Site-Selective Carbene-Induced C–H Functionalization Catalyzed by Dirhodium Tetrakis(triarylcyclopropanecarboxylate) Complexes
Liao, Kuangbiao; Liu, Wenbin; Niemeyer, Zachary L.; Ren, Zhi; Bacsa, John; Musaev, Djamaladdin G.; Sigman, Mathew S.; Davies, Huw M. L.; ACS Catalysis 8 (2017) 678–; doi:10.1021/acscatal.7b03421

data_4514318
_publ_section_title
;
 Site-Selective Carbene-Induced C--H Functionalization Catalyzed by
 Dirhodium Tetrakis(triarylcyclopropanecarboxylate) Complexes
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              678
_journal_paper_doi               10.1021/acscatal.7b03421
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C92 H76 Cl4 O10 Rh2'
_chemical_formula_sum            'C92 H76 Cl4 O10 Rh2'
_chemical_formula_weight         1689.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-16
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5416(5)
_cell_length_b                   22.2438(9)
_cell_length_c                   23.4880(12)
_cell_measurement_reflns_used    18181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2810
_cell_measurement_theta_min      1.5250
_cell_volume                     8119.9(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.1-1 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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    -13.76 194.24   0.50   59.99    --   25.00  73.80 -90.14  416
  2  \f   -175.11  24.58   0.50   60.00-165.76  25.00  73.80    --   399
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0298698000
_diffrn_orient_matrix_UB_12      -0.0050126000
_diffrn_orient_matrix_UB_13      0.0223321000
_diffrn_orient_matrix_UB_21      0.0336756000
_diffrn_orient_matrix_UB_22      0.0110636000
_diffrn_orient_matrix_UB_23      -0.0175043000
_diffrn_orient_matrix_UB_31      -0.0075072000
_diffrn_orient_matrix_UB_32      0.0294869000
_diffrn_orient_matrix_UB_33      0.0103266000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            43599
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.571
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           35
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           45
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       prism
_exptl_crystal_F_000             3464
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.092
_refine_diff_density_max         1.295
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 3954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1345
_refine_ls_number_reflns         16445
_refine_ls_number_restraints     3774
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.1076
_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^)+(0.0253P)^2^+106.3908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2137
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                13307
_reflns_number_total             16445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03421_si_002.cif
_cod_data_source_block           wl-ni-roct
_cod_depositor_comments
'Adding full bibliography for 4514318--4514319.cif.'
_cod_database_code               4514318
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C368 H304 Cl16 O40 Rh8'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.832
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H,H) groups
2. Restrained distances
 C27_9-C26_9
 1.52 with sigma of 0.005
 C25_9-C26_9
 2.35 with sigma of 0.01
 O3_10-C25_10 = O3_10-C26_10
 1.42 with sigma of 0.005
 C25_10-C24_10
 1.52 with sigma of 0.005
 C25_10-C26_9
 2.35 with sigma of 0.01
 Rh2-O2_3 \\sim Rh2-O2_4
 with sigma of 0.004
 Rh1-O1_3 \\sim Rh1-O1_4
 with sigma of 0.004
 Rh2-O2_1 \\sim Rh2-O2_2
 with sigma of 0.004
 Rh1-O1_2 \\sim Rh1-O1_1
 with sigma of 0.004
 C4_6-C3_6 \\sim C4_6-C2_6
 with sigma of 0.02
 Rh1-C25_10 \\sim Rh1-C26_10
 with sigma of 0.01
 Rh1-O3_9 \\sim Rh1-O3_10
 with sigma of 0.002
3. Restrained planarity
 C18_3, C19_3, C21_3, C22_3, C20_3, C17_3
 with sigma of 0.002
 C5_3, C10_3, C9_3, C8_3, C7_3, C6_3, C2_3
 with sigma of 0.002
 C3_2, C17_2, C18_2, C19_2, C20_2, C21_2, C22_2
 with sigma of 0.002
 Cl1_6, C5_6, C6_6, C7_6, C8_6, C9_6, C10_6, C2_6
 with sigma of 0.002
 C11_6, C12_6, C13_6, C14_6, C15_6, C16_6, C3_6
 with sigma of 0.002
 C11_3, C12_3, C13_3, C14_3, C15_3, C16_3, C3_3
 with sigma of 0.002
 Cl1_3, C5_3, C6_3, C7_3, C8_3, C9_3, C10_3
 with sigma of 0.002
 C17_4, C18_4, C19_4, C20_4, C21_4, C22_4
 with sigma of 0.002
 Cl1_4, C5_4, C6_4, C7_4, C8_4, C9_4, C10_4
 with sigma of 0.002
 C17_1, C18_1, C19_1, C20_1, C21_1, C22_1, C3_1
 with sigma of 0.002
 C5_1, C6_1, C7_1, C8_1, C9_1, C10_1, Cl1_1
 with sigma of 0.002
 C11_4, C12_4, C13_4, C14_4, C15_4, C16_4, C3_4
 with sigma of 0.002
 Cl1_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2, C2_2
 with sigma of 0.002
 C17_5, C18_5, C19_5, C22_5, C20_5, C21_5, C3_5
 with sigma of 0.002
 C11_5, C12_5, C13_5, C14_5, C15_5, C16_5, C3_5
 with sigma of 0.002
 Cl1_5, C5_5, C6_5, C7_5, C8_5, C9_5, C10_5
 with sigma of 0.002
 C17_7, C18_7, C19_7, C20_7, C21_7, C22_7, C3_7
 with sigma of 0.002
 C7_7, C8_7, C9_7, C10_7, C5_7, C6_7, Cl1_7
 with sigma of 0.002
 C17_8, C18_8, C19_8, C20_8, C21_8, C22_8, C3_8
 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(C1_2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C14_2) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C5_2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C16_2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C8_3) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(Cl1_3) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C9_6) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C8_4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C9_4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C7_4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C12_1) \\sim Ueq, Uanis(C19_1) \\sim Ueq: with sigma of 0.002 and sigma
for terminal atoms of 0.004
Uanis(C18_1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C16_1) \\sim Ueq, Uanis(C15_1) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C6_1) \\sim Ueq, Uanis(C5_1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(Cl1_1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C1_5) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C10_6) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C12_7) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C10_8) \\sim Ueq, Uanis(C10_7) \\sim Ueq: with sigma of 0.002 and sigma
for terminal atoms of 0.004
Uanis(C25_10) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C4_3) = Uanis(C4_4)
Uanis(C10_4) = Uanis(C10_3)
Uanis(C5_4) = Uanis(C5_3)
Uanis(C11_3) = Uanis(C11_4)
Uanis(C3_4) = Uanis(C3_3)
Uanis(C17_4) = Uanis(C17_3)
Uanis(C20_3) = Uanis(C20_4)
Uanis(C12_4) = Uanis(C12_3)
Uanis(C15_3) = Uanis(C15_4)
Uanis(C16_3) = Uanis(C16_4)
Uanis(C13_3) = Uanis(C13_4)
Uanis(O2_4) = Uanis(O2_3)
Uanis(C1_3) = Uanis(C1_4)
Uanis(C22_3) = Uanis(C22_4)
Uanis(C21_3) = Uanis(C21_4)
Uanis(O1_3) = Uanis(O1_4)
Uanis(C18_3) = Uanis(C18_4) = Uanis(C19_3) = Uanis(C19_4)
Uanis(C6_3) = Uanis(C6_4)
Uanis(C9_4) = Uanis(C9_3)
Uanis(C2_1) = Uanis(C2_2)
Uanis(O2_2) = Uanis(O2_1)
Uanis(C3_1) = Uanis(C3_2)
Uanis(C4_1) = Uanis(C4_2)
Uanis(C1_1) = Uanis(C1_2)
Uanis(C19_1) = Uanis(C19_2)
Uanis(C20_1) = Uanis(C20_2)
Uanis(C7_1) = Uanis(C7_2) = Uanis(C8_1) = Uanis(C8_2) = Uanis(C9_1) =
Uanis(C9_2) = Uanis(C10_1) = Uanis(C10_2)
Uanis(C20_1) = Uanis(C20_2) = Uanis(C21_1) = Uanis(C21_2)
Uanis(C12_1) = Uanis(C12_2)
Uanis(O1_1) = Uanis(O1_2)
Uanis(C18_1) = Uanis(C18_2)
Uanis(Cl1_1) = Uanis(Cl1_2)
Uanis(O2_5) = Uanis(O2_6)
Uanis(C1_5) = Uanis(C1_6)
Uanis(O1_5) = Uanis(O1_6)
Uanis(C6_5) = Uanis(C6_6)
Uanis(Cl1_5) = Uanis(Cl1_6)
Uanis(C7_5) = Uanis(C7_6)
Uanis(C5_5) = Uanis(C5_6)
Uanis(C3_6) = Uanis(C3_5)
Uanis(C17_6) = Uanis(C17_5)
Uanis(C22_6) = Uanis(C22_5)
Uanis(C21_5) = Uanis(C21_6)
Uanis(C20_5) = Uanis(C20_6)
Uanis(C19_5) = Uanis(C19_6)
Uanis(C18_5) = Uanis(C18_6)
Uanis(C9_5) = Uanis(C9_6)
Uanis(C8_5) = Uanis(C8_6)
Uanis(C4_6) = Uanis(C4_5)
Uanis(C11_6) = Uanis(C11_5)
Uanis(C12_5) = Uanis(C12_6)
Uanis(C13_5) = Uanis(C13_6)
Uanis(C14_5) = Uanis(C14_6)
Uanis(C15_5) = Uanis(C15_6)
Uanis(C6_7) = Uanis(C10_7) = Uanis(C9_7) = Uanis(C8_7) = Uanis(C7_7)
Uanis(O2_8) = Uanis(O2_7)
Uanis(O1_7) = Uanis(O1_8)
Uanis(C1_7) = Uanis(C1_8)
Uanis(C2_7) = Uanis(C2_8)
Uanis(C4_7) = Uanis(C4_8)
Uanis(C11_7) = Uanis(C11_8)
Uanis(C16_7) = Uanis(C16_8)
Uanis(C15_7) = Uanis(C15_8)
Uanis(C13_7) = Uanis(C13_8)
Uanis(C12_7) = Uanis(C12_8)
Uanis(Cl1_7) = Uanis(Cl1_8)
Uanis(C7_7) = Uanis(C7_8)
Uanis(C8_7) = Uanis(C8_8)
Uanis(C9_7) = Uanis(C9_8)
Uanis(C18_7) = Uanis(C18_8)
Uanis(C17_7) = Uanis(C17_8)
Uanis(C19_7) = Uanis(C19_8)
Uanis(C20_7) = Uanis(C20_8)
Uanis(C22_7) = Uanis(C22_8)
Uanis(C21_7) = Uanis(C21_8)
Uanis(C26_9) = Uanis(C27_10)
Uanis(C25_9) = Uanis(C26_10)
Uanis(C27_9) = Uanis(C24_10)
Uanis(C24_9) = Uanis(O3_10)
Uanis(O3_9) = Uanis(C25_10)
Uanis(O3_10) = Uanis(O3_9)
Uanis(C26_9) = Uanis(C26_10)
Uanis(C27_9) = Uanis(C27_10)
Uanis(C24_9) = Uanis(C24_10)
5. Rigid body (RIGU) restrains
 Rh2, O1W
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 Cl1_2, O1_2, O2_2, C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2,
 C10_2, C11_2, C12_2, C13_2, C14_2, C15_2, C16_2, C17_2, C18_2, C19_2, C20_2,
 C21_2, C22_2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Rh1, O1_3, Rh2, C1_3, O2_3, O1W, C2_3, C3_3, C4_3, C5_3, C11_3, C17_3, C6_3,
 C10_3, C12_3, C16_3, C18_3, C22_3, Cl1_3, C7_3, C9_3, C13_3, C15_3, C19_3,
 C21_3, C8_3, C14_3, C20_3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1_3, O1_3, O2_3, C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3,
 C10_3, C11_3, C12_3, C13_3, C14_3, C15_3, C16_3, C17_3, C18_3, C19_3, C20_3,
 C21_3, C22_3
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Cl1_6, O1_6, O2_6, C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6,
 C10_6, C11_6, C12_6, C13_6, C14_6, C15_6, C16_6, C17_6, C18_6, C19_6, C20_6,
 C21_6, C22_6
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Cl1_4, O1_4, O2_4, C1_4, C2_4, C3_4, C4_4, C5_4, C6_4, C7_4, C8_4, C9_4,
 C10_4, C11_4, C12_4, C13_4, C14_4, C15_4, C16_4, C17_4, C18_4, C19_4, C20_4,
 C21_4, C22_4
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 Cl1_1, O1_1, O2_1, C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1,
 C10_1, C11_1, C12_1, C13_1, C14_1, C15_1, C16_1, C17_1, C18_1, C19_1, C20_1,
 C21_1, C22_1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Cl1_6, O1_6, O2_6, C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6,
 C10_6, C11_6, C12_6, C13_6, C14_6, C15_6, C16_6, C17_6, C18_6, C19_6, C20_6,
 C21_6, C22_6, Cl1_7, O1_7, O2_7, C1_7, C2_7, C3_7, C4_7, C5_7, C6_7, C7_7,
 C8_7, C9_7, C10_7, C11_7, C12_7, C13_7, C14_7, C15_7, C16_7, C17_7, C18_7,
 C19_7, C20_7, C21_7, C22_7
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Cl1_7, O1_7, O2_7, C1_7, C2_7, C3_7, C4_7, C5_7, C6_7, C7_7, C8_7, C9_7,
 C10_7, C11_7, C12_7, C13_7, C14_7, C15_7, C16_7, C17_7, C18_7, C19_7, C20_7,
 C21_7, C22_7, Cl1_5, O1_5, O2_5, C1_5, C2_5, C3_5, C4_5, C5_5, C6_5, C7_5,
 C8_5, C9_5, C10_5, C11_5, C12_5, C13_5, C14_5, C15_5, C16_5, C17_5, C18_5,
 C19_5, C20_5, C21_5, C22_5
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Cl1_8, O1_8, O2_8, C1_8, C2_8, C3_8, C4_8, C5_8, C6_8, C7_8, C8_8, C9_8,
 C10_8, C11_8, C12_8, C13_8, C14_8, C15_8, C16_8, C17_8, C18_8, C19_8, C20_8,
 C21_8, C22_8
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O3_10, C24_10, C25_10, C26_10, C27_10
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
6. Same fragment restrains
{Cl1_6, O1_6, O2_6, C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6,
C10_6, C11_6, C12_6, C13_6, C14_6, C15_6, C16_6, C17_6, C18_6, C19_6, C20_6,
C21_6, C22_6}
{Cl1_2, O1_2, O2_2, C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2,
C10_2, C11_2, C12_2, C13_2, C14_2, C15_2, C16_2, C17_2, C18_2, C19_2, C20_2,
C21_2, C22_2}
{Cl1_4, O1_4, O2_4, C1_4, C2_4, C3_4, C4_4, C5_4, C6_4, C7_4, C8_4, C9_4,
C10_4, C11_4, C12_4, C13_4, C14_4, C15_4, C16_4, C17_4, C18_4, C19_4, C20_4,
C21_4, C22_4}
{Cl1_1, O1_1, O2_1, C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1,
C10_1, C11_1, C12_1, C13_1, C14_1, C15_1, C16_1, C17_1, C18_1, C19_1, C20_1,
C21_1, C22_1}
{Cl1_5, O1_5, O2_5, C1_5, C2_5, C3_5, C4_5, C5_5, C6_5, C7_5, C8_5, C9_5,
C10_5, C11_5, C12_5, C13_5, C14_5, C15_5, C16_5, C17_5, C18_5, C19_5, C20_5,
C21_5, C22_5}
{Cl1_7, O1_7, O2_7, C1_7, C2_7, C3_7, C4_7, C5_7, C6_7, C7_7, C8_7, C9_7,
C10_7, C11_7, C12_7, C13_7, C14_7, C15_7, C16_7, C17_7, C18_7, C19_7, C20_7,
C21_7, C22_7}
{Cl1_8, O1_8, O2_8, C1_8, C2_8, C3_8, C4_8, C5_8, C6_8, C7_8, C8_8, C9_8,
C10_8, C11_8, C12_8, C13_8, C14_8, C15_8, C16_8, C17_8, C18_8, C19_8, C20_8,
C21_8, C22_8}
as
{Cl1_3, O1_3, O2_3, C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3,
C10_3, C11_3, C12_3, C13_3, C14_3, C15_3, C16_3, C17_3, C18_3, C19_3, C20_3,
C21_3, C22_3} sigma for 1-2: 0.01 1-3: 0.02
{O3_10, C24_10, C25_10, C26_10, C27_10}
as
{O3_9, C24_9, C25_9, C26_9, C27_9} sigma for 1-2: 0.002 1-3: 0.004
7. Others
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=1-FVAR(1)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(1)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=1-FVAR(2)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(2)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=1-FVAR(3)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(3)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=1-FVAR(4)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(4)
 Sof(O3)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=1-FVAR(5)
 Sof(O3)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(5)
 Fixed X: O2(0.7491)
 Fixed Y: O2(0.44508)
 Fixed Z: O2(0.13885)
8.a Rotating group:
 O1W(H1WA,H1WB)
8.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4(H4A,H4B), C4(H4A,H4B), C4(H4A,H4B), C4(H4A,H4B), C4(H4A,H4B),
 C4(H4A,H4B), C4(H4A,H4B), C25(H25A,H25B), C26(H26A,H26B), C25(H25A,H25B),
 C26(H26A,H26B)
8.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C7(H7), C8(H8),
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C7(H7), C8(H8), C9(H9), C10(H10),
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
  C21(H21), C22(H22), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C7(H7), C8(H8),
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C7(H7), C8(H8), C9(H9), C10(H10),
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
  C21(H21), C22(H22), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
8.d Idealised Me refined with riding coordinates:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              24747
_shelx_hkl_checksum              26198
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id WL-NI-ROCT
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.228
_oxdiff_exptl_absorpt_empirical_full_min 0.654