# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
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data_STAN-DBA
_database_code_depnum_ccdc_archive 'CCDC 1863937'
_audit_update_record
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2017/1
_shelx_SHELXL_version_number 2017/1
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H33 N2 O, C7 H5 O4'
_chemical_formula_sum 'C28 H38 N2 O5'
_chemical_formula_weight 482.60
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 8.8708(18)
_cell_length_b 15.609(3)
_cell_length_c 18.593(4)
_cell_angle_alpha 90
_cell_angle_beta 90.01(3)
_cell_angle_gamma 90
_cell_volume 2574.5(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 11259
_cell_measurement_theta_min 3.4048
_cell_measurement_theta_max 27.4739
_exptl_crystal_description Block
_exptl_crystal_colour Colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.245
_exptl_crystal_F_000 1040
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.360
_exptl_crystal_size_min 0.350
_exptl_absorpt_coefficient_mu 0.085
_shelx_estimated_absorpt_T_min 0.967
_shelx_estimated_absorpt_T_max 0.971
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.8957
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details ?
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 9574
_diffrn_reflns_av_unetI/netI 0.0306
_diffrn_reflns_av_R_equivalents ?
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 3.174
_diffrn_reflns_theta_max 25.499
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 9574
_reflns_number_gt 9453
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.925
_reflns_Friedel_fraction_max 0.998
_reflns_Friedel_fraction_full 0.998
_reflns_special_details
;
_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 ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refined as a 2-component twin.
;
_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^)+(0.0360P)^2^+0.1231P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 4302 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.0(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns 9574
_refine_ls_number_parameters 674
_refine_ls_number_restraints 11
_refine_ls_R_factor_all 0.0309
_refine_ls_R_factor_gt 0.0304
_refine_ls_wR_factor_ref 0.0702
_refine_ls_wR_factor_gt 0.0698
_refine_ls_goodness_of_fit_ref 1.055
_refine_ls_restrained_S_all 1.055
_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 0.6687(3) 0.62401(15) 0.92622(11) 0.0253(5) Uani 1 1 d D . . . .
H1B H 0.755(2) 0.607(2) 0.9391(17) 0.023(9) Uiso 1 1 d D . . . .
O2 O -0.2494(3) 0.97206(15) 0.42609(11) 0.0249(5) Uani 1 1 d D . . . .
H2A H -0.338(3) 0.983(4) 0.439(3) 0.086(19) Uiso 1 1 d D . . . .
O3 O 0.5250(3) 0.52638(18) 0.52724(13) 0.0397(7) Uani 1 1 d . . . . .
O4 O 0.4695(3) 0.53909(17) 0.41085(14) 0.0369(6) Uani 1 1 d . . . . .
O5 O 0.7837(3) 0.5708(2) 0.57406(14) 0.0470(7) Uani 1 1 d D . . . .
H5A H 0.694(3) 0.551(3) 0.571(2) 0.056 Uiso 1 1 d D U . . .
O6 O 0.6685(3) 0.58542(19) 0.32187(14) 0.0453(7) Uani 1 1 d D . . . .
H6 H 0.585(3) 0.567(3) 0.339(2) 0.054 Uiso 1 1 d D U . . .
O7 O -0.0723(3) 0.55539(17) -0.02636(13) 0.0379(6) Uani 1 1 d . . . . .
O8 O -0.0952(3) 0.55864(16) 0.09242(13) 0.0331(6) Uani 1 1 d . . . . .
O9 O 0.1273(3) 0.52087(17) 0.17341(13) 0.0364(6) Uani 1 1 d D . . . .
H9 H 0.042(3) 0.540(3) 0.159(2) 0.053(14) Uiso 1 1 d D . . . .
O10 O 0.1732(3) 0.51093(17) -0.08403(13) 0.0347(6) Uani 1 1 d D . . . .
H10 H 0.081(2) 0.521(3) -0.077(3) 0.071(17) Uiso 1 1 d D . . . .
N1 N -0.2110(3) 0.96159(18) 0.60275(15) 0.0254(6) Uani 1 1 d D . . . .
H1A H -0.293(3) 0.9911(19) 0.5914(17) 0.024(9) Uiso 1 1 d D . . . .
N2 N -0.1153(3) 0.93224(18) 0.55215(14) 0.0248(6) Uani 1 1 d D . . . .
H2 H -0.137(5) 0.936(3) 0.5056(9) 0.053(13) Uiso 1 1 d D . . . .
N3 N 0.6435(3) 0.63986(17) 0.10186(14) 0.0224(6) Uani 1 1 d D . . . .
H3 H 0.732(2) 0.617(2) 0.0975(19) 0.027 Uiso 1 1 d D U . . .
N4 N 0.5446(3) 0.66584(17) 0.05196(14) 0.0219(6) Uani 1 1 d D . . . .
H4 H 0.563(4) 0.654(2) 0.0065(9) 0.026 Uiso 1 1 d D U . . .
C1 C -0.1515(4) 0.9481(2) 0.66767(18) 0.0272(7) Uani 1 1 d . . . . .
H1 H -0.196895 0.962823 0.712279 0.033 Uiso 1 1 calc R U . . .
C2 C -0.0122(4) 0.9091(2) 0.65899(17) 0.0240(7) Uani 1 1 d . . . . .
C3 C 0.0076(4) 0.89968(19) 0.58542(17) 0.0228(7) Uani 1 1 d . . . . .
C4 C 0.1397(4) 0.8585(2) 0.55027(17) 0.0248(7) Uani 1 1 d . . . . .
H4A H 0.176867 0.895294 0.510723 0.030 Uiso 1 1 calc R U . . .
H4B H 0.109356 0.802648 0.529526 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2670(4) 0.8446(2) 0.60633(17) 0.0223(7) Uani 1 1 d . . . . .
H5 H 0.314668 0.901797 0.614909 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2090(3) 0.81207(19) 0.68033(15) 0.0196(6) Uani 1 1 d . . . . .
C7 C 0.1041(4) 0.8809(2) 0.71290(17) 0.0260(7) Uani 1 1 d . . . . .
H7A H 0.053164 0.857332 0.755925 0.031 Uiso 1 1 calc R U . . .
H7B H 0.164842 0.930931 0.728168 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1202(4) 0.7282(2) 0.67156(17) 0.0267(7) Uani 1 1 d . . . . .
H8A H 0.093857 0.705549 0.719096 0.040 Uiso 1 1 calc R U . . .
H8B H 0.182232 0.686191 0.645850 0.040 Uiso 1 1 calc R U . . .
H8C H 0.027869 0.739215 0.644132 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3889(4) 0.7867(2) 0.57430(17) 0.0305(8) Uani 1 1 d . . . . .
H9A H 0.343186 0.731007 0.561131 0.037 Uiso 1 1 calc R U . . .
H9B H 0.428097 0.813331 0.529747 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5200(4) 0.7710(2) 0.62595(17) 0.0317(8) Uani 1 1 d . . . . .
H10A H 0.575817 0.825170 0.633392 0.038 Uiso 1 1 calc R U . . .
H10B H 0.590241 0.728912 0.604377 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4646(4) 0.7371(2) 0.69893(16) 0.0202(6) Uani 1 1 d . . . . .
H11 H 0.413500 0.680745 0.690988 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3480(4) 0.8007(2) 0.73048(16) 0.0207(6) Uani 1 1 d . . . . .
H12 H 0.399477 0.857723 0.731670 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3038(4) 0.7808(2) 0.80929(16) 0.0271(7) Uani 1 1 d . . . . .
H13A H 0.244768 0.829302 0.828804 0.033 Uiso 1 1 calc R U . . .
H13B H 0.238604 0.729297 0.810143 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4415(4) 0.7652(2) 0.85777(16) 0.0267(7) Uani 1 1 d . . . . .
H14A H 0.499589 0.819045 0.862642 0.032 Uiso 1 1 calc R U . . .
H14B H 0.407173 0.747819 0.906286 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5423(3) 0.69604(19) 0.82683(16) 0.0199(6) Uani 1 1 d . . . . .
C16 C 0.5947(4) 0.7238(2) 0.75167(16) 0.0231(7) Uani 1 1 d . . . . .
H16 H 0.646854 0.780191 0.757177 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4551(4) 0.6108(2) 0.82416(18) 0.0285(7) Uani 1 1 d . . . . .
H17A H 0.416248 0.597270 0.872180 0.043 Uiso 1 1 calc R U . . .
H17B H 0.522730 0.564912 0.808242 0.043 Uiso 1 1 calc R U . . .
H17C H 0.370779 0.615919 0.790364 0.043 Uiso 1 1 calc R U . . .
C18 C 0.7154(4) 0.6575(2) 0.73227(18) 0.0315(8) Uani 1 1 d . . . . .
H18A H 0.790129 0.681918 0.698459 0.038 Uiso 1 1 calc R U . . .
H18B H 0.669417 0.606038 0.710182 0.038 Uiso 1 1 calc R U . . .
C19 C 0.7906(4) 0.6350(2) 0.80602(17) 0.0269(7) Uani 1 1 d . . . . .
H19A H 0.791547 0.572253 0.813494 0.032 Uiso 1 1 calc R U . . .
H19B H 0.895757 0.656220 0.807334 0.032 Uiso 1 1 calc R U . . .
C20 C 0.6948(4) 0.67961(19) 0.86520(17) 0.0228(7) Uani 1 1 d . . . . .
C21 C 0.7730(4) 0.7607(2) 0.8922(2) 0.0369(8) Uani 1 1 d . . . . .
H21A H 0.713787 0.785960 0.931345 0.055 Uiso 1 1 calc R U . . .
H21B H 0.781569 0.802013 0.852733 0.055 Uiso 1 1 calc R U . . .
H21C H 0.873911 0.746211 0.909952 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5916(4) 0.6604(2) 0.16716(17) 0.0216(7) Uani 1 1 d . . . . .
H22 H 0.640407 0.648764 0.211575 0.026 Uiso 1 1 calc R U . . .
C23 C 0.4546(3) 0.7015(2) 0.15889(15) 0.0197(6) Uani 1 1 d . . . . .
C24 C 0.4262(3) 0.7031(2) 0.08497(16) 0.0210(6) Uani 1 1 d . . . . .
C25 C 0.2883(4) 0.7385(2) 0.05163(15) 0.0213(6) Uani 1 1 d . . . . .
H25A H 0.250804 0.698600 0.014291 0.026 Uiso 1 1 calc R U . . .
H25B H 0.311611 0.793924 0.028304 0.026 Uiso 1 1 calc R U . . .
C26 C 0.1666(3) 0.75148(19) 0.10953(16) 0.0198(6) Uani 1 1 d . . . . .
H26 H 0.133015 0.693155 0.124970 0.024 Uiso 1 1 calc R U . . .
C27 C 0.2292(3) 0.79750(19) 0.17806(15) 0.0177(6) Uani 1 1 d . . . . .
C28 C 0.3464(3) 0.7372(2) 0.21321(16) 0.0215(6) Uani 1 1 d . . . . .
H28A H 0.403304 0.769215 0.250296 0.026 Uiso 1 1 calc R U . . .
H28B H 0.293214 0.689405 0.237335 0.026 Uiso 1 1 calc R U . . .
C29 C 0.3040(3) 0.8828(2) 0.15743(16) 0.0221(6) Uani 1 1 d . . . . .
H29A H 0.390314 0.871719 0.125924 0.033 Uiso 1 1 calc R U . . .
H29B H 0.338447 0.912174 0.201036 0.033 Uiso 1 1 calc R U . . .
H29C H 0.230808 0.919029 0.132189 0.033 Uiso 1 1 calc R U . . .
C30 C 0.0975(3) 0.81059(19) 0.23233(15) 0.0185(6) Uani 1 1 d . . . . .
H30 H 0.062968 0.751680 0.245576 0.022 Uiso 1 1 calc R U . . .
C31 C -0.0411(3) 0.85513(19) 0.19936(16) 0.0183(6) Uani 1 1 d . . . . .
H31 H -0.011863 0.914449 0.184609 0.022 Uiso 1 1 calc R U . . .
C32 C -0.0960(4) 0.8068(2) 0.13328(16) 0.0249(7) Uani 1 1 d . . . . .
H32A H -0.181307 0.838390 0.111398 0.030 Uiso 1 1 calc R U . . .
H32B H -0.133131 0.749652 0.147990 0.030 Uiso 1 1 calc R U . . .
C33 C 0.0291(4) 0.7961(2) 0.07740(17) 0.0259(7) Uani 1 1 d . . . . .
H33A H -0.009365 0.762010 0.036420 0.031 Uiso 1 1 calc R U . . .
H33B H 0.059056 0.853103 0.058953 0.031 Uiso 1 1 calc R U . . .
C34 C 0.1501(3) 0.8524(2) 0.30365(16) 0.0235(7) Uani 1 1 d . . . . .
H34A H 0.230501 0.816725 0.325191 0.028 Uiso 1 1 calc R U . . .
H34B H 0.193618 0.909442 0.293034 0.028 Uiso 1 1 calc R U . . .
C35 C 0.0220(4) 0.8629(2) 0.35840(16) 0.0222(7) Uani 1 1 d . . . . .
H35A H -0.010266 0.805760 0.375584 0.027 Uiso 1 1 calc R U . . .
H35B H 0.059055 0.895823 0.400345 0.027 Uiso 1 1 calc R U . . .
C36 C -0.1130(3) 0.90943(19) 0.32512(16) 0.0189(6) Uani 1 1 d . . . . .
C37 C -0.1630(3) 0.86110(19) 0.25710(15) 0.0187(6) Uani 1 1 d . . . . .
H37 H -0.185566 0.801024 0.272371 0.022 Uiso 1 1 calc R U . . .
C38 C -0.0704(4) 1.00242(19) 0.30767(16) 0.0231(7) Uani 1 1 d . . . . .
H38A H -0.039218 1.031700 0.351869 0.035 Uiso 1 1 calc R U . . .
H38B H -0.157674 1.031931 0.286936 0.035 Uiso 1 1 calc R U . . .
H38C H 0.012940 1.003007 0.273078 0.035 Uiso 1 1 calc R U . . .
C39 C -0.3151(3) 0.9026(2) 0.23819(16) 0.0249(7) Uani 1 1 d . . . . .
H39A H -0.383369 0.860559 0.215244 0.030 Uiso 1 1 calc R U . . .
H39B H -0.300793 0.951664 0.205103 0.030 Uiso 1 1 calc R U . . .
C40 C -0.3798(4) 0.9332(2) 0.31153(17) 0.0268(7) Uani 1 1 d . . . . .
H40A H -0.396590 0.995860 0.310972 0.032 Uiso 1 1 calc R U . . .
H40B H -0.476867 0.904354 0.321693 0.032 Uiso 1 1 calc R U . . .
C41 C -0.2614(4) 0.9092(2) 0.36898(16) 0.0217(7) Uani 1 1 d . . . . .
C42 C -0.3015(4) 0.8239(2) 0.40417(18) 0.0320(8) Uani 1 1 d . . . . .
H42A H -0.220093 0.806603 0.436687 0.048 Uiso 1 1 calc R U . . .
H42B H -0.315015 0.780187 0.366920 0.048 Uiso 1 1 calc R U . . .
H42C H -0.395297 0.830263 0.431518 0.048 Uiso 1 1 calc R U . . .
C43 C 0.5609(4) 0.5461(2) 0.46400(19) 0.0277(7) Uani 1 1 d . . . . .
C44 C 0.7156(4) 0.5776(2) 0.44889(17) 0.0231(7) Uani 1 1 d . . . . .
C45 C 0.8197(4) 0.5887(2) 0.50516(18) 0.0283(8) Uani 1 1 d . . . . .
C46 C 0.9649(4) 0.6178(2) 0.4912(2) 0.0354(9) Uani 1 1 d . . . . .
H46 H 1.034026 0.626538 0.529556 0.043 Uiso 1 1 calc R U . . .
C47 C 1.0071(4) 0.6338(2) 0.4219(2) 0.0393(9) Uani 1 1 d . . . . .
H47 H 1.106729 0.653129 0.412524 0.047 Uiso 1 1 calc R U . . .
C48 C 0.9097(4) 0.6227(2) 0.3654(2) 0.0366(9) Uani 1 1 d . . . . .
H48 H 0.941859 0.634023 0.317602 0.044 Uiso 1 1 calc R U . . .
C49 C 0.7638(4) 0.5949(2) 0.37861(19) 0.0292(8) Uani 1 1 d . . . . .
C50 C -0.0195(4) 0.5454(2) 0.03603(18) 0.0257(7) Uani 1 1 d . . . . .
C51 C 0.1396(4) 0.51712(19) 0.04349(17) 0.0221(7) Uani 1 1 d . . . . .
C52 C 0.2073(4) 0.5070(2) 0.11211(18) 0.0257(7) Uani 1 1 d . . . . .
C53 C 0.3570(4) 0.4838(2) 0.1184(2) 0.0306(8) Uani 1 1 d . . . . .
H53 H 0.402305 0.478609 0.164542 0.037 Uiso 1 1 calc R U . . .
C54 C 0.4403(4) 0.4682(2) 0.0568(2) 0.0344(8) Uani 1 1 d . . . . .
H54 H 0.543038 0.451919 0.061169 0.041 Uiso 1 1 calc R U . . .
C55 C 0.3782(4) 0.4758(2) -0.0102(2) 0.0315(8) Uani 1 1 d . . . . .
H55 H 0.437003 0.463508 -0.051694 0.038 Uiso 1 1 calc R U . . .
C56 C 0.2294(4) 0.5013(2) -0.01755(17) 0.0251(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0232(12) 0.0352(13) 0.0174(10) 0.0021(10) -0.0016(9) 0.0100(10)
O2 0.0251(12) 0.0317(12) 0.0179(11) -0.0037(9) 0.0029(9) 0.0080(10)
O3 0.0316(14) 0.0583(17) 0.0293(13) 0.0093(12) 0.0058(11) -0.0107(13)
O4 0.0305(13) 0.0449(15) 0.0354(14) 0.0036(12) -0.0079(12) -0.0131(11)
O5 0.0413(15) 0.074(2) 0.0254(13) -0.0048(13) -0.0054(12) -0.0032(15)
O6 0.0475(17) 0.0638(19) 0.0245(13) 0.0117(13) -0.0050(12) -0.0102(15)
O7 0.0279(13) 0.0558(16) 0.0299(13) 0.0021(12) -0.0050(11) 0.0136(12)
O8 0.0250(12) 0.0438(15) 0.0306(13) 0.0030(11) 0.0049(10) 0.0143(11)
O9 0.0376(15) 0.0488(16) 0.0227(12) 0.0075(11) -0.0006(11) 0.0079(12)
O10 0.0326(15) 0.0465(15) 0.0251(12) -0.0018(11) 0.0032(11) 0.0016(12)
N1 0.0233(15) 0.0277(14) 0.0251(14) -0.0006(11) -0.0056(12) 0.0047(12)
N2 0.0265(15) 0.0280(14) 0.0201(13) 0.0017(12) -0.0036(12) 0.0009(12)
N3 0.0168(13) 0.0252(14) 0.0251(13) -0.0013(11) 0.0005(11) 0.0038(11)
N4 0.0206(13) 0.0258(14) 0.0192(13) -0.0007(11) 0.0003(11) 0.0018(11)
C1 0.0262(18) 0.0321(18) 0.0232(16) -0.0004(14) -0.0039(14) 0.0038(14)
C2 0.0263(18) 0.0247(16) 0.0210(16) 0.0001(12) -0.0030(14) 0.0020(13)
C3 0.0240(17) 0.0207(15) 0.0238(16) 0.0030(13) -0.0017(13) 0.0017(13)
C4 0.0263(18) 0.0266(17) 0.0215(16) 0.0066(13) -0.0034(14) 0.0026(14)
C5 0.0223(16) 0.0244(16) 0.0203(15) 0.0052(13) -0.0005(13) 0.0014(12)
C6 0.0213(15) 0.0227(15) 0.0146(14) 0.0013(12) -0.0013(12) 0.0006(13)
C7 0.0269(17) 0.0312(17) 0.0198(16) -0.0007(13) -0.0034(13) 0.0066(14)
C8 0.0249(17) 0.0286(17) 0.0265(17) 0.0044(14) -0.0058(14) -0.0045(14)
C9 0.0258(17) 0.048(2) 0.0178(15) 0.0091(15) 0.0033(14) 0.0076(15)
C10 0.0259(18) 0.046(2) 0.0233(17) 0.0094(15) 0.0055(14) 0.0097(16)
C11 0.0190(15) 0.0258(15) 0.0159(14) 0.0023(12) 0.0001(12) 0.0020(13)
C12 0.0220(16) 0.0206(14) 0.0196(14) 0.0011(12) -0.0012(13) 0.0028(13)
C13 0.0264(18) 0.0372(18) 0.0178(15) 0.0002(13) -0.0010(14) 0.0101(14)
C14 0.0317(19) 0.0342(17) 0.0143(14) -0.0010(13) -0.0038(13) 0.0111(15)
C15 0.0215(15) 0.0229(15) 0.0153(14) -0.0016(12) 0.0006(12) 0.0036(13)
C16 0.0231(16) 0.0265(16) 0.0198(15) 0.0037(12) 0.0033(13) -0.0010(13)
C17 0.0293(18) 0.0292(17) 0.0269(17) 0.0049(14) -0.0040(14) -0.0037(14)
C18 0.0234(17) 0.048(2) 0.0227(16) 0.0034(15) 0.0043(14) 0.0114(16)
C19 0.0220(17) 0.0334(18) 0.0254(16) 0.0025(14) 0.0047(14) 0.0081(14)
C20 0.0242(17) 0.0229(16) 0.0212(15) 0.0014(12) -0.0007(13) 0.0016(13)
C21 0.035(2) 0.0342(19) 0.042(2) -0.0004(16) -0.0142(17) 0.0022(16)
C22 0.0227(16) 0.0246(15) 0.0176(15) 0.0005(13) 0.0014(13) 0.0016(13)
C23 0.0207(15) 0.0208(15) 0.0175(15) 0.0018(12) 0.0003(12) 0.0003(12)
C24 0.0205(16) 0.0208(15) 0.0218(15) -0.0018(13) 0.0037(13) -0.0005(13)
C25 0.0234(16) 0.0223(15) 0.0183(15) -0.0016(12) -0.0022(13) 0.0030(13)
C26 0.0200(16) 0.0225(15) 0.0168(14) -0.0007(12) -0.0013(13) 0.0014(12)
C27 0.0174(15) 0.0209(14) 0.0148(14) -0.0010(12) -0.0010(12) 0.0023(12)
C28 0.0200(16) 0.0279(16) 0.0165(14) 0.0007(12) 0.0003(12) 0.0029(13)
C29 0.0194(15) 0.0245(16) 0.0224(15) -0.0017(12) 0.0002(13) -0.0002(13)
C30 0.0176(15) 0.0227(15) 0.0153(14) -0.0003(12) -0.0003(11) -0.0022(12)
C31 0.0174(15) 0.0195(14) 0.0181(15) 0.0002(12) -0.0002(12) 0.0010(12)
C32 0.0181(15) 0.0335(17) 0.0231(16) -0.0046(14) -0.0031(12) 0.0030(14)
C33 0.0234(17) 0.0340(18) 0.0202(15) -0.0069(14) -0.0011(14) 0.0044(14)
C34 0.0190(16) 0.0303(17) 0.0212(15) -0.0032(13) 0.0010(12) 0.0046(13)
C35 0.0210(16) 0.0296(17) 0.0159(14) -0.0013(12) -0.0010(12) 0.0054(13)
C36 0.0192(15) 0.0185(15) 0.0190(15) 0.0002(12) 0.0010(13) 0.0018(12)
C37 0.0166(15) 0.0201(14) 0.0194(15) 0.0004(11) 0.0006(12) 0.0022(12)
C38 0.0268(16) 0.0232(15) 0.0192(15) -0.0031(13) 0.0027(12) -0.0008(13)
C39 0.0175(15) 0.0356(18) 0.0217(15) -0.0021(14) 0.0019(13) 0.0042(14)
C40 0.0213(16) 0.0335(18) 0.0255(17) -0.0049(14) 0.0012(13) 0.0037(14)
C41 0.0209(16) 0.0258(16) 0.0183(15) -0.0009(13) 0.0028(12) 0.0027(13)
C42 0.0297(18) 0.0347(19) 0.0315(18) 0.0030(14) 0.0138(15) 0.0009(15)
C43 0.0283(17) 0.0272(17) 0.0275(18) -0.0014(14) -0.0026(15) -0.0048(14)
C44 0.0231(16) 0.0214(15) 0.0248(16) 0.0002(13) -0.0002(13) -0.0020(13)
C45 0.0294(18) 0.0288(17) 0.0268(17) -0.0033(13) -0.0027(14) 0.0019(15)
C46 0.0257(18) 0.0303(19) 0.050(2) -0.0067(17) -0.0093(17) -0.0024(15)
C47 0.0224(17) 0.0246(17) 0.071(3) 0.0048(18) 0.0039(18) -0.0004(15)
C48 0.037(2) 0.0294(18) 0.044(2) 0.0110(17) 0.0126(18) -0.0031(16)
C49 0.0321(19) 0.0277(17) 0.0278(18) 0.0041(14) -0.0002(15) -0.0017(15)
C50 0.0268(17) 0.0233(16) 0.0269(17) 0.0017(13) 0.0017(14) 0.0024(14)
C51 0.0237(16) 0.0176(14) 0.0252(16) 0.0022(13) -0.0006(13) 0.0004(12)
C52 0.0304(18) 0.0201(15) 0.0265(16) 0.0055(13) -0.0021(14) 0.0031(13)
C53 0.0300(18) 0.0286(17) 0.0332(19) 0.0079(14) -0.0082(15) 0.0025(15)
C54 0.0217(17) 0.0241(17) 0.057(2) 0.0098(17) 0.0005(17) 0.0035(14)
C55 0.0260(18) 0.0253(17) 0.043(2) 0.0012(15) 0.0101(16) 0.0035(14)
C56 0.0289(17) 0.0201(15) 0.0263(17) 0.0008(13) 0.0034(13) -0.0005(13)
_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 C20 1.447(4) . ?
O1 H1B 0.847(14) . ?
O2 C41 1.450(4) . ?
O2 H2A 0.845(15) . ?
O3 C43 1.257(4) . ?
O4 C43 1.283(4) . ?
O5 C45 1.350(4) . ?
O5 H5A 0.853(14) . ?
O6 C49 1.360(4) . ?
O6 H6 0.859(14) . ?
O7 C50 1.260(4) . ?
O8 C50 1.262(4) . ?
O9 C52 1.360(4) . ?
O9 H9 0.860(14) . ?
O10 C56 1.341(4) . ?
O10 H10 0.848(14) . ?
N1 C1 1.334(4) . ?
N1 N2 1.347(4) . ?
N1 H1A 0.890(14) . ?
N2 C3 1.352(4) . ?
N2 H2 0.888(14) . ?
N3 C22 1.338(4) . ?
N3 N4 1.340(4) . ?
N3 H3 0.871(14) . ?
N4 C24 1.349(4) . ?
N4 H4 0.882(14) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(5) . ?
C2 C7 1.504(4) . ?
C3 C4 1.488(4) . ?
C4 C5 1.552(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C9 1.530(5) . ?
C5 C6 1.554(4) . ?
C5 H5 1.0000 . ?
C6 C8 1.537(4) . ?
C6 C7 1.545(4) . ?
C6 C12 1.556(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.528(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.537(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.529(4) . ?
C11 C12 1.550(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.549(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.537(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.515(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.535(4) . ?
C15 C17 1.540(4) . ?
C15 C20 1.550(4) . ?
C16 C18 1.532(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.564(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.555(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.529(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(4) . ?
C23 C28 1.501(4) . ?
C24 C25 1.477(4) . ?
C25 C26 1.538(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C33 1.526(4) . ?
C26 C27 1.564(4) . ?
C26 H26 1.0000 . ?
C27 C29 1.537(4) . ?
C27 C28 1.547(4) . ?
C27 C30 1.557(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.539(4) . ?
C30 C34 1.550(4) . ?
C30 H30 1.0000 . ?
C31 C32 1.521(4) . ?
C31 C37 1.527(4) . ?
C31 H31 1.0000 . ?
C32 C33 1.530(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.534(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.530(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C38 1.534(4) . ?
C36 C37 1.538(4) . ?
C36 C41 1.549(4) . ?
C37 C39 1.538(4) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.554(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.544(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.525(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.485(5) . ?
C44 C49 1.401(5) . ?
C44 C45 1.406(4) . ?
C45 C46 1.390(5) . ?
C46 C47 1.366(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.370(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.387(5) . ?
C48 H48 0.9500 . ?
C50 C51 1.485(5) . ?
C51 C56 1.409(4) . ?
C51 C52 1.419(4) . ?
C52 C53 1.381(5) . ?
C53 C54 1.386(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.367(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.386(5) . ?
C55 H55 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
C20 O1 H1B 105(2) . . ?
C41 O2 H2A 106(4) . . ?
C45 O5 H5A 104(3) . . ?
C49 O6 H6 106(3) . . ?
C52 O9 H9 105(3) . . ?
C56 O10 H10 103(3) . . ?
C1 N1 N2 109.2(3) . . ?
C1 N1 H1A 128(2) . . ?
N2 N1 H1A 122(2) . . ?
N1 N2 C3 108.4(3) . . ?
N1 N2 H2 121(3) . . ?
C3 N2 H2 130(3) . . ?
C22 N3 N4 109.3(3) . . ?
C22 N3 H3 120(2) . . ?
N4 N3 H3 131(2) . . ?
N3 N4 C24 109.0(2) . . ?
N3 N4 H4 119(2) . . ?
C24 N4 H4 132(2) . . ?
N1 C1 C2 108.4(3) . . ?
N1 C1 H1 125.8 . . ?
C2 C1 H1 125.8 . . ?
C1 C2 C3 105.9(3) . . ?
C1 C2 C7 131.5(3) . . ?
C3 C2 C7 122.6(3) . . ?
N2 C3 C2 108.0(3) . . ?
N2 C3 C4 126.6(3) . . ?
C2 C3 C4 125.4(3) . . ?
C3 C4 C5 109.8(3) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C9 C5 C4 109.6(3) . . ?
C9 C5 C6 112.7(3) . . ?
C4 C5 C6 113.5(2) . . ?
C9 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C6 C5 H5 106.9 . . ?
C8 C6 C7 109.0(3) . . ?
C8 C6 C12 111.9(2) . . ?
C7 C6 C12 108.7(2) . . ?
C8 C6 C5 110.8(2) . . ?
C7 C6 C5 108.6(2) . . ?
C12 C6 C5 107.8(2) . . ?
C2 C7 C6 110.8(3) . . ?
C2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C5 112.8(3) . . ?
C10 C9 H9A 109.0 . . ?
C5 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C5 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 111.5(3) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C16 C11 C10 111.8(3) . . ?
C16 C11 C12 110.4(2) . . ?
C10 C11 C12 109.1(3) . . ?
C16 C11 H11 108.5 . . ?
C10 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C13 C12 C11 113.5(2) . . ?
C13 C12 C6 112.9(2) . . ?
C11 C12 C6 112.0(2) . . ?
C13 C12 H12 105.9 . . ?
C11 C12 H12 105.9 . . ?
C6 C12 H12 105.9 . . ?
C14 C13 C12 112.7(3) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 111.0(3) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 108.9(3) . . ?
C14 C15 C17 109.3(3) . . ?
C16 C15 C17 111.5(3) . . ?
C14 C15 C20 117.3(3) . . ?
C16 C15 C20 101.6(2) . . ?
C17 C15 C20 108.1(2) . . ?
C11 C16 C18 117.9(3) . . ?
C11 C16 C15 113.2(3) . . ?
C18 C16 C15 103.6(2) . . ?
C11 C16 H16 107.2 . . ?
C18 C16 H16 107.2 . . ?
C15 C16 H16 107.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 104.0(2) . . ?
C16 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C16 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 109.0 . . ?
C20 C19 C18 106.7(2) . . ?
C20 C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C18 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O1 C20 C21 108.2(3) . . ?
O1 C20 C15 108.7(2) . . ?
C21 C20 C15 114.2(3) . . ?
O1 C20 C19 112.0(2) . . ?
C21 C20 C19 110.8(3) . . ?
C15 C20 C19 103.0(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 108.2(3) . . ?
N3 C22 H22 125.9 . . ?
C23 C22 H22 125.9 . . ?
C22 C23 C24 106.1(3) . . ?
C22 C23 C28 131.3(3) . . ?
C24 C23 C28 122.6(3) . . ?
N4 C24 C23 107.4(3) . . ?
N4 C24 C25 127.9(3) . . ?
C23 C24 C25 124.7(3) . . ?
C24 C25 C26 109.7(2) . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C33 C26 C25 110.3(2) . . ?
C33 C26 C27 113.1(2) . . ?
C25 C26 C27 112.4(2) . . ?
C33 C26 H26 106.8 . . ?
C25 C26 H26 106.8 . . ?
C27 C26 H26 106.8 . . ?
C29 C27 C28 110.0(2) . . ?
C29 C27 C30 111.8(2) . . ?
C28 C27 C30 108.1(2) . . ?
C29 C27 C26 110.4(2) . . ?
C28 C27 C26 107.6(2) . . ?
C30 C27 C26 108.8(2) . . ?
C23 C28 C27 111.8(2) . . ?
C23 C28 H28A 109.3 . . ?
C27 C28 H28A 109.3 . . ?
C23 C28 H28B 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C34 113.0(2) . . ?
C31 C30 C27 113.6(2) . . ?
C34 C30 C27 112.6(2) . . ?
C31 C30 H30 105.6 . . ?
C34 C30 H30 105.6 . . ?
C27 C30 H30 105.6 . . ?
C32 C31 C37 111.8(2) . . ?
C32 C31 C30 110.7(2) . . ?
C37 C31 C30 108.3(2) . . ?
C32 C31 H31 108.7 . . ?
C37 C31 H31 108.7 . . ?
C30 C31 H31 108.7 . . ?
C31 C32 C33 111.7(3) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C26 C33 C32 111.4(3) . . ?
C26 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C26 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C30 112.9(3) . . ?
C35 C34 H34A 109.0 . . ?
C30 C34 H34A 109.0 . . ?
C35 C34 H34B 109.0 . . ?
C30 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C36 C35 C34 111.2(2) . . ?
C36 C35 H35A 109.4 . . ?
C34 C35 H35A 109.4 . . ?
C36 C35 H35B 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C35 C36 C38 110.0(3) . . ?
C35 C36 C37 109.0(2) . . ?
C38 C36 C37 111.2(2) . . ?
C35 C36 C41 116.8(2) . . ?
C38 C36 C41 108.9(2) . . ?
C37 C36 C41 100.8(2) . . ?
C31 C37 C39 119.1(2) . . ?
C31 C37 C36 113.8(2) . . ?
C39 C37 C36 103.5(2) . . ?
C31 C37 H37 106.5 . . ?
C39 C37 H37 106.5 . . ?
C36 C37 H37 106.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 104.6(2) . . ?
C37 C39 H39A 110.8 . . ?
C40 C39 H39A 110.8 . . ?
C37 C39 H39B 110.8 . . ?
C40 C39 H39B 110.8 . . ?
H39A C39 H39B 108.9 . . ?
C41 C40 C39 106.3(2) . . ?
C41 C40 H40A 110.5 . . ?
C39 C40 H40A 110.5 . . ?
C41 C40 H40B 110.5 . . ?
C39 C40 H40B 110.5 . . ?
H40A C40 H40B 108.7 . . ?
O2 C41 C42 107.1(2) . . ?
O2 C41 C40 113.1(3) . . ?
C42 C41 C40 110.5(3) . . ?
O2 C41 C36 108.8(2) . . ?
C42 C41 C36 115.3(3) . . ?
C40 C41 C36 102.3(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O3 C43 O4 122.6(3) . . ?
O3 C43 C44 119.5(3) . . ?
O4 C43 C44 117.8(3) . . ?
C49 C44 C45 118.0(3) . . ?
C49 C44 C43 121.5(3) . . ?
C45 C44 C43 120.5(3) . . ?
O5 C45 C46 117.7(3) . . ?
O5 C45 C44 121.6(3) . . ?
C46 C45 C44 120.7(3) . . ?
C47 C46 C45 119.3(3) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C46 C47 C48 121.8(3) . . ?
C46 C47 H47 119.1 . . ?
C48 C47 H47 119.1 . . ?
C47 C48 C49 119.5(3) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
O6 C49 C48 118.5(3) . . ?
O6 C49 C44 120.8(3) . . ?
C48 C49 C44 120.7(3) . . ?
O7 C50 O8 123.2(3) . . ?
O7 C50 C51 118.4(3) . . ?
O8 C50 C51 118.5(3) . . ?
C56 C51 C52 117.7(3) . . ?
C56 C51 C50 121.0(3) . . ?
C52 C51 C50 121.3(3) . . ?
O9 C52 C53 118.2(3) . . ?
O9 C52 C51 121.0(3) . . ?
C53 C52 C51 120.8(3) . . ?
C52 C53 C54 119.2(3) . . ?
C52 C53 H53 120.4 . . ?
C54 C53 H53 120.4 . . ?
C55 C54 C53 121.6(3) . . ?
C55 C54 H54 119.2 . . ?
C53 C54 H54 119.2 . . ?
C54 C55 C56 119.8(3) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
O10 C56 C55 118.4(3) . . ?
O10 C56 C51 120.9(3) . . ?
C55 C56 C51 120.7(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
C1 N1 N2 C3 -0.2(4) . . . . ?
C22 N3 N4 C24 -0.5(3) . . . . ?
N2 N1 C1 C2 0.3(4) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C7 178.9(3) . . . . ?
N1 N2 C3 C2 0.0(4) . . . . ?
N1 N2 C3 C4 178.3(3) . . . . ?
C1 C2 C3 N2 0.2(4) . . . . ?
C7 C2 C3 N2 -179.1(3) . . . . ?
C1 C2 C3 C4 -178.2(3) . . . . ?
C7 C2 C3 C4 2.6(5) . . . . ?
N2 C3 C4 C5 170.1(3) . . . . ?
C2 C3 C4 C5 -11.8(4) . . . . ?
C3 C4 C5 C9 168.7(3) . . . . ?
C3 C4 C5 C6 41.8(3) . . . . ?
C9 C5 C6 C8 -68.3(3) . . . . ?
C4 C5 C6 C8 57.0(3) . . . . ?
C9 C5 C6 C7 172.1(3) . . . . ?
C4 C5 C6 C7 -62.7(3) . . . . ?
C9 C5 C6 C12 54.4(3) . . . . ?
C4 C5 C6 C12 179.7(3) . . . . ?
C1 C2 C7 C6 158.6(3) . . . . ?
C3 C2 C7 C6 -22.3(4) . . . . ?
C8 C6 C7 C2 -70.9(3) . . . . ?
C12 C6 C7 C2 166.9(3) . . . . ?
C5 C6 C7 C2 49.8(3) . . . . ?
C4 C5 C9 C10 179.1(3) . . . . ?
C6 C5 C9 C10 -53.5(4) . . . . ?
C5 C9 C10 C11 53.6(4) . . . . ?
C9 C10 C11 C16 -178.2(3) . . . . ?
C9 C10 C11 C12 -55.9(4) . . . . ?
C16 C11 C12 C13 -47.4(3) . . . . ?
C10 C11 C12 C13 -170.6(3) . . . . ?
C16 C11 C12 C6 -176.7(2) . . . . ?
C10 C11 C12 C6 60.1(3) . . . . ?
C8 C6 C12 C13 -66.1(3) . . . . ?
C7 C6 C12 C13 54.4(3) . . . . ?
C5 C6 C12 C13 171.9(3) . . . . ?
C8 C6 C12 C11 63.5(3) . . . . ?
C7 C6 C12 C11 -176.1(3) . . . . ?
C5 C6 C12 C11 -58.5(3) . . . . ?
C11 C12 C13 C14 48.3(4) . . . . ?
C6 C12 C13 C14 177.1(3) . . . . ?
C12 C13 C14 C15 -54.2(4) . . . . ?
C13 C14 C15 C16 59.1(4) . . . . ?
C13 C14 C15 C17 -63.0(3) . . . . ?
C13 C14 C15 C20 173.6(3) . . . . ?
C10 C11 C16 C18 -63.0(4) . . . . ?
C12 C11 C16 C18 175.4(3) . . . . ?
C10 C11 C16 C15 175.9(3) . . . . ?
C12 C11 C16 C15 54.3(3) . . . . ?
C14 C15 C16 C11 -60.7(3) . . . . ?
C17 C15 C16 C11 60.0(3) . . . . ?
C20 C15 C16 C11 175.0(3) . . . . ?
C14 C15 C16 C18 170.4(3) . . . . ?
C17 C15 C16 C18 -68.9(3) . . . . ?
C20 C15 C16 C18 46.1(3) . . . . ?
C11 C16 C18 C19 -159.1(3) . . . . ?
C15 C16 C18 C19 -33.2(3) . . . . ?
C16 C18 C19 C20 7.8(3) . . . . ?
C14 C15 C20 O1 82.4(3) . . . . ?
C16 C15 C20 O1 -159.1(2) . . . . ?
C17 C15 C20 O1 -41.7(3) . . . . ?
C14 C15 C20 C21 -38.5(4) . . . . ?
C16 C15 C20 C21 80.1(3) . . . . ?
C17 C15 C20 C21 -162.5(3) . . . . ?
C14 C15 C20 C19 -158.7(3) . . . . ?
C16 C15 C20 C19 -40.2(3) . . . . ?
C17 C15 C20 C19 77.2(3) . . . . ?
C18 C19 C20 O1 136.6(3) . . . . ?
C18 C19 C20 C21 -102.5(3) . . . . ?
C18 C19 C20 C15 20.0(3) . . . . ?
N4 N3 C22 C23 -0.3(3) . . . . ?
N3 C22 C23 C24 1.0(3) . . . . ?
N3 C22 C23 C28 179.2(3) . . . . ?
N3 N4 C24 C23 1.1(3) . . . . ?
N3 N4 C24 C25 -177.8(3) . . . . ?
C22 C23 C24 N4 -1.3(3) . . . . ?
C28 C23 C24 N4 -179.7(3) . . . . ?
C22 C23 C24 C25 177.7(3) . . . . ?
C28 C23 C24 C25 -0.8(5) . . . . ?
N4 C24 C25 C26 164.4(3) . . . . ?
C23 C24 C25 C26 -14.3(4) . . . . ?
C24 C25 C26 C33 174.4(3) . . . . ?
C24 C25 C26 C27 47.1(3) . . . . ?
C33 C26 C27 C29 -70.7(3) . . . . ?
C25 C26 C27 C29 55.1(3) . . . . ?
C33 C26 C27 C28 169.2(2) . . . . ?
C25 C26 C27 C28 -65.0(3) . . . . ?
C33 C26 C27 C30 52.3(3) . . . . ?
C25 C26 C27 C30 178.1(2) . . . . ?
C22 C23 C28 C27 165.2(3) . . . . ?
C24 C23 C28 C27 -16.8(4) . . . . ?
C29 C27 C28 C23 -73.4(3) . . . . ?
C30 C27 C28 C23 164.3(2) . . . . ?
C26 C27 C28 C23 46.9(3) . . . . ?
C29 C27 C30 C31 69.7(3) . . . . ?
C28 C27 C30 C31 -169.0(2) . . . . ?
C26 C27 C30 C31 -52.4(3) . . . . ?
C29 C27 C30 C34 -60.3(3) . . . . ?
C28 C27 C30 C34 61.0(3) . . . . ?
C26 C27 C30 C34 177.5(2) . . . . ?
C34 C30 C31 C32 -175.0(3) . . . . ?
C27 C30 C31 C32 55.2(3) . . . . ?
C34 C30 C31 C37 -52.1(3) . . . . ?
C27 C30 C31 C37 178.0(2) . . . . ?
C37 C31 C32 C33 -176.5(2) . . . . ?
C30 C31 C32 C33 -55.7(3) . . . . ?
C25 C26 C33 C32 177.9(3) . . . . ?
C27 C26 C33 C32 -55.2(3) . . . . ?
C31 C32 C33 C26 56.2(4) . . . . ?
C31 C30 C34 C35 51.5(3) . . . . ?
C27 C30 C34 C35 -178.1(2) . . . . ?
C30 C34 C35 C36 -52.6(3) . . . . ?
C34 C35 C36 C38 -66.8(3) . . . . ?
C34 C35 C36 C37 55.3(3) . . . . ?
C34 C35 C36 C41 168.5(3) . . . . ?
C32 C31 C37 C39 -57.4(4) . . . . ?
C30 C31 C37 C39 -179.6(2) . . . . ?
C32 C31 C37 C36 -180.0(2) . . . . ?
C30 C31 C37 C36 57.8(3) . . . . ?
C35 C36 C37 C31 -60.2(3) . . . . ?
C38 C36 C37 C31 61.2(3) . . . . ?
C41 C36 C37 C31 176.4(2) . . . . ?
C35 C36 C37 C39 169.0(2) . . . . ?
C38 C36 C37 C39 -69.6(3) . . . . ?
C41 C36 C37 C39 45.6(3) . . . . ?
C31 C37 C39 C40 -156.3(3) . . . . ?
C36 C37 C39 C40 -28.8(3) . . . . ?
C37 C39 C40 C41 0.8(3) . . . . ?
C39 C40 C41 O2 143.8(3) . . . . ?
C39 C40 C41 C42 -96.2(3) . . . . ?
C39 C40 C41 C36 27.0(3) . . . . ?
C35 C36 C41 O2 77.9(3) . . . . ?
C38 C36 C41 O2 -47.3(3) . . . . ?
C37 C36 C41 O2 -164.3(2) . . . . ?
C35 C36 C41 C42 -42.3(4) . . . . ?
C38 C36 C41 C42 -167.5(3) . . . . ?
C37 C36 C41 C42 75.5(3) . . . . ?
C35 C36 C41 C40 -162.2(3) . . . . ?
C38 C36 C41 C40 72.6(3) . . . . ?
C37 C36 C41 C40 -44.4(3) . . . . ?
O3 C43 C44 C49 175.6(3) . . . . ?
O4 C43 C44 C49 -3.3(5) . . . . ?
O3 C43 C44 C45 -2.6(5) . . . . ?
O4 C43 C44 C45 178.4(3) . . . . ?
C49 C44 C45 O5 -177.8(3) . . . . ?
C43 C44 C45 O5 0.6(5) . . . . ?
C49 C44 C45 C46 1.4(5) . . . . ?
C43 C44 C45 C46 179.7(3) . . . . ?
O5 C45 C46 C47 177.7(3) . . . . ?
C44 C45 C46 C47 -1.5(5) . . . . ?
C45 C46 C47 C48 0.6(5) . . . . ?
C46 C47 C48 C49 0.3(5) . . . . ?
C47 C48 C49 O6 179.1(3) . . . . ?
C47 C48 C49 C44 -0.3(5) . . . . ?
C45 C44 C49 O6 -179.9(3) . . . . ?
C43 C44 C49 O6 1.8(5) . . . . ?
C45 C44 C49 C48 -0.5(5) . . . . ?
C43 C44 C49 C48 -178.8(3) . . . . ?
O7 C50 C51 C56 -0.3(5) . . . . ?
O8 C50 C51 C56 179.9(3) . . . . ?
O7 C50 C51 C52 178.2(3) . . . . ?
O8 C50 C51 C52 -1.6(5) . . . . ?
C56 C51 C52 O9 -179.7(3) . . . . ?
C50 C51 C52 O9 1.7(5) . . . . ?
C56 C51 C52 C53 1.0(4) . . . . ?
C50 C51 C52 C53 -177.5(3) . . . . ?
O9 C52 C53 C54 179.1(3) . . . . ?
C51 C52 C53 C54 -1.6(5) . . . . ?
C52 C53 C54 C55 0.4(5) . . . . ?
C53 C54 C55 C56 1.4(5) . . . . ?
C54 C55 C56 O10 177.8(3) . . . . ?
C54 C55 C56 C51 -2.0(5) . . . . ?
C52 C51 C56 O10 -179.0(3) . . . . ?
C50 C51 C56 O10 -0.4(5) . . . . ?
C52 C51 C56 C55 0.8(4) . . . . ?
C50 C51 C56 C55 179.3(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
_geom_hbond_publ_flag
N2 H2 O2 0.888(14) 1.87(2) 2.701(4) 155(4) . yes
N1 H1A O4 0.890(14) 1.732(16) 2.605(4) 166(3) 2_556 yes
N4 H4 O1 0.882(14) 1.822(18) 2.665(3) 159(3) 1_554 yes
N3 H3 O8 0.871(14) 1.781(15) 2.648(3) 174(4) 1_655 yes
O1 H1B O7 0.847(14) 1.845(15) 2.684(3) 171(3) 1_656 yes
O2 H2A O3 0.845(15) 1.893(18) 2.729(3) 170(6) 2_556 yes
O5 H5A O3 0.853(14) 1.75(2) 2.550(4) 154(4) . yes
O6 H6 O4 0.859(14) 1.74(3) 2.525(4) 152(5) . yes
O9 H9 O8 0.860(14) 1.76(2) 2.551(3) 152(4) . yes
O10 H10 O7 0.848(14) 1.73(3) 2.525(4) 155(5) . yes
_refine_diff_density_max 0.134
_refine_diff_density_min -0.123
_refine_diff_density_rms 0.028
_shelx_res_file
;
TITL b in P2(1)
T.res
created by SHELXL-2017/1 at 13:18:28 on 26-Aug-2018
CELL 0.71073 8.8708 15.6092 18.5927 90 90.0143 90
ZERR 4 0.00177 0.00312 0.00372 0 0.03 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 112 152 8 20
size 0.35 0.36 0.4
temp -153
EQIV $1 -X,0.5+Y,1-Z
EQIV $2 +X,+Y,-1+Z
EQIV $3 1+X,+Y,+Z
EQIV $4 1+X,+Y,1+Z
DFIX 0.85 0.01 O1 H1b O2 H2a O5 H5a O6 H6 O9 H9 O10 H10
DFIX 0.87 0.01 N1 H1a N2 H2 N3 H3 N4 H4
L.S. 40
PLAN 10
HTAB N2 O2
HTAB N1 O4_$1
HTAB N4 O1_$2
HTAB N3 O8_$3
HTAB O1 O7_$4
HTAB O2 O3_$1
HTAB O5 O3
HTAB O6 O4
HTAB O9 O8
HTAB O10 O7
BOND $h
fmap 2
acta
MORE -1
CONF
MERG 0
REM
REM
REM
WGHT 0.035968 0.123114
BASF 0.41405
FVAR 9.37840
O1 4 0.668683 0.624015 0.926216 11.00000 0.02322 0.03521 =
0.01737 0.00211 -0.00156 0.01004
H1B 2 0.755172 0.607023 0.939147 11.00000 0.02300
O2 4 -0.249389 0.972059 0.426094 11.00000 0.02508 0.03169 =
0.01787 -0.00366 0.00288 0.00802
H2A 2 -0.338435 0.983112 0.439203 11.00000 0.08594
O3 4 0.524951 0.526384 0.527238 11.00000 0.03156 0.05825 =
0.02928 0.00930 0.00583 -0.01070
O4 4 0.469462 0.539091 0.410851 11.00000 0.03049 0.04490 =
0.03535 0.00363 -0.00788 -0.01306
O5 4 0.783675 0.570767 0.574065 11.00000 0.04129 0.07428 =
0.02538 -0.00479 -0.00543 -0.00323
H5A 2 0.694325 0.550754 0.571466 11.00000 -1.20000
O6 4 0.668464 0.585416 0.321872 11.00000 0.04753 0.06375 =
0.02448 0.01166 -0.00498 -0.01021
H6 2 0.585023 0.566504 0.339155 11.00000 -1.20000
O7 4 -0.072285 0.555387 -0.026356 11.00000 0.02793 0.05581 =
0.02989 0.00214 -0.00500 0.01356
O8 4 -0.095183 0.558644 0.092418 11.00000 0.02501 0.04376 =
0.03065 0.00302 0.00486 0.01430
O9 4 0.127277 0.520871 0.173406 11.00000 0.03763 0.04884 =
0.02270 0.00752 -0.00057 0.00792
H9 2 0.041584 0.540164 0.159012 11.00000 0.05345
O10 4 0.173188 0.510934 -0.084027 11.00000 0.03262 0.04653 =
0.02508 -0.00177 0.00322 0.00160
H10 2 0.080618 0.521249 -0.076716 11.00000 0.07105
N1 3 -0.210968 0.961587 0.602747 11.00000 0.02327 0.02773 =
0.02509 -0.00058 -0.00562 0.00474
H1A 2 -0.293479 0.991091 0.591378 11.00000 0.02424
N2 3 -0.115296 0.932242 0.552155 11.00000 0.02648 0.02795 =
0.02007 0.00172 -0.00363 0.00090
H2 2 -0.137334 0.935706 0.505636 11.00000 0.05317
N3 3 0.643473 0.639855 0.101859 11.00000 0.01684 0.02517 =
0.02512 -0.00131 0.00046 0.00382
H3 2 0.732385 0.616725 0.097548 11.00000 -1.20000
N4 3 0.544598 0.665845 0.051956 11.00000 0.02061 0.02576 =
0.01920 -0.00074 0.00025 0.00184
H4 2 0.563203 0.653905 0.006462 11.00000 -1.20000
C1 1 -0.151541 0.948146 0.667668 11.00000 0.02621 0.03207 =
0.02322 -0.00043 -0.00385 0.00375
AFIX 43
H1 2 -0.196895 0.962823 0.712279 11.00000 -1.20000
AFIX 0
C2 1 -0.012233 0.909090 0.658991 11.00000 0.02627 0.02471 =
0.02104 0.00014 -0.00304 0.00197
C3 1 0.007570 0.899684 0.585415 11.00000 0.02397 0.02069 =
0.02384 0.00296 -0.00172 0.00172
C4 1 0.139713 0.858456 0.550272 11.00000 0.02632 0.02659 =
0.02147 0.00662 -0.00337 0.00255
AFIX 23
H4A 2 0.176867 0.895294 0.510723 11.00000 -1.20000
H4B 2 0.109356 0.802648 0.529526 11.00000 -1.20000
AFIX 0
C5 1 0.267017 0.844641 0.606334 11.00000 0.02232 0.02436 =
0.02033 0.00516 -0.00055 0.00145
AFIX 13
H5 2 0.314668 0.901797 0.614909 11.00000 -1.20000
AFIX 0
C6 1 0.209023 0.812070 0.680332 11.00000 0.02131 0.02272 =
0.01463 0.00132 -0.00127 0.00059
C7 1 0.104150 0.880906 0.712899 11.00000 0.02689 0.03117 =
0.01980 -0.00065 -0.00342 0.00659
AFIX 23
H7A 2 0.053164 0.857332 0.755925 11.00000 -1.20000
H7B 2 0.164842 0.930931 0.728168 11.00000 -1.20000
AFIX 0
C8 1 0.120195 0.728151 0.671557 11.00000 0.02492 0.02862 =
0.02649 0.00441 -0.00582 -0.00452
AFIX 137
H8A 2 0.093857 0.705549 0.719096 11.00000 -1.50000
H8B 2 0.182232 0.686191 0.645850 11.00000 -1.50000
H8C 2 0.027869 0.739215 0.644132 11.00000 -1.50000
AFIX 0
C9 1 0.388892 0.786703 0.574302 11.00000 0.02578 0.04802 =
0.01780 0.00907 0.00327 0.00762
AFIX 23
H9A 2 0.343186 0.731007 0.561131 11.00000 -1.20000
H9B 2 0.428097 0.813331 0.529747 11.00000 -1.20000
AFIX 0
C10 1 0.520006 0.770964 0.625954 11.00000 0.02591 0.04587 =
0.02329 0.00943 0.00547 0.00975
AFIX 23
H10A 2 0.575817 0.825170 0.633392 11.00000 -1.20000
H10B 2 0.590241 0.728912 0.604377 11.00000 -1.20000
AFIX 0
C11 1 0.464576 0.737069 0.698926 11.00000 0.01899 0.02582 =
0.01593 0.00231 0.00009 0.00198
AFIX 13
H11 2 0.413500 0.680745 0.690988 11.00000 -1.20000
AFIX 0
C12 1 0.347999 0.800745 0.730484 11.00000 0.02205 0.02058 =
0.01957 0.00110 -0.00119 0.00276
AFIX 13
H12 2 0.399477 0.857723 0.731670 11.00000 -1.20000
AFIX 0
C13 1 0.303808 0.780760 0.809294 11.00000 0.02639 0.03722 =
0.01775 0.00021 -0.00103 0.01014
AFIX 23
H13A 2 0.244768 0.829302 0.828804 11.00000 -1.20000
H13B 2 0.238604 0.729297 0.810143 11.00000 -1.20000
AFIX 0
C14 1 0.441534 0.765189 0.857774 11.00000 0.03174 0.03420 =
0.01425 -0.00097 -0.00381 0.01113
AFIX 23
H14A 2 0.499589 0.819045 0.862642 11.00000 -1.20000
H14B 2 0.407173 0.747819 0.906286 11.00000 -1.20000
AFIX 0
C15 1 0.542324 0.696036 0.826834 11.00000 0.02152 0.02287 =
0.01526 -0.00156 0.00062 0.00362
C16 1 0.594697 0.723775 0.751674 11.00000 0.02306 0.02646 =
0.01982 0.00369 0.00333 -0.00100
AFIX 13
H16 2 0.646854 0.780191 0.757177 11.00000 -1.20000
AFIX 0
C17 1 0.455088 0.610782 0.824162 11.00000 0.02933 0.02924 =
0.02692 0.00495 -0.00404 -0.00368
AFIX 137
H17A 2 0.416248 0.597270 0.872180 11.00000 -1.50000
H17B 2 0.522730 0.564912 0.808242 11.00000 -1.50000
H17C 2 0.370779 0.615919 0.790364 11.00000 -1.50000
AFIX 0
C18 1 0.715411 0.657491 0.732271 11.00000 0.02340 0.04844 =
0.02269 0.00341 0.00428 0.01144
AFIX 23
H18A 2 0.790129 0.681918 0.698459 11.00000 -1.20000
H18B 2 0.669417 0.606038 0.710182 11.00000 -1.20000
AFIX 0
C19 1 0.790593 0.635048 0.806022 11.00000 0.02195 0.03344 =
0.02538 0.00250 0.00474 0.00810
AFIX 23
H19A 2 0.791547 0.572253 0.813494 11.00000 -1.20000
H19B 2 0.895757 0.656220 0.807334 11.00000 -1.20000
AFIX 0
C20 1 0.694817 0.679612 0.865199 11.00000 0.02422 0.02294 =
0.02116 0.00141 -0.00065 0.00164
C21 1 0.773041 0.760729 0.892233 11.00000 0.03491 0.03416 =
0.04160 -0.00038 -0.01422 0.00219
AFIX 137
H21A 2 0.713787 0.785960 0.931345 11.00000 -1.50000
H21B 2 0.781569 0.802013 0.852733 11.00000 -1.50000
H21C 2 0.873911 0.746211 0.909952 11.00000 -1.50000
AFIX 0
C22 1 0.591560 0.660401 0.167160 11.00000 0.02273 0.02460 =
0.01762 0.00048 0.00143 0.00160
AFIX 43
H22 2 0.640407 0.648764 0.211575 11.00000 -1.20000
AFIX 0
C23 1 0.454634 0.701470 0.158891 11.00000 0.02070 0.02084 =
0.01749 0.00183 0.00028 0.00030
C24 1 0.426152 0.703130 0.084969 11.00000 0.02052 0.02081 =
0.02177 -0.00176 0.00366 -0.00050
C25 1 0.288338 0.738469 0.051634 11.00000 0.02338 0.02230 =
0.01828 -0.00155 -0.00218 0.00299
AFIX 23
H25A 2 0.250804 0.698600 0.014291 11.00000 -1.20000
H25B 2 0.311611 0.793924 0.028304 11.00000 -1.20000
AFIX 0
C26 1 0.166587 0.751480 0.109529 11.00000 0.02005 0.02247 =
0.01679 -0.00069 -0.00133 0.00135
AFIX 13
H26 2 0.133015 0.693155 0.124970 11.00000 -1.20000
AFIX 0
C27 1 0.229161 0.797502 0.178060 11.00000 0.01737 0.02095 =
0.01479 -0.00099 -0.00096 0.00232
C28 1 0.346369 0.737197 0.213212 11.00000 0.01995 0.02792 =
0.01649 0.00065 0.00034 0.00286
AFIX 23
H28A 2 0.403304 0.769215 0.250296 11.00000 -1.20000
H28B 2 0.293214 0.689405 0.237335 11.00000 -1.20000
AFIX 0
C29 1 0.303957 0.882835 0.157434 11.00000 0.01939 0.02451 =
0.02239 -0.00167 0.00022 -0.00019
AFIX 137
H29A 2 0.390314 0.871719 0.125924 11.00000 -1.50000
H29B 2 0.338447 0.912174 0.201036 11.00000 -1.50000
H29C 2 0.230808 0.919029 0.132189 11.00000 -1.50000
AFIX 0
C30 1 0.097484 0.810588 0.232325 11.00000 0.01761 0.02266 =
0.01528 -0.00031 -0.00034 -0.00223
AFIX 13
H30 2 0.062968 0.751680 0.245576 11.00000 -1.20000
AFIX 0
C31 1 -0.041104 0.855127 0.199364 11.00000 0.01739 0.01947 =
0.01811 0.00016 -0.00019 0.00096
AFIX 13
H31 2 -0.011863 0.914449 0.184609 11.00000 -1.20000
AFIX 0
C32 1 -0.096030 0.806844 0.133281 11.00000 0.01808 0.03353 =
0.02308 -0.00458 -0.00315 0.00304
AFIX 23
H32A 2 -0.181307 0.838390 0.111398 11.00000 -1.20000
H32B 2 -0.133131 0.749652 0.147990 11.00000 -1.20000
AFIX 0
C33 1 0.029121 0.796093 0.077403 11.00000 0.02338 0.03401 =
0.02023 -0.00689 -0.00112 0.00436
AFIX 23
H33A 2 -0.009365 0.762010 0.036420 11.00000 -1.20000
H33B 2 0.059056 0.853103 0.058953 11.00000 -1.20000
AFIX 0
C34 1 0.150061 0.852435 0.303653 11.00000 0.01898 0.03035 =
0.02124 -0.00315 0.00100 0.00461
AFIX 23
H34A 2 0.230501 0.816725 0.325191 11.00000 -1.20000
H34B 2 0.193618 0.909442 0.293034 11.00000 -1.20000
AFIX 0
C35 1 0.021979 0.862922 0.358396 11.00000 0.02101 0.02955 =
0.01595 -0.00126 -0.00100 0.00541
AFIX 23
H35A 2 -0.010266 0.805760 0.375584 11.00000 -1.20000
H35B 2 0.059055 0.895823 0.400345 11.00000 -1.20000
AFIX 0
C36 1 -0.112953 0.909434 0.325119 11.00000 0.01916 0.01847 =
0.01899 0.00021 0.00104 0.00176
C37 1 -0.162974 0.861096 0.257102 11.00000 0.01662 0.02010 =
0.01945 0.00044 0.00056 0.00216
AFIX 13
H37 2 -0.185566 0.801024 0.272371 11.00000 -1.20000
AFIX 0
C38 1 -0.070380 1.002417 0.307675 11.00000 0.02677 0.02321 =
0.01922 -0.00305 0.00267 -0.00077
AFIX 137
H38A 2 -0.039218 1.031700 0.351869 11.00000 -1.50000
H38B 2 -0.157674 1.031931 0.286936 11.00000 -1.50000
H38C 2 0.012940 1.003007 0.273078 11.00000 -1.50000
AFIX 0
C39 1 -0.315091 0.902638 0.238187 11.00000 0.01746 0.03561 =
0.02170 -0.00212 0.00194 0.00418
AFIX 23
H39A 2 -0.383369 0.860559 0.215244 11.00000 -1.20000
H39B 2 -0.300793 0.951664 0.205103 11.00000 -1.20000
AFIX 0
C40 1 -0.379759 0.933165 0.311528 11.00000 0.02130 0.03349 =
0.02552 -0.00492 0.00123 0.00367
AFIX 23
H40A 2 -0.396590 0.995860 0.310972 11.00000 -1.20000
H40B 2 -0.476867 0.904354 0.321693 11.00000 -1.20000
AFIX 0
C41 1 -0.261350 0.909171 0.368981 11.00000 0.02088 0.02581 =
0.01834 -0.00088 0.00283 0.00268
C42 1 -0.301527 0.823943 0.404170 11.00000 0.02972 0.03469 =
0.03153 0.00297 0.01382 0.00086
AFIX 137
H42A 2 -0.220093 0.806603 0.436687 11.00000 -1.50000
H42B 2 -0.315015 0.780187 0.366920 11.00000 -1.50000
H42C 2 -0.395297 0.830263 0.431518 11.00000 -1.50000
AFIX 0
C43 1 0.560856 0.546141 0.463996 11.00000 0.02826 0.02715 =
0.02753 -0.00142 -0.00262 -0.00478
C44 1 0.715586 0.577601 0.448887 11.00000 0.02313 0.02135 =
0.02476 0.00016 -0.00020 -0.00203
C45 1 0.819715 0.588739 0.505161 11.00000 0.02941 0.02879 =
0.02677 -0.00331 -0.00275 0.00193
C46 1 0.964869 0.617839 0.491224 11.00000 0.02570 0.03026 =
0.05031 -0.00669 -0.00930 -0.00244
AFIX 43
H46 2 1.034026 0.626538 0.529556 11.00000 -1.20000
AFIX 0
C47 1 1.007093 0.633804 0.421876 11.00000 0.02241 0.02457 =
0.07095 0.00483 0.00391 -0.00045
AFIX 43
H47 2 1.106729 0.653129 0.412524 11.00000 -1.20000
AFIX 0
C48 1 0.909715 0.622721 0.365405 11.00000 0.03671 0.02937 =
0.04362 0.01099 0.01263 -0.00306
AFIX 43
H48 2 0.941859 0.634023 0.317602 11.00000 -1.20000
AFIX 0
C49 1 0.763841 0.594867 0.378609 11.00000 0.03210 0.02769 =
0.02776 0.00415 -0.00023 -0.00167
C50 1 -0.019540 0.545423 0.036026 11.00000 0.02682 0.02328 =
0.02691 0.00170 0.00175 0.00240
C51 1 0.139564 0.517122 0.043493 11.00000 0.02370 0.01756 =
0.02517 0.00218 -0.00061 0.00041
C52 1 0.207317 0.507040 0.112107 11.00000 0.03040 0.02008 =
0.02651 0.00555 -0.00214 0.00306
C53 1 0.356995 0.483827 0.118448 11.00000 0.02995 0.02858 =
0.03317 0.00791 -0.00815 0.00246
AFIX 43
H53 2 0.402305 0.478609 0.164542 11.00000 -1.20000
AFIX 0
C54 1 0.440278 0.468239 0.056770 11.00000 0.02166 0.02411 =
0.05737 0.00985 0.00054 0.00349
AFIX 43
H54 2 0.543038 0.451919 0.061169 11.00000 -1.20000
AFIX 0
C55 1 0.378246 0.475763 -0.010240 11.00000 0.02600 0.02531 =
0.04310 0.00123 0.01006 0.00351
AFIX 43
H55 2 0.437003 0.463508 -0.051694 11.00000 -1.20000
AFIX 0
C56 1 0.229374 0.501322 -0.017545 11.00000 0.02892 0.02009 =
0.02631 0.00079 0.00338 -0.00046
HKLF 5
REM b in P2(1)
REM R1 = 0.0304 for 9453 Fo > 4sig(Fo) and 0.0309 for all 9574 data
REM 674 parameters refined using 11 restraints
END
WGHT 0.0347 0.1429
REM Highest difference peak 0.134, deepest hole -0.123, 1-sigma level 0.028
Q1 1 0.2398 0.8252 0.6383 11.00000 0.05 0.13
Q2 1 0.5691 0.7093 0.7869 11.00000 0.05 0.13
Q3 1 0.7465 0.6588 0.8335 11.00000 0.05 0.12
Q4 1 -0.1278 0.8802 0.2994 11.00000 0.05 0.12
Q5 1 0.1283 0.7179 0.1231 11.00000 0.05 0.12
Q6 1 0.4054 0.7759 0.7176 11.00000 0.05 0.11
Q7 1 0.0260 0.8333 0.2175 11.00000 0.05 0.11
Q8 1 0.2861 0.4620 -0.0076 11.00000 0.05 0.11
Q9 1 0.6869 0.6555 0.8909 11.00000 0.05 0.11
Q10 1 0.1390 0.4922 0.0706 11.00000 0.05 0.11
;
_shelx_res_checksum 92041
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_STAN-GA-CH3CN-H2O
_database_code_depnum_ccdc_archive 'CCDC 1863940'
_audit_update_record
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2017/1
_shelx_SHELXL_version_number 2017/1
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety
'C21 H32.5 N2 O, C3.5 H2.5 O2.5, H0.5 O0.25, C2 H3 N'
_chemical_formula_sum 'C26.50 H38.50 N3 O3.75'
_chemical_formula_weight 459.10
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 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 32.061(3)
_cell_length_b 11.0501(9)
_cell_length_c 7.0657(6)
_cell_angle_alpha 90
_cell_angle_beta 93.859(3)
_cell_angle_gamma 90
_cell_volume 2497.5(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 3226
_cell_measurement_theta_min 2.55
_cell_measurement_theta_max 27.35
_exptl_crystal_description BLOCK
_exptl_crystal_colour colourless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.221
_exptl_crystal_F_000 994
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.300
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 0.082
_shelx_estimated_absorpt_T_min 0.968
_shelx_estimated_absorpt_T_max 0.984
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.971
_exptl_absorpt_correction_T_max 0.984
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1117 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8767.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 11229
_diffrn_reflns_av_unetI/netI 0.0806
_diffrn_reflns_av_R_equivalents 0.0442
_diffrn_reflns_limit_h_min -41
_diffrn_reflns_limit_h_max 40
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 2.547
_diffrn_reflns_theta_max 27.548
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 5681
_reflns_number_gt 3855
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.902
_reflns_Friedel_fraction_max 0.997
_reflns_Friedel_fraction_full 0.999
_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 ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_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^)+(0.0527P)^2^+1.5918P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack 0(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns 5681
_refine_ls_number_parameters 332
_refine_ls_number_restraints 34
_refine_ls_R_factor_all 0.1047
_refine_ls_R_factor_gt 0.0619
_refine_ls_wR_factor_ref 0.1411
_refine_ls_wR_factor_gt 0.1230
_refine_ls_goodness_of_fit_ref 1.016
_refine_ls_restrained_S_all 1.025
_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 0.08401(8) 0.4464(3) 0.0477(4) 0.0352(7) Uani 1 1 d D . . . .
H1 H 0.0814(15) 0.5205(17) 0.074(7) 0.047(16) Uiso 1 1 d D . . . .
O2 O 0.4817(2) 1.2528(4) 0.3616(8) 0.114(2) Uani 1 1 d . . . . .
O3 O 0.46453(10) 0.8103(3) 0.1994(5) 0.0394(8) Uani 1 1 d D . . . .
H3 H 0.4525(14) 0.850(4) 0.108(5) 0.053(16) Uiso 1 1 d D . . . .
O4 O 0.500000 0.6918(4) 0.500000 0.0440(12) Uani 1 2 d DS T P . .
H4 H 0.5213(18) 0.667(8) 0.567(12) 0.04(3) Uiso 0.5 1 d D . P . .
O5 O 0.000000 1.1170(13) 0.000000 0.091(4) Uani 0.5 2 d DS T P . .
H5A H -0.013(5) 1.184(7) -0.02(3) 0.137 Uiso 0.5 1 d D U P . .
N1 N 0.43382(10) 0.5577(3) 0.3438(5) 0.0318(7) Uani 1 1 d D U . . .
H1A H 0.4578(13) 0.596(7) 0.360(12) 0.038 Uiso 0.5 1 d D U P . .
N2 N 0.42742(10) 0.4372(3) 0.3519(5) 0.0325(8) Uani 1 1 d D U . . .
H2 H 0.4460(11) 0.379(3) 0.360(6) 0.039 Uiso 1 1 d D U . . .
N3 N 0.08128(17) 0.7118(5) 0.1080(8) 0.0724(15) Uani 1 1 d . . . . .
C1 C 0.39653(12) 0.6117(4) 0.3208(6) 0.0313(8) Uani 1 1 d . U . . .
H1B H 0.392149 0.696648 0.312632 0.026(10) Uiso 1 1 calc R . . . .
C2 C 0.36524(12) 0.5251(4) 0.3108(6) 0.0290(9) Uani 1 1 d . U . . .
C3 C 0.38590(11) 0.4158(4) 0.3311(5) 0.0285(9) Uani 1 1 d . . . . .
C4 C 0.36528(13) 0.2952(4) 0.3281(7) 0.0350(11) Uani 1 1 d . . . . .
H4A H 0.377576 0.244871 0.433604 0.042 Uiso 1 1 calc R U . . .
H4B H 0.369846 0.253414 0.207311 0.042 Uiso 1 1 calc R U . . .
C5 C 0.31808(12) 0.3113(4) 0.3486(6) 0.0288(9) Uani 1 1 d . . . . .
H5 H 0.314485 0.334124 0.483508 0.035 Uiso 1 1 calc R U . . .
C6 C 0.29826(11) 0.4138(4) 0.2221(5) 0.0254(9) Uani 1 1 d . . . . .
C7 C 0.31829(11) 0.5345(4) 0.2855(6) 0.0298(10) Uani 1 1 d . . . . .
H7A H 0.310595 0.597367 0.189562 0.036 Uiso 1 1 calc R U . . .
H7B H 0.307214 0.559724 0.406840 0.036 Uiso 1 1 calc R U . . .
C8 C 0.30585(11) 0.3926(4) 0.0116(6) 0.0281(9) Uani 1 1 d . . . . .
H8A H 0.292386 0.457113 -0.065536 0.042 Uiso 1 1 calc R U . . .
H8B H 0.294025 0.314217 -0.028949 0.042 Uiso 1 1 calc R U . . .
H8C H 0.335968 0.392820 -0.004687 0.042 Uiso 1 1 calc R U . . .
C9 C 0.25056(11) 0.4193(4) 0.2527(6) 0.0255(9) Uani 1 1 d . . . . .
H9 H 0.248557 0.434923 0.391157 0.031 Uiso 1 1 calc R U . . .
C10 C 0.22808(12) 0.2970(4) 0.2125(6) 0.0289(9) Uani 1 1 d . . . . .
H10 H 0.230517 0.274968 0.076468 0.035 Uiso 1 1 calc R U . . .
C11 C 0.24906(12) 0.1985(4) 0.3377(6) 0.0341(10) Uani 1 1 d . . . . .
H11A H 0.244608 0.216115 0.472263 0.041 Uiso 1 1 calc R U . . .
H11B H 0.235843 0.119534 0.305431 0.041 Uiso 1 1 calc R U . . .
C12 C 0.29583(12) 0.1901(4) 0.3129(6) 0.0330(10) Uani 1 1 d . . . . .
H12A H 0.300201 0.162711 0.182293 0.040 Uiso 1 1 calc R U . . .
H12B H 0.308346 0.128954 0.401954 0.040 Uiso 1 1 calc R U . . .
C13 C 0.22843(12) 0.5255(4) 0.1508(7) 0.0321(10) Uani 1 1 d . . . . .
H13A H 0.232138 0.518952 0.013186 0.039 Uiso 1 1 calc R U . . .
H13B H 0.241800 0.601825 0.196448 0.039 Uiso 1 1 calc R U . . .
C14 C 0.18124(11) 0.5316(4) 0.1814(6) 0.0310(10) Uani 1 1 d . . . . .
H14A H 0.177294 0.551020 0.315777 0.037 Uiso 1 1 calc R U . . .
H14B H 0.168178 0.596912 0.101863 0.037 Uiso 1 1 calc R U . . .
C15 C 0.16009(11) 0.4125(4) 0.1303(5) 0.0255(9) Uani 1 1 d . . . . .
C16 C 0.18212(11) 0.3119(4) 0.2477(6) 0.0297(10) Uani 1 1 d . . . . .
H16 H 0.180942 0.335566 0.383798 0.036 Uiso 1 1 calc R U . . .
C17 C 0.16122(12) 0.3893(4) -0.0845(5) 0.0301(9) Uani 1 1 d . . . . .
H17A H 0.190304 0.388614 -0.119231 0.045 Uiso 1 1 calc R U . . .
H17B H 0.145858 0.453606 -0.154705 0.045 Uiso 1 1 calc R U . . .
H17C H 0.148217 0.310978 -0.116162 0.045 Uiso 1 1 calc R U . . .
C18 C 0.15286(12) 0.2016(4) 0.2157(7) 0.0360(11) Uani 1 1 d . . . . .
H18A H 0.154888 0.147077 0.327116 0.043 Uiso 1 1 calc R U . . .
H18B H 0.159869 0.155358 0.102076 0.043 Uiso 1 1 calc R U . . .
C19 C 0.10843(13) 0.2578(4) 0.1871(7) 0.0373(11) Uani 1 1 d . . . . .
H19A H 0.094456 0.230532 0.065348 0.045 Uiso 1 1 calc R U . . .
H19B H 0.091110 0.233121 0.291335 0.045 Uiso 1 1 calc R U . . .
C20 C 0.11416(12) 0.3971(4) 0.1867(6) 0.0321(10) Uani 1 1 d . . . . .
C21 C 0.10616(13) 0.4515(5) 0.3781(6) 0.0443(12) Uani 1 1 d . . . . .
H21A H 0.077411 0.433755 0.408407 0.066 Uiso 1 1 calc R U . . .
H21B H 0.110179 0.539370 0.373577 0.066 Uiso 1 1 calc R U . . .
H21C H 0.125707 0.416623 0.475819 0.066 Uiso 1 1 calc R U . . .
C22 C 0.500000 1.1995(7) 0.500000 0.058(2) Uani 1 2 d S T P . .
C23 C 0.500000 1.0643(6) 0.500000 0.0336(14) Uani 1 2 d S T P . .
C24 C 0.48224(12) 1.0028(4) 0.3442(6) 0.0300(10) Uani 1 1 d . . . . .
H24 H 0.470277 1.046218 0.237986 0.036 Uiso 1 1 calc R U . . .
C25 C 0.48202(12) 0.8783(4) 0.3442(6) 0.0286(10) Uani 1 1 d . . . . .
C26 C 0.500000 0.8152(5) 0.500000 0.0291(13) Uani 1 2 d S T P . .
C27 C 0.07266(17) 0.8101(6) 0.1268(8) 0.0556(14) Uani 1 1 d . . . . .
C28 C 0.0655(3) 0.9378(6) 0.1502(10) 0.099(3) Uani 1 1 d . . . . .
H28A H 0.066941 0.978706 0.027761 0.149 Uiso 1 1 calc R U . . .
H28B H 0.086958 0.971101 0.241106 0.149 Uiso 1 1 calc R U . . .
H28C H 0.037840 0.950432 0.197722 0.149 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 0.0217(13) 0.0432(19) 0.0392(18) -0.0070(16) -0.0101(12) -0.0007(15)
O2 0.216(6) 0.046(2) 0.085(4) 0.025(2) 0.051(4) 0.063(3)
O3 0.0405(18) 0.0377(18) 0.0369(19) 0.0038(15) -0.0195(14) -0.0019(15)
O4 0.045(3) 0.026(2) 0.055(3) 0.000 -0.034(2) 0.000
O5 0.087(10) 0.069(9) 0.121(12) 0.000 0.024(9) 0.000
N1 0.0283(11) 0.0327(12) 0.0338(13) 0.0021(11) -0.0021(10) -0.0025(10)
N2 0.0241(14) 0.0330(15) 0.0397(18) 0.0032(15) -0.0033(13) 0.0030(14)
N3 0.073(4) 0.060(3) 0.083(4) -0.001(3) 0.004(3) 0.006(3)
C1 0.0286(11) 0.0328(13) 0.0321(14) -0.0008(12) -0.0008(11) -0.0018(9)
C2 0.0264(13) 0.0318(14) 0.0288(14) -0.0019(11) 0.0004(11) -0.0005(10)
C3 0.0206(18) 0.037(2) 0.027(2) 0.0024(19) -0.0024(16) -0.0007(18)
C4 0.026(2) 0.038(3) 0.040(3) 0.004(2) -0.0082(18) -0.0012(19)
C5 0.022(2) 0.037(2) 0.027(2) 0.0023(19) -0.0026(16) -0.0017(19)
C6 0.0172(17) 0.034(2) 0.025(2) -0.0015(18) -0.0007(15) -0.0015(17)
C7 0.0177(19) 0.038(3) 0.033(2) -0.008(2) -0.0024(16) -0.0022(18)
C8 0.0192(18) 0.035(2) 0.030(2) 0.0011(19) -0.0001(16) -0.0023(18)
C9 0.0199(17) 0.033(2) 0.024(2) -0.0009(17) -0.0003(14) -0.0032(16)
C10 0.022(2) 0.037(3) 0.027(2) 0.0045(18) -0.0026(16) -0.0055(17)
C11 0.026(2) 0.041(3) 0.035(3) 0.011(2) -0.0018(18) -0.004(2)
C12 0.026(2) 0.037(3) 0.035(3) 0.012(2) -0.0075(18) -0.0005(19)
C13 0.0196(19) 0.034(2) 0.042(3) -0.004(2) -0.0040(17) -0.0018(18)
C14 0.0191(19) 0.043(3) 0.030(2) -0.007(2) -0.0024(16) 0.0015(19)
C15 0.0196(18) 0.034(2) 0.023(2) -0.0031(18) 0.0014(15) -0.0022(17)
C16 0.0191(19) 0.049(3) 0.021(2) 0.003(2) -0.0023(16) -0.002(2)
C17 0.030(2) 0.034(2) 0.025(2) 0.0000(19) -0.0026(16) 0.0007(19)
C18 0.025(2) 0.046(3) 0.036(3) 0.012(2) -0.0035(18) -0.006(2)
C19 0.024(2) 0.054(3) 0.034(3) 0.004(2) -0.0033(18) -0.010(2)
C20 0.0176(18) 0.049(3) 0.029(2) -0.004(2) -0.0014(15) -0.0017(19)
C21 0.023(2) 0.074(3) 0.036(3) -0.008(3) 0.0072(18) -0.002(2)
C22 0.079(6) 0.034(4) 0.062(6) 0.000 0.017(4) 0.000
C23 0.023(3) 0.031(3) 0.047(4) 0.000 0.009(3) 0.000
C24 0.0159(19) 0.032(2) 0.042(3) 0.007(2) 0.0005(18) 0.0021(17)
C25 0.0171(19) 0.034(2) 0.034(2) 0.0010(19) -0.0045(16) -0.0050(17)
C26 0.019(3) 0.023(3) 0.044(4) 0.000 -0.003(2) 0.000
C27 0.052(3) 0.066(4) 0.050(3) 0.005(3) 0.011(3) 0.001(3)
C28 0.182(8) 0.065(4) 0.056(4) 0.010(4) 0.033(4) 0.021(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 C20 1.438(5) . ?
O1 H1 0.845(14) . ?
O2 C22 1.253(6) . ?
O3 C25 1.360(5) . ?
O3 H3 0.852(14) . ?
O4 C26 1.364(7) . ?
O4 H4 0.850(14) . ?
O4 H4 0.850(14) 2_656 ?
O5 H5A 0.858(15) . ?
O5 H5A 0.858(15) 2 ?
N1 C1 1.337(5) . ?
N1 N2 1.349(5) . ?
N1 H1A 0.877(14) . ?
N2 C3 1.350(5) . ?
N2 H2 0.880(14) . ?
N3 C27 1.131(7) . ?
C1 C2 1.385(6) . ?
C1 H1B 0.9500 . ?
C2 C3 1.380(6) . ?
C2 C7 1.507(5) . ?
C3 C4 1.488(6) . ?
C4 C5 1.540(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.530(6) . ?
C5 C6 1.552(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.534(6) . ?
C6 C8 1.541(5) . ?
C6 C9 1.560(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C13 1.527(6) . ?
C9 C10 1.549(5) . ?
C9 H9 1.0000 . ?
C10 C16 1.519(5) . ?
C10 C11 1.530(6) . ?
C10 H10 1.0000 . ?
C11 C12 1.524(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.544(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.513(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.531(6) . ?
C15 C17 1.542(5) . ?
C15 C20 1.561(5) . ?
C16 C18 1.545(6) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.555(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.549(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.517(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.493(10) . ?
C23 C24 1.383(5) 2_656 ?
C23 C24 1.383(5) . ?
C24 C25 1.375(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(5) . ?
C27 C28 1.440(9) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C20 O1 H1 107(4) . . ?
C25 O3 H3 115(4) . . ?
C26 O4 H4 109(7) . . ?
C26 O4 H4 109(6) . 2_656 ?
H4 O4 H4 142(10) . 2_656 ?
H5A O5 H5A 60(10) . 2 ?
C1 N1 N2 108.0(3) . . ?
C1 N1 H1A 125(6) . . ?
N2 N1 H1A 127(6) . . ?
C3 N2 N1 108.7(3) . . ?
C3 N2 H2 122(3) . . ?
N1 N2 H2 129(3) . . ?
N1 C1 C2 109.7(4) . . ?
N1 C1 H1B 125.2 . . ?
C2 C1 H1B 125.2 . . ?
C3 C2 C1 105.0(3) . . ?
C3 C2 C7 122.7(4) . . ?
C1 C2 C7 132.3(4) . . ?
N2 C3 C2 108.7(4) . . ?
N2 C3 C4 126.3(4) . . ?
C2 C3 C4 125.0(3) . . ?
C3 C4 C5 109.5(3) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C12 C5 C4 109.5(3) . . ?
C12 C5 C6 112.0(3) . . ?
C4 C5 C6 113.4(3) . . ?
C12 C5 H5 107.2 . . ?
C4 C5 H5 107.2 . . ?
C6 C5 H5 107.2 . . ?
C7 C6 C8 108.9(3) . . ?
C7 C6 C5 108.6(3) . . ?
C8 C6 C5 111.1(3) . . ?
C7 C6 C9 108.7(3) . . ?
C8 C6 C9 111.1(3) . . ?
C5 C6 C9 108.4(3) . . ?
C2 C7 C6 111.7(3) . . ?
C2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 112.9(3) . . ?
C13 C9 C6 113.2(3) . . ?
C10 C9 C6 112.9(3) . . ?
C13 C9 H9 105.7 . . ?
C10 C9 H9 105.7 . . ?
C6 C9 H9 105.7 . . ?
C16 C10 C11 112.1(3) . . ?
C16 C10 C9 108.7(3) . . ?
C11 C10 C9 109.5(3) . . ?
C16 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C12 C11 C10 112.0(3) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C5 112.3(4) . . ?
C11 C12 H12A 109.1 . . ?
C5 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C5 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C9 C13 C14 113.3(3) . . ?
C9 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C9 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 110.9(3) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 108.6(3) . . ?
C14 C15 C17 109.8(3) . . ?
C16 C15 C17 111.8(3) . . ?
C14 C15 C20 116.7(3) . . ?
C16 C15 C20 101.0(3) . . ?
C17 C15 C20 108.6(3) . . ?
C10 C16 C15 114.0(3) . . ?
C10 C16 C18 118.5(4) . . ?
C15 C16 C18 103.9(3) . . ?
C10 C16 H16 106.6 . . ?
C15 C16 H16 106.6 . . ?
C18 C16 H16 106.6 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 104.2(4) . . ?
C16 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C16 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C20 C19 C18 106.8(3) . . ?
C20 C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C18 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O1 C20 C21 108.2(3) . . ?
O1 C20 C19 107.7(3) . . ?
C21 C20 C19 111.4(4) . . ?
O1 C20 C15 112.7(3) . . ?
C21 C20 C15 113.8(3) . . ?
C19 C20 C15 102.9(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 O2 123.8(9) . 2_656 ?
O2 C22 C23 118.1(4) . . ?
O2 C22 C23 118.1(4) 2_656 . ?
C24 C23 C24 121.1(6) 2_656 . ?
C24 C23 C22 119.4(3) 2_656 . ?
C24 C23 C22 119.4(3) . . ?
C25 C24 C23 119.6(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
O3 C25 C24 123.7(4) . . ?
O3 C25 C26 116.4(4) . . ?
C24 C25 C26 119.9(4) . . ?
O4 C26 C25 120.0(3) . 2_656 ?
O4 C26 C25 120.0(3) . . ?
C25 C26 C25 120.0(5) 2_656 . ?
N3 C27 C28 175.0(7) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C1 N1 N2 C3 0.9(5) . . . . ?
N2 N1 C1 C2 -1.0(5) . . . . ?
N1 C1 C2 C3 0.6(5) . . . . ?
N1 C1 C2 C7 -179.8(4) . . . . ?
N1 N2 C3 C2 -0.5(5) . . . . ?
N1 N2 C3 C4 178.9(4) . . . . ?
C1 C2 C3 N2 -0.1(5) . . . . ?
C7 C2 C3 N2 -179.7(4) . . . . ?
C1 C2 C3 C4 -179.5(4) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
N2 C3 C4 C5 166.8(4) . . . . ?
C2 C3 C4 C5 -13.8(6) . . . . ?
C3 C4 C5 C12 170.7(4) . . . . ?
C3 C4 C5 C6 44.8(5) . . . . ?
C12 C5 C6 C7 172.3(3) . . . . ?
C4 C5 C6 C7 -63.1(4) . . . . ?
C12 C5 C6 C8 -67.9(4) . . . . ?
C4 C5 C6 C8 56.6(4) . . . . ?
C12 C5 C6 C9 54.4(4) . . . . ?
C4 C5 C6 C9 178.9(3) . . . . ?
C3 C2 C7 C6 -18.3(6) . . . . ?
C1 C2 C7 C6 162.2(4) . . . . ?
C8 C6 C7 C2 -74.3(4) . . . . ?
C5 C6 C7 C2 46.7(4) . . . . ?
C9 C6 C7 C2 164.5(3) . . . . ?
C7 C6 C9 C13 56.2(4) . . . . ?
C8 C6 C9 C13 -63.7(4) . . . . ?
C5 C6 C9 C13 174.1(3) . . . . ?
C7 C6 C9 C10 -174.1(3) . . . . ?
C8 C6 C9 C10 66.1(4) . . . . ?
C5 C6 C9 C10 -56.2(4) . . . . ?
C13 C9 C10 C16 -50.5(4) . . . . ?
C6 C9 C10 C16 179.6(3) . . . . ?
C13 C9 C10 C11 -173.2(3) . . . . ?
C6 C9 C10 C11 56.9(4) . . . . ?
C16 C10 C11 C12 -175.8(4) . . . . ?
C9 C10 C11 C12 -55.1(5) . . . . ?
C10 C11 C12 C5 55.4(5) . . . . ?
C4 C5 C12 C11 178.0(3) . . . . ?
C6 C5 C12 C11 -55.3(5) . . . . ?
C10 C9 C13 C14 50.4(5) . . . . ?
C6 C9 C13 C14 -179.8(3) . . . . ?
C9 C13 C14 C15 -53.4(5) . . . . ?
C13 C14 C15 C16 56.4(4) . . . . ?
C13 C14 C15 C17 -66.2(4) . . . . ?
C13 C14 C15 C20 169.7(3) . . . . ?
C11 C10 C16 C15 178.1(4) . . . . ?
C9 C10 C16 C15 56.9(4) . . . . ?
C11 C10 C16 C18 -59.2(5) . . . . ?
C9 C10 C16 C18 179.6(3) . . . . ?
C14 C15 C16 C10 -60.9(4) . . . . ?
C17 C15 C16 C10 60.5(5) . . . . ?
C20 C15 C16 C10 175.8(3) . . . . ?
C14 C15 C16 C18 168.7(3) . . . . ?
C17 C15 C16 C18 -69.9(4) . . . . ?
C20 C15 C16 C18 45.4(4) . . . . ?
C10 C16 C18 C19 -158.9(4) . . . . ?
C15 C16 C18 C19 -31.2(4) . . . . ?
C16 C18 C19 C20 4.7(5) . . . . ?
C18 C19 C20 O1 142.1(3) . . . . ?
C18 C19 C20 C21 -99.4(4) . . . . ?
C18 C19 C20 C15 22.9(4) . . . . ?
C14 C15 C20 O1 85.1(4) . . . . ?
C16 C15 C20 O1 -157.4(3) . . . . ?
C17 C15 C20 O1 -39.7(5) . . . . ?
C14 C15 C20 C21 -38.6(5) . . . . ?
C16 C15 C20 C21 78.9(5) . . . . ?
C17 C15 C20 C21 -163.3(4) . . . . ?
C14 C15 C20 C19 -159.3(4) . . . . ?
C16 C15 C20 C19 -41.7(4) . . . . ?
C17 C15 C20 C19 76.0(4) . . . . ?
O2 C22 C23 C24 -176.2(4) . . . 2_656 ?
O2 C22 C23 C24 3.8(4) 2_656 . . 2_656 ?
O2 C22 C23 C24 3.8(4) . . . . ?
O2 C22 C23 C24 -176.2(4) 2_656 . . . ?
C24 C23 C24 C25 0.3(3) 2_656 . . . ?
C22 C23 C24 C25 -179.7(3) . . . . ?
C23 C24 C25 O3 178.6(3) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
O3 C25 C26 O4 1.1(4) . . . . ?
C24 C25 C26 O4 -179.7(3) . . . . ?
O3 C25 C26 C25 -178.9(4) . . . 2_656 ?
C24 C25 C26 C25 0.3(3) . . . 2_656 ?
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
_geom_hbond_publ_flag
O1 H1 N3 0.845(14) 2.128(17) 2.966(7) 171(5) . yes
N1 H1A O3 0.877(14) 2.64(7) 3.152(5) 118(6) . yes
N1 H1A O4 0.877(14) 1.94(4) 2.757(4) 155(8) . yes
O3 H3 O1 0.852(14) 1.882(19) 2.714(4) 165(5) 4 yes
O4 H4 N1 0.850(14) 1.95(4) 2.757(4) 158(9) 2_656 yes
N2 H2 O2 0.880(14) 1.800(16) 2.678(6) 175(5) 1_545 yes
_refine_diff_density_max 0.437
_refine_diff_density_min -0.458
_refine_diff_density_rms 0.048
_shelx_res_file
;
TITL 1 in C2
T.res
created by SHELXL-2017/1 at 11:47:26 on 26-Aug-2018
CELL 0.71073 32.061 11.0501 7.0657 90 93.8586 90
ZERR 4 0.0026 0.0009 0.0006 0 0.0028 0
LATT -7
SYMM -X,+Y,-Z
SFAC C H N O
UNIT 106 154 12 15
DELU 0.001 0.0005 N1 C1
DELU 0.002 0.001 N1 N2
DELU 0.001 0.0005 C2 C1
ISOR 0.001 0.0005 N1 C1
ISOR 0.002 0.001 N1 N2
ISOR 0.001 0.0005 C2 C1
SIZE 0.20 0.30 0.40
TEMP -153
DFIX 0.85 0.01 O1 H1 O3 H3 O4 H4 O5 H5A
DFIX 0.87 0.01 N1 H1A N2 H2
L.S. 40
PLAN 10
HTAB 2
HTAB O1 N3
HTAB N1 O3
HTAB N1 O4
HTAB O3 O1_$1
HTAB O4 N1_$2
HTAB N2 O2_$3
EQIV $1 -x+1/2, y+1/2, -z
EQIV $2 -x+1, y, -z+1
EQIV $3 x, y-1, z
MORE -1
BOND $H
CONF
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT -4 -4 4
OMIT 28 0 3
OMIT 29 -3 3
OMIT 3 -3 3
OMIT -32 0 1
REM
REM
REM
WGHT 0.052700 1.591800
BASF 0.04249
FVAR 0.12391
O1 4 0.084011 0.446426 0.047693 11.00000 0.02169 0.04317 =
0.03917 -0.00697 -0.01008 -0.00075
H1 2 0.081428 0.520488 0.074293 11.00000 0.04694
O2 4 0.481746 1.252842 0.361620 11.00000 0.21641 0.04567 =
0.08474 0.02468 0.05111 0.06320
O3 4 0.464533 0.810265 0.199396 11.00000 0.04047 0.03775 =
0.03689 0.00376 -0.01953 -0.00194
H3 2 0.452510 0.849979 0.107856 11.00000 0.05349
O4 4 0.500000 0.691758 0.500000 10.50000 0.04533 0.02635 =
0.05533 0.00000 -0.03417 0.00000
H4 2 0.521261 0.666562 0.566878 10.50000 0.04179
O5 4 0.000000 1.117039 0.000000 10.25000 0.08736 0.06863 =
0.12083 0.00000 0.02430 0.00000
H5A 2 -0.012877 1.184155 -0.021670 10.50000 -1.50000
N1 3 0.433823 0.557695 0.343783 11.00000 0.02833 0.03267 =
0.03385 0.00209 -0.00207 -0.00249
H1A 2 0.457773 0.595850 0.359579 10.50000 -1.20000
N2 3 0.427417 0.437233 0.351924 11.00000 0.02415 0.03296 =
0.03966 0.00322 -0.00329 0.00303
H2 2 0.446022 0.378589 0.360426 11.00000 -1.20000
N3 3 0.081281 0.711827 0.107987 11.00000 0.07314 0.06031 =
0.08350 -0.00118 0.00357 0.00602
C1 1 0.396527 0.611728 0.320817 11.00000 0.02857 0.03277 =
0.03207 -0.00084 -0.00082 -0.00182
AFIX 43
H1B 2 0.392149 0.696648 0.312632 11.00000 0.02602
AFIX 0
C2 1 0.365242 0.525145 0.310767 11.00000 0.02636 0.03177 =
0.02878 -0.00189 0.00044 -0.00055
C3 1 0.385903 0.415846 0.331110 11.00000 0.02063 0.03685 =
0.02746 0.00241 -0.00240 -0.00074
C4 1 0.365275 0.295167 0.328144 11.00000 0.02557 0.03801 =
0.03991 0.00377 -0.00818 -0.00122
AFIX 23
H4A 2 0.377576 0.244871 0.433604 11.00000 -1.20000
H4B 2 0.369846 0.253414 0.207311 11.00000 -1.20000
AFIX 0
C5 1 0.318081 0.311289 0.348627 11.00000 0.02250 0.03680 =
0.02660 0.00231 -0.00257 -0.00167
AFIX 13
H5 2 0.314485 0.334124 0.483508 11.00000 -1.20000
AFIX 0
C6 1 0.298264 0.413802 0.222098 11.00000 0.01722 0.03376 =
0.02507 -0.00154 -0.00066 -0.00150
C7 1 0.318289 0.534506 0.285473 11.00000 0.01773 0.03776 =
0.03337 -0.00771 -0.00239 -0.00224
AFIX 23
H7A 2 0.310595 0.597367 0.189562 11.00000 -1.20000
H7B 2 0.307214 0.559724 0.406840 11.00000 -1.20000
AFIX 0
C8 1 0.305852 0.392553 0.011561 11.00000 0.01917 0.03493 =
0.02983 0.00115 -0.00008 -0.00231
AFIX 137
H8A 2 0.292386 0.457113 -0.065536 11.00000 -1.50000
H8B 2 0.294025 0.314217 -0.028949 11.00000 -1.50000
H8C 2 0.335968 0.392820 -0.004687 11.00000 -1.50000
AFIX 0
C9 1 0.250558 0.419284 0.252663 11.00000 0.01992 0.03284 =
0.02354 -0.00089 -0.00027 -0.00319
AFIX 13
H9 2 0.248557 0.434923 0.391157 11.00000 -1.20000
AFIX 0
C10 1 0.228076 0.297004 0.212545 11.00000 0.02195 0.03658 =
0.02746 0.00447 -0.00259 -0.00552
AFIX 13
H10 2 0.230517 0.274968 0.076468 11.00000 -1.20000
AFIX 0
C11 1 0.249061 0.198502 0.337730 11.00000 0.02631 0.04071 =
0.03471 0.01063 -0.00184 -0.00418
AFIX 23
H11A 2 0.244608 0.216115 0.472263 11.00000 -1.20000
H11B 2 0.235843 0.119534 0.305431 11.00000 -1.20000
AFIX 0
C12 1 0.295831 0.190127 0.312875 11.00000 0.02556 0.03719 =
0.03487 0.01185 -0.00754 -0.00054
AFIX 23
H12A 2 0.300201 0.162711 0.182293 11.00000 -1.20000
H12B 2 0.308346 0.128954 0.401954 11.00000 -1.20000
AFIX 0
C13 1 0.228434 0.525520 0.150782 11.00000 0.01958 0.03394 =
0.04203 -0.00384 -0.00398 -0.00180
AFIX 23
H13A 2 0.232138 0.518952 0.013186 11.00000 -1.20000
H13B 2 0.241800 0.601825 0.196448 11.00000 -1.20000
AFIX 0
C14 1 0.181237 0.531599 0.181369 11.00000 0.01908 0.04322 =
0.03026 -0.00667 -0.00235 0.00146
AFIX 23
H14A 2 0.177294 0.551020 0.315777 11.00000 -1.20000
H14B 2 0.168178 0.596912 0.101863 11.00000 -1.20000
AFIX 0
C15 1 0.160090 0.412481 0.130299 11.00000 0.01956 0.03405 =
0.02292 -0.00315 0.00135 -0.00217
C16 1 0.182119 0.311888 0.247663 11.00000 0.01909 0.04870 =
0.02083 0.00323 -0.00232 -0.00247
AFIX 13
H16 2 0.180942 0.335566 0.383798 11.00000 -1.20000
AFIX 0
C17 1 0.161220 0.389308 -0.084528 11.00000 0.02987 0.03440 =
0.02531 0.00001 -0.00265 0.00073
AFIX 137
H17A 2 0.190304 0.388614 -0.119231 11.00000 -1.50000
H17B 2 0.145858 0.453606 -0.154705 11.00000 -1.50000
H17C 2 0.148217 0.310978 -0.116162 11.00000 -1.50000
AFIX 0
C18 1 0.152862 0.201591 0.215685 11.00000 0.02518 0.04565 =
0.03640 0.01249 -0.00346 -0.00564
AFIX 23
H18A 2 0.154888 0.147077 0.327116 11.00000 -1.20000
H18B 2 0.159869 0.155358 0.102076 11.00000 -1.20000
AFIX 0
C19 1 0.108426 0.257843 0.187119 11.00000 0.02387 0.05362 =
0.03383 0.00446 -0.00335 -0.01047
AFIX 23
H19A 2 0.094456 0.230532 0.065348 11.00000 -1.20000
H19B 2 0.091110 0.233121 0.291335 11.00000 -1.20000
AFIX 0
C20 1 0.114161 0.397075 0.186720 11.00000 0.01760 0.04900 =
0.02920 -0.00398 -0.00143 -0.00166
C21 1 0.106156 0.451527 0.378074 11.00000 0.02348 0.07385 =
0.03632 -0.00799 0.00718 -0.00166
AFIX 137
H21A 2 0.077411 0.433755 0.408407 11.00000 -1.50000
H21B 2 0.110179 0.539370 0.373577 11.00000 -1.50000
H21C 2 0.125707 0.416623 0.475819 11.00000 -1.50000
AFIX 0
C22 1 0.500000 1.199467 0.500000 10.50000 0.07897 0.03387 =
0.06224 0.00000 0.01743 0.00000
C23 1 0.500000 1.064312 0.500000 10.50000 0.02338 0.03107 =
0.04725 0.00000 0.00950 0.00000
C24 1 0.482244 1.002781 0.344243 11.00000 0.01590 0.03217 =
0.04179 0.00666 0.00050 0.00210
AFIX 43
H24 2 0.470277 1.046218 0.237986 11.00000 -1.20000
AFIX 0
C25 1 0.482023 0.878337 0.344167 11.00000 0.01710 0.03368 =
0.03404 0.00104 -0.00453 -0.00498
C26 1 0.500000 0.815219 0.500000 10.50000 0.01911 0.02318 =
0.04441 0.00000 -0.00337 0.00000
C27 1 0.072662 0.810139 0.126823 11.00000 0.05220 0.06601 =
0.04959 0.00477 0.01071 0.00093
C28 1 0.065530 0.937794 0.150223 11.00000 0.18151 0.06478 =
0.05560 0.01025 0.03312 0.02127
AFIX 137
H28A 2 0.066941 0.978706 0.027761 11.00000 -1.50000
H28B 2 0.086958 0.971101 0.241106 11.00000 -1.50000
H28C 2 0.037840 0.950432 0.197722 11.00000 -1.50000
AFIX 0
HKLF 4
REM 1 in C2
REM R1 = 0.0619 for 3855 Fo > 4sig(Fo) and 0.1047 for all 5681 data
REM 332 parameters refined using 34 restraints
END
WGHT 0.0523 1.6047
REM Instructions for potential hydrogen bonds
HTAB O1 N3
HTAB O3 O1_$1
HTAB O4 N1_$2
EQIV $5 x-1/2, y+1/2, z
HTAB O5 O3_$5
HTAB N1 O3
HTAB N1 O4
HTAB N2 O2_$3
REM Highest difference peak 0.437, deepest hole -0.458, 1-sigma level 0.048
Q1 1 0.4963 1.2583 0.3845 11.00000 0.05 0.44
Q2 1 0.4583 1.2284 0.4016 11.00000 0.05 0.40
Q3 1 0.4699 1.2432 0.2914 11.00000 0.05 0.29
Q4 1 0.1368 0.3936 0.1386 11.00000 0.05 0.21
Q5 1 0.0279 0.7747 0.1030 11.00000 0.05 0.20
Q6 1 0.0614 0.9626 0.3068 11.00000 0.05 0.19
Q7 1 0.2758 0.4163 0.2356 11.00000 0.05 0.19
Q8 1 0.0204 0.7986 0.0648 11.00000 0.05 0.19
Q9 1 0.0314 0.4567 0.0799 11.00000 0.05 0.17
Q10 1 0.4196 0.5817 0.4151 11.00000 0.05 0.16
;
_shelx_res_checksum 13603
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_STAN-DHA
_database_code_depnum_ccdc_archive 'CCDC 1863938'
_audit_update_record
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2017/1
_shelx_SHELXL_version_number 2017/1
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H32 N2 O, C7 H6 O4'
_chemical_formula_sum 'C28 H38 N2 O5'
_chemical_formula_weight 482.60
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 9.6635(3)
_cell_length_b 23.4950(6)
_cell_length_c 11.8249(3)
_cell_angle_alpha 90
_cell_angle_beta 113.7610(10)
_cell_angle_gamma 90
_cell_volume 2457.19(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 9262
_cell_measurement_theta_min 4.50
_cell_measurement_theta_max 74.56
_exptl_crystal_description BLOCK
_exptl_crystal_colour colourless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.305
_exptl_crystal_F_000 1040
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.300
_exptl_crystal_size_min 0.300
_exptl_absorpt_coefficient_mu 0.089
_shelx_estimated_absorpt_T_min 0.965
_shelx_estimated_absorpt_T_max 0.974
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.968
_exptl_absorpt_correction_T_max 0.9738
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type 'Bruker P4'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 42525
_diffrn_reflns_av_unetI/netI 0.0316
_diffrn_reflns_av_R_equivalents 0.0378
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_k_max 29
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 1.733
_diffrn_reflns_theta_max 26.380
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total 9891
_reflns_number_gt 9715
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.938
_reflns_Friedel_fraction_max 0.979
_reflns_Friedel_fraction_full 0.985
_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 ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_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^)+(0.0486P)^2^+0.5059P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 4583 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -1.5(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns 9891
_refine_ls_number_parameters 677
_refine_ls_number_restraints 9
_refine_ls_R_factor_all 0.0328
_refine_ls_R_factor_gt 0.0320
_refine_ls_wR_factor_ref 0.0846
_refine_ls_wR_factor_gt 0.0836
_refine_ls_goodness_of_fit_ref 1.043
_refine_ls_restrained_S_all 1.043
_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
C1 C 0.2123(2) 0.71127(9) -0.38098(19) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.153085 0.678409 -0.385354 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3175(2) 0.73483(9) -0.27103(18) 0.0171(4) Uani 1 1 d . . . . .
C3 C 0.3757(2) 0.78151(9) -0.30824(18) 0.0182(4) Uani 1 1 d . . . . .
C4 C 0.4954(2) 0.81998(9) -0.22497(18) 0.0198(4) Uani 1 1 d . . . . .
H4A H 0.468306 0.860067 -0.249835 0.024 Uiso 1 1 calc R U . . .
H4B H 0.592654 0.811563 -0.230818 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5112(2) 0.81104(8) -0.09143(18) 0.0174(4) Uani 1 1 d . . . . .
H5 H 0.418709 0.827521 -0.085939 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5176(2) 0.74704(8) -0.05482(18) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.3659(2) 0.71858(9) -0.13751(17) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.376948 0.676712 -0.129333 0.021 Uiso 1 1 calc R U . . .
H7B H 0.286813 0.730206 -0.109039 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6466(2) 0.71608(9) -0.07471(19) 0.0209(4) Uani 1 1 d . . . . .
H8A H 0.650679 0.676323 -0.048493 0.031 Uiso 1 1 calc R U . . .
H8B H 0.742979 0.734780 -0.025832 0.031 Uiso 1 1 calc R U . . .
H8C H 0.628248 0.717456 -0.162439 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5368(2) 0.74429(8) 0.08224(18) 0.0149(4) Uani 1 1 d . . . . .
H9 H 0.446387 0.763910 0.085036 0.018 Uiso 1 1 calc R U . . .
C10 C 0.6756(2) 0.77792(9) 0.17003(18) 0.0163(4) Uani 1 1 d . . . . .
H10 H 0.769048 0.761133 0.166848 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6628(3) 0.84036(9) 0.12956(19) 0.0233(4) Uani 1 1 d . . . . .
H11A H 0.573960 0.857879 0.137554 0.028 Uiso 1 1 calc R U . . .
H11B H 0.754101 0.861287 0.184377 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6462(3) 0.84548(9) -0.00385(19) 0.0227(4) Uani 1 1 d . . . . .
H12A H 0.739724 0.831660 -0.009984 0.027 Uiso 1 1 calc R U . . .
H12B H 0.632556 0.885999 -0.028932 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5341(2) 0.68302(8) 0.12907(18) 0.0169(4) Uani 1 1 d . . . . .
H13A H 0.437286 0.664718 0.076044 0.020 Uiso 1 1 calc R U . . .
H13B H 0.616902 0.660842 0.121284 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5517(2) 0.68102(9) 0.26480(18) 0.0168(4) Uani 1 1 d . . . . .
H14A H 0.463123 0.699313 0.271607 0.020 Uiso 1 1 calc R U . . .
H14B H 0.555587 0.640890 0.291464 0.020 Uiso 1 1 calc R U . . .
C15 C 0.6964(2) 0.71177(8) 0.34926(18) 0.0153(4) Uani 1 1 d . . . . .
C16 C 0.6853(2) 0.77349(8) 0.30148(18) 0.0168(4) Uani 1 1 d . . . . .
H16 H 0.589353 0.789773 0.300784 0.020 Uiso 1 1 calc R U . . .
C17 C 0.8365(2) 0.68091(9) 0.34873(18) 0.0176(4) Uani 1 1 d . . . . .
H17A H 0.834225 0.681667 0.265126 0.026 Uiso 1 1 calc R U . . .
H17B H 0.836463 0.641339 0.374916 0.026 Uiso 1 1 calc R U . . .
H17C H 0.928159 0.700058 0.405804 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8161(3) 0.80470(9) 0.40370(19) 0.0209(4) Uani 1 1 d . . . . .
H18A H 0.793972 0.845821 0.404088 0.025 Uiso 1 1 calc R U . . .
H18B H 0.911740 0.799950 0.392715 0.025 Uiso 1 1 calc R U . . .
C19 C 0.8257(2) 0.77574(9) 0.52397(19) 0.0209(4) Uani 1 1 d . . . . .
H19A H 0.791705 0.802318 0.572583 0.025 Uiso 1 1 calc R U . . .
H19B H 0.931187 0.764328 0.575058 0.025 Uiso 1 1 calc R U . . .
C20 C 0.7213(2) 0.72244(9) 0.48623(18) 0.0180(4) Uani 1 1 d . . . . .
C21 C 0.5756(3) 0.73265(11) 0.5043(2) 0.0268(5) Uani 1 1 d . . . . .
H21A H 0.600113 0.741219 0.591412 0.040 Uiso 1 1 calc R U . . .
H21B H 0.512243 0.698465 0.480135 0.040 Uiso 1 1 calc R U . . .
H21C H 0.520803 0.764818 0.453054 0.040 Uiso 1 1 calc R U . . .
C22 C 0.3241(2) 0.55234(9) 0.82806(19) 0.0205(4) Uani 1 1 d . . . . .
H22 H 0.268556 0.584565 0.834798 0.025 Uiso 1 1 calc R U . . .
C23 C 0.3155(2) 0.52924(9) 0.71576(18) 0.0189(4) Uani 1 1 d . . . . .
C24 C 0.4128(2) 0.48363(9) 0.74938(19) 0.0186(4) Uani 1 1 d . . . . .
C25 C 0.4486(2) 0.44650(9) 0.66266(18) 0.0198(4) Uani 1 1 d . . . . .
H25A H 0.447574 0.406064 0.685873 0.024 Uiso 1 1 calc R U . . .
H25B H 0.550742 0.455594 0.667124 0.024 Uiso 1 1 calc R U . . .
C26 C 0.3299(2) 0.45640(8) 0.53035(18) 0.0170(4) Uani 1 1 d . . . . .
H26 H 0.233438 0.438848 0.525543 0.020 Uiso 1 1 calc R U . . .
C27 C 0.2967(2) 0.52074(8) 0.49755(17) 0.0149(4) Uani 1 1 d . . . . .
C28 C 0.2272(2) 0.54639(9) 0.58368(19) 0.0189(4) Uani 1 1 d . . . . .
H28A H 0.226018 0.588413 0.577238 0.023 Uiso 1 1 calc R U . . .
H28B H 0.121376 0.533213 0.556719 0.023 Uiso 1 1 calc R U . . .
C29 C 0.4423(2) 0.55331(9) 0.51716(19) 0.0207(4) Uani 1 1 d . . . . .
H29A H 0.512790 0.550618 0.604103 0.031 Uiso 1 1 calc R U . . .
H29B H 0.418163 0.593380 0.494921 0.031 Uiso 1 1 calc R U . . .
H29C H 0.489028 0.536732 0.464982 0.031 Uiso 1 1 calc R U . . .
C30 C 0.1780(2) 0.52498(8) 0.36151(17) 0.0143(4) Uani 1 1 d . . . . .
H30 H 0.085316 0.505212 0.359288 0.017 Uiso 1 1 calc R U . . .
C31 C 0.2270(2) 0.49257(8) 0.27009(18) 0.0158(4) Uani 1 1 d . . . . .
H31 H 0.322473 0.509935 0.272249 0.019 Uiso 1 1 calc R U . . .
C32 C 0.2567(3) 0.42983(9) 0.30752(19) 0.0214(4) Uani 1 1 d . . . . .
H32A H 0.161779 0.411691 0.302053 0.026 Uiso 1 1 calc R U . . .
H32B H 0.291096 0.409814 0.249775 0.026 Uiso 1 1 calc R U . . .
C33 C 0.3769(3) 0.42426(9) 0.43911(19) 0.0220(4) Uani 1 1 d . . . . .
H33A H 0.474023 0.439651 0.442942 0.026 Uiso 1 1 calc R U . . .
H33B H 0.391950 0.383544 0.462442 0.026 Uiso 1 1 calc R U . . .
C34 C 0.1294(2) 0.58668(9) 0.31859(18) 0.0170(4) Uani 1 1 d . . . . .
H34A H 0.086102 0.604019 0.373447 0.020 Uiso 1 1 calc R U . . .
H34B H 0.219945 0.608995 0.327143 0.020 Uiso 1 1 calc R U . . .
C35 C 0.0120(2) 0.59073(9) 0.18358(18) 0.0169(4) Uani 1 1 d . . . . .
H35A H -0.083977 0.572897 0.176512 0.020 Uiso 1 1 calc R U . . .
H35B H -0.008487 0.631240 0.159620 0.020 Uiso 1 1 calc R U . . .
C36 C 0.0702(2) 0.56068(8) 0.09593(17) 0.0145(4) Uani 1 1 d . . . . .
C37 C 0.1050(2) 0.49837(8) 0.14016(18) 0.0159(4) Uani 1 1 d . . . . .
H37 H 0.010123 0.482235 0.141845 0.019 Uiso 1 1 calc R U . . .
C38 C 0.2111(2) 0.59138(9) 0.09628(18) 0.0179(4) Uani 1 1 d . . . . .
H38A H 0.292033 0.589862 0.179436 0.027 Uiso 1 1 calc R U . . .
H38B H 0.186007 0.631177 0.071802 0.027 Uiso 1 1 calc R U . . .
H38C H 0.244864 0.572636 0.037810 0.027 Uiso 1 1 calc R U . . .
C39 C 0.1305(2) 0.46832(9) 0.03531(19) 0.0201(4) Uani 1 1 d . . . . .
H39A H 0.107469 0.427194 0.033549 0.024 Uiso 1 1 calc R U . . .
H39B H 0.236216 0.473050 0.044136 0.024 Uiso 1 1 calc R U . . .
C40 C 0.0191(2) 0.49845(9) -0.08226(19) 0.0201(4) Uani 1 1 d . . . . .
H40A H -0.064911 0.472503 -0.129990 0.024 Uiso 1 1 calc R U . . .
H40B H 0.071611 0.509843 -0.135359 0.024 Uiso 1 1 calc R U . . .
C41 C -0.0430(2) 0.55184(9) -0.04052(18) 0.0174(4) Uani 1 1 d . . . . .
C42 C -0.2057(2) 0.54256(10) -0.0563(2) 0.0255(5) Uani 1 1 d . . . . .
H42A H -0.269130 0.534718 -0.143364 0.038 Uiso 1 1 calc R U . . .
H42B H -0.242687 0.576820 -0.030124 0.038 Uiso 1 1 calc R U . . .
H42C H -0.210167 0.510174 -0.005658 0.038 Uiso 1 1 calc R U . . .
C49 C 0.1738(2) 0.78439(9) 0.25065(19) 0.0191(4) Uani 1 1 d . . . . .
C50 C 0.1318(2) 0.79099(9) 0.11635(18) 0.0164(4) Uani 1 1 d . . . . .
C51 C 0.0549(2) 0.74734(8) 0.03404(19) 0.0167(4) Uani 1 1 d . . . . .
H51 H 0.030918 0.713095 0.064935 0.020 Uiso 1 1 calc R U . . .
C52 C 0.0136(2) 0.75371(9) -0.09154(19) 0.0178(4) Uani 1 1 d . . . . .
C53 C 0.0442(2) 0.80512(9) -0.13680(19) 0.0205(4) Uani 1 1 d . . . . .
H53 H 0.013632 0.810185 -0.223222 0.025 Uiso 1 1 calc R U . . .
C54 C 0.1185(2) 0.84837(9) -0.0568(2) 0.0208(4) Uani 1 1 d . . . . .
H54 H 0.137153 0.883269 -0.088688 0.025 Uiso 1 1 calc R U . . .
C55 C 0.1667(2) 0.84159(9) 0.07082(19) 0.0186(4) Uani 1 1 d . . . . .
C56 C 0.6558(2) 0.48572(9) 0.19880(19) 0.0182(4) Uani 1 1 d . . . . .
C57 C 0.7430(2) 0.48068(9) 0.33355(18) 0.0166(4) Uani 1 1 d . . . . .
C58 C 0.8232(2) 0.43042(9) 0.38316(19) 0.0188(4) Uani 1 1 d . . . . .
C59 C 0.8955(3) 0.42455(9) 0.5110(2) 0.0227(4) Uani 1 1 d . . . . .
H59 H 0.945122 0.389876 0.545493 0.027 Uiso 1 1 calc R U . . .
C60 C 0.8954(3) 0.46877(10) 0.58807(19) 0.0231(4) Uani 1 1 d . . . . .
H60 H 0.945497 0.464240 0.675063 0.028 Uiso 1 1 calc R U . . .
C61 C 0.8227(2) 0.52007(9) 0.53948(19) 0.0191(4) Uani 1 1 d . . . . .
C62 C 0.7443(2) 0.52519(9) 0.41314(19) 0.0173(4) Uani 1 1 d . . . . .
H62 H 0.690502 0.559278 0.379674 0.021 Uiso 1 1 calc R U . . .
H4 H 0.545(4) 0.4585(13) 0.928(3) 0.028(7) Uiso 1 1 d . . . . .
H2 H 0.322(3) 0.8060(12) -0.484(3) 0.020(6) Uiso 1 1 d . . . . .
N1 N 0.2065(2) 0.74128(8) -0.47897(16) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.3074(2) 0.78415(8) -0.43158(16) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.4206(2) 0.52300(8) 0.92382(16) 0.0212(4) Uani 1 1 d . . . . .
N4 N 0.4732(2) 0.48061(8) 0.87386(16) 0.0198(4) Uani 1 1 d . . . . .
O1 O 0.79756(19) 0.67443(7) 0.56326(13) 0.0230(3) Uani 1 1 d D . . . .
H1A H 0.842(4) 0.6889(14) 0.6344(18) 0.046(10) Uiso 1 1 d D . . . .
O2 O -0.04212(19) 0.60039(6) -0.11618(13) 0.0225(3) Uani 1 1 d D . . . .
H2A H -0.073(3) 0.5881(13) -0.1884(16) 0.030(7) Uiso 1 1 d D . . . .
O8 O 0.57354(18) 0.53140(7) 0.16145(13) 0.0232(3) Uani 1 1 d D . . . .
H8 H 0.516(4) 0.5308(17) 0.0835(15) 0.049(10) Uiso 1 1 d D . . . .
O7 O 0.65977(19) 0.44787(7) 0.12642(14) 0.0237(3) Uani 1 1 d . . . . .
O9 O 0.83317(19) 0.38634(7) 0.31238(14) 0.0249(3) Uani 1 1 d D . . . .
H9A H 0.777(3) 0.3955(14) 0.2382(16) 0.041(9) Uiso 1 1 d D . . . .
O10 O 0.83102(19) 0.56285(7) 0.62063(14) 0.0251(3) Uani 1 1 d D . . . .
H10A H 0.807(3) 0.5945(8) 0.582(3) 0.032(8) Uiso 1 1 d D . . . .
O3 O 0.24775(19) 0.82166(7) 0.32541(14) 0.0253(3) Uani 1 1 d . . . . .
O4 O 0.12756(19) 0.73778(7) 0.28419(13) 0.0237(3) Uani 1 1 d D . . . .
H4C H 0.152(4) 0.7367(18) 0.3626(14) 0.055(11) Uiso 1 1 d D . . . .
O6 O -0.0580(2) 0.71159(7) -0.17503(14) 0.0243(3) Uani 1 1 d D . . . .
H6 H -0.041(4) 0.6799(9) -0.138(3) 0.047(10) Uiso 1 1 d D . . . .
O5 O 0.24490(19) 0.88510(7) 0.14478(15) 0.0260(3) Uani 1 1 d D . . . .
H5A H 0.256(4) 0.8738(15) 0.2166(18) 0.047(10) Uiso 1 1 d D . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0198(9) 0.0214(10) 0.0155(10) -0.0010(8) 0.0037(8) -0.0007(8)
C2 0.0172(9) 0.0184(9) 0.0121(9) -0.0006(7) 0.0022(7) 0.0005(7)
C3 0.0199(9) 0.0210(10) 0.0130(9) 0.0003(8) 0.0058(8) 0.0005(8)
C4 0.0222(10) 0.0225(10) 0.0131(9) 0.0018(8) 0.0054(8) -0.0041(8)
C5 0.0220(10) 0.0160(9) 0.0125(9) 0.0000(7) 0.0053(8) -0.0028(7)
C6 0.0162(9) 0.0155(9) 0.0104(9) -0.0009(7) 0.0033(7) -0.0006(7)
C7 0.0184(9) 0.0190(9) 0.0099(9) -0.0008(7) 0.0013(7) -0.0040(7)
C8 0.0199(9) 0.0254(10) 0.0174(10) -0.0004(8) 0.0076(8) 0.0027(8)
C9 0.0157(9) 0.0164(9) 0.0097(9) -0.0006(7) 0.0021(7) -0.0021(7)
C10 0.0179(9) 0.0161(9) 0.0115(9) -0.0009(7) 0.0023(7) -0.0026(7)
C11 0.0329(11) 0.0163(10) 0.0146(10) -0.0021(8) 0.0033(8) -0.0075(8)
C12 0.0294(11) 0.0189(10) 0.0160(10) 0.0008(8) 0.0053(8) -0.0085(8)
C13 0.0188(9) 0.0157(9) 0.0116(9) -0.0003(7) 0.0013(7) -0.0032(7)
C14 0.0164(9) 0.0195(9) 0.0117(9) 0.0008(7) 0.0028(7) -0.0029(7)
C15 0.0165(9) 0.0164(9) 0.0107(9) -0.0002(7) 0.0030(7) 0.0002(7)
C16 0.0190(9) 0.0158(9) 0.0127(9) -0.0019(7) 0.0033(7) 0.0004(7)
C17 0.0184(9) 0.0185(9) 0.0141(9) -0.0013(7) 0.0045(7) 0.0013(7)
C18 0.0276(11) 0.0172(10) 0.0128(9) -0.0018(7) 0.0029(8) -0.0021(8)
C19 0.0259(10) 0.0205(10) 0.0115(9) -0.0032(8) 0.0027(8) 0.0028(8)
C20 0.0224(10) 0.0184(10) 0.0112(9) 0.0000(7) 0.0047(7) 0.0040(7)
C21 0.0290(11) 0.0363(12) 0.0175(10) 0.0005(9) 0.0121(9) 0.0052(9)
C22 0.0248(10) 0.0222(10) 0.0142(10) -0.0008(8) 0.0073(8) -0.0013(8)
C23 0.0221(9) 0.0217(10) 0.0117(9) 0.0002(8) 0.0054(7) -0.0011(8)
C24 0.0201(9) 0.0198(9) 0.0133(9) 0.0010(8) 0.0041(8) -0.0023(7)
C25 0.0228(10) 0.0205(9) 0.0123(9) 0.0032(7) 0.0031(8) 0.0030(8)
C26 0.0200(9) 0.0165(9) 0.0118(9) 0.0019(7) 0.0037(7) 0.0025(7)
C27 0.0177(9) 0.0153(9) 0.0095(9) 0.0005(7) 0.0032(7) 0.0008(7)
C28 0.0233(10) 0.0205(10) 0.0115(9) 0.0011(7) 0.0056(8) 0.0041(8)
C29 0.0203(10) 0.0217(10) 0.0170(10) 0.0015(8) 0.0044(8) -0.0034(8)
C30 0.0172(9) 0.0149(9) 0.0102(8) 0.0008(7) 0.0049(7) 0.0015(7)
C31 0.0183(9) 0.0157(9) 0.0109(9) -0.0005(7) 0.0035(7) 0.0028(7)
C32 0.0309(11) 0.0164(9) 0.0133(9) -0.0011(7) 0.0051(8) 0.0051(8)
C33 0.0289(11) 0.0180(10) 0.0159(10) 0.0014(8) 0.0056(8) 0.0075(8)
C34 0.0228(9) 0.0166(9) 0.0107(9) 0.0002(7) 0.0057(7) 0.0032(7)
C35 0.0189(9) 0.0179(9) 0.0136(9) 0.0025(7) 0.0063(7) 0.0046(7)
C36 0.0151(9) 0.0167(9) 0.0092(9) -0.0004(7) 0.0025(7) -0.0004(7)
C37 0.0173(9) 0.0161(9) 0.0126(9) -0.0003(7) 0.0042(7) 0.0001(7)
C38 0.0191(9) 0.0189(9) 0.0144(9) -0.0005(7) 0.0054(7) -0.0020(7)
C39 0.0283(10) 0.0177(9) 0.0120(9) -0.0023(7) 0.0059(8) 0.0003(8)
C40 0.0261(10) 0.0186(10) 0.0124(9) -0.0029(7) 0.0045(8) -0.0034(8)
C41 0.0218(10) 0.0166(9) 0.0108(9) 0.0011(7) 0.0033(7) -0.0038(7)
C42 0.0198(10) 0.0321(12) 0.0177(10) 0.0014(9) 0.0005(8) -0.0020(8)
C49 0.0206(9) 0.0207(10) 0.0133(9) -0.0007(8) 0.0039(7) 0.0006(8)
C50 0.0155(8) 0.0196(10) 0.0114(9) 0.0002(7) 0.0026(7) 0.0018(7)
C51 0.0182(9) 0.0162(9) 0.0150(10) 0.0017(7) 0.0059(7) 0.0005(7)
C52 0.0196(9) 0.0183(10) 0.0134(9) -0.0012(7) 0.0045(7) -0.0003(7)
C53 0.0259(10) 0.0224(10) 0.0117(9) 0.0032(8) 0.0060(8) 0.0020(8)
C54 0.0269(10) 0.0168(9) 0.0186(10) 0.0020(8) 0.0091(8) -0.0016(8)
C55 0.0195(9) 0.0186(10) 0.0152(9) -0.0022(8) 0.0043(7) 0.0004(7)
C56 0.0209(9) 0.0195(10) 0.0134(10) 0.0002(7) 0.0060(8) -0.0012(7)
C57 0.0179(9) 0.0185(9) 0.0131(9) -0.0010(7) 0.0060(7) -0.0020(7)
C58 0.0214(9) 0.0181(9) 0.0167(10) -0.0025(8) 0.0076(8) -0.0002(8)
C59 0.0262(10) 0.0199(10) 0.0179(10) 0.0028(8) 0.0044(8) 0.0059(8)
C60 0.0281(10) 0.0242(11) 0.0107(9) 0.0006(8) 0.0012(8) 0.0031(8)
C61 0.0224(10) 0.0195(10) 0.0131(9) -0.0018(8) 0.0049(7) -0.0006(8)
C62 0.0196(9) 0.0163(9) 0.0148(9) 0.0002(7) 0.0059(7) 0.0008(7)
N1 0.0209(8) 0.0242(9) 0.0123(8) -0.0010(7) 0.0028(7) -0.0004(7)
N2 0.0209(8) 0.0226(9) 0.0120(8) 0.0004(7) 0.0050(7) -0.0010(7)
N3 0.0268(9) 0.0230(9) 0.0121(8) -0.0012(7) 0.0059(7) -0.0042(7)
N4 0.0222(9) 0.0209(9) 0.0116(8) 0.0013(7) 0.0020(7) -0.0011(7)
O1 0.0336(9) 0.0199(7) 0.0092(7) 0.0000(6) 0.0019(6) 0.0040(6)
O2 0.0356(9) 0.0178(7) 0.0086(7) 0.0021(6) 0.0030(6) -0.0037(6)
O8 0.0297(8) 0.0229(8) 0.0105(7) -0.0006(6) 0.0014(6) 0.0061(6)
O7 0.0337(8) 0.0217(7) 0.0135(7) -0.0032(6) 0.0072(6) 0.0033(6)
O9 0.0356(9) 0.0198(7) 0.0175(7) -0.0028(6) 0.0089(7) 0.0060(6)
O10 0.0377(9) 0.0190(8) 0.0111(7) -0.0025(6) 0.0020(6) 0.0040(6)
O3 0.0342(9) 0.0225(8) 0.0121(7) -0.0021(6) 0.0021(6) -0.0052(6)
O4 0.0335(8) 0.0251(8) 0.0098(7) 0.0000(6) 0.0060(6) -0.0068(7)
O6 0.0395(9) 0.0184(7) 0.0103(7) -0.0003(6) 0.0051(6) -0.0057(6)
O5 0.0351(9) 0.0196(7) 0.0162(7) -0.0013(6) 0.0031(6) -0.0082(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
C1 N1 1.338(3) . ?
C1 C2 1.402(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 C7 1.504(3) . ?
C3 N2 1.338(3) . ?
C3 C4 1.485(3) . ?
C4 C5 1.538(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.530(3) . ?
C5 C6 1.559(3) . ?
C5 H5 1.0000 . ?
C6 C8 1.541(3) . ?
C6 C7 1.548(3) . ?
C6 C9 1.557(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.542(2) . ?
C9 C13 1.547(3) . ?
C9 H9 1.0000 . ?
C10 C16 1.523(3) . ?
C10 C11 1.533(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.545(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.533(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.538(3) . ?
C15 C16 1.544(3) . ?
C15 C20 1.559(3) . ?
C16 C18 1.538(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.545(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.556(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O1 1.450(2) . ?
C20 C21 1.527(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N3 1.333(3) . ?
C22 C23 1.406(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 C28 1.502(3) . ?
C24 N4 1.349(3) . ?
C24 C25 1.490(3) . ?
C25 C26 1.540(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C33 1.528(3) . ?
C26 C27 1.562(3) . ?
C26 H26 1.0000 . ?
C27 C29 1.535(3) . ?
C27 C28 1.550(3) . ?
C27 C30 1.558(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.544(3) . ?
C30 C34 1.545(3) . ?
C30 H30 1.0000 . ?
C31 C37 1.519(3) . ?
C31 C32 1.533(3) . ?
C31 H31 1.0000 . ?
C32 C33 1.526(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.544(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.536(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C38 1.539(3) . ?
C36 C37 1.545(3) . ?
C36 C41 1.556(3) . ?
C37 C39 1.531(3) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.545(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.554(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 O2 1.452(2) . ?
C41 C42 1.523(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C49 O3 1.245(3) . ?
C49 O4 1.303(3) . ?
C49 C50 1.480(3) . ?
C50 C55 1.401(3) . ?
C50 C51 1.403(3) . ?
C51 C52 1.382(3) . ?
C51 H51 0.9500 . ?
C52 O6 1.372(3) . ?
C52 C53 1.400(3) . ?
C53 C54 1.377(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.397(3) . ?
C54 H54 0.9500 . ?
C55 O5 1.360(3) . ?
C56 O7 1.246(3) . ?
C56 O8 1.302(3) . ?
C56 C57 1.477(3) . ?
C57 C62 1.404(3) . ?
C57 C58 1.404(3) . ?
C58 O9 1.359(3) . ?
C58 C59 1.394(3) . ?
C59 C60 1.382(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.397(3) . ?
C60 H60 0.9500 . ?
C61 O10 1.369(3) . ?
C61 C62 1.381(3) . ?
C62 H62 0.9500 . ?
N1 N2 1.356(3) . ?
N2 H2 0.86(3) . ?
N3 N4 1.357(3) . ?
N4 H4 0.90(3) . ?
O1 H1A 0.846(14) . ?
O2 H2A 0.834(14) . ?
O8 H8 0.863(14) . ?
O9 H9A 0.853(14) . ?
O10 H10A 0.854(14) . ?
O4 H4C 0.861(14) . ?
O6 H6 0.848(14) . ?
O5 H5A 0.853(14) . ?
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
N1 C1 C2 110.91(19) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C3 C2 C1 104.71(18) . . ?
C3 C2 C7 122.73(18) . . ?
C1 C2 C7 132.55(19) . . ?
N2 C3 C2 107.36(18) . . ?
N2 C3 C4 127.20(19) . . ?
C2 C3 C4 125.42(18) . . ?
C3 C4 C5 109.04(17) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C12 C5 C4 109.12(16) . . ?
C12 C5 C6 113.24(17) . . ?
C4 C5 C6 113.15(16) . . ?
C12 C5 H5 107.0 . . ?
C4 C5 H5 107.0 . . ?
C6 C5 H5 107.0 . . ?
C8 C6 C7 108.54(16) . . ?
C8 C6 C9 112.02(16) . . ?
C7 C6 C9 108.97(15) . . ?
C8 C6 C5 110.90(17) . . ?
C7 C6 C5 108.65(16) . . ?
C9 C6 C5 107.69(15) . . ?
C2 C7 C6 111.63(17) . . ?
C2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C13 111.81(15) . . ?
C10 C9 C6 112.71(15) . . ?
C13 C9 C6 113.53(15) . . ?
C10 C9 H9 106.0 . . ?
C13 C9 H9 106.0 . . ?
C6 C9 H9 106.0 . . ?
C16 C10 C11 110.37(17) . . ?
C16 C10 C9 109.35(16) . . ?
C11 C10 C9 109.95(16) . . ?
C16 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C12 C11 C10 111.11(17) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C5 111.34(17) . . ?
C11 C12 H12A 109.4 . . ?
C5 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C5 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C9 112.93(16) . . ?
C14 C13 H13A 109.0 . . ?
C9 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C9 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 110.65(16) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C17 110.39(16) . . ?
C14 C15 C16 107.08(15) . . ?
C17 C15 C16 111.89(16) . . ?
C14 C15 C20 118.12(16) . . ?
C17 C15 C20 108.20(15) . . ?
C16 C15 C20 100.84(15) . . ?
C10 C16 C18 117.57(17) . . ?
C10 C16 C15 113.84(16) . . ?
C18 C16 C15 104.25(15) . . ?
C10 C16 H16 106.8 . . ?
C18 C16 H16 106.8 . . ?
C15 C16 H16 106.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 103.82(17) . . ?
C16 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C16 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C18 C19 C20 107.38(16) . . ?
C18 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
C18 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
O1 C20 C21 107.33(17) . . ?
O1 C20 C19 109.84(17) . . ?
C21 C20 C19 111.17(18) . . ?
O1 C20 C15 110.74(15) . . ?
C21 C20 C15 113.95(17) . . ?
C19 C20 C15 103.79(16) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 110.97(19) . . ?
N3 C22 H22 124.5 . . ?
C23 C22 H22 124.5 . . ?
C24 C23 C22 104.75(18) . . ?
C24 C23 C28 123.08(19) . . ?
C22 C23 C28 132.2(2) . . ?
N4 C24 C23 107.54(18) . . ?
N4 C24 C25 127.01(19) . . ?
C23 C24 C25 125.40(19) . . ?
C24 C25 C26 109.04(17) . . ?
C24 C25 H25A 109.9 . . ?
C26 C25 H25A 109.9 . . ?
C24 C25 H25B 109.9 . . ?
C26 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C33 C26 C25 109.34(16) . . ?
C33 C26 C27 113.13(16) . . ?
C25 C26 C27 113.15(16) . . ?
C33 C26 H26 106.9 . . ?
C25 C26 H26 106.9 . . ?
C27 C26 H26 106.9 . . ?
C29 C27 C28 108.70(16) . . ?
C29 C27 C30 111.89(16) . . ?
C28 C27 C30 108.67(15) . . ?
C29 C27 C26 111.14(16) . . ?
C28 C27 C26 108.26(16) . . ?
C30 C27 C26 108.10(15) . . ?
C23 C28 C27 111.33(17) . . ?
C23 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
C23 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C34 111.79(15) . . ?
C31 C30 C27 112.69(15) . . ?
C34 C30 C27 113.53(16) . . ?
C31 C30 H30 106.0 . . ?
C34 C30 H30 106.0 . . ?
C27 C30 H30 106.0 . . ?
C37 C31 C32 110.92(16) . . ?
C37 C31 C30 109.41(16) . . ?
C32 C31 C30 110.31(16) . . ?
C37 C31 H31 108.7 . . ?
C32 C31 H31 108.7 . . ?
C30 C31 H31 108.7 . . ?
C33 C32 C31 110.73(17) . . ?
C33 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C32 C33 C26 110.94(17) . . ?
C32 C33 H33A 109.5 . . ?
C26 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C26 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C30 113.39(16) . . ?
C35 C34 H34A 108.9 . . ?
C30 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C30 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 110.67(15) . . ?
C36 C35 H35A 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C35 C36 C38 110.30(16) . . ?
C35 C36 C37 107.21(15) . . ?
C38 C36 C37 111.81(16) . . ?
C35 C36 C41 117.73(16) . . ?
C38 C36 C41 108.48(15) . . ?
C37 C36 C41 100.99(15) . . ?
C31 C37 C39 117.74(17) . . ?
C31 C37 C36 113.67(16) . . ?
C39 C37 C36 104.29(15) . . ?
C31 C37 H37 106.8 . . ?
C39 C37 H37 106.8 . . ?
C36 C37 H37 106.8 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 103.67(16) . . ?
C37 C39 H39A 111.0 . . ?
C40 C39 H39A 111.0 . . ?
C37 C39 H39B 111.0 . . ?
C40 C39 H39B 111.0 . . ?
H39A C39 H39B 109.0 . . ?
C39 C40 C41 107.60(16) . . ?
C39 C40 H40A 110.2 . . ?
C41 C40 H40A 110.2 . . ?
C39 C40 H40B 110.2 . . ?
C41 C40 H40B 110.2 . . ?
H40A C40 H40B 108.5 . . ?
O2 C41 C42 107.39(17) . . ?
O2 C41 C40 109.86(17) . . ?
C42 C41 C40 110.93(17) . . ?
O2 C41 C36 110.97(16) . . ?
C42 C41 C36 113.97(17) . . ?
C40 C41 C36 103.71(16) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O3 C49 O4 122.96(19) . . ?
O3 C49 C50 121.25(19) . . ?
O4 C49 C50 115.80(18) . . ?
C55 C50 C51 119.73(18) . . ?
C55 C50 C49 119.79(18) . . ?
C51 C50 C49 120.47(18) . . ?
C52 C51 C50 120.61(18) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
O6 C52 C51 122.60(18) . . ?
O6 C52 C53 118.04(18) . . ?
C51 C52 C53 119.36(19) . . ?
C54 C53 C52 120.38(19) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C53 C54 C55 120.9(2) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
O5 C55 C54 117.78(19) . . ?
O5 C55 C50 123.24(18) . . ?
C54 C55 C50 118.98(19) . . ?
O7 C56 O8 122.61(19) . . ?
O7 C56 C57 121.46(19) . . ?
O8 C56 C57 115.92(18) . . ?
C62 C57 C58 119.48(18) . . ?
C62 C57 C56 120.70(18) . . ?
C58 C57 C56 119.81(18) . . ?
O9 C58 C59 117.64(19) . . ?
O9 C58 C57 123.20(18) . . ?
C59 C58 C57 119.16(19) . . ?
C60 C59 C58 120.5(2) . . ?
C60 C59 H59 119.7 . . ?
C58 C59 H59 119.7 . . ?
C59 C60 C61 120.75(19) . . ?
C59 C60 H60 119.6 . . ?
C61 C60 H60 119.6 . . ?
O10 C61 C62 123.08(19) . . ?
O10 C61 C60 117.86(18) . . ?
C62 C61 C60 119.06(19) . . ?
C61 C62 C57 120.87(19) . . ?
C61 C62 H62 119.6 . . ?
C57 C62 H62 119.6 . . ?
C1 N1 N2 105.15(17) . . ?
C3 N2 N1 111.88(17) . . ?
C3 N2 H2 131.3(19) . . ?
N1 N2 H2 116.5(19) . . ?
C22 N3 N4 105.44(17) . . ?
C24 N4 N3 111.30(18) . . ?
C24 N4 H4 132(2) . . ?
N3 N4 H4 116(2) . . ?
C20 O1 H1A 104(2) . . ?
C41 O2 H2A 106(2) . . ?
C56 O8 H8 113(3) . . ?
C58 O9 H9A 105(2) . . ?
C61 O10 H10A 110(2) . . ?
C49 O4 H4C 112(3) . . ?
C52 O6 H6 109(3) . . ?
C55 O5 H5A 103(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
_geom_hbond_publ_flag
O9 H9A O7 0.853(14) 1.83(2) 2.601(2) 150(3) . yes
O10 H10A O1 0.854(14) 1.889(18) 2.695(2) 157(3) . yes
O6 H6 O2 0.848(14) 1.885(19) 2.692(2) 158(4) . yes
O5 H5A O3 0.853(14) 1.80(2) 2.596(2) 154(4) . yes
O4 H4C N1 0.861(14) 1.732(15) 2.590(2) 174(4) 1_556 yes
O4 H4C N2 0.861(14) 2.55(3) 3.286(2) 145(4) 1_556 yes
N4 H4 O7 0.90(3) 2.17(3) 2.902(2) 138(3) 1_556 yes
N2 H2 O3 0.86(3) 2.11(3) 2.834(2) 142(2) 1_554 yes
O1 H1A O6 0.846(14) 2.131(16) 2.968(2) 170(3) 1_656 yes
O2 H2A O10 0.834(14) 2.150(14) 2.982(2) 175(3) 1_454 yes
O8 H8 N3 0.863(14) 1.746(15) 2.602(2) 172(4) 1_554 yes
O8 H8 N4 0.863(14) 2.62(3) 3.357(2) 144(3) 1_554 yes
_refine_diff_density_max 0.258
_refine_diff_density_min -0.179
_refine_diff_density_rms 0.037
_shelx_res_file
;
TITL T in P2(1)
T.res
created by SHELXL-2017/1 at 11:20:41 on 26-Aug-2018
CELL 0.71073 9.6635 23.495 11.8249 90 113.761 90
ZERR 4 0.0003 0.0006 0.0003 0 0.001 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 112 152 8 20
dfix 0.85 0.01 O1 H1A O2 H2A O4 H4C O5 H5A O6 H6 O8 H8 O9 H9A O10 H10A
L.S. 40
PLAN 10
SIZE 0.3 0.3 0.4
TEMP -153.14
HTAB 2
HTAB O9 O7
HTAB O10 O1
HTAB O6 O2
HTAB O5 O3
HTAB O4 N1_$1
HTAB O4 N2_$1
HTAB N4 O7_$1
HTAB N2 O3_$2
HTAB O1 O6_$3
HTAB O2 O10_$4
HTAB O8 N3_$2
HTAB O8 N4_$2
EQIV $1 x, y, z+1
EQIV $2 x, y, z-1
EQIV $3 x+1, y, z+1
EQIV $4 x-1, y, z-1
FREE C3 H30
FREE N1 H30
BOND $H
fmap 2
acta
REM
REM
REM
WGHT 0.048600 0.505900
FVAR 0.26973
C1 1 0.212310 0.711270 -0.380985 11.00000 0.01977 0.02137 =
0.01546 -0.00096 0.00371 -0.00070
AFIX 43
H1 2 0.153085 0.678409 -0.385354 11.00000 -1.20000
AFIX 0
C2 1 0.317468 0.734827 -0.271035 11.00000 0.01723 0.01837 =
0.01212 -0.00060 0.00223 0.00055
C3 1 0.375661 0.781511 -0.308244 11.00000 0.01989 0.02102 =
0.01296 0.00029 0.00576 0.00049
C4 1 0.495370 0.819977 -0.224966 11.00000 0.02224 0.02254 =
0.01306 0.00176 0.00542 -0.00408
AFIX 23
H4A 2 0.468306 0.860067 -0.249835 11.00000 -1.20000
H4B 2 0.592654 0.811563 -0.230818 11.00000 -1.20000
AFIX 0
C5 1 0.511209 0.811036 -0.091429 11.00000 0.02202 0.01597 =
0.01251 -0.00001 0.00528 -0.00279
AFIX 13
H5 2 0.418709 0.827521 -0.085939 11.00000 -1.20000
AFIX 0
C6 1 0.517594 0.747040 -0.054821 11.00000 0.01624 0.01550 =
0.01036 -0.00088 0.00332 -0.00058
C7 1 0.365944 0.718581 -0.137507 11.00000 0.01837 0.01896 =
0.00992 -0.00082 0.00130 -0.00395
AFIX 23
H7A 2 0.376948 0.676712 -0.129333 11.00000 -1.20000
H7B 2 0.286813 0.730206 -0.109039 11.00000 -1.20000
AFIX 0
C8 1 0.646620 0.716082 -0.074706 11.00000 0.01993 0.02544 =
0.01737 -0.00038 0.00756 0.00272
AFIX 137
H8A 2 0.650679 0.676323 -0.048493 11.00000 -1.50000
H8B 2 0.742979 0.734780 -0.025832 11.00000 -1.50000
H8C 2 0.628248 0.717456 -0.162439 11.00000 -1.50000
AFIX 0
C9 1 0.536792 0.744293 0.082243 11.00000 0.01567 0.01636 =
0.00974 -0.00059 0.00208 -0.00206
AFIX 13
H9 2 0.446387 0.763910 0.085036 11.00000 -1.20000
AFIX 0
C10 1 0.675588 0.777916 0.170031 11.00000 0.01791 0.01607 =
0.01149 -0.00087 0.00232 -0.00258
AFIX 13
H10 2 0.769048 0.761133 0.166848 11.00000 -1.20000
AFIX 0
C11 1 0.662756 0.840358 0.129556 11.00000 0.03288 0.01628 =
0.01457 -0.00213 0.00329 -0.00753
AFIX 23
H11A 2 0.573960 0.857879 0.137554 11.00000 -1.20000
H11B 2 0.754101 0.861287 0.184377 11.00000 -1.20000
AFIX 0
C12 1 0.646209 0.845480 -0.003854 11.00000 0.02936 0.01890 =
0.01599 0.00083 0.00528 -0.00855
AFIX 23
H12A 2 0.739724 0.831660 -0.009984 11.00000 -1.20000
H12B 2 0.632556 0.885999 -0.028932 11.00000 -1.20000
AFIX 0
C13 1 0.534065 0.683017 0.129069 11.00000 0.01881 0.01567 =
0.01156 -0.00034 0.00128 -0.00319
AFIX 23
H13A 2 0.437286 0.664718 0.076044 11.00000 -1.20000
H13B 2 0.616902 0.660842 0.121284 11.00000 -1.20000
AFIX 0
C14 1 0.551736 0.681015 0.264801 11.00000 0.01637 0.01948 =
0.01170 0.00079 0.00280 -0.00285
AFIX 23
H14A 2 0.463123 0.699313 0.271607 11.00000 -1.20000
H14B 2 0.555587 0.640890 0.291464 11.00000 -1.20000
AFIX 0
C15 1 0.696419 0.711773 0.349262 11.00000 0.01649 0.01637 =
0.01065 -0.00019 0.00300 0.00017
C16 1 0.685306 0.773490 0.301485 11.00000 0.01898 0.01576 =
0.01270 -0.00190 0.00333 0.00035
AFIX 13
H16 2 0.589353 0.789773 0.300784 11.00000 -1.20000
AFIX 0
C17 1 0.836527 0.680909 0.348728 11.00000 0.01840 0.01846 =
0.01405 -0.00126 0.00447 0.00135
AFIX 137
H17A 2 0.834225 0.681667 0.265126 11.00000 -1.50000
H17B 2 0.836463 0.641339 0.374916 11.00000 -1.50000
H17C 2 0.928159 0.700058 0.405804 11.00000 -1.50000
AFIX 0
C18 1 0.816106 0.804697 0.403699 11.00000 0.02761 0.01718 =
0.01278 -0.00183 0.00294 -0.00213
AFIX 23
H18A 2 0.793972 0.845821 0.404088 11.00000 -1.20000
H18B 2 0.911740 0.799950 0.392715 11.00000 -1.20000
AFIX 0
C19 1 0.825679 0.775745 0.523970 11.00000 0.02591 0.02049 =
0.01154 -0.00322 0.00268 0.00283
AFIX 23
H19A 2 0.791705 0.802318 0.572583 11.00000 -1.20000
H19B 2 0.931187 0.764328 0.575058 11.00000 -1.20000
AFIX 0
C20 1 0.721342 0.722441 0.486233 11.00000 0.02239 0.01839 =
0.01122 0.00003 0.00472 0.00403
C21 1 0.575579 0.732650 0.504328 11.00000 0.02900 0.03633 =
0.01753 0.00054 0.01205 0.00521
AFIX 137
H21A 2 0.600113 0.741219 0.591412 11.00000 -1.50000
H21B 2 0.512243 0.698465 0.480135 11.00000 -1.50000
H21C 2 0.520803 0.764818 0.453054 11.00000 -1.50000
AFIX 0
C22 1 0.324123 0.552337 0.828062 11.00000 0.02477 0.02217 =
0.01415 -0.00078 0.00729 -0.00132
AFIX 43
H22 2 0.268556 0.584565 0.834798 11.00000 -1.20000
AFIX 0
C23 1 0.315524 0.529243 0.715762 11.00000 0.02213 0.02171 =
0.01165 0.00017 0.00539 -0.00106
C24 1 0.412808 0.483631 0.749376 11.00000 0.02014 0.01979 =
0.01329 0.00105 0.00415 -0.00235
C25 1 0.448636 0.446495 0.662662 11.00000 0.02275 0.02046 =
0.01230 0.00316 0.00309 0.00297
AFIX 23
H25A 2 0.447574 0.406064 0.685873 11.00000 -1.20000
H25B 2 0.550742 0.455594 0.667124 11.00000 -1.20000
AFIX 0
C26 1 0.329931 0.456399 0.530355 11.00000 0.02000 0.01646 =
0.01182 0.00190 0.00370 0.00254
AFIX 13
H26 2 0.233438 0.438848 0.525543 11.00000 -1.20000
AFIX 0
C27 1 0.296691 0.520743 0.497550 11.00000 0.01773 0.01534 =
0.00955 0.00050 0.00322 0.00076
C28 1 0.227175 0.546389 0.583680 11.00000 0.02325 0.02046 =
0.01152 0.00106 0.00558 0.00409
AFIX 23
H28A 2 0.226018 0.588413 0.577238 11.00000 -1.20000
H28B 2 0.121376 0.533213 0.556719 11.00000 -1.20000
AFIX 0
C29 1 0.442338 0.553314 0.517163 11.00000 0.02033 0.02170 =
0.01695 0.00148 0.00441 -0.00343
AFIX 137
H29A 2 0.512790 0.550618 0.604103 11.00000 -1.50000
H29B 2 0.418163 0.593380 0.494921 11.00000 -1.50000
H29C 2 0.489028 0.536732 0.464982 11.00000 -1.50000
AFIX 0
C30 1 0.178014 0.524984 0.361507 11.00000 0.01723 0.01489 =
0.01017 0.00076 0.00494 0.00147
AFIX 13
H30 2 0.085316 0.505212 0.359288 11.00000 -1.20000
AFIX 0
C31 1 0.226959 0.492574 0.270093 11.00000 0.01833 0.01575 =
0.01089 -0.00052 0.00350 0.00279
AFIX 13
H31 2 0.322473 0.509935 0.272249 11.00000 -1.20000
AFIX 0
C32 1 0.256745 0.429825 0.307517 11.00000 0.03094 0.01637 =
0.01328 -0.00112 0.00507 0.00514
AFIX 23
H32A 2 0.161779 0.411691 0.302053 11.00000 -1.20000
H32B 2 0.291096 0.409814 0.249775 11.00000 -1.20000
AFIX 0
C33 1 0.376860 0.424260 0.439106 11.00000 0.02890 0.01802 =
0.01593 0.00140 0.00564 0.00752
AFIX 23
H33A 2 0.474023 0.439651 0.442942 11.00000 -1.20000
H33B 2 0.391950 0.383544 0.462442 11.00000 -1.20000
AFIX 0
C34 1 0.129361 0.586677 0.318589 11.00000 0.02278 0.01661 =
0.01075 0.00021 0.00570 0.00320
AFIX 23
H34A 2 0.086102 0.604019 0.373447 11.00000 -1.20000
H34B 2 0.219945 0.608995 0.327143 11.00000 -1.20000
AFIX 0
C35 1 0.011989 0.590731 0.183582 11.00000 0.01888 0.01787 =
0.01363 0.00247 0.00627 0.00460
AFIX 23
H35A 2 -0.083977 0.572897 0.176512 11.00000 -1.20000
H35B 2 -0.008487 0.631240 0.159620 11.00000 -1.20000
AFIX 0
C36 1 0.070247 0.560685 0.095928 11.00000 0.01511 0.01673 =
0.00923 -0.00039 0.00250 -0.00038
C37 1 0.105034 0.498369 0.140162 11.00000 0.01735 0.01609 =
0.01263 -0.00029 0.00424 0.00012
AFIX 13
H37 2 0.010123 0.482235 0.141845 11.00000 -1.20000
AFIX 0
C38 1 0.211070 0.591376 0.096276 11.00000 0.01912 0.01886 =
0.01436 -0.00054 0.00543 -0.00203
AFIX 137
H38A 2 0.292033 0.589862 0.179436 11.00000 -1.50000
H38B 2 0.186007 0.631177 0.071802 11.00000 -1.50000
H38C 2 0.244864 0.572636 0.037810 11.00000 -1.50000
AFIX 0
C39 1 0.130545 0.468321 0.035311 11.00000 0.02828 0.01774 =
0.01203 -0.00231 0.00587 0.00029
AFIX 23
H39A 2 0.107469 0.427194 0.033549 11.00000 -1.20000
H39B 2 0.236216 0.473050 0.044136 11.00000 -1.20000
AFIX 0
C40 1 0.019112 0.498447 -0.082255 11.00000 0.02612 0.01857 =
0.01242 -0.00292 0.00450 -0.00341
AFIX 23
H40A 2 -0.064911 0.472503 -0.129990 11.00000 -1.20000
H40B 2 0.071611 0.509843 -0.135359 11.00000 -1.20000
AFIX 0
C41 1 -0.042970 0.551840 -0.040516 11.00000 0.02178 0.01664 =
0.01076 0.00114 0.00334 -0.00384
C42 1 -0.205750 0.542561 -0.056325 11.00000 0.01985 0.03213 =
0.01767 0.00139 0.00052 -0.00195
AFIX 137
H42A 2 -0.269130 0.534718 -0.143364 11.00000 -1.50000
H42B 2 -0.242687 0.576820 -0.030124 11.00000 -1.50000
H42C 2 -0.210167 0.510174 -0.005658 11.00000 -1.50000
AFIX 0
C49 1 0.173768 0.784390 0.250646 11.00000 0.02057 0.02066 =
0.01332 -0.00069 0.00392 0.00060
C50 1 0.131840 0.790987 0.116353 11.00000 0.01553 0.01961 =
0.01144 0.00020 0.00260 0.00180
C51 1 0.054867 0.747340 0.034041 11.00000 0.01820 0.01624 =
0.01501 0.00166 0.00593 0.00053
AFIX 43
H51 2 0.030918 0.713095 0.064935 11.00000 -1.20000
AFIX 0
C52 1 0.013583 0.753710 -0.091540 11.00000 0.01959 0.01829 =
0.01337 -0.00119 0.00453 -0.00031
C53 1 0.044231 0.805119 -0.136797 11.00000 0.02588 0.02238 =
0.01168 0.00319 0.00600 0.00198
AFIX 43
H53 2 0.013632 0.810185 -0.223222 11.00000 -1.20000
AFIX 0
C54 1 0.118468 0.848370 -0.056751 11.00000 0.02691 0.01679 =
0.01861 0.00196 0.00908 -0.00161
AFIX 43
H54 2 0.137153 0.883269 -0.088688 11.00000 -1.20000
AFIX 0
C55 1 0.166664 0.841594 0.070819 11.00000 0.01954 0.01863 =
0.01515 -0.00216 0.00433 0.00041
C56 1 0.655782 0.485720 0.198802 11.00000 0.02094 0.01950 =
0.01339 0.00016 0.00597 -0.00122
C57 1 0.743032 0.480678 0.333548 11.00000 0.01795 0.01848 =
0.01311 -0.00101 0.00603 -0.00195
C58 1 0.823203 0.430418 0.383156 11.00000 0.02138 0.01814 =
0.01670 -0.00252 0.00759 -0.00022
C59 1 0.895461 0.424550 0.511021 11.00000 0.02616 0.01991 =
0.01789 0.00281 0.00442 0.00586
AFIX 43
H59 2 0.945122 0.389876 0.545493 11.00000 -1.20000
AFIX 0
C60 1 0.895447 0.468773 0.588071 11.00000 0.02806 0.02424 =
0.01073 0.00064 0.00125 0.00309
AFIX 43
H60 2 0.945497 0.464240 0.675063 11.00000 -1.20000
AFIX 0
C61 1 0.822662 0.520071 0.539480 11.00000 0.02238 0.01955 =
0.01311 -0.00178 0.00491 -0.00064
C62 1 0.744277 0.525186 0.413138 11.00000 0.01963 0.01629 =
0.01480 0.00023 0.00585 0.00077
AFIX 43
H62 2 0.690502 0.559278 0.379674 11.00000 -1.20000
AFIX 0
H4 2 0.545390 0.458463 0.927623 11.00000 0.02819
H2 2 0.322210 0.805973 -0.483881 11.00000 0.01990
N1 3 0.206533 0.741279 -0.478974 11.00000 0.02094 0.02417 =
0.01232 -0.00097 0.00278 -0.00042
N2 3 0.307401 0.784147 -0.431582 11.00000 0.02091 0.02257 =
0.01201 0.00045 0.00499 -0.00099
N3 3 0.420605 0.523000 0.923818 11.00000 0.02675 0.02298 =
0.01207 -0.00120 0.00589 -0.00425
N4 3 0.473210 0.480615 0.873860 11.00000 0.02222 0.02088 =
0.01157 0.00135 0.00199 -0.00111
O1 4 0.797562 0.674430 0.563259 11.00000 0.03357 0.01985 =
0.00924 -0.00002 0.00194 0.00396
H1A 2 0.841859 0.688915 0.634351 11.00000 0.04648
O2 4 -0.042120 0.600385 -0.116177 11.00000 0.03559 0.01775 =
0.00858 0.00211 0.00301 -0.00375
H2A 2 -0.073435 0.588084 -0.188411 11.00000 0.02962
O8 4 0.573544 0.531400 0.161451 11.00000 0.02969 0.02294 =
0.01047 -0.00059 0.00144 0.00606
H8 2 0.516244 0.530811 0.083509 11.00000 0.04850
O7 4 0.659765 0.447871 0.126416 11.00000 0.03374 0.02174 =
0.01349 -0.00316 0.00723 0.00333
O9 4 0.833166 0.386338 0.312381 11.00000 0.03558 0.01978 =
0.01751 -0.00282 0.00892 0.00597
H9A 2 0.776588 0.395505 0.238243 11.00000 0.04055
O10 4 0.831020 0.562852 0.620627 11.00000 0.03773 0.01896 =
0.01109 -0.00248 0.00204 0.00405
H10A 2 0.806890 0.594482 0.581938 11.00000 0.03179
O3 4 0.247746 0.821660 0.325408 11.00000 0.03420 0.02249 =
0.01212 -0.00212 0.00210 -0.00524
O4 4 0.127557 0.737778 0.284186 11.00000 0.03352 0.02514 =
0.00983 -0.00002 0.00596 -0.00678
H4C 2 0.151589 0.736658 0.362636 11.00000 0.05515
O6 4 -0.057967 0.711586 -0.175031 11.00000 0.03951 0.01836 =
0.01035 -0.00032 0.00515 -0.00574
H6 2 -0.041463 0.679881 -0.137631 11.00000 0.04663
O5 4 0.244897 0.885096 0.144780 11.00000 0.03509 0.01964 =
0.01617 -0.00133 0.00306 -0.00817
H5A 2 0.256392 0.873823 0.216636 11.00000 0.04694
HKLF 4
REM T in P2(1)
REM R1 = 0.0320 for 9715 Fo > 4sig(Fo) and 0.0328 for all 9891 data
REM 677 parameters refined using 9 restraints
END
WGHT 0.0478 0.5118
REM Instructions for potential hydrogen bonds
EQIV $5 -x, y-1/2, -z
HTAB C40 O5_$5
EQIV $6 -x+1, y+1/2, -z
HTAB C54 O7_$6
HTAB N4 O7_$1
HTAB N2 O3_$2
HTAB O1 O6_$3
HTAB O2 O10_$4
HTAB O8 N3_$2
HTAB O8 N4_$2
HTAB O9 O7
HTAB O10 O1
HTAB O4 N1_$1
HTAB O4 N2_$1
HTAB O6 O2
HTAB O5 O3
REM Highest difference peak 0.258, deepest hole -0.179, 1-sigma level 0.037
Q1 1 0.7017 0.7151 0.4151 11.00000 0.05 0.26
Q2 1 0.2398 0.5261 0.4293 11.00000 0.05 0.25
Q3 1 0.5375 0.7448 0.0182 11.00000 0.05 0.25
Q4 1 0.6961 0.7774 0.2438 11.00000 0.05 0.25
Q5 1 0.1551 0.7879 0.1776 11.00000 0.05 0.25
Q6 1 0.7006 0.4872 0.2711 11.00000 0.05 0.24
Q7 1 0.3178 0.4901 0.5177 11.00000 0.05 0.23
Q8 1 0.7572 0.7893 0.3520 11.00000 0.05 0.22
Q9 1 0.3188 0.7664 -0.2790 11.00000 0.05 0.22
Q10 1 0.0148 0.5597 0.0299 11.00000 0.05 0.22
;
_shelx_res_checksum 49064
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_STAN-PHA
_database_code_depnum_ccdc_archive 'CCDC 1863939'
_audit_update_record
;
2018-08-26 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2017/1
_shelx_SHELXL_version_number 2017/1
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H32 N2 O, C8 H6 O4'
_chemical_formula_sum 'C29 H38 N2 O5'
_chemical_formula_weight 494.61
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 7.8660(5)
_cell_length_b 11.3879(8)
_cell_length_c 29.2351(17)
_cell_angle_alpha 90
_cell_angle_beta 95.638(2)
_cell_angle_gamma 90
_cell_volume 2606.1(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 6148
_cell_measurement_theta_min 2.27
_cell_measurement_theta_max 26.72
_exptl_crystal_description BLOCK
_exptl_crystal_colour COLORLESS
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.261
_exptl_crystal_F_000 1064
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.300
_exptl_crystal_size_min 0.250
_exptl_absorpt_coefficient_mu 0.086
_shelx_estimated_absorpt_T_min 0.966
_shelx_estimated_absorpt_T_max 0.979
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.5862
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1633 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.7862.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 19245
_diffrn_reflns_av_unetI/netI 0.0841
_diffrn_reflns_av_R_equivalents 0.0601
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_theta_min 2.100
_diffrn_reflns_theta_max 25.000
_diffrn_reflns_theta_full 25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total 8760
_reflns_number_gt 6766
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.805
_reflns_Friedel_fraction_max 0.899
_reflns_Friedel_fraction_full 0.899
_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 ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_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^)+(0.0544P)^2^+0.2599P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 2371 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -0.8(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns 8760
_refine_ls_number_parameters 687
_refine_ls_number_restraints 9
_refine_ls_R_factor_all 0.0764
_refine_ls_R_factor_gt 0.0511
_refine_ls_wR_factor_ref 0.1210
_refine_ls_wR_factor_gt 0.1119
_refine_ls_goodness_of_fit_ref 0.972
_refine_ls_restrained_S_all 0.971
_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 0.9766(4) 0.8513(3) 0.16498(10) 0.0319(8) Uani 1 1 d D . . . .
H1A H 1.042(5) 0.873(5) 0.1881(11) 0.060(18) Uiso 1 1 d D . . . .
O2 O 0.0991(4) 0.7716(3) 0.32100(9) 0.0361(8) Uani 1 1 d D . . . .
H2A H 0.003(3) 0.759(4) 0.3060(12) 0.032(13) Uiso 1 1 d D . . . .
O3 O 0.8343(3) 0.7092(3) 0.75409(9) 0.0288(8) Uani 1 1 d . . . . .
O4 O 0.7277(4) 0.7642(3) 0.81841(10) 0.0334(9) Uani 1 1 d D . . . .
H4C H 0.823(4) 0.801(5) 0.824(2) 0.08(2) Uiso 1 1 d D . . . .
O5 O 0.7890(4) 0.4574(3) 0.76947(10) 0.0369(9) Uani 1 1 d . . . . .
O6 O 0.6676(4) 0.4145(4) 0.69974(11) 0.0478(10) Uani 1 1 d D . . . .
H6 H 0.757(5) 0.375(5) 0.696(2) 0.10(3) Uiso 1 1 d D . . . .
O7 O 0.1933(4) 0.2399(3) 0.73720(10) 0.0372(9) Uani 1 1 d . . . . .
O8 O 0.2781(4) 0.2266(3) 0.81184(10) 0.0427(9) Uani 1 1 d D . . . .
H8 H 0.190(5) 0.263(5) 0.818(2) 0.08(2) Uiso 1 1 d D . . . .
O9 O 0.1615(3) -0.0204(3) 0.74418(9) 0.0272(7) Uani 1 1 d . . . . .
O10 O 0.2723(4) -0.0778(3) 0.68061(10) 0.0327(8) Uani 1 1 d D . . . .
H10A H 0.169(3) -0.101(5) 0.6745(16) 0.049(16) Uiso 1 1 d D . . . .
N1 N 0.0152(4) 0.8553(4) -0.14844(12) 0.0310(9) Uani 1 1 d . . . . .
N2 N 0.1518(4) 0.9138(4) -0.16145(12) 0.0266(9) Uani 1 1 d D . . . .
H2 H 0.148(5) 0.938(4) -0.1900(7) 0.029(13) Uiso 1 1 d D . . . .
N3 N 0.9826(4) 0.8221(4) 0.64958(12) 0.0298(9) Uani 1 1 d . . . . .
N4 N 0.8439(5) 0.7618(4) 0.66050(12) 0.0290(9) Uani 1 1 d D . . . .
H4 H 0.839(5) 0.740(4) 0.6889(7) 0.036(14) Uiso 1 1 d D . . . .
C1 C 0.0527(5) 0.8335(4) -0.10383(14) 0.0281(11) Uani 1 1 d . . . . .
H1 H -0.018837 0.793234 -0.085736 0.034 Uiso 1 1 calc R U . . .
C2 C 0.2108(5) 0.8782(4) -0.08767(14) 0.0247(10) Uani 1 1 d . . . . .
C3 C 0.2720(5) 0.9304(4) -0.12558(13) 0.0240(10) Uani 1 1 d . . . . .
C4 C 0.4429(5) 0.9832(4) -0.12648(14) 0.0272(11) Uani 1 1 d . . . . .
H4A H 0.432907 1.058200 -0.142255 0.033 Uiso 1 1 calc R U . . .
H4B H 0.513952 0.932229 -0.143159 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5263(5) 1.0011(4) -0.07715(13) 0.0222(10) Uani 1 1 d . . . . .
H5 H 0.470207 1.068801 -0.064427 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5011(5) 0.8942(4) -0.04475(13) 0.0231(10) Uani 1 1 d . . . . .
C7 C 0.3086(5) 0.8795(5) -0.04085(14) 0.0279(11) Uani 1 1 d . . . . .
H7A H 0.288735 0.806671 -0.025025 0.033 Uiso 1 1 calc R U . . .
H7B H 0.268265 0.943677 -0.022949 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5712(5) 0.7802(4) -0.06353(14) 0.0278(10) Uani 1 1 d . . . . .
H8A H 0.563883 0.718412 -0.041474 0.042 Uiso 1 1 calc R U . . .
H8B H 0.688281 0.791404 -0.069130 0.042 Uiso 1 1 calc R U . . .
H8C H 0.505129 0.759449 -0.091735 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5895(5) 0.9256(4) 0.00389(13) 0.0227(10) Uani 1 1 d . . . . .
H9 H 0.537925 0.999892 0.012315 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7814(5) 0.9517(4) 0.00286(13) 0.0215(9) Uani 1 1 d . . . . .
H10 H 0.837599 0.881464 -0.007822 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8061(5) 1.0525(4) -0.03029(14) 0.0289(11) Uani 1 1 d . . . . .
H11A H 0.927272 1.062339 -0.032861 0.035 Uiso 1 1 calc R U . . .
H11B H 0.764262 1.124435 -0.017631 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7143(5) 1.0333(4) -0.07840(14) 0.0264(10) Uani 1 1 d . . . . .
H12A H 0.722188 1.104397 -0.096319 0.032 Uiso 1 1 calc R U . . .
H12B H 0.771242 0.970958 -0.093587 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5527(5) 0.8381(4) 0.04157(13) 0.0296(11) Uani 1 1 d . . . . .
H13A H 0.430205 0.833420 0.043058 0.036 Uiso 1 1 calc R U . . .
H13B H 0.592398 0.760902 0.033512 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6388(5) 0.8724(4) 0.08895(14) 0.0286(11) Uani 1 1 d . . . . .
H14A H 0.617209 0.812163 0.111098 0.034 Uiso 1 1 calc R U . . .
H14B H 0.590008 0.945405 0.098721 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8322(5) 0.8875(4) 0.08783(13) 0.0234(10) Uani 1 1 d . . . . .
C16 C 0.8595(5) 0.9810(4) 0.05145(13) 0.0237(10) Uani 1 1 d . . . . .
H16 H 0.801416 1.052088 0.060700 0.028 Uiso 1 1 calc R U . . .
C17 C 0.9128(5) 0.7690(4) 0.07725(15) 0.0345(11) Uani 1 1 d . . . . .
H17A H 0.876375 0.746644 0.046162 0.052 Uiso 1 1 calc R U . . .
H17B H 0.877316 0.710385 0.097916 0.052 Uiso 1 1 calc R U . . .
H17C H 1.034968 0.775896 0.081052 0.052 Uiso 1 1 calc R U . . .
C18 C 1.0519(5) 1.0066(5) 0.05933(14) 0.0313(12) Uani 1 1 d . . . . .
H18A H 1.076614 1.086026 0.050043 0.038 Uiso 1 1 calc R U . . .
H18B H 1.116023 0.952011 0.042196 0.038 Uiso 1 1 calc R U . . .
C19 C 1.0960(5) 0.9904(5) 0.11153(14) 0.0318(12) Uani 1 1 d . . . . .
H19A H 1.129067 1.064857 0.125859 0.038 Uiso 1 1 calc R U . . .
H19B H 1.189965 0.935544 0.117473 0.038 Uiso 1 1 calc R U . . .
C20 C 0.9329(5) 0.9420(4) 0.13101(14) 0.0252(10) Uani 1 1 d . . . . .
C21 C 0.8393(5) 1.0383(4) 0.15382(14) 0.0345(12) Uani 1 1 d . . . . .
H21A H 0.914216 1.073076 0.177982 0.052 Uiso 1 1 calc R U . . .
H21B H 0.741476 1.005756 0.166454 0.052 Uiso 1 1 calc R U . . .
H21C H 0.802719 1.097184 0.131492 0.052 Uiso 1 1 calc R U . . .
C22 C 0.9475(5) 0.8518(4) 0.60582(14) 0.0273(11) Uani 1 1 d . . . . .
H22 H 1.021015 0.893588 0.588791 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7860(5) 0.8123(4) 0.58870(14) 0.0249(10) Uani 1 1 d . . . . .
C24 C 0.7235(5) 0.7558(4) 0.62478(13) 0.0253(11) Uani 1 1 d . . . . .
C25 C 0.5553(5) 0.6933(5) 0.62271(13) 0.0283(11) Uani 1 1 d . . . . .
H25A H 0.497434 0.713581 0.649434 0.034 Uiso 1 1 calc R U . . .
H25B H 0.573951 0.609107 0.622939 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4435(5) 0.7287(4) 0.57856(13) 0.0230(10) Uani 1 1 d . . . . .
H26 H 0.401636 0.808351 0.583447 0.028 Uiso 1 1 calc R U . . .
C27 C 0.5422(5) 0.7329(4) 0.53457(12) 0.0200(9) Uani 1 1 d . . . . .
C28 C 0.6862(5) 0.8259(4) 0.54251(14) 0.0261(11) Uani 1 1 d . . . . .
H28A H 0.762966 0.818426 0.518669 0.031 Uiso 1 1 calc R U . . .
H28B H 0.636189 0.903838 0.540212 0.031 Uiso 1 1 calc R U . . .
C29 C 0.6249(5) 0.6135(4) 0.52634(13) 0.0229(9) Uani 1 1 d . . . . .
H29A H 0.674162 0.615200 0.497580 0.034 Uiso 1 1 calc R U . . .
H29B H 0.539614 0.553068 0.525515 0.034 Uiso 1 1 calc R U . . .
H29C H 0.712551 0.597750 0.550782 0.034 Uiso 1 1 calc R U . . .
C30 C 0.4147(5) 0.7690(4) 0.49376(13) 0.0202(10) Uani 1 1 d . . . . .
H30 H 0.369761 0.845451 0.502158 0.024 Uiso 1 1 calc R U . . .
C31 C 0.2587(5) 0.6883(4) 0.48586(13) 0.0217(9) Uani 1 1 d . . . . .
H31 H 0.297074 0.609565 0.478065 0.026 Uiso 1 1 calc R U . . .
C32 C 0.1680(5) 0.6806(5) 0.52969(13) 0.0298(11) Uani 1 1 d . . . . .
H32A H 0.114682 0.755676 0.534849 0.036 Uiso 1 1 calc R U . . .
H32B H 0.078194 0.622137 0.525405 0.036 Uiso 1 1 calc R U . . .
C33 C 0.2871(5) 0.6489(4) 0.57194(14) 0.0292(11) Uani 1 1 d . . . . .
H33A H 0.324660 0.568287 0.569189 0.035 Uiso 1 1 calc R U . . .
H33B H 0.224877 0.653977 0.598912 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4984(5) 0.7904(4) 0.44871(13) 0.0244(10) Uani 1 1 d . . . . .
H34A H 0.588149 0.848489 0.454453 0.029 Uiso 1 1 calc R U . . .
H34B H 0.550892 0.717986 0.439764 0.029 Uiso 1 1 calc R U . . .
C35 C 0.3720(5) 0.8328(4) 0.40878(14) 0.0266(11) Uani 1 1 d . . . . .
H35A H 0.329331 0.909958 0.415831 0.032 Uiso 1 1 calc R U . . .
H35B H 0.430108 0.839169 0.381112 0.032 Uiso 1 1 calc R U . . .
C36 C 0.2221(5) 0.7469(4) 0.40053(13) 0.0225(10) Uani 1 1 d . . . . .
C37 C 0.1400(5) 0.7349(4) 0.44606(13) 0.0226(10) Uani 1 1 d . . . . .
H37 H 0.108051 0.814485 0.454695 0.027 Uiso 1 1 calc R U . . .
C38 C 0.2856(5) 0.6311(4) 0.38282(14) 0.0306(11) Uani 1 1 d . . . . .
H38A H 0.365182 0.596178 0.405898 0.046 Uiso 1 1 calc R U . . .
H38B H 0.341225 0.644844 0.355516 0.046 Uiso 1 1 calc R U . . .
H38C H 0.190641 0.578987 0.375859 0.046 Uiso 1 1 calc R U . . .
C39 C -0.0282(5) 0.6695(5) 0.43219(14) 0.0335(12) Uani 1 1 d . . . . .
H39A H -0.115824 0.693063 0.451462 0.040 Uiso 1 1 calc R U . . .
H39B H -0.011951 0.585285 0.434768 0.040 Uiso 1 1 calc R U . . .
C40 C -0.0777(5) 0.7055(5) 0.38172(15) 0.0405(14) Uani 1 1 d . . . . .
H40A H -0.084838 0.636774 0.361998 0.049 Uiso 1 1 calc R U . . .
H40B H -0.187483 0.744894 0.378674 0.049 Uiso 1 1 calc R U . . .
C41 C 0.0636(5) 0.7889(5) 0.36843(14) 0.0301(11) Uani 1 1 d . . . . .
C42 C 0.0159(6) 0.9164(5) 0.37383(16) 0.0427(13) Uani 1 1 d . . . . .
H42A H -0.088157 0.932839 0.354901 0.064 Uiso 1 1 calc R U . . .
H42B H 0.105615 0.965557 0.364610 0.064 Uiso 1 1 calc R U . . .
H42C H -0.000207 0.931812 0.405399 0.064 Uiso 1 1 calc R U . . .
C43 C 0.7185(5) 0.7114(4) 0.77867(14) 0.0221(10) Uani 1 1 d . . . . .
C44 C 0.5475(5) 0.6598(4) 0.76457(13) 0.0201(10) Uani 1 1 d . . . . .
C45 C 0.5285(5) 0.5524(4) 0.74174(13) 0.0211(10) Uani 1 1 d . . . . .
C46 C 0.6769(5) 0.4708(4) 0.73887(14) 0.0261(11) Uani 1 1 d . . . . .
C47 C 0.3664(5) 0.5145(4) 0.72406(14) 0.0274(11) Uani 1 1 d . . . . .
H47 H 0.353340 0.442961 0.708749 0.033 Uiso 1 1 calc R U . . .
C48 C 0.2248(5) 0.5842(5) 0.72947(15) 0.0290(12) Uani 1 1 d . . . . .
H48 H 0.116747 0.559212 0.717638 0.035 Uiso 1 1 calc R U . . .
C49 C 0.2431(5) 0.6893(4) 0.75209(14) 0.0256(10) Uani 1 1 d . . . . .
H49 H 0.147841 0.735824 0.755389 0.031 Uiso 1 1 calc R U . . .
C50 C 0.4034(5) 0.7264(4) 0.77003(14) 0.0253(10) Uani 1 1 d . . . . .
H50 H 0.414675 0.797073 0.785988 0.030 Uiso 1 1 calc R U . . .
C51 C 0.2931(5) 0.2051(4) 0.76819(14) 0.0247(10) Uani 1 1 d . . . . .
C52 C 0.4510(5) 0.1380(4) 0.76113(14) 0.0257(10) Uani 1 1 d . . . . .
C53 C 0.4447(5) 0.0381(4) 0.73365(14) 0.0242(10) Uani 1 1 d . . . . .
C54 C 0.2781(5) -0.0213(4) 0.71954(13) 0.0220(10) Uani 1 1 d . . . . .
C55 C 0.5961(5) -0.0159(5) 0.72376(15) 0.0304(11) Uani 1 1 d . . . . .
H55 H 0.592217 -0.081774 0.704885 0.036 Uiso 1 1 calc R U . . .
C56 C 0.7512(6) 0.0281(5) 0.74185(17) 0.0392(13) Uani 1 1 d . . . . .
H56 H 0.851837 -0.007645 0.734956 0.047 Uiso 1 1 calc R U . . .
C57 C 0.7576(6) 0.1246(5) 0.77001(19) 0.0437(14) Uani 1 1 d . . . . .
H57 H 0.862694 0.152869 0.782707 0.052 Uiso 1 1 calc R U . . .
C58 C 0.6086(5) 0.1802(5) 0.77971(16) 0.0339(12) Uani 1 1 d . . . . .
H58 H 0.614109 0.245926 0.798684 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 0.0326(16) 0.037(2) 0.0236(17) 0.0051(15) -0.0076(14) -0.0084(15)
O2 0.0315(17) 0.057(3) 0.0187(16) 0.0022(15) -0.0060(14) -0.0190(17)
O3 0.0185(14) 0.044(2) 0.0251(16) -0.0027(15) 0.0053(13) -0.0008(15)
O4 0.0195(16) 0.053(3) 0.0282(18) -0.0156(17) 0.0036(14) -0.0062(17)
O5 0.0343(17) 0.041(2) 0.0321(18) -0.0068(16) -0.0143(15) 0.0148(16)
O6 0.045(2) 0.065(3) 0.0309(19) -0.0180(18) -0.0077(16) 0.028(2)
O7 0.0352(17) 0.046(2) 0.0284(18) -0.0023(16) -0.0082(15) 0.0097(17)
O8 0.047(2) 0.055(3) 0.0253(17) -0.0096(17) -0.0042(16) 0.022(2)
O9 0.0159(14) 0.042(2) 0.0244(16) -0.0021(15) 0.0026(12) 0.0001(14)
O10 0.0268(17) 0.047(2) 0.0241(17) -0.0093(16) 0.0011(14) -0.0041(17)
N1 0.0207(18) 0.042(3) 0.029(2) -0.0039(19) -0.0005(16) -0.0003(19)
N2 0.0241(19) 0.038(3) 0.0171(19) -0.0017(18) -0.0018(16) 0.0012(18)
N3 0.028(2) 0.035(3) 0.025(2) -0.0056(18) -0.0040(16) 0.0018(18)
N4 0.031(2) 0.036(3) 0.019(2) -0.0039(18) 0.0005(17) 0.0020(19)
C1 0.020(2) 0.037(3) 0.028(2) -0.003(2) 0.0032(19) 0.001(2)
C2 0.022(2) 0.031(3) 0.021(2) -0.001(2) 0.0016(18) 0.005(2)
C3 0.020(2) 0.031(3) 0.021(2) -0.004(2) -0.0007(19) 0.004(2)
C4 0.029(2) 0.030(3) 0.022(2) -0.001(2) 0.0016(19) 0.000(2)
C5 0.022(2) 0.023(3) 0.021(2) -0.0029(18) 0.0017(17) -0.0022(19)
C6 0.022(2) 0.026(3) 0.021(2) -0.0021(18) 0.0008(17) -0.0020(19)
C7 0.024(2) 0.038(3) 0.022(2) 0.003(2) 0.0044(18) -0.005(2)
C8 0.030(2) 0.023(3) 0.030(2) -0.0023(19) -0.0030(19) -0.002(2)
C9 0.026(2) 0.023(3) 0.020(2) -0.0013(19) 0.0048(18) 0.000(2)
C10 0.022(2) 0.022(3) 0.020(2) -0.0034(18) 0.0011(17) -0.0015(18)
C11 0.026(2) 0.035(3) 0.026(2) 0.001(2) 0.0011(18) -0.008(2)
C12 0.026(2) 0.030(3) 0.023(2) 0.006(2) 0.0003(18) -0.005(2)
C13 0.025(2) 0.038(3) 0.024(2) 0.009(2) -0.0046(18) -0.012(2)
C14 0.028(2) 0.037(3) 0.020(2) 0.009(2) -0.0017(18) -0.009(2)
C15 0.023(2) 0.025(3) 0.021(2) -0.0002(18) 0.0002(17) -0.0047(19)
C16 0.025(2) 0.027(3) 0.019(2) -0.0037(19) 0.0032(18) -0.002(2)
C17 0.039(2) 0.029(3) 0.034(3) -0.003(2) -0.007(2) 0.002(2)
C18 0.025(2) 0.044(3) 0.025(2) 0.002(2) 0.0011(19) -0.010(2)
C19 0.027(2) 0.040(3) 0.028(2) -0.003(2) 0.0003(19) -0.012(2)
C20 0.027(2) 0.026(3) 0.022(2) 0.0019(19) -0.0013(18) -0.006(2)
C21 0.042(3) 0.039(3) 0.023(2) -0.007(2) 0.005(2) -0.008(2)
C22 0.031(2) 0.025(3) 0.026(2) -0.004(2) 0.0002(19) -0.002(2)
C23 0.026(2) 0.024(3) 0.024(2) -0.005(2) -0.0003(19) 0.000(2)
C24 0.030(2) 0.027(3) 0.018(2) -0.0040(19) -0.0018(19) 0.004(2)
C25 0.034(2) 0.035(3) 0.016(2) 0.002(2) 0.0029(18) 0.001(2)
C26 0.026(2) 0.025(3) 0.018(2) 0.0035(19) 0.0041(17) 0.007(2)
C27 0.0220(19) 0.020(2) 0.017(2) 0.0016(18) 0.0001(16) -0.0020(19)
C28 0.028(2) 0.025(3) 0.024(2) 0.001(2) -0.0041(19) -0.003(2)
C29 0.028(2) 0.023(3) 0.017(2) 0.0032(18) -0.0030(17) 0.0014(19)
C30 0.020(2) 0.021(3) 0.018(2) -0.0004(18) -0.0009(17) -0.0005(19)
C31 0.023(2) 0.025(3) 0.018(2) -0.0013(18) 0.0046(17) -0.0018(19)
C32 0.021(2) 0.046(3) 0.023(2) 0.003(2) 0.0035(18) -0.005(2)
C33 0.027(2) 0.040(3) 0.022(2) 0.002(2) 0.0080(19) -0.002(2)
C34 0.021(2) 0.026(3) 0.027(2) 0.0040(19) 0.0002(18) -0.0085(19)
C35 0.028(2) 0.027(3) 0.025(2) 0.004(2) 0.0024(19) -0.005(2)
C36 0.021(2) 0.024(3) 0.022(2) 0.0005(18) -0.0012(17) -0.0003(19)
C37 0.020(2) 0.027(3) 0.021(2) -0.0004(19) 0.0021(17) -0.0018(19)
C38 0.035(2) 0.032(3) 0.026(2) -0.003(2) 0.006(2) -0.005(2)
C39 0.025(2) 0.050(4) 0.025(2) 0.002(2) 0.0005(19) -0.009(2)
C40 0.024(2) 0.071(4) 0.026(2) 0.003(3) -0.004(2) -0.013(3)
C41 0.024(2) 0.044(3) 0.021(2) 0.002(2) -0.0011(19) -0.003(2)
C42 0.037(3) 0.055(4) 0.033(3) 0.009(2) -0.013(2) 0.012(3)
C43 0.021(2) 0.022(3) 0.022(2) 0.0035(19) -0.0013(18) 0.004(2)
C44 0.017(2) 0.025(3) 0.018(2) 0.0014(18) 0.0027(18) 0.0015(19)
C45 0.022(2) 0.027(3) 0.014(2) 0.0010(18) 0.0019(17) -0.001(2)
C46 0.024(2) 0.033(3) 0.021(2) 0.000(2) 0.0005(19) 0.000(2)
C47 0.027(2) 0.031(3) 0.023(2) -0.007(2) -0.0019(19) -0.006(2)
C48 0.015(2) 0.046(3) 0.025(2) -0.002(2) -0.0006(18) -0.004(2)
C49 0.016(2) 0.032(3) 0.030(2) 0.001(2) 0.0048(18) 0.003(2)
C50 0.021(2) 0.029(3) 0.027(2) 0.000(2) 0.0041(18) -0.001(2)
C51 0.027(2) 0.019(3) 0.027(2) 0.0003(19) -0.004(2) -0.003(2)
C52 0.022(2) 0.033(3) 0.022(2) 0.006(2) 0.0005(19) -0.001(2)
C53 0.021(2) 0.034(3) 0.017(2) 0.005(2) 0.0013(18) -0.001(2)
C54 0.021(2) 0.026(3) 0.019(2) 0.0000(19) -0.0015(18) 0.006(2)
C55 0.028(2) 0.032(3) 0.033(3) -0.001(2) 0.0096(19) 0.002(2)
C56 0.020(2) 0.052(4) 0.045(3) 0.010(3) 0.003(2) -0.001(2)
C57 0.018(2) 0.053(4) 0.059(4) 0.012(3) -0.003(2) -0.009(3)
C58 0.027(2) 0.036(3) 0.037(3) 0.005(2) -0.005(2) -0.004(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 C20 1.451(5) . ?
O1 H1A 0.846(14) . ?
O2 C41 1.454(5) . ?
O2 H2A 0.849(14) . ?
O3 C43 1.215(4) . ?
O4 C43 1.304(5) . ?
O4 H4C 0.855(14) . ?
O5 C46 1.203(5) . ?
O6 C46 1.307(5) . ?
O6 H6 0.855(14) . ?
O7 C51 1.206(5) . ?
O8 C51 1.316(5) . ?
O8 H8 0.851(14) . ?
O9 C54 1.221(5) . ?
O10 C54 1.304(5) . ?
O10 H10A 0.854(14) . ?
N1 C1 1.332(5) . ?
N1 N2 1.350(5) . ?
N2 C3 1.354(5) . ?
N2 H2 0.875(14) . ?
N3 C22 1.326(5) . ?
N3 N4 1.354(5) . ?
N4 C24 1.341(5) . ?
N4 H4 0.871(14) . ?
C1 C2 1.384(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(6) . ?
C2 C7 1.503(5) . ?
C3 C4 1.475(6) . ?
C4 C5 1.538(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.527(5) . ?
C5 C6 1.566(6) . ?
C5 H5 0.9800 . ?
C6 C8 1.533(6) . ?
C6 C7 1.539(5) . ?
C6 C9 1.561(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C13 1.534(6) . ?
C9 C10 1.542(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.526(6) . ?
C10 C16 1.528(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.532(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.532(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.535(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C17 1.535(6) . ?
C15 C16 1.535(6) . ?
C15 C20 1.552(6) . ?
C16 C18 1.536(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.543(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.555(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.512(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.393(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(6) . ?
C23 C28 1.502(6) . ?
C24 C25 1.498(6) . ?
C25 C26 1.543(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C33 1.526(6) . ?
C26 C27 1.567(5) . ?
C26 H26 0.9800 . ?
C27 C29 1.536(6) . ?
C27 C30 1.537(5) . ?
C27 C28 1.551(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.533(6) . ?
C30 C34 1.548(5) . ?
C30 H30 0.9800 . ?
C31 C37 1.515(5) . ?
C31 C32 1.529(5) . ?
C31 H31 0.9800 . ?
C32 C33 1.519(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.535(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.533(6) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C38 1.519(6) . ?
C36 C37 1.542(5) . ?
C36 C41 1.560(6) . ?
C37 C39 1.537(6) . ?
C37 H37 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.544(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.541(6) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.512(7) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.489(6) . ?
C44 C50 1.386(6) . ?
C44 C45 1.394(6) . ?
C45 C47 1.396(6) . ?
C45 C46 1.501(6) . ?
C47 C48 1.390(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.369(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.383(6) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C52 1.490(6) . ?
C52 C53 1.391(6) . ?
C52 C58 1.389(6) . ?
C53 C55 1.396(6) . ?
C53 C54 1.496(6) . ?
C55 C56 1.375(6) . ?
C55 H55 0.9300 . ?
C56 C57 1.371(8) . ?
C56 H56 0.9300 . ?
C57 C58 1.386(7) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
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
C20 O1 H1A 115(4) . . ?
C41 O2 H2A 106(3) . . ?
C43 O4 H4C 112(4) . . ?
C46 O6 H6 114(4) . . ?
C51 O8 H8 118(4) . . ?
C54 O10 H10A 107(3) . . ?
C1 N1 N2 105.2(3) . . ?
N1 N2 C3 111.4(3) . . ?
N1 N2 H2 118(3) . . ?
C3 N2 H2 130(3) . . ?
C22 N3 N4 105.1(4) . . ?
C24 N4 N3 111.5(4) . . ?
C24 N4 H4 129(3) . . ?
N3 N4 H4 119(3) . . ?
N1 C1 C2 111.8(4) . . ?
N1 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
C3 C2 C1 104.8(4) . . ?
C3 C2 C7 122.5(4) . . ?
C1 C2 C7 132.6(4) . . ?
N2 C3 C2 106.8(4) . . ?
N2 C3 C4 127.6(4) . . ?
C2 C3 C4 125.3(4) . . ?
C3 C4 C5 110.0(3) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C12 C5 C4 109.5(3) . . ?
C12 C5 C6 112.4(3) . . ?
C4 C5 C6 113.4(3) . . ?
C12 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C6 C5 H5 107.1 . . ?
C8 C6 C7 109.0(4) . . ?
C8 C6 C9 112.1(3) . . ?
C7 C6 C9 108.1(3) . . ?
C8 C6 C5 111.7(3) . . ?
C7 C6 C5 108.3(3) . . ?
C9 C6 C5 107.6(3) . . ?
C2 C7 C6 110.7(3) . . ?
C2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 113.2(3) . . ?
C13 C9 C6 114.0(3) . . ?
C10 C9 C6 112.0(3) . . ?
C13 C9 H9 105.6 . . ?
C10 C9 H9 105.6 . . ?
C6 C9 H9 105.6 . . ?
C11 C10 C16 111.2(3) . . ?
C11 C10 C9 110.1(3) . . ?
C16 C10 C9 109.2(3) . . ?
C11 C10 H10 108.8 . . ?
C16 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C10 C11 C12 113.4(4) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C5 C12 C11 112.5(3) . . ?
C5 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C5 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C9 112.7(4) . . ?
C14 C13 H13A 109.1 . . ?
C9 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C9 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 111.1(3) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C17 C15 C14 109.6(4) . . ?
C17 C15 C16 112.5(3) . . ?
C14 C15 C16 107.4(3) . . ?
C17 C15 C20 109.1(3) . . ?
C14 C15 C20 117.1(3) . . ?
C16 C15 C20 101.0(3) . . ?
C10 C16 C18 118.7(3) . . ?
C10 C16 C15 114.9(4) . . ?
C18 C16 C15 103.3(3) . . ?
C10 C16 H16 106.3 . . ?
C18 C16 H16 106.3 . . ?
C15 C16 H16 106.3 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 104.4(3) . . ?
C16 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C16 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C18 C19 C20 106.9(3) . . ?
C18 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
C18 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
O1 C20 C21 107.9(3) . . ?
O1 C20 C15 109.9(4) . . ?
C21 C20 C15 114.6(4) . . ?
O1 C20 C19 110.8(3) . . ?
C21 C20 C19 111.1(4) . . ?
C15 C20 C19 102.6(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 111.1(4) . . ?
N3 C22 H22 124.4 . . ?
C23 C22 H22 124.4 . . ?
C24 C23 C22 105.0(4) . . ?
C24 C23 C28 123.1(4) . . ?
C22 C23 C28 131.9(4) . . ?
N4 C24 C23 107.3(4) . . ?
N4 C24 C25 127.5(4) . . ?
C23 C24 C25 125.1(4) . . ?
C24 C25 C26 109.8(4) . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C33 C26 C25 109.7(3) . . ?
C33 C26 C27 111.9(3) . . ?
C25 C26 C27 114.0(3) . . ?
C33 C26 H26 107.0 . . ?
C25 C26 H26 107.0 . . ?
C27 C26 H26 107.0 . . ?
C29 C27 C30 111.6(3) . . ?
C29 C27 C28 108.3(3) . . ?
C30 C27 C28 110.2(3) . . ?
C29 C27 C26 110.7(3) . . ?
C30 C27 C26 107.9(3) . . ?
C28 C27 C26 108.2(3) . . ?
C23 C28 C27 111.9(3) . . ?
C23 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C23 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C27 114.1(3) . . ?
C31 C30 C34 111.5(3) . . ?
C27 C30 C34 113.8(3) . . ?
C31 C30 H30 105.5 . . ?
C27 C30 H30 105.5 . . ?
C34 C30 H30 105.5 . . ?
C37 C31 C32 111.1(3) . . ?
C37 C31 C30 109.2(3) . . ?
C32 C31 C30 109.9(3) . . ?
C37 C31 H31 108.8 . . ?
C32 C31 H31 108.8 . . ?
C30 C31 H31 108.8 . . ?
C33 C32 C31 113.2(3) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C26 112.7(4) . . ?
C32 C33 H33A 109.0 . . ?
C26 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C26 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 C30 113.5(3) . . ?
C35 C34 H34A 108.9 . . ?
C30 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C30 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 110.5(4) . . ?
C36 C35 H35A 109.6 . . ?
C34 C35 H35A 109.6 . . ?
C36 C35 H35B 109.6 . . ?
C34 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C38 C36 C35 109.5(3) . . ?
C38 C36 C37 113.4(4) . . ?
C35 C36 C37 107.6(3) . . ?
C38 C36 C41 109.4(3) . . ?
C35 C36 C41 117.1(4) . . ?
C37 C36 C41 99.7(3) . . ?
C31 C37 C39 118.8(4) . . ?
C31 C37 C36 114.5(3) . . ?
C39 C37 C36 103.8(3) . . ?
C31 C37 H37 106.3 . . ?
C39 C37 H37 106.3 . . ?
C36 C37 H37 106.3 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 104.7(4) . . ?
C37 C39 H39A 110.8 . . ?
C40 C39 H39A 110.8 . . ?
C37 C39 H39B 110.8 . . ?
C40 C39 H39B 110.8 . . ?
H39A C39 H39B 108.9 . . ?
C41 C40 C39 106.5(3) . . ?
C41 C40 H40A 110.4 . . ?
C39 C40 H40A 110.4 . . ?
C41 C40 H40B 110.4 . . ?
C39 C40 H40B 110.4 . . ?
H40A C40 H40B 108.6 . . ?
O2 C41 C42 107.6(4) . . ?
O2 C41 C40 111.5(4) . . ?
C42 C41 C40 111.9(4) . . ?
O2 C41 C36 108.4(3) . . ?
C42 C41 C36 115.1(4) . . ?
C40 C41 C36 102.3(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O3 C43 O4 123.9(4) . . ?
O3 C43 C44 122.5(4) . . ?
O4 C43 C44 113.5(3) . . ?
C50 C44 C45 119.0(4) . . ?
C50 C44 C43 118.6(4) . . ?
C45 C44 C43 122.0(4) . . ?
C44 C45 C47 120.0(4) . . ?
C44 C45 C46 121.5(4) . . ?
C47 C45 C46 118.3(4) . . ?
O5 C46 O6 124.2(4) . . ?
O5 C46 C45 123.7(4) . . ?
O6 C46 C45 112.1(4) . . ?
C48 C47 C45 119.6(4) . . ?
C48 C47 H47 120.2 . . ?
C45 C47 H47 120.2 . . ?
C49 C48 C47 120.5(4) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C48 C49 C50 119.9(4) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C49 C50 C44 121.0(4) . . ?
C49 C50 H50 119.5 . . ?
C44 C50 H50 119.5 . . ?
O7 C51 O8 123.6(4) . . ?
O7 C51 C52 123.7(4) . . ?
O8 C51 C52 112.6(4) . . ?
C53 C52 C58 119.3(4) . . ?
C53 C52 C51 121.1(4) . . ?
C58 C52 C51 119.5(4) . . ?
C52 C53 C55 119.8(4) . . ?
C52 C53 C54 120.6(4) . . ?
C55 C53 C54 119.1(4) . . ?
O9 C54 O10 123.7(4) . . ?
O9 C54 C53 121.5(4) . . ?
O10 C54 C53 114.7(3) . . ?
C56 C55 C53 120.2(5) . . ?
C56 C55 H55 119.9 . . ?
C53 C55 H55 119.9 . . ?
C57 C56 C55 120.1(5) . . ?
C57 C56 H56 119.9 . . ?
C55 C56 H56 119.9 . . ?
C56 C57 C58 120.5(5) . . ?
C56 C57 H57 119.8 . . ?
C58 C57 H57 119.8 . . ?
C57 C58 C52 120.1(5) . . ?
C57 C58 H58 119.9 . . ?
C52 C58 H58 119.9 . . ?
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
_geom_hbond_publ_flag
O1 H1A O5 0.846(14) 1.97(2) 2.800(4) 165(5) 2_756 yes
O2 H2A O7 0.849(14) 1.908(16) 2.747(4) 169(4) 2_556 yes
O4 H4C N1 0.855(14) 1.76(2) 2.588(5) 163(6) 1_656 yes
O6 H6 O2 0.855(14) 1.73(2) 2.570(4) 165(7) 2_646 yes
O8 H8 O1 0.851(14) 1.751(17) 2.599(4) 173(7) 2_646 yes
O10 H10A N3 0.854(14) 1.80(2) 2.628(5) 163(5) 1_445 yes
N2 H2 O9 0.875(14) 1.996(15) 2.867(5) 174(4) 1_564 yes
N4 H4 O3 0.871(14) 1.942(16) 2.809(4) 173(5) . yes
_refine_diff_density_max 0.187
_refine_diff_density_min -0.255
_refine_diff_density_rms 0.048
_shelx_res_file
;
TITL 2 in P2(1)
T.res
created by SHELXL-2017/1 at 13:04:21 on 26-Aug-2018
CELL 0.71073 7.866 11.3879 29.2351 90 95.638 90
ZERR 4 0.0005 0.0008 0.0017 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 116 152 8 20
DFIX 0.85 0.01 O1 H1A O2 H2A O4 H4C O6 H6 O8 H8 O10 H10A
DFIX 0.87 0.01 N2 H2 N4 H4
SIZE 0.25 0.30 0.40
TEMP -153
OMIT 0 50
L.S. 50
PLAN 10
TEMP 23
FREE N3 H4
BOND $H
fmap 2
HTAB 2
HTAB O1 O5_$1
HTAB O2 O7_$2
HTAB O4 N1_$3
HTAB O6 O2_$4
HTAB O8 O1_$4
HTAB O10 N3_$5
HTAB N2 O9_$6
HTAB N4 O3
EQIV $1 -x+2, y+1/2, -z+1
EQIV $2 -x, y+1/2, -z+1
EQIV $3 x+1, y, z+1
EQIV $4 -x+1, y-1/2, -z+1
EQIV $5 x-1, y-1, z
EQIV $6 x, y+1, z-1
acta
REM
REM
REM
WGHT 0.054400 0.259900
FVAR 0.16651
O1 4 0.976564 0.851256 0.164982 11.00000 0.03264 0.03740 =
0.02360 0.00508 -0.00761 -0.00839
H1A 2 1.042163 0.873225 0.188069 11.00000 0.05965
O2 4 0.099069 0.771598 0.320997 11.00000 0.03152 0.05650 =
0.01869 0.00217 -0.00597 -0.01903
H2A 2 0.002915 0.758596 0.306026 11.00000 0.03240
O3 4 0.834271 0.709183 0.754090 11.00000 0.01853 0.04353 =
0.02506 -0.00265 0.00527 -0.00076
O4 4 0.727747 0.764173 0.818409 11.00000 0.01952 0.05270 =
0.02817 -0.01560 0.00365 -0.00617
H4C 2 0.822505 0.800555 0.824191 11.00000 0.08183
O5 4 0.789029 0.457429 0.769466 11.00000 0.03426 0.04086 =
0.03210 -0.00680 -0.01431 0.01479
O6 4 0.667555 0.414514 0.699740 11.00000 0.04524 0.06507 =
0.03089 -0.01805 -0.00770 0.02818
H6 2 0.757172 0.375070 0.695578 11.00000 0.10231
O7 4 0.193333 0.239892 0.737197 11.00000 0.03525 0.04565 =
0.02843 -0.00226 -0.00822 0.00968
O8 4 0.278142 0.226620 0.811843 11.00000 0.04653 0.05482 =
0.02530 -0.00962 -0.00419 0.02220
H8 2 0.189582 0.263445 0.818439 11.00000 0.08327
O9 4 0.161499 -0.020352 0.744182 11.00000 0.01589 0.04159 =
0.02437 -0.00213 0.00262 0.00013
O10 4 0.272270 -0.077804 0.680609 11.00000 0.02680 0.04688 =
0.02410 -0.00933 0.00109 -0.00412
H10A 2 0.169444 -0.101416 0.674517 11.00000 0.04872
N1 3 0.015233 0.855285 -0.148441 11.00000 0.02071 0.04247 =
0.02917 -0.00392 -0.00048 -0.00030
N2 3 0.151806 0.913844 -0.161452 11.00000 0.02408 0.03792 =
0.01712 -0.00172 -0.00179 0.00124
H2 2 0.148432 0.937584 -0.189984 11.00000 0.02913
N3 3 0.982617 0.822081 0.649580 11.00000 0.02825 0.03466 =
0.02528 -0.00558 -0.00402 0.00176
N4 3 0.843917 0.761779 0.660499 11.00000 0.03107 0.03609 =
0.01948 -0.00389 0.00047 0.00200
H4 2 0.839448 0.739623 0.688867 11.00000 0.03612
C1 1 0.052650 0.833531 -0.103826 11.00000 0.01981 0.03691 =
0.02764 -0.00300 0.00317 0.00092
AFIX 43
H1 2 -0.018837 0.793234 -0.085736 11.00000 -1.20000
AFIX 0
C2 1 0.210838 0.878187 -0.087667 11.00000 0.02151 0.03117 =
0.02122 -0.00105 0.00163 0.00456
C3 1 0.271960 0.930390 -0.125576 11.00000 0.02015 0.03062 =
0.02066 -0.00379 -0.00066 0.00355
C4 1 0.442864 0.983209 -0.126485 11.00000 0.02933 0.03042 =
0.02161 -0.00058 0.00158 -0.00031
AFIX 23
H4A 2 0.432907 1.058200 -0.142255 11.00000 -1.20000
H4B 2 0.513952 0.932229 -0.143159 11.00000 -1.20000
AFIX 0
C5 1 0.526327 1.001070 -0.077150 11.00000 0.02163 0.02336 =
0.02147 -0.00292 0.00168 -0.00215
AFIX 13
H5 2 0.470207 1.068801 -0.064427 11.00000 -1.20000
AFIX 0
C6 1 0.501138 0.894245 -0.044745 11.00000 0.02214 0.02618 =
0.02075 -0.00214 0.00083 -0.00196
C7 1 0.308571 0.879520 -0.040853 11.00000 0.02424 0.03799 =
0.02183 0.00335 0.00440 -0.00464
AFIX 23
H7A 2 0.288735 0.806671 -0.025025 11.00000 -1.20000
H7B 2 0.268265 0.943677 -0.022949 11.00000 -1.20000
AFIX 0
C8 1 0.571150 0.780222 -0.063526 11.00000 0.03010 0.02250 =
0.02954 -0.00232 -0.00300 -0.00160
AFIX 137
H8A 2 0.563883 0.718412 -0.041474 11.00000 -1.50000
H8B 2 0.688281 0.791404 -0.069130 11.00000 -1.50000
H8C 2 0.505129 0.759449 -0.091735 11.00000 -1.50000
AFIX 0
C9 1 0.589462 0.925600 0.003889 11.00000 0.02586 0.02313 =
0.01958 -0.00130 0.00476 0.00036
AFIX 13
H9 2 0.537925 0.999892 0.012315 11.00000 -1.20000
AFIX 0
C10 1 0.781394 0.951733 0.002857 11.00000 0.02223 0.02236 =
0.01958 -0.00339 0.00108 -0.00154
AFIX 13
H10 2 0.837599 0.881464 -0.007822 11.00000 -1.20000
AFIX 0
C11 1 0.806096 1.052465 -0.030290 11.00000 0.02596 0.03490 =
0.02565 0.00063 0.00109 -0.00828
AFIX 23
H11A 2 0.927272 1.062339 -0.032861 11.00000 -1.20000
H11B 2 0.764262 1.124435 -0.017631 11.00000 -1.20000
AFIX 0
C12 1 0.714258 1.033274 -0.078395 11.00000 0.02596 0.02958 =
0.02309 0.00630 0.00025 -0.00473
AFIX 23
H12A 2 0.722188 1.104397 -0.096319 11.00000 -1.20000
H12B 2 0.771242 0.970958 -0.093587 11.00000 -1.20000
AFIX 0
C13 1 0.552665 0.838121 0.041568 11.00000 0.02480 0.03847 =
0.02425 0.00929 -0.00460 -0.01165
AFIX 23
H13A 2 0.430205 0.833420 0.043058 11.00000 -1.20000
H13B 2 0.592398 0.760902 0.033512 11.00000 -1.20000
AFIX 0
C14 1 0.638794 0.872438 0.088949 11.00000 0.02809 0.03703 =
0.01973 0.00882 -0.00173 -0.00854
AFIX 23
H14A 2 0.617209 0.812163 0.111098 11.00000 -1.20000
H14B 2 0.590008 0.945405 0.098721 11.00000 -1.20000
AFIX 0
C15 1 0.832198 0.887498 0.087826 11.00000 0.02300 0.02541 =
0.02140 -0.00016 0.00021 -0.00470
C16 1 0.859450 0.981038 0.051452 11.00000 0.02505 0.02691 =
0.01925 -0.00368 0.00320 -0.00153
AFIX 13
H16 2 0.801416 1.052088 0.060700 11.00000 -1.20000
AFIX 0
C17 1 0.912759 0.769009 0.077248 11.00000 0.03880 0.02903 =
0.03373 -0.00308 -0.00656 0.00205
AFIX 137
H17A 2 0.876375 0.746644 0.046162 11.00000 -1.50000
H17B 2 0.877316 0.710385 0.097916 11.00000 -1.50000
H17C 2 1.034968 0.775896 0.081052 11.00000 -1.50000
AFIX 0
C18 1 1.051875 1.006557 0.059326 11.00000 0.02521 0.04376 =
0.02465 0.00183 0.00108 -0.00987
AFIX 23
H18A 2 1.076614 1.086026 0.050043 11.00000 -1.20000
H18B 2 1.116023 0.952011 0.042196 11.00000 -1.20000
AFIX 0
C19 1 1.096031 0.990382 0.111531 11.00000 0.02704 0.03962 =
0.02827 -0.00346 0.00027 -0.01212
AFIX 23
H19A 2 1.129067 1.064857 0.125859 11.00000 -1.20000
H19B 2 1.189965 0.935544 0.117473 11.00000 -1.20000
AFIX 0
C20 1 0.932942 0.941974 0.131007 11.00000 0.02735 0.02558 =
0.02207 0.00191 -0.00132 -0.00581
C21 1 0.839287 1.038291 0.153816 11.00000 0.04194 0.03874 =
0.02307 -0.00653 0.00469 -0.00824
AFIX 137
H21A 2 0.914216 1.073076 0.177982 11.00000 -1.50000
H21B 2 0.741476 1.005756 0.166454 11.00000 -1.50000
H21C 2 0.802719 1.097184 0.131492 11.00000 -1.50000
AFIX 0
C22 1 0.947506 0.851831 0.605821 11.00000 0.03050 0.02487 =
0.02587 -0.00400 0.00016 -0.00233
AFIX 43
H22 2 1.021015 0.893588 0.588791 11.00000 -1.20000
AFIX 0
C23 1 0.786034 0.812323 0.588703 11.00000 0.02624 0.02393 =
0.02387 -0.00516 -0.00031 -0.00018
C24 1 0.723517 0.755797 0.624779 11.00000 0.03027 0.02689 =
0.01784 -0.00401 -0.00183 0.00371
C25 1 0.555345 0.693317 0.622714 11.00000 0.03392 0.03528 =
0.01580 0.00250 0.00290 0.00068
AFIX 23
H25A 2 0.497434 0.713581 0.649434 11.00000 -1.20000
H25B 2 0.573951 0.609107 0.622939 11.00000 -1.20000
AFIX 0
C26 1 0.443458 0.728711 0.578560 11.00000 0.02630 0.02458 =
0.01845 0.00353 0.00414 0.00681
AFIX 13
H26 2 0.401636 0.808351 0.583447 11.00000 -1.20000
AFIX 0
C27 1 0.542221 0.732925 0.534572 11.00000 0.02198 0.02020 =
0.01737 0.00159 0.00014 -0.00205
C28 1 0.686162 0.825934 0.542512 11.00000 0.02835 0.02521 =
0.02353 0.00060 -0.00413 -0.00274
AFIX 23
H28A 2 0.762966 0.818426 0.518669 11.00000 -1.20000
H28B 2 0.636189 0.903838 0.540212 11.00000 -1.20000
AFIX 0
C29 1 0.624888 0.613542 0.526340 11.00000 0.02762 0.02270 =
0.01731 0.00317 -0.00296 0.00136
AFIX 137
H29A 2 0.674162 0.615200 0.497580 11.00000 -1.50000
H29B 2 0.539614 0.553068 0.525515 11.00000 -1.50000
H29C 2 0.712551 0.597750 0.550782 11.00000 -1.50000
AFIX 0
C30 1 0.414727 0.768999 0.493762 11.00000 0.02002 0.02149 =
0.01841 -0.00044 -0.00093 -0.00055
AFIX 13
H30 2 0.369761 0.845451 0.502158 11.00000 -1.20000
AFIX 0
C31 1 0.258654 0.688282 0.485862 11.00000 0.02307 0.02480 =
0.01768 -0.00126 0.00456 -0.00177
AFIX 13
H31 2 0.297074 0.609565 0.478065 11.00000 -1.20000
AFIX 0
C32 1 0.167965 0.680648 0.529685 11.00000 0.02093 0.04595 =
0.02264 0.00275 0.00345 -0.00527
AFIX 23
H32A 2 0.114682 0.755676 0.534849 11.00000 -1.20000
H32B 2 0.078194 0.622137 0.525405 11.00000 -1.20000
AFIX 0
C33 1 0.287143 0.648896 0.571940 11.00000 0.02687 0.03976 =
0.02221 0.00222 0.00801 -0.00205
AFIX 23
H33A 2 0.324660 0.568287 0.569189 11.00000 -1.20000
H33B 2 0.224877 0.653977 0.598912 11.00000 -1.20000
AFIX 0
C34 1 0.498365 0.790423 0.448715 11.00000 0.02060 0.02562 =
0.02666 0.00397 0.00020 -0.00855
AFIX 23
H34A 2 0.588149 0.848489 0.454453 11.00000 -1.20000
H34B 2 0.550892 0.717986 0.439764 11.00000 -1.20000
AFIX 0
C35 1 0.371998 0.832798 0.408776 11.00000 0.02796 0.02694 =
0.02474 0.00382 0.00239 -0.00526
AFIX 23
H35A 2 0.329331 0.909958 0.415831 11.00000 -1.20000
H35B 2 0.430108 0.839169 0.381112 11.00000 -1.20000
AFIX 0
C36 1 0.222105 0.746889 0.400527 11.00000 0.02145 0.02365 =
0.02176 0.00055 -0.00119 -0.00029
C37 1 0.139955 0.734909 0.446057 11.00000 0.02002 0.02664 =
0.02127 -0.00038 0.00210 -0.00176
AFIX 13
H37 2 0.108051 0.814485 0.454695 11.00000 -1.20000
AFIX 0
C38 1 0.285635 0.631065 0.382821 11.00000 0.03495 0.03160 =
0.02590 -0.00273 0.00563 -0.00543
AFIX 137
H38A 2 0.365182 0.596178 0.405898 11.00000 -1.50000
H38B 2 0.341225 0.644844 0.355516 11.00000 -1.50000
H38C 2 0.190641 0.578987 0.375859 11.00000 -1.50000
AFIX 0
C39 1 -0.028177 0.669549 0.432186 11.00000 0.02471 0.05024 =
0.02507 0.00156 0.00052 -0.00895
AFIX 23
H39A 2 -0.115824 0.693063 0.451462 11.00000 -1.20000
H39B 2 -0.011951 0.585285 0.434768 11.00000 -1.20000
AFIX 0
C40 1 -0.077652 0.705456 0.381718 11.00000 0.02359 0.07060 =
0.02610 0.00290 -0.00372 -0.01284
AFIX 23
H40A 2 -0.084838 0.636774 0.361998 11.00000 -1.20000
H40B 2 -0.187483 0.744894 0.378674 11.00000 -1.20000
AFIX 0
C41 1 0.063610 0.788946 0.368427 11.00000 0.02444 0.04438 =
0.02090 0.00193 -0.00112 -0.00251
C42 1 0.015859 0.916417 0.373827 11.00000 0.03687 0.05540 =
0.03254 0.00950 -0.01313 0.01210
AFIX 137
H42A 2 -0.088157 0.932839 0.354901 11.00000 -1.50000
H42B 2 0.105615 0.965557 0.364610 11.00000 -1.50000
H42C 2 -0.000207 0.931812 0.405399 11.00000 -1.50000
AFIX 0
C43 1 0.718450 0.711401 0.778668 11.00000 0.02150 0.02213 =
0.02196 0.00348 -0.00130 0.00378
C44 1 0.547455 0.659766 0.764574 11.00000 0.01722 0.02528 =
0.01786 0.00135 0.00270 0.00154
C45 1 0.528482 0.552388 0.741742 11.00000 0.02169 0.02734 =
0.01420 0.00097 0.00188 -0.00072
C46 1 0.676864 0.470807 0.738865 11.00000 0.02358 0.03306 =
0.02123 -0.00040 0.00049 0.00027
C47 1 0.366428 0.514462 0.724060 11.00000 0.02740 0.03089 =
0.02299 -0.00654 -0.00195 -0.00617
AFIX 43
H47 2 0.353340 0.442961 0.708749 11.00000 -1.20000
AFIX 0
C48 1 0.224772 0.584193 0.729472 11.00000 0.01482 0.04626 =
0.02550 -0.00227 -0.00058 -0.00417
AFIX 43
H48 2 0.116747 0.559212 0.717638 11.00000 -1.20000
AFIX 0
C49 1 0.243077 0.689342 0.752087 11.00000 0.01566 0.03162 =
0.03010 0.00126 0.00485 0.00253
AFIX 43
H49 2 0.147841 0.735824 0.755389 11.00000 -1.20000
AFIX 0
C50 1 0.403395 0.726410 0.770031 11.00000 0.02082 0.02864 =
0.02676 0.00018 0.00412 -0.00131
AFIX 43
H50 2 0.414675 0.797073 0.785988 11.00000 -1.20000
AFIX 0
C51 1 0.293106 0.205103 0.768189 11.00000 0.02682 0.01914 =
0.02686 0.00029 -0.00381 -0.00336
C52 1 0.450997 0.137998 0.761129 11.00000 0.02227 0.03257 =
0.02191 0.00610 0.00048 -0.00133
C53 1 0.444665 0.038066 0.733647 11.00000 0.02128 0.03415 =
0.01695 0.00452 0.00127 -0.00067
C54 1 0.278096 -0.021283 0.719539 11.00000 0.02112 0.02552 =
0.01878 -0.00002 -0.00154 0.00551
C55 1 0.596147 -0.015892 0.723757 11.00000 0.02777 0.03210 =
0.03253 -0.00068 0.00956 0.00245
AFIX 43
H55 2 0.592217 -0.081774 0.704885 11.00000 -1.20000
AFIX 0
C56 1 0.751155 0.028109 0.741846 11.00000 0.02043 0.05211 =
0.04515 0.00988 0.00295 -0.00090
AFIX 43
H56 2 0.851837 -0.007645 0.734956 11.00000 -1.20000
AFIX 0
C57 1 0.757587 0.124565 0.770012 11.00000 0.01803 0.05261 =
0.05891 0.01187 -0.00337 -0.00921
AFIX 43
H57 2 0.862694 0.152869 0.782707 11.00000 -1.20000
AFIX 0
C58 1 0.608594 0.180213 0.779708 11.00000 0.02653 0.03638 =
0.03709 0.00479 -0.00543 -0.00450
AFIX 43
H58 2 0.614109 0.245926 0.798684 11.00000 -1.20000
AFIX 0
HKLF 4
REM 2 in P2(1)
REM R1 = 0.0511 for 6766 Fo > 4sig(Fo) and 0.0764 for all 8760 data
REM 687 parameters refined using 9 restraints
END
WGHT 0.0510 0.0000
REM Instructions for potential hydrogen bonds
HTAB O1 O5_$1
HTAB O2 O7_$2
HTAB O4 N1_$3
HTAB O6 O2_$4
HTAB O8 O1_$4
HTAB O10 N3_$5
HTAB N2 O9_$6
HTAB N4 O3
HTAB C4 O8_$6
REM Highest difference peak 0.187, deepest hole -0.255, 1-sigma level 0.048
Q1 1 -0.0929 0.8691 -0.1612 11.00000 0.05 0.19
Q2 1 0.0203 0.8378 0.5121 11.00000 0.05 0.18
Q3 1 0.8390 0.9378 0.0720 11.00000 0.05 0.17
Q4 1 0.7787 -0.0657 0.6778 11.00000 0.05 0.17
Q5 1 -0.2407 0.9353 0.3796 11.00000 0.05 0.16
Q6 1 0.5028 0.3901 0.8191 11.00000 0.05 0.16
Q7 1 0.4233 0.8719 0.0482 11.00000 0.05 0.16
Q8 1 0.5186 0.7576 0.7008 11.00000 0.05 0.16
Q9 1 -0.2578 0.9401 0.3380 11.00000 0.05 0.16
Q10 1 0.9300 0.7594 0.0083 11.00000 0.05 0.16
;
_shelx_res_checksum 49749