#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/12/7201200.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_7201200
loop_
_publ_author_name
'Dean, Pamela M.'
'Golding, Jacob J.'
'Pringle, Jennifer M.'
'Forsyth, Maria'
'Skelton, Brian W.'
'White, Allan H.'
'MacFarlane, Douglas R.'
_publ_section_title
;
 The effect of alkyl chain length in a series of novel
 N-alkyl-3-benzylimidazolium iodide salts
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2456
_journal_paper_doi               10.1039/b906142h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C13 H17 N2, I'
_chemical_formula_sum            'C13 H17 I N2'
_chemical_formula_weight         328.19
_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_date             2008-06-15T18:48:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 105.013(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            8
_cell_length_a                   18.041(2)
_cell_length_b                   11.0850(10)
_cell_length_c                   14.137(2)
_cell_measurement_reflns_used    4058
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.93
_cell_measurement_theta_min      2.46
_cell_volume                     2730.7(5)
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type
;
Bruker SMART CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  .027
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7865
_diffrn_reflns_theta_full        28.5
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  .77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Sheldrick, 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          .63
_exptl_crystal_size_mid          .5
_exptl_crystal_size_min          .12
_refine_diff_density_max         1.482
_refine_diff_density_min         -1.155
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         7865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+1.0111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                6013
_reflns_number_total             7865
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b906142h.txt
_cod_data_source_block           jak255
_cod_original_sg_symbol_Hall     -p_2ybc
_cod_original_sg_symbol_H-M      P_1_21/c_1
_cod_database_code               7201200
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.620038(11) 0.281890(19) 0.187622(15) 0.03074(7) Uani 1 1 d . . .
I2 I 0.933597(13) 0.85184(2) 0.187446(17) 0.04181(8) Uani 1 1 d . . .
C11 C 0.71394(17) 0.3540(3) 0.4828(2) 0.0295(6) Uani 1 1 d . . .
H11A H 0.7107 0.3176 0.5455 0.035 Uiso 0.797(5) 1 calc PR A 1
H11B H 0.6772 0.3108 0.4292 0.035 Uiso 0.797(5) 1 calc PR A 1
H11C H 0.6808 0.3072 0.5153 0.035 Uiso 0.203(5) 1 d PR A 2
H11D H 0.7035 0.325 0.4143 0.035 Uiso 0.203(5) 1 d PR A 2
C111 C 0.69084(16) 0.4851(3) 0.4811(2) 0.0242(6) Uani 1 1 d . A .
C112 C 0.74262(18) 0.5791(3) 0.4923(2) 0.0304(6) Uani 1 1 d . . .
H112 H 0.7957 0.562 0.5027 0.037 Uiso 1 1 calc R A .
C113 C 0.7181(2) 0.6987(3) 0.4885(3) 0.0381(8) Uani 1 1 d . A .
H113 H 0.7542 0.7626 0.4962 0.046 Uiso 1 1 calc R . .
C114 C 0.6410(2) 0.7234(3) 0.4736(3) 0.0404(8) Uani 1 1 d . . .
H114 H 0.6238 0.8047 0.47 0.049 Uiso 1 1 calc R A .
C115 C 0.5887(2) 0.6305(3) 0.4639(3) 0.0401(8) Uani 1 1 d . A .
H115 H 0.5358 0.6481 0.4545 0.048 Uiso 1 1 calc R . .
C116 C 0.61300(17) 0.5122(3) 0.4678(2) 0.0323(7) Uani 1 1 d . . .
H116 H 0.5767 0.4487 0.4615 0.039 Uiso 1 1 calc R A .
N11 N 0.79135(18) 0.3370(3) 0.4716(2) 0.0270(8) Uani 0.797(5) 1 d PD A 1
C12 C 0.8555(2) 0.3132(3) 0.5425(3) 0.0265(9) Uani 0.797(5) 1 d PD A 1
C121 C 0.8615(3) 0.3056(4) 0.6477(3) 0.0342(10) Uani 0.797(5) 1 d PD A 1
H12A H 0.9023 0.2487 0.6782 0.051 Uiso 0.797(5) 1 calc PR A 1
H12B H 0.8126 0.2775 0.6578 0.051 Uiso 0.797(5) 1 calc PR A 1
H12C H 0.8736 0.3854 0.6775 0.051 Uiso 0.797(5) 1 calc PR A 1
N13 N 0.91256(17) 0.2998(3) 0.4993(2) 0.0264(8) Uani 0.797(5) 1 d PD A 1
C14 C 0.8846(3) 0.3174(4) 0.3991(3) 0.0291(9) Uani 0.797(5) 1 d PD A 1
H14 H 0.9134 0.3138 0.3516 0.035 Uiso 0.797(5) 1 calc PR A 1
C15 C 0.8090(3) 0.3408(4) 0.3819(3) 0.0316(9) Uani 0.797(5) 1 d PD A 1
H15 H 0.7744 0.3568 0.32 0.038 Uiso 0.797(5) 1 calc PR A 1
C131 C 0.99174(18) 0.2652(3) 0.5470(2) 0.0332(7) Uani 1 1 d . . .
H13A H 1.0131 0.2213 0.499 0.04 Uiso 0.797(5) 1 calc PR A 1
H13B H 0.9913 0.2088 0.6012 0.04 Uiso 0.797(5) 1 calc PR A 1
H13F H 0.9896 0.253 0.4769 0.04 Uiso 0.203(5) 1 d PR A 2
H13G H 1.0113 0.1903 0.583 0.04 Uiso 0.203(5) 1 d PR A 2
C132 C 1.04406(19) 0.3695(4) 0.5874(3) 0.0413(8) Uani 1 1 d . A .
H13C H 1.0463 0.4247 0.5341 0.062 Uiso 1 1 calc R . .
H13D H 1.0957 0.339 0.6182 0.062 Uiso 1 1 calc R . .
H13E H 1.0242 0.4126 0.6363 0.062 Uiso 1 1 calc R . .
N31 N 0.7924(6) 0.3280(11) 0.5309(8) 0.023(3) Uiso 0.203(5) 1 d PD A 2
C32 C 0.8503(7) 0.3127(14) 0.4878(9) 0.028(3) Uiso 0.203(5) 1 d PD A 2
C321 C 0.8443(13) 0.3193(16) 0.3833(10) 0.027(4) Uiso 0.203(5) 1 d PD A 2
H32A H 0.8286 0.4008 0.3595 0.04 Uiso 0.203(5) 1 calc PR A 2
H32B H 0.8061 0.2609 0.3485 0.04 Uiso 0.203(5) 1 calc PR A 2
H32C H 0.8943 0.3006 0.3714 0.04 Uiso 0.203(5) 1 calc PR A 2
N33 N 0.9130(6) 0.2938(11) 0.5585(9) 0.025(3) Uiso 0.203(5) 1 d PD A 2
C34 C 0.8960(9) 0.2946(17) 0.6494(11) 0.033(4) Uiso 0.203(5) 1 d PD A 2
H34 H 0.9312 0.2827 0.7115 0.039 Uiso 0.203(5) 1 calc PR A 2
C35 C 0.8198(8) 0.3153(14) 0.6321(9) 0.023(3) Uiso 0.203(5) 1 d PD A 2
H35 H 0.7908 0.3203 0.6793 0.028 Uiso 0.203(5) 1 calc PR A 2
C21 C 0.7426(2) 0.9674(3) 0.2600(3) 0.0384(8) Uani 1 1 d . . .
H21A H 0.7853 0.9756 0.2284 0.046 Uiso 0.5 1 calc PR B 1
H21B H 0.7039 1.0301 0.2326 0.046 Uiso 0.5 1 calc PR B 1
H21C H 0.7341 1.0472 0.2276 0.046 Uiso 0.5 1 d PR B 2
H21D H 0.7817 0.9242 0.2351 0.046 Uiso 0.5 1 d PR B 2
C211 C 0.77231(19) 0.9850(3) 0.3690(3) 0.0336(7) Uani 1 1 d . C .
C212 C 0.7246(2) 1.0285(3) 0.4240(3) 0.0407(8) Uani 1 1 d . . .
H212 H 0.6734 1.0512 0.3922 0.049 Uiso 1 1 calc R C .
C213 C 0.7507(3) 1.0392(3) 0.5254(3) 0.0498(10) Uani 1 1 d . C .
H213 H 0.7173 1.0682 0.5623 0.06 Uiso 1 1 calc R . .
C214 C 0.8240(3) 1.0081(3) 0.5711(3) 0.0536(11) Uani 1 1 d . . .
H214 H 0.8414 1.0131 0.6405 0.064 Uiso 1 1 calc R C .
C215 C 0.8737(3) 0.9689(4) 0.5170(3) 0.0512(10) Uani 1 1 d . C .
H215 H 0.9256 0.9506 0.549 0.061 Uiso 1 1 calc R . .
C216 C 0.8475(2) 0.9565(3) 0.4163(3) 0.0432(9) Uani 1 1 d . . .
H216 H 0.8813 0.9284 0.3795 0.052 Uiso 1 1 calc R C .
N21 N 0.7053(3) 0.8391(5) 0.2377(4) 0.0217(10) Uani 0.5 1 d PD C 1
C22 C 0.6307(4) 0.8134(6) 0.2278(4) 0.0220(11) Uani 0.5 1 d PD C 1
C221 C 0.5683(5) 0.9017(8) 0.2230(7) 0.0329(18) Uani 0.5 1 d PD C 1
H22A H 0.5251 0.883 0.1668 0.049 Uiso 0.5 1 calc PR C 1
H22B H 0.5871 0.9832 0.2156 0.049 Uiso 0.5 1 calc PR C 1
H22C H 0.5513 0.8974 0.2834 0.049 Uiso 0.5 1 calc PR C 1
N23 N 0.6230(3) 0.6934(5) 0.2193(4) 0.0207(10) Uani 0.5 1 d PD C 1
C24 C 0.6933(4) 0.6419(6) 0.2242(5) 0.0238(12) Uani 0.5 1 d PD C 1
H24 H 0.7039 0.5582 0.2215 0.029 Uiso 0.5 1 calc PR C 1
C25 C 0.7440(7) 0.7328(11) 0.2334(15) 0.026(3) Uani 0.5 1 d PD C 1
H25 H 0.797 0.7252 0.2363 0.031 Uiso 0.5 1 calc PR C 1
C231 C 0.5562(3) 0.6274(3) 0.2054(3) 0.0467(9) Uani 1 1 d . . .
H23A H 0.5237 0.6673 0.2428 0.056 Uiso 0.5 1 calc PR C 1
H23B H 0.57 0.5469 0.2352 0.056 Uiso 0.5 1 calc PR C 1
H23F H 0.5935 0.5605 0.224 0.056 Uiso 0.5 1 d PR C 2
H23G H 0.523 0.6275 0.2512 0.056 Uiso 0.5 1 d PR C 2
C232 C 0.5091(2) 0.6088(4) 0.1051(3) 0.0557(11) Uani 1 1 d . C .
H23C H 0.4922 0.6871 0.075 0.084 Uiso 1 1 calc R . .
H23D H 0.4642 0.5598 0.1065 0.084 Uiso 1 1 calc R . .
H23E H 0.5395 0.5671 0.0668 0.084 Uiso 1 1 calc R . .
N41 N 0.6742(4) 0.9021(6) 0.2355(5) 0.0418(14) Uani 0.5 1 d PD C 2
C42 C 0.6720(6) 0.7846(7) 0.2298(5) 0.0397(18) Uani 0.5 1 d PD C 2
C421 C 0.7384(9) 0.7022(13) 0.2405(17) 0.045(5) Uani 0.5 1 d PD C 2
H42A H 0.7838 0.7489 0.2372 0.067 Uiso 0.5 1 calc PR C 2
H42B H 0.727 0.6426 0.1875 0.067 Uiso 0.5 1 calc PR C 2
H42C H 0.7484 0.6607 0.3037 0.067 Uiso 0.5 1 calc PR C 2
N43 N 0.5992(4) 0.7476(7) 0.2126(5) 0.0410(16) Uani 0.5 1 d PD C 2
C44 C 0.5529(5) 0.8500(7) 0.2108(7) 0.039(2) Uani 0.5 1 d PD C 2
H44 H 0.4989 0.8513 0.2023 0.047 Uiso 0.5 1 calc PR C 2
C45 C 0.5995(5) 0.9441(7) 0.2232(7) 0.0422(19) Uani 0.5 1 d PD C 2
H45 H 0.5847 1.0263 0.2237 0.051 Uiso 0.5 1 calc PR C 2
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 C11 C111 113.0(3) . . ?
N11 C11 H11A 109 . . ?
C111 C11 H11A 109 . . ?
N11 C11 H11B 109 . . ?
C111 C11 H11B 109 . . ?
H11A C11 H11B 107.8 . . ?
N31 C11 H11C 108.3 . . ?
C111 C11 H11C 108.3 . . ?
N31 C11 H11D 108.3 . . ?
C111 C11 H11D 108.3 . . ?
H11C C11 H11D 107.4 . . ?
C112 C111 C116 118.6(3) . . ?
C112 C111 C11 123.3(3) . . ?
C116 C111 C11 118.1(3) . . ?
C111 C112 C113 121.0(3) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.5 . . ?
C114 C113 C112 119.5(3) . . ?
C114 C113 H113 120.2 . . ?
C112 C113 H113 120.2 . . ?
C113 C114 C115 120.2(3) . . ?
C113 C114 H114 119.9 . . ?
C115 C114 H114 119.9 . . ?
C114 C115 C116 120.3(3) . . ?
C114 C115 H115 119.9 . . ?
C116 C115 H115 119.9 . . ?
C115 C116 C111 120.4(3) . . ?
C115 C116 H116 119.8 . . ?
C111 C116 H116 119.8 . . ?
C12 N11 C15 109.3(3) . . ?
C12 N11 C11 127.5(3) . . ?
C15 N11 C11 123.2(3) . . ?
N13 C12 N11 107.3(3) . . ?
N13 C12 C121 126.6(4) . . ?
N11 C12 C121 126.1(4) . . ?
C12 N13 C14 109.4(3) . . ?
C12 N13 C131 126.4(3) . . ?
C14 N13 C131 124.0(3) . . ?
C15 C14 N13 107.1(3) . . ?
C15 C14 H14 126.4 . . ?
N13 C14 H14 126.4 . . ?
C14 C15 N11 106.9(4) . . ?
C14 C15 H15 126.6 . . ?
N11 C15 H15 126.6 . . ?
N13 C131 C132 114.5(3) . . ?
N33 C131 C132 108.2(5) . . ?
N13 C131 H13A 108.6 . . ?
C132 C131 H13A 108.6 . . ?
N13 C131 H13B 108.6 . . ?
C132 C131 H13B 108.6 . . ?
H13A C131 H13B 107.6 . . ?
N33 C131 H13F 110.1 . . ?
C132 C131 H13F 110.1 . . ?
N13 C131 H13G 129.2 . . ?
N33 C131 H13G 110.1 . . ?
C132 C131 H13G 110.1 . . ?
H13F C131 H13G 108.4 . . ?
C131 C132 H13C 109.5 . . ?
C131 C132 H13D 109.5 . . ?
H13C C132 H13D 109.5 . . ?
C131 C132 H13E 109.5 . . ?
H13C C132 H13E 109.5 . . ?
H13D C132 H13E 109.5 . . ?
C32 N31 C35 109.9(10) . . ?
C32 N31 C11 126.6(10) . . ?
C35 N31 C11 123.5(10) . . ?
N33 C32 N31 106.9(10) . . ?
N33 C32 C321 127.0(14) . . ?
N31 C32 C321 126.1(13) . . ?
C32 C321 H32A 109.5 . . ?
C32 C321 H32B 109.5 . . ?
H32A C321 H32B 109.5 . . ?
C32 C321 H32C 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
C32 N33 C34 110.3(11) . . ?
C32 N33 C131 126.9(10) . . ?
C34 N33 C131 122.6(10) . . ?
C35 C34 N33 106.8(13) . . ?
C35 C34 H34 126.6 . . ?
N33 C34 H34 126.6 . . ?
C34 C35 N31 106.0(12) . . ?
C34 C35 H35 127 . . ?
N31 C35 H35 127 . . ?
N41 C21 C211 112.2(3) . . ?
C211 C21 N21 110.1(3) . . ?
C211 C21 H21A 109.6 . . ?
N21 C21 H21A 109.6 . . ?
C211 C21 H21B 109.6 . . ?
N21 C21 H21B 109.6 . . ?
H21A C21 H21B 108.2 . . ?
N41 C21 H21C 109.2 . . ?
C211 C21 H21C 109.2 . . ?
N41 C21 H21D 109.1 . . ?
C211 C21 H21D 109.1 . . ?
H21C C21 H21D 107.9 . . ?
C216 C211 C212 118.8(4) . . ?
C216 C211 C21 120.6(3) . . ?
C212 C211 C21 120.7(3) . . ?
C211 C212 C213 120.8(4) . . ?
C211 C212 H212 119.6 . . ?
C213 C212 H212 119.6 . . ?
C214 C213 C212 119.9(3) . . ?
C214 C213 H213 120.1 . . ?
C212 C213 H213 120.1 . . ?
C213 C214 C215 120.2(4) . . ?
C213 C214 H214 119.9 . . ?
C215 C214 H214 119.9 . . ?
C216 C215 C214 120.0(4) . . ?
C216 C215 H215 120 . . ?
C214 C215 H215 120 . . ?
C215 C216 C211 120.2(3) . . ?
C215 C216 H216 119.9 . . ?
C211 C216 H216 119.9 . . ?
C22 N21 C25 108.6(7) . . ?
C22 N21 C21 125.2(5) . . ?
C25 N21 C21 126.0(7) . . ?
N23 C22 N21 107.3(5) . . ?
N23 C22 C221 126.3(6) . . ?
N21 C22 C221 126.4(6) . . ?
C22 N23 C24 109.6(5) . . ?
C22 N23 C231 127.3(5) . . ?
C24 N23 C231 123.1(5) . . ?
C25 C24 N23 106.8(7) . . ?
C25 C24 H24 126.6 . . ?
N23 C24 H24 126.6 . . ?
C24 C25 N21 107.8(9) . . ?
C24 C25 H25 126.1 . . ?
N21 C25 H25 126.1 . . ?
N23 C231 C232 118.6(4) . . ?
C232 C231 N43 110.1(4) . . ?
N23 C231 H23A 107.7 . . ?
C232 C231 H23A 107.7 . . ?
N23 C231 H23B 107.7 . . ?
C232 C231 H23B 107.7 . . ?
H23A C231 H23B 107.1 . . ?
C232 C231 H23F 109.6 . . ?
N43 C231 H23F 109.6 . . ?
N23 C231 H23G 124 . . ?
C232 C231 H23G 109.7 . . ?
N43 C231 H23G 109.6 . . ?
H23F C231 H23G 108.2 . . ?
C231 C232 H23C 109.5 . . ?
C231 C232 H23D 109.5 . . ?
H23C C232 H23D 109.5 . . ?
C231 C232 H23E 109.5 . . ?
H23C C232 H23E 109.5 . . ?
H23D C232 H23E 109.5 . . ?
C42 N41 C45 108.2(7) . . ?
C42 N41 C21 123.0(7) . . ?
C45 N41 C21 128.5(6) . . ?
N41 C42 N43 109.3(7) . . ?
N41 C42 C421 126.6(11) . . ?
N43 C42 C421 124.1(9) . . ?
C42 C421 H42A 109.5 . . ?
C42 C421 H42B 109.5 . . ?
H42A C421 H42B 109.5 . . ?
C42 C421 H42C 109.5 . . ?
H42A C421 H42C 109.5 . . ?
H42B C421 H42C 109.5 . . ?
C42 N43 C44 107.9(7) . . ?
C42 N43 C231 137.4(7) . . ?
C44 N43 C231 114.3(6) . . ?
C45 C44 N43 106.2(8) . . ?
C45 C44 H44 126.9 . . ?
N43 C44 H44 126.9 . . ?
C44 C45 N41 108.3(7) . . ?
C44 C45 H45 125.8 . . ?
N41 C45 H45 125.8 . . ?
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
C11 N31 1.432(11) . ?
C11 N11 1.458(4) . ?
C11 C111 1.510(4) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C11 H11C 0.99 . ?
C11 H11D 0.99 . ?
C111 C112 1.381(4) . ?
C111 C116 1.400(4) . ?
C112 C113 1.394(5) . ?
C112 H112 0.95 . ?
C113 C114 1.379(5) . ?
C113 H113 0.95 . ?
C114 C115 1.379(5) . ?
C114 H114 0.95 . ?
C115 C116 1.379(5) . ?
C115 H115 0.95 . ?
C116 H116 0.95 . ?
N11 C12 1.347(5) . ?
N11 C15 1.387(5) . ?
C12 N13 1.335(4) . ?
C12 C121 1.465(5) . ?
C121 H12A 0.98 . ?
C121 H12B 0.98 . ?
C121 H12C 0.98 . ?
N13 C14 1.388(5) . ?
N13 C131 1.464(4) . ?
C14 C15 1.348(5) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C131 N33 1.505(11) . ?
C131 C132 1.509(5) . ?
C131 H13A 0.99 . ?
C131 H13B 0.99 . ?
C131 H13F 0.99 . ?
C131 H13G 0.99 . ?
C132 H13C 0.98 . ?
C132 H13D 0.98 . ?
C132 H13E 0.98 . ?
N31 C32 1.349(13) . ?
N31 C35 1.395(14) . ?
C32 N33 1.317(14) . ?
C32 C321 1.456(14) . ?
C321 H32A 0.98 . ?
C321 H32B 0.98 . ?
C321 H32C 0.98 . ?
N33 C34 1.397(15) . ?
C34 C35 1.353(16) . ?
C34 H34 0.95 . ?
C35 H35 0.95 . ?
C21 N41 1.394(7) . ?
C21 C211 1.508(5) . ?
C21 N21 1.570(7) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C21 H21C 0.99 . ?
C21 H21D 0.99 . ?
C211 C216 1.385(5) . ?
C211 C212 1.388(4) . ?
C212 C213 1.392(6) . ?
C212 H212 0.95 . ?
C213 C214 1.357(6) . ?
C213 H213 0.95 . ?
C214 C215 1.392(6) . ?
C214 H214 0.95 . ?
C215 C216 1.385(6) . ?
C215 H215 0.95 . ?
C216 H216 0.95 . ?
N21 C22 1.346(7) . ?
N21 C25 1.378(13) . ?
C22 N23 1.340(7) . ?
C22 C221 1.480(9) . ?
C221 H22A 0.98 . ?
C221 H22B 0.98 . ?
C221 H22C 0.98 . ?
N23 C24 1.376(7) . ?
N23 C231 1.380(6) . ?
C24 C25 1.345(12) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?
C231 C232 1.466(6) . ?
C231 N43 1.532(8) . ?
C231 H23A 0.99 . ?
C231 H23B 0.99 . ?
C231 H23F 0.99 . ?
C231 H23G 0.99 . ?
C232 H23C 0.98 . ?
C232 H23D 0.98 . ?
C232 H23E 0.98 . ?
N41 C42 1.305(9) . ?
N41 C45 1.393(9) . ?
C42 N43 1.335(10) . ?
C42 C421 1.483(14) . ?
C421 H42A 0.98 . ?
C421 H42B 0.98 . ?
C421 H42C 0.98 . ?
N43 C44 1.406(10) . ?
C44 C45 1.324(10) . ?
C44 H44 0.95 . ?
C45 H45 0.95 . ?
