Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp<sup>3</sup> C-H Arylation.
Li, Bo; Li, Xinghua; Han, Boyang; Chen, Zhijie; Zhang, Xuekai; He, Gang; Chen, Gong; Journal of the American Chemical Society 141 (2019) 9401–9407; doi:10.1021/jacs.9b04221

data_4128709
_publ_section_title
;
 Construction of Natural-Product-Like Cyclophane-Braced Peptide
 Macrocycles via sp<sup>3</sup> C-H Arylation.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9401
_journal_page_last               9407
_journal_paper_doi               10.1021/jacs.9b04221
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H46 N6 O5, C H4 O'
_chemical_formula_sum            'C39 H50 N6 O6'
_chemical_formula_weight         698.85
_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             2019-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.24120(10)
_cell_length_b                   10.54480(10)
_cell_length_c                   17.05050(10)
_cell_measurement_reflns_used    17425
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      79.0350
_cell_measurement_theta_min      4.1270
_cell_volume                     1931.51(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.976
_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    -84.00  94.00   0.50    0.50    --    5.00  -7.00   6.00  356
  2  \w   -140.00  39.00   0.50    0.50    --  -50.10   7.00-176.00  358
  3  \w   -199.00 -21.00   0.50    0.50    -- -110.00   7.00-176.00  356
  4  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00 -60.00  238
  5  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00 150.00  238
  6  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00-120.00  238
  7  \w   -141.00 -21.00   0.50    0.50    -- -110.00  38.00 150.00  240
  8  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  30.00  244
  9  \w   -199.00 -81.00   0.50    0.50    -- -110.00 -58.00 169.57  236
 10  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -90.00  244
 11  \w   -199.00 -81.00   0.50    0.50    -- -110.00 -45.00  52.35  236
 12  \w   -199.00 -84.00   0.50    0.50    -- -110.00 -44.00 127.59  230
 13  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  244
 14  \w   -131.00 -87.00   0.50    0.50    -- -110.00  72.00 -60.00   88
 15  \w    -73.00 -47.00   0.50    0.50    -- -110.00  72.00 -60.00   52
 16  \w   -177.00-151.00   0.50    0.50    -- -110.00 -44.00  34.66   52
 17  \w   -131.00 -85.00   0.50    0.50    -- -110.00 -44.00  34.66   92
 18  \w    -98.00 -72.00   0.50    0.50    -- -110.00  72.00   0.00   52
 19  \w    -51.00 -21.00   0.50    0.50    -- -110.00  57.00  90.00   60
 20  \w   -134.00-109.00   0.50    0.50    -- -110.00  -7.00   6.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1246472000
_diffrn_orient_matrix_UB_12      -0.0009534000
_diffrn_orient_matrix_UB_13      -0.0204646000
_diffrn_orient_matrix_UB_21      0.0706446000
_diffrn_orient_matrix_UB_22      0.0141105000
_diffrn_orient_matrix_UB_23      0.0918669000
_diffrn_orient_matrix_UB_31      0.0059782000
_diffrn_orient_matrix_UB_32      -0.1454045000
_diffrn_orient_matrix_UB_33      0.0090482000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25480
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.777
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.581
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       prism
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 2041 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         6533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0557P)^2^+0.1331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.509
_reflns_Friedel_fraction_full    0.583
_reflns_Friedel_fraction_max     0.555
_reflns_number_gt                6303
_reflns_number_total             6533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04221_si_003.cif
_cod_data_source_block           p20190326c
_cod_database_code               4128709
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C38H46N6O5
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C6(H6), C9(H9), C12(H12), C29(H29), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C8(H8A,H8B), C14(H14A,H14B), C21(H21A,
 H21B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24),
 C25(H25), C27(H27), C35(H35), C36(H36), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C30(H30A,H30B,H30C), C39(H39A,H39B,
 H39C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_shelx_res_checksum              69260
_shelx_hkl_checksum              90920
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.698