# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019
#######################################################################
#
# 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
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data_r20180611d
_audit_block_doi 10.5517/ccdc.csd.cc232nf9
_database_code_depnum_ccdc_archive 'CCDC 1938970'
loop_
_audit_author_name
_audit_author_address
'Jiaxu Feng'
;Nankai university
China
;
_audit_update_record
;
2019-07-08 deposited with the CCDC. 2019-10-25 downloaded from the CCDC.
;
_audit_creation_date 2018-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C24 H25 N3 O4'
_chemical_formula_sum 'C24 H25 N3 O4'
_chemical_formula_weight 419.47
_chemical_melting_point ?
_chemical_oxdiff_formula 'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 10.3195(5)
_cell_length_b 12.2231(5)
_cell_length_c 16.8849(7)
_cell_angle_alpha 90
_cell_angle_beta 98.881(4)
_cell_angle_gamma 90
_cell_volume 2104.26(16)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 10605
_cell_measurement_temperature 113.15
_cell_measurement_theta_max 32.8150
_cell_measurement_theta_min 2.0550
_shelx_estimated_absorpt_T_max 0.984
_shelx_estimated_absorpt_T_min 0.978
_exptl_absorpt_coefficient_mu 0.091
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.78085
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.324
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 888
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.18
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0609
_diffrn_reflns_av_unetI/netI 0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 21595
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.372
_diffrn_reflns_theta_min 2.065
_diffrn_ambient_temperature 113.15
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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 -115.00 65.00 1.00 1.00 -- -25.00 45.00 0.00 180
2 \w -115.00 65.00 1.00 1.00 -- -25.00 45.00 90.00 180
3 \w -115.00 65.00 1.00 1.00 -- -25.00 45.00 180.00 180
;
_diffrn_measurement_device 'abstract diffractometer'
_diffrn_measurement_device_type 'Rigaku Saturn 70'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0382280000
_diffrn_orient_matrix_UB_12 0.0303388000
_diffrn_orient_matrix_UB_13 0.0237622000
_diffrn_orient_matrix_UB_21 -0.0367818000
_diffrn_orient_matrix_UB_22 -0.0476701000
_diffrn_orient_matrix_UB_23 0.0054760000
_diffrn_orient_matrix_UB_31 0.0450214000
_diffrn_orient_matrix_UB_32 -0.0132095000
_diffrn_orient_matrix_UB_33 0.0348264000
_diffrn_radiation_monochromator confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3404
_reflns_number_total 4268
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 26.32
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 0.239
_refine_diff_density_min -0.192
_refine_diff_density_rms 0.038
_refine_ls_extinction_coef 0.017(3)
_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 1.042
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 284
_refine_ls_number_reflns 4268
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0579
_refine_ls_R_factor_gt 0.0437
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.6850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0988
_refine_ls_wR_factor_ref 0.1076
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
C13(H13A,H13B), C14(H14A,H14B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_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
O1 O 0.10709(12) 0.65490(9) 0.65871(8) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.06081(10) 0.31176(10) 0.61405(7) 0.0365(3) Uani 1 1 d . . . . .
O3 O 0.66104(12) 0.41562(13) 0.64755(7) 0.0566(4) Uani 1 1 d . . . . .
O4 O 0.67951(10) 0.40942(10) 0.51761(7) 0.0343(3) Uani 1 1 d . . . . .
N1 N -0.02591(12) 0.55911(11) 0.73118(8) 0.0300(3) Uani 1 1 d . . . . .
N2 N 0.22858(12) 0.43214(10) 0.65818(7) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.27411(12) 0.28587(10) 0.58968(8) 0.0272(3) Uani 1 1 d . . . . .
C1 C 0.08622(15) 0.57713(12) 0.70035(9) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.18256(15) 0.48285(12) 0.72775(9) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.10152(15) 0.41065(12) 0.77387(9) 0.0277(3) Uani 1 1 d . . . . .
C4 C -0.01982(15) 0.45981(12) 0.77453(9) 0.0279(3) Uani 1 1 d . . . . .
C5 C -0.11448(16) 0.41448(14) 0.81339(10) 0.0351(4) Uani 1 1 d . . . . .
H5 H -0.197128 0.448884 0.812983 0.042 Uiso 1 1 calc R . . . .
C6 C -0.08407(18) 0.31606(15) 0.85335(10) 0.0402(4) Uani 1 1 d . . . . .
H6 H -0.147265 0.282480 0.880833 0.048 Uiso 1 1 calc R . . . .
C7 C 0.03608(19) 0.26622(14) 0.85388(10) 0.0400(4) Uani 1 1 d . . . . .
H7 H 0.054447 0.198956 0.881527 0.048 Uiso 1 1 calc R . . . .
C8 C 0.13090(17) 0.31392(13) 0.81406(10) 0.0346(4) Uani 1 1 d . . . . .
H8 H 0.213978 0.280136 0.814776 0.042 Uiso 1 1 calc R . . . .
C9 C -0.13885(16) 0.63191(15) 0.71836(11) 0.0395(4) Uani 1 1 d . . . . .
H9A H -0.217182 0.590238 0.696097 0.059 Uiso 1 1 calc GR . . . .
H9B H -0.123576 0.689908 0.680799 0.059 Uiso 1 1 calc GR . . . .
H9C H -0.151821 0.664605 0.769549 0.059 Uiso 1 1 calc GR . . . .
C10 C 0.17494(14) 0.33978(12) 0.62034(9) 0.0267(3) Uani 1 1 d . . . . .
C11 C 0.40437(14) 0.33002(12) 0.62090(9) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.452287 0.278512 0.661201 0.030 Uiso 1 1 calc R . . . .
C12 C 0.37132(14) 0.43641(13) 0.66253(9) 0.0269(3) Uani 1 1 d . . . . .
H12 H 0.396594 0.501298 0.632228 0.032 Uiso 1 1 calc R . . . .
C13 C 0.41906(15) 0.45120(14) 0.75181(9) 0.0324(4) Uani 1 1 d . . . . .
H13A H 0.506185 0.486883 0.761607 0.039 Uiso 1 1 calc R . . . .
H13B H 0.423706 0.380334 0.780498 0.039 Uiso 1 1 calc R . . . .
C14 C 0.31282(15) 0.52518(14) 0.77686(10) 0.0324(4) Uani 1 1 d . . . . .
H14A H 0.328347 0.602565 0.763785 0.039 Uiso 1 1 calc R . . . .
H14B H 0.310797 0.518989 0.835117 0.039 Uiso 1 1 calc R . . . .
C15 C 0.25554(14) 0.18473(12) 0.54838(9) 0.0251(3) Uani 1 1 d . . . . .
C16 C 0.14127(15) 0.16445(13) 0.49519(9) 0.0305(4) Uani 1 1 d . . . . .
H16 H 0.076090 0.219622 0.484435 0.037 Uiso 1 1 calc R . . . .
C17 C 0.12274(16) 0.06323(14) 0.45781(10) 0.0351(4) Uani 1 1 d . . . . .
H17 H 0.043624 0.049793 0.422265 0.042 Uiso 1 1 calc R . . . .
C18 C 0.21682(17) -0.01911(13) 0.47096(10) 0.0352(4) Uani 1 1 d . . . . .
C19 C 0.33176(16) 0.00406(13) 0.52177(10) 0.0324(4) Uani 1 1 d . . . . .
H19 H 0.398724 -0.049885 0.530466 0.039 Uiso 1 1 calc R . . . .
C20 C 0.35171(15) 0.10404(12) 0.56032(9) 0.0277(3) Uani 1 1 d . . . . .
H20 H 0.431563 0.117629 0.595129 0.033 Uiso 1 1 calc R . . . .
C21 C 0.1941(2) -0.12991(16) 0.43145(13) 0.0547(5) Uani 1 1 d . . . . .
H21A H 0.264093 -0.145127 0.399825 0.082 Uiso 1 1 calc GR . . . .
H21B H 0.109234 -0.130114 0.396199 0.082 Uiso 1 1 calc GR . . . .
H21C H 0.194272 -0.186319 0.472712 0.082 Uiso 1 1 calc GR . . . .
C22 C 0.48240(14) 0.34769(13) 0.55245(9) 0.0272(3) Uani 1 1 d . . . . .
H22A H 0.491620 0.276843 0.525455 0.033 Uiso 1 1 calc R . . . .
H22B H 0.433012 0.397819 0.512703 0.033 Uiso 1 1 calc R . . . .
C23 C 0.61634(15) 0.39450(13) 0.57969(9) 0.0285(3) Uani 1 1 d . . . . .
C24 C 0.81350(16) 0.44869(16) 0.53491(11) 0.0418(4) Uani 1 1 d . . . . .
H24A H 0.856878 0.438014 0.487785 0.063 Uiso 1 1 calc GR . . . .
H24B H 0.860798 0.407873 0.580357 0.063 Uiso 1 1 calc GR . . . .
H24C H 0.813378 0.526706 0.548262 0.063 Uiso 1 1 calc GR . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0427(7) 0.0296(6) 0.0565(8) 0.0088(6) 0.0141(6) 0.0013(5)
O2 0.0228(6) 0.0454(7) 0.0418(7) -0.0127(6) 0.0062(5) -0.0006(5)
O3 0.0381(7) 0.0983(12) 0.0342(7) -0.0137(7) 0.0084(6) -0.0230(7)
O4 0.0259(6) 0.0447(7) 0.0337(6) 0.0044(5) 0.0090(5) -0.0012(5)
N1 0.0263(7) 0.0293(7) 0.0347(7) -0.0015(6) 0.0060(5) 0.0034(5)
N2 0.0237(7) 0.0291(7) 0.0286(7) -0.0046(6) 0.0059(5) 0.0018(5)
N3 0.0217(6) 0.0268(7) 0.0335(7) -0.0066(6) 0.0054(5) -0.0001(5)
C1 0.0322(9) 0.0235(8) 0.0337(8) -0.0045(7) 0.0059(7) 0.0004(6)
C2 0.0298(8) 0.0249(8) 0.0294(8) -0.0037(6) 0.0079(6) 0.0027(6)
C3 0.0302(8) 0.0269(8) 0.0267(8) -0.0059(6) 0.0066(6) -0.0008(6)
C4 0.0285(8) 0.0288(8) 0.0262(8) -0.0066(6) 0.0038(6) -0.0012(6)
C5 0.0297(9) 0.0415(10) 0.0348(9) -0.0050(8) 0.0071(7) -0.0049(7)
C6 0.0457(10) 0.0426(10) 0.0344(9) -0.0035(8) 0.0132(8) -0.0147(8)
C7 0.0581(12) 0.0293(9) 0.0343(9) 0.0003(7) 0.0119(8) -0.0044(8)
C8 0.0424(10) 0.0283(8) 0.0342(9) -0.0029(7) 0.0097(7) 0.0050(7)
C9 0.0306(9) 0.0381(10) 0.0494(10) -0.0023(8) 0.0046(8) 0.0078(7)
C10 0.0260(8) 0.0289(8) 0.0250(7) -0.0008(6) 0.0040(6) 0.0028(6)
C11 0.0229(7) 0.0259(8) 0.0263(7) -0.0019(6) 0.0044(6) 0.0000(6)
C12 0.0248(8) 0.0270(8) 0.0299(8) -0.0011(6) 0.0073(6) 0.0003(6)
C13 0.0271(8) 0.0404(9) 0.0296(8) -0.0080(7) 0.0042(6) 0.0004(7)
C14 0.0321(9) 0.0341(9) 0.0316(8) -0.0073(7) 0.0064(7) -0.0019(7)
C15 0.0275(8) 0.0248(8) 0.0247(7) 0.0005(6) 0.0096(6) -0.0023(6)
C16 0.0281(8) 0.0338(9) 0.0300(8) -0.0024(7) 0.0053(6) 0.0005(7)
C17 0.0328(9) 0.0399(10) 0.0332(9) -0.0075(7) 0.0071(7) -0.0076(7)
C18 0.0419(10) 0.0276(8) 0.0400(9) -0.0047(7) 0.0189(8) -0.0077(7)
C19 0.0364(9) 0.0257(8) 0.0386(9) 0.0030(7) 0.0166(7) 0.0020(7)
C20 0.0283(8) 0.0278(8) 0.0279(8) 0.0031(6) 0.0074(6) 0.0000(6)
C21 0.0596(13) 0.0376(11) 0.0711(14) -0.0186(10) 0.0235(11) -0.0116(9)
C22 0.0266(8) 0.0293(8) 0.0264(7) -0.0025(6) 0.0066(6) 0.0005(6)
C23 0.0281(8) 0.0284(8) 0.0303(8) -0.0006(7) 0.0090(6) 0.0013(6)
C24 0.0248(9) 0.0566(12) 0.0450(10) 0.0062(9) 0.0090(7) -0.0038(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2211(19) . ?
O2 C10 1.2153(18) . ?
O3 C23 1.1954(19) . ?
O4 C23 1.3296(18) . ?
O4 C24 1.4501(19) . ?
N1 C1 1.358(2) . ?
N1 C4 1.414(2) . ?
N1 C9 1.456(2) . ?
N2 C2 1.4703(18) . ?
N2 C10 1.3710(19) . ?
N2 C12 1.4644(18) . ?
N3 C10 1.3832(18) . ?
N3 C11 1.4688(18) . ?
N3 C15 1.4178(19) . ?
C1 C2 1.545(2) . ?
C2 C3 1.512(2) . ?
C2 C14 1.555(2) . ?
C3 C4 1.390(2) . ?
C3 C8 1.374(2) . ?
C4 C5 1.375(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(2) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.541(2) . ?
C11 C22 1.5226(19) . ?
C12 H12 1.0000 . ?
C12 C13 1.523(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.530(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.390(2) . ?
C15 C20 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(2) . ?
C18 C19 1.382(2) . ?
C18 C21 1.512(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.501(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O4 C24 117.06(13) . . ?
C1 N1 C4 111.42(12) . . ?
C1 N1 C9 123.63(14) . . ?
C4 N1 C9 124.92(13) . . ?
C10 N2 C2 124.22(12) . . ?
C10 N2 C12 112.54(12) . . ?
C12 N2 C2 113.04(12) . . ?
C10 N3 C11 112.31(12) . . ?
C10 N3 C15 123.22(12) . . ?
C15 N3 C11 122.93(12) . . ?
O1 C1 N1 125.69(15) . . ?
O1 C1 C2 126.18(14) . . ?
N1 C1 C2 108.13(13) . . ?
N2 C2 C1 110.33(12) . . ?
N2 C2 C3 115.98(12) . . ?
N2 C2 C14 101.95(11) . . ?
C1 C2 C14 112.00(13) . . ?
C3 C2 C1 102.01(12) . . ?
C3 C2 C14 114.89(13) . . ?
C4 C3 C2 108.80(13) . . ?
C8 C3 C2 131.26(14) . . ?
C8 C3 C4 119.89(15) . . ?
C3 C4 N1 109.57(13) . . ?
C5 C4 N1 127.96(14) . . ?
C5 C4 C3 122.47(15) . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.15(16) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.33(16) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.52(16) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.64(16) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N2 126.08(14) . . ?
O2 C10 N3 126.59(14) . . ?
N2 C10 N3 107.33(12) . . ?
N3 C11 H11 110.0 . . ?
N3 C11 C12 102.65(11) . . ?
N3 C11 C22 109.98(12) . . ?
C12 C11 H11 110.0 . . ?
C22 C11 H11 110.0 . . ?
C22 C11 C12 114.00(12) . . ?
N2 C12 C11 103.81(11) . . ?
N2 C12 H12 110.0 . . ?
N2 C12 C13 102.89(12) . . ?
C11 C12 H12 110.0 . . ?
C13 C12 C11 119.41(13) . . ?
C13 C12 H12 110.0 . . ?
C12 C13 H13A 111.4 . . ?
C12 C13 H13B 111.4 . . ?
C12 C13 C14 101.99(12) . . ?
H13A C13 H13B 109.2 . . ?
C14 C13 H13A 111.4 . . ?
C14 C13 H13B 111.4 . . ?
C2 C14 H14A 110.8 . . ?
C2 C14 H14B 110.8 . . ?
C13 C14 C2 104.67(12) . . ?
C13 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C16 C15 N3 120.67(13) . . ?
C16 C15 C20 118.83(14) . . ?
C20 C15 N3 120.50(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.75(15) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.87(16) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C21 121.36(17) . . ?
C19 C18 C17 117.48(15) . . ?
C19 C18 C21 121.15(16) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.59(15) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.42(15) . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 H22A 109.0 . . ?
C11 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C11 113.04(12) . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
O3 C23 O4 124.22(15) . . ?
O3 C23 C22 125.23(14) . . ?
O4 C23 C22 110.55(13) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C1 C2 N2 -54.0(2) . . . . ?
O1 C1 C2 C3 -177.86(16) . . . . ?
O1 C1 C2 C14 58.8(2) . . . . ?
N1 C1 C2 N2 126.43(13) . . . . ?
N1 C1 C2 C3 2.62(16) . . . . ?
N1 C1 C2 C14 -120.75(14) . . . . ?
N1 C4 C5 C6 -178.91(15) . . . . ?
N2 C2 C3 C4 -121.90(14) . . . . ?
N2 C2 C3 C8 60.7(2) . . . . ?
N2 C2 C14 C13 -25.27(15) . . . . ?
N2 C12 C13 C14 -36.20(15) . . . . ?
N3 C11 C12 N2 6.64(14) . . . . ?
N3 C11 C12 C13 120.36(14) . . . . ?
N3 C11 C22 C23 179.10(12) . . . . ?
N3 C15 C16 C17 -177.40(13) . . . . ?
N3 C15 C20 C19 178.05(13) . . . . ?
C1 N1 C4 C3 1.09(18) . . . . ?
C1 N1 C4 C5 -179.52(15) . . . . ?
C1 C2 C3 C4 -1.98(16) . . . . ?
C1 C2 C3 C8 -179.40(16) . . . . ?
C1 C2 C14 C13 -143.20(13) . . . . ?
C2 N2 C10 O2 31.4(2) . . . . ?
C2 N2 C10 N3 -149.66(13) . . . . ?
C2 N2 C12 C11 146.84(12) . . . . ?
C2 N2 C12 C13 21.73(16) . . . . ?
C2 C3 C4 N1 0.73(17) . . . . ?
C2 C3 C4 C5 -178.70(14) . . . . ?
C2 C3 C8 C7 178.20(15) . . . . ?
C3 C2 C14 C13 101.02(15) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 N1 C1 O1 178.09(15) . . . . ?
C4 N1 C1 C2 -2.38(17) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C3 -0.6(2) . . . . ?
C8 C3 C4 N1 178.49(14) . . . . ?
C8 C3 C4 C5 -0.9(2) . . . . ?
C9 N1 C1 O1 0.0(3) . . . . ?
C9 N1 C1 C2 179.52(14) . . . . ?
C9 N1 C4 C3 179.16(14) . . . . ?
C9 N1 C4 C5 -1.5(3) . . . . ?
C10 N2 C2 C1 -96.25(16) . . . . ?
C10 N2 C2 C3 19.1(2) . . . . ?
C10 N2 C2 C14 144.62(14) . . . . ?
C10 N2 C12 C11 -0.11(16) . . . . ?
C10 N2 C12 C13 -125.21(13) . . . . ?
C10 N3 C11 C12 -11.54(16) . . . . ?
C10 N3 C11 C22 -133.22(13) . . . . ?
C10 N3 C15 C16 39.4(2) . . . . ?
C10 N3 C15 C20 -140.69(15) . . . . ?
C11 N3 C10 O2 -169.12(15) . . . . ?
C11 N3 C10 N2 11.90(17) . . . . ?
C11 N3 C15 C16 -155.77(14) . . . . ?
C11 N3 C15 C20 24.1(2) . . . . ?
C11 C12 C13 C14 -150.42(13) . . . . ?
C11 C22 C23 O3 0.8(2) . . . . ?
C11 C22 C23 O4 -179.28(13) . . . . ?
C12 N2 C2 C1 121.28(13) . . . . ?
C12 N2 C2 C3 -123.42(14) . . . . ?
C12 N2 C2 C14 2.15(16) . . . . ?
C12 N2 C10 O2 173.98(15) . . . . ?
C12 N2 C10 N3 -7.03(17) . . . . ?
C12 C11 C22 C23 64.46(17) . . . . ?
C12 C13 C14 C2 38.47(16) . . . . ?
C14 C2 C3 C4 119.41(14) . . . . ?
C14 C2 C3 C8 -58.0(2) . . . . ?
C15 N3 C10 O2 -2.9(2) . . . . ?
C15 N3 C10 N2 178.12(13) . . . . ?
C15 N3 C11 C12 -177.81(13) . . . . ?
C15 N3 C11 C22 60.52(18) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C16 C15 C20 C19 -2.1(2) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
C16 C17 C18 C21 178.51(16) . . . . ?
C17 C18 C19 C20 2.0(2) . . . . ?
C18 C19 C20 C15 -0.3(2) . . . . ?
C20 C15 C16 C17 2.7(2) . . . . ?
C21 C18 C19 C20 -177.83(15) . . . . ?
C22 C11 C12 N2 125.54(13) . . . . ?
C22 C11 C12 C13 -120.74(15) . . . . ?
C24 O4 C23 O3 3.2(2) . . . . ?
C24 O4 C23 C22 -176.68(13) . . . . ?
_iucr_refine_instructions_details
;
TITL r20180611d_a.res in P2(1)/n
r20180611d.res
created by SHELXL-2016/6 at 07:48:26 on 13-Jun-2018
REM Old TITL r20180611d in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.161, Rweak 0.373, Alpha 0.034, Orientation as input
REM Formula found by SHELXT: C24 N3 O4
CELL 0.71073 10.3195 12.2231 16.8849 90 98.881 90
ZERR 4 0.0005 0.0005 0.0007 0 0.004 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 96 100 12 16
L.S. 10
PLAN 20
SIZE 0.24 0.22 0.18
TEMP -160
BOND $H
conf
htab
fmap 2
acta
REM
REM
REM
WGHT 0.042000 0.685000
EXTI 0.016765
FVAR 1.19273
O1 4 0.107092 0.654898 0.658715 11.00000 0.04271 0.02956 =
0.05652 0.00879 0.01410 0.00128
O2 4 0.060812 0.311763 0.614051 11.00000 0.02282 0.04535 =
0.04181 -0.01267 0.00625 -0.00062
O3 4 0.661039 0.415619 0.647546 11.00000 0.03809 0.09834 =
0.03417 -0.01369 0.00843 -0.02295
O4 4 0.679508 0.409420 0.517614 11.00000 0.02586 0.04473 =
0.03369 0.00436 0.00897 -0.00120
N1 3 -0.025912 0.559114 0.731178 11.00000 0.02625 0.02932 =
0.03474 -0.00151 0.00598 0.00338
N2 3 0.228581 0.432142 0.658177 11.00000 0.02367 0.02907 =
0.02862 -0.00456 0.00586 0.00178
N3 3 0.274109 0.285870 0.589682 11.00000 0.02170 0.02678 =
0.03350 -0.00660 0.00542 -0.00014
C1 1 0.086218 0.577131 0.700353 11.00000 0.03222 0.02354 =
0.03369 -0.00448 0.00591 0.00035
C2 1 0.182558 0.482846 0.727747 11.00000 0.02985 0.02491 =
0.02938 -0.00366 0.00792 0.00271
C3 1 0.101525 0.410654 0.773872 11.00000 0.03025 0.02685 =
0.02668 -0.00590 0.00665 -0.00085
C4 1 -0.019817 0.459807 0.774528 11.00000 0.02852 0.02884 =
0.02622 -0.00661 0.00382 -0.00122
C5 1 -0.114481 0.414477 0.813394 11.00000 0.02968 0.04146 =
0.03481 -0.00499 0.00714 -0.00489
AFIX 43
H5 2 -0.197128 0.448884 0.812983 11.00000 -1.20000
AFIX 0
C6 1 -0.084065 0.316057 0.853354 11.00000 0.04574 0.04259 =
0.03442 -0.00346 0.01322 -0.01471
AFIX 43
H6 2 -0.147265 0.282480 0.880833 11.00000 -1.20000
AFIX 0
C7 1 0.036075 0.266219 0.853879 11.00000 0.05805 0.02927 =
0.03425 0.00031 0.01193 -0.00441
AFIX 43
H7 2 0.054447 0.198956 0.881527 11.00000 -1.20000
AFIX 0
C8 1 0.130898 0.313916 0.814064 11.00000 0.04243 0.02834 =
0.03424 -0.00289 0.00968 0.00503
AFIX 43
H8 2 0.213978 0.280136 0.814776 11.00000 -1.20000
AFIX 0
C9 1 -0.138849 0.631914 0.718359 11.00000 0.03061 0.03813 =
0.04938 -0.00229 0.00458 0.00776
AFIX 137
H9A 2 -0.217182 0.590238 0.696097 11.00000 -1.50000
H9B 2 -0.123576 0.689908 0.680799 11.00000 -1.50000
H9C 2 -0.151821 0.664605 0.769549 11.00000 -1.50000
AFIX 0
C10 1 0.174938 0.339784 0.620342 11.00000 0.02603 0.02893 =
0.02504 -0.00080 0.00405 0.00280
C11 1 0.404370 0.330020 0.620903 11.00000 0.02287 0.02595 =
0.02631 -0.00194 0.00445 -0.00005
AFIX 13
H11 2 0.452287 0.278512 0.661201 11.00000 -1.20000
AFIX 0
C12 1 0.371324 0.436411 0.662529 11.00000 0.02478 0.02702 =
0.02987 -0.00114 0.00726 0.00033
AFIX 13
H12 2 0.396594 0.501298 0.632228 11.00000 -1.20000
AFIX 0
C13 1 0.419056 0.451200 0.751807 11.00000 0.02714 0.04041 =
0.02963 -0.00797 0.00421 0.00041
AFIX 23
H13A 2 0.506185 0.486883 0.761607 11.00000 -1.20000
H13B 2 0.423706 0.380334 0.780498 11.00000 -1.20000
AFIX 0
C14 1 0.312816 0.525177 0.776860 11.00000 0.03205 0.03408 =
0.03163 -0.00732 0.00643 -0.00185
AFIX 23
H14A 2 0.328347 0.602565 0.763785 11.00000 -1.20000
H14B 2 0.310797 0.518989 0.835117 11.00000 -1.20000
AFIX 0
C15 1 0.255544 0.184727 0.548383 11.00000 0.02754 0.02480 =
0.02474 0.00049 0.00957 -0.00229
C16 1 0.141269 0.164446 0.495185 11.00000 0.02806 0.03377 =
0.02997 -0.00239 0.00534 0.00055
AFIX 43
H16 2 0.076090 0.219622 0.484435 11.00000 -1.20000
AFIX 0
C17 1 0.122739 0.063233 0.457813 11.00000 0.03279 0.03989 =
0.03316 -0.00750 0.00709 -0.00761
AFIX 43
H17 2 0.043624 0.049793 0.422265 11.00000 -1.20000
AFIX 0
C18 1 0.216816 -0.019113 0.470960 11.00000 0.04189 0.02761 =
0.04004 -0.00474 0.01894 -0.00772
C19 1 0.331763 0.004059 0.521766 11.00000 0.03637 0.02567 =
0.03862 0.00298 0.01659 0.00201
AFIX 43
H19 2 0.398724 -0.049885 0.530466 11.00000 -1.20000
AFIX 0
C20 1 0.351714 0.104045 0.560317 11.00000 0.02833 0.02780 =
0.02790 0.00314 0.00745 0.00001
AFIX 43
H20 2 0.431563 0.117629 0.595129 11.00000 -1.20000
AFIX 0
C21 1 0.194106 -0.129914 0.431449 11.00000 0.05964 0.03763 =
0.07107 -0.01858 0.02348 -0.01161
AFIX 137
H21A 2 0.264093 -0.145127 0.399825 11.00000 -1.50000
H21B 2 0.109234 -0.130114 0.396199 11.00000 -1.50000
H21C 2 0.194272 -0.186319 0.472712 11.00000 -1.50000
AFIX 0
C22 1 0.482404 0.347688 0.552453 11.00000 0.02661 0.02935 =
0.02644 -0.00249 0.00663 0.00047
AFIX 23
H22A 2 0.491620 0.276843 0.525455 11.00000 -1.20000
H22B 2 0.433012 0.397819 0.512703 11.00000 -1.20000
AFIX 0
C23 1 0.616338 0.394498 0.579690 11.00000 0.02806 0.02842 =
0.03032 -0.00055 0.00898 0.00130
C24 1 0.813501 0.448686 0.534906 11.00000 0.02485 0.05664 =
0.04498 0.00624 0.00901 -0.00381
AFIX 137
H24A 2 0.856878 0.438014 0.487785 11.00000 -1.50000
H24B 2 0.860798 0.407873 0.580357 11.00000 -1.50000
H24C 2 0.813378 0.526706 0.548262 11.00000 -1.50000
AFIX 0
HKLF 4
REM r20180611d_a.res in P2(1)/n
REM R1 = 0.0437 for 3404 Fo > 4sig(Fo) and 0.0579 for all 4268 data
REM 284 parameters refined using 0 restraints
END
WGHT 0.0414 0.7020
REM Instructions for potential hydrogen bonds
EQIV $1 x-1, y, z
HTAB C9 O3_$1
EQIV $2 -x+1, -y+1, -z+1
HTAB C22 O4_$2
EQIV $3 x+1, y, z
HTAB C24 O2_$3
REM Highest difference peak 0.239, deepest hole -0.192, 1-sigma level 0.038
Q1 1 0.1034 -0.1587 0.4451 11.00000 0.05 0.24
Q2 1 0.1883 -0.1236 0.3649 11.00000 0.05 0.24
Q3 1 0.1575 0.4425 0.7598 11.00000 0.05 0.22
Q4 1 0.1338 0.5266 0.7129 11.00000 0.05 0.20
Q5 1 0.1998 0.4542 0.6917 11.00000 0.05 0.19
Q6 1 0.4038 0.4377 0.7063 11.00000 0.05 0.19
Q7 1 0.4397 0.3428 0.5865 11.00000 0.05 0.18
Q8 1 0.3866 0.3794 0.6426 11.00000 0.05 0.18
Q9 1 0.2855 -0.1964 0.4663 11.00000 0.05 0.18
Q10 1 0.6099 0.4619 0.6144 11.00000 0.05 0.18
Q11 1 -0.0213 0.5155 0.7631 11.00000 0.05 0.18
Q12 1 0.0428 0.4363 0.7787 11.00000 0.05 0.17
Q13 1 0.3206 0.1553 0.5349 11.00000 0.05 0.16
Q14 1 0.6421 0.3543 0.6249 11.00000 0.05 0.16
Q15 1 0.2816 -0.1830 0.4370 11.00000 0.05 0.16
Q16 1 0.2660 0.2356 0.5690 11.00000 0.05 0.15
Q17 1 0.3453 0.2979 0.6045 11.00000 0.05 0.15
Q18 1 0.2298 0.5026 0.7531 11.00000 0.05 0.15
Q19 1 0.1874 0.1494 0.5474 11.00000 0.05 0.14
Q20 1 0.1750 0.0180 0.4589 11.00000 0.05 0.14
REM The information below was added by Olex2.
REM
REM R1 = 0.0437 for 3404 Fo > 4sig(Fo) and 0.0579 for all 22238 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.24, deepest hole -0.19
REM Mean Shift 0, Max Shift -0.004.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0579
REM R1_gt = 0.0437
REM wR_ref = 0.1076
REM GOOF = 1.042
REM Shift_max = -0.004
REM Shift_mean = 0
REM Reflections_all = 22238
REM Reflections_gt = 3404
REM Parameters = n/a
REM Hole = -0.19
REM Peak = 0.24
REM Flack = n/a
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.597
_oxdiff_exptl_absorpt_empirical_full_min 0.677
#######################################################################
#
# 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_r20181026b1
_audit_block_doi 10.5517/ccdc.csd.cc232nnj
_database_code_depnum_ccdc_archive 'CCDC 1938977'
loop_
_audit_author_name
_audit_author_address
'Jiaxu Feng'
;Nankai university
China
;
_audit_update_record
;
2019-07-08 deposited with the CCDC. 2019-10-25 downloaded from the CCDC.
;
_audit_creation_date 2018-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C24 H25 N3 O4, C H Cl3'
_chemical_formula_sum 'C25 H26 Cl3 N3 O4'
_chemical_formula_weight 538.84
_chemical_absolute_configuration unk
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 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 10.740(2)
_cell_length_b 22.857(5)
_cell_length_c 10.909(2)
_cell_angle_alpha 90
_cell_angle_beta 104.54(3)
_cell_angle_gamma 90
_cell_volume 2592.2(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 4831
_cell_measurement_temperature 113.15
_cell_measurement_theta_max 27.8784
_cell_measurement_theta_min 1.9286
_shelx_estimated_absorpt_T_max 0.955
_shelx_estimated_absorpt_T_min 0.926
_exptl_absorpt_coefficient_mu 0.390
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8070
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrystalClear(Rigaku, 2008)'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.381
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 1120
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.12
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0777
_diffrn_reflns_av_unetI/netI 0.0959
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 29
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 31346
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.819
_diffrn_reflns_theta_min 1.959
_diffrn_ambient_temperature 113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Rigaku Saturn 70'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator confocal
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.895
_reflns_Friedel_fraction_full 0.966
_reflns_Friedel_fraction_max 0.939
_reflns_number_gt 8205
_reflns_number_total 11931
_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 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_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 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.296
_refine_diff_density_min -0.335
_refine_diff_density_rms 0.061
_refine_ls_abs_structure_details
;
Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.49(5)
_refine_ls_extinction_coef 0.0057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 642
_refine_ls_number_reflns 11931
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0997
_refine_ls_R_factor_gt 0.0713
_refine_ls_restrained_S_all 1.044
_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^)+(0.0752P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1584
_refine_ls_wR_factor_ref 0.1800
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Restrained distances
N3-H3 = N6-H6A
0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
C20(H20), C44(H44), C49(H49), C50(H50)
3.b Secondary CH2 refined with riding coordinates:
C11(H11A,H11B), C18(H18A,H18B), C19(H19A,H19B), C35(H35A,H35B), C42(H42A,
H42B), C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
C3(H3A), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
C17(H17), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C37(H37),
C38(H38), C39(H39), C40(H40), C41(H41), C45(H45), C46(H46)
3.d Idealised Me refined as rotating group:
C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C48(H48A,H48B,H48C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2042(4) 0.78234(17) 0.6129(4) 0.0370(9) Uani 1 1 d . . . . .
O2 O -0.0269(4) 0.67731(17) 0.5900(4) 0.0315(8) Uani 1 1 d . . . . .
O3 O 0.0819(4) 0.92328(18) 0.7317(4) 0.0433(11) Uani 1 1 d . . . . .
O4 O 0.2054(4) 0.93979(19) 0.5976(5) 0.0446(11) Uani 1 1 d . . . . .
O5 O 0.7588(4) 0.93775(18) 0.4117(4) 0.0391(10) Uani 1 1 d . . . . .
O6 O 0.5505(4) 1.03236(17) 0.4095(4) 0.0354(9) Uani 1 1 d . . . . .
O7 O 0.4553(4) 0.78351(18) 0.2864(4) 0.0411(10) Uani 1 1 d . . . . .
O8 O 0.3418(4) 0.76796(19) 0.4293(4) 0.0435(11) Uani 1 1 d . . . . .
N1 N -0.3227(4) 0.7033(2) 0.5130(5) 0.0346(11) Uani 1 1 d . . . . .
N2 N -0.0372(4) 0.7477(2) 0.4417(4) 0.0276(10) Uani 1 1 d . . . . .
N3 N 0.1610(4) 0.7137(2) 0.5583(5) 0.0353(11) Uani 1 1 d D . . . .
H3 H 0.197(6) 0.736(2) 0.508(5) 0.042 Uiso 1 1 d DR . . . .
N4 N 0.8621(4) 1.0177(2) 0.5223(5) 0.0335(11) Uani 1 1 d . . . . .
N5 N 0.5686(4) 0.9648(2) 0.5667(4) 0.0318(10) Uani 1 1 d . . . . .
N6 N 0.3681(5) 0.9894(2) 0.4394(5) 0.0359(11) Uani 1 1 d D . . . .
H6A H 0.334(6) 0.963(2) 0.483(5) 0.043 Uiso 1 1 d DR . . . .
C1 C -0.3928(6) 0.6911(3) 0.6087(6) 0.0456(16) Uani 1 1 d . . . . .
H1A H -0.379174 0.723190 0.670343 0.068 Uiso 1 1 calc GR . . . .
H1B H -0.361519 0.654473 0.652167 0.068 Uiso 1 1 calc GR . . . .
H1C H -0.484827 0.687608 0.567906 0.068 Uiso 1 1 calc GR . . . .
C2 C -0.3232(5) 0.6675(3) 0.4082(6) 0.0332(12) Uani 1 1 d . . . . .
C3 C -0.3926(6) 0.6171(3) 0.3718(7) 0.0436(15) Uani 1 1 d . . . . .
H3A H -0.449434 0.601965 0.418101 0.052 Uiso 1 1 calc R . . . .
C4 C -0.3752(6) 0.5892(3) 0.2635(7) 0.0441(16) Uani 1 1 d . . . . .
H4 H -0.420569 0.553969 0.236023 0.053 Uiso 1 1 calc R . . . .
C5 C -0.2935(6) 0.6117(3) 0.1949(6) 0.0389(14) Uani 1 1 d . . . . .
H5 H -0.285095 0.592002 0.120705 0.047 Uiso 1 1 calc R . . . .
C6 C -0.2234(6) 0.6628(3) 0.2335(5) 0.0335(13) Uani 1 1 d . . . . .
H6 H -0.167592 0.678175 0.186336 0.040 Uiso 1 1 calc R . . . .
C7 C -0.2374(5) 0.6905(2) 0.3421(5) 0.0279(11) Uani 1 1 d . . . . .
C8 C -0.1792(5) 0.7460(2) 0.4069(5) 0.0277(11) Uani 1 1 d . . . . .
C9 C -0.2330(5) 0.7470(2) 0.5261(5) 0.0309(12) Uani 1 1 d . . . . .
C10 C 0.0311(5) 0.7109(2) 0.5335(5) 0.0279(11) Uani 1 1 d . . . . .
C11 C 0.2441(6) 0.6767(3) 0.6524(7) 0.0443(15) Uani 1 1 d . . . . .
H11A H 0.293095 0.650428 0.609443 0.053 Uiso 1 1 calc R . . . .
H11B H 0.190132 0.651899 0.692880 0.053 Uiso 1 1 calc R . . . .
C12 C 0.3380(5) 0.7110(3) 0.7543(6) 0.0373(14) Uani 1 1 d . . . . .
C13 C 0.3243(6) 0.7698(3) 0.7777(6) 0.0435(15) Uani 1 1 d . . . . .
H13 H 0.252737 0.790572 0.727622 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4119(7) 0.7993(4) 0.8722(7) 0.0537(19) Uani 1 1 d . . . . .
H14 H 0.400880 0.839802 0.885678 0.064 Uiso 1 1 calc R . . . .
C15 C 0.5155(7) 0.7695(4) 0.9470(7) 0.058(2) Uani 1 1 d . . . . .
H15 H 0.575651 0.789429 1.012487 0.070 Uiso 1 1 calc R . . . .
C16 C 0.5311(7) 0.7110(4) 0.9261(7) 0.063(2) Uani 1 1 d . . . . .
H16 H 0.602354 0.690644 0.977666 0.076 Uiso 1 1 calc R . . . .
C17 C 0.4438(6) 0.6810(3) 0.8303(7) 0.0489(17) Uani 1 1 d . . . . .
H17 H 0.455906 0.640623 0.816535 0.059 Uiso 1 1 calc R . . . .
C18 C -0.2142(6) 0.8027(2) 0.3296(6) 0.0324(12) Uani 1 1 d . . . . .
H18A H -0.297315 0.798592 0.265516 0.039 Uiso 1 1 calc R . . . .
H18B H -0.219494 0.836308 0.385280 0.039 Uiso 1 1 calc R . . . .
C19 C -0.1028(6) 0.8102(3) 0.2663(5) 0.0344(13) Uani 1 1 d . . . . .
H19A H -0.095312 0.851429 0.241007 0.041 Uiso 1 1 calc R . . . .
H19B H -0.114333 0.784865 0.190790 0.041 Uiso 1 1 calc R . . . .
C20 C 0.0153(6) 0.7916(2) 0.3704(5) 0.0309(12) Uani 1 1 d . . . . .
H20 H 0.079784 0.772780 0.330867 0.037 Uiso 1 1 calc R . . . .
C21 C 0.0767(5) 0.8435(3) 0.4499(6) 0.0325(12) Uani 1 1 d . . . . .
H21 H 0.133482 0.867001 0.416822 0.039 Uiso 1 1 calc R . . . .
C22 C 0.0584(5) 0.8591(3) 0.5616(6) 0.0350(13) Uani 1 1 d . . . . .
H22 H 0.002753 0.836626 0.598337 0.042 Uiso 1 1 calc R . . . .
C23 C 0.1234(5) 0.9107(3) 0.6288(6) 0.0340(13) Uani 1 1 d . . . . .
C24 C 0.1412(7) 0.9735(3) 0.8049(7) 0.0545(19) Uani 1 1 d . . . . .
H24A H 0.137333 1.007234 0.748554 0.082 Uiso 1 1 calc GR . . . .
H24B H 0.231172 0.964578 0.846150 0.082 Uiso 1 1 calc GR . . . .
H24C H 0.095020 0.982705 0.869445 0.082 Uiso 1 1 calc GR . . . .
C25 C 0.9529(6) 1.0299(3) 0.4458(6) 0.0414(14) Uani 1 1 d . . . . .
H25A H 0.932824 1.067952 0.404189 0.062 Uiso 1 1 calc GR . . . .
H25B H 0.946271 0.999317 0.381514 0.062 Uiso 1 1 calc GR . . . .
H25C H 1.040617 1.030603 0.500435 0.062 Uiso 1 1 calc GR . . . .
C26 C 0.8483(5) 1.0524(3) 0.6250(5) 0.0304(12) Uani 1 1 d . . . . .
C27 C 0.9158(6) 1.1028(2) 0.6709(6) 0.0360(13) Uani 1 1 d . . . . .
H27 H 0.979722 1.118244 0.633643 0.043 Uiso 1 1 calc R . . . .
C28 C 0.8853(6) 1.1299(3) 0.7752(6) 0.0402(14) Uani 1 1 d . . . . .
H28 H 0.928948 1.164673 0.809051 0.048 Uiso 1 1 calc R . . . .
C29 C 0.7933(6) 1.1068(3) 0.8290(6) 0.0399(14) Uani 1 1 d . . . . .
H29 H 0.774376 1.125849 0.899546 0.048 Uiso 1 1 calc R . . . .
C30 C 0.7267(5) 1.0551(3) 0.7807(5) 0.0333(13) Uani 1 1 d . . . . .
H30 H 0.663526 1.039017 0.818299 0.040 Uiso 1 1 calc R . . . .
C31 C 0.7557(5) 1.0286(2) 0.6774(5) 0.0305(12) Uani 1 1 d . . . . .
C32 C 0.7077(5) 0.9723(2) 0.6086(5) 0.0293(11) Uani 1 1 d . . . . .
C33 C 0.7749(5) 0.9728(3) 0.4998(6) 0.0335(12) Uani 1 1 d . . . . .
C34 C 0.4969(5) 0.9981(2) 0.4673(5) 0.0308(12) Uani 1 1 d . . . . .
C35 C 0.2822(6) 1.0168(3) 0.3289(6) 0.0387(14) Uani 1 1 d . . . . .
H35A H 0.333347 1.042136 0.286488 0.046 Uiso 1 1 calc R . . . .
H35B H 0.219808 1.041943 0.357441 0.046 Uiso 1 1 calc R . . . .
C36 C 0.2092(6) 0.9725(3) 0.2345(6) 0.0376(13) Uani 1 1 d . . . . .
C37 C 0.2708(7) 0.9233(3) 0.2021(7) 0.0480(16) Uani 1 1 d . . . . .
H37 H 0.359712 0.917756 0.240349 0.058 Uiso 1 1 calc R . . . .
C38 C 0.2060(8) 0.8825(3) 0.1159(7) 0.058(2) Uani 1 1 d . . . . .
H38 H 0.249972 0.848902 0.097431 0.070 Uiso 1 1 calc R . . . .
C39 C 0.0768(8) 0.8905(4) 0.0563(7) 0.062(2) Uani 1 1 d . . . . .
H39 H 0.032449 0.863299 -0.005198 0.074 Uiso 1 1 calc R . . . .
C40 C 0.0132(7) 0.9393(4) 0.0884(7) 0.056(2) Uani 1 1 d . . . . .
H40 H -0.075844 0.944673 0.050192 0.068 Uiso 1 1 calc R . . . .
C41 C 0.0786(6) 0.9802(3) 0.1759(6) 0.0435(15) Uani 1 1 d . . . . .
H41 H 0.034428 1.013447 0.195728 0.052 Uiso 1 1 calc R . . . .
C42 C 0.7495(6) 0.9169(3) 0.6918(6) 0.0346(13) Uani 1 1 d . . . . .
H42A H 0.762861 0.883184 0.639600 0.041 Uiso 1 1 calc R . . . .
H42B H 0.829623 0.924168 0.758213 0.041 Uiso 1 1 calc R . . . .
C43 C 0.6357(6) 0.9060(3) 0.7504(6) 0.0416(15) Uani 1 1 d . . . . .
H43A H 0.639746 0.932089 0.823775 0.050 Uiso 1 1 calc R . . . .
H43B H 0.633382 0.864844 0.777677 0.050 Uiso 1 1 calc R . . . .
C44 C 0.5171(6) 0.9207(3) 0.6390(5) 0.0337(12) Uani 1 1 d . . . . .
H44 H 0.448531 0.938982 0.673759 0.040 Uiso 1 1 calc R . . . .
C45 C 0.4641(6) 0.8675(3) 0.5644(6) 0.0377(14) Uani 1 1 d . . . . .
H45 H 0.407729 0.844063 0.598380 0.045 Uiso 1 1 calc R . . . .
C46 C 0.4862(5) 0.8490(3) 0.4571(6) 0.0334(13) Uani 1 1 d . . . . .
H46 H 0.544996 0.869721 0.421047 0.040 Uiso 1 1 calc R . . . .
C47 C 0.4209(5) 0.7968(3) 0.3927(6) 0.0322(12) Uani 1 1 d . . . . .
C48 C 0.3905(7) 0.7335(3) 0.2172(7) 0.0507(17) Uani 1 1 d . . . . .
H48A H 0.299102 0.742581 0.183325 0.076 Uiso 1 1 calc GR . . . .
H48B H 0.399165 0.699751 0.274198 0.076 Uiso 1 1 calc GR . . . .
H48C H 0.429234 0.724226 0.147209 0.076 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.8422(2) 0.75841(12) 0.9245(2) 0.0753(7) Uani 1 1 d . . . . .
Cl2 Cl 1.09685(19) 0.72355(11) 0.9171(2) 0.0703(6) Uani 1 1 d . . . . .
Cl3 Cl 0.8963(3) 0.63667(11) 0.8925(2) 0.0847(8) Uani 1 1 d . . . . .
C49 C 0.9322(7) 0.7094(3) 0.8594(6) 0.0501(17) Uani 1 1 d . . . . .
H49 H 0.908929 0.714847 0.765418 0.060 Uiso 1 1 calc R . . . .
Cl4 Cl 0.5400(2) 0.52015(10) 0.9407(2) 0.0693(6) Uani 1 1 d . . . . .
Cl5 Cl 0.2659(2) 0.53419(11) 0.8771(2) 0.0697(6) Uani 1 1 d . . . . .
Cl6 Cl 0.3778(3) 0.41816(10) 0.8938(2) 0.0842(8) Uani 1 1 d . . . . .
C50 C 0.3934(7) 0.4909(3) 0.8514(6) 0.0460(16) Uani 1 1 d . . . . .
H50 H 0.392288 0.492582 0.759586 0.055 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
O1 0.048(2) 0.030(2) 0.036(2) -0.0025(17) 0.0138(19) 0.0059(18)
O2 0.032(2) 0.029(2) 0.033(2) 0.0041(16) 0.0080(17) -0.0018(16)
O3 0.054(3) 0.035(2) 0.044(3) -0.009(2) 0.019(2) -0.016(2)
O4 0.039(2) 0.039(2) 0.059(3) -0.006(2) 0.018(2) -0.0134(19)
O5 0.051(3) 0.032(2) 0.036(2) -0.0037(18) 0.012(2) 0.0003(18)
O6 0.034(2) 0.031(2) 0.040(2) 0.0020(18) 0.0082(18) -0.0011(17)
O7 0.046(2) 0.040(3) 0.040(2) -0.010(2) 0.016(2) -0.0105(19)
O8 0.045(2) 0.043(3) 0.047(3) -0.007(2) 0.019(2) -0.016(2)
N1 0.033(3) 0.035(3) 0.038(3) 0.005(2) 0.014(2) -0.004(2)
N2 0.022(2) 0.031(2) 0.026(2) 0.0036(18) 0.0002(18) -0.0022(18)
N3 0.023(2) 0.042(3) 0.039(3) 0.005(2) 0.004(2) -0.001(2)
N4 0.034(3) 0.034(3) 0.033(3) -0.005(2) 0.010(2) -0.002(2)
N5 0.030(2) 0.034(3) 0.031(2) 0.001(2) 0.007(2) -0.007(2)
N6 0.033(3) 0.034(3) 0.039(3) 0.002(2) 0.005(2) -0.005(2)
C1 0.047(4) 0.049(4) 0.047(4) 0.014(3) 0.024(3) -0.003(3)
C2 0.028(3) 0.034(3) 0.036(3) 0.001(2) 0.005(2) 0.000(2)
C3 0.036(3) 0.034(3) 0.059(4) 0.007(3) 0.007(3) -0.007(3)
C4 0.043(4) 0.030(3) 0.055(4) 0.001(3) 0.004(3) -0.004(3)
C5 0.042(3) 0.031(3) 0.039(3) -0.006(3) 0.002(3) 0.002(3)
C6 0.033(3) 0.035(3) 0.030(3) -0.003(2) 0.002(2) 0.003(2)
C7 0.023(2) 0.028(3) 0.032(3) 0.002(2) 0.005(2) 0.002(2)
C8 0.027(3) 0.031(3) 0.024(3) 0.001(2) 0.005(2) -0.002(2)
C9 0.032(3) 0.030(3) 0.031(3) 0.009(2) 0.007(2) 0.008(2)
C10 0.027(3) 0.025(3) 0.032(3) -0.002(2) 0.008(2) 0.000(2)
C11 0.032(3) 0.043(4) 0.053(4) 0.007(3) 0.003(3) 0.002(3)
C12 0.027(3) 0.045(4) 0.039(3) 0.009(3) 0.004(2) 0.001(3)
C13 0.037(3) 0.047(4) 0.044(4) 0.008(3) 0.005(3) -0.007(3)
C14 0.055(4) 0.064(5) 0.039(4) 0.000(3) 0.007(3) -0.021(4)
C15 0.051(4) 0.083(6) 0.036(4) 0.004(4) 0.003(3) -0.019(4)
C16 0.045(4) 0.091(7) 0.046(4) 0.024(4) -0.005(3) 0.001(4)
C17 0.036(3) 0.062(5) 0.046(4) 0.020(3) 0.006(3) 0.003(3)
C18 0.041(3) 0.024(3) 0.034(3) 0.004(2) 0.012(3) 0.004(2)
C19 0.041(3) 0.030(3) 0.032(3) 0.003(2) 0.008(3) -0.003(2)
C20 0.036(3) 0.030(3) 0.030(3) -0.001(2) 0.014(2) 0.001(2)
C21 0.031(3) 0.030(3) 0.037(3) 0.004(2) 0.009(2) -0.005(2)
C22 0.033(3) 0.030(3) 0.041(3) -0.001(2) 0.007(3) -0.004(2)
C23 0.029(3) 0.030(3) 0.041(3) 0.002(2) 0.005(2) -0.001(2)
C24 0.074(5) 0.042(4) 0.049(4) -0.019(3) 0.016(4) -0.024(4)
C25 0.043(3) 0.039(4) 0.045(4) 0.002(3) 0.016(3) 0.003(3)
C26 0.028(3) 0.033(3) 0.028(3) 0.001(2) 0.003(2) -0.001(2)
C27 0.037(3) 0.030(3) 0.038(3) -0.001(2) 0.004(3) -0.005(2)
C28 0.046(3) 0.032(3) 0.038(3) -0.005(3) 0.000(3) -0.006(3)
C29 0.047(4) 0.039(4) 0.032(3) -0.008(3) 0.006(3) -0.004(3)
C30 0.030(3) 0.037(3) 0.033(3) -0.004(2) 0.008(2) -0.006(2)
C31 0.028(3) 0.029(3) 0.034(3) -0.004(2) 0.005(2) -0.002(2)
C32 0.029(3) 0.029(3) 0.031(3) -0.002(2) 0.008(2) -0.004(2)
C33 0.036(3) 0.030(3) 0.034(3) -0.002(2) 0.008(2) 0.005(2)
C34 0.033(3) 0.026(3) 0.034(3) -0.001(2) 0.008(2) -0.002(2)
C35 0.037(3) 0.034(3) 0.042(3) 0.003(3) 0.004(3) -0.003(3)
C36 0.045(3) 0.033(3) 0.032(3) 0.003(2) 0.006(3) -0.004(3)
C37 0.056(4) 0.039(4) 0.046(4) -0.002(3) 0.007(3) 0.002(3)
C38 0.080(6) 0.038(4) 0.052(4) -0.001(3) 0.009(4) -0.001(4)
C39 0.081(6) 0.060(5) 0.042(4) -0.003(4) 0.010(4) -0.021(4)
C40 0.036(4) 0.084(6) 0.048(4) -0.006(4) 0.007(3) -0.018(4)
C41 0.035(3) 0.060(4) 0.036(3) 0.003(3) 0.010(3) -0.005(3)
C42 0.032(3) 0.028(3) 0.041(3) 0.001(2) 0.005(3) -0.001(2)
C43 0.047(4) 0.038(3) 0.037(3) 0.005(3) 0.005(3) -0.011(3)
C44 0.037(3) 0.034(3) 0.032(3) 0.004(2) 0.011(2) -0.005(2)
C45 0.035(3) 0.041(3) 0.037(3) 0.000(3) 0.009(3) -0.008(3)
C46 0.032(3) 0.031(3) 0.035(3) 0.000(2) 0.004(2) -0.008(2)
C47 0.032(3) 0.033(3) 0.033(3) 0.000(2) 0.010(2) -0.003(2)
C48 0.066(4) 0.041(4) 0.047(4) -0.015(3) 0.018(4) -0.014(3)
Cl1 0.0717(13) 0.1038(19) 0.0563(12) -0.0230(12) 0.0271(11) -0.0057(12)
Cl2 0.0480(10) 0.0904(16) 0.0678(13) 0.0145(11) 0.0057(9) -0.0094(10)
Cl3 0.1092(19) 0.0712(14) 0.0607(13) 0.0105(11) -0.0030(13) -0.0332(14)
C49 0.054(4) 0.065(5) 0.032(3) -0.003(3) 0.012(3) -0.011(4)
Cl4 0.0570(11) 0.0725(13) 0.0657(13) -0.0146(10) -0.0083(10) -0.0030(10)
Cl5 0.0613(12) 0.0899(16) 0.0601(12) -0.0083(11) 0.0195(10) 0.0020(11)
Cl6 0.137(2) 0.0516(12) 0.0550(12) 0.0060(10) 0.0080(13) -0.0162(13)
C50 0.055(4) 0.050(4) 0.030(3) -0.003(3) 0.005(3) -0.007(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.224(7) . ?
O2 C10 1.245(6) . ?
O3 C23 1.340(7) . ?
O3 C24 1.452(7) . ?
O4 C23 1.218(7) . ?
O5 C33 1.229(7) . ?
O6 C34 1.235(7) . ?
O7 C47 1.338(7) . ?
O7 C48 1.449(7) . ?
O8 C47 1.220(7) . ?
N1 C1 1.459(7) . ?
N1 C2 1.406(8) . ?
N1 C9 1.370(7) . ?
N2 C8 1.476(7) . ?
N2 C10 1.371(7) . ?
N2 C20 1.467(7) . ?
N3 H3 0.900(14) . ?
N3 C10 1.355(7) . ?
N3 C11 1.451(8) . ?
N4 C25 1.462(8) . ?
N4 C26 1.410(7) . ?
N4 C33 1.369(8) . ?
N5 C32 1.458(7) . ?
N5 C34 1.388(7) . ?
N5 C44 1.471(7) . ?
N6 H6A 0.898(14) . ?
N6 C34 1.355(7) . ?
N6 C35 1.463(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.375(8) . ?
C2 C7 1.407(8) . ?
C3 H3A 0.9500 . ?
C3 C4 1.395(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(8) . ?
C7 C8 1.510(8) . ?
C8 C9 1.550(7) . ?
C8 C18 1.541(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(9) . ?
C12 C13 1.384(9) . ?
C12 C17 1.405(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(12) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(11) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.533(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.535(8) . ?
C20 H20 1.0000 . ?
C20 C21 1.519(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.330(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.469(8) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.385(8) . ?
C26 C31 1.378(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.404(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.375(9) . ?
C29 H29 0.9500 . ?
C29 C30 1.413(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.383(8) . ?
C31 C32 1.513(8) . ?
C32 C33 1.537(8) . ?
C32 C42 1.558(8) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.516(8) . ?
C36 C37 1.393(9) . ?
C36 C41 1.398(9) . ?
C37 H37 0.9500 . ?
C37 C38 1.382(10) . ?
C38 H38 0.9500 . ?
C38 C39 1.389(12) . ?
C39 H39 0.9500 . ?
C39 C40 1.398(12) . ?
C40 H40 0.9500 . ?
C40 C41 1.393(10) . ?
C41 H41 0.9500 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.534(9) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.560(8) . ?
C44 H44 1.0000 . ?
C44 C45 1.495(8) . ?
C45 H45 0.9500 . ?
C45 C46 1.321(8) . ?
C46 H46 0.9500 . ?
C46 C47 1.470(8) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
Cl1 C49 1.744(8) . ?
Cl2 C49 1.752(7) . ?
Cl3 C49 1.764(8) . ?
C49 H49 1.0000 . ?
Cl4 C50 1.762(7) . ?
Cl5 C50 1.767(8) . ?
Cl6 C50 1.746(7) . ?
C50 H50 1.0000 . ?
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
C23 O3 C24 116.0(5) . . ?
C47 O7 C48 115.5(5) . . ?
C2 N1 C1 125.0(5) . . ?
C9 N1 C1 122.7(5) . . ?
C9 N1 C2 111.6(5) . . ?
C10 N2 C8 120.0(4) . . ?
C10 N2 C20 126.9(4) . . ?
C20 N2 C8 113.0(4) . . ?
C10 N3 H3 119(4) . . ?
C10 N3 C11 122.2(5) . . ?
C11 N3 H3 118(4) . . ?
C26 N4 C25 124.3(5) . . ?
C33 N4 C25 124.4(5) . . ?
C33 N4 C26 111.2(5) . . ?
C32 N5 C44 113.9(4) . . ?
C34 N5 C32 120.3(5) . . ?
C34 N5 C44 125.8(5) . . ?
C34 N6 H6A 121(4) . . ?
C34 N6 C35 121.3(5) . . ?
C35 N6 H6A 118(4) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C7 109.3(5) . . ?
C3 C2 N1 127.9(6) . . ?
C3 C2 C7 122.8(6) . . ?
C2 C3 H3A 121.7 . . ?
C2 C3 C4 116.7(6) . . ?
C4 C3 H3A 121.7 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.7(6) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(6) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.3(6) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C8 108.7(5) . . ?
C6 C7 C2 119.6(5) . . ?
C6 C7 C8 131.6(5) . . ?
N2 C8 C7 115.0(4) . . ?
N2 C8 C9 111.3(4) . . ?
N2 C8 C18 102.3(4) . . ?
C7 C8 C9 102.0(4) . . ?
C7 C8 C18 115.8(4) . . ?
C18 C8 C9 110.9(5) . . ?
O1 C9 N1 126.6(5) . . ?
O1 C9 C8 125.7(5) . . ?
N1 C9 C8 107.6(5) . . ?
O2 C10 N2 119.8(5) . . ?
O2 C10 N3 123.3(5) . . ?
N3 C10 N2 116.9(5) . . ?
N3 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
N3 C11 C12 113.2(5) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 123.7(5) . . ?
C13 C12 C17 118.2(6) . . ?
C17 C12 C11 118.1(6) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.7(7) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(8) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(7) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(7) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 H17 120.2 . . ?
C16 C17 C12 119.6(7) . . ?
C16 C17 H17 120.2 . . ?
C8 C18 H18A 111.1 . . ?
C8 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
C19 C18 C8 103.3(5) . . ?
C19 C18 H18A 111.1 . . ?
C19 C18 H18B 111.1 . . ?
C18 C19 H19A 111.1 . . ?
C18 C19 H19B 111.1 . . ?
C18 C19 C20 103.3(5) . . ?
H19A C19 H19B 109.1 . . ?
C20 C19 H19A 111.1 . . ?
C20 C19 H19B 111.1 . . ?
N2 C20 C19 103.0(4) . . ?
N2 C20 H20 109.5 . . ?
N2 C20 C21 113.6(5) . . ?
C19 C20 H20 109.5 . . ?
C21 C20 C19 111.4(5) . . ?
C21 C20 H20 109.5 . . ?
C20 C21 H21 116.9 . . ?
C22 C21 C20 126.2(5) . . ?
C22 C21 H21 116.9 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(6) . . ?
C23 C22 H22 119.6 . . ?
O3 C23 C22 111.9(5) . . ?
O4 C23 O3 122.2(6) . . ?
O4 C23 C22 125.8(6) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 H25A 109.5 . . ?
N4 C25 H25B 109.5 . . ?
N4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N4 127.2(6) . . ?
C31 C26 N4 109.7(5) . . ?
C31 C26 C27 123.0(6) . . ?
C26 C27 H27 121.6 . . ?
C26 C27 C28 116.9(6) . . ?
C28 C27 H27 121.6 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(6) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.9(6) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.9 . . ?
C31 C30 C29 118.3(6) . . ?
C31 C30 H30 120.9 . . ?
C26 C31 C30 119.9(5) . . ?
C26 C31 C32 108.8(5) . . ?
C30 C31 C32 131.2(5) . . ?
N5 C32 C31 116.7(5) . . ?
N5 C32 C33 113.7(5) . . ?
N5 C32 C42 102.1(4) . . ?
C31 C32 C33 102.1(4) . . ?
C31 C32 C42 113.0(5) . . ?
C33 C32 C42 109.5(5) . . ?
O5 C33 N4 125.8(6) . . ?
O5 C33 C32 126.7(5) . . ?
N4 C33 C32 107.4(5) . . ?
O6 C34 N5 120.5(5) . . ?
O6 C34 N6 124.0(5) . . ?
N6 C34 N5 115.5(5) . . ?
N6 C35 H35A 109.1 . . ?
N6 C35 H35B 109.1 . . ?
N6 C35 C36 112.7(5) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C37 C36 C35 120.9(6) . . ?
C37 C36 C41 118.1(6) . . ?
C41 C36 C35 121.0(6) . . ?
C36 C37 H37 119.1 . . ?
C38 C37 C36 121.8(7) . . ?
C38 C37 H37 119.1 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.2(8) . . ?
C39 C38 H38 119.9 . . ?
C38 C39 H39 120.6 . . ?
C38 C39 C40 118.7(7) . . ?
C40 C39 H39 120.6 . . ?
C39 C40 H40 119.6 . . ?
C41 C40 C39 120.8(7) . . ?
C41 C40 H40 119.6 . . ?
C36 C41 H41 119.8 . . ?
C40 C41 C36 120.3(7) . . ?
C40 C41 H41 119.8 . . ?
C32 C42 H42A 111.1 . . ?
C32 C42 H42B 111.1 . . ?
H42A C42 H42B 109.1 . . ?
C43 C42 C32 103.4(5) . . ?
C43 C42 H42A 111.1 . . ?
C43 C42 H42B 111.1 . . ?
C42 C43 H43A 111.2 . . ?
C42 C43 H43B 111.2 . . ?
C42 C43 C44 102.8(5) . . ?
H43A C43 H43B 109.1 . . ?
C44 C43 H43A 111.2 . . ?
C44 C43 H43B 111.2 . . ?
N5 C44 C43 102.8(4) . . ?
N5 C44 H44 109.3 . . ?
N5 C44 C45 114.2(5) . . ?
C43 C44 H44 109.3 . . ?
C45 C44 C43 111.9(5) . . ?
C45 C44 H44 109.3 . . ?
C44 C45 H45 116.1 . . ?
C46 C45 C44 127.9(6) . . ?
C46 C45 H45 116.1 . . ?
C45 C46 H46 119.6 . . ?
C45 C46 C47 120.8(6) . . ?
C47 C46 H46 119.6 . . ?
O7 C47 C46 113.4(5) . . ?
O8 C47 O7 121.8(5) . . ?
O8 C47 C46 124.8(6) . . ?
O7 C48 H48A 109.5 . . ?
O7 C48 H48B 109.5 . . ?
O7 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
Cl1 C49 Cl2 110.3(4) . . ?
Cl1 C49 Cl3 110.5(4) . . ?
Cl1 C49 H49 108.4 . . ?
Cl2 C49 Cl3 110.7(4) . . ?
Cl2 C49 H49 108.4 . . ?
Cl3 C49 H49 108.4 . . ?
Cl4 C50 Cl5 108.8(4) . . ?
Cl4 C50 H50 108.9 . . ?
Cl5 C50 H50 108.9 . . ?
Cl6 C50 Cl4 110.3(4) . . ?
Cl6 C50 Cl5 111.2(4) . . ?
Cl6 C50 H50 108.9 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O8 0.900(14) 2.09(3) 2.943(7) 158(6) . yes
N6 H6A O4 0.898(14) 2.15(3) 2.971(7) 151(6) . yes
C18 H18B O5 0.99 2.36 3.247(7) 149.5 1_455 yes
C19 H19B Cl1 0.99 2.89 3.815(6) 156.2 1_454 yes
C22 H22 O1 0.95 2.59 3.485(7) 158.1 . yes
C42 H42A O1 0.99 2.36 3.265(7) 151.5 1_655 yes
C44 H44 O4 1.00 2.53 3.292(7) 132.5 . yes
C49 H49 O1 1.00 2.37 3.190(8) 138.9 1_655 yes
C49 H49 O2 1.00 2.35 3.164(8) 137.7 1_655 yes
C50 H50 O5 1.00 2.48 3.168(8) 125.2 2_646 yes
C50 H50 O6 1.00 2.28 3.198(8) 152.9 2_646 yes
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
N1 C2 C3 C4 -179.7(6) . . . . ?
N1 C2 C7 C6 -178.9(5) . . . . ?
N1 C2 C7 C8 -1.3(6) . . . . ?
N2 C8 C9 O1 51.4(7) . . . . ?
N2 C8 C9 N1 -131.6(5) . . . . ?
N2 C8 C18 C19 31.8(5) . . . . ?
N2 C20 C21 C22 -18.0(8) . . . . ?
N3 C11 C12 C13 17.3(9) . . . . ?
N3 C11 C12 C17 -163.8(6) . . . . ?
N4 C26 C27 C28 -179.8(5) . . . . ?
N4 C26 C31 C30 179.4(5) . . . . ?
N4 C26 C31 C32 2.6(6) . . . . ?
N5 C32 C33 O5 -47.7(8) . . . . ?
N5 C32 C33 N4 135.6(5) . . . . ?
N5 C32 C42 C43 -33.1(6) . . . . ?
N5 C44 C45 C46 18.4(9) . . . . ?
N6 C35 C36 C37 -43.3(8) . . . . ?
N6 C35 C36 C41 137.7(6) . . . . ?
C1 N1 C2 C3 3.7(10) . . . . ?
C1 N1 C2 C7 -175.5(5) . . . . ?
C1 N1 C9 O1 -3.6(9) . . . . ?
C1 N1 C9 C8 179.5(5) . . . . ?
C2 N1 C9 O1 -174.6(5) . . . . ?
C2 N1 C9 C8 8.5(6) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
C2 C7 C8 N2 126.4(5) . . . . ?
C2 C7 C8 C9 5.9(5) . . . . ?
C2 C7 C8 C18 -114.5(5) . . . . ?
C3 C2 C7 C6 1.9(9) . . . . ?
C3 C2 C7 C8 179.5(5) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
C5 C6 C7 C2 -1.6(8) . . . . ?
C5 C6 C7 C8 -178.5(5) . . . . ?
C6 C7 C8 N2 -56.4(8) . . . . ?
C6 C7 C8 C9 -176.9(6) . . . . ?
C6 C7 C8 C18 62.7(8) . . . . ?
C7 C2 C3 C4 -0.6(9) . . . . ?
C7 C8 C9 O1 174.5(5) . . . . ?
C7 C8 C9 N1 -8.6(5) . . . . ?
C7 C8 C18 C19 -94.0(5) . . . . ?
C8 N2 C10 O2 -2.2(8) . . . . ?
C8 N2 C10 N3 178.3(5) . . . . ?
C8 N2 C20 C19 -11.1(6) . . . . ?
C8 N2 C20 C21 109.6(5) . . . . ?
C8 C18 C19 C20 -39.2(6) . . . . ?
C9 N1 C2 C3 174.5(6) . . . . ?
C9 N1 C2 C7 -4.7(6) . . . . ?
C9 C8 C18 C19 150.5(5) . . . . ?
C10 N2 C8 C7 -67.3(6) . . . . ?
C10 N2 C8 C9 47.9(6) . . . . ?
C10 N2 C8 C18 166.3(5) . . . . ?
C10 N2 C20 C19 169.6(5) . . . . ?
C10 N2 C20 C21 -69.7(7) . . . . ?
C10 N3 C11 C12 -123.0(6) . . . . ?
C11 N3 C10 O2 1.1(9) . . . . ?
C11 N3 C10 N2 -179.4(5) . . . . ?
C11 C12 C13 C14 179.5(6) . . . . ?
C11 C12 C17 C16 -179.0(7) . . . . ?
C12 C13 C14 C15 -0.9(11) . . . . ?
C13 C12 C17 C16 0.0(10) . . . . ?
C13 C14 C15 C16 0.5(11) . . . . ?
C14 C15 C16 C17 0.1(12) . . . . ?
C15 C16 C17 C12 -0.3(11) . . . . ?
C17 C12 C13 C14 0.6(10) . . . . ?
C18 C8 C9 O1 -61.7(7) . . . . ?
C18 C8 C9 N1 115.2(5) . . . . ?
C18 C19 C20 N2 30.7(5) . . . . ?
C18 C19 C20 C21 -91.4(5) . . . . ?
C19 C20 C21 C22 97.8(7) . . . . ?
C20 N2 C8 C7 113.3(5) . . . . ?
C20 N2 C8 C9 -131.4(5) . . . . ?
C20 N2 C8 C18 -13.0(6) . . . . ?
C20 N2 C10 O2 177.0(5) . . . . ?
C20 N2 C10 N3 -2.4(8) . . . . ?
C20 C21 C22 C23 -179.6(5) . . . . ?
C21 C22 C23 O3 172.8(5) . . . . ?
C21 C22 C23 O4 -7.1(10) . . . . ?
C24 O3 C23 O4 -0.4(9) . . . . ?
C24 O3 C23 C22 179.7(5) . . . . ?
C25 N4 C26 C27 0.0(9) . . . . ?
C25 N4 C26 C31 -179.4(5) . . . . ?
C25 N4 C33 O5 -1.8(9) . . . . ?
C25 N4 C33 C32 174.9(5) . . . . ?
C26 N4 C33 O5 175.2(6) . . . . ?
C26 N4 C33 C32 -8.1(6) . . . . ?
C26 C27 C28 C29 0.5(9) . . . . ?
C26 C31 C32 N5 -131.6(5) . . . . ?
C26 C31 C32 C33 -7.0(6) . . . . ?
C26 C31 C32 C42 110.5(5) . . . . ?
C27 C26 C31 C30 -0.1(9) . . . . ?
C27 C26 C31 C32 -176.8(5) . . . . ?
C27 C28 C29 C30 -0.1(10) . . . . ?
C28 C29 C30 C31 -0.5(9) . . . . ?
C29 C30 C31 C26 0.5(9) . . . . ?
C29 C30 C31 C32 176.4(6) . . . . ?
C30 C31 C32 N5 52.2(8) . . . . ?
C30 C31 C32 C33 176.8(6) . . . . ?
C30 C31 C32 C42 -65.8(8) . . . . ?
C31 C26 C27 C28 -0.5(9) . . . . ?
C31 C32 C33 O5 -174.3(6) . . . . ?
C31 C32 C33 N4 9.0(6) . . . . ?
C31 C32 C42 C43 93.1(5) . . . . ?
C32 N5 C34 O6 3.4(8) . . . . ?
C32 N5 C34 N6 -177.4(5) . . . . ?
C32 N5 C44 C43 8.8(6) . . . . ?
C32 N5 C44 C45 -112.6(6) . . . . ?
C32 C42 C43 C44 38.8(6) . . . . ?
C33 N4 C26 C27 -177.0(6) . . . . ?
C33 N4 C26 C31 3.6(7) . . . . ?
C33 C32 C42 C43 -153.9(5) . . . . ?
C34 N5 C32 C31 70.9(7) . . . . ?
C34 N5 C32 C33 -47.6(7) . . . . ?
C34 N5 C32 C42 -165.4(5) . . . . ?
C34 N5 C44 C43 -170.7(5) . . . . ?
C34 N5 C44 C45 67.9(7) . . . . ?
C34 N6 C35 C36 118.4(6) . . . . ?
C35 N6 C34 O6 5.6(9) . . . . ?
C35 N6 C34 N5 -173.5(5) . . . . ?
C35 C36 C37 C38 -179.8(6) . . . . ?
C35 C36 C41 C40 179.4(6) . . . . ?
C36 C37 C38 C39 1.7(11) . . . . ?
C37 C36 C41 C40 0.5(10) . . . . ?
C37 C38 C39 C40 -2.2(12) . . . . ?
C38 C39 C40 C41 1.8(12) . . . . ?
C39 C40 C41 C36 -1.0(11) . . . . ?
C41 C36 C37 C38 -0.8(10) . . . . ?
C42 C32 C33 O5 65.7(7) . . . . ?
C42 C32 C33 N4 -110.9(5) . . . . ?
C42 C43 C44 N5 -29.3(6) . . . . ?
C42 C43 C44 C45 93.6(6) . . . . ?
C43 C44 C45 C46 -97.8(7) . . . . ?
C44 N5 C32 C31 -108.7(6) . . . . ?
C44 N5 C32 C33 132.8(5) . . . . ?
C44 N5 C32 C42 15.1(6) . . . . ?
C44 N5 C34 O6 -177.1(5) . . . . ?
C44 N5 C34 N6 2.1(8) . . . . ?
C44 C45 C46 C47 -177.0(6) . . . . ?
C45 C46 C47 O7 -179.0(6) . . . . ?
C45 C46 C47 O8 1.7(10) . . . . ?
C48 O7 C47 O8 1.2(9) . . . . ?
C48 O7 C47 C46 -178.1(5) . . . . ?
_shelx_res_file
;
TITL R20181026B1 in P2(1)
r20181026b1.res
created by SHELXL-2018/3 at 16:11:24 on 13-Nov-2018
CELL 0.71073 10.7399 22.8569 10.9092 90 104.541 90
ZERR 4 0.0021 0.0046 0.0022 0 0.03 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Cl N O
UNIT 100 104 12 12 16
EQIV $1 -1+X,+Y,+Z
EQIV $2 -1+X,+Y,-1+Z
EQIV $3 1+X,+Y,+Z
EQIV $4 1-X,-0.5+Y,1-Z
DFIX 0.9 0.01 N3 H3 N6 H6a
L.S. 4
PLAN 20
SIZE 0.12 0.18 0.2
TEMP -160
HTAB C50 O6_$4
HTAB C50 O5_$4
HTAB C49 O2_$3
HTAB C49 O1_$3
HTAB C44 O4
HTAB C42 O1_$3
HTAB C22 O1
HTAB C19 Cl1_$2
HTAB C18 O5_$1
HTAB N6 O4
HTAB N3 O8
BOND $H
HTAB
CONF
fmap 2
acta
OMIT 1 2 0
REM
REM
REM
WGHT 0.075200
EXTI 0.005691
FVAR 0.24474
O1 5 -0.204219 0.782339 0.612925 11.00000 0.04771 0.02954 =
0.03551 -0.00245 0.01379 0.00587
O2 5 -0.026860 0.677307 0.590019 11.00000 0.03152 0.02942 =
0.03338 0.00407 0.00802 -0.00178
O3 5 0.081856 0.923280 0.731707 11.00000 0.05432 0.03523 =
0.04414 -0.00946 0.01924 -0.01593
O4 5 0.205421 0.939789 0.597632 11.00000 0.03892 0.03942 =
0.05852 -0.00610 0.01820 -0.01341
O5 5 0.758825 0.937747 0.411721 11.00000 0.05055 0.03216 =
0.03554 -0.00373 0.01244 0.00026
O6 5 0.550512 1.032362 0.409538 11.00000 0.03429 0.03126 =
0.03996 0.00204 0.00817 -0.00108
O7 5 0.455299 0.783514 0.286380 11.00000 0.04579 0.04050 =
0.03979 -0.01003 0.01606 -0.01054
O8 5 0.341806 0.767960 0.429314 11.00000 0.04464 0.04268 =
0.04733 -0.00738 0.01902 -0.01643
N1 4 -0.322737 0.703316 0.513039 11.00000 0.03342 0.03547 =
0.03755 0.00494 0.01392 -0.00446
N2 4 -0.037205 0.747701 0.441746 11.00000 0.02240 0.03088 =
0.02632 0.00364 0.00019 -0.00225
N3 4 0.161039 0.713698 0.558347 11.00000 0.02279 0.04169 =
0.03929 0.00489 0.00388 -0.00083
H3 2 0.197252 0.735555 0.507944 11.00000 -1.20000
N4 4 0.862069 1.017667 0.522349 11.00000 0.03441 0.03425 =
0.03278 -0.00462 0.01012 -0.00226
N5 4 0.568635 0.964831 0.566709 11.00000 0.03045 0.03370 =
0.03061 0.00056 0.00650 -0.00708
N6 4 0.368098 0.989365 0.439436 11.00000 0.03300 0.03406 =
0.03874 0.00180 0.00531 -0.00485
H6A 2 0.334082 0.963028 0.482753 11.00000 -1.20000
C1 1 -0.392812 0.691149 0.608712 11.00000 0.04713 0.04873 =
0.04734 0.01372 0.02355 -0.00346
AFIX 137
H1A 2 -0.379174 0.723190 0.670343 11.00000 -1.50000
H1B 2 -0.361519 0.654473 0.652167 11.00000 -1.50000
H1C 2 -0.484827 0.687608 0.567906 11.00000 -1.50000
AFIX 0
C2 1 -0.323194 0.667468 0.408183 11.00000 0.02834 0.03377 =
0.03578 0.00088 0.00510 0.00038
C3 1 -0.392554 0.617065 0.371792 11.00000 0.03569 0.03370 =
0.05858 0.00659 0.00655 -0.00736
AFIX 43
H3A 2 -0.449434 0.601965 0.418101 11.00000 -1.20000
AFIX 0
C4 1 -0.375234 0.589212 0.263493 11.00000 0.04350 0.02958 =
0.05454 0.00054 0.00372 -0.00397
AFIX 43
H4 2 -0.420569 0.553969 0.236023 11.00000 -1.20000
AFIX 0
C5 1 -0.293514 0.611668 0.194921 11.00000 0.04232 0.03070 =
0.03928 -0.00646 0.00228 0.00199
AFIX 43
H5 2 -0.285095 0.592002 0.120705 11.00000 -1.20000
AFIX 0
C6 1 -0.223433 0.662789 0.233465 11.00000 0.03287 0.03526 =
0.02952 -0.00264 0.00224 0.00309
AFIX 43
H6 2 -0.167592 0.678175 0.186336 11.00000 -1.20000
AFIX 0
C7 1 -0.237371 0.690482 0.342063 11.00000 0.02287 0.02776 =
0.03199 0.00239 0.00461 0.00203
C8 1 -0.179154 0.746009 0.406936 11.00000 0.02661 0.03146 =
0.02437 0.00057 0.00537 -0.00212
C9 1 -0.233024 0.746984 0.526126 11.00000 0.03164 0.02952 =
0.03093 0.00948 0.00673 0.00816
C10 1 0.031115 0.710877 0.533484 11.00000 0.02713 0.02520 =
0.03203 -0.00207 0.00840 -0.00004
C11 1 0.244070 0.676672 0.652366 11.00000 0.03178 0.04338 =
0.05329 0.00674 0.00257 0.00226
AFIX 23
H11A 2 0.293095 0.650428 0.609443 11.00000 -1.20000
H11B 2 0.190132 0.651899 0.692880 11.00000 -1.20000
AFIX 0
C12 1 0.338050 0.711007 0.754260 11.00000 0.02652 0.04454 =
0.03866 0.00884 0.00398 0.00126
C13 1 0.324263 0.769844 0.777726 11.00000 0.03703 0.04695 =
0.04406 0.00828 0.00535 -0.00742
AFIX 43
H13 2 0.252737 0.790572 0.727622 11.00000 -1.20000
AFIX 0
C14 1 0.411894 0.799271 0.872221 11.00000 0.05525 0.06425 =
0.03911 0.00015 0.00735 -0.02075
AFIX 43
H14 2 0.400880 0.839802 0.885678 11.00000 -1.20000
AFIX 0
C15 1 0.515532 0.769526 0.947008 11.00000 0.05079 0.08266 =
0.03642 0.00438 0.00349 -0.01896
AFIX 43
H15 2 0.575651 0.789429 1.012487 11.00000 -1.20000
AFIX 0
C16 1 0.531108 0.711015 0.926111 11.00000 0.04476 0.09098 =
0.04595 0.02409 -0.00504 0.00074
AFIX 43
H16 2 0.602354 0.690644 0.977666 11.00000 -1.20000
AFIX 0
C17 1 0.443843 0.681042 0.830279 11.00000 0.03595 0.06246 =
0.04610 0.01994 0.00641 0.00258
AFIX 43
H17 2 0.455906 0.640623 0.816535 11.00000 -1.20000
AFIX 0
C18 1 -0.214233 0.802697 0.329562 11.00000 0.04051 0.02384 =
0.03413 0.00398 0.01199 0.00393
AFIX 23
H18A 2 -0.297315 0.798592 0.265516 11.00000 -1.20000
H18B 2 -0.219494 0.836308 0.385280 11.00000 -1.20000
AFIX 0
C19 1 -0.102824 0.810248 0.266345 11.00000 0.04051 0.03040 =
0.03164 0.00278 0.00767 -0.00296
AFIX 23
H19A 2 -0.095312 0.851429 0.241007 11.00000 -1.20000
H19B 2 -0.114333 0.784865 0.190790 11.00000 -1.20000
AFIX 0
C20 1 0.015315 0.791612 0.370354 11.00000 0.03635 0.03006 =
0.02963 -0.00117 0.01429 0.00088
AFIX 13
H20 2 0.079784 0.772780 0.330867 11.00000 -1.20000
AFIX 0
C21 1 0.076672 0.843476 0.449929 11.00000 0.03084 0.02996 =
0.03682 0.00372 0.00894 -0.00522
AFIX 43
H21 2 0.133482 0.867001 0.416822 11.00000 -1.20000
AFIX 0
C22 1 0.058434 0.859100 0.561595 11.00000 0.03268 0.02952 =
0.04132 -0.00090 0.00651 -0.00385
AFIX 43
H22 2 0.002753 0.836626 0.598337 11.00000 -1.20000
AFIX 0
C23 1 0.123412 0.910712 0.628755 11.00000 0.02901 0.03032 =
0.04092 0.00196 0.00545 -0.00059
C24 1 0.141162 0.973531 0.804910 11.00000 0.07377 0.04169 =
0.04851 -0.01886 0.01635 -0.02374
AFIX 137
H24A 2 0.137333 1.007234 0.748554 11.00000 -1.50000
H24B 2 0.231172 0.964578 0.846150 11.00000 -1.50000
H24C 2 0.095020 0.982705 0.869445 11.00000 -1.50000
AFIX 0
C25 1 0.952931 1.029892 0.445817 11.00000 0.04279 0.03904 =
0.04502 0.00181 0.01611 0.00250
AFIX 137
H25A 2 0.932824 1.067952 0.404189 11.00000 -1.50000
H25B 2 0.946271 0.999317 0.381514 11.00000 -1.50000
H25C 2 1.040617 1.030603 0.500435 11.00000 -1.50000
AFIX 0
C26 1 0.848295 1.052400 0.624999 11.00000 0.02762 0.03348 =
0.02808 0.00106 0.00338 -0.00136
C27 1 0.915792 1.102764 0.670945 11.00000 0.03708 0.02988 =
0.03809 -0.00115 0.00372 -0.00529
AFIX 43
H27 2 0.979722 1.118244 0.633643 11.00000 -1.20000
AFIX 0
C28 1 0.885324 1.129855 0.775171 11.00000 0.04551 0.03185 =
0.03779 -0.00495 0.00025 -0.00579
AFIX 43
H28 2 0.928948 1.164673 0.809051 11.00000 -1.20000
AFIX 0
C29 1 0.793343 1.106791 0.828987 11.00000 0.04692 0.03887 =
0.03206 -0.00812 0.00625 -0.00405
AFIX 43
H29 2 0.774376 1.125849 0.899546 11.00000 -1.20000
AFIX 0
C30 1 0.726655 1.055117 0.780738 11.00000 0.02983 0.03719 =
0.03320 -0.00380 0.00828 -0.00619
AFIX 43
H30 2 0.663526 1.039017 0.818299 11.00000 -1.20000
AFIX 0
C31 1 0.755674 1.028589 0.677413 11.00000 0.02778 0.02877 =
0.03381 -0.00396 0.00538 -0.00248
C32 1 0.707702 0.972324 0.608639 11.00000 0.02851 0.02887 =
0.03075 -0.00168 0.00796 -0.00397
C33 1 0.774927 0.972785 0.499808 11.00000 0.03576 0.03045 =
0.03400 -0.00159 0.00832 0.00466
C34 1 0.496933 0.998081 0.467334 11.00000 0.03264 0.02602 =
0.03373 -0.00094 0.00809 -0.00215
C35 1 0.282151 1.016793 0.328930 11.00000 0.03711 0.03373 =
0.04219 0.00334 0.00406 -0.00274
AFIX 23
H35A 2 0.333347 1.042136 0.286488 11.00000 -1.20000
H35B 2 0.219808 1.041943 0.357441 11.00000 -1.20000
AFIX 0
C36 1 0.209151 0.972455 0.234493 11.00000 0.04532 0.03321 =
0.03222 0.00331 0.00611 -0.00351
C37 1 0.270774 0.923347 0.202146 11.00000 0.05600 0.03942 =
0.04569 -0.00166 0.00744 0.00204
AFIX 43
H37 2 0.359712 0.917756 0.240349 11.00000 -1.20000
AFIX 0
C38 1 0.205975 0.882523 0.115937 11.00000 0.08023 0.03817 =
0.05243 -0.00113 0.00926 -0.00077
AFIX 43
H38 2 0.249972 0.848902 0.097431 11.00000 -1.20000
AFIX 0
C39 1 0.076768 0.890494 0.056284 11.00000 0.08065 0.05951 =
0.04222 -0.00288 0.01010 -0.02147
AFIX 43
H39 2 0.032449 0.863299 -0.005198 11.00000 -1.20000
AFIX 0
C40 1 0.013155 0.939314 0.088446 11.00000 0.03609 0.08381 =
0.04762 -0.00631 0.00699 -0.01829
AFIX 43
H40 2 -0.075844 0.944673 0.050192 11.00000 -1.20000
AFIX 0
C41 1 0.078638 0.980175 0.175854 11.00000 0.03539 0.06025 =
0.03552 0.00339 0.01011 -0.00535
AFIX 43
H41 2 0.034428 1.013447 0.195728 11.00000 -1.20000
AFIX 0
C42 1 0.749468 0.916890 0.691835 11.00000 0.03226 0.02837 =
0.04070 0.00072 0.00480 -0.00125
AFIX 23
H42A 2 0.762861 0.883184 0.639600 11.00000 -1.20000
H42B 2 0.829623 0.924168 0.758213 11.00000 -1.20000
AFIX 0
C43 1 0.635705 0.906048 0.750363 11.00000 0.04737 0.03773 =
0.03681 0.00513 0.00536 -0.01073
AFIX 23
H43A 2 0.639746 0.932089 0.823775 11.00000 -1.20000
H43B 2 0.633382 0.864844 0.777677 11.00000 -1.20000
AFIX 0
C44 1 0.517107 0.920742 0.639019 11.00000 0.03653 0.03368 =
0.03198 0.00399 0.01074 -0.00479
AFIX 13
H44 2 0.448531 0.938982 0.673759 11.00000 -1.20000
AFIX 0
C45 1 0.464109 0.867469 0.564444 11.00000 0.03472 0.04133 =
0.03693 0.00047 0.00896 -0.00814
AFIX 43
H45 2 0.407729 0.844063 0.598380 11.00000 -1.20000
AFIX 0
C46 1 0.486180 0.849005 0.457086 11.00000 0.03227 0.03074 =
0.03512 0.00008 0.00444 -0.00795
AFIX 43
H46 2 0.544996 0.869721 0.421047 11.00000 -1.20000
AFIX 0
C47 1 0.420917 0.796831 0.392703 11.00000 0.03185 0.03286 =
0.03288 0.00019 0.01015 -0.00265
C48 1 0.390453 0.733469 0.217179 11.00000 0.06562 0.04137 =
0.04689 -0.01533 0.01759 -0.01354
AFIX 137
H48A 2 0.299102 0.742581 0.183325 11.00000 -1.50000
H48B 2 0.399165 0.699751 0.274198 11.00000 -1.50000
H48C 2 0.429234 0.724226 0.147209 11.00000 -1.50000
AFIX 0
CL1 3 0.842227 0.758410 0.924524 11.00000 0.07172 0.10381 =
0.05628 -0.02298 0.02711 -0.00568
CL2 3 1.096846 0.723552 0.917149 11.00000 0.04804 0.09043 =
0.06781 0.01449 0.00573 -0.00943
CL3 3 0.896350 0.636669 0.892456 11.00000 0.10917 0.07118 =
0.06074 0.01050 -0.00304 -0.03325
C49 1 0.932229 0.709389 0.859375 11.00000 0.05402 0.06502 =
0.03178 -0.00257 0.01163 -0.01120
AFIX 13
H49 2 0.908929 0.714847 0.765418 11.00000 -1.20000
AFIX 0
CL4 3 0.540014 0.520147 0.940686 11.00000 0.05703 0.07247 =
0.06568 -0.01459 -0.00826 -0.00302
CL5 3 0.265863 0.534193 0.877070 11.00000 0.06133 0.08995 =
0.06012 -0.00832 0.01953 0.00201
CL6 3 0.377781 0.418163 0.893844 11.00000 0.13746 0.05156 =
0.05503 0.00601 0.00800 -0.01625
C50 1 0.393354 0.490948 0.851445 11.00000 0.05523 0.05017 =
0.02974 -0.00273 0.00529 -0.00679
AFIX 13
H50 2 0.392288 0.492582 0.759586 11.00000 -1.20000
AFIX 0
HKLF 4
REM R20181026B1 in P2(1)
REM wR2 = 0.1800, GooF = S = 1.044, Restrained GooF = 1.044 for all data
REM R1 = 0.0713 for 8205 Fo > 4sig(Fo) and 0.0997 for all 11931 data
REM 642 parameters refined using 3 restraints
END
WGHT 0.0752 0.0000
REM Instructions for potential hydrogen bonds
HTAB N3 O8
HTAB N6 O4
HTAB C18 O5_$1
HTAB C19 Cl1_$2
HTAB C22 O1
HTAB C42 O1_$3
HTAB C44 O4
HTAB C49 O1_$3
HTAB C49 O2_$3
HTAB C50 O5_$4
HTAB C50 O6_$4
REM Highest difference peak 0.296, deepest hole -0.335, 1-sigma level 0.061
Q1 1 1.0499 0.6889 1.0303 11.00000 0.05 0.26
Q2 1 0.0428 1.0230 0.0559 11.00000 0.05 0.26
Q3 1 0.2926 0.4887 0.9061 11.00000 0.05 0.24
Q4 1 0.1429 0.9212 0.4199 11.00000 0.05 0.24
Q5 1 0.5750 0.9777 0.5931 11.00000 0.05 0.24
Q6 1 -0.0814 0.7498 0.4206 11.00000 0.05 0.24
Q7 1 0.1456 0.5308 0.9208 11.00000 0.05 0.24
Q8 1 0.5691 0.4553 0.8816 11.00000 0.05 0.23
Q9 1 0.8972 0.7016 0.8678 11.00000 0.05 0.22
Q10 1 0.2304 0.4763 0.9405 11.00000 0.05 0.22
Q11 1 0.9520 1.0287 0.3036 11.00000 0.05 0.21
Q12 1 0.3761 0.4165 1.0224 11.00000 0.05 0.21
Q13 1 0.1464 0.9699 0.4402 11.00000 0.05 0.21
Q14 1 -0.3471 0.6287 0.5960 11.00000 0.05 0.21
Q15 1 0.9524 1.1575 0.6816 11.00000 0.05 0.21
Q16 1 0.2599 0.6988 0.3599 11.00000 0.05 0.21
Q17 1 0.9187 0.7793 0.8216 11.00000 0.05 0.21
Q18 1 0.1663 0.9464 0.5683 11.00000 0.05 0.21
Q19 1 0.9143 0.7587 0.9824 11.00000 0.05 0.21
Q20 1 0.2067 0.8111 0.2012 11.00000 0.05 0.20
;
_shelx_res_checksum 61517
_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_r20180613a
_audit_block_doi 10.5517/ccdc.csd.cc232nlg
_database_code_depnum_ccdc_archive 'CCDC 1938975'
loop_
_audit_author_name
_audit_author_address
'Jiaxu Feng'
;Nankai university
China
;
_audit_update_record
;
2019-07-08 deposited with the CCDC. 2019-10-25 downloaded from the CCDC.
;
_audit_creation_date 2018-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C24 H25 N3 O4'
_chemical_formula_sum 'C24 H25 N3 O4'
_chemical_formula_weight 419.47
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.8382(9)
_cell_length_b 15.3232(10)
_cell_length_c 11.6575(9)
_cell_angle_alpha 90
_cell_angle_beta 98.841(7)
_cell_angle_gamma 90
_cell_volume 2089.5(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 7786
_cell_measurement_temperature 113.15
_cell_measurement_theta_max 32.4540
_cell_measurement_theta_min 2.1920
_shelx_estimated_absorpt_T_max 0.991
_shelx_estimated_absorpt_T_min 0.976
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.46075
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.333
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 888
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0911
_diffrn_reflns_av_unetI/netI 0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 21642
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.372
_diffrn_reflns_theta_min 1.741
_diffrn_ambient_temperature 113.15
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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 -115.00 65.00 1.00 8.00 -- -25.00 45.00 0.00 180
2 \w -115.00 65.00 1.00 8.00 -- -25.00 45.00 90.00 180
3 \w -115.00 65.00 1.00 8.00 -- -25.00 45.00 180.00 180
;
_diffrn_measurement_device 'abstract diffractometer'
_diffrn_measurement_device_type 'Rigaku Saturn 70'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0558716000
_diffrn_orient_matrix_UB_12 -0.0173294000
_diffrn_orient_matrix_UB_13 -0.0031408000
_diffrn_orient_matrix_UB_21 -0.0225321000
_diffrn_orient_matrix_UB_22 0.0429654000
_diffrn_orient_matrix_UB_23 -0.0008236000
_diffrn_orient_matrix_UB_31 -0.0061189000
_diffrn_orient_matrix_UB_32 0.0002634000
_diffrn_orient_matrix_UB_33 -0.0615204000
_diffrn_radiation_monochromator confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'rotating anode'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3174
_reflns_number_total 4254
_reflns_odcompleteness_completeness 92.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 32.91
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 0.390
_refine_diff_density_min -0.321
_refine_diff_density_rms 0.098
_refine_ls_extinction_coef 0.082(6)
_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 1.083
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 284
_refine_ls_number_reflns 4254
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0788
_refine_ls_R_factor_gt 0.0535
_refine_ls_restrained_S_all 1.083
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.4550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1313
_refine_ls_wR_factor_ref 0.1564
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
C13(H13A,H13B), C14(H14A,H14B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_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
O1 O 0.59102(14) 0.86617(10) 0.48762(13) 0.0384(4) Uani 1 1 d . . . . .
O2 O 0.51452(11) 0.67511(9) 0.44529(12) 0.0286(4) Uani 1 1 d . . . . .
O3 O 0.88373(14) 0.72343(11) 0.11963(15) 0.0460(5) Uani 1 1 d . . . . .
O4 O 0.88049(13) 0.58632(10) 0.05384(14) 0.0400(4) Uani 1 1 d . . . . .
N1 N 0.39649(16) 0.87680(12) 0.43396(16) 0.0360(5) Uani 1 1 d . . . . .
N2 N 0.55923(13) 0.74168(10) 0.28138(14) 0.0229(4) Uani 1 1 d . . . . .
N3 N 0.68403(14) 0.64771(11) 0.37481(14) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.50430(19) 0.85608(13) 0.41754(18) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.49968(16) 0.82456(12) 0.29114(17) 0.0248(5) Uani 1 1 d . . . . .
C3 C 0.37306(17) 0.82387(13) 0.24848(18) 0.0277(5) Uani 1 1 d . . . . .
C4 C 0.31230(19) 0.80112(14) 0.1427(2) 0.0351(5) Uani 1 1 d . . . . .
H4 H 0.350430 0.780864 0.081806 0.042 Uiso 1 1 calc R . . . .
C5 C 0.1937(2) 0.80837(16) 0.1266(3) 0.0482(7) Uani 1 1 d . . . . .
H5 H 0.150263 0.791438 0.054605 0.058 Uiso 1 1 calc R . . . .
C6 C 0.1389(2) 0.83962(17) 0.2132(3) 0.0559(8) Uani 1 1 d . . . . .
H6 H 0.057878 0.843508 0.200524 0.067 Uiso 1 1 calc R . . . .
C7 C 0.1992(2) 0.86584(15) 0.3196(3) 0.0499(7) Uani 1 1 d . . . . .
H7 H 0.161109 0.888994 0.378844 0.060 Uiso 1 1 calc R . . . .
C8 C 0.31699(19) 0.85683(13) 0.3356(2) 0.0344(5) Uani 1 1 d . . . . .
C9 C 0.3690(3) 0.91451(16) 0.5401(2) 0.0548(8) Uani 1 1 d . . . . .
H9A H 0.437475 0.915003 0.599198 0.082 Uiso 1 1 calc GR . . . .
H9B H 0.309237 0.879649 0.567870 0.082 Uiso 1 1 calc GR . . . .
H9C H 0.341577 0.974395 0.525142 0.082 Uiso 1 1 calc GR . . . .
C10 C 0.57956(16) 0.68647(12) 0.37503(17) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.74685(16) 0.68536(12) 0.28797(17) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.817475 0.714963 0.327667 0.029 Uiso 1 1 calc R . . . .
C12 C 0.66331(16) 0.75380(13) 0.22731(17) 0.0245(5) Uani 1 1 d . . . . .
H12 H 0.646038 0.740938 0.142318 0.029 Uiso 1 1 calc R . . . .
C13 C 0.68911(17) 0.84989(13) 0.24601(18) 0.0279(5) Uani 1 1 d . . . . .
H13A H 0.735693 0.872637 0.188983 0.034 Uiso 1 1 calc R . . . .
H13B H 0.728970 0.861528 0.325566 0.034 Uiso 1 1 calc R . . . .
C14 C 0.56906(17) 0.88865(13) 0.22677(18) 0.0264(5) Uani 1 1 d . . . . .
H14A H 0.537859 0.891339 0.143038 0.032 Uiso 1 1 calc R . . . .
H14B H 0.568817 0.948051 0.260145 0.032 Uiso 1 1 calc R . . . .
C15 C 0.72986(16) 0.58246(12) 0.45489(16) 0.0233(4) Uani 1 1 d . . . . .
C16 C 0.66123(17) 0.51698(12) 0.48739(17) 0.0255(4) Uani 1 1 d . . . . .
H16 H 0.582903 0.514369 0.453916 0.031 Uiso 1 1 calc R . . . .
C17 C 0.70553(18) 0.45536(13) 0.56804(18) 0.0303(5) Uani 1 1 d . . . . .
H17 H 0.656626 0.411711 0.591084 0.036 Uiso 1 1 calc R . . . .
C18 C 0.82032(18) 0.45591(13) 0.61625(18) 0.0296(5) Uani 1 1 d . . . . .
C19 C 0.88908(17) 0.52011(13) 0.58012(18) 0.0282(5) Uani 1 1 d . . . . .
H19 H 0.968298 0.520668 0.610411 0.034 Uiso 1 1 calc R . . . .
C20 C 0.84563(16) 0.58337(13) 0.50122(17) 0.0259(5) Uani 1 1 d . . . . .
H20 H 0.894382 0.627308 0.478604 0.031 Uiso 1 1 calc R . . . .
C21 C 0.8685(2) 0.38785(17) 0.7034(2) 0.0489(7) Uani 1 1 d . . . . .
H21A H 0.898650 0.416219 0.777070 0.073 Uiso 1 1 calc GR . . . .
H21B H 0.930255 0.356274 0.674154 0.073 Uiso 1 1 calc GR . . . .
H21C H 0.808063 0.346752 0.715543 0.073 Uiso 1 1 calc GR . . . .
C22 C 0.77919(17) 0.61488(13) 0.20758(18) 0.0281(5) Uani 1 1 d . . . . .
H22A H 0.821008 0.567860 0.254493 0.034 Uiso 1 1 calc R . . . .
H22B H 0.708752 0.589293 0.163647 0.034 Uiso 1 1 calc R . . . .
C23 C 0.85184(17) 0.64948(14) 0.12441(18) 0.0302(5) Uani 1 1 d . . . . .
C24 C 0.9553(2) 0.61329(19) -0.0261(2) 0.0486(7) Uani 1 1 d . . . . .
H24A H 0.966206 0.564718 -0.077933 0.073 Uiso 1 1 calc GR . . . .
H24B H 1.029387 0.630650 0.017459 0.073 Uiso 1 1 calc GR . . . .
H24C H 0.921213 0.662855 -0.072029 0.073 Uiso 1 1 calc GR . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0529(10) 0.0355(9) 0.0248(8) -0.0009(7) -0.0006(7) -0.0036(7)
O2 0.0270(7) 0.0314(8) 0.0296(8) 0.0043(6) 0.0111(6) 0.0010(6)
O3 0.0497(10) 0.0375(10) 0.0567(11) 0.0102(8) 0.0270(8) 0.0034(8)
O4 0.0411(9) 0.0454(10) 0.0380(9) -0.0011(7) 0.0205(7) 0.0076(7)
N1 0.0460(11) 0.0312(10) 0.0354(11) 0.0010(8) 0.0214(9) 0.0075(8)
N2 0.0222(8) 0.0259(8) 0.0214(9) 0.0016(7) 0.0054(6) 0.0022(6)
N3 0.0228(8) 0.0306(9) 0.0252(9) 0.0063(7) 0.0070(7) 0.0050(7)
C1 0.0402(12) 0.0231(10) 0.0265(11) 0.0031(9) 0.0088(10) 0.0021(8)
C2 0.0255(10) 0.0266(10) 0.0229(10) 0.0010(8) 0.0054(8) 0.0040(8)
C3 0.0259(10) 0.0230(10) 0.0343(12) 0.0077(9) 0.0051(9) 0.0034(8)
C4 0.0347(12) 0.0310(11) 0.0376(13) 0.0104(10) -0.0007(10) 0.0003(9)
C5 0.0333(13) 0.0419(14) 0.0640(18) 0.0221(13) -0.0092(12) -0.0037(10)
C6 0.0248(12) 0.0461(15) 0.096(2) 0.0328(16) 0.0052(14) 0.0047(11)
C7 0.0385(14) 0.0356(13) 0.082(2) 0.0184(13) 0.0302(14) 0.0102(10)
C8 0.0337(12) 0.0269(11) 0.0455(14) 0.0078(10) 0.0152(10) 0.0052(9)
C9 0.088(2) 0.0386(14) 0.0483(16) -0.0013(12) 0.0442(15) 0.0105(13)
C10 0.0233(9) 0.0246(10) 0.0232(10) -0.0003(8) 0.0042(8) -0.0015(8)
C11 0.0235(9) 0.0268(10) 0.0241(10) 0.0037(8) 0.0066(8) -0.0002(8)
C12 0.0243(10) 0.0290(10) 0.0213(10) 0.0025(8) 0.0066(8) 0.0033(8)
C13 0.0252(10) 0.0294(11) 0.0300(11) 0.0043(9) 0.0067(8) 0.0004(8)
C14 0.0296(10) 0.0264(10) 0.0235(10) 0.0022(8) 0.0055(8) 0.0023(8)
C15 0.0249(10) 0.0259(10) 0.0194(10) -0.0005(8) 0.0044(8) 0.0034(8)
C16 0.0248(10) 0.0236(10) 0.0276(11) -0.0022(8) 0.0027(8) 0.0001(8)
C17 0.0346(11) 0.0240(10) 0.0331(12) -0.0001(9) 0.0074(9) -0.0042(8)
C18 0.0355(11) 0.0255(10) 0.0277(11) 0.0022(9) 0.0046(9) 0.0060(8)
C19 0.0237(10) 0.0303(11) 0.0294(11) 0.0002(9) 0.0003(8) 0.0039(8)
C20 0.0243(10) 0.0258(10) 0.0283(11) 0.0015(8) 0.0064(8) -0.0004(8)
C21 0.0536(16) 0.0423(14) 0.0484(16) 0.0164(12) -0.0003(12) 0.0066(12)
C22 0.0279(10) 0.0294(10) 0.0277(11) 0.0025(9) 0.0071(9) 0.0054(8)
C23 0.0263(10) 0.0344(12) 0.0307(12) 0.0065(9) 0.0070(9) 0.0102(9)
C24 0.0419(14) 0.0701(17) 0.0381(14) 0.0094(13) 0.0192(11) 0.0145(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(3) . ?
O2 C10 1.220(2) . ?
O3 C23 1.198(3) . ?
O4 C23 1.347(3) . ?
O4 C24 1.441(3) . ?
N1 C1 1.357(3) . ?
N1 C8 1.401(3) . ?
N1 C9 1.447(3) . ?
N2 C2 1.465(2) . ?
N2 C10 1.373(2) . ?
N2 C12 1.479(2) . ?
N3 C10 1.372(2) . ?
N3 C11 1.464(2) . ?
N3 C15 1.418(2) . ?
C1 C2 1.544(3) . ?
C2 C3 1.505(3) . ?
C2 C14 1.546(3) . ?
C3 C4 1.374(3) . ?
C3 C8 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.537(3) . ?
C11 C22 1.517(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.513(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.525(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.380(3) . ?
C15 C20 1.394(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 C19 1.383(3) . ?
C18 C21 1.505(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.489(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O4 C24 115.23(19) . . ?
C1 N1 C8 111.19(18) . . ?
C1 N1 C9 123.7(2) . . ?
C8 N1 C9 125.2(2) . . ?
C2 N2 C12 111.49(14) . . ?
C10 N2 C2 120.00(15) . . ?
C10 N2 C12 111.13(15) . . ?
C10 N3 C11 112.62(15) . . ?
C10 N3 C15 123.90(16) . . ?
C15 N3 C11 123.35(15) . . ?
O1 C1 N1 126.1(2) . . ?
O1 C1 C2 125.57(19) . . ?
N1 C1 C2 108.17(18) . . ?
N2 C2 C1 113.48(16) . . ?
N2 C2 C3 115.77(16) . . ?
N2 C2 C14 102.42(14) . . ?
C1 C2 C14 108.72(16) . . ?
C3 C2 C1 101.83(16) . . ?
C3 C2 C14 114.86(16) . . ?
C4 C3 C2 130.99(19) . . ?
C4 C3 C8 120.3(2) . . ?
C8 C3 C2 108.61(18) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.3(2) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 N1 109.94(18) . . ?
C7 C8 N1 128.6(2) . . ?
C7 C8 C3 121.4(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N2 124.77(17) . . ?
O2 C10 N3 126.98(18) . . ?
N3 C10 N2 108.24(16) . . ?
N3 C11 H11 109.7 . . ?
N3 C11 C12 103.16(15) . . ?
N3 C11 C22 110.49(16) . . ?
C12 C11 H11 109.7 . . ?
C22 C11 H11 109.7 . . ?
C22 C11 C12 114.02(17) . . ?
N2 C12 C11 103.73(15) . . ?
N2 C12 H12 109.9 . . ?
N2 C12 C13 102.93(15) . . ?
C11 C12 H12 109.9 . . ?
C13 C12 C11 119.76(17) . . ?
C13 C12 H12 109.9 . . ?
C12 C13 H13A 111.5 . . ?
C12 C13 H13B 111.5 . . ?
C12 C13 C14 101.24(16) . . ?
H13A C13 H13B 109.3 . . ?
C14 C13 H13A 111.5 . . ?
C14 C13 H13B 111.5 . . ?
C2 C14 H14A 111.1 . . ?
C2 C14 H14B 111.1 . . ?
C13 C14 C2 103.52(15) . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
C16 C15 N3 120.77(17) . . ?
C16 C15 C20 119.09(18) . . ?
C20 C15 N3 120.14(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.47(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.21(19) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C21 121.0(2) . . ?
C19 C18 C17 117.79(19) . . ?
C19 C18 C21 121.2(2) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.74(19) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.65(18) . . ?
C19 C20 H20 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 H22A 109.2 . . ?
C11 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C11 112.01(17) . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
O3 C23 O4 122.71(19) . . ?
O3 C23 C22 125.8(2) . . ?
O4 C23 C22 111.52(18) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C1 C2 N2 54.3(3) . . . . ?
O1 C1 C2 C3 179.42(19) . . . . ?
O1 C1 C2 C14 -58.9(3) . . . . ?
N1 C1 C2 N2 -130.29(17) . . . . ?
N1 C1 C2 C3 -5.2(2) . . . . ?
N1 C1 C2 C14 116.46(17) . . . . ?
N2 C2 C3 C4 -55.7(3) . . . . ?
N2 C2 C3 C8 127.70(18) . . . . ?
N2 C2 C14 C13 -29.67(19) . . . . ?
N2 C12 C13 C14 -38.27(18) . . . . ?
N3 C11 C12 N2 -4.28(19) . . . . ?
N3 C11 C12 C13 109.62(19) . . . . ?
N3 C11 C22 C23 -175.10(16) . . . . ?
N3 C15 C16 C17 -177.94(18) . . . . ?
N3 C15 C20 C19 179.27(18) . . . . ?
C1 N1 C8 C3 -1.8(2) . . . . ?
C1 N1 C8 C7 177.9(2) . . . . ?
C1 C2 C3 C4 -179.3(2) . . . . ?
C1 C2 C3 C8 4.1(2) . . . . ?
C1 C2 C14 C13 90.68(18) . . . . ?
C2 N2 C10 O2 36.2(3) . . . . ?
C2 N2 C10 N3 -143.72(17) . . . . ?
C2 N2 C12 C11 146.27(15) . . . . ?
C2 N2 C12 C13 20.8(2) . . . . ?
C2 C3 C4 C5 -178.9(2) . . . . ?
C2 C3 C8 N1 -1.8(2) . . . . ?
C2 C3 C8 C7 178.48(19) . . . . ?
C3 C2 C14 C13 -156.02(17) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C3 C8 N1 -178.83(18) . . . . ?
C4 C3 C8 C7 1.5(3) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C6 C7 C8 N1 -178.9(2) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
C8 N1 C1 O1 179.85(19) . . . . ?
C8 N1 C1 C2 4.5(2) . . . . ?
C8 C3 C4 C5 -2.6(3) . . . . ?
C9 N1 C1 O1 -0.2(3) . . . . ?
C9 N1 C1 C2 -175.60(19) . . . . ?
C9 N1 C8 C3 178.3(2) . . . . ?
C9 N1 C8 C7 -2.0(3) . . . . ?
C10 N2 C2 C1 21.0(2) . . . . ?
C10 N2 C2 C3 -96.3(2) . . . . ?
C10 N2 C2 C14 137.99(17) . . . . ?
C10 N2 C12 C11 9.5(2) . . . . ?
C10 N2 C12 C13 -115.94(17) . . . . ?
C10 N3 C11 C12 -2.1(2) . . . . ?
C10 N3 C11 C22 -124.33(18) . . . . ?
C10 N3 C15 C16 40.8(3) . . . . ?
C10 N3 C15 C20 -139.7(2) . . . . ?
C11 N3 C10 O2 -171.68(19) . . . . ?
C11 N3 C10 N2 8.2(2) . . . . ?
C11 N3 C15 C16 -143.68(19) . . . . ?
C11 N3 C15 C20 35.8(3) . . . . ?
C11 C12 C13 C14 -152.59(16) . . . . ?
C11 C22 C23 O3 0.8(3) . . . . ?
C11 C22 C23 O4 179.71(17) . . . . ?
C12 N2 C2 C1 -111.44(18) . . . . ?
C12 N2 C2 C3 131.32(17) . . . . ?
C12 N2 C2 C14 5.6(2) . . . . ?
C12 N2 C10 O2 168.73(18) . . . . ?
C12 N2 C10 N3 -11.1(2) . . . . ?
C12 C11 C22 C23 69.3(2) . . . . ?
C12 C13 C14 C2 42.39(19) . . . . ?
C14 C2 C3 C4 63.4(3) . . . . ?
C14 C2 C3 C8 -113.16(19) . . . . ?
C15 N3 C10 O2 4.3(3) . . . . ?
C15 N3 C10 N2 -175.85(17) . . . . ?
C15 N3 C11 C12 -178.06(17) . . . . ?
C15 N3 C11 C22 59.7(2) . . . . ?
C15 C16 C17 C18 -1.8(3) . . . . ?
C16 C15 C20 C19 -1.2(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C16 C17 C18 C21 -179.3(2) . . . . ?
C17 C18 C19 C20 1.7(3) . . . . ?
C18 C19 C20 C15 -0.9(3) . . . . ?
C20 C15 C16 C17 2.6(3) . . . . ?
C21 C18 C19 C20 -179.3(2) . . . . ?
C22 C11 C12 N2 115.57(17) . . . . ?
C22 C11 C12 C13 -130.53(19) . . . . ?
C24 O4 C23 O3 1.7(3) . . . . ?
C24 O4 C23 C22 -177.25(18) . . . . ?
_iucr_refine_instructions_details
;
TITL r20180613a_a.res in P2(1)/c
r20180613a.res
created by SHELXL-2016/6 at 08:14:14 on 13-Jun-2018
REM Old TITL r20180613a in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.179, Rweak 0.093, Alpha 0.034, Orientation as input
REM Formula found by SHELXT: C25 N3 O3
CELL 0.71073 11.8382 15.3232 11.6575 90 98.841 90
ZERR 4 0.0009 0.001 0.0009 0 0.007 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 96 100 12 16
L.S. 10
PLAN 20
SIZE 0.26 0.12 0.1
TEMP -160
BOND $H
conf
htab
fmap 2
acta
SHEL 999 0.8
REM
REM
REM
WGHT 0.076000 0.455000
EXTI 0.081816
FVAR 1.23985
O1 4 0.591016 0.866168 0.487617 11.00000 0.05286 0.03547 =
0.02480 -0.00092 -0.00062 -0.00362
O2 4 0.514524 0.675111 0.445289 11.00000 0.02698 0.03140 =
0.02958 0.00425 0.01109 0.00103
O3 4 0.883734 0.723431 0.119634 11.00000 0.04974 0.03745 =
0.05673 0.01018 0.02700 0.00342
O4 4 0.880489 0.586322 0.053837 11.00000 0.04106 0.04543 =
0.03800 -0.00112 0.02054 0.00758
N1 3 0.396489 0.876799 0.433963 11.00000 0.04605 0.03121 =
0.03540 0.00104 0.02140 0.00752
N2 3 0.559226 0.741675 0.281380 11.00000 0.02215 0.02587 =
0.02137 0.00161 0.00541 0.00222
N3 3 0.684030 0.647707 0.374805 11.00000 0.02276 0.03056 =
0.02522 0.00629 0.00705 0.00499
C1 1 0.504299 0.856081 0.417540 11.00000 0.04021 0.02312 =
0.02650 0.00306 0.00878 0.00205
C2 1 0.499684 0.824563 0.291138 11.00000 0.02547 0.02657 =
0.02287 0.00098 0.00537 0.00403
C3 1 0.373062 0.823872 0.248481 11.00000 0.02594 0.02298 =
0.03434 0.00765 0.00513 0.00337
C4 1 0.312302 0.801123 0.142699 11.00000 0.03469 0.03105 =
0.03762 0.01042 -0.00071 0.00034
AFIX 43
H4 2 0.350430 0.780864 0.081806 11.00000 -1.20000
AFIX 0
C5 1 0.193654 0.808373 0.126568 11.00000 0.03330 0.04186 =
0.06405 0.02215 -0.00924 -0.00374
AFIX 43
H5 2 0.150263 0.791438 0.054605 11.00000 -1.20000
AFIX 0
C6 1 0.138932 0.839620 0.213238 11.00000 0.02476 0.04605 =
0.09551 0.03275 0.00516 0.00474
AFIX 43
H6 2 0.057878 0.843508 0.200524 11.00000 -1.20000
AFIX 0
C7 1 0.199212 0.865838 0.319577 11.00000 0.03851 0.03560 =
0.08221 0.01845 0.03017 0.01019
AFIX 43
H7 2 0.161109 0.888994 0.378844 11.00000 -1.20000
AFIX 0
C8 1 0.316988 0.856828 0.335573 11.00000 0.03369 0.02695 =
0.04547 0.00780 0.01519 0.00522
C9 1 0.368973 0.914506 0.540113 11.00000 0.08798 0.03861 =
0.04829 -0.00130 0.04415 0.01046
AFIX 137
H9A 2 0.437475 0.915003 0.599198 11.00000 -1.50000
H9B 2 0.309237 0.879649 0.567870 11.00000 -1.50000
H9C 2 0.341577 0.974395 0.525142 11.00000 -1.50000
AFIX 0
C10 1 0.579556 0.686467 0.375030 11.00000 0.02330 0.02459 =
0.02316 -0.00030 0.00417 -0.00154
C11 1 0.746852 0.685356 0.287974 11.00000 0.02352 0.02675 =
0.02405 0.00372 0.00656 -0.00017
AFIX 13
H11 2 0.817475 0.714963 0.327667 11.00000 -1.20000
AFIX 0
C12 1 0.663311 0.753795 0.227309 11.00000 0.02430 0.02896 =
0.02133 0.00246 0.00664 0.00329
AFIX 13
H12 2 0.646038 0.740938 0.142318 11.00000 -1.20000
AFIX 0
C13 1 0.689113 0.849893 0.246006 11.00000 0.02524 0.02938 =
0.02995 0.00430 0.00667 0.00041
AFIX 23
H13A 2 0.735693 0.872637 0.188983 11.00000 -1.20000
H13B 2 0.728970 0.861528 0.325566 11.00000 -1.20000
AFIX 0
C14 1 0.569062 0.888655 0.226770 11.00000 0.02961 0.02645 =
0.02352 0.00219 0.00549 0.00230
AFIX 23
H14A 2 0.537859 0.891339 0.143038 11.00000 -1.20000
H14B 2 0.568817 0.948051 0.260145 11.00000 -1.20000
AFIX 0
C15 1 0.729862 0.582464 0.454890 11.00000 0.02487 0.02594 =
0.01939 -0.00048 0.00442 0.00341
C16 1 0.661233 0.516980 0.487388 11.00000 0.02478 0.02358 =
0.02758 -0.00219 0.00266 0.00013
AFIX 43
H16 2 0.582903 0.514369 0.453916 11.00000 -1.20000
AFIX 0
C17 1 0.705528 0.455363 0.568042 11.00000 0.03461 0.02396 =
0.03313 -0.00010 0.00742 -0.00421
AFIX 43
H17 2 0.656626 0.411711 0.591084 11.00000 -1.20000
AFIX 0
C18 1 0.820319 0.455907 0.616247 11.00000 0.03547 0.02546 =
0.02770 0.00224 0.00459 0.00597
C19 1 0.889077 0.520106 0.580118 11.00000 0.02366 0.03031 =
0.02941 0.00024 0.00027 0.00391
AFIX 43
H19 2 0.968298 0.520668 0.610411 11.00000 -1.20000
AFIX 0
C20 1 0.845634 0.583373 0.501217 11.00000 0.02425 0.02578 =
0.02831 0.00148 0.00644 -0.00039
AFIX 43
H20 2 0.894382 0.627308 0.478604 11.00000 -1.20000
AFIX 0
C21 1 0.868528 0.387850 0.703354 11.00000 0.05361 0.04226 =
0.04839 0.01643 -0.00029 0.00656
AFIX 137
H21A 2 0.898650 0.416219 0.777070 11.00000 -1.50000
H21B 2 0.930255 0.356274 0.674154 11.00000 -1.50000
H21C 2 0.808063 0.346752 0.715543 11.00000 -1.50000
AFIX 0
C22 1 0.779192 0.614882 0.207579 11.00000 0.02792 0.02941 =
0.02771 0.00249 0.00708 0.00538
AFIX 23
H22A 2 0.821008 0.567860 0.254493 11.00000 -1.20000
H22B 2 0.708752 0.589293 0.163647 11.00000 -1.20000
AFIX 0
C23 1 0.851840 0.649479 0.124406 11.00000 0.02629 0.03437 =
0.03068 0.00654 0.00698 0.01018
C24 1 0.955307 0.613293 -0.026056 11.00000 0.04188 0.07007 =
0.03809 0.00938 0.01923 0.01453
AFIX 137
H24A 2 0.966206 0.564718 -0.077933 11.00000 -1.50000
H24B 2 1.029387 0.630650 0.017459 11.00000 -1.50000
H24C 2 0.921213 0.662855 -0.072029 11.00000 -1.50000
AFIX 0
HKLF 4
REM r20180613a_a.res in P2(1)/c
REM R1 = 0.0535 for 3174 Fo > 4sig(Fo) and 0.0788 for all 4254 data
REM 284 parameters refined using 0 restraints
END
WGHT 0.0741 0.4234
REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, -y+2, -z+1
HTAB C9 O1_$1
EQIV $2 x, -y+3/2, z-1/2
HTAB C12 O1_$2
HTAB C14 O2_$2
HTAB C22 O1_$2
REM Highest difference peak 0.390, deepest hole -0.321, 1-sigma level 0.098
Q1 1 0.9569 0.3922 0.7394 11.00000 0.05 0.39
Q2 1 0.8438 0.4987 0.6160 11.00000 0.05 0.33
Q3 1 0.8620 0.3316 0.6898 11.00000 0.05 0.28
Q4 1 0.9767 0.6716 0.0011 11.00000 0.05 0.27
Q5 1 0.1819 0.8431 0.3083 11.00000 0.05 0.27
Q6 1 1.0223 0.5684 -0.0217 11.00000 0.05 0.27
Q7 1 0.8423 0.4020 0.7754 11.00000 0.05 0.26
Q8 1 0.7991 0.3783 0.7599 11.00000 0.05 0.26
Q9 1 0.8706 0.5334 0.5097 11.00000 0.05 0.26
Q10 1 0.9952 0.7023 -0.0224 11.00000 0.05 0.26
Q11 1 0.8376 0.4344 0.6345 11.00000 0.05 0.25
Q12 1 0.1774 0.7338 0.0557 11.00000 0.05 0.25
Q13 1 0.1763 0.7947 0.1936 11.00000 0.05 0.25
Q14 1 1.1556 0.6568 0.0496 11.00000 0.05 0.25
Q15 1 0.9608 0.7227 0.0820 11.00000 0.05 0.25
Q16 1 0.9189 0.5673 -0.1235 11.00000 0.05 0.25
Q17 1 0.1275 0.7619 -0.0685 11.00000 0.05 0.25
Q18 1 0.0447 0.8310 0.2550 11.00000 0.05 0.25
Q19 1 0.1629 0.7167 -0.0437 11.00000 0.05 0.23
Q20 1 1.0624 0.6756 0.0389 11.00000 0.05 0.23
REM The information below was added by Olex2.
REM
REM R1 = 0.0535 for 3174 Fo > 4sig(Fo) and 0.0788 for all 31689 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.39, deepest hole -0.32
REM Mean Shift 0, Max Shift 0.003.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0788
REM R1_gt = 0.0535
REM wR_ref = 0.1564
REM GOOF = 1.083
REM Shift_max = 0.003
REM Shift_mean = 0
REM Reflections_all = 31689
REM Reflections_gt = 3174
REM Parameters = n/a
REM Hole = -0.32
REM Peak = 0.39
REM Flack = n/a
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.614