#------------------------------------------------------------------------------
#$Date: 2024-05-25 23:56:37 +0200 (Sat 25 de May de 2024) $
#$Revision: 292035 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/30/7133086.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7133086
loop_
_publ_author_name
'Möbs, Jakob'
'Tomori, Ajna'
'Heine, Johanna'
_publ_section_title
;
 Formation of iminium ions during the processing of metal halide
 perovskites.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d4cc01735h
_journal_year                    2024
_chemical_formula_moiety         'I, C5 H12 N'
_chemical_formula_sum            'C5 H12 I N'
_chemical_formula_weight         213.06
_space_group_crystal_system      tetragonal
_space_group_IT_number           87
_space_group_name_Hall           '-I 4'
_space_group_name_H-M_alt        'I 4/m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-04-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.38460(10)
_cell_length_b                   7.38460(10)
_cell_length_c                   7.2299(2)
_cell_measurement_reflns_used    27457
_cell_measurement_temperature    100
_cell_measurement_theta_max      39.03
_cell_measurement_theta_min      3.90
_cell_volume                     394.263(13)
_computing_cell_refinement
;
X-Area Recipe 1.34.0.0 (STOE, 2019)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.154.0 (STOE, 2019)
;
_computing_data_reduction
;
X-Area Integrate 1.77.0.0 (STOE, 2019)
X-Area LANA 1.77.1.0 (STOE, 2019)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.88, Darmstadt 2019
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
 2934 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  Stoe_Stadivari_Mo
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12242
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         42.627
_diffrn_reflns_theta_min         3.902
_diffrn_source                   'GeniX Mo'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.964
_exptl_absorpt_correction_T_max  0.8036
_exptl_absorpt_correction_T_min  0.2828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.798
_refine_diff_density_min         -1.563
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         755
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0172
_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/[σ²(Fo²)+(0.0213P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                719
_reflns_number_total             755
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01735h2.cif
_cod_data_source_block           jmx114
_cod_original_cell_volume        394.263(15)
_cod_database_code               7133086
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.592
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1_1-C1_1 \\sim N1_1-C2_1
 with sigma of 0.02
 C3_1-C4_1 \\sim C4_1-C5_1
 with sigma of 0.02
3. Restrained planarity
 C1_1, C2_1, C3_1, C4_1, C5_1, N1_1
 with sigma of 0.05
4. Uiso/Uaniso restraints and constraints
C1_1 \\sim C2_1 \\sim C3_1 \\sim C4_1 \\sim C5_1 \\sim N1_1: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 C1_1, C2_1, C3_1, C4_1, C5_1, N1_1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: C1(0.125) H1A(0.125) H1B(0.125) H1C(0.125) C2(0.125) H2A(0.125)
 H2B(0.125) H2C(0.125) C3(0.125) H3A(0.125) H3B(0.125) H3C(0.125) C4(0.125)
 C5(0.125) H5A(0.125) H5B(0.125) H5C(0.125) N1(0.125)
7.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_shelx_res_file
;
TITL jmx114_a.res in I4/m
    jmx114.res
    created by SHELXL-2018/3 at 15:51:10 on 04-Apr-2022
REM Old TITL jmx114 in I-4
REM SHELXT solution in I4/m: R1 0.066, Rweak 0.413, Alpha 0.023
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C4 N4 I
rem SADI_MEIM 0.04 N1 C3 N1 C5
rem SADI_MEIM 0.04 C1 C4 C2 C4
CELL 0.71073 7.3846 7.3846 7.2299 90 90 90
ZERR 2 0.0001 0.0001 0.0002 0 0 0
LATT 2
SYMM -X,-Y,+Z
SYMM -Y,+X,+Z
SYMM +Y,-X,+Z
SFAC C H I N
UNIT 10 24 2 2
FLAT_MEIM 0.05 C1 C2 C3 C4 C5 N1
SADI_MEIM N1 C1 N1 C2
SADI_MEIM C3 C4 C4 C5
SIMU_MEIM 0.01 0.02 2 C1 C2 C3 C4 C5 N1
RIGU_1 0.002 0.002 C1 C2 C3 C4 C5 N1

L.S. 10 0 0
PLAN  1
SIZE 0.037 0.055 0.148
TEMP 0
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\jmx114.hkl">
REM </olex2.extras>

WGHT    0.021300
FVAR       0.67645
I1    3    0.500000    0.500000    0.500000    10.12500    0.03223    0.03223 =
         0.01966    0.00000    0.00000    0.00000
RESI MEIM 1
PART -1
C1    1    0.474322    0.236473   -0.018255    10.12500    0.01470    0.01677 =
         0.01750    0.00075    0.00102   -0.00453
AFIX 137
H1A   2    0.383383    0.165977    0.043542    10.12500   -1.50000
H1B   2    0.590504    0.211912    0.035778    10.12500   -1.50000
H1C   2    0.476644    0.205127   -0.147097    10.12500   -1.50000
AFIX   0
C2    1    0.237127    0.473864    0.014819    10.12500    0.01655    0.01413 =
         0.02292   -0.00390   -0.00049   -0.00579
AFIX 137
H2A   2    0.184538    0.472485   -0.106605    10.12500   -1.50000
H2B   2    0.222216    0.591802    0.068560    10.12500   -1.50000
H2C   2    0.177960    0.385343    0.091003    10.12500   -1.50000
AFIX   0
C3    1    0.750581    0.506522   -0.006127    10.12500    0.01590    0.01575 =
         0.01309   -0.00358   -0.00262    0.00056
AFIX 137
H3A   2    0.820324    0.614450    0.013983    10.12500   -1.50000
H3B   2    0.776717    0.458989   -0.126798    10.12500   -1.50000
H3C   2    0.781351    0.418007    0.085903    10.12500   -1.50000
AFIX   0
C4    1    0.551697    0.550680    0.007270    10.12500    0.01556    0.01421 =
         0.01844   -0.00304   -0.00370    0.00012
C5    1    0.507304    0.748528    0.027695    10.12500    0.01746    0.01249 =
         0.02634    0.00192   -0.00736    0.00149
AFIX 137
H5A   2    0.456268    0.769811    0.147867    10.12500   -1.50000
H5B   2    0.421529    0.783142   -0.065608    10.12500   -1.50000
H5C   2    0.615790    0.818866    0.013860    10.12500   -1.50000
AFIX   0
N1    4    0.431957    0.430738    0.001745    10.12500    0.01638    0.01583 =
         0.01726   -0.00186   -0.00209   -0.00677
HKLF 4




REM  jmx114_a.res in I4/m
REM wR2 = 0.0375, GooF = S = 1.092, Restrained GooF = 1.048 for all data
REM R1 = 0.0172 for 719 Fo > 4sig(Fo) and 0.0205 for all 755 data
REM 61 parameters refined using 68 restraints

END

WGHT      0.0213      0.0000

REM Highest difference peak  0.798,  deepest hole -1.563,  1-sigma level  0.080
Q1    1   0.4339  0.5008  0.5000  10.50000  0.05    0.80
;
_shelx_res_checksum              41336
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.500000 0.500000 0.500000 0.02804(5) Uani 1 8 d S T P . .
C1_1 C 0.474(4) 0.236(3) -0.018(5) 0.016(5) Uani 0.125 1 d D U P A -1
H1A_1 H 0.383383 0.165977 0.043542 0.024 Uiso 0.125 1 calc R U P A -1
H1B_1 H 0.590504 0.211912 0.035778 0.024 Uiso 0.125 1 calc R U P A -1
H1C_1 H 0.476644 0.205127 -0.147097 0.024 Uiso 0.125 1 calc R U P A -1
C2_1 C 0.237(3) 0.474(4) 0.015(8) 0.018(5) Uani 0.125 1 d D U P A -1
H2A_1 H 0.184538 0.472485 -0.106605 0.027 Uiso 0.125 1 calc R U P A -1
H2B_1 H 0.222216 0.591802 0.068560 0.027 Uiso 0.125 1 calc R U P A -1
H2C_1 H 0.177960 0.385343 0.091003 0.027 Uiso 0.125 1 calc R U P A -1
C3_1 C 0.751(3) 0.507(6) -0.006(7) 0.015(5) Uani 0.125 1 d D U P A -1
H3A_1 H 0.820324 0.614450 0.013983 0.022 Uiso 0.125 1 calc R U P A -1
H3B_1 H 0.776717 0.458989 -0.126798 0.022 Uiso 0.125 1 calc R U P A -1
H3C_1 H 0.781351 0.418007 0.085903 0.022 Uiso 0.125 1 calc R U P A -1
C4_1 C 0.552(3) 0.551(3) 0.007(5) 0.016(2) Uani 0.125 1 d D U P A -1
C5_1 C 0.507(6) 0.749(3) 0.028(7) 0.019(6) Uani 0.125 1 d D U P A -1
H5A_1 H 0.456268 0.769811 0.147867 0.028 Uiso 0.125 1 calc R U P A -1
H5B_1 H 0.421529 0.783142 -0.065608 0.028 Uiso 0.125 1 calc R U P A -1
H5C_1 H 0.615790 0.818866 0.013860 0.028 Uiso 0.125 1 calc R U P A -1
N1_1 N 0.432(2) 0.431(2) 0.002(5) 0.0165(18) Uani 0.125 1 d D U P A -1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03223(6) 0.03223(6) 0.01966(7) 0.000 0.000 0.000
C1_1 0.015(5) 0.017(3) 0.018(13) 0.001(4) 0.001(5) -0.005(3)
C2_1 0.017(3) 0.014(5) 0.023(14) -0.004(6) 0.000(5) -0.006(2)
C3_1 0.016(4) 0.016(9) 0.013(11) -0.004(14) -0.003(7) 0.001(5)
C4_1 0.016(3) 0.014(3) 0.018(5) -0.003(4) -0.004(4) 0.000(2)
C5_1 0.017(9) 0.012(3) 0.026(13) 0.002(4) -0.007(9) 0.001(4)
N1_1 0.016(3) 0.016(3) 0.017(3) -0.002(5) -0.002(5) -0.0068(16)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A_1 C1_1 H1B_1 109.5 . . ?
H1A_1 C1_1 H1C_1 109.5 . . ?
H1B_1 C1_1 H1C_1 109.5 . . ?
N1_1 C1_1 H1A_1 109.5 . . ?
N1_1 C1_1 H1B_1 109.5 . . ?
N1_1 C1_1 H1C_1 109.5 . . ?
H2A_1 C2_1 H2B_1 109.5 . . ?
H2A_1 C2_1 H2C_1 109.5 . . ?
H2B_1 C2_1 H2C_1 109.5 . . ?
N1_1 C2_1 H2A_1 109.5 . . ?
N1_1 C2_1 H2B_1 109.5 . . ?
N1_1 C2_1 H2C_1 109.5 . . ?
H3A_1 C3_1 H3B_1 109.5 . . ?
H3A_1 C3_1 H3C_1 109.5 . . ?
H3B_1 C3_1 H3C_1 109.5 . . ?
C4_1 C3_1 H3A_1 109.5 . . ?
C4_1 C3_1 H3B_1 109.5 . . ?
C4_1 C3_1 H3C_1 109.5 . . ?
C5_1 C4_1 C3_1 115(3) . . ?
N1_1 C4_1 C3_1 122.2(19) . . ?
N1_1 C4_1 C5_1 122.4(19) . . ?
C4_1 C5_1 H5A_1 109.5 . . ?
C4_1 C5_1 H5B_1 109.5 . . ?
C4_1 C5_1 H5C_1 109.5 . . ?
H5A_1 C5_1 H5B_1 109.5 . . ?
H5A_1 C5_1 H5C_1 109.5 . . ?
H5B_1 C5_1 H5C_1 109.5 . . ?
C1_1 N1_1 C2_1 115(2) . . ?
C4_1 N1_1 C1_1 122.8(13) . . ?
C4_1 N1_1 C2_1 122.2(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1_1 H1A_1 0.9600 . ?
C1_1 H1B_1 0.9600 . ?
C1_1 H1C_1 0.9600 . ?
C1_1 N1_1 1.475(18) . ?
C2_1 H2A_1 0.9600 . ?
C2_1 H2B_1 0.9600 . ?
C2_1 H2C_1 0.9600 . ?
C2_1 N1_1 1.477(18) . ?
C3_1 H3A_1 0.9600 . ?
C3_1 H3B_1 0.9600 . ?
C3_1 H3C_1 0.9600 . ?
C3_1 C4_1 1.508(18) . ?
C4_1 C5_1 1.505(17) . ?
C4_1 N1_1 1.252(9) . ?
C5_1 H5A_1 0.9600 . ?
C5_1 H5B_1 0.9600 . ?
C5_1 H5C_1 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3_1 C4_1 N1_1 C1_1 0.0(11) . . . . ?
C3_1 C4_1 N1_1 C2_1 -180.0(5) . . . . ?
C5_1 C4_1 N1_1 C1_1 180.0(6) . . . . ?
C5_1 C4_1 N1_1 C2_1 0.0(11) . . . . ?
