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_4515138
_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         'C30 H24 O3'
_chemical_formula_sum            'C30 H24 O3'
_chemical_formula_weight         432.49
_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                 97.876(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4359(13)
_cell_length_b                   7.4145(5)
_cell_length_c                   17.9343(11)
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    130
_cell_measurement_theta_max      71.7850
_cell_measurement_theta_min      2.5310
_cell_volume                     2296.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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   -102.00  -6.00   1.00   10.00    --  -40.96 131.00 138.00   96
  2  \w    -67.00  35.00   1.00   10.00    --  -40.96  37.00 150.00  102
  3  \w      6.00 102.00   1.00   10.00    --   40.96-131.00  67.00   96
  4  \w      2.00  98.00   1.00   10.00    --   40.96-125.00-180.00   96
  5  \w    -35.00  67.00   1.00   10.00    --   40.96 -37.00 -30.00  102
  6  \w     15.00 117.00   1.00   10.00    --   40.96  37.00 150.00  102
  7  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00 150.00   36
  8  \w     33.00 113.00   1.00   50.00    --  111.05-111.00  90.00   80
  9  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00-180.00   36
 10  \w     33.00 113.00   1.00   50.00    --  111.05-111.00 150.00   80
 11  \w     77.00 158.00   1.00   50.00    --  111.05  77.00  30.00   81
 12  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00-120.00   36
 13  \w     33.00 113.00   1.00   50.00    --  111.05-111.00-120.00   80
 14  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00 -90.00   36
 15  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00-150.00   36
 16  \w     34.00 150.00   1.00   50.00    --  111.05 179.00-120.00  116
 17  \w     27.00 109.00   1.00   50.00    --  111.05 -94.00 -90.00   82
 18  \w     77.00 158.00   1.00   50.00    --  111.05  77.00 -90.00   81
 19  \w     81.00 158.00   1.00   50.00    --  111.05  30.00  30.00   77
 20  \w     32.00 145.00   1.00   50.00    --  111.05 -77.00 -90.00  113
 21  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00   0.00   36
 22  \w     36.00  77.00   1.00   50.00    --  111.05 -45.00  30.00   41
 23  \w     33.00 113.00   1.00   50.00    --  111.05-111.00 -60.00   80
 24  \w     33.00  69.00   1.00   50.00    --  111.05 -30.00 -30.00   36
 25  \w     34.00 138.00   1.00   50.00    --  111.05 179.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0563314000
_diffrn_orient_matrix_UB_12      0.0455029000
_diffrn_orient_matrix_UB_13      0.0713772000
_diffrn_orient_matrix_UB_21      0.0145896000
_diffrn_orient_matrix_UB_22      -0.2027850000
_diffrn_orient_matrix_UB_23      0.0148376000
_diffrn_orient_matrix_UB_31      0.0675796000
_diffrn_orient_matrix_UB_32      0.0055074000
_diffrn_orient_matrix_UB_33      -0.0470161000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20911
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         2.487
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.251
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         7985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.0995
_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^)+(0.1661P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2606
_refine_ls_wR_factor_ref         0.3057
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4867
_reflns_number_total             7985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03337_si_002.cif
_cod_data_source_block           10b
_cod_database_code               4515138
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21A(H21A), C22A(H22A), C21B(H21B), C22B(H22B)
2.b 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), C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A),
 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), C24B(H24B), C25B(H25B), C26B(H26B), C27B(H27B), C28B(H28B)
2.c Idealised Me refined as rotating group:
 C30A(H30A,H30B,H30C), C30B(H30D,H30E,H30F)
;
_shelx_res_checksum              38000
_shelx_hkl_checksum              9967
_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.595