#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180097 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/43/7054367.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_7054367
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         'C21 H18 N6'
_chemical_formula_sum            'C21 H18 N6'
_chemical_formula_weight         354.42
_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                 122.157(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.140(4)
_cell_length_b                   5.5409(5)
_cell_length_c                   13.9897(17)
_cell_measurement_temperature    150
_cell_volume                     1649.8(5)
_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)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9785
_diffrn_measured_fraction_theta_max 0.9779
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2878
_diffrn_reflns_theta_full        70.3768
_diffrn_reflns_theta_max         70.38
_diffrn_reflns_theta_min         4.15
_exptl_absorpt_coefficient_mu    0.712
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4268
_exptl_crystal_description       needle
_exptl_crystal_F_000             746.1955
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.2321
_refine_diff_density_min         -0.2986
_refine_diff_density_rms         0.0582
_refine_ls_d_res_high            0.8185
_refine_ls_d_res_low             10.6416
_refine_ls_goodness_of_fit_ref   1.0401
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0401
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+0.7096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              25
_reflns_limit_h_min              -30
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1281
_reflns_number_total             1547
_reflns_threshold_expression     I>=2u(I)
_cod_duplicate_entry             7054205
_cod_data_source_file            c4nj00351a2.cif
_cod_data_source_block           4
_cod_database_code               7054367
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H1a(0.5) H1b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C5(H5), C9(H9), C10(H10), C11(H11)
;
#END Tags that were not found in dictionaries
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
_atom_site_refinement_flags_adp
C1 C 0.500000 1.1963(4) 0.250000 0.0270(5) Uani 1.000000 S T
C2 C 0.57158(7) 0.9360(3) 0.23965(13) 0.0262(4) Uani 1.000000 . .
C3 C 0.58175(7) 0.8207(3) 0.34645(13) 0.0240(4) Uani 1.000000 . .
C4 C 0.54069(7) 0.8711(3) 0.38324(13) 0.0238(4) Uani 1.000000 . .
C5 C 0.54800(7) 0.7513(3) 0.47731(13) 0.0269(4) Uani 1.000000 . .
C6 C 0.59689(7) 0.5890(3) 0.53714(13) 0.0270(4) Uani 1.000000 . .
C7 C 0.63810(7) 0.5423(3) 0.50149(13) 0.0250(4) Uani 1.000000 . .
C8 C 0.63027(7) 0.6548(3) 0.40655(13) 0.0245(4) Uani 1.000000 . .
C9 C 0.75030(7) 0.4114(3) 0.59750(13) 0.0281(4) Uani 1.000000 . .
C10 C 0.74566(8) 0.0694(3) 0.66228(14) 0.0309(4) Uani 1.000000 . .
C11 C 0.68606(8) 0.1559(3) 0.60574(14) 0.0290(4) Uani 1.000000 . .
N1 N 0.50861(6) 1.0473(2) 0.17260(11) 0.0253(3) Uani 1.000000 . .
N2 N 0.68889(6) 0.3769(2) 0.56369(11) 0.0262(3) Uani 1.000000 . .
N3 N 0.78622(7) 0.2297(3) 0.65782(12) 0.0318(4) Uani 1.000000 . .
H8 H 0.65811(7) 0.6188(3) 0.38205(13) 0.0294(4) Uiso 1.000000 R .
H6 H 0.60222(7) 0.5102(3) 0.60201(13) 0.0324(5) Uiso 1.000000 R .
H5 H 0.51929(7) 0.7810(3) 0.50050(13) 0.0323(5) Uiso 1.000000 R .
H1a H 0.462807 1.3014(4) 0.205769 0.0324(6) Uiso 0.500000 R .
H1b H 0.537193 1.3014(4) 0.294231 0.0324(6) Uiso 0.500000 R .
H2a H 0.60407(7) 1.0610(3) 0.25991(13) 0.0315(5) Uiso 1.000000 R .
H2b H 0.57611(7) 0.8119(3) 0.19354(13) 0.0315(5) Uiso 1.000000 R .
H9 H 0.76534(7) 0.5506(3) 0.57949(13) 0.0337(5) Uiso 1.000000 R .
H10 H 0.75787(8) -0.0818(3) 0.70002(14) 0.0371(5) Uiso 1.000000 R .
H11 H 0.64985(8) 0.0798(3) 0.59698(14) 0.0348(5) Uiso 1.000000 R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
N1 C1 N1 111.45(18) . 2_655
N1 C2 C3 111.27(12) . .
C4 C3 C2 120.39(14) . .
C8 C3 C2 120.39(14) . .
C8 C3 C4 119.16(14) . .
C5 C4 C3 119.80(15) . .
N1 C4 C3 121.66(14) 2_655 .
N1 C4 C5 118.53(14) 2_655 .
C6 C5 C4 120.45(15) . .
C7 C6 C5 119.57(15) . .
C8 C7 C6 120.50(14) . .
N2 C7 C6 119.65(14) . .
N2 C7 C8 119.85(14) . .
C7 C8 C3 120.48(14) . .
N3 C9 N2 112.26(15) . .
N3 C10 C11 111.12(15) . .
N2 C11 C10 105.73(15) . .
C2 N1 C1 107.18(10) . 2_655
C4 N1 C1 111.09(11) 2_655 2_655
C4 N1 C2 112.59(12) 2_655 .
C9 N2 C7 126.85(14) . .
C11 N2 C7 126.70(14) . .
C11 N2 C9 106.39(14) . .
C10 N3 C9 104.50(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.4667(18) .
C1 N1 1.4667(18) 2_655
C2 C3 1.516(2) .
C2 N1 1.4782(19) .
C3 C4 1.405(2) .
C3 C8 1.396(2) .
C4 C5 1.396(2) .
C4 N1 1.4381(19) 2_655
C5 C6 1.387(2) .
C6 C7 1.392(2) .
C7 C8 1.383(2) .
C7 N2 1.4300(19) .
C9 N2 1.366(2) .
C9 N3 1.315(2) .
C10 C11 1.356(2) .
C10 N3 1.378(2) .
C11 N2 1.377(2) .
