#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227043.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_2227043
loop_
_publ_author_name
'Ramli, Youssef'
'Moussaif, Ahmed'
'Zouihri, Hafid'
'Lazar, Saïd'
'Essassi, E. M.'
_publ_section_title
;
 1-Benzyl-3-methylquinoxalin-2(1H)-one
;
_journal_coeditor_code           PV2301
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1922
_journal_paper_doi               10.1107/S1600536810025614
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H14 N2 O'
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_name_systematic
;
1-Benzyl-3-methylquinoxalin-2(1H)-one
;
_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                118.034(2)
_cell_angle_beta                 100.217(2)
_cell_angle_gamma                92.7260(10)
_cell_formula_units_Z            6
_cell_length_a                   7.4433(2)
_cell_length_b                   17.5444(5)
_cell_length_c                   18.0598(7)
_cell_measurement_pressure       101
_cell_measurement_reflns_used    4372
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.3
_cell_volume                     2025.27(12)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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    0.0234
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            46425
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.239
_refine_ls_extinction_coef       0.0084(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         9750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0860P)²+0.1960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                6445
_reflns_number_total             9750
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2301.cif
_cod_data_source_block           I
_cod_original_cell_volume        2025.27(11)
_cod_database_code               2227043
_cod_database_fobs_code          2227043
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
N N11 0.28817(17) 0.61727(8) 0.12094(8) 0.0539(3) Uani d . 1 . .
N N12 0.24494(17) 0.50211(9) -0.05373(8) 0.0535(3) Uani d . 1 . .
N N21 0.68069(17) 0.40186(8) 0.50730(7) 0.0473(3) Uani d . 1 . .
N N22 0.82004(17) 0.56626(8) 0.53631(8) 0.0535(3) Uani d . 1 . .
N N31 0.29515(17) 0.08130(8) 0.97102(8) 0.0497(3) Uani d . 1 . .
N N32 0.22062(16) -0.00511(8) 1.06097(8) 0.0496(3) Uani d . 1 . .
C C310 0.28440(18) -0.00937(9) 0.93170(9) 0.0452(3) Uani d . 1 . .
C C316 0.22919(19) 0.07835(10) 1.09571(9) 0.0485(3) Uani d . 1 . .
C C317 0.2642(2) 0.12871(10) 1.05228(10) 0.0518(4) Uani d . 1 . .
C C314 0.2368(2) -0.14167(10) 0.94073(10) 0.0557(4) Uani d . 1 . .
H H314 0.2116 -0.1693 0.9716 0.067 Uiso calc R 1 . .
C C311 0.3100(2) -0.05966(11) 0.84834(10) 0.0571(4) Uani d . 1 . .
H H311 0.3340 -0.0330 0.8164 0.069 Uiso calc R 1 . .
C C313 0.2644(2) -0.19009(11) 0.85939(11) 0.0635(4) Uani d . 1 . .
H H313 0.2595 -0.2503 0.8352 0.076 Uiso calc R 1 . .
C C312 0.2996(2) -0.14864(12) 0.81358(11) 0.0643(5) Uani d . 1 . .
H H312 0.3167 -0.1817 0.7580 0.077 Uiso calc R 1 . .
C C320 0.1937(2) 0.12140(10) 0.85582(10) 0.0562(4) Uani d . 1 . .
C C319 0.3461(2) 0.12854(12) 0.92698(12) 0.0637(4) Uani d . 1 . .
H H31A 0.4511 0.1063 0.9030 0.076 Uiso calc R 1 . .
H H31B 0.3847 0.1898 0.9692 0.076 Uiso calc R 1 . .
C C31 0.2052(3) 0.12919(12) 1.18591(11) 0.0657(4) Uani d . 1 . .
H H31C 0.1831 0.0899 1.2076 0.099 Uiso calc PR 0.50 . .
H H31D 0.1020 0.1601 1.1865 0.099 Uiso calc PR 0.50 . .
H H31E 0.3150 0.1702 1.2215 0.099 Uiso calc PR 0.50 . .
H H31F 0.2169 0.1902 1.2028 0.099 Uiso calc PR 0.50 . .
H H31G 0.2981 0.1200 1.2239 0.099 Uiso calc PR 0.50 . .
H H31H 0.0851 0.1100 1.1889 0.099 Uiso calc PR 0.50 . .
C C325 0.0106(3) 0.09773(12) 0.84936(12) 0.0684(5) Uani d . 1 . .
H H325 -0.0229 0.0836 0.8892 0.082 Uiso calc R 1 . .
C C323 -0.0772(4) 0.11456(15) 0.72508(15) 0.0924(7) Uani d . 1 . .
H H323 -0.1680 0.1115 0.6807 0.111 Uiso calc R 1 . .
C C321 0.2399(3) 0.14226(12) 0.79587(13) 0.0766(5) Uani d . 1 . .
H H321 0.3630 0.1586 0.7992 0.092 Uiso calc R 1 . .
C C322 0.1044(4) 0.13898(14) 0.73145(15) 0.0938(7) Uani d . 1 . .
H H322 0.1368 0.1535 0.6917 0.113 Uiso calc R 1 . .
C C324 -0.1241(3) 0.09471(15) 0.78441(14) 0.0856(6) Uani d . 1 . .
H H324 -0.2476 0.0790 0.7810 0.103 Uiso calc R 1 . .
C C210 0.64496(18) 0.42088(9) 0.43991(8) 0.0420(3) Uani d . 1 . .
C C215 0.71574(19) 0.50356(9) 0.45595(9) 0.0450(3) Uani d . 1 . .
C C217 0.7903(2) 0.46041(11) 0.58679(9) 0.0532(4) Uani d . 1 . .
C C211 0.54277(19) 0.36064(10) 0.35746(9) 0.0510(3) Uani d . 1 . .
H H211 0.4967 0.3050 0.3458 0.061 Uiso calc R 1 . .
C C216 0.85465(19) 0.54651(10) 0.59690(9) 0.0521(4) Uani d . 1 . .
C C212 0.5101(2) 0.38320(12) 0.29369(10) 0.0599(4) Uani d . 1 . .
H H212 0.4423 0.3426 0.2390 0.072 Uiso calc R 1 . .
C C214 0.6798(2) 0.52521(11) 0.39025(11) 0.0573(4) Uani d . 1 . .
H H214 0.7258 0.5805 0.4008 0.069 Uiso calc R 1 . .
C C213 0.5769(2) 0.46550(13) 0.30999(11) 0.0629(4) Uani d . 1 . .
H H213 0.5523 0.4806 0.2667 0.075 Uiso calc R 1 . .
C C219 0.6009(3) 0.31832(11) 0.49568(11) 0.0613(4) Uani d . 1 . .
H H21A 0.4733 0.3045 0.4643 0.074 Uiso calc R 1 . .
H H21B 0.6016 0.3240 0.5518 0.074 Uiso calc R 1 . .
C C21 0.9649(2) 0.61360(13) 0.68370(11) 0.0733(5) Uani d . 1 . .
H H21C 0.9990 0.6665 0.6826 0.110 Uiso calc PR 0.50 . .
H H21D 1.0744 0.5922 0.6985 0.110 Uiso calc PR 0.50 . .
H H21E 0.8923 0.6252 0.7258 0.110 Uiso calc PR 0.50 . .
H H21F 0.9781 0.5895 0.7220 0.110 Uiso calc PR 0.50 . .
H H21G 0.9027 0.6637 0.7061 0.110 Uiso calc PR 0.50 . .
H H21H 1.0848 0.6307 0.6788 0.110 Uiso calc PR 0.50 . .
C C220 0.7010(3) 0.24364(10) 0.44807(10) 0.0605(4) Uani d . 1 . .
C C225 0.8727(3) 0.25573(12) 0.43371(10) 0.0639(4) Uani d . 1 . .
H H225 0.9296 0.3119 0.4519 0.077 Uiso calc R 1 . .
C C224 0.9621(3) 0.18488(14) 0.39230(12) 0.0816(6) Uani d . 1 . .
H H224 1.0781 0.1938 0.3828 0.098 Uiso calc R 1 . .
C C222 0.7101(6) 0.08964(16) 0.37896(19) 0.1197(10) Uani d . 1 . .
H H222 0.6543 0.0332 0.3606 0.144 Uiso calc R 1 . .
C C223 0.8800(5) 0.10206(16) 0.36553(15) 0.1040(9) Uani d . 1 . .
H H223 0.9402 0.0546 0.3383 0.125 Uiso calc R 1 . .
C C221 0.6180(4) 0.15941(14) 0.41957(16) 0.0984(7) Uani d . 1 . .
H H221 0.5009 0.1497 0.4277 0.118 Uiso calc R 1 . .
C C115 0.21989(19) 0.47190(9) 0.00291(9) 0.0480(3) Uani d . 1 . .
C C110 0.24117(18) 0.52774(10) 0.09044(9) 0.0474(3) Uani d . 1 . .
C C116 0.2905(2) 0.58474(11) -0.02376(11) 0.0555(4) Uani d . 1 . .
C C117 0.3162(2) 0.64957(10) 0.06708(11) 0.0570(4) Uani d . 1 . .
C C114 0.1692(2) 0.38238(11) -0.03048(12) 0.0614(4) Uani d . 1 . .
H H114 0.1528 0.3451 -0.0893 0.074 Uiso calc R 1 . .
C C120 0.4972(2) 0.69464(11) 0.26728(10) 0.0568(4) Uani d . 1 . .
C C111 0.2174(2) 0.49301(13) 0.14423(11) 0.0643(4) Uani d . 1 . .
H H111 0.2334 0.5295 0.2032 0.077 Uiso calc R 1 . .
C C112 0.1700(3) 0.40430(15) 0.10900(15) 0.0759(6) Uani d . 1 . .
H H112 0.1554 0.3812 0.1449 0.091 Uiso calc R 1 . .
C C125 0.6317(2) 0.64524(12) 0.23666(12) 0.0652(4) Uani d . 1 . .
H H125 0.6074 0.6011 0.1796 0.078 Uiso calc R 1 . .
C C119 0.3077(3) 0.68063(12) 0.21185(11) 0.0708(5) Uani d . 1 . .
H H11A 0.2167 0.6609 0.2340 0.085 Uiso calc R 1 . .
H H11B 0.2811 0.7361 0.2165 0.085 Uiso calc R 1 . .
C C113 0.1435(3) 0.34875(13) 0.02172(16) 0.0758(5) Uani d . 1 . .
H H113 0.1085 0.2890 -0.0012 0.091 Uiso calc R 1 . .
C C11 0.3186(3) 0.61802(15) -0.08384(15) 0.0822(6) Uani d . 1 . .
H H11C 0.4464 0.6413 -0.0712 0.123 Uiso calc R 1 . .
H H11D 0.2444 0.6632 -0.0769 0.123 Uiso calc R 1 . .
H H11E 0.2831 0.5710 -0.1421 0.123 Uiso calc R 1 . .
C C124 0.8032(3) 0.66059(15) 0.29001(15) 0.0790(6) Uani d . 1 . .
H H124 0.8923 0.6260 0.2686 0.095 Uiso calc R 1 . .
C C122 0.7113(4) 0.77463(18) 0.40426(13) 0.0971(8) Uani d . 1 . .
H H122 0.7379 0.8190 0.4613 0.117 Uiso calc R 1 . .
C C123 0.8427(3) 0.72538(18) 0.37299(16) 0.0909(7) Uani d . 1 . .
H H123 0.9589 0.7360 0.4082 0.109 Uiso calc R 1 . .
C C121 0.5376(3) 0.75980(13) 0.35231(11) 0.0774(5) Uani d . 1 . .
H H121 0.4485 0.7937 0.3747 0.093 Uiso calc R 1 . .
C C315 0.24616(18) -0.05134(9) 0.97775(9) 0.0453(3) Uani d . 1 . .
O O3 0.2684(2) 0.20807(7) 1.08693(8) 0.0760(4) Uani d . 1 . .
O O2 0.8293(2) 0.44281(9) 0.64486(8) 0.0787(4) Uani d . 1 . .
O O1 0.3599(2) 0.72780(8) 0.09362(10) 0.0879(4) 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
C117 N11 C110 . . 121.79(13) ?
C117 N11 C119 . . 117.13(14) ?
C110 N11 C119 . . 121.08(14) ?
C116 N12 C115 . . 118.81(13) ?
C217 N21 C210 . . 121.92(13) ?
C217 N21 C219 . . 117.66(13) ?
C210 N21 C219 . . 120.41(12) ?
C216 N22 C215 . . 118.75(13) ?
C317 N31 C310 . . 121.23(12) ?
C317 N31 C319 . . 118.47(13) ?
C310 N31 C319 . . 120.27(13) ?
C316 N32 C315 . . 118.81(13) ?
N31 C310 C311 . . 122.63(14) ?
N31 C310 C315 . . 118.51(13) ?
C311 C310 C315 . . 118.85(14) ?
N32 C316 C317 . . 123.92(13) ?
N32 C316 C31 . . 119.39(15) ?
C317 C316 C31 . . 116.69(14) ?
O3 C317 N31 . . 122.14(15) ?
O3 C317 C316 . . 122.08(15) ?
N31 C317 C316 . . 115.77(13) ?
C313 C314 C315 . . 120.65(16) ?
C313 C314 H314 . . 119.7 ?
C315 C314 H314 . . 119.7 ?
C312 C311 C310 . . 119.83(16) ?
C312 C311 H311 . . 120.1 ?
C310 C311 H311 . . 120.1 ?
C314 C313 C312 . . 119.32(15) ?
C314 C313 H313 . . 120.3 ?
C312 C313 H313 . . 120.3 ?
C311 C312 C313 . . 121.41(16) ?
C311 C312 H312 . . 119.3 ?
C313 C312 H312 . . 119.3 ?
C325 C320 C321 . . 118.56(17) ?
C325 C320 C319 . . 122.91(15) ?
C321 C320 C319 . . 118.50(16) ?
N31 C319 C320 . . 114.42(13) ?
N31 C319 H31A . . 108.7 ?
C320 C319 H31A . . 108.7 ?
N31 C319 H31B . . 108.7 ?
C320 C319 H31B . . 108.7 ?
H31A C319 H31B . . 107.6 ?
C316 C31 H31C . . 109.5 ?
C316 C31 H31D . . 109.5 ?
H31C C31 H31D . . 109.5 ?
C316 C31 H31E . . 109.5 ?
H31C C31 H31E . . 109.5 ?
H31D C31 H31E . . 109.5 ?
C316 C31 H31F . . 109.5 ?
H31C C31 H31F . . 141.1 ?
H31D C31 H31F . . 56.3 ?
H31E C31 H31F . . 56.3 ?
C316 C31 H31G . . 109.5 ?
H31C C31 H31G . . 56.3 ?
H31D C31 H31G . . 141.1 ?
H31E C31 H31G . . 56.3 ?
H31F C31 H31G . . 109.5 ?
C316 C31 H31H . . 109.5 ?
H31C C31 H31H . . 56.3 ?
H31D C31 H31H . . 56.3 ?
H31E C31 H31H . . 141.1 ?
H31F C31 H31H . . 109.5 ?
H31G C31 H31H . . 109.5 ?
C320 C325 C324 . . 120.63(19) ?
C320 C325 H325 . . 119.7 ?
C324 C325 H325 . . 119.7 ?
C324 C323 C322 . . 119.4(2) ?
C324 C323 H323 . . 120.3 ?
C322 C323 H323 . . 120.3 ?
C322 C321 C320 . . 120.3(2) ?
C322 C321 H321 . . 119.9 ?
C320 C321 H321 . . 119.9 ?
C323 C322 C321 . . 120.7(2) ?
C323 C322 H322 . . 119.6 ?
C321 C322 H322 . . 119.6 ?
C323 C324 C325 . . 120.4(2) ?
C323 C324 H324 . . 119.8 ?
C325 C324 H324 . . 119.8 ?
N21 C210 C215 . . 118.06(12) ?
N21 C210 C211 . . 122.81(13) ?
C215 C210 C211 . . 119.13(13) ?
N22 C215 C210 . . 122.03(13) ?
N22 C215 C214 . . 118.47(14) ?
C210 C215 C214 . . 119.49(14) ?
O2 C217 N21 . . 122.38(16) ?
O2 C217 C216 . . 122.44(15) ?
N21 C217 C216 . . 115.18(13) ?
C212 C211 C210 . . 120.35(15) ?
C212 C211 H211 . . 119.8 ?
C210 C211 H211 . . 119.8 ?
N22 C216 C217 . . 123.92(13) ?
N22 C216 C21 . . 119.22(16) ?
C217 C216 C21 . . 116.85(15) ?
C211 C212 C213 . . 120.53(15) ?
C211 C212 H212 . . 119.7 ?
C213 C212 H212 . . 119.7 ?
C213 C214 C215 . . 120.48(16) ?
C213 C214 H214 . . 119.8 ?
C215 C214 H214 . . 119.8 ?
C214 C213 C212 . . 120.00(15) ?
C214 C213 H213 . . 120.0 ?
C212 C213 H213 . . 120.0 ?
N21 C219 C220 . . 113.86(14) ?
N21 C219 H21A . . 108.8 ?
C220 C219 H21A . . 108.8 ?
N21 C219 H21B . . 108.8 ?
C220 C219 H21B . . 108.8 ?
H21A C219 H21B . . 107.7 ?
C216 C21 H21C . . 109.5 ?
C216 C21 H21D . . 109.5 ?
H21C C21 H21D . . 109.5 ?
C216 C21 H21E . . 109.5 ?
H21C C21 H21E . . 109.5 ?
H21D C21 H21E . . 109.5 ?
C216 C21 H21F . . 109.5 ?
H21C C21 H21F . . 141.1 ?
H21D C21 H21F . . 56.3 ?
H21E C21 H21F . . 56.3 ?
C216 C21 H21G . . 109.5 ?
H21C C21 H21G . . 56.3 ?
H21D C21 H21G . . 141.1 ?
H21E C21 H21G . . 56.3 ?
H21F C21 H21G . . 109.5 ?
C216 C21 H21H . . 109.5 ?
H21C C21 H21H . . 56.3 ?
H21D C21 H21H . . 56.3 ?
H21E C21 H21H . . 141.1 ?
H21F C21 H21H . . 109.5 ?
H21G C21 H21H . . 109.5 ?
C225 C220 C221 . . 118.69(18) ?
C225 C220 C219 . . 122.86(16) ?
C221 C220 C219 . . 118.43(19) ?
C220 C225 C224 . . 120.62(19) ?
C220 C225 H225 . . 119.7 ?
C224 C225 H225 . . 119.7 ?
C223 C224 C225 . . 120.2(2) ?
C223 C224 H224 . . 119.9 ?
C225 C224 H224 . . 119.9 ?
C223 C222 C221 . . 121.2(3) ?
C223 C222 H222 . . 119.4 ?
C221 C222 H222 . . 119.4 ?
C222 C223 C224 . . 119.5(2) ?
C222 C223 H223 . . 120.3 ?
C224 C223 H223 . . 120.3 ?
C220 C221 C222 . . 119.8(3) ?
C220 C221 H221 . . 120.1 ?
C222 C221 H221 . . 120.1 ?
C110 C115 N12 . . 122.21(13) ?
C110 C115 C114 . . 119.57(14) ?
N12 C115 C114 . . 118.22(14) ?
C115 C110 C111 . . 119.38(15) ?
C115 C110 N11 . . 117.70(13) ?
C111 C110 N11 . . 122.91(14) ?
N12 C116 C117 . . 123.73(14) ?
N12 C116 C11 . . 119.35(16) ?
C117 C116 C11 . . 116.91(16) ?
O1 C117 N11 . . 122.09(16) ?
O1 C117 C116 . . 122.16(17) ?
N11 C117 C116 . . 115.74(13) ?
C113 C114 C115 . . 121.00(17) ?
C113 C114 H114 . . 119.5 ?
C115 C114 H114 . . 119.5 ?
C125 C120 C121 . . 118.34(17) ?
C125 C120 C119 . . 122.77(14) ?
C121 C120 C119 . . 118.90(16) ?
C112 C111 C110 . . 119.25(17) ?
C112 C111 H111 . . 120.4 ?
C110 C111 H111 . . 120.4 ?
C111 C112 C113 . . 121.61(17) ?
C111 C112 H112 . . 119.2 ?
C113 C112 H112 . . 119.2 ?
C120 C125 C124 . . 120.60(19) ?
C120 C125 H125 . . 119.7 ?
C124 C125 H125 . . 119.7 ?
N11 C119 C120 . . 113.91(14) ?
N11 C119 H11A . . 108.8 ?
C120 C119 H11A . . 108.8 ?
N11 C119 H11B . . 108.8 ?
C120 C119 H11B . . 108.8 ?
H11A C119 H11B . . 107.7 ?
C114 C113 C112 . . 119.15(17) ?
C114 C113 H113 . . 120.4 ?
C112 C113 H113 . . 120.4 ?
C116 C11 H11C . . 109.5 ?
C116 C11 H11D . . 109.5 ?
H11C C11 H11D . . 109.5 ?
C116 C11 H11E . . 109.5 ?
H11C C11 H11E . . 109.5 ?
H11D C11 H11E . . 109.5 ?
C123 C124 C125 . . 120.7(2) ?
C123 C124 H124 . . 119.6 ?
C125 C124 H124 . . 119.6 ?
C123 C122 C121 . . 120.9(2) ?
C123 C122 H122 . . 119.5 ?
C121 C122 H122 . . 119.5 ?
C124 C123 C122 . . 119.4(2) ?
C124 C123 H123 . . 120.3 ?
C122 C123 H123 . . 120.3 ?
C120 C121 C122 . . 120.0(2) ?
C120 C121 H121 . . 120.0 ?
C122 C121 H121 . . 120.0 ?
N32 C315 C314 . . 118.37(14) ?
N32 C315 C310 . . 121.69(13) ?
C314 C315 C310 . . 119.92(14) ?
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
N11 C117 . 1.375(2) ?
N11 C110 . 1.3996(19) ?
N11 C119 . 1.462(2) ?
N12 C116 . 1.288(2) ?
N12 C115 . 1.3891(19) ?
N21 C217 . 1.3784(19) ?
N21 C210 . 1.3925(18) ?
N21 C219 . 1.459(2) ?
N22 C216 . 1.284(2) ?
N22 C215 . 1.3920(19) ?
N31 C317 . 1.374(2) ?
N31 C310 . 1.3954(18) ?
N31 C319 . 1.470(2) ?
N32 C316 . 1.2866(19) ?
N32 C315 . 1.3868(18) ?
C310 C311 . 1.397(2) ?
C310 C315 . 1.398(2) ?
C316 C317 . 1.472(2) ?
C316 C31 . 1.495(2) ?
C317 O3 . 1.2251(18) ?
C314 C313 . 1.369(2) ?
C314 C315 . 1.393(2) ?
C314 H314 . 0.9300 ?
C311 C312 . 1.374(2) ?
C311 H311 . 0.9300 ?
C313 C312 . 1.381(3) ?
C313 H313 . 0.9300 ?
C312 H312 . 0.9300 ?
C320 C325 . 1.374(3) ?
C320 C321 . 1.384(2) ?
C320 C319 . 1.507(2) ?
C319 H31A . 0.9700 ?
C319 H31B . 0.9700 ?
C31 H31C . 0.9600 ?
C31 H31D . 0.9600 ?
C31 H31E . 0.9600 ?
C31 H31F . 0.9600 ?
C31 H31G . 0.9600 ?
C31 H31H . 0.9600 ?
C325 C324 . 1.379(3) ?
C325 H325 . 0.9300 ?
C323 C324 . 1.365(3) ?
C323 C322 . 1.367(4) ?
C323 H323 . 0.9300 ?
C321 C322 . 1.374(3) ?
C321 H321 . 0.9300 ?
C322 H322 . 0.9300 ?
C324 H324 . 0.9300 ?
C210 C215 . 1.394(2) ?
C210 C211 . 1.3983(19) ?
C215 C214 . 1.394(2) ?
C217 O2 . 1.2185(19) ?
C217 C216 . 1.478(2) ?
C211 C212 . 1.371(2) ?
C211 H211 . 0.9300 ?
C216 C21 . 1.495(2) ?
C212 C213 . 1.378(3) ?
C212 H212 . 0.9300 ?
C214 C213 . 1.374(2) ?
C214 H214 . 0.9300 ?
C213 H213 . 0.9300 ?
C219 C220 . 1.507(2) ?
C219 H21A . 0.9700 ?
C219 H21B . 0.9700 ?
C21 H21C . 0.9600 ?
C21 H21D . 0.9600 ?
C21 H21E . 0.9600 ?
C21 H21F . 0.9600 ?
C21 H21G . 0.9600 ?
C21 H21H . 0.9600 ?
C220 C225 . 1.375(3) ?
C220 C221 . 1.384(3) ?
C225 C224 . 1.388(2) ?
C225 H225 . 0.9300 ?
C224 C223 . 1.367(4) ?
C224 H224 . 0.9300 ?
C222 C223 . 1.355(4) ?
C222 C221 . 1.386(4) ?
C222 H222 . 0.9300 ?
C223 H223 . 0.9300 ?
C221 H221 . 0.9300 ?
C115 C110 . 1.387(2) ?
C115 C114 . 1.395(2) ?
C110 C111 . 1.398(2) ?
C116 C117 . 1.462(2) ?
C116 C11 . 1.492(2) ?
C117 O1 . 1.2261(19) ?
C114 C113 . 1.360(3) ?
C114 H114 . 0.9300 ?
C120 C125 . 1.374(2) ?
C120 C121 . 1.382(2) ?
C120 C119 . 1.512(2) ?
C111 C112 . 1.374(3) ?
C111 H111 . 0.9300 ?
C112 C113 . 1.379(3) ?
C112 H112 . 0.9300 ?
C125 C124 . 1.385(3) ?
C125 H125 . 0.9300 ?
C119 H11A . 0.9700 ?
C119 H11B . 0.9700 ?
C113 H113 . 0.9300 ?
C11 H11C . 0.9600 ?
C11 H11D . 0.9600 ?
C11 H11E . 0.9600 ?
C124 C123 . 1.355(3) ?
C124 H124 . 0.9300 ?
C122 C123 . 1.357(4) ?
C122 C121 . 1.388(3) ?
C122 H122 . 0.9300 ?
C123 H123 . 0.9300 ?
C121 H121 . 0.9300 ?
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
_geom_hbond_publ_flag
C119 H11B O1 . 0.97 2.34 2.706(3) 102 ?
C219 H21B O2 . 0.97 2.32 2.722(2) 104 ?
C21 H21F O2 . 0.96 2.37 2.824(3) 109 ?
C319 H31B O3 . 0.97 2.33 2.740(2) 105 ?
C31 H31F O3 . 0.96 2.35 2.810(3) 109 ?
C125 H125 N11 . 0.93 2.51 2.858(2) 102 ?
C125 H125 N12 2_665 0.93 2.62 3.423(2) 145 y
C225 H225 N21 . 0.93 2.53 2.864(3) 102 ?
C321 H321 O1 2_666 0.93 2.56 3.320(3) 140 y
C325 H325 N31 . 0.93 2.57 2.898(3) 101 ?
C325 H325 N32 2_557 0.93 2.51 3.380(3) 155 y
