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_4134095
_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      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   geom
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.2390(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1044(4)
_cell_length_b                   9.2541(3)
_cell_length_c                   24.6027(7)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.50
_cell_measurement_theta_min      3.86
_cell_volume                     2982.86(16)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            51161
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.670
_diffrn_reflns_theta_min         3.373
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 5060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     851
_refine_ls_number_reflns         12149
_refine_ls_number_restraints     547
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0551P)^2^+0.9180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                11505
_reflns_number_total             12149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12926_si_002.cif
_cod_data_source_block           nidab02_100K
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134095
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.864
_shelx_res_checksum              31616
_shelx_hkl_checksum              80506