Passive Membrane Permeability of Macrocycles Can Be Controlled by Exocyclic Amide Bonds.
Hickey, Jennifer L.; Zaretsky, Serge; St Denis, Megan A.; Kumar Chakka, Sai; Morshed, M. Monzur; Scully, Conor C. G.; Roughton, Andrew L.; Yudin, Andrei K.; Journal of medicinal chemistry 59 (2016) 5368–5376; doi:10.1021/acs.jmedchem.6b00222

data_1553251
_publ_section_title
;
 Passive Membrane Permeability of Macrocycles Can Be Controlled by
 Exocyclic Amide Bonds.
;
_journal_issue                   11
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              5368
_journal_page_last               5376
_journal_paper_doi               10.1021/acs.jmedchem.6b00222
_journal_volume                  59
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H57 N7 O8, 1.5(C H4 O), 3.5(H2 O)'
_chemical_formula_sum            'C41.5 H70 N7 O13'
_chemical_formula_weight         875.04
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5710(9)
_cell_length_b                   17.6203(11)
_cell_length_c                   21.2057(13)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      65.68
_cell_measurement_theta_min      3.87
_cell_volume                     5070.8(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31789
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.697
_diffrn_reflns_theta_min         3.867
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
; 
 Flack x determined using 3331 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         8708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0629
_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^)+(0.1299P)^2^+2.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                7960
_reflns_number_total             8708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm6b00222_si_003.cif
_cod_data_source_block           d13193
_cod_original_formula_sum        'C41.50 H70 N7 O13'
_cod_database_code               1553251
_shelx_estimated_absorpt_t_min   0.747
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           2013-3
_shelx_res_checksum              63380
_shelx_hkl_checksum              29528