# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_histamine-A0-NaOH-capillary
_database_code_depnum_ccdc_archive 'CCDC 1912450'
loop_
_audit_author_name
_audit_author_address
'Prof. Kohji Tashiro'
;Faculty of Science, Chiang Mai University, Chiang Mai, Thailand
Thailand
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H9 Cl N4 Na'
_chemical_formula_moiety         'C10 H9 Cl N4 Na'
_chemical_formula_weight         243.65
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.6228(3)
_cell_length_b                   9.2043(9)
_cell_length_c                   17.4130(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.3164(18)
_cell_angle_gamma                90.0000
_cell_volume                     740.32(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.43
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       histamine
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             250.00
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.377
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6937
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.222
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1675
_reflns_number_gt                1170
_reflns_threshold_expression     F²>4.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 4.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 4.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1170
_refine_ls_number_parameters     92
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    36479.9000    51270.5000    16954.8000
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.439
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Na Na 0.0362 0.0249
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.13626(13) -0.01458(7) 0.39149(3) 0.03463(15) Uani 1 4 d . . .
N2 N 0.5877(4) 0.1996(2) 0.51821(12) 0.0325(5) Uani 1 4 d . . .
N4 N -0.0225(5) 0.5173(3) 0.26937(12) 0.0434(6) Uani 1 4 d . . .
N5 N 0.1766(4) 0.5781(2) 0.38155(12) 0.0338(6) Uani 1 4 d . . .
C1 C -0.0115(6) 0.6155(3) 0.32544(14) 0.0363(7) Uani 1 4 d . . .
C2 C 0.1712(6) 0.4098(3) 0.28938(15) 0.0444(8) Uani 1 4 d . . .
C4 C 0.3693(5) 0.2725(3) 0.46582(14) 0.0319(6) Uani 1 4 d . . .
C5 C 0.2946(5) 0.4483(3) 0.35862(13) 0.0307(6) Uani 1 4 d . . .
C6 C 0.5140(5) 0.3676(3) 0.40729(15) 0.0360(7) Uani 1 4 d . . .
H1 H -0.12377 0.69927 0.32564 0.0434 Uiso 1 4 calc R . .
H2 H 0.21383 0.32776 0.26078 0.0533 Uiso 1 4 calc R . .
H3 H 0.25282 0.19848 0.43971 0.0382 Uiso 1 4 calc R . .
H4 H 0.24642 0.33259 0.49663 0.0382 Uiso 1 4 calc R . .
H5 H 0.64115 0.43765 0.43307 0.0434 Uiso 1 4 calc R . .
H6 H 0.62545 0.30736 0.37363 0.0434 Uiso 1 4 calc R . .
H7 H 0.49242 0.13224 0.55083 0.0392 Uiso 1 4 calc R . .
H8 H 0.72416 0.14841 0.48812 0.0390 Uiso 1 4 calc R . .
H9 H 0.68774 0.27132 0.54927 0.0392 Uiso 1 4 calc R . .
H10 H -0.1412 0.52058 0.22499 0.0519 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
N2 C4 1.492(3) yes .
N4 C1 1.330(3) yes .
N4 C2 1.370(4) yes .
N5 C1 1.327(3) yes .
N5 C5 1.379(3) yes .
C2 C5 1.360(3) yes .
C4 C6 1.519(4) yes .
C5 C6 1.493(3) yes .
N2 H7 0.960 no .
N2 H8 0.960 no .
N2 H9 0.960 no .
N4 H10 0.930 no .
C1 H1 0.930 no .
C2 H2 0.930 no .
C4 H3 0.970 no .
C4 H4 0.970 no .
C6 H5 0.970 no .
C6 H6 0.970 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N4 C2 107.4(2) yes . .
C1 N5 C5 105.4(2) yes . .
N4 C1 N5 111.7(2) yes . .
N4 C2 C5 106.5(2) yes . .
N2 C4 C6 111.32(19) yes . .
N5 C5 C2 109.0(2) yes . .
N5 C5 C6 122.3(2) yes . .
C2 C5 C6 128.7(2) yes . .
C4 C6 C5 111.08(19) yes . .
C4 N2 H7 109.684 no . .
C4 N2 H8 109.294 no . .
C4 N2 H9 109.527 no . .
H7 N2 H8 109.440 no . .
H7 N2 H9 109.444 no . .
H8 N2 H9 109.439 no . .
C1 N4 H10 126.306 no . .
C2 N4 H10 126.324 no . .
N4 C1 H1 124.152 no . .
N5 C1 H1 124.167 no . .
N4 C2 H2 126.913 no . .
C5 C2 H2 126.576 no . .
N2 C4 H3 108.655 no . .
N2 C4 H4 108.357 no . .
C6 C4 H3 109.968 no . .
C6 C4 H4 109.026 no . .
H3 C4 H4 109.481 no . .
C4 C6 H5 110.334 no . .
C4 C6 H6 109.559 no . .
C5 C6 H5 108.513 no . .
C5 C6 H6 107.851 no . .
H5 C6 H6 109.449 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N4 C2 C5 0.1(3) no . . . .
C2 N4 C1 N5 -0.6(3) no . . . .
C1 N5 C5 C2 -0.7(2) no . . . .
C1 N5 C5 C6 -178.69(19) no . . . .
C5 N5 C1 N4 0.8(3) no . . . .
N4 C2 C5 N5 0.4(3) no . . . .
N4 C2 C5 C6 178.2(2) no . . . .
N2 C4 C6 C5 -176.02(17) no . . . .
N5 C5 C6 C4 84.4(3) no . . . .
C2 C5 C6 C4 -93.1(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N5 C4 3.279(3) no . .
C1 C6 3.585(4) no . .
C2 C4 3.413(4) no . .
Cl1 N2 3.258(2) no . 1_455
Cl1 N2 3.161(2) no . 3_556
Cl1 N2 3.389(2) no . 3_656
Cl1 N4 3.172(2) no . 2_445
N2 Cl1 3.258(2) no . 1_655
N2 Cl1 3.161(2) no . 3_556
N2 Cl1 3.389(2) no . 3_656
N2 N5 2.875(3) no . 3_666
N4 Cl1 3.172(2) no . 2_455
N4 C6 3.560(3) no . 1_455
N5 N2 2.875(3) no . 3_666
N5 C4 3.593(3) no . 3_666
C1 C6 3.507(4) no . 1_455
C4 N5 3.593(3) no . 3_666
C6 N4 3.560(3) no . 1_655
C6 C1 3.507(4) no . 1_655
N2 H5 2.6623 no . .
N2 H6 2.7179 no . .
N5 H2 3.1289 no . .
N5 H4 3.0288 no . .
N5 H5 2.6328 no . .
N5 H6 3.2491 no . .
N5 H10 3.0898 no . .
C1 H2 3.0755 no . .
C2 H1 3.0703 no . .
C2 H3 3.2708 no . .
C2 H5 3.2567 no . .
C2 H6 2.6836 no . .
C5 H1 3.0525 no . .
C5 H3 2.7090 no . .
C5 H4 2.6460 no . .
C5 H10 3.0882 no . .
C6 H2 2.8780 no . .
C6 H7 3.3123 no . .
C6 H8 2.6240 no . .
C6 H9 2.7171 no . .
H1 H10 2.4025 no . .
H2 H3 3.3333 no . .
H2 H6 2.6861 no . .
H2 H10 2.4798 no . .
H3 H5 2.8459 no . .
H3 H6 2.3358 no . .
H3 H7 2.2736 no . .
H3 H8 2.3499 no . .
H3 H9 2.7967 no . .
H4 H5 2.3776 no . .
H4 H6 2.8310 no . .
H4 H7 2.3448 no . .
H4 H8 2.7928 no . .
H4 H9 2.2736 no . .
H5 H7 3.5628 no . .
H5 H8 2.8503 no . .
H5 H9 2.5395 no . .
H6 H7 3.5568 no . .
H6 H8 2.4999 no . .
H6 H9 3.0783 no . .
Cl1 H1 2.8741 no . 1_545
Cl1 H3 3.5663 no . 1_455
Cl1 H3 2.7684 no . .
Cl1 H3 3.4530 no . 3_556
Cl1 H4 3.5641 no . 3_556
Cl1 H6 3.1723 no . 1_455
Cl1 H7 3.5855 no . 1_455
Cl1 H7 2.2419 no . 3_556
Cl1 H7 3.2861 no . 3_656
Cl1 H8 2.3635 no . 1_455
Cl1 H8 3.0362 no . 3_656
Cl1 H9 3.2825 no . 3_656
Cl1 H10 2.2602 no . 2_445
N2 H3 3.4151 no . 1_655
N2 H4 3.3173 no . 1_655
N2 H7 3.2981 no . 3_656
N2 H8 3.5129 no . 3_656
N4 H2 3.2463 no . 2_555
N4 H5 3.3820 no . 1_455
N4 H6 3.1491 no . 1_455
N5 H1 3.5925 no . 1_655
N5 H2 3.4324 no . 2_555
N5 H4 3.0554 no . 3_566
N5 H4 3.4398 no . 3_666
N5 H5 2.9636 no . 1_455
N5 H5 3.3062 no . 3_666
N5 H6 3.5626 no . 1_455
N5 H7 3.2696 no . 3_666
N5 H8 3.4079 no . 3_666
N5 H9 1.9247 no . 3_666
C1 H2 2.8518 no . 2_555
C1 H4 3.3586 no . 3_566
C1 H5 3.0022 no . 1_455
C1 H6 3.4172 no . 1_455
C1 H9 2.7967 no . 3_666
C2 H1 3.5330 no . 2_545
C2 H5 3.5814 no . 1_455
C2 H6 3.1154 no . 1_455
C2 H10 3.5621 no . 1_655
C4 H5 3.1979 no . 3_666
C4 H8 3.2315 no . 1_455
C4 H9 3.5225 no . 1_455
C5 H5 3.3363 no . 1_455
C5 H6 3.3740 no . 1_455
C5 H9 3.0382 no . 3_666
C6 H4 3.3896 no . 3_666
C6 H5 3.4081 no . 3_666
C6 H9 3.5416 no . 3_666
H1 Cl1 2.8741 no . 1_565
H1 N5 3.5925 no . 1_455
H1 C2 3.5330 no . 2_555
H1 H2 3.2821 no . 2_455
H1 H2 2.7359 no . 2_555
H1 H4 3.1823 no . 3_566
H1 H5 3.2624 no . 1_455
H1 H7 3.1989 no . 3_566
H1 H9 3.4748 no . 3_566
H1 H9 2.9199 no . 3_666
H1 H10 3.2599 no . 2_455
H2 N4 3.2463 no . 2_545
H2 N5 3.4324 no . 2_545
H2 C1 2.8518 no . 2_545
H2 H1 3.2821 no . 2_445
H2 H1 2.7359 no . 2_545
H2 H6 3.4245 no . 1_455
H2 H10 3.5466 no . 1_655
H2 H10 3.4524 no . 2_545
H3 Cl1 2.7684 no . .
H3 Cl1 3.5663 no . 1_655
H3 Cl1 3.4530 no . 3_556
H3 N2 3.4151 no . 1_455
H3 H5 3.5817 no . 1_455
H3 H6 3.2357 no . 1_455
H3 H7 3.2657 no . 3_656
H3 H8 2.6575 no . 1_455
H3 H8 3.4314 no . 3_656
H3 H9 3.3639 no . 1_455
H4 Cl1 3.5641 no . 3_556
H4 N2 3.3173 no . 1_455
H4 N5 3.0554 no . 3_566
H4 N5 3.4398 no . 3_666
H4 C1 3.3586 no . 3_566
H4 C6 3.3896 no . 3_666
H4 H1 3.1823 no . 3_566
H4 H5 3.1207 no . 1_455
H4 H5 2.4879 no . 3_666
H4 H6 3.5192 no . 1_455
H4 H8 2.9489 no . 1_455
H4 H9 2.8319 no . 1_455
H5 N4 3.3820 no . 1_655
H5 N5 2.9636 no . 1_655
H5 N5 3.3062 no . 3_666
H5 C1 3.0022 no . 1_655
H5 C2 3.5814 no . 1_655
H5 C4 3.1979 no . 3_666
H5 C5 3.3363 no . 1_655
H5 C6 3.4081 no . 3_666
H5 H1 3.2624 no . 1_655
H5 H3 3.5817 no . 1_655
H5 H4 3.1207 no . 1_655
H5 H4 2.4879 no . 3_666
H5 H5 2.9495 no . 3_666
H5 H9 3.1015 no . 3_666
H6 Cl1 3.1723 no . 1_655
H6 N4 3.1491 no . 1_655
H6 N5 3.5626 no . 1_655
H6 C1 3.4172 no . 1_655
H6 C2 3.1154 no . 1_655
H6 C5 3.3740 no . 1_655
H6 H2 3.4245 no . 1_655
H6 H3 3.2357 no . 1_655
H6 H4 3.5192 no . 1_655
H6 H10 3.4554 no . 1_655
H6 H10 3.1515 no . 2_545
H7 Cl1 3.5855 no . 1_655
H7 Cl1 2.2419 no . 3_556
H7 Cl1 3.2861 no . 3_656
H7 N2 3.2981 no . 3_656
H7 N5 3.2696 no . 3_666
H7 H1 3.1989 no . 3_566
H7 H3 3.2657 no . 3_656
H7 H7 3.0124 no . 3_656
H7 H8 2.8426 no . 3_656
H7 H10 3.4218 no . 4_666
H8 Cl1 2.3635 no . 1_655
H8 Cl1 3.0362 no . 3_656
H8 N2 3.5129 no . 3_656
H8 N5 3.4079 no . 3_666
H8 C4 3.2315 no . 1_655
H8 H3 2.6575 no . 1_655
H8 H3 3.4314 no . 3_656
H8 H4 2.9489 no . 1_655
H8 H7 2.8426 no . 3_656
H8 H8 3.4641 no . 3_656
H9 Cl1 3.2825 no . 3_656
H9 N5 1.9247 no . 3_666
H9 C1 2.7967 no . 3_666
H9 C4 3.5225 no . 1_655
H9 C5 3.0382 no . 3_666
H9 C6 3.5416 no . 3_666
H9 H1 3.4748 no . 3_566
H9 H1 2.9199 no . 3_666
H9 H3 3.3639 no . 1_655
H9 H4 2.8319 no . 1_655
H9 H5 3.1015 no . 3_666
H10 Cl1 2.2602 no . 2_455
H10 C2 3.5621 no . 1_455
H10 H1 3.2599 no . 2_445
H10 H2 3.5466 no . 1_455
H10 H2 3.4524 no . 2_555
H10 H6 3.4554 no . 1_455
H10 H6 3.1515 no . 2_555
H10 H7 3.4218 no . 4_565

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H7 Cl1 . . 3_556 3.161(2) 0.960 2.242 160.0 no
N2 H8 Cl1 . . 1_655 3.258(2) 0.960 2.363 154.8 no
N2 H9 N5 . . 3_666 2.875(3) 0.960 1.925 170.0 no
N4 H10 Cl1 . . 2_455 3.172(2) 0.930 2.260 166.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        'Histamine monocation'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_histamine-A0-Base-capillary
_database_code_depnum_ccdc_archive 'CCDC 1912431'
loop_
_audit_author_name
_audit_author_address
'Kohji Tashiro'
;Faculty of Science, Chiang Mai University, Chiang Mai, Thailand
Thailand
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C5 H13 N3'
_chemical_formula_moiety         'C5 H13 N3'
_chemical_formula_weight         115.18
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.698(3)
_cell_length_b                   7.632(4)
_cell_length_c                   7.250(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.920(7)
_cell_angle_gamma                90.0000
_cell_volume                     304.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    189
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      27.32
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       freebase
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             128.00
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  ?
_diffrn_reflns_number            2997
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.701
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1277
_reflns_number_gt                555
_reflns_threshold_expression     F²>4.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 4.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 4.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         555
_refine_ls_number_parameters     92
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    1917.6000    2595.5500    0.0000
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.006
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  524 Friedel Pairs'
_refine_ls_abs_structure_Flack   -1(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7830(5) -0.3856(4) -0.1266(4) 0.0438(8) Uani 1 2 d . . .
N2 N 0.8937(5) -0.4496(4) 0.1812(4) 0.0546(9) Uani 1 2 d . . .
N3 N 0.1991(5) -0.7151(4) -0.5261(5) 0.0504(10) Uani 1 2 d . . .
C4 C 0.5955(5) -0.4791(4) -0.0918(4) 0.0388(9) Uani 1 2 d . . .
C5 C 0.9548(6) -0.3719(5) 0.0413(5) 0.0526(11) Uani 1 2 d . . .
C6 C 0.3744(5) -0.5256(5) -0.2440(5) 0.0486(10) Uani 1 2 d . . .
C7 C 0.6663(6) -0.5174(5) 0.0959(4) 0.0498(10) Uani 1 2 d . . .
C8 C 0.4200(6) -0.6455(4) -0.3950(5) 0.0469(11) Uani 1 2 d . . .
H1 H 1.10027 -0.31156 0.05632 0.0612 Uiso 1 2 calc R . .
H2 H 0.57522 -0.58208 0.1613 0.0609 Uiso 1 2 calc R . .
H3 H 0.26459 -0.58224 -0.18027 0.0574 Uiso 1 2 calc R . .
H4 H 0.30322 -0.4163 -0.30015 0.0575 Uiso 1 2 calc R . .
H5 H 0.51675 -0.74577 -0.33858 0.0553 Uiso 1 2 calc R . .
H6 H 0.50347 -0.58295 -0.47585 0.0554 Uiso 1 2 calc R . .
H7 H 0.113(6) -0.631(5) -0.590(5) 0.075(15) Uiso 1 2 d . . .
H8 H 0.099(6) -0.777(5) -0.463(6) 0.076(15) Uiso 1 2 d . . .
H9 H 0.782(6) -0.340(5) -0.241(5) 0.073(13) Uiso 1 2 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
N1 C4 1.362(4) yes .
N1 C5 1.355(4) yes .
N2 C5 1.298(5) yes .
N2 C7 1.385(4) yes .
N3 C8 1.468(4) yes .
C4 C6 1.488(4) yes .
C4 C7 1.348(4) yes .
C6 C8 1.500(5) yes .
N1 H9 0.90(4) no .
N3 H7 0.87(4) no .
N3 H8 0.94(4) no .
C5 H1 0.930 no .
C6 H3 0.970 no .
C6 H4 0.970 no .
C7 H2 0.930 no .
C8 H5 0.970 no .
C8 H6 0.970 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 C5 107.1(3) yes . .
C5 N2 C7 103.3(3) yes . .
N1 C4 C6 122.9(3) yes . .
N1 C4 C7 104.8(3) yes . .
C6 C4 C7 132.3(3) yes . .
N1 C5 N2 113.0(3) yes . .
C4 C6 C8 114.5(3) yes . .
N2 C7 C4 111.9(3) yes . .
N3 C8 C6 114.4(3) yes . .
C4 N1 H9 124(2) no . .
C5 N1 H9 129(2) no . .
C8 N3 H7 111(2) no . .
C8 N3 H8 113(2) no . .
H7 N3 H8 107(3) no . .
N1 C5 H1 124.012 no . .
N2 C5 H1 123.002 no . .
C4 C6 H3 106.250 no . .
C4 C6 H4 106.792 no . .
C8 C6 H3 109.271 no . .
C8 C6 H4 110.520 no . .
H3 C6 H4 109.380 no . .
N2 C7 H2 123.448 no . .
C4 C7 H2 124.665 no . .
N3 C8 H5 106.659 no . .
N3 C8 H6 105.008 no . .
C6 C8 H5 111.095 no . .
C6 C8 H6 110.177 no . .
H5 C8 H6 109.230 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 N1 C5 N2 0.3(4) no . . . .
C5 N1 C4 C6 -178.3(3) no . . . .
C5 N1 C4 C7 -0.4(3) no . . . .
C5 N2 C7 C4 -0.2(4) no . . . .
C7 N2 C5 N1 -0.1(4) no . . . .
N1 C4 C6 C8 64.3(4) no . . . .
N1 C4 C7 N2 0.3(4) no . . . .
C6 C4 C7 N2 178.0(3) no . . . .
C7 C4 C6 C8 -113.0(4) no . . . .
C4 C6 C8 N3 170.1(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C8 3.150(4) no . .
N1 N3 2.859(5) no . 2_654
N2 N3 3.121(4) no . 1_656
N2 N3 3.227(5) no . 2_655
N2 C8 3.523(5) no . 2_655
N3 N1 2.859(5) no . 2_644
N3 N2 3.121(4) no . 1_454
N3 N2 3.227(5) no . 2_645
C8 N2 3.523(5) no . 2_645
N1 H2 3.0466 no . .
N1 H3 3.2463 no . .
N1 H4 2.7094 no . .
N1 H5 3.3194 no . .
N1 H6 3.0231 no . .
N2 H9 3.08(4) no . .
N3 H3 2.6408 no . .
N3 H4 2.7816 no . .
C4 H1 3.0776 no . .
C4 H5 2.6702 no . .
C4 H6 2.8112 no . .
C5 H2 2.9961 no . .
C6 H2 2.8980 no . .
C6 H7 2.69(4) no . .
C6 H8 2.72(4) no . .
C6 H9 2.72(4) no . .
C7 H1 3.0050 no . .
C7 H3 2.6705 no . .
C7 H4 3.1716 no . .
C7 H5 3.5075 no . .
C7 H9 3.01(4) no . .
C8 H9 3.12(3) no . .
H1 H9 2.4436 no . .
H2 H3 2.6473 no . .
H2 H4 3.5391 no . .
H3 H5 2.4059 no . .
H3 H6 2.8190 no . .
H3 H7 2.8968 no . .
H3 H8 2.5132 no . .
H4 H5 2.8382 no . .
H4 H6 2.3001 no . .
H4 H7 2.6672 no . .
H4 H8 3.1025 no . .
H4 H9 2.7131 no . .
H5 H7 2.6880 no . .
H5 H8 2.3304 no . .
H5 H9 3.4408 no . .
H6 H7 2.1978 no . .
H6 H8 2.7603 no . .
H6 H9 2.7335 no . .
N1 H1 3.3311 no . 2_745
N1 H2 3.0548 no . 2_655
N1 H3 3.2376 no . 1_655
N1 H3 3.2705 no . 2_655
N1 H4 3.5132 no . 1_655
N1 H7 2.99(4) no . 2_654
N1 H8 3.32(4) no . 2_654
N2 H1 3.2606 no . 2_745
N2 H3 2.9443 no . 2_655
N2 H5 3.2502 no . 2_655
N2 H7 2.27(4) no . 1_656
N2 H8 3.56(4) no . 1_656
N2 H8 2.42(4) no . 2_655
N2 H9 3.47(4) no . 2_745
N3 H4 3.2062 no . 2_544
N3 H6 3.2770 no . 2_644
N3 H9 1.96(4) no . 2_644
C4 H1 3.5087 no . 1_455
C4 H1 3.0462 no . 2_745
C4 H2 3.1827 no . 2_655
C4 H3 3.5906 no . 2_655
C5 H1 3.4268 no . 2_745
C5 H3 3.1197 no . 1_655
C5 H3 2.8486 no . 2_655
C5 H4 3.5657 no . 1_655
C5 H5 3.3614 no . 2_755
C5 H7 3.26(4) no . 1_656
C5 H8 3.24(4) no . 2_655
C6 H1 3.4059 no . 1_455
C6 H2 3.4367 no . 2_655
C6 H8 3.53(3) no . 2_554
C7 H1 3.5320 no . 1_455
C7 H1 2.9637 no . 2_745
C7 H3 3.3815 no . 2_655
C7 H4 3.3706 no . 2_645
C7 H5 3.0703 no . 2_655
C7 H6 3.4980 no . 1_556
C7 H7 3.07(3) no . 1_656
C7 H8 3.23(4) no . 2_655
C8 H1 3.4134 no . 2_745
C8 H2 3.5817 no . 1_554
C8 H6 3.5248 no . 2_644
C8 H9 2.99(4) no . 2_644
H1 N1 3.3311 no . 2_755
H1 N2 3.2606 no . 2_755
H1 C4 3.5087 no . 1_655
H1 C4 3.0462 no . 2_755
H1 C5 3.4268 no . 2_755
H1 C6 3.4059 no . 1_655
H1 C7 3.5320 no . 1_655
H1 C7 2.9637 no . 2_755
H1 C8 3.4134 no . 2_755
H1 H2 3.3324 no . 1_655
H1 H2 3.2370 no . 2_755
H1 H3 2.9855 no . 1_655
H1 H3 3.0257 no . 2_655
H1 H4 3.1929 no . 1_655
H1 H5 2.6272 no . 2_755
H1 H7 3.5272 no . 1_656
H1 H7 3.5609 no . 2_654
H1 H8 3.4344 no . 2_655
H2 N1 3.0548 no . 2_645
H2 C4 3.1827 no . 2_645
H2 C6 3.4367 no . 2_645
H2 C8 3.5817 no . 1_556
H2 H1 3.3324 no . 1_455
H2 H1 3.2370 no . 2_745
H2 H4 2.7641 no . 2_645
H2 H5 2.9768 no . 2_655
H2 H6 2.7643 no . 1_556
H2 H7 3.5753 no . 1_556
H2 H7 3.1509 no . 1_656
H2 H8 3.4010 no . 2_655
H2 H9 2.9904 no . 2_645
H3 N1 3.2376 no . 1_455
H3 N1 3.2705 no . 2_645
H3 N2 2.9443 no . 2_645
H3 C4 3.5906 no . 2_645
H3 C5 3.1197 no . 1_455
H3 C5 2.8486 no . 2_645
H3 C7 3.3815 no . 2_645
H3 H1 2.9855 no . 1_455
H3 H1 3.0257 no . 2_645
H3 H9 3.2504 no . 1_455
H4 N1 3.5132 no . 1_455
H4 N3 3.2062 no . 2_554
H4 C5 3.5657 no . 1_455
H4 C7 3.3706 no . 2_655
H4 H1 3.1929 no . 1_455
H4 H2 2.7641 no . 2_655
H4 H5 3.3151 no . 2_654
H4 H6 3.3533 no . 2_654
H4 H7 3.1637 no . 2_554
H4 H8 2.7018 no . 2_554
H4 H9 3.1636 no . 1_455
H5 N2 3.2502 no . 2_645
H5 C5 3.3614 no . 2_745
H5 C7 3.0703 no . 2_645
H5 H1 2.6272 no . 2_745
H5 H2 2.9768 no . 2_645
H5 H4 3.3151 no . 2_644
H5 H6 2.8923 no . 2_644
H5 H9 3.1666 no . 2_644
H6 N3 3.2770 no . 2_654
H6 C7 3.4980 no . 1_554
H6 C8 3.5248 no . 2_654
H6 H2 2.7643 no . 1_554
H6 H4 3.3533 no . 2_644
H6 H5 2.8923 no . 2_654
H6 H8 3.3596 no . 2_654
H6 H9 2.9959 no . 2_644
H7 N1 2.99(4) no . 2_644
H7 N2 2.27(4) no . 1_454
H7 C5 3.26(4) no . 1_454
H7 C7 3.07(3) no . 1_454
H7 H1 3.5272 no . 1_454
H7 H1 3.5609 no . 2_644
H7 H2 3.1509 no . 1_454
H7 H2 3.5753 no . 1_554
H7 H4 3.1637 no . 2_544
H7 H8 3.03(6) no . 2_554
H7 H9 2.18(6) no . 2_644
H8 N1 3.32(4) no . 2_644
H8 N2 3.56(4) no . 1_454
H8 N2 2.42(4) no . 2_645
H8 C5 3.24(4) no . 2_645
H8 C6 3.53(3) no . 2_544
H8 C7 3.23(4) no . 2_645
H8 H1 3.4344 no . 2_645
H8 H2 3.4010 no . 2_645
H8 H4 2.7018 no . 2_544
H8 H6 3.3596 no . 2_644
H8 H7 3.03(6) no . 2_544
H8 H9 2.46(6) no . 2_644
H9 N2 3.47(4) no . 2_755
H9 N3 1.96(4) no . 2_654
H9 C8 2.99(4) no . 2_654
H9 H2 2.9904 no . 2_655
H9 H3 3.2504 no . 1_655
H9 H4 3.1636 no . 1_655
H9 H5 3.1666 no . 2_654
H9 H6 2.9959 no . 2_654
H9 H7 2.18(6) no . 2_654
H9 H8 2.46(6) no . 2_654

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H9 N3 . . 2_654 2.859(5) 0.90(4) 1.96(4) 173(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        'Histamine Free base'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_histamine-A0-HCl-needle
_database_code_depnum_ccdc_archive 'CCDC 1912432'
loop_
_audit_author_name
_audit_author_address
'Kohji Tashiro'
;Faculty of Science, Chiang Mai University, Chiang Mai, Thailand
Thailand
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C5 H13 Cl2 N3 O2'
_chemical_formula_moiety         'C5 H13 Cl2 N3 O2'
_chemical_formula_weight         218.08
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.449(6)
_cell_length_b                   12.694(16)
_cell_length_c                   7.577(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.45(3)
_cell_angle_gamma                90.0000
_cell_volume                     427.7(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    386
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.55
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       dication
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228.00
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.315
_exptl_absorpt_correction_T_max  0.930

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4129
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1948
_reflns_number_gt                1325
_reflns_threshold_expression     F²>4.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 4.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 4.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1325
_refine_ls_number_parameters     103
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    11342.3000    15975.1000    5431.7200
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         3.290
_refine_diff_density_min         -1.320
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  926 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.67(19)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.4408(4) -0.01146(16) 0.8770(2) 0.0422(4) Uani 1 2 d . . .
Cl2 Cl -0.4725(4) -0.18776(17) 0.4021(2) 0.0444(4) Uani 1 2 d . . .
N1 N -0.0221(13) -0.5407(4) 0.4345(7) 0.0396(15) Uani 1 2 d . . .
N2 N -0.1190(12) -0.3403(4) 0.9859(7) 0.0367(15) Uani 1 2 d . . .
N5 N 0.1840(13) -0.2131(4) 0.9492(8) 0.0429(16) Uani 1 2 d . . .
C1 C 0.0023(14) -0.3549(5) 0.8264(8) 0.0315(15) Uani 1 2 d . . .
C2 C 0.1970(16) -0.2751(6) 0.8035(9) 0.0415(18) Uani 1 2 d . . .
C8 C -0.0066(17) -0.2536(6) 1.0598(10) 0.046(2) Uani 1 2 d . . .
C9 C -0.058(2) -0.4542(6) 0.7221(9) 0.047(2) Uani 1 2 d . . .
C10 C 0.002(2) -0.4381(6) 0.5287(8) 0.043(2) Uani 1 2 d . . .
H1 H -0.25567 -0.38493 1.03888 0.0440 Uiso 1 2 calc R . .
H2 H 0.29516 -0.15196 0.96859 0.0516 Uiso 1 2 calc R . .
H3 H 0.3198 -0.26479 0.70757 0.0499 Uiso 1 2 calc R . .
H4 H -0.05681 -0.22487 1.16808 0.0554 Uiso 1 2 calc R . .
H5 H 0.07766 -0.50628 0.77304 0.0566 Uiso 1 2 calc R . .
H6 H -0.26436 -0.47659 0.73845 0.0565 Uiso 1 2 calc R . .
H7 H 0.20529 -0.41294 0.51154 0.0519 Uiso 1 2 calc R . .
H8 H -0.13995 -0.38886 0.47531 0.0520 Uiso 1 2 calc R . .
H9 H -0.22289 -0.56662 0.44818 0.0475 Uiso 1 2 calc R . .
H10 H 0.01557 -0.53141 0.31128 0.0475 Uiso 1 2 calc R . .
H11 H 0.11892 -0.59046 0.48405 0.0476 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
N1 C10 1.488(9) yes .
N2 C1 1.348(8) yes .
N2 C8 1.327(9) yes .
N5 C2 1.358(9) yes .
N5 C8 1.312(10) yes .
C1 C2 1.347(9) yes .
C1 C9 1.508(9) yes .
C9 C10 1.511(10) yes .
N1 H9 0.960 no .
N1 H10 0.960 no .
N1 H11 0.960 no .
N2 H1 0.930 no .
N5 H2 0.930 no .
C2 H3 0.930 no .
C8 H4 0.930 no .
C9 H5 0.970 no .
C9 H6 0.970 no .
C10 H7 0.970 no .
C10 H8 0.970 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N2 C8 109.8(6) yes . .
C2 N5 C8 109.5(6) yes . .
N2 C1 C2 106.5(6) yes . .
N2 C1 C9 121.0(6) yes . .
C2 C1 C9 131.9(6) yes . .
N5 C2 C1 106.9(6) yes . .
N2 C8 N5 107.3(6) yes . .
C1 C9 C10 111.2(6) yes . .
N1 C10 C9 109.5(6) yes . .
C10 N1 H9 107.741 no . .
C10 N1 H10 110.282 no . .
C10 N1 H11 110.466 no . .
H9 N1 H10 109.441 no . .
H9 N1 H11 109.442 no . .
H10 N1 H11 109.441 no . .
C1 N2 H1 125.705 no . .
C8 N2 H1 124.510 no . .
C2 N5 H2 125.395 no . .
C8 N5 H2 125.131 no . .
N5 C2 H3 126.249 no . .
C1 C2 H3 126.830 no . .
N2 C8 H4 126.981 no . .
N5 C8 H4 125.674 no . .
C1 C9 H5 105.029 no . .
C1 C9 H6 109.597 no . .
C10 C9 H5 110.680 no . .
C10 C9 H6 110.837 no . .
H5 C9 H6 109.358 no . .
N1 C10 H7 106.268 no . .
N1 C10 H8 108.969 no . .
C9 C10 H7 111.370 no . .
C9 C10 H8 111.186 no . .
H7 C10 H8 109.380 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C8 N5 0.1(7) no . . . .
C8 N2 C1 C2 0.6(7) no . . . .
C8 N2 C1 C9 172.9(5) no . . . .
C2 N5 C8 N2 -0.8(8) no . . . .
C8 N5 C2 C1 1.1(7) no . . . .
N2 C1 C2 N5 -1.0(7) no . . . .
N2 C1 C9 C10 159.7(5) no . . . .
C2 C1 C9 C10 -30.2(10) no . . . .
C9 C1 C2 N5 -172.2(6) no . . . .
C1 C9 C10 N1 172.8(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
C2 C10 3.045(10) no . .
Cl1 N1 3.337(6) no . 2_456
Cl1 N1 3.193(6) no . 2_556
Cl1 N2 3.121(6) no . 2_457
Cl1 N2 3.446(6) no . 2_557
Cl1 N5 3.112(7) no . 1_455
Cl1 C1 3.547(7) no . 2_557
Cl2 N1 3.196(6) no . 2_456
Cl2 N1 3.118(6) no . 2_556
Cl2 C2 3.588(8) no . 1_455
Cl2 C8 3.572(8) no . 1_454
Cl2 C8 3.463(8) no . 1_554
N1 Cl1 3.337(6) no . 2_446
N1 Cl1 3.193(6) no . 2_546
N1 Cl2 3.196(6) no . 2_446
N1 Cl2 3.118(6) no . 2_546
N1 C2 3.556(10) no . 2_546
N2 Cl1 3.121(6) no . 2_447
N2 Cl1 3.446(6) no . 2_547
N2 N5 3.500(9) no . 1_455
N2 C2 3.412(10) no . 1_455
N5 Cl1 3.112(7) no . 1_655
N5 N2 3.500(9) no . 1_655
C1 Cl1 3.547(7) no . 2_547
C2 Cl2 3.588(8) no . 1_655
C2 N1 3.556(10) no . 2_556
C2 N2 3.412(10) no . 1_655
C8 Cl2 3.463(8) no . 1_556
C8 Cl2 3.572(8) no . 1_656
N1 H5 2.6287 no . .
N1 H6 2.6932 no . .
N2 H2 3.0228 no . .
N2 H3 3.0631 no . .
N2 H5 2.8068 no . .
N2 H6 2.6203 no . .
N5 H1 3.0187 no . .
C1 H2 3.0700 no . .
C1 H4 3.0871 no . .
C1 H7 2.6757 no . .
C1 H8 2.7531 no . .
C2 H1 3.0590 no . .
C2 H4 3.0771 no . .
C2 H5 2.9896 no . .
C2 H6 3.3080 no . .
C2 H7 2.8215 no . .
C2 H8 3.2136 no . .
C8 H3 3.0739 no . .
C9 H1 2.7220 no . .
C9 H3 2.9382 no . .
C9 H9 2.6084 no . .
C9 H10 3.2882 no . .
C9 H11 2.6346 no . .
C10 H3 2.9282 no . .
H1 H4 2.4136 no . .
H1 H5 2.9631 no . .
H1 H6 2.5559 no . .
H2 H3 2.4466 no . .
H2 H4 2.3901 no . .
H3 H5 3.2910 no . .
H3 H7 2.4422 no . .
H3 H8 3.0949 no . .
H5 H7 2.3894 no . .
H5 H8 2.8527 no . .
H5 H9 2.8752 no . .
H5 H10 3.5172 no . .
H5 H11 2.4476 no . .
H6 H7 2.8558 no . .
H6 H8 2.3617 no . .
H6 H9 2.4896 no . .
H6 H10 3.5658 no . .
H6 H11 2.9796 no . .
H7 H9 2.7601 no . .
H7 H10 2.2829 no . .
H7 H11 2.2945 no . .
H8 H9 2.2948 no . .
H8 H10 2.3111 no . .
H8 H11 2.8064 no . .
Cl1 H1 2.2029 no . 2_457
Cl1 H1 3.5334 no . 2_557
Cl1 H2 2.2546 no . 1_455
Cl1 H5 3.0705 no . 2_557
Cl1 H6 3.2556 no . 2_457
Cl1 H7 3.3890 no . 2_556
Cl1 H8 3.5744 no . 2_456
Cl1 H9 2.9350 no . 2_456
Cl1 H10 2.9075 no . 2_456
Cl1 H10 2.4113 no . 2_556
Cl1 H11 3.2770 no . 2_556
Cl2 H2 3.4485 no . 1_454
Cl2 H3 2.6974 no . 1_455
Cl2 H4 3.1448 no . 1_454
Cl2 H4 2.6364 no . 1_554
Cl2 H5 3.2047 no . 2_556
Cl2 H6 3.1027 no . 2_456
Cl2 H7 3.3126 no . 1_455
Cl2 H8 2.9952 no . .
Cl2 H9 2.3593 no . 2_456
Cl2 H10 3.5446 no . 2_556
Cl2 H11 3.2657 no . 2_456
Cl2 H11 2.1622 no . 2_556
N1 H2 3.5512 no . 2_546
N1 H3 3.3064 no . 2_546
N1 H9 3.5693 no . 1_655
N2 H2 3.5363 no . 1_455
N2 H3 3.3661 no . 1_455
N2 H10 3.5002 no . 1_556
N5 H1 3.3686 no . 1_655
N5 H5 3.5779 no . 2_557
N5 H9 3.5466 no . 2_556
N5 H10 3.1486 no . 2_556
C1 H3 3.3467 no . 1_455
C2 H1 3.2911 no . 1_655
C2 H6 3.5475 no . 1_655
C2 H9 3.2663 no . 2_556
C2 H10 3.3439 no . 2_556
C2 H11 3.4734 no . 2_556
C8 H2 3.4177 no . 1_455
C8 H5 3.4030 no . 2_557
C9 H4 3.5693 no . 2_547
C9 H6 3.5430 no . 1_655
C10 H7 3.5584 no . 1_455
H1 Cl1 2.2029 no . 2_447
H1 Cl1 3.5334 no . 2_547
H1 N5 3.3686 no . 1_455
H1 C2 3.2911 no . 1_455
H1 H2 3.3946 no . 2_547
H1 H3 3.4576 no . 1_455
H1 H8 3.3342 no . 1_556
H1 H10 3.0079 no . 1_556
H2 Cl1 2.2546 no . 1_655
H2 Cl2 3.4485 no . 1_656
H2 N1 3.5512 no . 2_556
H2 N2 3.5363 no . 1_655
H2 C8 3.4177 no . 1_655
H2 H1 3.3946 no . 2_557
H2 H4 3.3513 no . 1_655
H2 H5 3.1886 no . 2_557
H2 H6 3.1492 no . 2_557
H2 H9 3.3463 no . 2_556
H2 H10 2.9328 no . 2_556
H3 Cl2 2.6974 no . 1_655
H3 N1 3.3064 no . 2_556
H3 N2 3.3661 no . 1_655
H3 C1 3.3467 no . 1_655
H3 H1 3.4576 no . 1_655
H3 H6 3.2685 no . 1_655
H3 H8 3.4011 no . 1_655
H3 H9 2.8073 no . 2_556
H3 H10 3.3184 no . 2_556
H3 H11 3.2666 no . 2_556
H4 Cl2 2.6364 no . 1_556
H4 Cl2 3.1448 no . 1_656
H4 C9 3.5693 no . 2_557
H4 H2 3.3513 no . 1_455
H4 H5 2.8123 no . 2_557
H4 H6 3.5249 no . 2_557
H4 H8 3.1517 no . 1_556
H4 H11 3.1578 no . 2_557
H5 Cl1 3.0705 no . 2_547
H5 Cl2 3.2047 no . 2_546
H5 N5 3.5779 no . 2_547
H5 C8 3.4030 no . 2_547
H5 H2 3.1886 no . 2_547
H5 H4 2.8123 no . 2_547
H5 H6 2.9693 no . 1_655
H6 Cl1 3.2556 no . 2_447
H6 Cl2 3.1027 no . 2_446
H6 C2 3.5475 no . 1_455
H6 C9 3.5430 no . 1_455
H6 H2 3.1492 no . 2_547
H6 H3 3.2685 no . 1_455
H6 H4 3.5249 no . 2_547
H6 H5 2.9693 no . 1_455
H6 H7 2.9950 no . 1_455
H7 Cl1 3.3890 no . 2_546
H7 Cl2 3.3126 no . 1_655
H7 C10 3.5584 no . 1_655
H7 H6 2.9950 no . 1_655
H7 H8 2.9484 no . 1_655
H7 H9 3.2509 no . 1_655
H8 Cl1 3.5744 no . 2_446
H8 Cl2 2.9952 no . .
H8 H1 3.3342 no . 1_554
H8 H3 3.4011 no . 1_455
H8 H4 3.1517 no . 1_554
H8 H7 2.9484 no . 1_455
H9 Cl1 2.9350 no . 2_446
H9 Cl2 2.3593 no . 2_446
H9 N1 3.5693 no . 1_455
H9 N5 3.5466 no . 2_546
H9 C2 3.2663 no . 2_546
H9 H2 3.3463 no . 2_546
H9 H3 2.8073 no . 2_546
H9 H7 3.2509 no . 1_455
H9 H10 3.5461 no . 1_455
H9 H11 2.9629 no . 1_455
H10 Cl1 2.9075 no . 2_446
H10 Cl1 2.4113 no . 2_546
H10 Cl2 3.5446 no . 2_546
H10 N2 3.5002 no . 1_554
H10 N5 3.1486 no . 2_546
H10 C2 3.3439 no . 2_546
H10 H1 3.0079 no . 1_554
H10 H2 2.9328 no . 2_546
H10 H3 3.3184 no . 2_546
H10 H9 3.5461 no . 1_655
H11 Cl1 3.2770 no . 2_546
H11 Cl2 3.2657 no . 2_446
H11 Cl2 2.1622 no . 2_546
H11 C2 3.4734 no . 2_546
H11 H3 3.2666 no . 2_546
H11 H4 3.1578 no . 2_547
H11 H9 2.9629 no . 1_655

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H9 Cl2 . . 2_446 3.196(6) 0.960 2.359 145.4 no
N1 H10 Cl1 . . 2_546 3.193(6) 0.960 2.411 138.3 no
N1 H11 Cl2 . . 2_546 3.118(6) 0.960 2.162 173.5 no
N2 H1 Cl1 . . 2_447 3.121(6) 0.930 2.203 169.0 no
N5 H2 Cl1 . . 1_655 3.112(7) 0.930 2.255 152.9 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        'Histamine dication form'
_chemical_properties_physical    Air-sensitive
