#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/25/7052534.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_7052534
loop_
_publ_author_name
'Domínguez, Oscar'
'Rodríguez-Molina, Braulio'
'Rodríguez, Mario'
'Ariza, Armando'
'Farfán, Norberto'
'Santillan, Rosa'
_publ_section_title
;
 X-Ray crystallographic and spectroscopic properties of eight Schiff
 bases as evidence of the proton transfer reaction. Role of the
 intermolecular hydrogen bond
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              156
_journal_paper_doi               10.1039/c0nj00179a
_journal_volume                  35
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H21 Cl1 N2 O2'
_chemical_formula_sum            'C18 H21 Cl N2 O2'
_chemical_formula_weight         332.82
_chemical_name_common
;2-((4-Chloro-2-hydroxymethyl-phenylimino)-methyl)-5-
diethylamino-phenol
;
_chemical_name_systematic
;
2-[(4-Chloro-2-hydroxymethyl-phenylimino)-methyl]-5-diethylamino-phenol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.8703(11)
_cell_angle_beta                 107.113(1)
_cell_angle_gamma                100.4799(14)
_cell_formula_units_Z            4
_cell_length_a                   9.5103(2)
_cell_length_b                   12.8864(4)
_cell_length_c                   15.2106(4)
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     1715.51(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.145589E-1
_diffrn_orient_matrix_UB_12      0.442597E-1
_diffrn_orient_matrix_UB_13      -0.471285E-1
_diffrn_orient_matrix_UB_21      0.317436E-1
_diffrn_orient_matrix_UB_22      0.670909E-1
_diffrn_orient_matrix_UB_23      0.495896E-1
_diffrn_orient_matrix_UB_31      0.107658
_diffrn_orient_matrix_UB_32      -0.58839E-2
_diffrn_orient_matrix_UB_33      0.159495E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14135
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7334
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0858
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1622P)²+0.2099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.238
_refine_ls_wR_factor_ref         0.2786
_reflns_number_gt                4472
_reflns_number_total             7334
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            C0NJ00179A.TXT
_cod_data_source_block           Compound8
_cod_original_sg_symbol_H-M      ' P -1'
_cod_original_formula_sum        'C18 H21 Cl1 N2 O2'
_cod_database_code               7052534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
H2A H 0.825(4) 0.994(3) 0.123(3) 0.067(12) Uiso 1 1 d . . .
H2B H 1.088(5) 1.179(3) -0.052(3) 0.085(12) Uiso 1 1 d . . .
H9B H 0.669(4) 0.957(3) -0.077(2) 0.069(10) Uiso 1 1 d . . .
C2B C 0.6020(3) 0.8200(2) 0.0057(2) 0.0507(7) Uani 1 1 d . . .
C3B C 0.5848(3) 0.7399(3) 0.0564(2) 0.0597(8) Uani 1 1 d . . .
H3B H 0.671 0.7245 0.0949 0.072 Uiso 1 1 calc R . .
C4B C 0.4418(3) 0.6808(2) 0.0520(2) 0.0576(7) Uani 1 1 d . . .
C5B C 0.3113(3) 0.7040(2) -0.0083(2) 0.0572(7) Uani 1 1 d . . .
H5B H 0.2157 0.6669 -0.0117 0.069 Uiso 1 1 calc R . .
C6B C 0.3245(3) 0.7793(2) -0.0605(2) 0.0531(7) Uani 1 1 d . . .
H6B H 0.237 0.792 -0.1003 0.064 Uiso 1 1 calc R . .
C7B C 0.4672(3) 0.8398(2) -0.0571(2) 0.0452(6) Uani 1 1 d . . .
C8B C 0.4727(3) 0.9151(2) -0.1128(2) 0.0490(7) Uani 1 1 d . . .
H8B H 0.3813 0.9241 -0.151 0.059 Uiso 1 1 calc R . .
C10B C 0.6113(3) 1.0519(2) -0.17341(19) 0.0455(6) Uani 1 1 d . . .
C11B C 0.4850(3) 1.0643(2) -0.2422(2) 0.0575(7) Uani 1 1 d . . .
H11B H 0.3897 1.0236 -0.249 0.069 Uiso 1 1 calc R . .
C12B C 0.4991(4) 1.1358(2) -0.3002(2) 0.0632(8) Uani 1 1 d . . .
H12B H 0.4145 1.1444 -0.3457 0.076 Uiso 1 1 calc R . .
C13B C 0.6428(4) 1.1948(2) -0.2892(2) 0.0577(7) Uani 1 1 d . . .
C14B C 0.7679(3) 1.1861(2) -0.2201(2) 0.0536(7) Uani 1 1 d . . .
H14B H 0.8626 1.2278 -0.2134 0.064 Uiso 1 1 calc R . .
C15B C 0.7546(3) 1.1154(2) -0.1602(2) 0.0458(6) Uani 1 1 d . . .
C16B C 0.8906(3) 1.1097(2) -0.0811(2) 0.0547(7) Uani 1 1 d . . .
H16C H 0.8662 1.1126 -0.0233 0.066 Uiso 1 1 calc R . .
H16D H 0.9188 1.0422 -0.0948 0.066 Uiso 1 1 calc R . .
C17B C 0.5534(5) 0.5525(4) 0.1427(3) 0.0970(13) Uani 1 1 d DU . .
H17D H 0.6267 0.561 0.1098 0.116 Uiso 1 1 calc R . .
H17C H 0.5168 0.4763 0.1395 0.116 Uiso 1 1 calc R . .
C18B C 0.6252(7) 0.6130(5) 0.2455(3) 0.133(2) Uani 1 1 d D . .
H18E H 0.642 0.6892 0.2479 0.2 Uiso 1 1 calc R . .
H18F H 0.7201 0.595 0.2728 0.2 Uiso 1 1 calc R . .
H18D H 0.5585 0.5925 0.28 0.2 Uiso 1 1 calc R . .
C19B C 0.2818(4) 0.5529(3) 0.1115(2) 0.0743(10) Uani 1 1 d D . .
H19E H 0.2202 0.6055 0.1075 0.089 Uiso 1 1 calc R . .
H19F H 0.3007 0.535 0.1732 0.089 Uiso 1 1 calc R . .
C20B C 0.1945(5) 0.4509(3) 0.0363(3) 0.0992(14) Uani 1 1 d D . .
H20G H 0.1731 0.4686 -0.0249 0.149 Uiso 1 1 calc R . .
H20I H 0.1012 0.4221 0.0462 0.149 Uiso 1 1 calc R . .
H20H H 0.2546 0.3983 0.0405 0.149 Uiso 1 1 calc R . .
N1B N 0.4268(3) 0.6008(3) 0.1007(3) 0.0800(9) Uani 1 1 d U . .
N9B N 0.5991(2) 0.97592(18) -0.11590(17) 0.0469(6) Uani 1 1 d . . .
O1B O 0.7342(2) 0.87682(17) 0.01204(16) 0.0614(6) Uani 1 1 d . . .
O2B O 1.0118(3) 1.19632(19) -0.0700(2) 0.0914(10) Uani 1 1 d . . .
Cl1B Cl 0.66244(12) 1.28254(8) -0.36441(7) 0.0852(4) Uani 1 1 d . . .
C2A C 0.9620(3) 0.8061(3) 0.4722(2) 0.0615(8) Uani 1 1 d . . .
C3A C 0.8916(4) 0.7248(3) 0.5066(3) 0.0726(9) Uani 1 1 d . . .
H3A H 0.7892 0.6934 0.4763 0.087 Uiso 1 1 calc R . .
C4A C 0.9684(4) 0.6888(3) 0.5844(3) 0.0701(9) Uani 1 1 d . A .
C5A C 1.1235(4) 0.7405(3) 0.6306(3) 0.0795(10) Uani 1 1 d . . .
H5A H 1.1781 0.721 0.6848 0.095 Uiso 1 1 calc R . .
C6A C 1.1917(4) 0.8193(3) 0.5947(3) 0.0712(9) Uani 1 1 d . . .
H6A H 1.294 0.8509 0.6252 0.085 Uiso 1 1 calc R . .
C7A C 1.1181(3) 0.8550(2) 0.5159(2) 0.0536(7) Uani 1 1 d . . .
C8A C 1.1938(3) 0.9368(2) 0.4807(2) 0.0574(8) Uani 1 1 d . . .
H8A H 1.2963 0.9669 0.5116 0.069 Uiso 1 1 calc R . .
C10A C 1.1980(3) 1.0514(2) 0.3706(2) 0.0528(7) Uani 1 1 d . . .
C11A C 1.3472(4) 1.1109(3) 0.4135(3) 0.0687(9) Uani 1 1 d . . .
H11A H 1.4063 1.0974 0.4695 0.082 Uiso 1 1 calc R . .
C12A C 1.4069(4) 1.1895(3) 0.3730(3) 0.0721(9) Uani 1 1 d . . .
H12A H 1.5057 1.2299 0.4023 0.087 Uiso 1 1 calc R . .
C13A C 1.3214(4) 1.2084(2) 0.2898(2) 0.0620(8) Uani 1 1 d . . .
C14A C 1.1716(4) 1.1507(2) 0.2469(2) 0.0588(8) Uani 1 1 d . . .
H14A H 1.1134 1.1648 0.1909 0.071 Uiso 1 1 calc R . .
C15A C 1.1098(3) 1.0728(2) 0.2872(2) 0.0508(7) Uani 1 1 d . . .
C16A C 0.9481(3) 1.0098(3) 0.2422(2) 0.0616(8) Uani 1 1 d . . .
H16A H 0.9464 0.9342 0.2247 0.074 Uiso 1 1 calc R . .
H16B H 0.8951 1.0163 0.2876 0.074 Uiso 1 1 calc R . .
C17A C 0.7398(4) 0.5544(3) 0.5704(3) 0.0897(12) Uani 1 1 d D A .
H17B H 0.682 0.6067 0.5507 0.108 Uiso 1 1 calc R . .
H17A H 0.6998 0.52 0.6137 0.108 Uiso 1 1 calc R . .
C18A C 0.7220(7) 0.4694(3) 0.4845(3) 0.131(2) Uani 1 1 d D . .
H18C H 0.7695 0.5022 0.4443 0.197 Uiso 1 1 calc R . .
H18B H 0.6164 0.4398 0.4507 0.197 Uiso 1 1 calc R . .
H18A H 0.7689 0.4129 0.5047 0.197 Uiso 1 1 calc R . .
C19A C 0.9883(10) 0.5433(7) 0.6704(6) 0.084(4) Uani 0.428(12) 1 d PD A 1
H19A H 1.0905 0.5601 0.6678 0.1 Uiso 0.428(12) 1 calc PR A 1
H19B H 0.9439 0.4674 0.6434 0.1 Uiso 0.428(12) 1 calc PR A 1
C20A C 0.9908(16) 0.5687(15) 0.7730(7) 0.127(6) Uani 0.428(12) 1 d PD A 1
H20A H 1.0369 0.6436 0.7993 0.19 Uiso 0.428(12) 1 calc PR A 1
H20C H 1.048 0.5255 0.8088 0.19 Uiso 0.428(12) 1 calc PR A 1
H20B H 0.8891 0.5528 0.7746 0.19 Uiso 0.428(12) 1 calc PR A 1
C19C C 0.9540(11) 0.6017(7) 0.7241(8) 0.103(3) Uani 0.572(12) 1 d PD A 2
H19C H 1.0171 0.6699 0.7632 0.124 Uiso 0.572(12) 1 calc PR A 2
H19D H 0.8698 0.5794 0.7463 0.124 Uiso 0.572(12) 1 calc PR A 2
C20C C 1.0458(13) 0.5150(9) 0.7222(11) 0.142(5) Uani 0.572(12) 1 d PD A 2
H20F H 0.985 0.4524 0.6755 0.213 Uiso 0.572(12) 1 calc PR A 2
H20D H 1.0748 0.4957 0.7827 0.213 Uiso 0.572(12) 1 calc PR A 2
H20E H 1.1348 0.5427 0.7073 0.213 Uiso 0.572(12) 1 calc PR A 2
N9A N 1.1260(3) 0.9707(2) 0.40780(19) 0.0592(7) Uani 1 1 d . . .
N1A N 0.8980(4) 0.6091(3) 0.6179(3) 0.1005(12) Uani 1 1 d D . .
O1A O 0.8797(3) 0.8378(2) 0.3978(2) 0.0945(9) Uani 1 1 d D . .
O2A O 0.8716(3) 1.0455(2) 0.1618(2) 0.0764(7) Uani 1 1 d . . .
Cl1A Cl 1.39949(12) 1.30590(8) 0.23854(8) 0.0895(4) Uani 1 1 d . . .
H1A H 0.942(4) 0.892(2) 0.392(3) 0.107 Uiso 1 1 d D . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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
O1B C2B C3B 122.6(3) . . ?
O1B C2B C7B 119.4(3) . . ?
C3B C2B C7B 118.0(2) . . ?
C2B C3B C4B 122.8(3) . . ?
C2B C3B H3B 118.6 . . ?
C4B C3B H3B 118.6 . . ?
N1B C4B C3B 122.0(3) . . ?
N1B C4B C5B 119.9(3) . . ?
C3B C4B C5B 118.0(3) . . ?
C6B C5B C4B 120.6(3) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C5B C6B C7B 122.3(3) . . ?
C5B C6B H6B 118.9 . . ?
C7B C6B H6B 118.9 . . ?
C8B C7B C6B 119.3(2) . . ?
C8B C7B C2B 122.4(2) . . ?
C6B C7B C2B 118.3(3) . . ?
N9B C8B C7B 124.7(3) . . ?
N9B C8B H8B 117.6 . . ?
C7B C8B H8B 117.6 . . ?
C11B C10B C15B 120.0(3) . . ?
C11B C10B N9B 121.6(2) . . ?
C15B C10B N9B 118.4(2) . . ?
C12B C11B C10B 121.0(3) . . ?
C12B C11B H11B 119.5 . . ?
C10B C11B H11B 119.5 . . ?
C11B C12B C13B 118.4(3) . . ?
C11B C12B H12B 120.8 . . ?
C13B C12B H12B 120.8 . . ?
C14B C13B C12B 121.5(3) . . ?
C14B C13B Cl1B 119.8(2) . . ?
C12B C13B Cl1B 118.7(3) . . ?
C13B C14B C15B 120.6(3) . . ?
C13B C14B H14B 119.7 . . ?
C15B C14B H14B 119.7 . . ?
C14B C15B C10B 118.4(3) . . ?
C14B C15B C16B 120.8(2) . . ?
C10B C15B C16B 120.8(3) . . ?
O2B C16B C15B 109.6(3) . . ?
O2B C16B H16C 109.7 . . ?
C15B C16B H16C 109.7 . . ?
O2B C16B H16D 109.7 . . ?
C15B C16B H16D 109.7 . . ?
H16C C16B H16D 108.2 . . ?
N1B C17B C18B 106.0(4) . . ?
N1B C17B H17D 110.5 . . ?
C18B C17B H17D 110.5 . . ?
N1B C17B H17C 110.5 . . ?
C18B C17B H17C 110.5 . . ?
H17D C17B H17C 108.7 . . ?
C17B C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C17B C18B H18D 109.5 . . ?
H18E C18B H18D 109.5 . . ?
H18F C18B H18D 109.5 . . ?
N1B C19B C20B 112.3(3) . . ?
N1B C19B H19E 109.2 . . ?
C20B C19B H19E 109.2 . . ?
N1B C19B H19F 109.2 . . ?
C20B C19B H19F 109.2 . . ?
H19E C19B H19F 107.9 . . ?
C19B C20B H20G 109.5 . . ?
C19B C20B H20I 109.5 . . ?
H20G C20B H20I 109.5 . . ?
C19B C20B H20H 109.5 . . ?
H20G C20B H20H 109.5 . . ?
H20I C20B H20H 109.5 . . ?
C4B N1B C19B 122.5(3) . . ?
C4B N1B C17B 122.2(3) . . ?
C19B N1B C17B 115.2(3) . . ?
C8B N9B C10B 127.0(2) . . ?
C8B N9B H9B 104(2) . . ?
C10B N9B H9B 129(2) . . ?
C16B O2B H2B 110(3) . . ?
O1A C2A C3A 118.7(3) . . ?
O1A C2A C7A 120.8(3) . . ?
C3A C2A C7A 120.4(3) . . ?
C4A C3A C2A 122.2(3) . . ?
C4A C3A H3A 118.9 . . ?
C2A C3A H3A 118.9 . . ?
N1A C4A C3A 121.8(3) . . ?
N1A C4A C5A 120.7(3) . . ?
C3A C4A C5A 117.5(3) . . ?
C6A C5A C4A 119.4(3) . . ?
C6A C5A H5A 120.3 . . ?
C4A C5A H5A 120.3 . . ?
C5A C6A C7A 124.1(3) . . ?
C5A C6A H6A 118 . . ?
C7A C6A H6A 118 . . ?
C6A C7A C2A 116.3(3) . . ?
C6A C7A C8A 122.1(3) . . ?
C2A C7A C8A 121.5(3) . . ?
N9A C8A C7A 122.5(3) . . ?
N9A C8A H8A 118.8 . . ?
C7A C8A H8A 118.8 . . ?
C15A C10A C11A 119.6(3) . . ?
C15A C10A N9A 116.3(2) . . ?
C11A C10A N9A 124.1(3) . . ?
C12A C11A C10A 120.0(3) . . ?
C12A C11A H11A 120 . . ?
C10A C11A H11A 120 . . ?
C13A C12A C11A 120.3(3) . . ?
C13A C12A H12A 119.9 . . ?
C11A C12A H12A 119.9 . . ?
C12A C13A C14A 120.3(3) . . ?
C12A C13A Cl1A 119.7(3) . . ?
C14A C13A Cl1A 120.0(3) . . ?
C15A C14A C13A 120.0(3) . . ?
C15A C14A H14A 120 . . ?
C13A C14A H14A 120 . . ?
C14A C15A C10A 119.7(3) . . ?
C14A C15A C16A 120.9(3) . . ?
C10A C15A C16A 119.4(3) . . ?
O2A C16A C15A 112.4(3) . . ?
O2A C16A H16A 109.1 . . ?
C15A C16A H16A 109.1 . . ?
O2A C16A H16B 109.1 . . ?
C15A C16A H16B 109.1 . . ?
H16A C16A H16B 107.9 . . ?
N1A C17A C18A 111.1(4) . . ?
N1A C17A H17B 109.4 . . ?
C18A C17A H17B 109.4 . . ?
N1A C17A H17A 109.4 . . ?
C18A C17A H17A 109.4 . . ?
H17B C17A H17A 108 . . ?
C17A C18A H18C 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18C C18A H18B 109.5 . . ?
C17A C18A H18A 109.5 . . ?
H18C C18A H18A 109.5 . . ?
H18B C18A H18A 109.5 . . ?
N1A C19A C20A 107.7(9) . . ?
N1A C19A H19A 110.2 . . ?
C20A C19A H19A 110.2 . . ?
N1A C19A H19B 110.2 . . ?
C20A C19A H19B 110.2 . . ?
H19A C19A H19B 108.5 . . ?
C20C C19C N1A 101.6(9) . . ?
C20C C19C H19C 111.4 . . ?
N1A C19C H19C 111.4 . . ?
C20C C19C H19D 111.4 . . ?
N1A C19C H19D 111.4 . . ?
H19C C19C H19D 109.3 . . ?
C19C C20C H20F 109.5 . . ?
C19C C20C H20D 109.5 . . ?
H20F C20C H20D 109.5 . . ?
C19C C20C H20E 109.5 . . ?
H20F C20C H20E 109.5 . . ?
H20D C20C H20E 109.5 . . ?
C8A N9A C10A 124.0(3) . . ?
C4A N1A C17A 121.2(3) . . ?
C4A N1A C19A 118.7(5) . . ?
C17A N1A C19A 113.9(5) . . ?
C4A N1A C19C 121.8(5) . . ?
C17A N1A C19C 112.8(5) . . ?
C19A N1A C19C 46.1(5) . . ?
C2A O1A H1A 103(3) . . ?
C16A O2A H2A 108(3) . . ?
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
C2B O1B 1.303(3) . ?
C2B C3B 1.385(4) . ?
C2B C7B 1.444(4) . ?
C3B C4B 1.410(4) . ?
C3B H3B 0.93 . ?
C4B N1B 1.360(4) . ?
C4B C5B 1.418(4) . ?
C5B C6B 1.347(4) . ?
C5B H5B 0.93 . ?
C6B C7B 1.420(4) . ?
C6B H6B 0.93 . ?
C7B C8B 1.377(4) . ?
C8B N9B 1.328(3) . ?
C8B H8B 0.93 . ?
C10B C11B 1.392(4) . ?
C10B C15B 1.398(4) . ?
C10B N9B 1.411(4) . ?
C11B C12B 1.376(4) . ?
C11B H11B 0.93 . ?
C12B C13B 1.387(4) . ?
C12B H12B 0.93 . ?
C13B C14B 1.370(4) . ?
C13B Cl1B 1.740(3) . ?
C14B C15B 1.389(4) . ?
C14B H14B 0.93 . ?
C15B C16B 1.506(4) . ?
C16B O2B 1.403(3) . ?
C16B H16C 0.97 . ?
C16B H16D 0.97 . ?
C17B N1B 1.475(5) . ?
C17B C18B 1.538(3) . ?
C17B H17D 0.97 . ?
C17B H17C 0.97 . ?
C18B H18E 0.96 . ?
C18B H18F 0.96 . ?
C18B H18D 0.96 . ?
C19B N1B 1.469(4) . ?
C19B C20B 1.536(3) . ?
C19B H19E 0.97 . ?
C19B H19F 0.97 . ?
C20B H20G 0.96 . ?
C20B H20I 0.96 . ?
C20B H20H 0.96 . ?
N9B H9B 0.85(3) . ?
O2B H2B 0.78(4) . ?
C2A O1A 1.335(4) . ?
C2A C3A 1.386(5) . ?
C2A C7A 1.416(4) . ?
C3A C4A 1.384(5) . ?
C3A H3A 0.93 . ?
C4A N1A 1.363(5) . ?
C4A C5A 1.420(5) . ?
C5A C6A 1.368(5) . ?
C5A H5A 0.93 . ?
C6A C7A 1.384(5) . ?
C6A H6A 0.93 . ?
C7A C8A 1.422(4) . ?
C8A N9A 1.285(4) . ?
C8A H8A 0.93 . ?
C10A C15A 1.394(4) . ?
C10A C11A 1.396(4) . ?
C10A N9A 1.415(4) . ?
C11A C12A 1.377(5) . ?
C11A H11A 0.93 . ?
C12A C13A 1.368(5) . ?
C12A H12A 0.93 . ?
C13A C14A 1.394(5) . ?
C13A Cl1A 1.735(3) . ?
C14A C15A 1.377(4) . ?
C14A H14A 0.93 . ?
C15A C16A 1.506(4) . ?
C16A O2A 1.410(4) . ?
C16A H16A 0.97 . ?
C16A H16B 0.97 . ?
C17A N1A 1.455(3) . ?
C17A C18A 1.531(3) . ?
C17A H17B 0.97 . ?
C17A H17A 0.97 . ?
C18A H18C 0.96 . ?
C18A H18B 0.96 . ?
C18A H18A 0.96 . ?
C19A N1A 1.464(3) . ?
C19A C20A 1.542(3) . ?
C19A H19A 0.97 . ?
C19A H19B 0.97 . ?
C20A H20A 0.96 . ?
C20A H20C 0.96 . ?
C20A H20B 0.96 . ?
C19C C20C 1.541(3) . ?
C19C N1A 1.567(12) . ?
C19C H19C 0.97 . ?
C19C H19D 0.97 . ?
C20C H20F 0.96 . ?
C20C H20D 0.96 . ?
C20C H20E 0.96 . ?
O1A H1A 0.863(19) . ?
O2A H2A 0.78(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1B C2B C3B C4B 177.8(3) . . . . ?
C7B C2B C3B C4B -2.8(5) . . . . ?
C2B C3B C4B N1B 178.6(3) . . . . ?
C2B C3B C4B C5B 1.1(5) . . . . ?
N1B C4B C5B C6B -176.6(3) . . . . ?
C3B C4B C5B C6B 0.9(5) . . . . ?
C4B C5B C6B C7B -1.1(5) . . . . ?
C5B C6B C7B C8B 179.6(3) . . . . ?
C5B C6B C7B C2B -0.7(4) . . . . ?
O1B C2B C7B C8B 1.7(4) . . . . ?
C3B C2B C7B C8B -177.8(3) . . . . ?
O1B C2B C7B C6B -178.0(3) . . . . ?
C3B C2B C7B C6B 2.5(4) . . . . ?
C6B C7B C8B N9B -179.6(3) . . . . ?
C2B C7B C8B N9B 0.7(4) . . . . ?
C15B C10B C11B C12B 2.3(4) . . . . ?
N9B C10B C11B C12B -177.5(3) . . . . ?
C10B C11B C12B C13B 0.6(5) . . . . ?
C11B C12B C13B C14B -2.5(5) . . . . ?
C11B C12B C13B Cl1B 178.1(2) . . . . ?
C12B C13B C14B C15B 1.5(4) . . . . ?
Cl1B C13B C14B C15B -179.1(2) . . . . ?
C13B C14B C15B C10B 1.4(4) . . . . ?
C13B C14B C15B C16B -176.8(3) . . . . ?
C11B C10B C15B C14B -3.3(4) . . . . ?
N9B C10B C15B C14B 176.5(2) . . . . ?
C11B C10B C15B C16B 174.9(3) . . . . ?
N9B C10B C15B C16B -5.3(4) . . . . ?
C14B C15B C16B O2B 11.1(4) . . . . ?
C10B C15B C16B O2B -167.0(3) . . . . ?
C3B C4B N1B C19B 168.0(3) . . . . ?
C5B C4B N1B C19B -14.6(5) . . . . ?
C3B C4B N1B C17B -15.0(6) . . . . ?
C5B C4B N1B C17B 162.5(3) . . . . ?
C20B C19B N1B C4B 94.1(4) . . . . ?
C20B C19B N1B C17B -83.1(4) . . . . ?
C18B C17B N1B C4B 95.3(5) . . . . ?
C18B C17B N1B C19B -87.5(4) . . . . ?
C7B C8B N9B C10B 178.1(2) . . . . ?
C11B C10B N9B C8B -6.1(4) . . . . ?
C15B C10B N9B C8B 174.1(2) . . . . ?
O1A C2A C3A C4A -178.8(3) . . . . ?
C7A C2A C3A C4A 0.7(6) . . . . ?
C2A C3A C4A N1A 179.7(4) . . . . ?
C2A C3A C4A C5A 1.8(6) . . . . ?
N1A C4A C5A C6A 179.2(4) . . . . ?
C3A C4A C5A C6A -2.9(6) . . . . ?
C4A C5A C6A C7A 1.6(6) . . . . ?
C5A C6A C7A C2A 0.9(5) . . . . ?
C5A C6A C7A C8A -179.6(3) . . . . ?
O1A C2A C7A C6A 177.5(3) . . . . ?
C3A C2A C7A C6A -2.0(5) . . . . ?
O1A C2A C7A C8A -2.0(5) . . . . ?
C3A C2A C7A C8A 178.5(3) . . . . ?
C6A C7A C8A N9A -179.6(3) . . . . ?
C2A C7A C8A N9A -0.1(5) . . . . ?
C15A C10A C11A C12A -0.6(5) . . . . ?
N9A C10A C11A C12A -178.6(3) . . . . ?
C10A C11A C12A C13A -1.1(5) . . . . ?
C11A C12A C13A C14A 2.0(5) . . . . ?
C11A C12A C13A Cl1A -178.7(3) . . . . ?
C12A C13A C14A C15A -1.2(5) . . . . ?
Cl1A C13A C14A C15A 179.6(2) . . . . ?
C13A C14A C15A C10A -0.6(4) . . . . ?
C13A C14A C15A C16A 179.8(3) . . . . ?
C11A C10A C15A C14A 1.4(4) . . . . ?
N9A C10A C15A C14A 179.6(2) . . . . ?
C11A C10A C15A C16A -178.9(3) . . . . ?
N9A C10A C15A C16A -0.7(4) . . . . ?
C14A C15A C16A O2A -4.0(4) . . . . ?
C10A C15A C16A O2A 176.3(3) . . . . ?
C7A C8A N9A C10A -179.6(3) . . . . ?
C15A C10A N9A C8A 175.5(3) . . . . ?
C11A C10A N9A C8A -6.4(5) . . . . ?
C3A C4A N1A C17A 3.2(6) . . . . ?
C5A C4A N1A C17A -179.1(4) . . . . ?
C3A C4A N1A C19A 153.9(6) . . . . ?
C5A C4A N1A C19A -28.3(7) . . . . ?
C3A C4A N1A C19C -152.2(5) . . . . ?
C5A C4A N1A C19C 25.5(6) . . . . ?
C18A C17A N1A C4A 78.8(5) . . . . ?
C18A C17A N1A C19A -73.2(6) . . . . ?
C18A C17A N1A C19C -123.8(5) . . . . ?
C20A C19A N1A C4A 112.9(8) . . . . ?
C20A C19A N1A C17A -94.3(9) . . . . ?
C20A C19A N1A C19C 5.0(9) . . . . ?
C20C C19C N1A C4A -99.5(7) . . . . ?
C20C C19C N1A C17A 103.2(7) . . . . ?
C20C C19C N1A C19A 1.3(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175954
