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_4517768
_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_formula_moiety         'Br, C30 H45 N2 O2'
_chemical_formula_sum            'C30 H45 Br N2 O2'
_chemical_formula_weight         545.59
_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             2019-08-16
_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                   8.50945(4)
_cell_length_b                   11.48583(6)
_cell_length_c                   28.11292(13)
_cell_measurement_reflns_used    36180
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1400
_cell_measurement_theta_min      3.1350
_cell_volume                     2747.70(2)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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    -24.00  51.00   0.50    1.00    --   47.45 -44.00 -15.00  150
  2  \w     32.00  72.00   0.50    3.00    --  104.75 -61.00 -30.00   80
  3  \w     36.00  72.00   0.50    3.00    --  104.75 -61.00 -90.00   72
  4  \w     46.00  71.00   0.50    3.00    --  104.75 -77.00-150.00   50
  5  \w     32.00 102.00   0.50    3.00    --  104.75 -77.00-120.00  140
  6  \w     32.00 119.00   0.50    3.00    --  104.75-135.00-115.27  174
  7  \w     82.00 111.00   0.50    3.00    --  104.75-125.00   0.00   58
  8  \w     58.00 105.00   0.50    3.00    --  104.75-105.00 128.82   94
  9  \w     68.00  93.00   0.50    3.00    --  104.75-114.00 130.70   50
 10  \w     50.00 102.00   0.50    3.00    --  104.75 -77.00 120.00  104
 11  \w     46.00  72.00   0.50    3.00    --  104.75-109.00  27.88   52
 12  \w     41.00  67.00   0.50    3.00    --  104.75-125.00   0.00   52
 13  \w     33.00  73.00   0.50    3.00    --  104.75 -77.00 -30.00   80
 14  \w     34.00  76.00   0.50    3.00    --  104.75 -77.00 -90.00   84
 15  \w     32.00  57.00   0.50    3.00    --  104.75 -61.00-120.00   50
 16  \w     33.00  65.00   0.50    3.00    --  104.75 -94.00 -90.00   64
 17  \w     18.00  95.00   0.50    1.00    --   47.45-125.00-120.00  154
 18  \w     37.00  63.00   0.50    3.00    --  104.75 -77.00  30.00   52
 19  \w     32.00  72.00   0.50    3.00    --  104.75 -61.00  90.00   80
 20  \w     32.00 131.00   0.50    3.00    --  104.75 -84.00 144.00  198
 21  \w     91.00 177.00   0.50    3.00    --  104.75  44.00 135.00  172
 22  \w    131.00 157.00   0.50    3.00    --  104.75 152.00 -13.12   52
 23  \w     89.00 178.00   0.50    3.00    --  104.75 103.00  -5.00  178
 24  \w    103.00 129.00   0.50    3.00    --  104.75  30.00-150.00   52
 25  \w    102.00 149.00   0.50    3.00    --  104.75  15.00-120.00   94
 26  \w    109.00 134.00   0.50    3.00    --  104.75  61.00-150.00   50
 27  \w     82.00 178.00   0.50    3.00    --  104.75  77.00-120.00  192
 28  \w     88.00 178.00   0.50    3.00    --  104.75  61.00  30.00  180
 29  \w     85.00 178.00   0.50    3.00    --  104.75  71.00 120.94  186
 30  \w     92.00 177.00   0.50    3.00    --  104.75  45.00  90.00  170
 31  \w     82.00 178.00   0.50    3.00    --  104.75  77.00  60.00  192
 32  \w     83.00 145.00   0.50    3.00    --  104.75  78.00  50.56  124
 33  \w     32.00  72.00   0.50    3.00    --  104.75 -61.00 120.00   80
 34  \w     33.00 105.00   0.50    3.00    --  104.75 -94.00  60.00  144
 35  \w    -49.00  25.00   0.50    1.00    --  -47.45  44.00 135.00  148
 36  \w   -106.00 -29.00   0.50    3.00    -- -102.00 103.00  -5.00  154
 37  \w   -120.00 -74.00   0.50    1.00    --  -47.45-125.00  60.00   92
;
_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      0.0491873000
_diffrn_orient_matrix_UB_12      0.1079082000
_diffrn_orient_matrix_UB_13      0.0288888000
_diffrn_orient_matrix_UB_21      0.0861842000
_diffrn_orient_matrix_UB_22      0.0487778000
_diffrn_orient_matrix_UB_23      -0.0438753000
_diffrn_orient_matrix_UB_31      -0.1514201000
_diffrn_orient_matrix_UB_32      0.0630182000
_diffrn_orient_matrix_UB_33      -0.0155768000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            40283
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.336
_diffrn_reflns_theta_min         3.144
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.254
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.511
_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    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2463 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0186
_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^+0.9489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0477
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5746
_reflns_number_total             5748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc0c03501_si_003.cif
_cod_data_source_block           mn06-qu
_cod_depositor_comments
;Adding full bibliography for 4517768--4517769.cif.

 Adding full bibliography for 4517768--4517769.cif.
;
_cod_database_code               4517768
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H45 Br N2 O2'
_chemical_oxdiff_usercomment     'sample TR5'
_diffrn_oxdiff_digest_frames
;
01377792ac1e52f3b5435aef7d8d1e078704098b9ae
;
_diffrn_oxdiff_digest_hkl
;
010ebeee630416304bf2042bb8c1defe28a9a3
;
_reflns_odcompleteness_completeness 99.13
_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)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B)
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), C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              60678
_shelx_hkl_checksum              40955
_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 1.755
_oxdiff_exptl_absorpt_empirical_full_min 0.683