#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150878.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_7150878
loop_
_publ_author_name
'Matsuhira, Takashi'
'Yamamoto, Hitoshi'
'Okamura, Taka-aki'
'Ueyama, Norikazu'
_publ_section_title
;
 Manipulation of an intramolecular NH⋯O hydrogen bond by
 photoswitching between stable E/Z isomers of the cinnamate framework
;
_journal_issue                   11
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1926
_journal_page_last               1933
_journal_paper_doi               10.1039/b719960k
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C18 H28 N2 O3'
_chemical_formula_sum            'C18 H28 N2 O3'
_chemical_formula_weight         320.42
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   21.127(5)
_cell_length_b                   21.127(5)
_cell_length_c                   7.5223(15)
_cell_measurement_reflns_used    18890
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     2907.7(11)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27887
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4440
_refine_ls_number_restraints     139
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.2749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                3638
_reflns_number_total             4440
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b719960k.txt
_cod_data_source_block           shelxl2
_cod_original_cell_volume        2907.8(12)
_cod_original_sg_symbol_H-M      'P 63 '
_cod_database_code               7150878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54729(7) 0.65887(6) 0.46508(18) 0.0551(3) Uani 1 1 d U . .
O2 O 0.45663(7) 0.57856(6) 0.63470(18) 0.0557(3) Uani 1 1 d U . .
O3 O 0.70876(7) 0.92278(7) 0.3694(2) 0.0646(4) Uani 1 1 d U . .
N1 N 0.62335(7) 0.80383(7) 0.39782(18) 0.0421(3) Uani 1 1 d U . .
H1 H 0.6091(10) 0.7602(10) 0.443(2) 0.051 Uiso 1 1 d . . .
N2 N 0.58756(7) 0.60589(6) 0.02001(18) 0.0367(3) Uani 1 1 d U . .
C1 C 0.49445(8) 0.64054(8) 0.56867(19) 0.0359(3) Uani 1 1 d U . .
C2 C 0.47385(9) 0.69586(8) 0.6262(2) 0.0406(3) Uani 1 1 d U . .
H2 H 0.4583 0.6921 0.7461 0.049 Uiso 1 1 calc R . .
C3 C 0.47440(8) 0.74951(8) 0.5321(2) 0.0405(3) Uani 1 1 d U . .
H3 H 0.4570 0.7770 0.5941 0.049 Uiso 1 1 calc R . .
C4 C 0.49766(9) 0.77336(8) 0.3468(2) 0.0389(3) Uani 1 1 d U . .
C5 C 0.44542(11) 0.77147(9) 0.2289(3) 0.0586(5) Uani 1 1 d U . .
H5 H 0.3965 0.7528 0.2679 0.070 Uiso 1 1 calc R . .
C6 C 0.46461(16) 0.79682(11) 0.0540(3) 0.0750(7) Uani 1 1 d U . .
H6 H 0.4283 0.7933 -0.0265 0.090 Uiso 1 1 calc R . .
C7 C 0.53538(16) 0.82647(11) -0.0007(3) 0.0714(7) Uani 1 1 d U . .
H7 H 0.5483 0.8444 -0.1187 0.086 Uiso 1 1 calc R . .
C8 C 0.58781(13) 0.83070(9) 0.1125(2) 0.0555(5) Uani 1 1 d U . .
H8 H 0.6370 0.8521 0.0734 0.067 Uiso 1 1 calc R . .
C9 C 0.56937(9) 0.80363(8) 0.28578(19) 0.0394(3) Uani 1 1 d U . .
C10 C 0.69042(9) 0.86148(9) 0.4263(2) 0.0446(4) Uani 1 1 d U . .
C11 C 0.74233(9) 0.84688(10) 0.5384(3) 0.0535(4) Uani 1 1 d U . .
C12 C 0.71986(15) 0.84416(17) 0.7332(3) 0.0865(7) Uani 1 1 d U . .
H12A H 0.7228 0.8905 0.7652 0.104 Uiso 1 1 calc R . .
H12B H 0.7528 0.8362 0.8096 0.104 Uiso 1 1 calc R . .
H12C H 0.6696 0.8041 0.7495 0.104 Uiso 1 1 calc R . .
C13 C 0.73680(16) 0.77454(15) 0.4927(4) 0.0962(9) Uani 1 1 d U . .
H13A H 0.6862 0.7351 0.5081 0.115 Uiso 1 1 calc R . .
H13B H 0.7689 0.7662 0.5715 0.115 Uiso 1 1 calc R . .
H13C H 0.7518 0.7755 0.3690 0.115 Uiso 1 1 calc R . .
C14 C 0.81961(13) 0.90952(17) 0.5173(5) 0.1174(12) Uani 1 1 d U . .
H14A H 0.8214 0.9555 0.5473 0.141 Uiso 1 1 calc R . .
H14B H 0.8354 0.9115 0.3939 0.141 Uiso 1 1 calc R . .
H14C H 0.8521 0.9022 0.5968 0.141 Uiso 1 1 calc R . .
C15 C 0.60481(14) 0.68295(10) 0.0150(3) 0.0644(5) Uani 1 1 d U . .
H15A H 0.5910 0.6955 0.1283 0.077 Uiso 1 1 calc R . .
H15B H 0.5775 0.6894 -0.0819 0.077 Uiso 1 1 calc R . .
H15C H 0.6573 0.7149 -0.0047 0.077 Uiso 1 1 calc R . .
C16 C 0.60858(10) 0.58626(11) -0.1516(2) 0.0523(4) Uani 1 1 d U . .
H16A H 0.6611 0.6184 -0.1718 0.063 Uiso 1 1 calc R . .
H16B H 0.5811 0.5922 -0.2488 0.063 Uiso 1 1 calc R . .
H16C H 0.5974 0.5353 -0.1470 0.063 Uiso 1 1 calc R . .
C17 C 0.62901(10) 0.59677(9) 0.1689(2) 0.0478(4) Uani 1 1 d U . .
H17A H 0.6148 0.6095 0.2815 0.057 Uiso 1 1 calc R . .
H17B H 0.6815 0.6289 0.1496 0.057 Uiso 1 1 calc R . .
H17C H 0.6179 0.5459 0.1735 0.057 Uiso 1 1 calc R . .
C18 C 0.50782(9) 0.55704(11) 0.0498(3) 0.0600(5) Uani 1 1 d U . .
H18A H 0.4938 0.5696 0.1630 0.072 Uiso 1 1 calc R . .
H18B H 0.4966 0.5061 0.0534 0.072 Uiso 1 1 calc R . .
H18C H 0.4805 0.5633 -0.0472 0.072 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'
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'
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
_geom_angle_publ_flag
C10 N1 C9 125.38(13) . . ?
C10 N1 H1 122.6(12) . . ?
C9 N1 H1 111.9(12) . . ?
C15 N2 C18 109.71(14) . . ?
C15 N2 C16 109.90(14) . . ?
C18 N2 C16 109.22(14) . . ?
C15 N2 C17 108.86(13) . . ?
C18 N2 C17 109.34(13) . . ?
C16 N2 C17 109.79(12) . . ?
O2 C1 O1 125.19(14) . . ?
O2 C1 C2 114.85(14) . . ?
O1 C1 C2 119.93(13) . . ?
C3 C2 C1 128.86(15) . . ?
C3 C2 H2 115.6 . . ?
C1 C2 H2 115.6 . . ?
C2 C3 C4 130.59(14) . . ?
C2 C3 H3 114.7 . . ?
C4 C3 H3 114.7 . . ?
C9 C4 C5 117.69(16) . . ?
C9 C4 C3 124.43(14) . . ?
C5 C4 C3 117.63(16) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.98(19) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.71(16) . . ?
C4 C9 N1 119.60(13) . . ?
C8 C9 N1 119.63(16) . . ?
O3 C10 N1 122.24(16) . . ?
O3 C10 C11 121.58(16) . . ?
N1 C10 C11 116.16(14) . . ?
C14 C11 C13 111.4(2) . . ?
C14 C11 C10 109.54(17) . . ?
C13 C11 C10 112.14(17) . . ?
C14 C11 C12 108.2(2) . . ?
C13 C11 C12 108.3(2) . . ?
C10 C11 C12 107.14(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2535(19) . ?
O2 C1 1.2463(18) . ?
O3 C10 1.228(2) . ?
N1 C10 1.346(2) . ?
N1 C9 1.416(2) . ?
N1 H1 0.882(19) . ?
N2 C15 1.481(2) . ?
N2 C18 1.488(2) . ?
N2 C16 1.490(2) . ?
N2 C17 1.492(2) . ?
C1 C2 1.500(2) . ?
C2 C3 1.331(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.480(2) . ?
C3 H3 0.9500 . ?
C4 C9 1.395(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.532(3) . ?
C11 C14 1.511(3) . ?
C11 C13 1.513(3) . ?
C11 C12 1.533(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -143.87(17) . . . . ?
O1 C1 C2 C3 37.7(2) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
C2 C3 C4 C9 -65.7(2) . . . . ?
C2 C3 C4 C5 120.27(19) . . . . ?
C9 C4 C5 C6 2.3(2) . . . . ?
C3 C4 C5 C6 176.71(14) . . . . ?
C4 C5 C6 C7 -2.8(3) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C3 C4 C9 C8 -174.28(14) . . . . ?
C5 C4 C9 N1 -177.30(14) . . . . ?
C3 C4 C9 N1 8.7(2) . . . . ?
C7 C8 C9 C4 -1.3(2) . . . . ?
C7 C8 C9 N1 175.69(15) . . . . ?
C10 N1 C9 C4 -133.42(16) . . . . ?
C10 N1 C9 C8 49.5(2) . . . . ?
C9 N1 C10 O3 7.5(3) . . . . ?
C9 N1 C10 C11 -174.16(14) . . . . ?
O3 C10 C11 C14 -16.8(3) . . . . ?
N1 C10 C11 C14 164.8(2) . . . . ?
O3 C10 C11 C13 -141.0(2) . . . . ?
N1 C10 C11 C13 40.6(2) . . . . ?
O3 C10 C11 C12 100.4(2) . . . . ?
N1 C10 C11 C12 -78.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653414
2 PubChem 139190265
