Well-defined coinage metal transfer agents for the synthesis of NHC-based nickel, rhodium and palladium macrocycles.
Andrew, Rhiann E.; Storey, Caroline M.; Chaplin, Adrian B.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 8937–8944; doi:10.1039/c6dt01263a

data_7039212
_publ_section_title
;
 Well-defined coinage metal transfer agents for the synthesis of NHC-based
 nickel, rhodium and palladium macrocycles.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8937
_journal_page_last               8944
_journal_paper_doi               10.1039/c6dt01263a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C25 H35 Cl N5 Ni, C32 H12 B F24'
_chemical_formula_sum            'C57 H47 B Cl F24 N5 Ni'
_chemical_formula_weight         1362.96
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-24 deposited with the CCDC.
2016-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                101.223(4)
_cell_angle_beta                 99.989(4)
_cell_angle_gamma                101.393(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7990(4)
_cell_length_b                   14.7487(6)
_cell_length_c                   21.7093(12)
_cell_measurement_reflns_used    6744
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.5910
_cell_measurement_theta_min      3.4830
_cell_volume                     2942.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6093
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -97.00   1.00   1.00   55.00    --  -23.00 -37.00   0.00   98
  2  \w    -96.00   7.00   1.00   55.00    --  -23.00 -65.00 133.25  103
  3  \w    -95.00   5.00   1.00   55.00    --  -23.00 -57.00-150.00  100
  4  \w    -64.00  57.00   1.00   55.00    --  -23.00  19.00  30.00  121
  5  \w    -87.00 -13.00   1.00   55.00    --  -23.00 -64.00  79.98   74
  6  \w      5.00  97.00   1.00   55.00    --   24.25  65.00   2.24   92
  7  \w     -5.00  21.00   1.00   55.00    --   24.25 -37.00   0.00   26
  8  \w     13.00  40.00   1.00   55.00    --   24.25  65.00 121.76   27
  9  \w    -45.00  54.00   1.00   55.00    --   24.25 -63.00-128.97   99
 10  \w     10.00  45.00   1.00   55.00    --   24.25  65.00  76.69   35
 11  \w     -3.00  23.00   1.00   55.00    --   24.25  65.00 167.65   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0139241000
_diffrn_orient_matrix_UB_12      -0.0116432000
_diffrn_orient_matrix_UB_13      0.0288662000
_diffrn_orient_matrix_UB_21      -0.0445838000
_diffrn_orient_matrix_UB_22      -0.0445617000
_diffrn_orient_matrix_UB_23      -0.0180265000
_diffrn_orient_matrix_UB_31      0.0595732000
_diffrn_orient_matrix_UB_32      -0.0207071000
_diffrn_orient_matrix_UB_33      0.0028187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1528
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13369
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.682
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         3.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1380
_exptl_crystal_recrystallization_method
;
Crystals grown from a mixture of toluene, pentane, cyclohexane and 
diethyl ether at 293 K
;
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.083
_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     858
_refine_ls_number_reflns         13369
_refine_ls_number_restraints     342
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+8.6773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10675
_reflns_number_total             13369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt01263a2.cif
_cod_data_source_block           0197abc15s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7039209--7039212.cif.
;
_cod_database_code               7039212
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5228(10) 0.4772(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 C215-F7 \\sim C215-F8 \\sim C215-F9 \\sim C215-F7A \\sim C215-F8A \\sim
C215-F9A
 with sigma of 0.01
 F7-F8 \\sim F8-F9 \\sim F9-F7 \\sim F7A-F8A \\sim F8A-F9A \\sim F9A-F7A
 with sigma of 0.01
 C211-F7 \\sim C211-F8 \\sim C211-F9 \\sim C211-F7A \\sim C211-F8A \\sim
C211-F9A
 with sigma of 0.01
 C231-F19 \\sim C231-F20 \\sim C231-F21 \\sim C231-F19A \\sim C231-F20A \\sim
C231-F21A
 with sigma of 0.01
 F19-F20 \\sim F20-F21 \\sim F21-F19 \\sim F19A-F20A \\sim F20A-F21A \\sim
F21A-F19A
 with sigma of 0.01
 C227-F19 \\sim C227-F20 \\sim C227-F21 \\sim C227-F19A \\sim C227-F20A \\sim
C227-F21A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F7A \\sim F8
\\sim F8A \\sim F9 \\sim F9A \\sim F10 \\sim F11 \\sim F12 \\sim F13 \\sim F14
\\sim F15 \\sim F16 \\sim F17 \\sim F18 \\sim F19 \\sim F19A \\sim F20 \\sim
F20A \\sim F21 \\sim F21A \\sim F22 \\sim F23 \\sim F24: within 2A with sigma
of 0.007 and sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F7A)
\\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F9) \\sim Ueq,
Uanis(F9A) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F12)
\\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15) \\sim Ueq,
Uanis(F16) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F18) \\sim Ueq, Uanis(F19)
\\sim Ueq, Uanis(F19A) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F20A) \\sim Ueq,
Uanis(F21) \\sim Ueq, Uanis(F21A) \\sim Ueq, Uanis(F22) \\sim Ueq, Uanis(F23)
\\sim Ueq, Uanis(F24) \\sim Ueq: with sigma of 0.007 and sigma for terminal
atoms of 0.02
5. Others
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(1)
 Fixed Sof: F19(0.5) F19A(0.5) F20(0.5) F20A(0.5) F21(0.5) F21A(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C22(H22A,H22B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,
 H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C20(H20), C21(H21), C26(H26), C27(H27),
 C202(H202), C204(H204), C206(H206), C210(H210), C212(H212), C214(H214),
 C218(H218), C220(H220), C222(H222), C226(H226), C228(H228), C230(H230)
;
_shelx_shelxl_version_number     2014/7
_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 2.660
_oxdiff_exptl_absorpt_empirical_full_min 0.335
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by -179.9906\% 
 around [-0.00 0.00 1.00] (reciprocal) or [0.42 0.30 0.86] (direct)
;