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#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/45/7114502.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.
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data_7114502
loop_
_publ_author_name
'Gibson (née Thomas), Susan E.'
'Jones, Jerome O.'
'Kalindjian, S. Barret'
'Knight, Jamie D.'
'Steed, Jonathan W.'
'Tozer, Matthew J.'
_publ_section_title
;
 Synthesis and structural analysis of dehydrophenylalanine cyclophanes
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1938
_journal_paper_doi               10.1039/b205752m
_journal_year                    2002
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_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                68.324(15)
_cell_angle_beta                 75.548(16)
_cell_angle_gamma                77.333(15)
_cell_formula_units_Z            2
_cell_length_a                   9.068(2)
_cell_length_b                   10.189(3)
_cell_length_c                   11.317(3)
_cell_measurement_temperature    100(2)
_cell_volume                     931.5(4)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'XSeed (Barbour, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '2o phi+omega 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  0.1335
_diffrn_reflns_av_sigmaI/netI    0.1977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4700
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   Scalepack
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.278
_refine_ls_R_factor_all          0.2153
_refine_ls_R_factor_gt           0.1500
_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)+(0.0000P)²+1.6841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2361
_reflns_number_gt                1970
_reflns_number_total             3015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b205752m.txt
_cod_data_source_block           jj291
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7114502
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C19 C -0.2510(7) 0.3426(8) 0.2293(8) 0.050(2) Uani 1 1 d .
H19A H -0.2845 0.3346 0.3207 0.075 Uiso 1 1 calc R
H19B H -0.3248 0.3067 0.2028 0.075 Uiso 1 1 calc R
H19C H -0.2452 0.4429 0.1764 0.075 Uiso 1 1 calc R
O2 O 0.1412(4) 0.6327(4) 0.2424(4) 0.0258(10) Uani 1 1 d .
O4 O 0.0223(4) 0.3182(4) 0.2372(4) 0.0278(10) Uani 1 1 d .
O1 O 0.3619(4) 0.6173(4) 0.1008(4) 0.0275(10) Uani 1 1 d .
N1 N 0.1533(5) 0.3549(4) 0.3622(4) 0.0187(11) Uani 1 1 d .
O3 O -0.0827(4) 0.2806(4) 0.4509(4) 0.0290(11) Uani 1 1 d .
C15 C 0.0193(6) 0.3152(5) 0.3579(6) 0.0211(13) Uani 1 1 d .
C6 C 0.5423(7) -0.0390(6) 0.1631(6) 0.0290(15) Uani 1 1 d .
H6 H 0.6160 -0.0743 0.1020 0.035 Uiso 1 1 calc R
C12 C 0.2642(6) 0.4028(5) 0.2480(5) 0.0192(13) Uani 1 1 d .
C8 C 0.3958(6) 0.1632(5) 0.2233(5) 0.0207(13) Uani 1 1 d .
C5 C 0.4751(7) -0.1346(6) 0.2769(5) 0.0235(13) Uani 1 1 d .
C7 C 0.5043(7) 0.1060(6) 0.1371(5) 0.0256(14) Uani 1 1 d .
H7 H 0.5531 0.1687 0.0586 0.031 Uiso 1 1 calc R
C4 C 0.5225(7) -0.2945(6) 0.3098(6) 0.0312(15) Uani 1 1 d .
H4A H 0.5300 -0.3206 0.2323 0.037 Uiso 1 1 calc R
H4B H 0.4419 -0.3441 0.3784 0.037 Uiso 1 1 calc R
C13 C 0.2647(6) 0.5616(6) 0.1869(5) 0.0206(13) Uani 1 1 d .
C11 C 0.3661(6) 0.3193(6) 0.1883(5) 0.0209(13) Uani 1 1 d .
H11 H 0.4294 0.3692 0.1109 0.025 Uiso 1 1 calc R
C10 C 0.3668(6) -0.0774(6) 0.3636(6) 0.0279(15) Uani 1 1 d .
H10 H 0.3188 -0.1402 0.4425 0.033 Uiso 1 1 calc R
C1 C 0.8331(6) -0.3782(6) 0.5205(5) 0.0245(14) Uani 1 1 d .
H1A H 0.8482 -0.4822 0.5366 0.029 Uiso 1 1 calc R
H1B H 0.9165 -0.3374 0.4493 0.029 Uiso 1 1 calc R
C3 C 0.6769(7) -0.3456(6) 0.3562(5) 0.0250(14) Uani 1 1 d .
H3A H 0.7022 -0.4499 0.3744 0.030 Uiso 1 1 calc R
H3B H 0.7580 -0.3000 0.2854 0.030 Uiso 1 1 calc R
C9 C 0.3281(6) 0.0677(6) 0.3377(6) 0.0252(14) Uani 1 1 d .
H9 H 0.2542 0.1030 0.3988 0.030 Uiso 1 1 calc R
C14 C 0.1357(7) 0.7851(5) 0.2050(6) 0.0296(15) Uani 1 1 d .
H14A H 0.2246 0.8155 0.1371 0.044 Uiso 1 1 calc R
H14B H 0.1383 0.8099 0.2803 0.044 Uiso 1 1 calc R
H14C H 0.0407 0.8335 0.1724 0.044 Uiso 1 1 calc R
C16 C -0.0933(7) 0.2554(7) 0.2105(7) 0.0366(17) Uani 1 1 d .
C17 C -0.0935(8) 0.1017(7) 0.2962(7) 0.048(2) Uani 1 1 d .
H17A H 0.0116 0.0509 0.2883 0.072 Uiso 1 1 calc R
H17B H -0.1594 0.0572 0.2698 0.072 Uiso 1 1 calc R
H17C H -0.1329 0.0971 0.3863 0.072 Uiso 1 1 calc R
C18 C -0.0340(8) 0.2689(9) 0.0692(7) 0.058(2) Uani 1 1 d .
H18A H -0.0290 0.3695 0.0172 0.087 Uiso 1 1 calc R
H18B H -0.1036 0.2317 0.0394 0.087 Uiso 1 1 calc R
H18C H 0.0690 0.2141 0.0598 0.087 Uiso 1 1 calc R
C2 C 0.6797(6) -0.3132(6) 0.4769(5) 0.0265(14) Uani 1 1 d .
H2A H 0.6644 -0.2087 0.4577 0.032 Uiso 1 1 calc R
H2B H 0.5950 -0.3530 0.5471 0.032 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
C13 O2 C14 117.1(4) . .
C15 O4 C16 121.0(4) . .
C15 N1 C12 121.1(5) . .
C15 N1 C1 119.3(4) . 2_656
C12 N1 C1 118.3(4) . 2_656
O3 C15 O4 126.3(5) . .
O3 C15 N1 123.9(5) . .
O4 C15 N1 109.8(5) . .
C7 C6 C5 121.2(5) . .
C11 C12 N1 125.8(5) . .
C11 C12 C13 117.2(5) . .
N1 C12 C13 117.0(5) . .
C9 C8 C7 117.4(5) . .
C9 C8 C11 125.1(5) . .
C7 C8 C11 117.5(5) . .
C6 C5 C10 117.2(5) . .
C6 C5 C4 121.6(5) . .
C10 C5 C4 121.1(5) . .
C6 C7 C8 121.6(5) . .
C5 C4 C3 112.6(5) . .
O1 C13 O2 124.3(5) . .
O1 C13 C12 124.8(5) . .
O2 C13 C12 110.8(5) . .
C12 C11 C8 130.5(5) . .
C9 C10 C5 121.8(5) . .
N1 C1 C2 114.2(4) 2_656 .
C2 C3 C4 114.2(5) . .
C10 C9 C8 120.8(5) . .
O4 C16 C17 110.0(5) . .
O4 C16 C18 101.9(5) . .
C17 C16 C18 111.7(6) . .
O4 C16 C19 109.8(5) . .
C17 C16 C19 111.6(6) . .
C18 C16 C19 111.4(6) . .
C1 C2 C3 109.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C19 C16 1.520(9) .
O2 C13 1.343(6) .
O2 C14 1.444(6) .
O4 C15 1.349(7) .
O4 C16 1.482(7) .
O1 C13 1.196(6) .
N1 C15 1.378(7) .
N1 C12 1.422(7) .
N1 C1 1.471(7) 2_656
O3 C15 1.213(6) .
C6 C7 1.377(8) .
C6 C5 1.386(8) .
C12 C11 1.343(7) .
C12 C13 1.507(7) .
C8 C9 1.391(7) .
C8 C7 1.395(7) .
C8 C11 1.470(7) .
C5 C10 1.399(8) .
C5 C4 1.518(8) .
C4 C3 1.534(8) .
C10 C9 1.377(7) .
C1 N1 1.471(7) 2_656
C1 C2 1.521(7) .
C3 C2 1.527(8) .
C16 C17 1.507(9) .
C16 C18 1.519(9) .
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
C16 O4 C15 O3 -10.0(8) .
C16 O4 C15 N1 168.7(4) .
C12 N1 C15 O3 -176.0(5) .
C1 N1 C15 O3 -9.5(7) 2_656
C12 N1 C15 O4 5.3(6) .
C1 N1 C15 O4 171.8(4) 2_656
C15 N1 C12 C11 -78.1(7) .
C1 N1 C12 C11 115.3(6) 2_656
C15 N1 C12 C13 100.4(6) .
C1 N1 C12 C13 -66.2(6) 2_656
C7 C6 C5 C10 0.2(9) .
C7 C6 C5 C4 -176.6(5) .
C5 C6 C7 C8 -0.6(9) .
C9 C8 C7 C6 0.6(8) .
C11 C8 C7 C6 178.4(5) .
C6 C5 C4 C3 76.3(7) .
C10 C5 C4 C3 -100.4(6) .
C14 O2 C13 O1 -7.3(8) .
C14 O2 C13 C12 172.5(5) .
C11 C12 C13 O1 -11.1(8) .
N1 C12 C13 O1 170.3(5) .
C11 C12 C13 O2 169.1(5) .
N1 C12 C13 O2 -9.6(7) .
N1 C12 C11 C8 -2.4(10) .
C13 C12 C11 C8 179.1(5) .
C9 C8 C11 C12 -6.3(9) .
C7 C8 C11 C12 176.1(6) .
C6 C5 C10 C9 0.0(9) .
C4 C5 C10 C9 176.9(6) .
C5 C4 C3 C2 59.5(7) .
C5 C10 C9 C8 0.1(9) .
C7 C8 C9 C10 -0.4(8) .
C11 C8 C9 C10 -178.0(5) .
C15 O4 C16 C17 -55.3(7) .
C15 O4 C16 C18 -173.9(5) .
C15 O4 C16 C19 67.9(7) .
N1 C1 C2 C3 -179.1(5) 2_656
C4 C3 C2 C1 175.6(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184990
