# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016
#######################################################################
#
# 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.
#
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data_ptac
_database_code_depnum_ccdc_archive 'CCDC 918727'
_audit_update_record
;
2016-08-25 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_date 2016-08-15
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C10 H7 N4 O8, C H9 N6'
_chemical_formula_sum 'C11 H16 N10 O8'
_chemical_formula_weight 416.34
_chemical_melting_point ?
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'
_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.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7785(4)
_cell_length_b 9.7547(4)
_cell_length_c 10.2957(5)
_cell_angle_alpha 93.527(2)
_cell_angle_beta 101.291(2)
_cell_angle_gamma 102.406(2)
_cell_volume 839.43(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3845
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 56.195
_cell_measurement_theta_min 4.864
_shelx_estimated_absorpt_T_max 0.959
_shelx_estimated_absorpt_T_min 0.946
_exptl_absorpt_coefficient_mu 0.141
_exptl_absorpt_correction_T_max 0.9590
_exptl_absorpt_correction_T_min 0.9459
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.647
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 432
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.3
_exptl_special_details
;
SADABS 1999, Bruker AXS, Madison, WI, USA
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0150
_diffrn_reflns_av_unetI/netI 0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 5492
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.997
_diffrn_reflns_theta_min 2.814
_diffrn_ambient_temperature 296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type
'Bruker Kappa APEX-II diffractometer with CCD detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2730
_reflns_number_total 3221
_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.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection 'APEX2 (Bruker, 2004)'
_computing_data_reduction 'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 0.293
_refine_diff_density_min -0.267
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_hydrogen_treatment refxyz
_refine_ls_matrix_type full
_refine_ls_number_parameters 318
_refine_ls_number_reflns 3221
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0437
_refine_ls_R_factor_gt 0.0373
_refine_ls_restrained_S_all 1.059
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1066
_refine_ls_wR_factor_ref 0.1137
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, H6 of N6, H1 of N1
At 1.5 times of:
All N(H,H) groups, H8A of N8, All O(H) groups
2. Restrained distances
N5-H5A
0.85 with sigma of 0.01
N5-H5B
0.85 with sigma of 0.01
H5A-H5B
1.388291 with sigma of 0.03
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary ?
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
O2 O 1.21416(12) 1.47343(11) -0.20622(11) 0.0359(3) Uani 1 1 d . . . . .
O3 O 1.13761(14) 1.01323(13) 0.23002(12) 0.0444(3) Uani 1 1 d . . . . .
O4 O 0.89409(14) 1.05570(13) 0.20824(12) 0.0412(3) Uani 1 1 d . . . . .
O1 O 1.40989(13) 1.36760(13) -0.12970(12) 0.0415(3) Uani 1 1 d . . . . .
N8 N 0.5284(2) 1.09717(17) 0.69711(17) 0.0490(4) Uani 1 1 d . . . . .
H8A H 0.628(3) 1.142(3) 0.742(2) 0.073 Uiso 1 1 d R . . . .
N7 N 0.48237(17) 0.99713(14) 0.78436(16) 0.0407(3) Uani 1 1 d . . . . .
N9 N 0.39121(15) 0.76516(14) 0.81526(13) 0.0341(3) Uani 1 1 d . . . . .
O8 O 0.56315(12) 0.50353(12) 0.72391(11) 0.0368(3) Uani 1 1 d . . . . .
H8 H 0.494(2) 0.4412(19) 0.7889(19) 0.055 Uiso 1 1 d R . . . .
O5 O 1.08096(14) 0.82760(15) 0.39563(14) 0.0502(3) Uani 1 1 d . . . . .
O6 O 0.83797(14) 0.86963(13) 0.37528(13) 0.0472(3) Uani 1 1 d . . . . .
O7 O 0.76547(13) 0.41207(12) 0.81453(11) 0.0384(3) Uani 1 1 d . . . . .
C1 C 1.27137(16) 1.38956(15) -0.13697(14) 0.0275(3) Uani 1 1 d . . . . .
C2 C 1.17301(16) 1.30622(14) -0.05454(14) 0.0268(3) Uani 1 1 d . . . . .
N6 N 0.42889(16) 0.82477(14) 0.60934(14) 0.0386(3) Uani 1 1 d . . . . .
H6 H 0.451(2) 0.899(2) 0.554(2) 0.046 Uiso 1 1 d R . . . .
N5 N 0.37084(17) 0.68652(14) 0.54699(14) 0.0375(3) Uani 1 1 d D . . . .
C3 C 1.20497(17) 1.21167(16) 0.03467(15) 0.0299(3) Uani 1 1 d . . . . .
H3 H 1.305(2) 1.1761(18) 0.0618(17) 0.036 Uiso 1 1 d R . . . .
C4 C 1.06525(17) 1.17213(15) 0.08192(14) 0.0281(3) Uani 1 1 d . . . . .
C5 C 1.03268(17) 1.07341(15) 0.18029(14) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.95324(15) 1.23672(14) 0.02588(13) 0.0327(3) Uani 1 1 d . . . . .
N1 N 1.02178(15) 1.31740(13) -0.05601(13) 0.0308(3) Uani 1 1 d . . . . .
H1 H 0.958(2) 1.3635(19) -0.1044(18) 0.037 Uiso 1 1 d R . . . .
C11 C 0.43258(16) 0.86223(15) 0.73606(15) 0.0317(3) Uani 1 1 d . . . . .
N10 N 0.39540(17) 0.80739(15) 0.95018(14) 0.0352(3) Uani 1 1 d . . . . .
C10 C 0.70801(16) 0.48847(15) 0.73927(14) 0.0270(3) Uani 1 1 d . . . . .
C9 C 0.80347(16) 0.57350(14) 0.65662(14) 0.0262(3) Uani 1 1 d . . . . .
C8 C 0.76823(18) 0.66363(16) 0.56413(15) 0.0307(3) Uani 1 1 d . . . . .
H8C H 0.672(2) 0.6926(18) 0.5312(17) 0.037 Uiso 1 1 d R . . . .
C7 C 0.91038(17) 0.70909(15) 0.52140(14) 0.0281(3) Uani 1 1 d . . . . .
C6 C 0.94263(18) 0.80902(16) 0.42430(15) 0.0316(3) Uani 1 1 d . . . . .
N3 N 1.02606(14) 0.65190(13) 0.58361(12) 0.0301(3) Uani 1 1 d . . . . .
N4 N 0.95798(15) 0.57029(13) 0.66441(12) 0.0283(3) Uani 1 1 d . . . . .
H5A H 0.420(2) 0.6315(17) 0.5920(16) 0.042 Uiso 1 1 d DR . . . .
H5B H 0.2711(12) 0.6575(18) 0.5461(18) 0.042 Uiso 1 1 d DR . . . .
H9 H 0.345(2) 0.676(2) 0.7793(19) 0.046(5) Uiso 1 1 d . . . . .
H7 H 0.492(3) 1.021(2) 0.882(2) 0.060(6) Uiso 1 1 d . . . . .
H10A H 0.289(2) 0.7943(19) 0.9616(18) 0.039(5) Uiso 1 1 d . . . . .
H10B H 0.435(2) 0.749(2) 1.001(2) 0.043(5) Uiso 1 1 d . . . . .
H8B H 0.462(3) 1.155(3) 0.694(2) 0.070(7) Uiso 1 1 d . . . . .
H4 H 1.017(2) 0.5270(19) 0.7117(18) 0.036(5) Uiso 1 1 d . . . . .
H4A H 0.871(3) 0.984(3) 0.267(3) 0.095(9) Uiso 1 1 d . . . . .
H5 H 1.108(4) 0.906(3) 0.330(3) 0.112(10) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0283(6) 0.0395(6) 0.0453(6) 0.0258(5) 0.0119(5) 0.0102(4)
O3 0.0388(6) 0.0560(7) 0.0510(7) 0.0349(6) 0.0199(5) 0.0205(5)
O4 0.0349(6) 0.0487(7) 0.0506(7) 0.0263(5) 0.0237(5) 0.0132(5)
O1 0.0264(6) 0.0564(7) 0.0527(7) 0.0359(6) 0.0192(5) 0.0155(5)
N8 0.0525(10) 0.0353(7) 0.0643(11) 0.0179(7) 0.0250(8) 0.0063(7)
N7 0.0439(8) 0.0310(7) 0.0485(9) 0.0093(6) 0.0172(6) 0.0036(6)
N9 0.0335(7) 0.0316(7) 0.0384(7) 0.0094(5) 0.0112(5) 0.0054(5)
O8 0.0260(5) 0.0495(6) 0.0450(6) 0.0285(5) 0.0170(5) 0.0151(5)
O5 0.0351(7) 0.0661(8) 0.0638(8) 0.0410(7) 0.0271(6) 0.0181(6)
O6 0.0378(7) 0.0589(8) 0.0586(8) 0.0401(6) 0.0218(6) 0.0208(6)
O7 0.0293(6) 0.0495(7) 0.0450(6) 0.0295(5) 0.0133(5) 0.0159(5)
C1 0.0237(7) 0.0310(7) 0.0296(7) 0.0133(6) 0.0086(6) 0.0050(5)
C2 0.0223(7) 0.0300(7) 0.0304(7) 0.0118(6) 0.0090(5) 0.0052(5)
N6 0.0414(8) 0.0348(7) 0.0399(7) 0.0113(6) 0.0126(6) 0.0038(6)
N5 0.0320(7) 0.0367(7) 0.0453(8) 0.0057(6) 0.0110(6) 0.0080(6)
C3 0.0237(7) 0.0356(8) 0.0340(8) 0.0167(6) 0.0095(6) 0.0078(6)
C4 0.0269(7) 0.0304(7) 0.0293(7) 0.0113(6) 0.0098(6) 0.0063(6)
C5 0.0277(7) 0.0329(7) 0.0308(7) 0.0117(6) 0.0112(6) 0.0060(6)
N2 0.0271(6) 0.0393(7) 0.0379(7) 0.0198(5) 0.0152(5) 0.0093(5)
N1 0.0258(6) 0.0373(7) 0.0356(7) 0.0203(5) 0.0127(5) 0.0107(5)
C11 0.0217(7) 0.0342(8) 0.0413(8) 0.0108(6) 0.0081(6) 0.0082(6)
N10 0.0299(7) 0.0412(7) 0.0374(7) 0.0109(6) 0.0113(6) 0.0092(6)
C10 0.0257(7) 0.0299(7) 0.0288(7) 0.0112(6) 0.0097(6) 0.0077(5)
C9 0.0236(7) 0.0288(7) 0.0283(7) 0.0094(5) 0.0091(5) 0.0058(5)
C8 0.0250(7) 0.0375(8) 0.0341(8) 0.0163(6) 0.0100(6) 0.0104(6)
C7 0.0263(7) 0.0311(7) 0.0301(7) 0.0126(6) 0.0101(6) 0.0073(6)
C6 0.0292(8) 0.0363(8) 0.0334(8) 0.0150(6) 0.0124(6) 0.0082(6)
N3 0.0264(6) 0.0347(6) 0.0340(7) 0.0162(5) 0.0131(5) 0.0077(5)
N4 0.0236(6) 0.0338(6) 0.0324(6) 0.0162(5) 0.0107(5) 0.0094(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
O2 C1 1.2402(17) . ?
O3 C5 1.2409(18) . ?
O4 C5 1.2829(17) . ?
O4 H4A 0.97(3) . ?
O1 C1 1.2681(17) . ?
N8 H8A 0.91(3) . ?
N8 N7 1.415(2) . ?
N8 H8B 0.89(3) . ?
N7 C11 1.326(2) . ?
N7 H7 1.01(2) . ?
N9 C11 1.325(2) . ?
N9 N10 1.4155(19) . ?
N9 H9 0.90(2) . ?
O8 H8 1.11(2) . ?
O8 C10 1.2916(17) . ?
O5 C6 1.2834(18) . ?
O5 H5 1.07(4) . ?
O6 C6 1.2398(19) . ?
O7 C10 1.2206(17) . ?
C1 C2 1.4822(18) . ?
C2 C3 1.3739(19) . ?
C2 N1 1.3524(18) . ?
N6 H6 0.96(2) . ?
N6 N5 1.4002(19) . ?
N6 C11 1.325(2) . ?
N5 H5A 0.859(9) . ?
N5 H5B 0.858(9) . ?
C3 H3 1.011(18) . ?
C3 C4 1.394(2) . ?
C4 C5 1.4662(19) . ?
C4 N2 1.3363(19) . ?
N2 N1 1.3301(16) . ?
N1 H1 0.889(19) . ?
N10 H10A 0.95(2) . ?
N10 H10B 0.88(2) . ?
C10 C9 1.4770(18) . ?
C9 C8 1.371(2) . ?
C9 N4 1.3501(18) . ?
C8 H8C 0.956(19) . ?
C8 C7 1.396(2) . ?
C7 C6 1.4635(19) . ?
C7 N3 1.3362(19) . ?
N3 N4 1.3247(16) . ?
N4 H4 0.842(19) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O4 H4A 115.1(17) . . ?
H8A N8 H8B 111(2) . . ?
N7 N8 H8A 101.6(16) . . ?
N7 N8 H8B 105.8(16) . . ?
N8 N7 H7 124.2(13) . . ?
C11 N7 N8 118.27(14) . . ?
C11 N7 H7 117.4(13) . . ?
C11 N9 N10 119.44(13) . . ?
C11 N9 H9 119.1(13) . . ?
N10 N9 H9 120.6(13) . . ?
C10 O8 H8 113.0(9) . . ?
C6 O5 H5 116.5(17) . . ?
O2 C1 O1 125.45(13) . . ?
O2 C1 C2 118.88(12) . . ?
O1 C1 C2 115.67(12) . . ?
C3 C2 C1 132.19(13) . . ?
N1 C2 C1 121.41(12) . . ?
N1 C2 C3 106.38(12) . . ?
N5 N6 H6 117.7(11) . . ?
C11 N6 H6 117.4(11) . . ?
C11 N6 N5 124.10(13) . . ?
N6 N5 H5A 109.0(12) . . ?
N6 N5 H5B 110.8(12) . . ?
H5A N5 H5B 106.9(17) . . ?
C2 C3 H3 129.4(10) . . ?
C2 C3 C4 104.57(12) . . ?
C4 C3 H3 126.1(10) . . ?
C3 C4 C5 128.08(13) . . ?
N2 C4 C3 111.72(12) . . ?
N2 C4 C5 120.20(13) . . ?
O3 C5 O4 124.66(13) . . ?
O3 C5 C4 119.21(13) . . ?
O4 C5 C4 116.13(13) . . ?
N1 N2 C4 104.39(11) . . ?
C2 N1 H1 132.6(12) . . ?
N2 N1 C2 112.93(12) . . ?
N2 N1 H1 114.3(12) . . ?
N9 C11 N7 120.02(15) . . ?
N9 C11 N6 120.31(14) . . ?
N6 C11 N7 119.63(14) . . ?
N9 N10 H10A 108.3(11) . . ?
N9 N10 H10B 109.4(12) . . ?
H10A N10 H10B 103.9(17) . . ?
O8 C10 C9 114.11(12) . . ?
O7 C10 O8 124.75(13) . . ?
O7 C10 C9 121.14(13) . . ?
C8 C9 C10 132.82(13) . . ?
N4 C9 C10 120.54(12) . . ?
N4 C9 C8 106.64(12) . . ?
C9 C8 H8C 131.5(11) . . ?
C9 C8 C7 104.29(12) . . ?
C7 C8 H8C 124.2(11) . . ?
C8 C7 C6 128.06(13) . . ?
N3 C7 C8 111.69(12) . . ?
N3 C7 C6 120.23(13) . . ?
O5 C6 C7 116.33(13) . . ?
O6 C6 O5 124.22(13) . . ?
O6 C6 C7 119.45(13) . . ?
N4 N3 C7 104.44(11) . . ?
C9 N4 H4 131.4(13) . . ?
N3 N4 C9 112.94(12) . . ?
N3 N4 H4 115.6(13) . . ?
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
N8 H8A O7 0.91(3) 2.64(3) 3.322(2) 132.2(19) 1_565
O8 H8 O1 1.11(2) 1.36(2) 2.4725(14) 178.6(17) 1_446
N6 H6 N8 0.96(2) 2.63(2) 3.363(2) 133.8(14) 2_676
N1 H1 O7 0.889(19) 1.902(19) 2.7499(16) 158.9(17) 1_564
N5 H5A O8 0.859(9) 2.281(10) 3.1377(17) 174.7(17) .
N5 H5B N3 0.858(9) 2.249(11) 3.0725(18) 160.8(17) 1_455
N9 H9 O2 0.90(2) 2.09(2) 2.9070(17) 150.3(17) 1_446
N7 H7 N10 1.01(2) 2.24(2) 3.097(2) 142.1(18) 2_677
N10 H10A N2 0.95(2) 2.11(2) 3.0587(18) 176.5(16) 2_676
N10 H10B O1 0.88(2) 2.25(2) 3.1075(17) 166.8(17) 2_776
N8 H8B O6 0.89(3) 2.54(3) 3.247(2) 136.4(19) 2_676
N4 H4 O2 0.842(19) 1.960(19) 2.7603(16) 158.5(18) 1_546
O4 H4A O6 0.97(3) 1.65(3) 2.6128(14) 176(3) .
O5 H5 O3 1.07(4) 1.53(4) 2.5997(15) 177(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
O2 C1 C2 C3 -176.83(15) . . . . ?
O2 C1 C2 N1 1.6(2) . . . . ?
O1 C1 C2 C3 3.2(2) . . . . ?
O1 C1 C2 N1 -178.36(14) . . . . ?
N8 N7 C11 N9 178.77(15) . . . . ?
N8 N7 C11 N6 0.7(2) . . . . ?
O8 C10 C9 C8 -1.6(2) . . . . ?
O8 C10 C9 N4 178.70(13) . . . . ?
O7 C10 C9 C8 178.51(15) . . . . ?
O7 C10 C9 N4 -1.2(2) . . . . ?
C1 C2 C3 C4 178.49(15) . . . . ?
C1 C2 N1 N2 -178.85(13) . . . . ?
C2 C3 C4 C5 -179.69(14) . . . . ?
C2 C3 C4 N2 0.29(18) . . . . ?
N5 N6 C11 N7 -176.61(14) . . . . ?
N5 N6 C11 N9 5.4(2) . . . . ?
C3 C2 N1 N2 -0.04(17) . . . . ?
C3 C4 C5 O3 -0.9(2) . . . . ?
C3 C4 C5 O4 179.33(15) . . . . ?
C3 C4 N2 N1 -0.31(17) . . . . ?
C4 N2 N1 C2 0.22(17) . . . . ?
C5 C4 N2 N1 179.67(13) . . . . ?
N2 C4 C5 O3 179.15(14) . . . . ?
N2 C4 C5 O4 -0.7(2) . . . . ?
N1 C2 C3 C4 -0.15(16) . . . . ?
N10 N9 C11 N7 2.2(2) . . . . ?
N10 N9 C11 N6 -179.77(13) . . . . ?
C10 C9 C8 C7 -179.50(15) . . . . ?
C10 C9 N4 N3 179.76(13) . . . . ?
C9 C8 C7 C6 -178.80(15) . . . . ?
C9 C8 C7 N3 -0.37(18) . . . . ?
C8 C9 N4 N3 0.00(17) . . . . ?
C8 C7 C6 O5 -175.98(15) . . . . ?
C8 C7 C6 O6 4.0(3) . . . . ?
C8 C7 N3 N4 0.37(17) . . . . ?
C7 N3 N4 C9 -0.22(16) . . . . ?
C6 C7 N3 N4 178.94(13) . . . . ?
N3 C7 C6 O5 5.7(2) . . . . ?
N3 C7 C6 O6 -174.33(15) . . . . ?
N4 C9 C8 C7 0.22(16) . . . . ?
_shelx_res_file
;
ptac.res created by SHELXL-2014/7
TITL PTAG in P-1
CELL 0.71073 8.7785 9.7547 10.2957 93.527 101.291 102.406
ZERR 2 0.0004 0.0004 0.0005 0.002 0.002 0.002
LATT 1
SFAC C H N O
UNIT 22 32 20 16
EQIV $1 -1+X,-1+Y,1+Z
EQIV $2 +X,1+Y,-1+Z
EQIV $3 +X,-1+Y,1+Z
EQIV $4 1-X,2-Y,1-Z
EQIV $5 +X,1+Y,+Z
EQIV $6 1-X,2-Y,2-Z
EQIV $7 -1+X,+Y,+Z
EQIV $8 2-X,2-Y,1-Z
DFIX 0.85 0.01 N5 H5a
DFIX 0.85 0.01 N5 H5b
DANG 1.388291 0.03 H5a H5b
L.S. 10
PLAN 20
SIZE 0.3 0.35 0.4
TEMP 23(2)
HTAB O4 O6
HTAB O8 O1_$1
HTAB O5 O3
HTAB N1 O7_$2
HTAB N4 O2_$3
HTAB N8 O6_$4
HTAB N8 O7_$5
HTAB N7 N10_$6
HTAB N9 O2_$1
HTAB N6 N8_$4
HTAB N5 O8
HTAB N5 N3_$7
HTAB N10 O1_$8
HTAB N10 N2_$4
BOND $H
CONF
MORE -1
fmap 2
acta
MERG 2
OMIT -3 52
OMIT 0 -1 1
OMIT -1 -5 7
REM
REM
REM
WGHT 0.067100 0.194400
FVAR 0.33592
O2 4 1.214158 1.473426 -0.206221 11.00000 0.02826 0.03952 =
0.04533 0.02576 0.01190 0.01018
O3 4 1.137606 1.013228 0.230018 11.00000 0.03876 0.05596 =
0.05098 0.03495 0.01994 0.02049
O4 4 0.894087 1.055705 0.208235 11.00000 0.03490 0.04867 =
0.05061 0.02634 0.02374 0.01315
O1 4 1.409888 1.367604 -0.129702 11.00000 0.02640 0.05640 =
0.05275 0.03588 0.01916 0.01548
N8 3 0.528421 1.097172 0.697113 11.00000 0.05251 0.03527 =
0.06426 0.01787 0.02501 0.00634
H8A 2 0.628147 1.141929 0.741936 11.00000 -1.50000
N7 3 0.482368 0.997127 0.784360 11.00000 0.04389 0.03095 =
0.04854 0.00933 0.01717 0.00360
N9 3 0.391211 0.765157 0.815263 11.00000 0.03347 0.03161 =
0.03842 0.00944 0.01119 0.00541
O8 4 0.563151 0.503529 0.723912 11.00000 0.02603 0.04948 =
0.04498 0.02855 0.01700 0.01513
H8 2 0.494449 0.441188 0.788882 11.00000 -1.50000
O5 4 1.080963 0.827595 0.395631 11.00000 0.03509 0.06613 =
0.06385 0.04099 0.02706 0.01815
O6 4 0.837974 0.869632 0.375280 11.00000 0.03783 0.05891 =
0.05863 0.04010 0.02175 0.02076
O7 4 0.765467 0.412065 0.814525 11.00000 0.02934 0.04952 =
0.04499 0.02949 0.01326 0.01590
C1 1 1.271374 1.389557 -0.136970 11.00000 0.02372 0.03104 =
0.02956 0.01334 0.00859 0.00497
C2 1 1.173009 1.306221 -0.054540 11.00000 0.02226 0.02996 =
0.03036 0.01181 0.00903 0.00517
N6 3 0.428890 0.824775 0.609335 11.00000 0.04143 0.03478 =
0.03992 0.01130 0.01259 0.00378
H6 2 0.451389 0.898641 0.554149 11.00000 -1.20000
N5 3 0.370839 0.686523 0.546992 11.00000 0.03196 0.03669 =
0.04527 0.00569 0.01100 0.00798
C3 1 1.204967 1.211665 0.034670 11.00000 0.02368 0.03560 =
0.03403 0.01667 0.00950 0.00780
H3 2 1.305419 1.176106 0.061812 11.00000 -1.20000
C4 1 1.065251 1.172129 0.081923 11.00000 0.02694 0.03043 =
0.02930 0.01129 0.00976 0.00633
C5 1 1.032681 1.073412 0.180291 11.00000 0.02768 0.03289 =
0.03080 0.01169 0.01118 0.00601
N2 3 0.953239 1.236720 0.025878 11.00000 0.02708 0.03926 =
0.03794 0.01983 0.01525 0.00929
N1 3 1.021780 1.317402 -0.056013 11.00000 0.02581 0.03731 =
0.03563 0.02032 0.01269 0.01070
H1 2 0.957936 1.363513 -0.104364 11.00000 -1.20000
C11 1 0.432576 0.862228 0.736058 11.00000 0.02174 0.03419 =
0.04130 0.01076 0.00810 0.00818
N10 3 0.395398 0.807388 0.950176 11.00000 0.02991 0.04123 =
0.03736 0.01094 0.01131 0.00920
C10 1 0.708014 0.488473 0.739269 11.00000 0.02571 0.02993 =
0.02878 0.01120 0.00974 0.00772
C9 1 0.803474 0.573497 0.656620 11.00000 0.02363 0.02884 =
0.02833 0.00939 0.00914 0.00582
C8 1 0.768234 0.663633 0.564128 11.00000 0.02501 0.03749 =
0.03409 0.01626 0.01004 0.01035
H8C 2 0.671743 0.692606 0.531174 11.00000 -1.20000
C7 1 0.910378 0.709090 0.521403 11.00000 0.02627 0.03106 =
0.03013 0.01257 0.01012 0.00728
C6 1 0.942633 0.809019 0.424304 11.00000 0.02916 0.03633 =
0.03344 0.01496 0.01238 0.00824
N3 3 1.026058 0.651899 0.583605 11.00000 0.02640 0.03469 =
0.03404 0.01620 0.01313 0.00768
N4 3 0.957976 0.570293 0.664410 11.00000 0.02363 0.03376 =
0.03241 0.01622 0.01075 0.00938
H5A 2 0.419690 0.631484 0.591997 11.00000 -1.50000
H5B 2 0.271149 0.657520 0.546082 11.00000 -1.50000
H9 2 0.345295 0.675894 0.779327 11.00000 0.04642
H7 2 0.491858 1.020708 0.882479 11.00000 0.05966
H10A 2 0.288628 0.794259 0.961555 11.00000 0.03923
H10B 2 0.434836 0.748872 1.000629 11.00000 0.04257
H8B 2 0.461725 1.154832 0.694288 11.00000 0.06991
H4 2 1.017420 0.526995 0.711750 11.00000 0.03649
H4A 2 0.870881 0.984082 0.267010 11.00000 0.09537
H5 2 1.107879 0.906010 0.329690 11.00000 0.11187
HKLF 4
REM PTAG in P-1
REM R1 = 0.0373 for 2730 Fo > 4sig(Fo) and 0.0437 for all 3221 data
REM 318 parameters refined using 3 restraints
END
WGHT 0.0671 0.1944
REM Highest difference peak 0.293, deepest hole -0.267, 1-sigma level 0.044
Q1 1 0.7595 0.5336 0.6877 11.00000 0.05 0.29
Q2 1 1.0543 1.1306 0.1284 11.00000 0.05 0.25
Q3 1 0.9234 0.7504 0.4842 11.00000 0.05 0.24
Q4 1 0.7907 0.6419 0.6367 11.00000 0.05 0.23
Q5 1 1.2157 1.3331 -0.0925 11.00000 0.05 0.23
Q6 1 0.8627 0.9249 0.3367 11.00000 0.05 0.22
Q7 1 1.2122 1.2821 0.0032 11.00000 0.05 0.21
Q8 1 1.1152 0.9603 0.2572 11.00000 0.05 0.20
Q9 1 0.7705 0.5961 0.5940 11.00000 0.05 0.20
Q10 1 1.0346 1.1072 0.1017 11.00000 0.05 0.20
Q11 1 0.4224 0.9124 0.9561 11.00000 0.05 0.20
Q12 1 1.1829 1.2363 -0.0344 11.00000 0.05 0.19
Q13 1 1.1424 1.1935 0.0827 11.00000 0.05 0.18
Q14 1 0.5423 1.0447 0.6215 11.00000 0.05 0.18
Q15 1 0.9497 0.6532 0.5189 11.00000 0.05 0.17
Q16 1 1.2607 1.4770 -0.1400 11.00000 0.05 0.17
Q17 1 0.8932 0.6019 0.6963 11.00000 0.05 0.17
Q18 1 0.8411 0.4436 0.8739 11.00000 0.05 0.16
Q19 1 0.8633 0.7322 0.5685 11.00000 0.05 0.16
Q20 1 1.0235 0.7884 0.3783 11.00000 0.05 0.16
;
_shelx_res_checksum 13385
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_preparation ', Luminescent'
#######################################################################
#
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 955243'
_audit_update_record
;
2016-08-25 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_date 2016-08-15
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'H2 O, C5 H3 N2 O4, C H6 N3'
_chemical_formula_sum 'C6 H11 N5 O5'
_chemical_formula_weight 233.20
_chemical_melting_point ?
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'
_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.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 12.7602(4)
_cell_length_b 9.0277(4)
_cell_length_c 17.1544(7)
_cell_angle_alpha 90
_cell_angle_beta 95.503(3)
_cell_angle_gamma 90
_cell_volume 1967.00(13)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 4663
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 56.212
_cell_measurement_theta_min 4.771
_shelx_estimated_absorpt_T_max 0.973
_shelx_estimated_absorpt_T_min 0.960
_exptl_absorpt_coefficient_mu 0.137
_exptl_absorpt_correction_T_max 0.9732
_exptl_absorpt_correction_T_min 0.9601
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.575
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 976
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
SADABS (1999) Bruker AXS, Madison, EI, USA
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0163
_diffrn_reflns_av_unetI/netI 0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 7327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.314
_diffrn_reflns_theta_min 2.768
_diffrn_ambient_temperature 296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type 'Bruker AXS Kappa Apex 2 CCD diffractomer'
_diffrn_measurement_method 'phi and omgea scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2118
_reflns_number_total 2410
_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.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection 'APEX2 (Bruker, 2004)'
_computing_data_reduction 'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'SIR97 (Burla et al., 2007)'
_refine_diff_density_max 0.356
_refine_diff_density_min -0.209
_refine_diff_density_rms 0.041
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.033
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 175
_refine_ls_number_reflns 2410
_refine_ls_number_restraints 10
_refine_ls_R_factor_all 0.0392
_refine_ls_R_factor_gt 0.0342
_refine_ls_restrained_S_all 1.033
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.9335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0955
_refine_ls_wR_factor_ref 0.0996
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H) groups, All
O(H,H) groups
2. Restrained distances
O1S-H1SA = O1S-H1SB = O1-H1
0.86 with sigma of 0.02
N3-H3A = N3-H3B = N4-H4A = N4-H4B = N5-H5A = N5-H5B = N1-H1A
0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
C3(H3)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
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
O1S O 0.14375(9) 0.45120(13) -0.07574(6) 0.0467(3) Uani 1 1 d D . . . .
H1SA H 0.1187(14) 0.3913(19) -0.1118(11) 0.056 Uiso 1 1 d DR . . . .
H1SB H 0.2077(12) 0.422(2) -0.0779(11) 0.056 Uiso 1 1 d DR . . . .
O1 O 0.13367(9) 0.85172(9) 0.17467(5) 0.0403(3) Uani 1 1 d D . . . .
H1 H 0.1326(13) 0.9445(17) 0.1956(10) 0.048 Uiso 1 1 d DR . . . .
O2 O 0.12982(8) 0.12231(9) 0.21471(5) 0.0336(2) Uani 1 1 d . . . . .
O3 O 0.11750(7) 0.75296(9) 0.29200(5) 0.0320(2) Uani 1 1 d . . . . .
O4 O 0.14267(8) 0.13903(9) 0.08569(5) 0.0347(2) Uani 1 1 d . . . . .
N5 N 0.37815(10) 0.71064(12) 0.12138(6) 0.0357(3) Uani 1 1 d D . . . .
H5A H 0.3696(12) 0.8057(16) 0.1096(10) 0.043 Uiso 1 1 d DR . . . .
H5B H 0.3775(12) 0.686(2) 0.1702(8) 0.043 Uiso 1 1 d DR . . . .
N3 N 0.37678(11) 0.64641(12) -0.00802(6) 0.0407(3) Uani 1 1 d D . . . .
H3A H 0.3744(14) 0.7360(16) -0.0243(11) 0.049 Uiso 1 1 d DR . . . .
H3B H 0.3762(14) 0.5769(18) -0.0433(10) 0.049 Uiso 1 1 d DR . . . .
C1 C 0.12383(9) 0.74155(11) 0.22202(6) 0.0243(2) Uani 1 1 d . . . . .
C2 C 0.12197(9) 0.59562(11) 0.18236(6) 0.0231(2) Uani 1 1 d . . . . .
C3 C 0.12590(9) 0.45566(11) 0.21718(6) 0.0258(2) Uani 1 1 d . . . . .
H3 H 0.1285 0.4335 0.2703 0.031 Uiso 1 1 calc R . . . .
C4 C 0.12517(8) 0.35768(11) 0.15572(6) 0.0229(2) Uani 1 1 d . . . . .
C5 C 0.13272(9) 0.19373(11) 0.15145(6) 0.0245(2) Uani 1 1 d . . . . .
N1 N 0.12010(8) 0.44046(10) 0.08999(5) 0.0263(2) Uani 1 1 d D . . . .
H1A H 0.1218(11) 0.4107(16) 0.0428(8) 0.032 Uiso 1 1 d DR . . . .
N2 N 0.11830(8) 0.58571(9) 0.10429(5) 0.0277(2) Uani 1 1 d . . . . .
C6 C 0.37975(9) 0.60879(12) 0.06625(6) 0.0268(2) Uani 1 1 d . . . . .
N4 N 0.38447(10) 0.46594(12) 0.08460(7) 0.0391(3) Uani 1 1 d D . . . .
H4A H 0.3847(13) 0.439(2) 0.1309(9) 0.047 Uiso 1 1 d DR . . . .
H4B H 0.3866(13) 0.4025(18) 0.0474(9) 0.047 Uiso 1 1 d DR . . . .
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
O1S 0.0535(6) 0.0550(6) 0.0314(5) -0.0131(4) 0.0030(4) 0.0020(5)
O1 0.0875(7) 0.0120(4) 0.0223(4) -0.0004(3) 0.0095(4) -0.0013(4)
O2 0.0618(6) 0.0146(4) 0.0248(4) 0.0011(3) 0.0066(4) 0.0013(3)
O3 0.0564(5) 0.0202(4) 0.0195(4) -0.0019(3) 0.0043(3) 0.0004(3)
O4 0.0621(6) 0.0181(4) 0.0246(4) -0.0034(3) 0.0071(4) 0.0024(4)
N5 0.0561(7) 0.0302(5) 0.0211(5) -0.0038(4) 0.0045(4) 0.0004(5)
N3 0.0808(9) 0.0216(5) 0.0197(5) 0.0024(4) 0.0050(5) 0.0000(5)
C1 0.0378(6) 0.0143(4) 0.0207(5) -0.0008(4) 0.0020(4) 0.0011(4)
C2 0.0367(5) 0.0129(5) 0.0197(5) -0.0007(4) 0.0037(4) 0.0008(4)
C3 0.0437(6) 0.0146(5) 0.0193(5) 0.0014(4) 0.0044(4) 0.0011(4)
C4 0.0333(5) 0.0141(5) 0.0215(5) 0.0004(3) 0.0039(4) -0.0002(4)
C5 0.0356(5) 0.0141(5) 0.0241(5) -0.0011(4) 0.0036(4) 0.0001(4)
N1 0.0464(5) 0.0141(4) 0.0186(4) -0.0018(3) 0.0046(4) -0.0002(4)
N2 0.0497(6) 0.0133(4) 0.0203(4) -0.0003(3) 0.0045(4) -0.0001(4)
C6 0.0359(6) 0.0233(5) 0.0212(5) 0.0014(4) 0.0030(4) -0.0001(4)
N4 0.0666(8) 0.0240(5) 0.0270(5) 0.0073(4) 0.0065(5) 0.0031(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
O1S H1SA 0.859(15) . ?
O1S H1SB 0.861(14) . ?
O1 H1 0.912(14) . ?
O1 C1 1.2978(13) . ?
O2 C5 1.2659(13) . ?
O3 C1 1.2154(14) . ?
O4 C5 1.2490(13) . ?
N5 H5A 0.886(14) . ?
N5 H5B 0.868(14) . ?
N5 C6 1.3205(15) . ?
N3 H3A 0.856(14) . ?
N3 H3B 0.871(14) . ?
N3 C6 1.3156(15) . ?
C1 C2 1.4818(14) . ?
C2 C3 1.3964(14) . ?
C2 N2 1.3386(14) . ?
C3 H3 0.9300 . ?
C3 C4 1.3755(15) . ?
C4 C5 1.4854(14) . ?
C4 N1 1.3492(13) . ?
N1 H1A 0.855(13) . ?
N1 N2 1.3346(12) . ?
C6 N4 1.3275(15) . ?
N4 H4A 0.830(14) . ?
N4 H4B 0.860(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
H1SA O1S H1SB 93.9(17) . . ?
C1 O1 H1 116.8(11) . . ?
H5A N5 H5B 117.1(17) . . ?
C6 N5 H5A 121.4(11) . . ?
C6 N5 H5B 121.1(12) . . ?
H3A N3 H3B 117.2(17) . . ?
C6 N3 H3A 123.9(13) . . ?
C6 N3 H3B 119.0(12) . . ?
O1 C1 C2 113.10(9) . . ?
O3 C1 O1 124.95(10) . . ?
O3 C1 C2 121.95(10) . . ?
C3 C2 C1 127.58(10) . . ?
N2 C2 C1 121.08(9) . . ?
N2 C2 C3 111.33(9) . . ?
C2 C3 H3 127.6 . . ?
C4 C3 C2 104.88(9) . . ?
C4 C3 H3 127.6 . . ?
C3 C4 C5 133.07(10) . . ?
N1 C4 C3 106.29(9) . . ?
N1 C4 C5 120.59(9) . . ?
O2 C5 C4 117.25(9) . . ?
O4 C5 O2 125.92(10) . . ?
O4 C5 C4 116.82(9) . . ?
C4 N1 H1A 127.9(10) . . ?
N2 N1 C4 113.01(9) . . ?
N2 N1 H1A 119.0(10) . . ?
N1 N2 C2 104.48(8) . . ?
N5 C6 N4 120.67(11) . . ?
N3 C6 N5 120.85(11) . . ?
N3 C6 N4 118.48(11) . . ?
C6 N4 H4A 120.4(13) . . ?
C6 N4 H4B 118.4(12) . . ?
H4A N4 H4B 121.3(17) . . ?
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
O1S H1SA O3 0.859(15) 2.102(16) 2.9173(13) 158.3(18) 6_565
O1S H1SB O4 0.861(14) 2.004(15) 2.8651(15) 177.8(19) 7
O1 H1 O2 0.912(14) 1.639(15) 2.5393(11) 168.3(17) 1_565
N5 H5A O1S 0.886(14) 2.273(14) 3.1573(17) 176.7(15) 7_565
N5 H5B O2 0.868(14) 2.067(14) 2.9338(14) 177.5(16) 4
N3 H3A N2 0.856(14) 2.123(15) 2.9325(14) 157.8(17) 7_565
N3 H3B O4 0.871(14) 2.087(15) 2.9006(14) 155.2(17) 7
N1 H1A O1S 0.855(13) 2.111(14) 2.8893(14) 151.1(13) .
N4 H4A O3 0.830(14) 2.141(16) 2.8616(13) 145.1(17) 4_545
N4 H4B O4 0.860(14) 2.308(15) 3.0590(15) 146.0(15) 7
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 171.08(12) . . . . ?
O1 C1 C2 N2 -7.40(16) . . . . ?
O3 C1 C2 C3 -8.34(19) . . . . ?
O3 C1 C2 N2 173.18(11) . . . . ?
C1 C2 C3 C4 -178.21(11) . . . . ?
C1 C2 N2 N1 178.60(10) . . . . ?
C2 C3 C4 C5 176.79(12) . . . . ?
C2 C3 C4 N1 -0.51(12) . . . . ?
C3 C2 N2 N1 -0.11(13) . . . . ?
C3 C4 C5 O2 7.80(19) . . . . ?
C3 C4 C5 O4 -171.35(12) . . . . ?
C3 C4 N1 N2 0.48(13) . . . . ?
C4 N1 N2 C2 -0.23(13) . . . . ?
C5 C4 N1 N2 -177.22(10) . . . . ?
N1 C4 C5 O2 -175.22(10) . . . . ?
N1 C4 C5 O4 5.63(16) . . . . ?
N2 C2 C3 C4 0.39(14) . . . . ?
_shelx_res_file
;
c1.res created by SHELXL-2014/7
TITL PYZG1 in C2/c
CELL 0.71073 12.7602 9.0277 17.1544 90 95.503 90
ZERR 8 0.0004 0.0004 0.0007 0 0.003 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 48 88 40 40
EQIV $1 +X,1-Y,-0.5+Z
EQIV $2 0.5-X,0.5-Y,-Z
EQIV $3 +X,1+Y,+Z
EQIV $4 0.5-X,1.5-Y,-Z
EQIV $5 0.5-X,0.5+Y,0.5-Z
EQIV $6 0.5-X,-0.5+Y,0.5-Z
DFIX 0.86 O1S H1Sa O1S H1Sb O1 H1
DFIX 0.86 N3 H3a N3 H3b N4 H4a N4 H4b N5 H5a N5 H5b N1 H1a
L.S. 10
PLAN 20
SIZE 0.2 0.2 0.3
TEMP 23(2)
HTAB O1S O3_$1
HTAB O1S O4_$2
HTAB O1 O2_$3
HTAB N5 O1S_$4
HTAB N5 O2_$5
HTAB N3 O4_$2
HTAB N3 N2_$4
HTAB N1 O1S
HTAB N4 O3_$6
HTAB N4 O4_$2
BOND $H
MORE -1
CONF
fmap 2
acta
MERG 2
REM
REM
REM
WGHT 0.057500 0.933500
FVAR 0.12792
O1S 4 0.143751 0.451200 -0.075744 11.00000 0.05349 0.05497 =
0.03143 -0.01310 0.00297 0.00201
H1SA 2 0.118727 0.391321 -0.111750 11.00000 -1.20000
H1SB 2 0.207717 0.422264 -0.077860 11.00000 -1.20000
O1 4 0.133674 0.851720 0.174665 11.00000 0.08754 0.01203 =
0.02229 -0.00041 0.00946 -0.00130
H1 2 0.132609 0.944483 0.195628 11.00000 -1.20000
O2 4 0.129820 0.122311 0.214711 11.00000 0.06180 0.01464 =
0.02479 0.00106 0.00658 0.00135
O3 4 0.117498 0.752961 0.292003 11.00000 0.05636 0.02020 =
0.01950 -0.00192 0.00426 0.00042
O4 4 0.142674 0.139025 0.085694 11.00000 0.06212 0.01805 =
0.02460 -0.00341 0.00707 0.00239
N5 3 0.378152 0.710639 0.121378 11.00000 0.05606 0.03018 =
0.02107 -0.00378 0.00455 0.00044
H5A 2 0.369623 0.805706 0.109636 11.00000 -1.20000
H5B 2 0.377534 0.686085 0.170232 11.00000 -1.20000
N3 3 0.376784 0.646407 -0.008021 11.00000 0.08083 0.02160 =
0.01969 0.00237 0.00498 0.00002
H3A 2 0.374411 0.736037 -0.024304 11.00000 -1.20000
H3B 2 0.376192 0.576949 -0.043272 11.00000 -1.20000
C1 1 0.123828 0.741550 0.222016 11.00000 0.03780 0.01435 =
0.02070 -0.00083 0.00198 0.00110
C2 1 0.121968 0.595616 0.182364 11.00000 0.03672 0.01292 =
0.01971 -0.00073 0.00371 0.00084
C3 1 0.125905 0.455657 0.217177 11.00000 0.04373 0.01463 =
0.01932 0.00138 0.00440 0.00108
AFIX 43
H3 2 0.128464 0.433539 0.270275 11.00000 -1.20000
AFIX 0
C4 1 0.125168 0.357675 0.155724 11.00000 0.03330 0.01411 =
0.02146 0.00044 0.00395 -0.00019
C5 1 0.132721 0.193732 0.151451 11.00000 0.03562 0.01407 =
0.02408 -0.00108 0.00359 0.00009
N1 3 0.120103 0.440461 0.089991 11.00000 0.04642 0.01408 =
0.01864 -0.00178 0.00460 -0.00024
H1A 2 0.121847 0.410737 0.042809 11.00000 -1.20000
N2 3 0.118296 0.585708 0.104291 11.00000 0.04972 0.01332 =
0.02031 -0.00028 0.00449 -0.00007
C6 1 0.379751 0.608790 0.066251 11.00000 0.03589 0.02330 =
0.02123 0.00139 0.00301 -0.00006
N4 3 0.384467 0.465939 0.084596 11.00000 0.06663 0.02403 =
0.02703 0.00732 0.00650 0.00308
H4A 2 0.384715 0.439181 0.130919 11.00000 -1.20000
H4B 2 0.386632 0.402507 0.047387 11.00000 -1.20000
HKLF 4
REM PYZG1 in C2/c
REM R1 = 0.0342 for 2118 Fo > 4sig(Fo) and 0.0392 for all 2410 data
REM 175 parameters refined using 10 restraints
END
WGHT 0.0575 0.9335
REM Highest difference peak 0.356, deepest hole -0.209, 1-sigma level 0.041
Q1 1 0.1196 0.6617 0.1996 11.00000 0.05 0.36
Q2 1 0.1209 0.5300 0.2029 11.00000 0.05 0.30
Q3 1 0.1359 0.3940 0.1893 11.00000 0.05 0.26
Q4 1 0.1330 0.2835 0.1541 11.00000 0.05 0.26
Q5 1 0.1084 0.5886 0.1434 11.00000 0.05 0.21
Q6 1 0.1523 0.3619 -0.0590 11.00000 0.05 0.20
Q7 1 0.1223 0.3932 0.1227 11.00000 0.05 0.20
Q8 1 0.3574 0.6623 0.0945 11.00000 0.05 0.18
Q9 1 0.3636 0.6352 0.0266 11.00000 0.05 0.16
Q10 1 0.3902 0.6331 0.0291 11.00000 0.05 0.15
Q11 1 0.1222 0.1892 0.0532 11.00000 0.05 0.15
Q12 1 0.1203 0.6333 0.0636 11.00000 0.05 0.15
Q13 1 0.1183 0.1437 0.1907 11.00000 0.05 0.15
Q14 1 0.1605 0.7497 0.2623 11.00000 0.05 0.14
Q15 1 0.3897 0.5404 0.0753 11.00000 0.05 0.14
Q16 1 0.1637 0.0496 0.0785 11.00000 0.05 0.14
Q17 1 0.1253 0.1559 0.1179 11.00000 0.05 0.14
Q18 1 0.1114 0.5227 0.0946 11.00000 0.05 0.12
Q19 1 0.1789 0.4402 0.2729 11.00000 0.05 0.12
Q20 1 0.1333 0.1504 0.2568 11.00000 0.05 0.12
;
_shelx_res_checksum 82975
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_preparation ', Luminescent'
#######################################################################
#
# 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_rpg
_database_code_depnum_ccdc_archive 'CCDC 955244'
_audit_update_record
;
2016-08-25 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_date 2016-08-15
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C5 H2 N2 O4, 2(C H6 N3), H2 O, 1.58(O)'
_chemical_formula_sum 'C7 H19.16 N8 O6.59'
_chemical_formula_weight 320.83
_chemical_melting_point ?
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'
_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.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.7868(14)
_cell_length_b 10.0032(18)
_cell_length_c 10.6058(19)
_cell_angle_alpha 72.744(6)
_cell_angle_beta 70.282(6)
_cell_angle_gamma 75.842(6)
_cell_volume 733.0(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1893
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 55.309
_cell_measurement_theta_min 5.270
_shelx_estimated_absorpt_T_max 0.963
_shelx_estimated_absorpt_T_min 0.957
_exptl_absorpt_coefficient_mu 0.126
_exptl_absorpt_correction_T_max 0.9672
_exptl_absorpt_correction_T_min 0.9619
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.454
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 340
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.3
_exptl_special_details
;
SADABS, Bruker AXS, Madison, WI, USA
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0253
_diffrn_reflns_av_unetI/netI 0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 3555
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full 24.993
_diffrn_reflns_theta_max 24.993
_diffrn_reflns_theta_min 2.160
_diffrn_ambient_temperature 296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type 'Bruker AXS Kappa Apex II with CCD detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1949
_reflns_number_total 2522
_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.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection 'APEX2 (Bruker, 2004)'
_computing_data_reduction 'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'SIR92 (Altomare et al. 1993)'
_refine_diff_density_max 0.183
_refine_diff_density_min -0.199
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.055
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 221
_refine_ls_number_reflns 2522
_refine_ls_number_restraints 15
_refine_ls_R_factor_all 0.0559
_refine_ls_R_factor_gt 0.0431
_refine_ls_restrained_S_all 1.056
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.0833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1234
_refine_ls_wR_factor_ref 0.1322
_refine_special_details ', Lattice water disorder'
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
N6-H6A
0.86 with sigma of 0.02
N6-H6B
0.86 with sigma of 0.02
N7-H7A
0.86 with sigma of 0.02
N7-H7B
0.86 with sigma of 0.02
H1SB-O1S = O1S-H1SA
0.85 with sigma of 0.02
H6A-H6B
1.36 with sigma of 0.04
H7A-H7B
1.36 with sigma of 0.04
H1SB-H1SA
1.349 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O2AA) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
Fixed Sof: O1AA(0.75) O0AA(0.3333) O2AA(0.5)
5.a Aromatic/amide H refined with riding coordinates:
C3(H3), N2(H2)
5.b X=CH2 refined with riding coordinates:
N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N7(H7A,H7B), N8(H8A,H8B)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
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 0.1742(2) 0.4631(2) 0.6286(2) 0.0383(5) Uani 1 1 d . . . . .
C2 C 0.2747(2) 0.32091(19) 0.67859(19) 0.0350(4) Uani 1 1 d . . . . .
C3 C 0.2200(2) 0.20584(19) 0.78135(19) 0.0367(4) Uani 1 1 d . . . . .
H3 H 0.1029 0.1986 0.8427 0.044 Uiso 1 1 calc R . . . .
C4 C 0.3764(3) 0.1020(2) 0.7746(2) 0.0373(4) Uani 1 1 d . . . . .
C5 C 0.3942(3) -0.0452(2) 0.8614(2) 0.0428(5) Uani 1 1 d . . . . .
C7 C -0.4649(3) 0.4214(2) 0.8562(2) 0.0400(5) Uani 1 1 d . . . . .
C8 C 0.8879(3) -0.1459(2) 0.4984(2) 0.0408(5) Uani 1 1 d . . . . .
N1 N 0.5220(2) 0.14953(17) 0.67357(18) 0.0446(4) Uani 1 1 d . . . . .
N2 N 0.4557(2) 0.28172(17) 0.61727(17) 0.0420(4) Uani 1 1 d . . . . .
H2 H 0.5215 0.3365 0.5489 0.050 Uiso 1 1 calc R . . . .
N3 N -0.3002(2) 0.34395(19) 0.84831(19) 0.0518(5) Uani 1 1 d . . . . .
H3A H -0.2861 0.2678 0.9108 0.062 Uiso 1 1 calc R . . . .
H3B H -0.2067 0.3694 0.7807 0.062 Uiso 1 1 calc R . . . .
N4 N -0.6069(2) 0.38260(19) 0.95900(18) 0.0502(5) Uani 1 1 d . . . . .
H4A H -0.5927 0.3065 1.0214 0.060 Uiso 1 1 calc R . . . .
H4B H -0.7145 0.4332 0.9642 0.060 Uiso 1 1 calc R . . . .
N5 N -0.4847(3) 0.5390(2) 0.76027(19) 0.0569(5) Uani 1 1 d . . . . .
H5A H -0.5917 0.5906 0.7652 0.068 Uiso 1 1 calc R . . . .
H5B H -0.3906 0.5638 0.6929 0.068 Uiso 1 1 calc R . . . .
N6 N 1.0402(3) -0.1969(2) 0.4138(2) 0.0472(4) Uani 1 1 d D . . . .
N7 N 0.8178(2) -0.2275(2) 0.6191(2) 0.0582(5) Uani 1 1 d D . . . .
H7A H 0.8715 -0.3133 0.6420 0.070 Uiso 1 1 calc DR . . . .
H7B H 0.7182 -0.1951 0.6751 0.070 Uiso 1 1 calc DR . . . .
N8 N 0.8038(3) -0.0147(2) 0.4608(2) 0.0573(5) Uani 1 1 d . . . . .
H8A H 0.8488 0.0374 0.3808 0.069 Uiso 1 1 calc R . . . .
H8B H 0.7042 0.0184 0.5163 0.069 Uiso 1 1 calc R . . . .
O1 O 0.00972(19) 0.49408(16) 0.69628(17) 0.0568(4) Uani 1 1 d . . . . .
O1S O 0.1173(3) 0.0490(2) 1.1741(2) 0.0781(6) Uani 1 1 d D . . . .
O2 O 0.2508(2) -0.08203(15) 0.95216(16) 0.0570(4) Uani 1 1 d . . . . .
O3 O 0.26023(18) 0.54170(16) 0.52167(16) 0.0554(4) Uani 1 1 d . . . . .
O4 O 0.5493(2) -0.12313(15) 0.84001(16) 0.0596(5) Uani 1 1 d . . . . .
H6A H 1.086(3) -0.138(2) 0.341(2) 0.062(8) Uiso 1 1 d D . . . .
H6B H 1.105(3) -0.2756(19) 0.439(2) 0.056(7) Uiso 1 1 d D . . . .
O1AA O -0.8306(8) 0.7414(5) 0.8091(8) 0.153(2) Uani 0.75 1 d . . . A 2
O0AA O -1.0000 0.5000 1.0000 0.156(3) Uani 0.6666 2 d S T P B 1
O2AA O -1.1081(13) 0.3508(11) 1.1406(11) 0.187(4) Uani 0.5 1 d . U . C 3
H1SA H 0.126(5) 0.034(5) 1.097(3) 0.147(17) Uiso 1 1 d D . . . .
H1SB H 0.217(4) 0.074(4) 1.170(4) 0.132(16) 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 0.0321(10) 0.0373(10) 0.0405(11) -0.0031(8) -0.0082(9) -0.0072(8)
C2 0.0302(9) 0.0370(10) 0.0354(10) -0.0066(8) -0.0073(8) -0.0065(8)
C3 0.0281(9) 0.0399(10) 0.0363(10) -0.0053(8) -0.0038(8) -0.0071(8)
C4 0.0362(10) 0.0358(10) 0.0368(10) -0.0072(8) -0.0060(8) -0.0081(8)
C5 0.0439(12) 0.0364(10) 0.0405(11) -0.0077(9) -0.0038(9) -0.0063(9)
C7 0.0443(11) 0.0390(10) 0.0361(10) -0.0095(8) -0.0074(9) -0.0110(9)
C8 0.0377(11) 0.0432(11) 0.0468(11) -0.0174(9) -0.0157(9) -0.0027(9)
N1 0.0365(9) 0.0368(9) 0.0469(10) -0.0013(7) -0.0039(8) -0.0035(7)
N2 0.0339(9) 0.0364(9) 0.0428(9) 0.0018(7) -0.0032(7) -0.0073(7)
N3 0.0444(10) 0.0434(10) 0.0492(11) -0.0009(8) 0.0013(8) -0.0069(8)
N4 0.0411(10) 0.0532(11) 0.0468(10) -0.0033(8) -0.0075(8) -0.0080(8)
N5 0.0565(11) 0.0540(11) 0.0461(11) 0.0013(9) -0.0091(9) -0.0078(9)
N6 0.0443(10) 0.0446(11) 0.0466(11) -0.0122(9) -0.0073(9) -0.0024(9)
N7 0.0501(11) 0.0532(11) 0.0522(11) -0.0122(9) 0.0002(9) 0.0044(9)
N8 0.0587(11) 0.0484(11) 0.0587(12) -0.0171(9) -0.0143(10) 0.0041(9)
O1 0.0353(8) 0.0451(9) 0.0633(10) 0.0031(7) 0.0028(7) -0.0025(6)
O1S 0.0828(15) 0.0894(15) 0.0595(12) -0.0185(11) -0.0062(10) -0.0281(11)
O2 0.0488(9) 0.0417(8) 0.0576(10) 0.0028(7) 0.0019(7) -0.0086(7)
O3 0.0377(8) 0.0491(9) 0.0560(9) 0.0126(7) -0.0052(7) -0.0077(7)
O4 0.0518(9) 0.0400(8) 0.0585(10) -0.0031(7) 0.0043(8) 0.0049(7)
O1AA 0.121(3) 0.094(3) 0.252(6) -0.015(4) -0.088(4) -0.011(3)
O0AA 0.060(3) 0.076(3) 0.267(9) 0.011(4) -0.016(4) 0.001(3)
O2AA 0.168(8) 0.196(9) 0.209(10) -0.122(8) -0.106(7) 0.114(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.485(3) . ?
C1 O1 1.253(2) . ?
C1 O3 1.253(2) . ?
C2 C3 1.370(3) . ?
C2 N2 1.352(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.489(3) . ?
C4 N1 1.342(2) . ?
C5 O2 1.255(2) . ?
C5 O4 1.256(2) . ?
C7 N3 1.316(3) . ?
C7 N4 1.307(3) . ?
C7 N5 1.323(3) . ?
C8 N6 1.315(3) . ?
C8 N7 1.315(3) . ?
C8 N8 1.325(3) . ?
N1 N2 1.333(2) . ?
N2 H2 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.850(16) . ?
N6 H6B 0.849(16) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
O1S H1SA 0.855(18) . ?
O1S H1SB 0.858(18) . ?
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
O1 C1 C2 117.24(17) . . ?
O1 C1 O3 125.37(18) . . ?
O3 C1 C2 117.38(17) . . ?
C3 C2 C1 132.76(17) . . ?
N2 C2 C1 121.34(16) . . ?
N2 C2 C3 105.87(16) . . ?
C2 C3 H3 127.2 . . ?
C2 C3 C4 105.58(16) . . ?
C4 C3 H3 127.2 . . ?
C3 C4 C5 128.22(17) . . ?
N1 C4 C3 111.03(16) . . ?
N1 C4 C5 120.74(16) . . ?
O2 C5 C4 116.73(17) . . ?
O2 C5 O4 124.64(18) . . ?
O4 C5 C4 118.62(17) . . ?
N3 C7 N5 119.50(19) . . ?
N4 C7 N3 119.98(18) . . ?
N4 C7 N5 120.52(19) . . ?
N6 C8 N7 119.3(2) . . ?
N6 C8 N8 120.2(2) . . ?
N7 C8 N8 120.45(19) . . ?
N2 N1 C4 104.36(15) . . ?
C2 N2 H2 123.4 . . ?
N1 N2 C2 113.16(15) . . ?
N1 N2 H2 123.4 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C8 N6 H6A 115.6(17) . . ?
C8 N6 H6B 122.0(16) . . ?
H6A N6 H6B 120(2) . . ?
C8 N7 H7A 120.0 . . ?
C8 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C8 N8 H8A 120.0 . . ?
C8 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
H1SA O1S H1SB 110(3) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.86 2.13 2.890(2) 146.7 2_666
N3 H3A O2 0.86 2.01 2.874(2) 176.2 2_557
N3 H3B O1 0.86 2.13 2.897(2) 147.9 .
N4 H4A O4 0.86 2.02 2.877(2) 176.9 2_557
N4 H4B O0AA 0.86 2.09 2.9299(18) 163.8 .
N4 H4B O2AA 0.86 2.44 3.189(7) 145.6 2_367
N5 H5A O1AA 0.86 2.10 2.939(6) 164.6 .
N5 H5A O2AA 0.86 2.22 3.017(8) 155.1 2_367
N5 H5B O3 0.86 2.58 3.141(3) 123.6 2_566
O1S H1SA O2 0.855(18) 3.05(4) 3.461(3) 112(3) 2_557
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 C2 C3 C4 177.91(19) . . . . ?
C1 C2 N2 N1 -178.48(17) . . . . ?
C2 C3 C4 C5 -178.91(19) . . . . ?
C2 C3 C4 N1 0.3(2) . . . . ?
C3 C2 N2 N1 -0.2(2) . . . . ?
C3 C4 C5 O2 0.3(3) . . . . ?
C3 C4 C5 O4 -179.3(2) . . . . ?
C3 C4 N1 N2 -0.4(2) . . . . ?
C4 N1 N2 C2 0.4(2) . . . . ?
C5 C4 N1 N2 178.85(18) . . . . ?
N1 C4 C5 O2 -178.84(18) . . . . ?
N1 C4 C5 O4 1.5(3) . . . . ?
N2 C2 C3 C4 -0.1(2) . . . . ?
O1 C1 C2 C3 6.5(3) . . . . ?
O1 C1 C2 N2 -175.79(18) . . . . ?
O3 C1 C2 C3 -172.9(2) . . . . ?
O3 C1 C2 N2 4.8(3) . . . . ?
_shelx_res_file
;
rpg.res created by SHELXL-2014/7
TITL RPG in P-1
CELL 0.71073 7.7868 10.0032 10.6058 72.744 70.282 75.842
ZERR 2 0.0014 0.0018 0.0019 0.006 0.006 0.006
LATT 1
SFAC C H N O
UNIT 14 38.33 16 13.17
EQIV $1 1-X,1-Y,1-Z
EQIV $2 -X,1-Y,1-Z
EQIV $3 -X,-Y,2-Z
EQIV $4 -2-X,1-Y,2-Z
DFIX 0.86 N6 H6a
DFIX 0.86 N6 H6b
DFIX 0.86 N7 H7a
DFIX 0.86 N7 H7b
DFIX 0.85 H1Sb O1S O1S H1Sa
DANG 1.36 H6a H6b
DANG 1.36 H7a H7b
DANG 1.349 H1Sb H1Sa
ISOR O2AA
L.S. 30
PLAN 4
SIZE 0.35 0.3 0.3
TEMP 23(2)
HTAB N2 O3_$1
HTAB N3 O1
HTAB N3 O2_$3
HTAB N4 O4_$3
HTAB N4 O0AA
HTAB N4 O2AA_$4
HTAB N5 O3_$2
HTAB N5 O1AA
HTAB N5 O2AA_$4
HTAB O1S O2_$3
HTAB
BOND $H
MORE -1
CONF
list 4
fmap 2
acta
MERG 2
OMIT -3 50
OMIT 0 1 1
OMIT 3 1 6
OMIT 0 -1 1
OMIT 1 -3 1
REM
REM
REM
WGHT 0.065500 0.083300
FVAR 0.21988
C1 1 0.174183 0.463088 0.628608 11.00000 0.03206 0.03734 =
0.04052 -0.00309 -0.00816 -0.00724
C2 1 0.274667 0.320905 0.678595 11.00000 0.03025 0.03696 =
0.03544 -0.00656 -0.00733 -0.00653
C3 1 0.220046 0.205837 0.781346 11.00000 0.02806 0.03988 =
0.03631 -0.00529 -0.00381 -0.00710
AFIX 43
H3 2 0.102887 0.198639 0.842737 11.00000 -1.20000
AFIX 0
C4 1 0.376446 0.102046 0.774642 11.00000 0.03618 0.03579 =
0.03677 -0.00717 -0.00599 -0.00812
C5 1 0.394224 -0.045204 0.861400 11.00000 0.04390 0.03638 =
0.04055 -0.00773 -0.00381 -0.00634
C7 1 -0.464860 0.421376 0.856216 11.00000 0.04428 0.03904 =
0.03615 -0.00947 -0.00740 -0.01101
C8 1 0.887920 -0.145893 0.498369 11.00000 0.03770 0.04325 =
0.04684 -0.01740 -0.01565 -0.00266
N1 3 0.521999 0.149525 0.673565 11.00000 0.03654 0.03684 =
0.04686 -0.00128 -0.00392 -0.00351
N2 3 0.455728 0.281716 0.617275 11.00000 0.03394 0.03641 =
0.04282 0.00178 -0.00319 -0.00733
AFIX 43
H2 2 0.521509 0.336500 0.548883 11.00000 -1.20000
AFIX 0
N3 3 -0.300226 0.343948 0.848310 11.00000 0.04435 0.04344 =
0.04915 -0.00090 0.00129 -0.00687
AFIX 93
H3A 2 -0.286106 0.267839 0.910778 11.00000 -1.20000
H3B 2 -0.206721 0.369441 0.780675 11.00000 -1.20000
AFIX 0
N4 3 -0.606891 0.382604 0.958997 11.00000 0.04110 0.05317 =
0.04677 -0.00332 -0.00749 -0.00802
AFIX 93
H4A 2 -0.592730 0.306490 1.021450 11.00000 -1.20000
H4B 2 -0.714533 0.433200 0.964192 11.00000 -1.20000
AFIX 0
N5 3 -0.484696 0.538998 0.760266 11.00000 0.05653 0.05397 =
0.04609 0.00131 -0.00906 -0.00777
AFIX 93
H5A 2 -0.591702 0.590602 0.765250 11.00000 -1.20000
H5B 2 -0.390584 0.563846 0.692917 11.00000 -1.20000
AFIX 0
N6 3 1.040226 -0.196877 0.413804 11.00000 0.04429 0.04459 =
0.04657 -0.01222 -0.00732 -0.00235
N7 3 0.817791 -0.227494 0.619099 11.00000 0.05007 0.05320 =
0.05219 -0.01219 0.00025 0.00436
AFIX 93
H7A 2 0.871515 -0.313266 0.642038 11.00000 -1.20000
H7B 2 0.718217 -0.195073 0.675095 11.00000 -1.20000
AFIX 0
N8 3 0.803833 -0.014717 0.460770 11.00000 0.05875 0.04837 =
0.05873 -0.01710 -0.01433 0.00409
AFIX 93
H8A 2 0.848849 0.037359 0.380847 11.00000 -1.20000
H8B 2 0.704231 0.018364 0.516285 11.00000 -1.20000
AFIX 0
O1 4 0.009716 0.494079 0.696279 11.00000 0.03532 0.04513 =
0.06333 0.00311 0.00282 -0.00255
O1S 4 0.117274 0.049006 1.174125 11.00000 0.08280 0.08940 =
0.05955 -0.01855 -0.00622 -0.02811
O2 4 0.250793 -0.082031 0.952161 11.00000 0.04877 0.04169 =
0.05758 0.00284 0.00191 -0.00858
O3 4 0.260226 0.541702 0.521672 11.00000 0.03774 0.04910 =
0.05603 0.01261 -0.00519 -0.00773
O4 4 0.549306 -0.123128 0.840006 11.00000 0.05179 0.03995 =
0.05849 -0.00309 0.00426 0.00489
H6A 2 1.086295 -0.137515 0.341087 11.00000 0.06235
H6B 2 1.105307 -0.275568 0.439391 11.00000 0.05557
PART 2
O1AA 4 -0.830604 0.741411 0.809081 10.75000 0.12084 0.09410 =
0.25206 -0.01504 -0.08834 -0.01083
PART 0
PART 1
O0AA 4 -1.000000 0.500000 1.000000 10.33330 0.06025 0.07620 =
0.26661 0.01070 -0.01594 0.00127
PART 0
PART 3
O2AA 4 -1.108113 0.350782 1.140559 10.50000 0.16800 0.19578 =
0.20890 -0.12197 -0.10643 0.11372
PART 0
H1SA 2 0.125514 0.033895 1.096915 11.00000 0.14701
H1SB 2 0.217129 0.074261 1.169756 11.00000 0.13156
HKLF 4
REM RPG in P-1
REM R1 = 0.0431 for 1949 Fo > 4sig(Fo) and 0.0559 for all 2522 data
REM 221 parameters refined using 15 restraints
END
WGHT 0.0658 0.0895
REM Instructions for potential hydrogen bonds
HTAB N2 O3_$1
HTAB N3 O2_$3
HTAB N3 O1
HTAB N4 O4_$3
HTAB N4 O0AA
HTAB N4 O2AA_$4
HTAB N5 O1AA
HTAB N5 O2AA_$4
HTAB N5 O3_$2
EQIV $5 x+1, y-1, z
HTAB N7 O1_$5
HTAB N7 O4
EQIV $6 x+1, y, z-1
HTAB N8 O1S_$6
HTAB N8 O1AA_$2
HTAB N8 N1
HTAB N6 O1S_$6
HTAB N6 O3_$5
HTAB O1S O2
EQIV $7 -x+1, -y, -z+2
HTAB O1S O4_$7
REM Highest difference peak 0.183, deepest hole -0.199, 1-sigma level 0.045
Q1 1 -1.0041 0.4774 0.9567 11.00000 0.05 0.18
Q2 1 -0.0101 0.1324 1.1599 11.00000 0.05 0.18
Q3 1 0.2638 0.5894 0.5897 11.00000 0.05 0.18
Q4 1 -0.9782 0.7813 0.8410 11.00000 0.05 0.17
;
_shelx_res_checksum 90895
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_preparation ', Luminescent'
#######################################################################
#
# 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_PAG
_database_code_depnum_ccdc_archive 'CCDC 1008628'
_audit_update_record
;
2014-06-16 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C5 H2 N2 O4, 2(C H7 N4), H2 O'
_chemical_formula_sum 'C7 H18 N10 O5'
_chemical_formula_weight 322.31
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 3.9966(2)
_cell_length_b 12.0312(6)
_cell_length_c 15.5723(9)
_cell_angle_alpha 71.941(2)
_cell_angle_beta 89.275(2)
_cell_angle_gamma 84.754(2)
_cell_volume 708.81(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 9924
_cell_measurement_theta_min 3.41
_cell_measurement_theta_max 30.46
_exptl_crystal_description plate
_exptl_crystal_colour white
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.510
_exptl_crystal_F_000 340
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.500
_exptl_crystal_size_mid 0.303
_exptl_crystal_size_min 0.070
_exptl_absorpt_coefficient_mu 0.127
_shelx_estimated_absorpt_T_min 0.470
_shelx_estimated_absorpt_T_max 0.916
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.695
_exptl_absorpt_correction_T_max 0.714
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
Bruker SAINT, Bruker AXS, wisconsin, USA
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type 'Bruker APEX-II Photon CCD'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 29616
_diffrn_reflns_av_unetI/netI 0.0322
_diffrn_reflns_av_R_equivalents 0.0573
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 3.411
_diffrn_reflns_theta_max 30.552
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total 4324
_reflns_number_gt 3575
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement 'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Structure solved by direct methods to reveal ann non-H atoms which
were refined anisotropically. All H atoms located in subsequent
difference maps and refined with DFIX constraints for E-H distances
and a riding model for their U(iso) parameters.
;
_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^)+(0.0693P)^2^+0.2559P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary 'direct methods'
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refxyz
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 4324
_refine_ls_number_parameters 258
_refine_ls_number_restraints 16
_refine_ls_R_factor_all 0.0532
_refine_ls_R_factor_gt 0.0413
_refine_ls_wR_factor_ref 0.1196
_refine_ls_wR_factor_gt 0.1095
_refine_ls_goodness_of_fit_ref 0.990
_refine_ls_restrained_S_all 0.988
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8147(2) 0.42518(7) 0.13454(6) 0.02309(19) Uani 1 1 d . . . . .
N1 N 0.5446(3) 0.26987(8) 0.35524(6) 0.0184(2) Uani 1 1 d . . . . .
C1 C 0.6884(3) 0.41362(9) 0.21073(7) 0.0163(2) Uani 1 1 d . . . . .
O2 O 0.5858(3) 0.49700(7) 0.23974(6) 0.0246(2) Uani 1 1 d . . . . .
N2 N 0.5486(3) 0.15250(8) 0.38761(6) 0.0181(2) Uani 1 1 d D . . . .
H2 H 0.494(4) 0.1217(13) 0.4437(7) 0.022 Uiso 1 1 d D U . . .
C2 C 0.6568(3) 0.29095(9) 0.27039(7) 0.0153(2) Uani 1 1 d . . . . .
O3 O 0.7461(2) -0.07175(7) 0.28325(5) 0.02034(18) Uani 1 1 d . . . . .
C3 C 0.7311(3) 0.18631(9) 0.24926(7) 0.0167(2) Uani 1 1 d D . . . .
H3 H 0.819(4) 0.1763(14) 0.1914(11) 0.025(4) Uiso 1 1 d D . . . .
O4 O 0.5919(3) -0.09010(7) 0.42502(6) 0.02361(19) Uani 1 1 d . . . . .
C4 C 0.6565(3) 0.09866(9) 0.32642(7) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.6679(3) -0.03035(9) 0.34693(7) 0.0159(2) Uani 1 1 d . . . . .
N11 N -0.0855(3) 0.85018(9) 0.02815(7) 0.0255(2) Uani 1 1 d D . . . .
H11A H -0.172(4) 0.8720(15) -0.0253(8) 0.031 Uiso 1 1 d D U . . .
H11B H 0.005(4) 0.8964(13) 0.0517(11) 0.031 Uiso 1 1 d D U . . .
C11 C -0.0287(3) 0.73595(9) 0.07060(7) 0.0168(2) Uani 1 1 d . . . . .
N12 N 0.1277(3) 0.69976(9) 0.15128(7) 0.0229(2) Uani 1 1 d D . . . .
H12A H 0.214(4) 0.7545(12) 0.1669(11) 0.028 Uiso 1 1 d D U . . .
H12B H 0.220(4) 0.6278(10) 0.1694(11) 0.028 Uiso 1 1 d D U . . .
N13 N -0.1273(3) 0.65738(8) 0.03512(6) 0.0195(2) Uani 1 1 d D . . . .
H13 H -0.133(4) 0.5854(10) 0.0699(10) 0.023 Uiso 1 1 d D U . . .
N14 N -0.3034(3) 0.69958(9) -0.04871(7) 0.0221(2) Uani 1 1 d D . . . .
H14A H -0.180(4) 0.6684(14) -0.0862(10) 0.026 Uiso 1 1 d D U . . .
H14B H -0.498(4) 0.6656(14) -0.0414(11) 0.026 Uiso 1 1 d D U . . .
N21 N 0.3132(3) 0.53618(8) 0.39094(7) 0.0195(2) Uani 1 1 d D . . . .
H21A H 0.381(4) 0.5033(13) 0.3503(9) 0.023 Uiso 1 1 d D U . . .
H21B H 0.186(4) 0.5040(13) 0.4354(9) 0.023 Uiso 1 1 d D U . . .
C21 C 0.3932(3) 0.64430(9) 0.37792(7) 0.0149(2) Uani 1 1 d . . . . .
N22 N 0.5920(3) 0.69403(8) 0.30984(7) 0.0192(2) Uani 1 1 d D . . . .
H22A H 0.658(4) 0.7625(10) 0.3051(11) 0.023 Uiso 1 1 d D U . . .
H22B H 0.685(4) 0.6499(13) 0.2799(10) 0.023 Uiso 1 1 d D U . . .
N23 N 0.2773(2) 0.70745(8) 0.43034(7) 0.01801(19) Uani 1 1 d D . . . .
H23 H 0.349(4) 0.7756(10) 0.4250(11) 0.022 Uiso 1 1 d D U . . .
N24 N 0.0622(3) 0.65950(9) 0.50190(7) 0.01874(19) Uani 1 1 d . . . . .
H24A H -0.115(4) 0.7120(14) 0.4944(11) 0.022 Uiso 1 1 d . U . . .
H24B H 0.165(4) 0.6582(14) 0.5552(11) 0.022 Uiso 1 1 d . U . . .
O1W O 0.2185(2) 0.96217(8) 0.15073(6) 0.0255(2) Uani 1 1 d D . . . .
H1W H 0.069(4) 0.9582(15) 0.1921(11) 0.031 Uiso 1 1 d D U . . .
H2W H 0.398(4) 0.9651(16) 0.1798(11) 0.031 Uiso 1 1 d D 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 0.0383(5) 0.0141(4) 0.0165(4) -0.0040(3) 0.0093(3) -0.0043(3)
N1 0.0294(5) 0.0118(4) 0.0143(4) -0.0041(3) 0.0041(3) -0.0041(3)
C1 0.0226(5) 0.0112(4) 0.0148(5) -0.0033(3) 0.0015(4) -0.0029(4)
O2 0.0418(5) 0.0123(4) 0.0202(4) -0.0063(3) 0.0079(4) -0.0014(3)
N2 0.0301(5) 0.0116(4) 0.0127(4) -0.0033(3) 0.0053(3) -0.0049(3)
C2 0.0209(5) 0.0119(4) 0.0131(4) -0.0038(3) 0.0019(4) -0.0025(4)
O3 0.0310(4) 0.0136(3) 0.0178(4) -0.0064(3) 0.0056(3) -0.0047(3)
C3 0.0244(5) 0.0122(4) 0.0135(4) -0.0039(3) 0.0038(4) -0.0024(4)
O4 0.0417(5) 0.0142(4) 0.0152(4) -0.0035(3) 0.0067(3) -0.0089(3)
C4 0.0217(5) 0.0120(4) 0.0133(4) -0.0047(3) 0.0024(4) -0.0037(4)
C5 0.0210(5) 0.0123(4) 0.0150(5) -0.0045(4) 0.0018(4) -0.0042(4)
N11 0.0408(6) 0.0140(4) 0.0206(5) -0.0038(4) -0.0063(4) -0.0019(4)
C11 0.0189(5) 0.0153(5) 0.0156(5) -0.0042(4) 0.0038(4) -0.0015(4)
N12 0.0308(5) 0.0182(4) 0.0187(5) -0.0047(4) -0.0044(4) 0.0001(4)
N13 0.0289(5) 0.0138(4) 0.0152(4) -0.0032(3) 0.0014(4) -0.0041(4)
N14 0.0248(5) 0.0250(5) 0.0182(5) -0.0093(4) -0.0013(4) -0.0024(4)
N21 0.0269(5) 0.0135(4) 0.0198(4) -0.0071(3) 0.0066(4) -0.0050(3)
C21 0.0149(5) 0.0133(4) 0.0162(5) -0.0045(4) -0.0029(4) 0.0002(3)
N22 0.0238(5) 0.0155(4) 0.0199(4) -0.0071(3) 0.0042(4) -0.0053(4)
N23 0.0214(5) 0.0137(4) 0.0213(4) -0.0082(3) 0.0033(4) -0.0044(3)
N24 0.0181(4) 0.0201(4) 0.0205(5) -0.0097(4) 0.0034(3) -0.0028(4)
O1W 0.0274(5) 0.0316(5) 0.0189(4) -0.0096(3) 0.0015(3) -0.0042(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2558(13) . ?
N1 N2 1.3427(12) . ?
N1 C2 1.3452(13) . ?
C1 O2 1.2569(13) . ?
C1 C2 1.4961(14) . ?
N2 C4 1.3546(13) . ?
N2 H2 0.869(10) . ?
C2 C3 1.4026(14) . ?
O3 C5 1.2646(13) . ?
C3 C4 1.3811(14) . ?
C3 H3 1.000(16) . ?
O4 C5 1.2555(13) . ?
C4 C5 1.4809(14) . ?
N11 C11 1.3270(14) . ?
N11 H11A 0.858(10) . ?
N11 H11B 0.861(10) . ?
C11 N13 1.3235(14) . ?
C11 N12 1.3377(15) . ?
N12 H12A 0.869(10) . ?
N12 H12B 0.871(10) . ?
N13 N14 1.4158(14) . ?
N13 H13 0.870(10) . ?
N14 H14A 0.905(13) . ?
N14 H14B 0.900(14) . ?
N21 C21 1.3215(14) . ?
N21 H21A 0.872(10) . ?
N21 H21B 0.864(10) . ?
C21 N23 1.3299(14) . ?
C21 N22 1.3362(14) . ?
N22 H22A 0.870(10) . ?
N22 H22B 0.865(10) . ?
N23 N24 1.4074(13) . ?
N23 H23 0.873(10) . ?
N24 H24A 0.887(18) . ?
N24 H24B 0.926(17) . ?
O1W H1W 0.867(14) . ?
O1W H2W 0.863(15) . ?
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
N2 N1 C2 104.56(8) . . ?
O1 C1 O2 124.89(10) . . ?
O1 C1 C2 116.91(9) . . ?
O2 C1 C2 118.19(9) . . ?
N1 N2 C4 112.74(9) . . ?
N1 N2 H2 117.9(10) . . ?
C4 N2 H2 129.3(10) . . ?
N1 C2 C3 111.35(9) . . ?
N1 C2 C1 121.02(9) . . ?
C3 C2 C1 127.63(9) . . ?
C4 C3 C2 104.77(9) . . ?
C4 C3 H3 127.0(9) . . ?
C2 C3 H3 128.2(9) . . ?
N2 C4 C3 106.58(9) . . ?
N2 C4 C5 121.64(9) . . ?
C3 C4 C5 131.75(10) . . ?
O4 C5 O3 124.86(10) . . ?
O4 C5 C4 118.03(9) . . ?
O3 C5 C4 117.08(9) . . ?
C11 N11 H11A 118.2(12) . . ?
C11 N11 H11B 116.6(12) . . ?
H11A N11 H11B 124.0(16) . . ?
N13 C11 N11 121.24(11) . . ?
N13 C11 N12 119.49(10) . . ?
N11 C11 N12 119.27(11) . . ?
C11 N12 H12A 114.9(11) . . ?
C11 N12 H12B 117.1(11) . . ?
H12A N12 H12B 120.6(16) . . ?
C11 N13 N14 117.61(9) . . ?
C11 N13 H13 118.5(11) . . ?
N14 N13 H13 121.6(11) . . ?
N13 N14 H14A 104.8(11) . . ?
N13 N14 H14B 107.2(11) . . ?
H14A N14 H14B 105.7(15) . . ?
C21 N21 H21A 116.5(11) . . ?
C21 N21 H21B 120.0(11) . . ?
H21A N21 H21B 123.3(15) . . ?
N21 C21 N23 121.86(10) . . ?
N21 C21 N22 120.18(10) . . ?
N23 C21 N22 117.95(10) . . ?
C21 N22 H22A 119.2(10) . . ?
C21 N22 H22B 117.3(11) . . ?
H22A N22 H22B 122.0(15) . . ?
C21 N23 N24 119.98(9) . . ?
C21 N23 H23 121.1(11) . . ?
N24 N23 H23 118.6(11) . . ?
N23 N24 H24A 105.4(10) . . ?
N23 N24 H24B 108.0(10) . . ?
H24A N24 H24B 105.3(14) . . ?
H1W O1W H2W 101.0(16) . . ?
_refine_diff_density_max 0.472
_refine_diff_density_min -0.267
_refine_diff_density_rms 0.058
_shelxl_version_number 2013-3
_shelx_res_file
;
TITL PAG in P-1
CELL 0.71073 3.99660 12.03120 15.57230 71.9411 89.2747 84.7538
ZERR 2.00 0.00020 0.00060 0.00090 0.0021 0.0024 0.0023
LATT 1
SFAC C H N O
UNIT 14 36 20 10
TEMP -100.030
SIZE 0.70 3.30 7.00
DFIX 21.0 0.01 N11 H11A N11 H11B N12 H12A N12 H12B N13 H13 N2 H2
DFIX 21.0 0.01 N21 H21A N21 H21B N22 H22A N22 H22B N23 H23
DFIX 31.0 0.01 C3 H3
DFIX 41.0 0.01 N14 H14A N14 H14B
DFIX 51.0 0.01 O1W H1W O1W H2W
L.S. 9
ACTA
LIST
BOND $H
FMAP 2
PLAN 5
WGHT 0.069300 0.255900
FVAR 0.27755 0.86749 0.99999 0.90219 0.86521
MOLE 1
O1 4 0.814714 1.425180 0.134540 11.00000 0.03829 0.01408 =
0.01654 -0.00404 0.00930 -0.00431
N1 3 0.544563 1.269865 0.355244 11.00000 0.02942 0.01176 =
0.01432 -0.00412 0.00411 -0.00408
C1 1 0.688435 1.413620 0.210728 11.00000 0.02263 0.01124 =
0.01480 -0.00325 0.00151 -0.00289
O2 4 0.585751 1.496997 0.239736 11.00000 0.04176 0.01232 =
0.02021 -0.00631 0.00787 -0.00139
N2 3 0.548568 1.152503 0.387612 11.00000 0.03005 0.01158 =
0.01272 -0.00326 0.00534 -0.00492
H2 2 0.494464 1.121723 0.443671 11.00000 -1.20000
C2 1 0.656802 1.290950 0.270394 11.00000 0.02086 0.01191 =
0.01309 -0.00377 0.00194 -0.00255
O3 4 0.746136 0.928250 0.283251 11.00000 0.03100 0.01363 =
0.01783 -0.00644 0.00564 -0.00465
C3 1 0.731059 1.186312 0.249261 11.00000 0.02439 0.01216 =
0.01348 -0.00389 0.00376 -0.00243
H3 2 0.819035 1.176322 0.191447 11.00000 0.02505
O4 4 0.591930 0.909903 0.425021 11.00000 0.04171 0.01422 =
0.01520 -0.00348 0.00672 -0.00889
C4 1 0.656473 1.098659 0.326415 11.00000 0.02175 0.01195 =
0.01333 -0.00475 0.00238 -0.00369
C5 1 0.667911 0.969654 0.346933 11.00000 0.02104 0.01225 =
0.01501 -0.00446 0.00180 -0.00417
MOLE 2
N11 3 -0.085549 1.850182 0.028145 11.00000 0.04076 0.01400 =
0.02059 -0.00376 -0.00630 -0.00192
H11A 2 -0.172284 1.871989 -0.025264 11.00000 -1.20000
H11B 2 0.005055 1.896376 0.051737 11.00000 -1.20000
C11 1 -0.028652 1.735950 0.070602 11.00000 0.01891 0.01533 =
0.01561 -0.00423 0.00384 -0.00145
N12 3 0.127740 1.699762 0.151276 11.00000 0.03082 0.01824 =
0.01872 -0.00467 -0.00438 0.00008
H12A 2 0.214260 1.754529 0.166856 11.00000 -1.20000
H12B 2 0.219936 1.627782 0.169390 11.00000 -1.20000
N13 3 -0.127320 1.657380 0.035124 11.00000 0.02893 0.01382 =
0.01520 -0.00319 0.00142 -0.00414
H13 2 -0.133360 1.585426 0.069944 11.00000 -1.20000
N14 3 -0.303441 1.699580 -0.048712 11.00000 0.02485 0.02499 =
0.01823 -0.00932 -0.00130 -0.00241
H14A 2 -0.180016 1.668394 -0.086162 11.00000 -1.20000
H14B 2 -0.497665 1.665640 -0.041414 11.00000 -1.20000
MOLE 3
N21 3 0.313199 1.536182 0.390937 11.00000 0.02690 0.01350 =
0.01979 -0.00714 0.00658 -0.00502
H21A 2 0.380508 1.503286 0.350308 11.00000 -1.20000
H21B 2 0.186267 1.503967 0.435363 11.00000 -1.20000
C21 1 0.393215 1.644299 0.377923 11.00000 0.01486 0.01329 =
0.01623 -0.00450 -0.00286 0.00015
N22 3 0.592000 1.694029 0.309844 11.00000 0.02378 0.01549 =
0.01994 -0.00706 0.00420 -0.00532
H22A 2 0.658253 1.762518 0.305111 11.00000 -1.20000
H22B 2 0.684597 1.649882 0.279934 11.00000 -1.20000
N23 3 0.277268 1.707446 0.430341 11.00000 0.02141 0.01373 =
0.02126 -0.00816 0.00333 -0.00442
H23 2 0.348860 1.775612 0.425040 11.00000 -1.20000
N24 3 0.062237 1.659503 0.501898 11.00000 0.01811 0.02011 =
0.02048 -0.00970 0.00341 -0.00281
H24A 2 -0.114600 1.712042 0.494434 11.00000 -1.20000
H24B 2 0.165243 1.658196 0.555188 11.00000 -1.20000
MOLE 4
O1W 4 0.218508 1.962166 0.150732 11.00000 0.02736 0.03160 =
0.01892 -0.00962 0.00152 -0.00418
H1W 2 0.068588 1.958184 0.192072 11.00000 -1.20000
H2W 2 0.398167 1.965094 0.179846 11.00000 -1.20000
HKLF 4
REM PAG in P-1
REM R1 = 0.0413 for 3575 Fo > 4sig(Fo) and 0.0532 for all 4324 data
REM 258 parameters refined using 16 restraints
END
WGHT 0.0563 0.2755
REM Highest difference peak 0.472, deepest hole -0.267, 1-sigma level 0.058
Q1 1 0.7089 1.1388 0.2892 11.00000 0.05 0.47
Q2 1 0.6736 1.3512 0.2394 11.00000 0.05 0.44
Q3 1 0.6580 1.0387 0.3309 11.00000 0.05 0.40
Q4 1 0.6922 1.2423 0.2608 11.00000 0.05 0.40
Q5 1 0.3151 1.6751 0.4040 11.00000 0.05 0.35
;
_shelx_res_checksum 70995