#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/52/2105236.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_2105236
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            'C15 H16 N2 O5'
_chemical_formula_weight         304.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 92.518(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.0796(10)
_cell_length_b                   6.1784(14)
_cell_length_c                   67.751(7)
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.8
_cell_volume                     2960.6(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.828
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device
;
CrystalLogic Kappa (3 circle)
;
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_source         DIAMOND
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       86
_diffrn_reflns_limit_l_min       -86
_diffrn_reflns_number            16192
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.459
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0885
_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)+(0.1662P)²+4.4702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2664
_refine_ls_wR_factor_ref         0.3083
_reflns_number_gt                3820
_reflns_number_total             5466
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            ry5045.cif
_cod_data_source_block           tyr4nb
_cod_original_cell_volume        2960.6(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2105236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.4844(6) 0.6759(6) 0.09533(5) 0.0295(9) Uani d . 1 1
H H1H 0.4492 0.7554 0.0858 0.044 Uiso calc R 1 1
O O2 -0.0043(6) 1.4343(6) -0.15761(4) 0.0276(8) Uani d . 1 1
H H2H 0.0345 1.5142 -0.1666 0.041 Uiso calc R 1 1
O O3 0.9701(6) 0.6059(6) 0.20541(4) 0.0282(9) Uani d . 1 1
O O4 0.9357(6) 0.3048(6) 0.18714(4) 0.0284(9) Uani d . 1 1
O O5 0.5851(6) 0.0717(6) 0.28449(4) 0.0315(9) Uani d . 1 1
O O6 0.6698(6) -0.2323(6) 0.27114(5) 0.0304(9) Uani d . 1 1
O O7 0.3860(6) 0.9163(6) 0.06410(4) 0.0312(9) Uani d . 1 1
O O8 0.3965(7) 0.5999(7) 0.04756(5) 0.0395(11) Uani d . 1 1
O O9 0.1277(7) 1.4248(7) -0.02442(5) 0.0382(11) Uani d . 1 1
O O10 0.1848(7) 1.1305(7) -0.04062(5) 0.0399(11) Uani d . 1 1
N N1 0.1364(7) 0.9149(7) 0.18123(5) 0.0253(10) Uani d . 1 1
H H1N 0.0992 0.8129 0.1899 0.038 Uiso calc R 1 1
H H2N 0.1227 0.8619 0.1687 0.038 Uiso calc R 1 1
H H3N 0.0638 1.0355 0.1823 0.038 Uiso calc R 1 1
N N2 0.4177(7) 1.6835(7) -0.07215(5) 0.0287(10) Uani d . 1 1
H H4N 0.4795 1.5822 -0.0646 0.043 Uiso calc R 1 1
H H5N 0.4731 1.8149 -0.0701 0.043 Uiso calc R 1 1
H H6N 0.4236 1.6469 -0.0851 0.043 Uiso calc R 1 1
N N3 0.6507(6) -0.0332(7) 0.27085(5) 0.0212(9) Uani d . 1 1
N N4 0.1732(7) 1.2330(7) -0.02503(5) 0.0266(10) Uani d . 1 1
C C1 0.4335(7) 0.9948(8) 0.14952(6) 0.0209(10) Uani d . 1 1
C C2 0.3658(7) 1.0904(8) 0.13191(6) 0.0226(10) Uani d . 1 1
H H2 0.3090 1.2295 0.1324 0.027 Uiso calc R 1 1
C C3 0.3787(7) 0.9886(8) 0.11362(6) 0.0213(10) Uani d . 1 1
H H3 0.3288 1.0558 0.1019 0.026 Uiso calc R 1 1
C C4 0.4662(7) 0.7867(8) 0.11282(6) 0.0221(10) Uani d . 1 1
C C5 0.5367(8) 0.6860(8) 0.13011(6) 0.0241(10) Uani d . 1 1
H H5 0.5949 0.5477 0.1295 0.029 Uiso calc R 1 1
C C6 0.5204(8) 0.7914(9) 0.14828(6) 0.0257(11) Uani d . 1 1
H H6 0.5692 0.7237 0.1600 0.031 Uiso calc R 1 1
C C7 0.4219(8) 1.1106(9) 0.16931(6) 0.0267(11) Uani d . 1 1
H H7A 0.3425 1.2415 0.1674 0.032 Uiso calc R 1 1
H H7B 0.5504 1.1588 0.1737 0.032 Uiso calc R 1 1
C C8 0.3403(9) 0.9716(9) 0.18569(6) 0.0291(12) Uani d . 1 1
H H8A 0.4151 0.8367 0.1872 0.035 Uiso calc R 1 1
H H8B 0.3514 1.0514 0.1984 0.035 Uiso calc R 1 1
C C9 0.0719(8) 1.7250(9) -0.10201(6) 0.0253(11) Uani d . 1 1
C C10 0.1328(7) 1.8320(8) -0.11882(6) 0.0223(10) Uani d . 1 1
H H10 0.1910 1.9701 -0.1175 0.027 Uiso calc R 1 1
C C11 0.1085(7) 1.7364(8) -0.13768(6) 0.0222(10) Uani d . 1 1
H H11 0.1491 1.8108 -0.1490 0.027 Uiso calc R 1 1
C C12 0.0258(7) 1.5349(8) -0.13965(6) 0.0200(10) Uani d . 1 1
C C13 -0.0314(8) 1.4250(9) -0.12293(6) 0.0258(11) Uani d . 1 1
H H13 -0.0860 1.2850 -0.1243 0.031 Uiso calc R 1 1
C C14 -0.0088(8) 1.5195(9) -0.10437(6) 0.0260(11) Uani d . 1 1
H H14 -0.0488 1.4433 -0.0931 0.031 Uiso calc R 1 1
C C15 0.0965(9) 1.8277(10) -0.08153(7) 0.0328(13) Uani d . 1 1
H H15A 0.1555 1.9719 -0.0829 0.039 Uiso calc R 1 1
H H15B -0.0300 1.8496 -0.0762 0.039 Uiso calc R 1 1
C C16 0.2169(9) 1.6942(10) -0.06676(6) 0.0343(13) Uani d . 1 1
H H16A 0.2099 1.7591 -0.0534 0.041 Uiso calc R 1 1
H H16B 0.1651 1.5456 -0.0662 0.041 Uiso calc R 1 1
C C17 0.8448(7) 0.2933(8) 0.22065(6) 0.0202(10) Uani d . 1 1
C C18 0.7797(8) 0.0817(8) 0.21900(6) 0.0225(10) Uani d . 1 1
H H18 0.7797 0.0108 0.2066 0.027 Uiso calc R 1 1
C C19 0.7146(8) -0.0281(8) 0.23527(6) 0.0222(10) Uani d . 1 1
H H19 0.6748 -0.1746 0.2342 0.027 Uiso calc R 1 1
C C20 0.7089(7) 0.0822(8) 0.25330(6) 0.0198(10) Uani d . 1 1
C C21 0.7694(7) 0.2955(8) 0.25531(6) 0.0214(10) Uani d . 1 1
H H21 0.7630 0.3686 0.2676 0.026 Uiso calc R 1 1
C C22 0.8397(7) 0.4002(8) 0.23894(6) 0.0215(10) Uani d . 1 1
H H22 0.8845 0.5447 0.2401 0.026 Uiso calc R 1 1
C C23 0.9232(7) 0.4134(8) 0.20315(6) 0.0214(10) Uani d . 1 1
C C24 0.3087(7) 0.9141(8) 0.02928(6) 0.0228(10) Uani d . 1 1
C C25 0.2410(8) 1.1271(8) 0.02923(6) 0.0247(11) Uani d . 1 1
H H25 0.2276 1.2007 0.0414 0.030 Uiso calc R 1 1
C C26 0.1932(7) 1.2320(8) 0.01153(6) 0.0217(10) Uani d . 1 1
H H26 0.1461 1.3760 0.0114 0.026 Uiso calc R 1 1
C C27 0.2169(7) 1.1176(8) -0.00629(6) 0.0225(10) Uani d . 1 1
C C28 0.2787(8) 0.9054(8) -0.00655(6) 0.0243(10) Uani d . 1 1
H H28 0.2896 0.8311 -0.0187 0.029 Uiso calc R 1 1
C C29 0.3247(8) 0.8019(8) 0.01134(6) 0.0238(10) Uani d . 1 1
H H29 0.3669 0.6559 0.0114 0.029 Uiso calc R 1 1
C C30 0.3676(8) 0.7990(8) 0.04861(6) 0.0244(10) Uani 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 109.5
C12 O2 H2H 109.5
C8 N1 H1N 109.5
C8 N1 H2N 109.5
H1N N1 H2N 109.5
C8 N1 H3N 109.5
H1N N1 H3N 109.5
H2N N1 H3N 109.5
C16 N2 H4N 109.5
C16 N2 H5N 109.5
H4N N2 H5N 109.5
C16 N2 H6N 109.5
H4N N2 H6N 109.5
H5N N2 H6N 109.5
O5 N3 O6 123.6(4)
O5 N3 C20 118.8(4)
O6 N3 C20 117.6(4)
O9 N4 O10 123.3(4)
O9 N4 C27 118.8(4)
O10 N4 C27 117.9(4)
C2 C1 C6 117.6(4)
C2 C1 C7 121.5(4)
C6 C1 C7 120.9(4)
C3 C2 C1 122.3(5)
C3 C2 H2 118.9
C1 C2 H2 118.9
C4 C3 C2 119.0(4)
C4 C3 H3 120.5
C2 C3 H3 120.5
O1 C4 C3 122.4(4)
O1 C4 C5 117.1(4)
C3 C4 C5 120.5(4)
C4 C5 C6 119.2(4)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C1 121.4(4)
C5 C6 H6 119.3
C1 C6 H6 119.3
C1 C7 C8 114.1(4)
C1 C7 H7A 108.7
C8 C7 H7A 108.7
C1 C7 H7B 108.7
C8 C7 H7B 108.7
H7A C7 H7B 107.6
N1 C8 C7 111.9(4)
N1 C8 H8A 109.2
C7 C8 H8A 109.2
N1 C8 H8B 109.2
C7 C8 H8B 109.2
H8A C8 H8B 107.9
C14 C9 C10 118.3(4)
C14 C9 C15 120.7(4)
C10 C9 C15 121.0(5)
C9 C10 C11 120.6(5)
C9 C10 H10 119.7
C11 C10 H10 119.7
C12 C11 C10 120.0(4)
C12 C11 H11 120.0
C10 C11 H11 120.0
O2 C12 C11 122.9(4)
O2 C12 C13 117.3(4)
C11 C12 C13 119.8(4)
C14 C13 C12 120.3(5)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C9 121.0(4)
C13 C14 H14 119.5
C9 C14 H14 119.5
C16 C15 C9 114.1(4)
C16 C15 H15A 108.7
C9 C15 H15A 108.7
C16 C15 H15B 108.7
C9 C15 H15B 108.7
H15A C15 H15B 107.6
N2 C16 C15 112.1(4)
N2 C16 H16A 109.2
C15 C16 H16A 109.2
N2 C16 H16B 109.2
C15 C16 H16B 109.2
H16A C16 H16B 107.9
C18 C17 C22 119.5(4)
C18 C17 C23 121.8(4)
C22 C17 C23 118.7(4)
C17 C18 C19 121.0(4)
C17 C18 H18 119.5
C19 C18 H18 119.5
C18 C19 C20 118.5(4)
C18 C19 H19 120.7
C20 C19 H19 120.7
C21 C20 C19 121.7(4)
C21 C20 N3 118.6(4)
C19 C20 N3 119.5(4)
C20 C21 C22 118.7(4)
C20 C21 H21 120.6
C22 C21 H21 120.6
C21 C22 C17 120.5(5)
C21 C22 H22 119.8
C17 C22 H22 119.8
O3 C23 O4 125.2(4)
O3 C23 C17 118.4(4)
O4 C23 C17 116.4(4)
C25 C24 C29 120.1(4)
C25 C24 C30 121.2(4)
C29 C24 C30 118.7(4)
C26 C25 C24 120.6(4)
C26 C25 H25 119.7
C24 C25 H25 119.7
C25 C26 C27 117.9(4)
C25 C26 H26 121.0
C27 C26 H26 121.0
C28 C27 C26 122.3(4)
C28 C27 N4 120.1(4)
C26 C27 N4 117.6(4)
C27 C28 C29 119.0(4)
C27 C28 H28 120.5
C29 C28 H28 120.5
C28 C29 C24 119.9(5)
C28 C29 H29 120.0
C24 C29 H29 120.0
O8 C30 O7 126.5(4)
O8 C30 C24 116.6(4)
O7 C30 C24 116.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.379(5)
O1 H1H 0.8400
O2 C12 1.374(5)
O2 H2H 0.8400
O3 C23 1.243(6)
O4 C23 1.282(5)
O5 N3 1.236(5)
O6 N3 1.238(6)
O7 C30 1.277(6)
O8 C30 1.250(6)
O9 N4 1.230(6)
O10 N4 1.237(5)
N1 C8 1.503(7)
N1 H1N 0.9100
N1 H2N 0.9100
N1 H3N 0.9100
N2 C16 1.485(8)
N2 H4N 0.9100
N2 H5N 0.9100
N2 H6N 0.9100
N3 C20 1.461(5)
N4 C27 1.477(6)
C1 C2 1.397(6)
C1 C6 1.403(7)
C1 C7 1.525(6)
C2 C3 1.397(6)
C2 H2 0.9500
C3 C4 1.395(7)
C3 H3 0.9500
C4 C5 1.399(6)
C5 C6 1.402(6)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.536(7)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C14 1.399(8)
C9 C10 1.402(6)
C9 C15 1.529(6)
C10 C11 1.411(6)
C10 H10 0.9500
C11 C12 1.380(7)
C11 H11 0.9500
C12 C13 1.396(6)
C13 C14 1.389(6)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.528(7)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.389(7)
C17 C22 1.406(6)
C17 C23 1.524(6)
C18 C19 1.390(6)
C18 H18 0.9500
C19 C20 1.401(6)
C19 H19 0.9500
C20 C21 1.391(7)
C21 C22 1.395(6)
C21 H21 0.9500
C22 H22 0.9500
C24 C25 1.400(7)
C24 C29 1.408(6)
C24 C30 1.532(6)
C25 C26 1.392(6)
C25 H25 0.9500
C26 C27 1.415(6)
C26 H26 0.9500
C27 C28 1.382(7)
C28 C29 1.397(6)
C28 H28 0.9500
C29 H29 0.9500
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 1.4(8)
C7 C1 C2 C3 178.6(5)
C1 C2 C3 C4 -1.5(8)
C2 C3 C4 O1 180.0(5)
C2 C3 C4 C5 1.1(8)
O1 C4 C5 C6 -179.6(5)
C3 C4 C5 C6 -0.7(8)
C4 C5 C6 C1 0.5(8)
C2 C1 C6 C5 -0.9(8)
C7 C1 C6 C5 -178.2(5)
C2 C1 C7 C8 131.3(5)
C6 C1 C7 C8 -51.5(7)
C1 C7 C8 N1 -65.5(6)
C14 C9 C10 C11 1.6(8)
C15 C9 C10 C11 -179.6(5)
C9 C10 C11 C12 -0.6(8)
C10 C11 C12 O2 179.1(5)
C10 C11 C12 C13 -0.8(7)
O2 C12 C13 C14 -178.6(5)
C11 C12 C13 C14 1.3(8)
C12 C13 C14 C9 -0.3(8)
C10 C9 C14 C13 -1.2(8)
C15 C9 C14 C13 -179.9(5)
C14 C9 C15 C16 58.5(7)
C10 C9 C15 C16 -120.2(6)
C9 C15 C16 N2 67.6(7)
C22 C17 C18 C19 -1.8(7)
C23 C17 C18 C19 177.8(5)
C17 C18 C19 C20 2.4(8)
C18 C19 C20 C21 -1.1(8)
C18 C19 C20 N3 -176.7(5)
O5 N3 C20 C21 28.3(7)
O6 N3 C20 C21 -151.8(5)
O5 N3 C20 C19 -155.9(5)
O6 N3 C20 C19 24.0(7)
C19 C20 C21 C22 -0.9(7)
N3 C20 C21 C22 174.8(5)
C20 C21 C22 C17 1.5(7)
C18 C17 C22 C21 -0.2(7)
C23 C17 C22 C21 -179.8(5)
C18 C17 C23 O3 176.4(5)
C22 C17 C23 O3 -4.0(7)
C18 C17 C23 O4 -3.8(7)
C22 C17 C23 O4 175.8(5)
C29 C24 C25 C26 -1.5(8)
C30 C24 C25 C26 178.1(5)
C24 C25 C26 C27 -0.6(8)
C25 C26 C27 C28 2.4(8)
C25 C26 C27 N4 -177.6(5)
O9 N4 C27 C28 -176.4(5)
O10 N4 C27 C28 3.5(7)
O9 N4 C27 C26 3.6(7)
O10 N4 C27 C26 -176.6(5)
C26 C27 C28 C29 -1.9(8)
N4 C27 C28 C29 178.0(5)
C27 C28 C29 C24 -0.3(8)
C25 C24 C29 C28 2.0(8)
C30 C24 C29 C28 -177.7(5)
C25 C24 C30 O8 168.7(5)
C29 C24 C30 O8 -11.7(8)
C25 C24 C30 O7 -12.7(7)
C29 C24 C30 O7 166.9(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064109
