Optically pure 2-(quinolin-8-yloxy)cyclohexan-1-ol as a practical agent for molecular recognition by NMR and fluorescence spectroscopy
Bedekar, Ashutosh; Khanvilkar, Aditya N.; Chemical Communications  (2018) –; doi:10.1039/C8CC06245E

data_7122315
_publ_section_title
;
 Optically pure 2-(quinolin-8-yloxy)cyclohexan-1-ol as a practical agent
 for molecular recognition by NMR and fluorescence spectroscopy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC06245E
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H18 N O2, C8 H7 O3'
_chemical_formula_sum            'C23 H25 N O5'
_chemical_formula_weight         395.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2018-07-03 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.908(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7133(9)
_cell_length_b                   12.3487(8)
_cell_length_c                   15.4466(15)
_cell_measurement_reflns_used    949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5470
_cell_measurement_theta_min      3.8720
_cell_volume                     2018.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1702
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8587
_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     -1.00  81.00   1.00   36.34    --   19.29  57.00-150.00   82
  2  \w      4.00  83.00   1.00   36.34    --   19.29  57.00 120.00   79
  3  \w     -4.00  43.00   1.00   36.34    --  -20.07  57.00-120.00   47
  4  \w    -21.00  18.00   1.00   36.34    --  -20.07 -99.00  30.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207136000
_diffrn_orient_matrix_UB_12      0.0035310000
_diffrn_orient_matrix_UB_13      -0.0458174000
_diffrn_orient_matrix_UB_21      -0.0631641000
_diffrn_orient_matrix_UB_22      -0.0088377000
_diffrn_orient_matrix_UB_23      0.0068827000
_diffrn_orient_matrix_UB_31      -0.0084596000
_diffrn_orient_matrix_UB_32      0.0566296000
_diffrn_orient_matrix_UB_33      0.0039232000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4426
_diffrn_reflns_theta_full        29.04
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(17)
_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                2199
_reflns_number_total             3392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06245e2.cif
_cod_data_source_block           exp_1311
_cod_database_code               7122315
_chemical_oxdiff_formula         'C H N O'
_diffrn_oxdiff_ac3_digest_frames
;
017e049784feef187a8aa5afeffa57bb2a000270204
;
_diffrn_oxdiff_ac3_digest_hkl
;
010b55cbabdc8f9974a95033bcde47d97e26a6
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.725