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_7122314
_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 unk
_chemical_formula_moiety         'C25 H25 N O5'
_chemical_formula_sum            'C25 H25 N O5'
_chemical_formula_weight         419.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           ' P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_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            4
_cell_length_a                   8.1390(5)
_cell_length_b                   15.8253(10)
_cell_length_c                   17.1850(17)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3520
_cell_measurement_theta_min      3.7770
_cell_volume                     2213.5(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    '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    'ShelXS (Sheldrick, 2008)'
_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 0.8671
_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     32.00  98.00   1.00    3.20    --   19.44-178.00 -60.00   66
  2  \w    -25.00  63.00   1.00    3.20    --   19.44 -99.00  30.00   88
  3  \w    -12.00  90.00   1.00    3.20    --   19.44  76.00  43.00  102
  4  \w     -2.00  69.00   1.00    3.20    --   19.44  57.00-180.00   71
;
_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      -0.0391333000
_diffrn_orient_matrix_UB_12      -0.0349301000
_diffrn_orient_matrix_UB_13      0.0180727000
_diffrn_orient_matrix_UB_21      0.0314727000
_diffrn_orient_matrix_UB_22      0.0129987000
_diffrn_orient_matrix_UB_23      0.0365910000
_diffrn_orient_matrix_UB_31      -0.0711825000
_diffrn_orient_matrix_UB_32      0.0249067000
_diffrn_orient_matrix_UB_33      0.0062339000
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13669
_diffrn_reflns_theta_full        28.8656
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93555
_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    1.2587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888.4862
_refine_diff_density_max         0.2841
_refine_diff_density_min         -0.2988
_refine_diff_density_rms         0.0724
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   1(10)
_refine_ls_d_res_high            0.7361
_refine_ls_d_res_low             5.9090
_refine_ls_goodness_of_fit_ref   0.9863
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9863
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0371P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.829
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              -20
_reflns_limit_l_max              22
_reflns_limit_l_min              -21
_reflns_number_gt                3103
_reflns_number_total             5032
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc06245e2.cif
_cod_data_source_block           exp_1245
_cod_database_code               7122314
_diffrn_oxdiff_ac3_digest_frames
;
01bd8ae0544bc4d94d08e5a8bc9ac5e31f000283e30
;
_diffrn_oxdiff_ac3_digest_hkl
;
011de6b872b189be47517514443d279e35b0c8
;
_reflns_odcompleteness_completeness 99.50
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C20(H20), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C14(H14a,H14b), C16(H16a,H16b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C27(H27), C31(H31), C10(H10), C6(H6), C28(H28), C5(H5), C8(H8),
 C9(H9), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
_olex2_date_sample_data_collection 2017-10-14
_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 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.942