#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/14/2221468.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_2221468
loop_
_publ_author_name
'NizamMohideen, M.'
'Thenmozhi, S.'
'SubbiahPandi, A.'
'Selvam, N. Panneer'
'Perumal, P. T.'
_publ_section_title
;
 N-[(2-Hydroxy-1-naphthyl)(2-hydroxyphenyl)methyl]acetamide
;
_journal_coeditor_code           PV2141
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o740
_journal_paper_doi               10.1107/S1600536809007983
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H17 N O3'
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.34
_chemical_name_systematic
;
N-[(2-Hydroxy-1-naphthyl)(2-hydroxyphenyl)methyl]acetamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.4280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   21.286(5)
_cell_length_b                   17.9288(4)
_cell_length_c                   19.524(7)
_cell_measurement_reflns_used    6464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     6358(3)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker Kappa APEXII CCD
;
_diffrn_measurement_method       'ω and φ'
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33278
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.495
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0747P)²+2.6626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                4384
_reflns_number_total             6464
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2141.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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 

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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2221468
_cod_database_fobs_code          2221468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O O1 0.05068(7) 0.50195(8) 0.59220(8) 0.0556(4) Uani d . 1 . .
H H1 0.0080 0.5100 0.5793 0.083 Uiso calc R 1 . .
O O2 0.30227(7) 0.59048(8) 0.70861(10) 0.0655(4) Uani d . 1 . .
H H2 0.3361 0.6207 0.7274 0.098 Uiso calc R 1 . .
O O3 0.09894(7) 0.46622(7) 0.47788(7) 0.0427(3) Uani d . 1 . .
N N1 0.17949(8) 0.53425(8) 0.58664(9) 0.0413(4) Uani d . 1 . .
H H1A 0.2011 0.5768 0.6017 0.050 Uiso calc R 1 . .
C C1 0.09638(10) 0.51566(10) 0.67223(11) 0.0415(4) Uani d . 1 . .
C C2 0.07009(11) 0.53887(11) 0.72002(13) 0.0531(5) Uani d . 1 . .
H H2A 0.0200 0.5475 0.6975 0.064 Uiso calc R 1 . .
C C3 0.11779(12) 0.54928(13) 0.80092(14) 0.0619(6) Uani d . 1 . .
H H3 0.1000 0.5648 0.8332 0.074 Uiso calc R 1 . .
C C4 0.19150(13) 0.53670(14) 0.83396(13) 0.0659(6) Uani d . 1 . .
H H4 0.2238 0.5436 0.8887 0.079 Uiso calc R 1 . .
C C5 0.21785(11) 0.51384(12) 0.78609(12) 0.0533(5) Uani d . 1 . .
H H5 0.2680 0.5051 0.8092 0.064 Uiso calc R 1 . .
C C6 0.17118(9) 0.50360(10) 0.70431(11) 0.0391(4) Uani d . 1 . .
C C7 0.19871(9) 0.47856(9) 0.65004(10) 0.0376(4) Uani d . 1 . .
H H7 0.1727 0.4323 0.6237 0.045 Uiso calc R 1 . .
C C8 0.28056(9) 0.46165(10) 0.69505(11) 0.0399(4) Uani d . 1 . .
C C9 0.33020(10) 0.52005(11) 0.72284(12) 0.0473(5) Uani d . 1 . .
C C10 0.40660(11) 0.50776(14) 0.76622(13) 0.0600(6) Uani d . 1 . .
H H10 0.4390 0.5479 0.7834 0.072 Uiso calc R 1 . .
C C11 0.43294(11) 0.43680(15) 0.78296(13) 0.0641(6) Uani d . 1 . .
H H11 0.4836 0.4290 0.8120 0.077 Uiso calc R 1 . .
C C12 0.38526(12) 0.37479(13) 0.75730(12) 0.0552(5) Uani d . 1 . .
C C13 0.30753(10) 0.38715(11) 0.71243(10) 0.0431(4) Uani d . 1 . .
C C14 0.26164(12) 0.32330(11) 0.68782(12) 0.0531(5) Uani d . 1 . .
H H14 0.2108 0.3296 0.6590 0.064 Uiso calc R 1 . .
C C15 0.28989(16) 0.25316(13) 0.70521(14) 0.0739(7) Uani d . 1 . .
H H15 0.2584 0.2123 0.6876 0.089 Uiso calc R 1 . .
C C16 0.36600(18) 0.24206(16) 0.74933(16) 0.0850(9) Uani d . 1 . .
H H16 0.3850 0.1939 0.7615 0.102 Uiso calc R 1 . .
C C17 0.41189(15) 0.30083(17) 0.77423(14) 0.0747(8) Uani d . 1 . .
H H17 0.4624 0.2926 0.8033 0.090 Uiso calc R 1 . .
C C18 0.13247(10) 0.52537(10) 0.50919(11) 0.0398(4) Uani d . 1 . .
C C19 0.12036(14) 0.59206(12) 0.45734(14) 0.0709(7) Uani d . 1 . .
H H19A 0.1426 0.5835 0.4261 0.106 Uiso calc R 1 . .
H H19B 0.1422 0.6352 0.4906 0.106 Uiso calc R 1 . .
H H19C 0.0685 0.6002 0.4221 0.106 Uiso calc R 1 . .
O O1A -0.04220(8) 0.82226(9) 0.16047(8) 0.0572(4) Uani d . 1 . .
H H1A1 0.0018 0.8190 0.1765 0.086 Uiso calc R 1 . .
O O2A 0.05897(8) 0.65781(7) 0.02450(8) 0.0532(4) Uani d . 1 . .
H H2A1 0.0688 0.6224 0.0051 0.080 Uiso calc R 1 . .
O O3A 0.11589(7) 0.79276(7) 0.26185(8) 0.0472(3) Uani d . 1 . .
N N1A 0.06323(8) 0.72763(8) 0.14574(8) 0.0364(3) Uani d . 1 . .
H H1A2 0.0553 0.6835 0.1257 0.044 Uiso calc R 1 . .
C C1A -0.08229(10) 0.80834(10) 0.08044(12) 0.0444(4) Uani d . 1 . .
C C2A -0.15812(11) 0.80967(13) 0.03873(14) 0.0591(6) Uani d . 1 . .
H H2A2 -0.1826 0.8196 0.0656 0.071 Uiso calc R 1 . .
C C3A -0.19743(13) 0.79645(16) -0.04221(16) 0.0768(8) Uani d . 1 . .
H H3A -0.2486 0.7973 -0.0700 0.092 Uiso calc R 1 . .
C C4A -0.16199(13) 0.78190(18) -0.08270(15) 0.0820(8) Uani d . 1 . .
H H4A -0.1888 0.7730 -0.1377 0.098 Uiso calc R 1 . .
C C5A -0.08569(12) 0.78056(14) -0.04061(12) 0.0613(6) Uani d . 1 . .
H H5A -0.0617 0.7708 -0.0680 0.074 Uiso calc R 1 . .
C C6A -0.04459(10) 0.79339(10) 0.04089(11) 0.0412(4) Uani d . 1 . .
C C7A 0.03910(9) 0.79041(9) 0.08923(10) 0.0361(4) Uani d . 1 . .
H H7A 0.0562 0.8361 0.1214 0.043 Uiso calc R 1 . .
C C8A 0.07419(9) 0.78832(9) 0.03854(10) 0.0361(4) Uani d . 1 . .
C C9A 0.08438(10) 0.72246(10) 0.00967(11) 0.0421(4) Uani d . 1 . .
C C10A 0.11902(12) 0.72005(12) -0.03502(12) 0.0547(5) Uani d . 1 . .
H H10A 0.1268 0.6744 -0.0520 0.066 Uiso calc R 1 . .
C C11A 0.14087(12) 0.78344(13) -0.05326(12) 0.0573(6) Uani d . 1 . .
H H11A 0.1644 0.7810 -0.0821 0.069 Uiso calc R 1 . .
C C12A 0.12871(10) 0.85341(11) -0.02947(11) 0.0471(5) Uani d . 1 . .
C C13A 0.09502(9) 0.85622(10) 0.01715(10) 0.0385(4) Uani d . 1 . .
C C14A 0.08239(10) 0.92775(10) 0.03835(12) 0.0478(5) Uani d . 1 . .
H H14A 0.0605 0.9315 0.0689 0.057 Uiso calc R 1 . .
C C15A 0.10157(12) 0.99152(12) 0.01502(14) 0.0618(6) Uani d . 1 . .
H H15A 0.0927 1.0378 0.0299 0.074 Uiso calc R 1 . .
C C16A 0.13439(13) 0.98752(14) -0.03111(15) 0.0678(7) Uani d . 1 . .
H H16A 0.1471 1.0310 -0.0471 0.081 Uiso calc R 1 . .
C C17A 0.14749(12) 0.92046(14) -0.05222(13) 0.0609(6) Uani d . 1 . .
H H17A 0.1695 0.9183 -0.0826 0.073 Uiso calc R 1 . .
C C18A 0.09592(9) 0.73285(9) 0.22438(10) 0.0376(4) Uani d . 1 . .
C C19A 0.10774(14) 0.66185(12) 0.26910(13) 0.0664(6) Uani d . 1 . .
H H19D 0.1576 0.6455 0.2912 0.100 Uiso calc R 1 . .
H H19E 0.0746 0.6245 0.2332 0.100 Uiso calc R 1 . .
H H19F 0.0986 0.6698 0.3118 0.100 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'
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
C1 O1 H1 . . 109.5 ?
C9 O2 H2 . . 109.5 ?
C18 N1 C7 . . 126.49(14) ?
C18 N1 H1A . . 116.8 ?
C7 N1 H1A . . 116.8 ?
O1 C1 C2 . . 122.04(16) ?
O1 C1 C6 . . 116.91(17) ?
C2 C1 C6 . . 121.03(17) ?
C3 C2 C1 . . 120.10(18) ?
C3 C2 H2A . . 120.0 ?
C1 C2 H2A . . 120.0 ?
C4 C3 C2 . . 119.9(2) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.1(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 121.34(19) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 117.60(18) ?
C5 C6 C7 . . 122.49(16) ?
C1 C6 C7 . . 119.90(16) ?
N1 C7 C8 . . 110.73(14) ?
N1 C7 C6 . . 110.26(14) ?
C8 C7 C6 . . 113.48(14) ?
N1 C7 H7 . . 107.4 ?
C8 C7 H7 . . 107.4 ?
C6 C7 H7 . . 107.4 ?
C9 C8 C13 . . 119.13(17) ?
C9 C8 C7 . . 119.21(16) ?
C13 C8 C7 . . 121.61(15) ?
O2 C9 C8 . . 117.37(16) ?
O2 C9 C10 . . 120.90(18) ?
C8 C9 C10 . . 121.71(19) ?
C11 C10 C9 . . 119.6(2) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 121.49(19) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C11 C12 C17 . . 122.1(2) ?
C11 C12 C13 . . 118.98(19) ?
C17 C12 C13 . . 119.0(2) ?
C14 C13 C8 . . 123.81(17) ?
C14 C13 C12 . . 117.12(18) ?
C8 C13 C12 . . 119.06(18) ?
C15 C14 C13 . . 121.8(2) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C14 C15 C16 . . 120.4(3) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C17 C16 C15 . . 120.1(2) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C12 . . 121.6(2) ?
C16 C17 H17 . . 119.2 ?
C12 C17 H17 . . 119.2 ?
O3 C18 N1 1 . 124.33(16) ?
O3 C18 N1 . . 124.33(16) ?
O3 C18 C19 1 . 119.64(17) ?
O3 C18 C19 . . 119.64(17) ?
N1 C18 C19 . . 116.02(17) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C1A O1A H1A1 . . 109.5 ?
C9A O2A H2A1 . . 109.5 ?
C18A N1A C7A . . 125.89(14) ?
C18A N1A H1A2 . . 117.1 ?
C7A N1A H1A2 . . 117.1 ?
O1A C1A C2A . . 121.13(18) ?
O1A C1A C6A . . 118.25(16) ?
C2A C1A C6A . . 120.61(19) ?
C3A C2A C1A . . 120.1(2) ?
C3A C2A H2A2 . . 119.9 ?
C1A C2A H2A2 . . 119.9 ?
C2A C3A C4A . . 120.6(2) ?
C2A C3A H3A . . 119.7 ?
C4A C3A H3A . . 119.7 ?
C3A C4A C5A . . 119.2(2) ?
C3A C4A H4A . . 120.4 ?
C5A C4A H4A . . 120.4 ?
C6A C5A C4A . . 121.6(2) ?
C6A C5A H5A . . 119.2 ?
C4A C5A H5A . . 119.2 ?
C5A C6A C1A . . 117.88(17) ?
C5A C6A C7A . . 122.95(17) ?
C1A C6A C7A . . 119.16(16) ?
N1A C7A C8A . . 111.85(13) ?
N1A C7A C6A . . 109.32(13) ?
C8A C7A C6A . . 114.26(14) ?
N1A C7A H7A . . 107.0 ?
C8A C7A H7A . . 107.0 ?
C6A C7A H7A . . 107.0 ?
C9A C8A C13A . . 118.19(16) ?
C9A C8A C7A . . 121.65(15) ?
C13A C8A C7A . . 120.11(15) ?
O2A C9A C8A . . 118.40(16) ?
O2A C9A C10A . . 119.78(16) ?
C8A C9A C10A . . 121.81(17) ?
C11A C10A C9A . . 120.26(18) ?
C11A C10A H10A . . 119.9 ?
C9A C10A H10A . . 119.9 ?
C10A C11A C12A . . 121.17(19) ?
C10A C11A H11A . . 119.4 ?
C12A C11A H11A . . 119.4 ?
C11A C12A C17A . . 121.7(2) ?
C11A C12A C13A . . 118.89(17) ?
C17A C12A C13A . . 119.44(19) ?
C14A C13A C12A . . 117.06(16) ?
C14A C13A C8A . . 123.40(17) ?
C12A C13A C8A . . 119.53(16) ?
C15A C14A C13A . . 121.6(2) ?
C15A C14A H14A . . 119.2 ?
C13A C14A H14A . . 119.2 ?
C14A C15A C16A . . 120.4(2) ?
C14A C15A H15A . . 119.8 ?
C16A C15A H15A . . 119.8 ?
C17A C16A C15A . . 119.7(2) ?
C17A C16A H16A . . 120.2 ?
C15A C16A H16A . . 120.2 ?
C16A C17A C12A . . 121.8(2) ?
C16A C17A H17A . . 119.1 ?
C12A C17A H17A . . 119.1 ?
O3A C18A N1A 1 . 123.91(16) ?
O3A C18A N1A . . 123.91(16) ?
O3A C18A N1A 1 . 123.91(16) ?
O3A C18A C19A 1 . 119.49(17) ?
O3A C18A C19A . . 119.49(17) ?
O3A C18A C19A 1 . 119.49(17) ?
N1A C18A C19A . . 116.59(16) ?
C18A C19A H19D . . 109.5 ?
C18A C19A H19E . . 109.5 ?
H19D C19A H19E . . 109.5 ?
C18A C19A H19F . . 109.5 ?
H19D C19A H19F . . 109.5 ?
H19E C19A H19F . . 109.5 ?
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
O1 C1 . 1.365(2) ?
O1 H1 . 0.8200 ?
O2 C9 . 1.361(2) ?
O2 H2 . 0.8200 ?
O3 C18 . 1.246(2) ?
N1 C18 . 1.317(2) ?
N1 C7 . 1.473(2) ?
N1 H1A . 0.8600 ?
C1 C2 . 1.379(3) ?
C1 C6 . 1.391(2) ?
C2 C3 . 1.374(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.369(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.521(3) ?
C7 C8 . 1.518(2) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.382(3) ?
C8 C13 . 1.423(3) ?
C9 C10 . 1.405(3) ?
C10 C11 . 1.360(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.410(3) ?
C11 H11 . 0.9300 ?
C12 C17 . 1.412(3) ?
C12 C13 . 1.429(3) ?
C13 C14 . 1.416(3) ?
C14 C15 . 1.358(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.397(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.344(4) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 O3 1 1.246(2) ?
C18 C19 . 1.499(3) ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
O1A C1A . 1.357(2) ?
O1A H1A1 . 0.8200 ?
O2A C9A . 1.372(2) ?
O2A H2A1 . 0.8200 ?
O3A C18A . 1.243(2) ?
N1A C18A . 1.318(2) ?
N1A C7A . 1.469(2) ?
N1A H1A2 . 0.8600 ?
C1A C2A . 1.378(3) ?
C1A C6A . 1.400(3) ?
C2A C3A . 1.369(3) ?
C2A H2A2 . 0.9300 ?
C3A C4A . 1.373(4) ?
C3A H3A . 0.9300 ?
C4A C5A . 1.386(3) ?
C4A H4A . 0.9300 ?
C5A C6A . 1.378(3) ?
C5A H5A . 0.9300 ?
C6A C7A . 1.521(2) ?
C7A C8A . 1.520(2) ?
C7A H7A . 0.9800 ?
C8A C9A . 1.374(2) ?
C8A C13A . 1.430(2) ?
C9A C10A . 1.406(3) ?
C10A C11A . 1.344(3) ?
C10A H10A . 0.9300 ?
C11A C12A . 1.408(3) ?
C11A H11A . 0.9300 ?
C12A C17A . 1.410(3) ?
C12A C13A . 1.423(3) ?
C13A C14A . 1.416(3) ?
C14A C15A . 1.370(3) ?
C14A H14A . 0.9300 ?
C15A C16A . 1.400(4) ?
C15A H15A . 0.9300 ?
C16A C17A . 1.347(3) ?
C16A H16A . 0.9300 ?
C17A H17A . 0.9300 ?
C18A O3A 1 1.243(2) ?
C18A O3A 1 1.243(2) ?
C18A C19A . 1.489(3) ?
C19A H19D . 0.9600 ?
C19A H19E . 0.9600 ?
C19A H19F . 0.9600 ?
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
O1 H1 O3 5_566 0.82 1.99 2.792(2) 166
O2A H2A1 O3 6_565 0.82 1.89 2.702(2) 170
O2 H2 O3A 7_566 0.82 1.81 2.588(2) 159
O1A H1A1 O3A 1 0.82 2.16 2.928(2) 156
C7 H7 O3 1 0.98 2.51 2.901(2) 104
C7A H7A O3A 1 0.98 2.47 2.879(2) 105
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
O1 C1 C2 C3 . . . . 177.50(19) ?
C6 C1 C2 C3 . . . . -1.1(3) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 0.2(4) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
C4 C5 C6 C1 . . . . -1.3(3) ?
C4 C5 C6 C7 . . . . 179.9(2) ?
O1 C1 C6 C5 . . . . -177.01(17) ?
C2 C1 C6 C5 . . . . 1.7(3) ?
O1 C1 C6 C7 . . . . 1.8(2) ?
C2 C1 C6 C7 . . . . -179.54(17) ?
C18 N1 C7 C8 . . . . 120.86(18) ?
C18 N1 C7 C6 . . . . -112.71(19) ?
C5 C6 C7 N1 . . . . -121.32(19) ?
C1 C6 C7 N1 . . . . 59.9(2) ?
C5 C6 C7 C8 . . . . 3.5(2) ?
C1 C6 C7 C8 . . . . -175.20(15) ?
N1 C7 C8 C9 . . . . 49.0(2) ?
C6 C7 C8 C9 . . . . -75.7(2) ?
N1 C7 C8 C13 . . . . -133.86(17) ?
C6 C7 C8 C13 . . . . 101.53(19) ?
C13 C8 C9 O2 . . . . -176.66(17) ?
C7 C8 C9 O2 . . . . 0.6(3) ?
C13 C8 C9 C10 . . . . 1.5(3) ?
C7 C8 C9 C10 . . . . 178.75(18) ?
O2 C9 C10 C11 . . . . 176.8(2) ?
C8 C9 C10 C11 . . . . -1.3(3) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C10 C11 C12 C17 . . . . 179.9(2) ?
C10 C11 C12 C13 . . . . 0.2(3) ?
C9 C8 C13 C14 . . . . 179.16(18) ?
C7 C8 C13 C14 . . . . 2.0(3) ?
C9 C8 C13 C12 . . . . -0.8(3) ?
C7 C8 C13 C12 . . . . -177.97(17) ?
C11 C12 C13 C14 . . . . 179.99(19) ?
C17 C12 C13 C14 . . . . 0.3(3) ?
C11 C12 C13 C8 . . . . -0.1(3) ?
C17 C12 C13 C8 . . . . -179.79(19) ?
C8 C13 C14 C15 . . . . 179.4(2) ?
C12 C13 C14 C15 . . . . -0.7(3) ?
C13 C14 C15 C16 . . . . 0.9(4) ?
C14 C15 C16 C17 . . . . -0.7(4) ?
C15 C16 C17 C12 . . . . 0.3(4) ?
C11 C12 C17 C16 . . . . -179.8(2) ?
C13 C12 C17 C16 . . . . -0.1(4) ?
C7 N1 C18 O3 . . . 1 -2.7(3) ?
C7 N1 C18 O3 . . . . -2.7(3) ?
C7 N1 C18 C19 . . . . 177.57(19) ?
O1A C1A C2A C3A . . . . 179.1(2) ?
C6A C1A C2A C3A . . . . -0.1(3) ?
C1A C2A C3A C4A . . . . -0.1(4) ?
C2A C3A C4A C5A . . . . 0.1(4) ?
C3A C4A C5A C6A . . . . 0.1(4) ?
C4A C5A C6A C1A . . . . -0.3(3) ?
C4A C5A C6A C7A . . . . 178.4(2) ?
O1A C1A C6A C5A . . . . -178.92(18) ?
C2A C1A C6A C5A . . . . 0.3(3) ?
O1A C1A C6A C7A . . . . 2.3(2) ?
C2A C1A C6A C7A . . . . -178.44(17) ?
C18A N1A C7A C8A . . . . 122.33(17) ?
C18A N1A C7A C6A . . . . -110.10(18) ?
C5A C6A C7A N1A . . . . -114.0(2) ?
C1A C6A C7A N1A . . . . 64.7(2) ?
C5A C6A C7A C8A . . . . 12.2(2) ?
C1A C6A C7A C8A . . . . -169.11(15) ?
N1A C7A C8A C9A . . . . 39.0(2) ?
C6A C7A C8A C9A . . . . -85.9(2) ?
N1A C7A C8A C13A . . . . -143.40(15) ?
C6A C7A C8A C13A . . . . 91.73(19) ?
C13A C8A C9A O2A . . . . -174.72(15) ?
C7A C8A C9A O2A . . . . 2.9(3) ?
C13A C8A C9A C10A . . . . 4.5(3) ?
C7A C8A C9A C10A . . . . -177.87(17) ?
O2A C9A C10A C11A . . . . 176.72(19) ?
C8A C9A C10A C11A . . . . -2.5(3) ?
C9A C10A C11A C12A . . . . -1.0(3) ?
C10A C11A C12A C17A . . . . -176.2(2) ?
C10A C11A C12A C13A . . . . 2.3(3) ?
C11A C12A C13A C14A . . . . -178.70(18) ?
C17A C12A C13A C14A . . . . -0.2(3) ?
C11A C12A C13A C8A . . . . -0.2(3) ?
C17A C12A C13A C8A . . . . 178.39(17) ?
C9A C8A C13A C14A . . . . 175.33(17) ?
C7A C8A C13A C14A . . . . -2.4(3) ?
C9A C8A C13A C12A . . . . -3.1(2) ?
C7A C8A C13A C12A . . . . 179.18(15) ?
C12A C13A C14A C15A . . . . 0.1(3) ?
C8A C13A C14A C15A . . . . -178.39(18) ?
C13A C14A C15A C16A . . . . 0.2(3) ?
C14A C15A C16A C17A . . . . -0.4(3) ?
C15A C16A C17A C12A . . . . 0.3(4) ?
C11A C12A C17A C16A . . . . 178.5(2) ?
C13A C12A C17A C16A . . . . -0.1(3) ?
C7A N1A C18A O3A . . . 1 -5.8(3) ?
C7A N1A C18A O3A . . . . -5.8(3) ?
C7A N1A C18A O3A . . . 1 -5.8(3) ?
C7A N1A C18A C19A . . . . 173.15(18) ?
