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_1553252
_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 O7, C H4 O, H2 O'
_chemical_formula_sum            'C41 H63 N7 O9'
_chemical_formula_weight         797.98
_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            8
_cell_length_a                   13.1244(10)
_cell_length_b                   13.6010(9)
_cell_length_c                   48.964(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.44
_cell_measurement_theta_min      3.82
_cell_volume                     8740.3(10)
_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 0.969
_diffrn_measured_fraction_theta_max 0.986
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            58403
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.847
_diffrn_reflns_theta_min         1.804
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  7528
_exptl_absorpt_correction_T_min  7036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             3440
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 6268 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1027
_refine_ls_number_reflns         15179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0472P)^2^+2.1010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                14547
_reflns_number_total             15179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm6b00222_si_002.cif
_cod_data_source_block           d13197
_cod_original_cell_volume        8740.2(11)
_cod_database_code               1553252
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2013-3
_shelx_res_checksum              9569
_shelx_hkl_checksum              99762