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_4134094
_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                 91.1697(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1005(4)
_cell_length_b                   9.2621(2)
_cell_length_c                   24.6121(6)
_cell_measurement_reflns_used    9762
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.53
_cell_measurement_theta_min      3.37
_cell_volume                     2985.76(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 0.997
_diffrn_measured_fraction_theta_max 0.990
_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  0.0152
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_number            12043
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.624
_diffrn_reflns_theta_min         3.374
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 5233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_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     851
_refine_ls_number_reflns         12043
_refine_ls_number_restraints     553
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0587P)^2^+1.1962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                11652
_reflns_number_total             12043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12926_si_003.cif
_cod_data_source_block           nidab04_100K
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134094
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.833
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              26938
_shelx_hkl_checksum              32243