# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_9841-11478_htk145
_database_code_depnum_ccdc_archive 'CCDC 1994003'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record
;
2020-03-31 deposited with the CCDC. 2020-06-15 downloaded from the CCDC.
;
_audit_creation_date 2020-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C30 H24 Cl3 N3 O6'
_chemical_formula_sum 'C30 H24 Cl3 N3 O6'
_chemical_formula_weight 628.87
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.9534(8)
_cell_length_b 12.5947(13)
_cell_length_c 13.2276(10)
_cell_angle_alpha 100.624(8)
_cell_angle_beta 113.849(7)
_cell_angle_gamma 110.012(8)
_cell_volume 1453.4(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4284
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 75.5020
_cell_measurement_theta_min 4.4040
_shelx_estimated_absorpt_T_max 0.590
_shelx_estimated_absorpt_T_min 0.403
_exptl_absorpt_coefficient_mu 3.272
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.26810
_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_lustre .
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.437
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 648
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.18
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0482
_diffrn_reflns_av_unetI/netI 0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 10997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 76.415
_diffrn_reflns_theta_min 3.942
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_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 -49.00 36.00 1.00 1.00 -- -40.25 38.00 60.00 85
2 \w 20.00 114.00 1.00 1.00 -- 40.25 38.00 150.00 94
3 \w 101.00 178.00 1.00 2.00 -- 113.00 112.00 90.00 77
4 \w 124.00 163.00 1.00 2.00 -- 113.00 112.00 60.00 39
5 \w 102.00 171.00 1.00 2.00 -- 113.00 112.00 150.00 69
6 \w 101.00 144.00 1.00 2.00 -- 113.00 45.00 30.00 43
7 \w 88.00 162.00 1.00 2.00 -- 113.00 45.00 -90.00 74
8 \w 89.00 160.00 1.00 2.00 -- 113.00 77.00-150.00 71
9 \w 82.00 169.00 1.00 2.00 -- 113.00 77.00 -30.00 87
10 \w 87.00 112.00 1.00 2.00 -- 113.00 -77.00-180.00 25
11 \w 78.00 115.00 1.00 2.00 -- 113.00-112.00-180.00 37
12 \w 53.00 114.00 1.00 2.00 -- 113.00-112.00 -60.00 61
13 \w 59.00 114.00 1.00 2.00 -- 113.00-112.00 30.00 55
14 \w 115.00 140.00 1.00 2.00 -- 113.00 -77.00 120.00 25
15 \w 57.00 113.00 1.00 2.00 -- 113.00-112.00 120.00 56
16 \w 46.00 137.00 1.00 2.00 -- 113.00 -30.00 30.00 91
17 \w 67.00 99.00 1.00 1.00 -- 40.25-129.00 -99.00 32
18 \w 35.00 86.00 1.00 2.00 -- 113.00 -77.00-180.00 51
19 \w -5.00 70.00 1.00 1.00 -- 40.25 -77.00-180.00 75
20 \w 42.00 91.00 1.00 2.00 -- 113.00-112.00 90.00 49
21 \w 42.00 97.00 1.00 2.00 -- 113.00 -77.00 120.00 55
22 \w -114.00 -15.00 1.00 1.00 -- -40.25 -57.00 -90.00 99
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4696
_reflns_number_total 5941
_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 1.252
_refine_diff_density_min -0.689
_refine_diff_density_rms 0.089
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 382
_refine_ls_number_reflns 5941
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0780
_refine_ls_R_factor_gt 0.0630
_refine_ls_restrained_S_all 1.059
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+2.6003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1702
_refine_ls_wR_factor_ref 0.1833
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C4(H4), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
N2(H2), C16(H16), C14(H14), C31(H31), C10(H10), C30(H30), C20(H20), C17(H17),
C27(H27), C13(H13), C28(H28), C11(H11), C19(H19)
2.c Idealised Me refined as rotating group:
C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.36525(9) 1.02087(7) 0.65977(8) 0.0307(2) Uani 1 1 d . . . . .
Cl3 Cl 1.18463(9) 0.85811(9) 1.23027(8) 0.0406(3) Uani 1 1 d . . . . .
Cl2 Cl -0.23696(14) -0.04405(10) 0.06795(9) 0.0573(4) Uani 1 1 d . . . . .
O6 O -0.0250(2) 0.4141(2) 0.7055(2) 0.0251(5) Uani 1 1 d . . . . .
O2 O 0.4242(2) 0.2292(2) 0.5570(2) 0.0242(5) Uani 1 1 d . . . . .
O1 O 0.4348(3) 0.3605(2) 0.4625(2) 0.0283(5) Uani 1 1 d . . . . .
O5 O 0.1653(3) 0.6049(2) 0.7941(2) 0.0316(6) Uani 1 1 d . . . . .
O4 O 0.6260(3) 0.3604(2) 0.8390(2) 0.0311(6) Uani 1 1 d . . . . .
O3 O 0.4170(3) 0.3220(3) 0.8501(2) 0.0356(6) Uani 1 1 d . . . . .
N2 N 0.3175(3) 0.4703(2) 0.5724(2) 0.0188(5) Uani 1 1 d . . . . .
H2 H 0.2990 0.4841 0.5062 0.023 Uiso 1 1 calc R . . . .
N3 N 0.4488(3) 0.5449(2) 0.7865(2) 0.0190(5) Uani 1 1 d . . . . .
N1 N 0.1290(3) 0.3329(2) 0.6342(2) 0.0197(5) Uani 1 1 d . . . . .
C5 C 0.4734(3) 0.4427(3) 0.7412(3) 0.0190(6) Uani 1 1 d . . . . .
C3 C 0.3521(3) 0.3761(3) 0.6054(3) 0.0188(6) Uani 1 1 d . . . . .
C15 C 0.0925(3) 0.1981(3) 0.4547(3) 0.0207(6) Uani 1 1 d . . . . .
C9 C 0.3329(3) 0.6594(3) 0.6778(3) 0.0208(6) Uani 1 1 d . . . . .
C4 C 0.2037(3) 0.2781(3) 0.5862(3) 0.0195(6) Uani 1 1 d . . . . .
H4 H 0.2290 0.2246 0.6294 0.023 Uiso 1 1 calc R . . . .
C21 C 0.4081(3) 0.3225(3) 0.5328(3) 0.0192(6) Uani 1 1 d . . . . .
C1 C 0.1821(3) 0.4478(3) 0.6753(3) 0.0203(6) Uani 1 1 d . . . . .
C7 C 0.1084(3) 0.4997(3) 0.7317(3) 0.0216(6) Uani 1 1 d . . . . .
C16 C 0.0215(3) 0.2439(3) 0.3742(3) 0.0220(6) Uani 1 1 d . . . . .
H16 H 0.0426 0.3268 0.4015 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2327(3) 0.6648(3) 0.5755(3) 0.0213(6) Uani 1 1 d . . . . .
H14 H 0.1572 0.5914 0.5087 0.026 Uiso 1 1 calc R . . . .
C2 C 0.3213(3) 0.5363(3) 0.6775(3) 0.0196(6) Uani 1 1 d . . . . .
C31 C 0.7469(3) 0.6386(3) 1.0001(3) 0.0220(6) Uani 1 1 d . . . . .
H31 H 0.6604 0.5918 1.0029 0.026 Uiso 1 1 calc R . . . .
C25 C 0.5866(3) 0.5716(3) 0.7772(3) 0.0195(6) Uani 1 1 d . . . . .
H25 H 0.5847 0.5970 0.7095 0.023 Uiso 1 1 calc R . . . .
C26 C 0.7330(3) 0.6400(3) 0.8910(3) 0.0216(6) Uani 1 1 d . . . . .
C12 C 0.3522(3) 0.8806(3) 0.6668(3) 0.0242(7) Uani 1 1 d . . . . .
C10 C 0.4437(4) 0.7669(3) 0.7752(3) 0.0267(7) Uani 1 1 d . . . . .
H10 H 0.5128 0.7639 0.8456 0.032 Uiso 1 1 calc R . . . .
C30 C 0.8853(4) 0.7044(3) 1.1044(3) 0.0258(7) Uani 1 1 d . . . . .
H30 H 0.8945 0.7023 1.1784 0.031 Uiso 1 1 calc R . . . .
C20 C 0.0618(3) 0.0767(3) 0.4138(3) 0.0255(7) Uani 1 1 d . . . . .
H20 H 0.1107 0.0449 0.4679 0.031 Uiso 1 1 calc R . . . .
C17 C -0.0797(3) 0.1702(3) 0.2546(3) 0.0257(7) Uani 1 1 d . . . . .
H17 H -0.1276 0.2018 0.1998 0.031 Uiso 1 1 calc R . . . .
C27 C 0.8600(3) 0.7122(3) 0.8886(3) 0.0259(7) Uani 1 1 d . . . . .
H27 H 0.8511 0.7159 0.8150 0.031 Uiso 1 1 calc R . . . .
C23 C 0.5012(4) 0.3680(3) 0.8158(3) 0.0270(7) Uani 1 1 d . . . . .
C13 C 0.2408(3) 0.7755(3) 0.5691(3) 0.0211(6) Uani 1 1 d . . . . .
H13 H 0.1714 0.7788 0.4992 0.025 Uiso 1 1 calc R . . . .
C28 C 0.9991(4) 0.7785(3) 0.9925(3) 0.0297(7) Uani 1 1 d . . . . .
H28 H 1.0857 0.8268 0.9903 0.036 Uiso 1 1 calc R . . . .
C11 C 0.4537(4) 0.8781(3) 0.7701(3) 0.0283(7) Uani 1 1 d . . . . .
H11 H 0.5292 0.9516 0.8366 0.034 Uiso 1 1 calc R . . . .
C29 C 1.0104(4) 0.7736(3) 1.0991(3) 0.0295(7) Uani 1 1 d . . . . .
C19 C -0.0399(4) 0.0016(3) 0.2944(3) 0.0331(8) Uani 1 1 d . . . . .
H19 H -0.0613 -0.0814 0.2666 0.040 Uiso 1 1 calc R . . . .
C18 C -0.1090(4) 0.0494(3) 0.2172(3) 0.0320(8) Uani 1 1 d . . . . .
C8 C -0.1008(4) 0.4569(4) 0.7586(4) 0.0348(8) Uani 1 1 d . . . . .
H8A H -0.1203 0.5193 0.7305 0.052 Uiso 1 1 calc GR . . . .
H8B H -0.0368 0.4918 0.8456 0.052 Uiso 1 1 calc GR . . . .
H8C H -0.1965 0.3883 0.7354 0.052 Uiso 1 1 calc GR . . . .
C22 C 0.4728(4) 0.1666(3) 0.4897(4) 0.0341(8) Uani 1 1 d . . . . .
H22A H 0.3984 0.1333 0.4044 0.051 Uiso 1 1 calc GR . . . .
H22B H 0.4823 0.1001 0.5150 0.051 Uiso 1 1 calc GR . . . .
H22C H 0.5705 0.2243 0.5042 0.051 Uiso 1 1 calc GR . . . .
C24 C 0.6627(6) 0.2982(5) 0.9213(4) 0.0516(12) Uani 1 1 d . . . . .
H24A H 0.5918 0.2109 0.8806 0.077 Uiso 1 1 calc GR . . . .
H24B H 0.6554 0.3322 0.9903 0.077 Uiso 1 1 calc GR . . . .
H24C H 0.7655 0.3097 0.9483 0.077 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
Cl1 0.0280(4) 0.0275(4) 0.0396(5) 0.0140(3) 0.0149(3) 0.0177(3)
Cl3 0.0194(4) 0.0468(5) 0.0298(4) 0.0012(4) -0.0001(3) 0.0109(4)
Cl2 0.0628(7) 0.0387(5) 0.0257(5) -0.0037(4) -0.0059(4) 0.0199(5)
O6 0.0193(10) 0.0339(12) 0.0283(12) 0.0085(10) 0.0155(9) 0.0160(10)
O2 0.0264(11) 0.0305(12) 0.0305(12) 0.0129(10) 0.0205(10) 0.0205(10)
O1 0.0360(13) 0.0299(12) 0.0312(13) 0.0120(10) 0.0247(11) 0.0180(11)
O5 0.0331(13) 0.0309(13) 0.0379(14) 0.0083(11) 0.0234(11) 0.0179(11)
O4 0.0229(11) 0.0377(14) 0.0344(13) 0.0158(11) 0.0100(10) 0.0202(11)
O3 0.0483(15) 0.0474(16) 0.0395(15) 0.0264(13) 0.0323(13) 0.0339(13)
N2 0.0173(12) 0.0249(13) 0.0172(12) 0.0078(10) 0.0089(10) 0.0129(10)
N3 0.0140(11) 0.0242(13) 0.0189(12) 0.0054(10) 0.0075(10) 0.0113(10)
N1 0.0167(12) 0.0294(14) 0.0187(12) 0.0097(11) 0.0103(10) 0.0145(11)
C5 0.0138(13) 0.0250(15) 0.0190(14) 0.0050(12) 0.0082(11) 0.0115(12)
C3 0.0133(13) 0.0254(15) 0.0194(14) 0.0068(12) 0.0076(11) 0.0127(12)
C15 0.0119(13) 0.0271(15) 0.0237(15) 0.0060(12) 0.0099(12) 0.0104(12)
C9 0.0163(13) 0.0277(16) 0.0221(15) 0.0087(12) 0.0106(12) 0.0132(12)
C4 0.0159(13) 0.0246(15) 0.0193(14) 0.0051(12) 0.0089(11) 0.0124(12)
C21 0.0122(13) 0.0247(15) 0.0193(14) 0.0047(12) 0.0077(11) 0.0090(11)
C1 0.0139(13) 0.0303(16) 0.0172(14) 0.0056(12) 0.0055(11) 0.0154(12)
C7 0.0210(14) 0.0302(16) 0.0206(14) 0.0108(13) 0.0111(12) 0.0178(13)
C16 0.0135(13) 0.0252(15) 0.0252(16) 0.0046(13) 0.0095(12) 0.0098(12)
C14 0.0129(13) 0.0299(16) 0.0205(14) 0.0067(12) 0.0073(11) 0.0122(12)
C2 0.0130(13) 0.0265(15) 0.0182(14) 0.0041(12) 0.0061(11) 0.0122(12)
C31 0.0206(14) 0.0283(16) 0.0196(15) 0.0085(12) 0.0103(12) 0.0140(13)
C25 0.0155(13) 0.0263(15) 0.0202(14) 0.0092(12) 0.0097(12) 0.0123(12)
C26 0.0152(13) 0.0252(15) 0.0222(15) 0.0034(12) 0.0074(12) 0.0124(12)
C12 0.0209(14) 0.0254(16) 0.0344(18) 0.0117(14) 0.0171(13) 0.0151(13)
C10 0.0207(15) 0.0303(17) 0.0232(16) 0.0061(13) 0.0049(13) 0.0153(13)
C30 0.0255(16) 0.0285(16) 0.0208(15) 0.0065(13) 0.0073(13) 0.0166(14)
C20 0.0188(14) 0.0284(16) 0.0276(17) 0.0085(14) 0.0094(13) 0.0132(13)
C17 0.0169(14) 0.0316(17) 0.0246(16) 0.0069(13) 0.0077(12) 0.0124(13)
C27 0.0197(15) 0.0344(18) 0.0247(16) 0.0072(14) 0.0123(13) 0.0142(14)
C23 0.0287(17) 0.0275(16) 0.0191(15) 0.0028(13) 0.0059(13) 0.0178(14)
C13 0.0162(13) 0.0310(16) 0.0219(15) 0.0117(13) 0.0102(12) 0.0154(12)
C28 0.0195(15) 0.0384(19) 0.0291(17) 0.0087(15) 0.0129(14) 0.0124(14)
C11 0.0216(15) 0.0278(16) 0.0264(17) 0.0037(14) 0.0058(13) 0.0131(13)
C29 0.0206(15) 0.0300(17) 0.0293(17) 0.0041(14) 0.0069(13) 0.0135(14)
C19 0.0306(17) 0.0269(17) 0.0325(19) 0.0030(15) 0.0104(15) 0.0146(15)
C18 0.0257(16) 0.0335(19) 0.0214(16) -0.0005(14) 0.0044(13) 0.0127(15)
C8 0.0290(17) 0.048(2) 0.043(2) 0.0140(17) 0.0266(16) 0.0258(17)
C22 0.042(2) 0.0357(19) 0.049(2) 0.0173(17) 0.0361(19) 0.0269(17)
C24 0.053(3) 0.057(3) 0.040(2) 0.019(2) 0.012(2) 0.035(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.746(3) . ?
Cl3 C29 1.743(4) . ?
Cl2 C18 1.739(3) . ?
O6 C7 1.338(4) . ?
O6 C8 1.453(3) . ?
O2 C21 1.323(4) . ?
O2 C22 1.452(4) . ?
O1 C21 1.211(4) . ?
O5 C7 1.201(4) . ?
O4 C23 1.316(4) . ?
O4 C24 1.462(5) . ?
O3 C23 1.209(5) . ?
N2 H2 0.8800 . ?
N2 C3 1.452(4) . ?
N2 C2 1.459(4) . ?
N3 C5 1.474(4) . ?
N3 C2 1.500(4) . ?
N3 C25 1.492(4) . ?
N1 C4 1.481(3) . ?
N1 C1 1.268(4) . ?
C5 C3 1.564(4) . ?
C5 C25 1.503(4) . ?
C5 C23 1.499(5) . ?
C3 C4 1.552(4) . ?
C3 C21 1.509(4) . ?
C15 C4 1.524(4) . ?
C15 C16 1.391(5) . ?
C15 C20 1.393(5) . ?
C9 C14 1.387(4) . ?
C9 C2 1.510(4) . ?
C9 C10 1.391(5) . ?
C4 H4 1.0000 . ?
C1 C7 1.518(4) . ?
C1 C2 1.535(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(5) . ?
C31 H31 0.9500 . ?
C31 C26 1.393(5) . ?
C31 C30 1.384(4) . ?
C25 H25 1.0000 . ?
C25 C26 1.484(4) . ?
C26 C27 1.394(5) . ?
C12 C13 1.379(5) . ?
C12 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
C30 H30 0.9500 . ?
C30 C29 1.388(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.392(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(5) . ?
C13 H13 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.380(5) . ?
C11 H11 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.376(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
C7 O6 C8 115.1(3) . . ?
C21 O2 C22 116.1(3) . . ?
C23 O4 C24 112.9(3) . . ?
C3 N2 H2 129.0 . . ?
C3 N2 C2 101.9(2) . . ?
C2 N2 H2 129.0 . . ?
C5 N3 C2 103.4(2) . . ?
C5 N3 C25 60.88(19) . . ?
C25 N3 C2 112.4(2) . . ?
C1 N1 C4 119.6(3) . . ?
N3 C5 C3 106.3(2) . . ?
N3 C5 C25 60.15(19) . . ?
N3 C5 C23 117.5(3) . . ?
C25 C5 C3 115.3(3) . . ?
C23 C5 C3 119.0(3) . . ?
C23 C5 C25 122.6(3) . . ?
N2 C3 C5 103.7(2) . . ?
N2 C3 C4 105.7(2) . . ?
N2 C3 C21 112.4(3) . . ?
C4 C3 C5 110.7(2) . . ?
C21 C3 C5 112.5(2) . . ?
C21 C3 C4 111.4(2) . . ?
C16 C15 C4 121.4(3) . . ?
C16 C15 C20 119.1(3) . . ?
C20 C15 C4 119.5(3) . . ?
C14 C9 C2 118.5(3) . . ?
C14 C9 C10 119.4(3) . . ?
C10 C9 C2 122.1(3) . . ?
N1 C4 C3 112.1(2) . . ?
N1 C4 C15 108.6(2) . . ?
N1 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
C15 C4 C3 111.8(3) . . ?
C15 C4 H4 108.1 . . ?
O2 C21 C3 110.6(3) . . ?
O1 C21 O2 125.1(3) . . ?
O1 C21 C3 124.3(3) . . ?
N1 C1 C7 117.5(3) . . ?
N1 C1 C2 123.6(2) . . ?
C7 C1 C2 118.8(3) . . ?
O6 C7 C1 112.1(3) . . ?
O5 C7 O6 124.5(3) . . ?
O5 C7 C1 123.4(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
N2 C2 N3 108.5(2) . . ?
N2 C2 C9 110.5(3) . . ?
N2 C2 C1 104.7(2) . . ?
N3 C2 C9 112.9(2) . . ?
N3 C2 C1 102.6(2) . . ?
C9 C2 C1 117.0(2) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C26 120.8(3) . . ?
N3 C25 C5 58.97(18) . . ?
N3 C25 H25 115.0 . . ?
C5 C25 H25 115.0 . . ?
C26 C25 N3 116.4(3) . . ?
C26 C25 C5 124.4(3) . . ?
C26 C25 H25 115.0 . . ?
C31 C26 C25 122.6(3) . . ?
C31 C26 C27 118.9(3) . . ?
C27 C26 C25 118.4(3) . . ?
C13 C12 Cl1 118.9(3) . . ?
C13 C12 C11 121.9(3) . . ?
C11 C12 Cl1 119.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C31 C30 H30 120.5 . . ?
C31 C30 C29 119.0(3) . . ?
C29 C30 H30 120.5 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 H17 120.8 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
O4 C23 C5 112.3(3) . . ?
O3 C23 O4 125.3(3) . . ?
O3 C23 C5 122.4(3) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 H13 120.9 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.2(3) . . ?
C29 C28 H28 120.4 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C30 C29 Cl3 119.2(3) . . ?
C28 C29 Cl3 119.4(3) . . ?
C28 C29 C30 121.4(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19 120.6 . . ?
C17 C18 Cl2 118.8(3) . . ?
C19 C18 Cl2 119.2(3) . . ?
C19 C18 C17 122.0(3) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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 . . ?
_shelx_res_file
;
9841-11478_htk145.res created by SHELXL-2014/7
TITL 9841-11478_htk145_a.res in P-1
REM Old TITL 9841-11478_HTK145 in P-1
REM SHELXT solution in P-1
REM R1 0.172, Rweak 0.015, Alpha 0.043, Orientation as input
REM Formula found by SHELXT: C7 N4 O5 Cl3
CELL 1.54184 10.9534 12.5947 13.2276 100.624 113.849 110.012
ZERR 2 0.0008 0.0013 0.001 0.008 0.007 0.008
LATT 1
SFAC C H Cl N O
UNIT 60 48 6 6 12
L.S. 4
PLAN 6
SIZE 0.18 0.34 0.28
TEMP -173(2)
BOND $H
LIST 6
fmap 2
acta
REM
REM
REM
WGHT 0.082900 2.600300
FVAR 0.56889
CL1 3 0.365251 1.020868 0.659769 11.00000 0.02795 0.02746 =
0.03960 0.01403 0.01495 0.01769
CL3 3 1.184633 0.858107 1.230275 11.00000 0.01944 0.04685 =
0.02982 0.00121 -0.00010 0.01092
CL2 3 -0.236965 -0.044046 0.067948 11.00000 0.06277 0.03865 =
0.02568 -0.00373 -0.00587 0.01988
O6 5 -0.024951 0.414074 0.705501 11.00000 0.01925 0.03386 =
0.02830 0.00855 0.01551 0.01597
O2 5 0.424245 0.229211 0.557044 11.00000 0.02644 0.03053 =
0.03053 0.01292 0.02047 0.02051
O1 5 0.434795 0.360467 0.462480 11.00000 0.03599 0.02989 =
0.03118 0.01205 0.02473 0.01803
O5 5 0.165337 0.604944 0.794066 11.00000 0.03307 0.03090 =
0.03793 0.00829 0.02341 0.01794
O4 5 0.625976 0.360399 0.838960 11.00000 0.02292 0.03771 =
0.03443 0.01577 0.00996 0.02016
O3 5 0.417007 0.321961 0.850070 11.00000 0.04830 0.04738 =
0.03947 0.02641 0.03232 0.03385
N2 4 0.317502 0.470330 0.572394 11.00000 0.01731 0.02493 =
0.01723 0.00780 0.00894 0.01293
AFIX 43
H2 2 0.299032 0.484066 0.506185 11.00000 -1.20000
AFIX 0
N3 4 0.448758 0.544942 0.786484 11.00000 0.01395 0.02424 =
0.01894 0.00540 0.00751 0.01134
N1 4 0.128953 0.332851 0.634224 11.00000 0.01666 0.02941 =
0.01868 0.00967 0.01031 0.01452
C5 1 0.473368 0.442720 0.741178 11.00000 0.01377 0.02498 =
0.01895 0.00504 0.00819 0.01150
C3 1 0.352109 0.376109 0.605420 11.00000 0.01334 0.02544 =
0.01943 0.00675 0.00759 0.01266
C15 1 0.092479 0.198100 0.454733 11.00000 0.01186 0.02707 =
0.02372 0.00599 0.00989 0.01045
C9 1 0.332932 0.659360 0.677778 11.00000 0.01632 0.02774 =
0.02212 0.00867 0.01064 0.01322
C4 1 0.203675 0.278062 0.586207 11.00000 0.01587 0.02459 =
0.01934 0.00509 0.00888 0.01241
AFIX 13
H4 2 0.229020 0.224561 0.629448 11.00000 -1.20000
AFIX 0
C21 1 0.408096 0.322507 0.532781 11.00000 0.01216 0.02467 =
0.01926 0.00467 0.00767 0.00904
C1 1 0.182090 0.447834 0.675302 11.00000 0.01388 0.03034 =
0.01716 0.00558 0.00551 0.01535
C7 1 0.108352 0.499666 0.731691 11.00000 0.02096 0.03017 =
0.02057 0.01076 0.01107 0.01779
C16 1 0.021518 0.243933 0.374233 11.00000 0.01355 0.02518 =
0.02521 0.00458 0.00952 0.00982
AFIX 43
H16 2 0.042570 0.326836 0.401459 11.00000 -1.20000
AFIX 0
C14 1 0.232689 0.664765 0.575490 11.00000 0.01289 0.02992 =
0.02053 0.00672 0.00734 0.01223
AFIX 43
H14 2 0.157237 0.591434 0.508731 11.00000 -1.20000
AFIX 0
C2 1 0.321301 0.536348 0.677523 11.00000 0.01296 0.02651 =
0.01816 0.00415 0.00612 0.01220
C31 1 0.746923 0.638557 1.000062 11.00000 0.02059 0.02829 =
0.01960 0.00853 0.01030 0.01400
AFIX 43
H31 2 0.660356 0.591765 1.002916 11.00000 -1.20000
AFIX 0
C25 1 0.586619 0.571574 0.777206 11.00000 0.01548 0.02629 =
0.02023 0.00917 0.00967 0.01225
AFIX 13
H25 2 0.584719 0.596999 0.709512 11.00000 -1.20000
AFIX 0
C26 1 0.732981 0.640001 0.890955 11.00000 0.01520 0.02525 =
0.02220 0.00342 0.00740 0.01245
C12 1 0.352229 0.880610 0.666799 11.00000 0.02093 0.02538 =
0.03438 0.01170 0.01708 0.01508
C10 1 0.443736 0.766875 0.775234 11.00000 0.02066 0.03033 =
0.02315 0.00613 0.00487 0.01530
AFIX 43
H10 2 0.512833 0.763934 0.845584 11.00000 -1.20000
AFIX 0
C30 1 0.885289 0.704427 1.104370 11.00000 0.02554 0.02849 =
0.02082 0.00651 0.00731 0.01658
AFIX 43
H30 2 0.894463 0.702301 1.178433 11.00000 -1.20000
AFIX 0
C20 1 0.061767 0.076703 0.413794 11.00000 0.01878 0.02844 =
0.02756 0.00847 0.00938 0.01322
AFIX 43
H20 2 0.110695 0.044898 0.467909 11.00000 -1.20000
AFIX 0
C17 1 -0.079680 0.170214 0.254611 11.00000 0.01688 0.03163 =
0.02463 0.00690 0.00775 0.01242
AFIX 43
H17 2 -0.127638 0.201833 0.199758 11.00000 -1.20000
AFIX 0
C27 1 0.860014 0.712184 0.888606 11.00000 0.01967 0.03440 =
0.02466 0.00724 0.01229 0.01419
AFIX 43
H27 2 0.851123 0.715942 0.815026 11.00000 -1.20000
AFIX 0
C23 1 0.501245 0.368045 0.815807 11.00000 0.02871 0.02751 =
0.01913 0.00276 0.00588 0.01775
C13 1 0.240816 0.775477 0.569089 11.00000 0.01619 0.03103 =
0.02194 0.01174 0.01017 0.01535
AFIX 43
H13 2 0.171386 0.778769 0.499164 11.00000 -1.20000
AFIX 0
C28 1 0.999124 0.778514 0.992483 11.00000 0.01951 0.03839 =
0.02910 0.00873 0.01291 0.01239
AFIX 43
H28 2 1.085660 0.826761 0.990330 11.00000 -1.20000
AFIX 0
C11 1 0.453726 0.878053 0.770134 11.00000 0.02156 0.02779 =
0.02637 0.00372 0.00576 0.01306
AFIX 43
H11 2 0.529169 0.951629 0.836598 11.00000 -1.20000
AFIX 0
C29 1 1.010400 0.773620 1.099070 11.00000 0.02063 0.03004 =
0.02932 0.00408 0.00691 0.01354
C19 1 -0.039923 0.001554 0.294358 11.00000 0.03058 0.02692 =
0.03248 0.00304 0.01038 0.01462
AFIX 43
H19 2 -0.061253 -0.081375 0.266600 11.00000 -1.20000
AFIX 0
C18 1 -0.109036 0.049382 0.217167 11.00000 0.02574 0.03355 =
0.02140 -0.00054 0.00438 0.01265
C8 1 -0.100785 0.456855 0.758570 11.00000 0.02897 0.04790 =
0.04339 0.01398 0.02657 0.02581
AFIX 137
H8A 2 -0.120268 0.519311 0.730525 11.00000 -1.50000
H8B 2 -0.036756 0.491758 0.845625 11.00000 -1.50000
H8C 2 -0.196478 0.388348 0.735350 11.00000 -1.50000
AFIX 0
C22 1 0.472811 0.166633 0.489678 11.00000 0.04249 0.03567 =
0.04874 0.01730 0.03613 0.02693
AFIX 137
H22A 2 0.398391 0.133330 0.404421 11.00000 -1.50000
H22B 2 0.482274 0.100072 0.514980 11.00000 -1.50000
H22C 2 0.570538 0.224273 0.504179 11.00000 -1.50000
AFIX 0
C24 1 0.662691 0.298195 0.921319 11.00000 0.05332 0.05732 =
0.03997 0.01913 0.01156 0.03540
AFIX 137
H24A 2 0.591789 0.210933 0.880608 11.00000 -1.50000
H24B 2 0.655404 0.332244 0.990279 11.00000 -1.50000
H24C 2 0.765485 0.309720 0.948265 11.00000 -1.50000
AFIX 0
HKLF 4
REM 9841-11478_htk145_a.res in P-1
REM R1 = 0.0630 for 4696 Fo > 4sig(Fo) and 0.0780 for all 5941 data
REM 382 parameters refined using 0 restraints
END
WGHT 0.0829 2.6065
REM Highest difference peak 1.252, deepest hole -0.689, 1-sigma level 0.089
Q1 1 0.4948 0.2751 0.9440 11.00000 0.05 1.25
Q2 1 -0.1596 -0.0189 0.0619 11.00000 0.05 0.66
Q3 1 0.4002 0.5121 0.5607 11.00000 0.05 0.56
Q4 1 0.4207 0.4029 0.6692 11.00000 0.05 0.52
Q5 1 0.6532 0.6044 0.8321 11.00000 0.05 0.43
Q6 1 0.2596 0.9777 0.5778 11.00000 0.05 0.39
;
_shelx_res_checksum 71083
_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
;
#######################################################################
#
# 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_15893_htk03
_database_code_depnum_ccdc_archive 'CCDC 1994004'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record
;
2020-03-31 deposited with the CCDC. 2020-06-15 downloaded from the CCDC.
;
_audit_creation_date 2020-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C22 H22 N2 O6'
_chemical_formula_sum 'C22 H22 N2 O6'
_chemical_formula_weight 410.41
_chemical_melting_point ?
_chemical_oxdiff_formula 'C22 H22 N2 O6'
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 14.0485(3)
_cell_length_b 13.9573(3)
_cell_length_c 10.3547(3)
_cell_angle_alpha 90
_cell_angle_beta 99.580(2)
_cell_angle_gamma 90
_cell_volume 2002.03(8)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 4354
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 28.3270
_cell_measurement_theta_min 3.0520
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.96739
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_lustre .
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.362
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 864
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max 0.41
_exptl_crystal_size_mid 0.32
_exptl_crystal_size_min 0.3
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0318
_diffrn_reflns_av_unetI/netI 0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 13770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.499
_diffrn_reflns_theta_min 2.701
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2096
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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 -88.00 -17.00 1.00 84.45 -- -19.04 -57.00 150.00 71
2 \w -93.00 27.00 1.00 84.45 -- -19.04 -19.00-180.00 120
3 \w 16.00 57.00 1.00 84.45 -- 20.06 -99.00 -30.00 41
4 \w -56.00 42.00 1.00 84.45 -- -19.04 19.00 -30.00 98
5 \w -81.00 -49.00 1.00 84.45 -- -19.04 -38.00 -30.00 32
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0319910000
_diffrn_orient_matrix_UB_12 -0.0030990000
_diffrn_orient_matrix_UB_13 -0.0460866000
_diffrn_orient_matrix_UB_21 0.0385909000
_diffrn_orient_matrix_UB_22 0.0155781000
_diffrn_orient_matrix_UB_23 0.0485410000
_diffrn_orient_matrix_UB_31 0.0104303000
_diffrn_orient_matrix_UB_32 -0.0482725000
_diffrn_orient_matrix_UB_33 0.0186321000
_diffrn_radiation_monochromator graphite
_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 3626
_reflns_number_total 4451
_reflns_odcompleteness_completeness 99.86
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection 'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction 'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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 ?
_refine_diff_density_max 0.293
_refine_diff_density_min -0.220
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 279
_refine_ls_number_reflns 4451
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0553
_refine_ls_R_factor_gt 0.0415
_refine_ls_restrained_S_all 1.022
_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^)+(0.0418P)^2^+0.7207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0923
_refine_ls_wR_factor_ref 0.0991
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
C7(H7), C10(H10), C17(H17), C14(H14), C9(H9), C16(H16), C8(H8), C15(H15)
2.c Idealised Me refined as rotating group:
C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C11(H11A,H11B,
H11C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.65997(7) 0.33180(7) 0.39204(10) 0.0192(2) Uani 1 1 d . . . . .
O1 O 0.47869(7) 0.34199(7) 0.56080(10) 0.0186(2) Uani 1 1 d . . . . .
O6 O 0.87286(7) 0.55520(7) 0.95719(10) 0.0216(2) Uani 1 1 d . . . . .
O4 O 0.88010(7) 0.56924(7) 0.50822(10) 0.0210(2) Uani 1 1 d . . . . .
O5 O 0.79122(8) 0.69248(8) 0.91236(12) 0.0298(3) Uani 1 1 d . . . . .
N2 N 0.62627(8) 0.46639(8) 0.59036(11) 0.0141(2) Uani 1 1 d . . . . .
N1 N 0.66365(8) 0.51897(8) 0.80780(11) 0.0160(2) Uani 1 1 d . . . . .
O3 O 0.91968(8) 0.63908(9) 0.70561(12) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.60371(9) 0.48068(9) 0.70905(13) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.74931(9) 0.55351(10) 0.77665(14) 0.0152(3) Uani 1 1 d . . . . .
C3 C 0.78033(9) 0.53953(10) 0.66127(14) 0.0154(3) Uani 1 1 d . . . . .
C21 C 0.80625(9) 0.61085(10) 0.88670(14) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.44311(9) 0.38948(10) 0.65867(13) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.50402(9) 0.45772(10) 0.73139(13) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.76997(9) 0.36803(10) 0.58007(13) 0.0146(3) Uani 1 1 d . . . . .
C19 C 0.86673(10) 0.58790(10) 0.63112(14) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.72701(9) 0.46860(10) 0.56651(13) 0.0136(3) Uani 1 1 d . . . . .
H2A H 0.7275 0.4919 0.4753 0.016 Uiso 1 1 calc R . . . .
C7 C 0.35201(10) 0.37082(10) 0.68907(14) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.3115 0.3242 0.6408 0.023 Uiso 1 1 calc R . . . .
C10 C 0.46965(10) 0.50551(10) 0.83260(14) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.5099 0.5514 0.8828 0.022 Uiso 1 1 calc R . . . .
C17 C 0.84240(10) 0.34133(10) 0.68181(14) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.8679 0.3873 0.7460 0.022 Uiso 1 1 calc R . . . .
C13 C 0.73274(9) 0.29918(10) 0.48664(14) 0.0169(3) Uani 1 1 d . . . . .
C14 C 0.76765(10) 0.20593(10) 0.49508(15) 0.0212(3) Uani 1 1 d . . . . .
H14 H 0.7422 0.1595 0.4315 0.025 Uiso 1 1 calc R . . . .
C9 C 0.37847(10) 0.48816(11) 0.86229(14) 0.0226(3) Uani 1 1 d . . . . .
H9 H 0.3562 0.5221 0.9310 0.027 Uiso 1 1 calc R . . . .
C16 C 0.87824(10) 0.24801(11) 0.69120(15) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.9280 0.2305 0.7609 0.027 Uiso 1 1 calc R . . . .
C8 C 0.32064(10) 0.42051(11) 0.78996(15) 0.0222(3) Uani 1 1 d . . . . .
H8 H 0.2582 0.4078 0.8098 0.027 Uiso 1 1 calc R . . . .
C18 C 0.62390(11) 0.26768(11) 0.28798(15) 0.0242(3) Uani 1 1 d . . . . .
H18A H 0.5711 0.2985 0.2288 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.6000 0.2093 0.3243 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.6758 0.2512 0.2394 0.036 Uiso 1 1 calc GR . . . .
C15 C 0.84063(11) 0.18140(11) 0.59816(16) 0.0239(3) Uani 1 1 d . . . . .
H15 H 0.8649 0.1177 0.6044 0.029 Uiso 1 1 calc R . . . .
C20 C 0.95949(11) 0.61832(11) 0.46414(16) 0.0265(3) Uani 1 1 d . . . . .
H20A H 0.9705 0.5906 0.3810 0.040 Uiso 1 1 calc GR . . . .
H20B H 1.0179 0.6112 0.5299 0.040 Uiso 1 1 calc GR . . . .
H20C H 0.9438 0.6865 0.4517 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.93615(11) 0.60231(12) 1.06311(15) 0.0260(3) Uani 1 1 d . . . . .
H22A H 0.9812 0.6440 1.0268 0.039 Uiso 1 1 calc GR . . . .
H22B H 0.9725 0.5540 1.1197 0.039 Uiso 1 1 calc GR . . . .
H22C H 0.8975 0.6408 1.1144 0.039 Uiso 1 1 calc GR . . . .
C11 C 0.41842(11) 0.27127(11) 0.48775(16) 0.0259(3) Uani 1 1 d . . . . .
H11A H 0.4529 0.2419 0.4231 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.3592 0.3017 0.4427 0.039 Uiso 1 1 calc GR . . . .
H11C H 0.4018 0.2219 0.5475 0.039 Uiso 1 1 calc GR . . . .
H2 H 0.5836(12) 0.4347(12) 0.5306(17) 0.028(5) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0233(5) 0.0179(5) 0.0154(5) -0.0043(4) 0.0005(4) 0.0000(4)
O1 0.0163(5) 0.0198(5) 0.0202(5) -0.0060(4) 0.0046(4) -0.0041(4)
O6 0.0207(5) 0.0217(5) 0.0198(6) -0.0018(4) -0.0045(4) 0.0001(4)
O4 0.0198(5) 0.0240(5) 0.0212(6) -0.0024(4) 0.0097(4) -0.0061(4)
O5 0.0268(6) 0.0220(6) 0.0369(7) -0.0120(5) -0.0053(5) 0.0043(5)
N2 0.0119(5) 0.0167(6) 0.0136(6) -0.0013(5) 0.0019(4) -0.0010(5)
N1 0.0142(6) 0.0189(6) 0.0149(6) -0.0010(5) 0.0029(4) -0.0013(5)
O3 0.0331(6) 0.0538(8) 0.0272(7) -0.0135(6) 0.0112(5) -0.0272(6)
C1 0.0150(6) 0.0127(6) 0.0145(7) 0.0024(5) 0.0035(5) 0.0020(5)
C4 0.0145(6) 0.0144(6) 0.0161(7) 0.0002(5) 0.0009(5) 0.0003(5)
C3 0.0142(6) 0.0153(6) 0.0166(7) 0.0002(5) 0.0023(5) -0.0011(5)
C21 0.0135(6) 0.0204(7) 0.0178(7) -0.0018(6) 0.0049(5) -0.0010(5)
C6 0.0152(6) 0.0166(7) 0.0154(7) 0.0035(6) 0.0018(5) 0.0024(5)
C5 0.0131(6) 0.0175(7) 0.0135(7) 0.0036(5) 0.0021(5) 0.0013(5)
C12 0.0132(6) 0.0170(7) 0.0154(7) 0.0012(5) 0.0077(5) 0.0001(5)
C19 0.0179(7) 0.0206(7) 0.0190(7) -0.0005(6) 0.0047(5) -0.0028(6)
C2 0.0128(6) 0.0162(7) 0.0123(7) 0.0006(5) 0.0035(5) -0.0006(5)
C7 0.0157(7) 0.0215(7) 0.0200(7) 0.0049(6) 0.0009(5) -0.0018(6)
C10 0.0177(7) 0.0222(7) 0.0158(7) 0.0001(6) 0.0024(5) 0.0007(6)
C17 0.0150(6) 0.0224(7) 0.0179(7) 0.0015(6) 0.0063(5) 0.0001(6)
C13 0.0163(6) 0.0200(7) 0.0157(7) 0.0010(6) 0.0065(5) -0.0001(6)
C14 0.0254(7) 0.0181(7) 0.0224(8) -0.0043(6) 0.0110(6) 0.0001(6)
C9 0.0199(7) 0.0318(8) 0.0172(7) 0.0012(6) 0.0067(5) 0.0051(6)
C16 0.0179(7) 0.0280(8) 0.0234(8) 0.0068(6) 0.0053(6) 0.0056(6)
C8 0.0138(7) 0.0320(8) 0.0220(8) 0.0076(7) 0.0063(5) 0.0008(6)
C18 0.0265(8) 0.0240(8) 0.0216(8) -0.0095(6) 0.0022(6) -0.0031(6)
C15 0.0267(8) 0.0192(7) 0.0284(9) 0.0041(6) 0.0125(6) 0.0079(6)
C20 0.0229(8) 0.0293(8) 0.0307(9) -0.0002(7) 0.0140(6) -0.0077(7)
C22 0.0213(7) 0.0339(9) 0.0199(8) -0.0044(7) -0.0046(6) -0.0034(7)
C11 0.0221(8) 0.0261(8) 0.0294(9) -0.0114(7) 0.0040(6) -0.0065(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C13 1.3707(17) . ?
O2 C18 1.4273(17) . ?
O1 C6 1.3729(16) . ?
O1 C11 1.4318(17) . ?
O6 C21 1.3358(17) . ?
O6 C22 1.4495(17) . ?
O4 C19 1.3424(17) . ?
O4 C20 1.4459(16) . ?
O5 C21 1.1967(17) . ?
N2 C1 1.3342(18) . ?
N2 C2 1.4769(16) . ?
N1 C1 1.3243(17) . ?
N1 C4 1.3833(17) . ?
O3 C19 1.2114(18) . ?
C1 C5 1.4918(18) . ?
C4 C3 1.3524(19) . ?
C4 C21 1.5085(19) . ?
C3 C19 1.4672(19) . ?
C3 C2 1.5031(18) . ?
C6 C5 1.4114(19) . ?
C6 C7 1.3925(19) . ?
C5 C10 1.395(2) . ?
C12 C2 1.5252(19) . ?
C12 C17 1.3883(19) . ?
C12 C13 1.4015(19) . ?
C7 C8 1.386(2) . ?
C10 C9 1.3875(19) . ?
C17 C16 1.394(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.394(2) . ?
C9 C8 1.382(2) . ?
C16 C15 1.379(2) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C18 117.39(11) . . ?
C6 O1 C11 117.82(11) . . ?
C21 O6 C22 115.81(11) . . ?
C19 O4 C20 116.37(11) . . ?
C1 N2 C2 122.15(11) . . ?
C1 N1 C4 115.26(12) . . ?
N2 C1 C5 118.94(12) . . ?
N1 C1 N2 123.61(12) . . ?
N1 C1 C5 117.37(12) . . ?
N1 C4 C21 112.42(12) . . ?
C3 C4 N1 125.20(12) . . ?
C3 C4 C21 122.38(12) . . ?
C4 C3 C19 121.42(12) . . ?
C4 C3 C2 118.22(12) . . ?
C19 C3 C2 120.28(12) . . ?
O6 C21 C4 109.85(11) . . ?
O5 C21 O6 124.45(13) . . ?
O5 C21 C4 125.58(13) . . ?
O1 C6 C5 117.18(11) . . ?
O1 C6 C7 122.54(12) . . ?
C7 C6 C5 120.27(13) . . ?
C6 C5 C1 124.31(12) . . ?
C10 C5 C1 117.72(12) . . ?
C10 C5 C6 117.95(12) . . ?
C17 C12 C2 123.07(12) . . ?
C17 C12 C13 118.81(13) . . ?
C13 C12 C2 118.10(12) . . ?
O4 C19 C3 111.32(12) . . ?
O3 C19 O4 123.37(13) . . ?
O3 C19 C3 125.30(14) . . ?
N2 C2 C3 106.97(11) . . ?
N2 C2 C12 109.93(11) . . ?
C3 C2 C12 113.55(11) . . ?
C8 C7 C6 119.76(13) . . ?
C9 C10 C5 122.06(14) . . ?
C12 C17 C16 120.95(14) . . ?
O2 C13 C12 114.44(12) . . ?
O2 C13 C14 124.75(13) . . ?
C14 C13 C12 120.79(13) . . ?
C13 C14 C15 119.04(14) . . ?
C8 C9 C10 118.71(14) . . ?
C15 C16 C17 119.29(14) . . ?
C9 C8 C7 121.24(13) . . ?
C16 C15 C14 121.12(14) . . ?
_shelx_res_file
;
15893_htk03.res created by SHELXL-2014/7
TITL 15893_htk03_a.res in P2(1)/c
REM Old TITL 15893_HTK03 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.124, Rweak 0.053, Alpha 0.019, Orientation as input
REM Formula found by SHELXT: C22 N2 O6
CELL 0.71073 14.0485 13.9573 10.3547 90 99.58 90
ZERR 4 0.0003 0.0003 0.0003 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 88 88 8 24
L.S. 4 0 0
PLAN 20
TEMP -173(2)
list 4
fmap 2 53
ACTA
OMIT -4 55
REM
REM
REM
WGHT 0.041800 0.720700
FVAR 0.49888
O2 4 0.659971 0.331804 0.392039 11.00000 0.02331 0.01793 =
0.01541 -0.00432 0.00053 -0.00004
O1 4 0.478692 0.341985 0.560797 11.00000 0.01633 0.01982 =
0.02023 -0.00603 0.00460 -0.00407
O6 4 0.872864 0.555204 0.957190 11.00000 0.02074 0.02166 =
0.01981 -0.00182 -0.00449 0.00006
O4 4 0.880101 0.569236 0.508220 11.00000 0.01981 0.02404 =
0.02119 -0.00242 0.00968 -0.00614
O5 4 0.791218 0.692479 0.912363 11.00000 0.02679 0.02195 =
0.03692 -0.01198 -0.00526 0.00427
N2 3 0.626274 0.466394 0.590364 11.00000 0.01186 0.01670 =
0.01365 -0.00128 0.00195 -0.00096
N1 3 0.663652 0.518970 0.807799 11.00000 0.01422 0.01891 =
0.01490 -0.00102 0.00286 -0.00131
O3 4 0.919675 0.639083 0.705606 11.00000 0.03308 0.05385 =
0.02717 -0.01354 0.01116 -0.02715
C1 1 0.603707 0.480682 0.709046 11.00000 0.01500 0.01266 =
0.01449 0.00244 0.00350 0.00198
C4 1 0.749308 0.553506 0.776654 11.00000 0.01449 0.01436 =
0.01610 0.00021 0.00091 0.00029
C3 1 0.780335 0.539527 0.661270 11.00000 0.01419 0.01534 =
0.01660 0.00017 0.00234 -0.00111
C21 1 0.806254 0.610850 0.886696 11.00000 0.01353 0.02036 =
0.01779 -0.00178 0.00487 -0.00105
C6 1 0.443110 0.389475 0.658670 11.00000 0.01524 0.01664 =
0.01538 0.00351 0.00178 0.00241
C5 1 0.504020 0.457721 0.731392 11.00000 0.01315 0.01748 =
0.01349 0.00359 0.00206 0.00128
C12 1 0.769972 0.368027 0.580067 11.00000 0.01318 0.01702 =
0.01544 0.00124 0.00773 0.00013
C19 1 0.866733 0.587900 0.631116 11.00000 0.01787 0.02061 =
0.01901 -0.00046 0.00465 -0.00276
C2 1 0.727015 0.468601 0.566507 11.00000 0.01282 0.01620 =
0.01232 0.00060 0.00352 -0.00057
AFIX 13
H2A 2 0.727466 0.491900 0.475285 11.00000 -1.20000
AFIX 0
C7 1 0.352008 0.370817 0.689070 11.00000 0.01567 0.02147 =
0.01996 0.00490 0.00094 -0.00181
AFIX 43
H7 2 0.311505 0.324183 0.640808 11.00000 -1.20000
AFIX 0
C10 1 0.469649 0.505514 0.832601 11.00000 0.01767 0.02217 =
0.01584 0.00009 0.00244 0.00071
AFIX 43
H10 2 0.509931 0.551392 0.882794 11.00000 -1.20000
AFIX 0
C17 1 0.842397 0.341328 0.681815 11.00000 0.01502 0.02243 =
0.01791 0.00154 0.00629 0.00013
AFIX 43
H17 2 0.867898 0.387319 0.745972 11.00000 -1.20000
AFIX 0
C13 1 0.732743 0.299181 0.486643 11.00000 0.01631 0.02002 =
0.01566 0.00102 0.00652 -0.00008
C14 1 0.767648 0.205926 0.495083 11.00000 0.02535 0.01812 =
0.02243 -0.00428 0.01103 0.00006
AFIX 43
H14 2 0.742162 0.159508 0.431536 11.00000 -1.20000
AFIX 0
C9 1 0.378465 0.488161 0.862287 11.00000 0.01993 0.03184 =
0.01720 0.00117 0.00673 0.00513
AFIX 43
H9 2 0.356217 0.522123 0.930991 11.00000 -1.20000
AFIX 0
C16 1 0.878241 0.248008 0.691199 11.00000 0.01786 0.02803 =
0.02337 0.00680 0.00530 0.00563
AFIX 43
H16 2 0.928037 0.230478 0.760932 11.00000 -1.20000
AFIX 0
C8 1 0.320641 0.420509 0.789960 11.00000 0.01382 0.03199 =
0.02200 0.00758 0.00633 0.00083
AFIX 43
H8 2 0.258214 0.407837 0.809787 11.00000 -1.20000
AFIX 0
C18 1 0.623900 0.267677 0.287977 11.00000 0.02651 0.02396 =
0.02159 -0.00949 0.00216 -0.00309
AFIX 137
H18A 2 0.571079 0.298532 0.228785 11.00000 -1.50000
H18B 2 0.600006 0.209273 0.324271 11.00000 -1.50000
H18C 2 0.675850 0.251196 0.239426 11.00000 -1.50000
AFIX 0
C15 1 0.840631 0.181404 0.598156 11.00000 0.02668 0.01918 =
0.02843 0.00414 0.01251 0.00792
AFIX 43
H15 2 0.864873 0.117736 0.604414 11.00000 -1.20000
AFIX 0
C20 1 0.959486 0.618317 0.464144 11.00000 0.02286 0.02932 =
0.03069 -0.00022 0.01397 -0.00769
AFIX 137
H20A 2 0.970531 0.590559 0.380970 11.00000 -1.50000
H20B 2 1.017893 0.611185 0.529862 11.00000 -1.50000
H20C 2 0.943837 0.686474 0.451727 11.00000 -1.50000
AFIX 0
C22 1 0.936151 0.602311 1.063112 11.00000 0.02132 0.03394 =
0.01991 -0.00438 -0.00459 -0.00339
AFIX 137
H22A 2 0.981204 0.644045 1.026810 11.00000 -1.50000
H22B 2 0.972500 0.553961 1.119745 11.00000 -1.50000
H22C 2 0.897534 0.640777 1.114394 11.00000 -1.50000
AFIX 0
C11 1 0.418419 0.271270 0.487753 11.00000 0.02211 0.02611 =
0.02938 -0.01138 0.00403 -0.00648
AFIX 137
H11A 2 0.452944 0.241853 0.423080 11.00000 -1.50000
H11B 2 0.359223 0.301684 0.442683 11.00000 -1.50000
H11C 2 0.401834 0.221871 0.547501 11.00000 -1.50000
AFIX 0
H2 2 0.583647 0.434683 0.530592 11.00000 0.02798
HKLF 4
REM 15893_htk03_a.res in P2(1)/c
REM R1 = 0.0415 for 3626 Fo > 4sig(Fo) and 0.0553 for all 4451 data
REM 279 parameters refined using 0 restraints
END
WGHT 0.0415 0.7322
REM Highest difference peak 0.293, deepest hole -0.220, 1-sigma level 0.045
Q1 1 0.8327 0.5394 0.6602 11.00000 0.05 0.29
Q2 1 0.5525 0.4610 0.7292 11.00000 0.05 0.28
Q3 1 0.8169 0.5599 0.6480 11.00000 0.05 0.28
Q4 1 0.5419 0.4785 0.7066 11.00000 0.05 0.27
Q5 1 0.7449 0.4133 0.5877 11.00000 0.05 0.26
Q6 1 0.7595 0.5023 0.6208 11.00000 0.05 0.24
Q7 1 0.6787 0.4639 0.5821 11.00000 0.05 0.24
Q8 1 0.4789 0.4194 0.7022 11.00000 0.05 0.24
Q9 1 0.7381 0.3340 0.5477 11.00000 0.05 0.22
Q10 1 0.7741 0.2632 0.4724 11.00000 0.05 0.22
Q11 1 0.4099 0.3585 0.6963 11.00000 0.05 0.21
Q12 1 0.8801 0.3017 0.6677 11.00000 0.05 0.21
Q13 1 0.3889 0.4021 0.6508 11.00000 0.05 0.20
Q14 1 0.7860 0.3428 0.6487 11.00000 0.05 0.20
Q15 1 0.4363 0.4642 0.8744 11.00000 0.05 0.20
Q16 1 0.4678 0.4350 0.6701 11.00000 0.05 0.20
Q17 1 0.6421 0.4809 0.7696 11.00000 0.05 0.20
Q18 1 0.7174 0.5195 0.7998 11.00000 0.05 0.20
Q19 1 0.7747 0.5826 0.8261 11.00000 0.05 0.19
Q20 1 0.5434 0.3138 0.5724 11.00000 0.05 0.19
;
_shelx_res_checksum 94169
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.097
_oxdiff_exptl_absorpt_empirical_full_min 0.912
#######################################################################
#
# 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_15289_htk-02
_database_code_depnum_ccdc_archive 'CCDC 1994005'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record
;
2020-03-31 deposited with the CCDC. 2020-06-15 downloaded from the CCDC.
;
_audit_creation_date 2020-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C20 H14 Cl4 N2 O4'
_chemical_formula_sum 'C20 H14 Cl4 N2 O4'
_chemical_formula_weight 488.13
_chemical_absolute_configuration unk
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H14 Cl4 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 10.82480(10)
_cell_length_b 16.44070(10)
_cell_length_c 12.04070(10)
_cell_angle_alpha 90
_cell_angle_beta 109.7710(10)
_cell_angle_gamma 90
_cell_volume 2016.53(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 19869
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 70.2600
_cell_measurement_theta_min 3.8950
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 5.619
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.83397
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.608
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 992
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0333
_diffrn_reflns_av_unetI/netI 0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 25202
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 70.448
_diffrn_reflns_theta_min 3.901
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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 -20.00 6.00 0.50 0.40 -- 38.95 -54.00-138.00 52
2 \w 29.00 64.00 0.50 0.40 -- 38.95 54.00 6.00 70
3 \w 67.00 102.00 0.50 0.40 -- 38.95 54.00 6.00 70
4 \w 80.00 141.00 0.50 0.90 -- 100.00 54.00 6.00 122
5 \w 70.00 118.00 0.50 0.90 -- 100.00 -54.00-138.00 96
6 \w 42.00 68.00 0.50 0.90 -- 100.00 -54.00-138.00 52
7 \w -7.00 21.00 0.50 0.40 -- -38.95 32.00 120.00 56
8 \w -46.00 -20.00 0.50 0.40 -- -38.95 32.00 120.00 52
9 \w -72.00 -46.00 0.50 0.40 -- -38.95 -21.00-120.00 52
10 \w -46.00 -21.00 0.50 0.40 -- -38.95 -54.00-138.00 50
11 \w -80.00 -54.00 0.50 0.40 -- -38.95 -54.00-138.00 52
12 \w -56.00 25.00 0.50 0.40 -- -38.95 43.00-180.00 162
13 \w -107.00 -79.00 0.50 0.40 -- -38.95 -21.00-120.00 56
14 \w -34.00 -8.00 0.50 0.40 -- -38.95 54.00 6.00 52
15 \w 23.00 49.00 0.50 0.40 -- 38.95 21.00 90.00 52
16 \w 76.00 106.00 0.50 0.40 -- 38.95 21.00 -30.00 60
17 \w 32.00 100.00 0.50 0.40 -- 38.95 65.00 30.00 136
18 \w 24.00 72.00 0.50 0.40 -- 38.95 21.00 -30.00 96
19 \w 22.00 49.00 0.50 0.40 -- 38.95 -54.00-138.00 54
20 \w 76.00 102.00 0.50 0.40 -- 38.95 21.00 90.00 52
21 \w -17.00 53.00 0.50 0.40 -- 38.95 -43.00 90.00 140
22 \w 35.00 61.00 0.50 0.40 -- 38.95 32.00 0.00 52
23 \w 31.00 80.00 0.50 0.90 -- 100.00-111.00 -90.00 98
24 \w 130.00 156.00 0.50 0.90 -- 100.00 7.00 -30.00 52
25 \w 78.00 124.00 0.50 0.90 -- 100.00 -69.00 0.00 92
26 \w 84.00 155.00 0.50 0.90 -- 100.00 133.00-120.00 142
27 \w 94.00 119.00 0.50 0.90 -- 100.00 -22.00 90.00 50
28 \w 61.00 93.00 0.50 0.90 -- 100.00 7.00 -30.00 64
29 \w 63.00 89.00 0.50 0.90 -- 100.00 -22.00 90.00 52
30 \w 83.00 114.00 0.50 0.90 -- 100.00 -30.00-180.00 62
31 \w 46.00 116.00 0.50 0.90 -- 100.00 -45.00 90.00 140
32 \w 32.00 63.00 0.50 0.90 -- 100.00 -30.00-180.00 62
33 \w 83.00 110.00 0.50 0.90 -- 100.00 -45.00 0.00 54
34 \w 108.00 156.00 0.50 0.90 -- 100.00 93.00 60.00 96
35 \w 78.00 125.00 0.50 0.90 -- 100.00 61.00 150.00 94
36 \w 31.00 75.00 0.50 0.90 -- 100.00 -30.00 30.00 88
37 \w 84.00 125.00 0.50 0.90 -- 100.00 111.00 60.00 82
38 \w 61.00 104.00 0.50 0.90 -- 100.00 -61.00 0.00 86
39 \w 107.00 133.00 0.50 0.90 -- 100.00 30.00 90.00 52
40 \w 101.00 157.00 0.50 0.90 -- 100.00 93.00-150.00 112
41 \w 86.00 134.00 0.50 0.90 -- 100.00 111.00 -90.00 96
42 \w 86.00 152.00 0.50 0.90 -- 100.00 53.00 -30.00 132
43 \w 93.00 147.00 0.50 0.90 -- 100.00 93.00 -30.00 108
44 \w 40.00 66.00 0.50 0.90 -- 100.00 -54.00-138.00 52
45 \w -77.00 -25.00 0.50 0.40 -- -38.95 -32.00 90.00 104
46 \w 18.00 56.00 0.50 0.40 -- 38.95 65.00 120.00 76
47 \w 82.00 108.00 0.50 0.40 -- 38.95 32.00-150.00 52
48 \w 61.00 101.00 0.50 0.40 -- 38.95 65.00 120.00 80
49 \w 21.00 90.00 0.50 0.40 -- 38.95 65.00 150.00 138
50 \w 15.00 59.00 0.50 0.40 -- 38.95 -11.00-150.00 88
51 \w -27.00 6.00 0.50 0.40 -- 38.95 -11.00-150.00 66
52 \w -3.00 48.00 0.50 0.40 -- 38.95 -32.00 120.00 102
53 \w 31.00 57.00 0.50 0.40 -- 38.95 65.00 90.00 52
54 \w 63.00 97.00 0.50 0.40 -- 38.95 65.00 90.00 68
55 \w 86.00 114.00 0.50 0.90 -- 100.00 53.00 -60.00 56
56 \w 76.00 101.00 0.50 0.90 -- 100.00 69.00 120.00 50
57 \w 78.00 110.00 0.50 0.90 -- 100.00 61.00 120.00 64
58 \w 106.00 153.00 0.50 0.90 -- 100.00 93.00 0.00 94
59 \w 114.00 157.00 0.50 0.90 -- 100.00 67.00 99.99 86
60 \w 121.00 154.00 0.50 0.90 -- 100.00 69.00 30.00 66
61 \w 132.00 157.00 0.50 0.90 -- 100.00 69.00 60.00 50
62 \w 93.00 119.00 0.50 0.90 -- 100.00 69.00 30.00 52
63 \w 84.00 110.00 0.50 0.90 -- 100.00 45.00 150.00 52
64 \w 110.00 136.00 0.50 0.90 -- 100.00 133.00 120.00 52
65 \w 118.00 157.00 0.50 0.90 -- 100.00 133.00 150.00 78
66 \w 76.00 102.00 0.50 0.90 -- 100.00 67.00 99.99 52
67 \w 113.00 149.00 0.50 0.90 -- 100.00 77.00 120.00 72
68 \w 80.00 121.00 0.50 0.90 -- 100.00 53.00 150.00 82
69 \w 127.00 153.00 0.50 0.90 -- 100.00 53.00 150.00 52
70 \w 75.00 108.00 0.50 0.90 -- 100.00-111.00-120.00 66
71 \w 132.00 157.00 0.50 0.90 -- 100.00 69.00 90.00 50
72 \w 120.00 146.00 0.50 0.90 -- 100.00 61.00 120.00 52
73 \w 76.00 112.00 0.50 0.90 -- 100.00 69.00 60.00 72
74 \w 36.00 61.00 0.50 0.90 -- 100.00-133.00 30.00 50
75 \w 80.00 120.00 0.50 0.90 -- 100.00 53.00-180.00 80
76 \w 86.00 115.00 0.50 0.90 -- 100.00 61.00-150.00 58
77 \w 80.00 106.00 0.50 0.90 -- 100.00 53.00 90.00 52
78 \w 76.00 105.00 0.50 0.90 -- 100.00 69.00 90.00 58
79 \w 83.00 109.00 0.50 0.90 -- 100.00 45.00 90.00 52
80 \w 132.00 157.00 0.50 0.90 -- 100.00 61.00-150.00 50
81 \w 78.00 107.00 0.50 0.90 -- 100.00 61.00 90.00 58
82 \w 43.00 94.00 0.50 0.90 -- 100.00 -93.00 60.00 102
83 \w 79.00 104.00 0.50 0.90 -- 100.00 61.00 60.00 50
84 \w 82.00 130.00 0.50 0.90 -- 100.00 -86.00-180.00 96
85 \w 76.00 101.00 0.50 0.90 -- 100.00 69.00 150.00 50
86 \w 26.00 51.00 0.50 0.90 -- 100.00 -93.00 -30.00 50
87 \w 108.00 140.00 0.50 0.90 -- 100.00 111.00 30.00 64
88 \w 83.00 109.00 0.50 0.90 -- 100.00 77.00 60.00 52
89 \w 83.00 108.00 0.50 0.90 -- 100.00 77.00 90.00 50
90 \w 83.00 109.00 0.50 0.90 -- 100.00 77.00 120.00 52
91 \w 130.00 156.00 0.50 0.90 -- 100.00 53.00 -60.00 52
92 \w 106.00 131.00 0.50 0.90 -- 100.00 22.00 -60.00 50
93 \w 82.00 108.00 0.50 0.90 -- 100.00-111.00-180.00 52
94 \w 37.00 65.00 0.50 0.90 -- 100.00-111.00 0.00 56
95 \w 86.00 120.00 0.50 0.90 -- 100.00 37.00 60.00 68
96 \w 80.00 110.00 0.50 0.90 -- 100.00 53.00 120.00 60
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.1369845000
_diffrn_orient_matrix_UB_12 -0.0247362000
_diffrn_orient_matrix_UB_13 0.0841085000
_diffrn_orient_matrix_UB_21 0.0640861000
_diffrn_orient_matrix_UB_22 0.0555530000
_diffrn_orient_matrix_UB_23 -0.0680923000
_diffrn_orient_matrix_UB_31 -0.0024101000
_diffrn_orient_matrix_UB_32 0.0712990000
_diffrn_orient_matrix_UB_33 0.0822795000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_special_details ?
_reflns_Friedel_coverage 0.895
_reflns_Friedel_fraction_full 0.967
_reflns_Friedel_fraction_max 0.963
_reflns_number_gt 7401
_reflns_number_total 7584
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 70.93
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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 ?
_refine_diff_density_max 0.179
_refine_diff_density_min -0.196
_refine_diff_density_rms 0.042
_refine_ls_abs_structure_details
;
Flack x determined using 3387 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -0.009(5)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 553
_refine_ls_number_reflns 7584
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0241
_refine_ls_R_factor_gt 0.0233
_refine_ls_restrained_S_all 1.031
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.0377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0580
_refine_ls_wR_factor_ref 0.0585
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C2(H2A), C2A(H2AB)
2.b Aromatic/amide H refined with riding coordinates:
C7A(H7A), C16(H16), C15(H15), C15A(H15A), C10A(H10A), C13(H13), C7(H7),
C10(H10), C9(H9), C13A(H13A), C9A(H9A), C16A(H16A)
2.c Idealised Me refined as rotating group:
C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C20A(H20D,
H20E,H20F)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl3 Cl 0.77991(6) 0.46437(4) 0.32231(5) 0.01716(13) Uani 1 1 d . . . . .
Cl2A Cl 0.00367(6) 0.31701(4) 0.31563(6) 0.02028(14) Uani 1 1 d . . . . .
Cl1 Cl 1.19783(6) 0.67109(4) 1.02248(6) 0.02126(14) Uani 1 1 d . . . . .
Cl2 Cl 0.97906(6) 0.57293(4) 0.57482(6) 0.02133(14) Uani 1 1 d . . . . .
Cl3A Cl 0.44331(6) 0.56415(4) 0.96937(6) 0.02088(14) Uani 1 1 d . . . . .
Cl1A Cl 0.24837(6) 0.42868(4) 0.75234(5) 0.02075(14) Uani 1 1 d . . . . .
Cl4 Cl 0.70510(7) 0.73016(4) 0.05012(6) 0.02208(14) Uani 1 1 d . . . . .
Cl4A Cl 0.46509(7) 0.29822(5) 1.23328(6) 0.02363(15) Uani 1 1 d . . . . .
O3A O 0.87425(19) 0.39077(12) 0.64542(16) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.31914(19) 0.71459(12) 0.53452(17) 0.0170(4) Uani 1 1 d . . . . .
O3 O 0.34142(19) 0.61153(12) 0.66256(17) 0.0178(4) Uani 1 1 d . . . . .
O4A O 0.88550(19) 0.28613(12) 0.76952(17) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.23209(18) 0.56183(13) 0.39381(17) 0.0187(4) Uani 1 1 d . . . . .
O1A O 0.8938(2) 0.50421(13) 1.02732(17) 0.0215(4) Uani 1 1 d . . . . .
O1 O 0.32953(19) 0.50158(13) 0.27740(17) 0.0212(4) Uani 1 1 d . . . . .
O2A O 0.98366(19) 0.42991(14) 0.91708(17) 0.0218(4) Uani 1 1 d . . . . .
N1A N 0.6117(2) 0.36403(14) 0.6889(2) 0.0159(5) Uani 1 1 d . . . . .
N2 N 0.6931(2) 0.53805(14) 0.5428(2) 0.0143(4) Uani 1 1 d . . . . .
N2A N 0.5259(2) 0.47524(14) 0.7592(2) 0.0152(4) Uani 1 1 d . . . . .
N1 N 0.6009(2) 0.64305(14) 0.61938(19) 0.0152(4) Uani 1 1 d . . . . .
C5 C 0.8305(3) 0.61725(16) 0.7118(2) 0.0151(5) Uani 1 1 d . . . . .
C17A C 0.8824(3) 0.46376(17) 0.9402(2) 0.0164(5) Uani 1 1 d . . . . .
C19A C 0.8406(3) 0.35694(16) 0.7202(2) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.7028(3) 0.59941(16) 0.6187(2) 0.0139(5) Uani 1 1 d . . . . .
C19 C 0.3711(3) 0.64540(16) 0.5861(2) 0.0140(5) Uani 1 1 d . . . . .
C4 C 0.4804(3) 0.61564(16) 0.5447(2) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.5848(2) 0.53703(16) 0.4289(2) 0.0145(5) Uani 1 1 d . . . . .
H2A H 0.5710 0.4796 0.4000 0.017 Uiso 1 1 calc R . . . .
C5A C 0.3821(3) 0.38916(16) 0.6014(2) 0.0151(5) Uani 1 1 d . . . . .
C7A C 0.1435(3) 0.37489(17) 0.5323(2) 0.0172(5) Uani 1 1 d . . . . .
H7A H 0.0620 0.3816 0.5447 0.021 Uiso 1 1 calc R . . . .
C16 C 0.5650(3) 0.66518(17) 0.3034(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.5072 0.6872 0.3399 0.019 Uiso 1 1 calc R . . . .
C15 C 0.5933(3) 0.71066(17) 0.2181(2) 0.0176(5) Uani 1 1 d . . . . .
H15 H 0.5558 0.7630 0.1964 0.021 Uiso 1 1 calc R . . . .
C15A C 0.6058(3) 0.31423(18) 1.0878(2) 0.0180(5) Uani 1 1 d . . . . .
H15A H 0.6379 0.2610 1.1120 0.022 Uiso 1 1 calc R . . . .
C20 C 0.2210(3) 0.74943(17) 0.5780(2) 0.0189(6) Uani 1 1 d . . . . .
H20A H 0.1906 0.8014 0.5383 0.028 Uiso 1 1 calc GR . . . .
H20B H 0.2596 0.7585 0.6633 0.028 Uiso 1 1 calc GR . . . .
H20C H 0.1466 0.7120 0.5618 0.028 Uiso 1 1 calc GR . . . .
C1A C 0.5121(3) 0.41006(16) 0.6889(2) 0.0148(5) Uani 1 1 d . . . . .
C10A C 0.3815(3) 0.35493(16) 0.4948(2) 0.0172(5) Uani 1 1 d . . . . .
H10A H 0.4626 0.3475 0.4818 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7359(3) 0.60234(17) 0.1969(2) 0.0160(5) Uani 1 1 d . . . . .
H13 H 0.7944 0.5809 0.1607 0.019 Uiso 1 1 calc R . . . .
C7 C 1.0696(3) 0.62117(17) 0.7988(3) 0.0180(5) Uani 1 1 d . . . . .
H7 H 1.1535 0.6107 0.7931 0.022 Uiso 1 1 calc R . . . .
C10 C 0.8249(3) 0.65176(16) 0.8168(2) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.7416 0.6631 0.8233 0.020 Uiso 1 1 calc R . . . .
C3A C 0.7543(3) 0.44370(16) 0.8512(2) 0.0147(5) Uani 1 1 d . . . . .
C12 C 0.7059(2) 0.55906(16) 0.2837(2) 0.0143(5) Uani 1 1 d . . . . .
C3 C 0.4628(3) 0.56485(17) 0.4521(2) 0.0147(5) Uani 1 1 d . . . . .
C11A C 0.5982(3) 0.43432(17) 0.9675(2) 0.0147(5) Uani 1 1 d . . . . .
C9 C 0.9370(3) 0.66972(18) 0.9109(2) 0.0182(5) Uani 1 1 d . . . . .
H9 H 0.9310 0.6933 0.9810 0.022 Uiso 1 1 calc R . . . .
C11 C 0.6185(3) 0.58834(16) 0.3373(2) 0.0146(5) Uani 1 1 d . . . . .
C13A C 0.4693(3) 0.42860(19) 1.0990(2) 0.0179(5) Uani 1 1 d . . . . .
H13A H 0.4104 0.4535 1.1318 0.021 Uiso 1 1 calc R . . . .
C6 C 0.9561(3) 0.60504(17) 0.7045(2) 0.0160(5) Uani 1 1 d . . . . .
C9A C 0.2665(3) 0.33148(17) 0.4077(2) 0.0181(6) Uani 1 1 d . . . . .
H9A H 0.2682 0.3081 0.3361 0.022 Uiso 1 1 calc R . . . .
C12A C 0.5092(3) 0.46826(17) 1.0154(2) 0.0163(5) Uani 1 1 d . . . . .
C4A C 0.7337(3) 0.39063(16) 0.7612(2) 0.0151(5) Uani 1 1 d . . . . .
C2A C 0.6351(3) 0.47848(16) 0.8723(2) 0.0147(5) Uani 1 1 d . . . . .
H2AB H 0.6530 0.5368 0.8960 0.018 Uiso 1 1 calc R . . . .
C8 C 1.0581(3) 0.65269(16) 0.9011(2) 0.0172(5) Uani 1 1 d . . . . .
C14 C 0.6777(3) 0.67779(17) 0.1649(2) 0.0164(5) Uani 1 1 d . . . . .
C17 C 0.3375(3) 0.53895(16) 0.3659(2) 0.0152(5) Uani 1 1 d . . . . .
C16A C 0.6456(3) 0.35692(17) 1.0056(2) 0.0170(5) Uani 1 1 d . . . . .
H16A H 0.7067 0.3325 0.9748 0.020 Uiso 1 1 calc R . . . .
C6A C 0.2604(3) 0.39675(16) 0.6185(2) 0.0157(5) Uani 1 1 d . . . . .
C8A C 0.1488(3) 0.34280(16) 0.4272(2) 0.0168(5) Uani 1 1 d . . . . .
C18 C 0.1072(3) 0.54193(18) 0.3060(3) 0.0206(6) Uani 1 1 d . . . . .
H18A H 0.0980 0.5711 0.2327 0.031 Uiso 1 1 calc GR . . . .
H18B H 0.0361 0.5580 0.3347 0.031 Uiso 1 1 calc GR . . . .
H18C H 0.1026 0.4832 0.2912 0.031 Uiso 1 1 calc GR . . . .
C14A C 0.5186(3) 0.35109(18) 1.1332(2) 0.0181(5) Uani 1 1 d . . . . .
C18A C 1.1104(3) 0.4375(2) 1.0078(3) 0.0252(6) Uani 1 1 d . . . . .
H18D H 1.1766 0.4100 0.9824 0.038 Uiso 1 1 calc GR . . . .
H18E H 1.1076 0.4125 1.0808 0.038 Uiso 1 1 calc GR . . . .
H18F H 1.1331 0.4952 1.0218 0.038 Uiso 1 1 calc GR . . . .
C20A C 0.9879(3) 0.25019(19) 0.7332(3) 0.0243(6) Uani 1 1 d . . . . .
H20D H 0.9506 0.2321 0.6510 0.036 Uiso 1 1 calc GR . . . .
H20E H 1.0257 0.2035 0.7838 0.036 Uiso 1 1 calc GR . . . .
H20F H 1.0566 0.2907 0.7401 0.036 Uiso 1 1 calc GR . . . .
H2 H 0.755(4) 0.507(3) 0.554(3) 0.027(10) Uiso 1 1 d . . . . .
H2AA H 0.465(4) 0.507(2) 0.749(3) 0.025(10) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl3 0.0167(3) 0.0167(3) 0.0191(3) -0.0011(2) 0.0074(2) 0.0032(2)
Cl2A 0.0148(3) 0.0233(3) 0.0217(3) -0.0062(2) 0.0049(2) -0.0025(2)
Cl1 0.0165(3) 0.0245(3) 0.0201(3) -0.0056(3) 0.0027(2) -0.0014(3)
Cl2 0.0175(3) 0.0303(3) 0.0198(3) -0.0069(3) 0.0110(2) -0.0041(3)
Cl3A 0.0194(3) 0.0206(3) 0.0212(3) -0.0036(3) 0.0049(2) 0.0060(3)
Cl1A 0.0186(3) 0.0303(3) 0.0164(3) -0.0048(3) 0.0099(2) -0.0035(3)
Cl4 0.0227(3) 0.0284(3) 0.0178(3) 0.0068(3) 0.0103(3) 0.0031(3)
Cl4A 0.0219(3) 0.0354(4) 0.0170(3) 0.0031(3) 0.0110(2) -0.0025(3)
O3A 0.0185(9) 0.0214(10) 0.0161(9) 0.0018(8) 0.0092(8) 0.0025(8)
O4 0.0188(9) 0.0179(9) 0.0165(9) 0.0018(7) 0.0090(8) 0.0052(8)
O3 0.0165(9) 0.0213(10) 0.0175(9) 0.0037(8) 0.0084(8) 0.0026(8)
O4A 0.0200(10) 0.0183(10) 0.0220(10) 0.0022(8) 0.0094(8) 0.0044(8)
O2 0.0128(9) 0.0252(10) 0.0186(9) -0.0046(8) 0.0059(7) -0.0001(8)
O1A 0.0202(10) 0.0252(10) 0.0184(10) -0.0052(8) 0.0056(8) 0.0002(8)
O1 0.0189(10) 0.0283(11) 0.0172(10) -0.0063(8) 0.0073(8) -0.0001(8)
O2A 0.0119(9) 0.0318(11) 0.0209(9) -0.0068(8) 0.0044(8) 0.0010(8)
N1A 0.0140(11) 0.0183(11) 0.0163(11) -0.0002(9) 0.0062(9) -0.0004(9)
N2 0.0127(11) 0.0152(11) 0.0158(11) 0.0004(8) 0.0058(9) 0.0034(9)
N2A 0.0135(11) 0.0168(11) 0.0156(11) 0.0018(9) 0.0053(9) 0.0026(9)
N1 0.0127(11) 0.0187(11) 0.0155(10) -0.0004(8) 0.0063(9) 0.0003(9)
C5 0.0154(13) 0.0147(12) 0.0158(12) 0.0017(10) 0.0063(10) -0.0011(10)
C17A 0.0160(13) 0.0181(12) 0.0160(12) 0.0022(10) 0.0065(10) -0.0010(11)
C19A 0.0142(13) 0.0168(13) 0.0132(13) -0.0022(10) 0.0038(10) -0.0012(10)
C1 0.0170(13) 0.0147(12) 0.0120(12) 0.0021(9) 0.0077(10) -0.0008(10)
C19 0.0110(12) 0.0174(13) 0.0127(12) -0.0022(10) 0.0028(10) 0.0004(10)
C4 0.0142(12) 0.0151(12) 0.0160(12) 0.0026(10) 0.0077(10) 0.0005(10)
C2 0.0130(12) 0.0153(12) 0.0151(12) -0.0017(10) 0.0048(10) -0.0003(10)
C5A 0.0150(13) 0.0152(13) 0.0161(12) 0.0019(10) 0.0064(11) -0.0001(10)
C7A 0.0151(13) 0.0165(13) 0.0222(14) -0.0003(10) 0.0093(11) -0.0010(10)
C16 0.0175(13) 0.0166(12) 0.0151(12) -0.0025(10) 0.0075(10) 0.0006(11)
C15 0.0179(13) 0.0179(13) 0.0169(13) -0.0017(10) 0.0057(11) 0.0009(10)
C15A 0.0167(13) 0.0216(13) 0.0159(12) 0.0005(10) 0.0059(10) 0.0002(11)
C20 0.0172(14) 0.0221(14) 0.0177(13) 0.0000(11) 0.0062(11) 0.0066(11)
C1A 0.0169(13) 0.0175(13) 0.0122(12) 0.0026(10) 0.0078(10) -0.0014(10)
C10A 0.0150(13) 0.0192(13) 0.0186(13) -0.0003(10) 0.0074(11) 0.0008(10)
C13 0.0139(12) 0.0219(13) 0.0124(12) -0.0023(10) 0.0049(10) 0.0000(10)
C7 0.0161(13) 0.0150(13) 0.0248(14) -0.0001(10) 0.0096(11) 0.0004(10)
C10 0.0156(13) 0.0176(13) 0.0174(13) 0.0006(10) 0.0073(11) 0.0010(10)
C3A 0.0134(13) 0.0181(13) 0.0141(12) 0.0040(10) 0.0067(10) 0.0002(10)
C12 0.0129(12) 0.0148(12) 0.0140(12) -0.0031(10) 0.0031(10) 0.0004(10)
C3 0.0150(12) 0.0154(12) 0.0149(12) 0.0012(10) 0.0067(10) 0.0001(10)
C11A 0.0131(12) 0.0188(12) 0.0122(11) -0.0032(10) 0.0045(10) -0.0009(10)
C9 0.0196(13) 0.0203(13) 0.0163(13) -0.0013(11) 0.0081(11) -0.0013(11)
C11 0.0130(12) 0.0172(13) 0.0127(12) -0.0024(10) 0.0032(10) -0.0007(10)
C13A 0.0123(12) 0.0281(14) 0.0129(12) -0.0048(11) 0.0038(10) 0.0008(11)
C6 0.0188(14) 0.0152(12) 0.0153(12) -0.0003(10) 0.0075(11) 0.0010(10)
C9A 0.0181(13) 0.0190(13) 0.0177(13) -0.0016(10) 0.0066(11) -0.0007(11)
C12A 0.0129(12) 0.0201(13) 0.0148(12) -0.0033(10) 0.0033(10) 0.0014(11)
C4A 0.0152(12) 0.0152(12) 0.0162(12) 0.0028(10) 0.0069(10) -0.0003(10)
C2A 0.0146(12) 0.0155(13) 0.0142(12) -0.0004(10) 0.0051(10) 0.0009(10)
C8 0.0172(13) 0.0151(13) 0.0176(13) 0.0006(10) 0.0039(11) -0.0008(10)
C14 0.0161(13) 0.0217(13) 0.0117(12) 0.0001(10) 0.0051(10) -0.0017(11)
C17 0.0162(13) 0.0160(12) 0.0166(13) 0.0019(10) 0.0096(10) 0.0005(10)
C16A 0.0156(13) 0.0196(14) 0.0163(12) -0.0029(10) 0.0062(10) -0.0009(10)
C6A 0.0189(13) 0.0156(12) 0.0148(12) 0.0001(10) 0.0087(10) 0.0000(10)
C8A 0.0159(13) 0.0166(13) 0.0175(13) -0.0013(10) 0.0051(10) -0.0021(10)
C18 0.0126(13) 0.0245(15) 0.0221(14) -0.0016(11) 0.0024(11) 0.0000(11)
C14A 0.0161(13) 0.0279(14) 0.0107(12) -0.0009(10) 0.0049(10) -0.0042(11)
C18A 0.0126(13) 0.0319(16) 0.0260(15) -0.0049(13) -0.0003(11) 0.0013(12)
C20A 0.0242(15) 0.0246(15) 0.0253(15) -0.0017(12) 0.0099(12) 0.0095(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl3 C12 1.741(3) . ?
Cl2A C8A 1.739(3) . ?
Cl1 C8 1.738(3) . ?
Cl2 C6 1.744(3) . ?
Cl3A C12A 1.742(3) . ?
Cl1A C6A 1.741(3) . ?
Cl4 C14 1.738(3) . ?
Cl4A C14A 1.736(3) . ?
O3A C19A 1.215(3) . ?
O4 C19 1.326(3) . ?
O4 C20 1.451(3) . ?
O3 C19 1.209(3) . ?
O4A C19A 1.323(3) . ?
O4A C20A 1.448(3) . ?
O2 C17 1.347(3) . ?
O2 C18 1.444(3) . ?
O1A C17A 1.213(4) . ?
O1 C17 1.208(4) . ?
O2A C17A 1.340(3) . ?
O2A C18A 1.441(3) . ?
N1A C1A 1.317(4) . ?
N1A C4A 1.384(4) . ?
N2 C1 1.341(4) . ?
N2 C2 1.473(3) . ?
N2A C1A 1.342(4) . ?
N2A C2A 1.471(3) . ?
N1 C1 1.318(4) . ?
N1 C4 1.385(4) . ?
C5 C1 1.485(4) . ?
C5 C10 1.405(4) . ?
C5 C6 1.407(4) . ?
C17A C3A 1.475(4) . ?
C19A C4A 1.508(4) . ?
C19 C4 1.512(4) . ?
C4 C3 1.354(4) . ?
C2 C3 1.510(4) . ?
C2 C11 1.528(4) . ?
C5A C1A 1.485(4) . ?
C5A C10A 1.399(4) . ?
C5A C6A 1.406(4) . ?
C7A C6A 1.386(4) . ?
C7A C8A 1.390(4) . ?
C16 C15 1.386(4) . ?
C16 C11 1.392(4) . ?
C15 C14 1.390(4) . ?
C15A C16A 1.395(4) . ?
C15A C14A 1.381(4) . ?
C10A C9A 1.384(4) . ?
C13 C12 1.390(4) . ?
C13 C14 1.386(4) . ?
C7 C6 1.387(4) . ?
C7 C8 1.380(4) . ?
C10 C9 1.383(4) . ?
C3A C4A 1.350(4) . ?
C3A C2A 1.509(3) . ?
C12 C11 1.398(4) . ?
C3 C17 1.465(4) . ?
C11A C12A 1.396(4) . ?
C11A C2A 1.520(4) . ?
C11A C16A 1.390(4) . ?
C9 C8 1.384(4) . ?
C13A C12A 1.385(4) . ?
C13A C14A 1.389(4) . ?
C9A C8A 1.384(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O4 C20 114.6(2) . . ?
C19A O4A C20A 115.2(2) . . ?
C17 O2 C18 114.6(2) . . ?
C17A O2A C18A 116.3(2) . . ?
C1A N1A C4A 115.2(2) . . ?
C1 N2 C2 119.8(2) . . ?
C1A N2A C2A 119.7(2) . . ?
C1 N1 C4 115.1(2) . . ?
C10 C5 C1 116.5(2) . . ?
C10 C5 C6 116.8(3) . . ?
C6 C5 C1 126.7(2) . . ?
O1A C17A O2A 123.9(2) . . ?
O1A C17A C3A 123.1(3) . . ?
O2A C17A C3A 113.0(2) . . ?
O3A C19A O4A 125.4(3) . . ?
O3A C19A C4A 122.0(2) . . ?
O4A C19A C4A 112.5(2) . . ?
N2 C1 C5 120.1(2) . . ?
N1 C1 N2 122.8(2) . . ?
N1 C1 C5 117.0(2) . . ?
O4 C19 C4 112.2(2) . . ?
O3 C19 O4 124.9(2) . . ?
O3 C19 C4 122.8(2) . . ?
N1 C4 C19 110.5(2) . . ?
C3 C4 N1 125.0(2) . . ?
C3 C4 C19 124.3(2) . . ?
N2 C2 C3 107.2(2) . . ?
N2 C2 C11 110.9(2) . . ?
C3 C2 C11 113.8(2) . . ?
C10A C5A C1A 117.0(2) . . ?
C10A C5A C6A 117.1(2) . . ?
C6A C5A C1A 125.8(2) . . ?
C6A C7A C8A 118.2(2) . . ?
C15 C16 C11 122.2(2) . . ?
C16 C15 C14 118.4(3) . . ?
C14A C15A C16A 118.5(3) . . ?
N1A C1A N2A 122.8(2) . . ?
N1A C1A C5A 116.5(2) . . ?
N2A C1A C5A 120.6(2) . . ?
C9A C10A C5A 122.1(3) . . ?
C14 C13 C12 117.8(2) . . ?
C8 C7 C6 118.7(3) . . ?
C9 C10 C5 122.1(3) . . ?
C17A C3A C2A 116.1(2) . . ?
C4A C3A C17A 126.0(2) . . ?
C4A C3A C2A 117.5(2) . . ?
C13 C12 Cl3 117.1(2) . . ?
C13 C12 C11 122.5(3) . . ?
C11 C12 Cl3 120.4(2) . . ?
C4 C3 C2 116.8(2) . . ?
C4 C3 C17 126.9(2) . . ?
C17 C3 C2 116.1(2) . . ?
C12A C11A C2A 121.0(2) . . ?
C16A C11A C12A 117.3(2) . . ?
C16A C11A C2A 121.6(2) . . ?
C10 C9 C8 118.7(3) . . ?
C16 C11 C2 122.4(2) . . ?
C16 C11 C12 117.1(2) . . ?
C12 C11 C2 120.5(2) . . ?
C12A C13A C14A 117.7(2) . . ?
C5 C6 Cl2 122.2(2) . . ?
C7 C6 Cl2 115.9(2) . . ?
C7 C6 C5 121.9(3) . . ?
C10A C9A C8A 118.6(3) . . ?
C11A C12A Cl3A 119.8(2) . . ?
C13A C12A Cl3A 117.5(2) . . ?
C13A C12A C11A 122.7(3) . . ?
N1A C4A C19A 110.7(2) . . ?
C3A C4A N1A 124.9(2) . . ?
C3A C4A C19A 124.3(2) . . ?
N2A C2A C3A 107.2(2) . . ?
N2A C2A C11A 110.3(2) . . ?
C3A C2A C11A 113.8(2) . . ?
C7 C8 Cl1 120.0(2) . . ?
C7 C8 C9 121.7(3) . . ?
C9 C8 Cl1 118.2(2) . . ?
C15 C14 Cl4 119.3(2) . . ?
C13 C14 Cl4 118.7(2) . . ?
C13 C14 C15 121.9(3) . . ?
O2 C17 C3 113.7(2) . . ?
O1 C17 O2 123.3(3) . . ?
O1 C17 C3 123.0(2) . . ?
C11A C16A C15A 121.8(3) . . ?
C5A C6A Cl1A 122.0(2) . . ?
C7A C6A Cl1A 115.9(2) . . ?
C7A C6A C5A 122.0(2) . . ?
C7A C8A Cl2A 119.4(2) . . ?
C9A C8A Cl2A 118.6(2) . . ?
C9A C8A C7A 122.0(3) . . ?
C15A C14A Cl4A 119.2(2) . . ?
C15A C14A C13A 122.0(3) . . ?
C13A C14A Cl4A 118.7(2) . . ?
_shelx_res_file
;
15289_htk-02.res created by SHELXL-2014/7
TITL 15289_htk-02_a.res in P2(1)
REM Old TITL 15289_HTK-02 in P21/m #11
REM SHELXT solution in P2(1)
REM R1 0.061, Rweak 0.026, Alpha 0.002, Orientation as input
REM Flack x = -0.007 ( 0.007 ) from Parsons' quotients
REM Formula found by SHELXT: C40 Cl8 N4 O8
CELL 1.54184 10.8248 16.4407 12.0407 90 109.771 90
ZERR 4 0.0001 0.0001 0.0001 0 0.001 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Cl N O
UNIT 80 56 16 8 16
L.S. 10
PLAN 20
TEMP -173(2)
LIST 6
fmap 2
ACTA
REM
REM
REM
WGHT 0.034000 0.037700
FVAR 0.52794
CL3 3 0.779909 0.464372 0.322306 11.00000 0.01673 0.01667 =
0.01909 -0.00112 0.00738 0.00318
CL2A 3 0.003665 0.317006 0.315632 11.00000 0.01478 0.02333 =
0.02174 -0.00623 0.00487 -0.00247
CL1 3 1.197827 0.671089 1.022485 11.00000 0.01652 0.02449 =
0.02008 -0.00559 0.00268 -0.00135
CL2 3 0.979059 0.572931 0.574823 11.00000 0.01749 0.03032 =
0.01976 -0.00694 0.01097 -0.00411
CL3A 3 0.443309 0.564150 0.969373 11.00000 0.01936 0.02060 =
0.02123 -0.00358 0.00494 0.00601
CL1A 3 0.248372 0.428681 0.752337 11.00000 0.01858 0.03029 =
0.01641 -0.00483 0.00990 -0.00347
CL4 3 0.705103 0.730161 0.050121 11.00000 0.02270 0.02838 =
0.01778 0.00684 0.01029 0.00307
CL4A 3 0.465093 0.298217 1.233275 11.00000 0.02188 0.03539 =
0.01697 0.00309 0.01098 -0.00251
O3A 5 0.874245 0.390766 0.645419 11.00000 0.01848 0.02137 =
0.01614 0.00177 0.00919 0.00250
O4 5 0.319144 0.714591 0.534522 11.00000 0.01876 0.01789 =
0.01651 0.00179 0.00896 0.00516
O3 5 0.341416 0.611532 0.662562 11.00000 0.01650 0.02128 =
0.01751 0.00369 0.00840 0.00257
O4A 5 0.885499 0.286125 0.769525 11.00000 0.02003 0.01833 =
0.02195 0.00223 0.00940 0.00440
O2 5 0.232088 0.561834 0.393815 11.00000 0.01278 0.02523 =
0.01863 -0.00455 0.00588 -0.00008
O1A 5 0.893755 0.504214 1.027321 11.00000 0.02025 0.02524 =
0.01843 -0.00521 0.00561 0.00016
O1 5 0.329525 0.501577 0.277399 11.00000 0.01890 0.02832 =
0.01724 -0.00629 0.00732 -0.00007
O2A 5 0.983662 0.429913 0.917083 11.00000 0.01189 0.03181 =
0.02094 -0.00679 0.00441 0.00099
N1A 4 0.611661 0.364026 0.688936 11.00000 0.01398 0.01829 =
0.01631 -0.00017 0.00623 -0.00040
N2 4 0.693149 0.538051 0.542831 11.00000 0.01269 0.01523 =
0.01583 0.00036 0.00576 0.00342
N2A 4 0.525919 0.475242 0.759212 11.00000 0.01347 0.01684 =
0.01557 0.00182 0.00529 0.00260
N1 4 0.600899 0.643055 0.619375 11.00000 0.01266 0.01865 =
0.01551 -0.00042 0.00629 0.00034
C5 1 0.830456 0.617252 0.711791 11.00000 0.01542 0.01469 =
0.01583 0.00166 0.00631 -0.00109
C17A 1 0.882423 0.463762 0.940200 11.00000 0.01599 0.01815 =
0.01599 0.00221 0.00653 -0.00098
C19A 1 0.840573 0.356940 0.720227 11.00000 0.01425 0.01677 =
0.01321 -0.00223 0.00381 -0.00122
C1 1 0.702781 0.599412 0.618665 11.00000 0.01701 0.01469 =
0.01201 0.00213 0.00773 -0.00077
C19 1 0.371067 0.645398 0.586081 11.00000 0.01095 0.01739 =
0.01270 -0.00218 0.00283 0.00041
C4 1 0.480407 0.615639 0.544715 11.00000 0.01421 0.01513 =
0.01602 0.00262 0.00771 0.00045
C2 1 0.584780 0.537032 0.428912 11.00000 0.01302 0.01533 =
0.01512 -0.00165 0.00476 -0.00029
AFIX 13
H2A 2 0.570969 0.479606 0.399954 11.00000 -1.20000
AFIX 0
C5A 1 0.382135 0.389165 0.601373 11.00000 0.01497 0.01518 =
0.01605 0.00185 0.00635 -0.00013
C7A 1 0.143489 0.374885 0.532297 11.00000 0.01508 0.01653 =
0.02222 -0.00028 0.00928 -0.00100
AFIX 43
H7A 2 0.061958 0.381644 0.544680 11.00000 -1.20000
AFIX 0
C16 1 0.565011 0.665180 0.303368 11.00000 0.01745 0.01659 =
0.01513 -0.00253 0.00747 0.00063
AFIX 43
H16 2 0.507201 0.687167 0.339933 11.00000 -1.20000
AFIX 0
C15 1 0.593262 0.710657 0.218052 11.00000 0.01790 0.01791 =
0.01695 -0.00170 0.00575 0.00089
AFIX 43
H15 2 0.555828 0.763044 0.196395 11.00000 -1.20000
AFIX 0
C15A 1 0.605782 0.314232 1.087793 11.00000 0.01673 0.02160 =
0.01590 0.00054 0.00589 0.00021
AFIX 43
H15A 2 0.637942 0.261028 1.111975 11.00000 -1.20000
AFIX 0
C20 1 0.221015 0.749430 0.578001 11.00000 0.01723 0.02213 =
0.01768 -0.00002 0.00618 0.00658
AFIX 137
H20A 2 0.190649 0.801388 0.538252 11.00000 -1.50000
H20B 2 0.259570 0.758452 0.663270 11.00000 -1.50000
H20C 2 0.146572 0.711972 0.561838 11.00000 -1.50000
AFIX 0
C1A 1 0.512073 0.410055 0.688886 11.00000 0.01685 0.01748 =
0.01225 0.00258 0.00776 -0.00137
C10A 1 0.381484 0.354927 0.494761 11.00000 0.01500 0.01922 =
0.01858 -0.00033 0.00744 0.00078
AFIX 43
H10A 2 0.462562 0.347550 0.481755 11.00000 -1.20000
AFIX 0
C13 1 0.735892 0.602343 0.196877 11.00000 0.01391 0.02195 =
0.01243 -0.00229 0.00491 0.00000
AFIX 43
H13 2 0.794405 0.580889 0.160667 11.00000 -1.20000
AFIX 0
C7 1 1.069565 0.621174 0.798799 11.00000 0.01610 0.01503 =
0.02485 -0.00008 0.00959 0.00039
AFIX 43
H7 2 1.153519 0.610734 0.793071 11.00000 -1.20000
AFIX 0
C10 1 0.824901 0.651755 0.816795 11.00000 0.01557 0.01755 =
0.01740 0.00065 0.00725 0.00103
AFIX 43
H10 2 0.741574 0.663097 0.823322 11.00000 -1.20000
AFIX 0
C3A 1 0.754293 0.443701 0.851200 11.00000 0.01343 0.01814 =
0.01405 0.00398 0.00667 0.00020
C12 1 0.705880 0.559063 0.283650 11.00000 0.01287 0.01485 =
0.01396 -0.00311 0.00311 0.00042
C3 1 0.462819 0.564848 0.452089 11.00000 0.01502 0.01536 =
0.01489 0.00117 0.00671 0.00014
C11A 1 0.598216 0.434321 0.967510 11.00000 0.01313 0.01883 =
0.01224 -0.00320 0.00446 -0.00090
C9 1 0.936990 0.669720 0.910948 11.00000 0.01963 0.02033 =
0.01627 -0.00133 0.00812 -0.00128
AFIX 43
H9 2 0.930960 0.693283 0.980974 11.00000 -1.20000
AFIX 0
C11 1 0.618529 0.588344 0.337274 11.00000 0.01302 0.01724 =
0.01267 -0.00239 0.00321 -0.00072
C13A 1 0.469332 0.428598 1.098990 11.00000 0.01232 0.02808 =
0.01286 -0.00479 0.00381 0.00079
AFIX 43
H13A 2 0.410361 0.453548 1.131804 11.00000 -1.20000
AFIX 0
C6 1 0.956141 0.605045 0.704504 11.00000 0.01880 0.01516 =
0.01535 -0.00033 0.00753 0.00099
C9A 1 0.266455 0.331482 0.407694 11.00000 0.01811 0.01903 =
0.01769 -0.00156 0.00658 -0.00072
AFIX 43
H9A 2 0.268232 0.308130 0.336081 11.00000 -1.20000
AFIX 0
C12A 1 0.509202 0.468265 1.015366 11.00000 0.01292 0.02013 =
0.01476 -0.00329 0.00328 0.00145
C4A 1 0.733677 0.390634 0.761162 11.00000 0.01516 0.01522 =
0.01618 0.00277 0.00686 -0.00029
C2A 1 0.635106 0.478479 0.872283 11.00000 0.01459 0.01554 =
0.01420 -0.00040 0.00510 0.00094
AFIX 13
H2AB 2 0.653041 0.536757 0.896046 11.00000 -1.20000
AFIX 0
C8 1 1.058095 0.652685 0.901116 11.00000 0.01718 0.01514 =
0.01760 0.00061 0.00385 -0.00085
C14 1 0.677663 0.677789 0.164945 11.00000 0.01611 0.02175 =
0.01172 0.00015 0.00509 -0.00166
C17 1 0.337456 0.538954 0.365936 11.00000 0.01619 0.01597 =
0.01661 0.00187 0.00962 0.00049
C16A 1 0.645596 0.356921 1.005591 11.00000 0.01559 0.01961 =
0.01629 -0.00286 0.00616 -0.00089
AFIX 43
H16A 2 0.706706 0.332457 0.974816 11.00000 -1.20000
AFIX 0
C6A 1 0.260428 0.396755 0.618524 11.00000 0.01892 0.01564 =
0.01476 0.00011 0.00866 0.00002
C8A 1 0.148763 0.342797 0.427220 11.00000 0.01589 0.01657 =
0.01750 -0.00132 0.00510 -0.00207
C18 1 0.107170 0.541932 0.306034 11.00000 0.01264 0.02453 =
0.02208 -0.00164 0.00241 -0.00005
AFIX 137
H18A 2 0.098001 0.571054 0.232655 11.00000 -1.50000
H18B 2 0.036103 0.558024 0.334688 11.00000 -1.50000
H18C 2 0.102642 0.483212 0.291193 11.00000 -1.50000
AFIX 0
C14A 1 0.518569 0.351086 1.133184 11.00000 0.01611 0.02791 =
0.01070 -0.00093 0.00493 -0.00423
C18A 1 1.110363 0.437481 1.007775 11.00000 0.01257 0.03192 =
0.02602 -0.00489 -0.00027 0.00131
AFIX 137
H18D 2 1.176618 0.409969 0.982411 11.00000 -1.50000
H18E 2 1.107587 0.412455 1.080763 11.00000 -1.50000
H18F 2 1.133067 0.495168 1.021838 11.00000 -1.50000
AFIX 0
C20A 1 0.987888 0.250190 0.733162 11.00000 0.02420 0.02462 =
0.02530 -0.00175 0.00992 0.00950
AFIX 137
H20D 2 0.950626 0.232121 0.650965 11.00000 -1.50000
H20E 2 1.025742 0.203476 0.783794 11.00000 -1.50000
H20F 2 1.056580 0.290657 0.740122 11.00000 -1.50000
AFIX 0
H2 2 0.755447 0.507117 0.554246 11.00000 0.02735
H2AA 2 0.465055 0.506950 0.748639 11.00000 0.02535
HKLF 4
REM 15289_htk-02_a.res in P2(1)
REM R1 = 0.0233 for 7401 Fo > 4sig(Fo) and 0.0241 for all 7584 data
REM 553 parameters refined using 1 restraints
END
WGHT 0.0340 0.0377
REM Highest difference peak 0.179, deepest hole -0.196, 1-sigma level 0.042
Q1 1 0.3992 0.5650 0.4024 11.00000 0.05 0.18
Q2 1 0.4392 0.4026 0.6387 11.00000 0.05 0.17
Q3 1 0.7812 0.3712 0.7480 11.00000 0.05 0.17
Q4 1 0.8711 0.6317 0.7006 11.00000 0.05 0.17
Q5 1 0.7116 0.4575 0.8626 11.00000 0.05 0.17
Q6 1 0.7433 0.4050 0.8266 11.00000 0.05 0.17
Q7 1 0.6869 0.6355 0.1757 11.00000 0.05 0.16
Q8 1 0.8320 0.6377 0.7445 11.00000 0.05 0.16
Q9 1 0.3830 0.3722 0.5557 11.00000 0.05 0.16
Q10 1 0.5968 0.5637 0.3839 11.00000 0.05 0.16
Q11 1 0.5372 0.4420 0.9676 11.00000 0.05 0.16
Q12 1 0.4252 0.6265 0.5584 11.00000 0.05 0.15
Q13 1 0.6205 0.4533 0.9236 11.00000 0.05 0.15
Q14 1 0.5009 0.3873 1.1173 11.00000 0.05 0.15
Q15 1 0.4553 0.5983 0.4829 11.00000 0.05 0.15
Q16 1 0.3544 0.4289 0.8256 11.00000 0.05 0.15
Q17 1 0.3279 0.3966 0.7803 11.00000 0.05 0.15
Q18 1 0.4609 0.4343 1.0373 11.00000 0.05 0.15
Q19 1 0.6180 0.4002 0.9859 11.00000 0.05 0.15
Q20 1 0.6172 0.6840 0.1796 11.00000 0.05 0.14
;
_shelx_res_checksum 50634
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.314
_oxdiff_exptl_absorpt_empirical_full_min 0.853