# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1874277'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record
;
2018-10-20 deposited with the CCDC. 2020-03-11 downloaded from the CCDC.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C15 H12 N4 O3 S'
_chemical_formula_weight 328.35
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 6.4901(2)
_cell_length_b 13.5853(4)
_cell_length_c 17.2054(6)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1517.00(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 7004
_cell_measurement_theta_min 2.37
_cell_measurement_theta_max 27.47
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.36
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.18
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.438
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 680
_exptl_absorpt_coefficient_mu 0.234
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9205
_exptl_absorpt_correction_T_max 0.9591
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Smart Apex II CCD'
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 17672
_diffrn_reflns_av_R_equivalents 0.0316
_diffrn_reflns_av_sigmaI/netI 0.0177
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 1.91
_diffrn_reflns_theta_max 25.01
_reflns_number_total 2673
_reflns_number_gt 2510
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.2743P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.01(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns 2673
_refine_ls_number_parameters 208
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0369
_refine_ls_R_factor_gt 0.0332
_refine_ls_wR_factor_ref 0.0922
_refine_ls_wR_factor_gt 0.0885
_refine_ls_goodness_of_fit_ref 1.055
_refine_ls_restrained_S_all 1.055
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97202(10) 0.40728(6) 0.99903(4) 0.0688(2) Uani 1 1 d . . .
O1 O 1.1846(4) 0.24230(15) 1.18721(17) 0.1035(8) Uani 1 1 d . . .
O2 O 1.4873(4) 0.27082(17) 1.22721(14) 0.1084(9) Uani 1 1 d . . .
O3 O 0.7033(2) 0.53418(12) 1.11922(10) 0.0519(4) Uani 1 1 d . . .
N1 N 1.3182(4) 0.29690(16) 1.20652(11) 0.0605(5) Uani 1 1 d . . .
N2 N 1.0029(3) 0.55486(13) 1.25598(10) 0.0478(4) Uani 1 1 d . . .
N3 N 0.8274(3) 0.52993(12) 1.27574(10) 0.0465(4) Uani 1 1 d . . .
N4 N 0.6732(4) 0.51170(16) 1.30216(13) 0.0683(6) Uani 1 1 d . . .
C1 C 0.8972(3) 0.68474(14) 1.10727(10) 0.0383(4) Uani 1 1 d . . .
C2 C 0.7593(3) 0.75361(16) 1.07788(12) 0.0477(5) Uani 1 1 d . . .
H2A H 0.6241 0.7363 1.0662 0.057 Uiso 1 1 calc R . .
C3 C 0.8295(4) 0.84857(17) 1.06651(14) 0.0558(6) Uani 1 1 d . . .
H3A H 0.7409 0.8963 1.0469 0.067 Uiso 1 1 calc R . .
C4 C 1.0305(4) 0.87281(17) 1.08409(13) 0.0565(6) Uani 1 1 d . . .
H4A H 1.0753 0.9370 1.0758 0.068 Uiso 1 1 calc R . .
C5 C 1.1672(4) 0.80450(15) 1.11361(12) 0.0485(5) Uani 1 1 d . . .
H5A H 1.3019 0.8223 1.1256 0.058 Uiso 1 1 calc R . .
C6 C 1.0999(3) 0.70934(14) 1.12496(11) 0.0379(4) Uani 1 1 d . . .
C7 C 1.2184(3) 0.62102(14) 1.15456(13) 0.0412(5) Uani 1 1 d . . .
H7A H 1.2941 0.6372 1.2015 0.049 Uiso 1 1 calc R . .
H7B H 1.3144 0.5973 1.1156 0.049 Uiso 1 1 calc R . .
C8 C 1.0520(3) 0.54428(14) 1.17121(11) 0.0361(4) Uani 1 1 d . . .
C9 C 0.8588(3) 0.58190(15) 1.12773(11) 0.0381(4) Uani 1 1 d . . .
C10 C 1.2805(3) 0.40535(15) 1.20699(12) 0.0455(5) Uani 1 1 d . . .
H10A H 1.4053 0.4390 1.1911 0.055 Uiso 1 1 calc R . .
H10B H 1.2483 0.4261 1.2596 0.055 Uiso 1 1 calc R . .
C11 C 1.1057(3) 0.43541(13) 1.15351(11) 0.0361(4) Uani 1 1 d . . .
H11A H 0.9853 0.3953 1.1668 0.043 Uiso 1 1 calc R . .
C12 C 1.1585(3) 0.41569(13) 1.06952(11) 0.0382(4) Uani 1 1 d . . .
C13 C 1.3477(3) 0.39592(16) 1.03731(12) 0.0471(5) Uani 1 1 d . . .
H13A H 1.4703 0.3975 1.0653 0.057 Uiso 1 1 calc R . .
C14 C 1.3370(5) 0.37279(18) 0.95708(14) 0.0614(6) Uani 1 1 d . . .
H14A H 1.4511 0.3569 0.9269 0.074 Uiso 1 1 calc R . .
C15 C 1.1456(5) 0.3763(2) 0.92983(14) 0.0705(8) Uani 1 1 d . . .
H15B H 1.1109 0.3633 0.8784 0.085 Uiso 1 1 calc R . .
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
S1 0.0608(4) 0.0908(5) 0.0549(3) -0.0177(4) -0.0194(3) 0.0093(3)
O1 0.1089(17) 0.0424(10) 0.159(2) 0.0237(12) -0.0107(18) -0.0096(12)
O2 0.1267(19) 0.0858(15) 0.1126(18) -0.0154(13) -0.0515(16) 0.0645(15)
O3 0.0356(7) 0.0505(8) 0.0697(10) -0.0025(7) -0.0087(7) -0.0038(7)
N1 0.0823(15) 0.0494(11) 0.0499(10) 0.0086(9) -0.0026(11) 0.0225(12)
N2 0.0460(10) 0.0537(11) 0.0438(9) -0.0084(8) -0.0013(8) 0.0027(9)
N3 0.0571(12) 0.0389(9) 0.0436(9) -0.0010(7) 0.0055(9) 0.0092(9)
N4 0.0680(14) 0.0711(14) 0.0657(13) 0.0039(11) 0.0170(12) -0.0019(12)
C1 0.0409(10) 0.0387(10) 0.0353(9) -0.0038(8) -0.0022(8) 0.0042(8)
C2 0.0482(12) 0.0522(13) 0.0427(11) -0.0026(9) -0.0076(8) 0.0122(10)
C3 0.0733(15) 0.0456(12) 0.0485(12) 0.0028(10) -0.0056(11) 0.0187(12)
C4 0.0812(17) 0.0363(11) 0.0520(12) -0.0009(9) -0.0022(12) 0.0049(11)
C5 0.0536(12) 0.0392(11) 0.0527(11) -0.0025(10) -0.0001(10) -0.0028(10)
C6 0.0400(10) 0.0353(10) 0.0384(9) -0.0059(8) -0.0012(8) 0.0018(8)
C7 0.0345(10) 0.0351(10) 0.0539(11) -0.0035(9) -0.0057(9) 0.0010(8)
C8 0.0347(9) 0.0343(9) 0.0393(9) -0.0020(8) -0.0054(8) 0.0022(8)
C9 0.0325(9) 0.0402(10) 0.0415(10) -0.0039(8) -0.0027(8) 0.0021(8)
C10 0.0535(12) 0.0394(11) 0.0434(10) 0.0004(9) -0.0073(9) 0.0090(10)
C11 0.0361(9) 0.0319(9) 0.0402(9) 0.0020(7) -0.0017(8) -0.0020(7)
C12 0.0446(10) 0.0285(9) 0.0416(9) -0.0007(8) -0.0066(8) -0.0039(9)
C13 0.0473(11) 0.0506(12) 0.0434(11) -0.0054(9) 0.0014(9) -0.0048(10)
C14 0.0774(17) 0.0565(14) 0.0503(13) -0.0058(10) 0.0146(13) -0.0002(13)
C15 0.101(2) 0.0676(16) 0.0434(12) -0.0110(11) -0.0072(14) 0.0096(15)
_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
S1 C15 1.692(3) . ?
S1 C12 1.7173(19) . ?
O1 N1 1.189(3) . ?
O2 N1 1.207(3) . ?
O3 C9 1.208(2) . ?
N1 C10 1.494(3) . ?
N2 N3 1.236(3) . ?
N2 C8 1.500(3) . ?
N3 N4 1.127(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.391(3) . ?
C1 C9 1.462(3) . ?
C2 C3 1.382(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.513(3) . ?
C7 C8 1.528(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.547(3) . ?
C8 C11 1.550(3) . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9800 . ?
C12 C13 1.374(3) . ?
C13 C14 1.417(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.329(4) . ?
C14 H14A 0.9300 . ?
C15 H15B 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
C15 S1 C12 92.53(12) . . ?
O1 N1 O2 124.2(2) . . ?
O1 N1 C10 119.8(2) . . ?
O2 N1 C10 115.9(2) . . ?
N3 N2 C8 115.90(17) . . ?
N4 N3 N2 171.8(2) . . ?
C2 C1 C6 121.80(19) . . ?
C2 C1 C9 128.37(19) . . ?
C6 C1 C9 109.77(17) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 119.61(19) . . ?
C5 C6 C7 129.06(19) . . ?
C1 C6 C7 111.33(17) . . ?
C6 C7 C8 104.17(15) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
N2 C8 C7 105.49(16) . . ?
N2 C8 C9 105.47(15) . . ?
C7 C8 C9 104.88(15) . . ?
N2 C8 C11 109.29(15) . . ?
C7 C8 C11 117.06(16) . . ?
C9 C8 C11 113.75(15) . . ?
O3 C9 C1 128.75(18) . . ?
O3 C9 C8 123.93(18) . . ?
C1 C9 C8 107.09(15) . . ?
N1 C10 C11 112.65(18) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 111.31(16) . . ?
C12 C11 C8 114.13(15) . . ?
C10 C11 C8 107.83(15) . . ?
C12 C11 H11A 107.8 . . ?
C10 C11 H11A 107.8 . . ?
C8 C11 H11A 107.8 . . ?
C13 C12 C11 128.60(18) . . ?
C13 C12 S1 109.40(15) . . ?
C11 C12 S1 121.87(15) . . ?
C12 C13 C14 113.1(2) . . ?
C12 C13 H13A 123.5 . . ?
C14 C13 H13A 123.5 . . ?
C15 C14 C13 112.4(2) . . ?
C15 C14 H14A 123.8 . . ?
C13 C14 H14A 123.8 . . ?
C14 C15 S1 112.53(19) . . ?
C14 C15 H15B 123.7 . . ?
S1 C15 H15B 123.7 . . ?
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
C8 N2 N3 N4 -172.6(15) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C9 C1 C2 C3 176.86(19) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C9 C1 C6 C5 -177.08(17) . . . . ?
C2 C1 C6 C7 -178.99(18) . . . . ?
C9 C1 C6 C7 3.6(2) . . . . ?
C5 C6 C7 C8 167.9(2) . . . . ?
C1 C6 C7 C8 -12.9(2) . . . . ?
N3 N2 C8 C7 153.11(17) . . . . ?
N3 N2 C8 C9 42.4(2) . . . . ?
N3 N2 C8 C11 -80.2(2) . . . . ?
C6 C7 C8 N2 -94.79(17) . . . . ?
C6 C7 C8 C9 16.3(2) . . . . ?
C6 C7 C8 C11 143.44(16) . . . . ?
C2 C1 C9 O3 4.7(3) . . . . ?
C6 C1 C9 O3 -178.1(2) . . . . ?
C2 C1 C9 C8 -169.93(19) . . . . ?
C6 C1 C9 C8 7.2(2) . . . . ?
N2 C8 C9 O3 -78.7(2) . . . . ?
C7 C8 C9 O3 170.21(18) . . . . ?
C11 C8 C9 O3 41.1(3) . . . . ?
N2 C8 C9 C1 96.26(17) . . . . ?
C7 C8 C9 C1 -14.9(2) . . . . ?
C11 C8 C9 C1 -143.99(16) . . . . ?
O1 N1 C10 C11 -22.7(3) . . . . ?
O2 N1 C10 C11 158.0(2) . . . . ?
N1 C10 C11 C12 -65.4(2) . . . . ?
N1 C10 C11 C8 168.68(18) . . . . ?
N2 C8 C11 C12 -179.89(16) . . . . ?
C7 C8 C11 C12 -60.1(2) . . . . ?
C9 C8 C11 C12 62.5(2) . . . . ?
N2 C8 C11 C10 -55.7(2) . . . . ?
C7 C8 C11 C10 64.1(2) . . . . ?
C9 C8 C11 C10 -173.24(16) . . . . ?
C10 C11 C12 C13 -15.0(3) . . . . ?
C8 C11 C12 C13 107.3(2) . . . . ?
C10 C11 C12 S1 160.51(14) . . . . ?
C8 C11 C12 S1 -77.2(2) . . . . ?
C15 S1 C12 C13 0.88(18) . . . . ?
C15 S1 C12 C11 -175.42(17) . . . . ?
C11 C12 C13 C14 174.90(19) . . . . ?
S1 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 S1 -0.1(3) . . . . ?
C12 S1 C15 C14 -0.5(2) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.221
_refine_diff_density_min -0.243
_refine_diff_density_rms 0.035
#######################################################################
#
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1874278'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record
;
2018-10-20 deposited with the CCDC. 2020-03-11 downloaded from the CCDC.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C25 H21 Cl N2 O3'
_chemical_formula_weight 432.89
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 6.2023(2)
_cell_length_b 15.1707(4)
_cell_length_c 23.3424(7)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2196.36(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 6102
_cell_measurement_theta_min 2.69
_cell_measurement_theta_max 23.02
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.33
_exptl_crystal_size_min 0.17
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.309
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 904
_exptl_absorpt_coefficient_mu 0.203
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9323
_exptl_absorpt_correction_T_max 0.9663
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Smart Apex II CCD'
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 25874
_diffrn_reflns_av_R_equivalents 0.0399
_diffrn_reflns_av_sigmaI/netI 0.0255
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 1.60
_diffrn_reflns_theta_max 25.01
_reflns_number_total 3885
_reflns_number_gt 3249
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.3348P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.01(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns 3885
_refine_ls_number_parameters 280
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0508
_refine_ls_R_factor_gt 0.0391
_refine_ls_wR_factor_ref 0.1092
_refine_ls_wR_factor_gt 0.1005
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.99399(15) 0.84045(5) 0.88806(4) 0.0884(3) Uani 1 1 d . . .
O1 O 0.5563(3) 0.44383(12) 0.96452(7) 0.0575(5) Uani 1 1 d . . .
O2 O 1.2797(4) 0.46267(16) 1.10066(10) 0.0837(7) Uani 1 1 d . . .
O3 O 1.0281(6) 0.52055(16) 1.15196(9) 0.1088(10) Uani 1 1 d . . .
N2 N 0.9200(3) 0.33860(12) 1.01176(8) 0.0446(5) Uani 1 1 d . . .
H2B H 0.9551 0.2840 1.0086 0.054 Uiso 1 1 calc R . .
N1 N 1.0947(5) 0.48829(14) 1.10798(9) 0.0623(6) Uani 1 1 d . . .
C1 C 0.7688(4) 0.44995(15) 0.87850(10) 0.0444(6) Uani 1 1 d . . .
C2 C 0.6349(5) 0.48852(17) 0.83734(11) 0.0577(7) Uani 1 1 d . . .
H2A H 0.4971 0.5076 0.8469 0.069 Uiso 1 1 calc R . .
C3 C 0.7116(6) 0.4975(2) 0.78261(12) 0.0729(9) Uani 1 1 d . . .
H3A H 0.6264 0.5234 0.7545 0.087 Uiso 1 1 calc R . .
C4 C 0.9184(6) 0.4675(2) 0.76943(12) 0.0746(9) Uani 1 1 d . . .
H4A H 0.9695 0.4744 0.7322 0.089 Uiso 1 1 calc R . .
C5 C 1.0491(5) 0.42816(18) 0.80935(11) 0.0605(7) Uani 1 1 d . . .
H5A H 1.1854 0.4077 0.7993 0.073 Uiso 1 1 calc R . .
C6 C 0.9732(4) 0.41947(15) 0.86521(10) 0.0451(6) Uani 1 1 d . . .
C7 C 1.0778(4) 0.37739(16) 0.91631(10) 0.0461(6) Uani 1 1 d . . .
H7A H 1.2248 0.3980 0.9208 0.055 Uiso 1 1 calc R . .
H7B H 1.0792 0.3137 0.9125 0.055 Uiso 1 1 calc R . .
C8 C 0.9394(3) 0.40544(13) 0.96724(9) 0.0373(5) Uani 1 1 d . . .
C9 C 0.7257(4) 0.43446(14) 0.93896(10) 0.0411(5) Uani 1 1 d . . .
C10 C 1.0195(4) 0.57463(13) 0.97449(9) 0.0377(5) Uani 1 1 d . . .
C11 C 0.8365(4) 0.62672(15) 0.97750(10) 0.0467(6) Uani 1 1 d . . .
H11A H 0.7172 0.6068 0.9978 0.056 Uiso 1 1 calc R . .
C12 C 0.8285(4) 0.70787(15) 0.95073(11) 0.0521(6) Uani 1 1 d . . .
H12A H 0.7047 0.7423 0.9531 0.062 Uiso 1 1 calc R . .
C13 C 1.0034(4) 0.73711(15) 0.92087(11) 0.0528(6) Uani 1 1 d . . .
C14 C 1.1869(4) 0.68744(18) 0.91659(12) 0.0605(7) Uani 1 1 d . . .
H14A H 1.3046 0.7077 0.8957 0.073 Uiso 1 1 calc R . .
C15 C 1.1939(4) 0.60659(16) 0.94387(10) 0.0499(6) Uani 1 1 d . . .
H15A H 1.3188 0.5729 0.9416 0.060 Uiso 1 1 calc R . .
C16 C 0.8298(4) 0.38104(14) 1.06299(10) 0.0436(5) Uani 1 1 d . . .
H16A H 0.6739 0.3870 1.0573 0.052 Uiso 1 1 calc R . .
C17 C 0.9302(4) 0.47505(14) 1.06074(9) 0.0446(6) Uani 1 1 d . . .
H17A H 0.8156 0.5191 1.0646 0.054 Uiso 1 1 calc R . .
C18 C 1.0347(4) 0.48402(13) 1.00202(9) 0.0374(5) Uani 1 1 d . . .
H18A H 1.1885 0.4716 1.0072 0.045 Uiso 1 1 calc R . .
C19 C 0.8652(4) 0.33125(14) 1.11840(10) 0.0423(5) Uani 1 1 d . . .
C20 C 1.0554(5) 0.28714(16) 1.12985(11) 0.0529(6) Uani 1 1 d . . .
H20A H 1.1611 0.2825 1.1018 0.063 Uiso 1 1 calc R . .
C21 C 1.0878(5) 0.24993(17) 1.18334(12) 0.0618(7) Uani 1 1 d . . .
H21A H 1.2160 0.2202 1.1906 0.074 Uiso 1 1 calc R . .
C22 C 0.9358(6) 0.25576(17) 1.22586(11) 0.0628(8) Uani 1 1 d . . .
C23 C 0.7470(5) 0.29759(18) 1.21361(12) 0.0612(7) Uani 1 1 d . . .
H23A H 0.6404 0.3011 1.2415 0.073 Uiso 1 1 calc R . .
C24 C 0.7108(4) 0.33507(16) 1.16028(11) 0.0535(6) Uani 1 1 d . . .
H24A H 0.5803 0.3631 1.1529 0.064 Uiso 1 1 calc R . .
C25 C 0.9764(7) 0.2168(2) 1.28472(13) 0.1019(13) Uani 1 1 d . . .
H25A H 0.8527 0.2266 1.3086 0.153 Uiso 1 1 calc R . .
H25B H 1.1002 0.2445 1.3016 0.153 Uiso 1 1 calc R . .
H25C H 1.0019 0.1546 1.2812 0.153 Uiso 1 1 calc R . .
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
Cl1 0.1084(7) 0.0570(4) 0.0997(6) 0.0332(4) -0.0256(5) -0.0082(4)
O1 0.0365(9) 0.0825(12) 0.0535(10) 0.0050(9) 0.0018(8) 0.0089(8)
O2 0.0891(17) 0.0887(16) 0.0734(15) 0.0130(12) -0.0346(14) -0.0167(13)
O3 0.193(3) 0.0879(15) 0.0459(12) -0.0242(11) 0.0114(16) -0.0317(19)
N2 0.0561(12) 0.0359(9) 0.0418(11) -0.0006(8) -0.0027(9) 0.0049(9)
N1 0.105(2) 0.0422(11) 0.0399(13) -0.0030(9) -0.0052(13) -0.0176(13)
C1 0.0466(14) 0.0465(12) 0.0402(13) -0.0025(10) -0.0076(11) 0.0005(10)
C2 0.0635(16) 0.0574(15) 0.0521(17) 0.0033(13) -0.0133(14) 0.0048(13)
C3 0.098(3) 0.0749(19) 0.0454(17) 0.0094(14) -0.0158(17) 0.0035(18)
C4 0.104(3) 0.0769(19) 0.0423(16) 0.0037(14) 0.0049(17) -0.0074(19)
C5 0.0667(18) 0.0654(16) 0.0493(16) -0.0089(13) 0.0085(14) -0.0013(15)
C6 0.0515(14) 0.0463(12) 0.0374(12) -0.0093(10) -0.0006(11) -0.0028(11)
C7 0.0449(13) 0.0502(13) 0.0432(13) -0.0111(11) 0.0004(11) 0.0080(11)
C8 0.0356(11) 0.0385(11) 0.0377(12) -0.0013(9) -0.0032(10) 0.0056(9)
C9 0.0374(13) 0.0427(12) 0.0433(13) -0.0040(10) -0.0023(11) 0.0000(10)
C10 0.0413(12) 0.0378(10) 0.0339(11) -0.0009(9) 0.0002(10) 0.0015(10)
C11 0.0434(13) 0.0475(12) 0.0492(15) 0.0023(11) 0.0035(11) 0.0051(11)
C12 0.0554(16) 0.0418(12) 0.0591(16) 0.0006(11) -0.0072(13) 0.0125(11)
C13 0.0635(17) 0.0425(12) 0.0525(15) 0.0083(11) -0.0125(13) -0.0031(12)
C14 0.0584(17) 0.0652(16) 0.0579(17) 0.0166(14) 0.0026(14) -0.0077(14)
C15 0.0430(14) 0.0554(14) 0.0514(15) 0.0082(12) 0.0022(11) 0.0062(11)
C16 0.0443(13) 0.0459(12) 0.0406(13) 0.0037(10) -0.0016(11) 0.0022(10)
C17 0.0579(15) 0.0382(11) 0.0377(13) 0.0004(10) 0.0044(11) 0.0102(11)
C18 0.0366(12) 0.0386(11) 0.0371(12) -0.0041(9) -0.0017(10) 0.0063(10)
C19 0.0474(13) 0.0358(11) 0.0437(14) 0.0032(10) -0.0039(11) -0.0033(10)
C20 0.0629(16) 0.0448(12) 0.0510(15) 0.0019(11) 0.0015(13) 0.0046(12)
C21 0.0773(19) 0.0491(14) 0.0588(17) 0.0039(13) -0.0153(15) 0.0101(14)
C22 0.097(2) 0.0444(13) 0.0469(15) 0.0052(12) -0.0079(16) -0.0076(15)
C23 0.0757(19) 0.0583(15) 0.0495(15) 0.0048(13) 0.0085(15) -0.0102(15)
C24 0.0551(15) 0.0536(14) 0.0517(15) 0.0030(13) 0.0023(13) -0.0051(13)
C25 0.156(4) 0.100(2) 0.0504(18) 0.0246(17) -0.017(2) 0.006(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
Cl1 C13 1.746(2) . ?
O1 C9 1.217(3) . ?
O2 N1 1.224(3) . ?
O3 N1 1.210(3) . ?
N2 C8 1.457(3) . ?
N2 C16 1.469(3) . ?
N2 H2B 0.8600 . ?
N1 C17 1.515(4) . ?
C1 C6 1.385(3) . ?
C1 C2 1.398(3) . ?
C1 C9 1.455(3) . ?
C2 C3 1.370(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.500(3) . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.545(3) . ?
C8 C18 1.559(3) . ?
C10 C15 1.384(3) . ?
C10 C11 1.385(3) . ?
C10 C18 1.520(3) . ?
C11 C12 1.381(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.364(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(4) . ?
C14 C15 1.383(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C19 1.514(3) . ?
C16 C17 1.557(3) . ?
C16 H16A 0.9800 . ?
C17 C18 1.522(3) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9800 . ?
C19 C24 1.370(3) . ?
C19 C20 1.382(4) . ?
C20 C21 1.385(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.372(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.362(4) . ?
C22 C25 1.517(4) . ?
C23 C24 1.387(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C8 N2 C16 107.89(16) . . ?
C8 N2 H2B 126.1 . . ?
C16 N2 H2B 126.1 . . ?
O3 N1 O2 124.5(3) . . ?
O3 N1 C17 116.2(3) . . ?
O2 N1 C17 119.2(2) . . ?
C6 C1 C2 122.0(2) . . ?
C6 C1 C9 109.3(2) . . ?
C2 C1 C9 128.7(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 122.4(3) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 111.1(2) . . ?
C5 C6 C7 129.7(2) . . ?
C6 C7 C8 104.94(18) . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
N2 C8 C7 114.09(18) . . ?
N2 C8 C9 115.59(18) . . ?
C7 C8 C9 103.23(17) . . ?
N2 C8 C18 101.09(16) . . ?
C7 C8 C18 113.94(19) . . ?
C9 C8 C18 109.26(17) . . ?
O1 C9 C1 128.0(2) . . ?
O1 C9 C8 124.4(2) . . ?
C1 C9 C8 107.64(19) . . ?
C15 C10 C11 117.8(2) . . ?
C15 C10 C18 119.13(19) . . ?
C11 C10 C18 123.0(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 121.3(2) . . ?
C12 C13 Cl1 119.3(2) . . ?
C14 C13 Cl1 119.4(2) . . ?
C13 C14 C15 118.7(2) . . ?
C13 C14 H14A 120.6 . . ?
C15 C14 H14A 120.6 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 H15A 119.2 . . ?
C10 C15 H15A 119.2 . . ?
N2 C16 C19 114.94(18) . . ?
N2 C16 C17 102.80(18) . . ?
C19 C16 C17 115.32(19) . . ?
N2 C16 H16A 107.8 . . ?
C19 C16 H16A 107.8 . . ?
C17 C16 H16A 107.8 . . ?
N1 C17 C18 110.9(2) . . ?
N1 C17 C16 111.48(18) . . ?
C18 C17 C16 106.40(17) . . ?
N1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C10 C18 C17 115.79(17) . . ?
C10 C18 C8 116.63(17) . . ?
C17 C18 C8 103.85(18) . . ?
C10 C18 H18A 106.6 . . ?
C17 C18 H18A 106.6 . . ?
C8 C18 H18A 106.6 . . ?
C24 C19 C20 118.6(2) . . ?
C24 C19 C16 119.2(2) . . ?
C20 C19 C16 122.1(2) . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 H21A 119.1 . . ?
C20 C21 H21A 119.1 . . ?
C23 C22 C21 118.0(2) . . ?
C23 C22 C25 121.0(3) . . ?
C21 C22 C25 121.1(3) . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 H23A 119.4 . . ?
C24 C23 H23A 119.4 . . ?
C19 C24 C23 120.7(3) . . ?
C19 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C6 C1 C2 C3 -1.2(4) . . . . ?
C9 C1 C2 C3 179.1(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C9 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C7 -177.3(2) . . . . ?
C9 C1 C6 C7 2.5(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C1 C6 C7 C8 -14.0(3) . . . . ?
C5 C6 C7 C8 168.4(2) . . . . ?
C16 N2 C8 C7 166.53(19) . . . . ?
C16 N2 C8 C9 -74.0(2) . . . . ?
C16 N2 C8 C18 43.8(2) . . . . ?
C6 C7 C8 N2 144.96(19) . . . . ?
C6 C7 C8 C9 18.7(2) . . . . ?
C6 C7 C8 C18 -99.6(2) . . . . ?
C6 C1 C9 O1 -171.5(2) . . . . ?
C2 C1 C9 O1 8.2(4) . . . . ?
C6 C1 C9 C8 10.0(2) . . . . ?
C2 C1 C9 C8 -170.2(2) . . . . ?
N2 C8 C9 O1 38.3(3) . . . . ?
C7 C8 C9 O1 163.6(2) . . . . ?
C18 C8 C9 O1 -74.8(3) . . . . ?
N2 C8 C9 C1 -143.21(18) . . . . ?
C7 C8 C9 C1 -17.9(2) . . . . ?
C18 C8 C9 C1 103.6(2) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C18 C10 C11 C12 -178.6(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C11 C12 C13 Cl1 -179.0(2) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
Cl1 C13 C14 C15 178.6(2) . . . . ?
C13 C14 C15 C10 0.9(4) . . . . ?
C11 C10 C15 C14 -0.5(4) . . . . ?
C18 C10 C15 C14 178.1(2) . . . . ?
C8 N2 C16 C19 -160.83(18) . . . . ?
C8 N2 C16 C17 -34.7(2) . . . . ?
O3 N1 C17 C18 148.6(2) . . . . ?
O2 N1 C17 C18 -34.7(3) . . . . ?
O3 N1 C17 C16 -93.0(2) . . . . ?
O2 N1 C17 C16 83.7(3) . . . . ?
N2 C16 C17 N1 -110.2(2) . . . . ?
C19 C16 C17 N1 15.7(3) . . . . ?
N2 C16 C17 C18 10.9(2) . . . . ?
C19 C16 C17 C18 136.7(2) . . . . ?
C15 C10 C18 C17 141.7(2) . . . . ?
C11 C10 C18 C17 -39.7(3) . . . . ?
C15 C10 C18 C8 -95.7(2) . . . . ?
C11 C10 C18 C8 82.9(3) . . . . ?
N1 C17 C18 C10 -95.0(2) . . . . ?
C16 C17 C18 C10 143.55(19) . . . . ?
N1 C17 C18 C8 135.78(18) . . . . ?
C16 C17 C18 C8 14.4(2) . . . . ?
N2 C8 C18 C10 -163.10(18) . . . . ?
C7 C8 C18 C10 74.1(2) . . . . ?
C9 C8 C18 C10 -40.8(2) . . . . ?
N2 C8 C18 C17 -34.4(2) . . . . ?
C7 C8 C18 C17 -157.26(18) . . . . ?
C9 C8 C18 C17 87.9(2) . . . . ?
N2 C16 C19 C24 -146.5(2) . . . . ?
C17 C16 C19 C24 94.1(3) . . . . ?
N2 C16 C19 C20 38.3(3) . . . . ?
C17 C16 C19 C20 -81.1(3) . . . . ?
C24 C19 C20 C21 -1.5(4) . . . . ?
C16 C19 C20 C21 173.7(2) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C23 1.7(4) . . . . ?
C20 C21 C22 C25 -178.3(3) . . . . ?
C21 C22 C23 C24 -1.5(4) . . . . ?
C25 C22 C23 C24 178.6(3) . . . . ?
C20 C19 C24 C23 1.8(4) . . . . ?
C16 C19 C24 C23 -173.6(2) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.226
_refine_diff_density_min -0.287
_refine_diff_density_rms 0.031
#######################################################################
#
# 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_exp_517
_database_code_depnum_ccdc_archive 'CCDC 1874283'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record
;
2018-10-20 deposited with the CCDC. 2020-03-11 downloaded from the CCDC.
;
_audit_creation_date 2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C18 H14 Br2 N4 O3'
_chemical_formula_sum 'C18 H14 Br2 N4 O3'
_chemical_formula_weight 494.15
_chemical_absolute_configuration ad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 7.63640(10)
_cell_length_b 11.6851(2)
_cell_length_c 11.5473(2)
_cell_angle_alpha 90
_cell_angle_beta 104.259(2)
_cell_angle_gamma 90
_cell_volume 998.65(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 12619
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 73.9920
_cell_measurement_theta_min 5.4150
_shelx_estimated_absorpt_T_max 0.445
_shelx_estimated_absorpt_T_min 0.278
_exptl_absorpt_coefficient_mu 5.374
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.46626
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.643
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 488
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.18
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0726
_diffrn_reflns_av_unetI/netI 0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 21816
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 74.458
_diffrn_reflns_theta_min 3.950
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -40.00 -14.00 1.00 2.00 -- 0.00 -52.00 -80.00 26
2 \w -22.00 45.00 1.00 2.00 -- 0.00 52.00 65.00 67
3 \w 42.00 67.00 1.00 2.00 -- 95.80 -52.00 -80.00 25
4 \w 76.00 172.00 1.00 2.00 -- 95.80 52.00 65.00 96
5 \w -21.00 23.00 1.00 2.00 -- 0.00 -57.00 60.00 44
6 \w 39.00 84.00 1.00 2.00 -- 0.00 38.00 0.00 45
7 \w -19.00 33.00 1.00 2.00 -- 0.00 38.00 0.00 52
8 \w 7.00 62.00 1.00 2.00 -- 0.00 77.00 60.00 55
9 \w -89.00 -51.00 1.00 2.00 -- 0.00 -38.00 -60.00 38
10 \w -89.00 -30.00 1.00 2.00 -- 0.00 -57.00 60.00 59
11 \w -11.00 24.00 1.00 2.00 -- 0.00 -19.00-150.00 35
12 \w -43.00 17.00 1.00 2.00 -- 0.00 -38.00 -60.00 60
13 \w -22.00 54.00 1.00 2.00 -- 0.00 57.00 -60.00 76
14 \w 39.00 75.00 1.00 2.00 -- 0.00 19.00-120.00 36
15 \w -19.00 31.00 1.00 2.00 -- 0.00 38.00 150.00 50
16 \w -50.00 -24.00 1.00 2.00 -- 0.00 -19.00-150.00 26
17 \w -19.00 33.00 1.00 2.00 -- 0.00 19.00-120.00 52
18 \w 65.00 118.00 1.00 2.00 -- 95.80 79.00 161.77 53
19 \w 72.00 107.00 1.00 2.00 -- 95.80 58.00 41.77 35
20 \w 41.00 126.00 1.00 2.00 -- 95.80 -82.00 150.00 85
21 \w 73.00 128.00 1.00 2.00 -- 95.80 -82.00 -60.00 55
22 \w 79.00 128.00 1.00 2.00 -- 95.80 -82.00-150.00 49
23 \w 11.00 37.00 1.00 2.00 -- 95.80 -82.00 150.00 26
24 \w 145.00 172.00 1.00 2.00 -- 95.80 77.00-150.00 27
25 \w 129.00 159.00 1.00 2.00 -- 95.80 45.00 30.00 30
26 \w 114.00 173.00 1.00 2.00 -- 95.80 79.00 -77.07 59
27 \w 75.00 119.00 1.00 2.00 -- 95.80 45.00 30.00 44
28 \w 71.00 96.00 1.00 2.00 -- 95.80 61.00-150.00 25
29 \w 65.00 99.00 1.00 2.00 -- 95.80 77.00 120.00 34
30 \w 75.00 114.00 1.00 2.00 -- 95.80 45.00 0.00 39
31 \w 116.00 141.00 1.00 2.00 -- 95.80 45.00 0.00 25
32 \w 149.00 185.00 1.00 2.00 -- 95.80 45.00 0.00 36
33 \w 64.00 89.00 1.00 2.00 -- 95.80 80.00 100.76 25
34 \w 67.00 93.00 1.00 2.00 -- 95.80 73.00 78.89 26
35 \w 75.00 121.00 1.00 2.00 -- 95.80 45.00 -90.00 46
36 \w 65.00 178.00 1.00 2.00 -- 95.80 77.00 90.00 113
37 \w 65.00 90.00 1.00 2.00 -- 95.80 77.00 -30.00 25
38 \w 146.00 171.00 1.00 2.00 -- 95.80 77.00 0.00 25
39 \w 75.00 185.00 1.00 2.00 -- 95.80 45.00 -30.00 110
40 \w 63.00 185.00 1.00 2.00 -- 95.80 82.00 130.09 122
41 \w 80.00 184.00 1.00 2.00 -- 95.80 45.00-120.00 104
42 \w 111.00 156.00 1.00 2.00 -- 95.80 82.00 150.00 45
43 \w 71.00 175.00 1.00 2.00 -- 95.80 59.00 76.40 104
44 \w 65.00 90.00 1.00 2.00 -- 95.80 77.00 60.00 25
45 \w 152.00 178.00 1.00 2.00 -- 95.80 77.00 60.00 26
46 \w 64.00 98.00 1.00 2.00 -- 95.80 79.00 -77.07 34
47 \w 116.00 185.00 1.00 2.00 -- 95.80 82.00-120.00 69
48 \w 69.00 95.00 1.00 2.00 -- 95.80 82.00 -30.00 26
49 \w 139.00 168.00 1.00 2.00 -- 95.80 82.00 -30.00 29
50 \w 64.00 89.00 1.00 2.00 -- 95.80 82.00 0.00 25
51 \w 63.00 99.00 1.00 2.00 -- 95.80 82.00 150.00 36
52 \w 68.00 123.00 1.00 2.00 -- 95.80 -77.00 -90.00 55
53 \w 12.00 49.00 1.00 2.00 -- 95.80 -77.00 -90.00 37
54 \w 65.00 91.00 1.00 2.00 -- 95.80 77.00 30.00 26
55 \w 76.00 102.00 1.00 2.00 -- 95.80 61.00 60.00 26
56 \w 66.00 92.00 1.00 2.00 -- 95.80 77.00 -90.00 26
57 \w 63.00 88.00 1.00 2.00 -- 95.80 82.00 120.00 25
58 \w 78.00 122.00 1.00 2.00 -- 95.80 -82.00 0.00 44
59 \w 71.00 96.00 1.00 2.00 -- 95.80 61.00-120.00 25
60 \w 65.00 91.00 1.00 2.00 -- 95.80 77.00-180.00 26
61 \w 139.00 169.00 1.00 2.00 -- 95.80 77.00-180.00 30
62 \w 61.00 105.00 1.00 2.00 -- 95.80 -82.00 90.00 44
63 \w 130.00 167.00 1.00 2.00 -- 95.80 79.00 161.77 37
64 \w 89.00 115.00 1.00 2.00 -- 95.80 30.00 -60.00 26
65 \w 63.00 88.00 1.00 2.00 -- 95.80 82.00-120.00 25
66 \w 65.00 91.00 1.00 2.00 -- 95.80 77.00 0.00 26
67 \w 65.00 90.00 1.00 2.00 -- 95.80 77.00-150.00 25
68 \w 65.00 90.00 1.00 2.00 -- 95.80 77.00 -60.00 25
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.1207180000
_diffrn_orient_matrix_UB_12 0.0873431000
_diffrn_orient_matrix_UB_13 0.0436225000
_diffrn_orient_matrix_UB_21 -0.1357054000
_diffrn_orient_matrix_UB_22 -0.0037369000
_diffrn_orient_matrix_UB_23 -0.1231976000
_diffrn_orient_matrix_UB_31 -0.1017326000
_diffrn_orient_matrix_UB_32 -0.0986824000
_diffrn_orient_matrix_UB_33 0.0431811000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.885
_reflns_Friedel_fraction_full 0.995
_reflns_Friedel_fraction_max 0.974
_reflns_number_gt 3735
_reflns_number_total 4011
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_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 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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 0.564
_refine_diff_density_min -0.552
_refine_diff_density_rms 0.054
_refine_ls_abs_structure_details
;
Flack x determined using 1583 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -0.015(12)
_refine_ls_extinction_coef 0.0081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 245
_refine_ls_number_reflns 4011
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0402
_refine_ls_R_factor_gt 0.0383
_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^)+(0.0605P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1042
_refine_ls_wR_factor_ref 0.1061
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens geom
_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
Br1 Br 0.14195(9) 0.23183(8) -0.03048(4) 0.0872(3) Uani 1 1 d . . . . .
Br2 Br 0.37674(17) 0.96481(8) 0.90308(9) 0.1152(4) Uani 1 1 d . . . . .
O1 O 0.1169(6) 0.0340(3) 0.5204(4) 0.0720(10) Uani 1 1 d . . . . .
O2 O 0.6661(6) 0.3077(4) 0.6254(4) 0.0764(11) Uani 1 1 d . . . . .
O3 O 0.6852(7) 0.2949(6) 0.8130(5) 0.0976(16) Uani 1 1 d . . . . .
N1 N 0.6083(6) 0.2766(4) 0.7092(4) 0.0629(11) Uani 1 1 d . . . . .
N2 N 0.0683(6) 0.1893(5) 0.6852(4) 0.0642(11) Uani 1 1 d . . . . .
N3 N -0.0588(6) 0.1218(4) 0.6746(4) 0.0625(10) Uani 1 1 d . . . . .
N4 N -0.1720(8) 0.0608(5) 0.6796(6) 0.0847(15) Uani 1 1 d . . . . .
C1 C 0.1556(6) 0.0717(5) 0.2900(4) 0.0579(11) Uani 1 1 d . . . . .
H1 H 0.170450 -0.002474 0.319985 0.069 Uiso 1 1 calc R . . . .
C2 C 0.1646(7) 0.0933(6) 0.1743(5) 0.0645(13) Uani 1 1 d . . . . .
H2 H 0.187173 0.034001 0.126153 0.077 Uiso 1 1 calc R . . . .
C3 C 0.1401(6) 0.2031(6) 0.1304(4) 0.0630(13) Uani 1 1 d . . . . .
C4 C 0.1066(7) 0.2925(5) 0.2005(5) 0.0614(12) Uani 1 1 d . . . . .
H4 H 0.089716 0.366487 0.170016 0.074 Uiso 1 1 calc R . . . .
C5 C 0.0986(7) 0.2703(5) 0.3162(4) 0.0583(12) Uani 1 1 d . . . . .
H5 H 0.075597 0.329612 0.364028 0.070 Uiso 1 1 calc R . . . .
C6 C 0.1244(6) 0.1609(4) 0.3618(4) 0.0513(10) Uani 1 1 d . . . . .
C7 C 0.1144(6) 0.1313(5) 0.4864(4) 0.0530(10) Uani 1 1 d . . . . .
C8 C 0.1056(5) 0.2304(5) 0.5727(3) 0.0508(9) Uani 1 1 d . . . . .
H8 H 0.010332 0.283890 0.533784 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2863(6) 0.2949(4) 0.6092(4) 0.0492(9) Uani 1 1 d . . . . .
H9 H 0.322271 0.315005 0.535899 0.059 Uiso 1 1 calc R . . . .
C10 C 0.2773(6) 0.4031(4) 0.6764(4) 0.0507(10) Uani 1 1 d . . . . .
H10 H 0.225688 0.400587 0.741396 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3391(6) 0.5017(4) 0.6481(4) 0.0512(10) Uani 1 1 d . . . . .
H11 H 0.382653 0.501961 0.579670 0.061 Uiso 1 1 calc R . . . .
C12 C 0.3476(6) 0.6111(4) 0.7111(4) 0.0497(9) Uani 1 1 d . . . . .
C13 C 0.3778(7) 0.7108(5) 0.6544(4) 0.0604(11) Uani 1 1 d . . . . .
H13 H 0.392595 0.706634 0.576966 0.073 Uiso 1 1 calc R . . . .
C14 C 0.3869(9) 0.8171(5) 0.7099(6) 0.0708(15) Uani 1 1 d . . . . .
H14 H 0.404554 0.883579 0.669984 0.085 Uiso 1 1 calc R . . . .
C15 C 0.3691(9) 0.8212(5) 0.8246(6) 0.0678(14) Uani 1 1 d . . . . .
C16 C 0.3406(7) 0.7234(5) 0.8850(4) 0.0628(11) Uani 1 1 d . . . . .
H16 H 0.329132 0.728246 0.963166 0.075 Uiso 1 1 calc R . . . .
C17 C 0.3294(7) 0.6198(4) 0.8288(4) 0.0557(11) Uani 1 1 d . . . . .
H17 H 0.309571 0.554057 0.869197 0.067 Uiso 1 1 calc R . . . .
C18 C 0.4330(6) 0.2161(5) 0.6834(5) 0.0607(11) Uani 1 1 d . . . . .
H18A H 0.402746 0.195751 0.757577 0.073 Uiso 1 1 calc R . . . .
H18B H 0.440540 0.146341 0.639405 0.073 Uiso 1 1 calc R . . . .
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
Br1 0.1033(4) 0.1188(6) 0.0407(3) 0.0024(3) 0.0197(2) 0.0167(4)
Br2 0.1909(10) 0.0572(4) 0.1029(6) -0.0246(4) 0.0466(6) -0.0126(5)
O1 0.108(3) 0.054(2) 0.057(2) -0.0018(17) 0.0243(19) 0.003(2)
O2 0.076(2) 0.078(3) 0.080(3) -0.005(2) 0.028(2) -0.004(2)
O3 0.084(3) 0.129(5) 0.067(3) -0.014(3) -0.007(2) -0.011(3)
N1 0.059(2) 0.065(3) 0.060(2) -0.0100(19) 0.0056(18) 0.0074(17)
N2 0.071(2) 0.079(3) 0.046(2) -0.0078(19) 0.0200(17) -0.014(2)
N3 0.079(3) 0.057(3) 0.057(2) 0.0035(19) 0.027(2) 0.006(2)
N4 0.104(4) 0.060(3) 0.099(4) 0.003(3) 0.042(3) -0.009(3)
C1 0.064(2) 0.059(3) 0.050(2) -0.008(2) 0.0139(19) 0.009(2)
C2 0.070(3) 0.072(3) 0.052(3) -0.013(2) 0.017(2) 0.011(2)
C3 0.060(2) 0.085(4) 0.040(2) -0.008(2) 0.0066(17) 0.008(2)
C4 0.075(3) 0.061(3) 0.046(2) 0.005(2) 0.011(2) 0.006(2)
C5 0.072(3) 0.058(3) 0.042(2) -0.0074(19) 0.0098(19) 0.001(2)
C6 0.058(2) 0.057(3) 0.038(2) -0.0085(18) 0.0104(17) -0.0002(19)
C7 0.059(2) 0.057(3) 0.042(2) -0.003(2) 0.0087(17) 0.001(2)
C8 0.0563(19) 0.057(3) 0.0392(17) -0.006(2) 0.0115(14) 0.001(2)
C9 0.056(2) 0.053(3) 0.038(2) -0.0058(17) 0.0121(16) 0.0026(18)
C10 0.058(2) 0.056(3) 0.039(2) -0.0061(18) 0.0127(17) 0.0033(19)
C11 0.062(2) 0.051(2) 0.038(2) -0.0020(17) 0.0088(17) 0.0071(18)
C12 0.056(2) 0.046(2) 0.044(2) -0.0002(17) 0.0074(17) 0.0044(17)
C13 0.076(3) 0.055(3) 0.053(2) 0.000(2) 0.022(2) -0.001(2)
C14 0.095(4) 0.049(3) 0.074(4) 0.002(3) 0.033(3) -0.006(3)
C15 0.086(4) 0.053(3) 0.064(3) -0.011(2) 0.017(3) -0.001(3)
C16 0.080(3) 0.061(3) 0.046(2) -0.003(2) 0.0129(19) 0.000(3)
C17 0.073(3) 0.054(3) 0.040(2) 0.0036(19) 0.0127(19) 0.003(2)
C18 0.061(2) 0.055(3) 0.062(2) 0.004(2) 0.0077(19) 0.000(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.892(5) . ?
Br2 C15 1.902(6) . ?
O1 C7 1.201(7) . ?
O2 N1 1.214(7) . ?
O3 N1 1.217(6) . ?
N1 C18 1.478(7) . ?
N2 N3 1.234(7) . ?
N2 C8 1.477(6) . ?
N3 N4 1.132(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(8) . ?
C1 C6 1.388(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(9) . ?
C3 C4 1.384(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(7) . ?
C6 C7 1.500(6) . ?
C7 C8 1.540(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.537(6) . ?
C9 H9 0.9800 . ?
C9 C10 1.494(6) . ?
C9 C18 1.537(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.317(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.464(7) . ?
C12 C13 1.383(8) . ?
C12 C17 1.404(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(10) . ?
C15 C16 1.383(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(8) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
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
O2 N1 O3 123.4(5) . . ?
O2 N1 C18 118.1(4) . . ?
O3 N1 C18 118.4(5) . . ?
N3 N2 C8 116.0(4) . . ?
N4 N3 N2 171.6(6) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.9(5) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 Br1 119.6(4) . . ?
C2 C3 C4 121.2(5) . . ?
C4 C3 Br1 119.2(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.9(5) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 117.2(5) . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C7 123.0(4) . . ?
O1 C7 C6 122.1(5) . . ?
O1 C7 C8 120.0(4) . . ?
C6 C7 C8 117.9(4) . . ?
N2 C8 C7 111.9(4) . . ?
N2 C8 H8 109.2 . . ?
N2 C8 C9 105.8(3) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 C7 111.5(3) . . ?
C9 C8 H8 109.2 . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C18 109.9(4) . . ?
C10 C9 C8 113.8(4) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C18 109.7(4) . . ?
C18 C9 H9 107.7 . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.1(4) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 H11 116.0 . . ?
C10 C11 C12 128.0(4) . . ?
C12 C11 H11 116.0 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 C17 117.7(4) . . ?
C17 C12 C11 122.8(4) . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 121.9(5) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.2(5) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 Br2 119.6(5) . . ?
C14 C15 C16 121.8(5) . . ?
C16 C15 Br2 118.6(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(5) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.9(5) . . ?
C16 C17 H17 119.5 . . ?
N1 C18 C9 109.0(4) . . ?
N1 C18 H18A 109.9 . . ?
N1 C18 H18B 109.9 . . ?
C9 C18 H18A 109.9 . . ?
C9 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
_shelx_res_file
;
TITL exp_517_a.res in P2(1)
exp_517.res
created by SHELXL-2016/6 at 16:16:35 on 17-Oct-2018
REM Old TITL exp_517 in P2(1)
REM SHELXT solution in P2(1)
REM R1 0.219, Rweak 0.093, Alpha 0.010, Orientation as input
REM Flack x = 0.154 ( 0.011 ) from Parsons' quotients
REM Formula found by SHELXT: C19 N4 O2 Br2
CELL 1.54184 7.6364 11.6851 11.5473 90 104.259 90
ZERR 2 0.0001 0.0002 0.0002 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Br N O
UNIT 36 28 4 8 6
L.S. 64
PLAN 6
SIZE 0.32 0.26 0.18
BOND $H
list 4
fmap 2 53
ACTA
OMIT -1 0 2
OMIT -1 0 5
OMIT -2 0 3
OMIT 1 0 0
OMIT 1 4 0
OMIT 0 0 7
OMIT 8 -3 4
OMIT 3 0 12
OMIT 2 0 4
OMIT -5 5 6
OMIT 1 0 1
OMIT 9 -1 1
OMIT 2 4 1
OMIT 3 0 5
OMIT 2 -6 11
REM
REM
REM
WGHT 0.060500 0.221100
EXTI 0.008083
FVAR 0.67627
BR1 3 0.141947 0.231833 -0.030478 11.00000 0.10330 0.11881 =
0.04066 0.00244 0.01970 0.01670
BR2 3 0.376744 0.964807 0.903076 11.00000 0.19090 0.05720 =
0.10291 -0.02461 0.04665 -0.01263
O1 5 0.116925 0.034015 0.520427 11.00000 0.10774 0.05373 =
0.05669 -0.00185 0.02429 0.00302
O2 5 0.666068 0.307749 0.625422 11.00000 0.07563 0.07781 =
0.08042 -0.00467 0.02815 -0.00375
O3 5 0.685240 0.294881 0.813014 11.00000 0.08354 0.12862 =
0.06739 -0.01354 -0.00694 -0.01113
N1 4 0.608296 0.276635 0.709233 11.00000 0.05875 0.06512 =
0.06008 -0.01005 0.00563 0.00735
N2 4 0.068330 0.189342 0.685175 11.00000 0.07059 0.07895 =
0.04597 -0.00778 0.02003 -0.01368
N3 4 -0.058824 0.121802 0.674622 11.00000 0.07887 0.05650 =
0.05746 0.00349 0.02690 0.00596
N4 4 -0.172002 0.060823 0.679604 11.00000 0.10376 0.06013 =
0.09896 0.00299 0.04187 -0.00940
C1 1 0.155635 0.071720 0.290015 11.00000 0.06420 0.05891 =
0.05037 -0.00784 0.01388 0.00859
AFIX 43
H1 2 0.170450 -0.002474 0.319985 11.00000 -1.20000
AFIX 0
C2 1 0.164647 0.093276 0.174253 11.00000 0.07026 0.07168 =
0.05235 -0.01319 0.01664 0.01062
AFIX 43
H2 2 0.187173 0.034001 0.126153 11.00000 -1.20000
AFIX 0
C3 1 0.140071 0.203120 0.130427 11.00000 0.06038 0.08510 =
0.04039 -0.00796 0.00662 0.00830
C4 1 0.106576 0.292545 0.200529 11.00000 0.07509 0.06141 =
0.04572 0.00500 0.01109 0.00577
AFIX 43
H4 2 0.089716 0.366487 0.170016 11.00000 -1.20000
AFIX 0
C5 1 0.098619 0.270253 0.316196 11.00000 0.07239 0.05849 =
0.04172 -0.00738 0.00978 0.00097
AFIX 43
H5 2 0.075597 0.329612 0.364028 11.00000 -1.20000
AFIX 0
C6 1 0.124420 0.160888 0.361790 11.00000 0.05834 0.05652 =
0.03832 -0.00848 0.01042 -0.00016
C7 1 0.114355 0.131293 0.486404 11.00000 0.05852 0.05700 =
0.04153 -0.00289 0.00875 0.00130
C8 1 0.105612 0.230436 0.572699 11.00000 0.05627 0.05672 =
0.03920 -0.00646 0.01153 0.00147
AFIX 13
H8 2 0.010332 0.283890 0.533784 11.00000 -1.20000
AFIX 0
C9 1 0.286330 0.294896 0.609151 11.00000 0.05620 0.05345 =
0.03809 -0.00575 0.01210 0.00258
AFIX 13
H9 2 0.322271 0.315005 0.535899 11.00000 -1.20000
AFIX 0
C10 1 0.277335 0.403052 0.676430 11.00000 0.05813 0.05573 =
0.03869 -0.00610 0.01270 0.00327
AFIX 43
H10 2 0.225688 0.400587 0.741396 11.00000 -1.20000
AFIX 0
C11 1 0.339074 0.501733 0.648111 11.00000 0.06194 0.05135 =
0.03835 -0.00205 0.00884 0.00707
AFIX 43
H11 2 0.382653 0.501961 0.579670 11.00000 -1.20000
AFIX 0
C12 1 0.347551 0.611115 0.711103 11.00000 0.05611 0.04575 =
0.04449 -0.00022 0.00736 0.00444
C13 1 0.377839 0.710776 0.654434 11.00000 0.07587 0.05539 =
0.05329 0.00029 0.02217 -0.00073
AFIX 43
H13 2 0.392595 0.706634 0.576966 11.00000 -1.20000
AFIX 0
C14 1 0.386890 0.817118 0.709946 11.00000 0.09535 0.04945 =
0.07403 0.00210 0.03335 -0.00636
AFIX 43
H14 2 0.404554 0.883579 0.669984 11.00000 -1.20000
AFIX 0
C15 1 0.369141 0.821162 0.824556 11.00000 0.08562 0.05295 =
0.06394 -0.01096 0.01650 -0.00065
C16 1 0.340615 0.723447 0.884983 11.00000 0.07955 0.06131 =
0.04621 -0.00292 0.01288 0.00048
AFIX 43
H16 2 0.329132 0.728246 0.963166 11.00000 -1.20000
AFIX 0
C17 1 0.329446 0.619780 0.828834 11.00000 0.07264 0.05378 =
0.03994 0.00359 0.01271 0.00335
AFIX 43
H17 2 0.309571 0.554057 0.869197 11.00000 -1.20000
AFIX 0
C18 1 0.432998 0.216125 0.683414 11.00000 0.06114 0.05492 =
0.06217 0.00415 0.00765 -0.00023
AFIX 23
H18A 2 0.402746 0.195751 0.757577 11.00000 -1.20000
H18B 2 0.440540 0.146341 0.639405 11.00000 -1.20000
AFIX 0
HKLF 4
REM exp_517_a.res in P2(1)
REM R1 = 0.0383 for 3735 Fo > 4sig(Fo) and 0.0402 for all 4011 data
REM 245 parameters refined using 1 restraints
END
WGHT 0.0606 0.2209
REM Highest difference peak 0.564, deepest hole -0.552, 1-sigma level 0.054
Q1 1 0.4849 0.9609 0.8780 11.00000 0.05 0.56
Q2 1 0.1013 0.3058 -0.0197 11.00000 0.05 0.42
Q3 1 0.4100 0.9172 0.9666 11.00000 0.05 0.38
Q4 1 0.0936 0.1539 -0.0215 11.00000 0.05 0.30
Q5 1 0.3884 1.0215 1.0029 11.00000 0.05 0.28
Q6 1 0.3580 0.8828 0.8462 11.00000 0.05 0.24
;
_shelx_res_checksum 13800
_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 4.897
_oxdiff_exptl_absorpt_empirical_full_min 0.287
#######################################################################
#
# 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_cu_dm16503_0m
_database_code_depnum_ccdc_archive 'CCDC 1874281'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record
;
2018-10-20 deposited with the CCDC. 2020-03-11 downloaded from the CCDC.
;
_audit_creation_date 2016-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C19 H15 F N4 O3'
_chemical_formula_sum 'C19 H15 F N4 O3'
_chemical_formula_weight 366.35
_chemical_absolute_configuration rmad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 19
_space_group_name_H-M_alt 'P 21 21 21'
_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'
_cell_length_a 10.3148(2)
_cell_length_b 11.9114(3)
_cell_length_c 14.6673(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1802.08(7)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3485
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 61.889
_cell_measurement_theta_min 3.711
_shelx_estimated_absorpt_T_max 0.883
_shelx_estimated_absorpt_T_min 0.816
_exptl_absorpt_coefficient_mu 0.848
_exptl_absorpt_correction_T_max 0.7531
_exptl_absorpt_correction_T_min 0.6639
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8816.
The \l/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.350
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 760
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.15
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0405
_diffrn_reflns_av_unetI/netI 0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 12680
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 68.605
_diffrn_reflns_theta_min 4.782
_diffrn_ambient_temperature 296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.719
_reflns_Friedel_fraction_full 0.970
_reflns_Friedel_fraction_max 0.954
_reflns_number_gt 2819
_reflns_number_total 3229
_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 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_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 0.846
_refine_diff_density_min -0.323
_refine_diff_density_rms 0.057
_refine_ls_abs_structure_details
;
Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.06(11)
_refine_ls_extinction_coef 0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 245
_refine_ls_number_reflns 3229
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0747
_refine_ls_R_factor_gt 0.0691
_refine_ls_restrained_S_all 1.048
_refine_ls_shift/su_max 0.006
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1729P)^2^+0.1627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2196
_refine_ls_wR_factor_ref 0.2314
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
C10(H10)
2.b Secondary CH2 refined with riding coordinates:
C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C16(H16), C17(H17),
C18(H18), C19(H19)
;
_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
F1 F 0.8690(5) 0.2750(4) 0.4148(4) 0.1503(19) Uani 1 1 d . . . . .
O1 O 0.3852(4) 0.6665(3) 0.2589(3) 0.0965(11) Uani 1 1 d . . . . .
O2 O 0.7432(5) 0.5702(5) 0.1188(3) 0.1203(16) Uani 1 1 d . . . . .
O3 O 0.7578(5) 0.3984(5) 0.0854(4) 0.1327(19) Uani 1 1 d . . . . .
N1 N 0.4770(5) 0.5284(5) 0.4185(3) 0.0891(12) Uani 1 1 d . . . . .
N2 N 0.5193(6) 0.6254(5) 0.4263(3) 0.1017(16) Uani 1 1 d . . . . .
N3 N 0.5593(10) 0.7108(6) 0.4442(5) 0.154(3) Uani 1 1 d . . . . .
N4 N 0.7063(4) 0.4748(5) 0.1240(3) 0.0891(13) Uani 1 1 d . . . . .
C1 C 0.4662(4) 0.4901(4) 0.3232(3) 0.0682(10) Uani 1 1 d . . . . .
C2 C 0.3682(4) 0.5672(4) 0.2724(3) 0.0719(11) Uani 1 1 d . . . . .
C3 C 0.2580(4) 0.4984(4) 0.2443(3) 0.0705(10) Uani 1 1 d . . . . .
C4 C 0.1475(5) 0.5299(5) 0.1951(3) 0.0890(15) Uani 1 1 d . . . . .
H4 H 0.1366 0.6040 0.1766 0.107 Uiso 1 1 calc R . . . .
C5 C 0.0579(5) 0.4527(7) 0.1749(4) 0.1056(19) Uani 1 1 d . . . . .
H5 H -0.0152 0.4725 0.1414 0.127 Uiso 1 1 calc R . . . .
C6 C 0.0747(6) 0.3427(7) 0.2043(4) 0.111(2) Uani 1 1 d . . . . .
H6 H 0.0109 0.2899 0.1914 0.134 Uiso 1 1 calc R . . . .
C7 C 0.1829(6) 0.3103(5) 0.2518(5) 0.0989(16) Uani 1 1 d . . . . .
H7 H 0.1930 0.2360 0.2700 0.119 Uiso 1 1 calc R . . . .
C8 C 0.2767(4) 0.3892(4) 0.2721(3) 0.0740(11) Uani 1 1 d . . . . .
C9 C 0.4001(4) 0.3745(4) 0.3244(4) 0.0805(12) Uani 1 1 d . . . . .
H9A H 0.4549 0.3185 0.2957 0.097 Uiso 1 1 calc R . . . .
H9B H 0.3822 0.3511 0.3865 0.097 Uiso 1 1 calc R . . . .
C10 C 0.5986(4) 0.4978(4) 0.2744(2) 0.0647(9) Uani 1 1 d . . . . .
H10 H 0.6207 0.5775 0.2685 0.078 Uiso 1 1 calc R . . . .
C11 C 0.5864(4) 0.4494(5) 0.1784(3) 0.0776(12) Uani 1 1 d . . . . .
H11A H 0.5740 0.3688 0.1819 0.093 Uiso 1 1 calc R . . . .
H11B H 0.5114 0.4817 0.1484 0.093 Uiso 1 1 calc R . . . .
C12 C 0.7059(4) 0.4419(4) 0.3259(3) 0.0664(9) Uani 1 1 d . . . . .
H12 H 0.7025 0.3646 0.3344 0.080 Uiso 1 1 calc R . . . .
C13 C 0.8051(4) 0.4980(4) 0.3597(3) 0.0683(10) Uani 1 1 d . . . . .
H13 H 0.8018 0.5752 0.3503 0.082 Uiso 1 1 calc R . . . .
C14 C 0.9205(4) 0.4585(4) 0.4101(3) 0.0707(11) Uani 1 1 d . . . . .
C15 C 0.9491(6) 0.3530(5) 0.4349(3) 0.0870(14) Uani 1 1 d . . . . .
C16 C 1.0604(8) 0.3202(7) 0.4809(4) 0.111(2) Uani 1 1 d . . . . .
H16 H 1.0756 0.2456 0.4963 0.133 Uiso 1 1 calc R . . . .
C17 C 1.1471(6) 0.4039(9) 0.5027(4) 0.112(2) Uani 1 1 d . . . . .
H17 H 1.2223 0.3854 0.5342 0.134 Uiso 1 1 calc R . . . .
C18 C 1.1264(6) 0.5091(8) 0.4802(4) 0.110(2) Uani 1 1 d . . . . .
H18 H 1.1883 0.5624 0.4961 0.132 Uiso 1 1 calc R . . . .
C19 C 1.0144(5) 0.5449(9) 0.4329(4) 0.118(3) Uani 1 1 d . . . . .
H19 H 1.0015 0.6198 0.4174 0.141 Uiso 1 1 calc R . . . .
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
F1 0.142(4) 0.114(3) 0.195(5) 0.011(3) -0.060(4) 0.002(3)
O1 0.082(2) 0.082(2) 0.126(3) 0.0111(19) -0.013(2) 0.0085(16)
O2 0.115(4) 0.154(4) 0.092(3) 0.016(3) 0.011(3) -0.033(3)
O3 0.092(3) 0.178(5) 0.127(4) -0.049(4) 0.025(3) 0.007(3)
N1 0.085(3) 0.121(3) 0.061(2) -0.008(2) 0.0015(19) 0.015(2)
N2 0.113(4) 0.111(4) 0.080(3) -0.023(3) -0.016(3) 0.032(3)
N3 0.206(8) 0.124(4) 0.134(5) -0.051(4) -0.067(6) 0.038(5)
N4 0.065(2) 0.139(4) 0.063(2) -0.008(2) -0.0066(18) 0.000(2)
C1 0.058(2) 0.084(2) 0.062(2) 0.0019(19) -0.0005(17) 0.0077(18)
C2 0.061(2) 0.083(2) 0.072(2) 0.0008(19) -0.0016(19) 0.0095(18)
C3 0.053(2) 0.099(3) 0.060(2) 0.004(2) 0.0036(17) 0.0045(18)
C4 0.060(2) 0.134(4) 0.073(3) 0.008(3) 0.002(2) 0.014(3)
C5 0.060(3) 0.177(6) 0.079(3) -0.001(4) -0.007(3) -0.006(3)
C6 0.071(3) 0.162(6) 0.102(4) -0.028(4) -0.003(3) -0.024(4)
C7 0.080(3) 0.109(3) 0.107(4) -0.019(3) 0.015(3) -0.015(3)
C8 0.058(2) 0.095(3) 0.069(2) -0.005(2) 0.0105(19) 0.000(2)
C9 0.061(2) 0.087(3) 0.094(3) 0.009(2) 0.002(2) 0.009(2)
C10 0.057(2) 0.080(2) 0.0571(19) -0.0035(17) -0.0075(17) 0.0007(17)
C11 0.057(2) 0.115(3) 0.061(2) -0.011(2) -0.0050(19) -0.006(2)
C12 0.057(2) 0.075(2) 0.067(2) 0.0024(18) -0.0049(18) 0.0029(17)
C13 0.061(2) 0.083(2) 0.061(2) -0.0021(18) -0.0092(17) 0.0005(19)
C14 0.058(2) 0.101(3) 0.0531(18) -0.0017(18) 0.0021(17) 0.012(2)
C15 0.087(3) 0.096(3) 0.078(3) -0.003(2) -0.010(2) 0.014(3)
C16 0.127(5) 0.131(5) 0.074(3) 0.013(3) 0.002(3) 0.049(4)
C17 0.077(4) 0.185(7) 0.074(3) -0.020(4) -0.006(3) 0.036(4)
C18 0.064(3) 0.184(7) 0.083(3) -0.016(4) -0.011(3) 0.004(4)
C19 0.051(2) 0.233(8) 0.070(3) -0.042(4) -0.016(2) -0.006(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
F1 C15 1.277(7) . ?
O1 C2 1.211(6) . ?
O2 N4 1.201(7) . ?
O3 N4 1.196(7) . ?
N1 N2 1.240(8) . ?
N1 C1 1.475(6) . ?
N2 N3 1.128(9) . ?
N4 C11 1.503(6) . ?
C1 C2 1.556(6) . ?
C1 C9 1.537(6) . ?
C1 C10 1.545(6) . ?
C2 C3 1.461(6) . ?
C3 C4 1.401(6) . ?
C3 C8 1.376(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.337(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(7) . ?
C8 C9 1.497(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C11 1.526(6) . ?
C10 C12 1.496(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.318(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.478(6) . ?
C14 C15 1.341(7) . ?
C14 C19 1.453(9) . ?
C15 C16 1.388(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.313(11) . ?
C18 H18 0.9300 . ?
C18 C19 1.414(9) . ?
C19 H19 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
N2 N1 C1 113.7(4) . . ?
N3 N2 N1 171.7(7) . . ?
O2 N4 C11 119.0(5) . . ?
O3 N4 O2 123.3(6) . . ?
O3 N4 C11 117.7(6) . . ?
N1 C1 C2 108.7(4) . . ?
N1 C1 C9 107.4(4) . . ?
N1 C1 C10 110.8(3) . . ?
C9 C1 C2 104.3(3) . . ?
C9 C1 C10 116.8(4) . . ?
C10 C1 C2 108.5(3) . . ?
O1 C2 C1 124.1(4) . . ?
O1 C2 C3 127.9(4) . . ?
C3 C2 C1 108.0(4) . . ?
C4 C3 C2 128.9(5) . . ?
C8 C3 C2 109.8(4) . . ?
C8 C3 C4 121.3(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(6) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(6) . . ?
C8 C7 H7 120.4 . . ?
C3 C8 C7 118.8(5) . . ?
C3 C8 C9 112.4(4) . . ?
C7 C8 C9 128.8(5) . . ?
C1 C9 H9A 110.7 . . ?
C1 C9 H9B 110.7 . . ?
C8 C9 C1 105.4(4) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C1 C10 H10 107.7 . . ?
C11 C10 C1 109.4(3) . . ?
C11 C10 H10 107.7 . . ?
C12 C10 C1 113.2(3) . . ?
C12 C10 H10 107.7 . . ?
C12 C10 C11 111.0(4) . . ?
N4 C11 C10 110.2(3) . . ?
N4 C11 H11A 109.6 . . ?
N4 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C10 C12 H12 118.7 . . ?
C13 C12 C10 122.5(4) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 114.7 . . ?
C12 C13 C14 130.6(4) . . ?
C14 C13 H13 114.7 . . ?
C15 C14 C13 127.7(5) . . ?
C15 C14 C19 117.0(5) . . ?
C19 C14 C13 115.3(5) . . ?
F1 C15 C14 118.5(5) . . ?
F1 C15 C16 116.2(6) . . ?
C14 C15 C16 125.3(6) . . ?
C15 C16 H16 121.8 . . ?
C17 C16 C15 116.5(6) . . ?
C17 C16 H16 121.8 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.9(6) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 118.5 . . ?
C17 C18 C19 122.9(8) . . ?
C19 C18 H18 118.5 . . ?
C14 C19 H19 121.8 . . ?
C18 C19 C14 116.4(8) . . ?
C18 C19 H19 121.8 . . ?
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
F1 C15 C16 C17 180.0(6) . . . . ?
O1 C2 C3 C4 0.6(8) . . . . ?
O1 C2 C3 C8 179.3(5) . . . . ?
O2 N4 C11 C10 -53.1(6) . . . . ?
O3 N4 C11 C10 129.3(5) . . . . ?
N1 C1 C2 O1 64.5(6) . . . . ?
N1 C1 C2 C3 -116.3(4) . . . . ?
N1 C1 C9 C8 118.1(4) . . . . ?
N1 C1 C10 C11 175.8(4) . . . . ?
N1 C1 C10 C12 51.4(5) . . . . ?
N2 N1 C1 C2 -62.2(6) . . . . ?
N2 N1 C1 C9 -174.4(4) . . . . ?
N2 N1 C1 C10 57.0(6) . . . . ?
C1 C2 C3 C4 -178.5(4) . . . . ?
C1 C2 C3 C8 0.2(5) . . . . ?
C1 C10 C11 N4 169.7(4) . . . . ?
C1 C10 C12 C13 -115.2(5) . . . . ?
C2 C1 C9 C8 2.9(5) . . . . ?
C2 C1 C10 C11 -65.0(5) . . . . ?
C2 C1 C10 C12 170.6(3) . . . . ?
C2 C3 C4 C5 178.9(5) . . . . ?
C2 C3 C8 C7 -179.8(4) . . . . ?
C2 C3 C8 C9 1.8(5) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C3 C8 C9 C1 -3.0(5) . . . . ?
C4 C3 C8 C7 -1.0(7) . . . . ?
C4 C3 C8 C9 -179.4(4) . . . . ?
C4 C5 C6 C7 -1.7(10) . . . . ?
C5 C6 C7 C8 1.0(9) . . . . ?
C6 C7 C8 C3 0.3(8) . . . . ?
C6 C7 C8 C9 178.5(5) . . . . ?
C7 C8 C9 C1 178.7(5) . . . . ?
C8 C3 C4 C5 0.3(7) . . . . ?
C9 C1 C2 O1 178.8(5) . . . . ?
C9 C1 C2 C3 -2.0(5) . . . . ?
C9 C1 C10 C11 52.4(5) . . . . ?
C9 C1 C10 C12 -72.0(5) . . . . ?
C10 C1 C2 O1 -56.1(6) . . . . ?
C10 C1 C2 C3 123.1(4) . . . . ?
C10 C1 C9 C8 -116.8(4) . . . . ?
C10 C12 C13 C14 -178.4(4) . . . . ?
C11 C10 C12 C13 121.3(5) . . . . ?
C12 C10 C11 N4 -64.6(5) . . . . ?
C12 C13 C14 C15 -1.5(8) . . . . ?
C12 C13 C14 C19 176.9(5) . . . . ?
C13 C14 C15 F1 -0.8(8) . . . . ?
C13 C14 C15 C16 178.8(5) . . . . ?
C13 C14 C19 C18 -179.3(4) . . . . ?
C14 C15 C16 C17 0.3(9) . . . . ?
C15 C14 C19 C18 -0.7(7) . . . . ?
C15 C16 C17 C18 -0.8(10) . . . . ?
C16 C17 C18 C19 0.5(10) . . . . ?
C17 C18 C19 C14 0.2(9) . . . . ?
C19 C14 C15 F1 -179.3(6) . . . . ?
C19 C14 C15 C16 0.4(8) . . . . ?
_shelx_res_file
;
cu_dm16503_0m.res created by SHELXL-2014/7
TITL cu_dm16503_0m_a.res in P2(1)2(1)2(1)
REM Old TITL cu_dm16503_0m in P212121 #19
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.225, Rweak 0.040, Alpha 0.006, Orientation as input
REM Flack x = 0.173 ( 0.136 ) from Parsons' quotients
REM Formula found by SHELXT: C22 N2 O3
CELL 1.54178 10.3148 11.9114 14.6673 90 90 90
ZERR 4 0.0002 0.0003 0.0003 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 F N O
UNIT 76 60 4 16 12
L.S. 5
PLAN -20 0 0
SIZE 0.15 0.2 0.25
TEMP 23
BOND $H
MORE -1
CONF
fmap 2
acta
REM
REM
REM
WGHT 0.172900 0.162700
EXTI 0.006741
FVAR 0.69743
F1 3 0.869043 0.275026 0.414821 11.00000 0.14158 0.11423 =
0.19518 0.01086 -0.06016 0.00163
O1 5 0.385168 0.666484 0.258901 11.00000 0.08197 0.08196 =
0.12565 0.01109 -0.01316 0.00849
O2 5 0.743210 0.570209 0.118832 11.00000 0.11505 0.15351 =
0.09236 0.01562 0.01051 -0.03261
O3 5 0.757769 0.398410 0.085392 11.00000 0.09231 0.17836 =
0.12735 -0.04909 0.02452 0.00661
N1 4 0.476955 0.528400 0.418533 11.00000 0.08534 0.12086 =
0.06123 -0.00753 0.00152 0.01506
N2 4 0.519336 0.625383 0.426338 11.00000 0.11339 0.11135 =
0.08047 -0.02266 -0.01618 0.03173
N3 4 0.559294 0.710757 0.444217 11.00000 0.20611 0.12358 =
0.13352 -0.05107 -0.06733 0.03809
N4 4 0.706293 0.474760 0.124024 11.00000 0.06530 0.13904 =
0.06298 -0.00776 -0.00660 0.00046
C1 1 0.466244 0.490145 0.323187 11.00000 0.05772 0.08448 =
0.06226 0.00190 -0.00046 0.00773
C2 1 0.368211 0.567239 0.272351 11.00000 0.06095 0.08318 =
0.07169 0.00084 -0.00156 0.00953
C3 1 0.258025 0.498400 0.244309 11.00000 0.05251 0.09858 =
0.06046 0.00371 0.00363 0.00454
C4 1 0.147541 0.529941 0.195070 11.00000 0.06047 0.13385 =
0.07255 0.00834 0.00164 0.01427
AFIX 43
H4 2 0.136582 0.604009 0.176553 11.00000 -1.20000
AFIX 0
C5 1 0.057929 0.452708 0.174894 11.00000 0.06045 0.17743 =
0.07896 -0.00136 -0.00714 -0.00612
AFIX 43
H5 2 -0.015151 0.472467 0.141405 11.00000 -1.20000
AFIX 0
C6 1 0.074673 0.342732 0.204276 11.00000 0.07111 0.16171 =
0.10158 -0.02823 -0.00299 -0.02371
AFIX 43
H6 2 0.010911 0.289851 0.191415 11.00000 -1.20000
AFIX 0
C7 1 0.182865 0.310267 0.251754 11.00000 0.08020 0.10925 =
0.10729 -0.01917 0.01548 -0.01533
AFIX 43
H7 2 0.192993 0.236025 0.270042 11.00000 -1.20000
AFIX 0
C8 1 0.276680 0.389214 0.272099 11.00000 0.05756 0.09550 =
0.06891 -0.00492 0.01045 -0.00010
C9 1 0.400150 0.374461 0.324418 11.00000 0.06083 0.08720 =
0.09359 0.00948 0.00232 0.00852
AFIX 23
H9A 2 0.454873 0.318498 0.295659 11.00000 -1.20000
H9B 2 0.382232 0.351085 0.386502 11.00000 -1.20000
AFIX 0
C10 1 0.598636 0.497772 0.274384 11.00000 0.05704 0.08009 =
0.05708 -0.00354 -0.00750 0.00068
AFIX 13
H10 2 0.620731 0.577459 0.268482 11.00000 -1.20000
AFIX 0
C11 1 0.586396 0.449396 0.178432 11.00000 0.05685 0.11511 =
0.06083 -0.01077 -0.00498 -0.00583
AFIX 23
H11A 2 0.574018 0.368786 0.181950 11.00000 -1.20000
H11B 2 0.511370 0.481654 0.148373 11.00000 -1.20000
AFIX 0
C12 1 0.705925 0.441884 0.325920 11.00000 0.05717 0.07480 =
0.06725 0.00241 -0.00486 0.00289
AFIX 43
H12 2 0.702543 0.364572 0.334445 11.00000 -1.20000
AFIX 0
C13 1 0.805051 0.498005 0.359702 11.00000 0.06072 0.08289 =
0.06139 -0.00208 -0.00924 0.00053
AFIX 43
H13 2 0.801828 0.575168 0.350298 11.00000 -1.20000
AFIX 0
C14 1 0.920460 0.458489 0.410060 11.00000 0.05844 0.10056 =
0.05305 -0.00174 0.00210 0.01156
C15 1 0.949064 0.352961 0.434867 11.00000 0.08743 0.09590 =
0.07760 -0.00251 -0.01020 0.01418
C16 1 1.060381 0.320161 0.480933 11.00000 0.12744 0.13067 =
0.07411 0.01316 0.00224 0.04855
AFIX 43
H16 2 1.075595 0.245564 0.496292 11.00000 -1.20000
AFIX 0
C17 1 1.147059 0.403879 0.502680 11.00000 0.07691 0.18542 =
0.07352 -0.02048 -0.00566 0.03566
AFIX 43
H17 2 1.222336 0.385401 0.534188 11.00000 -1.20000
AFIX 0
C18 1 1.126447 0.509052 0.480197 11.00000 0.06427 0.18419 =
0.08279 -0.01584 -0.01150 0.00353
AFIX 43
H18 2 1.188337 0.562362 0.496063 11.00000 -1.20000
AFIX 0
C19 1 1.014388 0.544917 0.432947 11.00000 0.05105 0.23267 =
0.06956 -0.04185 -0.01634 -0.00618
AFIX 43
H19 2 1.001494 0.619769 0.417359 11.00000 -1.20000
AFIX 0
HKLF 4
REM cu_dm16503_0m_a.res in P2(1)2(1)2(1)
REM R1 = 0.0691 for 2819 Fo > 4sig(Fo) and 0.0747 for all 3229 data
REM 245 parameters refined using 0 restraints
END
WGHT 0.1728 0.1637
REM Highest difference peak 0.846, deepest hole -0.323, 1-sigma level 0.057
Q1 1 1.0214 0.6235 0.3970 11.00000 0.05 0.85
Q2 1 1.0061 0.2546 0.4591 11.00000 0.05 0.20
Q3 1 1.1071 0.4413 0.4588 11.00000 0.05 0.17
Q4 1 0.7907 0.5124 0.2831 11.00000 0.05 0.16
Q5 1 0.0009 0.6283 0.0663 11.00000 0.05 0.16
Q6 1 0.7603 0.3590 0.1315 11.00000 0.05 0.15
Q7 1 0.7708 0.4787 0.0919 11.00000 0.05 0.14
Q8 1 -0.0067 0.5213 0.1151 11.00000 0.05 0.13
Q9 1 0.5164 0.3947 0.1377 11.00000 0.05 0.13
Q10 1 0.0101 0.4041 -0.0547 11.00000 0.05 0.13
Q11 1 0.6530 0.5791 0.1232 11.00000 0.05 0.13
Q12 1 0.2534 0.6096 0.4202 11.00000 0.05 0.13
Q13 1 0.0106 0.5539 0.0257 11.00000 0.05 0.13
Q14 1 0.5434 0.5123 0.2951 11.00000 0.05 0.12
Q15 1 0.7213 0.3459 0.2784 11.00000 0.05 0.12
Q16 1 0.1415 0.5380 -0.0240 11.00000 0.05 0.11
Q17 1 0.7829 0.6156 0.3856 11.00000 0.05 0.11
Q18 1 0.5726 0.5307 0.1252 11.00000 0.05 0.11
Q19 1 1.2318 0.3223 0.5307 11.00000 0.05 0.11
Q20 1 0.0683 0.4640 -0.0350 11.00000 0.05 0.10
;
_shelx_res_checksum 21676
_shelx_SHELXL_version_number 2014/7
_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_z_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1874279'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record
;
2018-10-20 deposited with the CCDC. 2020-03-11 downloaded from the CCDC.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C25 H21 Cl N2 O3'
_chemical_formula_weight 432.89
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 6.6447(5)
_cell_length_b 14.3101(11)
_cell_length_c 22.5008(17)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2139.5(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 3602
_cell_measurement_theta_min 2.3
_cell_measurement_theta_max 20.86
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.49
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.344
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 904
_exptl_absorpt_coefficient_mu 0.209
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9047
_exptl_absorpt_correction_T_max 0.9615
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex II CCD'
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 24886
_diffrn_reflns_av_R_equivalents 0.0587
_diffrn_reflns_av_sigmaI/netI 0.0379
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 1.69
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3762
_reflns_number_gt 2822
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.7313P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.14(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns 3762
_refine_ls_number_parameters 280
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0682
_refine_ls_R_factor_gt 0.0430
_refine_ls_wR_factor_ref 0.1084
_refine_ls_wR_factor_gt 0.0935
_refine_ls_goodness_of_fit_ref 0.996
_refine_ls_restrained_S_all 0.996
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3049(2) 0.83315(7) 0.88362(5) 0.0994(4) Uani 1 1 d . . .
O1 O 0.8832(3) 0.40382(15) 0.97765(9) 0.0544(5) Uani 1 1 d . . .
O2 O 0.3883(5) 0.5440(2) 1.12833(12) 0.0980(10) Uani 1 1 d . . .
O3 O 0.1074(4) 0.4738(2) 1.13565(11) 0.0860(8) Uani 1 1 d . . .
N1 N 0.5146(4) 0.31366(15) 1.02005(10) 0.0483(6) Uani 1 1 d . . .
H1A H 0.5833 0.2630 1.0166 0.058 Uiso 1 1 calc R . .
N2 N 0.2650(4) 0.49011(18) 1.11048(11) 0.0538(6) Uani 1 1 d . . .
C1 C 0.7260(4) 0.40552(18) 0.94982(12) 0.0396(6) Uani 1 1 d . . .
C2 C 0.7007(4) 0.42537(18) 0.88646(12) 0.0429(7) Uani 1 1 d . . .
C3 C 0.8442(5) 0.4543(2) 0.84553(14) 0.0584(8) Uani 1 1 d . . .
H3A H 0.9763 0.4657 0.8571 0.070 Uiso 1 1 calc R . .
C4 C 0.7850(7) 0.4656(3) 0.78744(15) 0.0747(11) Uani 1 1 d . . .
H4A H 0.8780 0.4844 0.7590 0.090 Uiso 1 1 calc R . .
C5 C 0.5875(7) 0.4491(3) 0.77124(15) 0.0756(12) Uani 1 1 d . . .
H5A H 0.5498 0.4576 0.7318 0.091 Uiso 1 1 calc R . .
C6 C 0.4450(6) 0.4204(2) 0.81176(14) 0.0641(9) Uani 1 1 d . . .
H6A H 0.3131 0.4092 0.7999 0.077 Uiso 1 1 calc R . .
C7 C 0.5016(4) 0.40842(19) 0.87074(12) 0.0450(7) Uani 1 1 d . . .
C8 C 0.3808(4) 0.3754(2) 0.92227(12) 0.0462(7) Uani 1 1 d . . .
H8A H 0.3451 0.3101 0.9176 0.055 Uiso 1 1 calc R . .
H8B H 0.2584 0.4118 0.9262 0.055 Uiso 1 1 calc R . .
C9 C 0.5180(4) 0.38916(18) 0.97682(12) 0.0374(6) Uani 1 1 d . . .
C10 C 0.4653(4) 0.47567(18) 1.01602(11) 0.0370(6) Uani 1 1 d . . .
H10A H 0.5826 0.4880 1.0412 0.044 Uiso 1 1 calc R . .
C11 C 0.3040(4) 0.43481(17) 1.05561(11) 0.0401(6) Uani 1 1 d . . .
H11A H 0.1787 0.4300 1.0329 0.048 Uiso 1 1 calc R . .
C12 C 0.3799(4) 0.33396(19) 1.07062(12) 0.0420(7) Uani 1 1 d . . .
H12A H 0.2650 0.2912 1.0687 0.050 Uiso 1 1 calc R . .
C13 C 0.4801(4) 0.32213(19) 1.12991(13) 0.0437(7) Uani 1 1 d . . .
C14 C 0.3735(5) 0.2860(2) 1.17734(14) 0.0583(9) Uani 1 1 d . . .
H14A H 0.2390 0.2700 1.1722 0.070 Uiso 1 1 calc R . .
C15 C 0.4617(6) 0.2732(2) 1.23209(15) 0.0699(10) Uani 1 1 d . . .
H15A H 0.3860 0.2494 1.2634 0.084 Uiso 1 1 calc R . .
C16 C 0.6622(6) 0.2955(2) 1.24108(15) 0.0649(10) Uani 1 1 d . . .
C17 C 0.7673(5) 0.3329(2) 1.19425(15) 0.0618(9) Uani 1 1 d . . .
H17A H 0.9011 0.3500 1.1997 0.074 Uiso 1 1 calc R . .
C18 C 0.6793(5) 0.3459(2) 1.13912(13) 0.0526(8) Uani 1 1 d . . .
H18A H 0.7546 0.3708 1.1081 0.063 Uiso 1 1 calc R . .
C19 C 0.7602(7) 0.2789(3) 1.30031(16) 0.0996(15) Uani 1 1 d . . .
H19A H 0.8989 0.2975 1.2985 0.149 Uiso 1 1 calc R . .
H19B H 0.7521 0.2137 1.3101 0.149 Uiso 1 1 calc R . .
H19C H 0.6923 0.3148 1.3302 0.149 Uiso 1 1 calc R . .
C20 C 0.4188(4) 0.56501(18) 0.98338(12) 0.0393(6) Uani 1 1 d . . .
C21 C 0.5712(5) 0.62860(19) 0.97320(13) 0.0489(7) Uani 1 1 d . . .
H21A H 0.6996 0.6158 0.9875 0.059 Uiso 1 1 calc R . .
C22 C 0.5384(6) 0.7107(2) 0.94239(14) 0.0581(9) Uani 1 1 d . . .
H22A H 0.6430 0.7527 0.9360 0.070 Uiso 1 1 calc R . .
C23 C 0.3484(6) 0.7292(2) 0.92147(14) 0.0618(9) Uani 1 1 d . . .
C24 C 0.1946(6) 0.6687(2) 0.93117(15) 0.0673(9) Uani 1 1 d . . .
H24A H 0.0666 0.6821 0.9167 0.081 Uiso 1 1 calc R . .
C25 C 0.2286(5) 0.5869(2) 0.96264(13) 0.0545(8) Uani 1 1 d . . .
H25A H 0.1222 0.5463 0.9699 0.065 Uiso 1 1 calc R . .
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
Cl1 0.1487(10) 0.0694(6) 0.0802(7) 0.0319(5) 0.0342(7) 0.0408(7)
O1 0.0378(11) 0.0749(14) 0.0506(12) 0.0003(11) -0.0072(11) 0.0034(10)
O2 0.116(2) 0.098(2) 0.0796(18) -0.0461(16) 0.0299(18) -0.0405(19)
O3 0.0819(17) 0.0983(19) 0.0778(17) -0.0077(15) 0.0412(16) 0.0053(15)
N1 0.0565(15) 0.0418(13) 0.0464(14) 0.0032(11) 0.0097(13) 0.0114(11)
N2 0.0621(17) 0.0529(15) 0.0465(15) -0.0005(12) 0.0174(14) 0.0042(14)
C1 0.0353(16) 0.0411(14) 0.0424(16) -0.0054(12) -0.0008(13) 0.0019(12)
C2 0.0460(17) 0.0430(15) 0.0396(16) 0.0003(13) 0.0043(14) 0.0085(13)
C3 0.061(2) 0.062(2) 0.052(2) 0.0067(16) 0.0122(16) 0.0078(16)
C4 0.091(3) 0.084(3) 0.049(2) 0.0189(18) 0.019(2) 0.012(2)
C5 0.107(3) 0.083(3) 0.0373(19) 0.0065(18) -0.007(2) 0.018(2)
C6 0.071(2) 0.077(2) 0.0452(19) -0.0061(17) -0.0121(18) 0.0114(19)
C7 0.0502(18) 0.0473(16) 0.0374(16) -0.0075(13) -0.0059(14) 0.0093(14)
C8 0.0387(16) 0.0557(17) 0.0442(17) -0.0110(14) -0.0053(14) -0.0016(13)
C9 0.0359(14) 0.0415(14) 0.0349(15) -0.0043(12) -0.0011(13) -0.0010(12)
C10 0.0333(14) 0.0437(14) 0.0339(14) -0.0049(12) -0.0011(12) 0.0001(12)
C11 0.0371(14) 0.0461(15) 0.0371(15) -0.0038(12) -0.0011(13) 0.0010(13)
C12 0.0399(15) 0.0410(15) 0.0451(17) -0.0015(13) 0.0028(14) -0.0068(13)
C13 0.0462(17) 0.0407(15) 0.0443(17) -0.0011(13) 0.0017(14) -0.0011(13)
C14 0.062(2) 0.061(2) 0.052(2) 0.0080(16) 0.0067(17) -0.0071(17)
C15 0.094(3) 0.068(2) 0.048(2) 0.0143(17) 0.007(2) -0.005(2)
C16 0.084(3) 0.062(2) 0.049(2) 0.0026(16) -0.008(2) 0.010(2)
C17 0.059(2) 0.066(2) 0.061(2) -0.0062(18) -0.0098(18) 0.0067(18)
C18 0.0539(18) 0.0571(18) 0.0468(18) 0.0006(15) 0.0026(16) 0.0020(16)
C19 0.131(4) 0.107(3) 0.061(2) 0.009(2) -0.025(3) 0.026(3)
C20 0.0420(16) 0.0416(15) 0.0343(14) -0.0036(12) 0.0034(13) 0.0005(12)
C21 0.0540(18) 0.0476(17) 0.0449(18) -0.0014(14) 0.0015(15) -0.0021(14)
C22 0.079(3) 0.0497(18) 0.0460(19) 0.0003(15) 0.0141(18) -0.0055(17)
C23 0.090(3) 0.0523(19) 0.0427(19) 0.0065(15) 0.0202(19) 0.0172(19)
C24 0.059(2) 0.074(2) 0.069(2) 0.014(2) -0.0009(19) 0.020(2)
C25 0.0460(18) 0.0566(18) 0.0610(19) 0.0057(15) 0.0039(16) 0.0042(15)
_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
Cl1 C23 1.738(3) . ?
O1 C1 1.218(3) . ?
O2 N2 1.195(3) . ?
O3 N2 1.213(3) . ?
N1 C9 1.454(3) . ?
N1 C12 1.476(3) . ?
N1 H1A 0.8600 . ?
N2 C11 1.489(3) . ?
C1 C2 1.463(4) . ?
C1 C9 1.528(4) . ?
C2 C3 1.389(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.375(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.487(4) . ?
C8 C9 1.542(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.560(4) . ?
C10 C20 1.506(4) . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9800 . ?
C11 C12 1.566(4) . ?
C11 H11A 0.9800 . ?
C12 C13 1.501(4) . ?
C12 H12A 0.9800 . ?
C13 C14 1.381(4) . ?
C13 C18 1.382(4) . ?
C14 C15 1.377(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.385(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(5) . ?
C16 C19 1.502(5) . ?
C17 C18 1.384(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.381(4) . ?
C20 C25 1.383(4) . ?
C21 C22 1.382(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.358(5) . ?
C24 C25 1.386(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 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
C9 N1 C12 112.3(2) . . ?
C9 N1 H1A 123.9 . . ?
C12 N1 H1A 123.9 . . ?
O2 N2 O3 124.0(3) . . ?
O2 N2 C11 120.2(3) . . ?
O3 N2 C11 115.8(3) . . ?
O1 C1 C2 127.1(3) . . ?
O1 C1 C9 124.6(2) . . ?
C2 C1 C9 108.3(2) . . ?
C3 C2 C7 122.4(3) . . ?
C3 C2 C1 128.7(3) . . ?
C7 C2 C1 108.8(3) . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
C6 C7 C2 118.6(3) . . ?
C6 C7 C8 129.6(3) . . ?
C2 C7 C8 111.8(2) . . ?
C7 C8 C9 105.1(2) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
N1 C9 C1 113.2(2) . . ?
N1 C9 C8 115.4(2) . . ?
C1 C9 C8 103.8(2) . . ?
N1 C9 C10 102.0(2) . . ?
C1 C9 C10 107.8(2) . . ?
C8 C9 C10 114.8(2) . . ?
C20 C10 C11 118.1(2) . . ?
C20 C10 C9 116.4(2) . . ?
C11 C10 C9 100.7(2) . . ?
C20 C10 H10A 107.0 . . ?
C11 C10 H10A 107.0 . . ?
C9 C10 H10A 107.0 . . ?
N2 C11 C10 114.0(2) . . ?
N2 C11 C12 111.5(2) . . ?
C10 C11 C12 104.8(2) . . ?
N2 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C12 C13 113.2(2) . . ?
N1 C12 C11 102.1(2) . . ?
C13 C12 C11 116.0(2) . . ?
N1 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C12 120.1(3) . . ?
C18 C13 C12 122.0(3) . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C17 C16 C15 117.8(3) . . ?
C17 C16 C19 121.5(4) . . ?
C15 C16 C19 120.7(4) . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17A 119.2 . . ?
C18 C17 H17A 119.2 . . ?
C13 C18 C17 120.4(3) . . ?
C13 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 117.7(3) . . ?
C21 C20 C10 119.3(2) . . ?
C25 C20 C10 123.0(2) . . ?
C20 C21 C22 121.9(3) . . ?
C20 C21 H21A 119.1 . . ?
C22 C21 H21A 119.1 . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
C24 C23 C22 121.0(3) . . ?
C24 C23 Cl1 120.0(3) . . ?
C22 C23 Cl1 119.1(3) . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C20 C25 C24 120.8(3) . . ?
C20 C25 H25A 119.6 . . ?
C24 C25 H25A 119.6 . . ?
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 -6.2(5) . . . . ?
C9 C1 C2 C3 172.3(3) . . . . ?
O1 C1 C2 C7 172.3(3) . . . . ?
C9 C1 C2 C7 -9.1(3) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C5 C6 C7 C8 -177.7(3) . . . . ?
C3 C2 C7 C6 0.4(4) . . . . ?
C1 C2 C7 C6 -178.3(3) . . . . ?
C3 C2 C7 C8 178.2(3) . . . . ?
C1 C2 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -172.9(3) . . . . ?
C2 C7 C8 C9 9.6(3) . . . . ?
C12 N1 C9 C1 142.6(2) . . . . ?
C12 N1 C9 C8 -98.1(3) . . . . ?
C12 N1 C9 C10 27.0(3) . . . . ?
O1 C1 C9 N1 -41.2(4) . . . . ?
C2 C1 C9 N1 140.2(2) . . . . ?
O1 C1 C9 C8 -167.0(3) . . . . ?
C2 C1 C9 C8 14.4(3) . . . . ?
O1 C1 C9 C10 70.9(3) . . . . ?
C2 C1 C9 C10 -107.7(2) . . . . ?
C7 C8 C9 N1 -138.6(2) . . . . ?
C7 C8 C9 C1 -14.2(3) . . . . ?
C7 C8 C9 C10 103.2(3) . . . . ?
N1 C9 C10 C20 -169.3(2) . . . . ?
C1 C9 C10 C20 71.3(3) . . . . ?
C8 C9 C10 C20 -43.8(3) . . . . ?
N1 C9 C10 C11 -40.5(2) . . . . ?
C1 C9 C10 C11 -159.9(2) . . . . ?
C8 C9 C10 C11 85.0(3) . . . . ?
O2 N2 C11 C10 -20.0(4) . . . . ?
O3 N2 C11 C10 162.5(3) . . . . ?
O2 N2 C11 C12 98.4(3) . . . . ?
O3 N2 C11 C12 -79.0(3) . . . . ?
C20 C10 C11 N2 -70.2(3) . . . . ?
C9 C10 C11 N2 162.1(2) . . . . ?
C20 C10 C11 C12 167.6(2) . . . . ?
C9 C10 C11 C12 39.9(2) . . . . ?
C9 N1 C12 C13 -127.9(3) . . . . ?
C9 N1 C12 C11 -2.4(3) . . . . ?
N2 C11 C12 N1 -148.1(2) . . . . ?
C10 C11 C12 N1 -24.3(2) . . . . ?
N2 C11 C12 C13 -24.4(3) . . . . ?
C10 C11 C12 C13 99.4(3) . . . . ?
N1 C12 C13 C14 -143.0(3) . . . . ?
C11 C12 C13 C14 99.3(3) . . . . ?
N1 C12 C13 C18 36.6(4) . . . . ?
C11 C12 C13 C18 -81.0(3) . . . . ?
C18 C13 C14 C15 -0.5(5) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 1.8(5) . . . . ?
C14 C15 C16 C19 -178.2(3) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C19 C16 C17 C18 178.2(3) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C12 C13 C18 C17 -179.2(3) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
C11 C10 C20 C21 146.6(3) . . . . ?
C9 C10 C20 C21 -93.5(3) . . . . ?
C11 C10 C20 C25 -33.5(4) . . . . ?
C9 C10 C20 C25 86.4(3) . . . . ?
C25 C20 C21 C22 -1.3(4) . . . . ?
C10 C20 C21 C22 178.6(3) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C21 C22 C23 Cl1 179.1(2) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
Cl1 C23 C24 C25 -178.4(2) . . . . ?
C21 C20 C25 C24 1.9(4) . . . . ?
C10 C20 C25 C24 -177.9(3) . . . . ?
C23 C24 C25 C20 -1.3(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.227
_refine_diff_density_min -0.246
_refine_diff_density_rms 0.034