#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227090.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2227090
loop_
_publ_author_name
'Khan, F. Nawaz'
'Manivel, P.'
'Roopan, S. Mohana'
'Hathwar, Venkatesha R.'
'Akkurt, Mehmet'
_publ_section_title
;
 1-(3,5-Diethyl-1H-pyrazol-1-yl)-3-phenylisoquinoline
;
_journal_coeditor_code           SU2194
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2063
_journal_page_last               o2064
_journal_paper_doi               10.1107/S1600536810028059
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H21 N3'
_chemical_formula_moiety         'C22 H21 N3'
_chemical_formula_sum            'C22 H21 N3'
_chemical_formula_weight         327.42
_chemical_name_systematic
;
1-(3,5-Diethyl-1H-pyrazol-1-yl)-3-phenylisoquinoline
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.071(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0736(17)
_cell_length_b                   20.819(2)
_cell_length_c                   10.8579(11)
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.36
_cell_measurement_theta_min      1.86
_cell_volume                     3632.8(6)
_computing_cell_refinement       'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Xcalibur Eos (Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17963
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.148
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0667P)²+0.6171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                2379
_reflns_number_total             3389
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2194.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227090
_cod_database_fobs_code          2227090
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.85495(7) 0.13529(6) 0.57519(11) 0.0503(4) Uani . . 1.000
N N2 0.74093(8) 0.08848(6) 0.66680(12) 0.0543(4) Uani . . 1.000
N N3 0.67528(9) 0.11249(7) 0.73249(14) 0.0693(5) Uani . . 1.000
C C1 0.77419(9) 0.12658(7) 0.57018(13) 0.0469(5) Uani . . 1.000
C C2 0.71957(8) 0.15187(7) 0.47772(13) 0.0452(5) Uani . . 1.000
C C3 0.63356(9) 0.13837(7) 0.46657(15) 0.0560(5) Uani . . 1.000
C C4 0.58747(10) 0.16524(8) 0.37411(17) 0.0641(6) Uani . . 1.000
C C5 0.62327(10) 0.20691(9) 0.28960(16) 0.0651(6) Uani . . 1.000
C C6 0.70590(9) 0.22017(8) 0.29663(15) 0.0581(5) Uani . . 1.000
C C7 0.75675(9) 0.19240(7) 0.39001(13) 0.0467(5) Uani . . 1.000
C C8 0.84337(9) 0.20270(7) 0.39824(14) 0.0513(5) Uani . . 1.000
C C9 0.89063(9) 0.17344(7) 0.48754(13) 0.0474(5) Uani . . 1.000
C C10 0.98262(9) 0.18012(8) 0.49702(13) 0.0517(5) Uani . . 1.000
C C11 1.02486(10) 0.22715(9) 0.43174(15) 0.0619(6) Uani . . 1.000
C C12 1.11065(10) 0.23165(10) 0.43877(16) 0.0692(7) Uani . . 1.000
C C13 1.15577(11) 0.18965(10) 0.51142(17) 0.0719(7) Uani . . 1.000
C C14 1.11534(11) 0.14448(11) 0.57762(19) 0.0815(8) Uani . . 1.000
C C15 1.02943(11) 0.13958(10) 0.57140(17) 0.0711(7) Uani . . 1.000
C C16 0.65965(12) 0.06812(10) 0.81487(18) 0.0749(7) Uani . . 1.000
C C17 0.71487(13) 0.01688(9) 0.80421(18) 0.0781(7) Uani . . 1.000
C C18 0.76646(11) 0.03038(8) 0.70880(16) 0.0642(6) Uani . . 1.000
C C19B 0.5866(3) 0.0755(2) 0.8999(4) 0.0936(16) Uani . . 0.836(7)
C C20B 0.6107(2) 0.0648(2) 1.0302(3) 0.1248(16) Uani . . 0.836(7)
C C21B 0.8444(7) -0.0011(5) 0.6591(13) 0.074(3) Uani . . 0.553(16)
C C22B 0.8635(6) -0.0631(3) 0.7263(6) 0.092(2) Uani . . 0.553(16)
C C20A 0.5561(14) 0.0333(11) 0.945(3) 0.168(10) Uiso . . 0.164(7)
C C21A 0.8228(9) -0.0155(7) 0.6459(16) 0.084(4) Uani . . 0.447(16)
C C22A 0.8969(7) -0.0292(9) 0.7276(10) 0.130(5) Uani . . 0.447(16)
C C19A 0.6194(13) 0.0870(14) 0.936(2) 0.139(15) Uani . . 0.164(7)
H H8 0.86860 0.22980 0.34200 0.0620 Uiso calc R 1.000
H H11 0.99490 0.25600 0.38270 0.0740 Uiso calc R 1.000
H H6 0.72930 0.24780 0.23950 0.0700 Uiso calc R 1.000
H H3 0.60850 0.11110 0.52260 0.0670 Uiso calc R 1.000
H H4 0.53110 0.15570 0.36700 0.0770 Uiso calc R 1.000
H H5 0.59040 0.22570 0.22810 0.0780 Uiso calc R 1.000
H H17 0.71640 -0.01980 0.85310 0.0940 Uiso calc R 1.000
H H19C 0.56360 0.11830 0.89080 0.1120 Uiso calc . 0.836(7)
H H19D 0.54360 0.04490 0.87620 0.1120 Uiso calc . 0.836(7)
H H20D 0.63820 0.02400 1.03830 0.1870 Uiso calc . 0.836(7)
H H20E 0.56190 0.06510 1.07980 0.1870 Uiso calc . 0.836(7)
H H20F 0.64780 0.09830 1.05710 0.1870 Uiso calc . 0.836(7)
H H21C 0.83650 -0.00980 0.57190 0.0890 Uiso calc . 0.553(16)
H H21D 0.89110 0.02810 0.66870 0.0890 Uiso calc . 0.553(16)
H H22D 0.87290 -0.05430 0.81220 0.1380 Uiso calc . 0.553(16)
H H22E 0.91240 -0.08230 0.69270 0.1380 Uiso calc . 0.553(16)
H H22F 0.81730 -0.09200 0.71670 0.1380 Uiso calc . 0.553(16)
H H12 1.13790 0.26320 0.39420 0.0830 Uiso calc R 1.000
H H13 1.21350 0.19220 0.51510 0.0860 Uiso calc R 1.000
H H14 1.14570 0.11650 0.62780 0.0980 Uiso calc R 1.000
H H15 1.00290 0.10850 0.61800 0.0850 Uiso calc R 1.000
H H19A 0.65910 0.08660 1.00400 0.1650 Uiso calc . 0.164(7)
H H19B 0.59300 0.12880 0.93020 0.1650 Uiso calc . 0.164(7)
H H20A 0.52560 0.02950 0.86890 0.2520 Uiso calc . 0.164(7)
H H20B 0.51840 0.04290 1.01040 0.2520 Uiso calc . 0.164(7)
H H20C 0.58430 -0.00630 0.96300 0.2520 Uiso calc . 0.164(7)
H H21A 0.84090 0.00290 0.56880 0.1010 Uiso calc . 0.447(16)
H H21B 0.79320 -0.05510 0.62770 0.1010 Uiso calc . 0.447(16)
H H22A 0.92540 0.01020 0.74650 0.1950 Uiso calc . 0.447(16)
H H22B 0.93390 -0.05790 0.68620 0.1950 Uiso calc . 0.447(16)
H H22C 0.87880 -0.04880 0.80260 0.1950 Uiso calc . 0.447(16)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C9 . . . 118.51(12) no
N3 N2 C1 . . . 118.67(12) no
N3 N2 C18 . . . 112.33(13) no
C1 N2 C18 . . . 128.97(13) no
N2 N3 C16 . . . 104.80(14) no
N1 C1 N2 . . . 115.51(13) no
N1 C1 C2 . . . 125.16(13) no
N2 C1 C2 . . . 119.33(13) no
C1 C2 C3 . . . 125.21(13) no
C1 C2 C7 . . . 115.69(12) no
C3 C2 C7 . . . 119.09(13) no
C2 C3 C4 . . . 120.05(14) no
C3 C4 C5 . . . 121.12(15) no
C4 C5 C6 . . . 120.32(16) no
C5 C6 C7 . . . 120.60(15) no
C2 C7 C6 . . . 118.77(13) no
C2 C7 C8 . . . 118.53(13) no
C6 C7 C8 . . . 122.70(13) no
C7 C8 C9 . . . 120.88(14) no
N1 C9 C8 . . . 121.11(13) no
N1 C9 C10 . . . 115.71(12) no
C8 C9 C10 . . . 123.18(13) no
C9 C10 C11 . . . 121.61(14) no
C9 C10 C15 . . . 120.90(14) no
C11 C10 C15 . . . 117.50(14) no
C10 C11 C12 . . . 120.97(16) no
C11 C12 C13 . . . 120.21(17) no
C12 C13 C14 . . . 119.47(17) no
C13 C14 C15 . . . 120.81(19) no
C10 C15 C14 . . . 121.01(18) no
N3 C16 C17 . . . 110.58(17) no
N3 C16 C19B . . . 120.3(2) no
N3 C16 C19A . . . 119.7(11) no
C17 C16 C19B . . . 129.1(2) no
C17 C16 C19A . . . 123.3(10) no
C16 C17 C18 . . . 107.55(17) no
N2 C18 C17 . . . 104.74(15) no
N2 C18 C21B . . . 120.8(5) no
N2 C18 C21A . . . 127.0(6) no
C17 C18 C21B . . . 134.0(5) no
C17 C18 C21A . . . 126.7(6) no
C16 C19A C20A . . . 99.3(19) no
C16 C19B C20B . . . 112.1(3) no
C18 C21A C22A . . . 109.5(12) no
C18 C21B C22B . . . 111.0(9) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 119.00 no
C5 C4 H4 . . . 119.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C7 C6 H6 . . . 120.00 no
C7 C8 H8 . . . 120.00 no
C9 C8 H8 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C12 C13 H13 . . . 120.00 no
C14 C13 H13 . . . 120.00 no
C13 C14 H14 . . . 120.00 no
C15 C14 H14 . . . 120.00 no
C10 C15 H15 . . . 120.00 no
C14 C15 H15 . . . 119.00 no
C16 C17 H17 . . . 126.00 no
C18 C17 H17 . . . 126.00 no
C16 C19A H19A . . . 112.00 no
C16 C19A H19B . . . 112.00 no
C20A C19A H19A . . . 112.00 no
C20A C19A H19B . . . 112.00 no
H19A C19A H19B . . . 110.00 no
C16 C19B H19D . . . 109.00 no
C20B C19B H19C . . . 109.00 no
C16 C19B H19C . . . 109.00 no
H19C C19B H19D . . . 108.00 no
C20B C19B H19D . . . 109.00 no
C19A C20A H20B . . . 109.00 no
C19A C20A H20A . . . 110.00 no
H20A C20A H20B . . . 110.00 no
H20A C20A H20C . . . 110.00 no
C19A C20A H20C . . . 109.00 no
H20B C20A H20C . . . 109.00 no
C19B C20B H20D . . . 109.00 no
C19B C20B H20E . . . 110.00 no
H20E C20B H20F . . . 110.00 no
C19B C20B H20F . . . 109.00 no
H20D C20B H20E . . . 109.00 no
H20D C20B H20F . . . 109.00 no
C18 C21A H21B . . . 110.00 no
C22A C21A H21A . . . 110.00 no
C22A C21A H21B . . . 110.00 no
C18 C21A H21A . . . 110.00 no
H21A C21A H21B . . . 108.00 no
C18 C21B H21C . . . 109.00 no
C22B C21B H21C . . . 109.00 no
C22B C21B H21D . . . 109.00 no
C18 C21B H21D . . . 109.00 no
H21C C21B H21D . . . 108.00 no
C21A C22A H22B . . . 109.00 no
C21A C22A H22C . . . 109.00 no
C21A C22A H22A . . . 110.00 no
H22A C22A H22C . . . 109.00 no
H22B C22A H22C . . . 109.00 no
H22A C22A H22B . . . 110.00 no
C21B C22B H22D . . . 109.00 no
C21B C22B H22E . . . 109.00 no
C21B C22B H22F . . . 109.00 no
H22D C22B H22E . . . 109.00 no
H22D C22B H22F . . . 109.00 no
H22E C22B H22F . . . 110.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . . 1.3108(18) no
N1 C9 . . 1.3733(19) no
N2 N3 . . 1.379(2) no
N2 C1 . . 1.4271(19) no
N2 C18 . . 1.354(2) no
N3 C16 . . 1.313(3) no
C1 C2 . . 1.422(2) no
C2 C3 . . 1.4137(19) no
C2 C7 . . 1.413(2) no
C3 C4 . . 1.357(2) no
C4 C5 . . 1.395(2) no
C5 C6 . . 1.357(2) no
C6 C7 . . 1.414(2) no
C7 C8 . . 1.410(2) no
C8 C9 . . 1.364(2) no
C9 C10 . . 1.487(2) no
C10 C11 . . 1.393(2) no
C10 C15 . . 1.381(2) no
C11 C12 . . 1.383(2) no
C12 C13 . . 1.375(3) no
C13 C14 . . 1.357(3) no
C14 C15 . . 1.385(3) no
C16 C17 . . 1.394(3) no
C16 C19B . . 1.515(5) no
C16 C19A . . 1.53(2) no
C17 C18 . . 1.368(3) no
C18 C21B . . 1.522(12) no
C18 C21A . . 1.491(15) no
C19A C20A . . 1.52(3) no
C19B C20B . . 1.477(5) no
C21A C22A . . 1.499(19) no
C21B C22B . . 1.511(13) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C8 H8 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C15 H15 . . 0.9300 no
C17 H17 . . 0.9300 no
C19A H19A . . 0.9700 no
C19A H19B . . 0.9700 no
C19B H19C . . 0.9700 no
C19B H19D . . 0.9700 no
C20A H20A . . 0.9600 no
C20A H20B . . 0.9600 no
C20A H20C . . 0.9600 no
C20B H20D . . 0.9600 no
C20B H20F . . 0.9600 no
C20B H20E . . 0.9600 no
C21A H21B . . 0.9700 no
C21A H21A . . 0.9700 no
C21B H21C . . 0.9700 no
C21B H21D . . 0.9700 no
C22A H22A . . 0.9600 no
C22A H22B . . 0.9600 no
C22A H22C . . 0.9600 no
C22B H22D . . 0.9600 no
C22B H22E . . 0.9600 no
C22B H22F . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 C21B 2.988(11) . . no
N1 C21A 3.275(15) . . no
N3 C3 3.001(2) . . no
N1 H21D 2.5200 . . no
N1 H15 2.4800 . . no
N1 H21A 2.7700 . . no
N2 H3 2.6600 . . no
N2 H14 2.9100 . 2_756 no
N3 H3 2.5000 . . no
C1 C6 3.515(2) . 7_656 no
C2 C7 3.564(2) . 7_656 no
C2 C8 3.472(2) . 7_656 no
C3 N3 3.001(2) . . no
C4 C11 3.587(2) . 7_656 no
C5 C9 3.483(2) . 7_656 no
C6 C9 3.597(2) . 7_656 no
C6 C1 3.515(2) . 7_656 no
C7 C8 3.575(2) . 7_656 no
C7 C7 3.395(2) . 7_656 no
C7 C2 3.564(2) . 7_656 no
C8 C7 3.575(2) . 7_656 no
C8 C22B 3.473(7) . 4_554 no
C8 C2 3.472(2) . 7_656 no
C9 C6 3.597(2) . 7_656 no
C9 C5 3.483(2) . 7_656 no
C11 C4 3.587(2) . 7_656 no
C20A C20A 2.59(4) . 3_657 no
C21A N1 3.275(15) . . no
C21B N1 2.988(11) . . no
C22A C22A 3.341(16) . 2_756 no
C22B C8 3.473(7) . 4_555 no
C1 H21C 3.0100 . . no
C1 H21A 2.7900 . . no
C1 H21D 2.9700 . . no
C2 H17 3.0600 . 4_554 no
C3 H17 3.0700 . 4_554 no
C3 H20C 2.8600 . 4_554 no
C7 H22F 2.9900 . 4_554 no
C8 H22F 3.0600 . 4_554 no
C8 H11 2.6800 . . no
C11 H8 2.6800 . . no
C12 H8 3.0700 . 2_755 no
C12 H19B 2.9200 . 8_554 no
C13 H6 3.0200 . 8_555 no
C17 H22C 2.9700 . . no
C17 H20C 2.7800 . . no
C17 H20D 2.8500 . . no
C17 H22F 2.9700 . . no
C17 H22D 2.9400 . . no
C18 H20D 2.9700 . 4_554 no
C18 H14 2.8700 . 2_756 no
C20A H17 2.9900 . . no
C20A H20C 2.5500 . 3_657 no
C20A H20B 2.0500 . 3_657 no
C20A H20A 2.7600 . 3_657 no
C22A H22B 2.9200 . 2_756 no
C22A H22A 2.9800 . 2_756 no
C22B H17 2.9000 . . no
H3 N3 2.5000 . . no
H3 N2 2.6600 . . no
H3 H20B 2.5100 . 2_656 no
H3 H20C 2.3100 . 4_554 no
H4 H20E 2.4800 . 2_656 no
H6 H8 2.5100 . . no
H6 C13 3.0200 . 8_454 no
H8 C11 2.6800 . . no
H8 H6 2.5100 . . no
H8 H11 2.1400 . . no
H8 C12 3.0700 . 2_755 no
H11 C8 2.6800 . . no
H11 H8 2.1400 . . no
H12 H19B 2.4000 . 8_554 no
H14 N2 2.9100 . 2_756 no
H14 C18 2.8700 . 2_756 no
H15 H21D 2.5200 . . no
H15 N1 2.4800 . . no
H17 C20A 2.9900 . . no
H17 C22B 2.9000 . . no
H17 H20D 2.5600 . . no
H17 C2 3.0600 . 4_555 no
H17 C3 3.0700 . 4_555 no
H17 H20C 2.4700 . . no
H19B H12 2.4000 . 8_455 no
H19B C12 2.9200 . 8_455 no
H20A C20A 2.7600 . 3_657 no
H20A H20B 2.1300 . 3_657 no
H20B H3 2.5100 . 2_656 no
H20B C20A 2.0500 . 3_657 no
H20B H20C 1.8500 . 3_657 no
H20B H20A 2.1300 . 3_657 no
H20B H20B 1.8900 . 3_657 no
H20C C20A 2.5500 . 3_657 no
H20C H3 2.3100 . 4_555 no
H20C H20B 1.8500 . 3_657 no
H20C C3 2.8600 . 4_555 no
H20C H17 2.4700 . . no
H20C C17 2.7800 . . no
H20D C17 2.8500 . . no
H20D H17 2.5600 . . no
H20D C18 2.9700 . 4_555 no
H20E H4 2.4800 . 2_656 no
H21A C1 2.7900 . . no
H21A N1 2.7700 . . no
H21C C1 3.0100 . . no
H21D C1 2.9700 . . no
H21D H15 2.5200 . . no
H21D N1 2.5200 . . no
H22A C22A 2.9800 . 2_756 no
H22A H22A 2.4000 . 2_756 no
H22B H22B 2.5100 . 2_756 no
H22B C22A 2.9200 . 2_756 no
H22C C17 2.9700 . . no
H22D C17 2.9400 . . no
H22F C17 2.9700 . . no
H22F C7 2.9900 . 4_555 no
H22F C8 3.0600 . 4_555 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 N3 . 0.93 2.50 3.001(2) 114 yes
C15 H15 N1 . 0.93 2.48 2.807(2) 101 yes
C14 H14 Cg1 2_756 0.93 2.88 3.755(2) 158 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 N2 . . . . -177.66(12) no
C9 N1 C1 C2 . . . . 2.3(2) no
C1 N1 C9 C8 . . . . 1.1(2) no
C1 N1 C9 C10 . . . . -178.72(13) no
C1 N2 N3 C16 . . . . -178.86(14) no
C18 N2 N3 C16 . . . . -0.80(19) no
N3 N2 C1 N1 . . . . 128.12(15) no
N3 N2 C1 C2 . . . . -51.86(19) no
C18 N2 C1 N1 . . . . -49.6(2) no
C18 N2 C1 C2 . . . . 130.45(17) no
N3 N2 C18 C17 . . . . 0.31(19) no
N3 N2 C18 C21B . . . . -172.9(6) no
C1 N2 C18 C17 . . . . 178.12(15) no
C1 N2 C18 C21B . . . . 5.0(6) no
N2 N3 C16 C17 . . . . 1.0(2) no
N2 N3 C16 C19B . . . . -175.9(2) no
N1 C1 C2 C3 . . . . 174.67(15) no
N1 C1 C2 C7 . . . . -3.9(2) no
N2 C1 C2 C3 . . . . -5.4(2) no
N2 C1 C2 C7 . . . . 176.11(13) no
C1 C2 C3 C4 . . . . -179.85(15) no
C7 C2 C3 C4 . . . . -1.4(2) no
C1 C2 C7 C6 . . . . -178.91(14) no
C1 C2 C7 C8 . . . . 2.0(2) no
C3 C2 C7 C6 . . . . 2.5(2) no
C3 C2 C7 C8 . . . . -176.61(14) no
C2 C3 C4 C5 . . . . -0.7(2) no
C3 C4 C5 C6 . . . . 1.6(3) no
C4 C5 C6 C7 . . . . -0.5(3) no
C5 C6 C7 C2 . . . . -1.6(2) no
C5 C6 C7 C8 . . . . 177.46(16) no
C2 C7 C8 C9 . . . . 1.1(2) no
C6 C7 C8 C9 . . . . -177.98(15) no
C7 C8 C9 N1 . . . . -2.8(2) no
C7 C8 C9 C10 . . . . 177.06(14) no
N1 C9 C10 C11 . . . . -166.37(14) no
N1 C9 C10 C15 . . . . 13.7(2) no
C8 C9 C10 C11 . . . . 13.8(2) no
C8 C9 C10 C15 . . . . -166.20(16) no
C9 C10 C11 C12 . . . . -178.17(16) no
C15 C10 C11 C12 . . . . 1.8(3) no
C9 C10 C15 C14 . . . . 178.09(17) no
C11 C10 C15 C14 . . . . -1.9(3) no
C10 C11 C12 C13 . . . . -0.4(3) no
C11 C12 C13 C14 . . . . -1.1(3) no
C12 C13 C14 C15 . . . . 1.0(3) no
C13 C14 C15 C10 . . . . 0.5(3) no
N3 C16 C17 C18 . . . . -0.8(2) no
C19B C16 C17 C18 . . . . 175.7(3) no
N3 C16 C19B C20B . . . . -130.4(3) no
C17 C16 C19B C20B . . . . 53.4(4) no
C16 C17 C18 N2 . . . . 0.3(2) no
C16 C17 C18 C21B . . . . 172.1(7) no
N2 C18 C21B C22B . . . . 175.9(5) no
C17 C18 C21B C22B . . . . 5.1(12) no
