# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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# fide research purposes only. It may contain copyright material
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data_sdnbdn(1)
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
strychninium N-(3,5-dinitrobenzoyl)-D-asparaginate 1.75-hydrate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H23 N2 O2, C11 H9 N4 O8, 1.75(H2 O)'
_chemical_formula_sum 'C32 H35.50 N6 O11.75'
_chemical_formula_weight 692.16
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'
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 8.006(2)
_cell_length_b 11.184(3)
_cell_length_c 34.465(5)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 3086.0(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9056
_cell_measurement_theta_min 2.98
_cell_measurement_theta_max 34.50
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.490
_exptl_crystal_F_000 1454
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.300
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 0.115
_shelx_estimated_absorpt_T_min ?
_shelx_estimated_absorpt_T_max ?
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Sapphire2'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 53657
_diffrn_reflns_av_unetI/netI 0.0806
_diffrn_reflns_av_R_equivalents 0.0809
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -53
_diffrn_reflns_limit_l_max 54
_diffrn_reflns_theta_min 2.984
_diffrn_reflns_theta_max 34.496
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total 12848
_reflns_number_gt 8799
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.773
_reflns_Friedel_fraction_max 0.964
_reflns_Friedel_fraction_full 1.000
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.7734P]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 2911 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack -0.3(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 12848
_refine_ls_number_parameters 524
_refine_ls_number_restraints 84
_refine_ls_R_factor_all 0.1026
_refine_ls_R_factor_gt 0.0681
_refine_ls_wR_factor_ref 0.1598
_refine_ls_wR_factor_gt 0.1489
_refine_ls_goodness_of_fit_ref 1.084
_refine_ls_restrained_S_all 1.082
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2372(3) 0.0391(2) 0.18131(6) 0.0254(4) Uani 1 1 d . . . . .
O2 O 0.6782(3) 0.1260(2) 0.26712(6) 0.0281(5) Uani 1 1 d . . . . .
N1 N 0.6498(3) 0.1993(2) 0.20550(6) 0.0194(5) Uani 1 1 d . . . . .
N2 N 0.4461(3) 0.3417(3) 0.08881(7) 0.0256(5) Uani 1 1 d . . . . .
H22 H 0.4660 0.4016 0.0678 0.031 Uiso 1 1 calc R U . . .
C1 C 0.8700(3) 0.3298(3) 0.23725(8) 0.0230(6) Uani 1 1 d . . . . .
H1 H 0.8863 0.2799 0.2592 0.028 Uiso 1 1 calc R U . . .
C2 C 0.9576(3) 0.4372(3) 0.23271(8) 0.0236(6) Uani 1 1 d . . . . .
H2 H 1.0337 0.4611 0.2524 0.028 Uiso 1 1 calc R U . . .
C3 C 0.9372(4) 0.5101(3) 0.20038(8) 0.0250(6) Uani 1 1 d . . . . .
H3 H 0.9985 0.5825 0.1982 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8264(4) 0.4766(3) 0.17123(8) 0.0240(6) Uani 1 1 d . . . . .
H4 H 0.8129 0.5251 0.1488 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7362(3) 0.3719(3) 0.17518(8) 0.0205(5) Uani 1 1 d . . . . .
C6 C 0.7581(3) 0.2999(3) 0.20798(7) 0.0192(5) Uani 1 1 d . . . . .
C7 C 0.6158(3) 0.3134(3) 0.14701(7) 0.0192(5) Uani 1 1 d . . . . .
C8 C 0.5336(3) 0.2148(3) 0.17216(7) 0.0171(5) Uani 1 1 d . . . . .
H8 H 0.5281 0.1387 0.1570 0.020 Uiso 1 1 calc R U . . .
C9 C 0.5979(4) 0.1314(3) 0.23687(8) 0.0221(5) Uani 1 1 d . . . . .
C10 C 0.4383(4) 0.0632(3) 0.23065(9) 0.0253(6) Uani 1 1 d . . . . .
H10A H 0.3939 0.0405 0.2564 0.030 Uiso 1 1 calc R U . . .
H10B H 0.4662 -0.0118 0.2168 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2967(3) 0.1263(3) 0.20793(8) 0.0214(5) Uani 1 1 d . . . . .
H11 H 0.2047 0.1468 0.2264 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0907(4) 0.0744(3) 0.16007(9) 0.0299(7) Uani 1 1 d . . . . .
H12A H 0.0228 0.1295 0.1761 0.036 Uiso 1 1 calc R U . . .
H12B H 0.0220 0.0030 0.1543 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1379(4) 0.1348(3) 0.12309(9) 0.0265(6) Uani 1 1 d . . . . .
H13 H 0.1133 0.0969 0.0991 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2141(3) 0.2409(3) 0.12304(8) 0.0230(6) Uani 1 1 d . . . . .
C15 C 0.2656(4) 0.3024(3) 0.08636(8) 0.0256(6) Uani 1 1 d . . . . .
H15A H 0.1934 0.3730 0.0820 0.031 Uiso 1 1 calc R U . . .
H15B H 0.2513 0.2472 0.0641 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5655(4) 0.2389(3) 0.08261(8) 0.0290(7) Uani 1 1 d . . . . .
H16A H 0.6092 0.2390 0.0557 0.035 Uiso 1 1 calc R U . . .
H16B H 0.5096 0.1615 0.0876 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7051(4) 0.2600(3) 0.11153(8) 0.0247(6) Uani 1 1 d . . . . .
H17A H 0.7888 0.3165 0.1010 0.030 Uiso 1 1 calc R U . . .
H17B H 0.7615 0.1840 0.1183 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3617(3) 0.2420(3) 0.18931(8) 0.0202(5) Uani 1 1 d . . . . .
H18 H 0.3816 0.2989 0.2112 0.024 Uiso 1 1 calc R U . . .
C19 C 0.2477(3) 0.3082(3) 0.16058(8) 0.0216(5) Uani 1 1 d . . . . .
H19 H 0.1387 0.3257 0.1736 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3341(4) 0.4262(3) 0.15110(8) 0.0248(6) Uani 1 1 d . . . . .
H20A H 0.2581 0.4779 0.1359 0.030 Uiso 1 1 calc R U . . .
H20B H 0.3630 0.4687 0.1754 0.030 Uiso 1 1 calc R U . . .
C21 C 0.4916(4) 0.4010(3) 0.12793(8) 0.0243(6) Uani 1 1 d . . . . .
H21 H 0.5502 0.4783 0.1227 0.029 Uiso 1 1 calc R U . . .
O3 O 0.4784(4) 0.5490(3) 0.05042(10) 0.0285(8) Uani 0.751(4) 1 d . U P A 1
O4 O 0.4500(5) 0.6873(3) 0.00454(10) 0.0243(7) Uani 0.751(4) 1 d . U P A 1
O5 O -0.0767(4) 0.4625(3) 0.06679(9) 0.0321(8) Uani 0.751(4) 1 d . . P A 1
N3 N -0.1848(4) 0.6386(3) 0.04751(10) 0.0290(8) Uani 0.751(4) 1 d . . P A 1
H37A H -0.2880 0.6120 0.0492 0.035 Uiso 0.751(4) 1 calc R U P A 1
H37B H -0.1657 0.7126 0.0401 0.035 Uiso 0.751(4) 1 calc R U P A 1
C22 C 0.3980(6) 0.6037(5) 0.02436(13) 0.0194(9) Uani 0.751(4) 1 d . U P A 1
C23 C 0.2146(11) 0.5621(14) 0.0186(4) 0.0187(14) Uani 0.751(4) 1 d . U P A 1
H23 H 0.2086 0.4729 0.0203 0.022 Uiso 0.751(4) 1 calc R U P A 1
C24 C 0.1170(5) 0.6178(4) 0.05253(10) 0.0197(7) Uani 0.751(4) 1 d . U P A 1
H24A H 0.1784 0.6031 0.0770 0.024 Uiso 0.751(4) 1 calc R U P A 1
H24B H 0.1103 0.7054 0.0487 0.024 Uiso 0.751(4) 1 calc R U P A 1
C25 C -0.0586(5) 0.5674(4) 0.05616(11) 0.0246(8) Uani 0.751(4) 1 d . U P A 1
O2W O -0.1872(5) 0.3606(5) -0.00320(12) 0.0627(13) Uani 0.751(4) 1 d . . P A 1
H21W H -0.2917 0.3648 -0.0088 0.094 Uiso 0.751(4) 1 d R U P A 1
H22W H -0.1677 0.4074 0.0161 0.094 Uiso 0.751(4) 1 d R U P A 1
O3A O 0.4043(16) 0.5762(11) 0.0601(3) 0.036(3) Uani 0.249(4) 1 d . U P A 2
O4A O 0.3892(15) 0.7140(13) 0.0124(4) 0.033(3) Uani 0.249(4) 1 d . U P A 2
O5A O -0.0941(16) 0.3975(11) 0.0439(4) 0.046(3) Uani 0.249(4) 1 d . U P A 2
N3A N -0.2423(17) 0.5538(14) 0.0205(4) 0.048(4) Uani 0.249(4) 1 d . U P A 2
H37C H -0.3314 0.5101 0.0158 0.058 Uiso 0.249(4) 1 calc R U P A 2
H37D H -0.2430 0.6308 0.0152 0.058 Uiso 0.249(4) 1 calc R U P A 2
C22A C 0.3329(18) 0.6183(14) 0.0294(4) 0.020(3) Uani 0.249(4) 1 d . U P A 2
C23A C 0.177(4) 0.566(4) 0.0189(14) 0.023(5) Uani 0.249(4) 1 d . U P A 2
H23A H 0.1948 0.4772 0.0178 0.028 Uiso 0.249(4) 1 calc R U P A 2
C24A C 0.0368(18) 0.5883(13) 0.0465(4) 0.026(2) Uani 0.249(4) 1 d . U P A 2
H24C H -0.0003 0.6725 0.0446 0.031 Uiso 0.249(4) 1 calc R U P A 2
H24D H 0.0734 0.5728 0.0735 0.031 Uiso 0.249(4) 1 calc R U P A 2
C25A C -0.1067(16) 0.5037(12) 0.0356(4) 0.027(3) Uani 0.249(4) 1 d . U P A 2
O6 O 0.2896(3) 0.4777(2) -0.05570(6) 0.0305(5) Uani 1 1 d . . . . .
O7 O 0.3702(3) 0.6686(3) -0.18645(7) 0.0440(7) Uani 1 1 d . . . . .
O8 O 0.1527(3) 0.7272(3) -0.21725(7) 0.0470(7) Uani 1 1 d . . . . .
O9 O -0.3667(3) 0.7857(3) -0.14441(7) 0.0431(7) Uani 1 1 d . . . . .
O10 O -0.4073(3) 0.6507(3) -0.09969(7) 0.0411(7) Uani 1 1 d . . . . .
N4 N 0.1360(3) 0.6035(2) -0.01840(7) 0.0226(5) Uani 1 1 d . . . . .
H47 H 0.0578 0.6587 -0.0179 0.027 Uiso 1 1 calc R U . A 1
N5 N 0.2213(3) 0.6915(3) -0.18807(7) 0.0279(6) Uani 1 1 d . . . . .
N6 N -0.3172(3) 0.7077(3) -0.12200(8) 0.0324(6) Uani 1 1 d . . . . .
C26 C 0.1839(3) 0.5569(3) -0.05194(8) 0.0226(6) Uani 1 1 d . . . . .
C27 C 0.0991(3) 0.6078(3) -0.08716(8) 0.0218(6) Uani 1 1 d . . . . .
C28 C 0.1944(4) 0.6270(3) -0.12043(8) 0.0232(6) Uani 1 1 d . . . . .
H28 H 0.3101 0.6078 -0.1206 0.028 Uiso 1 1 calc R U . . .
C29 C 0.1197(4) 0.6739(3) -0.15307(8) 0.0242(6) Uani 1 1 d . . . . .
C30 C -0.0472(4) 0.7050(3) -0.15453(8) 0.0253(6) Uani 1 1 d . . . . .
H30 H -0.0958 0.7402 -0.1769 0.030 Uiso 1 1 calc R U . . .
C31 C -0.1390(4) 0.6820(3) -0.12143(8) 0.0258(6) Uani 1 1 d . . . . .
C32 C -0.0712(4) 0.6344(3) -0.08783(8) 0.0242(6) Uani 1 1 d . . . . .
H32 H -0.1392 0.6201 -0.0657 0.029 Uiso 1 1 calc R U . . .
O1W O 0.4804(4) 0.3367(4) -0.00615(9) 0.0698(11) Uani 1 1 d . . . . .
H11W H 0.4267 0.3862 -0.0206 0.105 Uiso 1 1 d R U . . .
H12W H 0.4500 0.2653 -0.0121 0.105 Uiso 1 1 d R U . . .
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
O1 0.0241(10) 0.0307(12) 0.0213(9) -0.0002(9) 0.0009(8) -0.0018(9)
O2 0.0245(10) 0.0382(13) 0.0216(10) 0.0117(9) -0.0016(8) 0.0014(10)
N1 0.0177(10) 0.0265(12) 0.0139(9) 0.0055(9) 0.0008(8) 0.0021(9)
N2 0.0205(11) 0.0379(15) 0.0184(11) 0.0086(11) -0.0022(9) -0.0006(11)
C1 0.0168(12) 0.0340(16) 0.0182(12) 0.0010(11) 0.0000(10) 0.0033(11)
C2 0.0172(12) 0.0325(15) 0.0211(12) -0.0049(12) 0.0008(10) 0.0009(12)
C3 0.0223(13) 0.0267(15) 0.0260(14) -0.0026(12) 0.0034(11) -0.0027(12)
C4 0.0208(13) 0.0272(14) 0.0241(13) 0.0055(12) 0.0053(10) 0.0000(11)
C5 0.0165(12) 0.0265(14) 0.0185(11) 0.0031(11) 0.0006(9) 0.0024(11)
C6 0.0154(11) 0.0232(13) 0.0189(11) 0.0020(11) 0.0031(9) 0.0032(10)
C7 0.0194(12) 0.0254(14) 0.0127(10) 0.0035(10) 0.0002(9) 0.0033(11)
C8 0.0152(11) 0.0233(13) 0.0127(10) 0.0028(10) -0.0005(8) 0.0012(10)
C9 0.0217(13) 0.0254(14) 0.0193(12) 0.0066(11) 0.0021(10) 0.0056(11)
C10 0.0232(14) 0.0267(14) 0.0259(14) 0.0073(12) 0.0010(11) 0.0004(12)
C11 0.0190(12) 0.0276(14) 0.0176(11) 0.0036(11) 0.0035(9) -0.0011(11)
C12 0.0210(14) 0.0438(19) 0.0248(14) 0.0001(14) -0.0010(11) -0.0058(14)
C13 0.0206(13) 0.0380(17) 0.0208(12) -0.0016(13) -0.0036(11) -0.0011(13)
C14 0.0176(12) 0.0332(15) 0.0182(11) 0.0042(12) -0.0018(10) 0.0048(12)
C15 0.0208(13) 0.0351(16) 0.0210(12) 0.0051(12) -0.0038(10) 0.0012(12)
C16 0.0265(15) 0.0454(19) 0.0152(12) 0.0007(12) 0.0021(10) 0.0069(14)
C17 0.0191(13) 0.0383(17) 0.0167(11) 0.0042(12) 0.0022(9) -0.0003(12)
C18 0.0185(12) 0.0259(14) 0.0162(11) -0.0004(10) 0.0019(9) 0.0018(11)
C19 0.0172(12) 0.0296(15) 0.0179(11) 0.0007(11) 0.0001(9) 0.0039(11)
C20 0.0225(13) 0.0306(15) 0.0214(12) 0.0041(12) -0.0020(10) 0.0057(12)
C21 0.0242(14) 0.0276(15) 0.0210(13) 0.0070(11) -0.0035(10) 0.0006(12)
O3 0.0186(15) 0.039(2) 0.0276(16) 0.0155(15) -0.0036(12) -0.0015(14)
O4 0.0179(16) 0.0313(19) 0.0236(16) 0.0081(14) -0.0026(12) -0.0033(14)
O5 0.0269(15) 0.0318(18) 0.0374(17) 0.0155(15) 0.0018(13) -0.0038(13)
N3 0.0196(16) 0.0339(19) 0.0335(18) 0.0111(16) 0.0048(13) 0.0030(15)
C22 0.0107(18) 0.028(2) 0.0202(19) 0.0017(15) 0.0001(16) -0.0034(18)
C23 0.017(4) 0.025(2) 0.0145(19) 0.0079(17) 0.005(3) 0.001(3)
C24 0.0153(18) 0.0263(19) 0.0174(16) 0.0026(14) -0.0002(13) -0.0019(15)
C25 0.0216(19) 0.033(2) 0.0192(17) 0.0105(17) 0.0046(14) -0.0015(17)
O2W 0.046(2) 0.097(4) 0.046(2) -0.023(2) 0.0043(18) 0.000(2)
O3A 0.036(5) 0.041(5) 0.033(5) 0.009(4) -0.016(4) -0.007(5)
O4A 0.025(5) 0.044(6) 0.028(5) 0.013(4) -0.003(4) -0.001(5)
O5A 0.054(6) 0.040(6) 0.046(6) 0.000(5) 0.007(5) -0.015(5)
N3A 0.036(6) 0.055(7) 0.054(7) 0.011(6) 0.001(5) 0.006(6)
C22A 0.017(6) 0.029(6) 0.014(5) 0.017(4) -0.002(4) -0.004(5)
C23A 0.022(10) 0.022(7) 0.025(7) 0.003(6) -0.003(8) -0.003(9)
C24A 0.018(5) 0.033(5) 0.025(5) 0.006(4) 0.006(4) -0.001(5)
C25A 0.026(6) 0.026(6) 0.029(6) 0.005(5) 0.001(4) -0.004(5)
O6 0.0287(11) 0.0383(12) 0.0245(10) -0.0054(10) -0.0049(9) 0.0105(10)
O7 0.0307(13) 0.072(2) 0.0287(12) 0.0068(13) 0.0048(10) 0.0131(13)
O8 0.0374(14) 0.078(2) 0.0259(11) 0.0138(13) 0.0005(10) 0.0096(14)
O9 0.0295(12) 0.0618(18) 0.0380(13) 0.0072(13) -0.0071(10) 0.0144(13)
O10 0.0208(11) 0.0688(19) 0.0337(12) 0.0007(13) -0.0027(9) 0.0022(12)
N4 0.0202(11) 0.0285(12) 0.0191(10) 0.0037(10) 0.0014(9) 0.0028(10)
N5 0.0292(13) 0.0361(15) 0.0182(11) -0.0015(11) -0.0005(9) 0.0038(12)
N6 0.0209(12) 0.0527(18) 0.0235(12) -0.0041(13) -0.0081(10) 0.0079(13)
C26 0.0185(12) 0.0297(15) 0.0194(12) 0.0008(11) -0.0024(10) -0.0016(12)
C27 0.0188(12) 0.0275(14) 0.0190(12) -0.0041(11) -0.0041(10) 0.0015(11)
C28 0.0198(13) 0.0294(15) 0.0205(12) -0.0061(11) -0.0008(10) 0.0019(12)
C29 0.0270(15) 0.0302(15) 0.0154(12) -0.0039(11) -0.0009(10) 0.0016(12)
C30 0.0229(14) 0.0330(16) 0.0199(12) -0.0046(12) -0.0058(10) 0.0019(13)
C31 0.0176(12) 0.0394(17) 0.0204(12) -0.0060(13) -0.0043(10) 0.0043(13)
C32 0.0196(13) 0.0342(16) 0.0189(12) -0.0031(12) -0.0032(10) -0.0017(12)
O1W 0.057(2) 0.101(3) 0.0507(18) 0.0020(19) -0.0191(15) 0.038(2)
_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
O1 C11 1.421(4) . ?
O1 C12 1.438(4) . ?
O2 C9 1.226(3) . ?
N1 C9 1.385(4) . ?
N1 C6 1.423(4) . ?
N1 C8 1.488(3) . ?
N2 C16 1.510(4) . ?
N2 C15 1.513(4) . ?
N2 C21 1.547(4) . ?
N2 H22 1.0000 . ?
C1 C6 1.390(4) . ?
C1 C2 1.400(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(4) . ?
C5 C7 1.516(4) . ?
C7 C17 1.538(4) . ?
C7 C21 1.543(4) . ?
C7 C8 1.549(4) . ?
C8 C18 1.529(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.503(4) . ?
C10 C11 1.548(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.536(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.491(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.334(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.497(4) . ?
C14 C19 1.521(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.516(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.537(4) . ?
C18 H18 1.0000 . ?
C19 C20 1.525(4) . ?
C19 H19 1.0000 . ?
C20 C21 1.519(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
O3 C22 1.263(6) . ?
O4 C22 1.231(6) . ?
O5 C25 1.238(5) . ?
N3 C25 1.320(5) . ?
N3 H37A 0.8800 . ?
N3 H37B 0.8800 . ?
C22 C23 1.552(11) . ?
C23 N4 1.496(13) . ?
C23 C24 1.538(13) . ?
C23 H23 1.0000 . ?
C24 C25 1.521(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
O2W H21W 0.8601 . ?
O2W H22W 0.8600 . ?
O3A C22A 1.291(16) . ?
O4A C22A 1.301(19) . ?
O5A C25A 1.227(17) . ?
N3A C25A 1.327(18) . ?
N3A H37C 0.8800 . ?
N3A H37D 0.8800 . ?
C22A C23A 1.42(4) . ?
C23A N4 1.39(5) . ?
C23A C24A 1.49(4) . ?
C23A H23A 1.0000 . ?
C24A C25A 1.54(2) . ?
C24A H24C 0.9900 . ?
C24A H24D 0.9900 . ?
O6 C26 1.232(4) . ?
O7 N5 1.221(4) . ?
O8 N5 1.214(3) . ?
O9 N6 1.231(4) . ?
O10 N6 1.232(4) . ?
N4 C26 1.325(4) . ?
N4 H47 0.8800 . ?
N5 C29 1.468(4) . ?
N6 C31 1.455(4) . ?
C26 C27 1.503(4) . ?
C27 C28 1.394(4) . ?
C27 C32 1.396(4) . ?
C28 C29 1.378(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.382(4) . ?
C30 C31 1.381(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(4) . ?
C32 H32 0.9500 . ?
O1W H11W 0.8600 . ?
O1W H12W 0.8601 . ?
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
C11 O1 C12 114.5(2) . . ?
C9 N1 C6 124.7(2) . . ?
C9 N1 C8 118.6(2) . . ?
C6 N1 C8 109.6(2) . . ?
C16 N2 C15 112.1(3) . . ?
C16 N2 C21 107.5(2) . . ?
C15 N2 C21 113.5(2) . . ?
C16 N2 H22 107.9 . . ?
C15 N2 H22 107.9 . . ?
C21 N2 H22 107.9 . . ?
C6 C1 C2 116.7(3) . . ?
C6 C1 H1 121.7 . . ?
C2 C1 H1 121.7 . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C7 129.4(3) . . ?
C6 C5 C7 110.4(2) . . ?
C1 C6 C5 121.9(3) . . ?
C1 C6 N1 128.8(3) . . ?
C5 C6 N1 109.3(2) . . ?
C5 C7 C17 112.4(2) . . ?
C5 C7 C21 114.1(3) . . ?
C17 C7 C21 102.0(2) . . ?
C5 C7 C8 102.6(2) . . ?
C17 C7 C8 111.4(2) . . ?
C21 C7 C8 114.6(2) . . ?
N1 C8 C18 106.7(2) . . ?
N1 C8 C7 104.4(2) . . ?
C18 C8 C7 117.2(2) . . ?
N1 C8 H8 109.4 . . ?
C18 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
O2 C9 N1 122.2(3) . . ?
O2 C9 C10 122.8(3) . . ?
N1 C9 C10 115.0(2) . . ?
C9 C10 C11 117.6(3) . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 115.0(2) . . ?
O1 C11 C10 105.0(2) . . ?
C18 C11 C10 110.3(2) . . ?
O1 C11 H11 108.8 . . ?
C18 C11 H11 108.8 . . ?
C10 C11 H11 108.8 . . ?
O1 C12 C13 110.6(2) . . ?
O1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 122.4(3) . . ?
C13 C14 C19 121.4(3) . . ?
C15 C14 C19 116.2(3) . . ?
C14 C15 N2 110.4(2) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 104.8(3) . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.9(2) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 107.4(2) . . ?
C8 C18 C19 112.4(2) . . ?
C11 C18 C19 118.3(2) . . ?
C8 C18 H18 106.0 . . ?
C11 C18 H18 106.0 . . ?
C19 C18 H18 106.0 . . ?
C14 C19 C20 109.1(2) . . ?
C14 C19 C18 114.5(2) . . ?
C20 C19 C18 106.6(2) . . ?
C14 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C18 C19 H19 108.9 . . ?
C21 C20 C19 109.2(3) . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 C7 115.4(2) . . ?
C20 C21 N2 110.0(2) . . ?
C7 C21 N2 104.5(2) . . ?
C20 C21 H21 108.9 . . ?
C7 C21 H21 108.9 . . ?
N2 C21 H21 108.9 . . ?
C25 N3 H37A 120.0 . . ?
C25 N3 H37B 120.0 . . ?
H37A N3 H37B 120.0 . . ?
O4 C22 O3 126.1(4) . . ?
O4 C22 C23 118.5(6) . . ?
O3 C22 C23 115.3(6) . . ?
N4 C23 C24 108.0(7) . . ?
N4 C23 C22 114.5(8) . . ?
C24 C23 C22 105.2(9) . . ?
N4 C23 H23 109.7 . . ?
C24 C23 H23 109.7 . . ?
C22 C23 H23 109.7 . . ?
C25 C24 C23 112.5(6) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
O5 C25 N3 123.3(4) . . ?
O5 C25 C24 118.9(4) . . ?
N3 C25 C24 117.7(4) . . ?
H21W O2W H22W 108.5 . . ?
C25A N3A H37C 120.0 . . ?
C25A N3A H37D 120.0 . . ?
H37C N3A H37D 120.0 . . ?
O3A C22A O4A 121.0(13) . . ?
O3A C22A C23A 116(2) . . ?
O4A C22A C23A 122(2) . . ?
N4 C23A C22A 108(3) . . ?
N4 C23A C24A 111(2) . . ?
C22A C23A C24A 115(3) . . ?
N4 C23A H23A 107.3 . . ?
C22A C23A H23A 107.3 . . ?
C24A C23A H23A 107.3 . . ?
C23A C24A C25A 108(2) . . ?
C23A C24A H24C 110.2 . . ?
C25A C24A H24C 110.2 . . ?
C23A C24A H24D 110.2 . . ?
C25A C24A H24D 110.2 . . ?
H24C C24A H24D 108.5 . . ?
O5A C25A N3A 124.6(14) . . ?
O5A C25A C24A 118.5(12) . . ?
N3A C25A C24A 116.6(13) . . ?
C26 N4 C23A 128.1(18) . . ?
C26 N4 C23 120.1(5) . . ?
C26 N4 H47 120.0 . . ?
C23 N4 H47 120.0 . . ?
O8 N5 O7 123.3(3) . . ?
O8 N5 C29 118.3(3) . . ?
O7 N5 C29 118.4(2) . . ?
O9 N6 O10 124.7(3) . . ?
O9 N6 C31 117.7(3) . . ?
O10 N6 C31 117.6(3) . . ?
O6 C26 N4 125.0(3) . . ?
O6 C26 C27 119.9(3) . . ?
N4 C26 C27 115.1(3) . . ?
C28 C27 C32 119.3(3) . . ?
C28 C27 C26 118.3(3) . . ?
C32 C27 C26 122.4(3) . . ?
C29 C28 C27 119.5(3) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C30 123.1(3) . . ?
C28 C29 N5 118.7(3) . . ?
C30 C29 N5 118.2(3) . . ?
C31 C30 C29 115.9(3) . . ?
C31 C30 H30 122.0 . . ?
C29 C30 H30 122.0 . . ?
C30 C31 C32 123.6(3) . . ?
C30 C31 N6 118.3(3) . . ?
C32 C31 N6 118.1(3) . . ?
C31 C32 C27 118.6(3) . . ?
C31 C32 H32 120.7 . . ?
C27 C32 H32 120.7 . . ?
H11W O1W H12W 108.5 . . ?
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
C6 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C7 -176.6(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C6 N1 -177.9(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C7 C5 C6 C1 176.2(2) . . . . ?
C4 C5 C6 N1 179.0(2) . . . . ?
C7 C5 C6 N1 -4.5(3) . . . . ?
C9 N1 C6 C1 21.1(4) . . . . ?
C8 N1 C6 C1 170.9(3) . . . . ?
C9 N1 C6 C5 -158.3(3) . . . . ?
C8 N1 C6 C5 -8.4(3) . . . . ?
C4 C5 C7 C17 70.9(4) . . . . ?
C6 C5 C7 C17 -105.2(3) . . . . ?
C4 C5 C7 C21 -44.6(4) . . . . ?
C6 C5 C7 C21 139.3(2) . . . . ?
C4 C5 C7 C8 -169.3(3) . . . . ?
C6 C5 C7 C8 14.6(3) . . . . ?
C9 N1 C8 C18 44.4(3) . . . . ?
C6 N1 C8 C18 -107.5(2) . . . . ?
C9 N1 C8 C7 169.2(2) . . . . ?
C6 N1 C8 C7 17.2(3) . . . . ?
C5 C7 C8 N1 -18.5(3) . . . . ?
C17 C7 C8 N1 102.0(2) . . . . ?
C21 C7 C8 N1 -142.9(2) . . . . ?
C5 C7 C8 C18 99.2(3) . . . . ?
C17 C7 C8 C18 -140.3(2) . . . . ?
C21 C7 C8 C18 -25.1(3) . . . . ?
C6 N1 C9 O2 -24.0(4) . . . . ?
C8 N1 C9 O2 -171.4(3) . . . . ?
C6 N1 C9 C10 157.3(3) . . . . ?
C8 N1 C9 C10 9.9(4) . . . . ?
O2 C9 C10 C11 141.8(3) . . . . ?
N1 C9 C10 C11 -39.5(4) . . . . ?
C12 O1 C11 C18 -65.5(3) . . . . ?
C12 O1 C11 C10 173.0(2) . . . . ?
C9 C10 C11 O1 135.0(3) . . . . ?
C9 C10 C11 C18 10.5(4) . . . . ?
C11 O1 C12 C13 90.7(3) . . . . ?
O1 C12 C13 C14 -67.1(4) . . . . ?
C12 C13 C14 C15 178.9(3) . . . . ?
C12 C13 C14 C19 -3.4(4) . . . . ?
C13 C14 C15 N2 -129.9(3) . . . . ?
C19 C14 C15 N2 52.3(3) . . . . ?
C16 N2 C15 C14 77.5(3) . . . . ?
C21 N2 C15 C14 -44.5(4) . . . . ?
C15 N2 C16 C17 -140.4(2) . . . . ?
C21 N2 C16 C17 -15.0(3) . . . . ?
N2 C16 C17 C7 35.5(3) . . . . ?
C5 C7 C17 C16 -164.6(3) . . . . ?
C21 C7 C17 C16 -41.9(3) . . . . ?
C8 C7 C17 C16 80.8(3) . . . . ?
N1 C8 C18 C11 -71.2(3) . . . . ?
C7 C8 C18 C11 172.3(2) . . . . ?
N1 C8 C18 C19 157.0(2) . . . . ?
C7 C8 C18 C19 40.5(3) . . . . ?
O1 C11 C18 C8 -75.9(3) . . . . ?
C10 C11 C18 C8 42.6(3) . . . . ?
O1 C11 C18 C19 52.6(3) . . . . ?
C10 C11 C18 C19 171.1(2) . . . . ?
C13 C14 C19 C20 -179.4(3) . . . . ?
C15 C14 C19 C20 -1.6(3) . . . . ?
C13 C14 C19 C18 61.3(4) . . . . ?
C15 C14 C19 C18 -120.9(3) . . . . ?
C8 C18 C19 C14 59.5(3) . . . . ?
C11 C18 C19 C14 -66.5(3) . . . . ?
C8 C18 C19 C20 -61.1(3) . . . . ?
C11 C18 C19 C20 172.8(2) . . . . ?
C14 C19 C20 C21 -56.0(3) . . . . ?
C18 C19 C20 C21 68.1(3) . . . . ?
C19 C20 C21 C7 -55.0(3) . . . . ?
C19 C20 C21 N2 62.9(3) . . . . ?
C5 C7 C21 C20 -85.5(3) . . . . ?
C17 C7 C21 C20 153.0(3) . . . . ?
C8 C7 C21 C20 32.4(4) . . . . ?
C5 C7 C21 N2 153.5(2) . . . . ?
C17 C7 C21 N2 32.0(3) . . . . ?
C8 C7 C21 N2 -88.5(3) . . . . ?
C16 N2 C21 C20 -135.4(3) . . . . ?
C15 N2 C21 C20 -10.9(3) . . . . ?
C16 N2 C21 C7 -11.0(3) . . . . ?
C15 N2 C21 C7 113.6(3) . . . . ?
O4 C22 C23 N4 17.5(12) . . . . ?
O3 C22 C23 N4 -164.7(7) . . . . ?
O4 C22 C23 C24 -100.9(8) . . . . ?
O3 C22 C23 C24 76.9(9) . . . . ?
N4 C23 C24 C25 68.5(9) . . . . ?
C22 C23 C24 C25 -168.9(6) . . . . ?
C23 C24 C25 O5 69.4(7) . . . . ?
C23 C24 C25 N3 -110.3(7) . . . . ?
O3A C22A C23A N4 -168(2) . . . . ?
O4A C22A C23A N4 21(4) . . . . ?
O3A C22A C23A C24A 67(4) . . . . ?
O4A C22A C23A C24A -104(3) . . . . ?
N4 C23A C24A C25A 69(3) . . . . ?
C22A C23A C24A C25A -168(3) . . . . ?
C23A C24A C25A O5A 75(2) . . . . ?
C23A C24A C25A N3A -111(2) . . . . ?
C22A C23A N4 C26 85(3) . . . . ?
C24A C23A N4 C26 -147.5(18) . . . . ?
C22A C23A N4 C23 38(11) . . . . ?
C24A C23A N4 C23 165(16) . . . . ?
C24 C23 N4 C26 -171.9(5) . . . . ?
C22 C23 N4 C26 71.3(11) . . . . ?
C24 C23 N4 C23A -34(13) . . . . ?
C22 C23 N4 C23A -150(14) . . . . ?
C23A N4 C26 O6 -8(2) . . . . ?
C23 N4 C26 O6 1.5(7) . . . . ?
C23A N4 C26 C27 172(2) . . . . ?
C23 N4 C26 C27 -178.5(6) . . . . ?
O6 C26 C27 C28 -39.6(4) . . . . ?
N4 C26 C27 C28 140.5(3) . . . . ?
O6 C26 C27 C32 139.3(3) . . . . ?
N4 C26 C27 C32 -40.7(4) . . . . ?
C32 C27 C28 C29 1.3(5) . . . . ?
C26 C27 C28 C29 -179.8(3) . . . . ?
C27 C28 C29 C30 0.9(5) . . . . ?
C27 C28 C29 N5 -178.9(3) . . . . ?
O8 N5 C29 C28 176.4(3) . . . . ?
O7 N5 C29 C28 -3.1(5) . . . . ?
O8 N5 C29 C30 -3.5(5) . . . . ?
O7 N5 C29 C30 177.1(3) . . . . ?
C28 C29 C30 C31 -2.5(5) . . . . ?
N5 C29 C30 C31 177.3(3) . . . . ?
C29 C30 C31 C32 2.1(5) . . . . ?
C29 C30 C31 N6 -177.1(3) . . . . ?
O9 N6 C31 C30 -26.4(5) . . . . ?
O10 N6 C31 C30 154.4(3) . . . . ?
O9 N6 C31 C32 154.4(3) . . . . ?
O10 N6 C31 C32 -24.8(5) . . . . ?
C30 C31 C32 C27 0.0(5) . . . . ?
N6 C31 C32 C27 179.1(3) . . . . ?
C28 C27 C32 C31 -1.7(5) . . . . ?
C26 C27 C32 C31 179.5(3) . . . . ?
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
N2 H22 O3 1.00 1.76 2.682(4) 152.2 .
N2 H22 O3A 1.00 2.03 2.823(12) 134.4 .
N3 H37A O3 0.88 2.00 2.878(5) 177.3 1_455
N3 H37B O4 0.88 2.12 2.859(5) 141.8 4_465
O2W H21W O1W 0.86 1.85 2.676(6) 159.5 1_455
O2W H22W O5 0.86 1.99 2.811(5) 158.8 .
N3A H37C O1W 0.88 2.57 3.416(16) 161.6 1_455
N3A H37C O3A 0.88 2.71 3.152(19) 112.3 1_455
N3A H37D O4A 0.88 2.24 3.02(2) 147.3 4_465
N4 H47 O4 0.88 1.98 2.814(5) 157.8 4_465
O1W H11W O6 0.86 1.93 2.781(4) 171.9 .
O1W H12W O2W 0.86 1.86 2.603(7) 143.2 4
O1W H12W O5A 0.86 2.15 2.986(14) 162.4 4
_refine_diff_density_max 0.260
_refine_diff_density_min -0.281
_refine_diff_density_rms 0.061
_database_code_depnum_ccdc_archive 'CCDC 933059'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_sdnbln(2)
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
strychninium N-(3,5-dinitrobenzoyl)-L-asparaginate 5-hydrate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H23 N2 O2, C11 H9 N4 O8, 5(H2 O)'
_chemical_formula_sum 'C32 H42 N6 O15'
_chemical_formula_weight 750.71
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'
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 7.730(2)
_cell_length_b 11.896(3)
_cell_length_c 37.812(5)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 3477.0(13)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 12658
_cell_measurement_theta_min 3.091
_cell_measurement_theta_max 34.498
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.434
_exptl_crystal_F_000 1584
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.300
_exptl_crystal_size_mid 0.300
_exptl_crystal_size_min 0.300
_exptl_absorpt_coefficient_mu 0.115
_shelx_estimated_absorpt_T_min ?
_shelx_estimated_absorpt_T_max ?
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Sapphire2'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 65220
_diffrn_reflns_av_unetI/netI 0.0541
_diffrn_reflns_av_R_equivalents 0.0553
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -59
_diffrn_reflns_limit_l_max 59
_diffrn_reflns_theta_min 3.091
_diffrn_reflns_theta_max 34.498
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total 14546
_reflns_number_gt 11523
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.787
_reflns_Friedel_fraction_max 0.976
_reflns_Friedel_fraction_full 1.000
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0597P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 4152 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack 0.0(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 14546
_refine_ls_number_parameters 478
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0671
_refine_ls_R_factor_gt 0.0492
_refine_ls_wR_factor_ref 0.1129
_refine_ls_wR_factor_gt 0.1076
_refine_ls_goodness_of_fit_ref 1.038
_refine_ls_restrained_S_all 1.038
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.25972(18) -0.10621(11) 0.17775(4) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.17583(19) -0.04618(13) 0.26283(4) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.14597(19) 0.04598(12) 0.21032(4) 0.0156(3) Uani 1 1 d . . . . .
N2 N -0.0815(2) 0.23599(13) 0.11396(4) 0.0176(3) Uani 1 1 d . . . . .
H22 H -0.0640 0.3041 0.0989 0.021 Uiso 1 1 calc R U . . .
C1 C 0.3687(2) 0.15751(16) 0.24503(5) 0.0186(3) Uani 1 1 d . . . . .
H1 H 0.3855 0.1023 0.2629 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4586(2) 0.25916(16) 0.24564(5) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.5367 0.2738 0.2645 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4365(2) 0.33960(16) 0.21928(5) 0.0180(3) Uani 1 1 d . . . . .
H3 H 0.5010 0.4075 0.2201 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3202(2) 0.32100(15) 0.19171(5) 0.0164(3) Uani 1 1 d . . . . .
H4 H 0.3047 0.3757 0.1737 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2280(2) 0.22131(14) 0.19110(4) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.2528(2) 0.14010(14) 0.21717(4) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.1025(2) 0.17987(14) 0.16340(4) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.0259(2) 0.07196(14) 0.18080(4) 0.0134(3) Uani 1 1 d . . . . .
H8 H 0.0271 0.0089 0.1633 0.016 Uiso 1 1 calc R U . . .
C9 C 0.0961(2) -0.03243(16) 0.23513(5) 0.0196(3) Uani 1 1 d . . . . .
C10 C -0.0615(3) -0.10077(16) 0.22520(5) 0.0217(4) Uani 1 1 d . . . . .
H10A H -0.1067 -0.1367 0.2469 0.026 Uiso 1 1 calc R U . . .
H10B H -0.0239 -0.1617 0.2091 0.026 Uiso 1 1 calc R U . . .
C11 C -0.2117(2) -0.03728(15) 0.20731(5) 0.0175(3) Uani 1 1 d . . . . .
H11 H -0.3113 -0.0326 0.2241 0.021 Uiso 1 1 calc R U . . .
C12 C -0.4133(3) -0.06993(17) 0.15967(6) 0.0230(4) Uani 1 1 d . . . . .
H12A H -0.4933 -0.0349 0.1769 0.028 Uiso 1 1 calc R U . . .
H12B H -0.4722 -0.1361 0.1493 0.028 Uiso 1 1 calc R U . . .
C13 C -0.3732(2) 0.01329(16) 0.13074(5) 0.0202(3) Uani 1 1 d . . . . .
H13 H -0.3935 -0.0071 0.1068 0.024 Uiso 1 1 calc R U . . .
C14 C -0.3099(2) 0.11493(15) 0.13804(5) 0.0166(3) Uani 1 1 d . . . . .
C15 C -0.2666(2) 0.19848(17) 0.10961(5) 0.0191(3) Uani 1 1 d . . . . .
H15A H -0.3449 0.2641 0.1113 0.023 Uiso 1 1 calc R U . . .
H15B H -0.2824 0.1636 0.0861 0.023 Uiso 1 1 calc R U . . .
C16 C 0.0446(2) 0.14747(17) 0.10190(5) 0.0197(3) Uani 1 1 d . . . . .
H16A H 0.0854 0.1632 0.0776 0.024 Uiso 1 1 calc R U . . .
H16B H -0.0095 0.0720 0.1024 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1924(2) 0.15410(16) 0.12792(5) 0.0176(3) Uani 1 1 d . . . . .
H17A H 0.2741 0.2148 0.1214 0.021 Uiso 1 1 calc R U . . .
H17B H 0.2560 0.0820 0.1290 0.021 Uiso 1 1 calc R U . . .
C18 C -0.1543(2) 0.08179(14) 0.19733(4) 0.0139(3) Uani 1 1 d . . . . .
H18 H -0.1373 0.1223 0.2202 0.017 Uiso 1 1 calc R U . . .
C19 C -0.2782(2) 0.15516(15) 0.17565(5) 0.0151(3) Uani 1 1 d . . . . .
H19 H -0.3917 0.1596 0.1883 0.018 Uiso 1 1 calc R U . . .
C20 C -0.1968(2) 0.27222(15) 0.17478(5) 0.0164(3) Uani 1 1 d . . . . .
H20A H -0.2796 0.3269 0.1647 0.020 Uiso 1 1 calc R U . . .
H20B H -0.1675 0.2966 0.1991 0.020 Uiso 1 1 calc R U . . .
C21 C -0.0347(2) 0.26773(14) 0.15232(4) 0.0149(3) Uani 1 1 d . . . . .
H21 H 0.0203 0.3438 0.1523 0.018 Uiso 1 1 calc R U . . .
O3 O 0.63001(19) 1.00290(11) 0.04142(4) 0.0247(3) Uani 1 1 d . . . . .
O4 O 0.81545(19) 1.12650(11) 0.01832(4) 0.0256(3) Uani 1 1 d . . . . .
O5 O 1.13069(19) 0.81195(12) -0.02806(4) 0.0262(3) Uani 1 1 d . . . . .
O6 O 1.12074(18) 0.90716(12) 0.07654(4) 0.0253(3) Uani 1 1 d . . . . .
O7 O 1.3003(2) 0.71506(15) 0.18273(4) 0.0355(4) Uani 1 1 d . . . . .
O8 O 1.1559(2) 0.57496(15) 0.20382(4) 0.0363(4) Uani 1 1 d . . . . .
O9 O 0.5633(2) 0.52294(14) 0.16135(5) 0.0355(4) Uani 1 1 d . . . . .
O10 O 0.4745(2) 0.62331(14) 0.11704(4) 0.0311(3) Uani 1 1 d . . . . .
N3 N 0.9153(2) 0.68894(15) -0.03462(5) 0.0306(4) Uani 1 1 d . . . . .
H37A H 0.9881 0.6347 -0.0400 0.037 Uiso 1 1 calc R U . . .
H37B H 0.8034 0.6755 -0.0340 0.037 Uiso 1 1 calc R U . . .
N4 N 0.8898(2) 0.84499(13) 0.04527(4) 0.0177(3) Uani 1 1 d . . . . .
H47 H 0.8139 0.7903 0.0430 0.021 Uiso 1 1 calc R U . . .
N5 N 1.1768(2) 0.65140(15) 0.18269(4) 0.0239(3) Uani 1 1 d . . . . .
N6 N 0.5868(2) 0.59221(14) 0.13785(5) 0.0236(3) Uani 1 1 d . . . . .
C22 C 0.7699(2) 1.02919(15) 0.02677(5) 0.0183(3) Uani 1 1 d . . . . .
C23 C 0.8968(2) 0.93239(14) 0.01831(5) 0.0169(3) Uani 1 1 d . . . . .
H23 H 1.0171 0.9629 0.0169 0.020 Uiso 1 1 calc R U . . .
C24 C 0.8467(3) 0.88140(15) -0.01764(5) 0.0197(3) Uani 1 1 d . . . . .
H24A H 0.7285 0.8496 -0.0163 0.024 Uiso 1 1 calc R U . . .
H24B H 0.8473 0.9407 -0.0360 0.024 Uiso 1 1 calc R U . . .
C25 C 0.9737(3) 0.78998(15) -0.02747(5) 0.0196(3) Uani 1 1 d . . . . .
C26 C 0.9949(2) 0.84490(15) 0.07348(5) 0.0167(3) Uani 1 1 d . . . . .
C27 C 0.9526(2) 0.76229(14) 0.10257(5) 0.0160(3) Uani 1 1 d . . . . .
C28 C 1.0797(2) 0.74107(15) 0.12771(5) 0.0179(3) Uani 1 1 d . . . . .
H28 H 1.1902 0.7755 0.1259 0.021 Uiso 1 1 calc R U . . .
C29 C 1.0429(2) 0.66912(15) 0.15546(5) 0.0183(3) Uani 1 1 d . . . . .
C30 C 0.8840(2) 0.61629(16) 0.15985(5) 0.0197(3) Uani 1 1 d . . . . .
H30 H 0.8618 0.5662 0.1789 0.024 Uiso 1 1 calc R U . . .
C31 C 0.7600(2) 0.64171(15) 0.13460(5) 0.0187(3) Uani 1 1 d . . . . .
C32 C 0.7897(2) 0.71322(15) 0.10621(5) 0.0172(3) Uani 1 1 d . . . . .
H32 H 0.7006 0.7285 0.0896 0.021 Uiso 1 1 calc R U . . .
O1W O 0.7278(2) 0.47759(15) 0.05394(5) 0.0417(4) Uani 1 1 d . . . . .
H11W H 0.6920 0.5381 0.0439 0.062 Uiso 1 1 d R U . . .
H12W H 0.7261 0.4241 0.0387 0.062 Uiso 1 1 d R U . . .
O2W O 0.3841(2) 0.38553(14) 0.07957(4) 0.0372(4) Uani 1 1 d . . . . .
H21W H 0.3764 0.3289 0.0655 0.056 Uiso 1 1 d R U . . .
H22W H 0.4846 0.4155 0.0770 0.056 Uiso 1 1 d R U . . .
O3W O 0.0343(3) 0.43633(14) 0.08939(4) 0.0373(4) Uani 1 1 d . . . . .
H31W H 0.1404 0.4385 0.0826 0.056 Uiso 1 1 d R U . . .
H32W H -0.0311 0.4466 0.0713 0.056 Uiso 1 1 d R U . . .
O4W O 0.1503(2) 0.17501(12) -0.00241(4) 0.0270(3) Uani 1 1 d . . . . .
H41W H 0.1633 0.2420 -0.0105 0.040 Uiso 1 1 d R U . . .
H42W H 0.0441 0.1668 0.0039 0.040 Uiso 1 1 d R U . . .
O5W O 0.39357(19) 0.17415(12) 0.05176(4) 0.0261(3) Uani 1 1 d . . . . .
H51W H 0.3182 0.1626 0.0354 0.039 Uiso 1 1 d R U . . .
H52W H 0.4700 0.1217 0.0507 0.039 Uiso 1 1 d R U . . .
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
O1 0.0195(6) 0.0153(6) 0.0278(7) -0.0019(5) -0.0002(5) -0.0022(5)
O2 0.0245(7) 0.0291(8) 0.0285(7) 0.0141(6) -0.0040(6) -0.0007(6)
N1 0.0143(6) 0.0160(7) 0.0164(7) 0.0035(5) 0.0002(5) 0.0011(5)
N2 0.0173(7) 0.0196(7) 0.0159(7) 0.0023(5) -0.0011(5) 0.0003(6)
C1 0.0164(7) 0.0233(9) 0.0162(8) 0.0022(6) -0.0004(6) 0.0042(7)
C2 0.0146(8) 0.0263(9) 0.0176(8) -0.0038(6) -0.0008(6) 0.0024(7)
C3 0.0132(7) 0.0188(8) 0.0220(8) -0.0049(6) 0.0018(6) -0.0007(6)
C4 0.0146(7) 0.0169(8) 0.0176(8) -0.0006(6) 0.0016(6) 0.0000(6)
C5 0.0120(7) 0.0151(8) 0.0149(7) 0.0004(5) 0.0013(6) 0.0008(6)
C6 0.0120(7) 0.0163(8) 0.0162(8) 0.0015(5) 0.0019(6) 0.0028(6)
C7 0.0129(7) 0.0145(7) 0.0140(7) 0.0015(5) 0.0007(6) 0.0003(6)
C8 0.0118(7) 0.0132(7) 0.0154(7) 0.0007(5) 0.0017(6) 0.0013(6)
C9 0.0187(8) 0.0162(8) 0.0238(9) 0.0062(6) 0.0037(7) 0.0021(6)
C10 0.0234(9) 0.0148(8) 0.0270(9) 0.0056(6) 0.0023(7) 0.0000(7)
C11 0.0157(7) 0.0159(8) 0.0208(8) 0.0014(6) 0.0023(6) -0.0017(6)
C12 0.0181(8) 0.0198(9) 0.0313(10) -0.0017(7) -0.0020(7) -0.0051(7)
C13 0.0161(8) 0.0223(9) 0.0222(9) -0.0042(6) -0.0013(7) -0.0002(7)
C14 0.0127(7) 0.0198(8) 0.0174(8) -0.0010(6) -0.0014(6) 0.0020(6)
C15 0.0153(8) 0.0233(9) 0.0188(8) 0.0000(6) -0.0028(6) -0.0006(7)
C16 0.0175(8) 0.0252(9) 0.0164(8) -0.0029(6) 0.0010(7) 0.0031(7)
C17 0.0142(7) 0.0226(8) 0.0161(8) 0.0011(6) 0.0021(6) -0.0004(7)
C18 0.0125(7) 0.0127(7) 0.0165(8) 0.0003(5) 0.0016(6) -0.0002(6)
C19 0.0125(7) 0.0147(7) 0.0182(8) -0.0012(6) 0.0017(6) 0.0009(6)
C20 0.0150(7) 0.0137(8) 0.0206(8) -0.0005(6) 0.0000(6) 0.0018(6)
C21 0.0163(7) 0.0127(7) 0.0155(7) 0.0014(5) -0.0014(6) 0.0009(6)
O3 0.0242(7) 0.0163(6) 0.0335(8) -0.0028(5) 0.0074(6) 0.0007(5)
O4 0.0261(7) 0.0140(6) 0.0367(8) 0.0037(5) 0.0038(6) 0.0021(5)
O5 0.0257(7) 0.0180(6) 0.0348(8) -0.0033(5) 0.0089(6) 0.0016(5)
O6 0.0199(6) 0.0257(7) 0.0302(7) 0.0077(5) -0.0032(6) -0.0054(6)
O7 0.0324(9) 0.0428(10) 0.0314(8) 0.0037(7) -0.0136(7) -0.0084(7)
O8 0.0350(9) 0.0402(9) 0.0338(8) 0.0178(7) -0.0073(7) 0.0037(7)
O9 0.0293(8) 0.0314(9) 0.0458(10) 0.0195(7) 0.0012(7) -0.0054(7)
O10 0.0221(7) 0.0334(8) 0.0377(9) 0.0096(6) -0.0047(6) -0.0037(6)
N3 0.0270(9) 0.0179(8) 0.0468(11) -0.0071(7) -0.0094(8) 0.0026(7)
N4 0.0226(7) 0.0124(7) 0.0182(7) 0.0025(5) -0.0029(6) -0.0027(6)
N5 0.0250(8) 0.0264(8) 0.0203(8) -0.0004(6) -0.0034(6) 0.0039(7)
N6 0.0208(8) 0.0202(8) 0.0299(9) 0.0053(6) 0.0006(7) -0.0024(6)
C22 0.0215(8) 0.0145(8) 0.0189(8) -0.0010(6) -0.0017(7) 0.0018(6)
C23 0.0206(8) 0.0121(7) 0.0179(8) 0.0022(5) 0.0005(6) 0.0015(6)
C24 0.0241(9) 0.0167(8) 0.0183(8) 0.0009(6) -0.0019(7) 0.0020(7)
C25 0.0279(9) 0.0161(8) 0.0148(8) 0.0005(6) -0.0002(7) 0.0037(7)
C26 0.0174(8) 0.0144(8) 0.0185(8) 0.0008(6) 0.0012(6) 0.0029(6)
C27 0.0189(8) 0.0133(7) 0.0158(8) -0.0008(5) 0.0007(6) 0.0014(6)
C28 0.0169(8) 0.0173(8) 0.0195(8) -0.0010(6) -0.0004(6) 0.0009(6)
C29 0.0204(8) 0.0169(8) 0.0176(8) 0.0003(6) -0.0019(7) 0.0045(7)
C30 0.0230(8) 0.0167(8) 0.0193(8) 0.0011(6) 0.0006(7) 0.0028(7)
C31 0.0190(8) 0.0133(8) 0.0239(9) 0.0011(6) 0.0000(7) 0.0005(6)
C32 0.0177(8) 0.0152(8) 0.0187(8) 0.0005(6) -0.0010(6) 0.0014(6)
O1W 0.0467(10) 0.0260(9) 0.0523(11) -0.0027(7) -0.0141(9) 0.0047(8)
O2W 0.0491(10) 0.0238(8) 0.0387(9) -0.0027(6) 0.0054(8) 0.0002(7)
O3W 0.0435(10) 0.0321(9) 0.0363(9) 0.0123(7) 0.0001(8) 0.0002(8)
O4W 0.0250(7) 0.0182(7) 0.0377(8) 0.0059(6) -0.0025(6) -0.0022(5)
O5W 0.0255(7) 0.0248(7) 0.0279(7) -0.0037(5) -0.0005(6) 0.0054(6)
_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
O1 C11 1.435(2) . ?
O1 C12 1.436(2) . ?
O2 C9 1.226(2) . ?
N1 C9 1.378(2) . ?
N1 C6 1.415(2) . ?
N1 C8 1.484(2) . ?
N2 C16 1.506(2) . ?
N2 C15 1.508(2) . ?
N2 C21 1.542(2) . ?
N2 H22 1.0000 . ?
C1 C2 1.395(3) . ?
C1 C6 1.398(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 C7 1.510(2) . ?
C7 C17 1.542(2) . ?
C7 C21 1.547(2) . ?
C7 C8 1.559(2) . ?
C8 C18 1.531(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.512(3) . ?
C10 C11 1.542(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.532(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.333(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.502(3) . ?
C14 C19 1.520(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.534(2) . ?
C18 H18 1.0000 . ?
C19 C20 1.529(2) . ?
C19 H19 1.0000 . ?
C20 C21 1.515(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
O3 C22 1.255(2) . ?
O4 C22 1.251(2) . ?
O5 C25 1.241(3) . ?
O6 C26 1.228(2) . ?
O7 N5 1.219(2) . ?
O8 N5 1.221(2) . ?
O9 N6 1.225(2) . ?
O10 N6 1.229(2) . ?
N3 C25 1.312(3) . ?
N3 H37A 0.8800 . ?
N3 H37B 0.8800 . ?
N4 C26 1.341(2) . ?
N4 C23 1.457(2) . ?
N4 H47 0.8800 . ?
N5 C29 1.475(2) . ?
N6 C31 1.468(3) . ?
C22 C23 1.546(3) . ?
C23 C24 1.538(3) . ?
C23 H23 1.0000 . ?
C24 C25 1.512(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C26 C27 1.511(2) . ?
C27 C28 1.390(3) . ?
C27 C32 1.395(3) . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(3) . ?
C30 C31 1.386(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(3) . ?
C32 H32 0.9500 . ?
O1W H11W 0.8600 . ?
O1W H12W 0.8599 . ?
O2W H21W 0.8600 . ?
O2W H22W 0.8599 . ?
O3W H31W 0.8600 . ?
O3W H32W 0.8601 . ?
O4W H41W 0.8599 . ?
O4W H42W 0.8600 . ?
O5W H51W 0.8598 . ?
O5W H52W 0.8599 . ?
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
C11 O1 C12 114.38(14) . . ?
C9 N1 C6 125.05(15) . . ?
C9 N1 C8 118.57(15) . . ?
C6 N1 C8 109.74(13) . . ?
C16 N2 C15 111.99(15) . . ?
C16 N2 C21 107.70(13) . . ?
C15 N2 C21 113.46(14) . . ?
C16 N2 H22 107.8 . . ?
C15 N2 H22 107.8 . . ?
C21 N2 H22 107.8 . . ?
C2 C1 C6 117.39(16) . . ?
C2 C1 H1 121.3 . . ?
C6 C1 H1 121.3 . . ?
C3 C2 C1 121.53(17) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.36(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.72(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.75(16) . . ?
C4 C5 C7 128.48(15) . . ?
C6 C5 C7 110.65(15) . . ?
C5 C6 C1 121.24(16) . . ?
C5 C6 N1 109.79(15) . . ?
C1 C6 N1 128.97(16) . . ?
C5 C7 C17 112.25(14) . . ?
C5 C7 C21 114.06(14) . . ?
C17 C7 C21 101.98(13) . . ?
C5 C7 C8 102.70(13) . . ?
C17 C7 C8 112.00(14) . . ?
C21 C7 C8 114.25(14) . . ?
N1 C8 C18 106.12(13) . . ?
N1 C8 C7 104.58(13) . . ?
C18 C8 C7 117.04(14) . . ?
N1 C8 H8 109.6 . . ?
C18 C8 H8 109.6 . . ?
C7 C8 H8 109.6 . . ?
O2 C9 N1 122.10(18) . . ?
O2 C9 C10 123.04(16) . . ?
N1 C9 C10 114.85(16) . . ?
C9 C10 C11 116.91(15) . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 114.31(14) . . ?
O1 C11 C10 104.86(15) . . ?
C18 C11 C10 110.04(15) . . ?
O1 C11 H11 109.2 . . ?
C18 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
O1 C12 C13 111.90(15) . . ?
O1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 121.38(17) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 122.26(17) . . ?
C13 C14 C19 122.57(17) . . ?
C15 C14 C19 115.17(15) . . ?
C14 C15 N2 109.22(14) . . ?
C14 C15 H15A 109.8 . . ?
N2 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
N2 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C17 104.84(14) . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.67(14) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 107.08(14) . . ?
C8 C18 C19 113.18(14) . . ?
C11 C18 C19 118.48(14) . . ?
C8 C18 H18 105.7 . . ?
C11 C18 H18 105.7 . . ?
C19 C18 H18 105.7 . . ?
C14 C19 C20 109.45(15) . . ?
C14 C19 C18 114.93(14) . . ?
C20 C19 C18 105.82(14) . . ?
C14 C19 H19 108.8 . . ?
C20 C19 H19 108.8 . . ?
C18 C19 H19 108.8 . . ?
C21 C20 C19 108.70(14) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 109.98(14) . . ?
C20 C21 C7 116.04(14) . . ?
N2 C21 C7 104.50(13) . . ?
C20 C21 H21 108.7 . . ?
N2 C21 H21 108.7 . . ?
C7 C21 H21 108.7 . . ?
C25 N3 H37A 120.0 . . ?
C25 N3 H37B 120.0 . . ?
H37A N3 H37B 120.0 . . ?
C26 N4 C23 122.32(15) . . ?
C26 N4 H47 118.8 . . ?
C23 N4 H47 118.8 . . ?
O7 N5 O8 124.44(18) . . ?
O7 N5 C29 117.52(17) . . ?
O8 N5 C29 118.03(17) . . ?
O9 N6 O10 124.20(17) . . ?
O9 N6 C31 117.76(16) . . ?
O10 N6 C31 118.04(16) . . ?
O4 C22 O3 125.85(17) . . ?
O4 C22 C23 117.24(16) . . ?
O3 C22 C23 116.91(16) . . ?
N4 C23 C24 109.13(14) . . ?
N4 C23 C22 111.29(15) . . ?
C24 C23 C22 108.49(15) . . ?
N4 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
C22 C23 H23 109.3 . . ?
C25 C24 C23 109.73(15) . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
O5 C25 N3 121.70(18) . . ?
O5 C25 C24 119.20(17) . . ?
N3 C25 C24 119.10(19) . . ?
O6 C26 N4 123.68(17) . . ?
O6 C26 C27 119.67(16) . . ?
N4 C26 C27 116.66(15) . . ?
C28 C27 C32 119.64(16) . . ?
C28 C27 C26 117.59(16) . . ?
C32 C27 C26 122.64(16) . . ?
C29 C28 C27 119.06(17) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 123.50(17) . . ?
C28 C29 N5 118.26(17) . . ?
C30 C29 N5 118.19(16) . . ?
C31 C30 C29 115.47(17) . . ?
C31 C30 H30 122.3 . . ?
C29 C30 H30 122.3 . . ?
C30 C31 C32 123.51(17) . . ?
C30 C31 N6 119.04(16) . . ?
C32 C31 N6 117.45(16) . . ?
C31 C32 C27 118.80(17) . . ?
C31 C32 H32 120.6 . . ?
C27 C32 H32 120.6 . . ?
H11W O1W H12W 108.6 . . ?
H21W O2W H22W 108.6 . . ?
H31W O3W H32W 108.5 . . ?
H41W O4W H42W 108.4 . . ?
H51W O5W H52W 108.5 . . ?
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
C6 C1 C2 C3 -1.0(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 C7 -176.78(16) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C7 C5 C6 C1 177.63(15) . . . . ?
C4 C5 C6 N1 -179.08(15) . . . . ?
C7 C5 C6 N1 -2.71(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 N1 -179.75(17) . . . . ?
C9 N1 C6 C5 -158.75(16) . . . . ?
C8 N1 C6 C5 -8.02(19) . . . . ?
C9 N1 C6 C1 20.9(3) . . . . ?
C8 N1 C6 C1 171.60(17) . . . . ?
C4 C5 C7 C17 67.0(2) . . . . ?
C6 C5 C7 C17 -109.00(16) . . . . ?
C4 C5 C7 C21 -48.4(2) . . . . ?
C6 C5 C7 C21 135.64(15) . . . . ?
C4 C5 C7 C8 -172.53(17) . . . . ?
C6 C5 C7 C8 11.46(18) . . . . ?
C9 N1 C8 C18 43.4(2) . . . . ?
C6 N1 C8 C18 -109.52(15) . . . . ?
C9 N1 C8 C7 167.71(15) . . . . ?
C6 N1 C8 C7 14.82(17) . . . . ?
C5 C7 C8 N1 -15.33(16) . . . . ?
C17 C7 C8 N1 105.31(15) . . . . ?
C21 C7 C8 N1 -139.38(14) . . . . ?
C5 C7 C8 C18 101.72(16) . . . . ?
C17 C7 C8 C18 -137.63(15) . . . . ?
C21 C7 C8 C18 -22.3(2) . . . . ?
C6 N1 C9 O2 -20.6(3) . . . . ?
C8 N1 C9 O2 -169.00(17) . . . . ?
C6 N1 C9 C10 160.38(16) . . . . ?
C8 N1 C9 C10 12.0(2) . . . . ?
O2 C9 C10 C11 139.91(19) . . . . ?
N1 C9 C10 C11 -41.1(2) . . . . ?
C12 O1 C11 C18 -66.92(19) . . . . ?
C12 O1 C11 C10 172.48(14) . . . . ?
C9 C10 C11 O1 133.46(16) . . . . ?
C9 C10 C11 C18 10.1(2) . . . . ?
C11 O1 C12 C13 88.84(19) . . . . ?
O1 C12 C13 C14 -65.9(2) . . . . ?
C12 C13 C14 C15 179.07(17) . . . . ?
C12 C13 C14 C19 -1.6(3) . . . . ?
C13 C14 C15 N2 -125.49(18) . . . . ?
C19 C14 C15 N2 55.2(2) . . . . ?
C16 N2 C15 C14 75.12(18) . . . . ?
C21 N2 C15 C14 -47.07(19) . . . . ?
C15 N2 C16 C17 -142.25(15) . . . . ?
C21 N2 C16 C17 -16.84(18) . . . . ?
N2 C16 C17 C7 36.50(18) . . . . ?
C5 C7 C17 C16 -164.24(15) . . . . ?
C21 C7 C17 C16 -41.76(17) . . . . ?
C8 C7 C17 C16 80.83(17) . . . . ?
N1 C8 C18 C11 -72.37(16) . . . . ?
C7 C8 C18 C11 171.42(14) . . . . ?
N1 C8 C18 C19 155.24(14) . . . . ?
C7 C8 C18 C19 39.0(2) . . . . ?
O1 C11 C18 C8 -73.51(17) . . . . ?
C10 C11 C18 C8 44.15(19) . . . . ?
O1 C11 C18 C19 55.9(2) . . . . ?
C10 C11 C18 C19 173.59(15) . . . . ?
C13 C14 C19 C20 177.06(17) . . . . ?
C15 C14 C19 C20 -3.6(2) . . . . ?
C13 C14 C19 C18 58.2(2) . . . . ?
C15 C14 C19 C18 -122.48(16) . . . . ?
C8 C18 C19 C14 59.34(19) . . . . ?
C11 C18 C19 C14 -67.2(2) . . . . ?
C8 C18 C19 C20 -61.56(18) . . . . ?
C11 C18 C19 C20 171.87(14) . . . . ?
C14 C19 C20 C21 -55.26(18) . . . . ?
C18 C19 C20 C21 69.13(17) . . . . ?
C19 C20 C21 N2 62.64(17) . . . . ?
C19 C20 C21 C7 -55.67(19) . . . . ?
C16 N2 C21 C20 -134.39(15) . . . . ?
C15 N2 C21 C20 -9.9(2) . . . . ?
C16 N2 C21 C7 -9.18(17) . . . . ?
C15 N2 C21 C7 115.36(16) . . . . ?
C5 C7 C21 C20 -86.66(18) . . . . ?
C17 C7 C21 C20 152.09(15) . . . . ?
C8 C7 C21 C20 31.1(2) . . . . ?
C5 C7 C21 N2 152.06(14) . . . . ?
C17 C7 C21 N2 30.82(16) . . . . ?
C8 C7 C21 N2 -90.22(16) . . . . ?
C26 N4 C23 C24 148.40(17) . . . . ?
C26 N4 C23 C22 -91.9(2) . . . . ?
O4 C22 C23 N4 145.51(17) . . . . ?
O3 C22 C23 N4 -34.7(2) . . . . ?
O4 C22 C23 C24 -94.4(2) . . . . ?
O3 C22 C23 C24 85.36(19) . . . . ?
N4 C23 C24 C25 -61.2(2) . . . . ?
C22 C23 C24 C25 177.35(15) . . . . ?
C23 C24 C25 O5 -54.5(2) . . . . ?
C23 C24 C25 N3 124.50(19) . . . . ?
C23 N4 C26 O6 -11.1(3) . . . . ?
C23 N4 C26 C27 169.13(15) . . . . ?
O6 C26 C27 C28 -15.0(2) . . . . ?
N4 C26 C27 C28 164.85(16) . . . . ?
O6 C26 C27 C32 160.87(17) . . . . ?
N4 C26 C27 C32 -19.3(3) . . . . ?
C32 C27 C28 C29 1.6(3) . . . . ?
C26 C27 C28 C29 177.57(16) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C27 C28 C29 N5 -177.44(16) . . . . ?
O7 N5 C29 C28 12.4(3) . . . . ?
O8 N5 C29 C28 -168.35(18) . . . . ?
O7 N5 C29 C30 -165.01(18) . . . . ?
O8 N5 C29 C30 14.3(3) . . . . ?
C28 C29 C30 C31 -1.1(3) . . . . ?
N5 C29 C30 C31 176.14(16) . . . . ?
C29 C30 C31 C32 1.1(3) . . . . ?
C29 C30 C31 N6 -178.15(16) . . . . ?
O9 N6 C31 C30 -5.8(3) . . . . ?
O10 N6 C31 C30 173.75(18) . . . . ?
O9 N6 C31 C32 174.95(18) . . . . ?
O10 N6 C31 C32 -5.5(3) . . . . ?
C30 C31 C32 C27 0.2(3) . . . . ?
N6 C31 C32 C27 179.48(16) . . . . ?
C28 C27 C32 C31 -1.6(3) . . . . ?
C26 C27 C32 C31 -177.36(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
N2 H22 O3W 1.00 1.78 2.710(2) 152.5 .
N3 H37A O3 0.88 1.97 2.833(2) 166.2 4_565
N3 H37B O6 0.88 2.35 3.001(2) 130.4 4_465
N4 H47 O5 0.88 1.95 2.814(2) 166.8 4_465
O1W H11W O5 0.86 1.94 2.791(2) 170.0 4_465
O1W H12W O4W 0.86 1.90 2.730(2) 161.6 4
O2W H21W O5W 0.86 1.92 2.727(2) 156.1 .
O2W H22W O1W 0.86 2.20 3.033(3) 162.7 .
O3W H31W O2W 0.86 1.99 2.795(3) 155.5 .
O3W H32W O1W 0.86 2.01 2.766(3) 146.2 1_455
O4W H41W O4 0.86 1.98 2.751(2) 148.7 4_465
O4W H42W O4 0.86 1.91 2.765(2) 172.0 1_445
O5W H51W O4W 0.86 1.94 2.780(2) 166.3 .
O5W H52W O3 0.86 1.91 2.765(2) 171.6 1_545
_refine_diff_density_max 0.390
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.053
_database_code_depnum_ccdc_archive 'CCDC 933060'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_bdnbdn(1)
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
brucinium N-(3,5-dinitrobenzoyl)-D-asparaginate ethanol solvate hydrate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C23 H27 N2 O4, C11 H9 N4 O8, C2 H6 O, H2 O'
_chemical_formula_sum 'C36 H44 N6 O14'
_chemical_formula_weight 784.77
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'
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 21'
_space_group_name_Hall 'P 2yb'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 12.358(3)
_cell_length_b 8.354(2)
_cell_length_c 18.078(2)
_cell_angle_alpha 90
_cell_angle_beta 101.94(3)
_cell_angle_gamma 90
_cell_volume 1826.0(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 4526
_cell_measurement_theta_min 3.304
_cell_measurement_theta_max 26.978
_exptl_crystal_description plate
_exptl_crystal_colour orange
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.427
_exptl_crystal_F_000 828
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.300
_exptl_crystal_size_mid 0.300
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 0.111
_shelx_estimated_absorpt_T_min ?
_shelx_estimated_absorpt_T_max ?
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Sapphire2'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 13073
_diffrn_reflns_av_unetI/netI 0.1205
_diffrn_reflns_av_R_equivalents 0.0819
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 3.304
_diffrn_reflns_theta_max 26.978
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 0.868
_reflns_number_total 6811
_reflns_number_gt 4307
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.614
_reflns_Friedel_fraction_max 0.700
_reflns_Friedel_fraction_full 0.723
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.1140P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details
;
Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack -3.3(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 6811
_refine_ls_number_parameters 516
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1125
_refine_ls_R_factor_gt 0.0766
_refine_ls_wR_factor_ref 0.2120
_refine_ls_wR_factor_gt 0.1959
_refine_ls_goodness_of_fit_ref 1.037
_refine_ls_restrained_S_all 1.037
_refine_ls_shift/su_max 0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2812(4) 0.9649(6) 0.8685(3) 0.0334(13) Uani 1 1 d . . . . .
O2 O 0.3843(4) 1.3804(6) 0.9620(3) 0.0324(12) Uani 1 1 d . . . . .
O3 O 0.3031(4) 1.6293(6) 0.8872(3) 0.0324(12) Uani 1 1 d . . . . .
O4 O 0.1012(4) 0.9452(6) 0.9691(3) 0.0311(12) Uani 1 1 d . . . . .
N1 N 0.0224(4) 1.1092(7) 0.8739(3) 0.0229(13) Uani 1 1 d . . . . .
N2 N -0.2181(4) 1.4279(7) 0.7108(3) 0.0210(12) Uani 1 1 d . . . . .
H22 H -0.2224 1.5227 0.6765 0.025 Uiso 1 1 calc R U . . .
C1 C 0.2096(5) 1.2300(8) 0.9224(4) 0.0262(16) Uani 1 1 d . . . . .
H1 H 0.2370 1.1389 0.9519 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2755(6) 1.3665(9) 0.9230(4) 0.0289(16) Uani 1 1 d . . . . .
C3 C 0.2344(6) 1.5030(9) 0.8813(4) 0.0305(17) Uani 1 1 d . . . . .
C4 C 0.1250(5) 1.5007(8) 0.8372(4) 0.0213(14) Uani 1 1 d . . . . .
H4 H 0.0948 1.5923 0.8093 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0634(6) 1.3614(8) 0.8359(4) 0.0239(15) Uani 1 1 d . . . . .
C6 C 0.1041(5) 1.2299(8) 0.8784(4) 0.0236(15) Uani 1 1 d . . . . .
C7 C -0.0514(5) 1.3241(8) 0.7900(4) 0.0218(15) Uani 1 1 d . . . . .
C8 C -0.0853(5) 1.1743(8) 0.8306(4) 0.0251(15) Uani 1 1 d . . . . .
H8 H -0.1221 1.0941 0.7925 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0187(6) 0.9927(9) 0.9242(4) 0.0264(16) Uani 1 1 d . . . . .
C10 C -0.0930(6) 0.9191(9) 0.9198(4) 0.0323(18) Uani 1 1 d . . . . .
H10A H -0.0899 0.8496 0.9645 0.039 Uiso 1 1 calc R U . . .
H10B H -0.1099 0.8499 0.8744 0.039 Uiso 1 1 calc R U . . .
C11 C -0.1892(6) 1.0414(9) 0.9161(4) 0.0298(17) Uani 1 1 d . . . . .
H11 H -0.2052 1.0534 0.9678 0.036 Uiso 1 1 calc R U . . .
C12 C -0.3855(6) 1.0551(10) 0.8555(4) 0.0348(18) Uani 1 1 d . . . . .
H12A H -0.4487 0.9798 0.8469 0.042 Uiso 1 1 calc R U . . .
H12B H -0.3890 1.1203 0.9007 0.042 Uiso 1 1 calc R U . . .
C13 C -0.3928(6) 1.1593(9) 0.7898(4) 0.0311(17) Uani 1 1 d . . . . .
H13 H -0.4444 1.1355 0.7444 0.037 Uiso 1 1 calc R U . . .
C14 C -0.3275(5) 1.2882(8) 0.7929(4) 0.0246(15) Uani 1 1 d . . . . .
C15 C -0.3336(5) 1.3988(10) 0.7255(4) 0.0295(17) Uani 1 1 d . . . . .
H15A H -0.3671 1.5021 0.7356 0.035 Uiso 1 1 calc R U . . .
H15B H -0.3809 1.3501 0.6802 0.035 Uiso 1 1 calc R U . . .
C16 C -0.1753(5) 1.2898(9) 0.6726(4) 0.0265(16) Uani 1 1 d . . . . .
H16A H -0.1888 1.3063 0.6172 0.032 Uiso 1 1 calc R U . . .
H16B H -0.2109 1.1885 0.6831 0.032 Uiso 1 1 calc R U . . .
C17 C -0.0523(6) 1.2875(9) 0.7067(4) 0.0276(16) Uani 1 1 d . . . . .
H17A H -0.0124 1.3706 0.6839 0.033 Uiso 1 1 calc R U . . .
H17B H -0.0194 1.1815 0.7007 0.033 Uiso 1 1 calc R U . . .
C18 C -0.1568(5) 1.2054(8) 0.8891(4) 0.0235(15) Uani 1 1 d . . . . .
H18 H -0.1053 1.2527 0.9338 0.028 Uiso 1 1 calc R U . . .
C19 C -0.2447(5) 1.3338(8) 0.8635(4) 0.0236(15) Uani 1 1 d . . . . .
H19 H -0.2855 1.3519 0.9051 0.028 Uiso 1 1 calc R U . . .
C20 C -0.1876(5) 1.4875(8) 0.8503(4) 0.0241(15) Uani 1 1 d . . . . .
H20A H -0.1324 1.5164 0.8963 0.029 Uiso 1 1 calc R U . . .
H20B H -0.2425 1.5752 0.8393 0.029 Uiso 1 1 calc R U . . .
C21 C -0.1306(5) 1.4659(8) 0.7841(4) 0.0221(14) Uani 1 1 d . . . . .
H21 H -0.0904 1.5665 0.7766 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4284(6) 1.2434(11) 1.0064(5) 0.040(2) Uani 1 1 d . . . . .
H22A H 0.5055 1.2643 1.0311 0.060 Uiso 1 1 calc R U . . .
H22B H 0.4252 1.1497 0.9734 0.060 Uiso 1 1 calc R U . . .
H22C H 0.3847 1.2229 1.0448 0.060 Uiso 1 1 calc R U . . .
C23 C 0.2582(6) 1.7768(9) 0.8495(5) 0.0369(19) Uani 1 1 d . . . . .
H23A H 0.3156 1.8597 0.8576 0.055 Uiso 1 1 calc R U . . .
H23B H 0.1953 1.8128 0.8704 0.055 Uiso 1 1 calc R U . . .
H23C H 0.2338 1.7570 0.7952 0.055 Uiso 1 1 calc R U . . .
O5 O -0.1865(5) 1.6548(7) 0.6147(3) 0.0382(13) Uani 1 1 d . . . . .
O6 O -0.1092(5) 1.8146(7) 0.7101(3) 0.0411(14) Uani 1 1 d . . . . .
O7 O 0.0571(5) 2.1249(6) 0.5541(3) 0.0395(14) Uani 1 1 d . . . . .
O8 O -0.2357(4) 2.1154(6) 0.5087(3) 0.0365(13) Uani 1 1 d . . . . .
O9 O -0.2267(4) 1.5663(7) 0.2691(3) 0.0474(16) Uani 1 1 d . . . . .
O10 O -0.3670(4) 1.6320(7) 0.1825(3) 0.0362(13) Uani 1 1 d . . . . .
O11 O -0.5205(4) 2.1688(7) 0.1863(3) 0.0400(14) Uani 1 1 d . . . . .
O12 O -0.4383(4) 2.3324(7) 0.2730(3) 0.0434(15) Uani 1 1 d . . . . .
N3 N -0.1430(5) 1.8800(7) 0.5103(3) 0.0308(15) Uani 1 1 d . . . . .
H3 H -0.1299 1.7968 0.4837 0.037 Uiso 1 1 calc R U . . .
N4 N 0.1609(6) 1.9409(9) 0.5145(4) 0.0464(18) Uani 1 1 d . . . . .
H4A H 0.1914 2.0131 0.4898 0.056 Uiso 1 1 calc R U . . .
H4B H 0.1808 1.8398 0.5137 0.056 Uiso 1 1 calc R U . . .
N5 N -0.3024(5) 1.6602(8) 0.2420(3) 0.0328(15) Uani 1 1 d . . . . .
N6 N -0.4543(5) 2.2007(8) 0.2450(4) 0.0298(14) Uani 1 1 d . . . . .
C24 C -0.1327(7) 1.7795(10) 0.6419(5) 0.041(2) Uani 1 1 d . . . . .
C25 C -0.0873(7) 1.8901(9) 0.5892(4) 0.0339(18) Uani 1 1 d . . . . .
H25 H -0.0954 2.0024 0.6064 0.041 Uiso 1 1 calc R U . . .
C26 C 0.0346(7) 1.8585(9) 0.5958(4) 0.038(2) Uani 1 1 d . . . . .
H26A H 0.0450 1.7508 0.5755 0.046 Uiso 1 1 calc R U . . .
H26B H 0.0723 1.8605 0.6498 0.046 Uiso 1 1 calc R U . . .
C27 C 0.0858(7) 1.9839(10) 0.5525(4) 0.0377(19) Uani 1 1 d . . . . .
C28 C -0.2129(6) 1.9911(9) 0.4768(4) 0.0326(18) Uani 1 1 d . . . . .
C29 C -0.2658(6) 1.9632(9) 0.3944(4) 0.0304(17) Uani 1 1 d . . . . .
C30 C -0.2568(5) 1.8231(9) 0.3553(4) 0.0288(17) Uani 1 1 d . . . . .
H30 H -0.2119 1.7379 0.3792 0.035 Uiso 1 1 calc R U . . .
C31 C -0.3136(5) 1.8074(9) 0.2808(4) 0.0252(15) Uani 1 1 d . . . . .
C32 C -0.3803(5) 1.9279(9) 0.2438(4) 0.0292(17) Uani 1 1 d . . . . .
H32 H -0.4201 1.9157 0.1932 0.035 Uiso 1 1 calc R U . . .
C33 C -0.3862(5) 2.0671(9) 0.2841(4) 0.0254(16) Uani 1 1 d . . . . .
C34 C -0.3339(5) 2.0890(9) 0.3576(4) 0.0257(16) Uani 1 1 d . . . . .
H34 H -0.3428 2.1856 0.3835 0.031 Uiso 1 1 calc R U . . .
O35 O -0.5581(9) 1.2795(14) 0.4039(7) 0.067(4) Uani 0.621(16) 1 d . . P A 1
H35 H -0.5974 1.2913 0.3617 0.100 Uiso 0.6208 1 d . U P A 1
O351 O -0.3746(12) 1.4872(16) 0.5449(8) 0.039(5) Uani 0.379(16) 1 d . . P A 2
H351 H -0.3691 1.5670 0.5159 0.058 Uiso 0.379(16) 1 d R U P A 2
C35 C -0.5213(9) 1.4433(16) 0.4344(6) 0.076(3) Uani 1 1 d . . . . .
H35A H -0.4678 1.4881 0.4061 0.091 Uiso 0.6208 1 d . U P A 1
H35B H -0.5841 1.5142 0.4317 0.091 Uiso 0.6208 1 d . U P A 1
H35D H -0.5852 1.3747 0.4199 0.114 Uiso 0.3792 1 d . U P A 2
H35E H -0.5418 1.5514 0.4298 0.114 Uiso 0.3792 1 d . U P A 2
H35F H -0.4701 1.4187 0.4018 0.114 Uiso 0.3792 1 d . U P A 2
C36 C -0.4663(9) 1.4074(16) 0.5124(6) 0.069(3) Uani 1 1 d . . . . .
H36A H -0.4369 1.5051 0.5378 0.104 Uiso 0.6208 1 d . U P A 1
H36B H -0.4069 1.3290 0.5134 0.104 Uiso 0.6208 1 d . U P A 1
H36C H -0.5213 1.3605 0.5393 0.104 Uiso 0.6208 1 d . U P A 1
H36D H -0.4498 1.2938 0.5159 0.083 Uiso 0.3792 1 d . U P A 2
H36E H -0.5204 1.4244 0.5435 0.083 Uiso 0.3792 1 d . U P A 2
O1W O -0.6866(7) 1.2925(12) 0.2666(5) 0.089(3) Uani 1 1 d . . . . .
H11W H -0.6689 1.3588 0.2347 0.134 Uiso 1 1 d R U . . .
H12W H -0.7567 1.2994 0.2640 0.134 Uiso 1 1 d R U . . .
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
O1 0.025(3) 0.034(3) 0.038(3) 0.006(2) -0.003(2) -0.008(2)
O2 0.019(2) 0.035(3) 0.040(3) 0.003(2) -0.002(2) -0.006(2)
O3 0.022(3) 0.027(3) 0.046(3) -0.003(2) 0.002(2) -0.007(2)
O4 0.030(3) 0.027(3) 0.033(3) 0.006(2) -0.001(2) 0.006(2)
N1 0.022(3) 0.021(3) 0.022(3) 0.000(2) -0.002(2) 0.004(2)
N2 0.017(3) 0.020(3) 0.025(3) 0.003(2) 0.003(2) -0.004(2)
C1 0.020(3) 0.022(4) 0.036(4) 0.002(3) 0.006(3) 0.003(3)
C2 0.023(4) 0.030(4) 0.030(4) -0.007(3) -0.004(3) 0.000(3)
C3 0.036(4) 0.030(4) 0.023(4) -0.006(3) 0.000(3) -0.009(3)
C4 0.017(3) 0.021(4) 0.027(3) 0.002(3) 0.006(3) 0.003(3)
C5 0.026(4) 0.022(4) 0.024(4) -0.005(3) 0.004(3) 0.000(3)
C6 0.024(4) 0.017(3) 0.030(4) 0.000(3) 0.005(3) 0.004(3)
C7 0.020(3) 0.018(4) 0.029(4) 0.007(3) 0.006(3) 0.001(3)
C8 0.026(4) 0.020(4) 0.027(4) 0.001(3) -0.001(3) -0.002(3)
C9 0.025(4) 0.027(4) 0.024(4) 0.002(3) -0.003(3) -0.002(3)
C10 0.036(4) 0.023(4) 0.034(4) 0.011(3) -0.001(3) -0.003(3)
C11 0.029(4) 0.023(4) 0.034(4) 0.001(3) -0.002(3) -0.009(3)
C12 0.024(4) 0.037(4) 0.039(4) 0.003(4) -0.003(3) -0.013(3)
C13 0.022(4) 0.023(4) 0.045(5) -0.007(3) -0.004(3) -0.002(3)
C14 0.015(3) 0.018(3) 0.039(4) -0.001(3) 0.003(3) -0.004(3)
C15 0.017(3) 0.037(5) 0.032(4) 0.000(3) -0.001(3) 0.010(3)
C16 0.028(4) 0.022(4) 0.028(4) 0.001(3) 0.001(3) 0.004(3)
C17 0.034(4) 0.024(4) 0.023(4) 0.002(3) 0.002(3) -0.001(3)
C18 0.022(4) 0.022(4) 0.024(4) -0.002(3) -0.001(3) -0.005(3)
C19 0.019(3) 0.021(4) 0.031(4) -0.001(3) 0.005(3) -0.003(3)
C20 0.020(3) 0.014(3) 0.034(4) -0.002(3) -0.004(3) -0.004(3)
C21 0.024(3) 0.021(4) 0.019(3) 0.002(3) 0.000(3) 0.000(3)
C22 0.021(4) 0.055(6) 0.036(4) 0.003(4) -0.015(3) 0.008(4)
C23 0.038(4) 0.023(4) 0.052(5) 0.004(4) 0.013(4) -0.008(3)
O5 0.054(3) 0.024(3) 0.037(3) -0.004(2) 0.010(3) -0.011(3)
O6 0.055(4) 0.038(3) 0.027(3) -0.008(2) 0.001(3) 0.005(3)
O7 0.050(3) 0.019(3) 0.045(3) 0.000(2) 0.000(3) -0.005(3)
O8 0.047(3) 0.026(3) 0.033(3) -0.006(2) -0.001(2) -0.003(2)
O9 0.033(3) 0.046(4) 0.053(4) -0.013(3) -0.016(3) 0.023(3)
O10 0.027(3) 0.048(4) 0.030(3) -0.007(3) -0.001(2) -0.006(3)
O11 0.025(3) 0.050(4) 0.041(3) 0.007(3) -0.004(2) 0.012(3)
O12 0.037(3) 0.036(4) 0.052(4) -0.002(3) -0.004(3) 0.009(3)
N3 0.045(4) 0.015(3) 0.027(3) 0.003(2) -0.004(3) -0.003(3)
N4 0.074(5) 0.027(4) 0.041(4) 0.003(3) 0.016(4) 0.012(4)
N5 0.030(3) 0.033(4) 0.032(3) -0.006(3) -0.003(3) -0.002(3)
N6 0.021(3) 0.032(4) 0.036(4) 0.003(3) 0.004(3) 0.002(3)
C24 0.063(6) 0.027(4) 0.032(4) 0.001(4) 0.008(4) 0.010(4)
C25 0.056(5) 0.015(4) 0.027(4) -0.002(3) 0.001(3) 0.007(3)
C26 0.060(6) 0.024(4) 0.024(4) 0.003(3) -0.005(4) 0.007(4)
C27 0.056(5) 0.023(4) 0.030(4) -0.002(3) -0.001(4) -0.004(4)
C28 0.038(4) 0.021(4) 0.033(4) 0.000(3) -0.004(3) -0.007(3)
C29 0.039(4) 0.021(4) 0.030(4) -0.002(3) 0.004(3) -0.010(3)
C30 0.022(4) 0.032(4) 0.029(4) 0.004(3) -0.003(3) -0.003(3)
C31 0.011(3) 0.031(4) 0.033(4) -0.004(3) 0.002(3) 0.003(3)
C32 0.016(3) 0.032(4) 0.036(4) -0.004(3) -0.002(3) 0.002(3)
C33 0.018(3) 0.032(4) 0.028(4) 0.002(3) 0.009(3) 0.004(3)
C34 0.021(3) 0.023(4) 0.032(4) 0.001(3) 0.003(3) 0.001(3)
O35 0.066(8) 0.061(8) 0.073(8) 0.016(6) 0.012(6) 0.001(6)
O351 0.053(10) 0.022(8) 0.032(8) -0.012(6) -0.013(7) 0.000(7)
C35 0.075(7) 0.066(8) 0.076(8) -0.012(6) -0.008(6) 0.005(6)
C36 0.063(7) 0.081(8) 0.059(6) 0.010(6) 0.003(5) 0.001(6)
O1W 0.084(6) 0.097(7) 0.084(6) 0.005(5) 0.013(5) -0.011(5)
_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
O1 C11 1.427(8) . ?
O1 C12 1.470(9) . ?
O2 C2 1.388(8) . ?
O2 C22 1.438(9) . ?
O3 C3 1.344(9) . ?
O3 C23 1.460(9) . ?
O4 C9 1.231(8) . ?
N1 C9 1.339(9) . ?
N1 C6 1.417(8) . ?
N1 C8 1.500(8) . ?
N2 C16 1.496(9) . ?
N2 C15 1.524(8) . ?
N2 C21 1.560(8) . ?
N2 H22 1.0000 . ?
C1 C6 1.379(9) . ?
C1 C2 1.400(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(10) . ?
C3 C4 1.420(9) . ?
C4 C5 1.389(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(9) . ?
C5 C7 1.520(9) . ?
C7 C21 1.527(9) . ?
C7 C17 1.533(9) . ?
C7 C8 1.552(9) . ?
C8 C18 1.535(10) . ?
C8 H8 1.0000 . ?
C9 C10 1.498(10) . ?
C10 C11 1.559(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.535(10) . ?
C11 H11 1.0000 . ?
C12 C13 1.460(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.340(10) . ?
C13 H13 0.9500 . ?
C14 C19 1.510(9) . ?
C14 C15 1.519(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.528(9) . ?
C18 H18 1.0000 . ?
C19 C20 1.508(9) . ?
C19 H19 1.0000 . ?
C20 C21 1.519(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.278(10) . ?
O6 C24 1.243(9) . ?
O7 C27 1.232(9) . ?
O8 C28 1.249(9) . ?
O9 N5 1.241(8) . ?
O10 N5 1.223(7) . ?
O11 N6 1.227(8) . ?
O12 N6 1.211(8) . ?
N3 C28 1.326(9) . ?
N3 C25 1.451(9) . ?
N3 H3 0.8800 . ?
N4 C27 1.314(11) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C31 1.436(10) . ?
N6 C33 1.486(9) . ?
C24 C25 1.516(11) . ?
C25 C26 1.509(11) . ?
C25 H25 1.0000 . ?
C26 C27 1.523(11) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C28 C29 1.515(10) . ?
C29 C30 1.385(11) . ?
C29 C34 1.423(10) . ?
C30 C31 1.390(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.383(10) . ?
C32 C33 1.383(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.364(9) . ?
C34 H34 0.9500 . ?
O35 C35 1.510(17) . ?
O35 H35 0.8216 . ?
O351 C36 1.341(16) . ?
O351 H351 0.8601 . ?
C35 C36 1.464(14) . ?
C35 H35A 0.9889 . ?
C35 H35B 0.9698 . ?
C35 H35D 0.9673 . ?
C35 H35E 0.9366 . ?
C35 H35F 0.9725 . ?
C36 H36A 0.9697 . ?
C36 H36B 0.9802 . ?
C36 H36C 0.9949 . ?
C36 H36D 0.9696 . ?
C36 H36E 0.9693 . ?
O1W H11W 0.8600 . ?
O1W H12W 0.8600 . ?
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
C11 O1 C12 115.5(6) . . ?
C2 O2 C22 115.6(6) . . ?
C3 O3 C23 117.0(5) . . ?
C9 N1 C6 127.0(6) . . ?
C9 N1 C8 117.8(6) . . ?
C6 N1 C8 108.5(5) . . ?
C16 N2 C15 113.0(5) . . ?
C16 N2 C21 107.5(5) . . ?
C15 N2 C21 113.1(5) . . ?
C16 N2 H22 107.7 . . ?
C15 N2 H22 107.7 . . ?
C21 N2 H22 107.7 . . ?
C6 C1 C2 118.9(6) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
O2 C2 C1 125.0(6) . . ?
O2 C2 C3 114.2(6) . . ?
C1 C2 C3 120.9(6) . . ?
O3 C3 C2 116.4(6) . . ?
O3 C3 C4 124.5(6) . . ?
C2 C3 C4 119.1(6) . . ?
C5 C4 C3 118.4(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 C7 109.5(6) . . ?
C4 C5 C7 128.9(6) . . ?
C5 C6 C1 121.0(6) . . ?
C5 C6 N1 111.2(6) . . ?
C1 C6 N1 127.6(6) . . ?
C5 C7 C21 113.0(6) . . ?
C5 C7 C17 113.2(5) . . ?
C21 C7 C17 102.2(5) . . ?
C5 C7 C8 102.7(5) . . ?
C21 C7 C8 115.2(5) . . ?
C17 C7 C8 110.9(6) . . ?
N1 C8 C18 106.1(5) . . ?
N1 C8 C7 104.0(5) . . ?
C18 C8 C7 116.2(6) . . ?
N1 C8 H8 110.1 . . ?
C18 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
O4 C9 N1 122.9(6) . . ?
O4 C9 C10 122.1(6) . . ?
N1 C9 C10 115.0(6) . . ?
C9 C10 C11 114.8(6) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
O1 C11 C18 115.8(6) . . ?
O1 C11 C10 103.8(6) . . ?
C18 C11 C10 110.6(6) . . ?
O1 C11 H11 108.8 . . ?
C18 C11 H11 108.8 . . ?
C10 C11 H11 108.8 . . ?
C13 C12 O1 109.9(6) . . ?
C13 C12 H12A 109.7 . . ?
O1 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
O1 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 120.6(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C19 122.3(6) . . ?
C13 C14 C15 121.7(6) . . ?
C19 C14 C15 115.9(6) . . ?
C14 C15 N2 110.2(5) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 104.0(5) . . ?
N2 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
N2 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C16 C17 C7 101.6(6) . . ?
C16 C17 H17A 111.5 . . ?
C7 C17 H17A 111.5 . . ?
C16 C17 H17B 111.5 . . ?
C7 C17 H17B 111.5 . . ?
H17A C17 H17B 109.3 . . ?
C19 C18 C11 120.5(6) . . ?
C19 C18 C8 112.6(5) . . ?
C11 C18 C8 107.1(5) . . ?
C19 C18 H18 105.1 . . ?
C11 C18 H18 105.1 . . ?
C8 C18 H18 105.1 . . ?
C20 C19 C14 109.8(6) . . ?
C20 C19 C18 108.6(5) . . ?
C14 C19 C18 113.2(6) . . ?
C20 C19 H19 108.4 . . ?
C14 C19 H19 108.4 . . ?
C18 C19 H19 108.4 . . ?
C19 C20 C21 109.4(6) . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 C7 115.6(5) . . ?
C20 C21 N2 109.9(5) . . ?
C7 C21 N2 102.9(5) . . ?
C20 C21 H21 109.4 . . ?
C7 C21 H21 109.4 . . ?
N2 C21 H21 109.4 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C28 N3 C25 122.7(6) . . ?
C28 N3 H3 118.7 . . ?
C25 N3 H3 118.7 . . ?
C27 N4 H4A 120.0 . . ?
C27 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O10 N5 O9 121.8(7) . . ?
O10 N5 C31 118.9(6) . . ?
O9 N5 C31 119.3(6) . . ?
O12 N6 O11 125.5(6) . . ?
O12 N6 C33 117.1(6) . . ?
O11 N6 C33 117.4(6) . . ?
O6 C24 O5 124.8(8) . . ?
O6 C24 C25 116.1(8) . . ?
O5 C24 C25 119.1(7) . . ?
N3 C25 C26 109.3(6) . . ?
N3 C25 C24 114.8(7) . . ?
C26 C25 C24 109.6(6) . . ?
N3 C25 H25 107.6 . . ?
C26 C25 H25 107.6 . . ?
C24 C25 H25 107.6 . . ?
C25 C26 C27 110.7(6) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
O7 C27 N4 120.8(8) . . ?
O7 C27 C26 119.5(8) . . ?
N4 C27 C26 119.7(7) . . ?
O8 C28 N3 124.0(7) . . ?
O8 C28 C29 119.3(7) . . ?
N3 C28 C29 116.7(7) . . ?
C30 C29 C34 119.2(6) . . ?
C30 C29 C28 124.6(7) . . ?
C34 C29 C28 116.1(7) . . ?
C29 C30 C31 119.8(7) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 122.1(7) . . ?
C32 C31 N5 119.7(6) . . ?
C30 C31 N5 118.2(6) . . ?
C31 C32 C33 116.6(6) . . ?
C31 C32 H32 121.7 . . ?
C33 C32 H32 121.7 . . ?
C34 C33 C32 124.1(7) . . ?
C34 C33 N6 118.1(7) . . ?
C32 C33 N6 117.8(6) . . ?
C33 C34 C29 118.2(7) . . ?
C33 C34 H34 120.9 . . ?
C29 C34 H34 120.9 . . ?
C35 O35 H35 107.8 . . ?
C36 O351 H351 106.6 . . ?
C36 C35 O35 102.1(10) . . ?
C36 C35 H35A 110.5 . . ?
O35 C35 H35A 109.7 . . ?
C36 C35 H35B 112.4 . . ?
O35 C35 H35B 110.9 . . ?
H35A C35 H35B 110.9 . . ?
C36 C35 H35D 109.3 . . ?
C36 C35 H35E 110.3 . . ?
H35D C35 H35E 110.8 . . ?
C36 C35 H35F 108.1 . . ?
H35D C35 H35F 107.8 . . ?
H35E C35 H35F 110.4 . . ?
O351 C36 C35 120.1(12) . . ?
C35 C36 H36A 109.7 . . ?
C35 C36 H36B 110.6 . . ?
H36A C36 H36B 110.3 . . ?
C35 C36 H36C 108.9 . . ?
H36A C36 H36C 109.1 . . ?
H36B C36 H36C 108.2 . . ?
O351 C36 H36D 108.1 . . ?
C35 C36 H36D 108.2 . . ?
O351 C36 H36E 107.1 . . ?
C35 C36 H36E 106.8 . . ?
H36D C36 H36E 105.5 . . ?
H11W O1W H12W 108.3 . . ?
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
C22 O2 C2 C1 -2.0(10) . . . . ?
C22 O2 C2 C3 179.0(7) . . . . ?
C6 C1 C2 O2 -177.1(7) . . . . ?
C6 C1 C2 C3 1.8(11) . . . . ?
C23 O3 C3 C2 -174.7(6) . . . . ?
C23 O3 C3 C4 4.5(10) . . . . ?
O2 C2 C3 O3 -2.7(10) . . . . ?
C1 C2 C3 O3 178.3(6) . . . . ?
O2 C2 C3 C4 178.0(6) . . . . ?
C1 C2 C3 C4 -0.9(11) . . . . ?
O3 C3 C4 C5 179.6(7) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C3 C4 C5 C6 2.7(10) . . . . ?
C3 C4 C5 C7 -175.6(7) . . . . ?
C4 C5 C6 C1 -1.9(10) . . . . ?
C7 C5 C6 C1 176.7(6) . . . . ?
C4 C5 C6 N1 173.9(6) . . . . ?
C7 C5 C6 N1 -7.5(8) . . . . ?
C2 C1 C6 C5 -0.4(10) . . . . ?
C2 C1 C6 N1 -175.4(7) . . . . ?
C9 N1 C6 C5 -156.4(7) . . . . ?
C8 N1 C6 C5 -6.2(7) . . . . ?
C9 N1 C6 C1 19.1(11) . . . . ?
C8 N1 C6 C1 169.3(7) . . . . ?
C6 C5 C7 C21 142.0(6) . . . . ?
C4 C5 C7 C21 -39.5(9) . . . . ?
C6 C5 C7 C17 -102.3(7) . . . . ?
C4 C5 C7 C17 76.1(9) . . . . ?
C6 C5 C7 C8 17.3(7) . . . . ?
C4 C5 C7 C8 -164.3(7) . . . . ?
C9 N1 C8 C18 46.9(7) . . . . ?
C6 N1 C8 C18 -106.4(6) . . . . ?
C9 N1 C8 C7 169.9(6) . . . . ?
C6 N1 C8 C7 16.7(7) . . . . ?
C5 C7 C8 N1 -19.8(6) . . . . ?
C21 C7 C8 N1 -143.1(5) . . . . ?
C17 C7 C8 N1 101.4(6) . . . . ?
C5 C7 C8 C18 96.4(6) . . . . ?
C21 C7 C8 C18 -27.0(8) . . . . ?
C17 C7 C8 C18 -142.4(6) . . . . ?
C6 N1 C9 O4 -22.9(11) . . . . ?
C8 N1 C9 O4 -170.6(6) . . . . ?
C6 N1 C9 C10 159.6(6) . . . . ?
C8 N1 C9 C10 11.8(9) . . . . ?
O4 C9 C10 C11 134.3(7) . . . . ?
N1 C9 C10 C11 -48.1(9) . . . . ?
C12 O1 C11 C18 -59.1(8) . . . . ?
C12 O1 C11 C10 179.6(5) . . . . ?
C9 C10 C11 O1 145.5(6) . . . . ?
C9 C10 C11 C18 20.6(8) . . . . ?
C11 O1 C12 C13 89.0(7) . . . . ?
O1 C12 C13 C14 -70.6(9) . . . . ?
C12 C13 C14 C19 -0.7(11) . . . . ?
C12 C13 C14 C15 -179.8(7) . . . . ?
C13 C14 C15 N2 -130.4(7) . . . . ?
C19 C14 C15 N2 50.4(8) . . . . ?
C16 N2 C15 C14 76.8(7) . . . . ?
C21 N2 C15 C14 -45.6(8) . . . . ?
C15 N2 C16 C17 -144.5(5) . . . . ?
C21 N2 C16 C17 -19.0(7) . . . . ?
N2 C16 C17 C7 40.5(7) . . . . ?
C5 C7 C17 C16 -168.8(6) . . . . ?
C21 C7 C17 C16 -46.9(7) . . . . ?
C8 C7 C17 C16 76.4(7) . . . . ?
O1 C11 C18 C19 48.2(9) . . . . ?
C10 C11 C18 C19 165.9(6) . . . . ?
O1 C11 C18 C8 -82.1(7) . . . . ?
C10 C11 C18 C8 35.6(7) . . . . ?
N1 C8 C18 C19 155.1(5) . . . . ?
C7 C8 C18 C19 40.1(7) . . . . ?
N1 C8 C18 C11 -70.3(6) . . . . ?
C7 C8 C18 C11 174.7(6) . . . . ?
C13 C14 C19 C20 -177.5(6) . . . . ?
C15 C14 C19 C20 1.6(8) . . . . ?
C13 C14 C19 C18 60.9(8) . . . . ?
C15 C14 C19 C18 -119.9(6) . . . . ?
C11 C18 C19 C20 172.6(6) . . . . ?
C8 C18 C19 C20 -59.6(7) . . . . ?
C11 C18 C19 C14 -65.2(8) . . . . ?
C8 C18 C19 C14 62.6(7) . . . . ?
C14 C19 C20 C21 -58.4(7) . . . . ?
C18 C19 C20 C21 65.8(7) . . . . ?
C19 C20 C21 C7 -53.9(7) . . . . ?
C19 C20 C21 N2 62.0(7) . . . . ?
C5 C7 C21 C20 -83.6(7) . . . . ?
C17 C7 C21 C20 154.4(6) . . . . ?
C8 C7 C21 C20 34.0(8) . . . . ?
C5 C7 C21 N2 156.6(5) . . . . ?
C17 C7 C21 N2 34.5(6) . . . . ?
C8 C7 C21 N2 -85.8(6) . . . . ?
C16 N2 C21 C20 -133.6(5) . . . . ?
C15 N2 C21 C20 -8.1(7) . . . . ?
C16 N2 C21 C7 -9.9(6) . . . . ?
C15 N2 C21 C7 115.5(6) . . . . ?
C28 N3 C25 C26 -131.4(7) . . . . ?
C28 N3 C25 C24 104.9(8) . . . . ?
O6 C24 C25 N3 -160.8(7) . . . . ?
O5 C24 C25 N3 22.6(10) . . . . ?
O6 C24 C25 C26 75.6(9) . . . . ?
O5 C24 C25 C26 -100.9(8) . . . . ?
N3 C25 C26 C27 61.7(8) . . . . ?
C24 C25 C26 C27 -171.6(6) . . . . ?
C25 C26 C27 O7 39.7(9) . . . . ?
C25 C26 C27 N4 -141.1(7) . . . . ?
C25 N3 C28 O8 1.6(12) . . . . ?
C25 N3 C28 C29 -179.3(7) . . . . ?
O8 C28 C29 C30 -172.5(7) . . . . ?
N3 C28 C29 C30 8.3(11) . . . . ?
O8 C28 C29 C34 3.8(10) . . . . ?
N3 C28 C29 C34 -175.3(6) . . . . ?
C34 C29 C30 C31 0.3(10) . . . . ?
C28 C29 C30 C31 176.6(7) . . . . ?
C29 C30 C31 C32 -0.3(10) . . . . ?
C29 C30 C31 N5 -179.9(6) . . . . ?
O10 N5 C31 C32 -13.4(10) . . . . ?
O9 N5 C31 C32 165.6(7) . . . . ?
O10 N5 C31 C30 166.2(6) . . . . ?
O9 N5 C31 C30 -14.8(10) . . . . ?
C30 C31 C32 C33 1.2(10) . . . . ?
N5 C31 C32 C33 -179.2(6) . . . . ?
C31 C32 C33 C34 -2.3(10) . . . . ?
C31 C32 C33 N6 178.0(6) . . . . ?
O12 N6 C33 C34 17.8(9) . . . . ?
O11 N6 C33 C34 -163.5(6) . . . . ?
O12 N6 C33 C32 -162.6(7) . . . . ?
O11 N6 C33 C32 16.2(9) . . . . ?
C32 C33 C34 C29 2.4(10) . . . . ?
N6 C33 C34 C29 -178.0(6) . . . . ?
C30 C29 C34 C33 -1.3(10) . . . . ?
C28 C29 C34 C33 -177.9(6) . . . . ?
O35 C35 C36 O351 142.3(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
N2 H22 O5 1.00 1.69 2.654(8) 159.6 .
N2 H22 O351 1.00 2.73 3.252(14) 113.1 .
N3 H3 O7 0.88 1.90 2.746(8) 162.0 2_546
N4 H4A O5 0.88 2.22 3.009(9) 149.0 2_556
N4 H4A O351 0.88 2.48 3.074(18) 125.3 2_556
N4 H4B O8 0.88 2.06 2.930(9) 168.3 2_546
O35 H35 O1W 0.82 1.84 2.659(14) 173.4 .
O1W H11W O1 0.86 2.04 2.791(10) 145.2 2_456
O1W H12W O6 0.86 1.82 2.650(10) 162.4 2_446
_refine_diff_density_max 0.338
_refine_diff_density_min -0.583
_refine_diff_density_rms 0.087
_database_code_depnum_ccdc_archive 'CCDC 933061'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_bdnbln(2)
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
brucinium N-(3,5-dinitrobenzoyl)-L-asparaginate methanol 1.2-solvate 1.5-hydrate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety
;
C23 H27 N2 O4, C11 H9 N4 O8, 1.2(C H4 O), 1.5(H2 O)
;
_chemical_formula_sum 'C35.19 H43.75 N6 O14.69'
_chemical_formula_weight 785.76
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 5
_space_group_name_H-M_alt 'C 2'
_space_group_name_Hall 'C 2y'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a 38.752(5)
_cell_length_b 12.287(3)
_cell_length_c 7.909(2)
_cell_angle_alpha 90
_cell_angle_beta 100.63(3)
_cell_angle_gamma 90
_cell_volume 3701.2(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 4253
_cell_measurement_theta_min 3.062
_cell_measurement_theta_max 27.498
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.410
_exptl_crystal_F_000 1658
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.1
_exptl_absorpt_coefficient_mu 0.111
_shelx_estimated_absorpt_T_min ?
_shelx_estimated_absorpt_T_max ?
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Sapphire2'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 21991
_diffrn_reflns_av_unetI/netI 0.2441
_diffrn_reflns_av_R_equivalents 0.0882
_diffrn_reflns_limit_h_min -48
_diffrn_reflns_limit_h_max 49
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 3.062
_diffrn_reflns_theta_max 27.498
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total 8328
_reflns_number_gt 3548
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.883
_reflns_Friedel_fraction_max 0.966
_reflns_Friedel_fraction_full 0.983
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0552P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack -1.9(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 8328
_refine_ls_number_parameters 644
_refine_ls_number_restraints 266
_refine_ls_R_factor_all 0.1778
_refine_ls_R_factor_gt 0.0693
_refine_ls_wR_factor_ref 0.1457
_refine_ls_wR_factor_gt 0.1202
_refine_ls_goodness_of_fit_ref 0.873
_refine_ls_restrained_S_all 0.871
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30587(13) 0.1515(5) 0.7895(6) 0.0329(13) Uani 1 1 d . . . . .
O2 O 0.17781(13) 0.7325(5) 0.7589(6) 0.0361(14) Uani 1 1 d . . . . .
O3 O 0.23315(12) 0.8491(5) 0.7568(6) 0.0325(14) Uani 1 1 d . . . . .
O4 O 0.19813(13) 0.3335(5) 0.7376(7) 0.0463(16) Uani 1 1 d . . . . .
N1 N 0.25225(15) 0.4038(6) 0.8367(7) 0.0290(16) Uani 1 1 d . . . . .
N2 N 0.36960(15) 0.4966(6) 0.9211(8) 0.0333(16) Uani 1 1 d . . . . .
H24 H 0.3860 0.5598 0.9460 0.040 Uiso 1 1 calc R U . . .
C1 C 0.21081(18) 0.5660(8) 0.8001(8) 0.032(2) Uani 1 1 d . . . . .
H1 H 0.1904 0.5229 0.7982 0.039 Uiso 1 1 calc R U . . .
C2 C 0.2080(2) 0.6780(7) 0.7813(9) 0.0300(19) Uani 1 1 d . . . . .
C3 C 0.23894(19) 0.7404(7) 0.7865(9) 0.033(2) Uani 1 1 d . . . . .
C4 C 0.27132(18) 0.6908(7) 0.8172(8) 0.030(2) Uani 1 1 d . . . . .
H4 H 0.2921 0.7333 0.8259 0.036 Uiso 1 1 calc R U . . .
C5 C 0.27360(17) 0.5788(7) 0.8355(9) 0.028(2) Uani 1 1 d . . . . .
C6 C 0.2432(2) 0.5176(7) 0.8215(9) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.30610(18) 0.5072(6) 0.8855(8) 0.0250(18) Uani 1 1 d . . . . .
C8 C 0.29072(16) 0.3901(6) 0.8497(9) 0.0246(19) Uani 1 1 d . . . . .
H8 H 0.3003 0.3402 0.9469 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2302(2) 0.3239(7) 0.7673(10) 0.036(2) Uani 1 1 d . . . . .
C10 C 0.24768(19) 0.2135(7) 0.7425(9) 0.029(2) Uani 1 1 d . . . . .
H10A H 0.2311 0.1694 0.6597 0.035 Uiso 1 1 calc R U . . .
H10B H 0.2519 0.1743 0.8538 0.035 Uiso 1 1 calc R U . . .
C11 C 0.28311(18) 0.2221(7) 0.6765(9) 0.0260(18) Uani 1 1 d . . . . .
H11 H 0.2799 0.1932 0.5565 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3392(2) 0.1307(7) 0.7345(10) 0.039(2) Uani 1 1 d . . . . .
H12A H 0.3358 0.1343 0.6075 0.047 Uiso 1 1 calc R U . . .
H12B H 0.3475 0.0565 0.7705 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3670(2) 0.2135(7) 0.8123(10) 0.040(2) Uani 1 1 d . . . . .
H13 H 0.3872 0.1912 0.8916 0.048 Uiso 1 1 calc R U . . .
C14 C 0.36239(18) 0.3184(8) 0.7668(9) 0.035(2) Uani 1 1 d . . . . .
C15 C 0.3887(2) 0.4070(7) 0.8507(11) 0.044(2) Uani 1 1 d . . . . .
H15A H 0.4060 0.3742 0.9445 0.053 Uiso 1 1 calc R U . . .
H15B H 0.4015 0.4366 0.7638 0.053 Uiso 1 1 calc R U . . .
C16 C 0.35862(19) 0.4639(7) 1.0882(9) 0.035(2) Uani 1 1 d . . . . .
H16A H 0.3757 0.4905 1.1886 0.043 Uiso 1 1 calc R U . . .
H16B H 0.3566 0.3838 1.0963 0.043 Uiso 1 1 calc R U . . .
C17 C 0.32275(18) 0.5190(7) 1.0785(9) 0.0301(19) Uani 1 1 d . . . . .
H17A H 0.3254 0.5965 1.1128 0.036 Uiso 1 1 calc R U . . .
H17B H 0.3085 0.4814 1.1526 0.036 Uiso 1 1 calc R U . . .
C18 C 0.29512(18) 0.3401(6) 0.6784(9) 0.0269(19) Uani 1 1 d . . . . .
H18 H 0.2778 0.3782 0.5882 0.032 Uiso 1 1 calc R U . . .
C19 C 0.33226(19) 0.3632(7) 0.6335(10) 0.038(2) Uani 1 1 d . . . . .
H19 H 0.3333 0.3301 0.5190 0.046 Uiso 1 1 calc R U . . .
C20 C 0.33511(19) 0.4878(6) 0.6199(9) 0.0267(19) Uani 1 1 d . . . . .
H20A H 0.3565 0.5074 0.5749 0.032 Uiso 1 1 calc R U . . .
H20B H 0.3145 0.5168 0.5399 0.032 Uiso 1 1 calc R U . . .
C21 C 0.33676(17) 0.5356(6) 0.7944(8) 0.0240(18) Uani 1 1 d . . . . .
H21 H 0.3380 0.6166 0.7845 0.029 Uiso 1 1 calc R U . . .
C22 C 0.14654(17) 0.6687(7) 0.7601(9) 0.035(2) Uani 1 1 d . . . . .
H22A H 0.1260 0.7166 0.7420 0.053 Uiso 1 1 calc R U . . .
H22B H 0.1484 0.6318 0.8713 0.053 Uiso 1 1 calc R U . . .
H22C H 0.1440 0.6144 0.6679 0.053 Uiso 1 1 calc R U . . .
C23 C 0.2639(2) 0.9139(7) 0.7537(11) 0.045(2) Uani 1 1 d . . . . .
H23A H 0.2571 0.9902 0.7328 0.068 Uiso 1 1 calc R U . . .
H23B H 0.2757 0.8881 0.6616 0.068 Uiso 1 1 calc R U . . .
H23C H 0.2800 0.9077 0.8645 0.068 Uiso 1 1 calc R U . . .
O5 O 0.48073(13) 0.5294(5) 1.2593(6) 0.0301(13) Uani 1 1 d . . . . .
O6 O 0.42813(13) 0.5990(4) 1.1426(6) 0.0331(14) Uani 1 1 d . . . . .
O7 O 0.40274(12) 0.6585(5) 1.7142(6) 0.0294(12) Uani 1 1 d . U . . .
O8 O 0.40609(13) 0.3563(5) 1.4538(7) 0.0397(15) Uani 1 1 d . . . . .
O9 O 0.40088(19) -0.0151(6) 1.6151(10) 0.079(2) Uani 1 1 d . . . . .
N3 N 0.45850(15) 0.6413(5) 1.8501(7) 0.0287(15) Uani 1 1 d . U . . .
H37A H 0.4518 0.6341 1.9500 0.034 Uiso 1 1 calc R U . . .
H37B H 0.4810 0.6392 1.8445 0.034 Uiso 1 1 calc R U . . .
N4 N 0.45372(14) 0.4619(5) 1.5387(6) 0.0191(14) Uani 1 1 d . . . . .
H47 H 0.4744 0.4683 1.6058 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4497(2) 0.5641(6) 1.2639(9) 0.0244(18) Uani 1 1 d . . . . .
C25 C 0.43824(18) 0.5559(6) 1.4407(8) 0.0210(17) Uani 1 1 d . . . . .
H25 H 0.4121 0.5469 1.4195 0.025 Uiso 1 1 calc R U . . .
C26 C 0.44719(17) 0.6611(6) 1.5418(8) 0.0190(16) Uani 1 1 d . U . . .
H26A H 0.4729 0.6730 1.5623 0.023 Uiso 1 1 calc R U . . .
H26B H 0.4357 0.7233 1.4742 0.023 Uiso 1 1 calc R U . . .
C27 C 0.4350(2) 0.6552(6) 1.7099(9) 0.0225(16) Uani 1 1 d . U . . .
C28 C 0.43707(19) 0.3663(7) 1.5287(9) 0.0252(18) Uani 1 1 d . . . . .
C29 C 0.45578(19) 0.2707(6) 1.6138(9) 0.0271(19) Uani 1 1 d . . . . .
C30 C 0.4374(2) 0.1737(7) 1.6118(10) 0.036(2) Uani 1 1 d . U . . .
H30 H 0.4130 0.1714 1.5643 0.044 Uiso 1 1 calc R U . A 1
C34 C 0.4912(2) 0.2715(7) 1.6954(9) 0.0294(19) Uani 1 1 d . . . . .
H34 H 0.5044 0.3370 1.7056 0.035 Uiso 1 1 calc R U . B 1
O10 O 0.4497(3) -0.1049(7) 1.7246(19) 0.100(4) Uani 0.858(15) 1 d . . P C 1
O11 O 0.5552(5) 0.1006(8) 1.919(3) 0.080(4) Uani 0.858(15) 1 d D U P C 1
O12 O 0.56030(16) 0.2589(6) 1.8283(10) 0.047(3) Uani 0.858(15) 1 d D . P C 1
N5 N 0.4334(4) -0.0237(10) 1.6694(17) 0.065(4) Uani 0.858(15) 1 d . U P C 1
N6 N 0.5433(2) 0.1794(7) 1.8421(12) 0.032(2) Uani 0.858(15) 1 d D U P C 1
C31 C 0.4547(4) 0.0798(10) 1.6797(16) 0.033(3) Uani 0.858(15) 1 d . U P C 1
C32 C 0.4884(5) 0.0788(15) 1.7535(15) 0.035(3) Uani 0.858(15) 1 d . U P C 1
H32 H 0.4997 0.0138 1.7996 0.042 Uiso 0.858(15) 1 calc R U P C 1
C33 C 0.5062(2) 0.1752(11) 1.7603(12) 0.021(3) Uani 0.858(15) 1 d D U P C 1
O101 O 0.4449(13) -0.089(4) 1.838(6) 0.040(15) Uani 0.142(15) 1 d . U P C 2
O111 O 0.557(3) 0.100(3) 1.948(16) 0.069(8) Uani 0.142(15) 1 d D U P C 2
O121 O 0.5520(11) 0.269(3) 1.971(7) 0.062(18) Uani 0.142(15) 1 d D U P C 2
N51 N 0.426(2) -0.010(7) 1.754(11) 0.067(9) Uani 0.142(15) 1 d . U P C 2
N61 N 0.5409(13) 0.182(4) 1.917(7) 0.035(8) Uani 0.142(15) 1 d D U P C 2
C311 C 0.449(2) 0.100(7) 1.728(10) 0.027(8) Uani 0.142(15) 1 d . U P C 2
C321 C 0.486(3) 0.083(11) 1.806(11) 0.032(9) Uani 0.142(15) 1 d . U P C 2
H321 H 0.4967 0.0144 1.8415 0.039 Uiso 0.142(15) 1 calc R U P C 2
C331 C 0.5049(13) 0.186(8) 1.820(8) 0.022(8) Uani 0.142(15) 1 d D U P C 2
O1W O 0.5000 0.4032(12) 2.0000 0.160(6) Uani 1 2 d S TU P . .
H11W H 0.4938 0.4421 2.0830 0.240 Uiso 1 1 d R U . . .
O100 O 0.3910(5) 0.8631(17) 1.172(2) 0.062(4) Uani 0.357(13) 1 d D U P D 1
H100 H 0.3844 0.8278 1.2507 0.094 Uiso 0.357(13) 1 calc R U P D 1
C100 C 0.3672(7) 0.839(2) 1.004(3) 0.048(5) Uani 0.357(13) 1 d D U P D 1
H10H H 0.3682 0.7611 0.9781 0.073 Uiso 0.357(13) 1 calc R U P D 1
H10F H 0.3748 0.8811 0.9117 0.073 Uiso 0.357(13) 1 calc R U P D 1
H10G H 0.3431 0.8591 1.0112 0.073 Uiso 0.357(13) 1 calc R U P D 1
O110 O 0.3563(4) 0.8097(12) 0.885(2) 0.048(4) Uani 0.356(9) 1 d D U P E 2
H110 H 0.3738 0.7788 0.8576 0.072 Uiso 0.356(9) 1 calc R U P E 2
C110 C 0.3685(8) 0.8915(18) 1.024(3) 0.052(5) Uani 0.356(9) 1 d D U P E 2
H11A H 0.3747 0.9594 0.9714 0.078 Uiso 0.356(9) 1 calc R U P E 2
H11B H 0.3892 0.8632 1.1016 0.078 Uiso 0.356(9) 1 calc R U P E 2
H11C H 0.3497 0.9055 1.0883 0.078 Uiso 0.356(9) 1 calc R U P E 2
O120 O 0.4052(6) 0.8848(18) 1.243(2) 0.050(5) Uani 0.289(11) 1 d D U P F 3
H120 H 0.3948 0.8411 1.2981 0.075 Uiso 0.289(11) 1 calc R U P F 3
C120 C 0.3974(9) 0.857(3) 1.056(3) 0.051(4) Uani 0.289(11) 1 d D U P F 3
H12K H 0.3750 0.8897 1.0021 0.076 Uiso 0.289(11) 1 calc R U P F 3
H12I H 0.3958 0.7773 1.0424 0.076 Uiso 0.289(11) 1 calc R U P F 3
H12J H 0.4162 0.8843 1.0000 0.076 Uiso 0.289(11) 1 calc R U P F 3
O2W O 0.3364(2) 0.7518(10) 0.5693(13) 0.088(5) Uani 0.616(11) 1 d . . P G 1
H21W H 0.3427 0.8018 0.5012 0.132 Uiso 0.616(11) 1 d R U P G 1
H22W H 0.3569 0.7235 0.6141 0.132 Uiso 0.616(11) 1 d R U P G 1
O21W O 0.3636(3) 0.7155(11) 0.3903(16) 0.045(5) Uani 0.384(11) 1 d . U P G 2
H23W H 0.3406 0.7206 0.3753 0.067 Uiso 0.384(11) 1 d R U P G 2
H24W H 0.3759 0.6973 0.4910 0.067 Uiso 0.384(11) 1 d R U P G 2
O300 O 0.5331(8) -0.039(3) 1.591(4) 0.069(12) Uani 0.187(11) 1 d D U P H 2
H300 H 0.5379 -0.0650 1.4996 0.104 Uiso 0.187(11) 1 calc R U P H 2
C300 C 0.5184(12) -0.127(3) 1.688(5) 0.059(13) Uani 0.187(11) 1 d D U P H 2
H30A H 0.5230 -0.1979 1.6413 0.088 Uiso 0.187(11) 1 calc R U P H 2
H30B H 0.4930 -0.1164 1.6776 0.088 Uiso 0.187(11) 1 calc R U P H 2
H30C H 0.5295 -0.1232 1.8099 0.088 Uiso 0.187(11) 1 calc R U P H 2
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
O1 0.022(3) 0.043(3) 0.033(3) -0.002(3) 0.005(2) -0.015(3)
O2 0.014(3) 0.053(4) 0.041(3) 0.013(3) 0.004(3) 0.001(3)
O3 0.025(3) 0.039(4) 0.033(3) 0.001(3) 0.004(3) -0.009(3)
O4 0.015(3) 0.051(4) 0.070(4) 0.016(3) 0.000(3) -0.002(3)
N1 0.010(4) 0.046(5) 0.032(4) 0.003(3) 0.005(3) -0.008(3)
N2 0.021(4) 0.030(4) 0.049(4) -0.014(3) 0.010(3) -0.007(3)
C1 0.008(4) 0.074(7) 0.017(4) 0.007(4) 0.003(3) -0.004(4)
C2 0.020(5) 0.038(5) 0.034(5) 0.008(4) 0.008(4) -0.006(4)
C3 0.021(5) 0.053(6) 0.024(4) -0.004(4) 0.004(4) -0.004(5)
C4 0.011(4) 0.054(7) 0.022(4) -0.001(4) -0.003(3) -0.007(4)
C5 0.008(4) 0.053(6) 0.024(4) -0.004(4) 0.001(3) 0.014(4)
C6 0.020(5) 0.044(6) 0.027(4) -0.009(4) 0.010(4) -0.013(4)
C7 0.022(5) 0.034(5) 0.022(4) -0.002(4) 0.011(3) 0.000(4)
C8 0.005(4) 0.045(6) 0.023(4) -0.006(4) 0.000(3) -0.004(4)
C9 0.028(5) 0.049(6) 0.033(5) 0.014(4) 0.010(4) -0.009(5)
C10 0.020(4) 0.048(6) 0.019(4) -0.003(4) -0.001(3) -0.023(4)
C11 0.022(4) 0.034(5) 0.021(4) -0.006(4) 0.000(3) -0.011(4)
C12 0.039(5) 0.037(5) 0.043(5) 0.001(4) 0.012(4) -0.008(4)
C13 0.037(6) 0.041(6) 0.044(6) -0.003(5) 0.015(4) -0.011(4)
C14 0.016(4) 0.062(7) 0.027(5) -0.015(4) 0.007(4) -0.017(4)
C15 0.028(5) 0.053(6) 0.057(6) -0.031(5) 0.023(4) -0.010(5)
C16 0.034(5) 0.051(6) 0.023(4) -0.018(4) 0.009(4) -0.006(5)
C17 0.017(4) 0.037(5) 0.039(5) -0.008(4) 0.012(4) -0.003(4)
C18 0.024(4) 0.038(5) 0.019(4) -0.003(4) 0.004(3) -0.010(4)
C19 0.033(5) 0.048(6) 0.037(5) -0.002(4) 0.016(4) -0.013(4)
C20 0.025(5) 0.028(5) 0.030(5) -0.001(4) 0.014(4) -0.009(4)
C21 0.019(4) 0.023(4) 0.030(4) 0.006(4) 0.005(4) -0.010(3)
C22 0.013(4) 0.054(6) 0.038(5) 0.006(4) -0.001(4) -0.006(4)
C23 0.030(5) 0.039(5) 0.070(7) -0.009(5) 0.019(5) -0.014(4)
O5 0.021(3) 0.034(3) 0.035(3) -0.003(3) 0.008(3) 0.003(3)
O6 0.026(3) 0.044(4) 0.029(3) 0.011(3) 0.005(3) 0.008(3)
O7 0.022(3) 0.038(3) 0.030(3) 0.007(2) 0.008(2) 0.004(3)
O8 0.032(3) 0.031(3) 0.050(4) 0.004(3) -0.008(3) -0.006(3)
O9 0.057(5) 0.050(5) 0.112(6) 0.008(4) -0.028(4) -0.029(4)
N3 0.026(4) 0.036(4) 0.026(3) 0.006(3) 0.012(3) -0.003(3)
N4 0.012(3) 0.024(4) 0.017(3) 0.001(3) -0.008(2) 0.004(3)
C24 0.029(5) 0.023(4) 0.021(4) -0.001(4) 0.003(4) -0.004(4)
C25 0.020(4) 0.027(5) 0.014(4) 0.007(3) -0.003(3) 0.003(4)
C26 0.020(4) 0.012(4) 0.025(4) 0.009(3) 0.005(3) 0.003(3)
C27 0.029(4) 0.009(4) 0.027(4) 0.003(3) 0.000(3) 0.003(3)
C28 0.018(4) 0.022(5) 0.032(5) -0.005(4) -0.004(4) -0.005(4)
C29 0.023(5) 0.025(5) 0.033(5) 0.006(4) 0.002(4) -0.013(4)
C30 0.029(5) 0.041(5) 0.037(5) -0.011(4) 0.001(4) 0.000(4)
C34 0.033(5) 0.022(5) 0.034(5) -0.001(4) 0.010(4) -0.009(4)
O10 0.120(9) 0.015(5) 0.153(12) 0.022(6) -0.010(8) 0.006(5)
O11 0.068(6) 0.046(5) 0.106(10) 0.015(5) -0.035(6) 0.008(4)
O12 0.017(4) 0.045(5) 0.074(7) 0.024(4) -0.001(4) -0.002(3)
N5 0.076(8) 0.035(6) 0.081(9) 0.004(7) 0.005(7) -0.020(6)
N6 0.036(5) 0.038(5) 0.020(6) 0.014(4) 0.006(4) 0.010(5)
C31 0.041(6) 0.013(5) 0.043(7) 0.004(5) 0.001(5) -0.011(5)
C32 0.049(6) 0.020(5) 0.036(8) 0.015(7) 0.009(7) 0.015(5)
C33 0.023(5) 0.033(6) 0.006(6) 0.000(6) 0.000(4) 0.004(4)
O101 0.051(19) 0.034(18) 0.039(18) 0.012(13) 0.020(13) -0.003(12)
O111 0.063(11) 0.053(11) 0.082(13) 0.013(10) -0.011(10) 0.005(10)
O121 0.06(2) 0.06(2) 0.07(2) -0.004(13) 0.015(13) -0.006(13)
N51 0.072(12) 0.053(12) 0.073(14) 0.002(11) 0.008(11) -0.011(10)
N61 0.036(11) 0.039(11) 0.031(13) 0.006(10) 0.012(10) 0.007(10)
C311 0.030(12) 0.018(12) 0.033(13) 0.005(10) 0.004(10) -0.012(10)
C321 0.039(12) 0.023(11) 0.035(13) 0.008(11) 0.007(11) 0.012(10)
C331 0.022(11) 0.028(12) 0.016(13) -0.001(11) 0.003(10) 0.001(10)
O1W 0.210(11) 0.133(10) 0.149(10) 0.000 0.062(9) 0.000
O100 0.061(7) 0.063(7) 0.059(8) 0.004(7) 0.000(6) -0.001(6)
C100 0.049(7) 0.055(8) 0.043(7) 0.000(7) 0.014(7) -0.010(7)
O110 0.038(7) 0.060(7) 0.051(7) -0.004(6) 0.018(6) -0.014(6)
C110 0.052(7) 0.058(8) 0.049(7) 0.005(7) 0.020(7) -0.003(7)
O120 0.052(9) 0.049(8) 0.043(8) 0.001(7) -0.007(7) -0.015(7)
C120 0.051(7) 0.056(7) 0.048(7) 0.006(7) 0.016(7) -0.007(7)
O2W 0.055(8) 0.117(11) 0.097(9) 0.076(8) 0.027(7) 0.021(7)
O21W 0.031(8) 0.062(9) 0.038(8) 0.023(7) -0.005(6) 0.013(7)
O300 0.073(15) 0.067(15) 0.069(15) -0.013(10) 0.019(10) 0.014(10)
C300 0.058(16) 0.063(16) 0.061(16) -0.016(11) 0.022(11) 0.005(11)
_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
O1 C11 1.428(8) . ?
O1 C12 1.460(8) . ?
O2 C2 1.332(8) . ?
O2 C22 1.445(8) . ?
O3 C3 1.367(9) . ?
O3 C23 1.439(8) . ?
O4 C9 1.229(8) . ?
N1 C9 1.350(9) . ?
N1 C6 1.441(9) . ?
N1 C8 1.485(8) . ?
N2 C15 1.491(9) . ?
N2 C16 1.515(9) . ?
N2 C21 1.544(8) . ?
N2 H24 1.0000 . ?
C1 C6 1.372(10) . ?
C1 C2 1.387(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(10) . ?
C3 C4 1.375(10) . ?
C4 C5 1.385(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(10) . ?
C5 C7 1.527(9) . ?
C7 C21 1.539(9) . ?
C7 C17 1.551(9) . ?
C7 C8 1.564(10) . ?
C8 C18 1.525(9) . ?
C8 H8 1.0000 . ?
C9 C10 1.543(11) . ?
C10 C11 1.560(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.522(10) . ?
C11 H11 1.0000 . ?
C12 C13 1.526(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.340(10) . ?
C13 H13 0.9500 . ?
C14 C19 1.524(10) . ?
C14 C15 1.554(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.536(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.571(9) . ?
C18 H18 1.0000 . ?
C19 C20 1.541(10) . ?
C19 H19 1.0000 . ?
C20 C21 1.491(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.283(8) . ?
O6 C24 1.228(8) . ?
O7 C27 1.258(8) . ?
O8 C28 1.243(8) . ?
O9 N5 1.258(13) . ?
O9 N51 1.34(9) . ?
N3 C27 1.309(8) . ?
N3 H37A 0.8800 . ?
N3 H37B 0.8800 . ?
N4 C28 1.336(8) . ?
N4 C25 1.456(8) . ?
N4 H47 0.8800 . ?
C24 C25 1.546(9) . ?
C25 C26 1.526(9) . ?
C25 H25 1.0000 . ?
C26 C27 1.492(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C28 C29 1.476(10) . ?
C29 C30 1.388(10) . ?
C29 C34 1.404(9) . ?
C30 C311 1.31(9) . ?
C30 C31 1.392(15) . ?
C30 H30 0.9500 . ?
C34 C33 1.375(14) . ?
C34 C331 1.47(8) . ?
C34 H34 0.9500 . ?
O10 N5 1.218(13) . ?
O11 N6 1.193(8) . ?
O12 N6 1.195(7) . ?
N5 C31 1.510(17) . ?
N6 C33 1.465(10) . ?
C31 C32 1.33(2) . ?
C32 C33 1.37(2) . ?
C32 H32 0.9500 . ?
O101 N51 1.32(9) . ?
O111 N61 1.193(9) . ?
O121 N61 1.193(9) . ?
N51 C311 1.65(12) . ?
N61 C331 1.465(12) . ?
C311 C321 1.47(14) . ?
C321 C331 1.45(15) . ?
C321 H321 0.9500 . ?
O1W H11W 0.8801 . ?
O100 C100 1.501(6) . ?
O100 H100 0.8400 . ?
C100 H10H 0.9800 . ?
C100 H10F 0.9800 . ?
C100 H10G 0.9800 . ?
O110 C110 1.496(5) . ?
O110 H110 0.8400 . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
O120 C120 1.499(6) . ?
O120 H120 0.8400 . ?
C120 H12K 0.9800 . ?
C120 H12I 0.9800 . ?
C120 H12J 0.9800 . ?
O2W H21W 0.8800 . ?
O2W H22W 0.8804 . ?
O21W H23W 0.8798 . ?
O21W H24W 0.8801 . ?
O300 C300 1.500(7) . ?
O300 H300 0.8400 . ?
C300 H30A 0.9800 . ?
C300 H30B 0.9800 . ?
C300 H30C 0.9800 . ?
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
C11 O1 C12 113.5(5) . . ?
C2 O2 C22 116.3(6) . . ?
C3 O3 C23 115.7(6) . . ?
C9 N1 C6 123.2(6) . . ?
C9 N1 C8 119.7(6) . . ?
C6 N1 C8 110.0(6) . . ?
C15 N2 C16 111.6(6) . . ?
C15 N2 C21 113.1(6) . . ?
C16 N2 C21 108.6(5) . . ?
C15 N2 H24 107.8 . . ?
C16 N2 H24 107.8 . . ?
C21 N2 H24 107.8 . . ?
C6 C1 C2 119.7(7) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
O2 C2 C1 124.3(7) . . ?
O2 C2 C3 116.7(7) . . ?
C1 C2 C3 119.0(7) . . ?
O3 C3 C4 125.4(7) . . ?
O3 C3 C2 114.3(7) . . ?
C4 C3 C2 120.3(8) . . ?
C3 C4 C5 119.8(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.6(7) . . ?
C6 C5 C7 110.9(7) . . ?
C4 C5 C7 129.3(7) . . ?
C1 C6 C5 121.4(8) . . ?
C1 C6 N1 129.3(7) . . ?
C5 C6 N1 109.3(7) . . ?
C5 C7 C21 114.8(6) . . ?
C5 C7 C17 112.0(5) . . ?
C21 C7 C17 102.9(5) . . ?
C5 C7 C8 102.4(6) . . ?
C21 C7 C8 115.2(5) . . ?
C17 C7 C8 109.8(6) . . ?
N1 C8 C18 105.0(5) . . ?
N1 C8 C7 104.6(6) . . ?
C18 C8 C7 115.4(6) . . ?
N1 C8 H8 110.5 . . ?
C18 C8 H8 110.5 . . ?
C7 C8 H8 110.5 . . ?
O4 C9 N1 123.3(8) . . ?
O4 C9 C10 120.8(7) . . ?
N1 C9 C10 115.6(7) . . ?
C9 C10 C11 114.6(6) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O1 C11 C18 114.9(6) . . ?
O1 C11 C10 103.3(5) . . ?
C18 C11 C10 110.3(6) . . ?
O1 C11 H11 109.4 . . ?
C18 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
O1 C12 C13 111.1(6) . . ?
O1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 118.9(8) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C19 125.4(7) . . ?
C13 C14 C15 120.9(8) . . ?
C19 C14 C15 113.6(7) . . ?
N2 C15 C14 110.3(6) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 103.7(6) . . ?
N2 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
N2 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C16 C17 C7 102.5(5) . . ?
C16 C17 H17A 111.3 . . ?
C7 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C7 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C11 C18 C8 107.9(6) . . ?
C11 C18 C19 117.4(6) . . ?
C8 C18 C19 112.7(6) . . ?
C11 C18 H18 106.0 . . ?
C8 C18 H18 106.0 . . ?
C19 C18 H18 106.0 . . ?
C14 C19 C20 110.6(7) . . ?
C14 C19 C18 113.3(6) . . ?
C20 C19 C18 106.0(6) . . ?
C14 C19 H19 109.0 . . ?
C20 C19 H19 109.0 . . ?
C18 C19 H19 109.0 . . ?
C21 C20 C19 108.6(6) . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 C7 116.0(6) . . ?
C20 C21 N2 111.6(6) . . ?
C7 C21 N2 103.9(5) . . ?
C20 C21 H21 108.3 . . ?
C7 C21 H21 108.3 . . ?
N2 C21 H21 108.3 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 N3 H37A 120.0 . . ?
C27 N3 H37B 120.0 . . ?
H37A N3 H37B 120.0 . . ?
C28 N4 C25 121.2(6) . . ?
C28 N4 H47 119.4 . . ?
C25 N4 H47 119.4 . . ?
O6 C24 O5 126.9(7) . . ?
O6 C24 C25 117.5(7) . . ?
O5 C24 C25 115.6(6) . . ?
N4 C25 C26 111.2(5) . . ?
N4 C25 C24 112.0(6) . . ?
C26 C25 C24 110.1(5) . . ?
N4 C25 H25 107.8 . . ?
C26 C25 H25 107.8 . . ?
C24 C25 H25 107.8 . . ?
C27 C26 C25 110.3(5) . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26B 109.6 . . ?
C25 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
O7 C27 N3 121.4(6) . . ?
O7 C27 C26 120.1(6) . . ?
N3 C27 C26 118.5(6) . . ?
O8 C28 N4 121.9(7) . . ?
O8 C28 C29 119.2(7) . . ?
N4 C28 C29 118.8(6) . . ?
C30 C29 C34 117.9(7) . . ?
C30 C29 C28 118.0(7) . . ?
C34 C29 C28 124.1(7) . . ?
C311 C30 C29 118(4) . . ?
C29 C30 C31 119.8(9) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C33 C34 C29 118.4(8) . . ?
C29 C34 C331 120(3) . . ?
C33 C34 H34 120.8 . . ?
C29 C34 H34 120.8 . . ?
O10 N5 O9 127.8(11) . . ?
O10 N5 C31 115.3(12) . . ?
O9 N5 C31 116.8(11) . . ?
O11 N6 O12 122.7(9) . . ?
O11 N6 C33 117.1(11) . . ?
O12 N6 C33 120.2(9) . . ?
C32 C31 C30 122.8(13) . . ?
C32 C31 N5 119.9(14) . . ?
C30 C31 N5 117.2(12) . . ?
C31 C32 C33 117.2(15) . . ?
C31 C32 H32 121.4 . . ?
C33 C32 H32 121.4 . . ?
C32 C33 C34 123.8(11) . . ?
C32 C33 N6 119.6(12) . . ?
C34 C33 N6 116.6(10) . . ?
O101 N51 O9 129(7) . . ?
O101 N51 C311 115(7) . . ?
O9 N51 C311 106(6) . . ?
O111 N61 O121 123.0(14) . . ?
O111 N61 C331 123(6) . . ?
O121 N61 C331 114(6) . . ?
C30 C311 C321 126(8) . . ?
C30 C311 N51 122(7) . . ?
C321 C311 N51 110(8) . . ?
C331 C321 C311 110(9) . . ?
C331 C321 H321 125.2 . . ?
C311 C321 H321 125.2 . . ?
C321 C331 N61 115(8) . . ?
C321 C331 C34 118(6) . . ?
N61 C331 C34 124(6) . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H10H 109.5 . . ?
O100 C100 H10F 109.5 . . ?
H10H C100 H10F 109.5 . . ?
O100 C100 H10G 109.5 . . ?
H10H C100 H10G 109.5 . . ?
H10F C100 H10G 109.5 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H11A 109.5 . . ?
O110 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
O110 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
C120 O120 H120 109.5 . . ?
O120 C120 H12K 109.5 . . ?
O120 C120 H12I 109.5 . . ?
H12K C120 H12I 109.5 . . ?
O120 C120 H12J 109.5 . . ?
H12K C120 H12J 109.5 . . ?
H12I C120 H12J 109.5 . . ?
H21W O2W H22W 101.1 . . ?
H23W O21W H24W 120.6 . . ?
C300 O300 H300 109.5 . . ?
O300 C300 H30A 109.5 . . ?
O300 C300 H30B 109.5 . . ?
H30A C300 H30B 109.5 . . ?
O300 C300 H30C 109.5 . . ?
H30A C300 H30C 109.5 . . ?
H30B C300 H30C 109.5 . . ?
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
C22 O2 C2 C1 1.9(10) . . . . ?
C22 O2 C2 C3 -177.8(6) . . . . ?
C6 C1 C2 O2 179.6(6) . . . . ?
C6 C1 C2 C3 -0.7(11) . . . . ?
C23 O3 C3 C4 1.8(10) . . . . ?
C23 O3 C3 C2 -177.4(6) . . . . ?
O2 C2 C3 O3 -3.9(9) . . . . ?
C1 C2 C3 O3 176.4(6) . . . . ?
O2 C2 C3 C4 177.0(6) . . . . ?
C1 C2 C3 C4 -2.8(11) . . . . ?
O3 C3 C4 C5 -176.2(6) . . . . ?
C2 C3 C4 C5 2.9(11) . . . . ?
C3 C4 C5 C6 0.4(11) . . . . ?
C3 C4 C5 C7 -173.9(6) . . . . ?
C2 C1 C6 C5 4.0(11) . . . . ?
C2 C1 C6 N1 -177.3(7) . . . . ?
C4 C5 C6 C1 -3.9(11) . . . . ?
C7 C5 C6 C1 171.4(6) . . . . ?
C4 C5 C6 N1 177.2(6) . . . . ?
C7 C5 C6 N1 -7.5(8) . . . . ?
C9 N1 C6 C1 27.0(11) . . . . ?
C8 N1 C6 C1 177.3(7) . . . . ?
C9 N1 C6 C5 -154.2(6) . . . . ?
C8 N1 C6 C5 -4.0(8) . . . . ?
C6 C5 C7 C21 140.6(6) . . . . ?
C4 C5 C7 C21 -44.7(10) . . . . ?
C6 C5 C7 C17 -102.6(7) . . . . ?
C4 C5 C7 C17 72.1(9) . . . . ?
C6 C5 C7 C8 15.0(7) . . . . ?
C4 C5 C7 C8 -170.3(7) . . . . ?
C9 N1 C8 C18 42.6(8) . . . . ?
C6 N1 C8 C18 -108.8(6) . . . . ?
C9 N1 C8 C7 164.6(6) . . . . ?
C6 N1 C8 C7 13.1(7) . . . . ?
C5 C7 C8 N1 -16.3(6) . . . . ?
C21 C7 C8 N1 -141.6(6) . . . . ?
C17 C7 C8 N1 102.8(6) . . . . ?
C5 C7 C8 C18 98.6(6) . . . . ?
C21 C7 C8 C18 -26.7(9) . . . . ?
C17 C7 C8 C18 -142.3(6) . . . . ?
C6 N1 C9 O4 -25.4(11) . . . . ?
C8 N1 C9 O4 -173.0(6) . . . . ?
C6 N1 C9 C10 160.3(6) . . . . ?
C8 N1 C9 C10 12.8(9) . . . . ?
O4 C9 C10 C11 145.0(7) . . . . ?
N1 C9 C10 C11 -40.6(9) . . . . ?
C12 O1 C11 C18 -70.1(7) . . . . ?
C12 O1 C11 C10 169.7(5) . . . . ?
C9 C10 C11 O1 132.1(6) . . . . ?
C9 C10 C11 C18 8.9(8) . . . . ?
C11 O1 C12 C13 90.7(7) . . . . ?
O1 C12 C13 C14 -65.1(9) . . . . ?
C12 C13 C14 C19 -3.7(12) . . . . ?
C12 C13 C14 C15 176.1(6) . . . . ?
C16 N2 C15 C14 76.2(8) . . . . ?
C21 N2 C15 C14 -46.6(8) . . . . ?
C13 C14 C15 N2 -126.8(8) . . . . ?
C19 C14 C15 N2 53.1(9) . . . . ?
C15 N2 C16 C17 -143.6(6) . . . . ?
C21 N2 C16 C17 -18.2(7) . . . . ?
N2 C16 C17 C7 37.5(7) . . . . ?
C5 C7 C17 C16 -166.9(6) . . . . ?
C21 C7 C17 C16 -43.1(7) . . . . ?
C8 C7 C17 C16 80.0(7) . . . . ?
O1 C11 C18 C8 -70.8(7) . . . . ?
C10 C11 C18 C8 45.4(7) . . . . ?
O1 C11 C18 C19 57.8(8) . . . . ?
C10 C11 C18 C19 174.1(6) . . . . ?
N1 C8 C18 C11 -72.7(7) . . . . ?
C7 C8 C18 C11 172.7(6) . . . . ?
N1 C8 C18 C19 156.0(6) . . . . ?
C7 C8 C18 C19 41.3(8) . . . . ?
C13 C14 C19 C20 178.2(7) . . . . ?
C15 C14 C19 C20 -1.7(9) . . . . ?
C13 C14 C19 C18 59.4(11) . . . . ?
C15 C14 C19 C18 -120.5(7) . . . . ?
C11 C18 C19 C14 -66.5(9) . . . . ?
C8 C18 C19 C14 59.9(9) . . . . ?
C11 C18 C19 C20 172.1(6) . . . . ?
C8 C18 C19 C20 -61.5(8) . . . . ?
C14 C19 C20 C21 -55.2(8) . . . . ?
C18 C19 C20 C21 68.0(7) . . . . ?
C19 C20 C21 C7 -56.6(8) . . . . ?
C19 C20 C21 N2 62.3(7) . . . . ?
C5 C7 C21 C20 -83.7(8) . . . . ?
C17 C7 C21 C20 154.4(6) . . . . ?
C8 C7 C21 C20 34.9(9) . . . . ?
C5 C7 C21 N2 153.4(6) . . . . ?
C17 C7 C21 N2 31.4(7) . . . . ?
C8 C7 C21 N2 -88.0(7) . . . . ?
C15 N2 C21 C20 -9.8(8) . . . . ?
C16 N2 C21 C20 -134.2(6) . . . . ?
C15 N2 C21 C7 116.0(6) . . . . ?
C16 N2 C21 C7 -8.4(7) . . . . ?
C28 N4 C25 C26 144.6(6) . . . . ?
C28 N4 C25 C24 -91.9(7) . . . . ?
O6 C24 C25 N4 145.0(6) . . . . ?
O5 C24 C25 N4 -32.5(8) . . . . ?
O6 C24 C25 C26 -90.8(7) . . . . ?
O5 C24 C25 C26 91.7(7) . . . . ?
N4 C25 C26 C27 -57.4(7) . . . . ?
C24 C25 C26 C27 178.0(6) . . . . ?
C25 C26 C27 O7 -71.1(8) . . . . ?
C25 C26 C27 N3 105.7(7) . . . . ?
C25 N4 C28 O8 -9.3(10) . . . . ?
C25 N4 C28 C29 172.6(6) . . . . ?
O8 C28 C29 C30 -2.3(11) . . . . ?
N4 C28 C29 C30 175.8(7) . . . . ?
O8 C28 C29 C34 177.1(7) . . . . ?
N4 C28 C29 C34 -4.8(11) . . . . ?
C34 C29 C30 C311 22(4) . . . . ?
C28 C29 C30 C311 -159(4) . . . . ?
C34 C29 C30 C31 -4.0(12) . . . . ?
C28 C29 C30 C31 175.4(8) . . . . ?
C30 C29 C34 C33 3.6(10) . . . . ?
C28 C29 C34 C33 -175.9(7) . . . . ?
C30 C29 C34 C331 -19(3) . . . . ?
C28 C29 C34 C331 161(3) . . . . ?
N51 O9 N5 O10 89(7) . . . . ?
N51 O9 N5 C31 -86(7) . . . . ?
C311 C30 C31 C32 -89(12) . . . . ?
C29 C30 C31 C32 2.5(15) . . . . ?
C311 C30 C31 N5 90(12) . . . . ?
C29 C30 C31 N5 -178.4(8) . . . . ?
O10 N5 C31 C32 -3.4(17) . . . . ?
O9 N5 C31 C32 172.6(11) . . . . ?
O10 N5 C31 C30 177.5(11) . . . . ?
O9 N5 C31 C30 -6.5(15) . . . . ?
C30 C31 C32 C33 -0.3(16) . . . . ?
N5 C31 C32 C33 -179.4(9) . . . . ?
C31 C32 C33 C34 -0.1(15) . . . . ?
C31 C32 C33 N6 179.2(9) . . . . ?
C29 C34 C33 C32 -1.5(13) . . . . ?
C331 C34 C33 C32 100(8) . . . . ?
C29 C34 C33 N6 179.1(6) . . . . ?
C331 C34 C33 N6 -80(8) . . . . ?
O11 N6 C33 C32 -9.5(19) . . . . ?
O12 N6 C33 C32 169.7(9) . . . . ?
O11 N6 C33 C34 169.9(16) . . . . ?
O12 N6 C33 C34 -10.9(12) . . . . ?
N5 O9 N51 O101 -72(8) . . . . ?
N5 O9 N51 C311 70(6) . . . . ?
C29 C30 C311 C321 -31(8) . . . . ?
C31 C30 C311 C321 70(11) . . . . ?
C29 C30 C311 N51 171(4) . . . . ?
C31 C30 C311 N51 -88(12) . . . . ?
O101 N51 C311 C30 161(6) . . . . ?
O9 N51 C311 C30 14(8) . . . . ?
O101 N51 C311 C321 1(8) . . . . ?
O9 N51 C311 C321 -147(6) . . . . ?
C30 C311 C321 C331 33(10) . . . . ?
N51 C311 C321 C331 -167(6) . . . . ?
C311 C321 C331 N61 172(5) . . . . ?
C311 C321 C331 C34 -27(8) . . . . ?
O111 N61 C331 C321 17(7) . . . . ?
O121 N61 C331 C321 -159(6) . . . . ?
O111 N61 C331 C34 -143(8) . . . . ?
O121 N61 C331 C34 42(7) . . . . ?
C33 C34 C331 C321 -66(9) . . . . ?
C29 C34 C331 C321 24(7) . . . . ?
C33 C34 C331 N61 93(9) . . . . ?
C29 C34 C331 N61 -177(4) . . . . ?
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
N2 H24 O6 1.00 2.09 2.886(8) 134.9 .
N3 H37A O6 0.88 1.97 2.830(7) 167.0 1_556
N3 H37B O5 0.88 2.27 2.990(7) 139.0 2_658
N4 H47 O5 0.88 2.01 2.863(7) 163.0 2_658
O1W H11W O5 0.88 1.90 2.780(9) 178.5 1_556
O110 H110 O7 0.84 2.28 3.070(16) 156.6 1_554
O2W H21W O4 0.88 2.26 2.738(11) 113.7 4_556
O2W H22W O7 0.88 1.97 2.854(11) 179.4 1_554
O21W H23W O4 0.88 2.12 2.819(13) 136.4 4_556
O21W H24W O7 0.88 1.93 2.815(13) 179.2 1_554
_refine_diff_density_max 0.324
_refine_diff_density_min -0.398
_refine_diff_density_rms 0.060
_database_code_depnum_ccdc_archive 'CCDC 933062'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_BDNBLN
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
brucinium N-(3,5-dinitrobenzoyl)-L-asparaginate methanol 5-solvate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C23 H27 N2 O4, C11 H9 N6 O8, 5(C H4 O)'
_chemical_formula_sum 'C36.50 H46 N6 O14.50'
_chemical_formula_weight 800.79
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'
_space_group_crystal_system triclinic
_space_group_IT_number 1
_space_group_name_H-M_alt 'P 1'
_space_group_name_Hall 'P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
_cell_length_a 7.924(2)
_cell_length_b 12.140(3)
_cell_length_c 20.495(3)
_cell_angle_alpha 73.21(2)
_cell_angle_beta 79.37(2)
_cell_angle_gamma 80.53(3)
_cell_volume 1842.1(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 4068
_cell_measurement_theta_min 2.87
_cell_measurement_theta_max 28.74
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.444
_exptl_crystal_F_000 846
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.300
_exptl_crystal_size_mid 0.220
_exptl_crystal_size_min 0.040
_exptl_absorpt_coefficient_mu 0.113
_shelx_estimated_absorpt_T_min 0.967
_shelx_estimated_absorpt_T_max 0.996
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Ruby'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 17188
_diffrn_reflns_av_unetI/netI 0.1776
_diffrn_reflns_av_R_equivalents 0.0547
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 2.875
_diffrn_reflns_theta_max 28.799
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_point_group_measured_fraction_full 0.724
_reflns_number_total 12418
_reflns_number_gt 5490
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.417
_reflns_Friedel_fraction_max 0.380
_reflns_Friedel_fraction_full 0.453
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0524P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack 0.2(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 12418
_refine_ls_number_parameters 1302
_refine_ls_number_restraints 497
_refine_ls_R_factor_all 0.1573
_refine_ls_R_factor_gt 0.0631
_refine_ls_wR_factor_ref 0.1335
_refine_ls_wR_factor_gt 0.1103
_refine_ls_goodness_of_fit_ref 0.845
_refine_ls_restrained_S_all 0.846
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5196(5) -0.2871(4) 0.2963(2) 0.0301(11) Uani 1 1 d . . . . .
O2 O 0.5906(6) 0.4191(4) 0.0395(2) 0.0376(12) Uani 1 1 d . . . . .
O3 O 0.5774(6) 0.4821(4) 0.1505(2) 0.0349(11) Uani 1 1 d . . . . .
O4 O 0.5766(7) -0.0098(4) 0.0825(2) 0.0493(14) Uani 1 1 d . . . . .
N1 N 0.4704(6) 0.0284(5) 0.1854(2) 0.0275(13) Uani 1 1 d . . . . .
N2 N 0.3685(7) 0.0237(5) 0.4153(2) 0.0300(13) Uani 1 1 d . . . . .
H2A H 0.3444 0.0739 0.4478 0.036 Uiso 1 1 calc R U . . .
C1 C 0.5290(8) 0.2217(6) 0.1040(3) 0.0302(16) Uani 1 1 d . . . . .
H1A H 0.5385 0.1963 0.0636 0.036 Uiso 1 1 calc R U . . .
C2 C 0.5535(8) 0.3347(6) 0.0993(3) 0.0315(16) Uani 1 1 d . . . . .
C3 C 0.5445(8) 0.3712(6) 0.1598(3) 0.0259(15) Uani 1 1 d . . . . .
C4 C 0.5011(8) 0.2954(6) 0.2236(3) 0.0261(15) Uani 1 1 d . . . . .
H4A H 0.4898 0.3200 0.2644 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4744(8) 0.1843(6) 0.2277(3) 0.0270(16) Uani 1 1 d . . . . .
C6 C 0.4907(8) 0.1470(6) 0.1685(3) 0.0271(15) Uani 1 1 d . . . . .
C7 C 0.4166(8) 0.0883(5) 0.2894(3) 0.0249(15) Uani 1 1 d . . . . .
C8 C 0.4563(8) -0.0203(5) 0.2621(3) 0.0254(15) Uani 1 1 d . . . . .
H8A H 0.3577 -0.0681 0.2792 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5379(9) -0.0451(6) 0.1455(3) 0.0342(17) Uani 1 1 d . . . . .
C10 C 0.5592(8) -0.1711(6) 0.1817(3) 0.0306(16) Uani 1 1 d . . . . .
H10A H 0.6389 -0.2120 0.1507 0.037 Uiso 1 1 calc R U . . .
H10B H 0.4457 -0.2004 0.1897 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6288(8) -0.2041(6) 0.2516(3) 0.0312(16) Uani 1 1 d . . . . .
H11A H 0.7509 -0.2416 0.2462 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5699(9) -0.3422(6) 0.3626(3) 0.0400(18) Uani 1 1 d . . . . .
H12A H 0.6973 -0.3493 0.3591 0.048 Uiso 1 1 calc R U . . .
H12B H 0.5341 -0.4212 0.3793 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4865(8) -0.2723(6) 0.4139(3) 0.0336(17) Uani 1 1 d . . . . .
H13A H 0.4062 -0.3057 0.4522 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5232(8) -0.1663(6) 0.4062(3) 0.0291(16) Uani 1 1 d . . . . .
C15 C 0.4355(9) -0.0962(6) 0.4544(3) 0.0374(18) Uani 1 1 d . . . . .
H15A H 0.5182 -0.0905 0.4838 0.045 Uiso 1 1 calc R U . . .
H15B H 0.3381 -0.1352 0.4848 0.045 Uiso 1 1 calc R U . . .
C16 C 0.2019(8) 0.0261(6) 0.3887(3) 0.0356(17) Uani 1 1 d . . . . .
H16A H 0.1879 -0.0517 0.3856 0.043 Uiso 1 1 calc R U . . .
H16B H 0.1010 0.0527 0.4191 0.043 Uiso 1 1 calc R U . . .
C17 C 0.2204(8) 0.1107(6) 0.3183(3) 0.0268(15) Uani 1 1 d . . . . .
H17A H 0.1892 0.1915 0.3215 0.032 Uiso 1 1 calc R U . . .
H17B H 0.1463 0.0955 0.2886 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6220(8) -0.0948(6) 0.2754(3) 0.0308(16) Uani 1 1 d . . . . .
H18A H 0.7146 -0.0506 0.2437 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6608(9) -0.1105(6) 0.3493(3) 0.0321(16) Uani 1 1 d . . . . .
H19A H 0.7749 -0.1589 0.3551 0.039 Uiso 1 1 calc R U . . .
C20 C 0.6724(8) 0.0097(6) 0.3566(3) 0.0317(16) Uani 1 1 d . . . . .
H20A H 0.7125 0.0026 0.4007 0.038 Uiso 1 1 calc R U . . .
H20B H 0.7564 0.0495 0.3186 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4970(8) 0.0786(6) 0.3544(3) 0.0315(16) Uani 1 1 d . . . . .
H21A H 0.5065 0.1584 0.3567 0.038 Uiso 1 1 calc R U . . .
C22 C 0.5931(10) 0.3876(6) -0.0237(3) 0.0423(19) Uani 1 1 d . . . . .
H22A H 0.6205 0.4534 -0.0632 0.063 Uiso 1 1 calc R U . . .
H22B H 0.4795 0.3668 -0.0247 0.063 Uiso 1 1 calc R U . . .
H22C H 0.6811 0.3213 -0.0258 0.063 Uiso 1 1 calc R U . . .
C23 C 0.5753(9) 0.5151(6) 0.2116(3) 0.0338(17) Uani 1 1 d . . . . .
H23A H 0.6001 0.5956 0.1997 0.051 Uiso 1 1 calc R U . . .
H23B H 0.6634 0.4645 0.2379 0.051 Uiso 1 1 calc R U . . .
H23C H 0.4611 0.5081 0.2396 0.051 Uiso 1 1 calc R U . . .
O1A O 0.1258(6) -0.6458(4) 0.0661(2) 0.0399(12) Uani 1 1 d . . . . .
O2A O 0.0802(5) -0.1847(4) 0.3210(2) 0.0330(11) Uani 1 1 d . . . . .
O3A O 0.0436(6) -0.0101(4) 0.2136(2) 0.0340(11) Uani 1 1 d . . . . .
O4A O 0.1027(6) -0.5671(4) 0.2767(2) 0.0394(12) Uani 1 1 d . . . . .
N1A N 0.1647(7) -0.4460(5) 0.1707(2) 0.0288(13) Uani 1 1 d . . . . .
N2A N 0.2109(8) -0.2457(5) -0.0585(3) 0.0468(16) Uani 1 1 d . . . . .
H2AA H 0.2273 -0.1682 -0.0916 0.056 Uiso 1 1 calc R U . . .
C1A C 0.1246(8) -0.3232(6) 0.2545(3) 0.0288(16) Uani 1 1 d . . . . .
H1AA H 0.1311 -0.3869 0.2942 0.035 Uiso 1 1 calc R U . . .
C2A C 0.0969(8) -0.2108(6) 0.2588(3) 0.0275(16) Uani 1 1 d . . . . .
C3A C 0.0818(8) -0.1154(6) 0.2009(3) 0.0269(15) Uani 1 1 d . . . . .
C4A C 0.1088(8) -0.1353(5) 0.1362(3) 0.0270(15) Uani 1 1 d . . . . .
H4AA H 0.1049 -0.0719 0.0961 0.032 Uiso 1 1 calc R U . . .
C5A C 0.1410(8) -0.2471(6) 0.1302(3) 0.0293(16) Uani 1 1 d . . . . .
C6A C 0.1427(8) -0.3391(6) 0.1885(3) 0.0291(16) Uani 1 1 d . . . . .
C7A C 0.1891(9) -0.2914(5) 0.0668(3) 0.0280(15) Uani 1 1 d . . . . .
C8A C 0.1630(9) -0.4221(6) 0.0953(3) 0.0315(16) Uani 1 1 d . . . . .
H8AA H 0.2625 -0.4700 0.0750 0.038 Uiso 1 1 calc R U . . .
C9A C 0.1149(8) -0.5466(6) 0.2136(3) 0.0300(16) Uani 1 1 d . . . . .
C10A C 0.0782(8) -0.6351(6) 0.1808(3) 0.0321(16) Uani 1 1 d . . . . .
H10C H -0.0059 -0.6832 0.2140 0.039 Uiso 1 1 calc R U . . .
H10D H 0.1867 -0.6867 0.1740 0.039 Uiso 1 1 calc R U . . .
C11A C 0.0066(9) -0.5894(6) 0.1104(3) 0.0357(17) Uani 1 1 d . . . . .
H11B H -0.1102 -0.6147 0.1157 0.043 Uiso 1 1 calc R U . . .
C12A C 0.0705(10) -0.6317(7) 0.0001(4) 0.052(2) Uani 1 1 d . . . . .
H12C H -0.0572 -0.6265 0.0061 0.063 Uiso 1 1 calc R U . . .
H12D H 0.1191 -0.7002 -0.0172 0.063 Uiso 1 1 calc R U . . .
C13A C 0.1284(10) -0.5260(7) -0.0508(4) 0.048(2) Uani 1 1 d . . . . .
H13B H 0.2100 -0.5340 -0.0898 0.058 Uiso 1 1 calc R U . . .
C14A C 0.0709(10) -0.4206(7) -0.0440(3) 0.0429(19) Uani 1 1 d . . . . .
C15A C 0.1380(11) -0.3150(7) -0.0939(4) 0.050(2) Uani 1 1 d . . . . .
H15C H 0.2290 -0.3387 -0.1290 0.060 Uiso 1 1 calc R U . . .
H15D H 0.0428 -0.2663 -0.1178 0.060 Uiso 1 1 calc R U . . .
C16A C 0.3831(10) -0.3005(7) -0.0363(3) 0.048(2) Uani 1 1 d . . . . .
H16C H 0.4789 -0.2646 -0.0698 0.057 Uiso 1 1 calc R U . . .
H16D H 0.3991 -0.3847 -0.0322 0.057 Uiso 1 1 calc R U . . .
C17A C 0.3767(9) -0.2781(6) 0.0327(3) 0.0403(19) Uani 1 1 d . . . . .
H17C H 0.4046 -0.1991 0.0273 0.048 Uiso 1 1 calc R U . . .
H17D H 0.4586 -0.3352 0.0602 0.048 Uiso 1 1 calc R U . . .
C18A C -0.0075(9) -0.4573(6) 0.0871(3) 0.0334(17) Uani 1 1 d . . . . .
H18B H -0.0986 -0.4289 0.1212 0.040 Uiso 1 1 calc R U . . .
C19A C -0.0587(10) -0.3955(7) 0.0163(4) 0.0425(19) Uani 1 1 d . . . . .
H19B H -0.1720 -0.4192 0.0140 0.051 Uiso 1 1 calc R U . . .
C20A C -0.0841(9) -0.2666(6) 0.0105(4) 0.0424(19) Uani 1 1 d . . . . .
H20C H -0.1381 -0.2240 -0.0310 0.051 Uiso 1 1 calc R U . . .
H20D H -0.1619 -0.2511 0.0514 0.051 Uiso 1 1 calc R U . . .
C21A C 0.0877(9) -0.2261(6) 0.0056(3) 0.0404(18) Uani 1 1 d . . . . .
H21B H 0.0697 -0.1414 0.0027 0.049 Uiso 1 1 calc R U . . .
C22A C 0.0881(9) -0.2806(6) 0.3814(3) 0.0327(17) Uani 1 1 d . . . . .
H22D H 0.0774 -0.2514 0.4220 0.049 Uiso 1 1 calc R U . . .
H22E H 0.1990 -0.3292 0.3767 0.049 Uiso 1 1 calc R U . . .
H22F H -0.0066 -0.3266 0.3867 0.049 Uiso 1 1 calc R U . . .
C23A C 0.0195(10) 0.0859(6) 0.1556(4) 0.048(2) Uani 1 1 d . . . . .
H23D H -0.0073 0.1575 0.1704 0.073 Uiso 1 1 calc R U . . .
H23E H -0.0763 0.0766 0.1342 0.073 Uiso 1 1 calc R U . . .
H23F H 0.1255 0.0900 0.1221 0.073 Uiso 1 1 calc R U . . .
O5 O 1.0956(6) 0.0462(5) 0.5472(2) 0.0499(14) Uani 1 1 d . . . . .
O6 O 1.0136(5) -0.0806(4) 0.6473(2) 0.0304(11) Uani 1 1 d . . . . .
O7 O 0.5113(5) 0.1286(4) 0.4922(2) 0.0345(11) Uani 1 1 d . . . . .
O8 O 0.8405(7) -0.1962(5) 0.5063(3) 0.0607(16) Uani 1 1 d . . . . .
O9 O 0.709(4) -0.5607(17) 0.4969(9) 0.077(5) Uani 0.73(7) 1 d . U P . .
O91 O 0.634(10) -0.545(4) 0.494(3) 0.078(7) Uani 0.27(7) 1 d . U P . .
O10 O 0.5229(9) -0.6575(6) 0.5795(4) 0.086(2) Uani 1 1 d . . . . .
O12 O 0.4780(11) -0.4110(8) 0.8039(4) 0.071(3) Uani 0.778(11) 1 d . U P . .
O121 O 0.307(4) -0.350(3) 0.7738(13) 0.071(5) Uani 0.222(11) 1 d . U P A .
N3 N 0.3928(7) 0.0567(5) 0.6020(3) 0.0416(16) Uani 1 1 d . . . . .
H3A H 0.2934 0.0543 0.5894 0.050 Uiso 1 1 calc R U . . .
H3B H 0.4052 0.0335 0.6459 0.050 Uiso 1 1 calc R U . . .
N4 N 0.7404(6) -0.1202(5) 0.5950(3) 0.0306(13) Uani 1 1 d . . . . .
H4B H 0.6821 -0.1303 0.6368 0.037 Uiso 1 1 calc R U . . .
N5 N 0.6060(11) -0.5755(7) 0.5535(4) 0.065(2) Uani 1 1 d . . . . .
C24 C 0.9911(8) -0.0164(6) 0.5878(4) 0.0331(17) Uani 1 1 d . . . . .
C25 C 0.8158(8) -0.0132(6) 0.5634(3) 0.0332(17) Uani 1 1 d . . . . .
H25B H 0.8367 -0.0016 0.5124 0.040 Uiso 1 1 calc R U . . .
C26 C 0.6939(8) 0.0896(6) 0.5792(3) 0.0296(16) Uani 1 1 d . . . . .
H26C H 0.6747 0.0814 0.6294 0.036 Uiso 1 1 calc R U . . .
H26D H 0.7461 0.1622 0.5558 0.036 Uiso 1 1 calc R U . . .
C27 C 0.5240(9) 0.0952(6) 0.5548(4) 0.0336(17) Uani 1 1 d . . . . .
C28 C 0.7552(8) -0.2044(6) 0.5635(3) 0.0316(16) Uani 1 1 d . . . . .
C29 C 0.6713(8) -0.3093(6) 0.5986(3) 0.0318(17) Uani 1 1 d . . . . .
C30 C 0.6790(9) -0.3917(6) 0.5628(3) 0.0385(18) Uani 1 1 d . . . . .
H30C H 0.7384 -0.3796 0.5171 0.046 Uiso 1 1 calc R U . . .
C31 C 0.6015(10) -0.4897(7) 0.5933(4) 0.0435(18) Uani 1 1 d . U . . .
C34 C 0.5847(10) -0.3306(7) 0.6662(4) 0.050(2) Uani 1 1 d . . . . .
H341 H 0.5519 -0.2721 0.6900 0.060 Uiso 0.44(2) 1 calc R U P A 2
H34 H 0.5918 -0.2816 0.6941 0.060 Uiso 0.56(2) 1 calc R U P A 1
O11 O 0.314(2) -0.5162(13) 0.7843(6) 0.077(5) Uani 0.56(2) 1 d . U P A 1
N6 N 0.409(4) -0.442(2) 0.7598(11) 0.066(8) Uani 0.56(2) 1 d . U P A 1
C32 C 0.496(3) -0.508(2) 0.6592(13) 0.038(4) Uani 0.56(2) 1 d . U P A 1
H32C H 0.4346 -0.5734 0.6793 0.046 Uiso 0.56(2) 1 calc R U P A 1
C33 C 0.492(3) -0.4198(19) 0.6912(12) 0.036(4) Uani 0.56(2) 1 d . U P A 1
O111 O 0.460(4) -0.576(3) 0.8053(9) 0.133(12) Uani 0.44(2) 1 d . . P A 2
N61 N 0.468(7) -0.481(4) 0.7791(19) 0.084(9) Uani 0.44(2) 1 d . U P A 2
C321 C 0.548(3) -0.530(3) 0.6623(18) 0.040(4) Uani 0.44(2) 1 d . U P A 2
H32D H 0.5134 -0.6050 0.6833 0.048 Uiso 0.44(2) 1 calc R U P A 2
C331 C 0.549(3) -0.452(2) 0.6974(16) 0.039(4) Uani 0.44(2) 1 d . U P A 2
O5A O 0.4139(5) -0.0908(4) 0.8313(2) 0.0344(11) Uani 1 1 d . . . . .
O6A O 0.5300(5) -0.1023(4) 0.7253(2) 0.0328(11) Uani 1 1 d . . . . .
O7A O 0.9818(6) -0.0424(4) 0.8744(2) 0.0409(13) Uani 1 1 d . . . . .
N3A N 1.1074(7) -0.0360(6) 0.7659(3) 0.0483(18) Uani 1 1 d . . . . .
H3AA H 1.2118 -0.0515 0.7778 0.058 Uiso 1 1 calc R U . . .
H3AB H 1.0942 -0.0255 0.7228 0.058 Uiso 1 1 calc R U . . .
N4A N 0.8334(6) -0.2079(5) 0.7743(3) 0.0297(13) Uani 1 1 d . . . . .
H4AB H 0.9022 -0.1815 0.7358 0.036 Uiso 1 1 calc R U . . .
N6A N 1.1676(8) -0.3897(6) 0.5816(3) 0.0446(16) Uani 1 1 d . . . . .
C24A C 0.5403(8) -0.1073(6) 0.7877(3) 0.0309(16) Uani 1 1 d . . . . .
C25A C 0.7205(8) -0.1253(6) 0.8081(3) 0.0285(16) Uani 1 1 d . . . . .
H25A H 0.7113 -0.1592 0.8591 0.034 Uiso 1 1 calc R U . . .
C26A C 0.7974(7) -0.0111(6) 0.7897(3) 0.0269(15) Uani 1 1 d . . . . .
H26A H 0.8093 0.0230 0.7392 0.032 Uiso 1 1 calc R U . . .
H26B H 0.7181 0.0440 0.8119 0.032 Uiso 1 1 calc R U . . .
C27A C 0.9710(8) -0.0284(6) 0.8129(4) 0.0350(17) Uani 1 1 d . . . . .
C28A C 0.8336(10) -0.3206(7) 0.8005(4) 0.049(2) Uani 1 1 d . . . . .
C34A C 1.0143(8) -0.3588(6) 0.6915(3) 0.0349(17) Uani 1 1 d . . . . .
H34B H 0.9878 -0.2809 0.6659 0.042 Uiso 0.244(6) 1 calc R U P B 2
H34A H 1.0487 -0.2832 0.6786 0.042 Uiso 0.756(6) 1 calc R U P B 1
O8A O 0.7725(11) -0.3657(9) 0.8640(4) 0.048(2) Uani 0.756(6) 1 d . U P B 1
O9A O 0.8289(19) -0.7412(9) 0.8099(6) 0.173(7) Uani 0.756(6) 1 d . . P B 1
O10A O 0.896(2) -0.7447(15) 0.7044(8) 0.119(5) Uani 0.756(6) 1 d . U P B 1
O11A O 1.1942(11) -0.4450(8) 0.5392(4) 0.054(2) Uani 0.756(6) 1 d . U P B 1
O12A O 1.2267(11) -0.2931(8) 0.5689(4) 0.048(2) Uani 0.756(6) 1 d . U P B 1
N5A N 0.8879(15) -0.7028(9) 0.7538(8) 0.095(4) Uani 0.756(6) 1 d . U P B 1
C29A C 0.9142(19) -0.3977(18) 0.7527(8) 0.042(4) Uani 0.756(6) 1 d . U P B 1
C30A C 0.8810(15) -0.5133(10) 0.7730(6) 0.059(3) Uani 0.756(6) 1 d . . P B 1
H30A H 0.8203 -0.5442 0.8174 0.071 Uiso 0.756(6) 1 calc R U P B 1
C31A C 0.9355(14) -0.5816(9) 0.7290(7) 0.066(3) Uani 0.756(6) 1 d . U P B 1
C32A C 1.0304(12) -0.5425(8) 0.6629(5) 0.042(2) Uani 0.756(6) 1 d . U P B 1
H32A H 1.0657 -0.5898 0.6319 0.050 Uiso 0.756(6) 1 calc R U P B 1
C33A C 1.0665(17) -0.4319(16) 0.6474(7) 0.035(3) Uani 0.756(6) 1 d . U P B 1
O8B O 0.712(4) -0.363(3) 0.8433(15) 0.044(6) Uani 0.244(6) 1 d . U P B 2
O9B O 1.064(3) -0.737(2) 0.8642(14) 0.083(8) Uani 0.244(6) 1 d . U P B 2
O10B O 1.234(4) -0.769(3) 0.7713(13) 0.056(6) Uani 0.244(6) 1 d . U P B 2
O11B O 1.262(4) -0.473(3) 0.5615(15) 0.056(6) Uani 0.244(6) 1 d . U P B 2
O12B O 1.136(3) -0.292(3) 0.5583(14) 0.051(6) Uani 0.244(6) 1 d . U P B 2
N5B N 1.132(4) -0.712(3) 0.8055(17) 0.066(7) Uani 0.244(6) 1 d . U P B 2
C29B C 0.958(7) -0.401(6) 0.769(3) 0.034(8) Uani 0.244(6) 1 d . U P B 2
C30B C 0.982(4) -0.510(3) 0.7995(15) 0.037(8) Uani 0.244(6) 1 d . U P B 2
H30B H 0.9272 -0.5374 0.8455 0.044 Uiso 0.244(6) 1 calc R U P B 2
C31B C 1.085(5) -0.588(3) 0.7673(19) 0.066(6) Uani 0.244(6) 1 d . U P B 2
C32B C 1.145(4) -0.551(2) 0.6935(14) 0.034(4) Uani 0.244(6) 1 d . U P B 2
H32B H 1.2093 -0.6034 0.6686 0.041 Uiso 0.244(6) 1 calc R U P B 2
C33B C 1.102(6) -0.439(6) 0.663(2) 0.034(5) Uani 0.244(6) 1 d . U P B 2
O100 O 0.734(2) 0.0904(14) -0.0510(8) 0.122(5) Uani 0.489(12) 1 d D U P C 1
H100 H 0.6533 0.0712 -0.0186 0.183 Uiso 0.489(12) 1 calc R U P C 1
C100 C 0.884(3) 0.098(3) -0.0232(18) 0.118(5) Uani 0.489(12) 1 d D U P C 1
H10G H 0.9780 0.1216 -0.0610 0.177 Uiso 0.489(12) 1 calc R U P C 1
H10E H 0.9212 0.0229 0.0070 0.177 Uiso 0.489(12) 1 calc R U P C 1
H10F H 0.8560 0.1562 0.0032 0.177 Uiso 0.489(12) 1 calc R U P C 1
O101 O 1.084(3) 0.0636(15) -0.0250(9) 0.150(5) Uani 0.511(12) 1 d D U P C 2
H101 H 1.1064 0.1175 -0.0605 0.225 Uiso 0.511(12) 1 calc R U P C 2
C101 C 0.900(3) 0.057(3) -0.0106(18) 0.116(5) Uani 0.511(12) 1 d D U P C 2
H10K H 0.8613 0.0456 0.0389 0.174 Uiso 0.511(12) 1 calc R U P C 2
H10L H 0.8745 -0.0079 -0.0250 0.174 Uiso 0.511(12) 1 calc R U P C 2
H10J H 0.8399 0.1295 -0.0361 0.174 Uiso 0.511(12) 1 calc R U P C 2
O110 O 1.456(2) 0.1785(15) -0.0956(8) 0.141(5) Uani 0.599(13) 1 d D U P D 1
H110 H 1.4912 0.1989 -0.0651 0.212 Uiso 0.599(13) 1 calc R U P D 1
C110 C 1.367(4) 0.0775(19) -0.0642(15) 0.155(6) Uani 0.599(13) 1 d D U P D 1
H11C H 1.2479 0.0949 -0.0739 0.233 Uiso 0.599(13) 1 calc R U P D 1
H11D H 1.3678 0.0556 -0.0143 0.233 Uiso 0.599(13) 1 calc R U P D 1
H11E H 1.4263 0.0135 -0.0831 0.233 Uiso 0.599(13) 1 calc R U P D 1
O120 O 1.287(4) 0.195(2) -0.0964(13) 0.156(6) Uani 0.401(13) 1 d D U P D 3
H120 H 1.2671 0.2027 -0.1365 0.234 Uiso 0.401(13) 1 calc R U P D 3
C120 C 1.270(6) 0.077(3) -0.056(2) 0.152(6) Uani 0.401(13) 1 d D U P D 3
H12E H 1.3857 0.0344 -0.0507 0.229 Uiso 0.401(13) 1 calc R U P D 3
H12F H 1.2101 0.0390 -0.0799 0.229 Uiso 0.401(13) 1 calc R U P D 3
H12G H 1.2044 0.0767 -0.0108 0.229 Uiso 0.401(13) 1 calc R U P D 3
O200 O 0.5887(8) 0.3287(5) 0.3809(3) 0.0775(18) Uani 1 1 d D . . E 3
H200 H 0.5426 0.2767 0.4126 0.116 Uiso 1 1 calc R U . E 3
C200 C 0.7745(9) 0.3012(9) 0.3739(5) 0.073(3) Uani 1 1 d D . . E 3
H20I H 0.8277 0.3707 0.3699 0.110 Uiso 1 1 calc R U . E 3
H20E H 0.8158 0.2740 0.3325 0.110 Uiso 1 1 calc R U . E 3
H20F H 0.8061 0.2404 0.4144 0.110 Uiso 1 1 calc R U . E 3
O300 O 1.491(3) -0.760(2) 0.7560(14) 0.111(15) Uani 0.253(17) 1 d D U P B 3
H300 H 1.4506 -0.6958 0.7630 0.167 Uiso 0.253(17) 1 calc R U P B 3
O301 O 1.2875(18) -0.7082(12) 0.7604(7) 0.064(5) Uani 0.467(17) 1 d D U P B 4
H301 H 1.3645 -0.6839 0.7739 0.095 Uiso 0.467(17) 1 calc R U P B 4
C300 C 1.357(2) -0.8120(13) 0.7403(9) 0.115(6) Uani 0.756(6) 1 d D . P . .
H30G H 1.3069 -0.8801 0.7683 0.173 Uiso 0.467(17) 1 d R U P B 4
H30H H 1.4811 -0.8254 0.7308 0.173 Uiso 0.467(17) 1 d R U P B 4
H30I H 1.2923 -0.7621 0.6967 0.173 Uiso 0.467(17) 1 d R U P B 4
H30D H 1.2710 -0.8254 0.7804 0.173 Uiso 0.253(17) 1 d R U P B 3
H30E H 1.4025 -0.8862 0.7326 0.173 Uiso 0.253(17) 1 d R U P B 3
H30F H 1.2923 -0.7621 0.6967 0.173 Uiso 0.253(17) 1 d R U P B 3
O302 O 0.950(15) -0.772(11) 0.722(2) 0.119(10) Uani 0.127(17) 1 d D U P B 2
H302 H 1.0494 -0.7647 0.7286 0.179 Uiso 0.127(17) 1 calc R U P B 2
O303 O 0.937(5) -0.623(3) 0.6094(18) 0.069(16) Uani 0.152(14) 1 d D U P B 4
H303 H 0.8726 -0.6117 0.5792 0.103 Uiso 0.152(14) 1 calc R U P B 4
C302 C 0.942(6) -0.743(3) 0.650(2) 0.092(15) Uani 0.244(6) 1 d D U P . .
H30P H 0.9382 -0.7485 0.6976 0.137 Uiso 0.152(14) 1 d R U P B 4
H30O H 0.9335 -0.6608 0.6281 0.137 Uiso 0.152(14) 1 d R U P B 4
H30M H 0.8490 -0.7766 0.6420 0.137 Uiso 0.152(14) 1 d R U P B 4
H30N H 1.0479 -0.7820 0.6316 0.137 Uiso 0.127(17) 1 d R U P B 2
H30R H 0.9382 -0.7485 0.6976 0.137 Uiso 0.127(17) 1 d R U P B 2
H30S H 0.9335 -0.6608 0.6281 0.137 Uiso 0.127(17) 1 d R U P B 2
O310 O 1.1526(16) -0.7559(9) 0.4375(7) 0.076(4) Uani 0.530(11) 1 d D U P F 5
H310 H 1.1241 -0.8076 0.4735 0.114 Uiso 0.530(11) 1 calc R U P F 5
O320 O 1.247(3) -0.6989(19) 0.3971(8) 0.085(5) Uani 0.338(11) 1 d D U P F 6
H320 H 1.2242 -0.6488 0.3609 0.127 Uiso 0.338(11) 1 calc R U P F 6
C310 C 1.1775(14) -0.6544(8) 0.4558(5) 0.067(3) Uani 0.868(8) 1 d D U P . .
H31G H 1.0656 -0.6183 0.4739 0.101 Uiso 0.530(11) 1 calc R U P F 5
H31C H 1.2295 -0.5992 0.4149 0.101 Uiso 0.530(11) 1 calc R U P F 5
H31D H 1.2543 -0.6765 0.4910 0.101 Uiso 0.530(11) 1 calc R U P F 5
H32H H 1.0559 -0.6679 0.4701 0.101 Uiso 0.338(11) 1 calc R U P F 6
H32E H 1.1858 -0.5710 0.4434 0.101 Uiso 0.338(11) 1 calc R U P F 6
H32F H 1.2432 -0.6940 0.4938 0.101 Uiso 0.338(11) 1 calc R U P F 6
O330 O 1.023(7) -0.628(4) 0.481(2) 0.080(7) Uani 0.132(8) 1 d D U P B 7
H330 H 0.9552 -0.6510 0.4616 0.121 Uiso 0.132(8) 1 calc R U P B 7
C330 C 1.007(9) -0.697(6) 0.551(2) 0.077(10) Uani 0.132(8) 1 d D U P B 7
H33L H 0.9227 -0.6556 0.5800 0.115 Uiso 0.132(8) 1 calc R U P B 7
H33J H 1.1194 -0.7113 0.5674 0.115 Uiso 0.132(8) 1 calc R U P B 7
H33K H 0.9677 -0.7711 0.5544 0.115 Uiso 0.132(8) 1 calc R U P B 7
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
O1 0.036(3) 0.034(3) 0.025(2) -0.005(2) -0.009(2) -0.015(2)
O2 0.055(3) 0.038(3) 0.021(2) -0.006(2) -0.003(2) -0.014(2)
O3 0.045(3) 0.029(3) 0.031(3) -0.011(2) 0.001(2) -0.007(2)
O4 0.085(4) 0.041(3) 0.021(3) -0.009(2) 0.011(3) -0.025(3)
N1 0.034(3) 0.028(3) 0.025(3) -0.007(3) -0.007(2) -0.011(3)
N2 0.044(3) 0.030(3) 0.019(3) -0.008(3) -0.003(3) -0.012(3)
C1 0.035(4) 0.032(4) 0.028(4) -0.012(3) -0.005(3) -0.008(3)
C2 0.038(4) 0.032(4) 0.027(4) -0.004(3) -0.007(3) -0.018(3)
C3 0.026(4) 0.022(4) 0.031(4) -0.005(3) -0.002(3) -0.010(3)
C4 0.030(4) 0.025(4) 0.026(4) -0.012(3) -0.002(3) -0.005(3)
C5 0.021(4) 0.033(4) 0.024(4) -0.004(3) 0.000(3) -0.004(3)
C6 0.031(4) 0.030(4) 0.019(3) -0.003(3) -0.001(3) -0.010(3)
C7 0.027(4) 0.027(4) 0.023(3) -0.004(3) -0.010(3) -0.004(3)
C8 0.030(4) 0.025(4) 0.022(3) -0.008(3) -0.008(3) 0.000(3)
C9 0.037(4) 0.036(5) 0.034(4) -0.017(4) 0.003(3) -0.013(4)
C10 0.028(4) 0.030(4) 0.039(4) -0.019(3) -0.002(3) -0.003(3)
C11 0.025(4) 0.032(4) 0.040(4) -0.013(3) -0.012(3) 0.000(3)
C12 0.043(4) 0.030(4) 0.042(4) 0.002(4) -0.013(4) -0.007(4)
C13 0.033(4) 0.046(5) 0.021(3) -0.004(3) -0.007(3) -0.006(4)
C14 0.035(4) 0.025(4) 0.030(4) -0.002(3) -0.019(3) -0.003(3)
C15 0.055(5) 0.038(5) 0.023(4) -0.007(3) -0.013(3) -0.009(4)
C16 0.036(4) 0.048(5) 0.023(4) -0.009(3) -0.002(3) -0.011(4)
C17 0.029(4) 0.029(4) 0.024(4) -0.011(3) -0.004(3) -0.001(3)
C18 0.031(4) 0.032(4) 0.028(4) -0.005(3) -0.002(3) -0.007(3)
C19 0.037(4) 0.029(4) 0.031(4) -0.004(3) -0.014(3) -0.002(3)
C20 0.030(4) 0.037(4) 0.031(4) -0.008(3) -0.009(3) -0.010(3)
C21 0.038(4) 0.036(4) 0.024(4) -0.007(3) -0.006(3) -0.011(3)
C22 0.066(5) 0.043(5) 0.024(4) -0.011(3) -0.003(4) -0.021(4)
C23 0.046(4) 0.033(4) 0.031(4) -0.014(3) -0.003(3) -0.019(4)
O1A 0.050(3) 0.037(3) 0.039(3) -0.017(2) -0.016(2) 0.000(2)
O2A 0.034(3) 0.043(3) 0.024(2) -0.012(2) -0.005(2) -0.004(2)
O3A 0.046(3) 0.027(3) 0.033(3) -0.004(2) -0.018(2) -0.007(2)
O4A 0.053(3) 0.035(3) 0.030(3) -0.007(2) -0.004(2) -0.009(2)
N1A 0.038(3) 0.030(3) 0.021(3) -0.005(3) -0.010(2) -0.008(3)
N2A 0.063(4) 0.040(4) 0.033(3) -0.005(3) -0.002(3) -0.006(3)
C1A 0.035(4) 0.035(4) 0.019(3) -0.005(3) -0.011(3) -0.007(3)
C2A 0.022(4) 0.044(5) 0.020(4) -0.014(3) -0.001(3) -0.007(3)
C3A 0.026(4) 0.024(4) 0.031(4) -0.003(3) -0.008(3) -0.006(3)
C4A 0.038(4) 0.018(4) 0.025(4) -0.001(3) -0.012(3) -0.003(3)
C5A 0.029(4) 0.029(4) 0.028(4) 0.000(3) -0.011(3) -0.005(3)
C6A 0.029(4) 0.030(4) 0.031(4) -0.009(3) -0.006(3) -0.007(3)
C7A 0.041(4) 0.027(4) 0.018(3) -0.004(3) -0.009(3) -0.006(3)
C8A 0.040(4) 0.032(4) 0.025(4) -0.006(3) -0.011(3) -0.005(3)
C9A 0.031(4) 0.037(4) 0.023(4) -0.008(3) -0.003(3) -0.009(3)
C10A 0.029(4) 0.031(4) 0.039(4) -0.012(3) -0.004(3) -0.005(3)
C11A 0.031(4) 0.041(5) 0.046(4) -0.025(4) -0.018(3) 0.004(3)
C12A 0.067(6) 0.058(6) 0.046(5) -0.037(5) -0.019(4) 0.004(5)
C13A 0.066(6) 0.053(6) 0.031(4) -0.021(4) -0.020(4) 0.010(5)
C14A 0.061(5) 0.046(5) 0.024(4) -0.013(4) -0.017(4) 0.006(4)
C15A 0.068(6) 0.058(6) 0.030(4) -0.022(4) -0.017(4) 0.006(5)
C16A 0.055(5) 0.054(5) 0.028(4) -0.004(4) -0.001(4) -0.005(4)
C17A 0.052(5) 0.042(5) 0.024(4) 0.004(3) -0.004(3) -0.020(4)
C18A 0.034(4) 0.046(5) 0.027(4) -0.013(3) -0.015(3) -0.007(4)
C19A 0.046(5) 0.045(5) 0.038(4) -0.013(4) -0.014(4) 0.002(4)
C20A 0.053(5) 0.038(5) 0.037(4) -0.008(4) -0.024(4) 0.006(4)
C21A 0.057(5) 0.031(4) 0.034(4) -0.005(3) -0.017(4) -0.004(4)
C22A 0.034(4) 0.038(4) 0.025(4) -0.005(3) -0.008(3) -0.003(3)
C23A 0.067(6) 0.037(5) 0.041(5) -0.004(4) -0.016(4) -0.005(4)
O5 0.036(3) 0.073(4) 0.034(3) 0.015(3) -0.015(2) -0.027(3)
O6 0.027(3) 0.034(3) 0.025(2) 0.002(2) -0.007(2) -0.003(2)
O7 0.033(3) 0.044(3) 0.028(3) -0.007(2) -0.009(2) -0.006(2)
O8 0.075(4) 0.078(4) 0.036(3) -0.031(3) 0.013(3) -0.023(3)
O9 0.066(12) 0.098(7) 0.092(6) -0.075(6) 0.000(8) -0.005(8)
O91 0.076(12) 0.091(10) 0.080(9) -0.049(8) -0.007(10) -0.002(10)
O10 0.122(6) 0.046(4) 0.103(6) -0.037(4) -0.016(4) -0.020(4)
O12 0.093(6) 0.075(6) 0.047(5) -0.027(4) 0.024(4) -0.033(5)
O121 0.082(8) 0.076(8) 0.053(8) -0.014(7) 0.014(7) -0.030(7)
N3 0.028(3) 0.065(5) 0.031(3) 0.001(3) -0.012(3) -0.018(3)
N4 0.021(3) 0.040(4) 0.030(3) -0.010(3) 0.000(2) -0.003(3)
N5 0.085(6) 0.061(6) 0.063(5) -0.033(5) -0.029(5) 0.002(5)
C24 0.020(4) 0.044(5) 0.034(4) -0.002(4) -0.007(3) -0.012(3)
C25 0.027(4) 0.047(5) 0.027(4) -0.008(3) -0.005(3) -0.014(4)
C26 0.034(4) 0.038(4) 0.020(3) -0.004(3) -0.010(3) -0.011(3)
C27 0.043(5) 0.026(4) 0.035(4) -0.009(3) -0.012(4) -0.003(4)
C28 0.026(4) 0.046(5) 0.027(4) -0.015(4) -0.007(3) -0.003(3)
C29 0.026(4) 0.041(5) 0.029(4) -0.017(4) 0.001(3) 0.002(3)
C30 0.044(5) 0.047(5) 0.029(4) -0.017(4) -0.013(3) 0.002(4)
C31 0.048(5) 0.041(5) 0.051(4) -0.026(4) -0.015(4) -0.001(4)
C34 0.054(5) 0.057(6) 0.048(5) -0.033(4) 0.010(4) -0.019(4)
O11 0.091(10) 0.079(9) 0.045(7) 0.005(6) 0.012(6) -0.029(7)
N6 0.12(2) 0.058(19) 0.016(11) 0.002(9) 0.010(9) -0.052(16)
C32 0.036(8) 0.035(8) 0.040(5) -0.004(6) -0.009(7) -0.001(6)
C33 0.034(9) 0.037(9) 0.035(6) -0.006(7) -0.004(7) -0.004(7)
O111 0.17(3) 0.16(2) 0.059(11) 0.010(13) 0.010(13) -0.09(2)
N61 0.14(2) 0.07(2) 0.031(16) -0.003(13) 0.019(13) -0.053(19)
C321 0.041(9) 0.038(8) 0.042(6) -0.012(7) -0.003(8) -0.007(7)
C331 0.040(10) 0.036(10) 0.037(7) -0.007(7) 0.003(8) -0.005(8)
O5A 0.020(2) 0.056(3) 0.030(3) -0.018(2) 0.001(2) -0.005(2)
O6A 0.028(3) 0.047(3) 0.026(3) -0.013(2) -0.007(2) -0.002(2)
O7A 0.036(3) 0.067(4) 0.019(3) -0.006(2) -0.008(2) -0.011(3)
N3A 0.025(3) 0.087(5) 0.029(3) -0.009(3) -0.006(3) -0.004(3)
N4A 0.017(3) 0.038(4) 0.029(3) -0.004(3) 0.006(2) -0.007(3)
N6A 0.044(4) 0.046(5) 0.041(4) -0.018(4) 0.002(3) 0.002(4)
C24A 0.024(4) 0.032(4) 0.032(4) -0.002(3) -0.003(3) -0.003(3)
C25A 0.021(4) 0.037(4) 0.021(3) -0.002(3) 0.004(3) -0.007(3)
C26A 0.017(3) 0.041(4) 0.019(3) -0.004(3) -0.005(3) 0.003(3)
C27A 0.022(4) 0.039(4) 0.040(5) -0.001(4) -0.005(3) -0.012(3)
C28A 0.045(5) 0.040(5) 0.045(5) 0.004(4) 0.013(4) -0.005(4)
C34A 0.030(4) 0.030(4) 0.043(4) -0.006(4) -0.012(3) 0.002(3)
O8A 0.042(6) 0.050(4) 0.041(5) -0.003(4) 0.001(4) -0.002(4)
O9A 0.260(16) 0.066(7) 0.147(10) -0.026(7) 0.141(11) -0.084(9)
O10A 0.100(11) 0.085(10) 0.170(11) -0.051(9) 0.050(8) -0.052(8)
O11A 0.062(6) 0.054(6) 0.046(6) -0.021(5) 0.006(4) -0.003(5)
O12A 0.062(6) 0.039(4) 0.039(4) -0.009(3) 0.010(4) -0.020(5)
N5A 0.095(7) 0.041(6) 0.135(9) -0.038(7) 0.055(7) -0.024(6)
C29A 0.036(9) 0.023(5) 0.045(10) 0.011(7) 0.012(6) 0.006(7)
C30A 0.043(7) 0.045(8) 0.062(8) 0.008(6) 0.024(6) -0.002(6)
C31A 0.054(6) 0.028(5) 0.099(7) -0.017(6) 0.032(6) -0.005(5)
C32A 0.027(5) 0.035(5) 0.056(6) -0.007(5) 0.006(4) -0.003(4)
C33A 0.027(6) 0.028(5) 0.043(7) -0.003(5) 0.001(4) 0.000(5)
O8B 0.039(10) 0.034(8) 0.044(9) 0.000(8) 0.009(8) -0.003(8)
O9B 0.095(13) 0.076(12) 0.073(12) -0.029(10) 0.010(10) -0.007(10)
O10B 0.078(10) 0.046(10) 0.062(9) -0.033(8) -0.026(8) -0.010(8)
O11B 0.061(10) 0.058(9) 0.050(10) -0.021(8) -0.004(8) 0.001(8)
O12B 0.053(10) 0.051(9) 0.037(8) -0.002(7) 0.005(8) -0.001(9)
N5B 0.067(10) 0.060(10) 0.065(10) -0.012(8) 0.000(8) -0.009(9)
C29B 0.031(12) 0.027(9) 0.032(11) 0.003(9) 0.004(9) -0.003(9)
C30B 0.043(12) 0.038(13) 0.035(12) -0.019(10) -0.011(10) 0.003(10)
C31B 0.067(9) 0.051(8) 0.075(9) -0.019(7) 0.006(7) -0.009(8)
C32B 0.034(7) 0.030(7) 0.037(7) -0.011(6) 0.004(6) -0.004(6)
C33B 0.028(8) 0.032(7) 0.037(8) -0.009(7) 0.006(6) -0.003(7)
O100 0.131(8) 0.117(8) 0.115(8) -0.042(7) 0.001(6) -0.007(7)
C100 0.129(8) 0.114(8) 0.116(8) -0.047(7) -0.002(7) -0.013(7)
O101 0.147(8) 0.117(8) 0.158(8) -0.013(7) 0.012(7) -0.019(7)
C101 0.128(8) 0.111(8) 0.113(7) -0.047(7) -0.003(7) -0.012(7)
O110 0.149(10) 0.168(9) 0.136(8) -0.079(8) -0.046(8) -0.002(8)
C110 0.156(11) 0.166(10) 0.146(9) -0.051(9) -0.033(9) 0.006(9)
O120 0.156(10) 0.169(9) 0.148(8) -0.053(7) -0.031(8) -0.005(8)
C120 0.152(10) 0.166(9) 0.144(9) -0.053(8) -0.036(8) 0.005(8)
O200 0.093(5) 0.074(5) 0.070(4) -0.016(4) -0.015(4) -0.027(4)
C200 0.036(5) 0.100(8) 0.103(8) -0.057(6) 0.002(5) -0.021(5)
O300 0.110(18) 0.097(17) 0.111(17) -0.002(11) -0.020(11) -0.008(11)
O301 0.072(8) 0.057(8) 0.068(7) -0.017(6) -0.012(6) -0.021(6)
C300 0.087(12) 0.120(15) 0.144(15) -0.035(13) -0.024(11) -0.015(11)
O302 0.107(13) 0.100(13) 0.147(12) -0.039(10) 0.018(9) -0.034(10)
O303 0.075(19) 0.059(19) 0.072(19) -0.027(12) -0.009(11) 0.008(11)
C302 0.095(18) 0.088(19) 0.093(18) -0.022(12) -0.014(12) -0.019(12)
O310 0.091(8) 0.063(7) 0.081(7) -0.025(6) -0.028(6) 0.001(6)
O320 0.096(8) 0.078(8) 0.078(8) -0.024(6) -0.019(7) 0.009(7)
C310 0.080(6) 0.057(5) 0.072(5) -0.032(4) -0.022(5) 0.006(5)
O330 0.087(10) 0.075(10) 0.082(9) -0.026(8) -0.015(8) -0.004(8)
C330 0.081(12) 0.077(12) 0.078(12) -0.025(9) -0.021(10) -0.009(10)
_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
O1 C12 1.429(7) . ?
O1 C11 1.436(7) . ?
O2 C2 1.371(7) . ?
O2 C22 1.447(7) . ?
O3 C3 1.366(7) . ?
O3 C23 1.418(7) . ?
O4 C9 1.235(7) . ?
N1 C9 1.362(7) . ?
N1 C6 1.410(8) . ?
N1 C8 1.501(7) . ?
N2 C15 1.507(8) . ?
N2 C16 1.512(8) . ?
N2 C21 1.521(8) . ?
N2 H2A 1.0000 . ?
C1 C6 1.383(8) . ?
C1 C2 1.391(8) . ?
C1 H1A 0.9500 . ?
C2 C3 1.419(8) . ?
C3 C4 1.385(8) . ?
C4 C5 1.376(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(8) . ?
C5 C7 1.508(8) . ?
C7 C8 1.541(8) . ?
C7 C21 1.546(8) . ?
C7 C17 1.567(8) . ?
C8 C18 1.488(9) . ?
C8 H8A 1.0000 . ?
C9 C10 1.491(9) . ?
C10 C11 1.551(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.529(9) . ?
C11 H11A 1.0000 . ?
C12 C13 1.528(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.325(9) . ?
C13 H13A 0.9500 . ?
C14 C15 1.491(9) . ?
C14 C19 1.524(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.508(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.554(8) . ?
C18 H18A 1.0000 . ?
C19 C20 1.528(9) . ?
C19 H19A 1.0000 . ?
C20 C21 1.501(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1A C11A 1.419(8) . ?
O1A C12A 1.453(8) . ?
O2A C2A 1.380(7) . ?
O2A C22A 1.436(7) . ?
O3A C3A 1.353(7) . ?
O3A C23A 1.421(8) . ?
O4A C9A 1.233(7) . ?
N1A C9A 1.353(8) . ?
N1A C6A 1.422(8) . ?
N1A C8A 1.491(7) . ?
N2A C15A 1.495(9) . ?
N2A C16A 1.506(9) . ?
N2A C21A 1.539(8) . ?
N2A H2AA 1.0000 . ?
C1A C2A 1.372(9) . ?
C1A C6A 1.399(8) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.405(8) . ?
C3A C4A 1.389(8) . ?
C4A C5A 1.376(9) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.380(8) . ?
C5A C7A 1.509(8) . ?
C7A C17A 1.534(9) . ?
C7A C8A 1.558(9) . ?
C7A C21A 1.561(8) . ?
C8A C18A 1.533(9) . ?
C8A H8AA 1.0000 . ?
C9A C10A 1.511(9) . ?
C10A C11A 1.564(9) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C18A 1.526(9) . ?
C11A H11B 1.0000 . ?
C12A C13A 1.480(10) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.323(10) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.496(10) . ?
C14A C19A 1.523(9) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A C17A 1.507(9) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.524(9) . ?
C18A H18B 1.0000 . ?
C19A C20A 1.517(10) . ?
C19A H19B 1.0000 . ?
C20A C21A 1.499(9) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21B 1.0000 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
O5 C24 1.242(7) . ?
O6 C24 1.269(7) . ?
O7 C27 1.247(7) . ?
O8 C28 1.227(7) . ?
O9 O91 0.60(5) . ?
O9 N5 1.27(2) . ?
O91 N5 1.16(5) . ?
O10 N5 1.220(9) . ?
O12 N61 1.13(5) . ?
O12 N6 1.31(3) . ?
O12 O121 1.57(3) . ?
O121 N6 1.34(4) . ?
N3 C27 1.328(8) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C28 1.337(8) . ?
N4 C25 1.445(8) . ?
N4 H4B 0.8800 . ?
N5 C31 1.490(9) . ?
C24 C25 1.552(8) . ?
C25 C26 1.522(9) . ?
C25 H25B 1.0000 . ?
C26 C27 1.505(9) . ?
C26 H26C 0.9900 . ?
C26 H26D 0.9900 . ?
C28 C29 1.469(9) . ?
C29 C30 1.388(8) . ?
C29 C34 1.399(9) . ?
C30 C31 1.362(10) . ?
C30 H30C 0.9500 . ?
C31 C321 1.37(3) . ?
C31 C32 1.43(3) . ?
C34 C33 1.33(2) . ?
C34 C331 1.48(3) . ?
C34 H341 0.9500 . ?
C34 H34 0.9500 . ?
O11 N6 1.20(3) . ?
N6 C33 1.41(4) . ?
C32 C33 1.40(3) . ?
C32 H32C 0.9500 . ?
O111 N61 1.12(4) . ?
N61 C331 1.63(5) . ?
C321 C331 1.35(3) . ?
C321 H32D 0.9500 . ?
O5A C24A 1.244(7) . ?
O6A C24A 1.281(7) . ?
O7A C27A 1.241(7) . ?
N3A C27A 1.318(8) . ?
N3A H3AA 0.8800 . ?
N3A H3AB 0.8800 . ?
N4A C28A 1.318(9) . ?
N4A C25A 1.470(8) . ?
N4A H4AB 0.8800 . ?
N6A O12B 1.15(3) . ?
N6A O11A 1.215(10) . ?
N6A O12A 1.273(10) . ?
N6A O11B 1.27(3) . ?
N6A C33A 1.434(16) . ?
N6A C33B 1.62(5) . ?
C24A C25A 1.525(8) . ?
C25A C26A 1.526(8) . ?
C25A H25A 1.0000 . ?
C26A C27A 1.500(8) . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C28A O8B 1.24(3) . ?
C28A O8A 1.292(11) . ?
C28A C29B 1.47(7) . ?
C28A C29A 1.53(2) . ?
C34A C33B 1.31(6) . ?
C34A C29A 1.356(18) . ?
C34A C33A 1.408(18) . ?
C34A C29B 1.52(6) . ?
C34A H34B 0.9500 . ?
C34A H34A 0.9500 . ?
O9A N5A 1.151(14) . ?
O10A C302 1.11(4) . ?
O10A N5A 1.245(19) . ?
N5A C31A 1.499(14) . ?
C29A C30A 1.40(2) . ?
C30A C31A 1.363(15) . ?
C30A H30A 0.9500 . ?
C31A C32A 1.413(14) . ?
C32A C33A 1.35(2) . ?
C32A H32A 0.9500 . ?
O9B N5B 1.20(3) . ?
O10B C300 1.19(3) . ?
O10B N5B 1.24(4) . ?
N5B C31B 1.50(5) . ?
C29B C30B 1.29(7) . ?
C30B C31B 1.38(4) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.46(4) . ?
C32B C33B 1.35(6) . ?
C32B H32B 0.9500 . ?
O100 C100 1.440(8) . ?
O100 H100 0.8400 . ?
C100 H10G 0.9800 . ?
C100 H10E 0.9800 . ?
C100 H10F 0.9800 . ?
O101 C101 1.443(8) . ?
O101 H101 0.8400 . ?
C101 H10K 0.9800 . ?
C101 H10L 0.9800 . ?
C101 H10J 0.9800 . ?
O110 C110 1.440(8) . ?
O110 H110 0.8400 . ?
C110 H11C 0.9800 . ?
C110 H11D 0.9800 . ?
C110 H11E 0.9800 . ?
O120 C120 1.443(8) . ?
O120 H120 0.8400 . ?
C120 H12E 0.9800 . ?
C120 H12F 0.9800 . ?
C120 H12G 0.9800 . ?
O200 C200 1.445(7) . ?
O200 H200 0.8400 . ?
C200 H20I 0.9800 . ?
C200 H20E 0.9800 . ?
C200 H20F 0.9800 . ?
O300 C300 1.444(8) . ?
O300 H300 0.8400 . ?
O301 C300 1.431(8) . ?
O301 H301 0.8400 . ?
C300 H30G 0.9599 . ?
C300 H30H 0.9600 . ?
C300 H30I 1.0900 . ?
C300 H30D 0.9600 . ?
C300 H30E 0.9599 . ?
C300 H30F 1.0900 . ?
O302 C302 1.442(8) . ?
O302 H302 0.8400 . ?
O302 H30R 0.5252 . ?
O303 C302 1.442(8) . ?
O303 H303 0.8400 . ?
O303 H30O 0.5033 . ?
C302 C330 1.92(6) . ?
C302 H30P 0.9599 . ?
C302 H30O 0.9600 . ?
C302 H30M 0.9600 . ?
C302 H30N 0.9600 . ?
C302 H30R 0.9599 . ?
C302 H30S 0.9600 . ?
O310 C310 1.439(7) . ?
O310 H310 0.8400 . ?
O320 C310 1.441(8) . ?
O320 H320 0.8400 . ?
C310 O330 1.27(5) . ?
C310 H31G 0.9800 . ?
C310 H31C 0.9800 . ?
C310 H31D 0.9800 . ?
C310 H32H 0.9800 . ?
C310 H32E 0.9800 . ?
C310 H32F 0.9800 . ?
O330 C330 1.441(8) . ?
O330 H330 0.8400 . ?
C330 H33L 0.9800 . ?
C330 H33J 0.9800 . ?
C330 H33K 0.9800 . ?
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
C12 O1 C11 115.4(5) . . ?
C2 O2 C22 115.8(5) . . ?
C3 O3 C23 115.5(5) . . ?
C9 N1 C6 125.8(5) . . ?
C9 N1 C8 117.6(5) . . ?
C6 N1 C8 109.0(5) . . ?
C15 N2 C16 112.6(5) . . ?
C15 N2 C21 113.4(5) . . ?
C16 N2 C21 107.6(4) . . ?
C15 N2 H2A 107.7 . . ?
C16 N2 H2A 107.7 . . ?
C21 N2 H2A 107.7 . . ?
C6 C1 C2 118.8(6) . . ?
C6 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
O2 C2 C1 125.8(6) . . ?
O2 C2 C3 113.8(5) . . ?
C1 C2 C3 120.3(6) . . ?
O3 C3 C4 124.1(5) . . ?
O3 C3 C2 116.4(5) . . ?
C4 C3 C2 119.5(6) . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 C7 130.2(5) . . ?
C6 C5 C7 108.9(5) . . ?
C1 C6 C5 120.8(6) . . ?
C1 C6 N1 128.4(6) . . ?
C5 C6 N1 110.7(5) . . ?
C5 C7 C8 103.7(5) . . ?
C5 C7 C21 114.3(5) . . ?
C8 C7 C21 115.1(5) . . ?
C5 C7 C17 112.6(5) . . ?
C8 C7 C17 111.9(5) . . ?
C21 C7 C17 99.6(4) . . ?
C18 C8 N1 106.2(5) . . ?
C18 C8 C7 117.1(5) . . ?
N1 C8 C7 103.5(5) . . ?
C18 C8 H8A 109.9 . . ?
N1 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
O4 C9 N1 121.9(6) . . ?
O4 C9 C10 121.6(6) . . ?
N1 C9 C10 116.5(6) . . ?
C9 C10 C11 116.2(5) . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
O1 C11 C18 114.3(5) . . ?
O1 C11 C10 104.1(5) . . ?
C18 C11 C10 109.4(5) . . ?
O1 C11 H11A 109.6 . . ?
C18 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
O1 C12 C13 110.6(5) . . ?
O1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 121.6(6) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 121.5(6) . . ?
C13 C14 C19 122.3(6) . . ?
C15 C14 C19 116.2(6) . . ?
C14 C15 N2 110.8(5) . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 N2 104.3(5) . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
N2 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.9(5) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 109.3(5) . . ?
C8 C18 C19 112.2(5) . . ?
C11 C18 C19 117.7(5) . . ?
C8 C18 H18A 105.6 . . ?
C11 C18 H18A 105.6 . . ?
C19 C18 H18A 105.6 . . ?
C14 C19 C20 108.4(5) . . ?
C14 C19 C18 113.9(5) . . ?
C20 C19 C18 107.4(5) . . ?
C14 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C21 C20 C19 108.9(5) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 110.8(5) . . ?
C20 C21 C7 114.2(5) . . ?
N2 C21 C7 105.8(5) . . ?
C20 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11A O1A C12A 113.8(5) . . ?
C2A O2A C22A 117.0(5) . . ?
C3A O3A C23A 116.1(5) . . ?
C9A N1A C6A 124.9(5) . . ?
C9A N1A C8A 119.5(5) . . ?
C6A N1A C8A 109.2(5) . . ?
C15A N2A C16A 113.2(6) . . ?
C15A N2A C21A 111.8(6) . . ?
C16A N2A C21A 107.7(5) . . ?
C15A N2A H2AA 108.0 . . ?
C16A N2A H2AA 108.0 . . ?
C21A N2A H2AA 108.0 . . ?
C2A C1A C6A 116.5(6) . . ?
C2A C1A H1AA 121.8 . . ?
C6A C1A H1AA 121.8 . . ?
C1A C2A O2A 121.5(6) . . ?
C1A C2A C3A 122.7(5) . . ?
O2A C2A C3A 115.8(6) . . ?
O3A C3A C4A 125.3(6) . . ?
O3A C3A C2A 116.1(5) . . ?
C4A C3A C2A 118.6(6) . . ?
C5A C4A C3A 119.7(6) . . ?
C5A C4A H4AA 120.1 . . ?
C3A C4A H4AA 120.1 . . ?
C4A C5A C6A 120.1(6) . . ?
C4A C5A C7A 130.1(6) . . ?
C6A C5A C7A 109.7(6) . . ?
C5A C6A C1A 122.1(6) . . ?
C5A C6A N1A 110.5(5) . . ?
C1A C6A N1A 127.4(6) . . ?
C5A C7A C17A 113.1(5) . . ?
C5A C7A C8A 103.1(5) . . ?
C17A C7A C8A 110.4(5) . . ?
C5A C7A C21A 115.6(5) . . ?
C17A C7A C21A 101.5(5) . . ?
C8A C7A C21A 113.5(5) . . ?
N1A C8A C18A 106.6(5) . . ?
N1A C8A C7A 103.7(5) . . ?
C18A C8A C7A 117.3(5) . . ?
N1A C8A H8AA 109.6 . . ?
C18A C8A H8AA 109.6 . . ?
C7A C8A H8AA 109.6 . . ?
O4A C9A N1A 122.0(6) . . ?
O4A C9A C10A 120.9(6) . . ?
N1A C9A C10A 117.1(5) . . ?
C9A C10A C11A 117.7(6) . . ?
C9A C10A H10C 107.9 . . ?
C11A C10A H10C 107.9 . . ?
C9A C10A H10D 107.9 . . ?
C11A C10A H10D 107.9 . . ?
H10C C10A H10D 107.2 . . ?
O1A C11A C18A 114.5(6) . . ?
O1A C11A C10A 103.7(5) . . ?
C18A C11A C10A 110.0(5) . . ?
O1A C11A H11B 109.5 . . ?
C18A C11A H11B 109.5 . . ?
C10A C11A H11B 109.5 . . ?
O1A C12A C13A 110.9(6) . . ?
O1A C12A H12C 109.5 . . ?
C13A C12A H12C 109.5 . . ?
O1A C12A H12D 109.5 . . ?
C13A C12A H12D 109.5 . . ?
H12C C12A H12D 108.1 . . ?
C14A C13A C12A 122.6(7) . . ?
C14A C13A H13B 118.7 . . ?
C12A C13A H13B 118.7 . . ?
C13A C14A C15A 121.8(7) . . ?
C13A C14A C19A 124.1(7) . . ?
C15A C14A C19A 114.0(6) . . ?
N2A C15A C14A 111.5(5) . . ?
N2A C15A H15C 109.3 . . ?
C14A C15A H15C 109.3 . . ?
N2A C15A H15D 109.3 . . ?
C14A C15A H15D 109.3 . . ?
H15C C15A H15D 108.0 . . ?
N2A C16A C17A 104.7(6) . . ?
N2A C16A H16C 110.8 . . ?
C17A C16A H16C 110.8 . . ?
N2A C16A H16D 110.8 . . ?
C17A C16A H16D 110.8 . . ?
H16C C16A H16D 108.9 . . ?
C16A C17A C7A 103.8(5) . . ?
C16A C17A H17C 111.0 . . ?
C7A C17A H17C 111.0 . . ?
C16A C17A H17D 111.0 . . ?
C7A C17A H17D 111.0 . . ?
H17C C17A H17D 109.0 . . ?
C19A C18A C11A 118.5(5) . . ?
C19A C18A C8A 111.3(6) . . ?
C11A C18A C8A 107.4(5) . . ?
C19A C18A H18B 106.3 . . ?
C11A C18A H18B 106.3 . . ?
C8A C18A H18B 106.3 . . ?
C20A C19A C14A 109.9(6) . . ?
C20A C19A C18A 107.1(6) . . ?
C14A C19A C18A 114.7(6) . . ?
C20A C19A H19B 108.3 . . ?
C14A C19A H19B 108.3 . . ?
C18A C19A H19B 108.3 . . ?
C21A C20A C19A 109.3(6) . . ?
C21A C20A H20C 109.8 . . ?
C19A C20A H20C 109.8 . . ?
C21A C20A H20D 109.8 . . ?
C19A C20A H20D 109.8 . . ?
H20C C20A H20D 108.3 . . ?
C20A C21A N2A 111.4(6) . . ?
C20A C21A C7A 114.4(6) . . ?
N2A C21A C7A 104.2(5) . . ?
C20A C21A H21B 108.9 . . ?
N2A C21A H21B 108.9 . . ?
C7A C21A H21B 108.9 . . ?
O2A C22A H22D 109.5 . . ?
O2A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
O2A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
O3A C23A H23D 109.5 . . ?
O3A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
O3A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O91 O9 N5 65(6) . . ?
O9 O91 N5 87(7) . . ?
N61 O12 O121 85(3) . . ?
N6 O12 O121 54.3(18) . . ?
N6 O121 O12 52.6(16) . . ?
C27 N3 H3A 120.0 . . ?
C27 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C28 N4 C25 123.0(5) . . ?
C28 N4 H4B 118.5 . . ?
C25 N4 H4B 118.5 . . ?
O91 N5 O10 118(3) . . ?
O91 N5 O9 28(3) . . ?
O10 N5 O9 125.6(10) . . ?
O91 N5 C31 119(3) . . ?
O10 N5 C31 118.3(8) . . ?
O9 N5 C31 115.8(10) . . ?
O5 C24 O6 126.1(6) . . ?
O5 C24 C25 116.3(6) . . ?
O6 C24 C25 117.5(6) . . ?
N4 C25 C26 111.0(5) . . ?
N4 C25 C24 111.8(5) . . ?
C26 C25 C24 109.0(5) . . ?
N4 C25 H25B 108.3 . . ?
C26 C25 H25B 108.3 . . ?
C24 C25 H25B 108.3 . . ?
C27 C26 C25 109.7(5) . . ?
C27 C26 H26C 109.7 . . ?
C25 C26 H26C 109.7 . . ?
C27 C26 H26D 109.7 . . ?
C25 C26 H26D 109.7 . . ?
H26C C26 H26D 108.2 . . ?
O7 C27 N3 121.8(6) . . ?
O7 C27 C26 120.7(6) . . ?
N3 C27 C26 117.4(6) . . ?
O8 C28 N4 121.0(7) . . ?
O8 C28 C29 119.4(6) . . ?
N4 C28 C29 119.5(6) . . ?
C30 C29 C34 118.5(7) . . ?
C30 C29 C28 118.2(6) . . ?
C34 C29 C28 123.3(6) . . ?
C31 C30 C29 120.0(7) . . ?
C31 C30 H30C 120.0 . . ?
C29 C30 H30C 120.0 . . ?
C30 C31 C321 125.3(17) . . ?
C30 C31 C32 122.7(13) . . ?
C30 C31 N5 119.4(7) . . ?
C321 C31 N5 114.0(16) . . ?
C32 C31 N5 117.4(13) . . ?
C33 C34 C29 119.6(12) . . ?
C29 C34 C331 114.3(14) . . ?
C29 C34 H341 122.9 . . ?
C331 C34 H341 122.9 . . ?
C33 C34 H34 120.2 . . ?
C29 C34 H34 120.2 . . ?
O11 N6 O12 115.5(17) . . ?
O11 N6 O121 101(3) . . ?
O12 N6 O121 73(2) . . ?
O11 N6 C33 123(3) . . ?
O12 N6 C33 118(2) . . ?
O121 N6 C33 113.0(19) . . ?
C33 C32 C31 113.4(18) . . ?
C33 C32 H32C 123.3 . . ?
C31 C32 H32C 123.3 . . ?
C34 C33 C32 124.7(17) . . ?
C34 C33 N6 119(2) . . ?
C32 C33 N6 115.1(19) . . ?
O111 N61 O12 127(4) . . ?
O111 N61 C331 115(4) . . ?
O12 N61 C331 113(3) . . ?
C331 C321 C31 113(2) . . ?
C331 C321 H32D 123.5 . . ?
C31 C321 H32D 123.5 . . ?
C321 C331 C34 125(2) . . ?
C321 C331 N61 119(3) . . ?
C34 C331 N61 115(3) . . ?
C27A N3A H3AA 120.0 . . ?
C27A N3A H3AB 120.0 . . ?
H3AA N3A H3AB 120.0 . . ?
C28A N4A C25A 121.3(5) . . ?
C28A N4A H4AB 119.3 . . ?
C25A N4A H4AB 119.3 . . ?
O11A N6A O12A 121.2(8) . . ?
O12B N6A O11B 136(2) . . ?
O11A N6A C33A 120.3(10) . . ?
O12A N6A C33A 118.5(9) . . ?
O12B N6A C33B 116(3) . . ?
O11B N6A C33B 107(3) . . ?
O5A C24A O6A 124.2(6) . . ?
O5A C24A C25A 118.1(6) . . ?
O6A C24A C25A 117.5(5) . . ?
N4A C25A C24A 109.5(5) . . ?
N4A C25A C26A 110.6(5) . . ?
C24A C25A C26A 111.5(5) . . ?
N4A C25A H25A 108.4 . . ?
C24A C25A H25A 108.4 . . ?
C26A C25A H25A 108.4 . . ?
C27A C26A C25A 111.3(5) . . ?
C27A C26A H26A 109.4 . . ?
C25A C26A H26A 109.4 . . ?
C27A C26A H26B 109.4 . . ?
C25A C26A H26B 109.4 . . ?
H26A C26A H26B 108.0 . . ?
O7A C27A N3A 122.8(6) . . ?
O7A C27A C26A 120.3(6) . . ?
N3A C27A C26A 116.7(6) . . ?
O8B C28A N4A 121.9(16) . . ?
O8A C28A N4A 122.3(8) . . ?
O8B C28A C29B 117(3) . . ?
N4A C28A C29B 120(3) . . ?
O8A C28A C29A 120.8(10) . . ?
N4A C28A C29A 117.0(9) . . ?
C29A C34A C33A 119.2(13) . . ?
C33B C34A C29B 115(4) . . ?
C33B C34A H34B 122.6 . . ?
C29B C34A H34B 122.6 . . ?
C29A C34A H34A 120.4 . . ?
C33A C34A H34A 120.4 . . ?
C302 O10A N5A 150(3) . . ?
O9A N5A O10A 126.8(13) . . ?
O9A N5A C31A 121.8(14) . . ?
O10A N5A C31A 110.6(14) . . ?
C34A C29A C30A 118.6(16) . . ?
C34A C29A C28A 123.2(15) . . ?
C30A C29A C28A 118.2(13) . . ?
C31A C30A C29A 120.1(12) . . ?
C31A C30A H30A 119.9 . . ?
C29A C30A H30A 119.9 . . ?
C30A C31A C32A 123.1(10) . . ?
C30A C31A N5A 116.5(11) . . ?
C32A C31A N5A 120.4(11) . . ?
C33A C32A C31A 114.3(11) . . ?
C33A C32A H32A 122.9 . . ?
C31A C32A H32A 122.9 . . ?
C32A C33A C34A 124.4(12) . . ?
C32A C33A N6A 116.2(13) . . ?
C34A C33A N6A 119.3(13) . . ?
C300 O10B N5B 166(3) . . ?
O9B N5B O10B 131(3) . . ?
O9B N5B C31B 114(3) . . ?
O10B N5B C31B 115(3) . . ?
C30B C29B C28A 121(5) . . ?
C30B C29B C34A 120(5) . . ?
C28A C29B C34A 117(4) . . ?
C29B C30B C31B 122(4) . . ?
C29B C30B H30B 119.1 . . ?
C31B C30B H30B 119.1 . . ?
C30B C31B C32B 119(3) . . ?
C30B C31B N5B 122(3) . . ?
C32B C31B N5B 119(3) . . ?
C33B C32B C31B 115(3) . . ?
C33B C32B H32B 122.4 . . ?
C31B C32B H32B 122.4 . . ?
C34A C33B C32B 128(4) . . ?
C34A C33B N6A 113(4) . . ?
C32B C33B N6A 118(4) . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H10G 109.5 . . ?
O100 C100 H10E 109.5 . . ?
H10G C100 H10E 109.5 . . ?
O100 C100 H10F 109.5 . . ?
H10G C100 H10F 109.5 . . ?
H10E C100 H10F 109.5 . . ?
C101 O101 H101 109.5 . . ?
O101 C101 H10K 109.5 . . ?
O101 C101 H10L 109.5 . . ?
H10K C101 H10L 109.5 . . ?
O101 C101 H10J 109.5 . . ?
H10K C101 H10J 109.5 . . ?
H10L C101 H10J 109.5 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H11C 109.5 . . ?
O110 C110 H11D 109.5 . . ?
H11C C110 H11D 109.5 . . ?
O110 C110 H11E 109.5 . . ?
H11C C110 H11E 109.5 . . ?
H11D C110 H11E 109.5 . . ?
C120 O120 H120 109.5 . . ?
O120 C120 H12E 109.5 . . ?
O120 C120 H12F 109.5 . . ?
H12E C120 H12F 109.5 . . ?
O120 C120 H12G 109.5 . . ?
H12E C120 H12G 109.5 . . ?
H12F C120 H12G 109.5 . . ?
C200 O200 H200 109.5 . . ?
O200 C200 H20I 109.5 . . ?
O200 C200 H20E 109.5 . . ?
H20I C200 H20E 109.5 . . ?
O200 C200 H20F 109.5 . . ?
H20I C200 H20F 109.5 . . ?
H20E C200 H20F 109.5 . . ?
C300 O300 H300 109.5 . . ?
C300 O301 H301 109.5 . . ?
O301 C300 H30G 114.5 . . ?
O301 C300 H30H 116.2 . . ?
H30G C300 H30H 112.6 . . ?
O301 C300 H30I 78.2 . . ?
H30G C300 H30I 115.6 . . ?
H30H C300 H30I 115.6 . . ?
O300 C300 H30D 107.2 . . ?
O300 C300 H30E 110.1 . . ?
H30D C300 H30E 107.0 . . ?
O300 C300 H30F 117.0 . . ?
H30D C300 H30F 107.5 . . ?
H30E C300 H30F 107.5 . . ?
C302 O302 H302 109.5 . . ?
C302 O302 H30R 18.8 . . ?
H302 O302 H30R 110.8 . . ?
C302 O303 H303 109.5 . . ?
C302 O303 H30O 13.7 . . ?
H303 O303 H30O 116.0 . . ?
O303 C302 H30P 111.0 . . ?
O303 C302 H30O 7.1 . . ?
H30P C302 H30O 104.2 . . ?
O303 C302 H30M 109.6 . . ?
H30P C302 H30M 111.4 . . ?
H30O C302 H30M 111.4 . . ?
O302 C302 H30N 103.4 . . ?
O302 C302 H30R 10.2 . . ?
H30N C302 H30R 111.4 . . ?
O302 C302 H30S 113.7 . . ?
H30N C302 H30S 111.4 . . ?
H30R C302 H30S 104.2 . . ?
C310 O310 H310 109.5 . . ?
C310 O320 H320 109.5 . . ?
O310 C310 H31G 109.5 . . ?
O310 C310 H31C 109.5 . . ?
H31G C310 H31C 109.5 . . ?
O310 C310 H31D 109.5 . . ?
H31G C310 H31D 109.5 . . ?
H31C C310 H31D 109.5 . . ?
O320 C310 H32H 109.5 . . ?
O320 C310 H32E 109.5 . . ?
H32H C310 H32E 109.5 . . ?
O320 C310 H32F 109.5 . . ?
H32H C310 H32F 109.5 . . ?
H32E C310 H32F 109.5 . . ?
C310 O330 C330 104(4) . . ?
C310 O330 H330 109.5 . . ?
C330 O330 H330 106.4 . . ?
O330 C330 C302 161(5) . . ?
O330 C330 H33L 109.5 . . ?
C302 C330 H33L 51.9 . . ?
O330 C330 H33J 109.5 . . ?
C302 C330 H33J 78.2 . . ?
H33L C330 H33J 109.5 . . ?
O330 C330 H33K 109.5 . . ?
C302 C330 H33K 82.9 . . ?
H33L C330 H33K 109.5 . . ?
H33J C330 H33K 109.5 . . ?
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
C22 O2 C2 C1 4.0(9) . . . . ?
C22 O2 C2 C3 -177.2(5) . . . . ?
C6 C1 C2 O2 -179.4(6) . . . . ?
C6 C1 C2 C3 1.9(9) . . . . ?
C23 O3 C3 C4 3.8(8) . . . . ?
C23 O3 C3 C2 -177.3(5) . . . . ?
O2 C2 C3 O3 -1.5(8) . . . . ?
C1 C2 C3 O3 177.3(6) . . . . ?
O2 C2 C3 C4 177.4(5) . . . . ?
C1 C2 C3 C4 -3.8(9) . . . . ?
O3 C3 C4 C5 -178.4(6) . . . . ?
C2 C3 C4 C5 2.7(9) . . . . ?
C3 C4 C5 C6 0.1(9) . . . . ?
C3 C4 C5 C7 -175.9(6) . . . . ?
C2 C1 C6 C5 0.9(9) . . . . ?
C2 C1 C6 N1 -176.1(6) . . . . ?
C4 C5 C6 C1 -1.9(9) . . . . ?
C7 C5 C6 C1 174.9(5) . . . . ?
C4 C5 C6 N1 175.6(6) . . . . ?
C7 C5 C6 N1 -7.6(7) . . . . ?
C9 N1 C6 C1 23.0(10) . . . . ?
C8 N1 C6 C1 171.5(6) . . . . ?
C9 N1 C6 C5 -154.3(6) . . . . ?
C8 N1 C6 C5 -5.8(7) . . . . ?
C4 C5 C7 C8 -166.3(6) . . . . ?
C6 C5 C7 C8 17.3(6) . . . . ?
C4 C5 C7 C21 -40.3(9) . . . . ?
C6 C5 C7 C21 143.3(5) . . . . ?
C4 C5 C7 C17 72.4(8) . . . . ?
C6 C5 C7 C17 -103.9(6) . . . . ?
C9 N1 C8 C18 43.7(7) . . . . ?
C6 N1 C8 C18 -107.7(6) . . . . ?
C9 N1 C8 C7 167.6(5) . . . . ?
C6 N1 C8 C7 16.2(6) . . . . ?
C5 C7 C8 C18 96.8(6) . . . . ?
C21 C7 C8 C18 -28.8(8) . . . . ?
C17 C7 C8 C18 -141.5(5) . . . . ?
C5 C7 C8 N1 -19.6(6) . . . . ?
C21 C7 C8 N1 -145.2(5) . . . . ?
C17 C7 C8 N1 102.1(5) . . . . ?
C6 N1 C9 O4 -23.6(10) . . . . ?
C8 N1 C9 O4 -169.7(6) . . . . ?
C6 N1 C9 C10 157.6(6) . . . . ?
C8 N1 C9 C10 11.5(8) . . . . ?
O4 C9 C10 C11 139.7(6) . . . . ?
N1 C9 C10 C11 -41.5(8) . . . . ?
C12 O1 C11 C18 -67.8(7) . . . . ?
C12 O1 C11 C10 172.8(5) . . . . ?
C9 C10 C11 O1 135.2(6) . . . . ?
C9 C10 C11 C18 12.6(8) . . . . ?
C11 O1 C12 C13 89.3(6) . . . . ?
O1 C12 C13 C14 -64.1(8) . . . . ?
C12 C13 C14 C15 177.1(6) . . . . ?
C12 C13 C14 C19 -4.9(9) . . . . ?
C13 C14 C15 N2 -130.8(6) . . . . ?
C19 C14 C15 N2 51.1(7) . . . . ?
C16 N2 C15 C14 78.5(7) . . . . ?
C21 N2 C15 C14 -44.0(7) . . . . ?
C15 N2 C16 C17 -140.9(5) . . . . ?
C21 N2 C16 C17 -15.3(6) . . . . ?
N2 C16 C17 C7 36.7(6) . . . . ?
C5 C7 C17 C16 -164.7(5) . . . . ?
C8 C7 C17 C16 78.9(6) . . . . ?
C21 C7 C17 C16 -43.2(6) . . . . ?
N1 C8 C18 C11 -71.2(6) . . . . ?
C7 C8 C18 C11 173.9(5) . . . . ?
N1 C8 C18 C19 156.5(5) . . . . ?
C7 C8 C18 C19 41.5(7) . . . . ?
O1 C11 C18 C8 -74.4(6) . . . . ?
C10 C11 C18 C8 41.9(7) . . . . ?
O1 C11 C18 C19 55.0(7) . . . . ?
C10 C11 C18 C19 171.3(5) . . . . ?
C13 C14 C19 C20 -178.7(6) . . . . ?
C15 C14 C19 C20 -0.6(7) . . . . ?
C13 C14 C19 C18 61.8(8) . . . . ?
C15 C14 C19 C18 -120.1(6) . . . . ?
C8 C18 C19 C14 59.9(7) . . . . ?
C11 C18 C19 C14 -68.1(7) . . . . ?
C8 C18 C19 C20 -60.2(7) . . . . ?
C11 C18 C19 C20 171.7(5) . . . . ?
C14 C19 C20 C21 -56.4(6) . . . . ?
C18 C19 C20 C21 67.1(6) . . . . ?
C19 C20 C21 N2 63.6(6) . . . . ?
C19 C20 C21 C7 -55.8(7) . . . . ?
C15 N2 C21 C20 -11.5(7) . . . . ?
C16 N2 C21 C20 -136.7(5) . . . . ?
C15 N2 C21 C7 112.9(5) . . . . ?
C16 N2 C21 C7 -12.3(6) . . . . ?
C5 C7 C21 C20 -84.1(7) . . . . ?
C8 C7 C21 C20 35.8(8) . . . . ?
C17 C7 C21 C20 155.6(5) . . . . ?
C5 C7 C21 N2 153.6(5) . . . . ?
C8 C7 C21 N2 -86.4(6) . . . . ?
C17 C7 C21 N2 33.3(6) . . . . ?
C6A C1A C2A O2A -178.8(5) . . . . ?
C6A C1A C2A C3A 1.9(9) . . . . ?
C22A O2A C2A C1A -1.8(8) . . . . ?
C22A O2A C2A C3A 177.6(5) . . . . ?
C23A O3A C3A C4A 4.0(9) . . . . ?
C23A O3A C3A C2A -176.9(5) . . . . ?
C1A C2A C3A O3A 175.9(6) . . . . ?
O2A C2A C3A O3A -3.4(8) . . . . ?
C1A C2A C3A C4A -4.9(9) . . . . ?
O2A C2A C3A C4A 175.8(5) . . . . ?
O3A C3A C4A C5A -177.7(6) . . . . ?
C2A C3A C4A C5A 3.1(9) . . . . ?
C3A C4A C5A C6A 1.4(9) . . . . ?
C3A C4A C5A C7A -174.1(6) . . . . ?
C4A C5A C6A C1A -4.6(10) . . . . ?
C7A C5A C6A C1A 171.7(6) . . . . ?
C4A C5A C6A N1A 175.4(6) . . . . ?
C7A C5A C6A N1A -8.3(7) . . . . ?
C2A C1A C6A C5A 2.9(9) . . . . ?
C2A C1A C6A N1A -177.1(6) . . . . ?
C9A N1A C6A C5A -156.3(6) . . . . ?
C8A N1A C6A C5A -4.9(7) . . . . ?
C9A N1A C6A C1A 23.7(10) . . . . ?
C8A N1A C6A C1A 175.0(6) . . . . ?
C4A C5A C7A C17A 73.9(9) . . . . ?
C6A C5A C7A C17A -102.0(6) . . . . ?
C4A C5A C7A C8A -166.9(6) . . . . ?
C6A C5A C7A C8A 17.2(6) . . . . ?
C4A C5A C7A C21A -42.5(10) . . . . ?
C6A C5A C7A C21A 141.6(6) . . . . ?
C9A N1A C8A C18A 44.0(7) . . . . ?
C6A N1A C8A C18A -109.1(6) . . . . ?
C9A N1A C8A C7A 168.4(6) . . . . ?
C6A N1A C8A C7A 15.3(6) . . . . ?
C5A C7A C8A N1A -19.0(6) . . . . ?
C17A C7A C8A N1A 102.1(5) . . . . ?
C21A C7A C8A N1A -144.8(5) . . . . ?
C5A C7A C8A C18A 98.1(6) . . . . ?
C17A C7A C8A C18A -140.8(6) . . . . ?
C21A C7A C8A C18A -27.7(8) . . . . ?
C6A N1A C9A O4A -26.3(10) . . . . ?
C8A N1A C9A O4A -175.0(6) . . . . ?
C6A N1A C9A C10A 155.1(6) . . . . ?
C8A N1A C9A C10A 6.4(8) . . . . ?
O4A C9A C10A C11A 150.3(6) . . . . ?
N1A C9A C10A C11A -31.0(8) . . . . ?
C12A O1A C11A C18A -69.8(7) . . . . ?
C12A O1A C11A C10A 170.3(6) . . . . ?
C9A C10A C11A O1A 124.6(6) . . . . ?
C9A C10A C11A C18A 1.6(8) . . . . ?
C11A O1A C12A C13A 88.6(7) . . . . ?
O1A C12A C13A C14A -65.2(9) . . . . ?
C12A C13A C14A C15A 176.7(7) . . . . ?
C12A C13A C14A C19A 0.5(11) . . . . ?
C16A N2A C15A C14A 73.8(8) . . . . ?
C21A N2A C15A C14A -48.1(8) . . . . ?
C13A C14A C15A N2A -122.8(7) . . . . ?
C19A C14A C15A N2A 53.8(8) . . . . ?
C15A N2A C16A C17A -141.3(6) . . . . ?
C21A N2A C16A C17A -17.2(7) . . . . ?
N2A C16A C17A C7A 37.6(7) . . . . ?
C5A C7A C17A C16A -167.2(6) . . . . ?
C8A C7A C17A C16A 77.9(6) . . . . ?
C21A C7A C17A C16A -42.7(6) . . . . ?
O1A C11A C18A C19A 58.0(8) . . . . ?
C10A C11A C18A C19A 174.4(6) . . . . ?
O1A C11A C18A C8A -69.1(6) . . . . ?
C10A C11A C18A C8A 47.2(7) . . . . ?
N1A C8A C18A C19A 157.5(5) . . . . ?
C7A C8A C18A C19A 41.9(8) . . . . ?
N1A C8A C18A C11A -71.3(6) . . . . ?
C7A C8A C18A C11A 173.1(5) . . . . ?
C13A C14A C19A C20A 175.4(7) . . . . ?
C15A C14A C19A C20A -1.1(8) . . . . ?
C13A C14A C19A C18A 54.6(10) . . . . ?
C15A C14A C19A C18A -121.9(7) . . . . ?
C11A C18A C19A C20A 173.1(6) . . . . ?
C8A C18A C19A C20A -61.6(7) . . . . ?
C11A C18A C19A C14A -64.6(9) . . . . ?
C8A C18A C19A C14A 60.7(8) . . . . ?
C14A C19A C20A C21A -55.5(7) . . . . ?
C18A C19A C20A C21A 69.8(7) . . . . ?
C19A C20A C21A N2A 61.0(7) . . . . ?
C19A C20A C21A C7A -56.8(7) . . . . ?
C15A N2A C21A C20A -8.2(8) . . . . ?
C16A N2A C21A C20A -133.1(6) . . . . ?
C15A N2A C21A C7A 115.7(6) . . . . ?
C16A N2A C21A C7A -9.3(7) . . . . ?
C5A C7A C21A C20A -83.9(7) . . . . ?
C17A C7A C21A C20A 153.3(6) . . . . ?
C8A C7A C21A C20A 34.9(8) . . . . ?
C5A C7A C21A N2A 154.2(5) . . . . ?
C17A C7A C21A N2A 31.4(6) . . . . ?
C8A C7A C21A N2A -86.9(6) . . . . ?
N61 O12 O121 N6 -10(3) . . . . ?
O9 O91 N5 O10 -114(6) . . . . ?
O9 O91 N5 C31 92(6) . . . . ?
O91 O9 N5 O10 83(7) . . . . ?
O91 O9 N5 C31 -103(6) . . . . ?
C28 N4 C25 C26 139.9(6) . . . . ?
C28 N4 C25 C24 -98.1(7) . . . . ?
O5 C24 C25 N4 153.0(6) . . . . ?
O6 C24 C25 N4 -28.1(8) . . . . ?
O5 C24 C25 C26 -83.9(7) . . . . ?
O6 C24 C25 C26 95.0(7) . . . . ?
N4 C25 C26 C27 -57.3(7) . . . . ?
C24 C25 C26 C27 179.1(6) . . . . ?
C25 C26 C27 O7 -74.0(8) . . . . ?
C25 C26 C27 N3 102.0(7) . . . . ?
C25 N4 C28 O8 2.7(10) . . . . ?
C25 N4 C28 C29 -178.6(6) . . . . ?
O8 C28 C29 C30 -5.7(9) . . . . ?
N4 C28 C29 C30 175.7(6) . . . . ?
O8 C28 C29 C34 174.2(7) . . . . ?
N4 C28 C29 C34 -4.5(10) . . . . ?
C34 C29 C30 C31 0.8(10) . . . . ?
C28 C29 C30 C31 -179.4(6) . . . . ?
C29 C30 C31 C321 -15.9(17) . . . . ?
C29 C30 C31 C32 6.4(14) . . . . ?
C29 C30 C31 N5 178.0(6) . . . . ?
O91 N5 C31 C30 -20(4) . . . . ?
O10 N5 C31 C30 -173.6(8) . . . . ?
O9 N5 C31 C30 12(2) . . . . ?
O91 N5 C31 C321 173(5) . . . . ?
O10 N5 C31 C321 18.8(15) . . . . ?
O9 N5 C31 C321 -156(2) . . . . ?
O91 N5 C31 C32 152(4) . . . . ?
O10 N5 C31 C32 -1.4(14) . . . . ?
O9 N5 C31 C32 -176(2) . . . . ?
C30 C29 C34 C33 -9.2(14) . . . . ?
C28 C29 C34 C33 171.0(11) . . . . ?
C30 C29 C34 C331 14.5(15) . . . . ?
C28 C29 C34 C331 -165.3(13) . . . . ?
N61 O12 N6 O11 66(5) . . . . ?
O121 O12 N6 O11 -94(3) . . . . ?
N61 O12 N6 O121 160(7) . . . . ?
N61 O12 N6 C33 -92(7) . . . . ?
O121 O12 N6 C33 108(2) . . . . ?
O12 O121 N6 O11 113.6(17) . . . . ?
O12 O121 N6 C33 -114(3) . . . . ?
C30 C31 C32 C33 -4.9(17) . . . . ?
C321 C31 C32 C33 99(8) . . . . ?
N5 C31 C32 C33 -176.7(10) . . . . ?
C29 C34 C33 C32 11(2) . . . . ?
C331 C34 C33 C32 -70(6) . . . . ?
C29 C34 C33 N6 178.6(15) . . . . ?
C331 C34 C33 N6 97(6) . . . . ?
C31 C32 C33 C34 -4(2) . . . . ?
C31 C32 C33 N6 -172.0(17) . . . . ?
O11 N6 C33 C34 175(2) . . . . ?
O12 N6 C33 C34 -29(3) . . . . ?
O121 N6 C33 C34 54(3) . . . . ?
O11 N6 C33 C32 -16(3) . . . . ?
O12 N6 C33 C32 140(2) . . . . ?
O121 N6 C33 C32 -138(2) . . . . ?
N6 O12 N61 O111 -138(11) . . . . ?
O121 O12 N61 O111 -122(6) . . . . ?
N6 O12 N61 C331 68(4) . . . . ?
O121 O12 N61 C331 83(3) . . . . ?
C30 C31 C321 C331 12(2) . . . . ?
C32 C31 C321 C331 -77(8) . . . . ?
N5 C31 C321 C331 178.5(14) . . . . ?
C31 C321 C331 C34 6(3) . . . . ?
C31 C321 C331 N61 173(2) . . . . ?
C33 C34 C331 C321 90(6) . . . . ?
C29 C34 C331 C321 -19(2) . . . . ?
C33 C34 C331 N61 -77(6) . . . . ?
C29 C34 C331 N61 173(2) . . . . ?
O111 N61 C331 C321 21(5) . . . . ?
O12 N61 C331 C321 179(3) . . . . ?
O111 N61 C331 C34 -170(4) . . . . ?
O12 N61 C331 C34 -13(4) . . . . ?
C28A N4A C25A C24A -82.8(7) . . . . ?
C28A N4A C25A C26A 153.9(6) . . . . ?
O5A C24A C25A N4A 145.6(6) . . . . ?
O6A C24A C25A N4A -39.0(8) . . . . ?
O5A C24A C25A C26A -91.6(7) . . . . ?
O6A C24A C25A C26A 83.7(7) . . . . ?
N4A C25A C26A C27A -60.6(7) . . . . ?
C24A C25A C26A C27A 177.3(6) . . . . ?
C25A C26A C27A O7A -77.0(8) . . . . ?
C25A C26A C27A N3A 98.4(7) . . . . ?
C25A N4A C28A O8B 18.8(19) . . . . ?
C25A N4A C28A O8A -18.3(11) . . . . ?
C25A N4A C28A C29B -175(2) . . . . ?
C25A N4A C28A C29A 163.2(8) . . . . ?
C302 O10A N5A O9A -174(5) . . . . ?
C302 O10A N5A C31A 17(6) . . . . ?
C33B C34A C29A C30A -14(3) . . . . ?
C33A C34A C29A C30A 6.4(16) . . . . ?
C29B C34A C29A C30A -105(11) . . . . ?
C33B C34A C29A C28A 166(2) . . . . ?
C33A C34A C29A C28A -172.8(9) . . . . ?
C29B C34A C29A C28A 76(11) . . . . ?
O8B C28A C29A C34A 161.8(17) . . . . ?
O8A C28A C29A C34A -164.5(10) . . . . ?
N4A C28A C29A C34A 14.0(15) . . . . ?
C29B C28A C29A C34A -90(10) . . . . ?
O8B C28A C29A C30A -17.5(19) . . . . ?
O8A C28A C29A C30A 16.3(16) . . . . ?
N4A C28A C29A C30A -165.2(10) . . . . ?
C29B C28A C29A C30A 91(10) . . . . ?
C34A C29A C30A C31A -5.8(19) . . . . ?
C28A C29A C30A C31A 173.4(11) . . . . ?
C29A C30A C31A C32A 2(2) . . . . ?
C29A C30A C31A N5A -177.5(12) . . . . ?
O9A N5A C31A C30A -10(2) . . . . ?
O10A N5A C31A C30A 159.9(13) . . . . ?
O9A N5A C31A C32A 170.8(15) . . . . ?
O10A N5A C31A C32A -19.4(19) . . . . ?
C30A C31A C32A C33A 1.6(18) . . . . ?
N5A C31A C32A C33A -179.2(11) . . . . ?
C31A C32A C33A C34A -0.9(16) . . . . ?
C31A C32A C33A N6A 178.0(9) . . . . ?
C33B C34A C33A C32A 82(10) . . . . ?
C29A C34A C33A C32A -3.2(16) . . . . ?
C29B C34A C33A C32A 19(3) . . . . ?
C33B C34A C33A N6A -97(10) . . . . ?
C29A C34A C33A N6A 177.9(9) . . . . ?
C29B C34A C33A N6A -160(2) . . . . ?
O12B N6A C33A C32A 149.2(19) . . . . ?
O11A N6A C33A C32A 10.9(14) . . . . ?
O12A N6A C33A C32A -169.6(10) . . . . ?
O11B N6A C33A C32A -26.1(19) . . . . ?
C33B N6A C33A C32A -105(11) . . . . ?
O12B N6A C33A C34A -32(2) . . . . ?
O11A N6A C33A C34A -170.1(8) . . . . ?
O12A N6A C33A C34A 9.3(13) . . . . ?
O11B N6A C33A C34A 152.9(16) . . . . ?
C33B N6A C33A C34A 74(11) . . . . ?
C300 O10B N5B O9B -104(14) . . . . ?
C300 O10B N5B C31B 75(14) . . . . ?
O8B C28A C29B C30B -25(5) . . . . ?
O8A C28A C29B C30B 9(5) . . . . ?
N4A C28A C29B C30B 168(3) . . . . ?
C29A C28A C29B C30B -105(12) . . . . ?
O8B C28A C29B C34A 137(3) . . . . ?
O8A C28A C29B C34A 171(3) . . . . ?
N4A C28A C29B C34A -30(5) . . . . ?
C29A C28A C29B C34A 57(7) . . . . ?
C33B C34A C29B C30B -7(6) . . . . ?
C29A C34A C29B C30B 91(12) . . . . ?
C33A C34A C29B C30B 11(5) . . . . ?
C33B C34A C29B C28A -169(4) . . . . ?
C29A C34A C29B C28A -71(9) . . . . ?
C33A C34A C29B C28A -151(3) . . . . ?
C28A C29B C30B C31B 173(4) . . . . ?
C34A C29B C30B C31B 12(6) . . . . ?
C29B C30B C31B C32B -11(6) . . . . ?
C29B C30B C31B N5B 172(4) . . . . ?
O9B N5B C31B C30B 4(5) . . . . ?
O10B N5B C31B C30B -175(3) . . . . ?
O9B N5B C31B C32B -173(3) . . . . ?
O10B N5B C31B C32B 7(5) . . . . ?
C30B C31B C32B C33B 4(5) . . . . ?
N5B C31B C32B C33B -178(4) . . . . ?
C29A C34A C33B C32B -20(6) . . . . ?
C33A C34A C33B C32B -124(13) . . . . ?
C29B C34A C33B C32B 1(6) . . . . ?
C29A C34A C33B N6A 161(2) . . . . ?
C33A C34A C33B N6A 57(8) . . . . ?
C29B C34A C33B N6A -177(3) . . . . ?
C31B C32B C33B C34A 0(6) . . . . ?
C31B C32B C33B N6A 179(3) . . . . ?
O12B N6A C33B C34A 3(4) . . . . ?
O11A N6A C33B C34A -152(2) . . . . ?
O12A N6A C33B C34A 43(3) . . . . ?
O11B N6A C33B C34A 175(3) . . . . ?
C33A N6A C33B C34A -79(10) . . . . ?
O12B N6A C33B C32B -176(3) . . . . ?
O11A N6A C33B C32B 29(5) . . . . ?
O12A N6A C33B C32B -136(3) . . . . ?
O11B N6A C33B C32B -4(4) . . . . ?
C33A N6A C33B C32B 102(12) . . . . ?
N5B O10B C300 O301 -28(12) . . . . ?
N5B O10B C300 O300 7(14) . . . . ?
N5A O10A C302 O303 -37(8) . . . . ?
N5A O10A C302 O302 87(15) . . . . ?
N5A O10A C302 C330 -41(21) . . . . ?
O310 C310 O330 C330 85(4) . . . . ?
O320 C310 O330 C330 124(4) . . . . ?
C310 O330 C330 C302 140(15) . . . . ?
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
N2 H2A O7 1.00 2.03 2.771(6) 129.5 .
N2A H2AA O5A 1.00 2.07 2.902(7) 138.7 1_554
N3 H3A O5 0.88 1.95 2.825(7) 170.6 1_455
N3 H3B O6A 0.88 2.20 2.966(7) 144.8 .
N4 H4B O6A 0.88 2.07 2.921(6) 163.2 .
N3A H3AA O5A 0.88 2.02 2.879(7) 164.1 1_655
N3A H3AB O6 0.88 2.09 2.885(7) 150.4 .
N4A H4AB O6 0.88 2.01 2.870(6) 164.0 .
O100 H100 O4 0.84 2.05 2.799(16) 149.0 .
O101 H101 O9B 0.84 2.01 2.80(3) 158.3 1_564
O120 H120 O300 0.84 2.54 3.10(4) 124.7 1_564
O200 H200 O7 0.84 2.06 2.873(8) 161.6 .
O302 H302 O10B 0.84 1.83 2.63(11) 161.0 .
O302 H302 N5B 0.84 2.11 2.73(10) 131.4 .
O303 H303 O9 0.84 2.20 3.04(5) 173.6 .
O303 H303 N5 0.84 2.22 2.96(4) 147.8 .
O310 H310 O5 0.84 1.98 2.809(14) 166.6 1_545
O320 H320 O4A 0.84 2.05 2.850(19) 159.0 1_655
_refine_diff_density_max 0.369
_refine_diff_density_min -0.313
_refine_diff_density_rms 0.051
_database_code_depnum_ccdc_archive 'CCDC 933063'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_dnbdn
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
N-(3,5-dinitrobenzoyl)-D-asparagine
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C11 H10 N4 O8'
_chemical_formula_sum 'C11 H10 N4 O8'
_chemical_formula_weight 326.23
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'
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 6.371(2)
_cell_length_b 9.260(2)
_cell_length_c 22.629(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1335.0(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 2417
_cell_measurement_theta_min 2.8339
_cell_measurement_theta_max 28.5999
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.623
_exptl_crystal_F_000 672
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.600
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_min 0.060
_exptl_absorpt_coefficient_mu 0.141
_shelx_estimated_absorpt_T_min 0.920
_shelx_estimated_absorpt_T_max 0.992
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Sapphire2'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 4855
_diffrn_reflns_av_unetI/netI 0.0548
_diffrn_reflns_av_R_equivalents 0.0290
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 2.842
_diffrn_reflns_theta_max 26.992
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total 2786
_reflns_number_gt 2185
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.670
_reflns_Friedel_fraction_max 0.929
_reflns_Friedel_fraction_full 0.955
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0469P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack -0.6(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 2786
_refine_ls_number_parameters 208
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0598
_refine_ls_R_factor_gt 0.0423
_refine_ls_wR_factor_ref 0.0911
_refine_ls_wR_factor_gt 0.0859
_refine_ls_goodness_of_fit_ref 0.981
_refine_ls_restrained_S_all 0.981
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3738(3) 1.1482(2) 0.25826(11) 0.0245(6) Uani 1 1 d . . . . .
H1C H 0.2831 1.2066 0.2706 0.037 Uiso 1 1 calc R U . . .
O2 O 0.5845(3) 1.2651(2) 0.32139(10) 0.0241(5) Uani 1 1 d . . . . .
O3 O 0.9188(3) 0.8239(2) 0.20715(10) 0.0196(5) Uani 1 1 d . . . . .
O4 O 0.8779(3) 0.8207(2) 0.34447(10) 0.0210(5) Uani 1 1 d . . . . .
O5 O 1.3137(4) 1.3785(3) 0.43783(12) 0.0365(7) Uani 1 1 d . . . . .
O6 O 1.6265(5) 1.3043(3) 0.46156(15) 0.0556(9) Uani 1 1 d . . . . .
O7 O 1.7480(4) 0.7895(3) 0.47580(11) 0.0343(7) Uani 1 1 d . . . . .
O8 O 1.5651(4) 0.6493(2) 0.41866(12) 0.0300(6) Uani 1 1 d . . . . .
N1 N 1.0929(4) 0.9989(3) 0.15938(12) 0.0227(6) Uani 1 1 d . . . . .
H1A H 1.1886 0.9377 0.1468 0.027 Uiso 1 1 calc R U . . .
H1B H 1.1015 1.0908 0.1498 0.027 Uiso 1 1 calc R U . . .
N2 N 0.8802(4) 1.0542(3) 0.31519(12) 0.0183(6) Uani 1 1 d . . . . .
H2B H 0.9423 1.1384 0.3193 0.022 Uiso 1 1 calc R U . . .
N3 N 1.4456(5) 1.2833(3) 0.44479(13) 0.0309(8) Uani 1 1 d . . . . .
N4 N 1.6006(4) 0.7650(3) 0.44218(13) 0.0251(6) Uani 1 1 d . . . . .
C1 C 0.5492(5) 1.1647(3) 0.28871(15) 0.0182(7) Uani 1 1 d . . . . .
C2 C 0.7048(4) 1.0446(3) 0.27522(15) 0.0174(7) Uani 1 1 d . . . . .
H2A H 0.6343 0.9489 0.2802 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7742(5) 1.0626(3) 0.21067(15) 0.0184(7) Uani 1 1 d . . . . .
H3A H 0.6502 1.0530 0.1846 0.022 Uiso 1 1 calc R U . . .
H3B H 0.8323 1.1608 0.2052 0.022 Uiso 1 1 calc R U . . .
C4 C 0.9369(5) 0.9531(3) 0.19255(14) 0.0173(7) Uani 1 1 d . . . . .
C5 C 0.9545(5) 0.9423(3) 0.34660(15) 0.0179(7) Uani 1 1 d . . . . .
C6 C 1.1458(5) 0.9738(3) 0.38320(15) 0.0186(7) Uani 1 1 d . . . . .
C7 C 1.1998(5) 1.1132(3) 0.40059(15) 0.0198(7) Uani 1 1 d . . . . .
H7A H 1.1095 1.1924 0.3923 0.024 Uiso 1 1 calc R U . . .
C8 C 1.3859(5) 1.1341(3) 0.42993(15) 0.0228(7) Uani 1 1 d . . . . .
C9 C 1.5204(5) 1.0229(4) 0.44466(15) 0.0241(8) Uani 1 1 d . . . . .
H9A H 1.6484 1.0398 0.4651 0.029 Uiso 1 1 calc R U . . .
C10 C 1.4594(5) 0.8874(3) 0.42830(15) 0.0202(7) Uani 1 1 d . . . . .
C11 C 1.2741(5) 0.8596(3) 0.39862(15) 0.0195(7) Uani 1 1 d . . . . .
H11A H 1.2356 0.7633 0.3890 0.023 Uiso 1 1 calc R U . . .
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
O1 0.0159(11) 0.0244(12) 0.0331(15) -0.0061(10) -0.0013(11) 0.0055(10)
O2 0.0207(11) 0.0188(11) 0.0328(15) -0.0073(10) 0.0031(11) -0.0017(10)
O3 0.0184(11) 0.0133(10) 0.0270(13) -0.0012(9) 0.0015(11) 0.0011(9)
O4 0.0244(11) 0.0151(10) 0.0234(13) 0.0012(9) 0.0000(11) -0.0003(10)
O5 0.0528(17) 0.0205(12) 0.0364(17) -0.0041(12) 0.0023(13) -0.0025(13)
O6 0.067(2) 0.0342(16) 0.066(2) 0.0104(14) -0.0433(19) -0.0189(15)
O7 0.0259(12) 0.0469(16) 0.0300(16) 0.0040(13) -0.0085(13) 0.0043(13)
O8 0.0268(12) 0.0231(13) 0.0401(16) 0.0040(11) 0.0002(12) 0.0041(12)
N1 0.0209(14) 0.0154(13) 0.0319(18) -0.0016(12) 0.0048(15) -0.0022(12)
N2 0.0168(13) 0.0137(12) 0.0244(16) 0.0008(11) -0.0021(13) -0.0025(12)
N3 0.0458(18) 0.0240(15) 0.0230(18) 0.0025(13) -0.0095(16) -0.0121(16)
N4 0.0210(14) 0.0305(15) 0.0237(17) 0.0089(13) 0.0036(14) 0.0010(14)
C1 0.0180(15) 0.0164(14) 0.0202(17) 0.0047(14) 0.0048(15) -0.0024(14)
C2 0.0163(15) 0.0132(15) 0.023(2) 0.0000(13) 0.0001(14) -0.0003(13)
C3 0.0192(15) 0.0149(15) 0.0212(18) 0.0014(13) -0.0007(15) 0.0016(13)
C4 0.0169(15) 0.0156(14) 0.0193(17) -0.0026(13) -0.0048(14) -0.0015(14)
C5 0.0185(14) 0.0147(14) 0.0204(17) -0.0001(13) 0.0061(16) 0.0021(14)
C6 0.0218(16) 0.0171(15) 0.0169(18) 0.0029(13) 0.0019(14) -0.0010(13)
C7 0.0252(16) 0.0172(15) 0.0171(18) 0.0012(14) -0.0002(15) 0.0000(14)
C8 0.0314(18) 0.0203(16) 0.0166(17) 0.0027(14) -0.0005(16) -0.0058(15)
C9 0.0258(18) 0.0300(18) 0.0165(18) 0.0040(15) -0.0024(15) -0.0049(15)
C10 0.0213(16) 0.0215(15) 0.0179(18) 0.0052(14) 0.0022(15) 0.0024(15)
C11 0.0210(15) 0.0188(16) 0.0187(18) 0.0009(14) 0.0038(15) -0.0036(14)
_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
O1 C1 1.321(4) . ?
O1 H1C 0.8400 . ?
O2 C1 1.209(4) . ?
O3 C4 1.246(3) . ?
O4 C5 1.229(4) . ?
O5 N3 1.228(4) . ?
O6 N3 1.229(4) . ?
O7 N4 1.230(4) . ?
O8 N4 1.218(3) . ?
N1 C4 1.316(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C5 1.343(4) . ?
N2 C2 1.440(4) . ?
N2 H2B 0.8800 . ?
N3 C8 1.473(4) . ?
N4 C10 1.480(4) . ?
C1 C2 1.521(4) . ?
C2 C3 1.535(5) . ?
C2 H2A 1.0000 . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.502(4) . ?
C6 C11 1.381(4) . ?
C6 C7 1.393(4) . ?
C7 C8 1.373(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.380(4) . ?
C9 C10 1.365(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(4) . ?
C11 H11A 0.9500 . ?
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
C1 O1 H1C 109.5 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 N2 C2 124.0(3) . . ?
C5 N2 H2B 118.0 . . ?
C2 N2 H2B 118.0 . . ?
O5 N3 O6 124.6(3) . . ?
O5 N3 C8 117.9(3) . . ?
O6 N3 C8 117.5(3) . . ?
O8 N4 O7 125.0(3) . . ?
O8 N4 C10 117.9(3) . . ?
O7 N4 C10 117.0(3) . . ?
O2 C1 O1 124.4(3) . . ?
O2 C1 C2 124.3(3) . . ?
O1 C1 C2 111.2(3) . . ?
N2 C2 C1 109.5(3) . . ?
N2 C2 C3 111.6(2) . . ?
C1 C2 C3 107.4(2) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C4 C3 C2 112.6(3) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 N1 122.0(3) . . ?
O3 C4 C3 120.7(3) . . ?
N1 C4 C3 117.2(3) . . ?
O4 C5 N2 123.1(3) . . ?
O4 C5 C6 121.5(3) . . ?
N2 C5 C6 115.4(3) . . ?
C11 C6 C7 119.5(3) . . ?
C11 C6 C5 118.1(3) . . ?
C7 C6 C5 122.4(3) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7A 120.7 . . ?
C6 C7 H7A 120.7 . . ?
C7 C8 C9 123.3(3) . . ?
C7 C8 N3 117.7(3) . . ?
C9 C8 N3 119.0(3) . . ?
C10 C9 C8 116.3(3) . . ?
C10 C9 H9A 121.9 . . ?
C8 C9 H9A 121.9 . . ?
C9 C10 C11 123.1(3) . . ?
C9 C10 N4 118.2(3) . . ?
C11 C10 N4 118.6(3) . . ?
C6 C11 C10 119.0(3) . . ?
C6 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
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
C5 N2 C2 C1 129.9(3) . . . . ?
C5 N2 C2 C3 -111.3(3) . . . . ?
O2 C1 C2 N2 10.8(4) . . . . ?
O1 C1 C2 N2 -171.7(3) . . . . ?
O2 C1 C2 C3 -110.5(3) . . . . ?
O1 C1 C2 C3 67.0(3) . . . . ?
N2 C2 C3 C4 57.4(3) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
C2 C3 C4 O3 43.2(4) . . . . ?
C2 C3 C4 N1 -139.0(3) . . . . ?
C2 N2 C5 O4 -0.7(5) . . . . ?
C2 N2 C5 C6 176.9(3) . . . . ?
O4 C5 C6 C11 21.0(5) . . . . ?
N2 C5 C6 C11 -156.6(3) . . . . ?
O4 C5 C6 C7 -160.6(3) . . . . ?
N2 C5 C6 C7 21.8(4) . . . . ?
C11 C6 C7 C8 3.5(5) . . . . ?
C5 C6 C7 C8 -174.8(3) . . . . ?
C6 C7 C8 C9 -1.9(5) . . . . ?
C6 C7 C8 N3 176.5(3) . . . . ?
O5 N3 C8 C7 10.1(5) . . . . ?
O6 N3 C8 C7 -167.6(3) . . . . ?
O5 N3 C8 C9 -171.4(3) . . . . ?
O6 N3 C8 C9 10.8(5) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
N3 C8 C9 C10 -178.2(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C8 C9 C10 N4 178.9(3) . . . . ?
O8 N4 C10 C9 -167.2(3) . . . . ?
O7 N4 C10 C9 11.3(4) . . . . ?
O8 N4 C10 C11 11.8(4) . . . . ?
O7 N4 C10 C11 -169.7(3) . . . . ?
C7 C6 C11 C10 -3.5(5) . . . . ?
C5 C6 C11 C10 175.0(3) . . . . ?
C9 C10 C11 C6 1.7(5) . . . . ?
N4 C10 C11 C6 -177.2(3) . . . . ?
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
O1 H1C O3 0.84 1.76 2.596(3) 176.0 3_655
N1 H1A O2 0.88 2.27 3.017(3) 142.3 3_745
N1 H1B O4 0.88 2.14 2.986(3) 162.2 3_755
N2 H2B O3 0.88 2.02 2.852(3) 156.8 3_755
C7 H7A O3 0.95 2.57 3.212(4) 125.6 3_755
C9 H9A O5 0.95 2.55 3.376(4) 145.2 4_576
_refine_diff_density_max 0.249
_refine_diff_density_min -0.259
_refine_diff_density_rms 0.052
_database_code_depnum_ccdc_archive 'CCDC 933064'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_dnbn(chiral)
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
N-(3,5-dinitrobenzoyl)asparagine
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C11 H10 N4 O8'
_chemical_formula_sum 'C11 H10 N4 O8'
_chemical_formula_weight 326.23
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 6.381(2)
_cell_length_b 9.276(2)
_cell_length_c 22.660(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1341.2(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 758
_cell_measurement_theta_min 1.9480
_cell_measurement_theta_max 77.3158
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.616
_exptl_crystal_F_000 672
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.190
_exptl_crystal_size_mid 0.060
_exptl_crystal_size_min 0.020
_exptl_absorpt_coefficient_mu 1.229
_shelx_estimated_absorpt_T_min 0.800
_shelx_estimated_absorpt_T_max 0.976
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.867
_exptl_absorpt_correction_T_max 0.980
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 1.54175
_diffrn_radiation_type CuK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Xcalibur, Onyx'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 3963
_diffrn_reflns_av_unetI/netI 0.1126
_diffrn_reflns_av_R_equivalents 0.0672
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 3.901
_diffrn_reflns_theta_max 77.507
_diffrn_reflns_theta_full 67.676
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.900
_reflns_number_total 2454
_reflns_number_gt 1844
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.492
_reflns_Friedel_fraction_max 0.689
_reflns_Friedel_fraction_full 0.757
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.8926P]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 493 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack 0.7(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns 2454
_refine_ls_number_parameters 208
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0919
_refine_ls_R_factor_gt 0.0683
_refine_ls_wR_factor_ref 0.1964
_refine_ls_wR_factor_gt 0.1646
_refine_ls_goodness_of_fit_ref 1.060
_refine_ls_restrained_S_all 1.060
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6267(7) 0.6482(5) 0.2586(2) 0.0295(11) Uani 1 1 d . . . . .
H1C H 0.7171 0.7065 0.2711 0.044 Uiso 1 1 calc R U . . .
O2 O 0.4162(7) 0.7653(5) 0.3212(2) 0.0286(10) Uani 1 1 d . . . . .
O3 O 0.0819(7) 0.3232(4) 0.2068(2) 0.0257(10) Uani 1 1 d . . . . .
O4 O 0.1220(8) 0.3197(5) 0.3446(2) 0.0266(10) Uani 1 1 d . . . . .
O5 O -0.5646(9) 0.1489(5) 0.4187(2) 0.0338(11) Uani 1 1 d . . . . .
O6 O -0.7480(9) 0.2897(6) 0.4756(2) 0.0397(13) Uani 1 1 d . . . . .
O7 O -0.6258(12) 0.8050(7) 0.4613(3) 0.059(2) Uani 1 1 d . . . . .
O8 O -0.3141(10) 0.8783(6) 0.4380(3) 0.0425(14) Uani 1 1 d . . . . .
N1 N -0.0934(9) 0.4993(6) 0.1596(3) 0.0267(12) Uani 1 1 d . . . . .
H1A H -0.1894 0.4383 0.1473 0.032 Uiso 1 1 calc R U . . .
H1B H -0.1021 0.5911 0.1501 0.032 Uiso 1 1 calc R U . . .
N2 N 0.1199(9) 0.5550(6) 0.3151(2) 0.0230(11) Uani 1 1 d . . . . .
H2A H 0.0580 0.6392 0.3191 0.028 Uiso 1 1 calc R U . . .
N3 N -0.6000(9) 0.2651(7) 0.4422(3) 0.0292(12) Uani 1 1 d . . . . .
N4 N -0.4434(12) 0.7837(7) 0.4449(3) 0.0383(16) Uani 1 1 d . . . . .
C1 C 0.4499(10) 0.6658(7) 0.2885(3) 0.0264(13) Uani 1 1 d . . . . .
C2 C 0.2954(10) 0.5456(7) 0.2753(3) 0.0223(13) Uani 1 1 d . . . . .
H2B H 0.3665 0.4504 0.2807 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2246(10) 0.5609(7) 0.2111(3) 0.0254(13) Uani 1 1 d . . . . .
H3A H 0.1659 0.6586 0.2054 0.031 Uiso 1 1 calc R U . . .
H3B H 0.3487 0.5518 0.1852 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0652(10) 0.4528(7) 0.1926(3) 0.0227(12) Uani 1 1 d . . . . .
C5 C 0.0436(10) 0.4421(7) 0.3469(3) 0.0237(12) Uani 1 1 d . . . . .
C6 C -0.1449(11) 0.4723(7) 0.3837(3) 0.0234(13) Uani 1 1 d . . . . .
C7 C -0.2746(11) 0.3600(7) 0.3982(3) 0.0241(13) Uani 1 1 d . . . . .
H7A H -0.2372 0.2644 0.3875 0.029 Uiso 1 1 calc R U . . .
C8 C -0.4600(11) 0.3851(7) 0.4284(3) 0.0255(13) Uani 1 1 d . . . . .
C9 C -0.5205(12) 0.5243(8) 0.4446(3) 0.0295(15) Uani 1 1 d . . . . .
H9A H -0.6487 0.5416 0.4647 0.035 Uiso 1 1 calc R U . . .
C10 C -0.3875(13) 0.6350(7) 0.4303(3) 0.0289(15) Uani 1 1 d . . . . .
C11 C -0.2005(12) 0.6128(7) 0.4002(3) 0.0276(14) Uani 1 1 d . . . . .
H11A H -0.1116 0.6918 0.3909 0.033 Uiso 1 1 calc R U . . .
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
O1 0.018(2) 0.029(2) 0.042(3) -0.004(2) 0.006(2) -0.006(2)
O2 0.025(2) 0.021(2) 0.039(2) -0.008(2) -0.002(2) 0.003(2)
O3 0.025(2) 0.0143(19) 0.038(2) -0.0011(18) -0.002(2) 0.0018(18)
O4 0.034(3) 0.0149(19) 0.031(2) -0.0003(18) -0.002(2) 0.0038(19)
O5 0.034(3) 0.019(2) 0.048(3) 0.004(2) -0.003(2) -0.001(2)
O6 0.032(3) 0.048(3) 0.040(3) 0.005(3) 0.013(2) -0.002(3)
O7 0.070(4) 0.034(3) 0.075(4) 0.010(3) 0.037(4) 0.022(3)
O8 0.058(4) 0.023(2) 0.047(3) -0.007(2) -0.005(3) 0.004(3)
N1 0.016(3) 0.020(2) 0.044(3) 0.000(2) -0.007(2) 0.003(2)
N2 0.021(3) 0.016(2) 0.031(2) 0.003(2) 0.001(2) 0.003(2)
N3 0.027(3) 0.032(3) 0.029(3) 0.004(2) -0.002(2) -0.002(3)
N4 0.059(4) 0.024(3) 0.032(3) -0.001(2) 0.000(3) 0.013(3)
C1 0.023(3) 0.024(3) 0.033(3) 0.001(3) 0.002(3) -0.001(3)
C2 0.023(3) 0.017(3) 0.028(3) 0.000(2) 0.005(3) -0.001(2)
C3 0.023(3) 0.021(3) 0.032(3) -0.001(2) 0.005(3) -0.003(3)
C4 0.020(3) 0.014(3) 0.033(3) 0.005(2) 0.001(3) 0.003(3)
C5 0.020(3) 0.018(3) 0.033(3) -0.001(3) -0.004(3) -0.001(3)
C6 0.025(3) 0.018(3) 0.027(3) -0.005(2) 0.004(3) 0.004(2)
C7 0.026(3) 0.019(3) 0.027(3) 0.002(2) -0.002(3) 0.005(3)
C8 0.028(3) 0.019(3) 0.029(3) 0.007(3) 0.002(3) -0.002(3)
C9 0.033(4) 0.030(3) 0.025(3) 0.009(3) 0.000(3) 0.008(3)
C10 0.046(4) 0.014(3) 0.026(3) -0.003(2) -0.002(3) 0.009(3)
C11 0.034(4) 0.019(3) 0.030(3) -0.002(3) 0.004(3) 0.001(3)
_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
O1 C1 1.326(8) . ?
O1 H1C 0.8400 . ?
O2 C1 1.203(8) . ?
O3 C4 1.249(7) . ?
O4 C5 1.242(8) . ?
O5 N3 1.224(8) . ?
O6 N3 1.232(8) . ?
O7 N4 1.238(10) . ?
O8 N4 1.214(9) . ?
N1 C4 1.330(9) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C5 1.361(8) . ?
N2 C2 1.440(8) . ?
N2 H2A 0.8800 . ?
N3 C8 1.461(9) . ?
N4 C10 1.462(8) . ?
C1 C2 1.518(9) . ?
C2 C3 1.530(9) . ?
C2 H2B 1.0000 . ?
C3 C4 1.489(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.490(9) . ?
C6 C7 1.370(9) . ?
C6 C11 1.402(8) . ?
C7 C8 1.386(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.398(9) . ?
C9 C10 1.371(11) . ?
C9 H9A 0.9500 . ?
C10 C11 1.390(11) . ?
C11 H11A 0.9500 . ?
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
C1 O1 H1C 109.5 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 N2 C2 124.3(5) . . ?
C5 N2 H2A 117.9 . . ?
C2 N2 H2A 117.9 . . ?
O5 N3 O6 125.0(6) . . ?
O5 N3 C8 117.6(6) . . ?
O6 N3 C8 117.4(6) . . ?
O8 N4 O7 124.2(7) . . ?
O8 N4 C10 119.2(7) . . ?
O7 N4 C10 116.6(7) . . ?
O2 C1 O1 124.1(6) . . ?
O2 C1 C2 124.6(6) . . ?
O1 C1 C2 111.2(5) . . ?
N2 C2 C1 109.8(5) . . ?
N2 C2 C3 111.1(5) . . ?
C1 C2 C3 108.1(5) . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C4 C3 C2 114.1(6) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O3 C4 N1 121.5(6) . . ?
O3 C4 C3 121.1(6) . . ?
N1 C4 C3 117.4(6) . . ?
O4 C5 N2 122.5(6) . . ?
O4 C5 C6 121.4(6) . . ?
N2 C5 C6 116.1(6) . . ?
C7 C6 C11 119.3(6) . . ?
C7 C6 C5 118.6(6) . . ?
C11 C6 C5 121.9(6) . . ?
C6 C7 C8 120.4(6) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C7 C8 C9 121.4(6) . . ?
C7 C8 N3 120.0(6) . . ?
C9 C8 N3 118.6(6) . . ?
C10 C9 C8 117.3(6) . . ?
C10 C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C10 C11 122.4(6) . . ?
C9 C10 N4 120.2(7) . . ?
C11 C10 N4 117.4(7) . . ?
C10 C11 C6 119.1(6) . . ?
C10 C11 H11A 120.5 . . ?
C6 C11 H11A 120.5 . . ?
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
C5 N2 C2 C1 -130.3(6) . . . . ?
C5 N2 C2 C3 110.2(7) . . . . ?
O2 C1 C2 N2 -9.9(9) . . . . ?
O1 C1 C2 N2 171.0(5) . . . . ?
O2 C1 C2 C3 111.4(7) . . . . ?
O1 C1 C2 C3 -67.7(7) . . . . ?
N2 C2 C3 C4 -57.3(7) . . . . ?
C1 C2 C3 C4 -177.7(5) . . . . ?
C2 C3 C4 O3 -43.2(9) . . . . ?
C2 C3 C4 N1 137.9(6) . . . . ?
C2 N2 C5 O4 0.7(10) . . . . ?
C2 N2 C5 C6 -177.5(6) . . . . ?
O4 C5 C6 C7 -22.8(10) . . . . ?
N2 C5 C6 C7 155.4(6) . . . . ?
O4 C5 C6 C11 161.8(7) . . . . ?
N2 C5 C6 C11 -20.0(9) . . . . ?
C11 C6 C7 C8 0.6(10) . . . . ?
C5 C6 C7 C8 -174.9(6) . . . . ?
C6 C7 C8 C9 0.3(10) . . . . ?
C6 C7 C8 N3 178.3(6) . . . . ?
O5 N3 C8 C7 -11.1(9) . . . . ?
O6 N3 C8 C7 170.6(6) . . . . ?
O5 N3 C8 C9 167.0(7) . . . . ?
O6 N3 C8 C9 -11.2(9) . . . . ?
C7 C8 C9 C10 -1.0(10) . . . . ?
N3 C8 C9 C10 -179.1(6) . . . . ?
C8 C9 C10 C11 0.9(10) . . . . ?
C8 C9 C10 N4 178.7(6) . . . . ?
O8 N4 C10 C9 171.7(7) . . . . ?
O7 N4 C10 C9 -11.3(11) . . . . ?
O8 N4 C10 C11 -10.4(10) . . . . ?
O7 N4 C10 C11 166.6(7) . . . . ?
C9 C10 C11 C6 0.0(10) . . . . ?
N4 C10 C11 C6 -177.9(6) . . . . ?
C7 C6 C11 C10 -0.8(10) . . . . ?
C5 C6 C11 C10 174.6(6) . . . . ?
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
N1 H1A O2 0.88 2.28 3.024(7) 142.8 3_545
N1 H1B O4 0.88 2.13 2.979(7) 162.6 3
N2 H2A O3 0.88 2.01 2.845(7) 157.1 3
O1 H1C O3 0.84 1.75 2.590(6) 175.9 3_655
_refine_diff_density_max 0.333
_refine_diff_density_min -0.387
_refine_diff_density_rms 0.086
_database_code_depnum_ccdc_archive 'CCDC 933065'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_DNBN(RACEMIC)
#TrackingRef 'bialonska_cif.cif'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
N-(3,5-dinitrobenzoyl)asparagine
;
_chemical_name_common ?
_chemical_melting_point 468
_chemical_formula_moiety 'C11 H10 N4 O8'
_chemical_formula_sum 'C11 H10 N4 O8'
_chemical_formula_weight 326.23
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 21/c'
_space_group_name_Hall '-P 2ybc'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 4.583(2)
_cell_length_b 21.947(5)
_cell_length_c 12.852(3)
_cell_angle_alpha 90
_cell_angle_beta 92.76(2)
_cell_angle_gamma 90
_cell_volume 1291.2(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 440
_cell_measurement_theta_min 2.0113
_cell_measurement_theta_max 67.9955
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.678
_exptl_crystal_F_000 672
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.240
_exptl_crystal_size_mid 0.040
_exptl_crystal_size_min 0.010
_exptl_absorpt_coefficient_mu 1.276
_shelx_estimated_absorpt_T_min 0.749
_shelx_estimated_absorpt_T_max 0.987
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.25212
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 1.54175
_diffrn_radiation_type CuK\a
_diffrn_source 'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type 'Xcalibur, Onyx'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 4191
_diffrn_reflns_av_unetI/netI 0.2181
_diffrn_reflns_av_R_equivalents 0.1085
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 3.989
_diffrn_reflns_theta_max 62.479
_diffrn_reflns_theta_full 67.676
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.829
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.829
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.829
_reflns_number_total 1948
_reflns_number_gt 710
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0803P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 1948
_refine_ls_number_parameters 208
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1472
_refine_ls_R_factor_gt 0.0640
_refine_ls_wR_factor_ref 0.1674
_refine_ls_wR_factor_gt 0.1452
_refine_ls_goodness_of_fit_ref 0.706
_refine_ls_restrained_S_all 0.706
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2646(10) 0.7643(2) 0.4750(3) 0.0376(13) Uani 1 1 d . . . . .
H1C H 1.3104 0.7628 0.5391 0.056 Uiso 1 1 calc R U . . .
O2 O 0.8885(10) 0.7057(2) 0.5190(3) 0.0342(12) Uani 1 1 d . . . . .
O3 O 0.4692(9) 0.7326(2) 0.1700(3) 0.0353(12) Uani 1 1 d . . . . .
O4 O 0.8835(10) 0.8721(2) 0.3897(4) 0.0398(13) Uani 1 1 d . . . . .
O5 O 1.5984(14) 1.0414(3) 0.4175(4) 0.0660(19) Uani 1 1 d . . . . .
O6 O 1.8691(15) 1.0626(3) 0.2888(4) 0.069(2) Uani 1 1 d . . . . .
O7 O 1.7713(11) 0.9448(2) -0.0272(4) 0.0440(14) Uani 1 1 d . . . . .
O8 O 1.3931(10) 0.8853(2) -0.0490(3) 0.0380(13) Uani 1 1 d . . . . .
N1 N 0.7673(13) 0.6595(3) 0.1099(4) 0.0432(17) Uani 1 1 d . . . . .
H1A H 0.6810 0.6608 0.0473 0.052 Uiso 1 1 calc R U . . .
H1B H 0.9134 0.6341 0.1229 0.052 Uiso 1 1 calc R U . . .
N2 N 1.0371(12) 0.7947(3) 0.2895(4) 0.0316(14) Uani 1 1 d . . . . .
H2A H 1.1369 0.7837 0.2359 0.038 Uiso 1 1 calc R U . . .
N3 N 1.6830(17) 1.0317(3) 0.3308(5) 0.050(2) Uani 1 1 d . . . . .
N4 N 1.5614(14) 0.9179(3) 0.0055(4) 0.0366(16) Uani 1 1 d . . . . .
C1 C 1.0092(15) 0.7368(3) 0.4566(5) 0.0312(17) Uani 1 1 d . . . . .
C2 C 0.8749(15) 0.7495(3) 0.3461(5) 0.0353(19) Uani 1 1 d . . . . .
H2B H 0.6737 0.7660 0.3540 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8450(15) 0.6900(3) 0.2885(5) 0.0317(18) Uani 1 1 d . . . . .
H3A H 0.7434 0.6604 0.3323 0.038 Uiso 1 1 calc R U . . .
H3B H 1.0425 0.6737 0.2773 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6783(15) 0.6951(3) 0.1837(5) 0.0314(18) Uani 1 1 d . . . . .
C5 C 1.0336(15) 0.8531(3) 0.3196(5) 0.0302(18) Uani 1 1 d . . . . .
C6 C 1.2310(14) 0.8935(3) 0.2637(5) 0.0267(16) Uani 1 1 d . . . . .
C7 C 1.3517(15) 0.9431(3) 0.3190(5) 0.0317(18) Uani 1 1 d . . . . .
H7A H 1.3000 0.9509 0.3885 0.038 Uiso 1 1 calc R U . . .
C8 C 1.5468(16) 0.9807(3) 0.2714(5) 0.0350(19) Uani 1 1 d . . . . .
C9 C 1.6266(15) 0.9733(3) 0.1698(5) 0.0337(18) Uani 1 1 d . . . . .
H9A H 1.7632 0.9995 0.1391 0.040 Uiso 1 1 calc R U . . .
C10 C 1.4948(14) 0.9253(3) 0.1158(5) 0.0289(17) Uani 1 1 d . . . . .
C11 C 1.3036(15) 0.8857(3) 0.1601(5) 0.0343(19) Uani 1 1 d . . . . .
H11A H 1.2211 0.8530 0.1203 0.041 Uiso 1 1 calc R U . . .
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
O1 0.033(3) 0.053(3) 0.025(3) 0.006(2) -0.016(2) -0.004(2)
O2 0.038(3) 0.041(3) 0.022(2) 0.006(2) -0.015(2) -0.001(2)
O3 0.033(3) 0.047(3) 0.025(3) 0.001(2) -0.012(2) 0.005(3)
O4 0.038(3) 0.054(3) 0.027(3) 0.000(3) -0.009(2) 0.007(3)
O5 0.096(5) 0.059(4) 0.042(3) -0.016(3) -0.018(3) -0.008(4)
O6 0.100(5) 0.048(4) 0.056(4) -0.002(3) -0.020(4) -0.034(4)
O7 0.042(3) 0.046(3) 0.044(3) 0.011(3) -0.003(2) -0.005(3)
O8 0.042(3) 0.045(3) 0.025(3) -0.001(2) -0.008(2) 0.003(2)
N1 0.048(4) 0.058(4) 0.023(3) 0.001(3) -0.012(3) 0.016(3)
N2 0.037(3) 0.039(4) 0.018(3) 0.007(3) -0.011(2) -0.006(3)
N3 0.078(5) 0.033(4) 0.035(4) -0.002(3) -0.031(4) -0.005(4)
N4 0.043(4) 0.034(4) 0.031(4) 0.003(3) -0.013(3) 0.006(3)
C1 0.041(5) 0.038(4) 0.014(3) -0.002(3) -0.011(3) 0.000(4)
C2 0.038(4) 0.047(5) 0.020(4) 0.009(3) -0.008(3) 0.002(4)
C3 0.036(4) 0.036(4) 0.022(4) 0.003(3) -0.010(3) -0.003(3)
C4 0.038(5) 0.039(5) 0.016(3) 0.003(3) -0.006(3) -0.008(4)
C5 0.029(4) 0.043(5) 0.017(4) 0.005(3) -0.015(3) -0.004(4)
C6 0.029(4) 0.029(4) 0.021(4) 0.000(3) -0.010(3) 0.006(3)
C7 0.042(4) 0.029(4) 0.022(4) 0.002(3) -0.015(3) 0.001(3)
C8 0.052(5) 0.017(4) 0.033(4) -0.003(3) -0.022(4) -0.002(3)
C9 0.035(4) 0.028(4) 0.036(4) 0.010(3) -0.020(3) 0.000(3)
C10 0.041(4) 0.023(4) 0.022(4) 0.002(3) -0.012(3) 0.001(3)
C11 0.046(4) 0.026(4) 0.029(4) 0.001(3) -0.023(3) -0.003(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
O1 C1 1.328(8) . ?
O1 H1C 0.8400 . ?
O2 C1 1.207(8) . ?
O3 C4 1.268(8) . ?
O4 C5 1.233(8) . ?
O5 N3 1.215(8) . ?
O6 N3 1.233(8) . ?
O7 N4 1.220(7) . ?
O8 N4 1.243(7) . ?
N1 C4 1.310(8) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C5 1.339(8) . ?
N2 C2 1.455(8) . ?
N2 H2A 0.8800 . ?
N3 C8 1.478(8) . ?
N4 C10 1.474(8) . ?
C1 C2 1.546(8) . ?
C2 C3 1.506(9) . ?
C2 H2B 1.0000 . ?
C3 C4 1.520(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.477(9) . ?
C6 C11 1.398(9) . ?
C6 C7 1.400(8) . ?
C7 C8 1.381(10) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(10) . ?
C9 C10 1.384(9) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(9) . ?
C11 H11A 0.9500 . ?
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
C1 O1 H1C 109.5 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 N2 C2 119.7(6) . . ?
C5 N2 H2A 120.2 . . ?
C2 N2 H2A 120.2 . . ?
O5 N3 O6 124.2(7) . . ?
O5 N3 C8 117.5(7) . . ?
O6 N3 C8 118.3(7) . . ?
O7 N4 O8 124.2(6) . . ?
O7 N4 C10 118.7(6) . . ?
O8 N4 C10 117.0(6) . . ?
O2 C1 O1 124.5(5) . . ?
O2 C1 C2 122.5(6) . . ?
O1 C1 C2 112.9(6) . . ?
N2 C2 C3 112.5(6) . . ?
N2 C2 C1 113.1(6) . . ?
C3 C2 C1 108.5(5) . . ?
N2 C2 H2B 107.5 . . ?
C3 C2 H2B 107.5 . . ?
C1 C2 H2B 107.5 . . ?
C2 C3 C4 113.6(6) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O3 C4 N1 123.1(5) . . ?
O3 C4 C3 121.1(6) . . ?
N1 C4 C3 115.8(6) . . ?
O4 C5 N2 123.3(7) . . ?
O4 C5 C6 121.9(7) . . ?
N2 C5 C6 114.7(7) . . ?
C11 C6 C7 118.2(7) . . ?
C11 C6 C5 124.7(6) . . ?
C7 C6 C5 117.1(6) . . ?
C8 C7 C6 119.1(7) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C9 123.8(6) . . ?
C7 C8 N3 119.3(7) . . ?
C9 C8 N3 116.9(7) . . ?
C8 C9 C10 115.7(7) . . ?
C8 C9 H9A 122.2 . . ?
C10 C9 H9A 122.2 . . ?
C11 C10 C9 123.0(7) . . ?
C11 C10 N4 119.5(6) . . ?
C9 C10 N4 117.5(7) . . ?
C10 C11 C6 120.1(6) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
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
C5 N2 C2 C3 166.8(5) . . . . ?
C5 N2 C2 C1 -69.8(8) . . . . ?
O2 C1 C2 N2 172.0(7) . . . . ?
O1 C1 C2 N2 -7.0(9) . . . . ?
O2 C1 C2 C3 -62.5(9) . . . . ?
O1 C1 C2 C3 118.5(7) . . . . ?
N2 C2 C3 C4 -61.8(8) . . . . ?
C1 C2 C3 C4 172.3(6) . . . . ?
C2 C3 C4 O3 -34.0(10) . . . . ?
C2 C3 C4 N1 145.1(7) . . . . ?
C2 N2 C5 O4 -4.8(9) . . . . ?
C2 N2 C5 C6 173.7(5) . . . . ?
O4 C5 C6 C11 -149.9(6) . . . . ?
N2 C5 C6 C11 31.6(9) . . . . ?
O4 C5 C6 C7 29.8(9) . . . . ?
N2 C5 C6 C7 -148.7(5) . . . . ?
C11 C6 C7 C8 -2.9(9) . . . . ?
C5 C6 C7 C8 177.4(6) . . . . ?
C6 C7 C8 C9 1.8(10) . . . . ?
C6 C7 C8 N3 -177.8(6) . . . . ?
O5 N3 C8 C7 -5.8(10) . . . . ?
O6 N3 C8 C7 175.9(7) . . . . ?
O5 N3 C8 C9 174.7(6) . . . . ?
O6 N3 C8 C9 -3.6(9) . . . . ?
C7 C8 C9 C10 0.8(9) . . . . ?
N3 C8 C9 C10 -179.7(6) . . . . ?
C8 C9 C10 C11 -2.2(9) . . . . ?
C8 C9 C10 N4 176.8(6) . . . . ?
O7 N4 C10 C11 -165.5(6) . . . . ?
O8 N4 C10 C11 16.2(9) . . . . ?
O7 N4 C10 C9 15.5(8) . . . . ?
O8 N4 C10 C9 -162.8(5) . . . . ?
C9 C10 C11 C6 1.1(10) . . . . ?
N4 C10 C11 C6 -177.8(6) . . . . ?
C7 C6 C11 C10 1.5(9) . . . . ?
C5 C6 C11 C10 -178.7(6) . . . . ?
_refine_diff_density_max 0.326
_refine_diff_density_min -0.332
_refine_diff_density_rms 0.090
#===== end of cif
_database_code_depnum_ccdc_archive 'CCDC 933066'