Synthesis of chiral iron-based ionic liquids: modelling stable hybrid materials
Martin, Carmen; Cano, Israel; Scé, Fabio; Pérez-Aguirre, Rubén; Gimbert-Suriñach, Carolina; Lopez-Cornejo, Pilar; de Pedro, Imanol; New Journal of Chemistry 44 (2020) 6375–6383; doi:10.1039/D0NJ00349B

data_7059410
_publ_section_title
;
 Synthesis of chiral iron-based ionic liquids: modelling stable hybrid
 materials
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6375
_journal_page_last               6383
_journal_paper_doi               10.1039/D0NJ00349B
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H29 N2 O, Cl, H2 O'
_chemical_formula_sum            'C16 H31 Cl N2 O2'
_chemical_formula_weight         318.88
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2019-10-29 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.888(3)
_cell_angle_beta                 94.947(3)
_cell_angle_gamma                91.100(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6283(2)
_cell_length_b                   7.8369(3)
_cell_length_c                   17.6060(5)
_cell_measurement_reflns_used    30840
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6660
_cell_measurement_theta_min      5.0220
_cell_volume                     910.84(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_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    -40.00  -6.00   2.00    2.00    --  -38.50 -83.00 -29.99   17
  2  \w   -111.00 -17.00   2.00    2.00    --  -38.50 -38.00 -60.00   47
  3  \w     16.00 112.00   2.00    2.00    --   42.83  57.00  30.00   48
  4  \w    -27.00  69.00   2.00    2.00    --   42.83 -57.00 -30.00   48
  5  \w      2.00  98.00   2.00    2.00    --   42.83-125.00-120.00   48
  6  \w     14.00  46.00   2.00    2.00    --   46.00  79.00 -72.14   16
  7  \w     14.00  46.00   2.00    2.00    --   46.00  79.00  59.81   16
  8  \w     18.00  46.00   2.00    2.00    --   50.00  79.00 169.04   14
  9  \w     18.00  46.00   2.00    2.00    --   50.00  80.00 132.69   14
 10  \w     22.00  48.00   2.00    2.00    --   54.00  78.00 -55.35   13
 11  \w     24.00 126.00   2.00    2.00    --   54.00  72.00  37.36   51
 12  \w     23.00 127.00   2.00    2.00    --   54.00  77.00  77.81   52
 13  \w     31.00 135.00   2.00    2.00    --   62.00  76.00  81.37   52
 14  \w     31.00 135.00   2.00    2.00    --   62.00  75.00-147.23   52
 15  \w     36.00 138.00   2.00    2.00    --   66.00  72.00-118.29   51
 16  \w     35.00 139.00   2.00    2.00    --   66.00  74.00 146.52   52
 17  \w     35.00 139.00   2.00    2.00    --   66.00  77.00  88.05   52
 18  \w     39.00 143.00   2.00    2.00    --   70.00  77.00 -91.28   52
 19  \w     39.00 143.00   2.00    2.00    --   70.00  76.00 -26.89   52
 20  \w     44.00 146.00   2.00    2.00    --   74.00  73.00  14.04   51
 21  \w     43.00 147.00   2.00    2.00    --   74.00  76.00 -48.51   52
 22  \w     44.00 146.00   2.00    2.00    --   74.00  70.00-144.31   51
 23  \w     47.00 151.00   2.00    2.00    --   78.00  77.00 158.11   52
 24  \w     51.00 155.00   2.00    2.00    --   82.00  76.00  55.53   52
 25  \w     53.00 153.00   2.00    2.00    --   82.00  68.00 -84.75   50
 26  \w     57.00 157.00   2.00    2.00    --   86.00  67.00 -11.35   50
 27  \w     57.00 157.00   2.00    2.00    --   86.00  69.00 103.15   50
 28  \w     73.00 177.00   2.00    2.00    --  104.50  77.00  60.00   52
 29  \w     33.00 121.00   2.00    2.00    --  104.50-125.00  90.00   44
 30  \w     80.00 176.00   2.00    2.00    --  104.50  45.00  30.00   48
 31  \w     77.00 175.00   2.00    2.00    --  104.50  61.00 150.00   49
 32  \w     73.00 177.00   2.00    2.00    --  104.50  77.00-120.00   52
 33  \w     33.00  97.00   2.00    2.00    --  104.50 -45.00 150.00   32
 34  \w     73.00 177.00   2.00    2.00    --  104.50  77.00-180.00   52
 35  \w     33.00  97.00   2.00    2.00    --  104.50 -45.00 -60.00   32
 36  \w     23.00 109.00   2.00    2.00    --  104.50 -94.00 120.00   43
 37  \w     23.00 109.00   2.00    2.00    --  104.50 -94.00 -90.00   43
 38  \w     73.00 177.00   2.00    2.00    --  104.50  77.00 120.00   52
 39  \w     73.00 177.00   2.00    2.00    --  104.50  77.00  30.00   52
 40  \w     73.00 177.00   2.00    2.00    --  104.50  77.00-150.00   52
 41  \w     77.00 175.00   2.00    2.00    --  104.50  59.00 -50.10   49
 42  \w     73.00 177.00   2.00    2.00    --  104.50  77.00 -90.00   52
 43  \w     80.00 176.00   2.00    2.00    --  104.50  45.00   0.00   48
 44  \w     77.00 175.00   2.00    2.00    --  104.50  61.00-180.00   49
 45  \w     73.00 177.00   2.00    2.00    --  104.50  77.00  90.00   52
 46  \w     23.00 109.00   2.00    2.00    --  104.50 -94.00-180.00   43
 47  \w    -50.00  34.00   2.00    2.00    --  -38.50  38.00  90.00   42
 48  \w    -45.00  -7.00   2.00    2.00    --  -38.50 -82.00 -92.00   19
 49  \w    -44.00 128.00   2.00    2.00    --   42.83   0.00 -30.00   86
 50  \w     20.00 114.00   2.00    2.00    --   42.83  38.00  60.00   47
 51  \w    -44.00 128.00   2.00    2.00    --   42.83   0.00-180.00   86
 52  \w    -44.00 128.00   2.00    2.00    --   42.83   0.00-150.00   86
 53  \w     16.00 112.00   2.00    2.00    --   42.83  57.00-180.00   48
 54  \w    -44.00 128.00   2.00    2.00    --   42.83   0.00-120.00   86
 55  \w    -44.00 128.00   2.00    2.00    --   42.83   0.00 -90.00   86
 56  \w    -44.00 128.00   2.00    2.00    --   42.83   0.00 -60.00   86
 57  \w     13.00  39.00   2.00    2.00    --   46.00  83.00-112.72   13
 58  \w     22.00  48.00   2.00    2.00    --   54.00  78.00 -15.46   13
 59  \w     27.00 131.00   2.00    2.00    --   58.00  74.00-166.88   52
 60  \w     39.00 143.00   2.00    2.00    --   70.00  77.00 -42.62   52
 61  \w     43.00 147.00   2.00    2.00    --   74.00  77.00 -99.98   52
 62  \w     46.00 144.00   2.00    2.00    --   74.00  63.00  43.57   49
 63  \w     33.00  97.00   2.00    2.00    --  104.50 -45.00-120.00   32
 64  \w     18.00 178.00   2.00    2.00    --  104.50   0.00 -60.00   80
 65  \w     18.00 178.00   2.00    2.00    --  104.50   0.00 -90.00   80
 66  \w     18.00 178.00   2.00    2.00    --  104.50   0.00-120.00   80
 67  \w     18.00 178.00   2.00    2.00    --  104.50   0.00-150.00   80
 68  \w     18.00 178.00   2.00    2.00    --  104.50   0.00-180.00   80
 69  \w     73.00 177.00   2.00    2.00    --  104.50  77.00 150.00   52
 70  \w     77.00 175.00   2.00    2.00    --  104.50  61.00  60.00   49
 71  \w     77.00 175.00   2.00    2.00    --  104.50  61.00  30.00   49
 72  \w     77.00 175.00   2.00    2.00    --  104.50  61.00 -30.00   49
 73  \w     77.00 175.00   2.00    2.00    --  104.50  61.00-120.00   49
 74  \w     18.00 162.00   2.00    2.00    --  104.50   0.00  90.00   72
 75  \w     18.00 178.00   2.00    2.00    --  104.50   0.00 -30.00   80
 76  \w     18.00 178.00   2.00    2.00    --  104.50   0.00   0.00   80
 77  \w     74.00 178.00   2.00    2.00    --  104.50  78.00-161.68   52
 78  \w     18.00 178.00   2.00    2.00    --  104.50   0.00  60.00   80
 79  \w     18.00 178.00   2.00    2.00    --  104.50   0.00  30.00   80
 80  \w     77.00 175.00   2.00    2.00    --  104.50  61.00 120.00   49
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1246433000
_diffrn_orient_matrix_UB_12      0.1638302000
_diffrn_orient_matrix_UB_13      -0.0065961000
_diffrn_orient_matrix_UB_21      -0.0251016000
_diffrn_orient_matrix_UB_22      -0.0235130000
_diffrn_orient_matrix_UB_23      -0.0873656000
_diffrn_orient_matrix_UB_31      -0.1956536000
_diffrn_orient_matrix_UB_32      -0.1061865000
_diffrn_orient_matrix_UB_33      0.0063491000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49890
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.944
_diffrn_reflns_theta_min         5.044
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.900
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method
'Crystallised from acetonitrile at 4 degree celcius'
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6939
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+0.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                6812
_reflns_number_total             6939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00349b2.cif
_cod_data_source_block           icrjda
_cod_depositor_comments
;Adding full bibliography for 7059409--7059410.cif.

 Adding full bibliography for 7059409--7059410.cif.
;
_cod_original_cell_volume        910.84(6)
_cod_database_code               7059410
_nottingham_internal_coll_name   ICRJDA
_nottingham_internal_coll_number 16483
_nottingham_internal_coll_client ICR/JDU
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'ofand \w scans'
_nottingham_internal_coll_frame_time 'degrees,, 2.00'
_nottingham_internal_coll_frame_width 'in, 2.00'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   12/09/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 13/09/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 13/9/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 8/2/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 8/2/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 8/2/2017
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C16 H31 Cl N2 O2'
_chemical_oxdiff_usercomment
'ICRJDA #16483 GVB-1152 micromount in fomblin for ICR/JDU'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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,H) groups
2. Restrained distances
 O2W-H2WA = O2W-H2WB = O1W-H1WB = O1W-H1WA
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C28(H28), C29(H29), C32(H32), C34(H34)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C26(H26A,H26B),
 C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              8085
_olex2_date_sample_data_collection 2016-09-13
_olex2_date_sample_submission    2016-09-12
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.687