# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_a
_database_code_depnum_ccdc_archive 'CCDC 1544196'
_audit_update_record
;
2017-04-15 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_iucr_refine_instructions_details
;
TITL a in P2(1)/n
CELL 0.71073 13.6727 17.6172 14.8361 90.000 116.334 90.000
ZERR 4.00 0.0012 0.0015 0.0013 0.000 0.001 0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 148 132 20 24
TEMP -123
SIZE .30 .30 .20
EQIV $1 -0.5+X, 1.5-Y, -0.5+Z
EQIV $2 0.5-X, 0.5+Y,0.5-Z
EQIV $3 1.5-X, -0.5+Y, 1.5-Z
EQIV $4 1-X, 1-Y, 1-Z
EQIV $5 0.5-X, -0.5+Y, 0.5-Z
HTAB O5 O11_$1
HTAB O5 O21_$2
HTAB N1 O11_$3
HTAB N11 O21_$4
HTAB N21 O1_$5
HTAB O2 O5
HTAB O3 O1
L.S. 10
BOND $H
ACTA
CONF
FMAP 2
PLAN 10
OMIT -2 56
OMIT -1 0 1
OMIT -1 1 1
OMIT 0 8 1
OMIT 1 1 0
DELU .005 C33 C34
DELU .005 C42 C43 C44 C45
WGHT 0.047100 0.814800
FVAR 0.11037
O5 4 0.329805 0.520497 0.177672 11.00000 0.02468 0.05553 =
0.02322 0.00972 0.00863 0.00772
H51 2 0.260961 0.536416 0.160271 11.00000 0.05519
H52 2 0.346792 0.533593 0.127988 11.00000 0.05242
N1 3 0.948353 0.465287 0.730357 11.00000 0.02778 0.06305 =
0.02507 0.00859 0.00548 0.00527
H1 2 1.017169 0.459868 0.733775 11.00000 0.05161
H10 2 0.934456 0.447829 0.780933 11.00000 0.05229
O1 4 0.604449 0.528524 0.274968 11.00000 0.03681 0.04891 =
0.02118 0.00725 0.00941 0.00472
O2 4 0.496578 0.505205 0.349303 11.00000 0.02652 0.07228 =
0.02372 0.00736 0.00596 0.00867
H2 2 0.440387 0.512776 0.287233 11.00000 0.07374
O3 4 0.815679 0.521958 0.383257 11.00000 0.03668 0.05510 =
0.02494 0.00180 0.01629 -0.00312
H3 2 0.748456 0.530426 0.329889 11.00000 0.06449
C1 1 0.593246 0.513576 0.351564 11.00000 0.03077 0.03389 =
0.02218 0.00204 0.00851 0.00517
C2 1 0.685314 0.503374 0.449950 11.00000 0.02731 0.03275 =
0.02078 0.00224 0.00795 0.00188
C3 1 0.793315 0.507096 0.461942 11.00000 0.03131 0.03022 =
0.02351 0.00002 0.01323 -0.00040
C4 1 0.880919 0.495398 0.555089 11.00000 0.02440 0.04044 =
0.02746 0.00017 0.01050 -0.00038
C5 1 0.863581 0.478205 0.638781 11.00000 0.02717 0.03623 =
0.02262 0.00191 0.00630 0.00197
C6 1 0.755993 0.475080 0.627582 11.00000 0.03058 0.05239 =
0.02152 0.00679 0.01118 -0.00011
C7 1 0.669989 0.487108 0.535510 11.00000 0.02606 0.05039 =
0.02484 0.00441 0.01008 0.00090
H4 2 0.954956 0.496690 0.561255 11.00000 0.04066
H6 2 0.742237 0.461888 0.683652 11.00000 0.04589
H7 2 0.595899 0.483555 0.526950 11.00000 0.04188
O11 4 0.618718 0.920075 0.606204 11.00000 0.02554 0.04090 =
0.02682 -0.00979 0.01087 -0.00815
N11 3 0.625250 0.880420 0.463762 11.00000 0.02610 0.04846 =
0.03337 -0.01739 0.01534 -0.01305
H11 2 0.593638 0.857268 0.406572 11.00000 0.04877
H12 2 0.693459 0.895937 0.484113 11.00000 0.03997
N12 3 0.469685 0.863002 0.483689 11.00000 0.02294 0.03230 =
0.02335 -0.00557 0.00992 -0.00617
C10 1 0.574962 0.889230 0.522339 11.00000 0.02246 0.02584 =
0.02619 -0.00267 0.00935 -0.00234
C11 1 0.415799 0.855718 0.546819 11.00000 0.01992 0.03584 =
0.02031 -0.00281 0.00610 -0.00543
C12 1 0.422585 0.786486 0.595331 11.00000 0.02918 0.04152 =
0.02711 0.00498 0.00780 -0.00149
C13 1 0.371139 0.781789 0.658519 11.00000 0.04338 0.05685 =
0.03037 0.01214 0.01405 -0.00602
C14 1 0.312244 0.841782 0.668904 11.00000 0.03352 0.07299 =
0.02800 -0.00185 0.01657 -0.01083
C15 1 0.302900 0.908643 0.616646 11.00000 0.02510 0.05445 =
0.02959 -0.01183 0.01093 -0.00584
C16 1 0.355322 0.915699 0.555619 11.00000 0.02370 0.03615 =
0.02489 -0.00579 0.00780 -0.00511
C17 1 0.476707 0.719990 0.578702 11.00000 0.04679 0.03946 =
0.04856 0.01420 0.01699 0.00737
C21 1 0.420393 0.820171 0.391913 11.00000 0.02251 0.03677 =
0.02757 -0.00836 0.01177 -0.00793
C22 1 0.428230 0.741180 0.396729 11.00000 0.03426 0.03662 =
0.04514 -0.01142 0.02046 -0.00830
C23 1 0.379833 0.701088 0.305517 11.00000 0.05354 0.04796 =
0.06243 -0.02804 0.03387 -0.02191
C24 1 0.322936 0.738389 0.215316 11.00000 0.04798 0.07984 =
0.04487 -0.03502 0.02355 -0.03165
C25 1 0.314912 0.816470 0.212616 11.00000 0.03481 0.08189 =
0.02704 -0.01194 0.01162 -0.01454
C26 1 0.364409 0.858018 0.301298 11.00000 0.02912 0.04955 =
0.02773 -0.00482 0.01265 -0.00754
C27 1 0.479105 0.700318 0.492473 11.00000 0.04924 0.03167 =
0.06205 0.00075 0.02517 0.00505
H13 2 0.377219 0.734566 0.692208 11.00000 0.05466
H14 2 0.276507 0.834888 0.712955 11.00000 0.05491
H15 2 0.261341 0.951726 0.623080 11.00000 0.04322
H16 2 0.351791 0.962672 0.519380 11.00000 0.03439
H17 2 0.507778 0.683836 0.637170 11.00000 0.05478
H23 2 0.383781 0.645697 0.308107 11.00000 0.06682
H24 2 0.289175 0.708479 0.151890 11.00000 0.07008
H25 2 0.274963 0.842769 0.146699 11.00000 0.05783
H26 2 0.361143 0.913002 0.302987 11.00000 0.04147
H27 2 0.513000 0.651508 0.491283 11.00000 0.05570
O21 4 0.152195 0.072724 0.482410 11.00000 0.02485 0.05343 =
0.03497 -0.01916 0.01460 -0.00531
N21 3 -0.028595 0.091694 0.427279 11.00000 0.02444 0.05906 =
0.02933 -0.01825 0.00911 -0.00073
H21 2 -0.080439 0.114700 0.437158 11.00000 0.05345
H22 2 -0.042182 0.068566 0.369286 11.00000 0.04604
N22 3 0.095394 0.142829 0.577858 11.00000 0.02178 0.03146 =
0.02320 -0.00546 0.00890 -0.00065
C30 1 0.075838 0.101172 0.493980 11.00000 0.02500 0.03157 =
0.02378 -0.00436 0.01154 -0.00391
C31 1 0.204350 0.166478 0.642577 11.00000 0.02406 0.03455 =
0.02254 -0.00755 0.01114 -0.00295
C32 1 0.238230 0.238871 0.630928 11.00000 0.04168 0.03923 =
0.03301 -0.01065 0.02484 -0.01026
C33 1 0.347455 0.258690 0.694754 11.00000 0.05034 0.05688 =
0.05643 -0.03069 0.03787 -0.02691
C34 1 0.416117 0.209611 0.766593 11.00000 0.02798 0.08381 =
0.05041 -0.03660 0.01335 -0.00958
C35 1 0.380075 0.138990 0.777019 11.00000 0.03414 0.06982 =
0.03624 -0.01824 0.00101 0.01094
C36 1 0.274009 0.117331 0.715378 11.00000 0.03388 0.04175 =
0.02907 -0.00629 0.00788 0.00499
C37 1 0.164559 0.293898 0.560108 11.00000 0.07968 0.03633 =
0.04050 0.00299 0.03340 -0.00863
C41 1 0.010396 0.180519 0.591684 11.00000 0.02241 0.04289 =
0.02408 -0.01111 0.00630 0.00164
C42 1 -0.010116 0.256866 0.565540 11.00000 0.03824 0.04575 =
0.02895 -0.00827 0.00156 0.01298
C43 1 -0.098935 0.289629 0.575800 11.00000 0.04701 0.06543 =
0.05854 -0.02672 -0.00288 0.02575
C44 1 -0.158422 0.248775 0.613598 11.00000 0.02609 0.11625 =
0.07735 -0.06023 0.01350 0.00333
C45 1 -0.134369 0.174499 0.640508 11.00000 0.03181 0.10491 =
0.06263 -0.04949 0.02617 -0.01829
C46 1 -0.049993 0.139517 0.629407 11.00000 0.02855 0.06550 =
0.03857 -0.02404 0.01683 -0.01368
C47 1 0.058220 0.302133 0.533321 11.00000 0.07821 0.03723 =
0.03308 0.00758 0.01309 0.01351
H33 2 0.368803 0.308204 0.684661 11.00000 0.06157
H34 2 0.492006 0.225878 0.810609 11.00000 0.06351
H35 2 0.432258 0.104281 0.829195 11.00000 0.07278
H36 2 0.246380 0.067379 0.721667 11.00000 0.04901
H37 2 0.199955 0.331477 0.538083 11.00000 0.06696
H43 2 -0.111409 0.340853 0.555254 11.00000 0.07609
H44 2 -0.218553 0.273374 0.620461 11.00000 0.08342
H45 2 -0.179643 0.143723 0.666753 11.00000 0.08222
H46 2 -0.031117 0.083310 0.647961 11.00000 0.06216
H47 2 0.020142 0.345973 0.492738 11.00000 0.07367
HKLF 4
REM a in P2(1)/n
REM R1 = 0.0382 for 6313 Fo > 4sig(Fo) and 0.0486 for all 7715 data
REM 565 parameters refined using 6 restraints
END
WGHT 0.0471 0.8153
REM Highest difference peak 0.255, deepest hole -0.255, 1-sigma level 0.037
Q1 1 0.6414 0.5047 0.4019 11.00000 0.05 0.26
Q2 1 0.1059 0.2839 0.5165 11.00000 0.05 0.24
Q3 1 0.1996 0.2597 0.5932 11.00000 0.05 0.22
Q4 1 0.2213 0.2064 0.6399 11.00000 0.05 0.21
Q5 1 0.7374 0.5168 0.4600 11.00000 0.05 0.21
Q6 1 0.0047 0.2206 0.5709 11.00000 0.05 0.21
Q7 1 0.4029 0.7777 0.3993 11.00000 0.05 0.20
Q8 1 0.0049 0.2739 0.5207 11.00000 0.05 0.19
Q9 1 0.2391 0.1441 0.6845 11.00000 0.05 0.19
Q10 1 0.4500 0.8433 0.4360 11.00000 0.05 0.18
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C15 H12 N2 O), C7 H7 N O3, H2 O'
_chemical_formula_sum 'C37 H33 N5 O6'
_chemical_formula_weight 643.68
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 13.6727(12)
_cell_length_b 17.6172(15)
_cell_length_c 14.8361(13)
_cell_angle_alpha 90.00
_cell_angle_beta 116.334(1)
_cell_angle_gamma 90.00
_cell_volume 3202.8(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 9945
_cell_measurement_theta_min 2.312
_cell_measurement_theta_max 30.521
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.335
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1352
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9728
_exptl_absorpt_correction_T_max 0.9818
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 32373
_diffrn_reflns_av_R_equivalents 0.0271
_diffrn_reflns_av_sigmaI/netI 0.0236
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.31
_diffrn_reflns_theta_max 28.00
_reflns_number_total 7715
_reflns_number_gt 6313
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2008)'
_computing_cell_refinement 'SAINT (Bruker, 2008)'
_computing_data_reduction 'SAINT (Bruker, 2008)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_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^ > 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.8148P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7715
_refine_ls_number_parameters 565
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0486
_refine_ls_R_factor_gt 0.0382
_refine_ls_wR_factor_ref 0.1026
_refine_ls_wR_factor_gt 0.0955
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_restrained_S_all 1.027
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
O5 O 0.32981(7) 0.52050(6) 0.17767(6) 0.0352(2) Uani 1 1 d . . .
H51 H 0.2610(16) 0.5364(10) 0.1603(13) 0.055(5) Uiso 1 1 d . . .
H52 H 0.3468(14) 0.5336(10) 0.1280(13) 0.052(5) Uiso 1 1 d . . .
N1 N 0.94835(9) 0.46529(7) 0.73036(8) 0.0409(3) Uani 1 1 d . . .
H1 H 1.0172(15) 0.4599(9) 0.7338(12) 0.052(5) Uiso 1 1 d . . .
H10 H 0.9345(14) 0.4478(10) 0.7809(13) 0.052(5) Uiso 1 1 d . . .
O1 O 0.60445(7) 0.52852(5) 0.27497(6) 0.0369(2) Uani 1 1 d . . .
O2 O 0.49658(7) 0.50521(6) 0.34930(7) 0.0427(2) Uani 1 1 d . . .
H2 H 0.4404(17) 0.5128(11) 0.2872(17) 0.074(6) Uiso 1 1 d . . .
O3 O 0.81568(8) 0.52196(6) 0.38326(7) 0.0379(2) Uani 1 1 d . . .
H3 H 0.7485(17) 0.5304(10) 0.3299(15) 0.064(5) Uiso 1 1 d . . .
C1 C 0.59325(10) 0.51358(7) 0.35156(8) 0.0301(2) Uani 1 1 d . . .
C2 C 0.68531(9) 0.50337(6) 0.44995(8) 0.0279(2) Uani 1 1 d . . .
C3 C 0.79332(9) 0.50710(6) 0.46194(8) 0.0279(2) Uani 1 1 d . . .
C4 C 0.88092(10) 0.49540(7) 0.55509(9) 0.0311(2) Uani 1 1 d . . .
C5 C 0.86358(9) 0.47821(7) 0.63878(8) 0.0304(2) Uani 1 1 d . . .
C6 C 0.75599(10) 0.47508(8) 0.62758(9) 0.0350(3) Uani 1 1 d . . .
C7 C 0.66999(10) 0.48711(8) 0.53551(9) 0.0342(3) Uani 1 1 d . . .
H4 H 0.9550(13) 0.4967(8) 0.5613(11) 0.041(4) Uiso 1 1 d . . .
H6 H 0.7422(13) 0.4619(9) 0.6837(12) 0.046(4) Uiso 1 1 d . . .
H7 H 0.5959(13) 0.4836(8) 0.5270(11) 0.042(4) Uiso 1 1 d . . .
O11 O 0.61872(6) 0.92008(5) 0.60620(6) 0.03136(18) Uani 1 1 d . . .
N11 N 0.62525(9) 0.88042(7) 0.46376(8) 0.0352(2) Uani 1 1 d . . .
H11 H 0.5936(13) 0.8573(9) 0.4066(13) 0.049(4) Uiso 1 1 d . . .
H12 H 0.6935(14) 0.8959(8) 0.4841(11) 0.040(4) Uiso 1 1 d . . .
N12 N 0.46968(7) 0.86300(5) 0.48369(7) 0.0263(2) Uani 1 1 d . . .
C10 C 0.57496(9) 0.88923(6) 0.52234(8) 0.0254(2) Uani 1 1 d . . .
C11 C 0.41580(8) 0.85572(6) 0.54682(8) 0.0264(2) Uani 1 1 d . . .
C12 C 0.42258(10) 0.78649(7) 0.59533(9) 0.0343(3) Uani 1 1 d . . .
C13 C 0.37114(12) 0.78179(9) 0.65852(10) 0.0444(3) Uani 1 1 d . . .
C14 C 0.31224(11) 0.84178(10) 0.66890(10) 0.0438(3) Uani 1 1 d . . .
C15 C 0.30290(10) 0.90864(8) 0.61665(9) 0.0368(3) Uani 1 1 d . . .
C16 C 0.35532(9) 0.91570(7) 0.55562(8) 0.0293(2) Uani 1 1 d . . .
C17 C 0.47671(12) 0.71999(8) 0.57870(12) 0.0465(3) Uani 1 1 d . . .
C21 C 0.42039(9) 0.82017(7) 0.39191(8) 0.0287(2) Uani 1 1 d . . .
C22 C 0.42823(10) 0.74118(7) 0.39673(10) 0.0376(3) Uani 1 1 d . . .
C23 C 0.37983(13) 0.70109(9) 0.30552(13) 0.0516(4) Uani 1 1 d . . .
C24 C 0.32294(13) 0.73839(11) 0.21532(12) 0.0565(4) Uani 1 1 d . . .
C25 C 0.31491(12) 0.81647(10) 0.21262(10) 0.0487(4) Uani 1 1 d . . .
C26 C 0.36441(10) 0.85802(8) 0.30130(9) 0.0355(3) Uani 1 1 d . . .
C27 C 0.47911(13) 0.70032(8) 0.49247(12) 0.0475(3) Uani 1 1 d . . .
H13 H 0.3772(14) 0.7346(10) 0.6922(13) 0.055(5) Uiso 1 1 d . . .
H14 H 0.2765(14) 0.8349(9) 0.7130(13) 0.055(5) Uiso 1 1 d . . .
H15 H 0.2613(13) 0.9517(9) 0.6231(11) 0.043(4) Uiso 1 1 d . . .
H16 H 0.3518(11) 0.9627(8) 0.5194(10) 0.034(4) Uiso 1 1 d . . .
H17 H 0.5078(14) 0.6838(10) 0.6372(13) 0.055(5) Uiso 1 1 d . . .
H23 H 0.3838(15) 0.6457(11) 0.3081(14) 0.067(5) Uiso 1 1 d . . .
H24 H 0.2892(16) 0.7085(11) 0.1519(15) 0.070(6) Uiso 1 1 d . . .
H25 H 0.2750(14) 0.8428(10) 0.1467(14) 0.058(5) Uiso 1 1 d . . .
H26 H 0.3611(12) 0.9130(9) 0.3030(11) 0.041(4) Uiso 1 1 d . . .
H27 H 0.5130(14) 0.6515(10) 0.4913(13) 0.056(5) Uiso 1 1 d . . .
O21 O 0.15219(7) 0.07272(5) 0.48241(6) 0.0373(2) Uani 1 1 d . . .
N21 N -0.02859(9) 0.09169(7) 0.42728(8) 0.0386(3) Uani 1 1 d . . .
H21 H -0.0804(14) 0.1147(10) 0.4372(13) 0.053(5) Uiso 1 1 d . . .
H22 H -0.0422(13) 0.0686(9) 0.3693(13) 0.046(4) Uiso 1 1 d . . .
N22 N 0.09539(7) 0.14283(5) 0.57786(7) 0.02588(19) Uani 1 1 d . . .
C30 C 0.07584(9) 0.10117(6) 0.49398(8) 0.0265(2) Uani 1 1 d . . .
C31 C 0.20435(9) 0.16648(6) 0.64258(8) 0.0267(2) Uani 1 1 d . . .
C32 C 0.23823(11) 0.23887(7) 0.63093(9) 0.0349(3) Uani 1 1 d . . .
C33 C 0.34745(13) 0.25869(10) 0.69475(12) 0.0493(4) Uani 1 1 d U . .
C34 C 0.41612(12) 0.20961(11) 0.76659(12) 0.0556(4) Uani 1 1 d U . .
C35 C 0.38008(12) 0.13899(10) 0.77702(11) 0.0521(4) Uani 1 1 d . . .
C36 C 0.27401(11) 0.11733(8) 0.71538(9) 0.0371(3) Uani 1 1 d . . .
C37 C 0.16456(16) 0.29390(8) 0.56011(11) 0.0497(4) Uani 1 1 d . . .
C41 C 0.01040(9) 0.18052(7) 0.59168(8) 0.0313(3) Uani 1 1 d . . .
C42 C -0.01012(11) 0.25687(8) 0.56554(9) 0.0426(3) Uani 1 1 d U . .
C43 C -0.09894(14) 0.28963(12) 0.57580(14) 0.0667(5) Uani 1 1 d U . .
C44 C -0.15842(13) 0.24877(15) 0.61360(16) 0.0767(7) Uani 1 1 d U . .
C45 C -0.13437(12) 0.17450(13) 0.64051(14) 0.0645(5) Uani 1 1 d U . .
C46 C -0.04999(11) 0.13952(10) 0.62941(10) 0.0435(3) Uani 1 1 d . . .
C47 C 0.05822(16) 0.30213(9) 0.53332(11) 0.0538(4) Uani 1 1 d . . .
H33 H 0.3688(15) 0.3082(11) 0.6847(13) 0.062(5) Uiso 1 1 d . . .
H34 H 0.4920(16) 0.2259(10) 0.8106(14) 0.064(5) Uiso 1 1 d . . .
H35 H 0.4323(17) 0.1043(11) 0.8292(15) 0.073(6) Uiso 1 1 d . . .
H36 H 0.2464(14) 0.0674(10) 0.7217(12) 0.049(4) Uiso 1 1 d . . .
H37 H 0.2000(15) 0.3315(11) 0.5381(14) 0.067(5) Uiso 1 1 d . . .
H43 H -0.1114(17) 0.3409(12) 0.5553(16) 0.076(6) Uiso 1 1 d . . .
H44 H -0.2186(18) 0.2734(12) 0.6205(16) 0.083(6) Uiso 1 1 d . . .
H45 H -0.1796(18) 0.1437(12) 0.6668(16) 0.082(6) Uiso 1 1 d . . .
H46 H -0.0311(15) 0.0833(11) 0.6480(14) 0.062(5) Uiso 1 1 d . . .
H47 H 0.0201(16) 0.3460(12) 0.4927(15) 0.074(6) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O5 0.0247(4) 0.0555(6) 0.0232(4) 0.0097(4) 0.0086(3) 0.0077(4)
N1 0.0278(5) 0.0631(8) 0.0251(5) 0.0086(5) 0.0055(4) 0.0053(5)
O1 0.0368(5) 0.0489(5) 0.0212(4) 0.0073(3) 0.0094(3) 0.0047(4)
O2 0.0265(4) 0.0723(7) 0.0237(4) 0.0074(4) 0.0060(4) 0.0087(4)
O3 0.0367(5) 0.0551(6) 0.0249(4) 0.0018(4) 0.0163(4) -0.0031(4)
C1 0.0308(6) 0.0339(6) 0.0222(5) 0.0020(4) 0.0085(4) 0.0052(5)
C2 0.0273(5) 0.0328(6) 0.0208(5) 0.0022(4) 0.0080(4) 0.0019(4)
C3 0.0313(6) 0.0302(5) 0.0235(5) 0.0000(4) 0.0132(4) -0.0004(4)
C4 0.0244(5) 0.0404(6) 0.0275(5) 0.0002(5) 0.0105(5) -0.0004(5)
C5 0.0272(6) 0.0362(6) 0.0226(5) 0.0019(4) 0.0063(4) 0.0020(5)
C6 0.0306(6) 0.0524(7) 0.0215(5) 0.0068(5) 0.0112(5) -0.0001(5)
C7 0.0261(6) 0.0504(7) 0.0248(5) 0.0044(5) 0.0101(5) 0.0009(5)
O11 0.0255(4) 0.0409(5) 0.0268(4) -0.0098(3) 0.0109(3) -0.0081(3)
N11 0.0261(5) 0.0485(6) 0.0334(5) -0.0174(5) 0.0153(4) -0.0131(4)
N12 0.0229(4) 0.0323(5) 0.0233(4) -0.0056(4) 0.0099(4) -0.0062(4)
C10 0.0225(5) 0.0258(5) 0.0262(5) -0.0027(4) 0.0093(4) -0.0023(4)
C11 0.0199(5) 0.0358(6) 0.0203(5) -0.0028(4) 0.0061(4) -0.0054(4)
C12 0.0292(6) 0.0415(7) 0.0271(5) 0.0050(5) 0.0078(5) -0.0015(5)
C13 0.0434(7) 0.0569(9) 0.0304(6) 0.0121(6) 0.0141(6) -0.0060(6)
C14 0.0335(7) 0.0730(10) 0.0280(6) -0.0018(6) 0.0166(5) -0.0108(6)
C15 0.0251(6) 0.0545(8) 0.0296(6) -0.0118(5) 0.0109(5) -0.0058(5)
C16 0.0237(5) 0.0362(6) 0.0249(5) -0.0058(4) 0.0078(4) -0.0051(4)
C17 0.0468(8) 0.0395(7) 0.0486(8) 0.0142(6) 0.0170(6) 0.0074(6)
C21 0.0225(5) 0.0368(6) 0.0276(5) -0.0084(4) 0.0118(4) -0.0079(4)
C22 0.0343(6) 0.0366(6) 0.0451(7) -0.0114(5) 0.0205(6) -0.0083(5)
C23 0.0535(9) 0.0480(9) 0.0624(10) -0.0280(7) 0.0339(8) -0.0219(7)
C24 0.0480(8) 0.0798(12) 0.0449(8) -0.0350(8) 0.0235(7) -0.0317(8)
C25 0.0348(7) 0.0819(11) 0.0270(6) -0.0119(7) 0.0116(5) -0.0145(7)
C26 0.0291(6) 0.0495(8) 0.0277(6) -0.0048(5) 0.0126(5) -0.0075(5)
C27 0.0492(8) 0.0317(7) 0.0620(9) 0.0008(6) 0.0252(7) 0.0051(6)
O21 0.0248(4) 0.0534(5) 0.0350(4) -0.0192(4) 0.0146(3) -0.0053(4)
N21 0.0244(5) 0.0591(7) 0.0293(5) -0.0182(5) 0.0091(4) -0.0007(5)
N22 0.0218(4) 0.0315(5) 0.0232(4) -0.0055(4) 0.0089(4) -0.0006(4)
C30 0.0250(5) 0.0316(6) 0.0238(5) -0.0044(4) 0.0115(4) -0.0039(4)
C31 0.0241(5) 0.0345(6) 0.0225(5) -0.0076(4) 0.0111(4) -0.0030(4)
C32 0.0417(7) 0.0392(6) 0.0330(6) -0.0107(5) 0.0248(5) -0.0103(5)
C33 0.0503(8) 0.0569(9) 0.0564(9) -0.0307(7) 0.0379(7) -0.0269(7)
C34 0.0280(7) 0.0838(12) 0.0504(8) -0.0366(8) 0.0133(6) -0.0096(7)
C35 0.0341(7) 0.0698(10) 0.0362(7) -0.0182(7) 0.0010(6) 0.0109(7)
C36 0.0339(6) 0.0417(7) 0.0291(6) -0.0063(5) 0.0079(5) 0.0050(5)
C37 0.0797(12) 0.0363(7) 0.0405(7) 0.0030(6) 0.0334(8) -0.0086(7)
C41 0.0224(5) 0.0429(7) 0.0241(5) -0.0111(5) 0.0063(4) 0.0016(5)
C42 0.0382(7) 0.0457(7) 0.0289(6) -0.0083(5) 0.0016(5) 0.0130(6)
C43 0.0470(9) 0.0654(11) 0.0585(10) -0.0267(8) -0.0029(7) 0.0257(8)
C44 0.0261(7) 0.1163(16) 0.0774(12) -0.0602(12) 0.0135(8) 0.0033(9)
C45 0.0318(7) 0.1049(14) 0.0626(10) -0.0495(10) 0.0262(7) -0.0183(8)
C46 0.0285(6) 0.0655(10) 0.0386(7) -0.0240(6) 0.0168(5) -0.0137(6)
C47 0.0782(12) 0.0372(7) 0.0331(7) 0.0076(6) 0.0131(7) 0.0135(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O5 H51 0.903(19) . ?
O5 H52 0.896(18) . ?
N1 C5 1.3579(14) . ?
N1 H1 0.924(18) . ?
N1 H10 0.906(18) . ?
O1 C1 1.2404(14) . ?
O2 C1 1.3155(15) . ?
O2 H2 0.91(2) . ?
O3 C3 1.3570(14) . ?
O3 H3 0.92(2) . ?
C1 C2 1.4551(15) . ?
C2 C7 1.4047(16) . ?
C2 C3 1.4083(16) . ?
C3 C4 1.3850(16) . ?
C4 C5 1.3967(17) . ?
C4 H4 0.975(16) . ?
C5 C6 1.4063(17) . ?
C6 C7 1.3669(16) . ?
C6 H6 0.959(16) . ?
C7 H7 0.965(16) . ?
O11 C10 1.2413(13) . ?
N11 C10 1.3350(15) . ?
N11 H11 0.865(17) . ?
N11 H12 0.886(17) . ?
N12 C10 1.3719(14) . ?
N12 C11 1.4313(14) . ?
N12 C21 1.4364(14) . ?
C11 C16 1.3832(17) . ?
C11 C12 1.3982(17) . ?
C12 C13 1.4020(19) . ?
C12 C17 1.464(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.955(18) . ?
C14 C15 1.385(2) . ?
C14 H14 0.982(18) . ?
C15 C16 1.3873(17) . ?
C15 H15 0.978(16) . ?
C16 H16 0.976(15) . ?
C17 C27 1.340(2) . ?
C17 H17 1.006(17) . ?
C21 C26 1.3874(17) . ?
C21 C22 1.3951(18) . ?
C22 C23 1.4048(19) . ?
C22 C27 1.464(2) . ?
C23 C24 1.380(3) . ?
C23 H23 0.977(19) . ?
C24 C25 1.379(3) . ?
C24 H24 1.00(2) . ?
C25 C26 1.3910(18) . ?
C25 H25 0.998(18) . ?
C26 H26 0.971(15) . ?
C27 H27 0.981(18) . ?
O21 C30 1.2368(14) . ?
N21 C30 1.3388(15) . ?
N21 H21 0.883(18) . ?
N21 H22 0.894(17) . ?
N22 C30 1.3651(14) . ?
N22 C41 1.4301(14) . ?
N22 C31 1.4303(13) . ?
C31 C36 1.3823(17) . ?
C31 C32 1.3936(17) . ?
C32 C33 1.412(2) . ?
C32 C37 1.456(2) . ?
C33 C34 1.370(3) . ?
C33 H33 0.953(19) . ?
C34 C35 1.372(3) . ?
C34 H34 0.992(19) . ?
C35 C36 1.3815(19) . ?
C35 H35 1.00(2) . ?
C36 H36 0.978(17) . ?
C37 C47 1.334(3) . ?
C37 H37 0.96(2) . ?
C41 C46 1.388(2) . ?
C41 C42 1.3934(19) . ?
C42 C43 1.412(2) . ?
C42 C47 1.461(2) . ?
C43 C44 1.378(3) . ?
C43 H43 0.94(2) . ?
C44 C45 1.365(3) . ?
C44 H44 0.97(2) . ?
C45 C46 1.381(2) . ?
C45 H45 1.02(2) . ?
C46 H46 1.030(18) . ?
C47 H47 0.98(2) . ?
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
H51 O5 H52 107.6(15) . . ?
C5 N1 H1 117.9(10) . . ?
C5 N1 H10 119.1(11) . . ?
H1 N1 H10 120.1(15) . . ?
C1 O2 H2 113.4(13) . . ?
C3 O3 H3 104.5(12) . . ?
O1 C1 O2 122.10(10) . . ?
O1 C1 C2 122.80(11) . . ?
O2 C1 C2 115.09(10) . . ?
C7 C2 C3 117.63(10) . . ?
C7 C2 C1 121.48(11) . . ?
C3 C2 C1 120.86(10) . . ?
O3 C3 C4 117.51(11) . . ?
O3 C3 C2 121.61(10) . . ?
C4 C3 C2 120.89(10) . . ?
C3 C4 C5 120.44(11) . . ?
C3 C4 H4 119.5(9) . . ?
C5 C4 H4 120.0(9) . . ?
N1 C5 C4 121.31(11) . . ?
N1 C5 C6 119.70(11) . . ?
C4 C5 C6 118.99(10) . . ?
C7 C6 C5 120.20(11) . . ?
C7 C6 H6 119.4(10) . . ?
C5 C6 H6 120.3(10) . . ?
C6 C7 C2 121.84(11) . . ?
C6 C7 H7 120.6(9) . . ?
C2 C7 H7 117.6(9) . . ?
C10 N11 H11 121.1(11) . . ?
C10 N11 H12 120.7(10) . . ?
H11 N11 H12 118.2(15) . . ?
C10 N12 C11 120.39(9) . . ?
C10 N12 C21 122.50(9) . . ?
C11 N12 C21 114.33(9) . . ?
O11 C10 N11 123.02(10) . . ?
O11 C10 N12 121.08(10) . . ?
N11 C10 N12 115.89(10) . . ?
C16 C11 C12 121.59(11) . . ?
C16 C11 N12 119.74(10) . . ?
C12 C11 N12 118.63(10) . . ?
C11 C12 C13 117.21(12) . . ?
C11 C12 C17 122.30(12) . . ?
C13 C12 C17 120.43(12) . . ?
C14 C13 C12 121.39(13) . . ?
C14 C13 H13 121.9(11) . . ?
C12 C13 H13 116.6(11) . . ?
C13 C14 C15 120.21(12) . . ?
C13 C14 H14 117.9(10) . . ?
C15 C14 H14 121.9(10) . . ?
C14 C15 C16 119.71(13) . . ?
C14 C15 H15 121.3(9) . . ?
C16 C15 H15 119.0(9) . . ?
C11 C16 C15 119.78(12) . . ?
C11 C16 H16 118.8(8) . . ?
C15 C16 H16 121.4(8) . . ?
C27 C17 C12 126.60(13) . . ?
C27 C17 H17 118.7(10) . . ?
C12 C17 H17 114.4(10) . . ?
C26 C21 C22 121.72(11) . . ?
C26 C21 N12 119.42(11) . . ?
C22 C21 N12 118.84(11) . . ?
C21 C22 C23 117.36(13) . . ?
C21 C22 C27 122.20(12) . . ?
C23 C22 C27 120.36(13) . . ?
C24 C23 C22 121.11(15) . . ?
C24 C23 H23 120.7(11) . . ?
C22 C23 H23 118.0(11) . . ?
C25 C24 C23 120.43(13) . . ?
C25 C24 H24 120.2(11) . . ?
C23 C24 H24 119.4(11) . . ?
C24 C25 C26 119.89(15) . . ?
C24 C25 H25 119.6(10) . . ?
C26 C25 H25 120.5(10) . . ?
C21 C26 C25 119.44(14) . . ?
C21 C26 H26 117.8(9) . . ?
C25 C26 H26 122.8(9) . . ?
C17 C27 C22 126.65(13) . . ?
C17 C27 H27 117.1(10) . . ?
C22 C27 H27 116.0(10) . . ?
C30 N21 H21 119.4(11) . . ?
C30 N21 H22 117.8(10) . . ?
H21 N21 H22 122.0(15) . . ?
C30 N22 C41 122.50(9) . . ?
C30 N22 C31 119.54(9) . . ?
C41 N22 C31 116.05(9) . . ?
O21 C30 N21 122.42(10) . . ?
O21 C30 N22 120.55(10) . . ?
N21 C30 N22 117.02(10) . . ?
C36 C31 C32 121.23(11) . . ?
C36 C31 N22 119.57(11) . . ?
C32 C31 N22 119.20(10) . . ?
C31 C32 C33 117.00(13) . . ?
C31 C32 C37 122.50(12) . . ?
C33 C32 C37 120.44(13) . . ?
C34 C33 C32 121.43(15) . . ?
C34 C33 H33 123.2(11) . . ?
C32 C33 H33 115.3(11) . . ?
C33 C34 C35 120.24(13) . . ?
C33 C34 H34 119.0(11) . . ?
C35 C34 H34 120.7(11) . . ?
C34 C35 C36 120.00(15) . . ?
C34 C35 H35 118.4(11) . . ?
C36 C35 H35 121.6(12) . . ?
C35 C36 C31 120.09(14) . . ?
C35 C36 H36 121.4(10) . . ?
C31 C36 H36 118.5(10) . . ?
C47 C37 C32 126.94(14) . . ?
C47 C37 H37 118.1(11) . . ?
C32 C37 H37 114.4(12) . . ?
C46 C41 C42 122.16(12) . . ?
C46 C41 N22 118.87(12) . . ?
C42 C41 N22 118.97(12) . . ?
C41 C42 C43 116.16(16) . . ?
C41 C42 C47 122.62(13) . . ?
C43 C42 C47 121.17(16) . . ?
C44 C43 C42 121.42(18) . . ?
C44 C43 H43 125.2(13) . . ?
C42 C43 H43 113.4(13) . . ?
C45 C44 C43 120.71(15) . . ?
C45 C44 H44 120.1(13) . . ?
C43 C44 H44 119.2(13) . . ?
C44 C45 C46 119.91(19) . . ?
C44 C45 H45 120.8(12) . . ?
C46 C45 H45 119.2(13) . . ?
C45 C46 C41 119.59(17) . . ?
C45 C46 H46 121.4(11) . . ?
C41 C46 H46 119.0(10) . . ?
C37 C47 C42 127.87(13) . . ?
C37 C47 H47 118.9(12) . . ?
C42 C47 H47 113.0(12) . . ?
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
O1 C1 C2 C7 179.45(12) . . . . ?
O2 C1 C2 C7 -1.06(17) . . . . ?
O1 C1 C2 C3 -2.62(18) . . . . ?
O2 C1 C2 C3 176.87(11) . . . . ?
C7 C2 C3 O3 179.53(11) . . . . ?
C1 C2 C3 O3 1.53(18) . . . . ?
C7 C2 C3 C4 -0.27(17) . . . . ?
C1 C2 C3 C4 -178.28(11) . . . . ?
O3 C3 C4 C5 -178.59(11) . . . . ?
C2 C3 C4 C5 1.22(18) . . . . ?
C3 C4 C5 N1 178.88(12) . . . . ?
C3 C4 C5 C6 -1.78(19) . . . . ?
N1 C5 C6 C7 -179.23(13) . . . . ?
C4 C5 C6 C7 1.4(2) . . . . ?
C5 C6 C7 C2 -0.5(2) . . . . ?
C3 C2 C7 C6 -0.09(19) . . . . ?
C1 C2 C7 C6 177.90(12) . . . . ?
C11 N12 C10 O11 -13.40(16) . . . . ?
C21 N12 C10 O11 -173.41(10) . . . . ?
C11 N12 C10 N11 167.59(10) . . . . ?
C21 N12 C10 N11 7.58(16) . . . . ?
C10 N12 C11 C16 90.96(13) . . . . ?
C21 N12 C11 C16 -107.48(12) . . . . ?
C10 N12 C11 C12 -91.40(13) . . . . ?
C21 N12 C11 C12 70.15(13) . . . . ?
C16 C11 C12 C13 -3.91(17) . . . . ?
N12 C11 C12 C13 178.50(10) . . . . ?
C16 C11 C12 C17 173.55(11) . . . . ?
N12 C11 C12 C17 -4.04(17) . . . . ?
C11 C12 C13 C14 2.82(19) . . . . ?
C17 C12 C13 C14 -174.70(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -1.57(19) . . . . ?
C12 C11 C16 C15 2.32(16) . . . . ?
N12 C11 C16 C15 179.88(10) . . . . ?
C14 C15 C16 C11 0.50(17) . . . . ?
C11 C12 C17 C27 -34.3(2) . . . . ?
C13 C12 C17 C27 143.06(16) . . . . ?
C10 N12 C21 C26 -90.38(14) . . . . ?
C11 N12 C21 C26 108.51(12) . . . . ?
C10 N12 C21 C22 91.00(14) . . . . ?
C11 N12 C21 C22 -70.12(14) . . . . ?
C26 C21 C22 C23 1.88(19) . . . . ?
N12 C21 C22 C23 -179.53(11) . . . . ?
C26 C21 C22 C27 -174.76(12) . . . . ?
N12 C21 C22 C27 3.83(18) . . . . ?
C21 C22 C23 C24 -2.7(2) . . . . ?
C27 C22 C23 C24 174.05(14) . . . . ?
C22 C23 C24 C25 1.8(2) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C22 C21 C26 C25 -0.21(19) . . . . ?
N12 C21 C26 C25 -178.79(11) . . . . ?
C24 C25 C26 C21 -0.8(2) . . . . ?
C12 C17 C27 C22 0.1(3) . . . . ?
C21 C22 C27 C17 34.3(2) . . . . ?
C23 C22 C27 C17 -142.27(16) . . . . ?
C41 N22 C30 O21 176.19(11) . . . . ?
C31 N22 C30 O21 12.52(17) . . . . ?
C41 N22 C30 N21 -5.13(17) . . . . ?
C31 N22 C30 N21 -168.80(11) . . . . ?
C30 N22 C31 C36 -83.98(14) . . . . ?
C41 N22 C31 C36 111.32(12) . . . . ?
C30 N22 C31 C32 96.04(13) . . . . ?
C41 N22 C31 C32 -68.66(13) . . . . ?
C36 C31 C32 C33 1.77(17) . . . . ?
N22 C31 C32 C33 -178.25(10) . . . . ?
C36 C31 C32 C37 -175.33(12) . . . . ?
N22 C31 C32 C37 4.65(17) . . . . ?
C31 C32 C33 C34 -1.62(19) . . . . ?
C37 C32 C33 C34 175.54(13) . . . . ?
C32 C33 C34 C35 1.0(2) . . . . ?
C33 C34 C35 C36 -0.4(2) . . . . ?
C34 C35 C36 C31 0.6(2) . . . . ?
C32 C31 C36 C35 -1.29(18) . . . . ?
N22 C31 C36 C35 178.73(11) . . . . ?
C31 C32 C37 C47 33.1(2) . . . . ?
C33 C32 C37 C47 -143.91(16) . . . . ?
C30 N22 C41 C46 83.57(14) . . . . ?
C31 N22 C41 C46 -112.23(12) . . . . ?
C30 N22 C41 C42 -95.53(13) . . . . ?
C31 N22 C41 C42 68.67(13) . . . . ?
C46 C41 C42 C43 -2.44(18) . . . . ?
N22 C41 C42 C43 176.63(11) . . . . ?
C46 C41 C42 C47 175.04(12) . . . . ?
N22 C41 C42 C47 -5.89(17) . . . . ?
C41 C42 C43 C44 2.6(2) . . . . ?
C47 C42 C43 C44 -174.87(14) . . . . ?
C42 C43 C44 C45 -1.3(2) . . . . ?
C43 C44 C45 C46 -0.3(2) . . . . ?
C44 C45 C46 C41 0.6(2) . . . . ?
C42 C41 C46 C45 0.91(19) . . . . ?
N22 C41 C46 C45 -178.16(11) . . . . ?
C32 C37 C47 C42 -2.2(3) . . . . ?
C41 C42 C47 C37 -29.8(2) . . . . ?
C43 C42 C47 C37 147.55(16) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H51 O11 0.903(19) 1.91(2) 2.7991(12) 170.1(16) 4_575
O5 H52 O21 0.896(18) 1.783(18) 2.6583(12) 165.0(16) 2
N1 H10 O11 0.906(18) 2.157(18) 3.0542(15) 170.8(15) 2_646
N11 H12 O21 0.886(17) 2.019(17) 2.9022(14) 174.4(14) 3_666
N21 H22 O1 0.894(17) 2.046(17) 2.9252(13) 167.5(15) 2_545
O2 H2 O5 0.91(2) 1.66(2) 2.5699(12) 174(2) .
O3 H3 O1 0.92(2) 1.77(2) 2.6113(13) 151.3(17) .
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.255
_refine_diff_density_min -0.255
_refine_diff_density_rms 0.037
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_x
_database_code_depnum_ccdc_archive 'CCDC 1544195'
_audit_update_record
;
2017-04-15 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_iucr_refine_instructions_details
;
TITL x in C2/c
CELL 0.71073 27.4270 7.6402 21.0376 90.000 119.263 90.000
ZERR 8.00 0.0054 0.0015 0.0042 0.000 0.002 0.000
LATT 7
SYMM -X, Y, 0.5-Z
SFAC C H N O
UNIT 176 152 24 32
TEMP -123
SIZE .30 .20 .20
EQIV $1 1.5-X, -0.5+Y, 1.5-Z
HTAB N11 O1
HTAB O2 O11
HTAB O3 O1
HTAB N1 O3_$1
L.S. 10
BOND $H
ACTA
CONF
FMAP 2
PLAN 6
OMIT -2 58
OMIT 2 0 0
OMIT 0 0 2
WGHT 0.055100 1.998800
FVAR 0.07657
N1 3 0.711120 -0.251197 0.654232 11.00000 0.03234 0.03268 =
0.03842 -0.00831 0.00180 0.01406
O1 4 0.575874 0.441736 0.637280 11.00000 0.02299 0.02641 =
0.03072 -0.00860 0.00818 0.00218
O2 4 0.507793 0.271141 0.555224 11.00000 0.01755 0.02978 =
0.03290 -0.00927 0.00528 0.00330
O3 4 0.675723 0.319393 0.710913 11.00000 0.02167 0.02551 =
0.03406 -0.01027 0.00378 -0.00013
C1 1 0.560104 0.300320 0.604199 11.00000 0.01822 0.02571 =
0.01986 -0.00258 0.00829 0.00100
C2 1 0.598557 0.154894 0.617927 11.00000 0.01764 0.02170 =
0.01856 -0.00168 0.00729 0.00107
C3 1 0.655347 0.170365 0.671145 11.00000 0.01990 0.02285 =
0.01904 -0.00270 0.00756 -0.00142
C4 1 0.692562 0.034919 0.683722 11.00000 0.01824 0.02676 =
0.02168 -0.00110 0.00467 0.00186
C5 1 0.674311 -0.119805 0.643500 11.00000 0.02525 0.02471 =
0.02184 0.00072 0.00745 0.00586
C6 1 0.617271 -0.139107 0.591375 11.00000 0.02724 0.02390 =
0.02516 -0.00606 0.00438 0.00213
C7 1 0.580964 -0.003910 0.579524 11.00000 0.02029 0.02618 =
0.02267 -0.00455 0.00375 0.00052
H1 2 0.745831 -0.235250 0.686226 11.00000 0.04826
H2 2 0.484166 0.369045 0.550840 11.00000 0.06569
H3 2 0.644724 0.396662 0.691929 11.00000 0.05520
H4 2 0.730550 0.051349 0.719361 11.00000 0.03849
H6 2 0.604518 -0.246435 0.565394 11.00000 0.03911
H7 2 0.541452 -0.017855 0.543225 11.00000 0.04043
H10 2 0.700430 -0.341379 0.626212 11.00000 0.04295
N11 3 0.492190 0.695162 0.621806 11.00000 0.02228 0.04018 =
0.04832 -0.02066 0.01359 0.00068
N12 3 0.396418 0.713555 0.574058 11.00000 0.02198 0.02529 =
0.02628 -0.00389 0.01326 0.00242
O11 4 0.434484 0.499284 0.537719 11.00000 0.02190 0.03229 =
0.03357 -0.01006 0.01109 0.00393
C10 1 0.441323 0.629829 0.576557 11.00000 0.02245 0.02643 =
0.02615 -0.00176 0.01270 0.00340
C11 1 0.341374 0.642247 0.531410 11.00000 0.02079 0.02163 =
0.02622 -0.00182 0.01183 0.00471
C12 1 0.316837 0.551283 0.566182 11.00000 0.02671 0.01926 =
0.03175 0.00125 0.01570 0.00527
C13 1 0.263926 0.476445 0.522139 11.00000 0.02913 0.02439 =
0.04576 -0.00332 0.02108 0.00024
C14 1 0.236395 0.497880 0.447331 11.00000 0.02226 0.03001 =
0.04388 -0.00968 0.01162 0.00400
C15 1 0.260480 0.595755 0.414466 11.00000 0.02876 0.03424 =
0.02954 -0.00486 0.00896 0.01004
C16 1 0.313194 0.667167 0.456511 11.00000 0.02963 0.03117 =
0.02694 -0.00083 0.01517 0.00585
C17 1 0.342764 0.537215 0.645454 11.00000 0.03678 0.02546 =
0.03408 0.00790 0.01999 0.00459
C21 1 0.402683 0.855458 0.621992 11.00000 0.02214 0.02383 =
0.02410 -0.00159 0.01172 0.00447
C22 1 0.395170 0.822826 0.682287 11.00000 0.02585 0.02620 =
0.02188 0.00238 0.01041 0.00696
C23 1 0.404639 0.962272 0.730470 11.00000 0.03526 0.03423 =
0.02328 -0.00125 0.01394 0.00724
C24 1 0.419161 1.126722 0.717719 11.00000 0.03843 0.02993 =
0.03386 -0.00813 0.01590 0.00434
C25 1 0.424911 1.157355 0.656560 11.00000 0.03826 0.02504 =
0.04167 -0.00319 0.02081 -0.00057
C26 1 0.416594 1.021240 0.608568 11.00000 0.03192 0.02771 =
0.03232 -0.00042 0.01955 0.00092
C27 1 0.376491 0.653945 0.695292 11.00000 0.03845 0.03067 =
0.02526 0.00799 0.01658 0.00739
H11 2 0.495749 0.783863 0.649771 11.00000 0.04929
H12 2 0.521821 0.632398 0.625688 11.00000 0.05192
H13 2 0.246520 0.409237 0.545660 11.00000 0.03946
H14 2 0.200101 0.444853 0.419560 11.00000 0.04104
H15 2 0.240281 0.614053 0.361667 11.00000 0.03843
H16 2 0.331586 0.733524 0.435988 11.00000 0.04137
H17 2 0.330834 0.436076 0.662976 11.00000 0.04141
H23 2 0.400535 0.943527 0.772365 11.00000 0.03691
H24 2 0.425714 1.222301 0.751049 11.00000 0.04027
H25 2 0.435728 1.272348 0.646820 11.00000 0.04424
H26 2 0.420782 1.037452 0.566074 11.00000 0.03232
H27 2 0.386966 0.630449 0.746178 11.00000 0.04536
HKLF 4
REM x in C2/c
REM R1 = 0.0385 for 4512 Fo > 4sig(Fo) and 0.0435 for all 5123 data
REM 338 parameters refined using 0 restraints
END
WGHT 0.0551 1.9997
REM Highest difference peak 0.342, deepest hole -0.214, 1-sigma level 0.041
Q1 1 0.5906 0.0736 0.6000 11.00000 0.05 0.34
Q2 1 0.5794 0.2216 0.6127 11.00000 0.05 0.34
Q3 1 0.3967 0.8417 0.6509 11.00000 0.05 0.30
Q4 1 0.3276 0.5554 0.6024 11.00000 0.05 0.30
Q5 1 0.6734 0.0987 0.6776 11.00000 0.05 0.29
Q6 1 0.4067 0.8886 0.7083 11.00000 0.05 0.27
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H12 N2 O, C7 H7 N O3'
_chemical_formula_sum 'C22 H19 N3 O4'
_chemical_formula_weight 389.40
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
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'
_cell_length_a 27.427(5)
_cell_length_b 7.6402(15)
_cell_length_c 21.038(4)
_cell_angle_alpha 90.00
_cell_angle_beta 119.263(2)
_cell_angle_gamma 90.00
_cell_volume 3845.8(13)
_cell_formula_units_Z 8
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 9985
_cell_measurement_theta_min 2.220
_cell_measurement_theta_max 30.498
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.345
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1632
_exptl_absorpt_coefficient_mu 0.094
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9722
_exptl_absorpt_correction_T_max 0.9814
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time .
_diffrn_standards_decay_% 0
_diffrn_reflns_number 20588
_diffrn_reflns_av_R_equivalents 0.0199
_diffrn_reflns_av_sigmaI/netI 0.0162
_diffrn_reflns_limit_h_min -37
_diffrn_reflns_limit_h_max 37
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 2.03
_diffrn_reflns_theta_max 29.00
_reflns_number_total 5123
_reflns_number_gt 4512
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2008)'
_computing_cell_refinement 'SAINT (Bruker, 2008)'
_computing_data_reduction 'SAINT (Bruker, 2008)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_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^ > 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+1.9988P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5123
_refine_ls_number_parameters 338
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0435
_refine_ls_R_factor_gt 0.0385
_refine_ls_wR_factor_ref 0.1058
_refine_ls_wR_factor_gt 0.1018
_refine_ls_goodness_of_fit_ref 1.054
_refine_ls_restrained_S_all 1.054
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
N1 N 0.71112(5) -0.25120(15) 0.65423(6) 0.0411(3) Uani 1 1 d . . .
O1 O 0.57587(3) 0.44174(10) 0.63728(4) 0.02883(17) Uani 1 1 d . . .
O2 O 0.50779(3) 0.27114(10) 0.55522(4) 0.02976(18) Uani 1 1 d . . .
O3 O 0.67572(3) 0.31939(10) 0.71091(4) 0.03129(18) Uani 1 1 d . . .
C1 C 0.56010(4) 0.30032(13) 0.60420(5) 0.02170(18) Uani 1 1 d . . .
C2 C 0.59856(4) 0.15489(12) 0.61793(5) 0.01997(18) Uani 1 1 d . . .
C3 C 0.65535(4) 0.17037(13) 0.67114(5) 0.02144(18) Uani 1 1 d . . .
C4 C 0.69256(4) 0.03492(13) 0.68372(5) 0.0244(2) Uani 1 1 d . . .
C5 C 0.67431(4) -0.11980(14) 0.64350(5) 0.0257(2) Uani 1 1 d . . .
C6 C 0.61727(4) -0.13911(14) 0.59137(6) 0.0290(2) Uani 1 1 d . . .
C7 C 0.58096(4) -0.00391(14) 0.57952(5) 0.0259(2) Uani 1 1 d . . .
H1 H 0.7458(7) -0.235(2) 0.6862(9) 0.048(4) Uiso 1 1 d . . .
H2 H 0.4842(8) 0.369(3) 0.5508(10) 0.066(5) Uiso 1 1 d . . .
H3 H 0.6447(7) 0.397(2) 0.6919(9) 0.055(5) Uiso 1 1 d . . .
H4 H 0.7306(6) 0.051(2) 0.7194(8) 0.038(4) Uiso 1 1 d . . .
H6 H 0.6045(6) -0.246(2) 0.5654(8) 0.039(4) Uiso 1 1 d . . .
H7 H 0.5415(7) -0.018(2) 0.5432(8) 0.040(4) Uiso 1 1 d . . .
H10 H 0.7004(7) -0.341(2) 0.6262(9) 0.043(4) Uiso 1 1 d . . .
N11 N 0.49219(4) 0.69516(15) 0.62181(6) 0.0385(3) Uani 1 1 d . . .
N12 N 0.39642(3) 0.71355(11) 0.57406(5) 0.02389(18) Uani 1 1 d . . .
O11 O 0.43448(3) 0.49928(10) 0.53772(4) 0.03031(18) Uani 1 1 d . . .
C10 C 0.44132(4) 0.62983(13) 0.57656(5) 0.0247(2) Uani 1 1 d . . .
C11 C 0.34137(4) 0.64225(13) 0.53141(5) 0.02274(19) Uani 1 1 d . . .
C12 C 0.31684(4) 0.55128(13) 0.56618(6) 0.0253(2) Uani 1 1 d . . .
C13 C 0.26393(5) 0.47644(14) 0.52214(7) 0.0319(2) Uani 1 1 d . . .
C14 C 0.23639(5) 0.49788(15) 0.44733(7) 0.0340(3) Uani 1 1 d . . .
C15 C 0.26048(5) 0.59575(16) 0.41447(6) 0.0331(2) Uani 1 1 d . . .
C16 C 0.31319(5) 0.66717(15) 0.45651(6) 0.0287(2) Uani 1 1 d . . .
C17 C 0.34276(5) 0.53722(14) 0.64545(6) 0.0310(2) Uani 1 1 d . . .
C21 C 0.40268(4) 0.85546(13) 0.62199(5) 0.02318(19) Uani 1 1 d . . .
C22 C 0.39517(4) 0.82283(13) 0.68229(5) 0.0252(2) Uani 1 1 d . . .
C23 C 0.40464(5) 0.96227(15) 0.73047(6) 0.0311(2) Uani 1 1 d . . .
C24 C 0.41916(5) 1.12672(16) 0.71772(6) 0.0348(2) Uani 1 1 d . . .
C25 C 0.42491(5) 1.15736(15) 0.65656(7) 0.0344(2) Uani 1 1 d . . .
C26 C 0.41659(5) 1.02124(14) 0.60857(6) 0.0290(2) Uani 1 1 d . . .
C27 C 0.37649(5) 0.65395(15) 0.69529(6) 0.0310(2) Uani 1 1 d . . .
H11 H 0.4957(7) 0.784(2) 0.6498(9) 0.049(4) Uiso 1 1 d . . .
H12 H 0.5218(7) 0.632(2) 0.6257(9) 0.052(5) Uiso 1 1 d . . .
H13 H 0.2465(6) 0.409(2) 0.5457(8) 0.039(4) Uiso 1 1 d . . .
H14 H 0.2001(6) 0.445(2) 0.4196(8) 0.041(4) Uiso 1 1 d . . .
H15 H 0.2403(6) 0.614(2) 0.3617(8) 0.038(4) Uiso 1 1 d . . .
H16 H 0.3316(6) 0.734(2) 0.4360(8) 0.041(4) Uiso 1 1 d . . .
H17 H 0.3308(6) 0.436(2) 0.6630(8) 0.041(4) Uiso 1 1 d . . .
H23 H 0.4005(6) 0.9435(19) 0.7724(8) 0.037(4) Uiso 1 1 d . . .
H24 H 0.4257(6) 1.222(2) 0.7510(8) 0.040(4) Uiso 1 1 d . . .
H25 H 0.4357(6) 1.272(2) 0.6468(8) 0.044(4) Uiso 1 1 d . . .
H26 H 0.4208(6) 1.0375(19) 0.5661(8) 0.032(3) Uiso 1 1 d . . .
H27 H 0.3870(7) 0.630(2) 0.7462(9) 0.045(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0323(5) 0.0327(5) 0.0384(5) -0.0083(4) 0.0018(4) 0.0141(4)
O1 0.0230(3) 0.0264(4) 0.0307(4) -0.0086(3) 0.0082(3) 0.0022(3)
O2 0.0175(3) 0.0298(4) 0.0329(4) -0.0093(3) 0.0053(3) 0.0033(3)
O3 0.0217(3) 0.0255(4) 0.0341(4) -0.0103(3) 0.0038(3) -0.0001(3)
C1 0.0182(4) 0.0257(4) 0.0199(4) -0.0026(3) 0.0083(3) 0.0010(3)
C2 0.0176(4) 0.0217(4) 0.0186(4) -0.0017(3) 0.0073(3) 0.0011(3)
C3 0.0199(4) 0.0229(4) 0.0190(4) -0.0027(3) 0.0076(3) -0.0014(3)
C4 0.0182(4) 0.0268(5) 0.0217(4) -0.0011(4) 0.0047(3) 0.0019(4)
C5 0.0252(5) 0.0247(5) 0.0218(4) 0.0007(4) 0.0074(4) 0.0059(4)
C6 0.0272(5) 0.0239(5) 0.0252(5) -0.0061(4) 0.0044(4) 0.0021(4)
C7 0.0203(4) 0.0262(5) 0.0227(4) -0.0045(4) 0.0038(4) 0.0005(4)
N11 0.0223(4) 0.0402(6) 0.0483(6) -0.0207(5) 0.0136(4) 0.0007(4)
N12 0.0220(4) 0.0253(4) 0.0263(4) -0.0039(3) 0.0133(3) 0.0024(3)
O11 0.0219(3) 0.0323(4) 0.0336(4) -0.0101(3) 0.0111(3) 0.0039(3)
C10 0.0225(4) 0.0264(5) 0.0261(5) -0.0018(4) 0.0127(4) 0.0034(4)
C11 0.0208(4) 0.0216(4) 0.0262(5) -0.0018(3) 0.0118(4) 0.0047(3)
C12 0.0267(5) 0.0193(4) 0.0318(5) 0.0012(4) 0.0157(4) 0.0053(4)
C13 0.0291(5) 0.0244(5) 0.0458(6) -0.0033(4) 0.0211(5) 0.0002(4)
C14 0.0223(5) 0.0300(5) 0.0439(6) -0.0097(5) 0.0116(4) 0.0040(4)
C15 0.0288(5) 0.0342(6) 0.0295(5) -0.0049(4) 0.0090(4) 0.0100(4)
C16 0.0296(5) 0.0312(5) 0.0269(5) -0.0008(4) 0.0152(4) 0.0058(4)
C17 0.0368(6) 0.0255(5) 0.0341(5) 0.0079(4) 0.0200(5) 0.0046(4)
C21 0.0221(4) 0.0238(5) 0.0241(4) -0.0016(4) 0.0117(4) 0.0045(3)
C22 0.0258(5) 0.0262(5) 0.0219(4) 0.0024(4) 0.0104(4) 0.0070(4)
C23 0.0353(5) 0.0342(6) 0.0233(5) -0.0012(4) 0.0139(4) 0.0072(4)
C24 0.0384(6) 0.0299(5) 0.0339(6) -0.0081(4) 0.0159(5) 0.0043(5)
C25 0.0383(6) 0.0250(5) 0.0417(6) -0.0032(4) 0.0208(5) -0.0006(4)
C26 0.0319(5) 0.0277(5) 0.0323(5) -0.0004(4) 0.0196(4) 0.0009(4)
C27 0.0385(6) 0.0307(5) 0.0253(5) 0.0080(4) 0.0166(4) 0.0074(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N1 C5 1.3620(14) . ?
N1 H1 0.865(17) . ?
N1 H10 0.860(17) . ?
O1 C1 1.2428(12) . ?
O2 C1 1.3132(12) . ?
O2 H2 0.96(2) . ?
O3 C3 1.3607(12) . ?
O3 H3 0.948(18) . ?
C1 C2 1.4603(13) . ?
C2 C7 1.4059(13) . ?
C2 C3 1.4102(13) . ?
C3 C4 1.3852(13) . ?
C4 C5 1.3964(14) . ?
C4 H4 0.949(15) . ?
C5 C6 1.4123(14) . ?
C6 C7 1.3704(14) . ?
C6 H6 0.952(16) . ?
C7 H7 0.980(16) . ?
N11 C10 1.3429(14) . ?
N11 H11 0.871(18) . ?
N11 H12 0.912(18) . ?
N12 C10 1.3658(12) . ?
N12 C21 1.4326(12) . ?
N12 C11 1.4341(13) . ?
O11 C10 1.2441(12) . ?
C11 C16 1.3877(15) . ?
C11 C12 1.3972(14) . ?
C12 C13 1.4060(15) . ?
C12 C17 1.4625(15) . ?
C13 C14 1.3828(18) . ?
C13 H13 0.984(15) . ?
C14 C15 1.3857(18) . ?
C14 H14 0.963(16) . ?
C15 C16 1.3857(16) . ?
C15 H15 0.979(15) . ?
C16 H16 0.954(16) . ?
C17 C27 1.3425(17) . ?
C17 H17 0.979(16) . ?
C21 C26 1.3910(15) . ?
C21 C22 1.4032(14) . ?
C22 C23 1.4045(15) . ?
C22 C27 1.4626(15) . ?
C23 C24 1.3834(18) . ?
C23 H23 0.952(15) . ?
C24 C25 1.3905(18) . ?
C24 H24 0.966(15) . ?
C25 C26 1.3884(16) . ?
C25 H25 0.980(16) . ?
C26 H26 0.963(14) . ?
C27 H27 0.980(16) . ?
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
C5 N1 H1 118.0(12) . . ?
C5 N1 H10 120.0(11) . . ?
H1 N1 H10 121.6(16) . . ?
C1 O2 H2 111.6(11) . . ?
C3 O3 H3 104.3(11) . . ?
O1 C1 O2 122.32(9) . . ?
O1 C1 C2 122.05(8) . . ?
O2 C1 C2 115.62(8) . . ?
C7 C2 C3 117.66(8) . . ?
C7 C2 C1 122.08(8) . . ?
C3 C2 C1 120.26(8) . . ?
O3 C3 C4 117.70(8) . . ?
O3 C3 C2 121.37(8) . . ?
C4 C3 C2 120.92(9) . . ?
C3 C4 C5 120.28(9) . . ?
C3 C4 H4 118.3(9) . . ?
C5 C4 H4 121.4(9) . . ?
N1 C5 C4 120.42(10) . . ?
N1 C5 C6 120.11(10) . . ?
C4 C5 C6 119.46(9) . . ?
C7 C6 C5 119.55(10) . . ?
C7 C6 H6 121.0(9) . . ?
C5 C6 H6 119.5(9) . . ?
C6 C7 C2 122.08(9) . . ?
C6 C7 H7 119.2(9) . . ?
C2 C7 H7 118.7(9) . . ?
C10 N11 H11 120.2(11) . . ?
C10 N11 H12 116.1(11) . . ?
H11 N11 H12 123.2(15) . . ?
C10 N12 C21 122.12(8) . . ?
C10 N12 C11 119.99(8) . . ?
C21 N12 C11 117.08(8) . . ?
O11 C10 N11 122.31(9) . . ?
O11 C10 N12 120.44(9) . . ?
N11 C10 N12 117.26(9) . . ?
C16 C11 C12 121.28(10) . . ?
C16 C11 N12 119.34(9) . . ?
C12 C11 N12 119.38(9) . . ?
C11 C12 C13 117.61(10) . . ?
C11 C12 C17 122.91(10) . . ?
C13 C12 C17 119.44(10) . . ?
C14 C13 C12 121.02(11) . . ?
C14 C13 H13 120.3(9) . . ?
C12 C13 H13 118.6(9) . . ?
C13 C14 C15 120.23(11) . . ?
C13 C14 H14 117.9(9) . . ?
C15 C14 H14 121.9(9) . . ?
C14 C15 C16 119.81(11) . . ?
C14 C15 H15 120.0(9) . . ?
C16 C15 H15 120.2(9) . . ?
C15 C16 C11 119.93(11) . . ?
C15 C16 H16 122.5(9) . . ?
C11 C16 H16 117.5(9) . . ?
C27 C17 C12 127.38(10) . . ?
C27 C17 H17 117.4(9) . . ?
C12 C17 H17 114.9(9) . . ?
C26 C21 C22 121.42(9) . . ?
C26 C21 N12 119.78(9) . . ?
C22 C21 N12 118.80(9) . . ?
C21 C22 C23 117.42(10) . . ?
C21 C22 C27 123.06(9) . . ?
C23 C22 C27 119.49(9) . . ?
C24 C23 C22 121.21(10) . . ?
C24 C23 H23 119.4(9) . . ?
C22 C23 H23 119.3(9) . . ?
C23 C24 C25 120.39(10) . . ?
C23 C24 H24 121.0(9) . . ?
C25 C24 H24 118.6(9) . . ?
C26 C25 C24 119.61(11) . . ?
C26 C25 H25 118.6(9) . . ?
C24 C25 H25 121.8(9) . . ?
C25 C26 C21 119.88(10) . . ?
C25 C26 H26 121.8(9) . . ?
C21 C26 H26 118.3(9) . . ?
C17 C27 C22 127.63(10) . . ?
C17 C27 H27 117.0(9) . . ?
C22 C27 H27 115.1(9) . . ?
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
O1 C1 C2 C7 -178.74(10) . . . . ?
O2 C1 C2 C7 1.91(14) . . . . ?
O1 C1 C2 C3 1.37(15) . . . . ?
O2 C1 C2 C3 -177.98(9) . . . . ?
C7 C2 C3 O3 -179.76(9) . . . . ?
C1 C2 C3 O3 0.14(14) . . . . ?
C7 C2 C3 C4 1.46(14) . . . . ?
C1 C2 C3 C4 -178.65(9) . . . . ?
O3 C3 C4 C5 -178.66(9) . . . . ?
C2 C3 C4 C5 0.17(15) . . . . ?
C3 C4 C5 N1 178.05(11) . . . . ?
C3 C4 C5 C6 -1.85(16) . . . . ?
N1 C5 C6 C7 -178.03(11) . . . . ?
C4 C5 C6 C7 1.87(16) . . . . ?
C5 C6 C7 C2 -0.21(17) . . . . ?
C3 C2 C7 C6 -1.44(16) . . . . ?
C1 C2 C7 C6 178.66(10) . . . . ?
C21 N12 C10 O11 174.92(9) . . . . ?
C11 N12 C10 O11 5.54(15) . . . . ?
C21 N12 C10 N11 -5.55(15) . . . . ?
C11 N12 C10 N11 -174.92(10) . . . . ?
C10 N12 C11 C16 -78.88(12) . . . . ?
C21 N12 C11 C16 111.22(10) . . . . ?
C10 N12 C11 C12 102.06(11) . . . . ?
C21 N12 C11 C12 -67.84(12) . . . . ?
C16 C11 C12 C13 3.85(14) . . . . ?
N12 C11 C12 C13 -177.11(9) . . . . ?
C16 C11 C12 C17 -173.72(10) . . . . ?
N12 C11 C12 C17 5.32(14) . . . . ?
C11 C12 C13 C14 -2.34(15) . . . . ?
C17 C12 C13 C14 175.32(10) . . . . ?
C12 C13 C14 C15 -0.68(16) . . . . ?
C13 C14 C15 C16 2.27(16) . . . . ?
C14 C15 C16 C11 -0.78(16) . . . . ?
C12 C11 C16 C15 -2.35(15) . . . . ?
N12 C11 C16 C15 178.60(9) . . . . ?
C11 C12 C17 C27 30.33(17) . . . . ?
C13 C12 C17 C27 -147.20(12) . . . . ?
C10 N12 C21 C26 77.31(13) . . . . ?
C11 N12 C21 C26 -113.01(11) . . . . ?
C10 N12 C21 C22 -101.97(12) . . . . ?
C11 N12 C21 C22 67.70(12) . . . . ?
C26 C21 C22 C23 -2.73(15) . . . . ?
N12 C21 C22 C23 176.54(9) . . . . ?
C26 C21 C22 C27 175.29(10) . . . . ?
N12 C21 C22 C27 -5.44(15) . . . . ?
C21 C22 C23 C24 1.91(16) . . . . ?
C27 C22 C23 C24 -176.19(10) . . . . ?
C22 C23 C24 C25 -0.22(18) . . . . ?
C23 C24 C25 C26 -0.71(19) . . . . ?
C24 C25 C26 C21 -0.10(18) . . . . ?
C22 C21 C26 C25 1.87(16) . . . . ?
N12 C21 C26 C25 -177.39(10) . . . . ?
C12 C17 C27 C22 0.2(2) . . . . ?
C21 C22 C27 C17 -30.58(17) . . . . ?
C23 C22 C27 C17 147.40(12) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H12 O1 0.912(18) 2.006(18) 2.8970(13) 164.9(16) .
O2 H2 O11 0.96(2) 1.60(2) 2.5481(11) 167.4(18) .
O3 H3 O1 0.948(18) 1.698(18) 2.5740(11) 152.0(16) .
N1 H1 O3 0.865(17) 2.221(18) 3.0600(14) 163.4(15) 4_646
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 29.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.342
_refine_diff_density_min -0.214
_refine_diff_density_rms 0.041
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_a
_database_code_depnum_ccdc_archive 'CCDC 1544197'
_audit_update_record
;
2017-04-15 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_iucr_refine_instructions_details
;
TITL a in P2(1)/c
CELL 0.71073 12.6443 7.5232 34.6743 90.000 96.811 90.000
ZERR 4.00 0.0018 0.0011 0.0051 0.000 0.003 0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 152 140 20 24
TEMP -90
SIZE .40 .25 .20
EQIV $1 X, -1+Y, Z
EQIV $2 X, 1+Y, Z
EQIV $3 -1+X, Y, Z
HTAB O2 O4_$1
HTAB O3 O1
HTAB N1 O11
HTAB N1 O3_$2
HTAB N11 O21_$1
HTAB N21 O11_$2
HTAB O4 O21_$3
L.S. 10
BOND $H
ACTA
CONF
FMAP 2
PLAN 6
OMIT -2 52
OMIT 1 0 0
OMIT -2 1 8
OMIT 0 0 2
WGHT 0.037600 0.805800
EXTI 0.001292
FVAR 0.08891
O11 4 0.722828 0.245448 0.105902 11.00000 0.02640 0.03090 =
0.03411 0.00886 0.01119 0.00316
N11 3 0.875463 0.097755 0.099898 11.00000 0.02993 0.03471 =
0.04059 0.01623 0.01415 0.00828
N12 3 0.829447 0.346609 0.062406 11.00000 0.02475 0.02748 =
0.02782 0.00643 0.00888 0.00422
C10 1 0.805589 0.229192 0.090213 11.00000 0.02393 0.02438 =
0.02581 0.00143 0.00343 -0.00143
C11 1 0.757059 0.489625 0.051217 11.00000 0.02112 0.02590 =
0.02635 0.00516 0.00864 0.00003
C12 1 0.689218 0.477454 0.016437 11.00000 0.02511 0.03093 =
0.02868 0.00413 0.00673 -0.00164
C13 1 0.620259 0.620483 0.006600 11.00000 0.02810 0.04405 =
0.03175 0.00914 0.00188 0.00371
C14 1 0.619073 0.766813 0.030170 11.00000 0.03186 0.03155 =
0.05022 0.00994 0.00885 0.00823
C15 1 0.685960 0.775302 0.064732 11.00000 0.03159 0.02661 =
0.04669 -0.00150 0.01202 0.00036
C16 1 0.755344 0.637160 0.075027 11.00000 0.02558 0.03115 =
0.02896 0.00156 0.00636 -0.00178
C17 1 0.687869 0.322763 -0.009134 11.00000 0.03354 0.04209 =
0.03234 -0.00331 0.00169 -0.00404
C21 1 0.910941 0.311634 0.037812 11.00000 0.02792 0.02343 =
0.03490 0.00938 0.01302 0.00493
C22 1 0.881048 0.241099 0.000848 11.00000 0.04018 0.02265 =
0.03607 0.00456 0.01372 0.00286
C23 1 0.962595 0.197013 -0.021463 11.00000 0.05231 0.02918 =
0.04212 0.00403 0.02208 0.00580
C24 1 1.067907 0.226163 -0.007927 11.00000 0.04526 0.03416 =
0.05523 0.01434 0.03083 0.00897
C25 1 1.095450 0.301267 0.027977 11.00000 0.02978 0.04326 =
0.05656 0.01885 0.01709 0.00430
C26 1 1.016485 0.345300 0.050991 11.00000 0.02898 0.03838 =
0.03962 0.01002 0.00958 0.00226
C27 1 0.770080 0.219027 -0.015292 11.00000 0.04369 0.03622 =
0.03629 -0.00786 0.00912 -0.00385
H11 2 0.936969 0.089294 0.090461 11.00000 0.04528
H12 2 0.860851 0.022318 0.119055 11.00000 0.04044
H13 2 0.573570 0.613340 -0.017613 11.00000 0.03895
H14 2 0.570726 0.864833 0.022999 11.00000 0.04904
H15 2 0.684214 0.881171 0.081289 11.00000 0.03780
H16 2 0.804203 0.641225 0.098841 11.00000 0.03244
H17 2 0.620223 0.299652 -0.025821 11.00000 0.05253
H23 2 0.942273 0.146399 -0.047109 11.00000 0.04565
H24 2 1.121184 0.192577 -0.024306 11.00000 0.05422
H25 2 1.170113 0.324184 0.038253 11.00000 0.05182
H26 2 1.034412 0.402981 0.075745 11.00000 0.03247
H27 2 0.756304 0.130305 -0.035734 11.00000 0.04755
O21 4 0.816510 0.863301 0.163412 11.00000 0.03418 0.03108 =
0.04144 0.01133 0.01673 0.00584
N21 3 0.662255 1.007598 0.166915 11.00000 0.03335 0.03139 =
0.03948 0.01294 0.01531 0.00645
N22 3 0.697863 0.745222 0.200753 11.00000 0.02892 0.02677 =
0.02947 0.00632 0.00974 0.00302
C30 1 0.728822 0.872834 0.176325 11.00000 0.02866 0.02703 =
0.02595 0.00113 0.00754 0.00079
C31 1 0.598161 0.752390 0.216717 11.00000 0.02994 0.02268 =
0.03195 0.00475 0.01197 0.00112
C32 1 0.598983 0.783016 0.256473 11.00000 0.04262 0.02285 =
0.03343 0.00116 0.01144 0.00209
C33 1 0.499909 0.793813 0.270857 11.00000 0.05530 0.03088 =
0.03954 0.00180 0.02420 0.00668
C34 1 0.405862 0.774010 0.247044 11.00000 0.04202 0.03269 =
0.06137 0.00605 0.02988 0.00711
C35 1 0.407003 0.743983 0.207737 11.00000 0.03001 0.03329 =
0.05803 0.00504 0.01036 0.00269
C36 1 0.503388 0.730927 0.192674 11.00000 0.03328 0.03341 =
0.03562 0.00334 0.00849 0.00164
C37 1 0.697041 0.802410 0.282908 11.00000 0.05623 0.03362 =
0.03012 -0.00491 0.00347 0.00492
C41 1 0.767114 0.599599 0.212899 11.00000 0.02499 0.02518 =
0.03206 0.00577 0.00855 -0.00207
C42 1 0.814565 0.594106 0.251392 11.00000 0.02938 0.02808 =
0.03551 0.00459 0.00312 -0.00251
C43 1 0.884548 0.453266 0.262037 11.00000 0.03694 0.04151 =
0.04073 0.01099 0.00176 0.00191
C44 1 0.901836 0.321368 0.236124 11.00000 0.03598 0.03336 =
0.05563 0.01328 0.01309 0.01077
C45 1 0.851058 0.325681 0.198689 11.00000 0.03974 0.02877 =
0.04653 0.00128 0.01938 0.00107
C46 1 0.783845 0.465653 0.186968 11.00000 0.03378 0.03212 =
0.03303 0.00287 0.01331 -0.00113
C47 1 0.790077 0.722328 0.280672 11.00000 0.04886 0.03622 =
0.03348 -0.00176 -0.00635 0.00032
H21 2 0.599926 1.012969 0.176137 11.00000 0.05348
H22 2 0.681640 1.083370 0.149946 11.00000 0.04618
H33 2 0.500983 0.814674 0.299046 11.00000 0.04400
H34 2 0.337505 0.780352 0.257264 11.00000 0.05491
H35 2 0.341367 0.734261 0.190678 11.00000 0.04587
H36 2 0.506872 0.707279 0.165165 11.00000 0.04100
H37 2 0.689653 0.873393 0.306231 11.00000 0.05735
H43 2 0.919026 0.449666 0.287741 11.00000 0.04874
H44 2 0.948609 0.231958 0.244009 11.00000 0.04636
H45 2 0.863951 0.232524 0.180544 11.00000 0.04192
H46 2 0.746003 0.473461 0.160059 11.00000 0.04167
H47 2 0.846361 0.735112 0.301978 11.00000 0.04876
N1 3 0.518449 0.447990 0.095365 11.00000 0.02810 0.02786 =
0.05740 0.00453 0.01169 0.00036
O1 4 0.228812 -0.225882 0.119009 11.00000 0.03440 0.02589 =
0.06466 0.00271 0.01706 0.00042
O2 4 0.116447 -0.006886 0.128190 11.00000 0.02518 0.03206 =
0.05044 0.00505 0.01287 0.00262
O3 4 0.414134 -0.155922 0.099659 11.00000 0.02997 0.02366 =
0.05983 -0.00094 0.01312 0.00448
C1 1 0.210255 -0.065131 0.119982 11.00000 0.02732 0.02824 =
0.02853 0.00220 0.00396 0.00474
C2 1 0.287369 0.069068 0.112633 11.00000 0.02266 0.02699 =
0.02624 0.00134 0.00363 0.00366
C3 1 0.389036 0.018547 0.103307 11.00000 0.02651 0.02385 =
0.02748 0.00104 0.00276 0.00610
C4 1 0.464774 0.143663 0.097439 11.00000 0.02217 0.02988 =
0.03042 0.00032 0.00471 0.00361
C5 1 0.443091 0.324730 0.100656 11.00000 0.02673 0.02797 =
0.02480 0.00232 0.00326 0.00057
C6 1 0.341090 0.376213 0.109142 11.00000 0.02980 0.02371 =
0.04338 0.00054 0.00975 0.00357
C7 1 0.266880 0.251131 0.114939 11.00000 0.02452 0.03062 =
0.03730 0.00214 0.00834 0.00706
H1 2 0.582958 0.412656 0.093507 11.00000 0.04589
H2 2 0.076334 -0.105034 0.135188 11.00000 0.05981
H3 2 0.354896 -0.214858 0.105913 11.00000 0.06842
H4 2 0.534161 0.106138 0.090650 11.00000 0.03765
H6 2 0.324085 0.502195 0.111692 11.00000 0.03971
H7 2 0.197653 0.288682 0.121692 11.00000 0.03703
H10 2 0.502731 0.558925 0.096124 11.00000 0.04077
O4 4 0.000231 0.730721 0.147717 11.00000 0.02910 0.04017 =
0.06588 0.01364 0.01589 0.00355
C40 1 0.048716 0.570763 0.162130 11.00000 0.04542 0.03462 =
0.07445 0.00860 0.02493 0.00361
H41 2 -0.062021 0.755484 0.156547 11.00000 0.06991
H401 2 0.007988 0.466511 0.150437 11.00000 0.07823
H402 2 0.046114 0.560601 0.189922 11.00000 0.08620
H403 2 0.119709 0.567641 0.154579 11.00000 0.07533
HKLF 4
REM a in P2(1)/c
REM R1 = 0.0377 for 5050 Fo > 4sig(Fo) and 0.0520 for all 6390 data
REM 583 parameters refined using 0 restraints
END
WGHT 0.0376 0.8058
REM Highest difference peak 0.191, deepest hole -0.187, 1-sigma level 0.034
Q1 1 0.6025 0.8159 0.2345 11.00000 0.05 0.19
Q2 1 0.3459 0.0436 0.1207 11.00000 0.05 0.18
Q3 1 0.8984 0.3137 0.0151 11.00000 0.05 0.18
Q4 1 0.7634 0.5638 0.2346 11.00000 0.05 0.17
Q5 1 0.7021 0.4609 0.0387 11.00000 0.05 0.17
Q6 1 0.8149 0.6336 0.2290 11.00000 0.05 0.17
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C15 H12 N2 O), C7 H7 N O3, C H4 O'
_chemical_formula_sum 'C38 H35 N5 O6'
_chemical_formula_weight 657.71
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 12.6443(18)
_cell_length_b 7.5232(11)
_cell_length_c 34.674(5)
_cell_angle_alpha 90.00
_cell_angle_beta 96.811(3)
_cell_angle_gamma 90.00
_cell_volume 3275.1(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 183(2)
_cell_measurement_reflns_used 4863
_cell_measurement_theta_min 2.118
_cell_measurement_theta_max 26.714
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.334
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1384
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9642
_exptl_absorpt_correction_T_max 0.9819
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 183(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX II'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 24975
_diffrn_reflns_av_R_equivalents 0.0379
_diffrn_reflns_av_sigmaI/netI 0.0341
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -42
_diffrn_reflns_limit_l_max 42
_diffrn_reflns_theta_min 2.37
_diffrn_reflns_theta_max 26.00
_reflns_number_total 6390
_reflns_number_gt 5050
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2008)'
_computing_cell_refinement 'SAINT (Bruker, 2008)'
_computing_data_reduction 'SAINT (Bruker, 2008)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_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^ > 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+0.8058P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 6390
_refine_ls_number_parameters 583
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0520
_refine_ls_R_factor_gt 0.0377
_refine_ls_wR_factor_ref 0.0915
_refine_ls_wR_factor_gt 0.0839
_refine_ls_goodness_of_fit_ref 1.012
_refine_ls_restrained_S_all 1.012
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
O11 O 0.72283(8) 0.24545(13) 0.10590(3) 0.0299(2) Uani 1 1 d . . .
N11 N 0.87546(11) 0.09775(18) 0.09990(4) 0.0343(3) Uani 1 1 d . . .
N12 N 0.82945(9) 0.34661(15) 0.06241(3) 0.0262(3) Uani 1 1 d . . .
C10 C 0.80559(11) 0.22919(18) 0.09021(4) 0.0247(3) Uani 1 1 d . . .
C11 C 0.75706(11) 0.48963(18) 0.05122(4) 0.0240(3) Uani 1 1 d . . .
C12 C 0.68922(11) 0.47745(19) 0.01644(4) 0.0280(3) Uani 1 1 d . . .
C13 C 0.62026(13) 0.6205(2) 0.00660(5) 0.0348(4) Uani 1 1 d . . .
C14 C 0.61907(13) 0.7668(2) 0.03017(5) 0.0376(4) Uani 1 1 d . . .
C15 C 0.68596(13) 0.7753(2) 0.06473(5) 0.0344(4) Uani 1 1 d . . .
C16 C 0.75534(12) 0.6372(2) 0.07503(4) 0.0283(3) Uani 1 1 d . . .
C17 C 0.68787(14) 0.3228(2) -0.00913(5) 0.0362(4) Uani 1 1 d . . .
C21 C 0.91094(12) 0.31163(19) 0.03781(4) 0.0280(3) Uani 1 1 d . . .
C22 C 0.88105(13) 0.24110(19) 0.00085(5) 0.0322(4) Uani 1 1 d . . .
C23 C 0.96259(15) 0.1970(2) -0.02146(5) 0.0399(4) Uani 1 1 d . . .
C24 C 1.06791(15) 0.2262(2) -0.00793(6) 0.0429(4) Uani 1 1 d . . .
C25 C 1.09545(14) 0.3013(2) 0.02798(6) 0.0422(4) Uani 1 1 d . . .
C26 C 1.01649(12) 0.3453(2) 0.05099(5) 0.0352(4) Uani 1 1 d . . .
C27 C 0.77008(14) 0.2190(2) -0.01529(5) 0.0384(4) Uani 1 1 d . . .
H11 H 0.9370(15) 0.089(2) 0.0905(5) 0.045(5) Uiso 1 1 d . . .
H12 H 0.8609(13) 0.022(2) 0.1191(5) 0.040(5) Uiso 1 1 d . . .
H13 H 0.5736(13) 0.613(2) -0.0176(5) 0.039(5) Uiso 1 1 d . . .
H14 H 0.5707(14) 0.865(3) 0.0230(5) 0.049(5) Uiso 1 1 d . . .
H15 H 0.6842(12) 0.881(2) 0.0813(5) 0.038(4) Uiso 1 1 d . . .
H16 H 0.8042(12) 0.641(2) 0.0988(5) 0.032(4) Uiso 1 1 d . . .
H17 H 0.6202(15) 0.300(2) -0.0258(5) 0.053(5) Uiso 1 1 d . . .
H23 H 0.9423(13) 0.146(2) -0.0471(5) 0.046(5) Uiso 1 1 d . . .
H24 H 1.1212(15) 0.193(2) -0.0243(5) 0.054(5) Uiso 1 1 d . . .
H25 H 1.1701(16) 0.324(2) 0.0383(5) 0.052(5) Uiso 1 1 d . . .
H26 H 1.0344(12) 0.403(2) 0.0757(5) 0.032(4) Uiso 1 1 d . . .
H27 H 0.7563(14) 0.130(2) -0.0357(5) 0.048(5) Uiso 1 1 d . . .
O21 O 0.81651(8) 0.86330(14) 0.16341(3) 0.0346(3) Uani 1 1 d . . .
N21 N 0.66225(12) 1.00760(18) 0.16691(4) 0.0339(3) Uani 1 1 d . . .
N22 N 0.69786(10) 0.74522(15) 0.20075(3) 0.0279(3) Uani 1 1 d . . .
C30 C 0.72882(12) 0.87283(19) 0.17633(4) 0.0269(3) Uani 1 1 d . . .
C31 C 0.59816(12) 0.75239(18) 0.21672(4) 0.0275(3) Uani 1 1 d . . .
C32 C 0.59898(13) 0.78302(19) 0.25647(4) 0.0324(4) Uani 1 1 d . . .
C33 C 0.49991(15) 0.7938(2) 0.27086(5) 0.0404(4) Uani 1 1 d . . .
C34 C 0.40586(15) 0.7740(2) 0.24704(6) 0.0435(4) Uani 1 1 d . . .
C35 C 0.40700(14) 0.7440(2) 0.20774(6) 0.0400(4) Uani 1 1 d . . .
C36 C 0.50339(13) 0.7309(2) 0.19267(5) 0.0338(4) Uani 1 1 d . . .
C37 C 0.69704(15) 0.8024(2) 0.28291(5) 0.0401(4) Uani 1 1 d . . .
C41 C 0.76711(11) 0.59960(18) 0.21290(4) 0.0270(3) Uani 1 1 d . . .
C42 C 0.81456(12) 0.5941(2) 0.25139(4) 0.0311(3) Uani 1 1 d . . .
C43 C 0.88455(14) 0.4533(2) 0.26204(5) 0.0400(4) Uani 1 1 d . . .
C44 C 0.90184(14) 0.3214(2) 0.23612(5) 0.0410(4) Uani 1 1 d . . .
C45 C 0.85106(13) 0.3257(2) 0.19869(5) 0.0372(4) Uani 1 1 d . . .
C46 C 0.78384(13) 0.4657(2) 0.18697(5) 0.0322(4) Uani 1 1 d . . .
C47 C 0.79008(15) 0.7223(2) 0.28067(5) 0.0404(4) Uani 1 1 d . . .
H21 H 0.5999(16) 1.013(3) 0.1761(5) 0.053(6) Uiso 1 1 d . . .
H22 H 0.6816(14) 1.083(3) 0.1499(5) 0.046(5) Uiso 1 1 d . . .
H33 H 0.5010(13) 0.815(2) 0.2990(5) 0.044(5) Uiso 1 1 d . . .
H34 H 0.3375(16) 0.780(2) 0.2573(5) 0.055(5) Uiso 1 1 d . . .
H35 H 0.3414(15) 0.734(2) 0.1907(5) 0.046(5) Uiso 1 1 d . . .
H36 H 0.5069(13) 0.707(2) 0.1652(5) 0.041(5) Uiso 1 1 d . . .
H37 H 0.6897(15) 0.873(3) 0.3062(6) 0.057(5) Uiso 1 1 d . . .
H43 H 0.9190(14) 0.450(2) 0.2877(5) 0.049(5) Uiso 1 1 d . . .
H44 H 0.9486(14) 0.232(2) 0.2440(5) 0.046(5) Uiso 1 1 d . . .
H45 H 0.8640(13) 0.233(2) 0.1805(5) 0.042(5) Uiso 1 1 d . . .
H46 H 0.7460(13) 0.473(2) 0.1601(5) 0.042(5) Uiso 1 1 d . . .
H47 H 0.8464(15) 0.735(2) 0.3020(5) 0.049(5) Uiso 1 1 d . . .
N1 N 0.51845(12) 0.4480(2) 0.09537(4) 0.0373(3) Uani 1 1 d . . .
O1 O 0.22881(9) -0.22588(14) 0.11901(4) 0.0407(3) Uani 1 1 d . . .
O2 O 0.11645(8) -0.00689(15) 0.12819(3) 0.0352(3) Uani 1 1 d . . .
O3 O 0.41413(9) -0.15592(14) 0.09966(3) 0.0372(3) Uani 1 1 d . . .
C1 C 0.21025(12) -0.06513(19) 0.11998(4) 0.0280(3) Uani 1 1 d . . .
C2 C 0.28737(11) 0.06907(19) 0.11263(4) 0.0252(3) Uani 1 1 d . . .
C3 C 0.38904(11) 0.01855(18) 0.10331(4) 0.0260(3) Uani 1 1 d . . .
C4 C 0.46477(12) 0.14366(19) 0.09744(4) 0.0274(3) Uani 1 1 d . . .
C5 C 0.44309(11) 0.32473(19) 0.10066(4) 0.0265(3) Uani 1 1 d . . .
C6 C 0.34109(12) 0.3762(2) 0.10914(5) 0.0319(3) Uani 1 1 d . . .
C7 C 0.26688(12) 0.2511(2) 0.11494(4) 0.0304(3) Uani 1 1 d . . .
H1 H 0.5830(15) 0.413(2) 0.0935(5) 0.046(5) Uiso 1 1 d . . .
H2 H 0.0763(16) -0.105(3) 0.1352(6) 0.060(6) Uiso 1 1 d . . .
H3 H 0.3549(17) -0.215(3) 0.1059(6) 0.068(7) Uiso 1 1 d . . .
H4 H 0.5342(13) 0.106(2) 0.0907(5) 0.038(4) Uiso 1 1 d . . .
H6 H 0.3241(13) 0.502(2) 0.1117(5) 0.040(4) Uiso 1 1 d . . .
H7 H 0.1977(13) 0.289(2) 0.1217(5) 0.037(4) Uiso 1 1 d . . .
H10 H 0.5027(14) 0.559(3) 0.0961(5) 0.041(5) Uiso 1 1 d . . .
O4 O 0.00023(10) 0.73072(15) 0.14772(4) 0.0442(3) Uani 1 1 d . . .
C40 C 0.04872(17) 0.5708(3) 0.16213(7) 0.0501(5) Uani 1 1 d . . .
H41 H -0.0620(18) 0.755(3) 0.1565(6) 0.070(7) Uiso 1 1 d . . .
H401 H 0.0080(18) 0.467(3) 0.1504(6) 0.078(7) Uiso 1 1 d . . .
H402 H 0.0461(18) 0.561(3) 0.1899(7) 0.086(8) Uiso 1 1 d . . .
H403 H 0.1197(19) 0.568(3) 0.1546(6) 0.075(7) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0264(6) 0.0309(6) 0.0341(6) 0.0089(4) 0.0112(5) 0.0032(4)
N11 0.0299(8) 0.0347(7) 0.0406(8) 0.0162(6) 0.0142(6) 0.0083(6)
N12 0.0248(6) 0.0275(6) 0.0278(6) 0.0064(5) 0.0089(5) 0.0042(5)
C10 0.0239(8) 0.0244(7) 0.0258(7) 0.0014(6) 0.0034(6) -0.0014(6)
C11 0.0211(7) 0.0259(7) 0.0263(7) 0.0052(6) 0.0086(6) 0.0000(6)
C12 0.0251(8) 0.0309(8) 0.0287(8) 0.0041(6) 0.0067(6) -0.0016(6)
C13 0.0281(8) 0.0440(10) 0.0318(9) 0.0091(7) 0.0019(7) 0.0037(7)
C14 0.0319(9) 0.0316(9) 0.0502(10) 0.0099(8) 0.0088(8) 0.0082(7)
C15 0.0316(9) 0.0266(8) 0.0467(10) -0.0015(7) 0.0120(7) 0.0004(7)
C16 0.0256(8) 0.0312(8) 0.0290(8) 0.0016(6) 0.0064(6) -0.0018(6)
C17 0.0335(9) 0.0421(9) 0.0323(9) -0.0033(7) 0.0017(7) -0.0040(7)
C21 0.0279(8) 0.0234(7) 0.0349(8) 0.0094(6) 0.0130(6) 0.0049(6)
C22 0.0402(9) 0.0227(7) 0.0361(8) 0.0046(6) 0.0137(7) 0.0029(6)
C23 0.0523(12) 0.0292(8) 0.0421(10) 0.0040(7) 0.0221(9) 0.0058(8)
C24 0.0453(11) 0.0342(9) 0.0552(12) 0.0143(8) 0.0308(9) 0.0090(8)
C25 0.0298(10) 0.0433(10) 0.0566(11) 0.0188(9) 0.0171(8) 0.0043(8)
C26 0.0290(9) 0.0384(9) 0.0396(10) 0.0100(8) 0.0096(7) 0.0023(7)
C27 0.0437(10) 0.0362(9) 0.0363(9) -0.0079(7) 0.0091(8) -0.0038(8)
O21 0.0342(6) 0.0311(6) 0.0414(6) 0.0113(5) 0.0167(5) 0.0058(5)
N21 0.0334(8) 0.0314(7) 0.0395(8) 0.0129(6) 0.0153(6) 0.0064(6)
N22 0.0289(7) 0.0268(6) 0.0295(7) 0.0063(5) 0.0097(5) 0.0030(5)
C30 0.0287(8) 0.0270(7) 0.0259(8) 0.0011(6) 0.0075(6) 0.0008(6)
C31 0.0299(8) 0.0227(7) 0.0320(8) 0.0047(6) 0.0120(6) 0.0011(6)
C32 0.0426(9) 0.0228(7) 0.0334(8) 0.0012(6) 0.0114(7) 0.0021(7)
C33 0.0553(12) 0.0309(9) 0.0395(10) 0.0018(7) 0.0242(9) 0.0067(8)
C34 0.0420(11) 0.0327(9) 0.0614(12) 0.0060(8) 0.0299(10) 0.0071(8)
C35 0.0300(9) 0.0333(9) 0.0580(11) 0.0050(8) 0.0104(8) 0.0027(7)
C36 0.0333(9) 0.0334(8) 0.0356(9) 0.0033(7) 0.0085(7) 0.0016(7)
C37 0.0562(12) 0.0336(9) 0.0301(9) -0.0049(7) 0.0035(8) 0.0049(8)
C41 0.0250(8) 0.0252(7) 0.0321(8) 0.0058(6) 0.0085(6) -0.0021(6)
C42 0.0294(8) 0.0281(8) 0.0355(9) 0.0046(6) 0.0031(7) -0.0025(6)
C43 0.0369(10) 0.0415(10) 0.0407(10) 0.0110(8) 0.0018(8) 0.0019(7)
C44 0.0360(10) 0.0334(9) 0.0556(11) 0.0133(8) 0.0131(8) 0.0108(8)
C45 0.0397(10) 0.0288(8) 0.0465(10) 0.0013(7) 0.0194(8) 0.0011(7)
C46 0.0338(9) 0.0321(8) 0.0330(9) 0.0029(7) 0.0133(7) -0.0011(7)
C47 0.0489(11) 0.0362(9) 0.0335(9) -0.0018(7) -0.0064(8) 0.0003(8)
N1 0.0281(8) 0.0279(8) 0.0574(10) 0.0045(6) 0.0117(7) 0.0004(6)
O1 0.0344(6) 0.0259(6) 0.0647(8) 0.0027(5) 0.0171(6) 0.0004(5)
O2 0.0252(6) 0.0321(6) 0.0504(7) 0.0051(5) 0.0129(5) 0.0026(5)
O3 0.0300(6) 0.0237(6) 0.0598(8) -0.0009(5) 0.0131(5) 0.0045(5)
C1 0.0273(8) 0.0282(8) 0.0285(8) 0.0022(6) 0.0040(6) 0.0047(6)
C2 0.0227(7) 0.0270(7) 0.0262(7) 0.0013(6) 0.0036(6) 0.0037(6)
C3 0.0265(8) 0.0239(7) 0.0275(8) 0.0010(6) 0.0028(6) 0.0061(6)
C4 0.0222(8) 0.0299(8) 0.0304(8) 0.0003(6) 0.0047(6) 0.0036(6)
C5 0.0267(8) 0.0280(8) 0.0248(7) 0.0023(6) 0.0033(6) 0.0006(6)
C6 0.0298(8) 0.0237(8) 0.0434(9) 0.0005(7) 0.0098(7) 0.0036(6)
C7 0.0245(8) 0.0306(8) 0.0373(9) 0.0021(7) 0.0083(7) 0.0071(6)
O4 0.0291(7) 0.0402(7) 0.0659(8) 0.0136(6) 0.0159(6) 0.0036(5)
C40 0.0454(12) 0.0346(10) 0.0745(15) 0.0086(10) 0.0249(11) 0.0036(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O11 C10 1.2414(16) . ?
N11 C10 1.3419(19) . ?
N11 H11 0.881(19) . ?
N11 H12 0.909(18) . ?
N12 C10 1.3674(17) . ?
N12 C11 1.4359(18) . ?
N12 C21 1.4376(18) . ?
C11 C16 1.385(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.401(2) . ?
C12 C17 1.462(2) . ?
C13 C14 1.372(2) . ?
C13 H13 0.969(17) . ?
C14 C15 1.384(2) . ?
C14 H14 0.971(19) . ?
C15 C16 1.379(2) . ?
C15 H15 0.984(17) . ?
C16 H16 0.971(16) . ?
C17 C27 1.337(2) . ?
C17 H17 0.990(19) . ?
C21 C26 1.382(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.400(2) . ?
C22 C27 1.457(2) . ?
C23 C24 1.376(3) . ?
C23 H23 0.973(18) . ?
C24 C25 1.374(3) . ?
C24 H24 0.965(19) . ?
C25 C26 1.390(2) . ?
C25 H25 0.984(19) . ?
C26 H26 0.964(16) . ?
C27 H27 0.974(18) . ?
O21 C30 1.2461(17) . ?
N21 C30 1.3333(19) . ?
N21 H21 0.89(2) . ?
N21 H22 0.875(19) . ?
N22 C30 1.3678(18) . ?
N22 C41 1.4342(18) . ?
N22 C31 1.4367(18) . ?
C31 C36 1.386(2) . ?
C31 C32 1.396(2) . ?
C32 C33 1.405(2) . ?
C32 C37 1.459(2) . ?
C33 C34 1.373(3) . ?
C33 H33 0.988(17) . ?
C34 C35 1.383(3) . ?
C34 H34 0.973(19) . ?
C35 C36 1.385(2) . ?
C35 H35 0.963(18) . ?
C36 H36 0.976(17) . ?
C37 C47 1.332(2) . ?
C37 H37 0.983(19) . ?
C41 C46 1.383(2) . ?
C41 C42 1.398(2) . ?
C42 C43 1.402(2) . ?
C42 C47 1.460(2) . ?
C43 C44 1.373(3) . ?
C43 H43 0.945(18) . ?
C44 C45 1.379(3) . ?
C44 H44 0.916(18) . ?
C45 C46 1.384(2) . ?
C45 H45 0.968(17) . ?
C46 H46 0.999(17) . ?
C47 H47 0.968(19) . ?
N1 C5 1.3576(19) . ?
N1 H1 0.868(19) . ?
N1 H10 0.859(19) . ?
O1 C1 1.2331(17) . ?
O2 C1 1.3266(17) . ?
O2 H2 0.94(2) . ?
O3 C3 1.3598(17) . ?
O3 H3 0.92(2) . ?
C1 C2 1.447(2) . ?
C2 C7 1.398(2) . ?
C2 C3 1.4143(19) . ?
C3 C4 1.375(2) . ?
C4 C5 1.397(2) . ?
C4 H4 0.977(17) . ?
C5 C6 1.411(2) . ?
C6 C7 1.361(2) . ?
C6 H6 0.978(17) . ?
C7 H7 0.974(17) . ?
O4 C40 1.415(2) . ?
O4 H41 0.90(2) . ?
C40 H401 1.00(2) . ?
C40 H402 0.97(2) . ?
C40 H403 0.96(2) . ?
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
C10 N11 H11 123.0(12) . . ?
C10 N11 H12 117.3(11) . . ?
H11 N11 H12 119.4(16) . . ?
C10 N12 C11 119.19(11) . . ?
C10 N12 C21 122.25(11) . . ?
C11 N12 C21 117.11(11) . . ?
O11 C10 N11 121.81(13) . . ?
O11 C10 N12 120.88(12) . . ?
N11 C10 N12 117.30(13) . . ?
C16 C11 C12 121.03(13) . . ?
C16 C11 N12 119.60(13) . . ?
C12 C11 N12 119.37(12) . . ?
C11 C12 C13 117.40(14) . . ?
C11 C12 C17 122.50(13) . . ?
C13 C12 C17 120.10(14) . . ?
C14 C13 C12 121.43(15) . . ?
C14 C13 H13 120.8(10) . . ?
C12 C13 H13 117.8(10) . . ?
C13 C14 C15 120.27(15) . . ?
C13 C14 H14 120.5(10) . . ?
C15 C14 H14 119.2(10) . . ?
C16 C15 C14 119.60(15) . . ?
C16 C15 H15 121.1(9) . . ?
C14 C15 H15 119.3(9) . . ?
C15 C16 C11 120.26(15) . . ?
C15 C16 H16 121.1(9) . . ?
C11 C16 H16 118.6(9) . . ?
C27 C17 C12 127.45(16) . . ?
C27 C17 H17 116.0(11) . . ?
C12 C17 H17 116.2(11) . . ?
C26 C21 C22 121.24(14) . . ?
C26 C21 N12 120.16(14) . . ?
C22 C21 N12 118.60(13) . . ?
C21 C22 C23 117.38(15) . . ?
C21 C22 C27 122.62(14) . . ?
C23 C22 C27 119.96(15) . . ?
C24 C23 C22 121.33(17) . . ?
C24 C23 H23 120.9(10) . . ?
C22 C23 H23 117.7(10) . . ?
C25 C24 C23 120.38(16) . . ?
C25 C24 H24 121.4(11) . . ?
C23 C24 H24 118.2(11) . . ?
C24 C25 C26 119.74(17) . . ?
C24 C25 H25 122.0(11) . . ?
C26 C25 H25 118.3(11) . . ?
C21 C26 C25 119.85(17) . . ?
C21 C26 H26 119.5(9) . . ?
C25 C26 H26 120.6(9) . . ?
C17 C27 C22 127.13(16) . . ?
C17 C27 H27 116.2(10) . . ?
C22 C27 H27 116.0(10) . . ?
C30 N21 H21 120.6(12) . . ?
C30 N21 H22 116.2(12) . . ?
H21 N21 H22 123.0(17) . . ?
C30 N22 C41 120.56(12) . . ?
C30 N22 C31 122.74(12) . . ?
C41 N22 C31 116.65(11) . . ?
O21 C30 N21 121.24(13) . . ?
O21 C30 N22 120.95(13) . . ?
N21 C30 N22 117.81(13) . . ?
C36 C31 C32 121.18(14) . . ?
C36 C31 N22 119.97(13) . . ?
C32 C31 N22 118.84(14) . . ?
C31 C32 C33 117.23(15) . . ?
C31 C32 C37 122.88(14) . . ?
C33 C32 C37 119.89(15) . . ?
C34 C33 C32 121.70(16) . . ?
C34 C33 H33 121.4(10) . . ?
C32 C33 H33 116.9(10) . . ?
C33 C34 C35 120.05(16) . . ?
C33 C34 H34 121.3(11) . . ?
C35 C34 H34 118.7(11) . . ?
C34 C35 C36 119.71(17) . . ?
C34 C35 H35 120.6(11) . . ?
C36 C35 H35 119.7(11) . . ?
C35 C36 C31 120.11(16) . . ?
C35 C36 H36 121.7(10) . . ?
C31 C36 H36 118.2(10) . . ?
C47 C37 C32 127.49(16) . . ?
C47 C37 H37 117.7(11) . . ?
C32 C37 H37 114.5(11) . . ?
C46 C41 C42 121.18(14) . . ?
C46 C41 N22 120.04(14) . . ?
C42 C41 N22 118.75(13) . . ?
C41 C42 C43 117.38(14) . . ?
C41 C42 C47 122.83(14) . . ?
C43 C42 C47 119.71(15) . . ?
C44 C43 C42 121.23(17) . . ?
C44 C43 H43 120.3(11) . . ?
C42 C43 H43 118.4(11) . . ?
C43 C44 C45 120.43(16) . . ?
C43 C44 H44 118.9(11) . . ?
C45 C44 H44 120.7(11) . . ?
C44 C45 C46 119.72(16) . . ?
C44 C45 H45 119.9(10) . . ?
C46 C45 H45 120.3(10) . . ?
C41 C46 C45 119.96(16) . . ?
C41 C46 H46 118.1(10) . . ?
C45 C46 H46 121.9(10) . . ?
C37 C47 C42 126.93(16) . . ?
C37 C47 H47 119.0(11) . . ?
C42 C47 H47 113.5(11) . . ?
C5 N1 H1 118.8(12) . . ?
C5 N1 H10 119.4(12) . . ?
H1 N1 H10 121.5(17) . . ?
C1 O2 H2 108.6(12) . . ?
C3 O3 H3 103.8(13) . . ?
O1 C1 O2 120.51(14) . . ?
O1 C1 C2 123.03(13) . . ?
O2 C1 C2 116.46(13) . . ?
C7 C2 C3 117.13(13) . . ?
C7 C2 C1 122.70(13) . . ?
C3 C2 C1 120.17(13) . . ?
O3 C3 C4 118.21(13) . . ?
O3 C3 C2 120.61(13) . . ?
C4 C3 C2 121.18(13) . . ?
C3 C4 C5 120.60(14) . . ?
C3 C4 H4 119.9(10) . . ?
C5 C4 H4 119.4(10) . . ?
N1 C5 C4 120.52(14) . . ?
N1 C5 C6 120.96(14) . . ?
C4 C5 C6 118.52(13) . . ?
C7 C6 C5 120.30(14) . . ?
C7 C6 H6 119.6(10) . . ?
C5 C6 H6 120.1(10) . . ?
C6 C7 C2 122.24(14) . . ?
C6 C7 H7 119.3(10) . . ?
C2 C7 H7 118.4(10) . . ?
C40 O4 H41 114.6(14) . . ?
O4 C40 H401 110.1(13) . . ?
O4 C40 H402 110.7(14) . . ?
H401 C40 H402 105.4(19) . . ?
O4 C40 H403 107.6(13) . . ?
H401 C40 H403 108.8(18) . . ?
H402 C40 H403 114.2(19) . . ?
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
C11 N12 C10 O11 -0.4(2) . . . . ?
C21 N12 C10 O11 -166.20(13) . . . . ?
C11 N12 C10 N11 -179.84(13) . . . . ?
C21 N12 C10 N11 14.3(2) . . . . ?
C10 N12 C11 C16 77.53(17) . . . . ?
C21 N12 C11 C16 -115.91(15) . . . . ?
C10 N12 C11 C12 -102.35(15) . . . . ?
C21 N12 C11 C12 64.21(17) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
N12 C11 C12 C13 -179.72(12) . . . . ?
C16 C11 C12 C17 -179.16(14) . . . . ?
N12 C11 C12 C17 0.7(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C17 C12 C13 C14 179.45(15) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 C15 C16 C11 -0.9(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
N12 C11 C16 C15 -179.76(13) . . . . ?
C11 C12 C17 C27 -33.2(2) . . . . ?
C13 C12 C17 C27 147.21(17) . . . . ?
C10 N12 C21 C26 -82.32(18) . . . . ?
C11 N12 C21 C26 111.56(15) . . . . ?
C10 N12 C21 C22 96.78(16) . . . . ?
C11 N12 C21 C22 -69.33(17) . . . . ?
C26 C21 C22 C23 3.4(2) . . . . ?
N12 C21 C22 C23 -175.74(13) . . . . ?
C26 C21 C22 C27 -174.30(15) . . . . ?
N12 C21 C22 C27 6.6(2) . . . . ?
C21 C22 C23 C24 -1.6(2) . . . . ?
C27 C22 C23 C24 176.11(15) . . . . ?
C22 C23 C24 C25 -0.6(2) . . . . ?
C23 C24 C25 C26 1.1(2) . . . . ?
C22 C21 C26 C25 -2.9(2) . . . . ?
N12 C21 C26 C25 176.15(13) . . . . ?
C24 C25 C26 C21 0.7(2) . . . . ?
C12 C17 C27 C22 -2.9(3) . . . . ?
C21 C22 C27 C17 33.1(3) . . . . ?
C23 C22 C27 C17 -144.50(17) . . . . ?
C41 N22 C30 O21 1.7(2) . . . . ?
C31 N22 C30 O21 179.11(13) . . . . ?
C41 N22 C30 N21 -178.17(13) . . . . ?
C31 N22 C30 N21 -0.7(2) . . . . ?
C30 N22 C31 C36 68.22(19) . . . . ?
C41 N22 C31 C36 -114.24(15) . . . . ?
C30 N22 C31 C32 -111.11(16) . . . . ?
C41 N22 C31 C32 66.43(17) . . . . ?
C36 C31 C32 C33 -1.0(2) . . . . ?
N22 C31 C32 C33 178.36(13) . . . . ?
C36 C31 C32 C37 178.61(14) . . . . ?
N22 C31 C32 C37 -2.1(2) . . . . ?
C31 C32 C33 C34 0.4(2) . . . . ?
C37 C32 C33 C34 -179.15(15) . . . . ?
C32 C33 C34 C35 -0.5(2) . . . . ?
C33 C34 C35 C36 1.1(2) . . . . ?
C34 C35 C36 C31 -1.6(2) . . . . ?
C32 C31 C36 C35 1.6(2) . . . . ?
N22 C31 C36 C35 -177.73(13) . . . . ?
C31 C32 C37 C47 -32.9(3) . . . . ?
C33 C32 C37 C47 146.63(18) . . . . ?
C30 N22 C41 C46 -72.61(18) . . . . ?
C31 N22 C41 C46 109.79(15) . . . . ?
C30 N22 C41 C42 108.98(16) . . . . ?
C31 N22 C41 C42 -68.61(17) . . . . ?
C46 C41 C42 C43 3.7(2) . . . . ?
N22 C41 C42 C43 -177.95(13) . . . . ?
C46 C41 C42 C47 -173.25(15) . . . . ?
N22 C41 C42 C47 5.1(2) . . . . ?
C41 C42 C43 C44 -3.0(2) . . . . ?
C47 C42 C43 C44 174.00(16) . . . . ?
C42 C43 C44 C45 0.6(3) . . . . ?
C43 C44 C45 C46 1.2(2) . . . . ?
C42 C41 C46 C45 -1.9(2) . . . . ?
N22 C41 C46 C45 179.71(13) . . . . ?
C44 C45 C46 C41 -0.6(2) . . . . ?
C32 C37 C47 C42 -1.0(3) . . . . ?
C41 C42 C47 C37 32.6(3) . . . . ?
C43 C42 C47 C37 -144.20(18) . . . . ?
O1 C1 C2 C7 -178.02(15) . . . . ?
O2 C1 C2 C7 1.7(2) . . . . ?
O1 C1 C2 C3 0.9(2) . . . . ?
O2 C1 C2 C3 -179.41(13) . . . . ?
C7 C2 C3 O3 -178.50(13) . . . . ?
C1 C2 C3 O3 2.6(2) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -177.88(13) . . . . ?
O3 C3 C4 C5 179.73(13) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 N1 179.11(14) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
N1 C5 C6 C7 -179.03(15) . . . . ?
C4 C5 C6 C7 1.6(2) . . . . ?
C5 C6 C7 C2 -0.3(2) . . . . ?
C3 C2 C7 C6 -1.0(2) . . . . ?
C1 C2 C7 C6 177.94(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O4 0.94(2) 1.66(2) 2.5982(16) 176.7(19) 1_545
O3 H3 O1 0.92(2) 1.71(2) 2.5673(16) 153.9(19) .
N1 H1 O11 0.868(19) 2.17(2) 2.9849(19) 156.0(16) .
N1 H10 O3 0.859(19) 2.430(19) 3.2692(19) 165.7(15) 1_565
N11 H12 O21 0.909(18) 2.077(19) 2.9843(17) 175.2(15) 1_545
N21 H22 O11 0.875(19) 2.07(2) 2.9408(17) 174.7(17) 1_565
O4 H41 O21 0.90(2) 1.78(2) 2.6434(16) 161(2) 1_455
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.191
_refine_diff_density_min -0.187
_refine_diff_density_rms 0.034