#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226077.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_2226077
loop_
_publ_author_name
'Özel Güven, Özden'
'Bayraktar, Meral'
'Coles, Simon J.'
'Hökelek, Tuncer'
_publ_section_title
;
 1-[2-(4-Chlorobenzyloxy)-2-phenylethyl]-1H-benzotriazole
;
_journal_coeditor_code           CI5085
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1246
_journal_page_last               o1247
_journal_paper_doi               10.1107/S1600536810015692
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H18 Cl N3 O'
_chemical_formula_moiety         'C21 H18 Cl N3 O'
_chemical_formula_sum            'C21 H18 Cl N3 O'
_chemical_formula_weight         363.83
_chemical_name_systematic
;
1-[2-(4-Chlorobenzyloxy)-2-phenylethyl]-1H-benzotriazole
;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2163(2)
_cell_length_b                   36.8545(9)
_cell_length_c                   13.3019(3)
_cell_measurement_reflns_used    26277
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     3536.42(15)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26731
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.688
_refine_ls_extinction_coef       0.038(2)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         7993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1171P)²+0.2599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                5918
_reflns_number_total             7993
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5085.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226077
_cod_database_fobs_code          2226077
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_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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.22475(9) 0.476481(18) 0.55416(6) 0.0416(2) Uani d . 1 . .
O O1 0.3382(2) 0.34725(4) 0.40142(11) 0.0230(3) Uani d . 1 . .
N N1 0.3727(3) 0.38511(5) 0.07784(14) 0.0288(5) Uani d . 1 . .
N N2 0.4375(3) 0.35556(5) 0.12052(14) 0.0269(4) Uani d . 1 . .
N N3 0.4929(3) 0.36393(5) 0.21634(13) 0.0228(4) Uani d . 1 . .
C C1 0.3846(3) 0.41288(6) 0.14623(17) 0.0250(5) Uani d . 1 . .
C C2 0.3361(3) 0.44961(7) 0.13830(19) 0.0327(6) Uani d . 1 . .
H H2 0.2799 0.4591 0.0785 0.039 Uiso calc R 1 . .
C C3 0.3729(3) 0.47135(7) 0.2200(2) 0.0330(6) Uani d . 1 . .
H H3 0.3418 0.4964 0.2166 0.040 Uiso calc R 1 . .
C C4 0.4559(3) 0.45739(7) 0.30917(19) 0.0313(5) Uani d . 1 . .
H H4 0.4821 0.4734 0.3636 0.038 Uiso calc R 1 . .
C C5 0.4999(3) 0.42131(6) 0.31946(17) 0.0264(5) Uani d . 1 . .
H H5 0.5527 0.4118 0.3801 0.032 Uiso calc R 1 . .
C C6 0.4626(3) 0.39944(6) 0.23575(16) 0.0222(5) Uani d . 1 . .
C C7 0.5705(3) 0.33638(6) 0.28229(17) 0.0250(5) Uani d . 1 . .
H H7A 0.6674 0.3474 0.3266 0.030 Uiso calc R 1 . .
H H7B 0.6299 0.3174 0.2414 0.030 Uiso calc R 1 . .
C C8 0.4235(3) 0.31891(6) 0.34680(16) 0.0239(5) Uani d . 1 . .
H H8 0.3278 0.3074 0.3014 0.029 Uiso calc R 1 . .
C C9 0.5062(3) 0.29013(6) 0.41518(15) 0.0209(5) Uani d . 1 . .
C C10 0.6548(3) 0.29873(6) 0.48017(16) 0.0234(5) Uani d . 1 . .
H H10 0.7022 0.3228 0.4821 0.028 Uiso calc R 1 . .
C C11 0.7333(3) 0.27231(6) 0.54186(16) 0.0259(5) Uani d . 1 . .
H H11 0.8358 0.2782 0.5851 0.031 Uiso calc R 1 . .
C C12 0.6629(3) 0.23736(6) 0.54066(16) 0.0254(5) Uani d . 1 . .
H H12 0.7166 0.2193 0.5833 0.030 Uiso calc R 1 . .
C C13 0.5145(3) 0.22873(6) 0.47732(16) 0.0248(5) Uani d . 1 . .
H H13 0.4654 0.2048 0.4769 0.030 Uiso calc R 1 . .
C C14 0.4368(3) 0.25505(6) 0.41408(16) 0.0233(5) Uani d . 1 . .
H H14 0.3359 0.2489 0.3700 0.028 Uiso calc R 1 . .
C C15 0.1497(3) 0.33957(7) 0.4250(2) 0.0360(6) Uani d . 1 . .
H H15A 0.1459 0.3212 0.4791 0.043 Uiso calc R 1 . .
H H15B 0.0831 0.3297 0.3649 0.043 Uiso calc R 1 . .
C C16 0.0583(3) 0.37382(6) 0.45829(18) 0.0265(5) Uani d . 1 . .
C C17 0.0463(3) 0.40358(7) 0.39399(17) 0.0273(5) Uani d . 1 . .
H H17 0.0966 0.4020 0.3288 0.033 Uiso calc R 1 . .
C C18 -0.0374(3) 0.43532(6) 0.42360(18) 0.0291(5) Uani d . 1 . .
H H18 -0.0430 0.4557 0.3799 0.035 Uiso calc R 1 . .
C C19 -0.1137(3) 0.43699(6) 0.51846(18) 0.0278(5) Uani d . 1 . .
C C20 -0.1040(3) 0.40812(6) 0.58310(18) 0.0276(5) Uani d . 1 . .
H H20 -0.1553 0.4097 0.6480 0.033 Uiso calc R 1 . .
C C21 -0.0178(3) 0.37633(6) 0.55244(18) 0.0272(5) Uani d . 1 . .
H H21 -0.0113 0.3561 0.5967 0.033 Uiso calc R 1 . .
Cl Cl1' 0.19246(9) 0.026883(16) 0.22027(5) 0.0384(2) Uani d . 1 . .
O O1' 0.8366(2) 0.15017(4) 0.30657(11) 0.0248(4) Uani d . 1 . .
N N1' 0.9026(3) 0.12718(5) 0.65649(14) 0.0294(5) Uani d . 1 . .
N N2' 0.9650(3) 0.15280(5) 0.59942(14) 0.0274(4) Uani d . 1 . .
N N3' 0.9881(3) 0.13952(5) 0.50553(13) 0.0225(4) Uani d . 1 . .
C C1' 0.8871(3) 0.09601(6) 0.59982(17) 0.0247(5) Uani d . 1 . .
C C2' 0.8299(3) 0.06087(7) 0.62520(19) 0.0307(5) Uani d . 1 . .
H H2' 0.7928 0.0551 0.6913 0.037 Uiso calc R 1 . .
C C3' 0.8297(3) 0.03530(6) 0.5510(2) 0.0320(6) Uani d . 1 . .
H H3' 0.7897 0.0114 0.5658 0.038 Uiso calc R 1 . .
C C4' 0.8873(3) 0.04340(6) 0.45265(19) 0.0296(5) Uani d . 1 . .
H H4' 0.8868 0.0247 0.4035 0.036 Uiso calc R 1 . .
C C5' 0.9438(3) 0.07756(6) 0.42656(17) 0.0253(5) Uani d . 1 . .
H H5' 0.9818 0.0831 0.3605 0.030 Uiso calc R 1 . .
C C6' 0.9424(3) 0.10373(6) 0.50228(16) 0.0211(4) Uani d . 1 . .
C C7' 1.0704(3) 0.16200(6) 0.42962(16) 0.0235(5) Uani d . 1 . .
H H7C 1.1558 0.1471 0.3898 0.028 Uiso calc R 1 . .
H H7D 1.1442 0.1814 0.4629 0.028 Uiso calc R 1 . .
C C8' 0.9260(3) 0.17904(6) 0.35944(16) 0.0226(5) Uani d . 1 . .
H H8' 0.8322 0.1917 0.4010 0.027 Uiso calc R 1 . .
C C9' 1.0112(3) 0.20660(6) 0.29009(15) 0.0207(4) Uani d . 1 . .
C C10' 1.1563(3) 0.19730(6) 0.22767(17) 0.0241(5) Uani d . 1 . .
H H10' 1.2023 0.1731 0.2278 0.029 Uiso calc R 1 . .
C C11' 1.2337(3) 0.22296(7) 0.16565(17) 0.0290(5) Uani d . 1 . .
H H11' 1.3332 0.2165 0.1239 0.035 Uiso calc R 1 . .
C C12' 1.1663(3) 0.25810(6) 0.16425(16) 0.0262(5) Uani d . 1 . .
H H12' 1.2187 0.2757 0.1212 0.031 Uiso calc R 1 . .
C C13' 1.0226(3) 0.26762(6) 0.22557(16) 0.0243(5) Uani d . 1 . .
H H13' 0.9763 0.2917 0.2244 0.029 Uiso calc R 1 . .
C C14' 0.9455(3) 0.24203(6) 0.28896(16) 0.0228(5) Uani d . 1 . .
H H14' 0.8477 0.2488 0.3316 0.027 Uiso calc R 1 . .
C C15' 0.6640(3) 0.16060(6) 0.25888(18) 0.0287(5) Uani d . 1 . .
H H15C 0.6864 0.1714 0.1922 0.034 Uiso calc R 1 . .
H H15D 0.6006 0.1788 0.3005 0.034 Uiso calc R 1 . .
C C16' 0.5460(3) 0.12733(6) 0.24718(17) 0.0246(5) Uani d . 1 . .
C C17' 0.4741(3) 0.11645(7) 0.15453(17) 0.0265(5) Uani d . 1 . .
H H17' 0.4985 0.1305 0.0965 0.032 Uiso calc R 1 . .
C C18' 0.3671(3) 0.08540(6) 0.14502(18) 0.0267(5) Uani d . 1 . .
H H18' 0.3189 0.0780 0.0811 0.032 Uiso calc R 1 . .
C C19' 0.3319(3) 0.06545(6) 0.23027(18) 0.0272(5) Uani d . 1 . .
C C20' 0.4002(3) 0.07576(7) 0.32357(18) 0.0303(5) Uani d . 1 . .
H H20' 0.3738 0.0617 0.3814 0.036 Uiso calc R 1 . .
C C21' 0.5076(3) 0.10674(7) 0.33240(17) 0.0268(5) Uani d . 1 . .
H H21' 0.5553 0.1140 0.3965 0.032 Uiso calc R 1 . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C15 . . 113.13(17) ?
N2 N1 C1 . . 108.55(18) ?
N1 N2 N3 . . 108.07(18) ?
C6 N3 N2 . . 110.69(17) ?
C6 N3 C7 . . 128.75(18) ?
N2 N3 C7 . . 120.56(18) ?
N1 C1 C6 . . 108.6(2) ?
N1 C1 C2 . . 131.3(2) ?
C6 C1 C2 . . 120.1(2) ?
C3 C2 C1 . . 117.5(2) ?
C3 C2 H2 . . 121.2 ?
C1 C2 H2 . . 121.2 ?
C2 C3 C4 . . 121.5(2) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 121.9(2) ?
C5 C4 H4 . . 119.0 ?
C3 C4 H4 . . 119.0 ?
C4 C5 C6 . . 116.2(2) ?
C4 C5 H5 . . 121.9 ?
C6 C5 H5 . . 121.9 ?
N3 C6 C1 . . 104.13(19) ?
N3 C6 C5 . . 133.0(2) ?
C1 C6 C5 . . 122.8(2) ?
N3 C7 C8 . . 111.97(18) ?
N3 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
N3 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
O1 C8 C9 . . 112.19(17) ?
O1 C8 C7 . . 107.12(17) ?
C9 C8 C7 . . 111.46(18) ?
O1 C8 H8 . . 108.7 ?
C9 C8 H8 . . 108.7 ?
C7 C8 H8 . . 108.7 ?
C14 C9 C10 . . 119.3(2) ?
C14 C9 C8 . . 120.78(19) ?
C10 C9 C8 . . 119.91(19) ?
C11 C10 C9 . . 120.2(2) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 120.2(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.0(2) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.1(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C9 C14 C13 . . 120.3(2) ?
C9 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
O1 C15 C16 . . 109.06(18) ?
O1 C15 H15A . . 109.9 ?
C16 C15 H15A . . 109.9 ?
O1 C15 H15B . . 109.9 ?
C16 C15 H15B . . 109.9 ?
H15A C15 H15B . . 108.3 ?
C21 C16 C17 . . 118.9(2) ?
C21 C16 C15 . . 120.9(2) ?
C17 C16 C15 . . 120.2(2) ?
C18 C17 C16 . . 120.9(2) ?
C18 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
C17 C18 C19 . . 118.9(2) ?
C17 C18 H18 . . 120.5 ?
C19 C18 H18 . . 120.5 ?
C20 C19 C18 . . 121.4(2) ?
C20 C19 Cl1 . . 119.79(18) ?
C18 C19 Cl1 . . 118.85(19) ?
C19 C20 C21 . . 119.1(2) ?
C19 C20 H20 . . 120.5 ?
C21 C20 H20 . . 120.5 ?
C16 C21 C20 . . 120.8(2) ?
C16 C21 H21 . . 119.6 ?
C20 C21 H21 . . 119.6 ?
C8' O1' C15' . . 113.31(17) ?
N2' N1' C1' . . 108.11(18) ?
N1' N2' N3' . . 109.20(18) ?
N2' N3' C6' . . 110.10(18) ?
N2' N3' C7' . . 119.96(18) ?
C6' N3' C7' . . 129.59(19) ?
N1' C1' C6' . . 108.51(19) ?
N1' C1' C2' . . 131.2(2) ?
C6' C1' C2' . . 120.3(2) ?
C3' C2' C1' . . 117.2(2) ?
C3' C2' H2' . . 121.4 ?
C1' C2' H2' . . 121.4 ?
C2' C3' C4' . . 121.9(2) ?
C2' C3' H3' . . 119.0 ?
C4' C3' H3' . . 119.0 ?
C5' C4' C3' . . 121.6(2) ?
C5' C4' H4' . . 119.2 ?
C3' C4' H4' . . 119.2 ?
C4' C5' C6' . . 116.4(2) ?
C4' C5' H5' . . 121.8 ?
C6' C5' H5' . . 121.8 ?
N3' C6' C5' . . 133.4(2) ?
N3' C6' C1' . . 104.07(19) ?
C5' C6' C1' . . 122.5(2) ?
N3' C7' C8' . . 112.26(18) ?
N3' C7' H7C . . 109.2 ?
C8' C7' H7C . . 109.2 ?
N3' C7' H7D . . 109.2 ?
C8' C7' H7D . . 109.2 ?
H7C C7' H7D . . 107.9 ?
O1' C8' C9' . . 112.79(17) ?
O1' C8' C7' . . 106.87(17) ?
C9' C8' C7' . . 111.70(18) ?
O1' C8' H8' . . 108.4 ?
C9' C8' H8' . . 108.4 ?
C7' C8' H8' . . 108.4 ?
C14' C9' C10' . . 119.0(2) ?
C14' C9' C8' . . 119.57(19) ?
C10' C9' C8' . . 121.38(19) ?
C11' C10' C9' . . 120.5(2) ?
C11' C10' H10' . . 119.7 ?
C9' C10' H10' . . 119.7 ?
C10' C11' C12' . . 120.1(2) ?
C10' C11' H11' . . 120.0 ?
C12' C11' H11' . . 120.0 ?
C13' C12' C11' . . 119.9(2) ?
C13' C12' H12' . . 120.0 ?
C11' C12' H12' . . 120.0 ?
C12' C13' C14' . . 120.3(2) ?
C12' C13' H13' . . 119.9 ?
C14' C13' H13' . . 119.9 ?
C9' C14' C13' . . 120.1(2) ?
C9' C14' H14' . . 119.9 ?
C13' C14' H14' . . 119.9 ?
O1' C15' C16' . . 108.11(18) ?
O1' C15' H15C . . 110.1 ?
C16' C15' H15C . . 110.1 ?
O1' C15' H15D . . 110.1 ?
C16' C15' H15D . . 110.1 ?
H15C C15' H15D . . 108.4 ?
C17' C16' C21' . . 119.1(2) ?
C17' C16' C15' . . 121.9(2) ?
C21' C16' C15' . . 119.0(2) ?
C16' C17' C18' . . 121.1(2) ?
C16' C17' H17' . . 119.5 ?
C18' C17' H17' . . 119.5 ?
C19' C18' C17' . . 118.6(2) ?
C19' C18' H18' . . 120.7 ?
C17' C18' H18' . . 120.7 ?
C20' C19' C18' . . 121.6(2) ?
C20' C19' Cl1' . . 119.05(18) ?
C18' C19' Cl1' . . 119.30(18) ?
C19' C20' C21' . . 119.4(2) ?
C19' C20' H20' . . 120.3 ?
C21' C20' H20' . . 120.3 ?
C20' C21' C16' . . 120.1(2) ?
C20' C21' H21' . . 119.9 ?
C16' C21' H21' . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C19 . 1.734(2) ?
O1 C8 . 1.422(3) ?
O1 C15 . 1.432(3) ?
N1 N2 . 1.309(3) ?
N1 C1 . 1.371(3) ?
N2 N3 . 1.361(2) ?
N3 C6 . 1.353(3) ?
N3 C7 . 1.445(3) ?
C1 C6 . 1.394(3) ?
C1 C2 . 1.401(3) ?
C2 C3 . 1.371(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.411(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.373(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.395(3) ?
C5 H5 . 0.95 ?
C7 C8 . 1.525(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.510(3) ?
C8 H8 . 1.00 ?
C9 C14 . 1.387(3) ?
C9 C10 . 1.396(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.385(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.392(3) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C16 . 1.497(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C21 . 1.384(3) ?
C16 C17 . 1.392(3) ?
C17 C18 . 1.379(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.391(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.369(3) ?
C20 C21 . 1.393(3) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
Cl1' C19' . 1.745(2) ?
O1' C8' . 1.421(3) ?
O1' C15' . 1.435(3) ?
N1' N2' . 1.299(3) ?
N1' C1' . 1.377(3) ?
N2' N3' . 1.356(3) ?
N3' C6' . 1.360(3) ?
N3' C7' . 1.446(3) ?
C1' C6' . 1.397(3) ?
C1' C2' . 1.403(3) ?
C2' C3' . 1.365(4) ?
C2' H2' . 0.95 ?
C3' C4' . 1.415(3) ?
C3' H3' . 0.95 ?
C4' C5' . 1.371(3) ?
C4' H4' . 0.95 ?
C5' C6' . 1.395(3) ?
C5' H5' . 0.9500 ?
C7' C8' . 1.516(3) ?
C7' H7C . 0.99 ?
C7' H7D . 0.99 ?
C8' C9' . 1.514(3) ?
C8' H8' . 1.00 ?
C9' C14' . 1.389(3) ?
C9' C10' . 1.397(3) ?
C10' C11' . 1.382(3) ?
C10' H10' . 0.95 ?
C11' C12' . 1.383(3) ?
C11' H11' . 0.95 ?
C12' C13' . 1.381(3) ?
C12' H12' . 0.95 ?
C13' C14' . 1.391(3) ?
C13' H13' . 0.95 ?
C14' H14' . 0.95 ?
C15' C16' . 1.498(3) ?
C15' H15C . 0.99 ?
C15' H15D . 0.99 ?
C16' C17' . 1.384(3) ?
C16' C21' . 1.398(3) ?
C17' C18' . 1.384(3) ?
C17' H17' . 0.95 ?
C18' C19' . 1.380(3) ?
C18' H18' . 0.95 ?
C19' C20' . 1.377(3) ?
C20' C21' . 1.383(3) ?
C20' H20' . 0.95 ?
C21' H21' . 0.95 ?
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
C11 H11 Cg2 1_556 0.95 2.62 3.515(2) 157 yes
C11' H11' Cg1 1_654 0.95 2.79 3.635(2) 149 yes
C14 H14 Cg2 4_455 0.95 2.64 3.584(2) 172 yes
C14' H14' Cg1 4_554 0.95 2.81 3.755(2) 172 yes
C18' H18' Cg3 1_554 0.95 2.83 3.502(2) 129 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
C1 N1 N2 N3 . . . . -0.4(2) ?
N1 N2 N3 C6 . . . . 0.2(2) ?
N1 N2 N3 C7 . . . . 179.79(19) ?
N2 N1 C1 C6 . . . . 0.4(3) ?
N2 N1 C1 C2 . . . . 179.3(2) ?
N1 C1 C2 C3 . . . . -177.2(2) ?
C6 C1 C2 C3 . . . . 1.7(3) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
C2 C3 C4 C5 . . . . -1.6(4) ?
C3 C4 C5 C6 . . . . 1.7(3) ?
N2 N3 C6 C1 . . . . 0.1(2) ?
C7 N3 C6 C1 . . . . -179.5(2) ?
N2 N3 C6 C5 . . . . -177.4(2) ?
C7 N3 C6 C5 . . . . 3.0(4) ?
N1 C1 C6 N3 . . . . -0.3(2) ?
C2 C1 C6 N3 . . . . -179.4(2) ?
N1 C1 C6 C5 . . . . 177.6(2) ?
C2 C1 C6 C5 . . . . -1.5(3) ?
C4 C5 C6 N3 . . . . 176.9(2) ?
C4 C5 C6 C1 . . . . -0.2(3) ?
C6 N3 C7 C8 . . . . 85.9(3) ?
N2 N3 C7 C8 . . . . -93.6(2) ?
C15 O1 C8 C9 . . . . -86.2(2) ?
C15 O1 C8 C7 . . . . 151.18(19) ?
N3 C7 C8 O1 . . . . -57.0(2) ?
N3 C7 C8 C9 . . . . 179.89(17) ?
O1 C8 C9 C14 . . . . 115.0(2) ?
C7 C8 C9 C14 . . . . -124.9(2) ?
O1 C8 C9 C10 . . . . -65.3(2) ?
C7 C8 C9 C10 . . . . 54.9(3) ?
C14 C9 C10 C11 . . . . 0.8(3) ?
C8 C9 C10 C11 . . . . -178.91(19) ?
C9 C10 C11 C12 . . . . -1.1(3) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C12 C13 C14 . . . . 0.6(3) ?
C10 C9 C14 C13 . . . . 0.1(3) ?
C8 C9 C14 C13 . . . . 179.87(19) ?
C12 C13 C14 C9 . . . . -0.8(3) ?
C8 O1 C15 C16 . . . . -165.84(19) ?
O1 C15 C16 C21 . . . . -121.1(2) ?
O1 C15 C16 C17 . . . . 59.8(3) ?
C21 C16 C17 C18 . . . . 0.9(3) ?
C15 C16 C17 C18 . . . . 180.0(2) ?
C16 C17 C18 C19 . . . . -1.3(4) ?
C17 C18 C19 C20 . . . . 1.2(4) ?
C17 C18 C19 Cl1 . . . . -178.19(18) ?
C18 C19 C20 C21 . . . . -0.8(4) ?
Cl1 C19 C20 C21 . . . . 178.61(17) ?
C17 C16 C21 C20 . . . . -0.5(3) ?
C15 C16 C21 C20 . . . . -179.5(2) ?
C19 C20 C21 C16 . . . . 0.4(3) ?
C1' N1' N2' N3' . . . . 1.1(2) ?
N1' N2' N3' C6' . . . . -1.2(2) ?
N1' N2' N3' C7' . . . . -175.07(19) ?
N2' N1' C1' C6' . . . . -0.6(3) ?
N2' N1' C1' C2' . . . . 178.9(2) ?
N1' C1' C2' C3' . . . . -179.9(2) ?
C6' C1' C2' C3' . . . . -0.5(3) ?
C1' C2' C3' C4' . . . . 1.0(4) ?
C2' C3' C4' C5' . . . . -1.0(4) ?
C3' C4' C5' C6' . . . . 0.4(3) ?
N2' N3' C6' C5' . . . . -178.8(2) ?
C7' N3' C6' C5' . . . . -5.7(4) ?
N2' N3' C6' C1' . . . . 0.8(2) ?
C7' N3' C6' C1' . . . . 173.9(2) ?
C4' C5' C6' N3' . . . . 179.7(2) ?
C4' C5' C6' C1' . . . . 0.1(3) ?
N1' C1' C6' N3' . . . . -0.2(2) ?
C2' C1' C6' N3' . . . . -179.7(2) ?
N1' C1' C6' C5' . . . . 179.5(2) ?
C2' C1' C6' C5' . . . . 0.0(3) ?
N2' N3' C7' C8' . . . . -99.2(2) ?
C6' N3' C7' C8' . . . . 88.3(3) ?
C15' O1' C8' C9' . . . . -73.5(2) ?
C15' O1' C8' C7' . . . . 163.40(18) ?
N3' C7' C8' O1' . . . . -64.4(2) ?
N3' C7' C8' C9' . . . . 171.82(18) ?
O1' C8' C9' C14' . . . . 116.4(2) ?
C7' C8' C9' C14' . . . . -123.2(2) ?
O1' C8' C9' C10' . . . . -64.3(3) ?
C7' C8' C9' C10' . . . . 56.1(3) ?
C14' C9' C10' C11' . . . . 0.0(3) ?
C8' C9' C10' C11' . . . . -179.3(2) ?
C9' C10' C11' C12' . . . . -0.6(3) ?
C10' C11' C12' C13' . . . . 0.6(3) ?
C11' C12' C13' C14' . . . . 0.1(3) ?
C10' C9' C14' C13' . . . . 0.7(3) ?
C8' C9' C14' C13' . . . . 179.99(19) ?
C12' C13' C14' C9' . . . . -0.8(3) ?
C8' O1' C15' C16' . . . . -154.90(18) ?
O1' C15' C16' C17' . . . . -124.1(2) ?
O1' C15' C16' C21' . . . . 55.9(3) ?
C21' C16' C17' C18' . . . . -0.8(3) ?
C15' C16' C17' C18' . . . . 179.2(2) ?
C16' C17' C18' C19' . . . . 0.5(3) ?
C17' C18' C19' C20' . . . . 0.1(3) ?
C17' C18' C19' Cl1' . . . . 178.37(17) ?
C18' C19' C20' C21' . . . . -0.3(4) ?
Cl1' C19' C20' C21' . . . . -178.62(18) ?
C19' C20' C21' C16' . . . . 0.0(4) ?
C17' C16' C21' C20' . . . . 0.5(3) ?
C15' C16' C21' C20' . . . . -179.5(2) ?
