A shape changing tandem Rh(CNC) catalyst: preparation of bicyclo[4.2.0]octa-1,5,7-trienes from terminal aryl alkynes.
Storey, Caroline M.; Kalpokas, Audrius; Gyton, Matthew R.; Krämer, Tobias; Chaplin, Adrian B.; Chemical science 11 (2020) 2051–2057; doi:10.1039/c9sc06153c

data_1557121
_publ_section_title
;
 A shape changing tandem Rh(CNC) catalyst: preparation of
 bicyclo[4.2.0]octa-1,5,7-trienes from terminal aryl alkynes.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2051
_journal_page_last               2057
_journal_paper_doi               10.1039/c9sc06153c
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C22 H25 N5 Rh, C32 H12 B F24'
_chemical_formula_sum            'C54 H37 B F24 N5 Rh'
_chemical_formula_weight         1325.60
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-04 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7133(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.95902(18)
_cell_length_b                   18.45666(19)
_cell_length_c                   34.7576(3)
_cell_measurement_reflns_used    78066
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.3010
_cell_measurement_theta_min      2.8560
_cell_volume                     10753.81(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     -4.00  97.00   1.00    7.50    --   24.56  57.00   0.00  101
  2  \w     35.00 113.00   1.00    7.50    --   24.56 178.00-120.00   78
  3  \w     35.00 113.00   1.00    7.50    --   24.56 178.00   0.00   78
  4  \w    -20.00  65.00   1.00    7.50    --   24.56 -99.00-150.00   85
  5  \w   -110.00 -55.00   1.00    7.50    --  -23.16 178.00 -60.00   55
  6  \w    -20.00  65.00   1.00    7.50    --   24.56 -99.00 120.00   85
  7  \w     -4.00  97.00   1.00    7.50    --   24.56  57.00 -90.00  101
  8  \w     35.00 113.00   1.00    7.50    --   24.56 178.00  90.00   78
  9  \w     -4.00  97.00   1.00    7.50    --   24.56  57.00 120.00  101
 10  \w      0.00  99.00   1.00    7.50    --   24.56  37.00-120.00   99
 11  \w    -99.00 -74.00   1.00    7.50    --  -23.16 -77.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction: 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      0.0028646000
_diffrn_orient_matrix_UB_12      0.0146442000
_diffrn_orient_matrix_UB_13      0.0190278000
_diffrn_orient_matrix_UB_21      -0.0193650000
_diffrn_orient_matrix_UB_22      -0.0311106000
_diffrn_orient_matrix_UB_23      0.0060786000
_diffrn_orient_matrix_UB_31      0.0375045000
_diffrn_orient_matrix_UB_32      -0.0171830000
_diffrn_orient_matrix_UB_33      0.0052140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            128904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        29.575
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5296
_exptl_crystal_recrystallization_method
'Crystals grown from CH2Cl2-pentane at 293 K'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.860
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     880
_refine_ls_number_reflns         15104
_refine_ls_number_restraints     540
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0258P)^2^+43.6471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13714
_reflns_number_total             15104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06153c3.cif
_cod_data_source_block           0447abc18s
_cod_depositor_comments
;
The following automatic conversions were performed:

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

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

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1557116--1557122.cif.

 Adding full bibliography for 1557116--1557122.cif.
;
_cod_database_code               1557121
_shelx_shelxl_version_number     2014/7
_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
 C208-F4 \\sim C208-F5 \\sim C208-F6 \\sim C208-F4A \\sim C208-F5A \\sim
C208-F6A
 with sigma of 0.01
 F4-F5 \\sim F5-F6 \\sim F6-F4 \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.01
 C205-F4 \\sim C205-F5 \\sim C205-F6 \\sim C205-F4A \\sim C205-F5A \\sim
C205-F6A
 with sigma of 0.01
 C216-F10 \\sim C216-F11 \\sim C216-F12 \\sim C216-F10A \\sim C216-F11A \\sim
C216-F12A
 with sigma of 0.01
 F10-F11 \\sim F11-F12 \\sim F12-F10 \\sim F10A-F11A \\sim F11A-F12A \\sim
F12A-F10A
 with sigma of 0.01
 C213-F10 \\sim C213-F11 \\sim C213-F12 \\sim C213-F10A \\sim C213-F11A \\sim
C213-F12A
 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
 C232-F22 \\sim C232-F23 \\sim C232-F24 \\sim C232-F22A \\sim C232-F23A \\sim
C232-F24A
 with sigma of 0.01
 F22-F23 \\sim F23-F24 \\sim F24-F22 \\sim F22A-F23A \\sim F23A-F24A \\sim
F24A-F22A
 with sigma of 0.01
 C229-F22 \\sim C229-F23 \\sim C229-F24 \\sim C229-F22A \\sim C229-F23A \\sim
C229-F24A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F4A \\sim F5 \\sim F5A \\sim F6 \\sim F6A
\\sim F7 \\sim F8 \\sim F9 \\sim F10 \\sim F10A \\sim F11 \\sim F11A \\sim F12
\\sim F12A \\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 F22A
\\sim F23 \\sim F23A \\sim F24 \\sim F24A: within 2A with sigma of 0.01 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(F4A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F6)
\\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq,
Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F11)
\\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F12A) \\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(F22A) \\sim Ueq,
Uanis(F23) \\sim Ueq, Uanis(F23A) \\sim Ueq, Uanis(F24) \\sim Ueq, Uanis(F24A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
 Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(3)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(3)
 Sof(F19A)=Sof(F20A)=Sof(F21A)=1-FVAR(4)
 Sof(F19)=Sof(F20)=Sof(F21)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C107(H10A,H10B), C113(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C103(H103), C104(H104), C105(H105), C111(H111), C112(H112), C117(H117),
 C118(H118), C202(H202), C204(H204), C206(H206), C210(H210), C212(H212),
 C214(H214), C218(H218), C220(H220), C222(H222), C226(H226), C228(H228),
 C230(H230)
5.d Idealised Me refined as rotating group:
 C119(H11C,H11D,H11E), C120(H12A,H12B,H12C)
;
_shelx_res_checksum              6997
_shelx_fab_checksum              51439
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.568