# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
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# 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_K5
_database_code_depnum_ccdc_archive 'CCDC 1962326'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record
;
2019-10-29 deposited with the CCDC. 2019-12-12 downloaded from the CCDC.
;
_audit_creation_date 2018-06-04
_audit_creation_method
;
Olex2 1.2-beta
(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 'C15 H13 N2 O5 Re'
_chemical_formula_sum 'C15 H13 N2 O5 Re'
_chemical_formula_weight 487.47
_chemical_absolute_configuration ad
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 6.3450(2)
_cell_length_b 14.5492(5)
_cell_length_c 16.7909(7)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1550.05(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3384
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 23.820
_cell_measurement_theta_min 2.426
_shelx_estimated_absorpt_T_max 0.460
_shelx_estimated_absorpt_T_min 0.285
_exptl_absorpt_coefficient_mu 7.866
_exptl_absorpt_correction_T_max 0.0932
_exptl_absorpt_correction_T_min 0.0546
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0956 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.5858. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'Light Yellow'
_exptl_crystal_colour_modifier Light
_exptl_crystal_colour_primary Yellow
_exptl_crystal_density_diffrn 2.089
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Rod
_exptl_crystal_F_000 928
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.213
_exptl_crystal_size_mid 0.145
_exptl_crystal_size_min 0.117
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0536
_diffrn_reflns_av_unetI/netI 0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 17683
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 26.396
_diffrn_reflns_theta_min 1.852
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker X8 APEX II'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_source_type fine-focus
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.716
_reflns_Friedel_fraction_full 0.999
_reflns_Friedel_fraction_max 0.994
_reflns_number_gt 2054
_reflns_number_total 3161
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.494
_refine_diff_density_min -0.533
_refine_diff_density_rms 0.121
_refine_ls_abs_structure_details
;
Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.025(14)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.000
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 211
_refine_ls_number_reflns 3161
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0517
_refine_ls_R_factor_gt 0.0239
_refine_ls_restrained_S_all 1.000
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0072P)^2^+1.4757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0424
_refine_ls_wR_factor_ref 0.0501
_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,H,H,H) groups
2. Shared sites
{C8B, N2}
{C8, N2B}
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(N2)
Uanis(C8) = Uanis(N2B)
4. Others
Sof(N2B)=Sof(H4B)=Sof(H7B)=Sof(H9BD)=Sof(H9BE)=Sof(H9BF)=Sof(H10D)=Sof(H10E)=
Sof(H10F)=Sof(C8B)=1-FVAR(1)
Sof(N2)=Sof(H4A)=Sof(H7A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(H10A)=Sof(H10B)=
Sof(H10C)=Sof(C8)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
C4(H4A), C4(H4B), C7(H7A), C7(H7B), C11(H11), C12(H12), C13(H13), C14(H14),
C15(H15)
5.b Idealised Me refined as rotating group:
C9(H9AA,H9AB,H9AC), C9(H9BD,H9BE,H9BF), C10(H10A,H10B,H10C), C10(H10D,H10E,
H10F)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
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
Re1 Re 0.50183(6) -0.00029(3) 0.33915(2) 0.01650(9) Uani 1 1 d . . . . .
O1 O 0.6749(11) -0.1089(4) 0.4824(4) 0.0302(17) Uani 1 1 d . . . . .
O2 O 0.1216(10) -0.1292(4) 0.3505(4) 0.0371(19) Uani 1 1 d . . . . .
O3 O 0.7139(10) -0.1394(4) 0.2274(4) 0.0273(16) Uani 1 1 d . . . . .
O4 O 0.3664(9) 0.1093(4) 0.4052(3) 0.0168(14) Uani 1 1 d . . . . .
O5 O 0.7409(9) 0.1030(4) 0.3326(3) 0.0178(15) Uani 1 1 d . . . . .
N1 N 0.3767(12) 0.0843(5) 0.2398(4) 0.0173(18) Uani 1 1 d . . . . .
N2 N 0.5466(12) 0.3428(5) 0.4355(5) 0.017(3) Uani 0.64(8) 1 d . . P A 1
N2B N 0.7343(14) 0.3406(6) 0.3986(5) 0.017(3) Uani 0.36(8) 1 d . . P A 2
C1 C 0.6131(15) -0.0665(6) 0.4287(6) 0.023(2) Uani 1 1 d . . . . .
C2 C 0.2629(16) -0.0803(6) 0.3450(6) 0.026(2) Uani 1 1 d . . . . .
C3 C 0.6329(14) -0.0873(6) 0.2716(6) 0.021(2) Uani 1 1 d . . . . .
C4 C 0.4197(14) 0.2661(6) 0.4381(5) 0.017(2) Uani 1 1 d . . . . .
H4A H 0.287789 0.269284 0.464697 0.020 Uiso 0.64(8) 1 calc R . P A 1
H4B H 0.287789 0.269284 0.464697 0.020 Uiso 0.36(8) 1 calc R . P A 2
C5 C 0.4804(16) 0.1845(5) 0.4027(4) 0.0143(18) Uani 1 1 d . . . . .
C6 C 0.6812(13) 0.1810(6) 0.3639(5) 0.017(2) Uani 1 1 d . . . . .
C7 C 0.8018(14) 0.2599(6) 0.3628(5) 0.016(2) Uani 1 1 d . . . . .
H7A H 0.934817 0.258980 0.336855 0.020 Uiso 0.64(8) 1 calc R . P A 1
H7B H 0.934817 0.258980 0.336855 0.020 Uiso 0.36(8) 1 calc R . P A 2
C9 C 0.8731(14) 0.4235(5) 0.3994(5) 0.020(2) Uani 1 1 d . . . . .
H9AA H 0.800028 0.474923 0.373635 0.030 Uiso 0.64(8) 1 calc GR . P A 1
H9AB H 1.003708 0.410153 0.370441 0.030 Uiso 0.64(8) 1 calc GR . P A 1
H9AC H 0.906658 0.439984 0.454529 0.030 Uiso 0.64(8) 1 calc GR . P A 1
H9BD H 0.934728 0.431078 0.452487 0.030 Uiso 0.36(8) 1 calc GR . P A 2
H9BE H 0.789620 0.478080 0.386015 0.030 Uiso 0.36(8) 1 calc GR . P A 2
H9BF H 0.986048 0.415901 0.360102 0.030 Uiso 0.36(8) 1 calc GR . P A 2
C10 C 0.4712(15) 0.4278(5) 0.4755(5) 0.018(2) Uani 1 1 d . . . . .
H10A H 0.581639 0.451197 0.510898 0.027 Uiso 0.64(8) 1 calc GR . P A 1
H10B H 0.344697 0.413799 0.506768 0.027 Uiso 0.64(8) 1 calc GR . P A 1
H10C H 0.437451 0.474302 0.435305 0.027 Uiso 0.64(8) 1 calc GR . P A 1
H10D H 0.316762 0.427796 0.476952 0.027 Uiso 0.36(8) 1 calc GR . P A 2
H10E H 0.520826 0.481668 0.445990 0.027 Uiso 0.36(8) 1 calc GR . P A 2
H10F H 0.526200 0.429834 0.530029 0.027 Uiso 0.36(8) 1 calc GR . P A 2
C11 C 0.1746(14) 0.1141(6) 0.2415(6) 0.021(2) Uani 1 1 d . . . . .
H11 H 0.085368 0.095184 0.283932 0.025 Uiso 1 1 calc R . . . .
C12 C 0.0953(14) 0.1711(6) 0.1833(5) 0.022(2) Uani 1 1 d . . . . .
H12 H -0.046259 0.192039 0.186314 0.026 Uiso 1 1 calc R . . . .
C13 C 0.2212(15) 0.1975(6) 0.1210(7) 0.026(3) Uani 1 1 d . . . . .
H13 H 0.167593 0.235403 0.079685 0.031 Uiso 1 1 calc R . . . .
C14 C 0.4279(15) 0.1677(6) 0.1198(6) 0.026(2) Uani 1 1 d . . . . .
H14 H 0.519784 0.185692 0.077961 0.031 Uiso 1 1 calc R . . . .
C15 C 0.4978(18) 0.1121(5) 0.1793(4) 0.0218(18) Uani 1 1 d . . . . .
H15 H 0.640204 0.092059 0.177759 0.026 Uiso 1 1 calc R . . . .
C8 C 0.7343(14) 0.3406(6) 0.3986(5) 0.017(3) Uani 0.64(8) 1 d . . P A 1
C8B C 0.5466(12) 0.3428(5) 0.4355(5) 0.017(3) Uani 0.36(8) 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Re1 0.01535(13) 0.01550(16) 0.01866(14) -0.00242(19) 0.0004(2) -0.0015(3)
O1 0.042(4) 0.026(4) 0.022(4) -0.001(3) -0.005(3) 0.001(3)
O2 0.025(4) 0.027(5) 0.060(6) -0.002(4) 0.004(4) -0.011(3)
O3 0.030(4) 0.028(4) 0.024(4) -0.006(3) 0.003(3) 0.006(3)
O4 0.019(3) 0.014(3) 0.017(4) -0.003(3) 0.005(3) -0.001(3)
O5 0.012(3) 0.018(4) 0.023(4) -0.003(3) 0.002(3) -0.003(3)
N1 0.019(4) 0.011(4) 0.022(5) -0.009(3) -0.002(4) 0.000(3)
N2 0.021(6) 0.015(5) 0.015(4) 0.001(3) -0.003(3) 0.001(3)
N2B 0.029(6) 0.012(5) 0.012(5) 0.006(4) -0.005(4) -0.001(4)
C1 0.024(6) 0.020(6) 0.025(6) -0.013(5) 0.010(5) -0.002(4)
C2 0.033(6) 0.014(5) 0.030(6) 0.000(5) 0.001(5) 0.004(5)
C3 0.012(5) 0.026(6) 0.024(6) 0.002(5) -0.002(4) -0.010(4)
C4 0.020(5) 0.016(5) 0.015(5) 0.004(4) -0.001(4) 0.001(4)
C5 0.016(5) 0.015(4) 0.013(4) -0.003(3) -0.002(5) -0.004(5)
C6 0.011(5) 0.030(6) 0.008(5) -0.001(4) 0.000(4) 0.003(4)
C7 0.014(5) 0.014(5) 0.021(6) 0.003(4) 0.001(4) -0.001(4)
C9 0.026(5) 0.010(5) 0.024(6) 0.001(4) 0.002(4) -0.005(4)
C10 0.015(6) 0.020(5) 0.020(4) 0.001(4) 0.001(4) 0.001(4)
C11 0.017(5) 0.015(5) 0.032(6) -0.008(4) 0.000(4) -0.007(4)
C12 0.021(5) 0.013(5) 0.033(6) -0.001(4) -0.004(4) -0.001(4)
C13 0.022(6) 0.019(6) 0.036(7) 0.005(5) -0.008(5) -0.005(5)
C14 0.036(7) 0.026(6) 0.016(6) 0.001(4) 0.009(4) -0.010(4)
C15 0.014(4) 0.028(5) 0.023(5) -0.009(3) 0.009(6) -0.005(6)
C8 0.029(6) 0.012(5) 0.012(5) 0.006(4) -0.005(4) -0.001(4)
C8B 0.021(6) 0.015(5) 0.015(4) 0.001(3) -0.003(3) 0.001(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 2.124(5) . ?
Re1 O5 2.138(6) . ?
Re1 N1 2.220(7) . ?
Re1 C1 1.920(10) . ?
Re1 C2 1.914(10) . ?
Re1 C3 1.892(10) . ?
O1 C1 1.161(10) . ?
O2 C2 1.148(11) . ?
O3 C3 1.179(10) . ?
O4 C5 1.312(9) . ?
O5 C6 1.308(10) . ?
N1 C11 1.354(11) . ?
N1 C15 1.337(10) . ?
N2 C4 1.377(11) . ?
N2 C10 1.487(10) . ?
N2 C8 1.343(10) . ?
N2B C7 1.386(12) . ?
N2B C9 1.495(11) . ?
N2B C8B 1.343(10) . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C4 C5 1.382(11) . ?
C4 C8B 1.377(11) . ?
C5 C6 1.432(12) . ?
C6 C7 1.380(12) . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C7 C8 1.386(12) . ?
C9 H9AA 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C9 H9BD 0.9800 . ?
C9 H9BE 0.9800 . ?
C9 H9BF 0.9800 . ?
C9 C8 1.495(11) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C10 C8B 1.487(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(12) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(13) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.359(12) . ?
C15 H15 0.9500 . ?
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
O4 Re1 O5 77.7(2) . . ?
O4 Re1 N1 80.3(2) . . ?
O5 Re1 N1 79.9(2) . . ?
C1 Re1 O4 96.7(3) . . ?
C1 Re1 O5 97.6(3) . . ?
C1 Re1 N1 176.4(3) . . ?
C2 Re1 O4 96.3(3) . . ?
C2 Re1 O5 172.8(3) . . ?
C2 Re1 N1 95.3(3) . . ?
C2 Re1 C1 86.9(4) . . ?
C3 Re1 O4 173.2(3) . . ?
C3 Re1 O5 97.3(3) . . ?
C3 Re1 N1 94.4(4) . . ?
C3 Re1 C1 88.4(4) . . ?
C3 Re1 C2 88.4(4) . . ?
C5 O4 Re1 112.7(5) . . ?
C6 O5 Re1 112.6(5) . . ?
C11 N1 Re1 120.0(6) . . ?
C15 N1 Re1 122.3(7) . . ?
C15 N1 C11 117.6(8) . . ?
C4 N2 C10 118.1(7) . . ?
C8 N2 C4 120.9(8) . . ?
C8 N2 C10 120.9(8) . . ?
C7 N2B C9 120.3(8) . . ?
C8B N2B C7 119.6(8) . . ?
C8B N2B C9 120.0(8) . . ?
O1 C1 Re1 177.6(8) . . ?
O2 C2 Re1 178.1(9) . . ?
O3 C3 Re1 177.7(9) . . ?
N2 C4 H4A 119.4 . . ?
N2 C4 C5 121.3(8) . . ?
C5 C4 H4A 119.4 . . ?
C5 C4 H4B 119.4 . . ?
C8B C4 H4B 119.4 . . ?
C8B C4 C5 121.3(8) . . ?
O4 C5 C4 123.3(9) . . ?
O4 C5 C6 118.4(7) . . ?
C4 C5 C6 118.3(8) . . ?
O5 C6 C5 118.1(8) . . ?
O5 C6 C7 123.8(8) . . ?
C7 C6 C5 118.0(8) . . ?
N2B C7 H7B 119.1 . . ?
C6 C7 N2B 121.8(9) . . ?
C6 C7 H7A 119.1 . . ?
C6 C7 H7B 119.1 . . ?
C6 C7 C8 121.8(9) . . ?
C8 C7 H7A 119.1 . . ?
N2B C9 H9BD 109.5 . . ?
N2B C9 H9BE 109.5 . . ?
N2B C9 H9BF 109.5 . . ?
H9AA C9 H9AB 109.5 . . ?
H9AA C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
H9BD C9 H9BE 109.5 . . ?
H9BD C9 H9BF 109.5 . . ?
H9BE C9 H9BF 109.5 . . ?
C8 C9 H9AA 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
C8 C9 H9AC 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10D C10 H10E 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C8B C10 H10D 109.5 . . ?
C8B C10 H10E 109.5 . . ?
C8B C10 H10F 109.5 . . ?
N1 C11 H11 119.2 . . ?
N1 C11 C12 121.6(9) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(9) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.5(10) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(10) . . ?
C15 C14 H14 120.5 . . ?
N1 C15 C14 123.5(10) . . ?
N1 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N2 C8 C7 119.6(8) . . ?
N2 C8 C9 120.0(8) . . ?
C7 C8 C9 120.3(8) . . ?
N2B C8B C4 120.9(8) . . ?
N2B C8B C10 120.9(8) . . ?
C4 C8B C10 118.1(7) . . ?
_shelx_res_file
;
TITL CM26K in P2(1)2(1)2(1)
cm26k.res
created by SHELXL-2018/3 at 13:08:12 on 04-Jun-2018
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.160, Rweak 0.002, Alpha 0.035, Orientation as input
REM Flack x = 0.274 ( 0.022 ) from Parsons' quotients
REM Formula found by SHELXT: C23 N3 O3 Re
CELL 0.71073 6.345 14.5492 16.7909 90 90 90
ZERR 4 0.0002 0.0005 0.0007 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O Re
UNIT 60 52 8 20 4
EADP C8B N2
EADP C8 N2B
EXYZ C8B N2
EXYZ C8 N2B
L.S. 10
PLAN 20
SIZE 0.213 0.145 0.117
TEMP -173.15
BOND $H
fmap 2
ACTA 50
REM
REM
REM
WGHT 0.007200 1.475700
FVAR 0.33439 0.63514
RE1 5 0.501835 -0.000287 0.339153 11.00000 0.01535 0.01550 =
0.01866 -0.00242 0.00038 -0.00149
O1 4 0.674911 -0.108912 0.482411 11.00000 0.04224 0.02614 =
0.02221 -0.00088 -0.00456 0.00127
O2 4 0.121602 -0.129185 0.350514 11.00000 0.02481 0.02678 =
0.05959 -0.00178 0.00382 -0.01072
O3 4 0.713871 -0.139378 0.227374 11.00000 0.02964 0.02810 =
0.02412 -0.00605 0.00304 0.00630
O4 4 0.366387 0.109347 0.405163 11.00000 0.01945 0.01378 =
0.01703 -0.00312 0.00451 -0.00140
O5 4 0.740892 0.102951 0.332551 11.00000 0.01216 0.01805 =
0.02329 -0.00344 0.00207 -0.00297
N1 3 0.376740 0.084278 0.239803 11.00000 0.01882 0.01057 =
0.02243 -0.00851 -0.00229 -0.00009
PART 1
N2 3 0.546594 0.342763 0.435475 21.00000 0.02078 0.01513 =
0.01518 0.00074 -0.00296 0.00073
PART 0
PART 2
N2B 3 0.734264 0.340553 0.398587 -21.00000 0.02877 0.01178 =
0.01185 0.00616 -0.00498 -0.00073
PART 0
C1 1 0.613067 -0.066509 0.428675 11.00000 0.02389 0.02000 =
0.02460 -0.01263 0.00960 -0.00181
C2 1 0.262905 -0.080302 0.345002 11.00000 0.03330 0.01402 =
0.02984 -0.00031 0.00070 0.00351
C3 1 0.632870 -0.087264 0.271627 11.00000 0.01180 0.02618 =
0.02372 0.00154 -0.00206 -0.00950
C4 1 0.419688 0.266067 0.438069 11.00000 0.01966 0.01646 =
0.01458 0.00433 -0.00056 0.00147
PART 1
AFIX 43
H4A 2 0.287789 0.269284 0.464697 21.00000 -1.20000
AFIX 43
PART 0
PART 2
H4B 2 0.287789 0.269284 0.464697 -21.00000 -1.20000
AFIX 0
PART 0
C5 1 0.480410 0.184492 0.402696 11.00000 0.01557 0.01477 =
0.01267 -0.00268 -0.00191 -0.00355
C6 1 0.681206 0.180991 0.363909 11.00000 0.01106 0.03017 =
0.00847 -0.00133 0.00038 0.00310
C7 1 0.801822 0.259942 0.362830 11.00000 0.01402 0.01404 =
0.02119 0.00273 0.00111 -0.00142
PART 1
AFIX 43
H7A 2 0.934817 0.258980 0.336855 21.00000 -1.20000
AFIX 43
PART 0
PART 2
H7B 2 0.934817 0.258980 0.336855 -21.00000 -1.20000
AFIX 0
PART 0
C9 1 0.873121 0.423549 0.399365 11.00000 0.02563 0.01046 =
0.02439 0.00138 0.00212 -0.00457
PART 1
AFIX 137
H9AA 2 0.800028 0.474923 0.373635 21.00000 -1.50000
H9AB 2 1.003708 0.410153 0.370441 21.00000 -1.50000
H9AC 2 0.906658 0.439984 0.454529 21.00000 -1.50000
AFIX 137
PART 0
PART 2
H9BD 2 0.934728 0.431078 0.452487 -21.00000 -1.50000
H9BE 2 0.789620 0.478080 0.386015 -21.00000 -1.50000
H9BF 2 0.986048 0.415901 0.360102 -21.00000 -1.50000
AFIX 0
PART 0
C10 1 0.471168 0.427758 0.475524 11.00000 0.01511 0.01988 =
0.01979 0.00063 0.00076 0.00097
PART 1
AFIX 137
H10A 2 0.581639 0.451197 0.510898 21.00000 -1.50000
H10B 2 0.344697 0.413799 0.506768 21.00000 -1.50000
H10C 2 0.437451 0.474302 0.435305 21.00000 -1.50000
AFIX 137
PART 0
PART 2
H10D 2 0.316762 0.427796 0.476952 -21.00000 -1.50000
H10E 2 0.520826 0.481668 0.445990 -21.00000 -1.50000
H10F 2 0.526200 0.429834 0.530029 -21.00000 -1.50000
AFIX 0
PART 0
C11 1 0.174600 0.114060 0.241546 11.00000 0.01690 0.01489 =
0.03178 -0.00808 -0.00035 -0.00725
AFIX 43
H11 2 0.085368 0.095184 0.283932 11.00000 -1.20000
AFIX 0
C12 1 0.095311 0.171066 0.183324 11.00000 0.02058 0.01289 =
0.03266 -0.00136 -0.00369 -0.00129
AFIX 43
H12 2 -0.046259 0.192039 0.186314 11.00000 -1.20000
AFIX 0
C13 1 0.221232 0.197471 0.121036 11.00000 0.02209 0.01893 =
0.03561 0.00546 -0.00841 -0.00459
AFIX 43
H13 2 0.167593 0.235403 0.079685 11.00000 -1.20000
AFIX 0
C14 1 0.427860 0.167651 0.119795 11.00000 0.03584 0.02605 =
0.01606 0.00106 0.00879 -0.01002
AFIX 43
H14 2 0.519784 0.185692 0.077961 11.00000 -1.20000
AFIX 0
C15 1 0.497788 0.112133 0.179273 11.00000 0.01436 0.02822 =
0.02274 -0.00941 0.00897 -0.00478
AFIX 43
H15 2 0.640204 0.092059 0.177759 11.00000 -1.20000
AFIX 0
PART 1
C8 1 0.734264 0.340553 0.398587 21.00000 0.02877 0.01178 =
0.01185 0.00616 -0.00498 -0.00073
PART 0
PART 2
C8B 1 0.546594 0.342763 0.435475 -21.00000 0.02078 0.01513 =
0.01518 0.00074 -0.00296 0.00073
HKLF 4
REM CM26K in P2(1)2(1)2(1)
REM wR2 = 0.0501, GooF = S = 1.000, Restrained GooF = 1.000 for all data
REM R1 = 0.0239 for 2054 Fo > 4sig(Fo) and 0.0517 for all 3161 data
REM 211 parameters refined using 0 restraints
END
WGHT 0.0072 1.4757
REM Highest difference peak 0.494, deepest hole -0.533, 1-sigma level 0.121
Q1 1 -0.0106 0.0380 0.3643 11.00000 0.05 0.49
Q2 1 0.5918 -0.0563 0.3415 11.00000 0.05 0.43
Q3 1 0.4972 0.3817 0.4531 11.00000 0.05 0.40
Q4 1 0.3461 0.0000 0.3795 11.00000 0.05 0.40
Q5 1 0.4939 0.3005 0.4175 11.00000 0.05 0.40
Q6 1 0.8886 -0.1712 0.1808 11.00000 0.05 0.39
Q7 1 0.4214 -0.0699 0.3572 11.00000 0.05 0.39
Q8 1 0.8364 -0.1049 0.4982 11.00000 0.05 0.39
Q9 1 0.3102 0.4993 0.4091 11.00000 0.05 0.39
Q10 1 0.6133 0.0429 0.3191 11.00000 0.05 0.39
Q11 1 0.3517 -0.0362 0.2800 11.00000 0.05 0.39
Q12 1 1.0475 0.4931 0.3246 11.00000 0.05 0.38
Q13 1 0.6041 0.1242 0.1949 11.00000 0.05 0.38
Q14 1 1.0899 0.3389 0.4010 11.00000 0.05 0.38
Q15 1 0.1502 0.1009 0.1978 11.00000 0.05 0.37
Q16 1 -0.1323 0.1518 0.2351 11.00000 0.05 0.37
Q17 1 0.6437 0.4987 0.5347 11.00000 0.05 0.36
Q18 1 0.7328 -0.0989 0.2981 11.00000 0.05 0.36
Q19 1 0.8592 0.5575 0.4156 11.00000 0.05 0.36
Q20 1 0.3716 0.2338 -0.0239 11.00000 0.05 0.36
;
_shelx_res_checksum 16665
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, hexanes'
#######################################################################
#
# 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_K8
_database_code_depnum_ccdc_archive 'CCDC 1962327'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record
;
2019-10-29 deposited with the CCDC. 2019-12-12 downloaded from the CCDC.
;
_audit_creation_date 2018-06-04
_audit_creation_method
;
Olex2 1.2-beta
(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 'C13 H9 N2 O5 Re'
_chemical_formula_sum 'C13 H9 N2 O5 Re'
_chemical_formula_weight 459.42
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 '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 9.1929(5)
_cell_length_b 13.3161(7)
_cell_length_c 11.3352(6)
_cell_angle_alpha 90
_cell_angle_beta 106.800(2)
_cell_angle_gamma 90
_cell_volume 1328.36(12)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9925
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 26.384
_cell_measurement_theta_min 2.314
_shelx_estimated_absorpt_T_max 0.479
_shelx_estimated_absorpt_T_min 0.380
_exptl_absorpt_coefficient_mu 9.171
_exptl_absorpt_correction_T_max 0.0932
_exptl_absorpt_correction_T_min 0.0572
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0924 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.6137. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'Light Yellow'
_exptl_crystal_colour_modifier Light
_exptl_crystal_colour_primary Yellow
_exptl_crystal_density_diffrn 2.297
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 864
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.131
_exptl_crystal_size_mid 0.106
_exptl_crystal_size_min 0.094
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0373
_diffrn_reflns_av_unetI/netI 0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 25383
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 26.404
_diffrn_reflns_theta_min 2.314
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker X8 APEX II'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_source_type fine-focus
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2508
_reflns_number_total 2729
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction 'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.404
_refine_diff_density_min -0.587
_refine_diff_density_rms 0.089
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.068
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 191
_refine_ls_number_reflns 2729
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0175
_refine_ls_R_factor_gt 0.0145
_refine_ls_restrained_S_all 1.068
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0073P)^2^+1.6265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0302
_refine_ls_wR_factor_ref 0.0309
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Shared sites
{C4, N2B}
{C4B, N2}
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(N2B)
Uanis(C4B) = Uanis(N2)
4. Others
Sof(N2B)=Sof(H5B)=Sof(H8B)=Sof(C4B)=1-FVAR(1)
Sof(N2)=Sof(H5A)=Sof(H8A)=Sof(C4)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
C5(H5A), C5(H5B), C6(H6), C7(H7), C8(H8A), C8(H8B), C9(H9), C10(H10),
C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
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
Re1 Re 0.33901(2) 0.52165(2) 0.27449(2) 0.01268(4) Uani 1 1 d . . . . .
O1 O 0.4872(2) 0.31659(14) 0.35439(19) 0.0213(5) Uani 1 1 d . . . . .
O2 O 0.1678(2) 0.49735(15) 0.46784(18) 0.0216(5) Uani 1 1 d . . . . .
O3 O 0.0588(2) 0.41824(15) 0.10452(18) 0.0229(5) Uani 1 1 d . . . . .
O4 O 0.5433(2) 0.59874(14) 0.36732(16) 0.0151(4) Uani 1 1 d . . . . .
O5 O 0.4432(2) 0.55020(14) 0.13266(17) 0.0167(4) Uani 1 1 d . . . . .
N1 N 0.2624(3) 0.67963(17) 0.2424(2) 0.0143(5) Uani 1 1 d . . . . .
N2 N 0.6288(3) 0.61986(18) 0.2958(2) 0.0143(6) Uani 0.36(2) 1 d . . P A 1
N2B N 0.5799(3) 0.59289(17) 0.1749(2) 0.0145(6) Uani 0.64(2) 1 d . . P A 2
C1 C 0.4303(3) 0.3922(2) 0.3215(2) 0.0155(6) Uani 1 1 d . . . . .
C2 C 0.2381(3) 0.50683(19) 0.3986(3) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.1639(3) 0.4580(2) 0.1697(3) 0.0163(6) Uani 1 1 d . . . . .
C5 C 0.6681(3) 0.6085(2) 0.0966(3) 0.0167(6) Uani 1 1 d . . . . .
H5A H 0.632962 0.587434 0.013067 0.020 Uiso 0.36(2) 1 calc R . P A 1
H5B H 0.632962 0.587434 0.013067 0.020 Uiso 0.64(2) 1 calc R . P A 2
C6 C 0.8059(3) 0.6545(2) 0.1397(3) 0.0198(6) Uani 1 1 d . . . . .
H6 H 0.868083 0.664345 0.086740 0.024 Uiso 1 1 calc R . . . .
C7 C 0.8554(3) 0.6870(2) 0.2621(3) 0.0194(6) Uani 1 1 d . . . . .
H7 H 0.949789 0.720888 0.291924 0.023 Uiso 1 1 calc R . . . .
C8 C 0.7669(3) 0.6696(2) 0.3392(3) 0.0173(6) Uani 1 1 d . . . . .
H8A H 0.800295 0.691741 0.422369 0.021 Uiso 0.36(2) 1 calc R . P A 1
H8B H 0.800295 0.691741 0.422369 0.021 Uiso 0.64(2) 1 calc R . P A 2
C9 C 0.3009(3) 0.7448(2) 0.3370(3) 0.0177(6) Uani 1 1 d . . . . .
H9 H 0.360558 0.721336 0.415119 0.021 Uiso 1 1 calc R . . . .
C10 C 0.2574(3) 0.8446(2) 0.3252(3) 0.0189(6) Uani 1 1 d . . . . .
H10 H 0.286381 0.888586 0.393977 0.023 Uiso 1 1 calc R . . . .
C11 C 0.1706(3) 0.8793(2) 0.2110(3) 0.0197(6) Uani 1 1 d . . . . .
H11 H 0.138503 0.947317 0.200300 0.024 Uiso 1 1 calc R . . . .
C12 C 0.1319(3) 0.8127(2) 0.1133(3) 0.0182(6) Uani 1 1 d . . . . .
H12 H 0.072927 0.834601 0.034159 0.022 Uiso 1 1 calc R . . . .
C13 C 0.1794(3) 0.7145(2) 0.1317(3) 0.0165(6) Uani 1 1 d . . . . .
H13 H 0.152663 0.669471 0.063826 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5799(3) 0.59289(17) 0.1749(2) 0.0145(6) Uani 0.36(2) 1 d . . P A 1
C4B C 0.6288(3) 0.61986(18) 0.2958(2) 0.0143(6) Uani 0.64(2) 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Re1 0.01222(6) 0.01349(6) 0.01244(6) -0.00028(4) 0.00373(4) -0.00110(5)
O1 0.0192(11) 0.0165(10) 0.0271(11) -0.0007(9) 0.0050(9) 0.0019(9)
O2 0.0243(12) 0.0242(11) 0.0196(11) 0.0019(8) 0.0115(9) 0.0020(9)
O3 0.0201(11) 0.0269(12) 0.0193(11) -0.0004(9) 0.0017(9) -0.0072(9)
O4 0.0123(10) 0.0188(10) 0.0146(10) -0.0005(8) 0.0045(8) -0.0022(8)
O5 0.0141(10) 0.0223(10) 0.0140(10) -0.0033(8) 0.0043(8) -0.0068(8)
N1 0.0126(12) 0.0172(12) 0.0144(11) 0.0002(9) 0.0061(10) -0.0016(10)
N2 0.0131(14) 0.0138(13) 0.0158(13) -0.0006(10) 0.0038(11) 0.0000(10)
N2B 0.0144(13) 0.0132(12) 0.0155(13) 0.0002(10) 0.0040(10) -0.0007(10)
C1 0.0123(14) 0.0197(15) 0.0151(14) -0.0035(12) 0.0049(11) -0.0038(12)
C2 0.0180(15) 0.0117(13) 0.0175(14) -0.0009(11) 0.0022(12) 0.0009(11)
C3 0.0174(15) 0.0166(14) 0.0168(14) 0.0022(11) 0.0080(12) 0.0014(12)
C5 0.0183(15) 0.0176(14) 0.0151(14) 0.0002(11) 0.0066(12) -0.0006(12)
C6 0.0193(16) 0.0209(15) 0.0230(15) 0.0017(12) 0.0119(13) -0.0025(13)
C7 0.0136(15) 0.0187(14) 0.0241(16) 0.0027(12) 0.0027(12) -0.0025(12)
C8 0.0184(16) 0.0157(14) 0.0163(14) -0.0025(11) 0.0027(12) -0.0012(12)
C9 0.0172(15) 0.0193(14) 0.0168(14) -0.0001(11) 0.0055(12) -0.0014(12)
C10 0.0206(16) 0.0181(14) 0.0204(15) -0.0037(12) 0.0097(13) -0.0023(12)
C11 0.0169(15) 0.0166(14) 0.0276(16) 0.0043(12) 0.0098(13) -0.0008(12)
C12 0.0110(14) 0.0224(15) 0.0182(15) 0.0052(12) -0.0007(12) -0.0018(12)
C13 0.0131(14) 0.0209(15) 0.0151(14) -0.0004(11) 0.0031(11) -0.0057(12)
C4 0.0144(13) 0.0132(12) 0.0155(13) 0.0002(10) 0.0040(10) -0.0007(10)
C4B 0.0131(14) 0.0138(13) 0.0158(13) -0.0006(10) 0.0038(11) 0.0000(10)
_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
Re1 O4 2.1318(18) . ?
Re1 O5 2.1302(18) . ?
Re1 N1 2.215(2) . ?
Re1 C1 1.923(3) . ?
Re1 C2 1.906(3) . ?
Re1 C3 1.901(3) . ?
O1 C1 1.147(3) . ?
O2 C2 1.158(3) . ?
O3 C3 1.160(3) . ?
O4 N2 1.313(3) . ?
O4 C4B 1.313(3) . ?
O5 N2B 1.335(3) . ?
O5 C4 1.335(3) . ?
N1 C9 1.345(3) . ?
N1 C13 1.348(3) . ?
N2 C8 1.390(4) . ?
N2 C4 1.362(3) . ?
N2B C5 1.380(4) . ?
N2B C4B 1.362(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C5 C6 1.364(4) . ?
C5 C4 1.380(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(4) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C8 C4B 1.390(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9500 . ?
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
O4 Re1 N1 79.43(8) . . ?
O5 Re1 O4 76.26(7) . . ?
O5 Re1 N1 84.11(8) . . ?
C1 Re1 O4 92.48(9) . . ?
C1 Re1 O5 96.52(10) . . ?
C1 Re1 N1 171.52(10) . . ?
C2 Re1 O4 103.44(10) . . ?
C2 Re1 O5 175.24(9) . . ?
C2 Re1 N1 91.16(10) . . ?
C2 Re1 C1 88.23(11) . . ?
C3 Re1 O4 171.47(9) . . ?
C3 Re1 O5 95.32(10) . . ?
C3 Re1 N1 98.58(10) . . ?
C3 Re1 C1 89.79(11) . . ?
C3 Re1 C2 84.84(12) . . ?
N2 O4 Re1 113.44(15) . . ?
C4B O4 Re1 113.44(15) . . ?
N2B O5 Re1 112.80(15) . . ?
C4 O5 Re1 112.80(15) . . ?
C9 N1 Re1 118.95(18) . . ?
C9 N1 C13 117.9(2) . . ?
C13 N1 Re1 123.19(18) . . ?
O4 N2 C8 122.2(2) . . ?
O4 N2 C4 118.9(2) . . ?
C4 N2 C8 118.9(2) . . ?
O5 N2B C5 120.0(2) . . ?
O5 N2B C4B 118.4(2) . . ?
C4B N2B C5 121.5(2) . . ?
O1 C1 Re1 177.1(2) . . ?
O2 C2 Re1 175.4(2) . . ?
O3 C3 Re1 178.6(3) . . ?
N2B C5 H5B 120.2 . . ?
C6 C5 N2B 119.7(3) . . ?
C6 C5 H5A 120.2 . . ?
C6 C5 H5B 120.2 . . ?
C6 C5 C4 119.7(3) . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
N2 C8 H8A 119.9 . . ?
C7 C8 N2 120.2(3) . . ?
C7 C8 H8A 119.9 . . ?
C7 C8 H8B 119.9 . . ?
C7 C8 C4B 120.2(3) . . ?
C4B C8 H8B 119.9 . . ?
N1 C9 H9 118.6 . . ?
N1 C9 C10 122.8(3) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
N1 C13 C12 122.5(3) . . ?
N1 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
O5 C4 N2 118.4(2) . . ?
O5 C4 C5 120.0(2) . . ?
N2 C4 C5 121.5(2) . . ?
O4 C4B N2B 118.9(2) . . ?
O4 C4B C8 122.2(2) . . ?
N2B C4B C8 118.9(2) . . ?
_shelx_res_file
;
TITL CM31 in P2(1)/c
cm31.res
created by SHELXL-2018/3 at 13:28:45 on 04-Jun-2018
REM SHELXT solution in P2(1)/c
REM R1 0.031, Rweak 0.002, Alpha 0.017, Orientation as input
REM Formula found by SHELXT: C13 N O5 Re
CELL 0.71073 9.1929 13.3161 11.3352 90 106.8 90
ZERR 4 0.0005 0.0007 0.0006 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O Re
UNIT 52 36 8 20 4
EADP C4 N2B
EADP C4B N2
EXYZ C4 N2B
EXYZ C4B N2
L.S. 10
PLAN 20
SIZE 0.131 0.106 0.094
TEMP -173.15
BOND $H
list 4
fmap 2
ACTA 50
OMIT 0 0 2
REM
REM
REM
WGHT 0.007300 1.626500
FVAR 0.27862 0.36281
RE1 5 0.339005 0.521650 0.274493 11.00000 0.01222 0.01349 =
0.01244 -0.00028 0.00373 -0.00110
O1 4 0.487245 0.316591 0.354386 11.00000 0.01916 0.01652 =
0.02708 -0.00067 0.00501 0.00186
O2 4 0.167838 0.497354 0.467839 11.00000 0.02429 0.02419 =
0.01959 0.00187 0.01151 0.00199
O3 4 0.058840 0.418244 0.104516 11.00000 0.02007 0.02686 =
0.01933 -0.00043 0.00167 -0.00720
O4 4 0.543257 0.598741 0.367320 11.00000 0.01227 0.01875 =
0.01463 -0.00050 0.00454 -0.00224
O5 4 0.443242 0.550197 0.132664 11.00000 0.01410 0.02228 =
0.01398 -0.00328 0.00428 -0.00682
N1 3 0.262431 0.679628 0.242375 11.00000 0.01256 0.01721 =
0.01443 0.00018 0.00614 -0.00161
PART 1
N2 3 0.628805 0.619862 0.295813 21.00000 0.01310 0.01384 =
0.01583 -0.00059 0.00382 0.00002
PART 0
PART 2
N2B 3 0.579864 0.592894 0.174856 -21.00000 0.01442 0.01323 =
0.01551 0.00019 0.00403 -0.00067
PART 0
C1 1 0.430271 0.392234 0.321489 11.00000 0.01229 0.01972 =
0.01511 -0.00349 0.00486 -0.00383
C2 1 0.238127 0.506834 0.398639 11.00000 0.01798 0.01168 =
0.01751 -0.00095 0.00216 0.00088
C3 1 0.163862 0.457995 0.169750 11.00000 0.01744 0.01664 =
0.01676 0.00219 0.00797 0.00139
C5 1 0.668066 0.608541 0.096571 11.00000 0.01835 0.01763 =
0.01508 0.00020 0.00656 -0.00062
PART 1
AFIX 43
H5A 2 0.632962 0.587434 0.013067 21.00000 -1.20000
AFIX 43
PART 0
PART 2
H5B 2 0.632962 0.587434 0.013067 -21.00000 -1.20000
AFIX 0
PART 0
C6 1 0.805912 0.654468 0.139691 11.00000 0.01927 0.02086 =
0.02301 0.00175 0.01187 -0.00251
AFIX 43
H6 2 0.868083 0.664345 0.086740 11.00000 -1.20000
AFIX 0
C7 1 0.855352 0.686950 0.262125 11.00000 0.01360 0.01868 =
0.02407 0.00267 0.00273 -0.00247
AFIX 43
H7 2 0.949789 0.720888 0.291924 11.00000 -1.20000
AFIX 0
C8 1 0.766941 0.669636 0.339190 11.00000 0.01840 0.01568 =
0.01635 -0.00251 0.00266 -0.00118
PART 1
AFIX 43
H8A 2 0.800295 0.691741 0.422369 21.00000 -1.20000
AFIX 43
PART 0
PART 2
H8B 2 0.800295 0.691741 0.422369 -21.00000 -1.20000
AFIX 0
PART 0
C9 1 0.300943 0.744816 0.336950 11.00000 0.01723 0.01932 =
0.01684 -0.00005 0.00545 -0.00144
AFIX 43
H9 2 0.360558 0.721336 0.415119 11.00000 -1.20000
AFIX 0
C10 1 0.257412 0.844568 0.325184 11.00000 0.02061 0.01807 =
0.02040 -0.00368 0.00968 -0.00228
AFIX 43
H10 2 0.286381 0.888586 0.393977 11.00000 -1.20000
AFIX 0
C11 1 0.170606 0.879258 0.211034 11.00000 0.01691 0.01656 =
0.02761 0.00430 0.00978 -0.00080
AFIX 43
H11 2 0.138503 0.947317 0.200300 11.00000 -1.20000
AFIX 0
C12 1 0.131854 0.812702 0.113311 11.00000 0.01103 0.02242 =
0.01819 0.00518 -0.00067 -0.00181
AFIX 43
H12 2 0.072927 0.834601 0.034159 11.00000 -1.20000
AFIX 0
C13 1 0.179383 0.714485 0.131712 11.00000 0.01306 0.02090 =
0.01507 -0.00044 0.00312 -0.00574
AFIX 43
H13 2 0.152663 0.669471 0.063826 11.00000 -1.20000
AFIX 0
PART 1
C4 1 0.579864 0.592894 0.174856 21.00000 0.01442 0.01323 =
0.01551 0.00019 0.00403 -0.00067
PART 0
PART 2
C4B 1 0.628805 0.619862 0.295813 -21.00000 0.01310 0.01384 =
0.01583 -0.00059 0.00382 0.00002
HKLF 4
REM CM31 in P2(1)/c
REM wR2 = 0.0309, GooF = S = 1.068, Restrained GooF = 1.068 for all data
REM R1 = 0.0145 for 2508 Fo > 4sig(Fo) and 0.0175 for all 2729 data
REM 191 parameters refined using 0 restraints
END
WGHT 0.0073 1.6265
REM Highest difference peak 0.404, deepest hole -0.587, 1-sigma level 0.089
Q1 1 0.1828 0.8482 0.2689 11.00000 0.05 0.40
Q2 1 0.3640 0.4788 0.2319 11.00000 0.05 0.39
Q3 1 0.6216 0.6172 0.1389 11.00000 0.05 0.36
Q4 1 0.6155 0.6005 0.2427 11.00000 0.05 0.35
Q5 1 0.3780 0.6932 0.4319 11.00000 0.05 0.34
Q6 1 0.6859 0.5213 0.3584 11.00000 0.05 0.34
Q7 1 0.7252 0.6526 0.1150 11.00000 0.05 0.31
Q8 1 0.5785 0.6153 0.3300 11.00000 0.05 0.31
Q9 1 0.2655 0.7736 0.0603 11.00000 0.05 0.29
Q10 1 0.6463 0.3147 0.4518 11.00000 0.05 0.28
Q11 1 0.2563 0.5204 0.1859 11.00000 0.05 0.28
Q12 1 0.5599 0.4768 0.3017 11.00000 0.05 0.28
Q13 1 1.0019 0.6314 0.0800 11.00000 0.05 0.28
Q14 1 0.9070 0.8362 0.2394 11.00000 0.05 0.27
Q15 1 0.6824 0.6658 0.3099 11.00000 0.05 0.27
Q16 1 0.0920 0.8852 0.2034 11.00000 0.05 0.27
Q17 1 0.3080 0.9648 0.3831 11.00000 0.05 0.27
Q18 1 0.4728 0.2330 0.3454 11.00000 0.05 0.26
Q19 1 0.1810 0.8590 0.1648 11.00000 0.05 0.26
Q20 1 0.4305 0.5883 0.0797 11.00000 0.05 0.26
;
_shelx_res_checksum 29628
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, hexanes'
#######################################################################
#
# 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_K12
_database_code_depnum_ccdc_archive 'CCDC 1962330'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record
;
2019-10-29 deposited with the CCDC. 2019-12-12 downloaded from the CCDC.
;
_audit_creation_date 2018-06-04
_audit_creation_method
;
Olex2 1.2-beta
(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 'C15 H12 N O4 Re S'
_chemical_formula_sum 'C15 H12 N O4 Re S'
_chemical_formula_weight 488.52
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 8.5304(5)
_cell_length_b 8.1560(5)
_cell_length_c 22.7941(15)
_cell_angle_alpha 90
_cell_angle_beta 96.365(2)
_cell_angle_gamma 90
_cell_volume 1576.10(17)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 6720
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 25.959
_cell_measurement_theta_min 2.654
_shelx_estimated_absorpt_T_max 0.637
_shelx_estimated_absorpt_T_min 0.548
_exptl_absorpt_coefficient_mu 7.858
_exptl_absorpt_correction_T_max 0.2602
_exptl_absorpt_correction_T_min 0.2290
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0484 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8801. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'Light Yellow'
_exptl_crystal_colour_modifier Light
_exptl_crystal_colour_primary Yellow
_exptl_crystal_density_diffrn 2.059
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 928
_exptl_crystal_size_max 0.087
_exptl_crystal_size_mid 0.065
_exptl_crystal_size_min 0.063
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0421
_diffrn_reflns_av_unetI/netI 0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 21549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 26.379
_diffrn_reflns_theta_min 2.470
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker X8 APEX II'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_source_type fine-focus
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2783
_reflns_number_total 3228
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction 'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.465
_refine_diff_density_min -0.821
_refine_diff_density_rms 0.116
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 200
_refine_ls_number_reflns 3228
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0285
_refine_ls_R_factor_gt 0.0207
_refine_ls_restrained_S_all 1.051
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0136P)^2^+0.4010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0355
_refine_ls_wR_factor_ref 0.0372
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
C15(H15)
2.b Idealised Me refined as rotating group:
C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
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
Re1 Re 0.78499(2) 0.63031(2) 0.41457(2) 0.01371(5) Uani 1 1 d . . . . .
S1 S 0.79836(10) 0.72065(10) 0.31116(4) 0.01666(19) Uani 1 1 d . . . . .
O1 O 0.9972(3) 0.3283(3) 0.40652(11) 0.0255(6) Uani 1 1 d . . . . .
O2 O 1.0721(3) 0.8178(3) 0.47329(11) 0.0274(6) Uani 1 1 d . . . . .
O3 O 0.7084(3) 0.5038(3) 0.53522(10) 0.0241(6) Uani 1 1 d . . . . .
O4 O 0.5750(3) 0.5232(3) 0.37451(10) 0.0171(5) Uani 1 1 d . . . . .
N1 N 0.6339(3) 0.8521(3) 0.41544(12) 0.0152(6) Uani 1 1 d . . . . .
C1 C 0.9157(4) 0.4421(4) 0.40919(14) 0.0178(8) Uani 1 1 d . . . . .
C2 C 0.9649(4) 0.7468(4) 0.45125(15) 0.0179(8) Uani 1 1 d . . . . .
C3 C 0.7389(4) 0.5543(4) 0.49102(16) 0.0170(8) Uani 1 1 d . . . . .
C4 C 0.5293(4) 0.5405(4) 0.31758(15) 0.0160(7) Uani 1 1 d . . . . .
C5 C 0.6207(4) 0.6269(4) 0.27963(14) 0.0163(7) Uani 1 1 d . . . . .
C6 C 0.5707(4) 0.6443(4) 0.21958(15) 0.0198(8) Uani 1 1 d . . . . .
H6 H 0.633471 0.703434 0.194899 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4291(4) 0.5751(4) 0.19606(16) 0.0242(9) Uani 1 1 d . . . . .
H7 H 0.394839 0.585175 0.155122 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3375(4) 0.4907(4) 0.23295(16) 0.0243(8) Uani 1 1 d . . . . .
H8 H 0.239824 0.444453 0.216926 0.029 Uiso 1 1 calc R . . . .
C9 C 0.3860(4) 0.4732(4) 0.29226(16) 0.0208(8) Uani 1 1 d . . . . .
H9 H 0.321491 0.414605 0.316450 0.025 Uiso 1 1 calc R . . . .
C10 C 0.9495(4) 0.6089(4) 0.27806(16) 0.0248(8) Uani 1 1 d . . . . .
H10A H 1.053606 0.641124 0.297052 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.942180 0.634103 0.235813 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.934412 0.490926 0.283410 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.6925(4) 1.0032(4) 0.40769(14) 0.0188(8) Uani 1 1 d . . . . .
H11 H 0.800860 1.014097 0.402233 0.023 Uiso 1 1 calc R . . . .
C12 C 0.6005(4) 1.1426(4) 0.40740(15) 0.0218(8) Uani 1 1 d . . . . .
H12 H 0.645188 1.247106 0.401329 0.026 Uiso 1 1 calc R . . . .
C13 C 0.4445(4) 1.1294(4) 0.41592(15) 0.0226(8) Uani 1 1 d . . . . .
H13 H 0.379201 1.223902 0.415551 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3844(4) 0.9752(4) 0.42507(15) 0.0232(8) Uani 1 1 d . . . . .
H14 H 0.277337 0.962618 0.432100 0.028 Uiso 1 1 calc R . . . .
C15 C 0.4808(4) 0.8395(4) 0.42393(15) 0.0197(8) Uani 1 1 d . . . . .
H15 H 0.437688 0.733915 0.429310 0.024 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
Re1 0.01621(8) 0.01035(7) 0.01418(8) 0.00129(6) -0.00009(5) -0.00126(6)
S1 0.0200(5) 0.0127(4) 0.0172(5) 0.0022(3) 0.0016(4) -0.0022(3)
O1 0.0313(15) 0.0203(13) 0.0238(15) -0.0019(11) -0.0026(12) 0.0092(11)
O2 0.0237(14) 0.0285(14) 0.0284(15) -0.0017(12) -0.0037(12) -0.0101(11)
O3 0.0319(15) 0.0213(13) 0.0200(14) 0.0057(12) 0.0074(12) 0.0001(11)
O4 0.0205(13) 0.0124(11) 0.0175(13) 0.0021(10) -0.0018(10) -0.0050(10)
N1 0.0187(15) 0.0107(14) 0.0160(15) 0.0026(12) 0.0012(12) -0.0019(11)
C1 0.023(2) 0.0183(18) 0.0113(18) 0.0023(14) -0.0032(15) -0.0068(16)
C2 0.021(2) 0.0164(17) 0.0167(19) 0.0055(15) 0.0034(16) 0.0031(15)
C3 0.0184(19) 0.0083(16) 0.024(2) 0.0007(15) -0.0011(16) 0.0004(14)
C4 0.0184(18) 0.0113(16) 0.0182(19) -0.0007(14) 0.0010(15) 0.0031(14)
C5 0.0173(17) 0.0135(16) 0.0173(18) 0.0005(15) -0.0013(14) 0.0007(15)
C6 0.0251(19) 0.0158(17) 0.0186(19) 0.0028(15) 0.0023(16) 0.0048(16)
C7 0.027(2) 0.0244(19) 0.019(2) -0.0016(16) -0.0079(17) 0.0041(16)
C8 0.023(2) 0.0199(18) 0.029(2) -0.0010(17) -0.0053(17) 0.0011(16)
C9 0.0191(19) 0.0154(17) 0.028(2) 0.0023(16) 0.0020(16) 0.0001(15)
C10 0.023(2) 0.027(2) 0.026(2) 0.0019(18) 0.0096(16) 0.0018(17)
C11 0.0191(19) 0.0159(17) 0.021(2) 0.0021(15) 0.0018(16) -0.0051(15)
C12 0.027(2) 0.0122(17) 0.026(2) 0.0000(16) 0.0004(17) -0.0037(15)
C13 0.032(2) 0.0174(17) 0.0181(19) 0.0037(16) 0.0021(16) 0.0102(17)
C14 0.020(2) 0.027(2) 0.023(2) 0.0067(17) 0.0050(16) 0.0026(16)
C15 0.0182(19) 0.0200(19) 0.021(2) 0.0046(15) 0.0007(16) -0.0029(14)
_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
Re1 S1 2.4842(9) . ?
Re1 O4 2.108(2) . ?
Re1 N1 2.223(3) . ?
Re1 C1 1.909(4) . ?
Re1 C2 1.917(4) . ?
Re1 C3 1.931(4) . ?
S1 C5 1.777(3) . ?
S1 C10 1.810(3) . ?
O1 C1 1.166(4) . ?
O2 C2 1.149(4) . ?
O3 C3 1.145(4) . ?
O4 C4 1.320(4) . ?
N1 C11 1.349(4) . ?
N1 C15 1.345(4) . ?
C4 C5 1.415(4) . ?
C4 C9 1.405(5) . ?
C5 C6 1.395(5) . ?
C6 C7 1.386(5) . ?
C7 C8 1.391(5) . ?
C8 C9 1.377(5) . ?
C11 C12 1.381(4) . ?
C12 C13 1.371(5) . ?
C13 C14 1.383(5) . ?
C14 C15 1.381(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
O4 Re1 S1 80.68(6) . . ?
O4 Re1 N1 82.85(9) . . ?
N1 Re1 S1 81.65(7) . . ?
C1 Re1 S1 95.11(10) . . ?
C1 Re1 O4 96.50(11) . . ?
C1 Re1 N1 176.75(12) . . ?
C1 Re1 C2 88.93(14) . . ?
C1 Re1 C3 88.76(13) . . ?
C2 Re1 S1 98.52(10) . . ?
C2 Re1 O4 174.56(11) . . ?
C2 Re1 N1 91.70(12) . . ?
C2 Re1 C3 89.93(14) . . ?
C3 Re1 S1 170.76(10) . . ?
C3 Re1 O4 90.55(11) . . ?
C3 Re1 N1 94.43(11) . . ?
C5 S1 Re1 97.43(11) . . ?
C5 S1 C10 103.28(16) . . ?
C10 S1 Re1 110.84(12) . . ?
C4 O4 Re1 121.7(2) . . ?
C11 N1 Re1 121.2(2) . . ?
C15 N1 Re1 120.8(2) . . ?
C15 N1 C11 117.9(3) . . ?
O1 C1 Re1 179.0(3) . . ?
O2 C2 Re1 179.4(3) . . ?
O3 C3 Re1 177.2(3) . . ?
O4 C4 C5 122.1(3) . . ?
O4 C4 C9 120.7(3) . . ?
C9 C4 C5 117.2(3) . . ?
C4 C5 S1 118.0(2) . . ?
C6 C5 S1 120.5(3) . . ?
C6 C5 C4 121.4(3) . . ?
C7 C6 C5 119.8(3) . . ?
C6 C7 C8 119.4(3) . . ?
C9 C8 C7 121.1(3) . . ?
C8 C9 C4 121.1(3) . . ?
N1 C11 C12 122.3(3) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C14 118.3(3) . . ?
C15 C14 C13 119.6(3) . . ?
N1 C15 C14 122.1(3) . . ?
_shelx_res_file
;
TITL cm36_a.res in P2(1)/n
cm36.res
created by SHELXL-2018/3 at 14:44:43 on 04-Jun-2018
REM Old TITL CM36 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.051, Rweak 0.002, Alpha 0.040
REM 0.473 for 242 systematic absences, Orientation as input
REM Formula found by SHELXT: C15 N O4 S Re
CELL 0.71073 8.5304 8.156 22.7941 90 96.365 90
ZERR 4 0.0005 0.0005 0.0015 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O Re S
UNIT 60 48 4 16 4 4
L.S. 10
PLAN 20
SIZE 0.087 0.065 0.063
TEMP -173.15
BOND
list 4
fmap 2
ACTA 50
REM
REM
REM
WGHT 0.013600 0.401000
FVAR 0.26754
RE1 5 0.784992 0.630308 0.414567 11.00000 0.01621 0.01035 =
0.01418 0.00129 -0.00009 -0.00126
S1 6 0.798359 0.720647 0.311159 11.00000 0.02001 0.01266 =
0.01720 0.00218 0.00160 -0.00218
O1 4 0.997247 0.328294 0.406518 11.00000 0.03127 0.02026 =
0.02380 -0.00193 -0.00259 0.00925
O2 4 1.072120 0.817772 0.473286 11.00000 0.02371 0.02849 =
0.02844 -0.00172 -0.00366 -0.01014
O3 4 0.708444 0.503772 0.535221 11.00000 0.03192 0.02131 =
0.02002 0.00567 0.00743 0.00012
O4 4 0.575009 0.523175 0.374510 11.00000 0.02054 0.01238 =
0.01754 0.00207 -0.00180 -0.00503
N1 3 0.633931 0.852134 0.415439 11.00000 0.01875 0.01066 =
0.01600 0.00259 0.00121 -0.00189
C1 1 0.915688 0.442147 0.409193 11.00000 0.02275 0.01835 =
0.01127 0.00234 -0.00320 -0.00677
C2 1 0.964949 0.746799 0.451249 11.00000 0.02093 0.01635 =
0.01672 0.00549 0.00341 0.00307
C3 1 0.738924 0.554259 0.491023 11.00000 0.01837 0.00831 =
0.02365 0.00073 -0.00112 0.00045
C4 1 0.529337 0.540480 0.317580 11.00000 0.01837 0.01125 =
0.01815 -0.00066 0.00096 0.00314
C5 1 0.620659 0.626902 0.279625 11.00000 0.01732 0.01354 =
0.01731 0.00054 -0.00125 0.00070
C6 1 0.570693 0.644338 0.219584 11.00000 0.02513 0.01579 =
0.01856 0.00275 0.00231 0.00479
AFIX 43
H6 2 0.633471 0.703434 0.194899 11.00000 -1.20000
AFIX 0
C7 1 0.429063 0.575101 0.196064 11.00000 0.02719 0.02438 =
0.01881 -0.00165 -0.00794 0.00409
AFIX 43
H7 2 0.394839 0.585175 0.155122 11.00000 -1.20000
AFIX 0
C8 1 0.337493 0.490736 0.232945 11.00000 0.02267 0.01993 =
0.02853 -0.00105 -0.00528 0.00105
AFIX 43
H8 2 0.239824 0.444453 0.216926 11.00000 -1.20000
AFIX 0
C9 1 0.386006 0.473183 0.292258 11.00000 0.01915 0.01544 =
0.02762 0.00227 0.00200 0.00006
AFIX 43
H9 2 0.321491 0.414605 0.316450 11.00000 -1.20000
AFIX 0
C10 1 0.949465 0.608885 0.278064 11.00000 0.02325 0.02705 =
0.02573 0.00188 0.00957 0.00179
AFIX 137
H10A 2 1.053606 0.641124 0.297052 11.00000 -1.50000
H10B 2 0.942180 0.634103 0.235813 11.00000 -1.50000
H10C 2 0.934412 0.490926 0.283410 11.00000 -1.50000
AFIX 0
C11 1 0.692548 1.003193 0.407686 11.00000 0.01906 0.01590 =
0.02127 0.00207 0.00184 -0.00512
AFIX 43
H11 2 0.800860 1.014097 0.402233 11.00000 -1.20000
AFIX 0
C12 1 0.600528 1.142599 0.407401 11.00000 0.02708 0.01224 =
0.02560 0.00005 0.00041 -0.00365
AFIX 43
H12 2 0.645188 1.247106 0.401329 11.00000 -1.20000
AFIX 0
C13 1 0.444457 1.129437 0.415921 11.00000 0.03224 0.01737 =
0.01809 0.00372 0.00211 0.01016
AFIX 43
H13 2 0.379201 1.223902 0.415551 11.00000 -1.20000
AFIX 0
C14 1 0.384385 0.975178 0.425069 11.00000 0.01983 0.02694 =
0.02347 0.00673 0.00499 0.00259
AFIX 43
H14 2 0.277337 0.962618 0.432100 11.00000 -1.20000
AFIX 0
C15 1 0.480827 0.839531 0.423928 11.00000 0.01821 0.02002 =
0.02058 0.00459 0.00068 -0.00292
AFIX 43
H15 2 0.437688 0.733915 0.429310 11.00000 -1.20000
AFIX 0
HKLF 4
REM cm36_a.res in P2(1)/n
REM wR2 = 0.0372, GooF = S = 1.051, Restrained GooF = 1.051 for all data
REM R1 = 0.0207 for 2783 Fo > 4sig(Fo) and 0.0285 for all 3228 data
REM 200 parameters refined using 0 restraints
END
WGHT 0.0136 0.4011
REM Highest difference peak 0.465, deepest hole -0.821, 1-sigma level 0.116
Q1 1 0.8748 0.7038 0.3978 11.00000 0.05 0.47
Q2 1 0.2918 0.9390 0.4681 11.00000 0.05 0.46
Q3 1 0.3214 0.8689 0.4273 11.00000 0.05 0.44
Q4 1 0.3826 0.7054 0.2096 11.00000 0.05 0.43
Q5 1 0.6239 1.1863 0.4026 11.00000 0.05 0.43
Q6 1 0.5384 1.1418 0.4343 11.00000 0.05 0.42
Q7 1 0.3858 0.5011 0.3450 11.00000 0.05 0.40
Q8 1 0.8220 0.4441 0.6119 11.00000 0.05 0.39
Q9 1 0.8581 0.5675 0.3863 11.00000 0.05 0.39
Q10 1 0.0451 0.4086 0.1897 11.00000 0.05 0.38
Q11 1 0.4645 0.4824 0.3028 11.00000 0.05 0.38
Q12 1 0.6650 0.4133 0.3115 11.00000 0.05 0.37
Q13 1 0.2460 0.6296 0.2120 11.00000 0.05 0.36
Q14 1 0.6956 0.6451 0.2926 11.00000 0.05 0.36
Q15 1 0.6665 1.0937 0.4258 11.00000 0.05 0.36
Q16 1 0.3317 1.2749 0.3598 11.00000 0.05 0.36
Q17 1 0.8199 0.8836 0.2631 11.00000 0.05 0.36
Q18 1 0.3647 1.0361 0.4582 11.00000 0.05 0.36
Q19 1 0.4037 0.4624 0.2579 11.00000 0.05 0.36
Q20 1 0.4395 0.9218 0.4373 11.00000 0.05 0.35
;
_shelx_res_checksum 9699
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_K11
_database_code_depnum_ccdc_archive 'CCDC 1962329'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record
;
2019-10-29 deposited with the CCDC. 2019-12-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT307_K11
;
PROBLEM: Isolated Metal Atom found in Structure (Unusual) Re1B Check
RESPONSE: Heavy Atom Position from alternate site/disorder around 1.5%.
;
# Added during the CSD deposition process: Tuesday 29 October 2019 05:37 PM
# end Validation Reply Form
_audit_creation_date 2018-06-04
_audit_creation_method
;
Olex2 1.2-beta
(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 'C20 H14 N O5 Re, 0.5(C H2 Cl2)'
_chemical_formula_sum 'C20.50 H15 Cl N O5 Re'
_chemical_formula_weight 576.98
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 '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 20.753(2)
_cell_length_b 7.0352(8)
_cell_length_c 13.7941(18)
_cell_angle_alpha 90
_cell_angle_beta 105.388(7)
_cell_angle_gamma 90
_cell_volume 1941.8(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 4183
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 21.846
_cell_measurement_theta_min 3.054
_shelx_estimated_absorpt_T_max 0.475
_shelx_estimated_absorpt_T_min 0.440
_exptl_absorpt_coefficient_mu 6.428
_exptl_absorpt_correction_T_max 0.0439
_exptl_absorpt_correction_T_min 0.0166
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0802 after correction. The Ratio of minimum to maximum transmission is 0.3781. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'Light Yellow'
_exptl_crystal_colour_modifier Light
_exptl_crystal_colour_primary Yellow
_exptl_crystal_density_diffrn 1.974
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 1108
_exptl_crystal_size_max 0.153
_exptl_crystal_size_mid 0.147
_exptl_crystal_size_min 0.136
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0959
_diffrn_reflns_av_unetI/netI 0.0639
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 26253
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 25.381
_diffrn_reflns_theta_min 2.036
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker X8 APEX II'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_source_type fine-focus
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2886
_reflns_number_total 3563
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.923
_refine_diff_density_min -1.342
_refine_diff_density_rms 0.165
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 267
_refine_ls_number_reflns 3563
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0535
_refine_ls_R_factor_gt 0.0376
_refine_ls_restrained_S_all 1.056
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+4.8116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0759
_refine_ls_wR_factor_ref 0.0815
_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. Restrained distances
Cl1S-C1S
1.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Re1B) = Uanis(Re1)
4. Others
Sof(Re1B)=1-FVAR(1)
Sof(Re1)=FVAR(1)
Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5)
5.a Secondary CH2 refined with riding coordinates:
C1S(H1SA,H1SB)
5.b Aromatic/amide H refined with riding coordinates:
C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
C17(H17), C18(H18), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
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
Re1 Re 0.83548(2) 0.78123(4) 0.55271(2) 0.02089(10) Uani 0.9851(7) 1 d . . P A
1
O1 O 0.7707(3) 1.0345(7) 0.6830(4) 0.0356(13) Uani 1 1 d . . . A 1
O2 O 0.8984(3) 0.5341(7) 0.7362(4) 0.0303(12) Uani 1 1 d . . . A 1
O3 O 0.9572(3) 1.0456(7) 0.6157(4) 0.0306(12) Uani 1 1 d . . . A 1
O4 O 0.7536(2) 0.5988(6) 0.4999(4) 0.0258(11) Uani 1 1 d . . . A 1
O5 O 0.7936(2) 0.9243(6) 0.4139(4) 0.0255(11) Uani 1 1 d . . . A 1
N1 N 0.8814(3) 0.5966(8) 0.4598(4) 0.0214(13) Uani 1 1 d . . . A 1
C1 C 0.7936(4) 0.9385(11) 0.6320(6) 0.0302(18) Uani 1 1 d . . . A 1
C2 C 0.8737(4) 0.6325(10) 0.6673(6) 0.0273(17) Uani 1 1 d . . . A 1
C3 C 0.9114(4) 0.9452(10) 0.5926(5) 0.0247(17) Uani 1 1 d . . . A 1
C4 C 0.7318(4) 1.0269(10) 0.2552(6) 0.0316(18) Uani 1 1 d . . . A 1
H4A H 0.687413 1.083651 0.244913 0.047 Uiso 1 1 calc GR . . A 1
H4B H 0.734453 0.960756 0.193872 0.047 Uiso 1 1 calc GR . . A 1
H4C H 0.765845 1.127057 0.271152 0.047 Uiso 1 1 calc GR . . A 1
C5 C 0.7439(4) 0.8870(10) 0.3412(6) 0.0291(18) Uani 1 1 d . . . A 1
C6 C 0.7007(4) 0.7256(10) 0.3358(5) 0.0262(16) Uani 1 1 d . . . A 1
C7 C 0.7090(4) 0.5895(10) 0.4132(5) 0.0260(17) Uani 1 1 d . . . A 1
C8 C 0.6663(4) 0.4234(10) 0.3989(6) 0.0264(17) Uani 1 1 d . . . A 1
C9 C 0.6143(4) 0.4013(11) 0.3084(6) 0.0323(19) Uani 1 1 d . . . A 1
C10 C 0.6058(4) 0.5441(11) 0.2327(6) 0.035(2) Uani 1 1 d . . . A 1
H10 H 0.570525 0.532752 0.172884 0.043 Uiso 1 1 calc R . . A 1
C11 C 0.6472(4) 0.6952(11) 0.2452(6) 0.0359(19) Uani 1 1 d . . . A 1
H11 H 0.641023 0.785608 0.192382 0.043 Uiso 1 1 calc R . . A 1
C12 C 0.6756(4) 0.2789(10) 0.4719(6) 0.0300(18) Uani 1 1 d . . . A 1
H12 H 0.709786 0.291982 0.532839 0.036 Uiso 1 1 calc R . . A 1
C13 C 0.6357(4) 0.1174(12) 0.4563(7) 0.040(2) Uani 1 1 d . . . A 1
H13 H 0.643311 0.020226 0.505814 0.048 Uiso 1 1 calc R . . A 1
C14 C 0.5845(4) 0.0976(12) 0.3684(7) 0.041(2) Uani 1 1 d . . . A 1
H14 H 0.556852 -0.012014 0.358814 0.049 Uiso 1 1 calc R . . A 1
C15 C 0.5736(4) 0.2378(12) 0.2943(7) 0.043(2) Uani 1 1 d . . . A 1
H15 H 0.538730 0.223113 0.234239 0.052 Uiso 1 1 calc R . . A 1
C16 C 0.8678(4) 0.4084(10) 0.4503(5) 0.0240(16) Uani 1 1 d . . . A 1
H16 H 0.836012 0.356508 0.481447 0.029 Uiso 1 1 calc R . . A 1
C17 C 0.8988(3) 0.2886(10) 0.3964(5) 0.0269(16) Uani 1 1 d . . . A 1
H17 H 0.888528 0.156735 0.391307 0.032 Uiso 1 1 calc R . . A 1
C18 C 0.9448(4) 0.3631(10) 0.3502(5) 0.0257(17) Uani 1 1 d . . . A 1
H18 H 0.966371 0.283617 0.312727 0.031 Uiso 1 1 calc R . . A 1
C19 C 0.9589(3) 0.5550(10) 0.3597(5) 0.0270(17) Uani 1 1 d . . . A 1
H19 H 0.990299 0.609941 0.328823 0.032 Uiso 1 1 calc R . . A 1
C20 C 0.9268(3) 0.6649(10) 0.4142(5) 0.0232(16) Uani 1 1 d . . . A 1
H20 H 0.937036 0.796716 0.420331 0.028 Uiso 1 1 calc R . . A 1
Cl1S Cl 0.53727(15) -0.3261(4) 0.4899(2) 0.0752(8) Uani 1 1 d D . . . .
C1S C 0.5253(14) -0.515(3) 0.5538(17) 0.094(9) Uani 0.5 1 d D . P . .
H1SA H 0.520125 -0.468600 0.618947 0.112 Uiso 0.5 1 calc R . P . .
H1SB H 0.567512 -0.588825 0.568995 0.112 Uiso 0.5 1 calc R . P . .
Re1B Re 0.8301(9) 0.232(3) 0.5602(14) 0.02089(10) Uani 0.0149(7) 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Re1 0.02454(17) 0.02074(16) 0.01740(16) 0.00025(13) 0.00557(11) -0.00117(13)
O1 0.042(3) 0.039(3) 0.030(3) -0.008(3) 0.016(3) 0.003(3)
O2 0.037(3) 0.031(3) 0.022(3) 0.006(2) 0.006(3) -0.002(2)
O3 0.032(3) 0.036(3) 0.022(3) -0.003(2) 0.003(2) -0.014(3)
O4 0.029(3) 0.024(3) 0.024(3) 0.001(2) 0.006(2) -0.004(2)
O5 0.030(3) 0.026(3) 0.020(3) 0.004(2) 0.005(2) -0.002(2)
N1 0.032(3) 0.018(3) 0.014(3) -0.003(2) 0.005(3) -0.002(3)
C1 0.032(4) 0.032(4) 0.021(4) 0.008(3) -0.002(4) -0.006(4)
C2 0.040(5) 0.016(4) 0.029(5) -0.008(3) 0.015(4) -0.006(3)
C3 0.032(5) 0.029(4) 0.014(4) 0.007(3) 0.006(3) 0.012(4)
C4 0.032(5) 0.029(4) 0.030(5) 0.011(3) 0.002(4) 0.003(3)
C5 0.031(5) 0.031(5) 0.027(5) -0.002(3) 0.012(4) -0.002(3)
C6 0.027(4) 0.026(4) 0.027(4) -0.001(3) 0.008(3) 0.001(3)
C7 0.024(4) 0.031(4) 0.021(4) -0.003(3) 0.004(3) 0.002(3)
C8 0.029(4) 0.020(4) 0.030(5) -0.005(3) 0.009(4) -0.001(3)
C9 0.022(4) 0.037(5) 0.034(5) -0.002(4) 0.001(4) 0.000(3)
C10 0.024(4) 0.042(5) 0.034(5) -0.005(4) -0.005(4) -0.002(4)
C11 0.035(5) 0.035(5) 0.035(5) 0.003(4) 0.005(4) 0.005(4)
C12 0.029(4) 0.031(4) 0.030(5) -0.005(3) 0.008(3) 0.001(3)
C13 0.029(5) 0.039(5) 0.050(6) 0.002(4) 0.010(4) -0.007(4)
C14 0.034(5) 0.035(5) 0.051(6) 0.001(4) 0.007(4) -0.010(4)
C15 0.036(5) 0.043(5) 0.046(6) -0.013(4) 0.001(4) -0.007(4)
C16 0.028(4) 0.022(4) 0.019(4) -0.004(3) 0.001(3) -0.005(3)
C17 0.028(4) 0.020(4) 0.029(4) -0.004(3) 0.000(3) 0.002(3)
C18 0.034(4) 0.027(4) 0.018(4) 0.006(3) 0.011(3) 0.007(3)
C19 0.018(4) 0.039(5) 0.023(4) 0.005(3) 0.004(3) 0.000(3)
C20 0.030(4) 0.020(4) 0.020(4) -0.001(3) 0.007(3) -0.001(3)
Cl1S 0.0743(19) 0.095(2) 0.0556(18) -0.0162(15) 0.0156(15) -0.0287(16)
C1S 0.12(2) 0.061(15) 0.09(2) 0.025(14) 0.008(16) -0.040(15)
Re1B 0.02454(17) 0.02074(16) 0.01740(16) 0.00025(13) 0.00557(11) -0.00117(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 2.100(5) . ?
Re1 O5 2.134(5) . ?
Re1 N1 2.211(5) . ?
Re1 C1 1.919(8) . ?
Re1 C2 1.886(8) . ?
Re1 C3 1.912(8) . ?
O1 C1 1.163(9) . ?
O2 C2 1.177(9) . ?
O3 C3 1.158(8) . ?
O4 C7 1.305(8) . ?
O5 C5 1.260(8) . ?
N1 C16 1.353(8) . ?
N1 C20 1.353(8) . ?
C4 C5 1.510(10) . ?
C5 C6 1.436(10) . ?
C6 C7 1.411(10) . ?
C6 C11 1.450(10) . ?
C7 C8 1.447(10) . ?
C8 C9 1.425(10) . ?
C8 C12 1.408(10) . ?
C9 C10 1.426(11) . ?
C9 C15 1.409(11) . ?
C10 C11 1.349(10) . ?
C12 C13 1.389(10) . ?
C13 C14 1.389(11) . ?
C14 C15 1.396(12) . ?
C16 C17 1.390(9) . ?
C17 C18 1.384(9) . ?
C18 C19 1.380(10) . ?
C19 C20 1.368(9) . ?
Cl1S C1S 1.653(14) . ?
Cl1S C1S 1.70(2) 3_646 ?
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
O4 Re1 O5 82.96(18) . . ?
O4 Re1 N1 82.73(19) . . ?
O5 Re1 N1 83.83(19) . . ?
C1 Re1 O4 95.9(3) . . ?
C1 Re1 O5 95.8(2) . . ?
C1 Re1 N1 178.6(3) . . ?
C2 Re1 O4 94.2(3) . . ?
C2 Re1 O5 174.0(2) . . ?
C2 Re1 N1 90.5(3) . . ?
C2 Re1 C1 89.8(3) . . ?
C2 Re1 C3 87.8(3) . . ?
C3 Re1 O4 176.3(2) . . ?
C3 Re1 O5 94.7(2) . . ?
C3 Re1 N1 94.2(3) . . ?
C3 Re1 C1 87.2(3) . . ?
C7 O4 Re1 131.3(4) . . ?
C5 O5 Re1 132.0(5) . . ?
C16 N1 Re1 121.3(4) . . ?
C16 N1 C20 117.1(6) . . ?
C20 N1 Re1 121.4(4) . . ?
O1 C1 Re1 177.2(7) . . ?
O2 C2 Re1 177.2(6) . . ?
O3 C3 Re1 179.2(7) . . ?
O5 C5 C4 114.8(6) . . ?
O5 C5 C6 125.0(7) . . ?
C6 C5 C4 120.2(7) . . ?
C5 C6 C11 119.1(7) . . ?
C7 C6 C5 123.2(7) . . ?
C7 C6 C11 117.6(7) . . ?
O4 C7 C6 125.0(7) . . ?
O4 C7 C8 115.2(6) . . ?
C6 C7 C8 119.8(7) . . ?
C9 C8 C7 120.1(7) . . ?
C12 C8 C7 121.5(7) . . ?
C12 C8 C9 118.4(7) . . ?
C8 C9 C10 118.8(7) . . ?
C15 C9 C8 119.8(7) . . ?
C15 C9 C10 121.3(7) . . ?
C11 C10 C9 120.7(8) . . ?
C10 C11 C6 122.9(7) . . ?
C13 C12 C8 121.1(7) . . ?
C12 C13 C14 120.2(8) . . ?
C13 C14 C15 120.4(8) . . ?
C14 C15 C9 120.0(8) . . ?
N1 C16 C17 122.0(7) . . ?
C18 C17 C16 119.4(7) . . ?
C19 C18 C17 118.8(7) . . ?
C20 C19 C18 118.9(7) . . ?
N1 C20 C19 123.7(6) . . ?
C1S Cl1S C1S 56.6(13) . 3_646 ?
Cl1S C1S Cl1S 123.4(13) . 3_646 ?
_shelx_res_file
;
TITL cm34_a.res in P2(1)/c
cm34.res
created by SHELXL-2018/3 at 14:28:34 on 04-Jun-2018
REM Old TITL CM34 in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.083, Rweak 0.006, Alpha 0.046
REM 0.300 for 315 systematic absences, Orientation as input
REM Formula found by SHELXT: C20 N O6 Re1B
CELL 0.71073 20.7534 7.0352 13.7941 90 105.388 90
ZERR 4 0.0024 0.0008 0.0018 0 0.007 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O Re
UNIT 82 60 4 4 20 4
EQIV $1 1-X,-1-Y,1-Z
DFIX 1.8 Cl1S C1S
EADP Re1B Re1
L.S. 10
PLAN 20
SIZE 0.153 0.147 0.136
TEMP -173.15
FREE C1S C1S_$1
BOND
list 4
fmap 2
ACTA 50
OMIT 1 0 0
REM
REM
REM
WGHT 0.023800 4.811600
FVAR 0.23397 0.98514
PART 1
RE1 6 0.835476 0.781230 0.552715 21.00000 0.02454 0.02074 =
0.01740 0.00025 0.00557 -0.00117
O1 5 0.770658 1.034495 0.683005 11.00000 0.04152 0.03864 =
0.03009 -0.00802 0.01576 0.00323
O2 5 0.898372 0.534144 0.736196 11.00000 0.03690 0.03108 =
0.02186 0.00592 0.00576 -0.00167
O3 5 0.957160 1.045608 0.615673 11.00000 0.03187 0.03581 =
0.02176 -0.00311 0.00293 -0.01403
O4 5 0.753576 0.598756 0.499928 11.00000 0.02878 0.02428 =
0.02398 0.00062 0.00619 -0.00398
O5 5 0.793560 0.924252 0.413871 11.00000 0.03012 0.02551 =
0.01991 0.00427 0.00513 -0.00153
N1 4 0.881399 0.596572 0.459790 11.00000 0.03163 0.01829 =
0.01363 -0.00290 0.00495 -0.00167
C1 1 0.793572 0.938540 0.632047 11.00000 0.03180 0.03218 =
0.02142 0.00811 -0.00194 -0.00609
C2 1 0.873721 0.632497 0.667283 11.00000 0.04042 0.01633 =
0.02862 -0.00762 0.01547 -0.00592
C3 1 0.911389 0.945216 0.592645 11.00000 0.03185 0.02863 =
0.01376 0.00662 0.00645 0.01173
C4 1 0.731847 1.026890 0.255244 11.00000 0.03198 0.02947 =
0.02986 0.01062 0.00202 0.00282
AFIX 137
H4A 2 0.687413 1.083651 0.244913 11.00000 -1.50000
H4B 2 0.734453 0.960756 0.193872 11.00000 -1.50000
H4C 2 0.765845 1.127057 0.271152 11.00000 -1.50000
AFIX 0
C5 1 0.743914 0.886977 0.341226 11.00000 0.03095 0.03110 =
0.02742 -0.00213 0.01158 -0.00169
C6 1 0.700687 0.725640 0.335774 11.00000 0.02684 0.02587 =
0.02656 -0.00120 0.00823 0.00088
C7 1 0.708965 0.589510 0.413248 11.00000 0.02380 0.03146 =
0.02145 -0.00317 0.00365 0.00224
C8 1 0.666322 0.423422 0.398878 11.00000 0.02899 0.02039 =
0.03031 -0.00544 0.00870 -0.00060
C9 1 0.614332 0.401275 0.308430 11.00000 0.02230 0.03684 =
0.03422 -0.00238 0.00137 -0.00004
C10 1 0.605768 0.544114 0.232736 11.00000 0.02356 0.04209 =
0.03370 -0.00525 -0.00454 -0.00167
AFIX 43
H10 2 0.570525 0.532752 0.172884 11.00000 -1.20000
AFIX 0
C11 1 0.647178 0.695204 0.245213 11.00000 0.03511 0.03546 =
0.03460 0.00303 0.00502 0.00484
AFIX 43
H11 2 0.641023 0.785608 0.192382 11.00000 -1.20000
AFIX 0
C12 1 0.675605 0.278871 0.471864 11.00000 0.02908 0.03076 =
0.03028 -0.00517 0.00812 0.00053
AFIX 43
H12 2 0.709786 0.291982 0.532839 11.00000 -1.20000
AFIX 0
C13 1 0.635659 0.117442 0.456266 11.00000 0.02941 0.03912 =
0.04976 0.00209 0.00958 -0.00671
AFIX 43
H13 2 0.643311 0.020226 0.505814 11.00000 -1.20000
AFIX 0
C14 1 0.584541 0.097644 0.368440 11.00000 0.03361 0.03474 =
0.05117 0.00076 0.00718 -0.01047
AFIX 43
H14 2 0.556852 -0.012014 0.358814 11.00000 -1.20000
AFIX 0
C15 1 0.573615 0.237839 0.294274 11.00000 0.03562 0.04322 =
0.04566 -0.01251 0.00092 -0.00748
AFIX 43
H15 2 0.538730 0.223113 0.234239 11.00000 -1.20000
AFIX 0
C16 1 0.867775 0.408379 0.450306 11.00000 0.02770 0.02237 =
0.01902 -0.00400 0.00101 -0.00508
AFIX 43
H16 2 0.836012 0.356508 0.481447 11.00000 -1.20000
AFIX 0
C17 1 0.898811 0.288551 0.396404 11.00000 0.02836 0.01974 =
0.02860 -0.00407 0.00036 0.00219
AFIX 43
H17 2 0.888528 0.156735 0.391307 11.00000 -1.20000
AFIX 0
C18 1 0.944843 0.363099 0.350225 11.00000 0.03419 0.02703 =
0.01840 0.00624 0.01112 0.00674
AFIX 43
H18 2 0.966371 0.283617 0.312727 11.00000 -1.20000
AFIX 0
C19 1 0.958884 0.555048 0.359670 11.00000 0.01845 0.03874 =
0.02303 0.00454 0.00416 0.00034
AFIX 43
H19 2 0.990299 0.609941 0.328823 11.00000 -1.20000
AFIX 0
C20 1 0.926827 0.664903 0.414160 11.00000 0.03024 0.01970 =
0.01981 -0.00118 0.00683 -0.00149
AFIX 43
H20 2 0.937036 0.796716 0.420331 11.00000 -1.20000
AFIX 0
PART 0
CL1S 3 0.537273 -0.326052 0.489859 11.00000 0.07430 0.09487 =
0.05558 -0.01621 0.01562 -0.02874
C1S 1 0.525303 -0.515477 0.553762 10.50000 0.12016 0.06130 =
0.08851 0.02506 0.00831 -0.04004
AFIX 23
H1SA 2 0.520125 -0.468600 0.618947 10.50000 -1.20000
H1SB 2 0.567512 -0.588825 0.568995 10.50000 -1.20000
AFIX 0
PART 2
RE1B 6 0.830118 0.231754 0.560248 -21.00000 0.02454 0.02074 =
0.01740 0.00025 0.00557 -0.00117
HKLF 4
REM cm34_a.res in P2(1)/c
REM wR2 = 0.0815, GooF = S = 1.049, Restrained GooF = 1.056 for all data
REM R1 = 0.0376 for 2886 Fo > 4sig(Fo) and 0.0535 for all 3563 data
REM 267 parameters refined using 1 restraints
END
WGHT 0.0238 4.8010
REM Highest difference peak 0.923, deepest hole -1.342, 1-sigma level 0.165
Q1 1 0.8820 0.7841 0.5926 11.00000 0.05 0.92
Q2 1 0.8162 0.6249 0.5998 11.00000 0.05 0.88
Q3 1 0.8427 0.9354 0.5783 11.00000 0.05 0.85
Q4 1 0.7821 0.7509 0.5218 11.00000 0.05 0.77
Q5 1 0.5288 -0.4563 0.5400 11.00000 0.05 0.77
Q6 1 0.5169 0.2739 0.2229 11.00000 0.05 0.69
Q7 1 0.8437 0.2810 0.6040 11.00000 0.05 0.67
Q8 1 0.8789 0.6445 0.5203 11.00000 0.05 0.66
Q9 1 0.5896 0.5111 0.4192 11.00000 0.05 0.59
Q10 1 0.8354 0.6198 0.4877 11.00000 0.05 0.58
Q11 1 0.7682 0.8346 0.5766 11.00000 0.05 0.57
Q12 1 0.5355 -0.5568 0.4847 11.00000 0.05 0.57
Q13 1 0.8457 1.1968 0.2567 11.00000 0.05 0.56
Q14 1 1.0240 0.5187 0.2621 11.00000 0.05 0.56
Q15 1 0.6293 -0.4754 0.5259 11.00000 0.05 0.55
Q16 1 0.9420 0.7734 0.6232 11.00000 0.05 0.54
Q17 1 1.0375 0.5090 0.3992 11.00000 0.05 0.54
Q18 1 0.7893 1.0493 0.4210 11.00000 0.05 0.53
Q19 1 0.6757 0.1349 0.4789 11.00000 0.05 0.53
Q20 1 0.9114 0.1149 0.4592 11.00000 0.05 0.53
;
_shelx_res_checksum 67226
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_K9
_database_code_depnum_ccdc_archive 'CCDC 1962328'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;Ohio State University
United States of America
;
_audit_update_record
;
2019-10-29 deposited with the CCDC. 2019-12-12 downloaded from the CCDC.
;
_audit_creation_date 2018-06-04
_audit_creation_method
;
Olex2 1.2-beta
(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 'C13 H11 N2 O6 Re'
_chemical_formula_sum 'C13 H11 N2 O6 Re'
_chemical_formula_weight 477.44
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 '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 9.1080(5)
_cell_length_b 9.5099(5)
_cell_length_c 9.7673(5)
_cell_angle_alpha 70.669(2)
_cell_angle_beta 80.012(2)
_cell_angle_gamma 61.781(2)
_cell_volume 703.28(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5139
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 26.288
_cell_measurement_theta_min 2.538
_shelx_estimated_absorpt_T_max 0.523
_shelx_estimated_absorpt_T_min 0.406
_exptl_absorpt_coefficient_mu 8.671
_exptl_absorpt_correction_T_max 0.0932
_exptl_absorpt_correction_T_min 0.0602
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0785 before and 0.0368 after correction. The Ratio of minimum to maximum transmission is 0.6459. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'Light Yellow'
_exptl_crystal_colour_modifier Light
_exptl_crystal_colour_primary Yellow
_exptl_crystal_density_diffrn 2.255
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 452
_exptl_crystal_size_max 0.127
_exptl_crystal_size_mid 0.115
_exptl_crystal_size_min 0.086
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0300
_diffrn_reflns_av_unetI/netI 0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 10244
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 26.368
_diffrn_reflns_theta_min 2.210
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker X8 APEX II'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_source_type fine-focus
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2647
_reflns_number_total 2866
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction 'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.563
_refine_diff_density_min -0.513
_refine_diff_density_rms 0.120
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.047
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 245
_refine_ls_number_reflns 2866
_refine_ls_number_restraints 37
_refine_ls_R_factor_all 0.0233
_refine_ls_R_factor_gt 0.0200
_refine_ls_restrained_S_all 1.040
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0165P)^2^+0.0535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0378
_refine_ls_wR_factor_ref 0.0387
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Re1) = Uanis(Re1B)
Uanis(O4) = Uanis(O5B)
Uanis(O5) = Uanis(O4B)
Uanis(O6) = Uanis(O6B)
Uanis(C6B) = Uanis(C7)
Uanis(C7B) = Uanis(C6)
Uanis(C5) = Uanis(C8B)
Uanis(C8) = Uanis(C5B)
Uanis(C9) = Uanis(C9B)
Uanis(C4) = Uanis(C4B)
Uanis(C2B) = Uanis(C3)
Uanis(O3) = Uanis(O2B)
Uanis(C3B) = Uanis(C2)
Uanis(O3B) = Uanis(O2)
3. Same fragment restrains
{Re1, O2, O3, O4, O5, O6, C2, C3, C4, C5, C6, C7, C8, C9} sigma for 1-2: 0.005,
1-3: 0.005
as
{Re1B, O2B, O3B, O4B, O5B, O6B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B}
4. Others
Sof(Re1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(O5B)=Sof(O6B)=Sof(C2B)=Sof(C3B)=
Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(C8B)=Sof(C9B)=
Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=1-FVAR(1)
Sof(Re1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(C2)=Sof(C3)=Sof(C4)=
Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(C8)=Sof(C9)=Sof(H9A)=Sof(H9B)=
Sof(H9C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
C10(H10), C11(H11), C12(H12), C4(H4), C5(H5), C4B(H4B), C5B(H5B)
5.b Idealised Me refined as rotating group:
C13(H13A,H13B,H13C), C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1428(3) 0.8288(3) 0.4341(3) 0.0259(6) Uani 1 1 d . . . . .
N1 N 0.4687(4) 0.5127(4) 0.2469(3) 0.0225(7) Uani 1 1 d . . . . .
N2 N 0.7338(3) 0.3306(4) 0.2534(3) 0.0222(7) Uani 1 1 d . . . . .
C1 C -0.0109(4) 0.7587(4) 0.3902(4) 0.0196(8) Uani 1 1 d . . . . .
C10 C 0.5450(5) 0.5598(5) 0.1184(4) 0.0275(9) Uani 1 1 d . . . . .
H10 H 0.492038 0.655770 0.039837 0.033 Uiso 1 1 calc R . . . .
C11 C 0.7082(5) 0.4476(5) 0.1211(4) 0.0289(9) Uani 1 1 d . . . . .
H11 H 0.789021 0.449968 0.045607 0.035 Uiso 1 1 calc R . . . .
C12 C 0.5879(4) 0.3741(4) 0.3266(4) 0.0225(8) Uani 1 1 d . . . . .
H12 H 0.571514 0.314189 0.422423 0.027 Uiso 1 1 calc R . . . .
C13 C 0.8920(4) 0.1862(5) 0.3066(4) 0.0314(9) Uani 1 1 d . . . . .
H13A H 0.876629 0.126956 0.407074 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.976343 0.223821 0.302690 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.928815 0.111175 0.245734 0.047 Uiso 1 1 calc GR . . . .
Re1 Re 0.21082(7) 0.63902(6) 0.32135(7) 0.01602(8) Uani 0.928(3) 1 d D . P A 1
O2 O 0.0861(9) 0.4367(8) 0.2289(9) 0.0288(8) Uani 0.928(3) 1 d D . P A 1
O3 O 0.2750(11) 0.3894(5) 0.6254(5) 0.0229(10) Uani 0.928(3) 1 d D . P A 1
O4 O 0.1777(3) 0.8169(3) 0.1091(3) 0.0214(7) Uani 0.928(3) 1 d D . P A 1
O5 O 0.3012(3) 0.8009(3) 0.3458(3) 0.0184(6) Uani 0.928(3) 1 d D . P A 1
O6 O 0.3463(9) 1.1487(6) 0.0824(4) 0.0198(7) Uani 0.928(3) 1 d D . P A 1
C2 C 0.1354(7) 0.5095(5) 0.2678(4) 0.0211(9) Uani 0.928(3) 1 d D . P A 1
C3 C 0.2515(11) 0.4833(7) 0.5097(6) 0.0194(8) Uani 0.928(3) 1 d D . P A 1
C4 C 0.2723(5) 1.1618(5) -0.0328(4) 0.0226(9) Uani 0.928(3) 1 d D . P A 1
H4 H 0.262963 1.248741 -0.119544 0.027 Uiso 0.928(3) 1 calc R . P A 1
C5 C 0.2124(5) 1.0579(5) -0.0294(4) 0.0232(9) Uani 0.928(3) 1 d D . P A 1
H5 H 0.160502 1.071248 -0.112251 0.028 Uiso 0.928(3) 1 calc R . P A 1
C6 C 0.2264(4) 0.9256(5) 0.0999(4) 0.0188(9) Uani 0.928(3) 1 d D . P A 1
C7 C 0.2966(4) 0.9184(4) 0.2233(4) 0.0175(9) Uani 0.928(3) 1 d D . P A 1
C8 C 0.3575(4) 1.0285(4) 0.2108(4) 0.0175(8) Uani 0.928(3) 1 d D . P A 1
C9 C 0.4400(5) 1.0346(5) 0.3250(4) 0.0225(9) Uani 0.928(3) 1 d D . P A 1
H9A H 0.561194 0.975575 0.312817 0.034 Uiso 0.928(3) 1 calc GR . P A 1
H9B H 0.405889 0.981354 0.420642 0.034 Uiso 0.928(3) 1 calc GR . P A 1
H9C H 0.407590 1.150951 0.317266 0.034 Uiso 0.928(3) 1 calc GR . P A 1
Re1B Re 0.2125(10) 0.6482(9) 0.3460(8) 0.01602(8) Uani 0.072(3) 1 d D . P A 2
O2B O 0.286(16) 0.357(8) 0.624(6) 0.0229(10) Uani 0.072(3) 1 d D . P A 2
O3B O 0.092(13) 0.459(11) 0.229(13) 0.0288(8) Uani 0.072(3) 1 d D . P A 2
O4B O 0.316(4) 0.778(3) 0.4110(16) 0.0184(6) Uani 0.072(3) 1 d D . P A 2
O5B O 0.191(4) 0.851(3) 0.1550(17) 0.0214(7) Uani 0.072(3) 1 d D . P A 2
O6B O 0.336(11) 1.162(8) 0.084(4) 0.0198(7) Uani 0.072(3) 1 d D . P A 2
C2B C 0.263(14) 0.472(8) 0.522(5) 0.0194(8) Uani 0.072(3) 1 d D . P A 2
C3B C 0.130(8) 0.535(5) 0.276(3) 0.0211(9) Uani 0.072(3) 1 d D . P A 2
C4B C 0.406(5) 1.118(4) 0.212(3) 0.0226(9) Uani 0.072(3) 1 d D . P A 2
H4B H 0.455277 1.181283 0.224044 0.027 Uiso 0.072(3) 1 calc R . P A 2
C5B C 0.407(5) 0.990(4) 0.322(3) 0.0175(8) Uani 0.072(3) 1 d D . P A 2
H5B H 0.461099 0.959863 0.409227 0.021 Uiso 0.072(3) 1 calc R . P A 2
C6B C 0.328(4) 0.897(3) 0.307(2) 0.0175(9) Uani 0.072(3) 1 d D . P A 2
C7B C 0.264(5) 0.938(4) 0.169(2) 0.0188(9) Uani 0.072(3) 1 d D . P A 2
C8B C 0.269(5) 1.070(3) 0.060(2) 0.0232(9) Uani 0.072(3) 1 d D . P A 2
C9B C 0.202(6) 1.134(4) -0.087(2) 0.0225(9) Uani 0.072(3) 1 d D . P A 2
H9BA H 0.089217 1.144237 -0.080578 0.034 Uiso 0.072(3) 1 calc GR . P A 2
H9BB H 0.273985 1.056572 -0.143722 0.034 Uiso 0.072(3) 1 calc GR . P A 2
H9BC H 0.199517 1.243432 -0.135407 0.034 Uiso 0.072(3) 1 calc GR . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0184(14) 0.0273(15) 0.0314(15) -0.0089(12) 0.0027(12) -0.0104(12)
N1 0.0183(16) 0.0255(17) 0.0266(16) -0.0081(14) 0.0031(13) -0.0128(14)
N2 0.0159(16) 0.0179(16) 0.0346(18) -0.0104(14) 0.0001(14) -0.0072(13)
C1 0.021(2) 0.0185(19) 0.0205(18) -0.0011(15) -0.0021(16) -0.0121(16)
C10 0.027(2) 0.030(2) 0.026(2) -0.0065(17) 0.0020(17) -0.0149(18)
C11 0.020(2) 0.039(2) 0.030(2) -0.0168(19) 0.0097(17) -0.0134(19)
C12 0.0160(19) 0.0155(18) 0.035(2) -0.0091(16) 0.0029(16) -0.0062(16)
C13 0.023(2) 0.022(2) 0.046(2) -0.0110(19) 0.0046(19) -0.0085(18)
Re1 0.01404(8) 0.01661(11) 0.01817(18) -0.00455(11) 0.00113(13) -0.00822(7)
O2 0.0302(17) 0.034(3) 0.0315(15) -0.0146(19) 0.0043(13) -0.0194(17)
O3 0.026(2) 0.019(2) 0.0228(13) -0.0023(14) -0.0020(12) -0.011(3)
O4 0.0221(14) 0.0228(15) 0.0205(14) -0.0025(12) -0.0027(12) -0.0126(12)
O5 0.0205(14) 0.0192(14) 0.0165(15) -0.0049(12) 0.0007(13) -0.0101(12)
O6 0.0239(17) 0.0173(16) 0.0190(12) -0.0040(11) 0.0007(11) -0.0109(15)
C2 0.0163(19) 0.021(2) 0.0211(19) -0.0046(16) 0.0032(16) -0.0069(19)
C3 0.014(2) 0.023(2) 0.028(2) -0.0134(18) 0.0025(17) -0.0106(19)
C4 0.019(2) 0.022(2) 0.019(2) 0.0019(17) -0.0035(16) -0.0067(18)
C5 0.019(2) 0.029(2) 0.019(2) -0.0045(18) -0.0014(17) -0.0107(19)
C6 0.0114(19) 0.021(2) 0.018(2) -0.0039(17) 0.0026(16) -0.0050(16)
C7 0.009(2) 0.0168(19) 0.022(2) -0.0059(17) -0.0001(17) -0.0020(16)
C8 0.0129(19) 0.018(2) 0.0180(19) -0.0053(16) 0.0026(15) -0.0048(16)
C9 0.021(2) 0.021(2) 0.023(2) -0.0060(17) 0.0004(17) -0.0080(17)
Re1B 0.01404(8) 0.01661(11) 0.01817(18) -0.00455(11) 0.00113(13) -0.00822(7)
O2B 0.026(2) 0.019(2) 0.0228(13) -0.0023(14) -0.0020(12) -0.011(3)
O3B 0.0302(17) 0.034(3) 0.0315(15) -0.0146(19) 0.0043(13) -0.0194(17)
O4B 0.0205(14) 0.0192(14) 0.0165(15) -0.0049(12) 0.0007(13) -0.0101(12)
O5B 0.0221(14) 0.0228(15) 0.0205(14) -0.0025(12) -0.0027(12) -0.0126(12)
O6B 0.0239(17) 0.0173(16) 0.0190(12) -0.0040(11) 0.0007(11) -0.0109(15)
C2B 0.014(2) 0.023(2) 0.028(2) -0.0134(18) 0.0025(17) -0.0106(19)
C3B 0.0163(19) 0.021(2) 0.0211(19) -0.0046(16) 0.0032(16) -0.0069(19)
C4B 0.019(2) 0.022(2) 0.019(2) 0.0019(17) -0.0035(16) -0.0067(18)
C5B 0.0129(19) 0.018(2) 0.0180(19) -0.0053(16) 0.0026(15) -0.0048(16)
C6B 0.009(2) 0.0168(19) 0.022(2) -0.0059(17) -0.0001(17) -0.0020(16)
C7B 0.0114(19) 0.021(2) 0.018(2) -0.0039(17) 0.0026(16) -0.0050(16)
C8B 0.019(2) 0.029(2) 0.019(2) -0.0045(18) -0.0014(17) -0.0107(19)
C9B 0.021(2) 0.021(2) 0.023(2) -0.0060(17) 0.0004(17) -0.0080(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
O1 C1 1.151(4) . ?
N1 C10 1.371(4) . ?
N1 C12 1.335(4) . ?
N1 Re1 2.193(3) . ?
N1 Re1B 2.289(8) . ?
N2 C11 1.367(5) . ?
N2 C12 1.339(4) . ?
N2 C13 1.466(4) . ?
C1 Re1 1.920(4) . ?
C1 Re1B 1.845(9) . ?
C10 C11 1.358(5) . ?
Re1 O4 2.159(2) . ?
Re1 O5 2.148(2) . ?
Re1 C2 1.901(4) . ?
Re1 C3 1.905(4) . ?
O2 C2 1.163(5) . ?
O3 C3 1.164(5) . ?
O4 C6 1.277(4) . ?
O5 C7 1.331(4) . ?
O6 C4 1.352(5) . ?
O6 C8 1.370(4) . ?
C4 C5 1.326(5) . ?
C5 C6 1.431(5) . ?
C6 C7 1.427(5) . ?
C7 C8 1.364(5) . ?
C8 C9 1.479(5) . ?
Re1B O4B 2.159(5) . ?
Re1B O5B 2.149(5) . ?
Re1B C2B 1.903(6) . ?
Re1B C3B 1.906(6) . ?
O2B C2B 1.164(7) . ?
O3B C3B 1.165(7) . ?
O4B C6B 1.277(6) . ?
O5B C7B 1.332(6) . ?
O6B C4B 1.352(7) . ?
O6B C8B 1.369(6) . ?
C4B C5B 1.325(7) . ?
C5B C6B 1.431(6) . ?
C6B C7B 1.428(7) . ?
C7B C8B 1.364(6) . ?
C8B C9B 1.479(7) . ?
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
C10 N1 Re1 129.2(2) . . ?
C10 N1 Re1B 131.9(3) . . ?
C12 N1 C10 105.7(3) . . ?
C12 N1 Re1 124.9(2) . . ?
C12 N1 Re1B 121.3(3) . . ?
C11 N2 C13 126.5(3) . . ?
C12 N2 C11 107.3(3) . . ?
C12 N2 C13 126.2(3) . . ?
O1 C1 Re1 178.7(3) . . ?
O1 C1 Re1B 170.6(4) . . ?
C11 C10 N1 109.2(3) . . ?
C10 C11 N2 106.8(3) . . ?
N1 C12 N2 111.0(3) . . ?
C1 Re1 N1 176.26(13) . . ?
C1 Re1 O4 94.85(12) . . ?
C1 Re1 O5 94.60(13) . . ?
O4 Re1 N1 84.82(11) . . ?
O5 Re1 N1 81.70(11) . . ?
O5 Re1 O4 76.68(10) . . ?
C2 Re1 N1 94.87(19) . . ?
C2 Re1 C1 88.9(2) . . ?
C2 Re1 O4 94.76(13) . . ?
C2 Re1 O5 170.98(14) . . ?
C2 Re1 C3 88.01(15) . . ?
C3 Re1 N1 92.9(3) . . ?
C3 Re1 C1 87.2(3) . . ?
C3 Re1 O4 176.58(19) . . ?
C3 Re1 O5 100.46(13) . . ?
C6 O4 Re1 113.4(2) . . ?
C7 O5 Re1 112.9(2) . . ?
C4 O6 C8 120.6(3) . . ?
O2 C2 Re1 176.6(5) . . ?
O3 C3 Re1 179.3(9) . . ?
C5 C4 O6 122.5(3) . . ?
C4 C5 C6 119.6(4) . . ?
O4 C6 C5 123.0(3) . . ?
O4 C6 C7 119.6(3) . . ?
C7 C6 C5 117.5(4) . . ?
O5 C7 C6 117.4(3) . . ?
O5 C7 C8 123.1(3) . . ?
C8 C7 C6 119.5(3) . . ?
O6 C8 C9 113.0(3) . . ?
C7 C8 O6 120.3(3) . . ?
C7 C8 C9 126.7(3) . . ?
C1 Re1B N1 167.6(4) . . ?
C1 Re1B O4B 102.0(10) . . ?
C1 Re1B O5B 90.9(10) . . ?
C1 Re1B C2B 95(4) . . ?
C1 Re1B C3B 81(2) . . ?
O4B Re1B N1 87.4(10) . . ?
O5B Re1B N1 83.4(10) . . ?
O5B Re1B O4B 76.67(18) . . ?
C2B Re1B N1 92(4) . . ?
C2B Re1B O4B 94.7(3) . . ?
C2B Re1B O5B 170.3(18) . . ?
C2B Re1B C3B 87.9(3) . . ?
C3B Re1B N1 89(2) . . ?
C3B Re1B O4B 175.8(16) . . ?
C3B Re1B O5B 100.4(3) . . ?
C6B O4B Re1B 113.2(4) . . ?
C7B O5B Re1B 112.6(4) . . ?
C4B O6B C8B 120.5(5) . . ?
O2B C2B Re1B 173(4) . . ?
O3B C3B Re1B 175(6) . . ?
C5B C4B O6B 122.5(5) . . ?
C4B C5B C6B 119.5(5) . . ?
O4B C6B C5B 123.0(5) . . ?
O4B C6B C7B 119.6(4) . . ?
C7B C6B C5B 117.4(5) . . ?
O5B C7B C6B 117.4(5) . . ?
O5B C7B C8B 123.0(5) . . ?
C8B C7B C6B 119.4(5) . . ?
O6B C8B C9B 113.1(5) . . ?
C7B C8B O6B 120.3(5) . . ?
C7B C8B C9B 126.6(5) . . ?
_shelx_res_file
;
TITL cm32_a.res in P-1
cm32.res
created by SHELXL-2018/3 at 14:04:15 on 04-Jun-2018
REM Old TITL CM32 in P-1
REM SHELXT solution in P-1: R1 0.054, Rweak 0.011, Alpha 0.045
REM 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 N2 O6 Re
CELL 0.71073 9.108 9.5099 9.7673 70.669 80.012 61.781
ZERR 2 0.0005 0.0005 0.0005 0.002 0.002 0.002
LATT 1
SFAC C H N O Re
UNIT 26 22 4 12 2
EADP Re1 Re1B
EADP O4 O5B
EADP O5 O4B
EADP O6 O6B
EADP C6B C7
EADP C7B C6
EADP C5 C8B
EADP C8 C5B
EADP C9 C9B
EADP C4 C4B
EADP C2B C3
EADP O3 O2B
EADP C3B C2
EADP O3B O2
L.S. 99
PLAN 20
SIZE 0.127 0.115 0.086
TEMP -173.15
BOND
list 4
fmap 2
ACTA 50
REM
REM
REM
WGHT 0.016500 0.053500
FVAR 0.39474 0.92801
O1 4 -0.142809 0.828753 0.434136 11.00000 0.01841 0.02730 =
0.03145 -0.00889 0.00274 -0.01044
N1 3 0.468744 0.512655 0.246945 11.00000 0.01826 0.02548 =
0.02658 -0.00810 0.00315 -0.01282
N2 3 0.733770 0.330645 0.253355 11.00000 0.01587 0.01789 =
0.03457 -0.01039 0.00010 -0.00722
C1 1 -0.010898 0.758727 0.390178 11.00000 0.02092 0.01853 =
0.02055 -0.00115 -0.00209 -0.01206
C10 1 0.544990 0.559811 0.118377 11.00000 0.02703 0.03000 =
0.02588 -0.00649 0.00200 -0.01493
AFIX 43
H10 2 0.492038 0.655770 0.039837 11.00000 -1.20000
AFIX 0
C11 1 0.708185 0.447620 0.121092 11.00000 0.01979 0.03907 =
0.02972 -0.01680 0.00972 -0.01339
AFIX 43
H11 2 0.789021 0.449968 0.045607 11.00000 -1.20000
AFIX 0
C12 1 0.587946 0.374072 0.326552 11.00000 0.01596 0.01547 =
0.03514 -0.00910 0.00294 -0.00622
AFIX 43
H12 2 0.571514 0.314189 0.422423 11.00000 -1.20000
AFIX 0
C13 1 0.892008 0.186172 0.306630 11.00000 0.02275 0.02221 =
0.04607 -0.01103 0.00463 -0.00849
AFIX 137
H13A 2 0.876629 0.126956 0.407074 11.00000 -1.50000
H13B 2 0.976343 0.223821 0.302690 11.00000 -1.50000
H13C 2 0.928815 0.111175 0.245734 11.00000 -1.50000
AFIX 0
PART 1
RE1 5 0.210818 0.639017 0.321352 21.00000 0.01404 0.01661 =
0.01817 -0.00455 0.00113 -0.00822
O2 4 0.086079 0.436725 0.228878 21.00000 0.03018 0.03375 =
0.03149 -0.01462 0.00425 -0.01945
O3 4 0.275018 0.389423 0.625366 21.00000 0.02623 0.01890 =
0.02278 -0.00228 -0.00204 -0.01131
O4 4 0.177734 0.816925 0.109108 21.00000 0.02206 0.02282 =
0.02049 -0.00253 -0.00274 -0.01255
O5 4 0.301175 0.800883 0.345839 21.00000 0.02053 0.01918 =
0.01651 -0.00491 0.00069 -0.01009
O6 4 0.346330 1.148723 0.082401 21.00000 0.02387 0.01730 =
0.01904 -0.00404 0.00073 -0.01093
C2 1 0.135367 0.509473 0.267818 21.00000 0.01633 0.02120 =
0.02109 -0.00464 0.00324 -0.00689
C3 1 0.251521 0.483314 0.509696 21.00000 0.01396 0.02269 =
0.02846 -0.01340 0.00248 -0.01058
C4 1 0.272345 1.161824 -0.032847 21.00000 0.01881 0.02198 =
0.01883 0.00194 -0.00352 -0.00673
AFIX 43
H4 2 0.262963 1.248741 -0.119544 21.00000 -1.20000
AFIX 0
C5 1 0.212405 1.057936 -0.029408 21.00000 0.01925 0.02930 =
0.01929 -0.00455 -0.00141 -0.01070
AFIX 43
H5 2 0.160502 1.071248 -0.112251 21.00000 -1.20000
AFIX 0
C6 1 0.226401 0.925628 0.099902 21.00000 0.01136 0.02105 =
0.01831 -0.00389 0.00259 -0.00495
C7 1 0.296602 0.918411 0.223310 21.00000 0.00896 0.01678 =
0.02226 -0.00586 -0.00015 -0.00200
C8 1 0.357530 1.028500 0.210832 21.00000 0.01291 0.01796 =
0.01796 -0.00528 0.00259 -0.00478
C9 1 0.440004 1.034610 0.325015 21.00000 0.02120 0.02098 =
0.02296 -0.00604 0.00041 -0.00804
AFIX 137
H9A 2 0.561194 0.975575 0.312817 21.00000 -1.50000
H9B 2 0.405889 0.981354 0.420642 21.00000 -1.50000
H9C 2 0.407590 1.150951 0.317266 21.00000 -1.50000
AFIX 0
SAME 0.005 0.005 Re1 > C9
PART 0
PART 2
RE1B 5 0.212475 0.648180 0.345961 -21.00000 0.01404 0.01661 =
0.01817 -0.00455 0.00113 -0.00822
O2B 4 0.286001 0.357248 0.623722 -21.00000 0.02623 0.01890 =
0.02278 -0.00228 -0.00204 -0.01131
O3B 4 0.092013 0.458711 0.229279 -21.00000 0.03018 0.03375 =
0.03149 -0.01462 0.00425 -0.01945
O4B 4 0.316461 0.778083 0.411049 -21.00000 0.02053 0.01918 =
0.01651 -0.00491 0.00069 -0.01009
O5B 4 0.191046 0.850578 0.154989 -21.00000 0.02206 0.02282 =
0.02049 -0.00253 -0.00274 -0.01255
O6B 4 0.335500 1.162284 0.083785 -21.00000 0.02387 0.01730 =
0.01904 -0.00404 0.00073 -0.01093
C2B 1 0.263024 0.471825 0.522169 -21.00000 0.01396 0.02269 =
0.02846 -0.01340 0.00248 -0.01058
C3B 1 0.130103 0.534730 0.275695 -21.00000 0.01633 0.02120 =
0.02109 -0.00464 0.00324 -0.00689
C4B 1 0.405520 1.118092 0.212089 -21.00000 0.01881 0.02198 =
0.01883 0.00194 -0.00352 -0.00673
AFIX 43
H4B 2 0.455277 1.181283 0.224044 -21.00000 -1.20000
AFIX 0
C5B 1 0.407315 0.989916 0.321768 -21.00000 0.01291 0.01796 =
0.01796 -0.00528 0.00259 -0.00478
AFIX 43
H5B 2 0.461099 0.959863 0.409227 -21.00000 -1.20000
AFIX 0
C6B 1 0.327627 0.897152 0.307445 -21.00000 0.00896 0.01678 =
0.02226 -0.00586 -0.00015 -0.00200
C7B 1 0.264041 0.937841 0.168557 -21.00000 0.01136 0.02105 =
0.01831 -0.00389 0.00259 -0.00495
C8B 1 0.269008 1.070054 0.060060 -21.00000 0.01925 0.02930 =
0.01929 -0.00455 -0.00141 -0.01070
C9B 1 0.202309 1.133960 -0.087336 -21.00000 0.02120 0.02098 =
0.02296 -0.00604 0.00041 -0.00804
AFIX 137
H9BA 2 0.089217 1.144237 -0.080578 -21.00000 -1.50000
H9BB 2 0.273985 1.056572 -0.143722 -21.00000 -1.50000
H9BC 2 0.199517 1.243432 -0.135407 -21.00000 -1.50000
AFIX 0
HKLF 4
REM cm32_a.res in P-1
REM wR2 = 0.0387, GooF = S = 1.047, Restrained GooF = 1.040 for all data
REM R1 = 0.0200 for 2647 Fo > 4sig(Fo) and 0.0233 for all 2866 data
REM 245 parameters refined using 37 restraints
END
WGHT 0.0165 0.0535
REM Highest difference peak 0.563, deepest hole -0.513, 1-sigma level 0.120
Q1 1 0.5027 0.9235 0.3791 11.00000 0.05 0.56
Q2 1 0.0820 0.6470 0.4034 11.00000 0.05 0.53
Q3 1 0.2450 0.5520 0.2307 11.00000 0.05 0.52
Q4 1 0.3894 1.0702 0.3790 11.00000 0.05 0.48
Q5 1 0.4961 0.5990 0.0555 11.00000 0.05 0.47
Q6 1 0.3796 0.9238 0.2002 11.00000 0.05 0.47
Q7 1 0.0550 1.0728 -0.1393 11.00000 0.05 0.43
Q8 1 0.2097 0.7253 0.2476 11.00000 0.05 0.43
Q9 1 0.1332 0.6601 0.2418 11.00000 0.05 0.42
Q10 1 0.7637 0.3373 0.3555 11.00000 0.05 0.42
Q11 1 0.4787 0.5585 0.1772 11.00000 0.05 0.42
Q12 1 0.1760 0.8988 -0.0752 11.00000 0.05 0.41
Q13 1 0.1676 0.4753 0.6045 11.00000 0.05 0.41
Q14 1 0.6999 0.3558 0.1659 11.00000 0.05 0.41
Q15 1 0.1915 1.0014 0.0347 11.00000 0.05 0.40
Q16 1 0.2435 0.3055 0.6939 11.00000 0.05 0.39
Q17 1 0.5797 0.8460 0.3212 11.00000 0.05 0.38
Q18 1 0.5613 1.1554 0.1021 11.00000 0.05 0.38
Q19 1 -0.0374 1.0800 0.0623 11.00000 0.05 0.38
Q20 1 -0.0630 0.8751 0.3956 11.00000 0.05 0.38
;
_shelx_res_checksum 58396
_olex2_submission_special_instructions 'No special instructions were received'