#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/52/2105246.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2105246
loop_
_publ_author_name
'Briggs, Naomi E. B.'
'Kennedy, Alan R.'
'Morrison, Catriona A.'
_publ_section_title
;
 42 salt forms of tyramine: structural comparison and the occurrence of
 hydrate formation
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              453
_journal_page_last               464
_journal_paper_doi               10.1107/S0108768112026456
_journal_volume                  68
_journal_year                    2012
_chemical_formula_sum            'C12 H19 N O8'
_chemical_formula_weight         305.28
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.231(3)
_cell_angle_beta                 85.330(5)
_cell_angle_gamma                79.854(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2647(5)
_cell_length_b                   7.9475(6)
_cell_length_c                   12.5853(10)
_cell_measurement_reflns_used    42215
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     696.89(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius Roper CCD camera'
_diffrn_measurement_method       'φ&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  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14640
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0578
_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)+(0.0136P)²+0.4927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2247
_reflns_number_total             3037
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            ry5045.cif
_cod_data_source_block           tyrtar
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2105246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.5247(2) 0.2836(2) 1.03647(14) 0.0256(4) Uani d . 1 1
O O2 0.36394(19) 0.6232(2) 0.77652(12) 0.0201(4) Uani d . 1 1
O O1W 0.3294(2) 0.8355(2) 0.46240(13) 0.0201(4) Uani d . 1 1
O O3 0.4089(2) 0.4674(2) 0.64551(13) 0.0240(4) Uani d . 1 1
O O4 0.7680(2) 0.4576(2) 0.62433(13) 0.0184(4) Uani d . 1 1
O O5 0.6383(2) 0.8216(2) 0.58822(12) 0.0187(4) Uani d . 1 1
O O6 1.0127(2) 0.7668(2) 0.58745(12) 0.0249(4) Uani d . 1 1
O O7 1.0151(2) 0.6560(2) 0.76736(12) 0.0211(4) Uani d . 1 1
N N1 1.1382(3) 0.2865(3) 0.61164(17) 0.0173(4) Uani d . 1 1
C C1 1.0148(3) 0.1513(3) 0.85392(18) 0.0194(5) Uani d . 1 1
C C2 0.8529(3) 0.0843(3) 0.84725(19) 0.0245(5) Uani d . 1 1
H H2 0.8535 0.0058 0.8002 0.029 Uiso calc R 1 1
C C3 0.6900(3) 0.1294(3) 0.90774(19) 0.0227(5) Uani d . 1 1
H H3 0.5811 0.0815 0.9022 0.027 Uiso calc R 1 1
C C4 0.6876(3) 0.2452(3) 0.97649(18) 0.0202(5) Uani d . 1 1
C C5 0.8464(3) 0.3145(3) 0.98353(18) 0.0211(5) Uani d . 1 1
H H5 0.8453 0.3947 1.0296 0.025 Uiso calc R 1 1
C C6 1.0084(3) 0.2663(3) 0.92282(18) 0.0216(5) Uani d . 1 1
H H6 1.1175 0.3135 0.9288 0.026 Uiso calc R 1 1
C C7 1.1971(3) 0.0926(3) 0.79444(19) 0.0261(6) Uani d . 1 1
H H7A 1.2449 -0.0300 0.8296 0.031 Uiso calc R 1 1
H H7B 1.2897 0.1647 0.8047 0.031 Uiso calc R 1 1
C C8 1.1877(3) 0.1027(3) 0.67299(19) 0.0226(5) Uani d . 1 1
H H8A 1.3105 0.0503 0.6445 0.027 Uiso calc R 1 1
H H8B 1.0930 0.0338 0.6612 0.027 Uiso calc R 1 1
C C9 0.4654(3) 0.5434(3) 0.70941(18) 0.0160(5) Uani d . 1 1
C C10 0.6770(3) 0.5415(3) 0.70795(18) 0.0153(5) Uani d . 1 1
H H10 0.7257 0.4756 0.7801 0.018 Uiso calc R 1 1
C C11 0.7214(3) 0.7267(3) 0.68619(17) 0.0154(5) Uani d . 1 1
H H11 0.6690 0.7839 0.7478 0.018 Uiso calc R 1 1
C C12 0.9340(3) 0.7183(3) 0.67560(18) 0.0154(5) Uani d . 1 1
H H2N 1.015(4) 0.338(3) 0.629(2) 0.034(7) Uiso d . 1 1
H H3N 1.214(3) 0.359(3) 0.6233(19) 0.023(7) Uiso d . 1 1
H H1N 1.149(4) 0.288(4) 0.537(3) 0.047(9) Uiso d . 1 1
H H2W 0.240(4) 0.807(4) 0.508(2) 0.045(9) Uiso d . 1 1
H H1H 0.549(4) 0.336(4) 1.087(3) 0.057(10) Uiso d . 1 1
H H1W 0.432(5) 0.805(4) 0.503(3) 0.054(10) Uiso d . 1 1
H H5H 0.660(4) 0.928(4) 0.575(2) 0.048(9) Uiso d . 1 1
H H4H 0.693(4) 0.400(4) 0.609(3) 0.055(10) Uiso d . 1 1
H H7H 1.154(5) 0.642(4) 0.759(3) 0.072(11) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 H1H 108(2)
H2W O1W H1W 104(3)
C10 O4 H4H 106(2)
C11 O5 H5H 110(2)
C12 O7 H7H 113(2)
C8 N1 H2N 112.5(16)
C8 N1 H3N 114.1(16)
H2N N1 H3N 106(2)
C8 N1 H1N 109.0(18)
H2N N1 H1N 109(2)
H3N N1 H1N 106(2)
C6 C1 C2 117.6(2)
C6 C1 C7 120.4(2)
C2 C1 C7 121.9(2)
C1 C2 C3 121.6(2)
C1 C2 H2 119.2
C3 C2 H2 119.2
C2 C3 C4 119.6(2)
C2 C3 H3 120.2
C4 C3 H3 120.2
O1 C4 C5 122.6(2)
O1 C4 C3 117.7(2)
C5 C4 C3 119.7(2)
C4 C5 C6 119.7(2)
C4 C5 H5 120.2
C6 C5 H5 120.2
C1 C6 C5 121.8(2)
C1 C6 H6 119.1
C5 C6 H6 119.1
C1 C7 C8 116.4(2)
C1 C7 H7A 108.2
C8 C7 H7A 108.2
C1 C7 H7B 108.2
C8 C7 H7B 108.2
H7A C7 H7B 107.4
N1 C8 C7 111.80(19)
N1 C8 H8A 109.3
C7 C8 H8A 109.3
N1 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 107.9
O3 C9 O2 126.12(19)
O3 C9 C10 117.06(18)
O2 C9 C10 116.82(19)
O4 C10 C11 108.57(16)
O4 C10 C9 109.70(17)
C11 C10 C9 110.97(17)
O4 C10 H10 109.2
C11 C10 H10 109.2
C9 C10 H10 109.2
O5 C11 C10 108.23(17)
O5 C11 C12 110.49(17)
C10 C11 C12 108.89(17)
O5 C11 H11 109.7
C10 C11 H11 109.7
C12 C11 H11 109.7
O6 C12 O7 125.75(19)
O6 C12 C11 121.0(2)
O7 C12 C11 113.27(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.376(3)
O1 H1H 0.89(3)
O2 C9 1.277(3)
O1W H2W 0.86(3)
O1W H1W 0.91(3)
O3 C9 1.239(3)
O4 C10 1.425(2)
O4 H4H 0.83(3)
O5 C11 1.415(3)
O5 H5H 0.86(3)
O6 C12 1.221(2)
O7 C12 1.297(3)
O7 H7H 0.99(4)
N1 C8 1.491(3)
N1 H2N 0.94(3)
N1 H3N 0.91(3)
N1 H1N 0.94(3)
C1 C6 1.385(3)
C1 C2 1.390(3)
C1 C7 1.519(3)
C2 C3 1.390(3)
C2 H2 0.9500
C3 C4 1.392(3)
C3 H3 0.9500
C4 C5 1.380(3)
C5 C6 1.393(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.519(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.533(3)
C10 C11 1.523(3)
C10 H10 1.0000
C11 C12 1.531(3)
C11 H11 1.0000
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
C6 C1 C2 C3 -0.4(4)
C7 C1 C2 C3 175.5(2)
C1 C2 C3 C4 0.3(4)
C2 C3 C4 O1 -178.8(2)
C2 C3 C4 C5 0.3(3)
O1 C4 C5 C6 178.2(2)
C3 C4 C5 C6 -0.8(3)
C2 C1 C6 C5 -0.2(3)
C7 C1 C6 C5 -176.1(2)
C4 C5 C6 C1 0.8(3)
C6 C1 C7 C8 -131.6(2)
C2 C1 C7 C8 52.6(3)
C1 C7 C8 N1 64.6(3)
O3 C9 C10 O4 3.8(3)
O2 C9 C10 O4 -176.26(18)
O3 C9 C10 C11 123.7(2)
O2 C9 C10 C11 -56.3(2)
O4 C10 C11 O5 65.7(2)
C9 C10 C11 O5 -54.9(2)
O4 C10 C11 C12 -54.5(2)
C9 C10 C11 C12 -175.10(17)
O5 C11 C12 O6 -9.8(3)
C10 C11 C12 O6 108.9(2)
O5 C11 C12 O7 170.34(18)
C10 C11 C12 O7 -70.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064118
