#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:47:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180096 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/42/7054203.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_7054203
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, H2 O'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2013-11-08
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.436(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8104(4)
_cell_length_b                   9.7998(2)
_cell_length_c                   15.3326(4)
_cell_measurement_temperature    150
_cell_volume                     1766.05(9)
_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      150.15
_diffrn_measured_fraction_theta_full 0.980224
_diffrn_measured_fraction_theta_max 0.980224
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6629
_diffrn_reflns_theta_full        70.711752
_diffrn_reflns_theta_max         70.71
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4006
_exptl_crystal_description       needle
_exptl_crystal_F_000             786.4025
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.264012
_refine_diff_density_min         -0.265748
_refine_diff_density_rms         0.056071
_refine_ls_d_res_high            0.816766
_refine_ls_d_res_low             11.753533
_refine_ls_goodness_of_fit_ref   1.052801
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052801
_refine_ls_R_factor_all          0.044808
_refine_ls_R_factor_gt           0.040048
_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)+(0.0581P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.107918
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2957
_reflns_number_total             3321
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4nj00351a2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7054203--7054208.cif.'
_cod_original_cell_volume        1766.04(9)
_cod_database_code               7054203
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
C1 C 1.11583(12) 0.14952(15) 0.32054(9) 0.0292(3) Uani 1.000000 .
H1 H 1.10317(12) 0.24368(15) 0.32742(9) 0.0350(4) Uiso 1.000000 R
C2 C 1.11393(12) -0.05035(15) 0.25429(10) 0.0306(3) Uani 1.000000 .
H2 H 1.10147(12) -0.12244(15) 0.20984(10) 0.0368(4) Uiso 1.000000 R
C3 C 1.16892(13) -0.05750(15) 0.35064(10) 0.0336(3) Uani 1.000000 .
H3 H 1.20248(13) -0.13792(15) 0.38492(10) 0.0403(4) Uiso 1.000000 R
C4 C 1.02565(11) 0.14598(14) 0.14342(9) 0.0252(3) Uani 1.000000 .
C5 C 1.08121(11) 0.25241(14) 0.12028(10) 0.0275(3) Uani 1.000000 .
H5 H 1.15415(11) 0.28068(14) 0.16417(10) 0.0330(4) Uiso 1.000000 R
C6 C 1.03053(12) 0.31783(15) 0.03313(10) 0.0302(3) Uani 1.000000 .
H6 H 1.06899(12) 0.38983(15) 0.01671(10) 0.0362(4) Uiso 1.000000 R
C7 C 0.92357(12) 0.27720(14) -0.02953(10) 0.0287(3) Uani 1.000000 .
H7 H 0.88860(12) 0.32239(14) -0.08896(10) 0.0345(4) Uiso 1.000000 R
C8 C 0.86604(11) 0.17091(14) -0.00699(9) 0.0249(3) Uani 1.000000 .
C9 C 0.74466(11) 0.13785(14) -0.07377(9) 0.0268(3) Uani 1.000000 .
H9a H 0.70127(18) 0.2240(3) -0.0936(7) 0.0322(4) Uiso 1.000000 R
H9b H 0.7456(5) 0.0911(8) -0.1307(4) 0.0322(4) Uiso 1.000000 R
C10 C 0.65264(11) 0.12334(13) 0.03613(9) 0.0255(3) Uani 1.000000 .
C11 C 0.71195(11) 0.11204(14) 0.13468(9) 0.0269(3) Uani 1.000000 .
C12 C 0.81804(12) 0.02614(15) 0.17592(10) 0.0287(3) Uani 1.000000 .
H12a H 0.87695(12) 0.0766(9) 0.2285(5) 0.0344(4) Uiso 1.000000 R
H12b H 0.8011(7) -0.0581(4) 0.2035(7) 0.0344(4) Uiso 1.000000 R
C13 C 0.91783(11) 0.10188(13) 0.07967(9) 0.0240(3) Uani 1.000000 .
C14 C 0.76659(11) -0.06078(14) 0.02037(10) 0.0275(3) Uani 1.000000 .
H14a H 0.7952(4) -0.1040(10) -0.02421(13) 0.0330(4) Uiso 1.000000 R
H14b H 0.7256(2) -0.1320(8) 0.0401(5) 0.0330(4) Uiso 1.000000 R
C15 C 0.55606(12) 0.20805(14) 0.00097(10) 0.0289(3) Uani 1.000000 .
C16 C 0.52020(13) 0.27882(15) 0.06233(11) 0.0351(3) Uani 1.000000 .
H16 H 0.45515(13) 0.33616(15) 0.03768(11) 0.0422(4) Uiso 1.000000 R
C17 C 0.57978(13) 0.26568(16) 0.16029(11) 0.0370(4) Uani 1.000000 .
H17 H 0.55549(13) 0.31412(16) 0.20255(11) 0.0445(4) Uiso 1.000000 R
C18 C 0.67387(12) 0.18237(15) 0.19561(10) 0.0324(3) Uani 1.000000 .
H18 H 0.71348(12) 0.17258(15) 0.26242(10) 0.0389(4) Uiso 1.000000 R
C19 C 0.45278(12) 0.12288(15) -0.16503(10) 0.0296(3) Uani 1.000000 .
H19 H 0.47263(12) 0.02935(15) -0.15260(10) 0.0356(4) Uiso 1.000000 R
C20 C 0.44455(14) 0.34363(17) -0.14457(13) 0.0433(4) Uani 1.000000 .
H20 H 0.45550(14) 0.43233(17) -0.11738(13) 0.0519(5) Uiso 1.000000 R
C21 C 0.38005(13) 0.31008(18) -0.23500(12) 0.0438(4) Uani 1.000000 .
H21 H 0.33758(13) 0.37317(18) -0.28307(12) 0.0525(5) Uiso 1.000000 R
H1a H 0.3242(18) 0.051(2) 0.6365(16) 0.058(6) Uiso 1.000000 .
H1b H 0.2657(18) 0.035(2) 0.5340(16) 0.060(6) Uiso 1.000000 .
N1 N 1.16926(11) 0.06776(13) 0.39164(8) 0.0339(3) Uani 1.000000 .
N2 N 1.08026(9) 0.08360(12) 0.23506(8) 0.0259(3) Uani 1.000000 .
N3 N 0.86332(9) -0.01085(11) 0.10431(8) 0.0262(3) Uani 1.000000 .
N4 N 0.68764(9) 0.04917(11) -0.02844(8) 0.0255(3) Uani 1.000000 .
N5 N 0.49178(10) 0.22342(12) -0.09899(8) 0.0299(3) Uani 1.000000 .
N6 N 0.38401(10) 0.17083(14) -0.24853(9) 0.0362(3) Uani 1.000000 .
O1 O 0.30331(12) -0.01126(13) 0.58840(9) 0.0523(3) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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)'
O 0.05239 0.03377 '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
N1 C1 H1 124.00(8)
N2 C1 H1 124.00(8)
N2 C1 N1 112.01(12)
C3 C2 H2 127.34(9)
N2 C2 H2 127.34(7)
N2 C2 C3 105.32(12)
H3 C3 C2 124.60(9)
N1 C3 C2 110.81(13)
N1 C3 H3 124.60(8)
C13 C4 C5 121.06(12)
N2 C4 C5 118.14(12)
N2 C4 C13 120.79(12)
H5 C5 C4 119.91(8)
C6 C5 C4 120.17(13)
C6 C5 H5 119.91(8)
H6 C6 C5 120.31(8)
C7 C6 C5 119.37(13)
C7 C6 H6 120.31(8)
H7 C7 C6 119.42(8)
C8 C7 C6 121.17(13)
C8 C7 H7 119.42(8)
C9 C8 C7 119.47(12)
C13 C8 C7 119.84(12)
C13 C8 C9 120.56(12)
H9a C9 C8 108.9(3)
H9b C9 C8 108.9(3)
H9b C9 H9a 109.0(13)
N4 C9 C8 111.98(11)
N4 C9 H9a 108.9(3)
N4 C9 H9b 108.9(3)
C15 C10 C11 118.50(12)
N4 C10 C11 121.33(12)
N4 C10 C15 120.16(12)
C12 C11 C10 120.57(12)
C18 C11 C10 119.95(13)
C18 C11 C12 119.46(12)
H12a C12 C11 109.3(3)
H12b C12 C11 109.3(3)
H12b C12 H12a 107.1(13)
N3 C12 C11 112.37(11)
N3 C12 H12a 109.3(3)
N3 C12 H12b 109.3(3)
C8 C13 C4 118.35(12)
N3 C13 C4 119.99(11)
N3 C13 C8 121.66(11)
H14b C14 H14a 107.2(13)
N3 C14 H14a 109.4(3)
N3 C14 H14b 109.4(3)
N4 C14 H14a 109.4(3)
N4 C14 H14b 109.4(3)
N4 C14 N3 111.90(11)
C16 C15 C10 120.90(13)
N5 C15 C10 121.09(12)
N5 C15 C16 118.01(13)
H16 C16 C15 120.07(9)
C17 C16 C15 119.86(14)
C17 C16 H16 120.07(9)
H17 C17 C16 120.09(9)
C18 C17 C16 119.83(13)
C18 C17 H17 120.09(9)
C17 C18 C11 120.94(14)
H18 C18 C11 119.53(9)
H18 C18 C17 119.53(9)
N5 C19 H19 124.11(8)
N6 C19 H19 124.11(9)
N6 C19 N5 111.79(13)
C21 C20 H20 126.88(10)
N5 C20 H20 126.88(9)
N5 C20 C21 106.24(14)
H21 C21 C20 124.69(10)
N6 C21 C20 110.61(14)
N6 C21 H21 124.69(8)
C3 N1 C1 105.08(12)
C2 N2 C1 106.79(11)
C4 N2 C1 125.80(12)
C4 N2 C2 127.28(11)
C13 N3 C12 112.52(11)
C14 N3 C12 106.80(10)
C14 N3 C13 110.76(10)
C10 N4 C9 112.06(10)
C14 N4 C9 107.68(10)
C14 N4 C10 111.21(10)
C19 N5 C15 127.38(12)
C20 N5 C15 125.59(13)
C20 N5 C19 106.53(12)
C21 N6 C19 104.83(13)
H1b O1 H1a 106.9(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1 0.9500
C1 N1 1.3059(19)
C1 N2 1.3666(17)
C2 H2 0.9500
C2 C3 1.362(2)
C2 N2 1.3765(18)
C3 H3 0.9500
C3 N1 1.3784(19)
C4 C5 1.3860(19)
C4 C13 1.4057(18)
C4 N2 1.4338(17)
C5 H5 0.9500
C5 C6 1.3885(19)
C6 H6 0.9500
C6 C7 1.383(2)
C7 H7 0.9500
C7 C8 1.3964(19)
C8 C9 1.5181(18)
C8 C13 1.4007(18)
C9 H9a 0.9900
C9 H9b 0.9900
C9 N4 1.4751(17)
C10 C11 1.3999(19)
C10 C15 1.4071(19)
C10 N4 1.4361(17)
C11 C12 1.5073(19)
C11 C18 1.3957(19)
C12 H12a 0.9900
C12 H12b 0.9900
C12 N3 1.4764(17)
C13 N3 1.4355(17)
C14 H14a 0.9900
C14 H14b 0.9900
C14 N3 1.4707(17)
C14 N4 1.4635(17)
C15 C16 1.386(2)
C15 N5 1.4303(18)
C16 H16 0.9500
C16 C17 1.394(2)
C17 H17 0.9500
C17 C18 1.376(2)
C18 H18 0.9500
C19 H19 0.9500
C19 N5 1.3577(18)
C19 N6 1.3186(18)
C20 H20 0.9500
C20 C21 1.342(2)
C20 N5 1.381(2)
C21 H21 0.9500
C21 N6 1.384(2)
H1a O1 0.91(2)
H1b O1 0.90(2)
