#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/45/2224581.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_2224581
loop_
_publ_author_name
'Yazıcı, Serap'
'Albayrak, Çiğdem'
'Gümrükçüoğlu, İsmail'
'Şenel, İsmet'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (E)-2-Hydroxy-6-[(4-propylphenyl)iminiomethyl]phenolate
;
_journal_coeditor_code           CI2970
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o93
_journal_paper_doi               10.1107/S1600536809052246
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H17 N O2'
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.31
_chemical_name_systematic
;
(E)-2-Hydroxy-6-[(4-propylphenyl)iminiomethyl]phenolate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.418(3)
_cell_angle_beta                 103.259(3)
_cell_angle_gamma                95.540(3)
_cell_formula_units_Z            6
_cell_length_a                   11.5743(4)
_cell_length_b                   12.7635(4)
_cell_length_c                   14.1706(5)
_cell_measurement_reflns_used    36582
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      1.60
_cell_volume                     2027.15(12)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25371
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.2353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                6241
_reflns_number_total             7976
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2970.cif
_cod_data_source_block           I
_cod_original_cell_volume        2027.14(11)
_cod_database_code               2224581
_cod_database_fobs_code          2224581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C15B 1.2012(2) 0.92858(17) 0.75163(17) 0.0717(6) Uani d . 1 . .
H H15C 1.1547 0.9385 0.6867 0.086 Uiso calc R 1 . .
H H15D 1.2324 0.8608 0.7514 0.086 Uiso calc R 1 . .
C C16C 0.8117(3) 1.0067(2) 0.87450(19) 0.0926(8) Uani d . 1 . .
H H16A 0.8187 1.0279 0.8110 0.139 Uiso calc R 1 . .
H H16B 0.8864 0.9853 0.9097 0.139 Uiso calc R 1 . .
H H16C 0.7910 1.0649 0.9085 0.139 Uiso calc R 1 . .
C C1C 0.19899(13) 0.38530(11) 0.85202(11) 0.0367(3) Uani d . 1 . .
C C2C 0.18638(15) 0.29139(12) 0.79542(12) 0.0436(4) Uani d . 1 . .
H H2C 0.2466 0.2765 0.7653 0.052 Uiso calc R 1 . .
C C3C 0.08639(15) 0.22263(12) 0.78489(12) 0.0464(4) Uani d . 1 . .
H H3C 0.0789 0.1607 0.7481 0.056 Uiso calc R 1 . .
C C4C -0.00539(15) 0.24484(12) 0.82929(11) 0.0434(4) Uani d . 1 . .
H H4C -0.0737 0.1977 0.8209 0.052 Uiso calc R 1 . .
C C5C 0.00403(13) 0.33476(12) 0.88471(11) 0.0385(3) Uani d . 1 . .
C C6C 0.10763(13) 0.40783(11) 0.89947(10) 0.0356(3) Uani d . 1 . .
C C7C 0.30005(14) 0.45906(12) 0.85868(11) 0.0371(3) Uani d . 1 . .
C C8C 0.41020(13) 0.62687(11) 0.92008(10) 0.0353(3) Uani d . 1 . .
C C9C 0.39200(14) 0.72868(12) 0.94441(11) 0.0411(3) Uani d . 1 . .
H H9C 0.3171 0.7436 0.9509 0.049 Uiso calc R 1 . .
C C10C 0.48500(16) 0.80766(13) 0.95891(11) 0.0458(4) Uani d . 1 . .
H H10C 0.4717 0.8755 0.9750 0.055 Uiso calc R 1 . .
C C11C 0.59814(15) 0.78809(13) 0.94994(11) 0.0446(4) Uani d . 1 . .
C C12C 0.61472(15) 0.68592(13) 0.92674(12) 0.0453(4) Uani d . 1 . .
H H12C 0.6899 0.6709 0.9210 0.054 Uiso calc R 1 . .
C C13C 0.52270(14) 0.60541(12) 0.91182(11) 0.0416(3) Uani d . 1 . .
H H13C 0.5363 0.5374 0.8964 0.050 Uiso calc R 1 . .
C C14C 0.69818(18) 0.87517(15) 0.96110(13) 0.0579(5) Uani d . 1 . .
H H14E 0.7716 0.8494 0.9964 0.069 Uiso calc R 1 . .
H H14K 0.6814 0.9328 0.9993 0.069 Uiso calc R 1 . .
C C15C 0.7159(2) 0.91595(16) 0.86547(15) 0.0693(6) Uani d . 1 . .
H H15E 0.6411 0.9382 0.8290 0.083 Uiso calc R 1 . .
H H15K 0.7361 0.8588 0.8287 0.083 Uiso calc R 1 . .
N N1C 0.31247(11) 0.54844(9) 0.90723(9) 0.0364(3) Uani d . 1 . .
O O1C 0.11620(9) 0.49230(8) 0.95420(8) 0.0419(2) Uani d . 1 . .
O O2C -0.08724(9) 0.35566(9) 0.92583(8) 0.0444(3) Uani d . 1 . .
C C1B 0.63614(13) 0.42043(11) 0.74837(10) 0.0335(3) Uani d . 1 . .
C C2B 0.60523(14) 0.34026(12) 0.80990(11) 0.0411(3) Uani d . 1 . .
H H2B 0.6482 0.3393 0.8739 0.049 Uiso calc R 1 . .
C C3B 0.51316(14) 0.26497(12) 0.77577(11) 0.0420(3) Uani d . 1 . .
H H3B 0.4933 0.2132 0.8168 0.050 Uiso calc R 1 . .
C C4B 0.44776(13) 0.26496(11) 0.67878(11) 0.0365(3) Uani d . 1 . .
H H4B 0.3846 0.2135 0.6564 0.044 Uiso calc R 1 . .
C C5B 0.47644(12) 0.34010(11) 0.61725(10) 0.0333(3) Uani d . 1 . .
C C6B 0.57181(12) 0.42046(10) 0.65011(10) 0.0320(3) Uani d . 1 . .
C C7B 0.72796(13) 0.50219(11) 0.78451(10) 0.0345(3) Uani d . 1 . .
C C8B 0.84359(13) 0.66407(11) 0.75582(10) 0.0335(3) Uani d . 1 . .
C C9B 0.84990(14) 0.74062(11) 0.68709(11) 0.0387(3) Uani d . 1 . .
H H9B 0.7952 0.7354 0.6275 0.046 Uiso calc R 1 . .
C C10B 0.93783(15) 0.82436(12) 0.70778(12) 0.0445(4) Uani d . 1 . .
H H10B 0.9415 0.8749 0.6614 0.053 Uiso calc R 1 . .
C C11B 1.02074(15) 0.83477(11) 0.79620(11) 0.0416(3) Uani d . 1 . .
C C12B 1.01168(14) 0.75811(12) 0.86405(11) 0.0421(3) Uani d . 1 . .
H H12B 1.0654 0.7640 0.9241 0.051 Uiso calc R 1 . .
C C13B 0.92505(14) 0.67347(12) 0.84472(11) 0.0392(3) Uani d . 1 . .
H H13B 0.9214 0.6230 0.8912 0.047 Uiso calc R 1 . .
C C14B 1.11991(17) 0.92395(13) 0.81796(13) 0.0517(4) Uani d . 1 . .
H H14C 1.0845 0.9900 0.8156 0.062 Uiso calc R 1 . .
H H14D 1.1663 0.9173 0.8836 0.062 Uiso calc R 1 . .
C C16B 1.30486(17) 1.01232(13) 0.77300(14) 0.0547(4) Uani d . 1 . .
H H16K 1.3518 1.0070 0.7257 0.082 Uiso calc R 1 . .
H H16L 1.3532 1.0031 0.8366 0.082 Uiso calc R 1 . .
H H16M 1.2758 1.0804 0.7704 0.082 Uiso calc R 1 . .
N N1B 0.75502(10) 0.57790(9) 0.72934(9) 0.0333(3) Uani d . 1 . .
O O1B 0.59829(9) 0.49057(8) 0.59003(7) 0.0402(2) Uani d . 1 . .
O O2B 0.41492(9) 0.33925(9) 0.52316(7) 0.0400(2) Uani d . 1 . .
H H1A 0.023(2) 0.7711(18) 0.4586(16) 0.085(7) Uiso d . 1 . .
H H1B 0.701(2) 0.5644(18) 0.6580(17) 0.089(7) Uiso d . 1 . .
H H1C 0.235(2) 0.5505(19) 0.9370(18) 0.097(8) Uiso d . 1 . .
H H5A 0.101(2) 1.0706(16) 0.5252(15) 0.072(7) Uiso d . 1 . .
H H5B 0.440(2) 0.3985(18) 0.4978(16) 0.079(7) Uiso d . 1 . .
H H5C -0.069(2) 0.4157(19) 0.9650(18) 0.087(8) Uiso d . 1 . .
H H7A 0.1778(16) 0.6796(14) 0.3642(12) 0.050(5) Uiso d . 1 . .
H H7B 0.7716(15) 0.4995(12) 0.8521(12) 0.044(4) Uiso d . 1 . .
H H7C 0.3628(15) 0.4447(12) 0.8263(11) 0.037(4) Uiso d . 1 . .
C C1A 0.20614(13) 0.83448(11) 0.41888(10) 0.0362(3) Uani d . 1 . .
C C2A 0.31409(14) 0.85933(13) 0.38903(12) 0.0443(4) Uani d . 1 . .
H H2A 0.3450 0.8081 0.3578 0.053 Uiso calc R 1 . .
C C3A 0.37295(14) 0.95801(13) 0.40592(13) 0.0472(4) Uani d . 1 . .
H H3A 0.4439 0.9737 0.3864 0.057 Uiso calc R 1 . .
C C4A 0.32645(14) 1.03589(12) 0.45274(12) 0.0424(4) Uani d . 1 . .
H H4A 0.3676 1.1027 0.4645 0.051 Uiso calc R 1 . .
C C5A 0.22182(13) 1.01489(11) 0.48125(11) 0.0374(3) Uani d . 1 . .
C C6A 0.15744(13) 0.91300(11) 0.46528(10) 0.0351(3) Uani d . 1 . .
C C7A 0.14494(13) 0.73221(11) 0.40063(11) 0.0371(3) Uani d . 1 . .
C C8A -0.02951(13) 0.61121(10) 0.40566(10) 0.0339(3) Uani d . 1 . .
C C9A -0.13686(14) 0.60527(11) 0.43360(11) 0.0393(3) Uani d . 1 . .
H H9A -0.1566 0.6624 0.4656 0.047 Uiso calc R 1 . .
C C10A -0.21506(14) 0.51438(11) 0.41402(11) 0.0398(3) Uani d . 1 . .
H H10A -0.2867 0.5111 0.4336 0.048 Uiso calc R 1 . .
C C11A -0.18835(13) 0.42820(11) 0.36572(10) 0.0347(3) Uani d . 1 . .
C C12A -0.08046(14) 0.43637(11) 0.33756(11) 0.0402(3) Uani d . 1 . .
H H12A -0.0612 0.3798 0.3045 0.048 Uiso calc R 1 . .
C C13A -0.00149(14) 0.52570(11) 0.35715(12) 0.0409(3) Uani d . 1 . .
H H13A 0.0704 0.5289 0.3380 0.049 Uiso calc R 1 . .
C C14A -0.27040(14) 0.32742(11) 0.34356(11) 0.0393(3) Uani d . 1 . .
H H14A -0.2310 0.2721 0.3807 0.047 Uiso calc R 1 . .
H H14B -0.2804 0.3089 0.2755 0.047 Uiso calc R 1 . .
C C15A -0.39285(16) 0.32782(13) 0.36385(13) 0.0509(4) Uani d . 1 . .
H H15A -0.4341 0.3821 0.3266 0.061 Uiso calc R 1 . .
H H15B -0.3846 0.3448 0.4321 0.061 Uiso calc R 1 . .
C C16A -0.46688(18) 0.22241(15) 0.33830(15) 0.0619(5) Uani d . 1 . .
H H16D -0.5437 0.2259 0.3524 0.093 Uiso calc R 1 . .
H H16E -0.4270 0.1686 0.3758 0.093 Uiso calc R 1 . .
H H16F -0.4767 0.2061 0.2705 0.093 Uiso calc R 1 . .
N N1A 0.04501(11) 0.70683(9) 0.42637(9) 0.0357(3) Uani d . 1 . .
O O1A 0.05774(9) 0.89431(8) 0.49299(8) 0.0427(3) Uani d . 1 . .
O O2A 0.17798(11) 1.09159(8) 0.52600(9) 0.0464(3) Uani d . 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'
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
C14B C15B C16B . . 117.01(16) ?
C14B C15B H15C . . 108.0 ?
C16B C15B H15C . . 108.0 ?
C14B C15B H15D . . 108.0 ?
C16B C15B H15D . . 108.0 ?
H15C C15B H15D . . 107.3 ?
C15C C16C H16A . . 109.5 ?
C15C C16C H16B . . 109.5 ?
H16A C16C H16B . . 109.5 ?
C15C C16C H16C . . 109.5 ?
H16A C16C H16C . . 109.5 ?
H16B C16C H16C . . 109.5 ?
C7C C1C C2C . . 120.06(14) ?
C7C C1C C6C . . 119.77(13) ?
C2C C1C C6C . . 120.12(14) ?
C3C C2C C1C . . 120.24(15) ?
C3C C2C H2C . . 119.9 ?
C1C C2C H2C . . 119.9 ?
C2C C3C C4C . . 120.29(15) ?
C2C C3C H3C . . 119.9 ?
C4C C3C H3C . . 119.9 ?
C5C C4C C3C . . 120.98(15) ?
C5C C4C H4C . . 119.5 ?
C3C C4C H4C . . 119.5 ?
O2C C5C C4C . . 119.98(14) ?
O2C C5C C6C . . 119.21(14) ?
C4C C5C C6C . . 120.80(14) ?
O1C C6C C5C . . 120.01(13) ?
O1C C6C C1C . . 122.46(13) ?
C5C C6C C1C . . 117.53(13) ?
N1C C7C C1C . . 121.75(14) ?
N1C C7C H7C . . 117.8(9) ?
C1C C7C H7C . . 120.5(9) ?
C13C C8C C9C . . 119.41(14) ?
C13C C8C N1C . . 122.68(13) ?
C9C C8C N1C . . 117.88(13) ?
C10C C9C C8C . . 120.04(15) ?
C10C C9C H9C . . 120.0 ?
C8C C9C H9C . . 120.0 ?
C9C C10C C11C . . 121.47(15) ?
C9C C10C H10C . . 119.3 ?
C11C C10C H10C . . 119.3 ?
C12C C11C C10C . . 117.58(15) ?
C12C C11C C14C . . 120.88(16) ?
C10C C11C C14C . . 121.50(16) ?
C11C C12C C13C . . 121.96(15) ?
C11C C12C H12C . . 119.0 ?
C13C C12C H12C . . 119.0 ?
C12C C13C C8C . . 119.53(15) ?
C12C C13C H13C . . 120.2 ?
C8C C13C H13C . . 120.2 ?
C11C C14C C15C . . 112.95(15) ?
C11C C14C H14E . . 109.0 ?
C15C C14C H14E . . 109.0 ?
C11C C14C H14K . . 109.0 ?
C15C C14C H14K . . 109.0 ?
H14E C14C H14K . . 107.8 ?
C14C C15C C16C . . 114.12(18) ?
C14C C15C H15E . . 108.7 ?
C16C C15C H15E . . 108.7 ?
C14C C15C H15K . . 108.7 ?
C16C C15C H15K . . 108.7 ?
H15E C15C H15K . . 107.6 ?
C7C N1C C8C . . 126.57(13) ?
C7C N1C H1C . . 107.1(13) ?
C8C N1C H1C . . 126.3(13) ?
C5C O2C H5C . . 112.3(15) ?
C7B C1B C6B . . 119.51(13) ?
C7B C1B C2B . . 120.87(13) ?
C6B C1B C2B . . 119.60(13) ?
C3B C2B C1B . . 120.45(14) ?
C3B C2B H2B . . 119.8 ?
C1B C2B H2B . . 119.8 ?
C2B C3B C4B . . 120.46(14) ?
C2B C3B H3B . . 119.8 ?
C4B C3B H3B . . 119.8 ?
C5B C4B C3B . . 120.54(14) ?
C5B C4B H4B . . 119.7 ?
C3B C4B H4B . . 119.7 ?
O2B C5B C4B . . 120.72(13) ?
O2B C5B C6B . . 118.48(12) ?
C4B C5B C6B . . 120.80(13) ?
O1B C6B C1B . . 122.10(13) ?
O1B C6B C5B . . 119.75(12) ?
C1B C6B C5B . . 118.15(12) ?
N1B C7B C1B . . 121.44(13) ?
N1B C7B H7B . . 120.8(10) ?
C1B C7B H7B . . 117.7(10) ?
C13B C8B C9B . . 119.43(13) ?
C13B C8B N1B . . 123.12(13) ?
C9B C8B N1B . . 117.42(13) ?
C10B C9B C8B . . 119.80(14) ?
C10B C9B H9B . . 120.1 ?
C8B C9B H9B . . 120.1 ?
C9B C10B C11B . . 121.61(14) ?
C9B C10B H10B . . 119.2 ?
C11B C10B H10B . . 119.2 ?
C10B C11B C12B . . 117.52(14) ?
C10B C11B C14B . . 121.90(14) ?
C12B C11B C14B . . 120.55(15) ?
C13B C12B C11B . . 121.84(14) ?
C13B C12B H12B . . 119.1 ?
C11B C12B H12B . . 119.1 ?
C12B C13B C8B . . 119.78(14) ?
C12B C13B H13B . . 120.1 ?
C8B C13B H13B . . 120.1 ?
C15B C14B C11B . . 114.85(14) ?
C15B C14B H14C . . 108.6 ?
C11B C14B H14C . . 108.6 ?
C15B C14B H14D . . 108.6 ?
C11B C14B H14D . . 108.6 ?
H14C C14B H14D . . 107.5 ?
C15B C16B H16K . . 109.5 ?
C15B C16B H16L . . 109.5 ?
H16K C16B H16L . . 109.5 ?
C15B C16B H16M . . 109.5 ?
H16K C16B H16M . . 109.5 ?
H16L C16B H16M . . 109.5 ?
C7B N1B C8B . . 127.37(12) ?
C7B N1B H1B . . 109.2(13) ?
C8B N1B H1B . . 123.4(13) ?
C5B O2B H5B . . 107.0(14) ?
C7A C1A C2A . . 120.17(14) ?
C7A C1A C6A . . 119.76(13) ?
C2A C1A C6A . . 120.05(13) ?
C3A C2A C1A . . 120.36(15) ?
C3A C2A H2A . . 119.8 ?
C1A C2A H2A . . 119.8 ?
C2A C3A C4A . . 120.10(15) ?
C2A C3A H3A . . 119.9 ?
C4A C3A H3A . . 119.9 ?
C5A C4A C3A . . 120.99(14) ?
C5A C4A H4A . . 119.5 ?
C3A C4A H4A . . 119.5 ?
O2A C5A C4A . . 120.07(13) ?
O2A C5A C6A . . 119.07(13) ?
C4A C5A C6A . . 120.86(14) ?
O1A C6A C1A . . 122.32(13) ?
O1A C6A C5A . . 120.06(13) ?
C1A C6A C5A . . 117.63(13) ?
N1A C7A C1A . . 121.83(14) ?
N1A C7A H7A . . 119.6(10) ?
C1A C7A H7A . . 118.5(10) ?
C9A C8A C13A . . 119.41(13) ?
C9A C8A N1A . . 117.20(12) ?
C13A C8A N1A . . 123.37(13) ?
C8A C9A C10A . . 120.16(13) ?
C8A C9A H9A . . 119.9 ?
C10A C9A H9A . . 119.9 ?
C9A C10A C11A . . 121.14(14) ?
C9A C10A H10A . . 119.4 ?
C11A C10A H10A . . 119.4 ?
C10A C11A C12A . . 117.65(13) ?
C10A C11A C14A . . 122.92(13) ?
C12A C11A C14A . . 119.43(13) ?
C13A C12A C11A . . 121.90(13) ?
C13A C12A H12A . . 119.1 ?
C11A C12A H12A . . 119.1 ?
C12A C13A C8A . . 119.73(14) ?
C12A C13A H13A . . 120.1 ?
C8A C13A H13A . . 120.1 ?
C11A C14A C15A . . 117.08(13) ?
C11A C14A H14A . . 108.0 ?
C15A C14A H14A . . 108.0 ?
C11A C14A H14B . . 108.0 ?
C15A C14A H14B . . 108.0 ?
H14A C14A H14B . . 107.3 ?
C14A C15A C16A . . 112.08(15) ?
C14A C15A H15A . . 109.2 ?
C16A C15A H15A . . 109.2 ?
C14A C15A H15B . . 109.2 ?
C16A C15A H15B . . 109.2 ?
H15A C15A H15B . . 107.9 ?
C15A C16A H16D . . 109.5 ?
C15A C16A H16E . . 109.5 ?
H16D C16A H16E . . 109.5 ?
C15A C16A H16F . . 109.5 ?
H16D C16A H16F . . 109.5 ?
H16E C16A H16F . . 109.5 ?
C7A N1A C8A . . 127.46(13) ?
C7A N1A H1A . . 108.7(13) ?
C8A N1A H1A . . 123.5(13) ?
C5A O2A H5A . . 108.3(13) ?
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
C15B C14B . 1.472(3) ?
C15B C16B . 1.502(2) ?
C15B H15C . 0.97 ?
C15B H15D . 0.97 ?
C16C C15C . 1.508(3) ?
C16C H16A . 0.96 ?
C16C H16B . 0.96 ?
C16C H16C . 0.96 ?
C1C C7C . 1.414(2) ?
C1C C2C . 1.414(2) ?
C1C C6C . 1.426(2) ?
C2C C3C . 1.362(2) ?
C2C H2C . 0.93 ?
C3C C4C . 1.402(2) ?
C3C H3C . 0.93 ?
C4C C5C . 1.367(2) ?
C4C H4C . 0.93 ?
C5C O2C . 1.3642(19) ?
C5C C6C . 1.420(2) ?
C6C O1C . 1.3060(18) ?
C7C N1C . 1.3065(19) ?
C7C H7C . 0.974(17) ?
C8C C13C . 1.387(2) ?
C8C C9C . 1.390(2) ?
C8C N1C . 1.4139(19) ?
C9C C10C . 1.380(2) ?
C9C H9C . 0.93 ?
C10C C11C . 1.390(2) ?
C10C H10C . 0.93 ?
C11C C12C . 1.384(2) ?
C11C C14C . 1.505(2) ?
C12C C13C . 1.385(2) ?
C12C H12C . 0.93 ?
C13C H13C . 0.93 ?
C14C C15C . 1.505(3) ?
C14C H14E . 0.97 ?
C14C H14K . 0.97 ?
C15C H15E . 0.97 ?
C15C H15K . 0.97 ?
N1C H1C . 1.08(3) ?
O2C H5C . 0.92(2) ?
C1B C7B . 1.417(2) ?
C1B C6B . 1.4205(19) ?
C1B C2B . 1.421(2) ?
C2B C3B . 1.361(2) ?
C2B H2B . 0.93 ?
C3B C4B . 1.409(2) ?
C3B H3B . 0.93 ?
C4B C5B . 1.369(2) ?
C4B H4B . 0.93 ?
C5B O2B . 1.3593(17) ?
C5B C6B . 1.423(2) ?
C6B O1B . 1.3028(17) ?
C7B N1B . 1.3068(19) ?
C7B H7B . 0.977(17) ?
C8B C13B . 1.386(2) ?
C8B C9B . 1.393(2) ?
C8B N1B . 1.4146(18) ?
C9B C10B . 1.383(2) ?
C9B H9B . 0.93 ?
C10B C11B . 1.389(2) ?
C10B H10B . 0.93 ?
C11B C12B . 1.390(2) ?
C11B C14B . 1.513(2) ?
C12B C13B . 1.381(2) ?
C12B H12B . 0.93 ?
C13B H13B . 0.93 ?
C14B H14C . 0.97 ?
C14B H14D . 0.97 ?
C16B H16K . 0.96 ?
C16B H16L . 0.96 ?
C16B H16M . 0.96 ?
N1B H1B . 1.06(2) ?
O2B H5B . 0.89(2) ?
C1A C7A . 1.416(2) ?
C1A C2A . 1.417(2) ?
C1A C6A . 1.423(2) ?
C2A C3A . 1.365(2) ?
C2A H2A . 0.93 ?
C3A C4A . 1.405(2) ?
C3A H3A . 0.93 ?
C4A C5A . 1.366(2) ?
C4A H4A . 0.93 ?
C5A O2A . 1.3611(18) ?
C5A C6A . 1.424(2) ?
C6A O1A . 1.3034(18) ?
C7A N1A . 1.3034(19) ?
C7A H7A . 0.998(18) ?
C8A C9A . 1.384(2) ?
C8A C13A . 1.389(2) ?
C8A N1A . 1.4125(18) ?
C9A C10A . 1.385(2) ?
C9A H9A . 0.93 ?
C10A C11A . 1.388(2) ?
C10A H10A . 0.93 ?
C11A C12A . 1.390(2) ?
C11A C14A . 1.509(2) ?
C12A C13A . 1.375(2) ?
C12A H12A . 0.93 ?
C13A H13A . 0.93 ?
C14A C15A . 1.510(2) ?
C14A H14A . 0.97 ?
C14A H14B . 0.97 ?
C15A C16A . 1.518(2) ?
C15A H15A . 0.97 ?
C15A H15B . 0.97 ?
C16A H16D . 0.96 ?
C16A H16E . 0.96 ?
C16A H16F . 0.96 ?
N1A H1A . 1.02(2) ?
O2A H5A . 0.91(2) ?
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
N1A H1A O1A . 1.02(2) 1.63(2) 2.5444(16) 147(2)
N1B H1B O1B . 1.06(2) 1.57(2) 2.5229(16) 146(2)
N1C H1C O1C . 1.08(2) 1.57(2) 2.5502(17) 149(2)
O2A H5A O1A 2_576 0.90(2) 1.89(2) 2.7032(17) 148(2)
O2B H5B O1B 2_666 0.89(2) 1.91(2) 2.7049(15) 148(2)
O2C H5C O1C 2_567 0.92(2) 1.84(2) 2.6659(15) 148(2)
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
C7C C1C C2C C3C . . . . -176.72(15) ?
C6C C1C C2C C3C . . . . 0.8(2) ?
C1C C2C C3C C4C . . . . 0.6(2) ?
C2C C3C C4C C5C . . . . -0.8(2) ?
C3C C4C C5C O2C . . . . 178.86(13) ?
C3C C4C C5C C6C . . . . -0.5(2) ?
O2C C5C C6C O1C . . . . 2.0(2) ?
C4C C5C C6C O1C . . . . -178.63(13) ?
O2C C5C C6C C1C . . . . -177.47(12) ?
C4C C5C C6C C1C . . . . 1.9(2) ?
C7C C1C C6C O1C . . . . -4.0(2) ?
C2C C1C C6C O1C . . . . 178.48(13) ?
C7C C1C C6C C5C . . . . 175.51(13) ?
C2C C1C C6C C5C . . . . -2.1(2) ?
C2C C1C C7C N1C . . . . 177.33(14) ?
C6C C1C C7C N1C . . . . -0.2(2) ?
C13C C8C C9C C10C . . . . 0.8(2) ?
N1C C8C C9C C10C . . . . 179.19(13) ?
C8C C9C C10C C11C . . . . -0.1(2) ?
C9C C10C C11C C12C . . . . -0.6(2) ?
C9C C10C C11C C14C . . . . 177.07(15) ?
C10C C11C C12C C13C . . . . 0.6(2) ?
C14C C11C C12C C13C . . . . -177.05(15) ?
C11C C12C C13C C8C . . . . 0.1(2) ?
C9C C8C C13C C12C . . . . -0.8(2) ?
N1C C8C C13C C12C . . . . -179.07(13) ?
C12C C11C C14C C15C . . . . 79.4(2) ?
C10C C11C C14C C15C . . . . -98.2(2) ?
C11C C14C C15C C16C . . . . 177.3(2) ?
C1C C7C N1C C8C . . . . 178.85(13) ?
C13C C8C N1C C7C . . . . -23.0(2) ?
C9C C8C N1C C7C . . . . 158.72(14) ?
C7B C1B C2B C3B . . . . 176.83(14) ?
C6B C1B C2B C3B . . . . -1.3(2) ?
C1B C2B C3B C4B . . . . 0.5(2) ?
C2B C3B C4B C5B . . . . 0.5(2) ?
C3B C4B C5B O2B . . . . 178.82(13) ?
C3B C4B C5B C6B . . . . -0.8(2) ?
C7B C1B C6B O1B . . . . 3.6(2) ?
C2B C1B C6B O1B . . . . -178.32(13) ?
C7B C1B C6B C5B . . . . -177.09(12) ?
C2B C1B C6B C5B . . . . 1.0(2) ?
O2B C5B C6B O1B . . . . -0.26(19) ?
C4B C5B C6B O1B . . . . 179.34(13) ?
O2B C5B C6B C1B . . . . -179.63(12) ?
C4B C5B C6B C1B . . . . 0.0(2) ?
C6B C1B C7B N1B . . . . 0.0(2) ?
C2B C1B C7B N1B . . . . -178.13(14) ?
C13B C8B C9B C10B . . . . 0.7(2) ?
N1B C8B C9B C10B . . . . -177.44(13) ?
C8B C9B C10B C11B . . . . -0.2(2) ?
C9B C10B C11B C12B . . . . -0.6(2) ?
C9B C10B C11B C14B . . . . 177.71(15) ?
C10B C11B C12B C13B . . . . 1.0(2) ?
C14B C11B C12B C13B . . . . -177.33(15) ?
C11B C12B C13B C8B . . . . -0.6(2) ?
C9B C8B C13B C12B . . . . -0.3(2) ?
N1B C8B C13B C12B . . . . 177.72(14) ?
C16B C15B C14B C11B . . . . -176.99(18) ?
C10B C11B C14B C15B . . . . -59.4(2) ?
C12B C11B C14B C15B . . . . 118.8(2) ?
C1B C7B N1B C8B . . . . 179.71(13) ?
C13B C8B N1B C7B . . . . 7.4(2) ?
C9B C8B N1B C7B . . . . -174.52(14) ?
C7A C1A C2A C3A . . . . 179.57(15) ?
C6A C1A C2A C3A . . . . 1.1(2) ?
C1A C2A C3A C4A . . . . -0.3(3) ?
C2A C3A C4A C5A . . . . -0.6(2) ?
C3A C4A C5A O2A . . . . -179.63(14) ?
C3A C4A C5A C6A . . . . 0.7(2) ?
C7A C1A C6A O1A . . . . 0.6(2) ?
C2A C1A C6A O1A . . . . 179.17(14) ?
C7A C1A C6A C5A . . . . -179.45(13) ?
C2A C1A C6A C5A . . . . -0.9(2) ?
O2A C5A C6A O1A . . . . 0.3(2) ?
C4A C5A C6A O1A . . . . 179.97(14) ?
O2A C5A C6A C1A . . . . -179.61(13) ?
C4A C5A C6A C1A . . . . 0.1(2) ?
C2A C1A C7A N1A . . . . -179.46(14) ?
C6A C1A C7A N1A . . . . -0.9(2) ?
C13A C8A C9A C10A . . . . 0.6(2) ?
N1A C8A C9A C10A . . . . 178.91(13) ?
C8A C9A C10A C11A . . . . -0.5(2) ?
C9A C10A C11A C12A . . . . -0.1(2) ?
C9A C10A C11A C14A . . . . 179.53(14) ?
C10A C11A C12A C13A . . . . 0.6(2) ?
C14A C11A C12A C13A . . . . -179.01(14) ?
C11A C12A C13A C8A . . . . -0.6(2) ?
C9A C8A C13A C12A . . . . 0.0(2) ?
N1A C8A C13A C12A . . . . -178.28(14) ?
C10A C11A C14A C15A . . . . 8.2(2) ?
C12A C11A C14A C15A . . . . -172.20(14) ?
C11A C14A C15A C16A . . . . 179.78(14) ?
C1A C7A N1A C8A . . . . 174.36(13) ?
C9A C8A N1A C7A . . . . -174.64(14) ?
C13A C8A N1A C7A . . . . 3.6(2) ?
