Conversion of Quinine Derivatives into Biologically Active Ionic Liquids: Advantages, Multifunctionality, and Perspectives
Pernak, Juliusz; Rzemieniecki, Tomasz; Klejdysz, Tomasz; Qu, Fengrui; Rogers, Robin D.; ACS Sustainable Chemistry & Engineering 8 (2020) 9263–9267; doi:10.1021/acssuschemeng.0c03501

data_4517769
_publ_section_title
;
 Conversion of Quinine Derivatives into Biologically Active Ionic Liquids:
 Advantages, Multifunctionality, and Perspectives
;
_journal_issue                   25
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              9263
_journal_page_last               9267
_journal_paper_doi               10.1021/acssuschemeng.0c03501
_journal_volume                  8
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'Br, C22 H29 N2 O2, C3 H8 O'
_chemical_formula_sum            'C25 H37 Br N2 O3'
_chemical_formula_weight         493.47
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.25467(2)
_cell_length_b                   13.60583(4)
_cell_length_c                   22.29025(7)
_cell_measurement_reflns_used    31209
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1160
_cell_measurement_theta_min      3.2450
_cell_volume                     2503.454(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -27.00  20.00   0.50    0.50    --  -47.57  19.00 -60.00   94
  2  \w     62.00  87.00   0.50    0.50    --   47.57 166.00-129.00   50
  3  \w     94.00 124.00   0.50    3.00    --  104.75 166.00-129.00   60
  4  \w    108.00 134.00   0.50    3.00    --  104.75 125.00 -90.00   52
  5  \w    140.00 176.00   0.50    3.00    --  104.75 125.00 -30.00   72
  6  \w    152.00 178.00   0.50    3.00    --  104.75  77.00  30.00   52
  7  \w    149.00 178.00   0.50    3.00    --  104.75  15.00   0.00   58
  8  \w    140.00 177.00   0.50    3.00    --  104.75  15.00  30.00   74
  9  \w    123.00 148.00   0.50    3.00    --  104.75  77.00  30.00   50
 10  \w    117.00 177.00   0.50    3.00    --  104.75  45.00  60.00  120
 11  \w    120.00 146.00   0.50    3.00    --  104.75  30.00 150.00   52
 12  \w    134.00 160.00   0.50    3.00    --  104.75  79.00 175.32   52
 13  \w    107.00 132.00   0.50    3.00    --  104.75 115.00  84.00   50
 14  \w     81.00 112.00   0.50    3.00    --  104.75  79.00 175.32   62
 15  \w     98.00 124.00   0.50    3.00    --  104.75  15.00  30.00   52
 16  \w    116.00 142.00   0.50    3.00    --  104.75  15.00   0.00   52
 17  \w     95.00 120.00   0.50    3.00    --  104.75  45.00 -90.00   50
 18  \w    132.00 168.00   0.50    3.00    --  104.75  45.00 -90.00   72
 19  \w    117.00 143.00   0.50    3.00    --  104.75  30.00 -90.00   52
 20  \w     82.00 178.00   0.50    3.00    --  104.75 125.00-120.00  192
 21  \w     81.00 134.00   0.50    3.00    --  104.75 125.00 -30.00  106
 22  \w     46.00  71.00   0.50    3.00    --  104.75 -61.00  60.00   50
 23  \w     81.00 106.00   0.50    3.00    --  104.75 -94.00   0.00   50
 24  \w     69.00  95.00   0.50    3.00    --  104.75-101.00  -4.17   52
 25  \w     58.00 110.00   0.50    3.00    --  104.75-125.00   0.00  104
 26  \w     77.00 112.00   0.50    3.00    --  104.75-125.00 -90.00   70
 27  \w     65.00  91.00   0.50    0.50    --   47.57-166.00-151.00   52
 28  \w     38.00  68.00   0.50    3.00    --  104.75-125.00 -90.00   60
 29  \w     42.00  92.00   0.50    3.00    --  104.75 -94.00 -30.00  100
 30  \w     48.00  74.00   0.50    3.00    --  104.75 -77.00 -90.00   52
 31  \w     47.00  73.00   0.50    3.00    --  104.75-115.00  -5.00   52
 32  \w     54.00  93.00   0.50    3.00    --  104.75 -78.00   9.89   78
 33  \w     50.00 102.00   0.50    3.00    --  104.75 -77.00  90.00  104
 34  \w     46.00  71.00   0.50    3.00    --  104.75 -61.00 150.00   50
 35  \w     32.00  73.00   0.50    3.00    --  104.75 -77.00 150.00   82
 36  \w     13.00  51.00   0.50    0.50    --   47.57-115.00  -5.00   76
 37  \w     33.00  63.00   0.50    3.00    --  104.75 -61.00 -30.00   60
 38  \w     38.00  64.00   0.50    3.00    --  104.75 -94.00   0.00   52
 39  \w     33.00 102.00   0.50    3.00    --  104.75 -77.00 -30.00  138
 40  \w     37.00  70.00   0.50    3.00    --  104.75 -61.00 -90.00   66
 41  \w     36.00  62.00   0.50    3.00    --  104.75 -94.00-180.00   52
 42  \w     72.00  98.00   0.50    3.00    --  104.75 -94.00-180.00   52
 43  \w     64.00  90.00   0.50    3.00    --  104.75-125.00-180.00   52
 44  \w     39.00 109.00   0.50    3.00    --  104.75-125.00 -60.00  140
 45  \w    -15.00  27.00   0.50    0.50    --  -47.57  19.00 150.00   84
 46  \w    -89.00  -7.00   0.50    0.50    --  -47.57 115.00  84.00  164
 47  \w   -102.00 -77.00   0.50    0.50    --  -47.57 166.00-129.00   50
 48  \w   -111.00 -86.00   0.50    3.00    -- -102.00 166.00-129.00   50
 49  \w   -117.00 -91.00   0.50    3.00    -- -102.00 -54.00  27.36   52
 50  \w   -132.00-107.00   0.50    3.00    -- -102.00-115.00  -5.00   50
 51  \w   -119.00 -75.00   0.50    0.50    --  -47.57-125.00  60.00   88
 52  \w   -108.00 -83.00   0.50    0.50    --  -47.57-166.00-151.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1003366000
_diffrn_orient_matrix_UB_12      -0.0414097000
_diffrn_orient_matrix_UB_13      -0.0524987000
_diffrn_orient_matrix_UB_21      0.1395525000
_diffrn_orient_matrix_UB_22      0.0238392000
_diffrn_orient_matrix_UB_23      -0.0435272000
_diffrn_orient_matrix_UB_31      0.0727385000
_diffrn_orient_matrix_UB_32      -0.1026989000
_diffrn_orient_matrix_UB_33      0.0110478000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0075
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.367
_diffrn_reflns_theta_min         3.806
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.449
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(3)
_refine_ls_extinction_coef       0.00098(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0166
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+0.8545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0440
_refine_ls_wR_factor_ref         0.0440
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5237
_reflns_number_total             5240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc0c03501_si_002.cif
_cod_data_source_block           mn04-qu
_cod_depositor_comments
;Adding full bibliography for 4517768--4517769.cif.

 Adding full bibliography for 4517768--4517769.cif.
;
_cod_original_cell_volume        2503.453(12)
_cod_database_code               4517769
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H38BrN2O3
_diffrn_oxdiff_digest_frames
;
017f9d8c534767791e2de28ac1297791f7037064425
;
_diffrn_oxdiff_digest_hkl
;
0198959e70421707cff3e410bd2edcdc09cd60
;
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3A)
;
_shelx_res_checksum              98425
_shelx_hkl_checksum              17290
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.726