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_7122317
_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 H17 N O2, 0.5(H2 O)'
_chemical_formula_sum            'C15 H18 N O2.5'
_chemical_formula_weight         252.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           ' C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_Int_Tables_number      20
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-03 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.4035(9)
_cell_length_b                   22.609(2)
_cell_length_c                   14.0695(18)
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7530
_cell_measurement_theta_min      4.6010
_cell_volume                     2673.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8607
_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    -25.00  63.00   1.00    2.23    --   19.44 -99.00   0.00   88
  2  \w    -54.00  93.00   1.00    2.23    --   19.44   0.00-150.00  147
  3  \w    -30.00  59.00   1.00    2.23    --   19.44  19.00  30.00   89
;
_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      0.0004210000
_diffrn_orient_matrix_UB_12      -0.0267878000
_diffrn_orient_matrix_UB_13      -0.0262022000
_diffrn_orient_matrix_UB_21      -0.0196824000
_diffrn_orient_matrix_UB_22      0.0158625000
_diffrn_orient_matrix_UB_23      -0.0418617000
_diffrn_orient_matrix_UB_31      0.0821342000
_diffrn_orient_matrix_UB_32      0.0039425000
_diffrn_orient_matrix_UB_33      -0.0098888000
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8210
_diffrn_reflns_theta_full        28.6677
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2538
_exptl_crystal_F_000             1080.5420
_refine_diff_density_max         0.1517
_refine_diff_density_min         -0.1477
_refine_diff_density_rms         0.0321
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1.5(5)
_refine_ls_d_res_high            0.7408
_refine_ls_d_res_low             5.9727
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0419
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0419
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.3874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.792
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              30
_reflns_limit_k_min              -29
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                2425
_reflns_number_total             2971
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc06245e2.cif
_cod_data_source_block           exp_965
_cod_depositor_comments
;

2025-03-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C15 H17 N O2), H2 O'
_cod_original_formula_sum        'C30 H36 N2 O5'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     504.61
_cod_database_code               7122317
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 O(H) groups
2. Others
 Fixed Sof: H1a(0.5) H1b(0.5)
3.a Ternary CH refined with riding coordinates:
 C12(H12), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C16(H16a,H16b), C15(H15a,H15b), C14(H14a,H14b)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C9(H9), C10(H10), C8(H8)
3.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_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 1.138
_oxdiff_exptl_absorpt_empirical_full_min 0.799