##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
# cif/home.html #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
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##############################################################################
data_global
_audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic 2010-03-19
_journal_date_accepted 2010-04-11
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2010
_journal_volume 66
_journal_issue 5
_journal_page_first o1107
_journal_page_last o1107
_journal_paper_category QO
_journal_coeditor_code SU2170
_publ_contact_author_name 'Santiago Gar\'ia-Granda'
_publ_contact_author_address
;
Departamento de Qu\'imica F\'isica y Anal\'itica
Facultad de Qu\'imica
Universidad de Oviedo
C/ Juli\'an Claver\'ia, 8
33006 Oviedo
Spain
;
_publ_contact_author_email 'sgg@uniovi.es'
_publ_contact_author_fax '+34 985 103125'
_publ_contact_author_phone '+34 985 103477'
_publ_section_title
;
1,2-Diphenyl-2-(m-tolylamino)ethanone
;
_publ_section_title_footnote
;
Dedicated to the memory of Professor Jos\'e Manuel Concell\'on.
;
loop_
_publ_author_name
_publ_author_address
'Rafael Mendoza Mero\~no'
;
Departamento de Qu\'imica F\'isica y Anal\'itica
Facultad de Qu\'imica
Universidad de Oviedo
C/ Juli\'an Claver\'ia, 8
33006 Oviedo
Spain
;
'Felix N\'apoles Esculary'
;
Departamento de Qu\'imica
Facultad de Ciencias Naturales
Universidad de Oriente
Santiago de Cuba
Cuba
;
'Laura Men\'endez Taboada'
;
Departamento de Qu\'imica F\'isica y Anal\'itica
Facultad de Qu\'imica
Universidad de Oviedo
C/ Juli\'an Claver\'ia, 8
33006 Oviedo
Spain
;
'Santiago Garc\'ia-Granda'
;
Departamento de Qu\'imica F\'isica y Anal\'itica
Facultad de Qu\'imica
Universidad de Oviedo
C/ Juli\'an Claver\'ia, 8
33006 Oviedo
Spain
;
_publ_section_synopsis .
data_I
_chemical_name_systematic
;
1,2-Diphenyl-2-(m-tolylamino)ethanone
;
_chemical_name_common ?
_chemical_formula_moiety 'C21 H19 N O'
_chemical_formula_sum 'C21 H19 N O'
_chemical_formula_iupac 'C21 H19 N O'
_chemical_formula_weight 301.37
_chemical_melting_point 385.14
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a 6.0510(3)
_cell_length_b 11.5745(4)
_cell_length_c 12.9458(7)
_cell_angle_alpha 112.542(5)
_cell_angle_beta 97.396(4)
_cell_angle_gamma 99.960(4)
_cell_volume 805.62(8)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4346
_cell_measurement_theta_min 3.7903
_cell_measurement_theta_max 66.7168
_cell_measurement_temperature 293(2)
_exptl_crystal_description needle
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.07
_exptl_crystal_density_diffrn 1.242
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 320
_exptl_absorpt_coefficient_mu 0.590
_exptl_absorpt_correction_type refdelf
_exptl_absorpt_process_details
;
[cubic fit to sin(theta)/lambda - 24 parameters; Parkin et al.
(1995)]
;
_exptl_absorpt_correction_T_min 0.919
_exptl_absorpt_correction_T_max 0.960
_exptl_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based on F,
with F set to zero for negative F^2^. The threshold expression of F^2^ >
2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not
relevant to the choice of reflections for refinement. R-factors based on F^2^
are statistically about twice as large as those based on F, and R- factors
based on ALL data will be even larger.
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Gemini S'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number 8027
_diffrn_reflns_av_R_equivalents 0.0274
_diffrn_reflns_av_sigmaI/netI 0.0247
_diffrn_reflns_theta_min 3.78
_diffrn_reflns_theta_max 66.73
_diffrn_reflns_theta_full 66.73
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F^2^ are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total 2833
_reflns_number_gt 2174
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0532
_refine_ls_R_factor_gt 0.0430
_refine_ls_wR_factor_gt 0.1310
_refine_ls_wR_factor_ref 0.1368
_refine_ls_goodness_of_fit_ref 1.091
_refine_ls_restrained_S_all 1.091
_refine_ls_number_reflns 2833
_refine_ls_number_parameters 213
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0863P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.245
_refine_diff_density_min -0.159
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef 0.0041(11)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0181 0.0091
'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'
'O' 'O' 0.0492 0.0322
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0311 0.0180
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.52659(18) 0.50924(11) 0.14596(9) 0.0662(4) Uani . . 1.000
N N1 0.1300(2) 0.38301(13) 0.00199(11) 0.0529(4) Uani . . 1.000
C C1 0.6200(3) 0.63202(19) 0.38272(15) 0.0714(6) Uani . . 1.000
C C2 0.6620(4) 0.6946(2) 0.50033(17) 0.0880(8) Uani . . 1.000
C C3 0.4898(4) 0.6891(2) 0.55688(17) 0.0847(8) Uani . . 1.000
C C4 0.2717(4) 0.6232(2) 0.49658(17) 0.0863(8) Uani . . 1.000
C C5 0.2260(3) 0.56261(18) 0.37817(15) 0.0707(6) Uani . . 1.000
C C6 0.4006(3) 0.56467(14) 0.31949(13) 0.0497(5) Uani . . 1.000
C C7 0.3671(2) 0.49865(14) 0.19224(13) 0.0480(5) Uani . . 1.000
C C8 0.1322(2) 0.41085(13) 0.12058(12) 0.0452(4) Uani . . 1.000
C C9 0.0958(2) 0.28933(13) 0.14383(11) 0.0454(4) Uani . . 1.000
C C10 -0.0802(3) 0.25707(16) 0.19337(14) 0.0586(5) Uani . . 1.000
C C11 -0.1102(3) 0.14576(19) 0.21171(17) 0.0757(7) Uani . . 1.000
C C12 0.0364(4) 0.06604(19) 0.18093(18) 0.0819(7) Uani . . 1.000
C C13 0.2102(3) 0.09623(17) 0.13051(17) 0.0742(7) Uani . . 1.000
C C14 0.2411(3) 0.20731(15) 0.11226(14) 0.0574(5) Uani . . 1.000
C C15 -0.0560(2) 0.30252(13) -0.08485(12) 0.0452(4) Uani . . 1.000
C C16 -0.2728(3) 0.26933(15) -0.06433(14) 0.0540(5) Uani . . 1.000
C C17 -0.4522(3) 0.18600(16) -0.15360(14) 0.0597(6) Uani . . 1.000
C C18 -0.4218(3) 0.13398(16) -0.26408(15) 0.0633(6) Uani . . 1.000
C C19 -0.2086(3) 0.16684(16) -0.28761(14) 0.0578(5) Uani . . 1.000
C C20 -0.0286(3) 0.25155(14) -0.19799(13) 0.0510(5) Uani . . 1.000
C C21 -0.1709(4) 0.1084(2) -0.40766(16) 0.0896(8) Uani . . 1.000
H H1 0.74080 0.63510 0.34540 0.0860 Uiso calc R 1.000
H H2 0.81000 0.74100 0.54130 0.1060 Uiso calc R 1.000
H H3 0.52000 0.73000 0.63640 0.1020 Uiso calc R 1.000
H H4 0.15330 0.61900 0.53520 0.1040 Uiso calc R 1.000
H H5 0.07610 0.52010 0.33780 0.0850 Uiso calc R 1.000
H H8 0.01180 0.45580 0.14410 0.0540 Uiso calc R 1.000
H H10 -0.17960 0.31080 0.21460 0.0700 Uiso calc R 1.000
H H11 -0.22970 0.12480 0.24490 0.0910 Uiso calc R 1.000
H H12 0.01770 -0.00810 0.19430 0.0980 Uiso calc R 1.000
H H13 0.30790 0.04160 0.10850 0.0890 Uiso calc R 1.000
H H14 0.36020 0.22730 0.07850 0.0690 Uiso calc R 1.000
H H16 -0.29700 0.30340 0.00980 0.0650 Uiso calc R 1.000
H H17 -0.59640 0.16470 -0.13870 0.0720 Uiso calc R 1.000
H H18 -0.54410 0.07680 -0.32300 0.0760 Uiso calc R 1.000
H H20 0.11400 0.27500 -0.21360 0.0610 Uiso calc R 1.000
H H21A -0.31250 0.05270 -0.45850 0.1340 Uiso calc R 1.000
H H21B -0.05730 0.05940 -0.40990 0.1340 Uiso calc R 1.000
H H21C -0.11860 0.17570 -0.43120 0.1340 Uiso calc R 1.000
H H22 0.262(3) 0.4037(17) -0.0130(15) 0.062(5) Uiso . . 1.000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0533(7) 0.0727(8) 0.0548(7) -0.0058(6) 0.0118(5) 0.0167(6)
N1 0.0473(7) 0.0602(8) 0.0438(7) 0.0004(6) 0.0051(6) 0.0207(6)
C1 0.0584(10) 0.0864(13) 0.0546(10) 0.0023(9) 0.0014(8) 0.0235(9)
C2 0.0714(12) 0.1108(17) 0.0540(11) -0.0008(11) -0.0099(10) 0.0220(11)
C3 0.1014(16) 0.0868(14) 0.0459(10) 0.0088(12) 0.0028(10) 0.0164(10)
C4 0.0896(14) 0.0886(14) 0.0559(11) 0.0028(12) 0.0230(10) 0.0096(10)
C5 0.0637(10) 0.0698(11) 0.0536(10) 0.0000(9) 0.0116(8) 0.0066(9)
C6 0.0528(8) 0.0442(8) 0.0467(8) 0.0051(6) 0.0043(7) 0.0180(7)
C7 0.0482(8) 0.0424(8) 0.0495(9) 0.0043(6) 0.0072(7) 0.0189(7)
C8 0.0449(7) 0.0435(7) 0.0419(8) 0.0067(6) 0.0063(6) 0.0148(6)
C9 0.0449(7) 0.0429(8) 0.0373(7) 0.0024(6) -0.0008(6) 0.0114(6)
C10 0.0547(9) 0.0597(9) 0.0553(10) 0.0018(7) 0.0080(7) 0.0239(8)
C11 0.0766(12) 0.0717(12) 0.0716(13) -0.0114(10) 0.0029(10) 0.0387(10)
C12 0.0939(14) 0.0551(10) 0.0810(14) -0.0101(10) -0.0212(11) 0.0360(10)
C13 0.0802(12) 0.0503(10) 0.0758(12) 0.0156(9) -0.0107(10) 0.0177(9)
C14 0.0583(9) 0.0513(9) 0.0527(9) 0.0100(7) 0.0032(7) 0.0152(7)
C15 0.0466(8) 0.0422(7) 0.0455(8) 0.0090(6) 0.0030(6) 0.0199(6)
C16 0.0487(8) 0.0590(9) 0.0502(9) 0.0106(7) 0.0078(7) 0.0202(7)
C17 0.0452(8) 0.0632(10) 0.0640(11) 0.0057(7) 0.0031(7) 0.0253(9)
C18 0.0583(10) 0.0554(9) 0.0591(10) 0.0013(8) -0.0093(8) 0.0178(8)
C19 0.0662(10) 0.0531(9) 0.0479(9) 0.0111(7) 0.0037(7) 0.0187(7)
C20 0.0531(8) 0.0517(8) 0.0481(9) 0.0092(7) 0.0085(7) 0.0230(7)
C21 0.0968(15) 0.0917(15) 0.0515(11) 0.0013(12) 0.0072(10) 0.0113(10)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . . 1.2123(18) no
N1 C8 . . 1.4405(19) no
N1 C15 . . 1.3810(19) no
N1 H22 . . 0.862(19) no
C1 C6 . . 1.383(3) no
C1 C2 . . 1.378(3) no
C2 C3 . . 1.355(3) no
C3 C4 . . 1.365(3) no
C4 C5 . . 1.385(3) no
C5 C6 . . 1.381(3) no
C6 C7 . . 1.495(2) no
C7 C8 . . 1.534(2) no
C8 C9 . . 1.534(2) no
C9 C14 . . 1.388(2) no
C9 C10 . . 1.381(2) no
C10 C11 . . 1.383(3) no
C11 C12 . . 1.375(3) no
C12 C13 . . 1.371(3) no
C13 C14 . . 1.380(3) no
C15 C20 . . 1.398(2) no
C15 C16 . . 1.390(2) no
C16 C17 . . 1.380(2) no
C17 C18 . . 1.374(2) no
C18 C19 . . 1.386(3) no
C19 C20 . . 1.388(2) no
C19 C21 . . 1.505(3) no
C1 H1 . . 0.9300 no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C8 H8 . . 0.9800 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C16 H16 . . 0.9300 no
C17 H17 . . 0.9300 no
C18 H18 . . 0.9300 no
C20 H20 . . 0.9300 no
C21 H21A . . 0.9600 no
C21 H21B . . 0.9600 no
C21 H21C . . 0.9600 no
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C15 . . . 122.36(13) no
C8 N1 H22 . . . 115.3(12) no
C15 N1 H22 . . . 120.7(12) no
C2 C1 C6 . . . 120.89(18) no
C1 C2 C3 . . . 120.6(2) no
C2 C3 C4 . . . 119.66(19) no
C3 C4 C5 . . . 120.3(2) no
C4 C5 C6 . . . 120.71(18) no
C1 C6 C7 . . . 118.15(15) no
C1 C6 C5 . . . 117.76(15) no
C5 C6 C7 . . . 124.08(15) no
O1 C7 C8 . . . 119.84(13) no
O1 C7 C6 . . . 120.53(14) no
C6 C7 C8 . . . 119.55(13) no
N1 C8 C9 . . . 112.77(13) no
C7 C8 C9 . . . 107.94(12) no
N1 C8 C7 . . . 108.31(12) no
C10 C9 C14 . . . 118.55(16) no
C8 C9 C10 . . . 122.18(13) no
C8 C9 C14 . . . 119.26(13) no
C9 C10 C11 . . . 120.72(17) no
C10 C11 C12 . . . 120.06(19) no
C11 C12 C13 . . . 119.8(2) no
C12 C13 C14 . . . 120.36(19) no
C9 C14 C13 . . . 120.52(16) no
C16 C15 C20 . . . 117.97(14) no
N1 C15 C16 . . . 122.36(13) no
N1 C15 C20 . . . 119.68(13) no
C15 C16 C17 . . . 120.25(15) no
C16 C17 C18 . . . 121.25(17) no
C17 C18 C19 . . . 119.89(17) no
C18 C19 C20 . . . 118.88(16) no
C18 C19 C21 . . . 120.58(17) no
C20 C19 C21 . . . 120.51(17) no
C15 C20 C19 . . . 121.73(16) no
C2 C1 H1 . . . 120.00 no
C6 C1 H1 . . . 120.00 no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
N1 C8 H8 . . . 109.00 no
C7 C8 H8 . . . 109.00 no
C9 C8 H8 . . . 109.00 no
C9 C10 H10 . . . 120.00 no
C11 C10 H10 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C12 C13 H13 . . . 120.00 no
C14 C13 H13 . . . 120.00 no
C9 C14 H14 . . . 120.00 no
C13 C14 H14 . . . 120.00 no
C15 C16 H16 . . . 120.00 no
C17 C16 H16 . . . 120.00 no
C16 C17 H17 . . . 119.00 no
C18 C17 H17 . . . 119.00 no
C17 C18 H18 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C15 C20 H20 . . . 119.00 no
C19 C20 H20 . . . 119.00 no
C19 C21 H21A . . . 109.00 no
C19 C21 H21B . . . 109.00 no
C19 C21 H21C . . . 110.00 no
H21A C21 H21B . . . 109.00 no
H21A C21 H21C . . . 110.00 no
H21B C21 H21C . . . 109.00 no
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
C15 N1 C8 C7 . . . . 177.87(14) no
C15 N1 C8 C9 . . . . 58.48(18) no
C8 N1 C15 C16 . . . . 17.0(2) no
C8 N1 C15 C20 . . . . -162.92(15) no
C6 C1 C2 C3 . . . . 1.5(4) no
C2 C1 C6 C5 . . . . 0.1(3) no
C2 C1 C6 C7 . . . . -179.82(19) no
C1 C2 C3 C4 . . . . -1.4(4) no
C2 C3 C4 C5 . . . . -0.3(4) no
C3 C4 C5 C6 . . . . 1.9(4) no
C4 C5 C6 C1 . . . . -1.8(3) no
C4 C5 C6 C7 . . . . 178.17(19) no
C1 C6 C7 O1 . . . . -3.4(3) no
C1 C6 C7 C8 . . . . 173.22(17) no
C5 C6 C7 O1 . . . . 176.72(18) no
C5 C6 C7 C8 . . . . -6.7(3) no
O1 C7 C8 N1 . . . . -16.0(2) no
O1 C7 C8 C9 . . . . 106.37(17) no
C6 C7 C8 N1 . . . . 167.39(14) no
C6 C7 C8 C9 . . . . -70.22(17) no
N1 C8 C9 C10 . . . . -123.21(14) no
N1 C8 C9 C14 . . . . 55.51(17) no
C7 C8 C9 C10 . . . . 117.19(14) no
C7 C8 C9 C14 . . . . -64.09(16) no
C8 C9 C10 C11 . . . . 179.09(15) no
C14 C9 C10 C11 . . . . 0.4(2) no
C8 C9 C14 C13 . . . . -178.99(15) no
C10 C9 C14 C13 . . . . -0.2(2) no
C9 C10 C11 C12 . . . . 0.2(3) no
C10 C11 C12 C13 . . . . -1.0(3) no
C11 C12 C13 C14 . . . . 1.1(3) no
C12 C13 C14 C9 . . . . -0.5(3) no
N1 C15 C16 C17 . . . . -178.40(17) no
C20 C15 C16 C17 . . . . 1.5(3) no
N1 C15 C20 C19 . . . . 177.80(17) no
C16 C15 C20 C19 . . . . -2.2(3) no
C15 C16 C17 C18 . . . . 0.1(3) no
C16 C17 C18 C19 . . . . -1.1(3) no
C17 C18 C19 C20 . . . . 0.5(3) no
C17 C18 C19 C21 . . . . 178.57(19) no
C18 C19 C20 C15 . . . . 1.1(3) no
C21 C19 C20 C15 . . . . -176.92(18) no
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
N1 H22 O1 2_665 0.859(17) 2.660(17) 3.3913(17) 143.8(15)