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_1557116
_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         'C64 H88'
_chemical_formula_sum            'C64 H88'
_chemical_formula_weight         857.34
_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                79.631(4)
_cell_angle_beta                 75.201(4)
_cell_angle_gamma                74.120(4)
_cell_formula_units_Z            4
_cell_length_a                   14.6350(7)
_cell_length_b                   18.1373(9)
_cell_length_c                   22.0161(10)
_cell_measurement_reflns_used    20066
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.3270
_cell_measurement_theta_min      4.4980
_cell_volume                     5396.2(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -121.00  -5.00   1.00   10.00    --  -42.36 -19.00-120.00  116
  2  \w    -96.00  -2.00   1.00   10.00    --  -42.36 125.00 150.00   94
  3  \w    -96.00  -2.00   1.00   10.00    --  -42.36 125.00-120.00   94
  4  \w    -65.00  31.00   1.00   10.00    --  -42.36  37.00  60.00   96
  5  \w      1.00  82.00   1.00   10.00    --   42.36 -99.00 120.00   81
  6  \w     36.00 134.00   1.00   40.00    --  106.00 -61.00 150.00   98
  7  \w     34.00 121.00   1.00   40.00    --  106.00-125.00-150.00   87
  8  \w     78.00 176.00   1.00   40.00    --  106.00  61.00   0.00   98
  9  \w     36.00 134.00   1.00   40.00    --  106.00 -61.00 -60.00   98
 10  \w     26.00 151.00   1.00   40.00    --  106.00 -15.00-180.00  125
 11  \w     25.00 109.00   1.00   40.00    --  106.00 -94.00  90.00   84
 12  \w     25.00 109.00   1.00   40.00    --  106.00 -94.00-150.00   84
 13  \w     82.00 178.00   1.00   40.00    --  106.00  30.00 150.00   96
 14  \w     34.00 121.00   1.00   40.00    --  106.00-125.00  90.00   87
 15  \w     82.00 178.00   1.00   40.00    --  106.00  30.00-150.00   96
 16  \w     94.00 178.00   1.00   40.00    --  106.00 125.00 150.00   84
 17  \w     32.00 137.00   1.00   40.00    --  106.00 -77.00  30.00  105
 18  \w     25.00 109.00   1.00   40.00    --  106.00 -94.00 -90.00   84
 19  \w     34.00 121.00   1.00   40.00    --  106.00-125.00  30.00   87
 20  \w     78.00 176.00   1.00   40.00    --  106.00  61.00-120.00   98
 21  \w     25.00 109.00   1.00   40.00    --  106.00 -94.00 -60.00   84
 22  \w     34.00 121.00   1.00   40.00    --  106.00-125.00-120.00   87
 23  \w     25.00 109.00   1.00   40.00    --  106.00 -94.00 -30.00   84
 24  \w     35.00 130.00   1.00   40.00    --  106.00 -45.00 -60.00   95
 25  \w     26.00 151.00   1.00   40.00    --  106.00 -15.00 -30.00  125
 26  \w     34.00 121.00   1.00   40.00    --  106.00-125.00-180.00   87
 27  \w     32.00 137.00   1.00   40.00    --  106.00 -77.00-150.00  105
 28  \w     26.00 151.00   1.00   40.00    --  106.00 -15.00 120.00  125
 29  \w     34.00 121.00   1.00   40.00    --  106.00-125.00 -60.00   87
 30  \w     35.00 130.00   1.00   40.00    --  106.00 -45.00  30.00   95
 31  \w     94.00 178.00   1.00   40.00    --  106.00 125.00  60.00   84
 32  \w   -116.00 -58.00   1.00   10.00    --  -42.36 -77.00  60.00   58
 33  \w     43.00  69.00   1.00   40.00    --  106.00 -45.00  60.00   26
 34  \w     75.00 101.00   1.00   40.00    --  106.00 -45.00  60.00   26
 35  \w    105.00 130.00   1.00   40.00    --  106.00 -45.00 150.00   25
 36  \w   -115.00 -20.00   1.00   10.00    --  -42.36 -37.00 150.00   95
 37  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00 120.00  105
 38  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00 -60.00  105
 39  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00  30.00  105
 40  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00-150.00  105
 41  \w     78.00 176.00   1.00   40.00    --  106.00  61.00  60.00   98
 42  \w     78.00 176.00   1.00   40.00    --  106.00  61.00 150.00   98
 43  \w     78.00 176.00   1.00   40.00    --  106.00  61.00 -60.00   98
 44  \w     78.00 176.00   1.00   40.00    --  106.00  61.00  30.00   98
 45  \w     78.00 176.00   1.00   40.00    --  106.00  61.00 -90.00   98
 46  \w     78.00 176.00   1.00   40.00    --  106.00  61.00 -30.00   98
 47  \w     78.00 176.00   1.00   40.00    --  106.00  61.00-150.00   98
 48  \w     78.00 176.00   1.00   40.00    --  106.00  61.00 120.00   98
 49  \w     78.00 176.00   1.00   40.00    --  106.00  61.00-180.00   98
 50  \w     75.00 161.00   1.00   40.00    --  106.00  77.00 -30.00   86
 51  \w     75.00 178.00   1.00   40.00    --  106.00  77.00   0.00  103
 52  \w     78.00 176.00   1.00   40.00    --  106.00  61.00  90.00   98
 53  \w   -115.00 -53.00   1.00   10.00    --  -42.36 -37.00  30.00   62
 54  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00 150.00  105
 55  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00  90.00  105
 56  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00-120.00  105
 57  \w   -113.00 -16.00   1.00   10.00    --  -42.36 -57.00 150.00   97
 58  \w   -113.00 -16.00   1.00   10.00    --  -42.36 -57.00 -30.00   97
 59  \w     20.00 115.00   1.00   10.00    --   42.36  37.00 -30.00   95
 60  \w     16.00 113.00   1.00   10.00    --   42.36  57.00   0.00   97
 61  \w   -115.00 -20.00   1.00   10.00    --  -42.36 -37.00-150.00   95
 62  \w   -115.00 -20.00   1.00   10.00    --  -42.36 -37.00-120.00   95
 63  \w   -113.00 -18.00   1.00   10.00    --  -42.36 -57.00 -90.00   95
 64  \w   -116.00 -11.00   1.00   10.00    --  -42.36 -77.00 -30.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0481011000
_diffrn_orient_matrix_UB_12      -0.0509636000
_diffrn_orient_matrix_UB_13      -0.0245407000
_diffrn_orient_matrix_UB_21      -0.0972144000
_diffrn_orient_matrix_UB_22      0.0304953000
_diffrn_orient_matrix_UB_23      0.0454044000
_diffrn_orient_matrix_UB_31      -0.0282436000
_diffrn_orient_matrix_UB_32      0.0661419000
_diffrn_orient_matrix_UB_33      -0.0515436000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31197
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         6.326
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  -0.010
_exptl_absorpt_correction_T_min  10000000.000
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_recrystallization_method 'Crystals grown from SiMe4 at 293 K'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.066
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1202
_refine_ls_number_reflns         31197
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.1066
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.2812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22736
_reflns_number_total             31197
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9303\% 
 around [-0.31 -0.00 0.95] (reciprocal) or [-0.71 0.00 0.71] (direct)
;
_cod_data_source_file            c9sc06153c3.cif
_cod_data_source_block           0311abc17s
_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               1557116
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6841(12)
 0.3159(12)
2. 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
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C58 \\sim C59 \\sim C60 \\sim C116 \\sim C117
\\sim C118 \\sim C144 \\sim C145 \\sim C146 \\sim C162 \\sim C163 \\sim C164:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C58)
\\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C116) \\sim Ueq,
Uanis(C117) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C144) \\sim Ueq,
Uanis(C145) \\sim Ueq, Uanis(C146) \\sim Ueq, Uanis(C162) \\sim Ueq,
Uanis(C163) \\sim Ueq, Uanis(C164) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C103(H10A,H10B), C104(H10C,H10D)
4.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C14(H14), C24(H24), C26(H26), C28(H28), C38(H38),
 C40(H40), C42(H42), C52(H52), C54(H54), C56(H56), C110(H110), C112(H112),
 C114(H114), C124(H124), C126(H126), C128(H128), C138(H138), C140(H140),
 C142(H142), C152(H152), C154(H154), C156(H156)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C58(H58A,
 H58B,H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C),
 C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C116(H11A,H11B,H11C), C117(H11D,H11E,
 H11F), C118(H11G,H11H,H11I), C120(H12A,H12B,H12C), C121(H12D,H12E,H12F),
 C122(H12G,H12H,H12I), C130(H13A,H13B,H13C), C131(H13D,H13E,H13F), C132(H13G,
 H13H,H13I), C134(H13J,H13K,H13L), C135(H13M,H13N,H13O), C136(H13P,H13Q,H13R),
 C144(H14A,H14B,H14C), C145(H14D,H14E,H14F), C146(H14G,H14H,H14I), C148(H14J,
 H14K,H14L), C149(H14M,H14N,H14O), C150(H15A,H15B,H15C), C158(H15D,H15E,H15F),
 C159(H15G,H15H,H15I), C160(H16D,H16E,H16F), C162(H16G,H16H,H16I), C163(H16J,
 H16K,H16L), C164(H16M,H16N,H16O)
;
_shelx_res_checksum              77203
_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 2.512
_oxdiff_exptl_absorpt_empirical_full_min 0.701
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2