Organometallic nucleoside analogues: effect of the metallocene metal atom on cancer cell line toxicity.
Ismail, Media K.; Armstrong, Katie A.; Hodder, Samantha L.; Horswell, Sarah L.; Male, Louise; Nguyen, Huy V.; Wilkinson, Edward A.; Hodges, Nikolas J.; Tucker, James H. R.; Dalton transactions (Cambridge, England : 2003) 49 (2020) 1181–1190; doi:10.1039/c9dt04174e

data_7702963
_publ_section_title
;
 Organometallic nucleoside analogues: effect of the metallocene metal atom
 on cancer cell line toxicity.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1181
_journal_page_last               1190
_journal_paper_doi               10.1039/c9dt04174e
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C21 H26 N2 O3 Ru, C2 H3 N'
_chemical_formula_sum            'C23 H29 N3 O3 Ru'
_chemical_formula_weight         496.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-12 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                70.115(5)
_cell_angle_beta                 84.171(4)
_cell_angle_gamma                84.068(4)
_cell_formula_units_Z            4
_cell_length_a                   12.1133(5)
_cell_length_b                   12.9420(7)
_cell_length_c                   15.0302(8)
_cell_measurement_reflns_used    7314
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2210
_cell_measurement_theta_min      3.9030
_cell_volume                     2198.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -112.00  -6.00   1.00    6.70    --  -42.56 -19.00-120.00  106
  2  \w   -115.00 -21.00   1.00    6.70    --  -42.56 -38.00-180.00   94
  3  \w    -74.00 -12.00   1.00    6.70    --  -42.56 125.00 -30.00   62
  4  \w     23.00  98.00   1.00    6.70    --   42.56-125.00 150.00   75
  5  \w     59.00  88.00   1.00    6.70    --   42.56-140.00  34.00   29
  6  \w     46.00 108.00   1.00   27.00    --  106.63 -94.00  30.00   62
  7  \w    110.00 178.00   1.00   27.00    --  106.63  30.00 -30.00   68
  8  \w     41.00 111.00   1.00   27.00    --  106.63-125.00 -60.00   70
  9  \w     35.00 120.00   1.00   27.00    --  106.63-125.00-180.00   85
 10  \w    102.00 129.00   1.00   27.00    --  106.63  30.00-120.00   27
 11  \w     68.00 106.00   1.00   27.00    --  106.63 -94.00 -60.00   38
 12  \w     85.00 178.00   1.00   27.00    --  106.63  30.00 -90.00   93
 13  \w     42.00  71.00   1.00   27.00    --  106.63 -61.00  60.00   29
 14  \w    101.00 132.00   1.00   27.00    --  106.63 -61.00  60.00   31
 15  \w     94.00 172.00   1.00   27.00    --  106.63 125.00 -30.00   78
 16  \w     33.00 107.00   1.00   27.00    --  106.63 -30.00 -30.00   74
 17  \w     98.00 123.00   1.00   27.00    --  106.63 125.00 120.00   25
 18  \w     36.00 131.00   1.00   27.00    --  106.63 -45.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0153629000
_diffrn_orient_matrix_UB_12      0.0879059000
_diffrn_orient_matrix_UB_13      0.0491083000
_diffrn_orient_matrix_UB_21      -0.0072662000
_diffrn_orient_matrix_UB_22      -0.0914713000
_diffrn_orient_matrix_UB_23      0.0975461000
_diffrn_orient_matrix_UB_31      0.1270565000
_diffrn_orient_matrix_UB_32      -0.0040209000
_diffrn_orient_matrix_UB_33      0.0036890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15146
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.642
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.008
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.027
_refine_diff_density_max         2.281
_refine_diff_density_min         -1.025
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8029
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0410P)^2^+12.7920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7174
_reflns_number_total             8029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt04174e2.cif
_cod_data_source_block           1-(S_Rp)-Ru
_cod_depositor_comments
'Adding full bibliography for 7702963--7702968.cif.'
_cod_database_code               7702963
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C23 H29 N3 O3 Ru'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N3-H3 = N103-H103
 0.87 with sigma of 0.02
3. Rigid bond restraints
 C115, C116, C117, C118, C119
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C115 \\sim C116 \\sim C117 \\sim C118 \\sim C119: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.08
5.a Ternary CH refined with riding coordinates:
 C20(H20), C120(H120)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C22(H22A,H22B), C23(H23A,H23B), C108(H10D,H10E),
 C109(H10F,H10G), C122(H12D,H12E), C123(H12F,H12G)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C106(H106), C112(H112), C113(H113), C114(H114), C115(H115),
 C116(H116), C117(H117), C118(H118), C119(H119)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C21(H21A,H21B,H21C), C107(H10A,H10B,H10C), C121(H12A,H12B,
 H12C), C202(H20A,H20B,H20C), C302(H30A,H30B,H30C)
;
_shelx_res_checksum              30543
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.834