Dysoxylactam A: A Macrocyclolipopeptide Reverses P-Glycoprotein-Mediated Multidrug Resistance in Cancer Cells.
Liu, Cui-Ping; Xie, Cheng-Ying; Zhao, Jin-Xin; Ji, Kai-Long; Lei, Xin-Xiang; Sun, Han; Lou, Li-Guang; Yue, Jian-Min; Journal of the American Chemical Society 141 (2019) 6812–6816; doi:10.1021/jacs.9b02259

data_4128120
_publ_section_title
;
 Dysoxylactam A: A Macrocyclolipopeptide Reverses P-Glycoprotein-Mediated
 Multidrug Resistance in Cancer Cells.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6812
_journal_page_last               6816
_journal_paper_doi               10.1021/jacs.9b02259
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C31 H48 Br N O5'
_chemical_formula_sum            'C31 H48 Br N O5'
_chemical_formula_weight         594.61
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9802(6)
_cell_length_b                   22.130(3)
_cell_length_c                   28.504(3)
_cell_measurement_reflns_used    3522
_cell_measurement_temperature    100
_cell_measurement_theta_max      18.962
_cell_measurement_theta_min      2.333
_cell_volume                     3141.5(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23384
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.700
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0801 before and 0.0721 after correction. The Ratio of minimum to maximum transmission is 0.8821. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1074 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5302
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0107P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3537
_reflns_number_total             5302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02259_si_002.cif
_cod_data_source_block           2013114_0m
_cod_original_cell_volume        3141.5(6)
_cod_database_code               4128120
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.688
_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
2. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1') \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C3'(H3'), C2'(H2'), C13(H13), C12(H12), C10(H10), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,
 H6B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C3''(H3''), C4''(H4''), C7''(H7''), C6''(H6'')
3.d Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C), C19(H19A,H19B,H19C), C18(H18A,H18B,
 H18C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'