Iron-Catalyzed Trimerization of Terminal Alkynes Enabled by Pyrimidinediimine Ligands: A Regioselective Method for the Synthesis of 1,3,5-Substituted Arenes
Doll, Julianna S.; Eichelmann, Robert; Hertwig, Leif E.; Bender, Thilo; Kohler, Vincenz J.; Bill, Eckhard; Wadepohl, Hubert; Roşca, Dragoş-Adrian; ACS Catalysis  (2021) 5593–5600; doi:10.1021/acscatal.1c00978

data_4518620
_publ_section_title
;
 Iron-Catalyzed Trimerization of Terminal Alkynes Enabled by
 Pyrimidinediimine Ligands: A Regioselective Method for the Synthesis of
 1,3,5-Substituted Arenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5593
_journal_page_last               5600
_journal_paper_doi               10.1021/acscatal.1c00978
_journal_year                    2021
_chemical_formula_moiety         'C43 H48 Cl2 Fe N4, 1.769(C H2 Cl2)'
_chemical_formula_sum            'C44.77 H51.54 Cl5.54 Fe N4'
_chemical_formula_weight         897.80
_chemical_properties_physical    'air-sensitive, moisture-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_block_code                ro_dr20
_audit_creation_date             2019-12-06
_audit_creation_method
;
encif (version 1.111)

encifer (version_id = 257312.64)

Olex2 1.3
(compiled 2019.11.22 svn.r41b7951 for OlexSys, GUI svn.r6003)
;
_audit_update_record
'06.12.2019 14:17:23 CET UTC+01:00  encif 1.111'
_cell_angle_alpha                90
_cell_angle_beta                 110.7855(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.71615(14)
_cell_length_b                   20.52625(18)
_cell_length_c                   17.35612(18)
_cell_measurement_reflns_used    32786
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.4390
_cell_measurement_theta_min      3.4650
_cell_volume                     4568.43(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_publication_material
'encif (Wadepohl, 2009-19); encifer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'DIRDIF (Beurskens et al., 1999-2008)'
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -21.00  69.00   1.00    3.00    --    0.00  57.00 -90.00   90
  2  \w    -30.00  70.00   1.00    3.00    --    0.00  77.00 150.00  100
  3  \w    -34.00  11.00   1.00    3.00    --   14.00 110.00 -79.44   45
  4  \w    -55.00  35.00   1.00    3.00    --   14.00 -56.00  99.27   90
  5  \w    -26.00  11.00   1.00    3.00    --   22.00 110.00 -17.08   37
  6  \w    -34.00  -5.00   1.00    3.00    --   26.00 129.00  98.27   29
  7  \w    -26.00   0.00   1.00    8.00    --   30.00 123.00 -51.47   26
  8  \w     -2.00  24.00   1.00    8.00    --   38.00  96.00  11.81   26
  9  \w      5.00  32.00   1.00    8.00    --   42.00  90.00  71.33   27
 10  \w      5.00  32.00   1.00    8.00    --   42.00  90.00 174.12   27
 11  \w     13.00  40.00   1.00    8.00    --   46.00  83.00-160.18   27
 12  \w     14.00  45.00   1.00    8.00    --   46.00  81.00 -47.10   31
 13  \w     13.00  40.00   1.00    8.00    --   46.00  83.00 158.01   27
 14  \w     13.00  45.00   1.00    8.00    --   46.00  82.00  32.71   32
 15  \w     17.00  45.00   1.00    8.00    --   50.00  82.00 -90.84   28
 16  \w     18.00  45.00   1.00    8.00    --   50.00  80.00  13.82   27
 17  \w     18.00  45.00   1.00    8.00    --   50.00  80.00 170.23   27
 18  \w     17.00  45.00   1.00    8.00    --   50.00  82.00-152.20   28
 19  \w     18.00  45.00   1.00    8.00    --   50.00  80.00-130.32   27
 20  \w     19.00  45.00   1.00    8.00    --   50.00  79.00  87.79   26
 21  \w     18.00  45.00   1.00    8.00    --   50.00  81.00  53.72   27
 22  \w     18.00  45.00   1.00    8.00    --   50.00  81.00 119.94   27
 23  \w     17.00  45.00   1.00    8.00    --   50.00  82.00 -14.86   28
 24  \w     24.00 124.00   1.00    8.00    --   54.00  77.00  60.00  100
 25  \w    -15.00  75.00   1.00    8.00    --   54.00 -57.00  30.00   90
 26  \w     26.00 124.00   1.00    8.00    --   54.00  74.00  26.31   98
 27  \w     24.00  66.00   1.00    8.00    --   54.00  77.00-150.00   42
 28  \w     24.00 111.00   1.00    8.00    --   54.00-125.00-150.00   87
 29  \w    -14.00  77.00   1.00    8.00    --   54.00 -68.00 -51.00   91
 30  \w     24.00  51.00   1.00    8.00    --   54.00  77.00 -60.00   27
 31  \w    -14.00  68.00   1.00    8.00    --   54.00 -57.00 150.00   82
 32  \w     25.00  50.00   1.00    8.00    --   54.00  77.00 141.46   25
 33  \w     26.00  51.00   1.00    8.00    --   54.00  76.00  47.07   25
 34  \w     31.00  57.00   1.00    8.00    --   58.00  75.00  92.02   26
 35  \w     29.00  55.00   1.00    8.00    --   58.00  77.00 102.92   26
 36  \w     30.00  56.00   1.00    8.00    --   58.00  75.00  71.84   26
 37  \w     28.00  55.00   1.00    8.00    --   58.00  77.00 -47.94   27
 38  \w     32.00  59.00   1.00    8.00    --   58.00  76.00 136.90   27
 39  \w     29.00  66.00   1.00    8.00    --   58.00  76.00 162.16   37
 40  \w     29.00  56.00   1.00    8.00    --   58.00  76.00  -3.61   27
 41  \w     30.00  55.00   1.00    8.00    --   58.00  76.00 -89.35   25
 42  \w     30.00  57.00   1.00    8.00    --   58.00  76.00 176.58   27
 43  \w     30.00  56.00   1.00    8.00    --   58.00  77.00-137.33   26
 44  \w     28.00  55.00   1.00    8.00    --   58.00  77.00  36.52   27
 45  \w     29.00  54.00   1.00    8.00    --   58.00  77.00-104.86   25
 46  \w     38.00  64.00   1.00    8.00    --   62.00  74.00-121.53   26
 47  \w     36.00  62.00   1.00    8.00    --   62.00  75.00 124.68   26
 48  \w     35.00  61.00   1.00    8.00    --   62.00  71.00-159.79   26
 49  \w     39.00  65.00   1.00    8.00    --   62.00  73.00 -98.40   26
 50  \w     32.00  58.00   1.00    8.00    --   62.00  77.00 -34.42   26
 51  \w     33.00  63.00   1.00    8.00    --   62.00  76.00  34.55   30
 52  \w     37.00  64.00   1.00    8.00    --   62.00  74.00 -22.57   27
 53  \w     38.00  79.00   1.00    8.00    --   62.00  77.00 148.78   41
 54  \w     40.00  65.00   1.00    8.00    --   62.00  65.00 100.19   25
 55  \w     33.00  59.00   1.00    8.00    --   62.00  76.00-156.95   26
 56  \w    107.00 132.00   1.00    8.00    --   62.00  77.00 -78.38   25
 57  \w     34.00  61.00   1.00    8.00    --   62.00  77.00 -78.38   27
 58  \w     35.00  61.00   1.00    8.00    --   62.00  77.00  -3.94   26
 59  \w     38.00  65.00   1.00    8.00    --   62.00  68.00-126.69   27
 60  \w     43.00  68.00   1.00    8.00    --   66.00  69.00-146.37   25
 61  \w     44.00  71.00   1.00    8.00    --   66.00  64.00  81.26   27
 62  \w    104.00 130.00   1.00    8.00    --   66.00  64.00  81.26   26
 63  \w     40.00  65.00   1.00    8.00    --   66.00  72.00 100.46   25
 64  \w     44.00  73.00   1.00    8.00    --   66.00  69.00  40.48   29
 65  \w     44.00  75.00   1.00    8.00    --   66.00  71.00   4.50   31
 66  \w     49.00  75.00   1.00    8.00    --   66.00  69.00 164.63   26
 67  \w     39.00  65.00   1.00    8.00    --   66.00  74.00 -18.63   26
 68  \w     50.00  77.00   1.00    8.00    --   70.00  57.00-109.40   27
 69  \w     43.00  69.00   1.00    8.00    --   70.00  75.00 104.42   26
 70  \w     44.00  78.00   1.00    8.00    --   70.00  73.00  19.64   34
 71  \w     89.00 138.00   1.00    8.00    --   70.00  71.00  49.10   49
 72  \w     43.00  69.00   1.00    8.00    --   70.00  71.00  49.10   26
 73  \w     41.00  67.00   1.00    8.00    --   70.00  76.00 131.18   26
 74  \w     42.00  68.00   1.00    8.00    --   70.00  74.00   5.56   26
 75  \w     43.00  68.00   1.00    8.00    --   70.00  71.00 -70.09   25
 76  \w     40.00  66.00   1.00    8.00    --   70.00  77.00 -60.83   26
 77  \w     57.00  83.00   1.00    8.00    --   74.00  48.00  95.14   26
 78  \w     48.00  80.00   1.00    8.00    --   74.00  71.00  -1.04   32
 79  \w     49.00  74.00   1.00    8.00    --   74.00  71.00 -76.21   25
 80  \w     53.00  78.00   1.00    8.00    --   74.00  51.00 106.16   25
 81  \w     44.00  69.00   1.00    8.00    --   74.00  77.00 -29.89   25
 82  \w     47.00  73.00   1.00    8.00    --   74.00  73.00-161.81   26
 83  \w     48.00  78.00   1.00    8.00    --   74.00  70.00 174.77   30
 84  \w     52.00  77.00   1.00    8.00    --   74.00  66.00-122.95   25
 85  \w     51.00 108.00   1.00    8.00    --   74.00  65.00-163.98   57
 86  \w     47.00  72.00   1.00    8.00    --   74.00  73.00-123.96   25
 87  \w     57.00 112.00   1.00    8.00    --   78.00  60.00  98.93   55
 88  \w     52.00  77.00   1.00    8.00    --   78.00  72.00 106.40   25
 89  \w     53.00  79.00   1.00   16.00    --   82.00  75.00 -65.63   26
 90  \w     57.00 117.00   1.00   16.00    --   82.00  71.00   0.49   60
 91  \w     52.00 145.00   1.00   16.00    --   82.00  77.00 129.52   93
 92  \w     54.00 151.00   1.00   16.00    --   82.00  73.00-116.72   97
 93  \w     58.00 115.00   1.00   16.00    --   82.00  73.00 -60.08   57
 94  \w     62.00 126.00   1.00   16.00    --   82.00  56.00 -22.76   64
 95  \w     60.00 103.00   1.00   16.00    --   86.00  70.00-153.57   43
 96  \w     57.00  83.00   1.00   16.00    --   86.00  75.00  84.13   26
 97  \w     58.00 107.00   1.00   16.00    --   86.00  74.00 108.14   49
 98  \w     63.00 109.00   1.00   16.00    --   90.00  71.00-168.22   46
 99  \w     61.00 158.00   1.00   16.00    --   90.00  75.00  27.98   97
100  \w     63.00  94.00   1.00   16.00    --   90.00  71.00 -14.49   31
101  \w     71.00  97.00   1.00   16.00    --   94.00  68.00  82.21   26
102  \w     72.00  98.00   1.00   16.00    --   98.00  70.00  57.36   26
103  \w     71.00  97.00   1.00   16.00    --   98.00  72.00-146.98   26
104  \w     81.00 108.00   1.00   16.00    --  102.00  55.00  99.84   27
105  \w    132.00 171.00   1.00   16.00    --  102.00  72.00  29.39   39
106  \w     75.00 101.00   1.00   16.00    --  102.00  72.00  29.39   26
107  \w     72.00 106.00   1.00   16.00    --  102.00  77.00  96.75   34
108  \w     85.00 174.00   1.00   16.00    --  108.00  64.00 -30.00   89
109  \w     85.00 135.00   1.00   16.00    --  108.00  64.00 -90.00   50
110  \w     85.00 111.00   1.00   16.00    --  108.00  64.00   0.00   26
111  \w     85.00 174.00   1.00   16.00    --  108.00  64.00 120.00   89
112  \w     71.00 110.00   1.00   16.00    --  108.00-111.00-150.00   39
113  \w     73.00 112.00   1.00   16.00    --  108.00-111.00 -30.00   39
114  \w     86.00 115.00   1.00   16.00    --  108.00  64.00-180.00   29
115  \w     78.00 104.00   1.00   16.00    --  108.00  77.00  30.00   26
116  \w    142.00 168.00   1.00   16.00    --  108.00  77.00-120.00   26
117  \w     78.00 104.00   1.00   16.00    --  108.00  77.00-120.00   26
118  \w    139.00 165.00   1.00   16.00    --  108.00  77.00   0.00   26
119  \w     78.00 105.00   1.00   16.00    --  108.00  77.00   0.00   27
120  \w     78.00 104.00   1.00   16.00    --  108.00  77.00 -60.00   26
121  \w     79.00 104.00   1.00   16.00    --  108.00  77.00-150.00   25
122  \w    136.00 162.00   1.00   16.00    --  108.00  77.00 150.00   26
123  \w     78.00 104.00   1.00   16.00    --  108.00  77.00 150.00   26
124  \w     78.00 104.00   1.00   16.00    --  108.00  77.00 -30.00   26
125  \w    108.00 178.00   1.00   16.00    --  108.00  77.00 -90.00   70
126  \w     78.00 105.00   1.00   16.00    --  108.00  77.00 -90.00   27
127  \w    143.00 169.00   1.00   16.00    --  108.00  77.00  60.00   26
128  \w     78.00 104.00   1.00   16.00    --  108.00  77.00  60.00   26
129  \w     78.00 104.00   1.00   16.00    --  108.00  77.00 120.00   26
130  \w     85.00 171.00   1.00   16.00    --  108.00  64.00-120.00   86
131  \w     78.00 177.00   1.00   16.00    --  108.00  77.00-180.00   99
132  \w     97.00 128.00   1.00   16.00    --  108.00 -64.00  60.00   31
133  \w     41.00  86.00   1.00   16.00    --  108.00 -64.00  60.00   45
134  \w     85.00 111.00   1.00   16.00    --  108.00  64.00 150.00   26
135  \w     85.00 174.00   1.00   16.00    --  108.00  64.00 -60.00   89
136  \w     37.00 102.00   1.00   16.00    --  108.00 -92.00-150.00   65
137  \w     37.00  73.00   1.00   16.00    --  108.00 -92.00   0.00   36
138  \w     67.00 113.00   1.00   16.00    --  108.00-111.00 150.00   46
139  \w     82.00 137.00   1.00   16.00    --  108.00  38.00 -90.00   55
140  \w     85.00 110.00   1.00   16.00    --  108.00  68.00  81.00   25
141  \w    120.00 175.00   1.00   16.00    --  108.00  64.00-150.00   55
142  \w     86.00 114.00   1.00   16.00    --  108.00  64.00-150.00   28
143  \w     36.00 108.00   1.00   16.00    --  108.00 -92.00  30.00   72
144  \w     82.00 165.00   1.00   16.00    --  108.00  38.00  30.00   83
145  \w     82.00 161.00   1.00   16.00    --  108.00  38.00-180.00   79
146  \w     42.00 131.00   1.00   16.00    --  108.00 -64.00-150.00   89
147  \w     85.00 172.00   1.00   16.00    --  108.00  64.00  90.00   87
148  \w     86.00 173.00   1.00   16.00    --  108.00  64.00  60.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0290614000
_diffrn_orient_matrix_UB_12      -0.0558277000
_diffrn_orient_matrix_UB_13      0.0635072000
_diffrn_orient_matrix_UB_21      0.0968359000
_diffrn_orient_matrix_UB_22      -0.0152435000
_diffrn_orient_matrix_UB_23      -0.0221627000
_diffrn_orient_matrix_UB_31      0.0648370000
_diffrn_orient_matrix_UB_32      0.0478483000
_diffrn_orient_matrix_UB_33      0.0669475000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            121931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.778
_diffrn_reflns_theta_min         4.157
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.893
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model (Busing & Levy, 1957).
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    1.305
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1873
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.092
_refine_diff_density_max         1.548
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         8750
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0808P)^2^+7.4217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7705
_reflns_number_total             8750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00978_si_006.cif
_cod_data_source_block           ro_dr20
_cod_original_cell_volume        4568.43(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518620
_audit_block_refno               3468
_audit_block_usercomment         'DAR-JD-011, irregular, green'
_shelx_estimated_absorpt_t_max   0.590
_shelx_estimated_absorpt_t_min   0.590
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelxl_version_number           2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C61-Cl11 \\sim C61-Cl12 \\sim C61-Cl13 \\sim C71-Cl21 \\sim C71-Cl22
 with sigma of 0.01
 Cl11-Cl13 \\sim Cl12-Cl13 \\sim Cl21-Cl22
 with sigma of 0.02
 C3-C41A \\sim C3-C41B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10
\\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18
\\sim C19 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27
\\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C41A \\sim
C42A \\sim C43A \\sim C44A \\sim C45A \\sim C46A \\sim C41B \\sim C42B \\sim
C43B \\sim C44B \\sim C45B \\sim C46B \\sim C47 \\sim C48 \\sim C49 \\sim C50
\\sim C51 \\sim C52 \\sim C61 \\sim C71: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.01 within 1A
4. Rigid body (RIGU) restrains
 C41A, C42A, C43A, C44A, C45A, C46A, C41B, C42B, C43B, C44B, C45B, C46B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C61, Cl1, Cl2, Cl13, Cl11, Cl12, Cl21, Cl22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C41A, C42A, C43A, C44A, C45A, C46A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C41B, C42B, C43B, C44B, C45B, C46B}
6. Others
 Sof(C41B)=Sof(C42B)=Sof(H42B)=Sof(C43B)=Sof(H43B)=Sof(C44B)=Sof(H44B)=
 Sof(C45B)=Sof(H45B)=Sof(C46B)=Sof(H46B)=1-FVAR(1)
 Sof(C41A)=Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=
 Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=Sof(Cl21)=Sof(Cl22)=Sof(C71)=Sof(H71A)=
 Sof(H71B)=FVAR(1)
 Sof(H61C)=Sof(H61D)=Sof(Cl12)=1-FVAR(2)
 Sof(H61A)=Sof(H61B)=Sof(Cl11)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C23(H23), C30(H30)
7.b Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C61(H61C,H61D), C71(H71A,H71B)
7.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C17(H17), C26(H26), C27(H27), C28(H28),
 C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A), C46A(H46A), C42B(H42B),
 C43B(H43B), C44B(H44B), C45B(H45B), C46B(H46B), C48(H48), C49(H49), C50(H50),
 C51(H51), C52(H52)
7.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C),
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.858
_shelx_res_checksum              30695
_cell_oxdiff_length_a            13.7172(2)
_cell_oxdiff_length_b            20.5161(3)
_cell_oxdiff_length_c            17.3604(3)
_cell_oxdiff_angle_alpha         89.9539(13)
_cell_oxdiff_angle_beta          110.7598(15)
_cell_oxdiff_angle_gamma         90.0389(13)
_cell_oxdiff_volume              4568.43(13)
_cell_oxdiff_measurement_reflns_used 32786