# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_jm1902
_database_code_depnum_ccdc_archive 'CCDC 1964614'
loop_
_audit_author_name
_audit_author_address
'Frank W. Heinemann'
;Friedrich Alexander Universitaet Erlangen Nuernberg
Germany
;
_audit_update_record
;
2019-11-08 deposited with the CCDC. 2020-03-30 downloaded from the CCDC.
;
_audit_creation_date 2019-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H39 N3, C F3 O3 S'
_chemical_formula_sum 'C26 H39 F3 N3 O3 S'
_chemical_formula_weight 530.66
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 11.3959(4)
_cell_length_b 8.8582(3)
_cell_length_c 26.7626(10)
_cell_angle_alpha 90
_cell_angle_beta 91.5800(10)
_cell_angle_gamma 90
_cell_volume 2700.58(17)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9879
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 29.51
_cell_measurement_theta_min 2.38
_shelx_estimated_absorpt_T_max 0.981
_shelx_estimated_absorpt_T_min 0.971
_exptl_absorpt_coefficient_mu 0.173
_exptl_absorpt_correction_T_max 0.7459
_exptl_absorpt_correction_T_min 0.7205
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.9659.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour red
_exptl_crystal_density_diffrn 1.305
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 1132
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.11
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0389
_diffrn_reflns_av_unetI/netI 0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 36
_diffrn_reflns_limit_l_min -36
_diffrn_reflns_number 44464
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.700
_diffrn_reflns_theta_min 2.380
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_source 'ImuS high brilliance micro-focus tube'
_diffrn_radiation_monochromator 'Quazar focussing montel optics'
_diffrn_measurement_device_type 'Bruker Kappa ImuS Duo Photon II CPAD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5762
_reflns_number_total 6963
_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_data_collection 'Bruker APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_reduction 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max 0.412
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.043
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 408
_refine_ls_number_reflns 6963
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0538
_refine_ls_R_factor_gt 0.0416
_refine_ls_restrained_S_all 1.051
_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^)+(0.0459P)^2^+1.1702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1005
_refine_ls_wR_factor_ref 0.1100
_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. Uiso/Uaniso restraints and constraints
C26 \\sim C26A: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
3. Others
Sof(S1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(C26A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=1-
FVAR(1)
Sof(S1)=Sof(O1)=Sof(O2)=Sof(O3)=Sof(C26)=Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
C20(H20), C23(H23)
4.b Secondary CH2 refined with riding coordinates:
C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C16(H16), C17(H17), C18(H18)
4.d Idealised Me refined as rotating group:
C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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
N1 N 0.72604(9) 0.19694(12) 0.55231(4) 0.0188(2) Uani 1 1 d . . . . .
N2 N 0.58359(9) 0.31379(13) 0.58753(4) 0.0221(2) Uani 1 1 d . . . . .
N3 N 0.81175(8) 0.47690(11) 0.64305(4) 0.01415(19) Uani 1 1 d . . . . .
C1 C 0.70005(10) 0.28306(13) 0.59254(4) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.62645(12) 0.17515(15) 0.52271(5) 0.0248(3) Uani 1 1 d . . . . .
H2 H 0.621184 0.118878 0.492517 0.030 Uiso 1 1 calc R . . . .
C3 C 0.53851(12) 0.24819(16) 0.54452(5) 0.0276(3) Uani 1 1 d . . . . .
H3 H 0.459420 0.253675 0.532487 0.033 Uiso 1 1 calc R . . . .
C4 C 0.84191(11) 0.14382(16) 0.53836(5) 0.0240(3) Uani 1 1 d . . . . .
H4A H 0.850416 0.155401 0.502222 0.036 Uiso 1 1 calc GR . . . .
H4B H 0.850599 0.037143 0.547430 0.036 Uiso 1 1 calc GR . . . .
H4C H 0.902500 0.203264 0.556061 0.036 Uiso 1 1 calc GR . . . .
C5 C 0.51283(12) 0.39390(19) 0.62360(6) 0.0333(3) Uani 1 1 d . . . . .
H5A H 0.436592 0.343731 0.626187 0.050 Uiso 1 1 calc GR . . . .
H5B H 0.500871 0.498339 0.612508 0.050 Uiso 1 1 calc GR . . . .
H5C H 0.553499 0.393436 0.656349 0.050 Uiso 1 1 calc GR . . . .
C6 C 0.78133(10) 0.32880(13) 0.63216(4) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.93259(10) 0.47542(13) 0.66735(4) 0.0159(2) Uani 1 1 d . . . . .
C8 C 0.92662(11) 0.32954(14) 0.69822(5) 0.0204(2) Uani 1 1 d . . . . .
H8A H 0.904171 0.352761 0.732853 0.025 Uiso 1 1 calc R . . . .
H8B H 1.004125 0.278999 0.699412 0.025 Uiso 1 1 calc R . . . .
C9 C 0.83327(10) 0.22532(13) 0.67261(4) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.95824(11) 0.61423(15) 0.69904(5) 0.0240(3) Uani 1 1 d . . . . .
H10A H 1.040194 0.611774 0.711108 0.036 Uiso 1 1 calc GR . . . .
H10B H 0.906317 0.615372 0.727619 0.036 Uiso 1 1 calc GR . . . .
H10C H 0.944784 0.705200 0.678840 0.036 Uiso 1 1 calc GR . . . .
C11 C 1.02649(10) 0.46200(15) 0.62777(5) 0.0215(3) Uani 1 1 d . . . . .
H11A H 1.103656 0.448712 0.644253 0.032 Uiso 1 1 calc GR . . . .
H11B H 1.026786 0.553949 0.607408 0.032 Uiso 1 1 calc GR . . . .
H11C H 1.009134 0.374741 0.606298 0.032 Uiso 1 1 calc GR . . . .
C12 C 0.73490(11) 0.18832(15) 0.70914(5) 0.0236(3) Uani 1 1 d . . . . .
H12A H 0.767678 0.130749 0.737510 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.674014 0.128308 0.691850 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.700511 0.282400 0.721268 0.035 Uiso 1 1 calc GR . . . .
C13 C 0.88707(12) 0.07687(14) 0.65514(5) 0.0232(3) Uani 1 1 d . . . . .
H13A H 0.916543 0.019674 0.684212 0.035 Uiso 1 1 calc GR . . . .
H13B H 0.952018 0.098429 0.632974 0.035 Uiso 1 1 calc GR . . . .
H13C H 0.827130 0.017407 0.637046 0.035 Uiso 1 1 calc GR . . . .
C14 C 0.74674(9) 0.60825(13) 0.62673(4) 0.0143(2) Uani 1 1 d . . . . .
C15 C 0.74919(9) 0.65644(13) 0.57656(4) 0.0148(2) Uani 1 1 d . . . . .
C16 C 0.67930(10) 0.77913(14) 0.56168(4) 0.0177(2) Uani 1 1 d . . . . .
H16 H 0.681108 0.813326 0.528061 0.021 Uiso 1 1 calc R . . . .
C17 C 0.60752(10) 0.85172(14) 0.59501(5) 0.0196(2) Uani 1 1 d . . . . .
H17 H 0.558742 0.932854 0.584047 0.023 Uiso 1 1 calc R . . . .
C18 C 0.60731(10) 0.80530(14) 0.64436(5) 0.0199(2) Uani 1 1 d . . . . .
H18 H 0.558730 0.856590 0.667122 0.024 Uiso 1 1 calc R . . . .
C19 C 0.67651(10) 0.68517(14) 0.66163(4) 0.0170(2) Uani 1 1 d . . . . .
C20 C 0.82544(10) 0.58251(13) 0.53786(4) 0.0163(2) Uani 1 1 d . . . . .
H20 H 0.863110 0.491251 0.553357 0.020 Uiso 1 1 calc R . . . .
C21 C 0.75429(12) 0.53204(15) 0.49113(5) 0.0226(3) Uani 1 1 d . . . . .
H21A H 0.803239 0.467681 0.470427 0.034 Uiso 1 1 calc GR . . . .
H21B H 0.729160 0.621021 0.471891 0.034 Uiso 1 1 calc GR . . . .
H21C H 0.685117 0.475249 0.501312 0.034 Uiso 1 1 calc GR . . . .
C22 C 0.92294(11) 0.69065(15) 0.52207(5) 0.0226(3) Uani 1 1 d . . . . .
H22A H 0.978122 0.636534 0.501081 0.034 Uiso 1 1 calc GR . . . .
H22B H 0.964700 0.729394 0.551898 0.034 Uiso 1 1 calc GR . . . .
H22C H 0.888236 0.775050 0.503167 0.034 Uiso 1 1 calc GR . . . .
C23 C 0.67242(11) 0.64726(14) 0.71718(5) 0.0211(2) Uani 1 1 d . . . . .
H23 H 0.725221 0.559045 0.724008 0.025 Uiso 1 1 calc R . . . .
C24 C 0.54897(13) 0.60711(18) 0.73455(5) 0.0311(3) Uani 1 1 d . . . . .
H24A H 0.550945 0.593190 0.770891 0.047 Uiso 1 1 calc GR . . . .
H24B H 0.522622 0.513500 0.718264 0.047 Uiso 1 1 calc GR . . . .
H24C H 0.494539 0.689002 0.725579 0.047 Uiso 1 1 calc GR . . . .
C25 C 0.71722(13) 0.78201(15) 0.74891(5) 0.0262(3) Uani 1 1 d . . . . .
H25A H 0.728004 0.750260 0.783815 0.039 Uiso 1 1 calc GR . . . .
H25B H 0.659776 0.864248 0.746837 0.039 Uiso 1 1 calc GR . . . .
H25C H 0.792338 0.817061 0.736228 0.039 Uiso 1 1 calc GR . . . .
S1 S 0.27820(11) 1.06252(8) 0.60980(3) 0.0193(2) Uani 0.492(2) 1 d . . P A 1
O1 O 0.39114(17) 1.0774(2) 0.63454(8) 0.0279(5) Uani 0.492(2) 1 d . . P A 1
O2 O 0.1875(3) 1.1549(7) 0.6298(3) 0.0414(10) Uani 0.492(2) 1 d . . P A 1
O3 O 0.2823(4) 1.0554(6) 0.55582(16) 0.0315(8) Uani 0.492(2) 1 d . . P A 1
C26 C 0.2341(11) 0.8692(10) 0.6269(3) 0.0263(13) Uani 0.492(2) 1 d . U P A 1
F1 F 0.12639(19) 0.8412(3) 0.60799(9) 0.0531(7) Uani 0.492(2) 1 d . . P A 1
F2 F 0.3051(3) 0.7707(5) 0.6112(2) 0.0567(9) Uani 0.492(2) 1 d . . P A 1
F3 F 0.2268(3) 0.8577(4) 0.67623(9) 0.0701(9) Uani 0.492(2) 1 d . . P A 1
S1A S 0.22370(11) 1.06058(8) 0.59673(3) 0.0229(2) Uani 0.508(2) 1 d . . P A 2
O1A O 0.11280(19) 1.0354(3) 0.57186(8) 0.0443(7) Uani 0.508(2) 1 d . . P A 2
O2A O 0.3223(3) 1.0486(7) 0.56529(19) 0.0457(11) Uani 0.508(2) 1 d . . P A 2
O3A O 0.2290(4) 1.1852(6) 0.6297(2) 0.0562(13) Uani 0.508(2) 1 d . . P A 2
C26A C 0.2388(11) 0.9008(12) 0.6374(4) 0.0317(14) Uani 0.508(2) 1 d . U P A 2
F1A F 0.33782(17) 0.9006(3) 0.66477(9) 0.0567(7) Uani 0.508(2) 1 d . . P A 2
F2A F 0.2433(5) 0.7688(6) 0.6096(2) 0.0895(16) Uani 0.508(2) 1 d . . P A 2
F3A F 0.1531(2) 0.8858(4) 0.66801(11) 0.0845(12) Uani 0.508(2) 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0216(5) 0.0176(5) 0.0171(5) -0.0006(4) -0.0001(4) -0.0042(4)
N2 0.0162(5) 0.0238(5) 0.0259(5) -0.0008(4) -0.0031(4) -0.0013(4)
N3 0.0133(4) 0.0127(4) 0.0164(4) 0.0003(4) -0.0014(3) 0.0002(3)
C1 0.0163(5) 0.0144(5) 0.0181(5) 0.0012(4) 0.0001(4) -0.0017(4)
C2 0.0310(7) 0.0223(6) 0.0206(6) 0.0008(5) -0.0079(5) -0.0099(5)
C3 0.0242(6) 0.0268(7) 0.0313(7) 0.0015(6) -0.0110(5) -0.0069(5)
C4 0.0255(6) 0.0239(6) 0.0229(6) -0.0052(5) 0.0074(5) -0.0034(5)
C5 0.0181(6) 0.0376(8) 0.0445(9) -0.0080(7) 0.0035(6) 0.0028(6)
C6 0.0156(5) 0.0139(5) 0.0159(5) 0.0000(4) -0.0004(4) 0.0001(4)
C7 0.0148(5) 0.0155(5) 0.0172(5) 0.0010(4) -0.0031(4) -0.0005(4)
C8 0.0232(6) 0.0183(6) 0.0195(6) 0.0035(5) -0.0053(5) -0.0020(5)
C9 0.0190(5) 0.0145(5) 0.0183(5) 0.0023(4) -0.0015(4) -0.0003(4)
C10 0.0235(6) 0.0197(6) 0.0286(7) -0.0054(5) -0.0067(5) -0.0020(5)
C11 0.0148(5) 0.0262(6) 0.0235(6) 0.0023(5) -0.0008(4) -0.0007(5)
C12 0.0256(6) 0.0205(6) 0.0248(6) 0.0044(5) 0.0028(5) -0.0025(5)
C13 0.0259(6) 0.0160(6) 0.0276(6) 0.0022(5) -0.0009(5) 0.0036(5)
C14 0.0128(5) 0.0129(5) 0.0172(5) 0.0013(4) 0.0002(4) 0.0001(4)
C15 0.0137(5) 0.0149(5) 0.0157(5) 0.0001(4) 0.0003(4) -0.0018(4)
C16 0.0177(5) 0.0177(6) 0.0175(5) 0.0018(4) -0.0019(4) 0.0006(4)
C17 0.0181(5) 0.0164(6) 0.0241(6) 0.0018(5) -0.0012(4) 0.0036(4)
C18 0.0186(5) 0.0181(6) 0.0231(6) -0.0011(5) 0.0049(4) 0.0030(4)
C19 0.0175(5) 0.0163(5) 0.0173(5) 0.0004(4) 0.0033(4) -0.0004(4)
C20 0.0171(5) 0.0163(5) 0.0156(5) 0.0014(4) 0.0022(4) 0.0022(4)
C21 0.0275(6) 0.0236(6) 0.0166(5) -0.0009(5) -0.0007(5) 0.0025(5)
C22 0.0212(6) 0.0214(6) 0.0254(6) 0.0048(5) 0.0061(5) 0.0003(5)
C23 0.0264(6) 0.0195(6) 0.0177(5) 0.0015(5) 0.0066(5) 0.0022(5)
C24 0.0329(7) 0.0338(8) 0.0273(7) 0.0011(6) 0.0139(6) -0.0017(6)
C25 0.0367(7) 0.0216(6) 0.0206(6) -0.0018(5) 0.0038(5) 0.0027(5)
S1 0.0229(5) 0.0170(3) 0.0181(3) -0.0020(2) 0.0020(3) 0.0013(3)
O1 0.0260(10) 0.0284(11) 0.0294(10) -0.0037(8) -0.0002(8) -0.0036(8)
O2 0.0297(17) 0.040(3) 0.055(2) -0.0155(18) 0.0101(17) 0.0110(14)
O3 0.048(2) 0.0298(15) 0.0167(12) 0.0017(10) -0.0001(14) -0.0005(17)
C26 0.0335(18) 0.023(4) 0.022(3) -0.001(2) 0.002(2) -0.009(3)
F1 0.0438(12) 0.0547(14) 0.0604(14) 0.0054(11) -0.0064(10) -0.0298(11)
F2 0.070(2) 0.0186(12) 0.081(2) 0.0046(12) -0.005(2) 0.0010(16)
F3 0.096(2) 0.085(2) 0.0292(12) 0.0280(12) 0.0016(14) -0.0385(19)
S1A 0.0240(5) 0.0241(3) 0.0207(4) -0.0023(3) 0.0027(3) 0.0026(3)
O1A 0.0309(11) 0.0749(18) 0.0267(11) 0.0105(11) -0.0051(9) -0.0026(11)
O2A 0.040(2) 0.0506(18) 0.048(3) 0.0184(19) 0.0241(17) 0.0052(19)
O3A 0.090(4) 0.032(2) 0.0459(19) -0.0164(16) -0.010(3) 0.017(3)
C26A 0.032(2) 0.028(4) 0.035(4) -0.003(2) 0.004(3) -0.003(2)
F1A 0.0323(10) 0.0727(16) 0.0641(15) 0.0236(12) -0.0134(10) 0.0112(10)
F2A 0.145(5) 0.0266(16) 0.095(3) 0.0081(16) -0.016(4) -0.018(3)
F3A 0.0389(13) 0.153(3) 0.0619(17) 0.0718(19) 0.0162(12) 0.0095(16)
_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
N1 C1 1.3589(15) . ?
N1 C2 1.3795(16) . ?
N1 C4 1.4600(16) . ?
N2 C1 1.3578(15) . ?
N2 C3 1.3760(17) . ?
N2 C5 1.4591(18) . ?
N3 C6 1.3859(15) . ?
N3 C7 1.5067(14) . ?
N3 C14 1.4407(14) . ?
C1 C6 1.4464(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.340(2) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C9 1.5255(16) . ?
C7 C8 1.5362(16) . ?
C7 C10 1.5174(17) . ?
C7 C11 1.5311(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5535(17) . ?
C9 C12 1.5429(17) . ?
C9 C13 1.5296(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.4099(15) . ?
C14 C19 1.4207(16) . ?
C15 C16 1.3988(16) . ?
C15 C20 1.5186(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3852(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3835(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3957(17) . ?
C19 C23 1.5261(16) . ?
C20 H20 1.0000 . ?
C20 C21 1.5379(17) . ?
C20 C22 1.5351(17) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 1.0000 . ?
C23 C24 1.5355(18) . ?
C23 C25 1.5436(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
S1 O1 1.437(2) . ?
S1 O2 1.433(5) . ?
S1 O3 1.448(4) . ?
S1 C26 1.846(10) . ?
C26 F1 1.339(11) . ?
C26 F2 1.269(11) . ?
C26 F3 1.328(10) . ?
S1A O1A 1.430(2) . ?
S1A O2A 1.426(5) . ?
S1A O3A 1.414(6) . ?
S1A C26A 1.791(13) . ?
C26A F1A 1.329(12) . ?
C26A F2A 1.387(8) . ?
C26A F3A 1.299(12) . ?
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
C1 N1 C2 109.86(11) . . ?
C1 N1 C4 127.01(10) . . ?
C2 N1 C4 122.93(11) . . ?
C1 N2 C3 109.84(11) . . ?
C1 N2 C5 126.06(11) . . ?
C3 N2 C5 123.95(11) . . ?
C6 N3 C7 107.64(9) . . ?
C6 N3 C14 125.24(9) . . ?
C14 N3 C7 126.45(9) . . ?
N1 C1 C6 126.09(10) . . ?
N2 C1 N1 105.54(10) . . ?
N2 C1 C6 128.36(11) . . ?
N1 C2 H2 126.4 . . ?
C3 C2 N1 107.20(11) . . ?
C3 C2 H2 126.4 . . ?
N2 C3 H3 126.2 . . ?
C2 C3 N2 107.56(11) . . ?
C2 C3 H3 126.2 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C1 124.81(10) . . ?
N3 C6 C9 109.24(9) . . ?
C1 C6 C9 125.45(10) . . ?
N3 C7 C8 100.71(9) . . ?
N3 C7 C10 113.19(10) . . ?
N3 C7 C11 110.48(9) . . ?
C10 C7 C8 113.08(10) . . ?
C10 C7 C11 108.79(10) . . ?
C11 C7 C8 110.42(10) . . ?
C7 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
C7 C8 C9 107.62(9) . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C6 C9 C8 101.74(9) . . ?
C6 C9 C12 107.63(10) . . ?
C6 C9 C13 116.79(10) . . ?
C12 C9 C8 110.33(10) . . ?
C13 C9 C8 111.74(10) . . ?
C13 C9 C12 108.39(10) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 120.65(10) . . ?
C15 C14 C19 120.48(10) . . ?
C19 C14 N3 118.83(10) . . ?
C14 C15 C20 123.07(10) . . ?
C16 C15 C14 118.71(10) . . ?
C16 C15 C20 118.22(10) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.27(11) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.57(11) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.80(11) . . ?
C19 C18 H18 119.1 . . ?
C14 C19 C23 124.60(11) . . ?
C18 C19 C14 118.12(11) . . ?
C18 C19 C23 117.27(10) . . ?
C15 C20 H20 108.2 . . ?
C15 C20 C21 112.40(10) . . ?
C15 C20 C22 110.53(10) . . ?
C21 C20 H20 108.2 . . ?
C22 C20 H20 108.2 . . ?
C22 C20 C21 109.09(10) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23 108.4 . . ?
C19 C23 C24 113.50(11) . . ?
C19 C23 C25 110.32(10) . . ?
C24 C23 H23 108.4 . . ?
C24 C23 C25 107.73(11) . . ?
C25 C23 H23 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 S1 O3 114.2(2) . . ?
O1 S1 C26 102.5(4) . . ?
O2 S1 O1 114.9(2) . . ?
O2 S1 O3 116.2(3) . . ?
O2 S1 C26 103.5(4) . . ?
O3 S1 C26 102.9(3) . . ?
F1 C26 S1 109.3(7) . . ?
F2 C26 S1 112.1(8) . . ?
F2 C26 F1 109.5(5) . . ?
F2 C26 F3 109.5(9) . . ?
F3 C26 S1 110.1(4) . . ?
F3 C26 F1 106.3(8) . . ?
O1A S1A C26A 103.2(4) . . ?
O2A S1A O1A 114.5(2) . . ?
O2A S1A C26A 103.6(4) . . ?
O3A S1A O1A 115.8(3) . . ?
O3A S1A O2A 113.9(3) . . ?
O3A S1A C26A 103.6(3) . . ?
F1A C26A S1A 113.7(7) . . ?
F1A C26A F2A 104.5(9) . . ?
F2A C26A S1A 110.1(7) . . ?
F3A C26A S1A 113.8(8) . . ?
F3A C26A F1A 107.1(7) . . ?
F3A C26A F2A 107.0(8) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 N3 117.19(14) . . . . ?
N1 C1 C6 C9 -71.82(17) . . . . ?
N1 C2 C3 N2 -0.40(15) . . . . ?
N2 C1 C6 N3 -63.72(18) . . . . ?
N2 C1 C6 C9 107.28(15) . . . . ?
N3 C6 C9 C8 -16.41(12) . . . . ?
N3 C6 C9 C12 99.59(11) . . . . ?
N3 C6 C9 C13 -138.32(11) . . . . ?
N3 C7 C8 C9 25.09(12) . . . . ?
N3 C14 C15 C16 176.25(10) . . . . ?
N3 C14 C15 C20 -4.50(17) . . . . ?
N3 C14 C19 C18 -175.31(10) . . . . ?
N3 C14 C19 C23 5.58(17) . . . . ?
C1 N1 C2 C3 0.16(15) . . . . ?
C1 N2 C3 C2 0.50(15) . . . . ?
C1 C6 C9 C8 171.41(11) . . . . ?
C1 C6 C9 C12 -72.58(14) . . . . ?
C1 C6 C9 C13 49.50(16) . . . . ?
C2 N1 C1 N2 0.14(13) . . . . ?
C2 N1 C1 C6 179.40(11) . . . . ?
C3 N2 C1 N1 -0.39(14) . . . . ?
C3 N2 C1 C6 -179.63(12) . . . . ?
C4 N1 C1 N2 175.05(11) . . . . ?
C4 N1 C1 C6 -5.69(19) . . . . ?
C4 N1 C2 C3 -174.99(12) . . . . ?
C5 N2 C1 N1 175.17(12) . . . . ?
C5 N2 C1 C6 -4.1(2) . . . . ?
C5 N2 C3 C2 -175.18(13) . . . . ?
C6 N3 C7 C8 -36.36(11) . . . . ?
C6 N3 C7 C10 -157.36(10) . . . . ?
C6 N3 C7 C11 80.36(11) . . . . ?
C6 N3 C14 C15 -73.76(15) . . . . ?
C6 N3 C14 C19 103.90(13) . . . . ?
C7 N3 C6 C1 -153.49(11) . . . . ?
C7 N3 C6 C9 34.27(12) . . . . ?
C7 N3 C14 C15 95.71(13) . . . . ?
C7 N3 C14 C19 -86.63(14) . . . . ?
C7 C8 C9 C6 -6.82(12) . . . . ?
C7 C8 C9 C12 -120.83(11) . . . . ?
C7 C8 C9 C13 118.52(11) . . . . ?
C10 C7 C8 C9 146.17(10) . . . . ?
C11 C7 C8 C9 -91.68(11) . . . . ?
C14 N3 C6 C1 17.65(17) . . . . ?
C14 N3 C6 C9 -154.59(10) . . . . ?
C14 N3 C7 C8 152.64(10) . . . . ?
C14 N3 C7 C10 31.64(15) . . . . ?
C14 N3 C7 C11 -90.64(13) . . . . ?
C14 C15 C16 C17 -0.82(17) . . . . ?
C14 C15 C20 C21 125.92(12) . . . . ?
C14 C15 C20 C22 -111.94(12) . . . . ?
C14 C19 C23 C24 -121.90(13) . . . . ?
C14 C19 C23 C25 117.10(13) . . . . ?
C15 C14 C19 C18 2.35(17) . . . . ?
C15 C14 C19 C23 -176.75(11) . . . . ?
C15 C16 C17 C18 1.98(18) . . . . ?
C16 C15 C20 C21 -54.83(14) . . . . ?
C16 C15 C20 C22 67.31(13) . . . . ?
C16 C17 C18 C19 -0.94(19) . . . . ?
C17 C18 C19 C14 -1.20(18) . . . . ?
C17 C18 C19 C23 177.97(11) . . . . ?
C18 C19 C23 C24 58.99(15) . . . . ?
C18 C19 C23 C25 -62.01(15) . . . . ?
C19 C14 C15 C16 -1.37(17) . . . . ?
C19 C14 C15 C20 177.88(10) . . . . ?
C20 C15 C16 C17 179.89(11) . . . . ?
O1 S1 C26 F1 177.3(4) . . . . ?
O1 S1 C26 F2 -61.1(7) . . . . ?
O1 S1 C26 F3 61.0(8) . . . . ?
O2 S1 C26 F1 57.5(6) . . . . ?
O2 S1 C26 F2 179.0(6) . . . . ?
O2 S1 C26 F3 -58.9(9) . . . . ?
O3 S1 C26 F1 -63.9(6) . . . . ?
O3 S1 C26 F2 57.7(7) . . . . ?
O3 S1 C26 F3 179.8(7) . . . . ?
O1A S1A C26A F1A 180.0(5) . . . . ?
O1A S1A C26A F2A 63.1(8) . . . . ?
O1A S1A C26A F3A -57.1(5) . . . . ?
O2A S1A C26A F1A 60.3(6) . . . . ?
O2A S1A C26A F2A -56.6(8) . . . . ?
O2A S1A C26A F3A -176.7(5) . . . . ?
O3A S1A C26A F1A -58.9(7) . . . . ?
O3A S1A C26A F2A -175.9(7) . . . . ?
O3A S1A C26A F3A 64.0(6) . . . . ?
_shelx_res_file
;
TITL JM1902 in P2(1)/c,MESSELBERGER/MUNZ, MJ154
jm1902.res
created by SHELXL-2016/6 at 10:56:24 on 22-Mar-2019
CELL 0.71073 11.3959 8.8582 26.7626 90 91.58 90
ZERR 4 0.0004 0.0003 0.001 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O S
UNIT 104 156 12 12 12 4
SIMU 0.005 0.01 2 C26 C26A
L.S. 10
PLAN 20
SIZE 0.17 0.15 0.11
TEMP -173
BOND $H
CONF
HTAB
WPDB -1
LIST 4
fmap 2
acta
SHEL 10 0.74
REM
REM
REM
WGHT 0.045900 1.170200
FVAR 0.62727 0.49192
N1 4 0.726039 0.196943 0.552308 11.00000 0.02161 0.01755 =
0.01706 -0.00058 -0.00009 -0.00422
N2 4 0.583592 0.313794 0.587525 11.00000 0.01623 0.02383 =
0.02591 -0.00080 -0.00311 -0.00130
N3 4 0.811754 0.476900 0.643054 11.00000 0.01331 0.01268 =
0.01636 0.00034 -0.00137 0.00020
C1 1 0.700054 0.283063 0.592540 11.00000 0.01635 0.01440 =
0.01810 0.00121 0.00011 -0.00169
C2 1 0.626446 0.175149 0.522714 11.00000 0.03098 0.02233 =
0.02057 0.00077 -0.00790 -0.00993
AFIX 43
H2 2 0.621184 0.118878 0.492517 11.00000 -1.20000
AFIX 0
C3 1 0.538510 0.248188 0.544525 11.00000 0.02415 0.02677 =
0.03125 0.00145 -0.01104 -0.00688
AFIX 43
H3 2 0.459420 0.253675 0.532487 11.00000 -1.20000
AFIX 0
C4 1 0.841913 0.143821 0.538359 11.00000 0.02553 0.02391 =
0.02292 -0.00521 0.00738 -0.00343
AFIX 137
H4A 2 0.850416 0.155401 0.502222 11.00000 -1.50000
H4B 2 0.850599 0.037143 0.547430 11.00000 -1.50000
H4C 2 0.902500 0.203264 0.556061 11.00000 -1.50000
AFIX 0
C5 1 0.512830 0.393901 0.623604 11.00000 0.01809 0.03762 =
0.04448 -0.00798 0.00355 0.00277
AFIX 137
H5A 2 0.436592 0.343731 0.626187 11.00000 -1.50000
H5B 2 0.500871 0.498339 0.612508 11.00000 -1.50000
H5C 2 0.553499 0.393436 0.656349 11.00000 -1.50000
AFIX 0
C6 1 0.781326 0.328804 0.632160 11.00000 0.01560 0.01394 =
0.01587 0.00001 -0.00036 0.00007
C7 1 0.932594 0.475423 0.667355 11.00000 0.01481 0.01547 =
0.01721 0.00099 -0.00310 -0.00045
C8 1 0.926615 0.329538 0.698215 11.00000 0.02320 0.01828 =
0.01953 0.00348 -0.00530 -0.00200
AFIX 23
H8A 2 0.904171 0.352761 0.732853 11.00000 -1.20000
H8B 2 1.004125 0.278999 0.699412 11.00000 -1.20000
AFIX 0
C9 1 0.833268 0.225323 0.672611 11.00000 0.01903 0.01454 =
0.01826 0.00231 -0.00146 -0.00027
C10 1 0.958243 0.614233 0.699035 11.00000 0.02350 0.01968 =
0.02855 -0.00538 -0.00674 -0.00196
AFIX 137
H10A 2 1.040194 0.611774 0.711108 11.00000 -1.50000
H10B 2 0.906317 0.615372 0.727619 11.00000 -1.50000
H10C 2 0.944784 0.705200 0.678840 11.00000 -1.50000
AFIX 0
C11 1 1.026492 0.461998 0.627766 11.00000 0.01476 0.02618 =
0.02348 0.00234 -0.00084 -0.00065
AFIX 137
H11A 2 1.103656 0.448712 0.644253 11.00000 -1.50000
H11B 2 1.026786 0.553949 0.607408 11.00000 -1.50000
H11C 2 1.009134 0.374741 0.606298 11.00000 -1.50000
AFIX 0
C12 1 0.734896 0.188320 0.709141 11.00000 0.02558 0.02052 =
0.02481 0.00445 0.00283 -0.00250
AFIX 137
H12A 2 0.767678 0.130749 0.737510 11.00000 -1.50000
H12B 2 0.674014 0.128308 0.691850 11.00000 -1.50000
H12C 2 0.700511 0.282400 0.721268 11.00000 -1.50000
AFIX 0
C13 1 0.887073 0.076874 0.655142 11.00000 0.02588 0.01598 =
0.02763 0.00219 -0.00091 0.00361
AFIX 137
H13A 2 0.916543 0.019674 0.684212 11.00000 -1.50000
H13B 2 0.952018 0.098429 0.632974 11.00000 -1.50000
H13C 2 0.827130 0.017407 0.637046 11.00000 -1.50000
AFIX 0
C14 1 0.746737 0.608248 0.626729 11.00000 0.01277 0.01286 =
0.01722 0.00133 0.00021 0.00006
C15 1 0.749192 0.656441 0.576559 11.00000 0.01373 0.01493 =
0.01568 0.00014 0.00034 -0.00175
C16 1 0.679304 0.779129 0.561675 11.00000 0.01773 0.01767 =
0.01750 0.00177 -0.00186 0.00058
AFIX 43
H16 2 0.681108 0.813326 0.528061 11.00000 -1.20000
AFIX 0
C17 1 0.607516 0.851721 0.595007 11.00000 0.01809 0.01641 =
0.02412 0.00175 -0.00125 0.00356
AFIX 43
H17 2 0.558742 0.932854 0.584047 11.00000 -1.20000
AFIX 0
C18 1 0.607308 0.805296 0.644363 11.00000 0.01860 0.01807 =
0.02312 -0.00108 0.00488 0.00303
AFIX 43
H18 2 0.558730 0.856590 0.667122 11.00000 -1.20000
AFIX 0
C19 1 0.676514 0.685166 0.661631 11.00000 0.01747 0.01632 =
0.01729 0.00043 0.00332 -0.00036
C20 1 0.825440 0.582511 0.537860 11.00000 0.01712 0.01627 =
0.01562 0.00140 0.00223 0.00215
AFIX 13
H20 2 0.863110 0.491251 0.553357 11.00000 -1.20000
AFIX 0
C21 1 0.754286 0.532038 0.491135 11.00000 0.02754 0.02362 =
0.01662 -0.00088 -0.00073 0.00251
AFIX 137
H21A 2 0.803239 0.467681 0.470427 11.00000 -1.50000
H21B 2 0.729160 0.621021 0.471891 11.00000 -1.50000
H21C 2 0.685117 0.475249 0.501312 11.00000 -1.50000
AFIX 0
C22 1 0.922938 0.690648 0.522074 11.00000 0.02124 0.02139 =
0.02540 0.00480 0.00612 0.00034
AFIX 137
H22A 2 0.978122 0.636534 0.501081 11.00000 -1.50000
H22B 2 0.964700 0.729394 0.551898 11.00000 -1.50000
H22C 2 0.888236 0.775050 0.503167 11.00000 -1.50000
AFIX 0
C23 1 0.672415 0.647256 0.717182 11.00000 0.02638 0.01950 =
0.01772 0.00151 0.00656 0.00217
AFIX 13
H23 2 0.725221 0.559045 0.724008 11.00000 -1.20000
AFIX 0
C24 1 0.548965 0.607106 0.734550 11.00000 0.03295 0.03384 =
0.02733 0.00108 0.01395 -0.00168
AFIX 137
H24A 2 0.550945 0.593190 0.770891 11.00000 -1.50000
H24B 2 0.522622 0.513500 0.718264 11.00000 -1.50000
H24C 2 0.494539 0.689002 0.725579 11.00000 -1.50000
AFIX 0
C25 1 0.717223 0.782006 0.748912 11.00000 0.03667 0.02155 =
0.02060 -0.00183 0.00376 0.00266
AFIX 137
H25A 2 0.728004 0.750260 0.783815 11.00000 -1.50000
H25B 2 0.659776 0.864248 0.746837 11.00000 -1.50000
H25C 2 0.792338 0.817061 0.736228 11.00000 -1.50000
AFIX 0
PART 1
S1 6 0.278198 1.062523 0.609802 21.00000 0.02291 0.01697 =
0.01815 -0.00204 0.00197 0.00128
O1 5 0.391143 1.077393 0.634536 21.00000 0.02597 0.02839 =
0.02943 -0.00365 -0.00018 -0.00360
O2 5 0.187545 1.154912 0.629798 21.00000 0.02972 0.04035 =
0.05463 -0.01549 0.01006 0.01097
O3 5 0.282299 1.055394 0.555822 21.00000 0.04787 0.02977 =
0.01674 0.00172 -0.00010 -0.00054
C26 1 0.234142 0.869245 0.626930 21.00000 0.03354 0.02319 =
0.02238 -0.00104 0.00183 -0.00945
F1 3 0.126389 0.841249 0.607993 21.00000 0.04382 0.05471 =
0.06043 0.00541 -0.00643 -0.02980
F2 3 0.305092 0.770705 0.611234 21.00000 0.07035 0.01861 =
0.08087 0.00464 -0.00503 0.00103
F3 3 0.226850 0.857717 0.676230 21.00000 0.09564 0.08548 =
0.02915 0.02796 0.00161 -0.03849
PART 0
PART 2
S1A 6 0.223702 1.060584 0.596727 -21.00000 0.02397 0.02410 =
0.02071 -0.00229 0.00268 0.00263
O1A 5 0.112799 1.035399 0.571859 -21.00000 0.03093 0.07488 =
0.02674 0.01053 -0.00514 -0.00256
O2A 5 0.322314 1.048635 0.565292 -21.00000 0.03970 0.05056 =
0.04819 0.01836 0.02413 0.00520
O3A 5 0.228982 1.185155 0.629721 -21.00000 0.09003 0.03198 =
0.04594 -0.01643 -0.00998 0.01692
C26A 1 0.238777 0.900769 0.637392 -21.00000 0.03244 0.02804 =
0.03468 -0.00285 0.00374 -0.00252
F1A 3 0.337823 0.900553 0.664765 -21.00000 0.03232 0.07273 =
0.06410 0.02357 -0.01340 0.01115
F2A 3 0.243342 0.768849 0.609576 -21.00000 0.14546 0.02662 =
0.09528 0.00815 -0.01648 -0.01756
F3A 3 0.153099 0.885813 0.668005 -21.00000 0.03891 0.15345 =
0.06186 0.07176 0.01615 0.00946
HKLF 4
REM JM1902 in P2(1)/c,MESSELBERGER/MUNZ, MJ154
REM R1 = 0.0416 for 5762 Fo > 4sig(Fo) and 0.0538 for all 6963 data
REM 408 parameters refined using 6 restraints
END
WGHT 0.0459 1.1702
REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, -y+1, -z+1
HTAB C2 O3_$1
HTAB C2 O2A_$1
EQIV $2 x, y-1, z
HTAB C3 O2A_$2
HTAB C4 O1A_$1
HTAB C5 O1_$2
REM Highest difference peak 0.412, deepest hole -0.291, 1-sigma level 0.043
Q1 1 0.7834 0.6132 0.5574 11.00000 0.05 0.41
Q2 1 0.7556 0.6388 0.6026 11.00000 0.05 0.32
Q3 1 0.6367 0.8050 0.5789 11.00000 0.05 0.32
Q4 1 0.9769 0.4637 0.6479 11.00000 0.05 0.32
Q5 1 0.9425 0.5399 0.6824 11.00000 0.05 0.32
Q6 1 0.8136 0.2711 0.6488 11.00000 0.05 0.31
Q7 1 0.6796 0.6661 0.6887 11.00000 0.05 0.31
Q8 1 0.7062 0.7066 0.5680 11.00000 0.05 0.31
Q9 1 0.6091 0.8104 0.6174 11.00000 0.05 0.29
Q10 1 0.2509 0.9714 0.6206 11.00000 0.05 0.29
Q11 1 0.8791 0.2770 0.6853 11.00000 0.05 0.28
Q12 1 0.7203 0.6519 0.6450 11.00000 0.05 0.28
Q13 1 0.7438 0.3002 0.6136 11.00000 0.05 0.28
Q14 1 0.9254 0.4035 0.6832 11.00000 0.05 0.27
Q15 1 0.8601 0.1528 0.6608 11.00000 0.05 0.27
Q16 1 0.6798 0.1820 0.5355 11.00000 0.05 0.26
Q17 1 0.7917 0.5559 0.5164 11.00000 0.05 0.26
Q18 1 0.5766 0.1691 0.5435 11.00000 0.05 0.25
Q19 1 0.8685 0.6356 0.5277 11.00000 0.05 0.25
Q20 1 0.7900 0.2020 0.6913 11.00000 0.05 0.24
;
_shelx_res_checksum 40755
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: tetrahydrofuran, diethyl ether'
_chemical_properties_physical Moisture-sensitive,Oxygen-sensitive
#######################################################################
#
# 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_jm1903
_database_code_depnum_ccdc_archive 'CCDC 1964615'
loop_
_audit_author_name
_audit_author_address
'Frank W. Heinemann'
;Friedrich Alexander Universitaet Erlangen Nuernberg
Germany
;
_audit_update_record
;
2019-11-08 deposited with the CCDC. 2020-03-30 downloaded from the CCDC.
;
_audit_creation_date 2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H39 N3, C F3 O3 S'
_chemical_formula_sum 'C26 H39 F3 N3 O3 S'
_chemical_formula_weight 530.66
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 14.9305(9)
_cell_length_b 11.6700(7)
_cell_length_c 16.4062(9)
_cell_angle_alpha 90
_cell_angle_beta 109.508(2)
_cell_angle_gamma 90
_cell_volume 2694.5(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9691
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 29.50
_cell_measurement_theta_min 2.27
_shelx_estimated_absorpt_T_max 0.991
_shelx_estimated_absorpt_T_min 0.960
_exptl_absorpt_coefficient_mu 0.173
_exptl_absorpt_correction_T_max 0.7459
_exptl_absorpt_correction_T_min 0.7196
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.9647.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour orange
_exptl_crystal_density_diffrn 1.308
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 1132
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.05
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0433
_diffrn_reflns_av_unetI/netI 0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_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 94277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.875
_diffrn_reflns_theta_min 2.186
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_source 'ImuS high brilliance micro-focus tube'
_diffrn_radiation_monochromator 'Quazar focussing montel optics'
_diffrn_measurement_device_type 'Bruker Kappa ImuS Duo Photon II CPAD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5782
_reflns_number_total 6421
_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_data_collection 'Bruker APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_reduction 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max 0.679
_refine_diff_density_min -0.649
_refine_diff_density_rms 0.056
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.083
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 365
_refine_ls_number_reflns 6421
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0642
_refine_ls_R_factor_gt 0.0577
_refine_ls_restrained_S_all 1.083
_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^)+(0.0374P)^2^+3.6010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1268
_refine_ls_wR_factor_ref 0.1305
_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. Others
Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=
Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C11)=
Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
C20(H20), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
C8(H8A,H8B), C8A(H8AA,H8AB)
3.c Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C16(H16), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C10A(H10D,H10E,H10F),
C11A(H11D,H11E,H11F)
;
_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
N1 N 0.64121(11) 0.23941(14) 0.52294(10) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.70709(12) 0.11113(14) 0.46649(10) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.84967(10) 0.31805(12) 0.62271(9) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.72441(13) 0.21063(15) 0.51170(11) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.57370(14) 0.15720(18) 0.48600(13) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.509893 0.156859 0.485502 0.033 Uiso 1 1 calc R . . . .
C3 C 0.61443(15) 0.07782(18) 0.45092(13) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.584848 0.010917 0.420847 0.034 Uiso 1 1 calc R . . . .
C4 C 0.61712(14) 0.35394(17) 0.54602(13) 0.0250(4) Uani 1 1 d . . . . .
H4A H 0.564137 0.348224 0.568470 0.037 Uiso 1 1 calc GR . . . .
H4B H 0.598686 0.403046 0.494614 0.037 Uiso 1 1 calc GR . . . .
H4C H 0.672430 0.387108 0.590406 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.77262(16) 0.0463(2) 0.43491(16) 0.0357(5) Uani 1 1 d . . . . .
H5A H 0.768839 -0.035211 0.447691 0.054 Uiso 1 1 calc GR . . . .
H5B H 0.837598 0.073783 0.463562 0.054 Uiso 1 1 calc GR . . . .
H5C H 0.755346 0.056938 0.372285 0.054 Uiso 1 1 calc GR . . . .
C6 C 0.81168(13) 0.27647(15) 0.53834(11) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.90548(14) 0.42658(16) 0.62393(12) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.9238(4) 0.4178(4) 0.5428(3) 0.0257(10) Uani 0.474(5) 1 d . . P A 1
H8A H 0.986022 0.380188 0.552814 0.031 Uiso 0.474(5) 1 calc R . P A 1
H8B H 0.926916 0.495609 0.519762 0.031 Uiso 0.474(5) 1 calc R . P A 1
C9 C 0.84370(14) 0.34687(16) 0.47475(12) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.9889(3) 0.4365(4) 0.7061(3) 0.0302(11) Uani 0.474(5) 1 d . . P A 1
H10A H 0.966410 0.435848 0.755788 0.045 Uiso 0.474(5) 1 calc GR . P A 1
H10B H 1.022734 0.508321 0.705651 0.045 Uiso 0.474(5) 1 calc GR . P A 1
H10C H 1.032042 0.371677 0.710453 0.045 Uiso 0.474(5) 1 calc GR . P A 1
C11 C 0.8371(4) 0.5325(4) 0.6236(3) 0.0276(11) Uani 0.474(5) 1 d . . P A 1
H11A H 0.826322 0.536207 0.679261 0.041 Uiso 0.474(5) 1 calc GR . P A 1
H11B H 0.776245 0.522395 0.577019 0.041 Uiso 0.474(5) 1 calc GR . P A 1
H11C H 0.867020 0.603856 0.614295 0.041 Uiso 0.474(5) 1 calc GR . P A 1
C12 C 0.9093(2) 0.2866(3) 0.43482(19) 0.0600(9) Uani 1 1 d . . . . .
H12A H 0.962986 0.252945 0.480720 0.090 Uiso 1 1 calc GR . . . .
H12B H 0.933062 0.342089 0.402090 0.090 Uiso 1 1 calc GR . . . .
H12C H 0.874201 0.225916 0.395903 0.090 Uiso 1 1 calc GR . . . .
C13 C 0.7601(2) 0.3910(4) 0.4003(2) 0.0765(13) Uani 1 1 d . . . . .
H13A H 0.716014 0.431483 0.423079 0.115 Uiso 1 1 calc GR . . . .
H13B H 0.727269 0.326440 0.364541 0.115 Uiso 1 1 calc GR . . . .
H13C H 0.782969 0.443751 0.365068 0.115 Uiso 1 1 calc GR . . . .
C14 C 0.87311(12) 0.24390(15) 0.69830(11) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.83562(13) 0.26749(15) 0.76488(11) 0.0179(3) Uani 1 1 d . . . . .
C16 C 0.86268(14) 0.19785(16) 0.83856(11) 0.0219(4) Uani 1 1 d . . . . .
H16 H 0.836735 0.212300 0.883132 0.026 Uiso 1 1 calc R . . . .
C17 C 0.92612(14) 0.10872(17) 0.84808(12) 0.0231(4) Uani 1 1 d . . . . .
H17 H 0.943821 0.062782 0.898789 0.028 Uiso 1 1 calc R . . . .
C18 C 0.96363(13) 0.08687(16) 0.78333(12) 0.0219(4) Uani 1 1 d . . . . .
H18 H 1.008152 0.026320 0.790598 0.026 Uiso 1 1 calc R . . . .
C19 C 0.93779(12) 0.15144(15) 0.70750(12) 0.0189(3) Uani 1 1 d . . . . .
C20 C 0.76379(13) 0.36096(16) 0.76164(11) 0.0196(4) Uani 1 1 d . . . . .
H20 H 0.752436 0.405373 0.706981 0.023 Uiso 1 1 calc R . . . .
C21 C 0.66893(15) 0.30762(18) 0.75944(14) 0.0285(4) Uani 1 1 d . . . . .
H21A H 0.620143 0.367422 0.747359 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.676400 0.272301 0.815524 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.649732 0.249127 0.714040 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.79884(16) 0.44489(17) 0.83801(13) 0.0279(4) Uani 1 1 d . . . . .
H22A H 0.753153 0.507765 0.829826 0.042 Uiso 1 1 calc GR . . . .
H22B H 0.860831 0.475875 0.840904 0.042 Uiso 1 1 calc GR . . . .
H22C H 0.804856 0.404528 0.891964 0.042 Uiso 1 1 calc GR . . . .
C23 C 0.98126(14) 0.11546(17) 0.63964(13) 0.0243(4) Uani 1 1 d . . . . .
H23 H 0.953958 0.165209 0.587584 0.029 Uiso 1 1 calc R . . . .
C24 C 0.95591(19) -0.00933(19) 0.61246(15) 0.0369(5) Uani 1 1 d . . . . .
H24A H 0.974748 -0.027054 0.562075 0.055 Uiso 1 1 calc GR . . . .
H24B H 0.887233 -0.020356 0.597579 0.055 Uiso 1 1 calc GR . . . .
H24C H 0.989545 -0.060349 0.660342 0.055 Uiso 1 1 calc GR . . . .
C25 C 1.08987(16) 0.1285(3) 0.67103(17) 0.0467(7) Uani 1 1 d . . . . .
H25A H 1.113282 0.113973 0.622845 0.070 Uiso 1 1 calc GR . . . .
H25B H 1.118507 0.073309 0.717482 0.070 Uiso 1 1 calc GR . . . .
H25C H 1.107107 0.206450 0.692800 0.070 Uiso 1 1 calc GR . . . .
S1 S 0.35217(4) 0.27634(4) 0.57503(3) 0.02992(14) Uani 1 1 d . . . . .
O1 O 0.38626(13) 0.38986(14) 0.56936(11) 0.0401(4) Uani 1 1 d . . . . .
O2 O 0.41807(17) 0.18812(15) 0.57314(14) 0.0555(6) Uani 1 1 d . . . . .
O3 O 0.25643(16) 0.2536(2) 0.52429(13) 0.0662(7) Uani 1 1 d . . . . .
C26 C 0.35211(17) 0.26519(19) 0.68573(14) 0.0318(5) Uani 1 1 d . . . . .
F1 F 0.32228(10) 0.16314(11) 0.70185(8) 0.0359(3) Uani 1 1 d . . . . .
F2 F 0.29686(17) 0.34229(15) 0.70353(13) 0.0719(6) Uani 1 1 d . . . . .
F3 F 0.43969(13) 0.27894(17) 0.74219(10) 0.0641(5) Uani 1 1 d . . . . .
C8A C 0.8735(3) 0.4591(3) 0.5253(2) 0.0217(8) Uani 0.526(5) 1 d . . P A 2
H8AA H 0.819567 0.513445 0.510528 0.026 Uiso 0.526(5) 1 calc R . P A 2
H8AB H 0.926643 0.495211 0.511379 0.026 Uiso 0.526(5) 1 calc R . P A 2
C10A C 1.0171(3) 0.4014(3) 0.6566(3) 0.0258(9) Uani 0.526(5) 1 d . . P A 2
H10D H 1.031404 0.345628 0.618073 0.039 Uiso 0.526(5) 1 calc GR . P A 2
H10E H 1.036670 0.370452 0.715500 0.039 Uiso 0.526(5) 1 calc GR . P A 2
H10F H 1.051586 0.472783 0.656371 0.039 Uiso 0.526(5) 1 calc GR . P A 2
C11A C 0.8893(3) 0.5223(3) 0.6758(3) 0.0266(10) Uani 0.526(5) 1 d . . P A 2
H11D H 0.923644 0.590203 0.666993 0.040 Uiso 0.526(5) 1 calc GR . P A 2
H11E H 0.912298 0.501208 0.737117 0.040 Uiso 0.526(5) 1 calc GR . P A 2
H11F H 0.821175 0.539342 0.657760 0.040 Uiso 0.526(5) 1 calc GR . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0218(8) 0.0203(8) 0.0215(7) -0.0014(6) 0.0052(6) 0.0018(6)
N2 0.0265(8) 0.0178(7) 0.0222(8) -0.0036(6) 0.0043(6) 0.0012(6)
N3 0.0205(7) 0.0129(7) 0.0147(7) 0.0008(5) 0.0054(6) 0.0002(6)
C1 0.0234(9) 0.0175(8) 0.0140(7) 0.0015(6) 0.0043(6) 0.0040(7)
C2 0.0229(9) 0.0278(10) 0.0276(10) 0.0006(8) 0.0041(8) -0.0026(8)
C3 0.0296(10) 0.0216(9) 0.0274(10) -0.0020(8) 0.0013(8) -0.0026(8)
C4 0.0227(9) 0.0243(10) 0.0259(9) -0.0051(8) 0.0053(7) 0.0044(7)
C5 0.0359(12) 0.0284(11) 0.0419(12) -0.0157(9) 0.0118(10) 0.0030(9)
C6 0.0228(8) 0.0152(8) 0.0152(8) 0.0012(6) 0.0072(7) 0.0038(7)
C7 0.0299(10) 0.0148(8) 0.0246(9) 0.0014(7) 0.0098(8) -0.0035(7)
C8 0.036(3) 0.019(2) 0.031(2) 0.0059(17) 0.022(2) 0.002(2)
C9 0.0336(10) 0.0191(9) 0.0215(9) 0.0017(7) 0.0166(8) 0.0023(8)
C10 0.031(2) 0.028(2) 0.032(2) -0.0021(18) 0.0105(18) -0.0113(18)
C11 0.044(3) 0.0143(19) 0.031(3) 0.0000(17) 0.021(2) -0.0013(18)
C12 0.097(2) 0.0549(17) 0.0567(17) 0.0329(14) 0.0632(18) 0.0443(17)
C13 0.0510(17) 0.112(3) 0.075(2) 0.079(2) 0.0325(16) 0.0352(18)
C14 0.0178(8) 0.0152(8) 0.0146(7) 0.0008(6) 0.0034(6) -0.0012(6)
C15 0.0200(8) 0.0160(8) 0.0164(8) -0.0011(6) 0.0045(6) -0.0021(7)
C16 0.0284(9) 0.0229(9) 0.0140(8) -0.0005(7) 0.0065(7) -0.0025(7)
C17 0.0267(9) 0.0213(9) 0.0171(8) 0.0045(7) 0.0017(7) -0.0025(7)
C18 0.0206(9) 0.0185(9) 0.0233(9) 0.0040(7) 0.0030(7) 0.0024(7)
C19 0.0180(8) 0.0181(8) 0.0204(8) 0.0014(7) 0.0062(7) 0.0006(7)
C20 0.0249(9) 0.0179(8) 0.0186(8) -0.0011(7) 0.0107(7) 0.0005(7)
C21 0.0280(10) 0.0251(10) 0.0377(11) 0.0044(8) 0.0180(9) 0.0014(8)
C22 0.0419(12) 0.0225(9) 0.0232(9) -0.0048(8) 0.0161(9) -0.0002(8)
C23 0.0239(9) 0.0258(10) 0.0266(9) 0.0069(8) 0.0131(8) 0.0093(8)
C24 0.0629(16) 0.0250(11) 0.0310(11) 0.0053(9) 0.0264(11) 0.0154(10)
C25 0.0254(11) 0.0742(19) 0.0456(14) 0.0086(13) 0.0186(10) 0.0122(12)
S1 0.0480(3) 0.0240(3) 0.0220(2) -0.00448(19) 0.0174(2) -0.0100(2)
O1 0.0623(11) 0.0252(8) 0.0442(9) -0.0008(7) 0.0330(9) -0.0096(8)
O2 0.0973(16) 0.0301(9) 0.0649(13) 0.0008(9) 0.0614(12) 0.0059(10)
O3 0.0650(13) 0.0799(16) 0.0368(10) 0.0147(10) -0.0057(9) -0.0345(12)
C26 0.0458(13) 0.0291(11) 0.0269(10) -0.0107(8) 0.0205(9) -0.0157(9)
F1 0.0474(8) 0.0351(7) 0.0287(6) -0.0007(5) 0.0175(6) -0.0178(6)
F2 0.1278(17) 0.0418(9) 0.0847(13) -0.0006(9) 0.0866(13) 0.0109(10)
F3 0.0670(11) 0.0873(13) 0.0304(7) -0.0077(8) 0.0062(7) -0.0495(10)
C8A 0.029(2) 0.0153(17) 0.0245(18) 0.0032(14) 0.0148(16) 0.0006(16)
C10A 0.0259(19) 0.0225(18) 0.030(2) -0.0017(15) 0.0099(15) -0.0060(15)
C11A 0.038(2) 0.0167(17) 0.033(2) -0.0056(16) 0.022(2) -0.0086(16)
_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
N1 C1 1.357(2) . ?
N1 C2 1.377(3) . ?
N1 C4 1.466(2) . ?
N2 C1 1.355(2) . ?
N2 C3 1.376(3) . ?
N2 C5 1.462(3) . ?
N3 C6 1.396(2) . ?
N3 C7 1.513(2) . ?
N3 C14 1.456(2) . ?
C1 C6 1.449(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.339(3) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C9 1.525(2) . ?
C7 C8 1.450(4) . ?
C7 C10 1.504(5) . ?
C7 C11 1.602(5) . ?
C7 C8A 1.573(4) . ?
C7 C10A 1.598(4) . ?
C7 C11A 1.473(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.572(5) . ?
C9 C12 1.521(3) . ?
C9 C13 1.516(3) . ?
C9 C8A 1.534(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.411(2) . ?
C14 C19 1.422(2) . ?
C15 C16 1.399(2) . ?
C15 C20 1.518(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(2) . ?
C19 C23 1.523(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.536(3) . ?
C20 C22 1.538(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 1.0000 . ?
C23 C24 1.533(3) . ?
C23 C25 1.536(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
S1 O1 1.4333(16) . ?
S1 O2 1.432(2) . ?
S1 O3 1.418(2) . ?
S1 C26 1.821(2) . ?
C26 F1 1.329(2) . ?
C26 F2 1.318(3) . ?
C26 F3 1.336(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 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
C1 N1 C2 109.66(16) . . ?
C1 N1 C4 125.11(16) . . ?
C2 N1 C4 122.83(16) . . ?
C1 N2 C3 109.86(16) . . ?
C1 N2 C5 127.54(17) . . ?
C3 N2 C5 122.57(17) . . ?
C6 N3 C7 110.11(14) . . ?
C6 N3 C14 122.72(14) . . ?
C14 N3 C7 120.78(14) . . ?
N1 C1 C6 126.83(16) . . ?
N2 C1 N1 105.68(16) . . ?
N2 C1 C6 127.40(17) . . ?
N1 C2 H2 126.3 . . ?
C3 C2 N1 107.49(18) . . ?
C3 C2 H2 126.3 . . ?
N2 C3 H3 126.3 . . ?
C2 C3 N2 107.30(18) . . ?
C2 C3 H3 126.3 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C1 120.68(15) . . ?
N3 C6 C9 112.01(15) . . ?
C1 C6 C9 122.36(15) . . ?
N3 C7 C11 107.4(2) . . ?
N3 C7 C8A 102.22(18) . . ?
N3 C7 C10A 111.02(19) . . ?
C8 C7 N3 101.6(2) . . ?
C8 C7 C10 118.3(3) . . ?
C8 C7 C11 111.5(3) . . ?
C10 C7 N3 111.3(2) . . ?
C10 C7 C11 106.3(3) . . ?
C8A C7 C10A 108.3(2) . . ?
C11A C7 N3 116.6(2) . . ?
C11A C7 C8A 111.1(3) . . ?
C11A C7 C10A 107.4(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 C9 110.9(3) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C6 C9 C8 97.82(19) . . ?
C6 C9 C8A 100.99(18) . . ?
C12 C9 C6 116.09(17) . . ?
C12 C9 C8 95.9(3) . . ?
C12 C9 C8A 121.0(3) . . ?
C13 C9 C6 111.89(18) . . ?
C13 C9 C8 128.3(3) . . ?
C13 C9 C12 106.6(2) . . ?
C13 C9 C8A 99.1(3) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 119.93(15) . . ?
C15 C14 C19 119.79(16) . . ?
C19 C14 N3 120.19(15) . . ?
C14 C15 C20 124.84(16) . . ?
C16 C15 C14 118.73(17) . . ?
C16 C15 C20 116.38(16) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.65(17) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.45(17) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.64(17) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C23 124.87(16) . . ?
C18 C19 C14 118.72(17) . . ?
C18 C19 C23 116.41(16) . . ?
C15 C20 H20 108.1 . . ?
C15 C20 C21 110.16(15) . . ?
C15 C20 C22 112.64(16) . . ?
C21 C20 H20 108.1 . . ?
C21 C20 C22 109.71(16) . . ?
C22 C20 H20 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23 108.2 . . ?
C19 C23 C24 110.52(16) . . ?
C19 C23 C25 112.79(18) . . ?
C24 C23 H23 108.2 . . ?
C24 C23 C25 108.78(19) . . ?
C25 C23 H23 108.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 S1 C26 104.43(10) . . ?
O2 S1 O1 113.68(11) . . ?
O2 S1 C26 101.51(11) . . ?
O3 S1 O1 116.43(13) . . ?
O3 S1 O2 114.70(15) . . ?
O3 S1 C26 103.65(12) . . ?
F1 C26 S1 111.99(14) . . ?
F1 C26 F3 106.6(2) . . ?
F2 C26 S1 112.40(17) . . ?
F2 C26 F1 106.96(18) . . ?
F2 C26 F3 107.7(2) . . ?
F3 C26 S1 110.89(15) . . ?
C7 C8A H8AA 110.4 . . ?
C7 C8A H8AB 110.4 . . ?
C9 C8A C7 106.5(2) . . ?
C9 C8A H8AA 110.4 . . ?
C9 C8A H8AB 110.4 . . ?
H8AA C8A H8AB 108.6 . . ?
C7 C10A H10D 109.5 . . ?
C7 C10A H10E 109.5 . . ?
C7 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C7 C11A H11D 109.5 . . ?
C7 C11A H11E 109.5 . . ?
C7 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 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
N1 C1 C6 N3 50.3(3) . . . . ?
N1 C1 C6 C9 -102.7(2) . . . . ?
N1 C2 C3 N2 0.1(2) . . . . ?
N2 C1 C6 N3 -133.53(19) . . . . ?
N2 C1 C6 C9 73.4(2) . . . . ?
N3 C6 C9 C8 11.8(3) . . . . ?
N3 C6 C9 C12 112.3(2) . . . . ?
N3 C6 C9 C13 -125.0(2) . . . . ?
N3 C6 C9 C8A -20.5(3) . . . . ?
N3 C7 C8 C9 28.1(4) . . . . ?
N3 C7 C8A C9 -26.2(3) . . . . ?
N3 C14 C15 C16 -177.18(16) . . . . ?
N3 C14 C15 C20 5.5(3) . . . . ?
N3 C14 C19 C18 175.73(16) . . . . ?
N3 C14 C19 C23 -5.0(3) . . . . ?
C1 N1 C2 C3 -0.7(2) . . . . ?
C1 N2 C3 C2 0.4(2) . . . . ?
C1 C6 C9 C8 167.0(2) . . . . ?
C1 C6 C9 C12 -92.5(3) . . . . ?
C1 C6 C9 C13 30.1(3) . . . . ?
C1 C6 C9 C8A 134.7(2) . . . . ?
C2 N1 C1 N2 0.9(2) . . . . ?
C2 N1 C1 C6 177.70(17) . . . . ?
C3 N2 C1 N1 -0.8(2) . . . . ?
C3 N2 C1 C6 -177.58(17) . . . . ?
C4 N1 C1 N2 -161.82(17) . . . . ?
C4 N1 C1 C6 15.0(3) . . . . ?
C4 N1 C2 C3 162.52(18) . . . . ?
C5 N2 C1 N1 177.53(19) . . . . ?
C5 N2 C1 C6 0.8(3) . . . . ?
C5 N2 C3 C2 -178.02(19) . . . . ?
C6 N3 C7 C8 -19.8(3) . . . . ?
C6 N3 C7 C10 -146.7(2) . . . . ?
C6 N3 C7 C11 97.4(2) . . . . ?
C6 N3 C7 C8A 13.5(2) . . . . ?
C6 N3 C7 C10A -101.8(2) . . . . ?
C6 N3 C7 C11A 134.8(3) . . . . ?
C6 N3 C14 C15 -126.23(18) . . . . ?
C6 N3 C14 C19 57.2(2) . . . . ?
C6 C9 C8A C7 28.0(3) . . . . ?
C7 N3 C6 C1 -151.34(16) . . . . ?
C7 N3 C6 C9 4.3(2) . . . . ?
C7 N3 C14 C15 84.6(2) . . . . ?
C7 N3 C14 C19 -91.9(2) . . . . ?
C7 C8 C9 C6 -25.2(4) . . . . ?
C7 C8 C9 C12 -142.6(3) . . . . ?
C7 C8 C9 C13 100.8(4) . . . . ?
C10 C7 C8 C9 150.3(3) . . . . ?
C11 C7 C8 C9 -86.1(4) . . . . ?
C12 C9 C8A C7 -101.8(3) . . . . ?
C13 C9 C8A C7 142.5(2) . . . . ?
C14 N3 C6 C1 56.6(2) . . . . ?
C14 N3 C6 C9 -147.72(16) . . . . ?
C14 N3 C7 C8 132.8(3) . . . . ?
C14 N3 C7 C10 5.9(3) . . . . ?
C14 N3 C7 C11 -110.0(2) . . . . ?
C14 N3 C7 C8A 166.2(2) . . . . ?
C14 N3 C7 C10A 50.9(2) . . . . ?
C14 N3 C7 C11A -72.5(3) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C14 C15 C20 C21 113.5(2) . . . . ?
C14 C15 C20 C22 -123.68(19) . . . . ?
C14 C19 C23 C24 -121.1(2) . . . . ?
C14 C19 C23 C25 116.9(2) . . . . ?
C15 C14 C19 C18 -0.8(3) . . . . ?
C15 C14 C19 C23 178.43(17) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C15 C20 C21 -63.9(2) . . . . ?
C16 C15 C20 C22 59.0(2) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C17 C18 C19 C14 1.7(3) . . . . ?
C17 C18 C19 C23 -177.59(18) . . . . ?
C18 C19 C23 C24 58.2(2) . . . . ?
C18 C19 C23 C25 -63.8(2) . . . . ?
C19 C14 C15 C16 -0.6(3) . . . . ?
C19 C14 C15 C20 -177.91(16) . . . . ?
C20 C15 C16 C17 178.77(17) . . . . ?
O1 S1 C26 F1 -179.70(17) . . . . ?
O1 S1 C26 F2 59.86(19) . . . . ?
O1 S1 C26 F3 -60.80(19) . . . . ?
O2 S1 C26 F1 -61.29(19) . . . . ?
O2 S1 C26 F2 178.27(18) . . . . ?
O2 S1 C26 F3 57.61(19) . . . . ?
O3 S1 C26 F1 57.9(2) . . . . ?
O3 S1 C26 F2 -62.5(2) . . . . ?
O3 S1 C26 F3 176.84(19) . . . . ?
C10A C7 C8A C9 91.1(3) . . . . ?
C11A C7 C8A C9 -151.2(3) . . . . ?
_shelx_res_file
;
TITL JM1903 in P2(1)/n, MESSELBERGER/MUNZ, MJ154, orange crystals
jm1903.res
created by SHELXL-2016/6 at 17:44:28 on 06-Mar-2019
CELL 0.71073 14.9305 11.67 16.4062 90 109.508 90
ZERR 4 0.0009 0.0007 0.0009 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F N O S
UNIT 104 156 12 12 12 4
L.S. 10
PLAN 20
SIZE 0.24 0.07 0.05
TEMP -173
BOND $H
WPDB -1
CONF
HTAB
fmap 2
acta
SHEL 10 0.76
REM
REM
REM
WGHT 0.037400 3.601000
FVAR 0.52426 0.47434
N1 4 0.641209 0.239408 0.522942 11.00000 0.02177 0.02033 =
0.02148 -0.00144 0.00517 0.00179
N2 4 0.707092 0.111130 0.466492 11.00000 0.02649 0.01779 =
0.02216 -0.00362 0.00433 0.00124
N3 4 0.849671 0.318049 0.622711 11.00000 0.02052 0.01294 =
0.01468 0.00079 0.00538 0.00025
C1 1 0.724407 0.210628 0.511702 11.00000 0.02338 0.01750 =
0.01403 0.00148 0.00432 0.00404
C2 1 0.573703 0.157203 0.486004 11.00000 0.02292 0.02782 =
0.02762 0.00056 0.00406 -0.00258
AFIX 43
H2 2 0.509893 0.156859 0.485502 11.00000 -1.20000
AFIX 0
C3 1 0.614429 0.077821 0.450916 11.00000 0.02959 0.02160 =
0.02735 -0.00200 0.00134 -0.00263
AFIX 43
H3 2 0.584848 0.010917 0.420847 11.00000 -1.20000
AFIX 0
C4 1 0.617117 0.353944 0.546022 11.00000 0.02267 0.02428 =
0.02590 -0.00507 0.00529 0.00442
AFIX 137
H4A 2 0.564137 0.348224 0.568470 11.00000 -1.50000
H4B 2 0.598686 0.403046 0.494614 11.00000 -1.50000
H4C 2 0.672430 0.387108 0.590406 11.00000 -1.50000
AFIX 0
C5 1 0.772616 0.046321 0.434906 11.00000 0.03594 0.02838 =
0.04185 -0.01573 0.01177 0.00298
AFIX 137
H5A 2 0.768839 -0.035211 0.447691 11.00000 -1.50000
H5B 2 0.837598 0.073783 0.463562 11.00000 -1.50000
H5C 2 0.755346 0.056938 0.372285 11.00000 -1.50000
AFIX 0
C6 1 0.811685 0.276465 0.538344 11.00000 0.02281 0.01519 =
0.01518 0.00122 0.00723 0.00382
C7 1 0.905484 0.426579 0.623934 11.00000 0.02993 0.01485 =
0.02456 0.00144 0.00979 -0.00346
PART 1
C8 1 0.923842 0.417844 0.542796 21.00000 0.03560 0.01852 =
0.03083 0.00592 0.02155 0.00210
AFIX 23
H8A 2 0.986022 0.380188 0.552814 21.00000 -1.20000
H8B 2 0.926916 0.495609 0.519762 21.00000 -1.20000
AFIX 0
PART 0
C9 1 0.843700 0.346869 0.474748 11.00000 0.03358 0.01908 =
0.02145 0.00165 0.01656 0.00234
PART 1
C10 1 0.988935 0.436467 0.706113 21.00000 0.03103 0.02787 =
0.03161 -0.00207 0.01047 -0.01135
AFIX 137
H10A 2 0.966410 0.435848 0.755788 21.00000 -1.50000
H10B 2 1.022734 0.508321 0.705651 21.00000 -1.50000
H10C 2 1.032042 0.371677 0.710453 21.00000 -1.50000
AFIX 0
C11 1 0.837132 0.532547 0.623595 21.00000 0.04415 0.01432 =
0.03071 0.00003 0.02099 -0.00132
AFIX 137
H11A 2 0.826322 0.536207 0.679261 21.00000 -1.50000
H11B 2 0.776245 0.522395 0.577019 21.00000 -1.50000
H11C 2 0.867020 0.603856 0.614295 21.00000 -1.50000
AFIX 0
PART 0
C12 1 0.909320 0.286597 0.434816 11.00000 0.09671 0.05490 =
0.05669 0.03295 0.06317 0.04428
AFIX 137
H12A 2 0.962986 0.252945 0.480720 11.00000 -1.50000
H12B 2 0.933062 0.342089 0.402090 11.00000 -1.50000
H12C 2 0.874201 0.225916 0.395903 11.00000 -1.50000
AFIX 0
C13 1 0.760100 0.391039 0.400277 11.00000 0.05096 0.11189 =
0.07515 0.07917 0.03255 0.03523
AFIX 137
H13A 2 0.716014 0.431483 0.423079 11.00000 -1.50000
H13B 2 0.727269 0.326440 0.364541 11.00000 -1.50000
H13C 2 0.782969 0.443751 0.365068 11.00000 -1.50000
AFIX 0
C14 1 0.873109 0.243903 0.698299 11.00000 0.01781 0.01521 =
0.01460 0.00076 0.00342 -0.00119
C15 1 0.835620 0.267489 0.764881 11.00000 0.02000 0.01603 =
0.01638 -0.00109 0.00454 -0.00210
C16 1 0.862681 0.197853 0.838558 11.00000 0.02836 0.02287 =
0.01399 -0.00047 0.00646 -0.00247
AFIX 43
H16 2 0.836735 0.212300 0.883132 11.00000 -1.20000
AFIX 0
C17 1 0.926119 0.108717 0.848080 11.00000 0.02669 0.02127 =
0.01708 0.00453 0.00174 -0.00247
AFIX 43
H17 2 0.943821 0.062782 0.898789 11.00000 -1.20000
AFIX 0
C18 1 0.963625 0.086868 0.783325 11.00000 0.02057 0.01848 =
0.02330 0.00404 0.00299 0.00236
AFIX 43
H18 2 1.008152 0.026320 0.790598 11.00000 -1.20000
AFIX 0
C19 1 0.937794 0.151443 0.707499 11.00000 0.01802 0.01810 =
0.02042 0.00139 0.00624 0.00063
C20 1 0.763788 0.360956 0.761638 11.00000 0.02489 0.01789 =
0.01855 -0.00106 0.01075 0.00047
AFIX 13
H20 2 0.752436 0.405373 0.706981 11.00000 -1.20000
AFIX 0
C21 1 0.668928 0.307623 0.759441 11.00000 0.02804 0.02507 =
0.03771 0.00436 0.01803 0.00140
AFIX 137
H21A 2 0.620143 0.367422 0.747359 11.00000 -1.50000
H21B 2 0.676400 0.272301 0.815524 11.00000 -1.50000
H21C 2 0.649732 0.249127 0.714040 11.00000 -1.50000
AFIX 0
C22 1 0.798836 0.444894 0.838010 11.00000 0.04189 0.02254 =
0.02325 -0.00484 0.01611 -0.00017
AFIX 137
H22A 2 0.753153 0.507765 0.829826 11.00000 -1.50000
H22B 2 0.860831 0.475875 0.840904 11.00000 -1.50000
H22C 2 0.804856 0.404528 0.891964 11.00000 -1.50000
AFIX 0
C23 1 0.981258 0.115458 0.639635 11.00000 0.02394 0.02576 =
0.02662 0.00692 0.01311 0.00935
AFIX 13
H23 2 0.953958 0.165209 0.587584 11.00000 -1.20000
AFIX 0
C24 1 0.955910 -0.009329 0.612457 11.00000 0.06286 0.02501 =
0.03096 0.00528 0.02637 0.01544
AFIX 137
H24A 2 0.974748 -0.027054 0.562075 11.00000 -1.50000
H24B 2 0.887233 -0.020356 0.597579 11.00000 -1.50000
H24C 2 0.989545 -0.060349 0.660342 11.00000 -1.50000
AFIX 0
C25 1 1.089871 0.128476 0.671033 11.00000 0.02536 0.07420 =
0.04562 0.00858 0.01859 0.01218
AFIX 137
H25A 2 1.113282 0.113973 0.622845 11.00000 -1.50000
H25B 2 1.118507 0.073309 0.717482 11.00000 -1.50000
H25C 2 1.107107 0.206450 0.692800 11.00000 -1.50000
AFIX 0
S1 6 0.352168 0.276341 0.575033 11.00000 0.04800 0.02401 =
0.02202 -0.00448 0.01736 -0.00999
O1 5 0.386261 0.389863 0.569363 11.00000 0.06232 0.02523 =
0.04420 -0.00082 0.03303 -0.00955
O2 5 0.418072 0.188125 0.573140 11.00000 0.09731 0.03015 =
0.06491 0.00076 0.06136 0.00590
O3 5 0.256433 0.253591 0.524293 11.00000 0.06498 0.07990 =
0.03678 0.01469 -0.00566 -0.03448
C26 1 0.352109 0.265194 0.685733 11.00000 0.04584 0.02914 =
0.02685 -0.01067 0.02051 -0.01572
F1 3 0.322275 0.163143 0.701852 11.00000 0.04744 0.03509 =
0.02869 -0.00068 0.01749 -0.01782
F2 3 0.296857 0.342291 0.703532 11.00000 0.12783 0.04180 =
0.08466 -0.00063 0.08663 0.01091
F3 3 0.439691 0.278944 0.742195 11.00000 0.06695 0.08726 =
0.03037 -0.00766 0.00616 -0.04947
PART 2
C8A 1 0.873528 0.459068 0.525311 -21.00000 0.02948 0.01531 =
0.02454 0.00316 0.01479 0.00060
AFIX 23
H8AA 2 0.819567 0.513445 0.510528 -21.00000 -1.20000
H8AB 2 0.926643 0.495211 0.511379 -21.00000 -1.20000
AFIX 0
C10A 1 1.017072 0.401430 0.656630 -21.00000 0.02586 0.02252 =
0.02960 -0.00169 0.00994 -0.00605
AFIX 137
H10D 2 1.031404 0.345628 0.618073 -21.00000 -1.50000
H10E 2 1.036670 0.370452 0.715500 -21.00000 -1.50000
H10F 2 1.051586 0.472783 0.656371 -21.00000 -1.50000
AFIX 0
C11A 1 0.889297 0.522340 0.675787 -21.00000 0.03770 0.01667 =
0.03311 -0.00560 0.02213 -0.00863
AFIX 137
H11D 2 0.923644 0.590203 0.666993 -21.00000 -1.50000
H11E 2 0.912298 0.501208 0.737117 -21.00000 -1.50000
H11F 2 0.821175 0.539342 0.657760 -21.00000 -1.50000
AFIX 0
HKLF 4
REM JM1903 in P2(1)/n, MESSELBERGER/MUNZ, MJ154, orange crystals
REM R1 = 0.0577 for 5782 Fo > 4sig(Fo) and 0.0642 for all 6421 data
REM 365 parameters refined using 0 restraints
END
WGHT 0.0374 3.6026
REM Instructions for potential hydrogen bonds
HTAB C2 O2
EQIV $1 -x+1, -y, -z+1
HTAB C3 O2_$1
HTAB C4 N3
HTAB C5 O3_$1
REM Highest difference peak 0.679, deepest hole -0.649, 1-sigma level 0.056
Q1 1 0.3872 0.3333 0.7274 11.00000 0.05 0.68
Q2 1 0.2408 0.3421 0.6509 11.00000 0.05 0.58
Q3 1 0.7582 0.3627 0.3885 11.00000 0.05 0.51
Q4 1 0.3610 0.1677 0.5537 11.00000 0.05 0.39
Q5 1 0.2229 0.2739 0.5504 11.00000 0.05 0.39
Q6 1 0.7833 0.4330 0.4198 11.00000 0.05 0.35
Q7 1 0.6961 0.3930 0.3935 11.00000 0.05 0.34
Q8 1 0.8577 0.2733 0.4175 11.00000 0.05 0.34
Q9 1 0.9615 0.1248 0.6738 11.00000 0.05 0.34
Q10 1 0.7823 0.3992 0.7992 11.00000 0.05 0.34
Q11 1 0.9197 0.2174 0.4326 11.00000 0.05 0.33
Q12 1 0.8439 0.2201 0.7948 11.00000 0.05 0.33
Q13 1 0.3411 0.2759 0.6284 11.00000 0.05 0.32
Q14 1 0.8018 0.3113 0.7625 11.00000 0.05 0.32
Q15 1 0.4412 0.1871 0.6232 11.00000 0.05 0.31
Q16 1 0.9183 0.3110 0.4472 11.00000 0.05 0.29
Q17 1 0.2977 0.2660 0.5725 11.00000 0.05 0.29
Q18 1 0.8195 0.3140 0.5000 11.00000 0.05 0.28
Q19 1 0.9094 0.1958 0.7015 11.00000 0.05 0.27
Q20 1 0.5948 0.0982 0.4908 11.00000 0.05 0.27
;
_shelx_res_checksum 26686
_olex2_submission_special_instructions 'No special instructions were received'
#===END OF ALL DATA
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: tetrahydrofuran, diethyl ether'
_chemical_properties_physical Moisture-sensitive,Oxygen-sensitive