 119.1(4)
N22 C25 C26 C27 . . -60.3(4)
C31 C26 C27 C28 . . -1.1(5)
C25 C26 C27 C28 . . 178.3(3)
C26 C27 C28 C29 . . 0.5(6)
C27 C28 C29 C30 . . 0.3(6)
C28 C29 C30 C31 . . -0.4(6)
C27 C26 C31 C30 . . 1.0(5)
C25 C26 C31 C30 . . -178.4(3)
C29 C30 C31 C26 . . -0.3(6)
