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_4515135
_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         'C48 H60 O'
_chemical_formula_sum            'C48 H60 O'
_chemical_formula_weight         652.96
_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                 99.503(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0028(2)
_cell_length_b                   6.94336(16)
_cell_length_c                   25.5705(5)
_cell_measurement_reflns_used    5303
_cell_measurement_temperature    130
_cell_measurement_theta_max      74.8440
_cell_measurement_theta_min      3.5090
_cell_volume                     1926.69(7)
_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -115.00 -11.00   1.00   15.00    --  -40.71 -57.00 150.00  104
  2  \w    -98.00  -2.00   1.00   15.00    --  -40.71 125.00 120.00   96
  3  \w    -74.00  38.00   1.00   15.00    --  -40.71  77.00   0.00  112
  4  \w   -115.00 -11.00   1.00   15.00    --  -40.71 -57.00 -30.00  104
  5  \w     56.00 116.00   1.00   15.00    --   40.71 152.00  47.00   60
  6  \w    -33.00  70.00   1.00   15.00    --   40.71 -57.00 120.00  103
  7  \w     33.00  69.00   1.00   45.00    --  111.05 -30.00 150.00   36
  8  \w     27.00 109.00   1.00   45.00    --  111.05 -94.00  30.00   82
  9  \w     33.00 116.00   1.00   45.00    --  111.05-111.00 -30.00   83
 10  \w     36.00  77.00   1.00   45.00    --  111.05 -45.00  30.00   41
 11  \w     50.00 158.00   1.00   45.00    --  111.05  15.00-150.00  108
 12  \w     27.00 109.00   1.00   45.00    --  111.05 -94.00  60.00   82
;
_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      0.0029875000
_diffrn_orient_matrix_UB_12      0.0952753000
_diffrn_orient_matrix_UB_13      -0.0542035000
_diffrn_orient_matrix_UB_21      -0.0230840000
_diffrn_orient_matrix_UB_22      -0.1974393000
_diffrn_orient_matrix_UB_23      -0.0273763000
_diffrn_orient_matrix_UB_31      -0.1400068000
_diffrn_orient_matrix_UB_32      0.0346924000
_diffrn_orient_matrix_UB_33      -0.0068906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20872
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.217
_diffrn_reflns_theta_min         3.505
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69597
_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    1.126
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(17)
_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     447
_refine_ls_number_reflns         7058
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0610P)^2^+0.0925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6532
_reflns_number_total             7058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03337_si_002.cif
_cod_data_source_block           6b
_cod_original_cell_volume        1926.68(7)
_cod_database_code               4515135
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.794
_reflns_odcompleteness_completeness 86.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.a Ternary CH refined with riding coordinates:
 C21(H21), C22(H22), C31(H31), C32(H32), C36(H36), C40(H40), C41(H41), C46(H46)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C27(H27A,H27B), C30(H30A,H30B), C33(H33A,
 H33B), C34(H34A,H34B), C38(H38A,H38B), C39(H39A,H39B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C29(H29)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C37(H37A,H37B,H37C), C42(H42A,H42B,H42C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              21114
_shelx_hkl_checksum              83762
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.606