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_1557117
_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         'C29 H27 N7 Rh, C32 H12 B F24'
_chemical_formula_sum            'C61 H39 B F24 N7 Rh'
_chemical_formula_weight         1439.71
_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'
_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                74.898(6)
_cell_angle_beta                 79.351(5)
_cell_angle_gamma                89.459(4)
_cell_formula_units_Z            2
_cell_length_a                   12.9083(7)
_cell_length_b                   14.2464(8)
_cell_length_c                   20.1480(15)
_cell_measurement_reflns_used    4028
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.4070
_cell_measurement_theta_min      3.1820
_cell_volume                     3512.7(4)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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    -66.00  33.00   1.00   16.00    --  -41.82  37.00 -90.00   99
  2  \w    -92.00  -2.00   1.00   16.00    --  -41.82 125.00-180.00   90
  3  \w   -114.00 -14.00   1.00   16.00    --  -41.82 -57.00 -30.00  100
  4  \w    -70.00  31.00   1.00   16.00    --  -41.82  57.00 120.00  101
  5  \w   -116.00 -17.00   1.00   16.00    --  -41.82 -37.00  90.00   99
  6  \w     80.00 178.00   1.00   80.00    --  105.98  45.00 -60.00   98
  7  \w     94.00 178.00   1.00   80.00    --  105.98 125.00-150.00   84
  8  \w     33.00 132.00   1.00   80.00    --  105.98 -45.00  30.00   99
  9  \w     80.00 178.00   1.00   80.00    --  105.98  45.00 -30.00   98
;
_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      -0.1124803000
_diffrn_orient_matrix_UB_12      0.0302838000
_diffrn_orient_matrix_UB_13      0.0245864000
_diffrn_orient_matrix_UB_21      -0.0163956000
_diffrn_orient_matrix_UB_22      0.0302354000
_diffrn_orient_matrix_UB_23      -0.0764061000
_diffrn_orient_matrix_UB_31      -0.0430254000
_diffrn_orient_matrix_UB_32      -0.1036087000
_diffrn_orient_matrix_UB_33      0.0078685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9021
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        39.960
_diffrn_reflns_theta_max         39.960
_diffrn_reflns_theta_min         6.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46493
_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            'pale yellow'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_recrystallization_method
'Crystals grown from CH2Cl2-hexane at 243 K'
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.953
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1045
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     1977
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0997
_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^)+(0.1364P)^2^+69.5046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2466
_refine_ls_wR_factor_ref         0.2619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3302
_reflns_number_total             4155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06153c3.cif
_cod_data_source_block           0461abc18s
_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               1557117
_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
 C207-F1 \\sim C207-F2 \\sim C207-F3 \\sim C207-F1A \\sim C207-F2A \\sim
C207-F3A
 with sigma of 0.01
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.01
 C203-F1 \\sim C203-F2 \\sim C203-F3 \\sim C203-F1A \\sim C203-F2A \\sim
C203-F3A
 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
 C223-F13 \\sim C223-F14 \\sim C223-F15 \\sim C223-F13A \\sim C223-F14A \\sim
C223-F15A
 with sigma of 0.01
 F13-F14 \\sim F14-F15 \\sim F15-F13 \\sim F13A-F14A \\sim F14A-F15A \\sim
F15A-F13A
 with sigma of 0.01
 C219-F13 \\sim C219-F14 \\sim C219-F15 \\sim C219-F13A \\sim C219-F14A \\sim
C219-F15A
 with sigma of 0.01
 C224-F16 \\sim C224-F17 \\sim C224-F18 \\sim C224-F16A \\sim C224-F17A \\sim
C224-F18A
 with sigma of 0.01
 F16-F17 \\sim F17-F18 \\sim F18-F16 \\sim F16A-F17A \\sim F17A-F18A \\sim
F18A-F16A
 with sigma of 0.01
 C221-F16 \\sim C221-F17 \\sim C221-F18 \\sim C221-F16A \\sim C221-F17A \\sim
C221-F18A
 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
 C215-F7A \\sim C215-F8A \\sim C215-F9A \\sim C215-F7 \\sim C215-F8 \\sim
C215-F9
 with sigma of 0.01
 F7A-F8A \\sim F8A-F9A \\sim F9A-F7A \\sim F7-F8 \\sim F8-F9 \\sim F9-F7
 with sigma of 0.01
 C211-F7A \\sim C211-F8A \\sim C211-F9A \\sim C211-F7 \\sim C211-F8 \\sim
C211-F9
 with sigma of 0.01
 C208-F4A \\sim C208-F5A \\sim C208-F6A \\sim C208-F4 \\sim C208-F5 \\sim
C208-F6
 with sigma of 0.01
 F4A-F5A \\sim F5A-F6A \\sim F6A-F4A \\sim F4-F5 \\sim F5-F6 \\sim F6-F4
 with sigma of 0.01
 C205-F4A \\sim C205-F5A \\sim C205-F6A \\sim C205-F4 \\sim C205-F5 \\sim
C205-F6
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Others
 Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(1)
 Sof(F16)=Sof(F17)=Sof(F18)=FVAR(1)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=1-FVAR(2)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(2)
 Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(3)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(3)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(4)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(4)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(5)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(5)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(6)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(6)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(7)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(7)
5.a Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C113(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 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.c X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
5.d Idealised Me refined as rotating group:
 C119(H11C,H11D,H11E), C120(H12A,H12B,H12C)
;
_shelx_res_checksum              8416
_shelx_fab_checksum              16172
_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 1.928
_oxdiff_exptl_absorpt_empirical_full_min 0.646