#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/13/7051369.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_7051369
loop_
_publ_author_name
'Pal, Pankaj K.'
'Chowdhury, Shubhamoy'
'Drew, Michael G. B.'
'Datta, Dipankar'
_publ_section_title
;
 Metal-assisted electrocyclic reaction in a
 CN--NC--CN system
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              931
_journal_paper_doi               10.1039/b006547l
_journal_volume                  24
_journal_year                    2000
_chemical_formula_sum            'C26 H20 N6'
_chemical_formula_weight         416.48
_chemical_name_systematic
;
 ?
;
_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                 105.800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.404(14)
_cell_length_b                   18.94(2)
_cell_length_c                   11.673(14)
_cell_measurement_temperature    293(2)
_cell_volume                     2213(5)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1991)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,1994)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2^o intervals, counting time 2 min.'
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7894
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1349P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.2214
_reflns_number_gt                2576
_reflns_number_total             4337
_reflns_threshold_expression     2sigma(I)
_cod_data_source_file            b006547l.txt
_cod_data_source_block           L
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 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^2^)+(0.1349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C26 H20 N6 '
_cod_database_code               7051369
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_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5387(2) 0.11859(12) 0.4437(2) 0.0512(6) Uani 1 d . . .
C2 C 0.5386(2) 0.13843(11) 0.3183(2) 0.0504(6) Uani 1 d . . .
N3 N 0.6153(2) 0.06998(10) 0.50286(18) 0.0576(6) Uani 1 d . . .
N4 N 0.6921(2) 0.03859(11) 0.43372(19) 0.0628(6) Uani 1 d . . .
C5 C 0.7720(3) -0.00838(12) 0.4897(2) 0.0574(6) Uani 1 d . . .
H5 H 0.7765 -0.0177 0.5689 0.069 Uiso 1 calc R . .
N6 N 0.6033(2) 0.19313(11) 0.29756(18) 0.0557(5) Uani 1 d . . .
N7 N 0.6689(2) 0.22904(10) 0.40329(18) 0.0594(6) Uani 1 d . . .
C8 C 0.7492(3) 0.27558(12) 0.3889(2) 0.0572(6) Uani 1 d . . .
H8 H 0.7564 0.2849 0.3126 0.069 Uiso 1 calc R . .
C11 C 0.8568(3) -0.04795(12) 0.4314(2) 0.0572(6) Uani 1 d . . .
C12 C 0.8477(3) -0.04008(16) 0.3114(3) 0.0746(8) Uani 1 d . . .
H12 H 0.7874 -0.0082 0.2650 0.090 Uiso 1 calc R . .
C13 C 0.9294(4) -0.08025(19) 0.2620(3) 0.0901(10) Uani 1 d . . .
H13 H 0.9246 -0.0762 0.1815 0.108 Uiso 1 calc R . .
C14 C 1.0174(3) -0.12598(18) 0.3327(3) 0.0888(10) Uani 1 d . . .
H14 H 1.0727 -0.1541 0.3012 0.107 Uiso 1 calc R . .
C15 C 1.0226(3) -0.12968(16) 0.4511(4) 0.0870(10) Uani 1 d . . .
H15 H 1.0851 -0.1599 0.4990 0.104 Uiso 1 calc R . .
N16 N 0.9437(2) -0.09269(12) 0.5023(2) 0.0703(7) Uani 1 d . . .
C21 C 0.4627(2) 0.09488(12) 0.2179(2) 0.0528(6) Uani 1 d . . .
C22 C 0.4526(3) 0.11407(15) 0.1002(2) 0.0647(7) Uani 1 d . . .
H22 H 0.4935 0.1551 0.0841 0.078 Uiso 1 calc R . .
C23 C 0.4000(3) 0.03343(13) 0.2384(2) 0.0645(7) Uani 1 d . . .
H23 H 0.4061 0.0198 0.3163 0.077 Uiso 1 calc R . .
C24 C 0.3818(3) 0.07213(17) 0.0079(3) 0.0767(8) Uani 1 d . . .
H24 H 0.3754 0.0852 -0.0702 0.092 Uiso 1 calc R . .
C25 C 0.3283(3) -0.00816(15) 0.1448(3) 0.0767(8) Uani 1 d . . .
H25 H 0.2857 -0.0489 0.1598 0.092 Uiso 1 calc R . .
C26 C 0.3207(3) 0.01121(16) 0.0299(3) 0.0778(9) Uani 1 d . . .
H26 H 0.2742 -0.0169 -0.0332 0.093 Uiso 1 calc R . .
C36 C 0.4580(3) 0.15146(14) 0.6200(2) 0.0670(7) Uani 1 d . . .
H36 H 0.5261 0.1242 0.6679 0.080 Uiso 1 calc R . .
C32 C 0.3419(3) 0.19692(14) 0.4286(3) 0.0668(7) Uani 1 d . . .
H32 H 0.3317 0.2006 0.3471 0.080 Uiso 1 calc R . .
C33 C 0.2539(3) 0.23182(16) 0.4793(3) 0.0804(9) Uani 1 d . . .
H33 H 0.1845 0.2586 0.4320 0.096 Uiso 1 calc R . .
C34 C 0.2698(3) 0.22667(16) 0.6003(3) 0.0809(9) Uani 1 d . . .
H34 H 0.2118 0.2505 0.6349 0.097 Uiso 1 calc R . .
C35 C 0.3708(4) 0.18650(15) 0.6694(3) 0.0789(9) Uani 1 d . . .
H35 H 0.3804 0.1829 0.7507 0.095 Uiso 1 calc R . .
C31 C 0.4450(3) 0.15653(12) 0.4983(2) 0.0534(6) Uani 1 d . . .
C41 C 0.8325(3) 0.31581(12) 0.4907(2) 0.0548(6) Uani 1 d . . .
N42 N 0.9331(3) 0.35147(14) 0.4676(2) 0.0806(7) Uani 1 d . . .
C43 C 1.0149(4) 0.38557(19) 0.5597(3) 0.0968(11) Uani 1 d . . .
H43 H 1.0877 0.4093 0.5465 0.116 Uiso 1 calc R . .
C44 C 0.9979(4) 0.38775(18) 0.6730(3) 0.0893(10) Uani 1 d . . .
H44 H 1.0572 0.4124 0.7339 0.107 Uiso 1 calc R . .
C45 C 0.8919(4) 0.35270(18) 0.6924(3) 0.0881(10) Uani 1 d . . .
H45 H 0.8763 0.3537 0.7671 0.106 Uiso 1 calc R . .
C46 C 0.8081(3) 0.31580(15) 0.6009(2) 0.0705(8) Uani 1 d . . .
H46 H 0.7357 0.2911 0.6131 0.085 Uiso 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 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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C31 119.9(2) . . ?
N3 C1 C2 122.3(2) . . ?
C31 C1 C2 117.9(2) . . ?
N6 C2 C21 119.5(2) . . ?
N6 C2 C1 121.1(2) . . ?
C21 C2 C1 119.3(2) . . ?
C1 N3 N4 111.0(2) . . ?
C5 N4 N3 113.2(2) . . ?
N4 C5 C11 120.9(2) . . ?
C2 N6 N7 112.0(2) . . ?
C8 N7 N6 113.7(2) . . ?
N7 C8 C41 121.3(2) . . ?
N16 C11 C12 122.6(3) . . ?
N16 C11 C5 115.2(2) . . ?
C12 C11 C5 122.2(2) . . ?
C13 C12 C11 118.9(3) . . ?
C14 C13 C12 119.1(3) . . ?
C13 C14 C15 118.6(3) . . ?
N16 C15 C14 124.3(3) . . ?
C15 N16 C11 116.5(3) . . ?
C23 C21 C22 118.4(2) . . ?
C23 C21 C2 120.5(2) . . ?
C22 C21 C2 121.1(2) . . ?
C24 C22 C21 120.0(3) . . ?
C21 C23 C25 121.1(3) . . ?
C26 C24 C22 120.9(3) . . ?
C26 C25 C23 119.6(3) . . ?
C25 C26 C24 120.0(3) . . ?
C35 C36 C31 120.2(3) . . ?
C33 C32 C31 120.5(3) . . ?
C34 C33 C32 119.6(3) . . ?
C35 C34 C33 120.1(3) . . ?
C34 C35 C36 120.7(3) . . ?
C32 C31 C36 118.8(2) . . ?
C32 C31 C1 120.5(2) . . ?
C36 C31 C1 120.7(2) . . ?
N42 C41 C46 122.9(2) . . ?
N42 C41 C8 114.8(2) . . ?
C46 C41 C8 122.3(2) . . ?
C41 N42 C43 116.3(3) . . ?
N42 C43 C44 124.3(3) . . ?
C45 C44 C43 117.8(3) . . ?
C44 C45 C46 119.5(3) . . ?
C45 C46 C41 119.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.288(3) . ?
C1 C31 1.488(4) . ?
C1 C2 1.512(4) . ?
C2 N6 1.293(3) . ?
C2 C21 1.474(3) . ?
N3 N4 1.413(3) . ?
N4 C5 1.270(3) . ?
C5 C11 1.459(4) . ?
N6 N7 1.411(3) . ?
N7 C8 1.258(3) . ?
C8 C41 1.477(4) . ?
C11 N16 1.347(3) . ?
C11 C12 1.386(4) . ?
C12 C13 1.379(4) . ?
C13 C14 1.363(5) . ?
C14 C15 1.370(5) . ?
C15 N16 1.337(4) . ?
C21 C23 1.387(4) . ?
C21 C22 1.396(4) . ?
C22 C24 1.379(4) . ?
C23 C25 1.389(4) . ?
C24 C26 1.375(5) . ?
C25 C26 1.372(5) . ?
C36 C35 1.371(4) . ?
C36 C31 1.393(4) . ?
C32 C33 1.386(4) . ?
C32 C31 1.387(4) . ?
C33 C34 1.380(5) . ?
C34 C35 1.368(5) . ?
C41 N42 1.333(4) . ?
C41 C46 1.378(4) . ?
N42 C43 1.341(4) . ?
C43 C44 1.381(5) . ?
C44 C45 1.359(5) . ?
C45 C46 1.372(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 C2 N6 -99.5(3) . . . . ?
C31 C1 C2 N6 81.4(3) . . . . ?
N3 C1 C2 C21 80.9(3) . . . . ?
C31 C1 C2 C21 -98.2(3) . . . . ?
C31 C1 N3 N4 177.50(19) . . . . ?
C2 C1 N3 N4 -1.6(3) . . . . ?
C1 N3 N4 C5 178.1(2) . . . . ?
N3 N4 C5 C11 178.2(2) . . . . ?
C21 C2 N6 N7 179.32(19) . . . . ?
C1 C2 N6 N7 -0.3(3) . . . . ?
C2 N6 N7 C8 169.4(2) . . . . ?
N6 N7 C8 C41 -176.5(2) . . . . ?
N4 C5 C11 N16 175.5(2) . . . . ?
N4 C5 C11 C12 -4.8(4) . . . . ?
N16 C11 C12 C13 0.9(4) . . . . ?
C5 C11 C12 C13 -178.8(3) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 N16 2.1(5) . . . . ?
C14 C15 N16 C11 -1.8(5) . . . . ?
C12 C11 N16 C15 0.2(4) . . . . ?
C5 C11 N16 C15 179.9(2) . . . . ?
N6 C2 C21 C23 175.7(2) . . . . ?
C1 C2 C21 C23 -4.7(3) . . . . ?
N6 C2 C21 C22 -4.0(4) . . . . ?
C1 C2 C21 C22 175.6(2) . . . . ?
C23 C21 C22 C24 -0.2(4) . . . . ?
C2 C21 C22 C24 179.5(2) . . . . ?
C22 C21 C23 C25 -0.2(4) . . . . ?
C2 C21 C23 C25 -179.9(2) . . . . ?
C21 C22 C24 C26 -0.1(4) . . . . ?
C21 C23 C25 C26 0.9(4) . . . . ?
C23 C25 C26 C24 -1.2(5) . . . . ?
C22 C24 C26 C25 0.8(5) . . . . ?
C31 C32 C33 C34 0.5(4) . . . . ?
C32 C33 C34 C35 -0.9(5) . . . . ?
C33 C34 C35 C36 0.6(4) . . . . ?
C31 C36 C35 C34 0.2(4) . . . . ?
C33 C32 C31 C36 0.3(4) . . . . ?
C33 C32 C31 C1 179.5(2) . . . . ?
C35 C36 C31 C32 -0.6(4) . . . . ?
C35 C36 C31 C1 -179.8(2) . . . . ?
N3 C1 C31 C32 -165.3(2) . . . . ?
C2 C1 C31 C32 13.8(3) . . . . ?
N3 C1 C31 C36 13.9(3) . . . . ?
C2 C1 C31 C36 -167.0(2) . . . . ?
N7 C8 C41 N42 165.6(2) . . . . ?
N7 C8 C41 C46 -13.9(4) . . . . ?
C46 C41 N42 C43 2.9(4) . . . . ?
C8 C41 N42 C43 -176.6(3) . . . . ?
C41 N42 C43 C44 -2.4(5) . . . . ?
N42 C43 C44 C45 0.4(6) . . . . ?
C43 C44 C45 C46 1.2(5) . . . . ?
C44 C45 C46 C41 -0.7(5) . . . . ?
N42 C41 C46 C45 -1.4(5) . . . . ?
C8 C41 C46 C45 178.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652880
