# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_20151204-xiayi-zzw
_database_code_depnum_ccdc_archive 'CCDC 1441152'
_audit_update_record
;
2017-06-07 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date 2017-06-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H13 F3 N4 O3'
_chemical_formula_sum 'C15 H13 F3 N4 O3'
_chemical_formula_weight 354.29
_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'
F F 0.0171 0.0103 '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 35.076(3)
_cell_length_b 10.0258(6)
_cell_length_c 8.8087(5)
_cell_angle_alpha 90
_cell_angle_beta 94.027(6)
_cell_angle_gamma 90
_cell_volume 3090.1(4)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 2216
_cell_measurement_temperature 293(2)
_cell_measurement_theta_min 4.3380
_cell_measurement_theta_max 28.7480
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.132
_exptl_absorpt_correction_T_min 0.72307
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.737
_oxdiff_exptl_absorpt_empirical_full_max 1.433
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour Colorless
_exptl_crystal_density_diffrn 1.523
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 1456
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.2
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0143
_diffrn_reflns_av_unetI/netI 0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 41
_diffrn_reflns_limit_h_min -43
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 6
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 5809
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.361
_diffrn_reflns_theta_min 3.462
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'SuperNova (Mo) X-ray Source'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2479
_reflns_number_total 3153
_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 ?
_computing_data_collection ?
_computing_data_reduction ?
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.351
_refine_diff_density_min -0.390
_refine_diff_density_rms 0.048
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.070
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 240
_refine_ls_number_reflns 3153
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0693
_refine_ls_R_factor_gt 0.0545
_refine_ls_restrained_S_all 1.070
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+4.5816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1397
_refine_ls_wR_factor_ref 0.1516
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H,H) groups
At 1.5 times of:
All O(H) groups
2. Others
Sof(F1)=Sof(F2)=Sof(F3)=1-FVAR(1)
Sof(F1')=Sof(F2')=Sof(F3')=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
C3(H3A,H3B), C2(H2A,H2B), C1(H1C,H1D)
3.b Aromatic/amide H refined with riding coordinates:
C11(H11), C10(H10), C12(H12), C13(H13)
3.c X=CH2 refined with riding coordinates:
N1(H1A,H1B)
3.d Idealised tetrahedral OH refined as rotating group:
O3(H3)
;
_atom_sites_solution_hydrogens geom
_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
O2 O 0.70615(5) 0.41500(16) 1.20410(17) 0.0426(4) Uani 1 1 d . . . . .
O1 O 0.68948(5) 0.12857(16) 1.28264(16) 0.0440(4) Uani 1 1 d . . . . .
O3 O 0.72503(5) 0.70544(18) 1.2143(2) 0.0504(5) Uani 1 1 d . . . . .
H3 H 0.7484 0.7030 1.2292 0.076 Uiso 1 1 calc GR . . . .
N2 N 0.64840(5) 0.13936(18) 0.89847(19) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.68832(6) -0.03228(18) 1.1008(2) 0.0411(5) Uani 1 1 d . . . . .
H1A H 0.6997 -0.0901 1.1600 0.049 Uiso 1 1 calc R . . . .
H1B H 0.6816 -0.0528 1.0080 0.049 Uiso 1 1 calc R . . . .
N4 N 0.65560(5) 0.30926(18) 1.05529(18) 0.0332(4) Uani 1 1 d . . . . .
N3 N 0.63800(5) 0.36099(19) 0.9262(2) 0.0390(4) Uani 1 1 d . . . . .
C4 C 0.68117(6) 0.0878(2) 1.1523(2) 0.0335(5) Uani 1 1 d . . . . .
C5 C 0.66167(6) 0.1779(2) 1.0361(2) 0.0314(5) Uani 1 1 d . . . . .
C6 C 0.63419(6) 0.2548(2) 0.8361(2) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.66668(7) 0.3976(2) 1.1846(2) 0.0385(5) Uani 1 1 d . . . . .
H3A H 0.6546 0.4838 1.1677 0.046 Uiso 1 1 calc R . . . .
H3B H 0.6575 0.3600 1.2767 0.046 Uiso 1 1 calc R . . . .
C2 C 0.72315(7) 0.4868(3) 1.0854(3) 0.0460(6) Uani 1 1 d . . . . .
H2A H 0.7149 0.4467 0.9884 0.055 Uiso 1 1 calc R . . . .
H2B H 0.7507 0.4771 1.0992 0.055 Uiso 1 1 calc R . . . .
C9 C 0.58628(6) 0.2570(2) 0.4028(2) 0.0409(5) Uani 1 1 d . . . . .
C8 C 0.60385(7) 0.2607(3) 0.5553(3) 0.0436(6) Uani 1 1 d . . . . .
C7 C 0.61715(7) 0.2613(2) 0.6831(3) 0.0415(5) Uani 1 1 d . . . . .
C1 C 0.71369(8) 0.6319(3) 1.0791(3) 0.0498(6) Uani 1 1 d . . . . .
H1C H 0.7259 0.6714 0.9944 0.060 Uiso 1 1 calc R . . . .
H1D H 0.6863 0.6414 1.0586 0.060 Uiso 1 1 calc R . . . .
C14 C 0.54821(7) 0.2453(3) 0.1168(3) 0.0460(6) Uani 1 1 d . . . . .
C11 C 0.57094(8) 0.3721(3) 0.3351(3) 0.0497(6) Uani 1 1 d . . . . .
H11 H 0.5735 0.4534 0.3857 0.060 Uiso 1 1 calc R . . . .
C10 C 0.58377(8) 0.1370(3) 0.3234(3) 0.0531(7) Uani 1 1 d . . . . .
H10 H 0.5952 0.0606 0.3658 0.064 Uiso 1 1 calc R . . . .
C12 C 0.55188(8) 0.3658(3) 0.1923(3) 0.0526(7) Uani 1 1 d . . . . .
H12 H 0.5415 0.4427 0.1471 0.063 Uiso 1 1 calc R . . . .
C13 C 0.56439(8) 0.1313(3) 0.1815(3) 0.0564(7) Uani 1 1 d . . . . .
H13 H 0.5622 0.0507 0.1295 0.068 Uiso 1 1 calc R . . . .
C15 C 0.52622(8) 0.2369(3) -0.0351(3) 0.0575(7) Uani 1 1 d . . . . .
F1' F 0.5220(5) 0.1176(15) -0.0890(18) 0.075(5) Uiso 0.144(5) 1 d . . P A 1
F2' F 0.5433(3) 0.3036(12) -0.1361(12) 0.041(3) Uiso 0.144(5) 1 d . . P A 1
F3' F 0.4955(3) 0.2906(15) -0.0438(14) 0.054(4) Uiso 0.144(5) 1 d . . P A 1
F1 F 0.49531(8) 0.1667(4) -0.0310(3) 0.1124(15) Uani 0.856(5) 1 d . . P A 2
F2 F 0.54494(8) 0.1800(6) -0.1378(3) 0.143(2) Uani 0.856(5) 1 d . . P A 2
F3 F 0.51416(18) 0.3529(3) -0.0868(4) 0.173(3) Uani 0.856(5) 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0521(10) 0.0403(9) 0.0341(8) 0.0034(7) -0.0055(7) -0.0123(7)
O1 0.0698(11) 0.0351(9) 0.0252(7) 0.0005(6) -0.0092(7) -0.0033(8)
O3 0.0567(11) 0.0416(9) 0.0521(10) 0.0001(8) -0.0029(8) -0.0018(9)
N2 0.0460(10) 0.0348(10) 0.0250(8) 0.0006(7) -0.0051(7) -0.0028(8)
N1 0.0634(13) 0.0315(10) 0.0269(9) 0.0019(8) -0.0067(8) 0.0044(9)
N4 0.0418(10) 0.0304(9) 0.0267(8) 0.0014(7) -0.0034(7) -0.0014(8)
N3 0.0470(11) 0.0367(10) 0.0320(9) 0.0061(8) -0.0066(8) 0.0020(8)
C4 0.0434(12) 0.0306(11) 0.0259(10) 0.0040(9) -0.0027(8) -0.0049(9)
C5 0.0391(11) 0.0295(10) 0.0250(9) 0.0020(8) -0.0020(8) -0.0046(9)
C6 0.0390(11) 0.0384(12) 0.0284(10) 0.0040(9) -0.0047(8) -0.0012(9)
C3 0.0542(13) 0.0322(11) 0.0290(10) -0.0049(9) 0.0022(9) -0.0010(10)
C2 0.0499(14) 0.0500(14) 0.0379(12) -0.0009(11) 0.0028(10) -0.0105(11)
C9 0.0385(12) 0.0527(14) 0.0305(11) 0.0042(10) -0.0057(9) -0.0004(10)
C8 0.0430(13) 0.0515(15) 0.0352(12) 0.0047(10) -0.0058(10) -0.0002(11)
C7 0.0456(13) 0.0445(13) 0.0333(12) 0.0040(10) -0.0054(9) -0.0006(10)
C1 0.0604(16) 0.0467(14) 0.0413(13) 0.0094(11) -0.0032(11) -0.0105(12)
C14 0.0442(13) 0.0599(16) 0.0325(12) 0.0022(11) -0.0077(10) -0.0031(11)
C11 0.0621(16) 0.0472(14) 0.0378(12) -0.0009(11) -0.0108(11) 0.0027(12)
C10 0.0650(17) 0.0498(15) 0.0425(13) 0.0044(12) -0.0113(12) 0.0093(13)
C12 0.0604(16) 0.0534(16) 0.0415(13) 0.0092(12) -0.0137(11) 0.0064(13)
C13 0.0727(18) 0.0525(16) 0.0418(13) -0.0068(12) -0.0103(12) 0.0019(14)
C15 0.0574(17) 0.074(2) 0.0392(14) 0.0004(14) -0.0114(12) -0.0033(15)
F1 0.0726(17) 0.191(4) 0.0689(16) 0.0062(18) -0.0270(12) -0.055(2)
F2 0.0809(18) 0.307(6) 0.0374(12) -0.047(2) -0.0089(11) 0.040(3)
F3 0.298(6) 0.083(2) 0.115(3) 0.020(2) -0.150(4) -0.008(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.394(3) . ?
O2 C2 1.434(3) . ?
O1 C4 1.234(2) . ?
O3 H3 0.8200 . ?
O3 C1 1.433(3) . ?
N2 C5 1.325(3) . ?
N2 C6 1.361(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C4 1.317(3) . ?
N4 N3 1.358(2) . ?
N4 C5 1.346(3) . ?
N4 C3 1.473(3) . ?
N3 C6 1.329(3) . ?
C4 C5 1.495(3) . ?
C6 C7 1.437(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.492(4) . ?
C9 C8 1.439(3) . ?
C9 C11 1.390(3) . ?
C9 C10 1.391(4) . ?
C8 C7 1.188(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C14 C12 1.380(4) . ?
C14 C13 1.381(4) . ?
C14 C15 1.499(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 F1' 1.291(15) . ?
C15 F2' 1.294(11) . ?
C15 F3' 1.201(12) . ?
C15 F1 1.295(4) . ?
C15 F2 1.288(4) . ?
C15 F3 1.309(4) . ?
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
C3 O2 C2 115.65(17) . . ?
C1 O3 H3 109.5 . . ?
C5 N2 C6 102.48(18) . . ?
H1A N1 H1B 120.0 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
N3 N4 C3 119.82(18) . . ?
C5 N4 N3 109.55(16) . . ?
C5 N4 C3 130.53(17) . . ?
C6 N3 N4 102.41(17) . . ?
O1 C4 N1 125.8(2) . . ?
O1 C4 C5 120.27(19) . . ?
N1 C4 C5 113.94(18) . . ?
N2 C5 N4 110.61(18) . . ?
N2 C5 C4 124.37(19) . . ?
N4 C5 C4 125.01(18) . . ?
N2 C6 C7 122.3(2) . . ?
N3 C6 N2 114.94(18) . . ?
N3 C6 C7 122.8(2) . . ?
O2 C3 N4 112.11(17) . . ?
O2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
N4 C3 H3A 109.2 . . ?
N4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C2 H2A 108.6 . . ?
O2 C2 H2B 108.6 . . ?
O2 C2 C1 114.5(2) . . ?
H2A C2 H2B 107.6 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C11 C9 C8 120.4(2) . . ?
C11 C9 C10 119.5(2) . . ?
C10 C9 C8 120.0(2) . . ?
C7 C8 C9 177.5(3) . . ?
C8 C7 C6 176.7(3) . . ?
O3 C1 C2 115.0(2) . . ?
O3 C1 H1C 108.5 . . ?
O3 C1 H1D 108.5 . . ?
C2 C1 H1C 108.5 . . ?
C2 C1 H1D 108.5 . . ?
H1C C1 H1D 107.5 . . ?
C12 C14 C13 120.2(2) . . ?
C12 C14 C15 120.3(2) . . ?
C13 C14 C15 119.5(2) . . ?
C9 C11 H11 120.0 . . ?
C12 C11 C9 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C13 C10 C9 120.0(2) . . ?
C13 C10 H10 120.0 . . ?
C14 C12 C11 120.1(2) . . ?
C14 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C10 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C10 C13 H13 120.0 . . ?
F1' C15 C14 114.8(7) . . ?
F1' C15 F2' 105.8(9) . . ?
F2' C15 C14 110.5(5) . . ?
F3' C15 C14 115.7(6) . . ?
F3' C15 F1' 108.3(10) . . ?
F3' C15 F2' 100.3(8) . . ?
F1 C15 C14 112.6(2) . . ?
F1 C15 F3 104.0(4) . . ?
F2 C15 C14 113.4(2) . . ?
F2 C15 F1 104.4(3) . . ?
F2 C15 F3 108.5(4) . . ?
F3 C15 C14 113.2(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 C2 C1 O3 59.6(3) . . . . ?
O1 C4 C5 N2 -173.2(2) . . . . ?
O1 C4 C5 N4 7.8(3) . . . . ?
N1 C4 C5 N2 7.6(3) . . . . ?
N1 C4 C5 N4 -171.4(2) . . . . ?
N4 N3 C6 N2 -0.5(3) . . . . ?
N4 N3 C6 C7 -179.1(2) . . . . ?
N3 N4 C5 N2 -0.5(2) . . . . ?
N3 N4 C5 C4 178.58(19) . . . . ?
N3 N4 C3 O2 -108.7(2) . . . . ?
C5 N2 C6 N3 0.2(3) . . . . ?
C5 N2 C6 C7 178.8(2) . . . . ?
C5 N4 N3 C6 0.6(2) . . . . ?
C5 N4 C3 O2 67.4(3) . . . . ?
C6 N2 C5 N4 0.2(2) . . . . ?
C6 N2 C5 C4 -178.9(2) . . . . ?
C3 O2 C2 C1 70.2(3) . . . . ?
C3 N4 N3 C6 177.41(18) . . . . ?
C3 N4 C5 N2 -176.9(2) . . . . ?
C3 N4 C5 C4 2.2(4) . . . . ?
C2 O2 C3 N4 67.2(2) . . . . ?
C9 C11 C12 C14 -0.2(4) . . . . ?
C9 C10 C13 C14 1.5(4) . . . . ?
C8 C9 C11 C12 -175.7(2) . . . . ?
C8 C9 C10 C13 175.1(2) . . . . ?
C11 C9 C10 C13 -3.4(4) . . . . ?
C10 C9 C11 C12 2.8(4) . . . . ?
C12 C14 C13 C10 1.1(4) . . . . ?
C12 C14 C15 F1' -174.6(10) . . . . ?
C12 C14 C15 F2' 65.9(7) . . . . ?
C12 C14 C15 F3' -47.3(9) . . . . ?
C12 C14 C15 F1 -113.5(4) . . . . ?
C12 C14 C15 F2 128.2(4) . . . . ?
C12 C14 C15 F3 4.1(5) . . . . ?
C13 C14 C12 C11 -1.7(4) . . . . ?
C13 C14 C15 F1' 4.7(10) . . . . ?
C13 C14 C15 F2' -114.9(7) . . . . ?
C13 C14 C15 F3' 132.0(9) . . . . ?
C13 C14 C15 F1 65.8(4) . . . . ?
C13 C14 C15 F2 -52.5(5) . . . . ?
C13 C14 C15 F3 -176.6(4) . . . . ?
C15 C14 C12 C11 177.5(3) . . . . ?
C15 C14 C13 C10 -178.1(3) . . . . ?
_iucr_refine_instructions_details
;
20151204-xiayi-zzw.res created by SHELXL-2014/7
TITL 20151204-xiayi-zzw_a.res in C2/c
CELL 0.71073 35.076294 10.025787 8.808661 90 94.0269 90
ZERR 8 0.003197 0.000631 0.000478 0 0.0064 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H F N O
UNIT 120 104 24 32 24
L.S. 30
PLAN 20
MORE -1
BOND $H
CONF
LIST 6
fmap 2
acta
MERG 2
SHEL 999 0.8
REM
REM
REM
WGHT 0.058600 4.581600
FVAR 0.35963 0.14351
O2 5 0.706150 0.414996 1.204102 11.00000 0.05214 0.04027 =
0.03405 0.00338 -0.00553 -0.01234
O1 5 0.689480 0.128573 1.282639 11.00000 0.06983 0.03513 =
0.02524 0.00054 -0.00922 -0.00327
O3 5 0.725026 0.705439 1.214262 11.00000 0.05671 0.04156 =
0.05210 0.00014 -0.00290 -0.00182
AFIX 147
H3 2 0.748356 0.702992 1.229173 11.00000 -1.50000
AFIX 0
N2 4 0.648398 0.139365 0.898468 11.00000 0.04599 0.03484 =
0.02500 0.00057 -0.00507 -0.00285
N1 4 0.688321 -0.032279 1.100826 11.00000 0.06339 0.03148 =
0.02693 0.00192 -0.00672 0.00443
AFIX 93
H1A 2 0.699748 -0.090146 1.160002 11.00000 -1.20000
H1B 2 0.681562 -0.052843 1.008034 11.00000 -1.20000
AFIX 0
N4 4 0.655604 0.309265 1.055294 11.00000 0.04177 0.03043 =
0.02670 0.00136 -0.00343 -0.00135
N3 4 0.638003 0.360985 0.926210 11.00000 0.04704 0.03671 =
0.03196 0.00613 -0.00664 0.00202
C4 1 0.681174 0.087834 1.152307 11.00000 0.04340 0.03055 =
0.02594 0.00401 -0.00268 -0.00488
C5 1 0.661665 0.177942 1.036075 11.00000 0.03914 0.02952 =
0.02504 0.00195 -0.00196 -0.00457
C6 1 0.634189 0.254816 0.836121 11.00000 0.03902 0.03843 =
0.02842 0.00405 -0.00472 -0.00120
C3 1 0.666679 0.397618 1.184556 11.00000 0.05421 0.03216 =
0.02902 -0.00486 0.00215 -0.00097
AFIX 23
H3A 2 0.654550 0.483814 1.167738 11.00000 -1.20000
H3B 2 0.657548 0.359997 1.276750 11.00000 -1.20000
AFIX 0
C2 1 0.723145 0.486830 1.085384 11.00000 0.04988 0.05004 =
0.03794 -0.00089 0.00279 -0.01054
AFIX 23
H2A 2 0.714867 0.446680 0.988428 11.00000 -1.20000
H2B 2 0.750684 0.477091 1.099151 11.00000 -1.20000
AFIX 0
C9 1 0.586276 0.256979 0.402818 11.00000 0.03846 0.05271 =
0.03054 0.00420 -0.00567 -0.00041
C8 1 0.603846 0.260660 0.555317 11.00000 0.04295 0.05150 =
0.03522 0.00473 -0.00577 -0.00016
C7 1 0.617150 0.261332 0.683071 11.00000 0.04562 0.04451 =
0.03326 0.00399 -0.00543 -0.00056
C1 1 0.713687 0.631881 1.079074 11.00000 0.06040 0.04674 =
0.04127 0.00937 -0.00324 -0.01055
AFIX 23
H1C 2 0.725873 0.671363 0.994369 11.00000 -1.20000
H1D 2 0.686289 0.641393 1.058578 11.00000 -1.20000
AFIX 0
C14 1 0.548210 0.245306 0.116843 11.00000 0.04417 0.05990 =
0.03250 0.00222 -0.00774 -0.00311
C11 1 0.570940 0.372147 0.335100 11.00000 0.06214 0.04720 =
0.03778 -0.00094 -0.01078 0.00272
AFIX 43
H11 2 0.573488 0.453398 0.385734 11.00000 -1.20000
AFIX 0
C10 1 0.583769 0.137033 0.323356 11.00000 0.06496 0.04979 =
0.04251 0.00437 -0.01126 0.00933
AFIX 43
H10 2 0.595151 0.060626 0.365779 11.00000 -1.20000
AFIX 0
C12 1 0.551884 0.365775 0.192309 11.00000 0.06038 0.05339 =
0.04148 0.00923 -0.01375 0.00636
AFIX 43
H12 2 0.541542 0.442734 0.147146 11.00000 -1.20000
AFIX 0
C13 1 0.564389 0.131347 0.181522 11.00000 0.07269 0.05255 =
0.04180 -0.00676 -0.01034 0.00186
AFIX 43
H13 2 0.562232 0.050677 0.129508 11.00000 -1.20000
AFIX 0
C15 1 0.526218 0.236853 -0.035088 11.00000 0.05740 0.07367 =
0.03921 0.00036 -0.01143 -0.00329
PART 1
F1' 3 0.522022 0.117603 -0.088968 21.00000 0.07527
F2' 3 0.543293 0.303646 -0.136073 21.00000 0.04121
F3' 3 0.495545 0.290628 -0.043815 21.00000 0.05440
PART 0
PART 2
F1 3 0.495308 0.166747 -0.030954 -21.00000 0.07257 0.19117 =
0.06892 0.00622 -0.02705 -0.05477
F2 3 0.544937 0.180025 -0.137838 -21.00000 0.08089 0.30740 =
0.03743 -0.04735 -0.00890 0.03967
F3 3 0.514159 0.352880 -0.086822 -21.00000 0.29808 0.08348 =
0.11517 0.02038 -0.15033 -0.00777
HKLF 4
REM 20151204-xiayi-zzw_a.res in C2/c
REM R1 = 0.0545 for 2479 Fo > 4sig(Fo) and 0.0693 for all 3153 data
REM 240 parameters refined using 0 restraints
END
WGHT 0.0586 4.5815
REM Highest difference peak 0.351, deepest hole -0.390, 1-sigma level 0.048
Q1 1 0.6957 0.5536 1.0791 11.00000 0.05 0.35
Q2 1 0.5434 0.3556 -0.1174 11.00000 0.05 0.29
Q3 1 0.6861 0.4830 1.1926 11.00000 0.05 0.28
Q4 1 0.5009 0.3474 -0.0600 11.00000 0.05 0.27
Q5 1 0.5414 0.2529 -0.1458 11.00000 0.05 0.26
Q6 1 0.5400 0.1329 -0.1209 11.00000 0.05 0.25
Q7 1 0.6769 0.1425 1.0808 11.00000 0.05 0.20
Q8 1 0.7412 0.5985 1.1265 11.00000 0.05 0.19
Q9 1 0.4923 0.2412 -0.0343 11.00000 0.05 0.19
Q10 1 0.5089 0.1194 -0.0609 11.00000 0.05 0.18
Q11 1 0.6567 0.1480 0.9703 11.00000 0.05 0.17
Q12 1 0.5594 0.2043 0.1272 11.00000 0.05 0.16
Q13 1 0.6424 0.4455 1.1948 11.00000 0.05 0.16
Q14 1 0.6626 0.1428 1.2934 11.00000 0.05 0.16
Q15 1 0.5129 0.4123 -0.0766 11.00000 0.05 0.16
Q16 1 0.5762 0.3076 0.3738 11.00000 0.05 0.14
Q17 1 0.5432 0.2456 0.0555 11.00000 0.05 0.14
Q18 1 0.5425 0.2808 0.1584 11.00000 0.05 0.14
Q19 1 0.5534 0.2960 0.1345 11.00000 0.05 0.14
Q20 1 0.7522 0.4823 1.1606 11.00000 0.05 0.13
REM The information below was added by Olex2.
REM
REM R1 = 0.0545 for 2479 Fo > 4sig(Fo) and 0.0693 for all 6557 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.35, deepest hole -0.39
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0693
REM R1_gt = 0.0545
REM wR_ref = 0.1516
REM GOOF = 1.070
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 6557
REM Reflections_gt = 2479
REM Parameters = n/a
REM Hole = -0.39
REM Peak = 0.35
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_cmm5
_database_code_depnum_ccdc_archive 'CCDC 1441261'
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date 2017-06-14
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H16 N4 O4'
_chemical_formula_sum 'C15 H16 N4 O4'
_chemical_formula_weight 316.32
_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 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 17.5680(9)
_cell_length_b 9.9977(5)
_cell_length_c 8.8328(5)
_cell_angle_alpha 90
_cell_angle_beta 104.264(6)
_cell_angle_gamma 90
_cell_volume 1503.55(15)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 1475
_cell_measurement_temperature 294(2)
_cell_measurement_theta_min 4.1170
_cell_measurement_theta_max 26.0770
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.104
_exptl_absorpt_correction_T_min 0.79740
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.641
_oxdiff_exptl_absorpt_empirical_full_max 1.295
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour Colorless
_exptl_crystal_density_diffrn 1.397
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 664
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0229
_diffrn_reflns_av_unetI/netI 0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 6130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 3.557
_diffrn_ambient_temperature 294(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2071
_reflns_number_total 3071
_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 ?
_computing_data_collection ?
_computing_data_reduction ?
_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 'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max 0.226
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 218
_refine_ls_number_reflns 3071
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0803
_refine_ls_R_factor_gt 0.0518
_refine_ls_restrained_S_all 1.052
_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^)+(0.0603P)^2^+0.2474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1228
_refine_ls_wR_factor_ref 0.1418
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C4(H4C), C6(H6), C3(H3)
2.c X=CH2 refined with riding coordinates:
N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
O4(H4)
;
_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
O3 O 0.41225(9) 0.33598(14) 0.23942(17) 0.0437(4) Uani 1 1 d . . . . .
O2 O 0.37602(9) 0.62388(15) 0.14131(16) 0.0465(4) Uani 1 1 d . . . . .
O4 O 0.44777(9) 0.04424(16) 0.25213(19) 0.0528(4) Uani 1 1 d . . . . .
H4 H 0.4957 0.0451 0.2674 0.079 Uiso 1 1 calc GR . . . .
N3 N 0.30821(10) 0.44025(17) 0.32282(18) 0.0357(4) Uani 1 1 d . . . . .
N1 N 0.28990(10) 0.60814(17) 0.46893(19) 0.0391(4) Uani 1 1 d . . . . .
N2 N 0.27151(10) 0.38598(18) 0.4267(2) 0.0408(4) Uani 1 1 d . . . . .
N4 N 0.37169(11) 0.78393(17) 0.3209(2) 0.0453(5) Uani 1 1 d . . . . .
H4A H 0.3946 0.8428 0.2766 0.054 Uiso 1 1 calc R . . . .
H4B H 0.3575 0.8039 0.4046 0.054 Uiso 1 1 calc R . . . .
O1 O 0.06028(11) 0.4732(2) 1.2559(2) 0.0700(6) Uani 1 1 d . . . . .
C12 C 0.35825(12) 0.6631(2) 0.2605(2) 0.0370(5) Uani 1 1 d . . . . .
C11 C 0.31901(11) 0.5718(2) 0.3505(2) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.26152(12) 0.4912(2) 0.5114(2) 0.0374(5) Uani 1 1 d . . . . .
C13 C 0.33144(14) 0.3531(2) 0.2069(3) 0.0395(5) Uani 1 1 d . . . . .
C7 C 0.16578(12) 0.4784(2) 0.8850(2) 0.0424(5) Uani 1 1 d . . . . .
C9 C 0.22559(13) 0.4817(2) 0.6401(3) 0.0441(5) Uani 1 1 d . . . . .
C8 C 0.19892(13) 0.4788(2) 0.7513(3) 0.0457(6) Uani 1 1 d . . . . .
C5 C 0.13206(13) 0.3630(2) 0.9285(3) 0.0483(6) Uani 1 1 d . . . . .
H5 H 0.1325 0.2840 0.8732 0.058 Uiso 1 1 calc R . . . .
C15 C 0.42537(14) 0.1178(2) 0.3723(3) 0.0511(6) Uani 1 1 d . . . . .
H15A H 0.4500 0.0773 0.4721 0.061 Uiso 1 1 calc R . . . .
H15B H 0.3690 0.1099 0.3575 0.061 Uiso 1 1 calc R . . . .
C4 C 0.09811(14) 0.3656(3) 1.0528(3) 0.0535(6) Uani 1 1 d . . . . .
H4C H 0.0756 0.2881 1.0807 0.064 Uiso 1 1 calc R . . . .
C2 C 0.09692(13) 0.4819(3) 1.1372(3) 0.0497(6) Uani 1 1 d . . . . .
C14 C 0.44640(14) 0.2632(2) 0.3792(3) 0.0478(6) Uani 1 1 d . . . . .
H14A H 0.4298 0.3039 0.4654 0.057 Uiso 1 1 calc R . . . .
H14B H 0.5031 0.2713 0.4009 0.057 Uiso 1 1 calc R . . . .
C6 C 0.16656(14) 0.5928(3) 0.9725(3) 0.0521(6) Uani 1 1 d . . . . .
H6 H 0.1903 0.6697 0.9465 0.063 Uiso 1 1 calc R . . . .
C3 C 0.13250(14) 0.5956(3) 1.0987(3) 0.0540(6) Uani 1 1 d . . . . .
H3 H 0.1337 0.6735 1.1568 0.065 Uiso 1 1 calc R . . . .
C1 C 0.05491(19) 0.5912(4) 1.3424(3) 0.0827(10) Uani 1 1 d . . . . .
H1A H 0.0333 0.6623 1.2719 0.124 Uiso 1 1 calc GR . . . .
H1B H 0.1063 0.6161 1.4022 0.124 Uiso 1 1 calc GR . . . .
H1C H 0.0215 0.5748 1.4117 0.124 Uiso 1 1 calc GR . . . .
H13A H 0.3015(11) 0.270(2) 0.213(2) 0.038(6) Uiso 1 1 d . . . . .
H13B H 0.3144(12) 0.397(2) 0.107(3) 0.039(6) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0554(9) 0.0410(9) 0.0397(8) 0.0055(7) 0.0215(7) 0.0103(7)
O2 0.0730(11) 0.0400(9) 0.0352(8) 0.0016(7) 0.0300(8) 0.0023(7)
O4 0.0626(10) 0.0447(9) 0.0553(10) 0.0003(8) 0.0226(9) 0.0031(8)
N3 0.0461(10) 0.0326(9) 0.0321(9) 0.0020(8) 0.0166(8) 0.0013(7)
N1 0.0530(10) 0.0360(10) 0.0337(9) 0.0028(8) 0.0209(8) 0.0034(8)
N2 0.0493(10) 0.0390(10) 0.0392(10) 0.0073(9) 0.0206(8) -0.0010(8)
N4 0.0724(13) 0.0334(10) 0.0379(10) 0.0003(8) 0.0286(9) -0.0051(9)
O1 0.0828(13) 0.0857(14) 0.0557(11) 0.0035(11) 0.0441(10) 0.0005(11)
C12 0.0497(12) 0.0335(11) 0.0313(11) 0.0041(9) 0.0164(9) 0.0047(9)
C11 0.0436(11) 0.0340(11) 0.0280(10) 0.0016(9) 0.0137(9) 0.0042(9)
C10 0.0406(11) 0.0399(12) 0.0358(11) 0.0049(10) 0.0169(9) 0.0006(9)
C13 0.0542(13) 0.0352(12) 0.0313(12) -0.0021(10) 0.0149(10) 0.0011(10)
C7 0.0415(11) 0.0537(14) 0.0361(11) 0.0087(11) 0.0174(9) 0.0028(10)
C9 0.0506(12) 0.0465(13) 0.0405(12) 0.0055(11) 0.0212(11) 0.0024(10)
C8 0.0488(12) 0.0502(14) 0.0429(13) 0.0067(11) 0.0208(11) 0.0009(10)
C5 0.0578(14) 0.0491(13) 0.0430(13) 0.0020(11) 0.0218(11) 0.0000(11)
C15 0.0618(15) 0.0494(14) 0.0471(13) 0.0138(12) 0.0229(12) 0.0121(11)
C4 0.0602(15) 0.0569(15) 0.0497(14) 0.0114(13) 0.0260(12) -0.0067(12)
C2 0.0474(13) 0.0684(17) 0.0384(12) 0.0088(12) 0.0205(10) 0.0046(12)
C14 0.0541(13) 0.0517(14) 0.0388(12) 0.0028(11) 0.0134(10) 0.0106(11)
C6 0.0576(14) 0.0516(14) 0.0538(14) 0.0061(13) 0.0265(12) -0.0014(11)
C3 0.0622(15) 0.0562(15) 0.0487(14) -0.0019(12) 0.0234(12) 0.0064(12)
C1 0.088(2) 0.113(3) 0.0577(17) -0.0043(19) 0.0381(16) 0.0239(19)
_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
O3 C13 1.388(3) . ?
O3 C14 1.431(3) . ?
O2 C12 1.233(2) . ?
O4 H4 0.8200 . ?
O4 C15 1.424(3) . ?
N3 N2 1.358(2) . ?
N3 C11 1.343(3) . ?
N3 C13 1.476(3) . ?
N1 C11 1.323(2) . ?
N1 C10 1.359(3) . ?
N2 C10 1.328(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C12 1.318(3) . ?
O1 C2 1.361(3) . ?
O1 C1 1.421(3) . ?
C12 C11 1.487(3) . ?
C10 C9 1.432(3) . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.97(2) . ?
C7 C8 1.440(3) . ?
C7 C5 1.393(3) . ?
C7 C6 1.379(3) . ?
C9 C8 1.189(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.497(3) . ?
C4 H4C 0.9300 . ?
C4 C2 1.384(3) . ?
C2 C3 1.380(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
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
C13 O3 C14 115.55(17) . . ?
C15 O4 H4 109.5 . . ?
N2 N3 C13 119.42(17) . . ?
C11 N3 N2 109.73(16) . . ?
C11 N3 C13 130.81(17) . . ?
C11 N1 C10 102.84(17) . . ?
C10 N2 N3 102.41(16) . . ?
H4A N4 H4B 120.0 . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
C2 O1 C1 117.9(2) . . ?
O2 C12 N4 125.40(19) . . ?
O2 C12 C11 120.64(18) . . ?
N4 C12 C11 113.96(17) . . ?
N3 C11 C12 124.53(17) . . ?
N1 C11 N3 110.36(18) . . ?
N1 C11 C12 125.11(19) . . ?
N1 C10 C9 122.7(2) . . ?
N2 C10 N1 114.65(17) . . ?
N2 C10 C9 122.68(19) . . ?
O3 C13 N3 111.89(17) . . ?
O3 C13 H13A 114.7(11) . . ?
O3 C13 H13B 108.4(12) . . ?
N3 C13 H13A 102.5(12) . . ?
N3 C13 H13B 106.9(12) . . ?
H13A C13 H13B 112.2(17) . . ?
C5 C7 C8 121.0(2) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 C5 118.6(2) . . ?
C8 C9 C10 176.3(3) . . ?
C9 C8 C7 178.6(3) . . ?
C7 C5 H5 119.9 . . ?
C4 C5 C7 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
O4 C15 H15A 108.5 . . ?
O4 C15 H15B 108.5 . . ?
O4 C15 C14 114.88(19) . . ?
H15A C15 H15B 107.5 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C5 C4 H4C 119.5 . . ?
C5 C4 C2 120.9(2) . . ?
C2 C4 H4C 119.5 . . ?
O1 C2 C4 115.7(2) . . ?
O1 C2 C3 124.8(2) . . ?
C3 C2 C4 119.4(2) . . ?
O3 C14 C15 114.33(19) . . ?
O3 C14 H14A 108.7 . . ?
O3 C14 H14B 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C7 C6 H6 119.4 . . ?
C7 C6 C3 121.3(2) . . ?
C3 C6 H6 119.4 . . ?
C2 C3 C6 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C6 C3 H3 120.3 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O2 C12 C11 N3 8.0(3) . . . . ?
O2 C12 C11 N1 -172.07(19) . . . . ?
O4 C15 C14 O3 59.5(3) . . . . ?
N3 N2 C10 N1 -0.5(2) . . . . ?
N3 N2 C10 C9 -178.86(18) . . . . ?
N2 N3 C11 N1 -0.7(2) . . . . ?
N2 N3 C11 C12 179.26(18) . . . . ?
N2 N3 C13 O3 -108.7(2) . . . . ?
N4 C12 C11 N3 -171.41(19) . . . . ?
N4 C12 C11 N1 8.5(3) . . . . ?
O1 C2 C3 C6 -178.6(2) . . . . ?
C11 N3 N2 C10 0.7(2) . . . . ?
C11 N3 C13 O3 69.0(3) . . . . ?
C11 N1 C10 N2 0.1(2) . . . . ?
C11 N1 C10 C9 178.47(19) . . . . ?
C10 N1 C11 N3 0.4(2) . . . . ?
C10 N1 C11 C12 -179.57(19) . . . . ?
C13 O3 C14 C15 68.9(2) . . . . ?
C13 N3 N2 C10 178.83(17) . . . . ?
C13 N3 C11 N1 -178.57(18) . . . . ?
C13 N3 C11 C12 1.4(3) . . . . ?
C7 C5 C4 C2 -0.2(4) . . . . ?
C7 C6 C3 C2 -0.2(4) . . . . ?
C8 C7 C5 C4 -177.6(2) . . . . ?
C8 C7 C6 C3 177.8(2) . . . . ?
C5 C7 C6 C3 -2.0(3) . . . . ?
C5 C4 C2 O1 178.7(2) . . . . ?
C5 C4 C2 C3 -2.0(4) . . . . ?
C4 C2 C3 C6 2.2(4) . . . . ?
C14 O3 C13 N3 66.8(2) . . . . ?
C6 C7 C5 C4 2.2(3) . . . . ?
C1 O1 C2 C4 -177.7(2) . . . . ?
C1 O1 C2 C3 3.1(4) . . . . ?
_iucr_refine_instructions_details
;
cmm5.res created by SHELXL-2014/7
TITL 20170614-xiayi-zzw-cmm5_a.res in P2(1)/c
REM Old TITL 20170614-Xia Yi-ZZW-CMM5 in P2/c #13
REM SHELXT solution in P2(1)/c
REM R1 0.198, Rweak 0.240, Alpha 0.020, Orientation as input
REM Formula found by SHELXT: C14 N6 O3
CELL 0.71073 17.567952 9.997696 8.832788 90 104.2641 90
ZERR 4 0.000949 0.000519 0.000506 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 60 64 16 16
L.S. 30
PLAN 20
BOND $H
LIST 6
MORE -1
CONF
fmap 2
acta 52
SHEL 999 0.8
REM
REM
REM
WGHT 0.060300 0.247400
FVAR 0.40826
O3 4 0.412247 0.335981 0.239418 11.00000 0.05541 0.04100 =
0.03968 0.00549 0.02151 0.01030
O2 4 0.376018 0.623880 0.141315 11.00000 0.07300 0.03999 =
0.03517 0.00165 0.02998 0.00231
O4 4 0.447775 0.044237 0.252130 11.00000 0.06260 0.04468 =
0.05528 0.00030 0.02257 0.00315
AFIX 147
H4 2 0.495743 0.045100 0.267414 11.00000 -1.50000
AFIX 0
N3 3 0.308213 0.440254 0.322825 11.00000 0.04608 0.03256 =
0.03212 0.00202 0.01656 0.00133
N1 3 0.289903 0.608137 0.468929 11.00000 0.05297 0.03597 =
0.03369 0.00279 0.02090 0.00344
N2 3 0.271513 0.385978 0.426701 11.00000 0.04933 0.03901 =
0.03918 0.00733 0.02065 -0.00104
N4 3 0.371688 0.783934 0.320877 11.00000 0.07238 0.03338 =
0.03791 0.00033 0.02857 -0.00505
AFIX 93
H4A 2 0.394629 0.842793 0.276567 11.00000 -1.20000
H4B 2 0.357513 0.803902 0.404607 11.00000 -1.20000
AFIX 0
O1 4 0.060280 0.473214 1.255873 11.00000 0.08280 0.08566 =
0.05567 0.00350 0.04406 0.00049
C12 1 0.358253 0.663106 0.260452 11.00000 0.04967 0.03354 =
0.03127 0.00412 0.01640 0.00467
C11 1 0.319010 0.571843 0.350524 11.00000 0.04363 0.03397 =
0.02802 0.00165 0.01370 0.00419
C10 1 0.261517 0.491243 0.511449 11.00000 0.04058 0.03987 =
0.03578 0.00492 0.01687 0.00063
C13 1 0.331443 0.353121 0.206914 11.00000 0.05422 0.03517 =
0.03134 -0.00212 0.01486 0.00115
C7 1 0.165780 0.478362 0.885023 11.00000 0.04154 0.05371 =
0.03612 0.00867 0.01740 0.00277
C9 1 0.225590 0.481744 0.640061 11.00000 0.05055 0.04646 =
0.04048 0.00550 0.02116 0.00244
C8 1 0.198923 0.478827 0.751300 11.00000 0.04884 0.05024 =
0.04290 0.00669 0.02083 0.00090
C5 1 0.132061 0.363044 0.928512 11.00000 0.05782 0.04906 =
0.04305 0.00196 0.02175 0.00000
AFIX 43
H5 2 0.132550 0.284046 0.873168 11.00000 -1.20000
AFIX 0
C15 1 0.425371 0.117825 0.372319 11.00000 0.06184 0.04943 =
0.04713 0.01383 0.02288 0.01208
AFIX 23
H15A 2 0.450039 0.077310 0.472134 11.00000 -1.20000
H15B 2 0.368980 0.109938 0.357514 11.00000 -1.20000
AFIX 0
C4 1 0.098115 0.365615 1.052774 11.00000 0.06021 0.05693 =
0.04975 0.01139 0.02596 -0.00668
AFIX 43
H4C 2 0.075603 0.288146 1.080653 11.00000 -1.20000
AFIX 0
C2 1 0.096920 0.481916 1.137180 11.00000 0.04739 0.06836 =
0.03844 0.00879 0.02050 0.00464
C14 1 0.446404 0.263171 0.379163 11.00000 0.05409 0.05168 =
0.03880 0.00279 0.01343 0.01064
AFIX 23
H14A 2 0.429776 0.303908 0.465389 11.00000 -1.20000
H14B 2 0.503090 0.271271 0.400921 11.00000 -1.20000
AFIX 0
C6 1 0.166559 0.592847 0.972517 11.00000 0.05756 0.05161 =
0.05384 0.00612 0.02651 -0.00139
AFIX 43
H6 2 0.190349 0.669690 0.946520 11.00000 -1.20000
AFIX 0
C3 1 0.132503 0.595623 1.098714 11.00000 0.06218 0.05621 =
0.04873 -0.00191 0.02340 0.00644
AFIX 43
H3 2 0.133683 0.673515 1.156804 11.00000 -1.20000
AFIX 0
C1 1 0.054912 0.591185 1.342439 11.00000 0.08795 0.11299 =
0.05770 -0.00430 0.03811 0.02387
AFIX 137
H1A 2 0.033269 0.662286 1.271872 11.00000 -1.50000
H1B 2 0.106317 0.616119 1.402233 11.00000 -1.50000
H1C 2 0.021525 0.574830 1.411681 11.00000 -1.50000
AFIX 0
H13A 2 0.301472 0.270496 0.212591 11.00000 0.03778
H13B 2 0.314369 0.397163 0.106551 11.00000 0.03883
HKLF 4
REM 20170614-xiayi-zzw-cmm5_a.res in P2(1)/c
REM R1 = 0.0518 for 2071 Fo > 4sig(Fo) and 0.0803 for all 3071 data
REM 218 parameters refined using 0 restraints
END
WGHT 0.0603 0.2474
REM Highest difference peak 0.226, deepest hole -0.181, 1-sigma level 0.044
Q1 1 0.3215 0.6161 0.1190 11.00000 0.05 0.23
Q2 1 0.2213 0.3842 0.3923 11.00000 0.05 0.18
Q3 1 0.3655 0.2731 0.2299 11.00000 0.05 0.18
Q4 1 0.3735 0.1974 0.3208 11.00000 0.05 0.17
Q5 1 0.0499 0.5004 1.2942 11.00000 0.05 0.16
Q6 1 0.4310 0.3415 0.5964 11.00000 0.05 0.16
Q7 1 0.3068 0.6981 0.5062 11.00000 0.05 0.16
Q8 1 0.4496 0.6515 0.1400 11.00000 0.05 0.16
Q9 1 0.3569 0.0880 0.3105 11.00000 0.05 0.15
Q10 1 0.5718 0.3346 0.4046 11.00000 0.05 0.15
Q11 1 0.1656 0.4833 0.7988 11.00000 0.05 0.14
Q12 1 0.0899 0.5436 1.0971 11.00000 0.05 0.14
Q13 1 0.3125 0.7803 0.3103 11.00000 0.05 0.13
Q14 1 0.1541 0.5211 0.8841 11.00000 0.05 0.13
Q15 1 0.2990 0.1110 0.3683 11.00000 0.05 0.13
Q16 1 0.4398 0.6325 0.2450 11.00000 0.05 0.13
Q17 1 0.2704 0.6782 0.9310 11.00000 0.05 0.13
Q18 1 0.2568 0.6788 0.6548 11.00000 0.05 0.13
Q19 1 0.1484 0.3652 1.0320 11.00000 0.05 0.13
Q20 1 0.2312 0.6443 1.0275 11.00000 0.05 0.13
REM The information below was added by Olex2.
REM
REM R1 = 0.0518 for 2071 Fo > 4sig(Fo) and 0.0803 for all 6907 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.23, deepest hole -0.18
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0803
REM R1_gt = 0.0518
REM wR_ref = 0.1418
REM GOOF = 1.052
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 6907
REM Reflections_gt = 2071
REM Parameters = n/a
REM Hole = -0.18
REM Peak = 0.23
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_20170623-xiayi-zzw-1
_database_code_depnum_ccdc_archive 'CCDC 1441262'
_audit_update_record
;
2017-06-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date 2017-06-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H14 N4 O3'
_chemical_formula_sum 'C14 H14 N4 O3'
_chemical_formula_weight 286.29
_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 orthorhombic
_space_group_IT_number 61
_space_group_name_H-M_alt 'P b c a'
_space_group_name_Hall '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 11.4857(7)
_cell_length_b 6.9956(4)
_cell_length_c 33.950(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2727.8(3)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 2452
_cell_measurement_temperature 175(2)
_cell_measurement_theta_max 28.6860
_cell_measurement_theta_min 3.7190
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.101
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.84069
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour Colorless
_exptl_crystal_density_diffrn 1.394
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 1200
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.15
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0226
_diffrn_reflns_av_unetI/netI 0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 42
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 7406
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.372
_diffrn_reflns_theta_min 3.462
_diffrn_ambient_temperature 175(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2304
_reflns_number_total 2788
_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 ?
_computing_data_collection ?
_computing_data_reduction ?
_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 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.367
_refine_diff_density_min -0.228
_refine_diff_density_rms 0.052
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.165
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 199
_refine_ls_number_reflns 2788
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0596
_refine_ls_R_factor_gt 0.0487
_refine_ls_restrained_S_all 1.165
_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^)+(0.0399P)^2^+3.3858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1321
_refine_ls_wR_factor_ref 0.1368
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H,H) groups
At 1.5 times of:
All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
C00H(H00E,H00H), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
C00F(H00F), C00G(H00G), C00J(H00K), C00K(H00L), C00L(H00M)
2.c X=CH2 refined with riding coordinates:
N007(H00A,H00B)
2.d Idealised tetrahedral OH refined as rotating group:
O003(H003)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_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
O001 O 0.53618(14) 0.7574(2) 0.43971(4) 0.0230(4) Uani 1 1 d . . . . .
O002 O 0.31239(15) 0.6646(3) 0.49955(5) 0.0313(4) Uani 1 1 d . . . . .
O003 O 0.60085(16) 1.1466(3) 0.43430(6) 0.0336(5) Uani 1 1 d . . . . .
H003 H 0.6425 1.1817 0.4525 0.050 Uiso 1 1 calc GR . . . .
N004 N 0.18523(16) 0.5810(3) 0.40452(5) 0.0205(4) Uani 1 1 d . . . . .
N005 N 0.37243(16) 0.5754(3) 0.41802(5) 0.0189(4) Uani 1 1 d . . . . .
N006 N 0.36571(16) 0.5385(3) 0.37876(5) 0.0203(4) Uani 1 1 d . . . . .
N007 N 0.12201(17) 0.6535(3) 0.48162(6) 0.0257(5) Uani 1 1 d . . . . .
H00A H 0.0970 0.6790 0.5049 0.031 Uiso 1 1 calc R . . . .
H00B H 0.0734 0.6356 0.4627 0.031 Uiso 1 1 calc R . . . .
C008 C 0.2515(2) 0.5433(3) 0.37213(6) 0.0186(5) Uani 1 1 d . . . . .
C009 C 0.26412(19) 0.5998(3) 0.43273(6) 0.0182(5) Uani 1 1 d . . . . .
C00A C 0.2044(2) 0.5081(3) 0.33355(7) 0.0223(5) Uani 1 1 d . . . . .
C00B C 0.1391(2) 0.4371(3) 0.26062(6) 0.0202(5) Uani 1 1 d . . . . .
C00C C 0.2351(2) 0.6418(3) 0.47488(6) 0.0215(5) Uani 1 1 d . . . . .
C00D C 0.4876(2) 0.5748(3) 0.43670(7) 0.0222(5) Uani 1 1 d . . . . .
C00E C 0.1710(2) 0.4748(3) 0.30112(7) 0.0209(5) Uani 1 1 d . . . . .
C00F C 0.2184(2) 0.3477(3) 0.23578(7) 0.0243(5) Uani 1 1 d . . . . .
H00F H 0.2905 0.3090 0.2454 0.029 Uiso 1 1 calc R . . . .
C00G C 0.0318(2) 0.4963(3) 0.24589(7) 0.0246(5) Uani 1 1 d . . . . .
H00G H -0.0217 0.5557 0.2624 0.030 Uiso 1 1 calc R . . . .
C00H C 0.5743(2) 0.8411(3) 0.40319(6) 0.0219(5) Uani 1 1 d . . . . .
H00E H 0.5082 0.8916 0.3888 0.026 Uiso 1 1 calc R . . . .
H00H H 0.6121 0.7453 0.3870 0.026 Uiso 1 1 calc R . . . .
C00I C 0.6583(2) 0.9991(4) 0.41274(7) 0.0271(5) Uani 1 1 d . . . . .
H00I H 0.7223 0.9487 0.4282 0.033 Uiso 1 1 calc R . . . .
H00J H 0.6901 1.0513 0.3885 0.033 Uiso 1 1 calc R . . . .
C00J C 0.1901(2) 0.3159(4) 0.19651(7) 0.0287(6) Uani 1 1 d . . . . .
H00K H 0.2429 0.2548 0.1800 0.034 Uiso 1 1 calc R . . . .
C00K C 0.0834(2) 0.3752(4) 0.18193(7) 0.0327(6) Uani 1 1 d . . . . .
H00L H 0.0646 0.3535 0.1557 0.039 Uiso 1 1 calc R . . . .
C00L C 0.0049(2) 0.4664(4) 0.20638(7) 0.0311(6) Uani 1 1 d . . . . .
H00M H -0.0662 0.5079 0.1964 0.037 Uiso 1 1 calc R . . . .
H00C H 0.479(2) 0.528(3) 0.4634(7) 0.018(6) Uiso 1 1 d . . . . .
H00D H 0.533(2) 0.486(4) 0.4202(7) 0.022(6) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0254(8) 0.0276(9) 0.0161(8) -0.0016(7) -0.0004(7) -0.0075(7)
O002 0.0323(10) 0.0419(10) 0.0196(8) -0.0089(8) -0.0041(7) 0.0004(8)
O003 0.0341(10) 0.0299(10) 0.0368(11) -0.0083(8) -0.0098(8) -0.0002(8)
N004 0.0222(10) 0.0254(10) 0.0138(9) -0.0016(8) 0.0004(7) -0.0023(8)
N005 0.0194(9) 0.0220(9) 0.0153(9) -0.0024(8) -0.0011(7) -0.0025(8)
N006 0.0217(10) 0.0240(10) 0.0152(9) -0.0026(8) -0.0003(8) -0.0019(8)
N007 0.0269(11) 0.0347(12) 0.0155(9) -0.0045(8) 0.0025(8) 0.0028(9)
C008 0.0218(11) 0.0176(11) 0.0164(10) -0.0006(9) 0.0003(9) -0.0023(9)
C009 0.0215(11) 0.0178(10) 0.0153(10) -0.0013(9) -0.0003(9) -0.0027(9)
C00A 0.0223(12) 0.0210(11) 0.0234(12) 0.0004(9) 0.0025(9) -0.0011(10)
C00B 0.0239(12) 0.0205(11) 0.0160(11) 0.0017(9) -0.0041(9) -0.0026(9)
C00C 0.0304(13) 0.0180(11) 0.0159(11) -0.0013(9) 0.0013(10) 0.0000(10)
C00D 0.0216(12) 0.0248(12) 0.0203(12) -0.0005(10) -0.0051(9) -0.0006(10)
C00E 0.0198(11) 0.0205(11) 0.0224(12) 0.0018(9) -0.0024(9) -0.0026(9)
C00F 0.0241(13) 0.0228(12) 0.0260(12) 0.0019(10) -0.0033(10) 0.0019(10)
C00G 0.0243(12) 0.0281(12) 0.0215(12) -0.0017(10) -0.0021(10) 0.0016(10)
C00H 0.0238(12) 0.0280(12) 0.0139(10) -0.0010(9) 0.0009(9) 0.0001(10)
C00I 0.0264(13) 0.0270(13) 0.0281(13) 0.0024(10) 0.0045(10) -0.0035(11)
C00J 0.0359(14) 0.0292(13) 0.0209(12) -0.0032(10) 0.0028(11) 0.0025(11)
C00K 0.0430(16) 0.0368(14) 0.0183(12) 0.0000(11) -0.0080(11) -0.0023(13)
C00L 0.0281(13) 0.0406(16) 0.0247(13) 0.0017(11) -0.0096(10) 0.0021(12)
_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
O001 C00D 1.398(3) . ?
O001 C00H 1.440(3) . ?
O002 C00C 1.231(3) . ?
O003 H003 0.8200 . ?
O003 C00I 1.427(3) . ?
N004 C008 1.363(3) . ?
N004 C009 1.325(3) . ?
N005 N006 1.360(2) . ?
N005 C009 1.351(3) . ?
N005 C00D 1.467(3) . ?
N006 C008 1.331(3) . ?
N007 H00A 0.8600 . ?
N007 H00B 0.8600 . ?
N007 C00C 1.322(3) . ?
C008 C00A 1.438(3) . ?
C009 C00C 1.498(3) . ?
C00A C00E 1.189(3) . ?
C00B C00E 1.447(3) . ?
C00B C00F 1.390(3) . ?
C00B C00G 1.394(3) . ?
C00D H00C 0.97(2) . ?
C00D H00D 0.99(3) . ?
C00F H00F 0.9300 . ?
C00F C00J 1.390(3) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.392(3) . ?
C00H H00E 0.9700 . ?
C00H H00H 0.9700 . ?
C00H C00I 1.502(3) . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00J H00K 0.9300 . ?
C00J C00K 1.385(4) . ?
C00K H00L 0.9300 . ?
C00K C00L 1.382(4) . ?
C00L H00M 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
C00D O001 C00H 115.48(17) . . ?
C00I O003 H003 109.5 . . ?
C009 N004 C008 102.74(18) . . ?
N006 N005 C00D 118.31(18) . . ?
C009 N005 N006 109.51(17) . . ?
C009 N005 C00D 132.13(18) . . ?
C008 N006 N005 102.53(17) . . ?
H00A N007 H00B 120.0 . . ?
C00C N007 H00A 120.0 . . ?
C00C N007 H00B 120.0 . . ?
N004 C008 C00A 123.9(2) . . ?
N006 C008 N004 114.74(19) . . ?
N006 C008 C00A 121.3(2) . . ?
N004 C009 N005 110.49(18) . . ?
N004 C009 C00C 123.9(2) . . ?
N005 C009 C00C 125.6(2) . . ?
C00E C00A C008 176.5(3) . . ?
C00F C00B C00E 119.5(2) . . ?
C00F C00B C00G 119.7(2) . . ?
C00G C00B C00E 120.7(2) . . ?
O002 C00C N007 125.6(2) . . ?
O002 C00C C009 121.0(2) . . ?
N007 C00C C009 113.3(2) . . ?
O001 C00D N005 112.89(19) . . ?
O001 C00D H00C 106.4(14) . . ?
O001 C00D H00D 113.7(15) . . ?
N005 C00D H00C 108.1(14) . . ?
N005 C00D H00D 103.8(15) . . ?
H00C C00D H00D 112(2) . . ?
C00A C00E C00B 175.7(2) . . ?
C00B C00F H00F 120.0 . . ?
C00B C00F C00J 120.0(2) . . ?
C00J C00F H00F 120.0 . . ?
C00B C00G H00G 120.1 . . ?
C00L C00G C00B 119.8(2) . . ?
C00L C00G H00G 120.1 . . ?
O001 C00H H00E 110.1 . . ?
O001 C00H H00H 110.1 . . ?
O001 C00H C00I 107.99(18) . . ?
H00E C00H H00H 108.4 . . ?
C00I C00H H00E 110.1 . . ?
C00I C00H H00H 110.1 . . ?
O003 C00I C00H 110.2(2) . . ?
O003 C00I H00I 109.6 . . ?
O003 C00I H00J 109.6 . . ?
C00H C00I H00I 109.6 . . ?
C00H C00I H00J 109.6 . . ?
H00I C00I H00J 108.1 . . ?
C00F C00J H00K 119.9 . . ?
C00K C00J C00F 120.1(2) . . ?
C00K C00J H00K 119.9 . . ?
C00J C00K H00L 120.0 . . ?
C00L C00K C00J 120.1(2) . . ?
C00L C00K H00L 120.0 . . ?
C00G C00L H00M 119.9 . . ?
C00K C00L C00G 120.2(2) . . ?
C00K C00L H00M 119.9 . . ?
_shelx_res_file
;
20170623-xiayi-zzw-1.res created by SHELXL-2014/7
TITL 20170623-xiayi-zzw-1_a.res in Pbca
REM Old TITL 20170623-Xia Yi-ZZW-1 in Pbca
REM SHELXT solution in Pbca
REM R1 0.134, Rweak 0.282, Alpha 0.025, Orientation as input
REM Formula found by SHELXT: C13 N6 O2
CELL 0.71073 11.4857 6.9956 33.9498 90 90 90
ZERR 8 0.0007 0.0004 0.0031 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 112 112 32 24
L.S. 30
PLAN 20
BOND $H
LIST 6
fmap 2
ACTA
SHEL 999 0.8
REM
REM
REM
WGHT 0.039900 3.385800
FVAR 0.36112
O001 4 0.536177 0.757439 0.439715 11.00000 0.02542 0.02756 =
0.01614 -0.00159 -0.00038 -0.00753
O002 4 0.312389 0.664611 0.499548 11.00000 0.03235 0.04190 =
0.01959 -0.00890 -0.00409 0.00040
O003 4 0.600850 1.146638 0.434297 11.00000 0.03413 0.02987 =
0.03681 -0.00833 -0.00983 -0.00019
AFIX 147
H003 2 0.642527 1.181694 0.452529 11.00000 -1.50000
AFIX 0
N004 3 0.185232 0.580974 0.404525 11.00000 0.02221 0.02538 =
0.01384 -0.00159 0.00045 -0.00232
N005 3 0.372427 0.575350 0.418021 11.00000 0.01936 0.02200 =
0.01527 -0.00241 -0.00110 -0.00250
N006 3 0.365713 0.538532 0.378763 11.00000 0.02172 0.02401 =
0.01516 -0.00260 -0.00027 -0.00187
N007 3 0.122013 0.653499 0.481621 11.00000 0.02690 0.03468 =
0.01546 -0.00451 0.00249 0.00284
AFIX 93
H00A 2 0.097036 0.678974 0.504918 11.00000 -1.20000
H00B 2 0.073391 0.635614 0.462713 11.00000 -1.20000
AFIX 0
C008 1 0.251492 0.543278 0.372132 11.00000 0.02183 0.01755 =
0.01640 -0.00059 0.00034 -0.00232
C009 1 0.264116 0.599753 0.432729 11.00000 0.02146 0.01776 =
0.01526 -0.00130 -0.00026 -0.00270
C00A 1 0.204389 0.508051 0.333551 11.00000 0.02234 0.02104 =
0.02344 0.00043 0.00249 -0.00112
C00B 1 0.139142 0.437089 0.260622 11.00000 0.02392 0.02053 =
0.01600 0.00165 -0.00414 -0.00264
C00C 1 0.235142 0.641832 0.474876 11.00000 0.03043 0.01801 =
0.01592 -0.00133 0.00126 0.00002
C00D 1 0.487629 0.574793 0.436700 11.00000 0.02156 0.02482 =
0.02028 -0.00046 -0.00513 -0.00057
C00E 1 0.170999 0.474813 0.301120 11.00000 0.01975 0.02048 =
0.02243 0.00180 -0.00241 -0.00257
C00F 1 0.218441 0.347652 0.235778 11.00000 0.02415 0.02282 =
0.02600 0.00195 -0.00326 0.00186
AFIX 43
H00F 2 0.290479 0.309038 0.245427 11.00000 -1.20000
AFIX 0
C00G 1 0.031797 0.496308 0.245889 11.00000 0.02432 0.02809 =
0.02147 -0.00173 -0.00209 0.00159
AFIX 43
H00G 2 -0.021728 0.555674 0.262407 11.00000 -1.20000
AFIX 0
C00H 1 0.574331 0.841144 0.403195 11.00000 0.02384 0.02802 =
0.01393 -0.00101 0.00086 0.00011
AFIX 23
H00E 2 0.508186 0.891647 0.388798 11.00000 -1.20000
H00H 2 0.612105 0.745288 0.386981 11.00000 -1.20000
AFIX 0
C00I 1 0.658326 0.999118 0.412741 11.00000 0.02636 0.02696 =
0.02809 0.00241 0.00453 -0.00347
AFIX 23
H00I 2 0.722302 0.948660 0.428225 11.00000 -1.20000
H00J 2 0.690059 1.051343 0.388548 11.00000 -1.20000
AFIX 0
C00J 1 0.190075 0.315923 0.196509 11.00000 0.03590 0.02923 =
0.02093 -0.00322 0.00281 0.00245
AFIX 43
H00K 2 0.242855 0.254782 0.179991 11.00000 -1.20000
AFIX 0
C00K 1 0.083375 0.375173 0.181931 11.00000 0.04301 0.03685 =
0.01834 0.00003 -0.00803 -0.00231
AFIX 43
H00L 2 0.064556 0.353544 0.155663 11.00000 -1.20000
AFIX 0
C00L 1 0.004874 0.466385 0.206383 11.00000 0.02807 0.04055 =
0.02468 0.00171 -0.00963 0.00209
AFIX 43
H00M 2 -0.066179 0.507925 0.196418 11.00000 -1.20000
AFIX 0
H00C 2 0.478822 0.527775 0.463449 11.00000 0.01809
H00D 2 0.533465 0.486231 0.420224 11.00000 0.02210
HKLF 4
REM 20170623-xiayi-zzw-1_a.res in Pbca
REM R1 = 0.0487 for 2304 Fo > 4sig(Fo) and 0.0596 for all 2788 data
REM 199 parameters refined using 0 restraints
END
WGHT 0.0398 3.3881
REM Highest difference peak 0.367, deepest hole -0.228, 1-sigma level 0.052
Q1 1 0.1368 0.5016 0.3212 11.00000 0.05 0.37
Q2 1 0.2438 0.5943 0.4525 11.00000 0.05 0.28
Q3 1 0.5622 1.1525 0.4083 11.00000 0.05 0.26
Q4 1 0.1229 0.5080 0.4109 11.00000 0.05 0.22
Q5 1 0.1455 0.4453 0.2818 11.00000 0.05 0.20
Q6 1 0.1969 0.4924 0.2498 11.00000 0.05 0.20
Q7 1 0.3631 0.5340 0.4800 11.00000 0.05 0.20
Q8 1 0.6343 1.0149 0.3593 11.00000 0.05 0.18
Q9 1 0.1536 0.3416 0.2507 11.00000 0.05 0.18
Q10 1 0.1210 0.3561 0.1405 11.00000 0.05 0.17
Q11 1 0.0177 0.6505 0.3033 11.00000 0.05 0.17
Q12 1 0.0081 0.4012 0.2309 11.00000 0.05 0.16
Q13 1 0.0093 0.6196 0.5199 11.00000 0.05 0.16
Q14 1 0.1006 0.6098 0.4015 11.00000 0.05 0.16
Q15 1 0.4726 1.1291 0.4105 11.00000 0.05 0.16
Q16 1 0.3071 0.5204 0.4303 11.00000 0.05 0.16
Q17 1 0.4764 0.3675 0.4742 11.00000 0.05 0.16
Q18 1 0.3671 0.1681 0.2487 11.00000 0.05 0.15
Q19 1 0.3829 0.6819 0.4888 11.00000 0.05 0.15
Q20 1 0.0627 0.4645 0.1912 11.00000 0.05 0.15
;
_shelx_res_checksum 9981
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.755