Optical Activity and Helicity Enhancement of Highly Sensitive Dinaphthylmethane-Based Stereodynamic Probes for Secondary Alcohols.
Mądry, Tomasz; Czapik, Agnieszka; Kwit, Marcin; ACS omega 4 (2019) 3244–3256; doi:10.1021/acsomega.8b03337

data_4515134
_publ_section_title
;
 Optical Activity and Helicity Enhancement of Highly Sensitive
 Dinaphthylmethane-Based Stereodynamic Probes for Secondary Alcohols.
;
_journal_issue                   2
_journal_name_full               'ACS omega'
_journal_page_first              3244
_journal_page_last               3256
_journal_paper_doi               10.1021/acsomega.8b03337
_journal_volume                  4
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H24 O'
_chemical_formula_sum            'C25 H24 O'
_chemical_formula_weight         340.44
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.78990(10)
_cell_length_b                   10.69210(10)
_cell_length_c                   16.10540(10)
_cell_measurement_reflns_used    26877
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      76.4320
_cell_measurement_theta_min      4.0800
_cell_volume                     1857.52(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -117.00 -14.00   1.00    2.50    --  -40.71 -37.00 150.00  103
  2  \w   -114.00 -67.00   1.00    2.50    --  -40.71-136.00 -37.00   47
  3  \w   -117.00 -14.00   1.00    2.50    --  -40.71 -37.00-120.00  103
  4  \w   -117.00 -14.00   1.00    2.50    --  -40.71 -37.00  60.00  103
  5  \w    -70.00  33.00   1.00    2.50    --  -40.71  57.00-150.00  103
  6  \w     67.00 114.00   1.00    2.50    --   40.71 136.00  27.00   47
  7  \w      2.00  98.00   1.00    2.50    --   40.71-125.00  90.00   96
  8  \w     35.00  69.00   1.00    7.50    --  113.00 -30.00  90.00   34
  9  \w     83.00 158.00   1.00    7.50    --  113.00  61.00  30.00   75
 10  \w     83.00 158.00   1.00    7.50    --  113.00  61.00 -90.00   75
 11  \w     83.00 158.00   1.00    7.50    --  113.00  61.00 150.00   75
 12  \w     38.00  77.00   1.00    7.50    --  113.00 -45.00  60.00   39
 13  \w     83.00 158.00   1.00    7.50    --  113.00  61.00  60.00   75
 14  \w     35.00  69.00   1.00    7.50    --  113.00 -30.00 -30.00   34
 15  \w     79.00 158.00   1.00    7.50    --  113.00  77.00-150.00   79
 16  \w     82.00 158.00   1.00    7.50    --  113.00  30.00-150.00   76
 17  \w     83.00 158.00   1.00    7.50    --  113.00  61.00-120.00   75
 18  \w     85.00 158.00   1.00    7.50    --  113.00  45.00 -60.00   73
 19  \w     38.00  77.00   1.00    7.50    --  113.00 -45.00   0.00   39
 20  \w     79.00 158.00   1.00    7.50    --  113.00  77.00-120.00   79
 21  \w     38.00  77.00   1.00    7.50    --  113.00 -45.00-150.00   39
 22  \w     38.00  77.00   1.00    7.50    --  113.00 -45.00 -60.00   39
 23  \w     35.00  69.00   1.00    7.50    --  113.00 -30.00  60.00   34
 24  \w     85.00 158.00   1.00    7.50    --  113.00  45.00 -90.00   73
 25  \w     83.00 158.00   1.00    7.50    --  113.00  61.00-150.00   75
 26  \w     35.00  69.00   1.00    7.50    --  113.00 -30.00-120.00   34
 27  \w     30.00 158.00   1.00    7.50    --  113.00 -15.00-120.00  128
 28  \w     35.00  69.00   1.00    7.50    --  113.00 -30.00-150.00   34
 29  \w     39.00 143.00   1.00    7.50    --  113.00 -61.00-120.00  104
 30  \w     83.00 158.00   1.00    7.50    --  113.00  61.00 120.00   75
 31  \w     83.00 158.00   1.00    7.50    --  113.00  61.00 -60.00   75
 32  \w     38.00  77.00   1.00    7.50    --  113.00 -45.00 -90.00   39
 33  \w     29.00 109.00   1.00    7.50    --  113.00 -94.00 120.00   80
 34  \w     85.00 158.00   1.00    7.50    --  113.00  45.00  60.00   73
 35  \w     85.00 158.00   1.00    7.50    --  113.00  45.00-120.00   73
 36  \w     82.00 158.00   1.00    7.50    --  113.00  30.00 -90.00   76
 37  \w     82.00 158.00   1.00    7.50    --  113.00  30.00 -60.00   76
 38  \w     83.00 158.00   1.00    7.50    --  113.00  61.00  90.00   75
 39  \w     29.00 109.00   1.00    7.50    --  113.00 -94.00  90.00   80
 40  \w   -115.00 -11.00   1.00    2.50    --  -40.71 -57.00   0.00  104
 41  \w    -98.00  -2.00   1.00    2.50    --  -40.71 125.00 -90.00   96
 42  \w   -119.00  -7.00   1.00    2.50    --  -40.71 -77.00 -30.00  112
 43  \w   -119.00  -7.00   1.00    2.50    --  -40.71 -77.00  60.00  112
 44  \w      2.00  98.00   1.00    2.50    --   40.71-125.00 -90.00   96
 45  \w      1.00  27.00   1.00    2.50    --   40.71  93.00 -45.24   26
 46  \w    -33.00  70.00   1.00    2.50    --   40.71 -57.00  30.00  103
 47  \w      7.00 119.00   1.00    2.50    --   40.71  77.00 150.00  112
 48  \w      7.00 119.00   1.00    2.50    --   40.71  77.00-120.00  112
 49  \w     35.00 116.00   1.00    7.50    --  113.00-111.00 -90.00   81
 50  \w     79.00 158.00   1.00    7.50    --  113.00  77.00 -30.00   79
 51  \w     38.00  77.00   1.00    7.50    --  113.00 -45.00 150.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0111262000
_diffrn_orient_matrix_UB_12      -0.0099164000
_diffrn_orient_matrix_UB_13      -0.0953813000
_diffrn_orient_matrix_UB_21      -0.0979550000
_diffrn_orient_matrix_UB_22      -0.1038439000
_diffrn_orient_matrix_UB_23      0.0083762000
_diffrn_orient_matrix_UB_31      -0.1032506000
_diffrn_orient_matrix_UB_32      0.0993248000
_diffrn_orient_matrix_UB_33      -0.0008215000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         2.744
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plank
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         6771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0476P)^2^+0.2257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6690
_reflns_number_total             6771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03337_si_002.cif
_cod_data_source_block           1e
_cod_database_code               4515134
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H24 O'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.698
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Others
 Sof(H22B)=Sof(C23C)=Sof(H23C)=Sof(H23D)=Sof(C24C)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=1-FVAR(1)
 Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C21A(H21A), C22A(H22A), C22A(H22B), C21B(H21B), C22B(H22C)
3.b Secondary CH2 refined with riding coordinates:
 C23A(H23A,H23B), C23C(H23C,H23D), C23B(H23E,H23F)
3.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A),
 C18A(H18A), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B),
 C8B(H8B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B),
 C17B(H17B), C18B(H18B)
3.d Idealised Me refined as rotating group:
 C25A(H25A,H25B,H25C), C24A(H24A,H24B,H24C), C24C(H24D,H24E,H24F), C24B(H24G,
 H24H,H24I), C25B(H25D,H25E,H25F)
;
_shelx_res_checksum              99017
_shelx_hkl_checksum              81902
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.559
_oxdiff_exptl_absorpt_empirical_full_min 0.626