#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180097 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/43/7054369.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_7054369
loop_
_publ_author_name
'Sathyanarayana, Arruri'
'Prabusankar, Ganesan'
_publ_section_title
;
 Facile access to imidazole and imidazolium substituted dibenzo-diazocines
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3613
_journal_paper_doi               10.1039/C4NJ00351A
_journal_volume                  38
_journal_year                    2014
_chemical_formula_moiety         '0.5(C54 H64 N12), 0.25(I8)'
_chemical_formula_sum            'C27 H32 I2 N6'
_chemical_formula_weight         694.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2014-04-20
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.629(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1807(5)
_cell_length_b                   13.9648(7)
_cell_length_c                   20.5397(9)
_cell_measurement_temperature    150
_cell_volume                     2860.2(2)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.979378
_diffrn_measured_fraction_theta_max 0.979378
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5536
_diffrn_reflns_theta_full        70.692082
_diffrn_reflns_theta_max         70.69
_diffrn_reflns_theta_min         4.40
_exptl_absorpt_coefficient_mu    17.468
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6125
_exptl_crystal_description       needle
_exptl_crystal_F_000             1370.2893
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.710422
_refine_diff_density_min         -0.763886
_refine_diff_density_rms         0.120288
_refine_ls_d_res_high            0.816864
_refine_ls_d_res_low             10.059025
_refine_ls_goodness_of_fit_ref   1.020541
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020541
_refine_ls_R_factor_all          0.041248
_refine_ls_R_factor_gt           0.032518
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0392P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.083808
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2283
_reflns_number_total             2707
_reflns_threshold_expression     I>=2u(I)
_cod_duplicate_entry             7054207
_cod_data_source_file            c4nj00351a2.cif
_cod_data_source_block           6
_cod_database_code               7054369
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 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_refinement_flags_posn
N2 N 0.5837(3) 0.3075(2) 0.43799(15) 0.0299(7) Uani 1.000000 .
C4 C 0.5540(4) 0.3656(3) 0.48513(18) 0.0328(9) Uani 1.000000 .
H4 H 0.5642(4) 0.4332(3) 0.48635(18) 0.0394(10) Uiso 1.000000 R
C13 C 0.500000 0.1720(4) 0.250000 0.0354(13) Uani 1.000000 S
H13a H 0.581(3) 0.132(3) 0.2597(3) 0.0425(16) Uiso 0.500000 R
H13b H 0.419(3) 0.132(3) 0.2403(3) 0.0425(16) Uiso 0.500000 R
N3 N 0.4953(4) 0.2316(2) 0.30861(15) 0.0324(7) Uani 1.000000 .
C11 C 0.3291(4) 0.3274(3) 0.22903(19) 0.0325(9) Uani 1.000000 .
C5 C 0.5076(4) 0.2189(3) 0.51098(19) 0.0343(9) Uani 1.000000 .
H5 H 0.4795(4) 0.1662(3) 0.53403(19) 0.0412(11) Uiso 1.000000 R
C6 C 0.5545(4) 0.2148(3) 0.45389(19) 0.0346(9) Uani 1.000000 .
H6 H 0.5653(4) 0.1587(3) 0.42933(19) 0.0415(11) Uiso 1.000000 R
C12 C 0.6033(4) 0.2988(3) 0.32034(18) 0.0303(8) Uani 1.000000 .
C7 C 0.6448(4) 0.3397(3) 0.38417(18) 0.0290(8) Uani 1.000000 .
C2 C 0.4629(5) 0.3535(3) 0.5884(2) 0.0384(10) Uani 1.000000 .
H2 H 0.4761(5) 0.4244(3) 0.5886(2) 0.0461(12) Uiso 1.000000 R
C8 C 0.2562(4) 0.4090(3) 0.1027(2) 0.0357(9) Uani 1.000000 .
H8 H 0.2312(4) 0.4361(3) 0.0596(2) 0.0429(11) Uiso 1.000000 R
N1 N 0.5083(3) 0.3138(2) 0.52944(16) 0.0324(7) Uani 1.000000 .
C3 C 0.3160(5) 0.3344(4) 0.5818(2) 0.0508(13) Uani 1.000000 .
H3a H 0.2672(6) 0.360(2) 0.5394(8) 0.0762(19) Uiso 1.000000 G
H3b H 0.3008(6) 0.2652(4) 0.5831(17) 0.0762(19) Uiso 1.000000 G
H3c H 0.2840(9) 0.365(2) 0.6185(10) 0.0762(19) Uiso 1.000000 G
C10 C 0.2296(4) 0.3971(3) 0.2159(2) 0.0379(9) Uani 1.000000 .
H10 H 0.1856(4) 0.4168(3) 0.2503(2) 0.0455(11) Uiso 1.000000 R
C1 C 0.5484(6) 0.3135(4) 0.6514(2) 0.0591(15) Uani 1.000000 .
H1a H 0.532(3) 0.2445(7) 0.6538(10) 0.089(2) Uiso 1.000000 G
H1b H 0.6433(6) 0.325(3) 0.6511(9) 0.089(2) Uiso 1.000000 G
H1c H 0.525(3) 0.345(2) 0.6900(2) 0.089(2) Uiso 1.000000 G
C14 C 0.3651(4) 0.2805(3) 0.29745(19) 0.0343(9) Uani 1.000000 .
H14a H 0.2946(7) 0.2335(12) 0.3019(12) 0.0412(11) Uiso 1.000000 R
H14b H 0.367(2) 0.3301(11) 0.3320(5) 0.0412(11) Uiso 1.000000 R
C9 C 0.1937(4) 0.4382(3) 0.1538(2) 0.0377(9) Uani 1.000000 .
H9 H 0.1265(4) 0.4864(3) 0.1459(2) 0.0453(11) Uiso 1.000000 R
I1 I 0.28969(3) 0.024687(19) 0.594103(13) 0.03896(11) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I -0.19206 6.94430 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
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
C6 N2 C4 107.7(3) . .
C7 N2 C4 123.9(3) . .
C7 N2 C6 128.2(3) . .
H4 C4 N2 125.4(2) . .
N1 C4 N2 109.2(4) . .
N1 C4 H4 125.4(2) . .
H13a C13 H13a 110(5) . 2_655
H13b C13 H13a 0.0 2_655 .
H13b C13 H13a 110(5) 2_655 2_655
H13b C13 H13a 110(5) . .
H13b C13 H13a 0.0 . 2_655
H13b C13 H13b 110(5) 2_655 .
N3 C13 H13a 108.8(13) 2_655 2_655
N3 C13 H13a 108.8(13) 2_655 .
N3 C13 H13a 108.8(13) . .
N3 C13 H13a 108.8(13) . 2_655
N3 C13 H13b 108.8(13) 2_655 .
N3 C13 H13b 108.8(13) 2_655 2_655
N3 C13 H13b 108.8(13) . .
N3 C13 H13b 108.8(13) . 2_655
N3 C13 N3 111.1(5) 2_655 .
C12 N3 C13 111.0(3) . .
C14 N3 C13 108.2(3) . .
C14 N3 C12 111.2(3) . .
C10 C11 C12 120.4(4) . 2_655
C14 C11 C12 119.0(4) . 2_655
C14 C11 C10 120.6(4) . .
C6 C5 H5 126.4(2) . .
N1 C5 H5 126.4(2) . .
N1 C5 C6 107.2(3) . .
C5 C6 N2 107.2(3) . .
H6 C6 N2 126.4(2) . .
H6 C6 C5 126.4(2) . .
C11 C12 N3 122.8(3) 2_655 .
C7 C12 N3 119.8(3) . .
C7 C12 C11 117.4(4) . 2_655
C12 C7 N2 119.3(4) . .
C8 C7 N2 118.5(3) 2_655 .
C8 C7 C12 122.2(4) 2_655 .
N1 C2 H2 108.0(2) . .
C3 C2 H2 108.0(2) . .
C3 C2 N1 109.2(4) . .
C1 C2 H2 108.0(3) . .
C1 C2 N1 109.8(4) . .
C1 C2 C3 113.8(4) . .
H8 C8 C7 120.6(2) . 2_655
C9 C8 C7 118.9(4) . 2_655
C9 C8 H8 120.6(3) . .
C5 N1 C4 108.7(3) . .
C2 N1 C4 124.6(3) . .
C2 N1 C5 126.7(3) . .
H3a C3 C2 109.5 . .
H3b C3 C2 109.5 . .
H3b C3 H3a 109.5 . .
H3c C3 C2 109.5 . .
H3c C3 H3a 109.5 . .
H3c C3 H3b 109.5 . .
H10 C10 C11 119.4(2) . .
C9 C10 C11 121.2(4) . .
C9 C10 H10 119.4(3) . .
H1a C1 C2 109.5 . .
H1b C1 C2 109.5 . .
H1b C1 H1a 109.5 . .
H1c C1 C2 109.5 . .
H1c C1 H1a 109.5 . .
H1c C1 H1b 109.5 . .
C11 C14 N3 112.7(3) . .
H14a C14 N3 109.0(9) . .
H14a C14 C11 109.0(9) . .
H14b C14 N3 109.0(9) . .
H14b C14 C11 109.0(9) . .
H14b C14 H14a 108(4) . .
C10 C9 C8 119.9(4) . .
H9 C9 C8 120.1(3) . .
H9 C9 C10 120.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C4 1.343(5) .
N2 C6 1.382(5) .
N2 C7 1.445(5) .
C4 H4 0.9500 .
C4 N1 1.318(5) .
C13 H13a 0.9900 .
C13 H13a 0.9900 2_655
C13 H13b 0.9900 2_655
C13 H13b 0.9900 .
C13 N3 1.473(4) 2_655
C13 N3 1.473(4) .
H13a H13b 0.0000 2_655
N3 C12 1.429(5) .
N3 C14 1.467(5) .
C11 C12 1.394(5) 2_655
C11 C10 1.391(6) .
C11 C14 1.527(5) .
C5 H5 0.9500 .
C5 C6 1.353(5) .
C5 N1 1.378(5) .
C6 H6 0.9500 .
C12 C7 1.414(5) .
C7 C8 1.384(6) 2_655
C2 H2 1.0000 .
C2 N1 1.487(5) .
C2 C3 1.498(7) .
C2 C1 1.514(6) .
C8 H8 0.9500 .
C8 C9 1.394(6) .
C3 H3a 0.9800 .
C3 H3b 0.9800 .
C3 H3c 0.9800 .
C10 H10 0.9500 .
C10 C9 1.378(6) .
C1 H1a 0.9800 .
C1 H1b 0.9800 .
C1 H1c 0.9800 .
C14 H14a 0.9900 .
C14 H14b 0.9900 .
C9 H9 0.9500 .
