A room temperature ferroelectric material with photoluminescence: (1,3-dicyclohexylimidazole)<sub>2</sub>MnCl<sub>4</sub>.
Chen, Peng; Jiao, Shulin; Tang, Zheng; Sun, Xiaofan; Li, Dong; Yang, Zhu; Lu, Yanzhou; Zhang, Wentao; Cai, Hong-Ling; Wu, X. S.; Dalton transactions (Cambridge, England : 2003)  (2023) –; doi:10.1039/d3dt01260c

data_7713242
_publ_section_title
;
 A room temperature ferroelectric material with photoluminescence:
 (1,3-dicyclohexylimidazole)<sub>2</sub>MnCl<sub>4</sub>.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt01260c
_journal_year                    2023
_chemical_formula_moiety
'4(Cl4 Mn), 3(C15 H27 N2), C13 H25 N4, C15 H21 N2, 2(C15 H26 N2)'
_chemical_formula_sum            'C103 H179 Cl16 Mn4 N16'
_chemical_formula_weight         2428.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-24
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2022-11-15 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                81.600(3)
_cell_angle_beta                 78.332(3)
_cell_angle_gamma                67.560(4)
_cell_formula_units_Z            2
_cell_length_a                   16.9646(7)
_cell_length_b                   17.3879(7)
_cell_length_c                   26.9590(11)
_cell_measurement_reflns_used    17993
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0290
_cell_measurement_theta_min      2.1570
_cell_volume                     7177.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     -2.00  24.00   0.50    2.00    --   20.00  54.00-113.80   52
  2  \w    -74.00   9.00   0.50    2.00    --   20.00  54.00-180.00  166
  3  \w     32.00  64.00   0.50    2.00    --   20.00  54.00-180.00   64
  4  \w    -70.00  76.00   0.50    2.00    --   20.00  54.00  90.00  292
  5  \w     84.00 110.00   0.50    2.00    --   20.00  54.00  90.00   52
  6  \w    -74.00  84.00   0.50    2.00    --   20.00  54.00 -30.00  316
  7  \w    -63.00 -25.00   0.50    2.00    --   20.00  54.00  30.00   76
  8  \w     74.00 100.00   0.50    2.00    --   20.00  54.00  30.00   52
  9  \w    -73.00  -4.00   0.50    2.00    --   20.00  54.00 120.00  138
 10  \w     56.00  87.00   0.50    2.00    --   20.00  54.00 120.00   62
 11  \w    -67.00 -18.00   0.50    2.00    --   20.00  54.00-150.00   98
 12  \w    -12.00  15.00   0.50    2.00    --   20.00  54.00-150.00   54
 13  \w     25.00  51.00   0.50    2.00    --   20.00  54.00-150.00   52
 14  \w     85.00 110.00   0.50    2.00    --   20.00  54.00-150.00   50
 15  \w    -66.00 101.00   0.50    2.00    --   20.00  54.00   0.00  334
 16  \w    -69.00  62.00   0.50    2.00    --   20.00  54.00 -90.00  262
 17  \w     71.00  96.00   0.50    2.00    --   20.00  54.00 -90.00   50
 18  \w    -67.00  12.00   0.50    2.00    --   20.00  54.00 150.00  158
 19  \w     43.00  68.00   0.50    2.00    --   20.00  54.00-120.00   50
 20  \w    -66.00 -39.00   0.50    2.00    --   20.00  54.00 -60.00   54
 21  \w    -63.00 -37.00   0.50    2.00    --   20.00  54.00  60.00   52
 22  \w    -66.00 -40.00   0.50    2.00    --   20.00  54.00-113.80   52
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0160379000
_diffrn_orient_matrix_UB_12      0.0300458000
_diffrn_orient_matrix_UB_13      -0.0143205000
_diffrn_orient_matrix_UB_21      -0.0429244000
_diffrn_orient_matrix_UB_22      0.0286498000
_diffrn_orient_matrix_UB_23      -0.0003769000
_diffrn_orient_matrix_UB_31      0.0006875000
_diffrn_orient_matrix_UB_32      0.0153511000
_diffrn_orient_matrix_UB_33      0.0228197000
_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  0.0514
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            117157
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.790
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       block
_exptl_crystal_F_000             2562
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.479
_refine_diff_density_min         -1.389
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1252
_refine_ls_number_reflns         25136
_refine_ls_number_restraints     4283
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.1022
_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^)+(0.1698P)^2^+17.1578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2859
_refine_ls_wR_factor_ref         0.3378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13741
_reflns_number_total             25136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01260c2.cif
_cod_data_source_block           mncl3-cp-12-23
_cod_database_code               7713242
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'Mn1 Cl1 N1 C1 H1'
_chemical_oxdiff_usercomment     Mn1Cl1N1C1H1
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.875
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C49-C99 = C49-C103 = C99-C25 = C25-C101 = C101-C51 = C51-C103
 1.54 with sigma of 0.02
 C1-C4 = C1-C1D = C4-C1A = C1A-C1B = C1B-C1C = C1C-C1D
 1.54 with sigma of 0.02
 H1BB-H5A_$1
 2.2 with sigma of 0.01
 C49-C25 = C49-C51 = C99-C101 = C25-C51 = C101-C103
 2.54 with sigma of 0.04
 C1-C1A = C1-C1C = C4-C1B = C1A-C1C = C1B-C1D
 2.54 with sigma of 0.04
 C49-C99 \\sim C99-C25 \\sim C25-C101 \\sim C101-C51 \\sim C51-C103 \\sim
C103-C49
 with sigma of 0.02
 C49-C51 \\sim C25-C51 \\sim C99-C103 \\sim C99-C101 \\sim C101-C103 \\sim
C49-C25
 with sigma of 0.04
 C1-C4 \\sim C4-C1A \\sim C1A-C1B \\sim C1B-C1C \\sim C1C-C1D \\sim C1D-C1
 with sigma of 0.02
 C1-C1C \\sim C1A-C1C \\sim C4-C1D \\sim C4-C1B \\sim C1B-C1D \\sim C1-C1A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C44 \\sim C6 \\sim C8 \\sim C10 \\sim C12 \\sim C14 \\sim C16 \\sim C18 \\sim
C20 \\sim C22 \\sim C24 \\sim C26 \\sim C28 \\sim C30 \\sim C32 \\sim C34 \\sim
C36 \\sim C38 \\sim C40 \\sim C42 \\sim C105 \\sim C46 \\sim C48 \\sim C50
\\sim C52 \\sim C54 \\sim C56 \\sim C58 \\sim C60 \\sim C62 \\sim C64 \\sim C66
\\sim C68 \\sim C70 \\sim C72 \\sim C74 \\sim C76 \\sim C78 \\sim C80 \\sim C82
\\sim C84 \\sim C86 \\sim C88 \\sim C90 \\sim C92 \\sim C94 \\sim C96 \\sim C98
\\sim C100 \\sim C102 \\sim C104 \\sim C13 \\sim C53 \\sim C27 \\sim C55 \\sim
C7 \\sim C57 \\sim C29 \\sim C59 \\sim C15 \\sim C61 \\sim C63 \\sim C2 \\sim
C65 \\sim C33 \\sim C67 \\sim C17 \\sim C69 \\sim C35 \\sim C71 \\sim C9 \\sim
C73 \\sim C37 \\sim C75 \\sim C19 \\sim C77 \\sim C39 \\sim C79 \\sim C5 \\sim
C81 \\sim C41 \\sim C83 \\sim C21 \\sim C85 \\sim C43 \\sim C11 \\sim C89 \\sim
C45 \\sim C91 \\sim C23 \\sim C93 \\sim C49 \\sim C99 \\sim C25 \\sim C101
\\sim C51 \\sim C103 \\sim C1 \\sim C4 \\sim C1A \\sim C1B \\sim C1C \\sim C1D
\\sim N31 \\sim N1 \\sim N63 \\sim N78 \\sim N4 \\sim N96 \\sim N28 \\sim N94
\\sim N80 \\sim N111 \\sim N131 \\sim N128 \\sim N38 \\sim N61 \\sim N49 \\sim
N113: within 5A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
5A
C49 \\sim C99 \\sim C25 \\sim C101 \\sim C51 \\sim C103: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
C1 \\sim C4 \\sim C1A \\sim C1B \\sim C1C \\sim C1D: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C49, C99, C25, C101, C51, C103
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, C4, C1A, C1B, C1C, C1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C10(H10), C18(H18), C68(H68), C76(H76), C84(H84), C86(H86),
 C63(H63), C41(H41)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C22(H22A,H22B), C26(H26A,H26B), C30(H30A,
 H30B), C32(H32A,H32B), C34(H34A,H34B), C36(H36A,H36B), C38(H38A,H38B),
 C40(H40A,H40B), C42(H42A,H42B), C105(H10E,H10F), C46(H46A,H46B), C48(H48A,
 H48B), C50(H50A,H50B), C54(H54A,H54B), C56(H56A,H56B), C58(H58A,H58B),
 C62(H62A,H62B), C64(H64A,H64B), C66(H66A,H66B), C70(H70A,H70B), C72(H72A,H72B),
  C74(H74A,H74B), C78(H78A,H78B), C80(H80A,H80B), C82(H82A,H82B), C88(H88A,
 H88B), C90(H90A,H90B), C92(H92A,H92B), C94(H94A,H94B), C96(H96A,H96B),
 C98(H98A,H98B), C100(H10C,H10D), C102(H10A,H10B), C104(H10G,H10H), C13(H13A,
 H13B), C53(H53A,H53B), C27(H27A,H27B), C55(H55A,H55B), C7(H7A,H7B), C57(H57A,
 H57B), C29(H29A,H29B), C15(H15A,H15B), C61(H61A,H61B), C2(H2A,H2B), C65(H65A,
 H65B), C33(H33A,H33B), C17(H17A,H17B), C69(H69A,H69B), C35(H35A,H35B),
 C71(H71A,H71B), C9(H9A,H9B), C73(H73A,H73B), C37(H37A,H37B), C75(H75A,H75B),
 C19(H19A,H19B), C77(H77A,H77B), C79(H79A,H79B), C5(H5A,H5B), C81(H81A,H81B),
 C83(H83A,H83B), C43(H43A,H43B), C89(H89A,H89B), C45(H45A,H45B), C91(H91A,H91B),
  C23(H23A,H23B), C93(H93A,H93B), C99(H99A,H99B), C25(H25A,H25B), C101(H10I,
 H10J), C51(H51A,H51B), C103(H10K,H10L), C1(H1A,H1B), C4(H4A,H4B), C1A(H1AA,
 H1AB), C1B(H1BA,H1BB), C1D(H1DA,H1DB)
5.c Aromatic/amide H refined with riding coordinates:
 C44(H44), C12(H12), C20(H20), C24(H24), C28(H28), C52(H52), C60(H60),
 C59(H59), C67(H67), C39(H39), C21(H21), C85(H85), C11(H11)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              37147
_shelx_hkl_checksum              54417
_shelx_fab_checksum              89984
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.626