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_7059409
_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         'C10 H19 N2, Cl'
_chemical_formula_sum            'C10 H19 Cl N2'
_chemical_formula_weight         202.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_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
;
2019-10-28 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.664(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0742(3)
_cell_length_b                   10.8811(4)
_cell_length_c                   11.8127(4)
_cell_measurement_reflns_used    5917
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6750
_cell_measurement_theta_min      4.0650
_cell_volume                     1137.98(7)
_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      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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   -114.00 -22.00   2.00    2.00    --  -43.31 -38.00  30.00   46
  2  \w    -50.00  26.00   2.00    2.00    --  -43.31  38.00-150.00   38
  3  \w    -20.00  82.00   2.00    2.00    --   43.31 -99.00-150.00   51
  4  \w     35.00  97.00   2.00    2.00    --  103.95 -45.00 150.00   31
  5  \w     31.00  91.00   2.00    2.00    --  103.95 -30.00 -60.00   30
  6  \w     35.00  97.00   2.00    2.00    --  103.95 -45.00  60.00   31
  7  \w     31.00  91.00   2.00    2.00    --  103.95 -30.00 -90.00   30
  8  \w     35.00  97.00   2.00    2.00    --  103.95 -45.00  90.00   31
  9  \w     23.00 107.00   2.00    2.00    --  103.95 -94.00  90.00   42
 10  \w     35.00  97.00   2.00    2.00    --  103.95 -45.00-150.00   31
 11  \w     31.00  91.00   2.00    2.00    --  103.95 -30.00 120.00   30
 12  \w     23.00 107.00   2.00    2.00    --  103.95 -94.00  60.00   42
 13  \w     35.00  89.00   2.00    2.00    --  103.95 -45.00-120.00   27
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_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      0.1068545000
_diffrn_orient_matrix_UB_12      -0.0146813000
_diffrn_orient_matrix_UB_13      0.1202055000
_diffrn_orient_matrix_UB_21      -0.0243880000
_diffrn_orient_matrix_UB_22      0.1360557000
_diffrn_orient_matrix_UB_23      0.0267787000
_diffrn_orient_matrix_UB_31      -0.1351280000
_diffrn_orient_matrix_UB_32      -0.0360669000
_diffrn_orient_matrix_UB_33      0.0522557000
_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  0.0290
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.866
_diffrn_reflns_theta_min         3.835
_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    2.635
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.668
_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    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'diffusion of ethyl acetate vapour into a acetonitrle solution of the compound'
_exptl_crystal_size_max          0.856
_exptl_crystal_size_mid          0.794
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.033(14)
_refine_ls_extinction_coef       0.0081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0635P)^2^+0.0992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3508
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00349b2.cif
_cod_data_source_block           icrjdc
_cod_depositor_comments
;Adding full bibliography for 7059409--7059410.cif.

 Adding full bibliography for 7059409--7059410.cif.
;
_cod_database_code               7059409
_nottingham_internal_coll_name   ICRJDC
_nottingham_internal_coll_number 16550
_nottingham_internal_coll_client ICR/JDU
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 2.00
_nottingham_internal_coll_frame_width 2.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   17/10/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 08/02/2017
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 8/2/2017
_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         'C14 N4 H24'
_chemical_oxdiff_usercomment
'ICRJDC #16550 GVA-1082 IN FOMBLIN FILM ON MICROMOUNT FOR ICR/JDU'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.967(14) 0.033(14)
2. 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
3.a Ternary CH refined with riding coordinates:
 C7(H7), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C26(H26A,H26B), C29(H29A,H29B)
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:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
;
_shelx_res_checksum              3176
_olex2_date_sample_data_collection 2016-10-17
_olex2_date_sample_submission    2016-10-13
_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 3.456
_oxdiff_exptl_absorpt_empirical_full_min 0.579