# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_exp_15643
_database_code_depnum_ccdc_archive 'CCDC 1917274'
_audit_update_record
;
2019-05-20 deposited with the CCDC. 2019-08-14 downloaded from the CCDC.
;
_audit_creation_date 2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C22 H15 F5 N2 O)'
_chemical_formula_sum 'C44 H30 F10 N4 O2'
_chemical_formula_weight 836.72
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system 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 14.0842(5)
_cell_length_b 6.3205(2)
_cell_length_c 42.4385(15)
_cell_angle_alpha 90
_cell_angle_beta 92.560(3)
_cell_angle_gamma 90
_cell_volume 3774.0(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 7990
_cell_measurement_temperature 298
_cell_measurement_theta_max 71.3570
_cell_measurement_theta_min 3.8250
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 1.087
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.69981
_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 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.473
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1712
_exptl_crystal_size_max ?
_exptl_crystal_size_mid ?
_exptl_crystal_size_min ?
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0294
_diffrn_reflns_av_unetI/netI 0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_l_max 51
_diffrn_reflns_limit_l_min -52
_diffrn_reflns_number 35658
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.945
_diffrn_reflns_theta_min 3.692
_diffrn_ambient_temperature 298
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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 -30.00 65.00 1.00 6.91 -- 37.91 -77.00-150.00 95
2 \w 21.00 105.00 1.00 6.91 -- 37.91 57.00 -60.00 84
3 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00 -90.00 95
4 \w -31.00 57.00 1.00 6.91 -- 37.91 -37.00 -60.00 88
5 \w -29.00 55.00 1.00 6.91 -- 37.91 -57.00-150.00 84
6 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00 0.00 95
7 \w 91.00 176.00 1.00 27.65 -- 108.00 45.00 -60.00 85
8 \w 39.00 109.00 1.00 27.65 -- 108.00 -94.00 120.00 70
9 \w 38.00 129.00 1.00 27.65 -- 108.00 -30.00-150.00 91
10 \w 41.00 126.00 1.00 27.65 -- 108.00 -61.00 30.00 85
11 \w 38.00 129.00 1.00 27.65 -- 108.00 -30.00 120.00 91
12 \w 100.00 178.00 1.00 27.65 -- 108.00 111.00-120.00 78
13 \w 38.00 116.00 1.00 27.65 -- 108.00-111.00-150.00 78
14 \w 39.00 109.00 1.00 27.65 -- 108.00 -94.00-120.00 70
15 \w 11.00 105.00 1.00 6.91 -- 37.91 77.00-180.00 94
16 \w 21.00 105.00 1.00 6.91 -- 37.91 57.00 120.00 84
17 \w 11.00 105.00 1.00 6.91 -- 37.91 77.00 30.00 94
18 \w 21.00 105.00 1.00 6.91 -- 37.91 57.00 0.00 84
19 \w 11.00 105.00 1.00 6.91 -- 37.91 77.00-150.00 94
20 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00 90.00 95
21 \w 90.00 175.00 1.00 27.65 -- 108.00 61.00-180.00 85
22 \w 91.00 176.00 1.00 27.65 -- 108.00 45.00-120.00 85
23 \w 39.00 109.00 1.00 27.65 -- 108.00 -94.00 0.00 70
24 \w 70.00 178.00 1.00 27.65 -- 108.00 15.00 150.00 108
25 \w 70.00 178.00 1.00 27.65 -- 108.00 15.00 60.00 108
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.1040722000
_diffrn_orient_matrix_UB_12 0.0243403000
_diffrn_orient_matrix_UB_13 0.0122212000
_diffrn_orient_matrix_UB_21 0.0315333000
_diffrn_orient_matrix_UB_22 0.0175284000
_diffrn_orient_matrix_UB_23 -0.0341855000
_diffrn_orient_matrix_UB_31 -0.0126845000
_diffrn_orient_matrix_UB_32 0.2419934000
_diffrn_orient_matrix_UB_33 0.0012389000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5491
_reflns_number_total 7320
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'CrysAlisPro 1.171.38.46 (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 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.158
_refine_diff_density_min -0.195
_refine_diff_density_rms 0.040
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.012
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 543
_refine_ls_number_reflns 7320
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0669
_refine_ls_R_factor_gt 0.0503
_refine_ls_restrained_S_all 1.012
_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^)+(0.0617P)^2^+1.0971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1268
_refine_ls_wR_factor_ref 0.1410
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C27(H27), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
C39(H39A,H39B), C53(H53A,H53B)
2.c Aromatic/amide H refined with riding coordinates:
C3(H3), C15(H15), C17(H17), C24(H24), C29(H29), C43(H43), C49(H49), C55(H55),
C59(H59), C18(H18), C41(H41), C42(H42), C46(H46), C52(H52), C54(H54), C56(H56),
C57(H57), C60(H60)
2.d Idealised Me refined as rotating group:
C51(H51A,H51B,H51C), C58(H58A,H58B,H58C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43188(9) 0.7784(2) 0.23667(3) 0.0833(4) Uani 1 1 d . . . . .
N2 N 0.39281(11) 1.4077(3) 0.17516(4) 0.0592(4) Uani 1 1 d . . . . .
C3 C 0.27799(13) 1.6803(3) 0.15989(5) 0.0563(4) Uani 1 1 d . . . . .
H3 H 0.239508 1.638224 0.175996 0.068 Uiso 1 1 calc R . . . .
C5 C 0.36138(12) 1.5709(3) 0.15493(4) 0.0522(4) Uani 1 1 d . . . . .
C6 C 0.30145(14) 1.0048(3) 0.22420(4) 0.0563(5) Uani 1 1 d . . . . .
F7 F 0.16014(9) 1.2036(3) 0.21567(4) 0.0934(5) Uani 1 1 d . . . . .
N8 N 0.32754(11) 1.3203(3) 0.19438(4) 0.0598(4) Uani 1 1 d . . . . .
O9 O 0.28936(13) 2.0856(3) 0.09749(4) 0.0860(5) Uani 1 1 d . . . . .
F10 F 0.32789(12) 0.5115(3) 0.26799(4) 0.1003(5) Uani 1 1 d . . . . .
C11 C 0.33948(15) 0.8237(4) 0.23854(5) 0.0633(5) Uani 1 1 d . . . . .
C12 C 0.56605(13) 1.3422(3) 0.16776(4) 0.0530(4) Uani 1 1 d . . . . .
C13 C 0.35756(13) 1.1381(3) 0.20386(4) 0.0548(4) Uani 1 1 d . . . . .
C15 C 0.59330(15) 1.5204(4) 0.18422(6) 0.0672(5) Uani 1 1 d . . . . .
H15 H 0.549245 1.592866 0.195829 0.081 Uiso 1 1 calc R . . . .
C17 C 0.25143(14) 1.8511(3) 0.14118(5) 0.0613(5) Uani 1 1 d . . . . .
H17 H 0.195752 1.924087 0.144985 0.074 Uiso 1 1 calc R . . . .
C19 C 0.30694(15) 1.9143(3) 0.11688(5) 0.0614(5) Uani 1 1 d . . . . .
F21 F 0.05918(10) 0.9371(3) 0.24832(4) 0.1108(6) Uani 1 1 d . . . . .
F22 F 0.14030(12) 0.5878(3) 0.27514(4) 0.1167(6) Uani 1 1 d . . . . .
C24 C 0.41500(14) 1.6314(3) 0.12961(5) 0.0602(5) Uani 1 1 d . . . . .
H24 H 0.469618 1.556135 0.125256 0.072 Uiso 1 1 calc R . . . .
C27 C 0.46623(13) 1.2543(3) 0.16684(5) 0.0546(4) Uani 1 1 d . . . . .
H27 H 0.450639 1.197843 0.145735 0.065 Uiso 1 1 calc R . . . .
C29 C 0.38802(15) 1.8017(4) 0.11093(5) 0.0648(5) Uani 1 1 d . . . . .
H29 H 0.424773 1.840711 0.094216 0.078 Uiso 1 1 calc R . . . .
C30 C 0.20521(15) 1.0373(4) 0.22864(5) 0.0668(5) Uani 1 1 d . . . . .
C33 C 0.28650(18) 0.6840(4) 0.25520(5) 0.0734(6) Uani 1 1 d . . . . .
C38 C 0.15159(16) 0.8999(5) 0.24556(5) 0.0779(7) Uani 1 1 d . . . . .
C39 C 0.45225(13) 1.0798(3) 0.19137(5) 0.0609(5) Uani 1 1 d . . . . .
H39A H 0.450423 0.940763 0.181674 0.073 Uiso 1 1 calc R . . . .
H39B H 0.502083 1.082900 0.207896 0.073 Uiso 1 1 calc R . . . .
C43 C 0.68609(18) 1.5935(4) 0.18368(6) 0.0819(7) Uani 1 1 d . . . . .
H43 H 0.703912 1.715482 0.194682 0.098 Uiso 1 1 calc R . . . .
C49 C 0.63324(16) 1.2359(4) 0.15147(6) 0.0795(7) Uani 1 1 d . . . . .
H49 H 0.616121 1.113683 0.140404 0.095 Uiso 1 1 calc R . . . .
C50 C 0.19215(18) 0.7219(5) 0.25885(5) 0.0801(7) Uani 1 1 d . . . . .
C51 C 0.21445(19) 2.2217(4) 0.10500(7) 0.0883(8) Uani 1 1 d . . . . .
H51A H 0.215019 2.344274 0.091664 0.132 Uiso 1 1 calc GR . . . .
H51B H 0.222321 2.264502 0.126666 0.132 Uiso 1 1 calc GR . . . .
H51C H 0.154970 2.148907 0.101802 0.132 Uiso 1 1 calc GR . . . .
C55 C 0.75140(18) 1.4856(5) 0.16691(7) 0.0892(8) Uani 1 1 d . . . . .
H55 H 0.813488 1.534995 0.166276 0.107 Uiso 1 1 calc R . . . .
C59 C 0.72528(18) 1.3069(6) 0.15126(7) 0.0996(9) Uani 1 1 d . . . . .
H59 H 0.769977 1.231732 0.140291 0.120 Uiso 1 1 calc R . . . .
F4 F 0.05335(11) 0.2797(2) 0.01227(3) 0.0874(4) Uani 1 1 d . . . . .
N14 N -0.01058(14) 0.0053(3) 0.05317(4) 0.0689(5) Uani 1 1 d . . . . .
C16 C 0.06563(17) -0.1026(4) 0.04929(5) 0.0660(5) Uani 1 1 d . . . . .
C18 C -0.19688(16) 0.1418(4) 0.05924(5) 0.0670(5) Uani 1 1 d . . . . .
H18 H -0.153893 0.231255 0.049907 0.080 Uiso 1 1 calc R . . . .
C20 C 0.14344(17) -0.0147(4) 0.03175(5) 0.0680(6) Uani 1 1 d . . . . .
N23 N -0.06950(15) -0.1062(3) 0.07156(5) 0.0781(5) Uani 1 1 d . . . . .
C25 C -0.02148(15) -0.3454(3) 0.11598(5) 0.0617(5) Uani 1 1 d . . . . .
F26 F 0.24750(11) -0.2961(3) 0.04612(4) 0.0996(5) Uani 1 1 d . . . . .
C28 C -0.16519(17) -0.0478(4) 0.07228(5) 0.0673(5) Uani 1 1 d . . . . .
C31 C 0.23268(19) -0.1089(5) 0.03146(5) 0.0797(7) Uani 1 1 d . . . . .
O32 O -0.45035(13) 0.1116(4) 0.07564(5) 0.1006(6) Uani 1 1 d . . . . .
C34 C 0.13605(19) 0.1757(4) 0.01513(5) 0.0732(6) Uani 1 1 d . . . . .
F35 F 0.19960(15) 0.4497(3) -0.01456(4) 0.1138(6) Uani 1 1 d . . . . .
C36 C -0.35567(17) 0.0683(4) 0.07372(6) 0.0764(6) Uani 1 1 d . . . . .
C37 C -0.03168(19) -0.3148(4) 0.08063(5) 0.0735(6) Uani 1 1 d . . . . .
H37 H -0.071961 -0.426432 0.071159 0.088 Uiso 1 1 calc R . . . .
C40 C 0.2114(2) 0.2662(5) 0.00079(6) 0.0863(7) Uani 1 1 d . . . . .
C41 C -0.32399(19) -0.1201(4) 0.08699(6) 0.0834(7) Uani 1 1 d . . . . .
H41 H -0.366970 -0.209160 0.096423 0.100 Uiso 1 1 calc R . . . .
C42 C -0.23028(19) -0.1777(4) 0.08647(6) 0.0793(7) Uani 1 1 d . . . . .
H42 H -0.210188 -0.304427 0.095681 0.095 Uiso 1 1 calc R . . . .
F44 F 0.37268(14) 0.2580(4) -0.01130(4) 0.1312(7) Uani 1 1 d . . . . .
C45 C 0.30922(19) -0.0204(6) 0.01727(6) 0.0927(9) Uani 1 1 d . . . . .
C46 C -0.29113(17) 0.1999(4) 0.05988(5) 0.0735(6) Uani 1 1 d . . . . .
H46 H -0.311278 0.327641 0.050999 0.088 Uiso 1 1 calc R . . . .
C47 C 0.2985(2) 0.1699(6) 0.00219(6) 0.0957(9) Uani 1 1 d . . . . .
F48 F 0.39226(13) -0.1216(4) 0.01855(4) 0.1282(7) Uani 1 1 d . . . . .
C52 C 0.01649(18) -0.4185(5) 0.17950(7) 0.0883(8) Uani 1 1 d . . . . .
H52 H 0.030945 -0.443249 0.200777 0.106 Uiso 1 1 calc R . . . .
C53 C 0.0657(2) -0.3133(4) 0.06541(6) 0.0877(8) Uani 1 1 d . . . . .
H53A H 0.117377 -0.323844 0.081242 0.105 Uiso 1 1 calc R . . . .
H53B H 0.070804 -0.427986 0.050397 0.105 Uiso 1 1 calc R . . . .
C54 C -0.02331(18) -0.1809(4) 0.13701(6) 0.0782(6) Uani 1 1 d . . . . .
H54 H -0.037002 -0.044613 0.129900 0.094 Uiso 1 1 calc R . . . .
C56 C -0.00320(18) -0.5459(4) 0.12740(6) 0.0786(6) Uani 1 1 d . . . . .
H56 H -0.004118 -0.659824 0.113520 0.094 Uiso 1 1 calc R . . . .
C57 C 0.0163(2) -0.5801(5) 0.15888(7) 0.0945(8) Uani 1 1 d . . . . .
H57 H 0.029555 -0.716347 0.166078 0.113 Uiso 1 1 calc R . . . .
C58 C -0.4863(2) 0.2985(6) 0.06133(8) 0.1037(9) Uani 1 1 d . . . . .
H58A H -0.475236 0.295323 0.039178 0.156 Uiso 1 1 calc GR . . . .
H58B H -0.454675 0.418866 0.070780 0.156 Uiso 1 1 calc GR . . . .
H58C H -0.553278 0.308374 0.064313 0.156 Uiso 1 1 calc GR . . . .
C60 C -0.00446(19) -0.2186(5) 0.16931(6) 0.0883(8) Uani 1 1 d . . . . .
H60 H -0.006259 -0.107670 0.183679 0.106 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0708(8) 0.0825(9) 0.0966(9) 0.0269(8) 0.0056(7) 0.0108(7)
N2 0.0499(8) 0.0575(10) 0.0707(10) 0.0081(8) 0.0095(7) 0.0051(7)
C3 0.0465(9) 0.0585(11) 0.0638(11) -0.0032(9) 0.0014(8) -0.0005(9)
C5 0.0462(9) 0.0507(10) 0.0593(10) -0.0015(8) -0.0022(8) -0.0012(8)
C6 0.0548(10) 0.0637(12) 0.0501(9) -0.0021(9) 0.0001(8) -0.0058(9)
F7 0.0637(8) 0.1121(12) 0.1056(11) 0.0311(9) 0.0154(7) 0.0196(8)
N8 0.0530(9) 0.0632(10) 0.0637(9) 0.0048(8) 0.0087(7) 0.0023(8)
O9 0.0930(12) 0.0822(11) 0.0824(11) 0.0183(9) -0.0022(9) 0.0256(10)
F10 0.1127(12) 0.0868(10) 0.1004(11) 0.0359(9) -0.0069(9) -0.0133(9)
C11 0.0622(12) 0.0677(13) 0.0595(11) 0.0039(10) -0.0008(9) -0.0059(10)
C12 0.0489(9) 0.0530(11) 0.0573(10) 0.0020(8) 0.0037(8) -0.0004(8)
C13 0.0533(10) 0.0536(11) 0.0574(10) -0.0019(9) -0.0010(8) -0.0018(9)
C15 0.0604(12) 0.0605(12) 0.0804(14) -0.0091(11) 0.0002(10) 0.0035(10)
C17 0.0513(10) 0.0625(12) 0.0693(12) -0.0084(10) -0.0068(9) 0.0094(9)
C19 0.0616(11) 0.0593(12) 0.0623(11) 0.0016(9) -0.0103(9) 0.0043(10)
F21 0.0649(8) 0.1633(17) 0.1058(11) 0.0206(11) 0.0212(8) -0.0086(10)
F22 0.1060(12) 0.1424(16) 0.1020(11) 0.0390(11) 0.0092(9) -0.0477(11)
C24 0.0524(10) 0.0635(12) 0.0649(11) 0.0017(10) 0.0043(8) 0.0080(9)
C27 0.0500(10) 0.0526(11) 0.0610(10) -0.0036(9) 0.0015(8) 0.0018(8)
C29 0.0603(11) 0.0724(14) 0.0618(11) 0.0064(10) 0.0035(9) 0.0024(10)
C30 0.0614(12) 0.0805(15) 0.0586(11) 0.0051(11) 0.0015(9) -0.0007(11)
C33 0.0855(16) 0.0708(14) 0.0626(12) 0.0107(11) -0.0097(11) -0.0138(12)
C38 0.0589(12) 0.111(2) 0.0640(12) 0.0016(13) 0.0068(10) -0.0142(13)
C39 0.0504(10) 0.0520(11) 0.0802(13) 0.0033(10) 0.0028(9) -0.0011(9)
C43 0.0763(15) 0.0705(15) 0.0976(17) -0.0070(13) -0.0113(13) -0.0170(13)
C49 0.0644(13) 0.0856(17) 0.0896(16) -0.0255(14) 0.0162(11) -0.0052(12)
C50 0.0781(15) 0.0997(19) 0.0622(12) 0.0132(13) 0.0001(11) -0.0315(14)
C51 0.0929(18) 0.0706(15) 0.0989(18) 0.0008(14) -0.0231(14) 0.0232(14)
C55 0.0561(13) 0.111(2) 0.1009(19) 0.0043(17) 0.0061(12) -0.0193(14)
C59 0.0620(14) 0.129(3) 0.111(2) -0.023(2) 0.0305(14) -0.0033(16)
F4 0.1080(11) 0.0742(9) 0.0801(9) 0.0083(7) 0.0072(8) 0.0099(8)
N14 0.0718(11) 0.0685(11) 0.0658(10) 0.0086(9) -0.0046(8) -0.0022(10)
C16 0.0807(14) 0.0643(13) 0.0521(10) -0.0055(9) -0.0063(10) 0.0046(12)
C18 0.0698(13) 0.0684(13) 0.0626(12) 0.0072(10) 0.0001(10) -0.0035(11)
C20 0.0801(14) 0.0746(14) 0.0488(10) -0.0110(10) -0.0034(9) 0.0020(12)
N23 0.0787(12) 0.0713(12) 0.0844(13) 0.0225(10) 0.0044(10) 0.0063(10)
C25 0.0590(11) 0.0576(12) 0.0683(12) 0.0047(10) 0.0006(9) -0.0043(9)
F26 0.0976(11) 0.1115(12) 0.0892(10) 0.0066(9) -0.0017(8) 0.0294(9)
C28 0.0768(14) 0.0658(13) 0.0586(11) 0.0036(10) -0.0036(10) -0.0046(11)
C31 0.0905(17) 0.0918(18) 0.0557(12) -0.0054(12) -0.0082(11) 0.0145(15)
O32 0.0703(10) 0.1242(17) 0.1076(14) 0.0183(13) 0.0080(9) -0.0084(11)
C34 0.0904(16) 0.0754(15) 0.0530(11) -0.0064(11) -0.0046(11) 0.0010(13)
F35 0.1499(16) 0.1027(12) 0.0899(11) 0.0198(10) 0.0177(10) -0.0178(11)
C36 0.0678(13) 0.0922(18) 0.0690(13) 0.0011(13) -0.0001(11) -0.0084(13)
C37 0.0944(17) 0.0535(12) 0.0718(13) 0.0029(10) -0.0063(12) 0.0011(12)
C40 0.105(2) 0.097(2) 0.0573(12) -0.0031(13) 0.0025(13) -0.0105(17)
C41 0.0873(17) 0.0875(18) 0.0754(15) 0.0083(13) 0.0023(12) -0.0244(15)
C42 0.0859(16) 0.0726(15) 0.0789(15) 0.0129(12) -0.0041(12) -0.0087(13)
F44 0.1101(13) 0.191(2) 0.0942(11) 0.0047(13) 0.0218(10) -0.0364(14)
C45 0.0750(16) 0.142(3) 0.0615(13) -0.0129(16) 0.0014(12) 0.0058(17)
C46 0.0738(14) 0.0765(15) 0.0700(13) 0.0076(12) 0.0021(11) 0.0009(12)
C47 0.100(2) 0.127(3) 0.0595(13) -0.0042(16) 0.0019(13) -0.018(2)
F48 0.0881(11) 0.193(2) 0.1037(12) -0.0004(13) 0.0061(9) 0.0250(13)
C52 0.0671(14) 0.120(2) 0.0773(15) 0.0257(17) -0.0046(12) -0.0101(15)
C53 0.119(2) 0.0694(15) 0.0766(15) 0.0022(12) 0.0225(14) 0.0213(15)
C54 0.0887(16) 0.0638(14) 0.0816(15) -0.0010(12) -0.0022(12) -0.0114(12)
C56 0.0848(16) 0.0657(14) 0.0854(16) 0.0136(12) 0.0048(12) 0.0096(12)
C57 0.099(2) 0.091(2) 0.0927(19) 0.0312(17) -0.0019(15) 0.0099(16)
C58 0.0755(17) 0.128(3) 0.108(2) -0.001(2) 0.0080(15) 0.0107(18)
C60 0.0822(16) 0.105(2) 0.0772(16) -0.0165(15) 0.0000(13) -0.0219(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
F1 C11 1.338(2) . ?
N2 C5 1.401(2) . ?
N2 N8 1.372(2) . ?
N2 C27 1.472(2) . ?
C3 C5 1.387(3) . ?
C3 C17 1.382(3) . ?
C5 C24 1.394(3) . ?
C6 C11 1.392(3) . ?
C6 C13 1.463(3) . ?
C6 C30 1.392(3) . ?
F7 C30 1.334(3) . ?
N8 C13 1.285(3) . ?
O9 C19 1.376(3) . ?
O9 C51 1.408(3) . ?
F10 C33 1.340(3) . ?
C11 C33 1.372(3) . ?
C12 C15 1.371(3) . ?
C12 C27 1.511(3) . ?
C12 C49 1.372(3) . ?
C13 C39 1.503(3) . ?
C15 C43 1.387(3) . ?
C17 C19 1.381(3) . ?
C19 C29 1.378(3) . ?
F21 C38 1.333(3) . ?
F22 C50 1.332(3) . ?
C24 C29 1.380(3) . ?
C27 C39 1.535(3) . ?
C30 C38 1.374(3) . ?
C33 C50 1.366(4) . ?
C38 C50 1.372(4) . ?
C43 C55 1.370(4) . ?
C49 C59 1.372(3) . ?
C55 C59 1.353(4) . ?
F4 C34 1.338(3) . ?
N14 C16 1.288(3) . ?
N14 N23 1.361(3) . ?
C16 C20 1.462(3) . ?
C16 C53 1.497(3) . ?
C18 C28 1.386(3) . ?
C18 C46 1.379(3) . ?
C20 C31 1.391(3) . ?
C20 C34 1.396(3) . ?
N23 C28 1.399(3) . ?
N23 C37 1.467(3) . ?
C25 C37 1.513(3) . ?
C25 C54 1.371(3) . ?
C25 C56 1.377(3) . ?
F26 C31 1.348(3) . ?
C28 C42 1.388(3) . ?
C31 C45 1.377(4) . ?
O32 C36 1.367(3) . ?
O32 C58 1.412(4) . ?
C34 C40 1.372(4) . ?
F35 C40 1.337(3) . ?
C36 C41 1.383(4) . ?
C36 C46 1.382(3) . ?
C37 C53 1.542(4) . ?
C40 C47 1.369(4) . ?
C41 C42 1.370(4) . ?
F44 C47 1.335(3) . ?
C45 C47 1.367(4) . ?
C45 F48 1.332(3) . ?
C52 C57 1.344(4) . ?
C52 C60 1.364(4) . ?
C54 C60 1.405(4) . ?
C56 C57 1.369(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
C5 N2 C27 122.97(16) . . ?
N8 N2 C5 117.32(15) . . ?
N8 N2 C27 111.95(15) . . ?
C17 C3 C5 120.78(19) . . ?
C3 C5 N2 121.37(18) . . ?
C3 C5 C24 118.13(18) . . ?
C24 C5 N2 120.48(17) . . ?
C11 C6 C13 121.61(18) . . ?
C30 C6 C11 114.84(19) . . ?
C30 C6 C13 123.34(19) . . ?
C13 N8 N2 109.09(16) . . ?
C19 O9 C51 117.5(2) . . ?
F1 C11 C6 120.39(18) . . ?
F1 C11 C33 116.5(2) . . ?
C33 C11 C6 123.1(2) . . ?
C15 C12 C27 123.67(18) . . ?
C15 C12 C49 118.4(2) . . ?
C49 C12 C27 117.95(18) . . ?
C6 C13 C39 125.29(18) . . ?
N8 C13 C6 121.46(18) . . ?
N8 C13 C39 113.23(17) . . ?
C12 C15 C43 120.5(2) . . ?
C19 C17 C3 120.48(19) . . ?
O9 C19 C17 125.6(2) . . ?
O9 C19 C29 115.2(2) . . ?
C29 C19 C17 119.28(19) . . ?
C29 C24 C5 120.80(19) . . ?
N2 C27 C12 114.49(16) . . ?
N2 C27 C39 101.42(15) . . ?
C12 C27 C39 113.22(16) . . ?
C19 C29 C24 120.4(2) . . ?
F7 C30 C6 120.6(2) . . ?
F7 C30 C38 116.8(2) . . ?
C38 C30 C6 122.6(2) . . ?
F10 C33 C11 119.7(2) . . ?
F10 C33 C50 120.3(2) . . ?
C50 C33 C11 120.0(2) . . ?
F21 C38 C30 119.7(3) . . ?
F21 C38 C50 119.9(2) . . ?
C50 C38 C30 120.3(2) . . ?
C13 C39 C27 101.85(16) . . ?
C55 C43 C15 119.8(2) . . ?
C59 C49 C12 121.0(2) . . ?
F22 C50 C33 120.4(3) . . ?
F22 C50 C38 120.5(2) . . ?
C33 C50 C38 119.1(2) . . ?
C59 C55 C43 119.8(2) . . ?
C55 C59 C49 120.4(3) . . ?
C16 N14 N23 109.37(19) . . ?
N14 C16 C20 120.8(2) . . ?
N14 C16 C53 113.3(2) . . ?
C20 C16 C53 125.8(2) . . ?
C46 C18 C28 121.1(2) . . ?
C31 C20 C16 122.7(2) . . ?
C31 C20 C34 114.3(2) . . ?
C34 C20 C16 123.0(2) . . ?
N14 N23 C28 119.24(18) . . ?
N14 N23 C37 113.11(19) . . ?
C28 N23 C37 124.8(2) . . ?
C54 C25 C37 123.0(2) . . ?
C54 C25 C56 118.5(2) . . ?
C56 C25 C37 118.3(2) . . ?
C18 C28 N23 120.9(2) . . ?
C18 C28 C42 118.5(2) . . ?
C42 C28 N23 120.6(2) . . ?
F26 C31 C20 119.5(2) . . ?
F26 C31 C45 116.8(3) . . ?
C45 C31 C20 123.7(3) . . ?
C36 O32 C58 118.2(2) . . ?
F4 C34 C20 120.9(2) . . ?
F4 C34 C40 116.3(2) . . ?
C40 C34 C20 122.8(3) . . ?
O32 C36 C41 116.5(2) . . ?
O32 C36 C46 124.5(2) . . ?
C46 C36 C41 119.0(2) . . ?
N23 C37 C25 113.08(19) . . ?
N23 C37 C53 101.76(19) . . ?
C25 C37 C53 111.7(2) . . ?
F35 C40 C34 119.7(3) . . ?
F35 C40 C47 119.9(3) . . ?
C47 C40 C34 120.3(3) . . ?
C42 C41 C36 121.0(2) . . ?
C41 C42 C28 120.4(2) . . ?
C47 C45 C31 119.3(3) . . ?
F48 C45 C31 119.4(3) . . ?
F48 C45 C47 121.3(3) . . ?
C18 C46 C36 120.0(2) . . ?
F44 C47 C40 120.8(3) . . ?
F44 C47 C45 119.7(3) . . ?
C45 C47 C40 119.4(3) . . ?
C57 C52 C60 120.2(3) . . ?
C16 C53 C37 102.4(2) . . ?
C25 C54 C60 119.9(2) . . ?
C57 C56 C25 121.0(3) . . ?
C52 C57 C56 120.6(3) . . ?
C52 C60 C54 119.7(3) . . ?
_iucr_refine_instructions_details
;
TITL exp_15643 in P21/c #14
exp_15643.res
created by SHELXL-2018/3 at 10:53:50 on 27-Feb-2019
REM reset to P21/c #14
CELL 1.54184 14.08417 6.32046 42.43851 90 92.5604 90
ZERR 4 0.00048 0.00021 0.00149 0 0.0031 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O
UNIT 176 120 40 16 8
L.S. 10
PLAN 5
TEMP 24.85
BOND
fmap 2
acta
REM
REM
REM
WGHT 0.061700 1.097100
FVAR 2.17334
F1 3 0.431878 0.778432 0.236675 11.00000 0.07082 0.08254 =
0.09661 0.02688 0.00557 0.01078
N2 4 0.392805 1.407721 0.175157 11.00000 0.04989 0.05748 =
0.07074 0.00806 0.00951 0.00506
C3 1 0.277992 1.680310 0.159889 11.00000 0.04646 0.05845 =
0.06379 -0.00320 0.00144 -0.00047
AFIX 43
H3 2 0.239508 1.638224 0.175996 11.00000 -1.20000
AFIX 0
C5 1 0.361379 1.570859 0.154929 11.00000 0.04621 0.05074 =
0.05926 -0.00150 -0.00217 -0.00121
C6 1 0.301447 1.004790 0.224197 11.00000 0.05476 0.06371 =
0.05013 -0.00211 0.00007 -0.00578
F7 3 0.160139 1.203607 0.215667 11.00000 0.06372 0.11205 =
0.10559 0.03106 0.01544 0.01955
N8 4 0.327537 1.320312 0.194379 11.00000 0.05299 0.06320 =
0.06371 0.00481 0.00874 0.00230
O9 5 0.289360 2.085623 0.097494 11.00000 0.09298 0.08217 =
0.08244 0.01834 -0.00219 0.02565
F10 3 0.327891 0.511487 0.267988 11.00000 0.11268 0.08682 =
0.10042 0.03589 -0.00693 -0.01332
C11 1 0.339480 0.823663 0.238540 11.00000 0.06220 0.06773 =
0.05955 0.00386 -0.00082 -0.00587
C12 1 0.566053 1.342227 0.167758 11.00000 0.04887 0.05296 =
0.05729 0.00200 0.00375 -0.00036
C13 1 0.357563 1.138142 0.203857 11.00000 0.05326 0.05359 =
0.05738 -0.00193 -0.00100 -0.00176
C15 1 0.593305 1.520428 0.184216 11.00000 0.06036 0.06054 =
0.08043 -0.00913 0.00019 0.00348
AFIX 43
H15 2 0.549245 1.592866 0.195829 11.00000 -1.20000
AFIX 0
C17 1 0.251426 1.851128 0.141180 11.00000 0.05130 0.06253 =
0.06928 -0.00840 -0.00680 0.00945
AFIX 43
H17 2 0.195752 1.924087 0.144985 11.00000 -1.20000
AFIX 0
C19 1 0.306936 1.914263 0.116882 11.00000 0.06160 0.05925 =
0.06229 0.00163 -0.01034 0.00431
F21 3 0.059181 0.937148 0.248318 11.00000 0.06495 0.16325 =
0.10584 0.02059 0.02122 -0.00860
F22 3 0.140300 0.587754 0.275142 11.00000 0.10604 0.14242 =
0.10203 0.03897 0.00924 -0.04770
C24 1 0.415002 1.631412 0.129609 11.00000 0.05239 0.06347 =
0.06488 0.00174 0.00433 0.00803
AFIX 43
H24 2 0.469618 1.556135 0.125256 11.00000 -1.20000
AFIX 0
C27 1 0.466233 1.254297 0.166842 11.00000 0.05001 0.05255 =
0.06101 -0.00357 0.00154 0.00178
AFIX 13
H27 2 0.450639 1.197843 0.145735 11.00000 -1.20000
AFIX 0
C29 1 0.388016 1.801666 0.110931 11.00000 0.06030 0.07236 =
0.06179 0.00636 0.00349 0.00240
AFIX 43
H29 2 0.424773 1.840711 0.094216 11.00000 -1.20000
AFIX 0
C30 1 0.205208 1.037340 0.228641 11.00000 0.06136 0.08047 =
0.05855 0.00506 0.00145 -0.00075
C33 1 0.286504 0.684036 0.255196 11.00000 0.08547 0.07079 =
0.06262 0.01068 -0.00971 -0.01384
C38 1 0.151586 0.899941 0.245556 11.00000 0.05888 0.11120 =
0.06398 0.00163 0.00677 -0.01416
C39 1 0.452247 1.079763 0.191370 11.00000 0.05044 0.05196 =
0.08022 0.00326 0.00280 -0.00108
AFIX 23
H39A 2 0.450423 0.940763 0.181674 11.00000 -1.20000
H39B 2 0.502083 1.082900 0.207896 11.00000 -1.20000
AFIX 0
C43 1 0.686087 1.593507 0.183680 11.00000 0.07630 0.07054 =
0.09762 -0.00698 -0.01128 -0.01699
AFIX 43
H43 2 0.703912 1.715482 0.194682 11.00000 -1.20000
AFIX 0
C49 1 0.633241 1.235853 0.151472 11.00000 0.06442 0.08560 =
0.08960 -0.02555 0.01624 -0.00523
AFIX 43
H49 2 0.616121 1.113683 0.140404 11.00000 -1.20000
AFIX 0
C50 1 0.192153 0.721876 0.258846 11.00000 0.07807 0.09970 =
0.06221 0.01323 0.00013 -0.03150
C51 1 0.214455 2.221655 0.105004 11.00000 0.09290 0.07058 =
0.09894 0.00075 -0.02309 0.02321
AFIX 137
H51A 2 0.215019 2.344274 0.091664 11.00000 -1.50000
H51B 2 0.222321 2.264502 0.126666 11.00000 -1.50000
H51C 2 0.154970 2.148907 0.101802 11.00000 -1.50000
AFIX 0
C55 1 0.751404 1.485584 0.166905 11.00000 0.05605 0.11098 =
0.10091 0.00430 0.00606 -0.01928
AFIX 43
H55 2 0.813488 1.534995 0.166276 11.00000 -1.20000
AFIX 0
C59 1 0.725280 1.306901 0.151260 11.00000 0.06201 0.12859 =
0.11064 -0.02298 0.03053 -0.00330
AFIX 43
H59 2 0.769977 1.231732 0.140291 11.00000 -1.20000
AFIX 0
F4 3 0.053348 0.279672 0.012265 11.00000 0.10803 0.07424 =
0.08005 0.00833 0.00721 0.00992
N14 4 -0.010578 0.005341 0.053168 11.00000 0.07182 0.06852 =
0.06581 0.00864 -0.00456 -0.00225
C16 1 0.065630 -0.102561 0.049289 11.00000 0.08070 0.06429 =
0.05209 -0.00548 -0.00625 0.00462
C18 1 -0.196882 0.141762 0.059242 11.00000 0.06976 0.06843 =
0.06264 0.00724 0.00013 -0.00351
AFIX 43
H18 2 -0.153893 0.231255 0.049907 11.00000 -1.20000
AFIX 0
C20 1 0.143440 -0.014702 0.031754 11.00000 0.08006 0.07463 =
0.04883 -0.01095 -0.00344 0.00195
N23 4 -0.069502 -0.106241 0.071561 11.00000 0.07866 0.07127 =
0.08442 0.02254 0.00445 0.00632
C25 1 -0.021475 -0.345375 0.115979 11.00000 0.05901 0.05763 =
0.06827 0.00469 0.00057 -0.00433
F26 3 0.247496 -0.296051 0.046115 11.00000 0.09756 0.11150 =
0.08918 0.00663 -0.00171 0.02935
C28 1 -0.165187 -0.047841 0.072284 11.00000 0.07677 0.06583 =
0.05860 0.00356 -0.00362 -0.00456
C31 1 0.232685 -0.108946 0.031460 11.00000 0.09049 0.09179 =
0.05571 -0.00536 -0.00821 0.01448
O32 5 -0.450352 0.111569 0.075638 11.00000 0.07028 0.12423 =
0.10762 0.01828 0.00795 -0.00839
C34 1 0.136055 0.175693 0.015133 11.00000 0.09040 0.07536 =
0.05305 -0.00643 -0.00455 0.00104
F35 3 0.199605 0.449723 -0.014559 11.00000 0.14989 0.10268 =
0.08989 0.01982 0.01767 -0.01784
C36 1 -0.355666 0.068317 0.073717 11.00000 0.06780 0.09216 =
0.06896 0.00106 -0.00013 -0.00836
C37 1 -0.031680 -0.314848 0.080629 11.00000 0.09442 0.05347 =
0.07178 0.00288 -0.00627 0.00112
AFIX 13
H37 2 -0.071961 -0.426432 0.071159 11.00000 -1.20000
AFIX 0
C40 1 0.211409 0.266218 0.000786 11.00000 0.10478 0.09674 =
0.05735 -0.00313 0.00254 -0.01054
C41 1 -0.323994 -0.120113 0.086994 11.00000 0.08726 0.08747 =
0.07538 0.00827 0.00227 -0.02435
AFIX 43
H41 2 -0.366970 -0.209160 0.096423 11.00000 -1.20000
AFIX 0
C42 1 -0.230282 -0.177657 0.086474 11.00000 0.08586 0.07259 =
0.07888 0.01289 -0.00406 -0.00866
AFIX 43
H42 2 -0.210188 -0.304427 0.095681 11.00000 -1.20000
AFIX 0
F44 3 0.372678 0.258041 -0.011296 11.00000 0.11009 0.19086 =
0.09421 0.00469 0.02177 -0.03635
C45 1 0.309216 -0.020392 0.017274 11.00000 0.07503 0.14156 =
0.06151 -0.01294 0.00139 0.00576
C46 1 -0.291130 0.199897 0.059879 11.00000 0.07381 0.07647 =
0.07005 0.00757 0.00210 0.00090
AFIX 43
H46 2 -0.311278 0.327641 0.050999 11.00000 -1.20000
AFIX 0
C47 1 0.298516 0.169856 0.002191 11.00000 0.10019 0.12743 =
0.05945 -0.00424 0.00191 -0.01797
F48 3 0.392263 -0.121560 0.018551 11.00000 0.08806 0.19291 =
0.10370 -0.00039 0.00606 0.02504
C52 1 0.016486 -0.418534 0.179498 11.00000 0.06709 0.11971 =
0.07731 0.02568 -0.00457 -0.01007
AFIX 43
H52 2 0.030945 -0.443249 0.200777 11.00000 -1.20000
AFIX 0
C53 1 0.065741 -0.313281 0.065414 11.00000 0.11866 0.06943 =
0.07660 0.00223 0.02253 0.02134
AFIX 23
H53A 2 0.117377 -0.323844 0.081242 11.00000 -1.20000
H53B 2 0.070804 -0.427986 0.050397 11.00000 -1.20000
AFIX 0
C54 1 -0.023307 -0.180891 0.137008 11.00000 0.08874 0.06382 =
0.08162 -0.00098 -0.00222 -0.01139
AFIX 43
H54 2 -0.037002 -0.044613 0.129900 11.00000 -1.20000
AFIX 0
C56 1 -0.003199 -0.545905 0.127401 11.00000 0.08481 0.06570 =
0.08540 0.01365 0.00482 0.00957
AFIX 43
H56 2 -0.004118 -0.659824 0.113520 11.00000 -1.20000
AFIX 0
C57 1 0.016303 -0.580070 0.158882 11.00000 0.09941 0.09084 =
0.09268 0.03117 -0.00190 0.00989
AFIX 43
H57 2 0.029555 -0.716347 0.166078 11.00000 -1.20000
AFIX 0
C58 1 -0.486257 0.298481 0.061333 11.00000 0.07551 0.12762 =
0.10843 -0.00094 0.00800 0.01068
AFIX 137
H58A 2 -0.475236 0.295323 0.039178 11.00000 -1.50000
H58B 2 -0.454675 0.418866 0.070780 11.00000 -1.50000
H58C 2 -0.553278 0.308374 0.064313 11.00000 -1.50000
AFIX 0
C60 1 -0.004460 -0.218554 0.169313 11.00000 0.08221 0.10503 =
0.07721 -0.01648 0.00004 -0.02194
AFIX 43
H60 2 -0.006259 -0.107670 0.183679 11.00000 -1.20000
AFIX 0
HKLF 4
REM exp_15643 in P21/c #14
REM wR2 = 0.1410, GooF = S = 1.012, Restrained GooF = 1.012 for all data
REM R1 = 0.0503 for 5491 Fo > 4sig(Fo) and 0.0669 for all 7320 data
REM 543 parameters refined using 0 restraints
END
WGHT 0.0616 1.0970
REM Highest difference peak 0.158, deepest hole -0.195, 1-sigma level 0.040
Q1 1 0.0771 1.1002 0.2613 11.00000 0.05 0.16
Q2 1 0.3669 -0.2827 0.0183 11.00000 0.05 0.15
Q3 1 0.0030 -0.3649 0.0584 11.00000 0.05 0.14
Q4 1 0.0118 -0.2405 0.1246 11.00000 0.05 0.13
Q5 1 -0.1198 -0.1306 0.0589 11.00000 0.05 0.13
REM The information below was added by Olex2.
REM
REM R1 = 0.0503 for 5491 Fo > 4sig(Fo) and 0.0669 for all 38295 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.16, deepest hole -0.20
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0669
REM R1_gt = 0.0503
REM wR_ref = 0.1410
REM GOOF = 1.012
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 38295
REM Reflections_gt = 5491
REM Parameters = n/a
REM Hole = -0.20
REM Peak = 0.16
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.663
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_exp_15560
_database_code_depnum_ccdc_archive 'CCDC 1917276'
_audit_update_record
;
2019-05-20 deposited with the CCDC. 2019-08-14 downloaded from the CCDC.
;
_audit_creation_date 2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H22 F5 N3'
_chemical_formula_sum 'C25 H22 F5 N3'
_chemical_formula_weight 459.45
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 19.5027(9)
_cell_length_b 5.9539(3)
_cell_length_c 20.2366(9)
_cell_angle_alpha 90
_cell_angle_beta 111.013(5)
_cell_angle_gamma 90
_cell_volume 2193.54(19)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 5153
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 71.1180
_cell_measurement_theta_min 3.9230
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.961
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.50945
_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 ?
_exptl_crystal_density_diffrn 1.391
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 952
_exptl_crystal_size_max ?
_exptl_crystal_size_mid ?
_exptl_crystal_size_min ?
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0248
_diffrn_reflns_av_unetI/netI 0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 23
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 20846
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.872
_diffrn_reflns_theta_min 3.930
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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 -4.00 77.00 1.00 5.25 -- 37.78 -99.00 -60.00 81
2 \w -29.00 55.00 1.00 5.25 -- 37.78 -57.00-120.00 84
3 \w -30.00 65.00 1.00 5.25 -- 37.78 -77.00 150.00 95
4 \w -4.00 77.00 1.00 5.25 -- 37.78 -99.00 30.00 81
5 \w 11.00 105.00 1.00 5.25 -- 37.78 77.00 -90.00 94
6 \w -29.00 55.00 1.00 5.25 -- 37.78 -57.00 30.00 84
7 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00 0.00 84
8 \w 40.00 125.00 1.00 21.00 -- 108.00 -45.00-150.00 85
9 \w 41.00 126.00 1.00 21.00 -- 108.00 -61.00 120.00 85
10 \w 39.00 109.00 1.00 21.00 -- 108.00 -94.00 90.00 70
11 \w 70.00 178.00 1.00 21.00 -- 108.00 15.00 -60.00 108
12 \w 38.00 116.00 1.00 21.00 -- 108.00-111.00-120.00 78
13 \w 37.00 146.00 1.00 21.00 -- 108.00 -15.00 90.00 109
14 \w -34.00 67.00 1.00 5.25 -- 37.78 -19.00 -90.00 101
15 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00 30.00 84
16 \w 11.00 105.00 1.00 5.25 -- 37.78 77.00 150.00 94
17 \w 11.00 105.00 1.00 5.25 -- 37.78 77.00 90.00 94
18 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00-120.00 84
19 \w 21.00 105.00 1.00 5.25 -- 37.78 57.00 90.00 84
20 \w 91.00 176.00 1.00 21.00 -- 108.00 45.00-180.00 85
21 \w 81.00 172.00 1.00 21.00 -- 108.00 77.00 120.00 91
22 \w 81.00 176.00 1.00 21.00 -- 108.00 77.00-150.00 95
23 \w 70.00 178.00 1.00 21.00 -- 108.00 15.00 30.00 108
24 \w 41.00 126.00 1.00 21.00 -- 108.00 -61.00 -30.00 85
25 \w 87.00 178.00 1.00 21.00 -- 108.00 30.00 120.00 91
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0842448000
_diffrn_orient_matrix_UB_12 0.0166173000
_diffrn_orient_matrix_UB_13 0.0238500000
_diffrn_orient_matrix_UB_21 0.0053752000
_diffrn_orient_matrix_UB_22 0.0216306000
_diffrn_orient_matrix_UB_23 0.0775771000
_diffrn_orient_matrix_UB_31 0.0058849000
_diffrn_orient_matrix_UB_32 -0.2572623000
_diffrn_orient_matrix_UB_33 0.0080403000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2869
_reflns_number_total 4257
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'CrysAlisPro 1.171.38.46 (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 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.920
_refine_diff_density_min -0.235
_refine_diff_density_rms 0.053
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.054
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 300
_refine_ls_number_reflns 4257
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0925
_refine_ls_R_factor_gt 0.0700
_refine_ls_restrained_S_all 1.054
_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^)+(0.1611P)^2^+0.4132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2284
_refine_ls_wR_factor_ref 0.2659
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C15(H15)
2.b Secondary CH2 refined with riding coordinates:
C9BA(H9BA,H9BB), C2CA(H2CA,H2CB), C6CA(H6CA,H6CB)
2.c Aromatic/amide H refined with riding coordinates:
C19(H19), C23(H23), C21(H21), C22(H22), C24(H24), C20(H20), C26(H26),
C28(H28), C25(H25)
2.d Idealised Me refined as rotating group:
C32(H32A,H32B,H32C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.18865(12) 0.8929(4) 0.10585(10) 0.1030(7) Uani 1 1 d . . . . .
F7 F 0.20187(12) 0.7760(4) 0.23569(9) 0.1125(8) Uani 1 1 d . . . . .
F11 F 0.05006(10) 0.2340(3) 0.01850(9) 0.0897(6) Uani 1 1 d . . . . .
C3 C 0.12027(12) 0.5673(5) 0.05483(13) 0.0661(7) Uani 1 1 d . . . . .
N9 N 0.08354(12) 0.4968(5) -0.06954(11) 0.0766(7) Uani 1 1 d . . . . .
F13 F 0.14153(11) 0.3862(4) 0.25990(9) 0.1062(7) Uani 1 1 d . . . . .
F19 F 0.06456(12) 0.1247(4) 0.14854(11) 0.1074(7) Uani 1 1 d . . . . .
C5 C 0.11676(13) 0.6270(5) -0.01629(13) 0.0689(7) Uani 1 1 d . . . . .
C4 C 0.16486(15) 0.6394(6) 0.18165(14) 0.0807(8) Uani 1 1 d . . . . .
C8 C 0.13424(15) 0.4462(6) 0.19404(14) 0.0807(9) Uani 1 1 d . . . . .
C2 C 0.15750(15) 0.6997(5) 0.11364(14) 0.0737(7) Uani 1 1 d . . . . .
C6 C 0.08908(14) 0.3742(5) 0.06982(13) 0.0706(7) Uani 1 1 d . . . . .
C17 C 0.05114(13) 0.4891(6) -0.19509(13) 0.0728(8) Uani 1 1 d . . . . .
C12 C 0.09563(16) 0.3128(6) 0.13789(15) 0.0784(8) Uani 1 1 d . . . . .
C18 C 0.20195(14) 0.7596(5) -0.13343(12) 0.0688(7) Uani 1 1 d . . . . .
N14 N 0.08897(14) 0.5872(6) -0.12912(12) 0.0901(8) Uani 1 1 d . . . . .
C19 C 0.01245(14) 0.2920(6) -0.19992(14) 0.0759(8) Uani 1 1 d . . . . .
H19 H 0.011760 0.222859 -0.158949 0.091 Uiso 1 1 calc R . . . .
C27 C -0.02688(15) 0.2962(7) -0.32827(14) 0.0843(9) Uani 1 1 d . . . . .
C23 C -0.02526(16) 0.1965(6) -0.26506(15) 0.0831(8) Uani 1 1 d . . . . .
H23 H -0.050287 0.062226 -0.267003 0.100 Uiso 1 1 calc R . . . .
C21 C 0.24239(18) 0.5653(6) -0.11463(16) 0.0854(9) Uani 1 1 d . . . . .
H21 H 0.226586 0.450984 -0.092197 0.103 Uiso 1 1 calc R . . . .
C22 C 0.22618(18) 0.9271(6) -0.16693(16) 0.0874(9) Uani 1 1 d . . . . .
H22 H 0.199048 1.058699 -0.180522 0.105 Uiso 1 1 calc R . . . .
C24 C 0.01137(16) 0.4936(7) -0.32202(15) 0.0905(10) Uani 1 1 d . . . . .
H24 H 0.010789 0.566299 -0.362886 0.109 Uiso 1 1 calc R . . . .
C15 C 0.13359(17) 0.7906(5) -0.11703(15) 0.0785(8) Uani 1 1 d . . . . .
H15 H 0.104398 0.913892 -0.145565 0.094 Uiso 1 1 calc R . . . .
N29 N -0.06361(19) 0.1939(7) -0.39355(14) 0.1126(11) Uani 1 1 d . . . . .
C9BA C 0.14792(19) 0.8339(6) -0.03755(17) 0.0876(9) Uani 1 1 d . . . . .
H9BA H 0.200028 0.848623 -0.010535 0.105 Uiso 1 1 calc R . . . .
H9BB H 0.122783 0.968151 -0.031211 0.105 Uiso 1 1 calc R . . . .
C20 C 0.05060(16) 0.5874(7) -0.25715(15) 0.0901(10) Uani 1 1 d . . . . .
H20 H 0.077078 0.718808 -0.255121 0.108 Uiso 1 1 calc R . . . .
C26 C 0.2903(2) 0.9013(8) -0.1805(2) 0.1044(12) Uani 1 1 d . . . . .
H26 H 0.306680 1.015685 -0.202410 0.125 Uiso 1 1 calc R . . . .
C2CA C -0.0678(4) 0.2976(13) -0.4583(2) 0.166(3) Uani 1 1 d . . . . .
H2CA H -0.022131 0.376245 -0.451136 0.199 Uiso 1 1 calc R . . . .
H2CB H -0.073178 0.181861 -0.493590 0.199 Uiso 1 1 calc R . . . .
C28 C 0.3298(2) 0.7054(9) -0.1613(2) 0.1056(13) Uani 1 1 d . . . . .
H28 H 0.372792 0.687524 -0.170630 0.127 Uiso 1 1 calc R . . . .
C25 C 0.30668(19) 0.5375(8) -0.12873(19) 0.0999(11) Uani 1 1 d . . . . .
H25 H 0.333592 0.405223 -0.116017 0.120 Uiso 1 1 calc R . . . .
C32 C -0.1844(4) 0.082(2) -0.3959(3) 0.282(7) Uani 1 1 d . . . . .
H32A H -0.176929 0.139859 -0.349543 0.424 Uiso 1 1 calc GR . . . .
H32B H -0.215652 -0.047891 -0.404593 0.424 Uiso 1 1 calc GR . . . .
H32C H -0.207111 0.194780 -0.430703 0.424 Uiso 1 1 calc GR . . . .
C6CA C -0.1116(4) 0.0171(11) -0.4002(2) 0.167(3) Uani 1 1 d . . . . .
H6CA H -0.088297 -0.091639 -0.363270 0.200 Uiso 1 1 calc R . . . .
H6CB H -0.120435 -0.056092 -0.445333 0.200 Uiso 1 1 calc R . . . .
C1 C -0.1249(9) 0.446(2) -0.4837(6) 0.395(11) Uani 1 1 d . . . . .
H1A H -0.151963 0.449467 -0.452357 0.592 Uiso 1 1 calc GR . . . .
H1B H -0.156676 0.399359 -0.529919 0.592 Uiso 1 1 calc GR . . . .
H1C H -0.105952 0.593060 -0.486487 0.592 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
F1 0.1165(14) 0.1114(15) 0.0768(11) -0.0146(10) 0.0294(10) -0.0337(12)
F7 0.1103(14) 0.153(2) 0.0657(11) -0.0266(11) 0.0217(10) -0.0281(13)
F11 0.0979(11) 0.1020(14) 0.0726(10) -0.0133(9) 0.0345(9) -0.0213(10)
C3 0.0553(12) 0.0831(18) 0.0590(13) -0.0026(12) 0.0194(10) 0.0046(11)
N9 0.0631(11) 0.1091(19) 0.0541(12) 0.0019(11) 0.0167(9) -0.0114(12)
F13 0.1088(13) 0.152(2) 0.0607(9) 0.0151(10) 0.0336(9) 0.0117(13)
F19 0.1303(16) 0.1088(16) 0.0959(13) 0.0075(11) 0.0561(12) -0.0160(12)
C5 0.0576(12) 0.0867(19) 0.0599(13) -0.0014(12) 0.0180(10) 0.0013(12)
C4 0.0685(15) 0.110(2) 0.0577(14) -0.0117(14) 0.0155(11) -0.0003(15)
C8 0.0730(15) 0.113(3) 0.0564(14) 0.0068(14) 0.0236(12) 0.0144(16)
C2 0.0675(14) 0.087(2) 0.0642(15) -0.0043(13) 0.0210(12) -0.0062(13)
C6 0.0643(13) 0.0870(19) 0.0602(14) -0.0062(12) 0.0220(11) 0.0008(13)
C17 0.0538(12) 0.107(2) 0.0532(13) 0.0008(13) 0.0136(10) 0.0015(13)
C12 0.0763(16) 0.093(2) 0.0713(17) 0.0051(15) 0.0334(13) 0.0055(15)
C18 0.0754(15) 0.0725(17) 0.0519(12) 0.0043(11) 0.0150(11) -0.0073(12)
N14 0.0852(15) 0.128(2) 0.0537(12) 0.0029(12) 0.0208(10) -0.0319(15)
C19 0.0644(13) 0.105(2) 0.0542(13) 0.0063(13) 0.0163(11) 0.0056(15)
C27 0.0641(14) 0.130(3) 0.0535(14) -0.0004(15) 0.0149(11) 0.0094(17)
C23 0.0759(15) 0.107(2) 0.0588(15) -0.0019(14) 0.0148(12) 0.0011(16)
C21 0.0946(19) 0.087(2) 0.0703(16) 0.0117(14) 0.0237(14) 0.0024(16)
C22 0.101(2) 0.083(2) 0.0758(17) 0.0076(15) 0.0278(15) -0.0162(16)
C24 0.0733(16) 0.142(3) 0.0548(14) 0.0111(17) 0.0214(12) 0.0014(19)
C15 0.0814(16) 0.085(2) 0.0664(15) 0.0087(13) 0.0227(13) 0.0034(15)
N29 0.113(2) 0.156(3) 0.0578(15) -0.0141(16) 0.0172(14) -0.015(2)
C9BA 0.100(2) 0.093(2) 0.0736(18) -0.0027(15) 0.0365(15) -0.0053(17)
C20 0.0757(16) 0.129(3) 0.0614(15) 0.0096(16) 0.0202(12) -0.0132(17)
C26 0.103(2) 0.123(3) 0.093(2) -0.003(2) 0.0420(19) -0.037(2)
C2CA 0.198(6) 0.214(7) 0.057(2) -0.004(3) 0.012(3) -0.049(5)
C28 0.0801(19) 0.155(4) 0.083(2) -0.019(2) 0.0304(16) -0.019(2)
C25 0.086(2) 0.118(3) 0.085(2) -0.007(2) 0.0171(16) 0.014(2)
C32 0.149(5) 0.58(2) 0.117(5) -0.074(8) 0.052(4) -0.155(9)
C6CA 0.228(6) 0.180(5) 0.068(2) -0.031(3) 0.023(3) -0.072(5)
C1 0.57(2) 0.267(13) 0.191(10) 0.067(10) -0.054(13) -0.029(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
F1 C2 1.337(4) . ?
F7 C4 1.346(3) . ?
F11 C6 1.337(3) . ?
C3 C5 1.460(4) . ?
C3 C2 1.395(4) . ?
C3 C6 1.384(4) . ?
N9 C5 1.297(4) . ?
N9 N14 1.359(3) . ?
F13 C8 1.337(3) . ?
F19 C12 1.327(4) . ?
C5 C9BA 1.503(4) . ?
C4 C8 1.361(5) . ?
C4 C2 1.379(4) . ?
C8 C12 1.370(4) . ?
C6 C12 1.386(4) . ?
C17 N14 1.400(4) . ?
C17 C19 1.380(4) . ?
C17 C20 1.382(4) . ?
C18 C21 1.375(4) . ?
C18 C22 1.381(4) . ?
C18 C15 1.496(4) . ?
N14 C15 1.460(4) . ?
C19 C23 1.381(4) . ?
C27 C23 1.400(5) . ?
C27 C24 1.373(5) . ?
C27 N29 1.397(4) . ?
C21 C25 1.392(5) . ?
C22 C26 1.382(5) . ?
C24 C20 1.379(4) . ?
C15 C9BA 1.552(4) . ?
N29 C2CA 1.425(6) . ?
N29 C6CA 1.383(7) . ?
C26 C28 1.374(6) . ?
C2CA C1 1.368(13) . ?
C28 C25 1.360(6) . ?
C32 C6CA 1.503(9) . ?
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
C2 C3 C5 122.0(3) . . ?
C6 C3 C5 123.3(2) . . ?
C6 C3 C2 114.7(2) . . ?
C5 N9 N14 109.0(3) . . ?
C3 C5 C9BA 126.9(2) . . ?
N9 C5 C3 120.4(3) . . ?
N9 C5 C9BA 112.6(2) . . ?
F7 C4 C8 120.3(3) . . ?
F7 C4 C2 119.2(3) . . ?
C8 C4 C2 120.6(3) . . ?
F13 C8 C4 120.9(3) . . ?
F13 C8 C12 120.2(3) . . ?
C4 C8 C12 119.0(3) . . ?
F1 C2 C3 120.4(3) . . ?
F1 C2 C4 116.9(3) . . ?
C4 C2 C3 122.7(3) . . ?
F11 C6 C3 121.4(2) . . ?
F11 C6 C12 115.6(3) . . ?
C3 C6 C12 123.1(3) . . ?
C19 C17 N14 120.7(3) . . ?
C19 C17 C20 118.0(3) . . ?
C20 C17 N14 121.3(3) . . ?
F19 C12 C8 120.1(3) . . ?
F19 C12 C6 119.9(3) . . ?
C8 C12 C6 119.9(3) . . ?
C21 C18 C22 118.7(3) . . ?
C21 C18 C15 120.7(3) . . ?
C22 C18 C15 120.6(3) . . ?
N9 N14 C17 119.9(3) . . ?
N9 N14 C15 114.3(2) . . ?
C17 N14 C15 125.8(2) . . ?
C17 C19 C23 120.6(3) . . ?
C24 C27 C23 116.4(3) . . ?
C24 C27 N29 122.5(3) . . ?
N29 C27 C23 121.0(4) . . ?
C19 C23 C27 121.8(3) . . ?
C18 C21 C25 120.9(3) . . ?
C18 C22 C26 120.7(4) . . ?
C27 C24 C20 122.2(3) . . ?
C18 C15 C9BA 114.0(2) . . ?
N14 C15 C18 112.7(3) . . ?
N14 C15 C9BA 100.7(2) . . ?
C27 N29 C2CA 121.5(4) . . ?
C6CA N29 C27 121.6(3) . . ?
C6CA N29 C2CA 115.3(4) . . ?
C5 C9BA C15 102.7(2) . . ?
C24 C20 C17 120.9(3) . . ?
C28 C26 C22 119.6(4) . . ?
C1 C2CA N29 113.3(8) . . ?
C25 C28 C26 120.8(3) . . ?
C28 C25 C21 119.4(4) . . ?
N29 C6CA C32 114.8(7) . . ?
_iucr_refine_instructions_details
;
TITL exp_15560 in P21/n #14
exp_15560.res
created by SHELXL-2018/3 at 10:56:22 on 27-Feb-2019
REM reset to P21/n #14
CELL 1.54184 19.50267 5.95388 20.23661 90 111.0131 90
ZERR 4 0.00091 0.00031 0.00088 0 0.0051 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F N
UNIT 100 88 20 12
L.S. 5
PLAN 5
BOND
fmap 2
acta
REM
REM
REM
WGHT 0.161100 0.413200
FVAR 4.68624
F1 3 0.188647 0.892909 0.105846 11.00000 0.11647 0.11136 =
0.07677 -0.01461 0.02942 -0.03369
F7 3 0.201869 0.775983 0.235689 11.00000 0.11027 0.15348 =
0.06567 -0.02663 0.02171 -0.02809
F11 3 0.050063 0.234012 0.018504 11.00000 0.09788 0.10196 =
0.07263 -0.01328 0.03454 -0.02129
C3 1 0.120267 0.567252 0.054828 11.00000 0.05535 0.08307 =
0.05895 -0.00260 0.01941 0.00457
N9 4 0.083540 0.496768 -0.069538 11.00000 0.06309 0.10910 =
0.05405 0.00191 0.01666 -0.01138
F13 3 0.141529 0.386213 0.259901 11.00000 0.10877 0.15161 =
0.06069 0.01508 0.03355 0.01173
F19 3 0.064564 0.124726 0.148539 11.00000 0.13027 0.10876 =
0.09588 0.00754 0.05611 -0.01596
C5 1 0.116762 0.626986 -0.016286 11.00000 0.05764 0.08665 =
0.05993 -0.00138 0.01803 0.00126
C4 1 0.164862 0.639437 0.181646 11.00000 0.06853 0.11016 =
0.05766 -0.01168 0.01551 -0.00029
C8 1 0.134240 0.446180 0.194045 11.00000 0.07305 0.11289 =
0.05636 0.00681 0.02360 0.01438
C2 1 0.157501 0.699663 0.113640 11.00000 0.06747 0.08737 =
0.06418 -0.00434 0.02101 -0.00617
C6 1 0.089082 0.374152 0.069819 11.00000 0.06426 0.08701 =
0.06024 -0.00624 0.02201 0.00081
C17 1 0.051137 0.489118 -0.195085 11.00000 0.05377 0.10671 =
0.05323 0.00079 0.01363 0.00152
C12 1 0.095635 0.312763 0.137888 11.00000 0.07629 0.09326 =
0.07134 0.00511 0.03341 0.00545
C18 1 0.201949 0.759635 -0.133425 11.00000 0.07539 0.07251 =
0.05191 0.00433 0.01499 -0.00726
N14 4 0.088968 0.587187 -0.129119 11.00000 0.08520 0.12815 =
0.05367 0.00293 0.02082 -0.03192
C19 1 0.012447 0.292000 -0.199916 11.00000 0.06444 0.10501 =
0.05422 0.00630 0.01625 0.00557
AFIX 43
H19 2 0.011760 0.222859 -0.158949 11.00000 -1.20000
AFIX 0
C27 1 -0.026878 0.296163 -0.328268 11.00000 0.06405 0.13014 =
0.05349 -0.00038 0.01491 0.00942
C23 1 -0.025265 0.196486 -0.265059 11.00000 0.07586 0.10678 =
0.05884 -0.00190 0.01480 0.00112
AFIX 43
H23 2 -0.050287 0.062226 -0.267003 11.00000 -1.20000
AFIX 0
C21 1 0.242390 0.565331 -0.114629 11.00000 0.09465 0.08657 =
0.07027 0.01173 0.02371 0.00239
AFIX 43
H21 2 0.226586 0.450984 -0.092197 11.00000 -1.20000
AFIX 0
C22 1 0.226183 0.927136 -0.166927 11.00000 0.10061 0.08265 =
0.07579 0.00759 0.02778 -0.01619
AFIX 43
H22 2 0.199048 1.058699 -0.180522 11.00000 -1.20000
AFIX 0
C24 1 0.011370 0.493566 -0.322019 11.00000 0.07330 0.14207 =
0.05482 0.01113 0.02141 0.00136
AFIX 43
H24 2 0.010789 0.566299 -0.362886 11.00000 -1.20000
AFIX 0
C15 1 0.133588 0.790633 -0.117025 11.00000 0.08142 0.08451 =
0.06636 0.00873 0.02272 0.00344
AFIX 13
H15 2 0.104398 0.913892 -0.145565 11.00000 -1.20000
AFIX 0
N29 4 -0.063609 0.193868 -0.393548 11.00000 0.11284 0.15620 =
0.05777 -0.01414 0.01717 -0.01509
C9BA 1 0.147920 0.833892 -0.037553 11.00000 0.10013 0.09344 =
0.07362 -0.00273 0.03649 -0.00525
AFIX 23
H9BA 2 0.200028 0.848623 -0.010535 11.00000 -1.20000
H9BB 2 0.122783 0.968151 -0.031211 11.00000 -1.20000
AFIX 0
C20 1 0.050598 0.587443 -0.257152 11.00000 0.07571 0.12948 =
0.06135 0.00956 0.02017 -0.01315
AFIX 43
H20 2 0.077078 0.718808 -0.255121 11.00000 -1.20000
AFIX 0
C26 1 0.290317 0.901278 -0.180455 11.00000 0.10269 0.12342 =
0.09274 -0.00294 0.04201 -0.03695
AFIX 43
H26 2 0.306680 1.015685 -0.202410 11.00000 -1.20000
AFIX 0
C2CA 1 -0.067806 0.297587 -0.458343 11.00000 0.19803 0.21442 =
0.05724 -0.00355 0.01228 -0.04889
AFIX 23
H2CA 2 -0.022131 0.376245 -0.451136 11.00000 -1.20000
H2CB 2 -0.073178 0.181861 -0.493590 11.00000 -1.20000
AFIX 0
C28 1 0.329784 0.705410 -0.161259 11.00000 0.08009 0.15484 =
0.08289 -0.01930 0.03036 -0.01879
AFIX 43
H28 2 0.372792 0.687524 -0.170630 11.00000 -1.20000
AFIX 0
C25 1 0.306683 0.537487 -0.128731 11.00000 0.08568 0.11823 =
0.08456 -0.00658 0.01706 0.01371
AFIX 43
H25 2 0.333592 0.405223 -0.116017 11.00000 -1.20000
AFIX 0
C32 1 -0.184407 0.081802 -0.395870 11.00000 0.14885 0.58462 =
0.11743 -0.07407 0.05187 -0.15522
AFIX 137
H32A 2 -0.176929 0.139859 -0.349543 11.00000 -1.50000
H32B 2 -0.215652 -0.047891 -0.404593 11.00000 -1.50000
H32C 2 -0.207111 0.194780 -0.430703 11.00000 -1.50000
AFIX 0
C6CA 1 -0.111647 0.017075 -0.400205 11.00000 0.22791 0.18007 =
0.06803 -0.03101 0.02274 -0.07171
AFIX 23
H6CA 2 -0.088297 -0.091639 -0.363270 11.00000 -1.20000
H6CB 2 -0.120435 -0.056092 -0.445333 11.00000 -1.20000
AFIX 0
C1 1 -0.124853 0.445930 -0.483665 11.00000 0.56917 0.26749 =
0.19126 0.06737 -0.05368 -0.02933
AFIX 137
H1A 2 -0.151963 0.449467 -0.452357 11.00000 -1.50000
H1B 2 -0.156676 0.399359 -0.529919 11.00000 -1.50000
H1C 2 -0.105952 0.593060 -0.486487 11.00000 -1.50000
AFIX 0
HKLF 4
REM exp_15560 in P21/n #14
REM wR2 = 0.2659, GooF = S = 1.054, Restrained GooF = 1.054 for all data
REM R1 = 0.0700 for 2869 Fo > 4sig(Fo) and 0.0925 for all 4257 data
REM 300 parameters refined using 0 restraints
END
WGHT 0.1611 0.4132
REM Highest difference peak 0.920, deepest hole -0.235, 1-sigma level 0.053
Q1 1 -0.0198 0.1873 -0.4903 11.00000 0.05 0.92
Q2 1 -0.0827 0.3161 -0.3828 11.00000 0.05 0.13
Q3 1 0.0814 0.3738 0.1001 11.00000 0.05 0.13
Q4 1 0.0030 0.5829 -0.2963 11.00000 0.05 0.13
Q5 1 0.2411 0.9356 -0.1236 11.00000 0.05 0.12
REM The information below was added by Olex2.
REM
REM R1 = 0.0700 for 2869 Fo > 4sig(Fo) and 0.0925 for all 22534 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.92, deepest hole -0.23
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0925
REM R1_gt = 0.0700
REM wR_ref = 0.2659
REM GOOF = 1.054
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 22534
REM Reflections_gt = 2869
REM Parameters = n/a
REM Hole = -0.23
REM Peak = 0.92
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.544
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_exp_15640
_database_code_depnum_ccdc_archive 'CCDC 1917277'
_audit_update_record
;
2019-05-20 deposited with the CCDC. 2019-08-14 downloaded from the CCDC.
;
_audit_creation_date 2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C22 H15 F5 N2)'
_chemical_formula_sum 'C44 H30 F10 N4'
_chemical_formula_weight 804.72
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 11.1225(4)
_cell_length_b 12.8307(5)
_cell_length_c 13.8928(5)
_cell_angle_alpha 100.865(3)
_cell_angle_beta 91.711(3)
_cell_angle_gamma 103.357(3)
_cell_volume 1888.83(12)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 12472
_cell_measurement_temperature 298
_cell_measurement_theta_max 71.7230
_cell_measurement_theta_min 4.0900
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 1.022
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.39403
_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 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.415
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 824
_exptl_crystal_size_max ?
_exptl_crystal_size_mid ?
_exptl_crystal_size_min ?
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0375
_diffrn_reflns_av_unetI/netI 0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 34588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.740
_diffrn_reflns_theta_min 4.097
_diffrn_ambient_temperature 298
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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 7.00 107.00 1.00 1.00 -- 35.91 19.00 -60.00 100
2 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00 -30.00 79
3 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 -90.00 94
4 \w 56.00 108.00 1.00 1.00 -- 35.91 179.00-120.00 52
5 \w -35.00 65.00 1.00 1.00 -- 35.91 -19.00 90.00 100
6 \w 53.00 108.00 1.00 1.00 -- 35.91-179.00 -60.00 55
7 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00 150.00 79
8 \w -31.00 53.00 1.00 1.00 -- 35.91 -57.00-120.00 84
9 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00 120.00 79
10 \w 56.00 108.00 1.00 1.00 -- 35.91 179.00 60.00 52
11 \w -31.00 53.00 1.00 1.00 -- 35.91 -57.00 0.00 84
12 \w 87.00 178.00 1.00 1.00 -- 108.00 30.00 0.00 91
13 \w 41.00 125.00 1.00 1.00 -- 108.00 -59.00-150.00 84
14 \w 39.00 109.00 1.00 1.00 -- 108.00 -94.00-180.00 70
15 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00 120.00 85
16 \w 39.00 109.00 1.00 1.00 -- 108.00 -94.00 0.00 70
17 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00 -30.00 85
18 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00-150.00 85
19 \w 90.00 175.00 1.00 1.00 -- 108.00 61.00 150.00 85
20 \w 38.00 116.00 1.00 1.00 -- 108.00-111.00 120.00 78
21 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00 30.00 85
22 \w 38.00 116.00 1.00 1.00 -- 108.00-111.00 -60.00 78
23 \w 39.00 109.00 1.00 1.00 -- 108.00 -94.00 120.00 70
24 \w 39.00 177.00 1.00 1.00 -- 108.00 0.00 -30.00 138
25 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00-120.00 84
26 \w 7.00 107.00 1.00 1.00 -- 35.91 19.00-180.00 100
27 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 120.00 94
28 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 90.00 84
29 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 30.00 94
30 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00-180.00 94
31 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 30.00 84
32 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 -30.00 84
33 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 -30.00 94
34 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00-150.00 79
35 \w 91.00 176.00 1.00 1.00 -- 108.00 45.00 120.00 85
36 \w 91.00 176.00 1.00 1.00 -- 108.00 45.00 30.00 85
37 \w 87.00 178.00 1.00 1.00 -- 108.00 30.00-150.00 91
38 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 -90.00 95
39 \w 87.00 178.00 1.00 1.00 -- 108.00 30.00 90.00 91
40 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 30.00 95
41 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 -60.00 95
42 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00-120.00 95
43 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 120.00 95
44 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00-150.00 95
45 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 60.00 94
46 \w 17.00 105.00 1.00 1.00 -- 35.91 37.00 -30.00 88
47 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 -60.00 84
48 \w 17.00 105.00 1.00 1.00 -- 35.91 37.00-150.00 88
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0471714000
_diffrn_orient_matrix_UB_12 0.1007823000
_diffrn_orient_matrix_UB_13 -0.0127745000
_diffrn_orient_matrix_UB_21 -0.0927513000
_diffrn_orient_matrix_UB_22 -0.0216866000
_diffrn_orient_matrix_UB_23 0.0782955000
_diffrn_orient_matrix_UB_31 0.0977681000
_diffrn_orient_matrix_UB_32 0.0724043000
_diffrn_orient_matrix_UB_33 0.0808193000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_diffrn_special_details ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5870
_reflns_number_total 7310
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'CrysAlisPro 1.171.38.46 (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 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.228
_refine_diff_density_min -0.313
_refine_diff_density_rms 0.060
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 525
_refine_ls_number_reflns 7310
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0725
_refine_ls_R_factor_gt 0.0614
_refine_ls_restrained_S_all 1.045
_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^)+(0.0983P)^2^+0.4424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1672
_refine_ls_wR_factor_ref 0.1799
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C12(H12), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
C19(H19A,H19B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
C11(H11), C15(H15), C16(H16), C17(H17), C24(H24), C25(H25), C29(H29),
C32(H32), C34(H34), C36(H36), C39(H39), C40(H40), C42(H42), C47(H47), C48(H48),
C56(H56), C57(H57), C58(H58)
2.d Idealised Me refined as rotating group:
C26(H26A,H26B,H26C), C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29264(11) 0.35770(10) 0.11747(11) 0.0713(4) Uani 1 1 d . . . . .
F2 F -0.14211(11) 0.27051(10) 0.13689(11) 0.0741(4) Uani 1 1 d . . . . .
N3 N -0.01352(14) 0.12481(11) 0.15671(11) 0.0485(4) Uani 1 1 d . . . . .
N4 N 0.01465(14) 0.02570(11) 0.15711(12) 0.0488(4) Uani 1 1 d . . . . .
F5 F 0.28692(14) 0.55982(11) 0.10953(15) 0.1018(6) Uani 1 1 d . . . . .
C6 C -0.08748(16) -0.06504(13) 0.14828(13) 0.0444(4) Uani 1 1 d . . . . .
F7 F -0.14401(14) 0.47427(12) 0.13119(15) 0.0971(5) Uani 1 1 d . . . . .
C8 C 0.07585(18) 0.30341(14) 0.12910(13) 0.0484(4) Uani 1 1 d . . . . .
C9 C 0.21091(16) -0.03792(14) 0.15836(14) 0.0490(4) Uani 1 1 d . . . . .
C10 C -0.03334(19) 0.33872(15) 0.13163(16) 0.0553(5) Uani 1 1 d . . . . .
C11 C -0.20671(18) -0.05127(15) 0.16025(15) 0.0531(4) Uani 1 1 d . . . . .
H11 H -0.219991 0.018801 0.173922 0.064 Uiso 1 1 calc R . . . .
C12 C 0.13083(16) 0.01975(14) 0.10968(13) 0.0458(4) Uani 1 1 d . . . . .
H12 H 0.110324 -0.017640 0.040835 0.055 Uiso 1 1 calc R . . . .
C13 C 0.18235(19) 0.38256(16) 0.12091(15) 0.0554(5) Uani 1 1 d . . . . .
C14 C 0.08064(16) 0.19058(13) 0.13229(13) 0.0452(4) Uani 1 1 d . . . . .
C15 C -0.17151(18) -0.25927(15) 0.12148(15) 0.0538(5) Uani 1 1 d . . . . .
H15 H -0.158522 -0.329467 0.108946 0.065 Uiso 1 1 calc R . . . .
C16 C -0.30546(18) -0.14076(16) 0.15200(16) 0.0574(5) Uani 1 1 d . . . . .
H16 H -0.384578 -0.129667 0.160038 0.069 Uiso 1 1 calc R . . . .
C17 C -0.07051(17) -0.17100(14) 0.12880(15) 0.0516(4) Uani 1 1 d . . . . .
H17 H 0.008471 -0.182427 0.120734 0.062 Uiso 1 1 calc R . . . .
F18 F 0.06940(16) 0.62303(11) 0.11742(16) 0.1086(6) Uani 1 1 d . . . . .
C19 C 0.18986(17) 0.14138(14) 0.11348(15) 0.0493(4) Uani 1 1 d . . . . .
H19A H 0.254793 0.170631 0.166340 0.059 Uiso 1 1 calc R . . . .
H19B H 0.223433 0.153203 0.051712 0.059 Uiso 1 1 calc R . . . .
C20 C -0.29048(18) -0.24701(15) 0.13206(15) 0.0529(4) Uani 1 1 d . . . . .
C21 C 0.1811(2) 0.48834(16) 0.11679(18) 0.0671(6) Uani 1 1 d . . . . .
N22 N -0.4820(2) -0.42017(17) 0.36452(15) 0.0732(5) Uani 1 1 d . . . . .
C23 C 0.0718(2) 0.51987(17) 0.1209(2) 0.0730(6) Uani 1 1 d . . . . .
C24 C -0.7112(2) -0.67271(19) 0.37166(16) 0.0638(5) Uani 1 1 d . . . . .
H24 H -0.661008 -0.721675 0.370318 0.077 Uiso 1 1 calc R . . . .
C25 C 0.26288(19) -0.11454(17) 0.10071(19) 0.0631(5) Uani 1 1 d . . . . .
H25 H 0.249224 -0.127804 0.032649 0.076 Uiso 1 1 calc R . . . .
C26 C -0.3996(2) -0.34480(18) 0.1209(2) 0.0729(6) Uani 1 1 d . . . . .
H26A H -0.443134 -0.356561 0.057635 0.109 Uiso 1 1 calc GR . . . .
H26B H -0.454466 -0.331581 0.171433 0.109 Uiso 1 1 calc GR . . . .
H26C H -0.370539 -0.408393 0.126710 0.109 Uiso 1 1 calc GR . . . .
N27 N -0.53246(18) -0.52950(16) 0.35428(15) 0.0710(5) Uani 1 1 d . . . . .
C28 C -0.0355(2) 0.44482(17) 0.12837(19) 0.0668(6) Uani 1 1 d . . . . .
C29 C 0.2342(2) -0.0178(2) 0.25829(18) 0.0701(6) Uani 1 1 d . . . . .
H29 H 0.201864 0.034259 0.298142 0.084 Uiso 1 1 calc R . . . .
C30 C -0.44590(19) -0.69038(18) 0.29202(17) 0.0633(5) Uani 1 1 d . . . . .
C31 C -0.3629(2) -0.4026(2) 0.37503(16) 0.0721(6) Uani 1 1 d . . . . .
C32 C -0.8372(2) -0.7073(2) 0.38083(16) 0.0698(6) Uani 1 1 d . . . . .
H32 H -0.870023 -0.779501 0.385647 0.084 Uiso 1 1 calc R . . . .
C33 C -0.6594(2) -0.56498(19) 0.36445(15) 0.0618(5) Uani 1 1 d . . . . .
C34 C -0.4630(2) -0.6873(2) 0.19438(18) 0.0748(6) Uani 1 1 d . . . . .
H34 H -0.472437 -0.623523 0.175825 0.090 Uiso 1 1 calc R . . . .
F35 F -0.4496(2) -0.20494(15) 0.42259(16) 0.1224(7) Uani 1 1 d . . . . .
C36 C -0.7379(2) -0.4942(2) 0.36588(18) 0.0733(6) Uani 1 1 d . . . . .
H36 H -0.705935 -0.422050 0.360538 0.088 Uiso 1 1 calc R . . . .
F37 F -0.1044(2) -0.3569(2) 0.35188(19) 0.1413(9) Uani 1 1 d . . . . .
C38 C -0.4388(2) -0.5910(2) 0.37045(17) 0.0673(6) Uani 1 1 d . . . . .
H38 H -0.447296 -0.612325 0.434496 0.081 Uiso 1 1 calc R . . . .
C39 C 0.3546(2) -0.1524(3) 0.2409(3) 0.0956(10) Uani 1 1 d . . . . .
H39 H 0.401589 -0.191790 0.268928 0.115 Uiso 1 1 calc R . . . .
C40 C 0.3067(3) -0.0759(3) 0.3003(2) 0.0951(9) Uani 1 1 d . . . . .
H40 H 0.322565 -0.062682 0.368203 0.114 Uiso 1 1 calc R . . . .
C41 C -0.3177(2) -0.5032(2) 0.37415(19) 0.0778(7) Uani 1 1 d . . . . .
H41A H -0.265103 -0.496401 0.433055 0.093 Uiso 1 1 calc R . . . .
H41B H -0.272344 -0.519338 0.316888 0.093 Uiso 1 1 calc R . . . .
C42 C 0.3340(2) -0.1709(2) 0.1427(3) 0.0845(8) Uani 1 1 d . . . . .
H42 H 0.367979 -0.221863 0.103113 0.101 Uiso 1 1 calc R . . . .
F43 F -0.3051(4) -0.0081(2) 0.43226(19) 0.1798(13) Uani 1 1 d . . . . .
C44 C -0.1568(4) -0.2736(3) 0.3724(2) 0.1052(12) Uani 1 1 d . . . . .
C45 C -0.2532(6) -0.0952(3) 0.4133(3) 0.1287(16) Uani 1 1 d . . . . .
C46 C -0.9154(2) -0.6378(2) 0.38302(17) 0.0765(7) Uani 1 1 d . . . . .
C47 C -0.8630(3) -0.5314(2) 0.37525(18) 0.0808(7) Uani 1 1 d . . . . .
H47 H -0.913773 -0.482976 0.376354 0.097 Uiso 1 1 calc R . . . .
C48 C -0.4313(3) -0.8761(3) 0.2458(4) 0.1150(12) Uani 1 1 d . . . . .
H48 H -0.420013 -0.939583 0.263838 0.138 Uiso 1 1 calc R . . . .
C49 C -0.2849(3) -0.2919(3) 0.38451(18) 0.0859(8) Uani 1 1 d . . . . .
C50 C -0.3280(4) -0.1985(3) 0.4056(2) 0.1025(11) Uani 1 1 d . . . . .
F51 F -0.0585(3) 0.0195(2) 0.40651(18) 0.1956(16) Uani 1 1 d . . . . .
C52 C -0.1284(6) -0.0816(4) 0.3999(3) 0.140(2) Uani 1 1 d . . . . .
C53 C -0.0825(4) -0.1708(5) 0.3817(3) 0.1335(18) Uani 1 1 d . . . . .
C54 C -1.0526(3) -0.6773(3) 0.3928(3) 0.1090(11) Uani 1 1 d . . . . .
H54A H -1.087420 -0.737787 0.339961 0.164 Uiso 1 1 calc GR . . . .
H54B H -1.092536 -0.618951 0.390294 0.164 Uiso 1 1 calc GR . . . .
H54C H -1.064871 -0.700166 0.454474 0.164 Uiso 1 1 calc GR . . . .
F55 F 0.0371(2) -0.1569(3) 0.3698(2) 0.1922(15) Uani 1 1 d . . . . .
C56 C -0.4484(3) -0.8734(3) 0.1513(4) 0.1126(13) Uani 1 1 d . . . . .
H56 H -0.448504 -0.934966 0.103647 0.135 Uiso 1 1 calc R . . . .
C57 C -0.4303(3) -0.7863(3) 0.3166(3) 0.0937(9) Uani 1 1 d . . . . .
H57 H -0.418910 -0.789639 0.382404 0.112 Uiso 1 1 calc R . . . .
C58 C -0.4659(3) -0.7803(3) 0.1236(2) 0.0988(10) Uani 1 1 d . . . . .
H58 H -0.479740 -0.779523 0.057386 0.119 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0527(7) 0.0512(7) 0.1098(10) 0.0226(6) 0.0041(6) 0.0073(5)
F2 0.0523(7) 0.0486(7) 0.1245(11) 0.0257(7) 0.0016(7) 0.0121(5)
N3 0.0508(8) 0.0332(7) 0.0632(9) 0.0113(6) 0.0010(7) 0.0125(6)
N4 0.0450(8) 0.0335(7) 0.0705(10) 0.0144(7) 0.0030(7) 0.0118(6)
F5 0.0774(10) 0.0498(8) 0.1770(17) 0.0429(9) 0.0073(10) -0.0033(7)
C6 0.0463(9) 0.0357(8) 0.0526(9) 0.0138(7) -0.0016(7) 0.0090(7)
F7 0.0745(9) 0.0609(8) 0.1695(16) 0.0373(9) 0.0037(9) 0.0329(7)
C8 0.0548(10) 0.0347(9) 0.0537(10) 0.0086(7) -0.0044(8) 0.0085(8)
C9 0.0402(9) 0.0408(9) 0.0673(11) 0.0158(8) 0.0009(8) 0.0084(7)
C10 0.0557(11) 0.0390(9) 0.0715(12) 0.0150(9) -0.0033(9) 0.0098(8)
C11 0.0504(10) 0.0407(9) 0.0713(12) 0.0155(8) 0.0072(9) 0.0134(8)
C12 0.0451(9) 0.0381(9) 0.0540(10) 0.0094(7) 0.0000(7) 0.0102(7)
C13 0.0541(11) 0.0419(10) 0.0688(12) 0.0132(9) -0.0036(9) 0.0081(8)
C14 0.0481(9) 0.0340(8) 0.0523(9) 0.0081(7) -0.0031(7) 0.0089(7)
C15 0.0573(11) 0.0363(9) 0.0693(12) 0.0172(8) -0.0033(9) 0.0098(8)
C16 0.0481(10) 0.0496(11) 0.0776(13) 0.0192(9) 0.0092(9) 0.0125(8)
C17 0.0461(10) 0.0398(9) 0.0721(12) 0.0172(8) -0.0020(8) 0.0129(7)
F18 0.1021(12) 0.0411(7) 0.1906(18) 0.0422(9) -0.0005(11) 0.0196(7)
C19 0.0472(10) 0.0386(9) 0.0623(11) 0.0142(8) 0.0007(8) 0.0077(7)
C20 0.0509(10) 0.0441(10) 0.0632(11) 0.0195(8) 0.0005(8) 0.0037(8)
C21 0.0676(13) 0.0392(10) 0.0906(16) 0.0197(10) -0.0035(11) 0.0009(9)
N22 0.0806(14) 0.0643(12) 0.0678(11) 0.0084(9) 0.0020(9) 0.0082(10)
C23 0.0794(15) 0.0364(10) 0.1057(18) 0.0238(11) -0.0057(13) 0.0131(10)
C24 0.0619(12) 0.0667(13) 0.0601(12) 0.0039(10) 0.0046(9) 0.0172(10)
C25 0.0538(11) 0.0464(10) 0.0900(15) 0.0120(10) 0.0046(10) 0.0152(9)
C26 0.0613(13) 0.0554(13) 0.1002(17) 0.0287(12) 0.0044(12) 0.0000(10)
N27 0.0624(11) 0.0584(11) 0.0863(13) 0.0037(9) 0.0055(9) 0.0118(9)
C28 0.0658(13) 0.0459(11) 0.0931(16) 0.0185(10) -0.0042(11) 0.0202(10)
C29 0.0603(13) 0.0850(16) 0.0716(14) 0.0246(12) -0.0011(10) 0.0243(11)
C30 0.0507(11) 0.0647(13) 0.0751(13) 0.0138(10) 0.0065(10) 0.0154(9)
C31 0.0726(15) 0.0790(16) 0.0523(11) 0.0103(11) -0.0023(10) -0.0031(12)
C32 0.0644(13) 0.0766(15) 0.0596(12) 0.0020(11) 0.0047(10) 0.0092(11)
C33 0.0608(12) 0.0653(13) 0.0538(11) -0.0016(9) -0.0008(9) 0.0158(10)
C34 0.0677(14) 0.0820(16) 0.0737(14) 0.0051(12) -0.0031(11) 0.0257(12)
F35 0.155(2) 0.0777(11) 0.1292(16) 0.0227(10) -0.0169(14) 0.0203(12)
C36 0.0763(15) 0.0691(14) 0.0721(14) 0.0005(11) -0.0048(11) 0.0251(12)
F37 0.0874(13) 0.162(2) 0.1448(19) 0.0126(16) 0.0246(12) -0.0175(14)
C38 0.0626(13) 0.0754(15) 0.0628(12) 0.0123(11) 0.0033(10) 0.0162(11)
C39 0.0618(15) 0.101(2) 0.151(3) 0.072(2) 0.0121(16) 0.0363(14)
C40 0.0742(17) 0.136(3) 0.0911(19) 0.0570(19) -0.0036(14) 0.0306(17)
C41 0.0631(14) 0.0877(18) 0.0722(14) 0.0019(13) 0.0001(11) 0.0092(12)
C42 0.0619(14) 0.0606(14) 0.142(3) 0.0326(16) 0.0142(15) 0.0265(11)
F43 0.285(4) 0.0834(15) 0.143(2) 0.0345(14) -0.047(2) -0.0130(19)
C44 0.099(2) 0.121(3) 0.0680(16) 0.0238(17) -0.0036(15) -0.033(2)
C45 0.206(5) 0.076(2) 0.080(2) 0.0278(17) -0.029(2) -0.021(3)
C46 0.0623(14) 0.098(2) 0.0613(13) -0.0037(12) 0.0010(10) 0.0201(13)
C47 0.0733(15) 0.095(2) 0.0723(15) -0.0068(13) -0.0059(12) 0.0367(14)
C48 0.113(3) 0.074(2) 0.169(4) 0.025(2) 0.057(3) 0.0374(18)
C49 0.105(2) 0.0826(19) 0.0531(13) 0.0175(12) -0.0070(12) -0.0126(16)
C50 0.123(3) 0.092(2) 0.0721(17) 0.0286(16) -0.0162(17) -0.020(2)
F51 0.264(3) 0.137(2) 0.1137(16) 0.0462(14) -0.0367(18) -0.106(2)
C52 0.188(5) 0.114(3) 0.0707(19) 0.034(2) -0.025(2) -0.069(4)
C53 0.132(3) 0.149(4) 0.077(2) 0.032(2) -0.0073(19) -0.060(3)
C54 0.0632(16) 0.149(3) 0.103(2) 0.000(2) 0.0084(15) 0.0219(18)
F55 0.129(2) 0.237(3) 0.147(2) 0.043(2) 0.0123(15) -0.087(2)
C56 0.0769(19) 0.078(2) 0.163(4) -0.023(2) 0.025(2) 0.0153(15)
C57 0.0920(19) 0.0867(19) 0.120(2) 0.0404(17) 0.0308(17) 0.0369(16)
C58 0.0730(17) 0.124(3) 0.0857(18) -0.0129(18) -0.0010(14) 0.0249(17)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.337(2) . ?
F2 C10 1.332(2) . ?
N3 N4 1.3791(19) . ?
N3 C14 1.282(2) . ?
N4 C6 1.410(2) . ?
N4 C12 1.479(2) . ?
F5 C21 1.334(3) . ?
C6 C11 1.388(2) . ?
C6 C17 1.393(2) . ?
F7 C28 1.345(3) . ?
C8 C10 1.390(3) . ?
C8 C13 1.394(3) . ?
C8 C14 1.470(2) . ?
C9 C12 1.502(2) . ?
C9 C25 1.391(3) . ?
C9 C29 1.369(3) . ?
C10 C28 1.376(3) . ?
C11 C16 1.378(3) . ?
C12 C19 1.537(2) . ?
C13 C21 1.373(3) . ?
C14 C19 1.501(2) . ?
C15 C17 1.385(3) . ?
C15 C20 1.377(3) . ?
C16 C20 1.389(3) . ?
F18 C23 1.340(2) . ?
C20 C26 1.511(3) . ?
C21 C23 1.367(3) . ?
N22 N27 1.363(3) . ?
N22 C31 1.291(3) . ?
C23 C28 1.370(3) . ?
C24 C32 1.387(3) . ?
C24 C33 1.393(3) . ?
C25 C42 1.372(3) . ?
N27 C33 1.400(3) . ?
N27 C38 1.480(3) . ?
C29 C40 1.401(3) . ?
C30 C34 1.373(3) . ?
C30 C38 1.498(3) . ?
C30 C57 1.384(3) . ?
C31 C41 1.487(4) . ?
C31 C49 1.463(4) . ?
C32 C46 1.379(4) . ?
C33 C36 1.395(3) . ?
C34 C58 1.389(4) . ?
F35 C50 1.367(4) . ?
C36 C47 1.381(4) . ?
F37 C44 1.321(5) . ?
C38 C41 1.536(3) . ?
C39 C40 1.375(5) . ?
C39 C42 1.343(4) . ?
F43 C45 1.360(6) . ?
C44 C49 1.410(5) . ?
C44 C53 1.365(5) . ?
C45 C50 1.375(5) . ?
C45 C52 1.382(7) . ?
C46 C47 1.381(4) . ?
C46 C54 1.512(4) . ?
C48 C56 1.329(5) . ?
C48 C57 1.363(5) . ?
C49 C50 1.377(5) . ?
F51 C52 1.334(4) . ?
C52 C53 1.343(7) . ?
C53 F55 1.321(5) . ?
C56 C58 1.376(5) . ?
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
C14 N3 N4 109.13(14) . . ?
N3 N4 C6 115.85(14) . . ?
N3 N4 C12 111.01(13) . . ?
C6 N4 C12 122.97(14) . . ?
C11 C6 N4 121.11(15) . . ?
C11 C6 C17 118.40(16) . . ?
C17 C6 N4 120.49(16) . . ?
C10 C8 C13 115.16(16) . . ?
C10 C8 C14 123.36(17) . . ?
C13 C8 C14 121.46(17) . . ?
C25 C9 C12 119.37(18) . . ?
C29 C9 C12 121.95(18) . . ?
C29 C9 C25 118.67(19) . . ?
F2 C10 C8 121.22(16) . . ?
F2 C10 C28 116.50(18) . . ?
C28 C10 C8 122.29(19) . . ?
C16 C11 C6 120.41(17) . . ?
N4 C12 C9 114.12(14) . . ?
N4 C12 C19 101.31(13) . . ?
C9 C12 C19 114.28(15) . . ?
F1 C13 C8 120.37(17) . . ?
F1 C13 C21 116.62(18) . . ?
C21 C13 C8 123.0(2) . . ?
N3 C14 C8 119.97(16) . . ?
N3 C14 C19 113.43(14) . . ?
C8 C14 C19 126.55(16) . . ?
C20 C15 C17 122.46(17) . . ?
C11 C16 C20 122.02(18) . . ?
C15 C17 C6 119.83(17) . . ?
C14 C19 C12 101.43(14) . . ?
C15 C20 C16 116.86(17) . . ?
C15 C20 C26 121.43(18) . . ?
C16 C20 C26 121.70(19) . . ?
F5 C21 C13 119.6(2) . . ?
F5 C21 C23 120.52(19) . . ?
C23 C21 C13 119.8(2) . . ?
C31 N22 N27 108.9(2) . . ?
F18 C23 C21 120.4(2) . . ?
F18 C23 C28 120.3(2) . . ?
C21 C23 C28 119.30(18) . . ?
C32 C24 C33 120.3(2) . . ?
C42 C25 C9 121.0(2) . . ?
N22 N27 C33 118.66(19) . . ?
N22 N27 C38 112.50(19) . . ?
C33 N27 C38 124.8(2) . . ?
F7 C28 C10 119.6(2) . . ?
F7 C28 C23 119.98(18) . . ?
C23 C28 C10 120.4(2) . . ?
C9 C29 C40 119.8(2) . . ?
C34 C30 C38 121.0(2) . . ?
C34 C30 C57 118.5(2) . . ?
C57 C30 C38 120.4(2) . . ?
N22 C31 C41 113.8(2) . . ?
N22 C31 C49 120.4(3) . . ?
C49 C31 C41 125.7(2) . . ?
C46 C32 C24 122.0(2) . . ?
C24 C33 N27 120.8(2) . . ?
C24 C33 C36 118.1(2) . . ?
C36 C33 N27 121.1(2) . . ?
C30 C34 C58 119.4(3) . . ?
C47 C36 C33 120.0(3) . . ?
N27 C38 C30 113.90(19) . . ?
N27 C38 C41 101.39(19) . . ?
C30 C38 C41 112.86(19) . . ?
C42 C39 C40 120.6(2) . . ?
C39 C40 C29 119.8(3) . . ?
C31 C41 C38 102.5(2) . . ?
C39 C42 C25 120.1(3) . . ?
F37 C44 C49 120.3(3) . . ?
F37 C44 C53 117.7(4) . . ?
C53 C44 C49 122.0(5) . . ?
F43 C45 C50 118.7(5) . . ?
F43 C45 C52 121.2(4) . . ?
C50 C45 C52 120.0(5) . . ?
C32 C46 C47 117.1(2) . . ?
C32 C46 C54 121.1(3) . . ?
C47 C46 C54 121.8(3) . . ?
C46 C47 C36 122.4(2) . . ?
C56 C48 C57 120.5(3) . . ?
C44 C49 C31 121.3(3) . . ?
C50 C49 C31 124.1(3) . . ?
C50 C49 C44 114.6(3) . . ?
F35 C50 C45 116.5(4) . . ?
F35 C50 C49 120.3(3) . . ?
C45 C50 C49 123.2(4) . . ?
F51 C52 C45 118.6(6) . . ?
F51 C52 C53 122.9(6) . . ?
C53 C52 C45 118.4(4) . . ?
C52 C53 C44 121.7(5) . . ?
F55 C53 C44 120.3(6) . . ?
F55 C53 C52 117.9(5) . . ?
C48 C56 C58 120.4(3) . . ?
C48 C57 C30 121.1(3) . . ?
C56 C58 C34 120.0(3) . . ?
_iucr_refine_instructions_details
;
TITL exp_15640 in P-1 #2
exp_15640.res
created by SHELXL-2018/3 at 10:51:04 on 27-Feb-2019
REM reset to P-1 #2
CELL 1.54184 11.12251 12.83072 13.89277 100.8646 91.7108 103.3573
ZERR 2 0.00039 0.00052 0.00046 0.0031 0.0028 0.0032
LATT 1
SFAC C H F N
UNIT 88 60 20 8
L.S. 10
PLAN 5
TEMP 24.85
BOND
fmap 2
acta
REM
REM
REM
WGHT 0.098300 0.442400
FVAR 6.49363
F1 3 0.292642 0.357702 0.117469 11.00000 0.05273 0.05125 =
0.10982 0.02260 0.00408 0.00731
F2 3 -0.142107 0.270513 0.136891 11.00000 0.05233 0.04856 =
0.12453 0.02574 0.00159 0.01205
N3 4 -0.013517 0.124810 0.156707 11.00000 0.05079 0.03322 =
0.06315 0.01130 0.00095 0.01253
N4 4 0.014645 0.025695 0.157105 11.00000 0.04496 0.03348 =
0.07047 0.01439 0.00302 0.01177
F5 3 0.286919 0.559823 0.109531 11.00000 0.07739 0.04978 =
0.17695 0.04294 0.00734 -0.00331
C6 1 -0.087481 -0.065044 0.148278 11.00000 0.04630 0.03566 =
0.05255 0.01376 -0.00161 0.00899
F7 3 -0.144005 0.474273 0.131192 11.00000 0.07448 0.06093 =
0.16953 0.03726 0.00367 0.03290
C8 1 0.075846 0.303405 0.129097 11.00000 0.05484 0.03470 =
0.05371 0.00859 -0.00443 0.00848
C9 1 0.210908 -0.037920 0.158365 11.00000 0.04021 0.04078 =
0.06727 0.01583 0.00089 0.00840
C10 1 -0.033344 0.338719 0.131629 11.00000 0.05570 0.03900 =
0.07153 0.01496 -0.00333 0.00978
C11 1 -0.206708 -0.051271 0.160250 11.00000 0.05043 0.04074 =
0.07126 0.01553 0.00717 0.01340
AFIX 43
H11 2 -0.219991 0.018801 0.173922 11.00000 -1.20000
AFIX 0
C12 1 0.130832 0.019751 0.109679 11.00000 0.04506 0.03809 =
0.05401 0.00938 0.00003 0.01018
AFIX 13
H12 2 0.110324 -0.017640 0.040835 11.00000 -1.20000
AFIX 0
C13 1 0.182349 0.382558 0.120905 11.00000 0.05408 0.04186 =
0.06876 0.01320 -0.00357 0.00806
C14 1 0.080637 0.190583 0.132293 11.00000 0.04811 0.03401 =
0.05230 0.00813 -0.00306 0.00886
C15 1 -0.171509 -0.259270 0.121478 11.00000 0.05728 0.03628 =
0.06929 0.01716 -0.00329 0.00977
AFIX 43
H15 2 -0.158522 -0.329467 0.108946 11.00000 -1.20000
AFIX 0
C16 1 -0.305457 -0.140759 0.152002 11.00000 0.04813 0.04959 =
0.07763 0.01921 0.00916 0.01248
AFIX 43
H16 2 -0.384578 -0.129667 0.160038 11.00000 -1.20000
AFIX 0
C17 1 -0.070508 -0.171001 0.128801 11.00000 0.04612 0.03979 =
0.07206 0.01716 -0.00205 0.01290
AFIX 43
H17 2 0.008471 -0.182427 0.120734 11.00000 -1.20000
AFIX 0
F18 3 0.069399 0.623031 0.117421 11.00000 0.10211 0.04112 =
0.19064 0.04220 -0.00054 0.01961
C19 1 0.189862 0.141379 0.113482 11.00000 0.04716 0.03858 =
0.06230 0.01421 0.00068 0.00773
AFIX 23
H19A 2 0.254793 0.170631 0.166340 11.00000 -1.20000
H19B 2 0.223433 0.153203 0.051712 11.00000 -1.20000
AFIX 0
C20 1 -0.290485 -0.247011 0.132059 11.00000 0.05086 0.04407 =
0.06323 0.01950 0.00047 0.00373
C21 1 0.181079 0.488343 0.116785 11.00000 0.06759 0.03916 =
0.09064 0.01974 -0.00345 0.00093
N22 4 -0.482027 -0.420172 0.364518 11.00000 0.08062 0.06430 =
0.06784 0.00844 0.00204 0.00817
C23 1 0.071772 0.519871 0.120869 11.00000 0.07945 0.03638 =
0.10569 0.02378 -0.00573 0.01311
C24 1 -0.711191 -0.672705 0.371660 11.00000 0.06187 0.06674 =
0.06008 0.00394 0.00457 0.01725
AFIX 43
H24 2 -0.661008 -0.721675 0.370318 11.00000 -1.20000
AFIX 0
C25 1 0.262882 -0.114541 0.100709 11.00000 0.05381 0.04639 =
0.09003 0.01200 0.00465 0.01517
AFIX 43
H25 2 0.249224 -0.127804 0.032649 11.00000 -1.20000
AFIX 0
C26 1 -0.399605 -0.344802 0.120946 11.00000 0.06130 0.05540 =
0.10023 0.02872 0.00442 -0.00002
AFIX 137
H26A 2 -0.443134 -0.356561 0.057635 11.00000 -1.50000
H26B 2 -0.454466 -0.331581 0.171433 11.00000 -1.50000
H26C 2 -0.370539 -0.408393 0.126710 11.00000 -1.50000
AFIX 0
N27 4 -0.532464 -0.529499 0.354275 11.00000 0.06239 0.05840 =
0.08633 0.00370 0.00548 0.01184
C28 1 -0.035491 0.444821 0.128367 11.00000 0.06583 0.04591 =
0.09315 0.01847 -0.00417 0.02022
C29 1 0.234158 -0.017793 0.258292 11.00000 0.06025 0.08498 =
0.07157 0.02461 -0.00110 0.02429
AFIX 43
H29 2 0.201864 0.034259 0.298142 11.00000 -1.20000
AFIX 0
C30 1 -0.445904 -0.690382 0.292022 11.00000 0.05072 0.06472 =
0.07509 0.01379 0.00649 0.01539
C31 1 -0.362876 -0.402598 0.375026 11.00000 0.07260 0.07905 =
0.05232 0.01029 -0.00228 -0.00311
C32 1 -0.837224 -0.707278 0.380831 11.00000 0.06445 0.07665 =
0.05964 0.00199 0.00471 0.00921
AFIX 43
H32 2 -0.870023 -0.779501 0.385647 11.00000 -1.20000
AFIX 0
C33 1 -0.659393 -0.564981 0.364449 11.00000 0.06079 0.06529 =
0.05379 -0.00157 -0.00082 0.01576
C34 1 -0.462955 -0.687299 0.194376 11.00000 0.06768 0.08204 =
0.07369 0.00510 -0.00306 0.02571
AFIX 43
H34 2 -0.472437 -0.623523 0.175825 11.00000 -1.20000
AFIX 0
F35 3 -0.449620 -0.204935 0.422594 11.00000 0.15548 0.07770 =
0.12916 0.02274 -0.01689 0.02026
C36 1 -0.737855 -0.494233 0.365885 11.00000 0.07635 0.06908 =
0.07210 0.00051 -0.00478 0.02515
AFIX 43
H36 2 -0.705935 -0.422050 0.360538 11.00000 -1.20000
AFIX 0
F37 3 -0.104430 -0.356904 0.351876 11.00000 0.08740 0.16160 =
0.14477 0.01263 0.02463 -0.01748
C38 1 -0.438831 -0.591001 0.370446 11.00000 0.06262 0.07535 =
0.06282 0.01228 0.00328 0.01616
AFIX 13
H38 2 -0.447296 -0.612325 0.434496 11.00000 -1.20000
AFIX 0
C39 1 0.354562 -0.152416 0.240872 11.00000 0.06180 0.10118 =
0.15127 0.07234 0.01211 0.03627
AFIX 43
H39 2 0.401589 -0.191790 0.268928 11.00000 -1.20000
AFIX 0
C40 1 0.306749 -0.075851 0.300331 11.00000 0.07424 0.13565 =
0.09115 0.05699 -0.00356 0.03060
AFIX 43
H40 2 0.322565 -0.062682 0.368203 11.00000 -1.20000
AFIX 0
C41 1 -0.317730 -0.503177 0.374152 11.00000 0.06314 0.08769 =
0.07220 0.00193 0.00011 0.00921
AFIX 23
H41A 2 -0.265103 -0.496401 0.433055 11.00000 -1.20000
H41B 2 -0.272344 -0.519338 0.316888 11.00000 -1.20000
AFIX 0
C42 1 0.333988 -0.170852 0.142706 11.00000 0.06187 0.06056 =
0.14219 0.03258 0.01420 0.02651
AFIX 43
H42 2 0.367979 -0.221863 0.103113 11.00000 -1.20000
AFIX 0
F43 3 -0.305088 -0.008056 0.432257 11.00000 0.28470 0.08344 =
0.14328 0.03454 -0.04686 -0.01297
C44 1 -0.156778 -0.273606 0.372442 11.00000 0.09861 0.12056 =
0.06795 0.02381 -0.00361 -0.03319
C45 1 -0.253235 -0.095211 0.413269 11.00000 0.20556 0.07613 =
0.07962 0.02785 -0.02881 -0.02063
C46 1 -0.915370 -0.637778 0.383025 11.00000 0.06230 0.09796 =
0.06134 -0.00370 0.00096 0.02007
C47 1 -0.862963 -0.531404 0.375248 11.00000 0.07327 0.09466 =
0.07234 -0.00676 -0.00589 0.03665
AFIX 43
H47 2 -0.913773 -0.482976 0.376354 11.00000 -1.20000
AFIX 0
C48 1 -0.431330 -0.876070 0.245831 11.00000 0.11272 0.07374 =
0.16917 0.02508 0.05669 0.03738
AFIX 43
H48 2 -0.420013 -0.939583 0.263838 11.00000 -1.20000
AFIX 0
C49 1 -0.284863 -0.291921 0.384508 11.00000 0.10509 0.08263 =
0.05313 0.01746 -0.00705 -0.01255
C50 1 -0.327970 -0.198463 0.405553 11.00000 0.12342 0.09232 =
0.07209 0.02863 -0.01620 -0.01997
F51 3 -0.058502 0.019538 0.406510 11.00000 0.26400 0.13710 =
0.11366 0.04624 -0.03670 -0.10647
C52 1 -0.128361 -0.081591 0.399912 11.00000 0.18752 0.11433 =
0.07070 0.03443 -0.02533 -0.06940
C53 1 -0.082546 -0.170837 0.381737 11.00000 0.13151 0.14851 =
0.07679 0.03238 -0.00727 -0.05959
C54 1 -1.052566 -0.677274 0.392833 11.00000 0.06316 0.14894 =
0.10299 -0.00001 0.00837 0.02186
AFIX 137
H54A 2 -1.087420 -0.737787 0.339961 11.00000 -1.50000
H54B 2 -1.092536 -0.618951 0.390294 11.00000 -1.50000
H54C 2 -1.064871 -0.700166 0.454474 11.00000 -1.50000
AFIX 0
F55 3 0.037143 -0.156867 0.369813 11.00000 0.12900 0.23726 =
0.14680 0.04317 0.01228 -0.08668
C56 1 -0.448398 -0.873420 0.151342 11.00000 0.07692 0.07792 =
0.16320 -0.02310 0.02523 0.01527
AFIX 43
H56 2 -0.448504 -0.934966 0.103647 11.00000 -1.20000
AFIX 0
C57 1 -0.430296 -0.786332 0.316556 11.00000 0.09199 0.08665 =
0.11955 0.04045 0.03080 0.03688
AFIX 43
H57 2 -0.418910 -0.789639 0.382404 11.00000 -1.20000
AFIX 0
C58 1 -0.465914 -0.780256 0.123579 11.00000 0.07300 0.12401 =
0.08573 -0.01289 -0.00102 0.02488
AFIX 43
H58 2 -0.479740 -0.779523 0.057386 11.00000 -1.20000
AFIX 0
HKLF 4
REM exp_15640 in P-1 #2
REM wR2 = 0.1799, GooF = S = 1.045, Restrained GooF = 1.045 for all data
REM R1 = 0.0614 for 5870 Fo > 4sig(Fo) and 0.0725 for all 7310 data
REM 525 parameters refined using 0 restraints
END
WGHT 0.0983 0.4424
REM Highest difference peak 0.228, deepest hole -0.313, 1-sigma level 0.060
Q1 1 -0.4166 -0.2071 0.3625 11.00000 0.05 0.23
Q2 1 0.0163 -0.1788 0.1735 11.00000 0.05 0.21
Q3 1 0.1216 0.3337 0.0858 11.00000 0.05 0.20
Q4 1 -0.4003 -0.4158 0.0534 11.00000 0.05 0.20
Q5 1 0.1266 0.3428 0.1540 11.00000 0.05 0.18
REM The information below was added by Olex2.
REM
REM R1 = 0.0614 for 5870 Fo > 4sig(Fo) and 0.0725 for all 34588 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.23, deepest hole -0.31
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0725
REM R1_gt = 0.0614
REM wR_ref = 0.1799
REM GOOF = 1.045
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 34588
REM Reflections_gt = 5870
REM Parameters = n/a
REM Hole = -0.31
REM Peak = 0.23
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.673