#------------------------------------------------------------------------------
#$Date: 2023-10-13 02:11:27 +0300 (Fri, 13 Oct 2023) $
#$Revision: 286947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/42/7714215.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7714215
loop_
_publ_author_name
'Battistin, Federica'
'Fernandes, Célia'
'Raposinho, Paula D.'
'Blacque, Olivier'
'Paulo, António Rocha'
'Alberto, Roger'
_publ_section_title
;
 In vivo and in vitro studies of [M(η6-pseudoerlotinib)2]+ sandwich
 complexes (M = Re, 99mTc)
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT03011C
_journal_year                    2023
_chemical_formula_moiety         'C12 H13 N Re, F6 P'
_chemical_formula_sum            'C12 H13 F6 N P Re'
_chemical_formula_weight         502.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           71
_space_group_name_Hall           '-I 2 2'
_space_group_name_H-M_alt        'I m m m'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2023-09-06 deposited with the CCDC.	2023-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0918(1)
_cell_length_b                   12.2476(2)
_cell_length_c                   7.0155(1)
_cell_measurement_reflns_used    3609
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.1430
_cell_measurement_theta_min      6.5190
_cell_volume                     695.272(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 123.00   0.50    0.10    --   52.02  66.00 -55.00  178
  2  ω   -101.00 -13.00   0.50    0.20    --  -86.25  57.00 149.00  176
  3  ω   -162.00 -80.00   0.50    0.20    --  -86.25-112.00 -69.00  164
  4  ω     37.00 126.00   0.50    0.20    --  107.75 -66.00 169.00  178
  5  ω    -86.00 -12.00   0.50    0.10    --  -52.02 125.00 -90.00  148
  6  ω   -127.00 -73.00   0.50    0.10    --  -52.02-125.00  90.00  108
  7  ω     94.00 178.00   0.50    0.20    --  107.75  30.00 -90.00  168
  8  ω    102.00 178.00   0.50    0.20    --  107.75 111.00 150.00  152
  9  ω     31.00 106.00   0.50    0.20    --  107.75 -94.00  90.00  150
 10  ω     94.00 178.00   0.50    0.20    --  107.75  30.00 -60.00  168
 11  ω     94.00 178.00   0.50    0.20    --  107.75  30.00-120.00  168
 12  ω     31.00 106.00   0.50    0.20    --  107.75 -94.00-180.00  150
 13  ω     93.00 178.00   0.50    0.20    --  107.75  57.00 149.00  170
 14  ω   -125.00 -30.00   0.50    0.10    --  -52.02 -77.00 120.00  190
 15  ω   -125.00 -37.00   0.50    0.10    --  -52.02 -57.00   8.00  176
 16  ω   -125.00 -30.00   0.50    0.10    --  -52.02 -77.00-150.00  190
 17  ω     94.00 119.00   0.50    0.20    --  107.75  30.00   0.00   50
 18  ω     96.00 178.00   0.50    0.20    --  107.75  15.00  90.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999, Acta A55, 543--557)'
_diffrn_orient_matrix_UB_11      0.0255588000
_diffrn_orient_matrix_UB_12      0.1134496000
_diffrn_orient_matrix_UB_13      -0.0901376000
_diffrn_orient_matrix_UB_21      0.1277001000
_diffrn_orient_matrix_UB_22      -0.0487417000
_diffrn_orient_matrix_UB_23      -0.1388673000
_diffrn_orient_matrix_UB_31      -0.1388626000
_diffrn_orient_matrix_UB_32      -0.0240256000
_diffrn_orient_matrix_UB_33      -0.1442506000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3744
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.320
_diffrn_reflns_theta_min         6.557
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.792
_exptl_absorpt_correction_T_max  0.337
_exptl_absorpt_correction_T_min  0.133
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.400
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0087(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         436
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0162
_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/[σ²(Fo²)+(0.0216P)²+1.3906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0396
_refine_ls_wR_factor_ref         0.0396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                436
_reflns_number_total             436
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt03011c2.cif
_cod_data_source_block           2
_cod_database_code               7714215
_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.
;
_shelx_estimated_absorpt_t_max   0.283
_shelx_estimated_absorpt_t_min   0.133
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All F(H,H) groups
2. Restrained distances
 C1A-C2A = C2B-C1B
 1.4 with sigma of 0.01
 C1B_$1-C1B_$2
 1.4 with sigma of 0.01
 N1-H1D = N1-H1C
 0.82 with sigma of 0.005
 H1D-H1C
 1.34 with sigma of 0.01
 P1-F2A \\sim P1-F1A \\sim P1-F1B \\sim P1-F2B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Re1 \\sim C1A \\sim C2A \\sim C1B \\sim C2B: within 3A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 3A
F1A \\sim F2A \\sim F1B \\sim F2B: within 3A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 3A
4. Others
 Sof(F1B)=0.5*(1-FVAR(2))
 Sof(F2B)=0.25*(1-FVAR(2))
 Sof(F1A)=0.25*FVAR(2)
 Sof(F2A)=0.5*FVAR(2)
 Sof(C2A)=Sof(H2A)=1-FVAR(2)
 Sof(C1A)=0.5*(1-FVAR(3))
 Sof(C2B)=Sof(H2B)=0.5*FVAR(3)
 Sof(C1B)=Sof(H1B)=FVAR(2)
 Fixed Sof: H1A(0.28425) H1D(0.125) H1C(0.125) N1(0.125)
5.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
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 1.000000 0.500000 1.000000 0.0379(2) Uani 1 8 d S TU P . .
P1 P 0.500000 0.500000 0.500000 0.0354(4) Uani 1 8 d DS T P . .
F1A F 0.6953(5) 0.500000 0.500000 0.073(2) Uani 0.750(9) 4 d DS TU P A 1
F2A F 0.500000 0.4098(5) 0.6605(8) 0.096(2) Uani 0.750(9) 2 d DS TU P A 1
C1A C 0.8260(8) 0.6432(5) 1.000000 0.0455(15) Uani 0.818(14) 2 d DS TU P B 1
H1A H 0.708659 0.645478 0.999999 0.055 Uiso 0.5685 2 calc R U P B 1
C2A C 0.9128(6) 0.6415(3) 0.8258(6) 0.0463(14) Uani 0.818(14) 1 d D U P B 1
H2A H 0.854047 0.640370 0.708577 0.056 Uiso 0.818(14) 1 calc R U P B 1
F1B F 0.6378(19) 0.5912(12) 0.500000 0.094(5) Uani 0.250(9) 2 d DS TU P A 2
H1D H 0.63(4) 0.63(2) 1.095(19) 0.113 Uiso 0.125 1 d D U P C 3
H1C H 0.63(4) 0.63(2) 0.905(19) 0.113 Uiso 0.125 1 d D U P D 3
F2B F 0.500000 0.500000 0.7248(8) 0.081(5) Uani 0.250(9) 4 d DS TU P A 2
C1B C 0.8478(19) 0.6417(14) 0.9004(8) 0.042(3) Uani 0.182(14) 1 d D U P B 2
H1B H 0.747221 0.641628 0.830495 0.050 Uiso 0.182(14) 1 calc R U P B 2
C2B C 1.000000 0.642(2) 0.808(4) 0.043(3) Uani 0.182(14) 2 d DS TU P B 2
H2B H 1.000000 0.642090 0.672220 0.052 Uiso 0.182(14) 2 calc R U P B 2
N1 N 0.6701(18) 0.6585(12) 1.000000 0.047(3) Uani 0.25 2 d DS T P E 3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0506
0 -1 0 0.0406
-3 0 4 0.0660
4 0 -3 0.0504
-1 -1 -4 0.0367
-3 2 -3 0.0710
-2 -7 -2 0.0470
4 0 3 0.0807
-1 1 -2 0.0485
2 -5 -2 0.0468
-1 -5 1 0.0430
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
C2A Re1 C2A 101.7(2) . 11_565 ?
C2A Re1 C2A 143.2(2) 3_757 2_765 ?
C2A Re1 C2A 36.8(2) 4_567 9_767 ?
C2A Re1 C2A 113.7(2) 3_757 4_567 ?
C2A Re1 C2A 36.8(2) . 12_755 ?
C2A Re1 C2A 66.3(2) 3_757 12_755 ?
C2A Re1 C2A 36.8(2) 11_565 2_765 ?
C2A Re1 C2A 66.3(2) 11_565 4_567 ?
C2A Re1 C2A 180.0 10_557 2_765 ?
C2A Re1 C2A 180.0 . 9_767 ?
C2A Re1 C2A 36.8(2) 3_757 10_557 ?
C2A Re1 C2A 113.7(2) 10_557 9_767 ?
C2A Re1 C2A 101.7(2) 3_757 9_767 ?
C2A Re1 C2A 143.2(2) . 4_567 ?
C2A Re1 C2A 66.3(2) . 10_557 ?
C2A Re1 C2A 78.3(2) . 3_757 ?
C2A Re1 C2A 101.7(2) 10_557 4_567 ?
C2A Re1 C2A 78.3(2) 2_765 4_567 ?
C2A Re1 C2A 143.2(2) 11_565 10_557 ?
C2A Re1 C2A 180.00(12) 12_755 4_567 ?
C2A Re1 C2A 78.3(2) 11_565 9_767 ?
C2A Re1 C2A 113.7(2) 11_565 12_755 ?
C2A Re1 C2A 78.3(2) 10_557 12_755 ?
C2A Re1 C2A 180.00(12) 11_565 3_757 ?
C2A Re1 C2A 113.7(2) . 2_765 ?
C2A Re1 C2A 66.3(2) 2_765 9_767 ?
C2A Re1 C2A 101.7(2) 2_765 12_755 ?
C2A Re1 C2A 143.2(2) 12_755 9_767 ?
C2B Re1 C2B 104.3(15) 2_765 . ?
C2B Re1 C2B 180.0 9_767 . ?
C2B Re1 C2B 75.7(15) 10_557 . ?
F1A P1 F1A 180.0 . 9_666 ?
F2A P1 F1A 90.000(2) . 9_666 ?
F2A P1 F1A 90.000(1) 10_556 . ?
F2A P1 F1A 90.000(2) 9_666 9_666 ?
F2A P1 F1A 90.000(1) 2_665 . ?
F2A P1 F1A 90.000(1) 2_665 9_666 ?
F2A P1 F1A 90.000(2) 9_666 . ?
F2A P1 F1A 90.000(2) . . ?
F2A P1 F1A 90.000(1) 10_556 9_666 ?
F2A P1 F2A 180.0(3) 10_556 2_665 ?
F2A P1 F2A 88.9(5) . 2_665 ?
F2A P1 F2A 180.0(3) . 9_666 ?
F2A P1 F2A 91.1(5) 2_665 9_666 ?
F2A P1 F2A 91.1(5) . 10_556 ?
F2A P1 F2A 88.9(5) 10_556 9_666 ?
F2A P1 F1B 60.3(4) . 9_666 ?
F2A P1 F1B 119.7(4) 2_665 11_565 ?
F2A P1 F1B 60.3(4) . 11_565 ?
F2A P1 F1B 60.3(4) 9_666 3_656 ?
F2A P1 F1B 60.3(4) 10_556 11_565 ?
F2A P1 F1B 60.3(4) 2_665 3_656 ?
F2A P1 F1B 60.3(4) 10_556 9_666 ?
F2A P1 F1B 119.7(4) 10_556 3_656 ?
F2A P1 F1B 119.7(4) 9_666 9_666 ?
F2A P1 F1B 119.7(4) 2_665 9_666 ?
F2A P1 F1B 119.7(4) 9_666 11_565 ?
F2A P1 F1B 119.7(4) . 3_656 ?
F2B P1 F1B 90.000(2) . . ?
F2B P1 F1B 90.000(1) 9_666 . ?
F2B P1 F2B 180.0 9_666 . ?
Re1 C1A H1A 130.4 . . ?
C2A C1A Re1 71.1(3) . . ?
C2A C1A Re1 71.1(3) 10_557 . ?
C2A C1A H1A 119.9 . . ?
C2A C1A H1A 119.9 10_557 . ?
C2A C1A C2A 120.2(6) . 10_557 ?
Re1 C2A H2A 128.3 . . ?
C1A C2A Re1 72.2(3) . . ?
C1A C2A C2A 119.9(3) . 12_755 ?
C1A C2A H2A 120.1 . . ?
C2A C2A Re1 71.61(12) 12_755 . ?
C2A C2A H2A 120.1 12_755 . ?
Re1 C1B H1B 129.1 . . ?
C1B C1B Re1 71.83(18) 10_557 . ?
C1B C1B H1B 121.1 10_557 . ?
C2B C1B Re1 70.2(15) . . ?
C2B C1B H1B 121.1 . . ?
Re1 C2B H2B 128.0 . . ?
C1B C2B Re1 73.3(14) . . ?
C1B C2B Re1 73.3(14) 12_755 . ?
C1B C2B C1B 124(3) 12_755 . ?
C1B C2B H2B 117.8 . . ?
C1B C2B H2B 117.8 12_755 . ?
H1D N1 H1C 109.6(16) . . ?
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 C2A 2.235(4) . ?
Re1 C2A 2.235(4) 10_557 ?
Re1 C2A 2.235(4) 3_757 ?
Re1 C2A 2.235(4) 4_567 ?
Re1 C2A 2.235(4) 11_565 ?
Re1 C2A 2.235(4) 2_765 ?
Re1 C2A 2.235(4) 12_755 ?
Re1 C2A 2.235(4) 9_767 ?
Re1 C2B 2.20(3) 9_767 ?
Re1 C2B 2.20(3) 10_557 ?
Re1 C2B 2.20(3) 2_765 ?
Re1 C2B 2.20(3) . ?
P1 F1A 1.580(4) 9_666 ?
P1 F1A 1.580(4) . ?
P1 F2A 1.578(4) 2_665 ?
P1 F2A 1.578(4) 10_556 ?
P1 F2A 1.578(4) . ?
P1 F2A 1.578(4) 9_666 ?
P1 F1B 1.579(5) . ?
P1 F1B 1.579(5) 3_656 ?
P1 F1B 1.579(5) 9_666 ?
P1 F1B 1.579(5) 11_565 ?
P1 F2B 1.577(5) . ?
P1 F2B 1.577(5) 9_666 ?
C1A H1A 0.9500 . ?
C1A C2A 1.410(5) 10_557 ?
C1A C2A 1.410(5) . ?
C2A C2A 1.410(9) 12_755 ?
C2A H2A 0.9500 . ?
C1B C1B 1.398(11) 10_557 ?
C1B H1B 0.9500 . ?
C1B C2B 1.393(10) . ?
C2B H2B 0.9500 . ?
N1 H1D 0.820(6) . ?
N1 H1C 0.820(6) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 C1A C2A C2A -55.5(2) . . . 12_755 ?
Re1 C1B C2B C1B -55(3) . . . 12_755 ?
C2A C1A C2A Re1 53.5(5) 10_557 . . . ?
C2A C1A C2A C2A -1.9(6) 10_557 . . 12_755 ?
C1B C1B C2B Re1 55.5(10) 10_557 . . . ?
C1B C1B C2B C1B 0(4) 10_557 . . 12_755 ?
