#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/31/4503115.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_4503115
loop_
_publ_author_name
'Ergaz, Itzhak'
'Toscano, Rubén Alfredo'
'Delgado, Guillermo'
'Steinberg, Avital'
'Glaser, Robert'
_publ_section_title
;
 The Effect of Environment on Molecular Structure: The Crystalline-State
 Stereochemistry ofN-Methylated Adamantane 1,3-Diammonium Salts
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1399
_journal_paper_doi               10.1021/cg0704908
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C10 H20 N2, 2(Cl)'
_chemical_formula_sum            'C10 H20 Cl2 N2'
_chemical_formula_weight         239.18
_chemical_name_systematic
; 
1,3-diaminoadamantane dihydrochloride
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9101(11)
_cell_length_b                   15.5148(15)
_cell_length_c                   7.2463(7)
_cell_measurement_reflns_used    6425
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.28
_cell_volume                     1226.6(2)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23C (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 0.661
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9808
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.8951
_exptl_absorpt_correction_T_min  0.8331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.218
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0370P)²+0.0837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                2187
_reflns_number_total             2254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0704908-file007.cif
_cod_data_source_block           282DLG05
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4503115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.44459(4) 0.24679(3) 0.16088(8) 0.04393(15) Uani 1 1 d .
Cl2 Cl 0.64553(4) 0.42586(2) 0.63327(9) 0.04110(14) Uani 1 1 d .
N1 N 0.19692(14) 0.24254(10) 0.3974(2) 0.0324(4) Uani 1 1 d D
H1A H 0.1925(18) 0.1940(11) 0.469(3) 0.039 Uiso 1 1 d D
H1B H 0.2679(16) 0.2409(12) 0.333(3) 0.039 Uiso 1 1 d D
H1C H 0.1284(17) 0.2430(12) 0.328(3) 0.039 Uiso 1 1 d D
N2 N 0.41182(14) 0.40516(10) 0.8884(2) 0.0315(3) Uani 1 1 d D
H2D H 0.4794(15) 0.4095(12) 0.816(3) 0.038 Uiso 1 1 d D
H2E H 0.404(2) 0.4535(11) 0.962(2) 0.038 Uiso 1 1 d D
H2F H 0.4163(19) 0.3578(11) 0.962(2) 0.038 Uiso 1 1 d D
C1 C 0.19336(14) 0.32002(11) 0.5215(2) 0.0258(4) Uani 1 1 d .
C2 C 0.30792(12) 0.32137(9) 0.6432(3) 0.0256(3) Uani 1 1 d .
H2A H 0.3810 0.3240 0.5671 0.031 Uiso 1 1 calc R
H2B H 0.3117 0.2695 0.7178 0.031 Uiso 1 1 calc R
C3 C 0.30046(14) 0.40110(11) 0.7674(2) 0.0261(4) Uani 1 1 d .
C4 C 0.18686(16) 0.39538(13) 0.8898(3) 0.0306(4) Uani 1 1 d .
H4A H 0.1838 0.4446 0.9723 0.037 Uiso 1 1 calc R
H4B H 0.1901 0.3434 0.9640 0.037 Uiso 1 1 calc R
C5 C 0.07282(15) 0.39406(11) 0.7671(2) 0.0314(4) Uani 1 1 d .
H5 H -0.0008 0.3911 0.8444 0.038 Uiso 1 1 calc R
C6 C 0.06855(14) 0.47597(10) 0.6485(3) 0.0370(4) Uani 1 1 d .
H6A H -0.0044 0.4754 0.5719 0.044 Uiso 1 1 calc R
H6B H 0.0650 0.5264 0.7276 0.044 Uiso 1 1 calc R
C7 C 0.18294(16) 0.48036(11) 0.5264(3) 0.0320(4) Uani 1 1 d .
H7 H 0.1798 0.5326 0.4504 0.038 Uiso 1 1 calc R
C8 C 0.18942(16) 0.40108(12) 0.4013(3) 0.0296(4) Uani 1 1 d .
H8A H 0.2622 0.4039 0.3247 0.036 Uiso 1 1 calc R
H8B H 0.1182 0.3993 0.3211 0.036 Uiso 1 1 calc R
C9 C 0.07813(13) 0.31501(9) 0.6410(3) 0.0316(3) Uani 1 1 d .
H9A H 0.0798 0.2629 0.7149 0.038 Uiso 1 1 calc R
H9B H 0.0059 0.3133 0.5631 0.038 Uiso 1 1 calc R
C10 C 0.29697(13) 0.48284(9) 0.6489(3) 0.0312(3) Uani 1 1 d .
H10A H 0.2946 0.5334 0.7275 0.037 Uiso 1 1 calc R
H10B H 0.3700 0.4860 0.5729 0.037 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
Cl1 0.0380(2) 0.0566(3) 0.0372(3) 0.0096(2) 0.0020(2) 0.01044(18)
Cl2 0.0457(3) 0.0361(2) 0.0415(3) 0.0017(2) 0.0080(2) -0.00455(16)
N1 0.0331(9) 0.0341(8) 0.0301(9) -0.0053(7) 0.0011(6) -0.0027(6)
N2 0.0293(8) 0.0375(8) 0.0277(8) 0.0012(6) -0.0046(7) 0.0000(7)
C1 0.0253(8) 0.0277(8) 0.0244(9) -0.0019(7) 0.0005(6) 0.0009(6)
C2 0.0248(7) 0.0276(7) 0.0245(8) 0.0021(8) 0.0015(8) 0.0029(5)
C3 0.0248(8) 0.0295(8) 0.0240(9) -0.0004(7) -0.0006(7) 0.0009(6)
C4 0.0321(10) 0.0360(11) 0.0237(9) -0.0014(8) 0.0022(8) 0.0018(8)
C5 0.0248(8) 0.0410(9) 0.0283(10) -0.0022(7) 0.0054(7) 0.0033(7)
C6 0.0340(8) 0.0395(9) 0.0375(10) -0.0003(10) -0.0013(9) 0.0132(6)
C7 0.0355(9) 0.0296(9) 0.0309(10) 0.0046(8) -0.0010(8) 0.0060(7)
C8 0.0285(9) 0.0373(11) 0.0232(9) 0.0032(8) -0.0013(7) 0.0021(7)
C9 0.0248(7) 0.0381(8) 0.0320(8) 0.0007(10) 0.0036(9) -0.0030(6)
C10 0.0350(8) 0.0286(7) 0.0302(9) 0.0003(9) -0.0005(9) -0.0009(6)
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N1 C1 C9 108.66(13)
N1 C1 C2 109.57(13)
C9 C1 C2 110.23(15)
N1 C1 C8 108.54(15)
C9 C1 C8 109.95(13)
C2 C1 C8 109.86(13)
C1 C2 C3 107.85(12)
N2 C3 C4 108.70(15)
N2 C3 C2 109.54(13)
C4 C3 C2 109.73(13)
N2 C3 C10 108.25(13)
C4 C3 C10 110.71(14)
C2 C3 C10 109.87(14)
C3 C4 C5 108.87(15)
C4 C5 C9 109.09(14)
C4 C5 C6 109.83(14)
C9 C5 C6 109.30(15)
C7 C6 C5 109.61(12)
C10 C7 C8 109.07(14)
C10 C7 C6 109.19(17)
C8 C7 C6 110.14(15)
C7 C8 C1 108.96(15)
C1 C9 C5 109.19(12)
C7 C10 C3 108.97(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.501(2)
N2 C3 1.499(2)
C1 C9 1.529(2)
C1 C2 1.530(2)
C1 C8 1.530(2)
C2 C3 1.532(2)
C3 C4 1.527(2)
C3 C10 1.532(2)
C4 C5 1.530(3)
C5 C9 1.530(2)
C5 C6 1.535(2)
C6 C7 1.532(3)
C7 C10 1.529(2)
C7 C8 1.529(3)
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 Cl2 0.914(15) 2.269(16) 3.1721(17) 169.8(17) 3_455
N1 H1B Cl1 0.906(15) 2.296(16) 3.2006(17) 175.8(17) .
N1 H1C Cl1 0.902(15) 2.347(16) 3.2470(17) 175.6(19) 3_455
N2 H2F Cl1 0.908(14) 2.268(15) 3.1722(16) 173.7(18) 1_556
N2 H2D Cl2 0.907(15) 2.259(15) 3.1659(17) 177.7(18) .
N2 H2E Cl2 0.925(14) 2.309(14) 3.2269(17) 172.0(19) 2_665
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
N1 C1 C2 C3 -179.89(13)
C9 C1 C2 C3 -60.36(16)
C8 C1 C2 C3 60.95(18)
C1 C2 C3 N2 -179.62(13)
C1 C2 C3 C4 61.13(17)
C1 C2 C3 C10 -60.82(16)
N2 C3 C4 C5 178.25(14)
C2 C3 C4 C5 -61.98(18)
C10 C3 C4 C5 59.47(19)
C3 C4 C5 C9 60.77(18)
C3 C4 C5 C6 -59.00(19)
C4 C5 C6 C7 60.1(2)
C9 C5 C6 C7 -59.51(18)
C5 C6 C7 C10 -60.41(19)
C5 C6 C7 C8 59.3(2)
C10 C7 C8 C1 60.60(19)
C6 C7 C8 C1 -59.21(19)
N1 C1 C8 C7 178.78(13)
C9 C1 C8 C7 60.05(18)
C2 C1 C8 C7 -61.43(18)
N1 C1 C9 C5 -179.53(14)
C2 C1 C9 C5 60.39(17)
C8 C1 C9 C5 -60.87(19)
C4 C5 C9 C1 -59.91(18)
C6 C5 C9 C1 60.19(17)
C8 C7 C10 C3 -60.5(2)
C6 C7 C10 C3 59.93(18)
N2 C3 C10 C7 -179.24(14)
C4 C3 C10 C7 -60.19(19)
C2 C3 C10 C7 61.17(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 45027602
