#------------------------------------------------------------------------------
#$Date: 2023-01-25 09:46:15 +0100 (Wed 25 de Jan de 2023) $
#$Revision: 280581 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/65/8106575.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_8106575
loop_
_publ_author_name
'Arderne, Charmaine'
'Batchelor, Kyle F.'
_publ_section_title
;
 The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              477
_journal_page_last               478
_journal_paper_doi               10.1515/ncrs-2016-0327
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C3 H11 N2, I'
_chemical_formula_sum            'C3 H11 I N2'
_chemical_formula_weight         202.04
_chemical_name_common
;
3-aminopropylazanium iodide
;
_chemical_name_systematic
;
3-aminopropan-1-aminium iodide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 96.501(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0152(2)
_cell_length_b                   10.1470(4)
_cell_length_c                   14.1852(5)
_cell_measurement_reflns_used    7836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.224
_cell_measurement_theta_min      2.474
_cell_volume                     717.23(5)
_computing_cell_refinement       'SAINT v7.53A (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_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    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14021
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_min         2.473
_exptl_absorpt_coefficient_mu    4.356
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.6874.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0830(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0182P)²+0.1644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0390
_refine_ls_wR_factor_ref         0.0411
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1521
_reflns_number_total             1788
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL 8cvb46_a in P2(1)/n
 8cvb46_a.res created by SHELXL-2016/4 at 11:52:18 on 13-Oct-2016
CELL 0.71073 5.0152 10.147 14.1852 90 96.501 90
ZERR 4 0.0002 0.0004 0.0005 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H I N
UNIT 12 44 4 8
DFIX 0.88 0.015 N1 H1a N1 H1b N1 H1c N2 H2a N2 H2b

L.S. 20
PLAN  10
SIZE 0.12 0.2 0.36
TEMP 21
HTAB 2.0000
BOND $H
CONF
MORE -1
fmap 2
acta
MERG 2
OMIT -2 60
REM <olex2.extras>
REM <HklSrc "%.\\8cvb46_a.hkl">
REM </olex2.extras>

WGHT    0.018200    0.164300
EXTI    0.082969
FVAR       0.25945
I1    3    0.863900    0.175928    0.406088    11.00000    0.04376    0.04137 =
         0.04203    0.00281    0.00734    0.00031
N1    4    0.641373    0.076188    0.639244    11.00000    0.04993    0.03439 =
         0.04810   -0.00683    0.00229   -0.00160
H1A   2    0.724631    0.068461    0.698853    11.00000    0.07860
H1B   2    0.527383    0.010714    0.626342    11.00000    0.08017
H1C   2    0.763304    0.079759    0.598118    11.00000    0.06939
N2    4    0.642496    0.561461    0.668083    11.00000    0.06589    0.03299 =
         0.05891    0.00567   -0.00834   -0.00028
H2A   2    0.543949    0.629934    0.654023    11.00000    0.06489
H2B   2    0.779874    0.563265    0.635188    11.00000    0.06550
C1    1    0.477932    0.444864    0.639542    11.00000    0.05315    0.03838 =
         0.04225    0.00398   -0.00525    0.00248
AFIX  23
H1D   2    0.404499    0.453109    0.573549    11.00000   -1.20000
H1E   2    0.329471    0.439237    0.677645    11.00000   -1.20000
AFIX   0
C2    1    0.647557    0.320190    0.652732    11.00000    0.04236    0.03313 =
         0.04061   -0.00260    0.00209   -0.00090
AFIX  23
H2C   2    0.734198    0.316327    0.717373    11.00000   -1.20000
H2D   2    0.786410    0.322516    0.610394    11.00000   -1.20000
AFIX   0
C3    1    0.474355    0.197766    0.632014    11.00000    0.04090    0.03831 =
         0.04254   -0.00211   -0.00120   -0.00024
AFIX  23
H3A   2    0.342147    0.192788    0.676786    11.00000   -1.20000
H3B   2    0.379435    0.204182    0.568690    11.00000   -1.20000
AFIX   0
HKLF 4




REM  8cvb46_a in P2(1)/n
REM R1 =  0.0174 for    1521 Fo > 4sig(Fo)  and  0.0240 for all    1788 data
REM     76 parameters refined using      5 restraints

END  
     
WGHT      0.0182      0.1643 

REM Instructions for potential hydrogen bonds
EQIV $1 -x+3/2, y-1/2, -z+3/
HTAB N1 N2_$1
EQIV $2 -x+1, -y, -z+
HTAB N1 I1_$2
HTAB N1 I1
EQIV $3 -x+2, -y, -z+
HTAB N1 I1_$3
EQIV $4 -x+1, -y+1, -z+
HTAB N2 I1_$4
EQIV $5 -x+2, -y+1, -z+
HTAB N2 I1_$5
HTAB C2 I1

REM Highest difference peak  0.585,  deepest hole -0.394,  1-sigma level  0.070
Q1    1   0.7874  0.1637  0.3531  11.00000  0.05    0.59
Q2    1   0.8397  0.2607  0.4076  11.00000  0.05    0.43
Q3    1   0.9207  0.1488  0.4801  11.00000  0.05    0.30
Q4    1   0.2631  0.4808  0.7606  11.00000  0.05    0.21
Q5    1   0.7589  0.5776  0.7174  11.00000  0.05    0.21
Q6    1   0.7880  0.0402  0.7630  11.00000  0.05    0.21
Q7    1   0.7803  0.1111  0.4248  11.00000  0.05    0.21
Q8    1   0.2971  0.3935  0.5216  11.00000  0.05    0.20
Q9    1   0.4540  0.3659  0.4863  11.00000  0.05    0.19
Q10   1   0.6712  0.3045  0.7630  11.00000  0.05    0.19

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0174 for 1521 Fo > 4sig(Fo) and 0.0240 for all 14518 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.59, deepest hole -0.39
  REM Mean Shift 0, Max Shift -0.001.
  
  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0240
  REM R1_gt = 0.0174
  REM wR_ref = 0.0411
  REM GOOF = 1.097
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 14518
  REM Reflections_gt = 1521
  REM Parameters = n/a
  REM Hole = -0.39
  REM Peak = 0.59
  REM Flack = n/a
;
_cod_data_source_file            suppl_ncrs-2016-0327_suppl.cif
_cod_data_source_block           8cvb46_a
_cod_database_code               8106575
_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   0.623
_shelx_estimated_absorpt_t_min   0.303
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N1-H1C = N2-H2A = N2-H2B
 0.88 with sigma of 0.015
3.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2C,H2D), C3(H3A,H3B)
;
_shelx_shelxl_version_number     2016/4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-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 0.86390(3) 0.17593(2) 0.40609(2) 0.04220(8) Uani 1 1 d . . . . .
N1 N 0.6414(4) 0.07619(19) 0.63924(16) 0.0444(4) Uani 1 1 d D . . . .
H1A H 0.725(6) 0.068(3) 0.6989(13) 0.079(10) Uiso 1 1 d D . . . .
H1B H 0.527(5) 0.011(2) 0.626(2) 0.080(10) Uiso 1 1 d D . . . .
H1C H 0.763(5) 0.080(3) 0.5981(16) 0.069(9) Uiso 1 1 d D . . . .
N2 N 0.6425(5) 0.5615(2) 0.66808(17) 0.0538(5) Uani 1 1 d D . . . .
H2A H 0.544(5) 0.630(2) 0.654(2) 0.065(9) Uiso 1 1 d D . . . .
H2B H 0.780(4) 0.563(3) 0.6352(19) 0.065(9) Uiso 1 1 d D . . . .
C1 C 0.4779(5) 0.4449(2) 0.63954(17) 0.0454(5) Uani 1 1 d . . . . .
H1D H 0.404499 0.453109 0.573549 0.054 Uiso 1 1 calc R . . . .
H1E H 0.329471 0.439237 0.677645 0.054 Uiso 1 1 calc R . . . .
C2 C 0.6476(4) 0.32019(19) 0.65273(17) 0.0389(5) Uani 1 1 d . . . . .
H2C H 0.734198 0.316327 0.717373 0.047 Uiso 1 1 calc R . . . .
H2D H 0.786410 0.322516 0.610394 0.047 Uiso 1 1 calc R . . . .
C3 C 0.4744(5) 0.1978(2) 0.63201(17) 0.0410(5) Uani 1 1 d . . . . .
H3A H 0.342147 0.192788 0.676786 0.049 Uiso 1 1 calc R . . . .
H3B H 0.379435 0.204182 0.568690 0.049 Uiso 1 1 calc R . . . .
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 0.04376(11) 0.04137(11) 0.04203(11) 0.00281(6) 0.00734(6) 0.00031(6)
N1 0.0499(11) 0.0344(10) 0.0481(12) -0.0068(9) 0.0023(10) -0.0016(9)
N2 0.0659(14) 0.0330(11) 0.0589(14) 0.0057(9) -0.0083(11) -0.0003(10)
C1 0.0531(13) 0.0384(12) 0.0422(12) 0.0040(9) -0.0053(10) 0.0025(10)
C2 0.0424(11) 0.0331(11) 0.0406(12) -0.0026(9) 0.0021(9) -0.0009(9)
C3 0.0409(11) 0.0383(12) 0.0425(12) -0.0021(9) -0.0012(9) -0.0002(9)
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
H1A N1 H1B 110(3) . .
H1A N1 H1C 110(3) . .
H1B N1 H1C 112(3) . .
C3 N1 H1A 109.5(19) . .
C3 N1 H1B 105(2) . .
C3 N1 H1C 110(2) . .
H2A N2 H2B 109(3) . .
C1 N2 H2A 107(2) . .
C1 N2 H2B 109(2) . .
N2 C1 H1D 109.6 . .
N2 C1 H1E 109.6 . .
N2 C1 C2 110.21(19) . .
H1D C1 H1E 108.1 . .
C2 C1 H1D 109.6 . .
C2 C1 H1E 109.6 . .
C1 C2 H2C 109.5 . .
C1 C2 H2D 109.5 . .
C1 C2 C3 110.77(18) . .
H2C C2 H2D 108.1 . .
C3 C2 H2C 109.5 . .
C3 C2 H2D 109.5 . .
N1 C3 C2 110.98(18) . .
N1 C3 H3A 109.4 . .
N1 C3 H3B 109.4 . .
C2 C3 H3A 109.4 . .
C2 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1A 0.903(14) .
N1 H1B 0.882(14) .
N1 H1C 0.892(14) .
N1 C3 1.488(3) .
N2 H2A 0.863(14) .
N2 H2B 0.875(14) .
N2 C1 1.473(3) .
C1 H1D 0.9700 .
C1 H1E 0.9700 .
C1 C2 1.524(3) .
C2 H2C 0.9700 .
C2 H2D 0.9700 .
C2 C3 1.525(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.903(14) 1.931(15) 2.828(3) 172(3) 2_646
N1 H1B I1 0.882(14) 2.729(15) 3.607(2) 174(3) 3_656
N1 H1C I1 0.892(14) 2.99(2) 3.748(2) 144(2) .
N1 H1C I1 0.892(14) 3.20(3) 3.671(2) 115(2) 3_756
N2 H2A I1 0.863(14) 2.898(15) 3.749(2) 169(3) 3_666
N2 H2B I1 0.875(14) 3.28(3) 3.863(2) 126(2) 3_766
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
N2 C1 C2 C3 174.9(2) . . . .
C1 C2 C3 N1 176.66(18) . . . .
