X-ray Crystallography and Unexpected Chiroptical Properties Reassign the Configuration of Haliclonadiamine.
Liu, Hong-Bing; Imler, Gregory H.; Baldridge, Kim K.; O'Connor, Robert D; Siegel, Jay S.; Deschamps, Jeffrey R.; Bewley, Carole A.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12926

data_4134096
_publ_section_title
;
 X-ray Crystallography and Unexpected Chiroptical Properties Reassign the
 Configuration of Haliclonadiamine.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12926
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H42 N2, 2(C2 F3 O2)'
_chemical_formula_sum            'C29 H42 F6 N2 O4'
_chemical_formula_weight         596.64
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.3959(17)
_cell_angle_beta                 97.1969(19)
_cell_angle_gamma                92.7279(16)
_cell_formula_units_Z            3
_cell_length_a                   9.4985(3)
_cell_length_b                   15.8907(5)
_cell_length_c                   16.0857(5)
_cell_measurement_reflns_used    7240
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.46
_cell_measurement_theta_min      2.83
_cell_volume                     2354.78(13)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Photon II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Montel multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_unetI/netI     0.1128
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38964
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         2.829
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 3717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(8)
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1247
_refine_ls_number_reflns         15811
_refine_ls_number_restraints     681
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0773P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                10940
_reflns_number_total             15811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12926_si_004.cif
_cod_data_source_block           nidab03_100K
_cod_database_code               4134096
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              1556
_shelx_hkl_checksum              73386