Catalyst-Controlled Selective Functionalization of Unactivated C-H Bonds in the Presence of Electronically Activated C-H Bonds.
Liu, Wenbin; Ren, Zhi; Bosse, Aaron T.; Liao, Kuangbiao; Goldstein, Elizabeth L.; Bacsa, John; Musaev, Djamaladdin G.; Stoltz, Brian M.; Davies, Huw M. L.; Journal of the American Chemical Society 140 (2018) 12247–12255; doi:10.1021/jacs.8b07534

data_4132944
_publ_section_title
;
 Catalyst-Controlled Selective Functionalization of Unactivated C-H Bonds
 in the Presence of Electronically Activated C-H Bonds.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12247
_journal_page_last               12255
_journal_paper_doi               10.1021/jacs.8b07534
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C90 H65 Br4 Cl4 N O9 Rh2, C92 H66 Br4 Cl4 N2 O8 Rh2'
_chemical_formula_sum            'C182 H131 Br8 Cl8 N3 O17 Rh4'
_chemical_formula_weight         3966.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-03
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.965(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   21.4690(3)
_cell_length_b                   17.1974(3)
_cell_length_c                   29.1637(4)
_cell_measurement_reflns_used    49303
_cell_measurement_temperature    100.3(5)
_cell_measurement_theta_max      72.4860
_cell_measurement_theta_min      2.3110
_cell_volume                     10299.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_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     51.00  77.00   0.50    3.00    --   47.12-125.00 -90.00   52
  2  \w     41.00  95.00   0.50    3.00    --   47.12-125.00 -30.00  108
  3  \w     35.00 112.00   0.50    7.21    --  103.57-125.00   0.00  154
  4  \w   -115.00 -70.00   0.50    7.21    --  -47.12-125.00   0.00   90
  5  \w     73.00  99.00   0.50    7.21    --  103.57 -99.00  60.00   52
  6  \w     31.00  72.00   0.50    7.21    --  103.57 -99.00-150.00   82
  7  \w     31.00  57.00   0.50    7.21    --  103.57 -99.00  60.00   52
  8  \w     38.00 110.00   0.50    7.21    --  103.57 -99.00 150.00  144
  9  \w   -151.00 -85.00   0.50    7.21    --  -88.50 -99.00 -60.00  132
 10  \w     43.00 101.00   0.50    7.21    --  103.57 -77.00   0.00  116
 11  \w     31.00 105.00   0.50    7.21    --  103.57 -77.00-120.00  148
 12  \w     50.00  87.00   0.50    7.21    --  103.57 -73.00-149.00   74
 13  \w    -10.00  68.00   0.50    7.21    --   47.12 -73.00-149.00  156
 14  \w   -118.00 -28.00   0.50    7.21    --  -47.12 -73.00-149.00  180
 15  \w   -146.00-120.00   0.50    7.21    --  -88.50 -73.00-149.00   52
 16  \w     31.00  81.00   0.50    7.21    --  103.57 -57.00   0.00  100
 17  \w     31.00  56.00   0.50    7.21    --  103.57 -57.00  90.00   50
 18  \w   -128.00 -77.00   0.50    7.21    --  -88.50 -38.00  90.00  102
 19  \w   -154.00 -74.00   0.50    7.21    --  -88.50 -38.00  60.00  160
 20  \w   -157.00 -77.00   0.50    7.21    --  -88.50 -38.00  30.00  160
 21  \w     30.00 118.00   0.50    7.21    --  103.57 -19.00-150.00  176
 22  \w   -116.00 -74.00   0.50    7.21    --  -88.50 -19.00  90.00   84
 23  \w   -159.00-123.00   0.50    7.21    --  -88.50 -19.00  90.00   72
 24  \w    -58.00  28.00   0.50    7.21    --  -47.12  19.00   0.00  172
 25  \w    152.00 177.00   0.50    7.21    --  103.57  38.00-120.00   50
 26  \w    106.00 132.00   0.50    7.21    --  103.57  38.00-120.00   52
 27  \w     92.00 117.00   0.50    7.21    --  103.57  38.00-180.00   50
 28  \w    -47.00 -22.00   0.50    7.21    --  -88.50  38.00 -90.00   50
 29  \w   -101.00 -67.00   0.50    7.21    --  -88.50  38.00 -90.00   68
 30  \w     33.00  84.00   0.50    7.21    --   47.12  57.00-150.00  102
 31  \w     82.00 176.00   0.50    7.21    --  103.57  73.00 -19.00  188
 32  \w     48.00  73.00   0.50    7.21    --   47.12  73.00 -19.00   50
 33  \w    -47.00  11.00   0.50    7.21    --  -47.12  73.00 -19.00  116
 34  \w    -57.00 -16.00   0.50    7.21    --  -88.50  73.00 -19.00   82
 35  \w    139.00 165.00   0.50    7.21    --  103.57 125.00  60.00   52
 36  \w     98.00 123.00   0.50    7.21    --  103.57 125.00  60.00   50
 37  \w    -50.00 -17.00   0.50    7.21    --  -88.50 125.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0245598000
_diffrn_orient_matrix_UB_12      -0.0068574000
_diffrn_orient_matrix_UB_13      -0.0550512000
_diffrn_orient_matrix_UB_21      -0.0434837000
_diffrn_orient_matrix_UB_22      0.0719489000
_diffrn_orient_matrix_UB_23      -0.0021849000
_diffrn_orient_matrix_UB_31      0.0560074000
_diffrn_orient_matrix_UB_32      0.0528385000
_diffrn_orient_matrix_UB_33      -0.0042044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            121262
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.741
_exptl_absorpt_correction_T_max  0.486
_exptl_absorpt_correction_T_min  0.028
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33a (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       needle
_exptl_crystal_F_000             3952
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.084
_platon_squeeze_details
;
TITL wl-2cl5br_a.res in P2(1)
CELL   21.4690   17.1974   29.1637     90.00    106.96     90.00
SPGR P21
C101 0.030 0.911 0.376 !       4.17 eA-3
C102 0.025 0.036 0.768 !       3.58 eA-3
C103 0.123 0.110 0.808 !       3.51 eA-3
C104 0.304 0.648 0.912 !       2.93 eA-3
Q105 0.664 0.011 0.592 !       2.88 eA-3
C106 0.023 0.893 0.412 !       2.88 eA-3
C107 0.991 0.326 0.599 !       2.77 eA-3
C108 0.992 0.470 0.294 !       2.73 eA-3
C109 0.376 0.599 0.261 !       2.68 eA-3
C110 0.328 0.718 0.911 !       2.61 eA-3
Q111 0.743 0.607 0.714 !       2.55 eA-3
C112 0.874 0.661 0.345 !       2.43 eA-3
C113 0.025 0.404 0.341 !       2.43 eA-3
C114 0.451 0.988 0.978 !       2.40 eA-3
C115 0.307 0.764 0.857 !       2.35 eA-3
C116 0.704 0.030 0.040 !       2.32 eA-3
C117 0.085 0.751 0.500 !       2.29 eA-3
C118 0.585 0.928 0.625 !       2.27 eA-3
C119 0.117 0.155 0.633 !       2.25 eA-3
C120 0.976 0.313 0.570 !       2.24 eA-3
C121 0.727 0.496 0.231 !       2.18 eA-3
C122 0.351 0.500 0.040 !       2.14 eA-3
Q123 0.024 0.266 0.301 !       2.13 eA-3
C124 0.381 0.565 0.240 !       2.12 eA-3
C125 0.260 0.978 0.787 !       2.09 eA-3
Q126 0.436 0.011 0.365 !       2.08 eA-3
C127 0.328 0.455 0.012 !       2.07 eA-3
C128 0.320 0.433 0.355 !       2.06 eA-3
C129 0.671 0.880 0.625 !       2.04 eA-3
Q130 0.134 0.454 0.114 !       2.03 eA-3
C131 0.320 0.567 0.967 !       2.03 eA-3
C132 0.596 0.421 0.087 !       2.02 eA-3
C133 0.353 0.479 0.329 !       1.99 eA-3
C134 0.968 0.482 0.661 !       1.98 eA-3
C135 0.287 0.052 0.760 !       1.98 eA-3
C136 0.045 0.287 0.631 !       1.90 eA-3
C137 0.047 0.941 0.435 !       1.89 eA-3
C138 0.529 0.044 0.985 !       1.87 eA-3
C139 0.936 0.703 0.384 !       1.87 eA-3
Q140 0.735 0.093 0.049 !       1.85 eA-3
C141 0.304 0.338 0.367 !       1.84 eA-3
C142 0.593 0.017 0.683 !       1.83 eA-3
C143 0.641 0.043 0.830 !       1.82 eA-3
C144 0.889 0.594 0.377 !       1.82 eA-3
C145 0.619 0.959 0.652 !       1.81 eA-3
C146 0.372 0.413 0.363 !       1.80 eA-3
C147 0.406 0.522 0.300 !       1.78 eA-3
C148 1.001 0.786 0.463 !       1.78 eA-3
C149 0.732 0.599 0.223 !       1.77 eA-3
C150 0.600 0.070 0.693 !       1.72 eA-3
C151 0.298 0.094 0.814 !       1.72 eA-3
C152 0.704 0.664 0.269 !       1.70 eA-3
C153 0.866 0.573 0.383 !       1.69 eA-3
C154 0.951 0.313 0.482 !       1.68 eA-3
C155 0.172 0.151 0.824 !       1.68 eA-3
C156 0.360 0.308 0.394 !       1.66 eA-3
C157 0.687 0.017 0.019 !       1.65 eA-3
C158 0.881 0.567 0.439 !       1.63 eA-3
C159 0.233 0.501 0.114 !       1.61 eA-3
C160 0.640 0.818 0.613 !       1.61 eA-3
C161 0.983 0.483 0.327 !       1.61 eA-3
Q162 0.789 0.033 0.853 !       1.60 eA-3
C163 0.732 0.019 0.841 !       1.59 eA-3
Q164 0.998 0.926 0.502 !       1.59 eA-3
C165 0.689 0.016 0.856 !       1.56 eA-3
Q166 0.617 0.465 0.486 !       1.55 eA-3
C167 0.618 0.008 0.818 !       1.54 eA-3
C168 0.350 0.870 0.930 !       1.52 eA-3
C169 0.797 0.664 0.184 !       1.52 eA-3
Q170 0.804 0.943 0.870 !       1.50 eA-3
C171 0.345 0.865 0.886 !       1.50 eA-3
C172 0.937 0.381 0.483 !       1.49 eA-3
Q173 0.588 0.938 0.535 !       1.49 eA-3
C174 0.522 0.968 0.972 !       1.48 eA-3
C175 0.280 0.113 0.749 !       1.47 eA-3
Q176 0.438 0.029 0.181 !       1.47 eA-3
C177 0.361 0.489 0.300 !       1.47 eA-3
C178 0.893 0.589 0.403 !       1.46 eA-3
C179 0.691 0.543 0.160 !       1.45 eA-3
C180 0.024 0.858 0.706 !       1.44 eA-3
C181 0.306 0.924 0.904 !       1.43 eA-3
C182 0.280 0.645 0.877 !       1.40 eA-3
C183 0.291 0.048 0.807 !       1.39 eA-3
Q184 0.469 0.606 0.791 !       1.39 eA-3
C185 0.901 0.734 0.320 !       1.37 eA-3
C186 0.852 0.611 0.409 !       1.37 eA-3
C187 0.857 0.721 0.263 !       1.37 eA-3
Q188 0.532 0.063 0.938 !       1.37 eA-3
C189 0.357 0.536 0.008 !       1.35 eA-3
C190 0.962 0.969 0.737 !       1.33 eA-3
C191 0.609 0.467 0.058 !       1.33 eA-3
C192 0.062 0.984 0.708 !       1.31 eA-3
C193 0.352 0.936 0.926 !       1.30 eA-3
C194 0.431 0.514 0.018 !       1.30 eA-3
Q195 0.407 0.454 0.079 !       1.30 eA-3
C196 0.720 0.980 0.984 !       1.29 eA-3
C197 0.250 0.015 0.827 !       1.28 eA-3
Q198 0.561 0.516 0.368 !       1.27 eA-3
C199 0.358 0.291 0.362 !       1.27 eA-3
;
_refine_diff_density_max         2.315
_refine_diff_density_min         -2.101
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.066(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2131
_refine_ls_number_reflns         36989
_refine_ls_number_restraints     4101
_refine_ls_restrained_S_all      1.225
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1417P)^2^+19.4469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2229
_refine_ls_wR_factor_ref         0.2353
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                30571
_reflns_number_total             36989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07534_si_004.cif
_cod_data_source_block           wl-2cl5br_sq
_cod_database_code               4132944
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C350  H462  O112  Cl56  Br28  Rh28  '
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.934(12)
 0.066(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, All O(H,H) groups
3. Restrained distances
 Rh2-O1_12 \\sim Rh2-O1_4
 with sigma of 0.002
 Rh1-O2_4 \\sim Rh1-O2_12
 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(C23_10) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C21_2) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(Br1_8) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C4_8) \\sim Ueq, Uanis(C9_8) \\sim Ueq, Uanis(C8_8) \\sim Ueq,
Uanis(C7_8) \\sim Ueq, Uanis(C6_8) \\sim Ueq, Uanis(C5_8) \\sim Ueq,
Uanis(Cl1_8) \\sim Ueq, Uanis(Br1_8) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C18_7) \\sim Ueq, Uanis(C19_7) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C23_11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C11_4) = Uanis(C11_12)
Uanis(C15_12) = Uanis(C15_4)
Uanis(C22_4) = Uanis(C22_12)
Uanis(C18_12) = Uanis(C18_4)
Uanis(C17_12) = Uanis(C17_4)
Uanis(C21_12) = Uanis(C21_4)
Uanis(C10_4) = Uanis(C10_12)
Uanis(Cl1_12) = Uanis(Cl1_4)
Uanis(C5_12) = Uanis(C5_4)
Uanis(C6_12) = Uanis(C7_4)
Uanis(C1_4) = Uanis(C1_12)
Uanis(C2_4) = Uanis(C2_12)
Uanis(O2_12) = Uanis(O2_4)
Uanis(O1_12) = Uanis(O1_4)
Uanis(C3_12) = Uanis(C3_4)
Uanis(Br1_12) = Uanis(Br1_4)
Uanis(C7_12) = Uanis(C8_4)
Uanis(C6_12) = Uanis(C6_4)
5. Rigid body (RIGU) restrains
 C1_8, Br1_8, C8_8, C7_8, C9_8, C6_8, C4_8, C5_8, C2_8, Cl1_8, C3_8, C10_8,
 O1_8, O2_8, C11_8, C17_8, C12_8, C16_8, C18_8, C22_8, C13_8, C15_8, C19_8,
 C21_8, C14_8, C20_8, Br1_8, C8_8, C8_8, C7_8, C9_8, C8_8, C7_8, C6_8, C9_8,
 C4_8, C6_8, C5_8, C4_8, C2_8, C5_8, C4_8, Cl1_8, C5_8, C2_8, C1_8, C3_8, C2_8,
 C2_8, C10_8, O1_8, C1_8, O2_8, C1_8, C3_8, C10_8, C3_8, C11_8, C3_8, C17_8,
 C12_8, C11_8, C16_8, C11_8, C18_8, C17_8, C22_8, C17_8, C13_8, C12_8, C16_8,
 C15_8, C19_8, C18_8, C22_8, C21_8, C14_8, C13_8, C15_8, C14_8, C20_8, C19_8,
 C21_8, C20_8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C15_7, Br1_7, C8_7, C7_7, C9_7, C6_7, C4_7, C5_7, C2_7, Cl1_7, C1_7, C3_7,
 C10_7, O1_7, O2_7, C11_7, C17_7, C12_7, C16_7, C18_7, C22_7, C13_7, C19_7,
 C21_7, C14_7, C20_7, Br1_7, C8_7, C8_7, C7_7, C9_7, C8_7, C7_7, C6_7, C9_7,
 C4_7, C6_7, C5_7, C4_7, C2_7, C5_7, C4_7, Cl1_7, C5_7, C2_7, C1_7, C3_7, C2_7,
 C2_7, C10_7, O1_7, C1_7, O2_7, C1_7, C3_7, C10_7, C3_7, C11_7, C3_7, C17_7,
 C12_7, C11_7, C16_7, C11_7, C18_7, C17_7, C22_7, C17_7, C13_7, C12_7, C16_7,
 C15_7, C19_7, C18_7, C22_7, C21_7, C14_7, C13_7, C15_7, C14_7, C20_7, C19_7,
 C21_7, C20_7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Br1_6, C8_6, C7_6, C9_6, C6_6, C4_6, C5_6, C2_6, Cl1_6, C1_6, C3_6, C10_6,
 O1_6, O2_6, C11_6, C17_6, C12_6, C16_6, C18_6, C22_6, C13_6, C15_6, C19_6,
 C21_6, C14_6, C20_6, Br1_6, C8_6, C8_6, C7_6, C9_6, C8_6, C7_6, C6_6, C9_6,
 C4_6, C6_6, C5_6, C4_6, C2_6, C5_6, C4_6, Cl1_6, C5_6, C2_6, C1_6, C3_6, C2_6,
 C2_6, C10_6, O1_6, C1_6, O2_6, C1_6, C3_6, C10_6, C3_6, C11_6, C3_6, C17_6,
 C12_6, C11_6, C16_6, C11_6, C18_6, C17_6, C22_6, C17_6, C13_6, C12_6, C16_6,
 C15_6, C19_6, C18_6, C22_6, C21_6, C14_6, C13_6, C15_6, C14_6, C20_6, C19_6,
 C21_6, C20_6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C23_10, N1_10, C24_10, N1_10, C23_10, C24_10, C23_10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N1_9, C23_9, C24_9, N1_9, C23_9, C24_9, C23_9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C3_3, Br1_3, C8_3, C7_3, C9_3, C6_3, C4_3, C5_3, C2_3, Cl1_3, C1_3, C10_3,
 O1_3, O2_3, C11_3, C17_3, C12_3, C16_3, C18_3, C22_3, C13_3, C15_3, C19_3,
 C21_3, C14_3, C20_3, Br1_3, C8_3, C8_3, C7_3, C9_3, C8_3, C7_3, C6_3, C9_3,
 C4_3, C6_3, C5_3, C4_3, C2_3, C5_3, C4_3, Cl1_3, C5_3, C2_3, C1_3, C3_3, C2_3,
 C2_3, C10_3, O1_3, C1_3, O2_3, C1_3, C3_3, C10_3, C3_3, C11_3, C3_3, C17_3,
 C12_3, C11_3, C16_3, C11_3, C18_3, C17_3, C22_3, C17_3, C13_3, C12_3, C16_3,
 C15_3, C19_3, C18_3, C22_3, C21_3, C14_3, C13_3, C15_3, C14_3, C20_3, C19_3,
 C21_3, C20_3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Br1_5, 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 0.001 and sigma for 1-3 distances of 0.001
 C17_2, C22_2, C21_2, C20_2, C19_2, C18_2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 Br1_12, Cl1_12, O1_12, O2_12, C1_12, C2_12, C3_12, C4_12, C5_12, C6_12, H6_12,
  C7_12, H7_12, C8_12, C9_12, H9_12, C10_12, H10A_12, H10B_12, C11_12, C12_12,
 H12_12, C13_12, H13_12, C14_12, H14_12, C15_12, H15_12, C16_12, H16_12, C17_12,
  C18_12, H18_12, C19_12, H19_12, C20_12, H20_12, C21_12, H21_12, C22_12, H22_12
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Br1_4, Cl1_4, O1_4, O2_4, C1_4, C2_4, C3_4, C4_4, C5_4, C6_4, H6_4, C7_4,
 H7_4, C8_4, C9_4, H9_4, C10_4, H10A_4, H10B_4, C11_4, C12_4, H12_4, C13_4,
 H13_4, C14_4, H14_4, C15_4, H15_4, C16_4, H16_4, C17_4, C18_4, H18_4, C19_4,
 H19_4, C20_4, H20_4, C21_4, H21_4, C22_4, H22_4
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C17_7, C22_7, C21_7, C20_7, C19_7, C18_7
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C3_7, C17_7
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N1_11, C23_11, C24_11
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
6. Same fragment restrains
{Br1_2, 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}
{Br1_3, 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}
{Br1_4, 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}
{Br1_5, 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}
{Br1_6, 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}
{Br1_7, 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}
{Br1_8, 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}
{Br1_12, Cl1_12, O1_12, O2_12, C1_12, C2_12, C3_12, C4_12, C5_12, C6_12, C7_12,
C8_12, C9_12, C10_12, C11_12, C12_12, C13_12, C14_12, C15_12, C16_12, C17_12,
C18_12, C19_12, C20_12, C21_12, C22_12}
as
{Br1_1, 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} sigma for 1-2: 0.001 1-3: 0.002
{N1_10, C23_10, C24_10}
{N1_11, C23_11, C24_11}
as
{N1_9, C23_9, C24_9} sigma for 1-2: 0.001 1-3: 0.002
7. Others
 Sof(Br1)=Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=
 Sof(H10B)=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(Br1)=Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=
 Sof(H10B)=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)
8.a Rotating group:
 O4(H4A,H4B)
8.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10A,H10B), C10(H10A,H10B), C10(H10A,H10B), C10(H10A,
 H10B), C10(H10A,H10B), C10(H10A,H10B), C10(H10A,H10B), C10(H10A,H10B)
8.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6(H6), C7(H7), C9(H9),
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
  C21(H21), C22(H22), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6(H6),
 C7(H7), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C6(H6), C7(H7), C9(H9), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6(H6), C7(H7),
 C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C6(H6), C7(H7), C9(H9), 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 as rotating group:
 C24(H24A,H24B,H24C), C24(H24A,H24B,H24C), C24(H24A,H24B,H24C)
;
_platon_squeeze_void_probe_radius 1.20
_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-2CL5BR
_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 2.183
_oxdiff_exptl_absorpt_empirical_full_min 0.504