Highly selective acid-catalyzed olefin isomerization of limonene to terpinolene by kinetic suppression of overreactions in a confined space of porous metal–macrocycle frameworks
He, Wei; Tashiro, Shohei; Shionoya, Mitsuhiko; Chemical Science  (2022) –; doi:10.1039/D2SC01561G

data_1567103
_publ_section_title
;
 Highly selective acid-catalyzed olefin isomerization of limonene to
 terpinolene by kinetic suppression of overreactions in a confined space
 of porous metal--macrocycle frameworks
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01561G
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         '4(C42 H42 Cl6 N6 Pd3), 4.463(O), 0.6(C10 H16)'
_chemical_formula_sum            'C174 H177.6 Cl24 N24 O4.46 Pd12'
_chemical_formula_weight         4804.03
_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   geom
_audit_creation_date             2021-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.26470(10)
_cell_length_b                   52.2312(10)
_cell_length_c                   19.5113(3)
_cell_measurement_reflns_used    58729
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.7180
_cell_measurement_theta_min      2.3700
_cell_volume                     14533.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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    -39.00   6.00   0.50    1.08    --    0.00 -19.00-180.00   90
  2  \w    -19.00  87.00   0.50    1.08    --    0.00  57.00 -60.00  212
  3  \w    -69.00 -42.00   0.50    1.08    --    0.00 -57.00 -30.00   54
  4  \w    -85.00 -44.00   0.50    1.08    --    0.00 -19.00-180.00   82
  5  \w    -39.00  19.00   0.50    1.08    --    0.00 -57.00 -30.00  116
  6  \w     23.00  48.00   0.50    1.08    --    0.00  19.00   0.00   50
  7  \w     93.00 151.00   0.50    4.32    --   92.10  15.00  60.00  116
  8  \w     80.00 126.00   0.50    4.32    --   92.10  77.00-120.00   92
  9  \w    109.00 179.00   0.50    4.32    --   92.10  45.00-120.00  140
 10  \w     36.00  88.00   0.50    4.32    --   92.10 -61.00 120.00  104
 11  \w     18.00 113.00   0.50    4.32    --   92.10 -61.00-120.00  190
 12  \w     88.00 150.00   0.50    4.32    --   92.10  45.00  90.00  124
 13  \w     77.00 167.00   0.50    4.32    --   92.10  45.00 150.00  180
 14  \w      3.00 107.00   0.50    4.32    --   92.10 -45.00 120.00  208
 15  \w      9.00  69.00   0.50    4.32    --   92.10 -77.00   0.00  120
 16  \w    139.00 180.00   0.50    4.32    --   92.10  82.00-150.00   82
 17  \w     76.00 102.00   0.50    4.32    --   92.10  82.00-150.00   52
 18  \w     80.00 116.00   0.50    4.32    --   92.10 -77.00   0.00   72
 19  \w      4.00  33.00   0.50    4.32    --   92.10 -15.00-180.00   58
 20  \w      4.00 103.00   0.50    4.32    --   92.10 -45.00-120.00  198
 21  \w    116.00 182.00   0.50    4.32    --   92.10  15.00 -60.00  132
 22  \w     76.00 170.00   0.50    4.32    --   92.10  45.00 120.00  188
 23  \w     81.00 107.00   0.50    4.32    --   92.10  45.00-120.00   52
 24  \w     81.00 114.00   0.50    4.32    --   92.10  30.00  90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0323250000
_diffrn_orient_matrix_UB_12      0.0013623000
_diffrn_orient_matrix_UB_13      -0.0747401000
_diffrn_orient_matrix_UB_21      -0.0692312000
_diffrn_orient_matrix_UB_22      0.0221294000
_diffrn_orient_matrix_UB_23      -0.0143723000
_diffrn_orient_matrix_UB_31      0.0763516000
_diffrn_orient_matrix_UB_32      0.0194656000
_diffrn_orient_matrix_UB_33      0.0210282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       64
_diffrn_reflns_limit_k_min       -64
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            160911
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         73.644
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    8.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       block
_exptl_crystal_F_000             4771
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         3.339
_refine_diff_density_min         -1.949
_refine_diff_density_rms         0.173
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.245(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2007
_refine_ls_number_reflns         56440
_refine_ls_number_restraints     1136
_refine_ls_restrained_S_all      2.444
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.1006
_refine_ls_shift/su_max          0.001
_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          0.2805
_refine_ls_wR_factor_ref         0.3087
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                37135
_reflns_number_total             56440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01561g2.cif
_cod_data_source_block           limonene@MMF
_cod_original_formula_sum        'C174 H177.60 Cl24 N24 O4.46 Pd12'
_cod_database_code               1567103
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNPdCl
_chemical_oxdiff_usercomment     10922
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.755(15)
 0.245(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 Pd8-N16
 2 with sigma of 0.02
 Pd8-N15
 2 with sigma of 0.02
 C8G-C9G
 1.5 with sigma of 0.02
 C8G-C5G
 1.5 with sigma of 0.02
 C5G-C4G
 1.5 with sigma of 0.02
 C6G-C5G
 1.5 with sigma of 0.02
 C9G-C5G
 2.55 with sigma of 0.02
 C8G-C4G
 2.55 with sigma of 0.02
 C6G-C8G
 2.55 with sigma of 0.02
 N18-C118
 1.5 with sigma of 0.02
 C4G-C2G
 2.55 with sigma of 0.02
 C6G-C2G
 2.55 with sigma of 0.02
 C5G-C7G
 2.55 with sigma of 0.02
 C7G-C2G
 1.55 with sigma of 0.02
 C113-Pd9
 2.88 with sigma of 0.02
 C6G-C7G
 1.55 with sigma of 0.02
 C10G-C8G
 1.5 with sigma of 0.02
 C10G-C5G
 2.55 with sigma of 0.02
 C7G-C1G
 2.55 with sigma of 0.02
 C2G-C1G
 1.55 with sigma of 0.02
 C118-Pd9
 2.88 with sigma of 0.02
 C5G-C3G
 2.55 with sigma of 0.02
 C2G-C3G
 1.55 with sigma of 0.02
 C4G-C3G
 1.55 with sigma of 0.02
 C3G-C1G
 2.55 with sigma of 0.02
 C155-Pd9_$1 = Pd9-C113
 2.88 with sigma of 0.02
 Pd9-C118
 2.88 with sigma of 0.02
 N24-Pd12
 2 with sigma of 0.02
 N17-C113
 1.5 with sigma of 0.01
 N22-Pd11
 2 with sigma of 0.02
 C147-N23
 1.5 with sigma of 0.02
 N23-Pd12
 2 with sigma of 0.02
 Pd12-N24
 2 with sigma of 0.02
 C155-N22
 1.5 with sigma of 0.02
 N23-C146
 1.5 with sigma of 0.02
 C154-C151
 1.5 with sigma of 0.02
 N23-C141
 2.5 with sigma of 0.02
 N23-C145
 2.5 with sigma of 0.02
 N22-C154
 1.5 with sigma of 0.02
 C148-C147
 1.5 with sigma of 0.02
 C147-C148
 1.5 with sigma of 0.02
 N17-C112
 1.5 with sigma of 0.02
 N21-Pd11
 2 with sigma of 0.02
 C160-N21
 1.5 with sigma of 0.02
 C140-N24
 1.5 with sigma of 0.02
 C146-C142
 1.5 with sigma of 0.02
 C145-C146
 1.5 with sigma of 0.02
 N24-C141
 1.5 with sigma of 0.02
 N24-C146
 2.5 with sigma of 0.02
 N24-C142
 2.5 with sigma of 0.02
 Pd11-C160
 2.8 with sigma of 0.02
 Pd11-C155
 2.8 with sigma of 0.01
 N22-C155
 1.5 with sigma of 0.02
 N17-Pd9
 2 with sigma of 0.01
 C91-C92
 1.4 with sigma of 0.01
 N15-C98
 1.5 with sigma of 0.02
 N21-C161
 1.5 with sigma of 0.02
 C112-N17
 1.5 with sigma of 0.02
 C105-C106
 1.4 with sigma of 0.02
 N13-C126
 1.5 with sigma of 0.02
 C123-C126
 1.4 with sigma of 0.02
 C105-N16
 1.5 with sigma of 0.02
 C109-C112
 1.4 with sigma of 0.02
 C91-N14
 1.5 with sigma of 0.02
 C98-C95
 1.4 with sigma of 0.02
 C92-C91
 1.4 with sigma of 0.02
 C119-C120
 1.4 with sigma of 0.01
 C95-C98
 1.4 with sigma of 0.01
 C118-N18
 1.4 with sigma of 0.02
 C113-N17
 1.4 with sigma of 0.02
 Pd12-Cl24
 2.3 with sigma of 0.02
 C119-N18
 1.5 with sigma of 0.01
 N14-C93
 2.9 with sigma of 0.01
 C119_$2-C117_$2
 2.9 with sigma of 0.02
 C106-C105
 1.5 with sigma of 0.02
 C96-C98 \\sim C98-C94
 with sigma of 0.02
 C94-C98 \\sim C98-C96
 with sigma of 0.02
 C149-C147 \\sim C147-C153
 with sigma of 0.02
 C110-C112 \\sim C112-C108
 with sigma of 0.01
4. Restrained planarity
 C5G, C8G, C10G, C9G
 with sigma of 0.01
 N23, C146, C142, N24
 with sigma of 0.1
 C105, C106, C107, C111, C110, C108, C109, C112
 with sigma of 0.1
 C126, C123, C124, C122, C125, C121, C120, C119
 with sigma of 0.1
 C98, C95, C93, C92, C97, C96, C94, C91
 with sigma of 0.1
 C147, C148, C153, C152, C151, C154, C150, C149
 with sigma of 0.1
5. Rigid bond restraints
 Pd8
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N22, C155
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C95, C94
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C138, C139, C134
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C59, C60
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C7, C8, C11, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N17, C113
 with sigma for 1-2 distances of 0.00005 and sigma for 1-3 distances of 0.00005
 N24, N23, Pd12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Pd12, Cl24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N14, C91
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Uiso/Uaniso restraints and constraints
N22 \\sim C155 \\sim C154: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C155 \\sim N22 \\sim C160: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C135 \\sim C136: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C97 \\sim C96 \\sim C92: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C26 \\sim C25: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
Pd8 \\sim N15: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C26 \\sim C25 \\sim C27: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C106 \\sim C109 \\sim C112 \\sim C105 \\sim C111 \\sim C110: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C15 \\sim C20: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C93 \\sim C94: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C44 \\sim C45: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02 within 2A
C61 \\sim C62: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02 within 2A
C82 \\sim C81: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02 within 2A
C152 \\sim C151 \\sim C153 \\sim C150 \\sim C149 \\sim C148 \\sim C147 \\sim
C154 \\sim N22 \\sim N23: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.004 within 2A
C113 \\sim N17 \\sim C118 \\sim C114 \\sim C115 \\sim C116 \\sim C117: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C98 \\sim C95: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
Uanis(Cl15) \\sim Ueq, Uanis(Cl16) \\sim Ueq, Uanis(Pd8) \\sim Ueq, Uanis(C147)
\\sim Ueq, Uanis(N23) \\sim Ueq, Uanis(N24) \\sim Ueq, Uanis(C140) \\sim Ueq:
with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(Cl15) \\sim Ueq, Uanis(Cl16) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C98)
\\sim Ueq, Uanis(O6G) \\sim Ueq, Uanis(N21) \\sim Ueq, Uanis(C161) \\sim Ueq,
Uanis(Cl23) \\sim Ueq, Uanis(Pd12) \\sim Ueq, Uanis(C105) \\sim Ueq, Uanis(N16)
\\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C99) \\sim Ueq,
Uanis(C100) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(N15)
\\sim Ueq, Uanis(O4G) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Cl17) \\sim Ueq, Uanis(Cl18) \\sim Ueq, Uanis(Cl16) \\sim Ueq,
Uanis(Cl15) \\sim Ueq, Uanis(Cl23) \\sim Ueq, Uanis(Cl24) \\sim Ueq: with sigma
of 0.05 and sigma for terminal atoms of 0.1
Uanis(C3G) \\sim Ueq, Uanis(C9G) \\sim Ueq, Uanis(C8G) \\sim Ueq, Uanis(C5G)
\\sim Ueq, Uanis(C10G) \\sim Ueq, Uanis(C4G) \\sim Ueq, Uanis(C6G) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C155) \\sim Ueq, Uanis(C160) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(N17)
\\sim Ueq, Uanis(N18) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C146) \\sim Ueq, Uanis(C141) \\sim Ueq, Uanis(C143) \\sim Ueq,
Uanis(C142) \\sim Ueq, Uanis(C145) \\sim Ueq, Uanis(C144) \\sim Ueq, Uanis(N22)
\\sim Ueq, Uanis(C155) \\sim Ueq, Uanis(C160) \\sim Ueq, Uanis(N21) \\sim Ueq,
Uanis(C159) \\sim Ueq, Uanis(C158) \\sim Ueq, Uanis(C157) \\sim Ueq,
Uanis(C156) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C140) \\sim Ueq, Uanis(N24) \\sim Ueq, Uanis(N23) \\sim Ueq, Uanis(C147)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(N18) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C113) \\sim Ueq, Uanis(N17)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C125) \\sim Ueq, Uanis(C120) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
7. Rigid body (RIGU) restrains
 N18, C34, C29, C30, C31, C32, C33, C105, N16, C104, C99, N15, C98, C159, C160
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C154, C151, C150, C149, C148, C153, C152, C105, C106, C111, C110, C109, C108,
 C107, C112, C20, C19, C18, C17, C16, C15, C103, C104, C99, C100, C102, C101
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C104, Cl23, Cl24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C155, C156, C157, C158, C159, C160, C73, C74, C75, C76, C71, C72
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C141, C145, C144, C143, C142, C146, C147, N23, N24, C140
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C4G, C9G, C8G, C5G, C10G, C6G, C3G, C7G, C2G, C1G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.0001
 C113, C114, C115, C116, C117, C118
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
8. Others
 Fixed Sof: C9G(0.6) H9GA(0.6) H9GB(0.6) C5G(0.6) H5G(0.6) C8G(0.6) C4G(0.6)
 H4GA(0.6) H4GB(0.6) C10G(0.6) H10D(0.6) H10E(0.6) H10F(0.6) C6G(0.6) H6GA(0.6)
 H6GB(0.6) C2G(0.6) C3G(0.6) H3G(0.6) C1G(0.6) H1GA(0.6) H1GB(0.6) H1GC(0.6)
 C7G(0.6) H7GA(0.6) H7GB(0.6) O4G(0.5) O6G(0.4)
9.a Ternary CH refined with riding coordinates:
 N11(H11), N4(H4), N20(H20), N3(H3), N9(H9A), N1(H1), N12(H12A), N2(H2),
 N14(H14), N10(H10A), N8(H8), N13(H13C), N18(H18A), N19(H19A), N7(H7), N5(H5),
 N6(H6), N21(H21), N22(H22), N15(H15), N16(H16E), N23(H23A), N24(H24A),
 C5G(H5G), N17(H17A)
9.b Secondary CH2 refined with riding coordinates:
 C70(H70A,H70B), C21(H21A,H21B), C168(H16A,H16B), C14(H14A,H14B), C7(H7A,H7B),
 C42(H42A,H42B), C56(H56A,H56B), C91(H91A,H91B), C63(H63A,H63B), C28(H28A,H28B),
  C49(H49A,H49B), C77(H77A,H77B), C133(H13A,H13B), C35(H35A,H35B), C84(H84A,
 H84B), C119(H11A,H11B), C112(H11C,H11D), C126(H12B,H12C), C140(H14C,H14D),
 C161(H16C,H16D), C147(H14E,H14F), C98(H98A,H98B), C154(H15A,H15B), C105(H10B,
 H10C), C4G(H4GA,H4GB), C6G(H6GA,H6GB), C7G(H7GA,H7GB)
9.c Aromatic/amide H refined with riding coordinates:
 C41(H41), C159(H159), C158(H158), C157(H157), C156(H156), C19(H19), C18(H18),
 C17(H17), C16(H16), C54(H54), C55(H55), C128(H128), C80(H80), C124(H124),
 C125(H125), C121(H121), C122(H122), C52(H52), C51(H51), C79(H79), C82(H82),
 C58(H58), C59(H59), C60(H60), C61(H61), C66(H66), C40(H40), C38(H38), C9(H9),
 C26(H26), C129(H129), C89(H89), C88(H88), C87(H87), C86(H86), C12(H12),
 C65(H65), C96(H96), C97(H97), C93(H93), C94(H94), C83(H83), C69(H69), C13(H13),
  C5(H5A), C4(H4A), C3(H3A), C2(H2A), C131(H131), C37(H37), C167(H167),
 C10(H10), C27(H27), C114(H114), C115(H115), C116(H116), C117(H117), C23(H23),
 C136(H136), C135(H135), C139(H139), C138(H138), C130(H130), C163(H163),
 C166(H166), C164(H164), C68(H68), C72(H72), C75(H75), C74(H74), C73(H73),
 C44(H44), C45(H45), C46(H46), C47(H47), C24(H24), C33(H33), C30(H30), C31(H31),
  C32(H32), C100(H100), C101(H101), C102(H102), C103(H103), C110(H110),
 C111(H111), C107(H107), C108(H108), C150(H150), C149(H149), C153(H153),
 C152(H152), C145(H145), C144(H144), C143(H143), C142(H142), C3G(H3G)
9.d Fitted hexagon refined as free rotating group:
 C155(C160,C159,C158,C157,C156), C20(C19,C18,C17,C16,C15), C124(C125,C120,C121,
 C122,C123), C62(C57,C58,C59,C60,C61), C90(C89,C88,C87,C86,C85), C96(C97,C92,
 C93,C94,C95), C6(C5,C4,C3,C2,C1), C118(C113,C114,C115,C116,C117), C137(C136,
 C135,C134,C139,C138), C72(C71,C76,C75,C74,C73), C44(C45,C46,C47,C48,C43),
 C33(C34,C29,C30,C31,C32), C104(C99,C100,C101,C102,C103), C109(C110,C111,C106,
 C107,C108), C151(C150,C149,C148,C153,C152), C141(C146,C145,C144,C143,C142)
9.e X=CH2 refined with riding coordinates:
 C9G(H9GA,H9GB)
9.f Idealised Me refined with riding coordinates:
 C10G(H10D,H10E,H10F), C1G(H1GA,H1GB,H1GC)
;
_shelx_res_checksum              1253
_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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.585