N-Nitrosamine-{cis-Re[CO]2}(2+) cobalamin conjugates as mixed CO/NO-releasing molecules.
Santoro, Giuseppe; Beltrami, Ruben; Kottelat, Emmanuel; Blacque, Olivier; Bogdanova, Anna Yu; Zobi, Fabio; Dalton transactions (Cambridge, England : 2003) 45 (2016) 1504–1513; doi:10.1039/c5dt03402g

data_7037529
_publ_section_title
;
 N-Nitrosamine-{cis-Re[CO]2}(2+) cobalamin conjugates as mixed
 CO/NO-releasing molecules.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1504
_journal_page_last               1513
_journal_paper_doi               10.1039/c5dt03402g
_journal_volume                  45
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety
'2(C68 H95 Co N17 O16 P), C3 H6 O, 23 (H2 O) '
_chemical_formula_sum            'C139 H242 Co2 N34 O56 P2'
_chemical_formula_weight         3465.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-03-18 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.299(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.6019(4)
_cell_length_b                   21.4078(4)
_cell_length_c                   28.0537(7)
_cell_measurement_reflns_used    26528
_cell_measurement_temperature    183(1)
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      2.8
_cell_volume                     9330.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(1)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -41.00   62.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5599   57.0000  120.0000 206

  2 omega  -67.00    4.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5599  -38.0000 -180.0000 142

  3 omega  -33.00   43.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5599   38.0000   60.0000 152

  4 omega   -7.00   66.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1849   57.0000 -150.0000 146

  5 omega   -9.00   16.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1849   38.0000 -180.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0128793000
_diffrn_orient_matrix_UB_12      0.0005526000
_diffrn_orient_matrix_UB_13      -0.0249076000
_diffrn_orient_matrix_UB_21      -0.0421739000
_diffrn_orient_matrix_UB_22      0.0088092000
_diffrn_orient_matrix_UB_23      0.0047938000
_diffrn_orient_matrix_UB_31      0.0118096000
_diffrn_orient_matrix_UB_32      0.0319591000
_diffrn_orient_matrix_UB_33      -0.0008904000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            85003
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.786
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             3692
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 12258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1927
_refine_ls_number_reflns         37195
_refine_ls_number_restraints     760
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1110P)^2^+4.3939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.1928
_reflns_Friedel_coverage         0.902
_reflns_friedel_fraction_full    0.955
_reflns_friedel_fraction_max     0.951
_reflns_number_gt                31747
_reflns_number_total             37195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt03402g2.cif
_cod_data_source_block           1p
_cod_depositor_comments
'Adding full bibliography for 7037528--7037529.cif.'
_cod_database_code               7037529
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N32A-C133 = N32A-C136 = C133-C134 = C135-C136 = N33A-C134 = N33A-C135
 1.47393 with sigma of 0.01
 N32B-C233 = N32B-C236 = C233-C234 = C235-C236 = N33B-C134 = N33B-C235
 1.47393 with sigma of 0.01
 N32A-C134 = N32A-C135 = N32B-C234 = N32B-C235
 2.3793 with sigma of 0.02
 N33A-C133 = N33A-C136 = N33B-C233 = N33B-C236
 2.3793 with sigma of 0.02
 N16-N17 = C17-N8
 1.32 with sigma of 0.01
 C17-O1
 1.25 with sigma of 0.01
 N33A-N34 \\sim N33B-N34
 with sigma of 0.01
 C132-N32A \\sim C132-N32B
 with sigma of 0.01
 N16-C67A \\sim N16-C67B
 with sigma of 0.005
 C67A-C68 \\sim C67A-C68
 with sigma of 0.005
3. Rigid bond restraints
 C133, C134, C135, C136, N32A, N33A, C233, C234, C235, C236, N32B, N33B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 N15, N16, N17, O16, C65, C66, C67A, C67B, C68
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C27, O2, N9
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C133 \\sim C134 \\sim C135 \\sim C136 \\sim N32A \\sim N33A \\sim C233 \\sim
C234 \\sim C235 \\sim C236 \\sim N32B \\sim N33B: within 4A with sigma of 0.005
and sigma for terminal atoms of 0.01
N15 \\sim N16 \\sim N17 \\sim O16 \\sim C65 \\sim C66 \\sim C67A \\sim C67B
\\sim C68: within 4A with sigma of 0.005 and sigma for terminal atoms of 0.01
C26 \\sim C27 \\sim O2 \\sim N9: within 3A with sigma of 0.005 and sigma for
terminal atoms of 0.01
N26 \\sim C95 \\sim O18: within 3A with sigma of 0.005 and sigma for terminal
atoms of 0.01
C38 \\sim C39 \\sim O4 \\sim N11: within 3A with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(N8) = Uanis(C17) = Uanis(O1)
Uanis(C67A) = Uanis(C67B)
5. Others
 Sof(C233)=Sof(H23A)=Sof(H23B)=Sof(C234)=Sof(H23C)=Sof(H23D)=Sof(C235)=
 Sof(H23E)=Sof(H23F)=Sof(C236)=Sof(H23G)=Sof(H23H)=Sof(N32B)=Sof(N33B)=1-FVAR(1)
 Sof(C133)=Sof(H13C)=Sof(H13D)=Sof(C134)=Sof(H13E)=Sof(H13F)=Sof(C135)=
 Sof(H13G)=Sof(H13H)=Sof(C136)=Sof(H13I)=Sof(H13J)=Sof(N32A)=Sof(N33A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
 1(DFIX)=1(DFIX)=FVAR(3)
 Sof(C67B)=Sof(H67C)=Sof(H67D)=Sof(H68C)=Sof(H68D)=1-FVAR(4)
 Sof(C67A)=Sof(H67A)=Sof(H67B)=Sof(H68A)=Sof(H68B)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C12(H12), C22(H22), C34(H34), C44(H44), C45(H45), C57(H57), C59(H59),
 C60(H60), C61(H61), C62(H62), C80(H80), C90(H90), C102(H102), C112(H112),
 C113(H113), C125(H125), C127(H127), C128(H128), C129(H129), C130(H130)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C25(H25C,H25D), C26(H26C,H26D), C29(H29C,
 H29D), C37(H37A,H37B), C38(H38A,H38B), C41(H41A,H41B), C50(H50A,H50B),
 C53(H53A,H53B), C54(H54A,H54B), C56(H56A,H56B), C63(H63A,H63B), C65(H65A,H65B),
  C66(H66A,H66B), C67A(H67A,H67B), C67B(H67C,H67D), C68(H68A,H68B), C68(H68C,
 H68D), C83(H83A,H83B), C84(H84A,H84B), C93(H93A,H93B), C94(H94A,H94B),
 C97(H97A,H97B), C105(H10D,H10E), C106(H10F,H10G), C108(H10H,H10I), C116(H11G,
 H11H), C121(H12D,H12E), C122(H12F,H12G), C124(H12H,H12I), C131(H13A,H13B),
 C133(H13C,H13D), C134(H13E,H13F), C135(H13G,H13H), C136(H13I,H13J), C233(H23A,
 H23B), C234(H23C,H23D), C235(H23E,H23F), C236(H23G,H23H)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C20(H20), N14(H14), C70(H70), C72(H72), C75(H75),
 C88(H88), N31(H31)
6.d Tetrahedral OH refined with riding coordinates:
 O13(H13)
6.e X=CH2 refined with riding coordinates:
 N8(H8A,H8B), N11(H11L,H11M), N12(H12M,H12N), N13(H13K,H13L), N9(H9D,H9E),
 N10(H10M,H10N), N25(H25A,H25B), N26(H26A,H26B), N27(H27A,H27B), N28(H28A,H28B),
  N29(H29A,H29B), N30(H30A,H30B)
6.f Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10J,H10K,H10L), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C28(H28C,H28D,H28E), C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C43(H43A,
 H43B,H43C), C49(H49A,H49B,H49C), C52(H52A,H52B,H52C), C58(H58A,H58B,H58C),
 C77(H77A,H77B,H77C), C78(H78A,H78B,H78C), C86(H86A,H86B,H86C), C87(H87A,H87B,
 H87C), C96(H96A,H96B,H96C), C100(H10A,H10B,H10C), C110(H11A,H11B,H11C),
 C111(H11D,H11E,H11F), C118(H11I,H11J,H11K), C120(H12A,H12B,H12C), C126(H12J,
 H12K,H12L)
6.g Idealised tetrahedral OH refined as rotating group:
 O29(H29)
;
_shelx_res_checksum              98286
_shelx_hkl_checksum              17528
_shelx_fab_checksum              9387
_olex2_submission_special_instructions 'No special instructions were received'