#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:26:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180079 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/25/7052533.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_7052533
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_formula_moiety         'C22 H29 N1 O2'
_chemical_formula_sum            'C22 H29 N O2'
_chemical_formula_weight         339.46
_chemical_name_common
'2,4-ditertbutyl-6-((2-hydroxymethylphenylimino)methyl) phenol'
_chemical_name_systematic
;
2,4-ditertbutyl-6-[(2-hydroxymethylphenylimino)methyl] 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                95.9376(7)
_cell_angle_beta                 104.1553(8)
_cell_angle_gamma                92.2975(8)
_cell_formula_units_Z            4
_cell_length_a                   10.2518(2)
_cell_length_b                   10.4845(2)
_cell_length_c                   19.6987(4)
_cell_measurement_reflns_used    14677
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_measurement_wavelength     0.71073
_cell_volume                     2037.31(7)
_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    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23875
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.07
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         9270
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0719
_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)+(0.0846P)²+0.2356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.2251
_reflns_number_gt                5174
_reflns_number_total             9270
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            C0NJ00179A.TXT
_cod_data_source_block           Compound2
_cod_database_code               7052533
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
H1B H 0.094(3) 0.375(3) 0.7784(15) 0.091(9) Uiso 1 1 d . . .
H1A H 0.379(3) 0.791(3) 0.8443(16) 0.093(10) Uiso 1 1 d . . .
H16B H 0.263(3) 0.921(3) 0.9202(14) 0.082(8) Uiso 1 1 d . . .
H16A H 0.210(3) 0.781(3) 0.9329(14) 0.087(9) Uiso 1 1 d . . .
C2A C 0.48393(19) 0.78422(19) 0.78453(11) 0.0476(5) Uani 1 1 d . . .
C3A C 0.4931(2) 0.7893(2) 0.71452(11) 0.0495(5) Uani 1 1 d . . .
O2C O 0.1533(7) 0.9579(7) 0.9813(5) 0.076(2) Uani 0.374(2) 1 d PD A 1
H2C H 0.0976 0.9844 0.9493 0.114 Uiso 0.374(2) 1 calc PR A 1
O2A O 0.1073(4) 0.8981(4) 0.9613(3) 0.0715(13) Uani 0.627(4) 1 d PD A 2
H2A H 0.1047 0.9763 0.9684 0.107 Uiso 0.627(4) 1 calc PR A 2
C4A C 0.6215(2) 0.7941(2) 0.70376(11) 0.0539(5) Uani 1 1 d . . .
H4A H 0.6289 0.7953 0.6577 0.065 Uiso 1 1 calc R . .
C5A C 0.7414(2) 0.7973(2) 0.75687(11) 0.0511(5) Uani 1 1 d . B .
C6A C 0.72747(19) 0.7963(2) 0.82453(10) 0.0490(5) Uani 1 1 d . . .
H6A H 0.8046 0.8006 0.8614 0.059 Uiso 1 1 calc R . .
C7A C 0.60111(19) 0.78922(19) 0.83961(10) 0.0457(5) Uani 1 1 d . . .
C8A C 0.5956(2) 0.80291(19) 0.91289(11) 0.0485(5) Uani 1 1 d . . .
H8A H 0.6761 0.8117 0.9478 0.058 Uiso 1 1 calc R . .
C10A C 0.4801(2) 0.83204(19) 1.00295(11) 0.0509(5) Uani 1 1 d U . .
C15A C 0.3547(2) 0.86549(19) 1.01377(12) 0.0567(6) Uani 1 1 d U A .
C14A C 0.3450(3) 0.8947(2) 1.08257(15) 0.0716(7) Uani 1 1 d U . .
H14A H 0.2628 0.9171 1.0907 0.086 Uiso 1 1 calc R . .
C13A C 0.4536(3) 0.8912(2) 1.13906(14) 0.0764(8) Uani 1 1 d U . .
H13A H 0.4442 0.9104 1.1847 0.092 Uiso 1 1 calc R . .
C12A C 0.5758(3) 0.8595(2) 1.12805(13) 0.0747(7) Uani 1 1 d U . .
H12A H 0.6500 0.8588 1.1662 0.090 Uiso 1 1 calc R . .
C11A C 0.5887(3) 0.8288(2) 1.06028(12) 0.0647(6) Uani 1 1 d U . .
H11A H 0.6713 0.8056 1.0531 0.078 Uiso 1 1 calc R . .
C16A C 0.2372(3) 0.8678(3) 0.95088(16) 0.0721(7) Uani 1 1 d D . .
C21A C 0.3662(2) 0.7922(2) 0.65418(12) 0.0621(6) Uani 1 1 d U . .
C17A C 0.8810(2) 0.8073(3) 0.74120(13) 0.0718(6) Uani 1 1 d DU . .
C23A C 0.2922(3) 0.9125(3) 0.66827(15) 0.0836(8) Uani 1 1 d U . .
H23A H 0.2666 0.9106 0.7119 0.125 Uiso 1 1 calc R . .
H23B H 0.2129 0.9144 0.6305 0.125 Uiso 1 1 calc R . .
H23C H 0.3506 0.9878 0.6712 0.125 Uiso 1 1 calc R . .
C24A C 0.2727(2) 0.6707(3) 0.64719(14) 0.0784(7) Uani 1 1 d U . .
H24A H 0.3193 0.5961 0.6372 0.118 Uiso 1 1 calc R . .
H24B H 0.1937 0.6742 0.6095 0.118 Uiso 1 1 calc R . .
H24C H 0.2466 0.6657 0.6905 0.118 Uiso 1 1 calc R . .
C22A C 0.4017(3) 0.7981(3) 0.58325(13) 0.0882(9) Uani 1 1 d U . .
H22A H 0.4602 0.8733 0.5860 0.132 Uiso 1 1 calc R . .
H22B H 0.3207 0.8019 0.5469 0.132 Uiso 1 1 calc R . .
H22C H 0.4465 0.7228 0.5724 0.132 Uiso 1 1 calc R . .
C18A C 0.9694(3) 0.7058(4) 0.7777(2) 0.0718(6) Uani 0.707(3) 1 d PDU B 1
H18A H 0.9291 0.6213 0.7587 0.108 Uiso 0.707(3) 1 calc PR B 1
H18B H 0.9762 0.7183 0.8274 0.108 Uiso 0.707(3) 1 calc PR B 1
H18C H 1.0577 0.7146 0.7696 0.108 Uiso 0.707(3) 1 calc PR B 1
C20A C 0.8764(5) 0.7902(6) 0.6633(2) 0.0991(10) Uani 0.707(3) 1 d PDU B 1
H20A H 0.9665 0.7882 0.6574 0.149 Uiso 0.707(3) 1 calc PR B 1
H20B H 0.8335 0.8607 0.6415 0.149 Uiso 0.707(3) 1 calc PR B 1
H20C H 0.8262 0.7111 0.6416 0.149 Uiso 0.707(3) 1 calc PR B 1
C19A C 0.9496(4) 0.9434(5) 0.7721(3) 0.0991(10) Uani 0.707(3) 1 d PDU B 1
H19A H 1.0353 0.9524 0.7609 0.149 Uiso 0.707(3) 1 calc PR B 1
H19B H 0.9628 0.9538 0.8224 0.149 Uiso 0.707(3) 1 calc PR B 1
H19C H 0.8930 1.0077 0.7521 0.149 Uiso 0.707(3) 1 calc PR B 1
C18C C 0.9950(9) 0.7902(14) 0.8040(5) 0.0991(10) Uani 0.293(3) 1 d PD B 2
H18D H 0.9756 0.7135 0.8235 0.149 Uiso 0.293(3) 1 calc PR B 2
H18E H 1.0045 0.8630 0.8390 0.149 Uiso 0.293(3) 1 calc PR B 2
H18F H 1.0774 0.7831 0.7893 0.149 Uiso 0.293(3) 1 calc PR B 2
C20C C 0.8769(11) 0.7083(13) 0.6759(6) 0.0991(10) Uani 0.293(3) 1 d PD B 2
H20D H 0.8122 0.7315 0.6357 0.149 Uiso 0.293(3) 1 calc PR B 2
H20E H 0.8515 0.6241 0.6853 0.149 Uiso 0.293(3) 1 calc PR B 2
H20F H 0.9644 0.7084 0.6664 0.149 Uiso 0.293(3) 1 calc PR B 2
C19C C 0.9018(11) 0.9414(10) 0.7221(6) 0.0991(10) Uani 0.293(3) 1 d PD B 2
H19D H 0.9959 0.9607 0.7262 0.149 Uiso 0.293(3) 1 calc PR B 2
H19E H 0.8708 1.0023 0.7535 0.149 Uiso 0.293(3) 1 calc PR B 2
H19F H 0.8517 0.9463 0.6745 0.149 Uiso 0.293(3) 1 calc PR B 2
N9A N 0.48419(17) 0.80341(16) 0.93143(9) 0.0512(4) Uani 1 1 d . . .
O1A O 0.36120(14) 0.77888(17) 0.79871(9) 0.0647(5) Uani 1 1 d . . .
C2B C 0.1903(2) 0.3492(2) 0.71105(11) 0.0504(5) Uani 1 1 d . . .
C3B C 0.1963(2) 0.3077(2) 0.64187(11) 0.0533(5) Uani 1 1 d . . .
C4B C 0.3236(2) 0.3059(2) 0.62982(11) 0.0584(6) Uani 1 1 d . . .
H4B H 0.3294 0.2781 0.5843 0.070 Uiso 1 1 calc R . .
C5B C 0.4447(2) 0.3427(2) 0.68066(12) 0.0573(6) Uani 1 1 d . . .
C6B C 0.4331(2) 0.3851(2) 0.74692(11) 0.0564(5) Uani 1 1 d . . .
H6B H 0.5108 0.4128 0.7819 0.068 Uiso 1 1 calc R . .
C7B C 0.3083(2) 0.3879(2) 0.76362(10) 0.0504(5) Uani 1 1 d . . .
C8B C 0.3051(2) 0.4210(2) 0.83632(11) 0.0535(5) Uani 1 1 d . . .
H8B H 0.3854 0.4490 0.8693 0.064 Uiso 1 1 calc R . .
C10B C 0.2000(2) 0.43614(19) 0.93006(10) 0.0489(5) Uani 1 1 d . . .
C15B C 0.1117(2) 0.3602(2) 0.95535(11) 0.0522(5) Uani 1 1 d . . .
C14B C 0.1128(3) 0.3827(2) 1.02617(12) 0.0657(6) Uani 1 1 d . . .
H14B H 0.0535 0.3338 1.0436 0.079 Uiso 1 1 calc R . .
C13B C 0.1996(3) 0.4756(3) 1.07133(13) 0.0715(7) Uani 1 1 d . . .
H13B H 0.1990 0.4885 1.1187 0.086 Uiso 1 1 calc R . .
C12B C 0.2867(3) 0.5488(2) 1.04627(13) 0.0709(7) Uani 1 1 d . . .
H12B H 0.3456 0.6115 1.0767 0.085 Uiso 1 1 calc R . .
C11B C 0.2875(2) 0.5301(2) 0.97597(12) 0.0638(6) Uani 1 1 d . . .
H11B H 0.3467 0.5805 0.9592 0.077 Uiso 1 1 calc R . .
C16B C 0.0213(3) 0.2527(2) 0.90841(13) 0.0698(7) Uani 1 1 d . . .
H16C H -0.0695 0.2809 0.8947 0.084 Uiso 1 1 calc R . .
H16D H 0.0522 0.2342 0.8659 0.084 Uiso 1 1 calc R . .
C21B C 0.0673(2) 0.2694(3) 0.58286(12) 0.0643(6) Uani 1 1 d U . .
C17B C 0.5798(2) 0.3353(3) 0.66071(13) 0.0712(7) Uani 1 1 d D . .
C22B C -0.0220(2) 0.3831(3) 0.57478(14) 0.0800(8) Uani 1 1 d . . .
H22D H -0.0443 0.4083 0.6186 0.120 Uiso 1 1 calc R . .
H22F H -0.1032 0.3585 0.5386 0.120 Uiso 1 1 calc R . .
H22E H 0.0256 0.4539 0.5620 0.120 Uiso 1 1 calc R . .
C23B C -0.0104(3) 0.1538(3) 0.60037(16) 0.0863(8) Uani 1 1 d . . .
H23D H 0.0447 0.0818 0.6038 0.130 Uiso 1 1 calc R . .
H23E H -0.0916 0.1320 0.5638 0.130 Uiso 1 1 calc R . .
H23F H -0.0329 0.1756 0.6445 0.130 Uiso 1 1 calc R . .
C24B C 0.0993(3) 0.2313(4) 0.51158(14) 0.1088(12) Uani 1 1 d . . .
H24F H 0.1457 0.3029 0.4988 0.163 Uiso 1 1 calc R . .
H24D H 0.0169 0.2074 0.4762 0.163 Uiso 1 1 calc R . .
H24E H 0.1555 0.1600 0.5152 0.163 Uiso 1 1 calc R . .
C19B C 0.6989(3) 0.3772(4) 0.72339(17) 0.1180(14) Uani 1 1 d DU . .
H19G H 0.6902 0.4638 0.7421 0.177 Uiso 1 1 calc R . .
H19H H 0.7812 0.3730 0.7085 0.177 Uiso 1 1 calc R . .
H19I H 0.7003 0.3212 0.7591 0.177 Uiso 1 1 calc R . .
C20B C 0.5947(3) 0.1968(4) 0.6316(2) 0.1188(13) Uani 1 1 d DU . .
H20G H 0.5955 0.1413 0.6675 0.178 Uiso 1 1 calc R . .
H20H H 0.6776 0.1926 0.6172 0.178 Uiso 1 1 calc R . .
H20I H 0.5203 0.1697 0.5917 0.178 Uiso 1 1 calc R . .
C18B C 0.5830(3) 0.4234(4) 0.60410(18) 0.1075(11) Uani 1 1 d DU . .
H18G H 0.5078 0.3994 0.5643 0.161 Uiso 1 1 calc R . .
H18H H 0.6655 0.4155 0.5896 0.147(13) Uiso 1 1 calc R . .
H18I H 0.5778 0.5108 0.6228 0.21(2) Uiso 1 1 calc R . .
N9B N 0.19669(17) 0.41362(17) 0.85728(9) 0.0519(4) Uani 1 1 d . . .
O2B O 0.0176(2) 0.13949(17) 0.94041(12) 0.0949(6) Uani 1 1 d D . .
H2B H -0.0180 0.1519 0.9733 0.142 Uiso 1 1 calc RD . .
O1B O 0.06850(14) 0.34947(17) 0.72697(9) 0.0644(5) Uani 1 1 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 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A C2A C7A 119.98(18) . . ?
O1A C2A C3A 119.58(18) . . ?
C7A C2A C3A 120.40(17) . . ?
C4A C3A C2A 116.54(18) . . ?
C4A C3A C21A 122.30(19) . . ?
C2A C3A C21A 121.16(18) . . ?
C16A O2C H2C 109.5 . . ?
C16A O2A H2A 109.5 . . ?
C3A C4A C5A 125.12(19) . . ?
C3A C4A H4A 117.4 . . ?
C5A C4A H4A 117.4 . . ?
C6A C5A C4A 116.18(18) . . ?
C6A C5A C17A 121.58(19) . . ?
C4A C5A C17A 122.19(19) . . ?
C5A C6A C7A 122.15(18) . . ?
C5A C6A H6A 118.9 . . ?
C7A C6A H6A 118.9 . . ?
C6A C7A C2A 119.55(18) . . ?
C6A C7A C8A 118.45(18) . . ?
C2A C7A C8A 121.57(17) . . ?
N9A C8A C7A 122.58(19) . . ?
N9A C8A H8A 118.7 . . ?
C7A C8A H8A 118.7 . . ?
C11A C10A C15A 119.71(19) . . ?
C11A C10A N9A 124.69(19) . . ?
C15A C10A N9A 115.61(19) . . ?
C14A C15A C10A 118.0(2) . . ?
C14A C15A C16A 122.9(2) . . ?
C10A C15A C16A 119.09(19) . . ?
C13A C14A C15A 121.7(2) . . ?
C13A C14A H14A 119.1 . . ?
C15A C14A H14A 119.1 . . ?
C12A C13A C14A 119.9(2) . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A H13A 120.1 . . ?
C13A C12A C11A 119.9(3) . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
C12A C11A C10A 120.7(2) . . ?
C12A C11A H11A 119.6 . . ?
C10A C11A H11A 119.6 . . ?
O2A C16A C15A 119.7(3) . . ?
O2C C16A C15A 100.3(4) . . ?
O2A C16A H16B 110.3(16) . . ?
O2C C16A H16B 97.8(16) . . ?
C15A C16A H16B 108.4(16) . . ?
O2A C16A H16A 94.5(17) . . ?
O2C C16A H16A 124.7(17) . . ?
C15A C16A H16A 106.5(17) . . ?
H16B C16A H16A 117(2) . . ?
C23A C21A C22A 107.5(2) . . ?
C23A C21A C3A 109.44(19) . . ?
C22A C21A C3A 111.56(19) . . ?
C23A C21A C24A 110.2(2) . . ?
C22A C21A C24A 107.6(2) . . ?
C3A C21A C24A 110.5(2) . . ?
C18C C17A C19C 107.2(7) . . ?
C18C C17A C20A 129.8(4) . . ?
C19C C17A C20A 74.5(5) . . ?
C18C C17A C5A 113.1(4) . . ?
C19C C17A C5A 107.1(4) . . ?
C20A C17A C5A 113.8(2) . . ?
C19C C17A C18A 137.3(5) . . ?
C20A C17A C18A 108.9(3) . . ?
C5A C17A C18A 109.5(2) . . ?
C18C C17A C20C 112.9(7) . . ?
C19C C17A C20C 108.9(7) . . ?
C5A C17A C20C 107.4(4) . . ?
C18A C17A C20C 80.3(6) . . ?
C18C C17A C19A 72.8(5) . . ?
C20A C17A C19A 107.4(3) . . ?
C5A C17A C19A 108.5(2) . . ?
C18A C17A C19A 108.5(3) . . ?
C20C C17A C19A 137.1(5) . . ?
C21A C23A H23A 109.5 . . ?
C21A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C21A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C21A C24A H24A 109.5 . . ?
C21A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C21A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C21A C22A H22A 109.5 . . ?
C21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
C17A C20A H20A 109.5 . . ?
C17A C20A H20B 109.5 . . ?
C17A C20A H20C 109.5 . . ?
C17A C19A H19A 109.5 . . ?
C17A C19A H19B 109.5 . . ?
C17A C19A H19C 109.5 . . ?
C17A C18C H18D 109.5 . . ?
C17A C18C H18E 109.5 . . ?
H18D C18C H18E 109.5 . . ?
C17A C18C H18F 109.5 . . ?
H18D C18C H18F 109.5 . . ?
H18E C18C H18F 109.5 . . ?
C17A C20C H20D 109.5 . . ?
C17A C20C H20E 109.5 . . ?
H20D C20C H20E 109.5 . . ?
C17A C20C H20F 109.5 . . ?
H20D C20C H20F 109.5 . . ?
H20E C20C H20F 109.5 . . ?
C17A C19C H19D 109.5 . . ?
C17A C19C H19E 109.5 . . ?
H19D C19C H19E 109.5 . . ?
C17A C19C H19F 109.5 . . ?
H19D C19C H19F 109.5 . . ?
H19E C19C H19F 109.5 . . ?
C8A N9A C10A 121.93(18) . . ?
C2A O1A H1A 104.0(19) . . ?
O1B C2B C7B 120.08(18) . . ?
O1B C2B C3B 119.30(18) . . ?
C7B C2B C3B 120.61(18) . . ?
C4B C3B C2B 116.31(19) . . ?
C4B C3B C21B 122.41(19) . . ?
C2B C3B C21B 121.27(18) . . ?
C3B C4B C5B 125.27(19) . . ?
C3B C4B H4B 117.4 . . ?
C5B C4B H4B 117.4 . . ?
C6B C5B C4B 116.11(19) . . ?
C6B C5B C17B 123.64(19) . . ?
C4B C5B C17B 120.25(19) . . ?
C5B C6B C7B 122.08(19) . . ?
C5B C6B H6B 119.0 . . ?
C7B C6B H6B 119.0 . . ?
C6B C7B C2B 119.58(18) . . ?
C6B C7B C8B 118.85(19) . . ?
C2B C7B C8B 121.38(18) . . ?
N9B C8B C7B 122.90(19) . . ?
N9B C8B H8B 118.5 . . ?
C7B C8B H8B 118.5 . . ?
C11B C10B C15B 119.82(19) . . ?
C11B C10B N9B 122.4(2) . . ?
C15B C10B N9B 117.79(18) . . ?
C14B C15B C10B 118.2(2) . . ?
C14B C15B C16B 120.3(2) . . ?
C10B C15B C16B 121.43(19) . . ?
C13B C14B C15B 121.7(2) . . ?
C13B C14B H14B 119.2 . . ?
C15B C14B H14B 119.2 . . ?
C12B C13B C14B 119.7(2) . . ?
C12B C13B H13B 120.1 . . ?
C14B C13B H13B 120.1 . . ?
C13B C12B C11B 120.2(2) . . ?
C13B C12B H12B 119.9 . . ?
C11B C12B H12B 119.9 . . ?
C12B C11B C10B 120.3(2) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
O2B C16B C15B 113.4(2) . . ?
O2B C16B H16C 108.9 . . ?
C15B C16B H16C 108.9 . . ?
O2B C16B H16D 108.9 . . ?
C15B C16B H16D 108.9 . . ?
H16C C16B H16D 107.7 . . ?
C22B C21B C24B 107.8(2) . . ?
C22B C21B C23B 109.7(2) . . ?
C24B C21B C23B 107.8(2) . . ?
C22B C21B C3B 109.60(19) . . ?
C24B C21B C3B 111.68(19) . . ?
C23B C21B C3B 110.2(2) . . ?
C19B C17B C18B 108.1(3) . . ?
C19B C17B C5B 112.1(2) . . ?
C18B C17B C5B 109.2(2) . . ?
C19B C17B C20B 108.9(3) . . ?
C18B C17B C20B 109.1(3) . . ?
C5B C17B C20B 109.3(2) . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22F C22B H22E 109.5 . . ?
C21B C23B H23D 109.5 . . ?
C21B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C21B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C21B C24B H24F 109.5 . . ?
C21B C24B H24D 109.5 . . ?
H24F C24B H24D 109.5 . . ?
C21B C24B H24E 109.5 . . ?
H24F C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C17B C19B H19G 109.5 . . ?
C17B C19B H19H 109.5 . . ?
H19G C19B H19H 109.5 . . ?
C17B C19B H19I 109.5 . . ?
H19G C19B H19I 109.5 . . ?
H19H C19B H19I 109.5 . . ?
C17B C20B H20G 109.5 . . ?
C17B C20B H20H 109.5 . . ?
H20G C20B H20H 109.5 . . ?
C17B C20B H20I 109.5 . . ?
H20G C20B H20I 109.5 . . ?
H20H C20B H20I 109.5 . . ?
C17B C18B H18G 109.5 . . ?
C17B C18B H18H 109.5 . . ?
H18G C18B H18H 109.5 . . ?
C17B C18B H18I 109.5 . . ?
H18G C18B H18I 109.5 . . ?
H18H C18B H18I 109.5 . . ?
C8B N9B C10B 120.92(18) . . ?
C16B O2B H2B 109.5 . . ?
C2B O1B H1B 102.4(16) . . ?
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
C2A O1A 1.354(2) . ?
C2A C7A 1.403(3) . ?
C2A C3A 1.411(3) . ?
C3A C4A 1.384(3) . ?
C3A C21A 1.536(3) . ?
O2C C16A 1.480(7) . ?
O2C H2C 0.8200 . ?
O2A C16A 1.439(4) . ?
O2A H2A 0.8200 . ?
C4A C5A 1.402(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.376(3) . ?
C5A C17A 1.538(3) . ?
C6A C7A 1.399(3) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.451(3) . ?
C8A N9A 1.281(2) . ?
C8A H8A 0.9300 . ?
C10A C11A 1.383(3) . ?
C10A C15A 1.406(3) . ?
C10A N9A 1.421(2) . ?
C15A C14A 1.387(3) . ?
C15A C16A 1.505(4) . ?
C14A C13A 1.373(4) . ?
C14A H14A 0.9300 . ?
C13A C12A 1.371(4) . ?
C13A H13A 0.9300 . ?
C12A C11A 1.380(3) . ?
C12A H12A 0.9300 . ?
C11A H11A 0.9300 . ?
C16A H16B 0.94(3) . ?
C16A H16A 0.94(3) . ?
C21A C23A 1.534(3) . ?
C21A C22A 1.534(3) . ?
C21A C24A 1.537(3) . ?
C17A C18C 1.511(10) . ?
C17A C19C 1.512(10) . ?
C17A C20A 1.515(5) . ?
C17A C18A 1.545(5) . ?
C17A C20C 1.558(10) . ?
C17A C19A 1.559(5) . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C24A H24A 0.9600 . ?
C24A H24B 0.9600 . ?
C24A H24C 0.9600 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C18C H18D 0.9600 . ?
C18C H18E 0.9600 . ?
C18C H18F 0.9600 . ?
C20C H20D 0.9600 . ?
C20C H20E 0.9600 . ?
C20C H20F 0.9600 . ?
C19C H19D 0.9600 . ?
C19C H19E 0.9600 . ?
C19C H19F 0.9600 . ?
O1A H1A 0.87(3) . ?
C2B O1B 1.360(2) . ?
C2B C7B 1.400(3) . ?
C2B C3B 1.404(3) . ?
C3B C4B 1.383(3) . ?
C3B C21B 1.540(3) . ?
C4B C5B 1.402(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.369(3) . ?
C5B C17B 1.532(3) . ?
C6B C7B 1.398(3) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.447(3) . ?
C8B N9B 1.279(2) . ?
C8B H8B 0.9300 . ?
C10B C11B 1.393(3) . ?
C10B C15B 1.396(3) . ?
C10B N9B 1.420(2) . ?
C15B C14B 1.387(3) . ?
C15B C16B 1.505(3) . ?
C14B C13B 1.377(4) . ?
C14B H14B 0.9300 . ?
C13B C12B 1.367(4) . ?
C13B H13B 0.9300 . ?
C12B C11B 1.380(3) . ?
C12B H12B 0.9300 . ?
C11B H11B 0.9300 . ?
C16B O2B 1.404(3) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C21B C22B 1.530(4) . ?
C21B C24B 1.536(3) . ?
C21B C23B 1.538(4) . ?
C17B C19B 1.522(4) . ?
C17B C18B 1.525(4) . ?
C17B C20B 1.533(4) . ?
C22B H22D 0.9600 . ?
C22B H22F 0.9600 . ?
C22B H22E 0.9600 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
C24B H24F 0.9600 . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C19B H19G 0.9600 . ?
C19B H19H 0.9600 . ?
C19B H19I 0.9600 . ?
C20B H20G 0.9600 . ?
C20B H20H 0.9600 . ?
C20B H20I 0.9600 . ?
C18B H18G 0.9600 . ?
C18B H18H 0.9600 . ?
C18B H18I 0.9600 . ?
O2B H2B 0.8200 . ?
O1B H1B 0.99(3) . ?
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
O1A C2A C3A C4A -179.75(19) . . . . ?
C7A C2A C3A C4A 2.5(3) . . . . ?
O1A C2A C3A C21A 1.5(3) . . . . ?
C7A C2A C3A C21A -176.26(19) . . . . ?
C2A C3A C4A C5A -1.6(3) . . . . ?
C21A C3A C4A C5A 177.2(2) . . . . ?
C3A C4A C5A C6A -0.5(3) . . . . ?
C3A C4A C5A C17A -177.8(2) . . . . ?
C4A C5A C6A C7A 1.6(3) . . . . ?
C17A C5A C6A C7A 179.0(2) . . . . ?
C5A C6A C7A C2A -0.7(3) . . . . ?
C5A C6A C7A C8A -173.36(19) . . . . ?
O1A C2A C7A C6A -179.20(18) . . . . ?
C3A C2A C7A C6A -1.5(3) . . . . ?
O1A C2A C7A C8A -6.8(3) . . . . ?
C3A C2A C7A C8A 170.95(18) . . . . ?
C6A C7A C8A N9A 176.79(19) . . . . ?
C2A C7A C8A N9A 4.3(3) . . . . ?
C11A C10A C15A C14A 0.2(3) . . . . ?
N9A C10A C15A C14A -179.87(18) . . . . ?
C11A C10A C15A C16A -179.6(2) . . . . ?
N9A C10A C15A C16A 0.3(3) . . . . ?
C10A C15A C14A C13A -0.1(3) . . . . ?
C16A C15A C14A C13A 179.7(2) . . . . ?
C15A C14A C13A C12A 0.6(4) . . . . ?
C14A C13A C12A C11A -1.2(4) . . . . ?
C13A C12A C11A C10A 1.3(4) . . . . ?
C15A C10A C11A C12A -0.8(3) . . . . ?
N9A C10A C11A C12A 179.3(2) . . . . ?
C14A C15A C16A O2A -1.6(4) . . . . ?
C10A C15A C16A O2A 178.1(3) . . . . ?
C14A C15A C16A O2C 24.1(4) . . . . ?
C10A C15A C16A O2C -156.1(4) . . . . ?
C4A C3A C21A C23A -117.7(2) . . . . ?
C2A C3A C21A C23A 61.0(3) . . . . ?
C4A C3A C21A C22A 1.1(3) . . . . ?
C2A C3A C21A C22A 179.8(2) . . . . ?
C4A C3A C21A C24A 120.8(2) . . . . ?
C2A C3A C21A C24A -60.5(3) . . . . ?
C6A C5A C17A C18C 11.0(7) . . . . ?
C4A C5A C17A C18C -171.8(6) . . . . ?
C6A C5A C17A C19C -106.9(5) . . . . ?
C4A C5A C17A C19C 70.3(5) . . . . ?
C6A C5A C17A C20A 172.8(3) . . . . ?
C4A C5A C17A C20A -10.0(4) . . . . ?
C6A C5A C17A C18A 50.6(3) . . . . ?
C4A C5A C17A C18A -132.1(3) . . . . ?
C6A C5A C17A C20C 136.3(6) . . . . ?
C4A C5A C17A C20C -46.5(7) . . . . ?
C6A C5A C17A C19A -67.7(3) . . . . ?
C4A C5A C17A C19A 109.6(3) . . . . ?
C7A C8A N9A C10A -172.38(17) . . . . ?
C11A C10A N9A C8A -17.7(3) . . . . ?
C15A C10A N9A C8A 162.35(19) . . . . ?
O1B C2B C3B C4B -178.0(2) . . . . ?
C7B C2B C3B C4B 0.9(3) . . . . ?
O1B C2B C3B C21B 3.3(3) . . . . ?
C7B C2B C3B C21B -177.8(2) . . . . ?
C2B C3B C4B C5B -0.4(4) . . . . ?
C21B C3B C4B C5B 178.3(2) . . . . ?
C3B C4B C5B C6B -0.9(4) . . . . ?
C3B C4B C5B C17B 179.5(2) . . . . ?
C4B C5B C6B C7B 1.9(3) . . . . ?
C17B C5B C6B C7B -178.6(2) . . . . ?
C5B C6B C7B C2B -1.5(3) . . . . ?
C5B C6B C7B C8B 173.6(2) . . . . ?
O1B C2B C7B C6B 178.9(2) . . . . ?
C3B C2B C7B C6B 0.0(3) . . . . ?
O1B C2B C7B C8B 3.9(3) . . . . ?
C3B C2B C7B C8B -174.9(2) . . . . ?
C6B C7B C8B N9B -172.9(2) . . . . ?
C2B C7B C8B N9B 2.1(3) . . . . ?
C11B C10B C15B C14B 0.9(3) . . . . ?
N9B C10B C15B C14B -179.10(18) . . . . ?
C11B C10B C15B C16B -176.5(2) . . . . ?
N9B C10B C15B C16B 3.5(3) . . . . ?
C10B C15B C14B C13B -1.0(3) . . . . ?
C16B C15B C14B C13B 176.4(2) . . . . ?
C15B C14B C13B C12B 0.5(4) . . . . ?
C14B C13B C12B C11B 0.2(4) . . . . ?
C13B C12B C11B C10B -0.3(4) . . . . ?
C15B C10B C11B C12B -0.3(3) . . . . ?
N9B C10B C11B C12B 179.7(2) . . . . ?
C14B C15B C16B O2B -41.5(3) . . . . ?
C10B C15B C16B O2B 135.8(2) . . . . ?
C4B C3B C21B C22B -119.7(2) . . . . ?
C2B C3B C21B C22B 58.9(3) . . . . ?
C4B C3B C21B C24B -0.4(4) . . . . ?
C2B C3B C21B C24B 178.3(2) . . . . ?
C4B C3B C21B C23B 119.4(3) . . . . ?
C2B C3B C21B C23B -61.9(3) . . . . ?
C6B C5B C17B C19B 1.5(4) . . . . ?
C4B C5B C17B C19B -179.0(3) . . . . ?
C6B C5B C17B C18B -118.4(3) . . . . ?
C4B C5B C17B C18B 61.1(3) . . . . ?
C6B C5B C17B C20B 122.3(3) . . . . ?
C4B C5B C17B C20B -58.2(3) . . . . ?
C7B C8B N9B C10B 174.35(19) . . . . ?
C11B C10B N9B C8B 37.6(3) . . . . ?
C15B C10B N9B C8B -142.4(2) . . . . ?
