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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/43/4504355.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_4504355
loop_
_publ_author_name
'Mori, Yutaka'
'Chiba, Tsuyoshi'
'Odani, Toru'
'Matsumoto, Akikazu'
_publ_section_title
;
 Molecular Arrangement and Photoreaction of Sorbamides and Hexadienyl
 Carbamates with Various N-Substituents in the Solid State
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1356
_journal_paper_doi               10.1021/cg070366o
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C13 H15 N O '
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   9.0770(9)
_cell_length_b                   13.2357(15)
_cell_length_c                   19.652(2)
_cell_measurement_reflns_used    11314
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      3.1
_cell_volume                     2361.0(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_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  'Mo Kα'
_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  0.0814
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21112
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0749
_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)+(0.0507P)²+0.8628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                1717
_reflns_number_total             2688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070366osi20070416_123153.cif
_cod_data_source_block           8
_cod_database_code               4504355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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
O1 O 0.37863(16) 0.45776(13) 0.19251(9) 0.0637(5) Uani 1 1 d .
N1 N 0.16536(18) 0.50932(13) 0.24099(9) 0.0511(5) Uani 1 1 d .
H1 H 0.0716 0.5001 0.2425 0.061 Uiso 1 1 calc R
C1 C 0.1927(4) 0.0687(2) 0.01539(16) 0.1028(11) Uani 1 1 d .
H1A H 0.0929 0.0823 0.0021 0.154 Uiso 1 1 calc R
H1B H 0.1959 0.0078 0.0419 0.154 Uiso 1 1 calc R
H1C H 0.2526 0.0606 -0.0245 0.154 Uiso 1 1 calc R
C2 C 0.2491(4) 0.1533(2) 0.05619(13) 0.0786(8) Uani 1 1 d .
H2 H 0.3482 0.1514 0.0681 0.094 Uiso 1 1 calc R
C3 C 0.1721(3) 0.23172(19) 0.07754(12) 0.0635(7) Uani 1 1 d .
H3 H 0.0743 0.2365 0.0639 0.076 Uiso 1 1 calc R
C4 C 0.2299(3) 0.31043(17) 0.12062(11) 0.0546(6) Uani 1 1 d .
H4 H 0.3311 0.3091 0.1280 0.065 Uiso 1 1 calc R
C5 C 0.1563(2) 0.38495(18) 0.15118(11) 0.0514(6) Uani 1 1 d .
C6 C -0.0063(3) 0.4023(3) 0.14312(17) 0.0953(11) Uani 1 1 d .
H6A H -0.0419 0.3643 0.1049 0.143 Uiso 1 1 calc R
H6B H -0.0244 0.4729 0.1357 0.143 Uiso 1 1 calc R
H6C H -0.0564 0.3808 0.1836 0.143 Uiso 1 1 calc R
C7 C 0.2437(2) 0.45345(16) 0.19598(11) 0.0483(5) Uani 1 1 d .
C8 C 0.2273(2) 0.58200(16) 0.28577(11) 0.0470(5) Uani 1 1 d .
C9 C 0.3328(3) 0.64986(17) 0.26360(12) 0.0579(6) Uani 1 1 d .
H9 H 0.3659 0.6477 0.2188 0.070 Uiso 1 1 calc R
C10 C 0.3887(3) 0.7207(2) 0.30816(15) 0.0713(7) Uani 1 1 d .
H10 H 0.4591 0.7667 0.2932 0.086 Uiso 1 1 calc R
C11 C 0.3413(3) 0.7237(2) 0.37426(16) 0.0754(8) Uani 1 1 d .
H11 H 0.3803 0.7711 0.4042 0.090 Uiso 1 1 calc R
C12 C 0.2360(3) 0.6568(2) 0.39628(13) 0.0731(8) Uani 1 1 d .
H12 H 0.2036 0.6591 0.4411 0.088 Uiso 1 1 calc R
C13 C 0.1780(3) 0.58597(19) 0.35212(12) 0.0597(6) Uani 1 1 d .
H13 H 0.1061 0.5411 0.3671 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'
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
C7 N1 C8 124.55(18)
C7 N1 H1 117.7
C8 N1 H1 117.7
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C1 126.1(3)
C3 C2 H2 117.0
C1 C2 H2 117.0
C2 C3 C4 124.3(3)
C2 C3 H3 117.9
C4 C3 H3 117.9
C5 C4 C3 128.1(2)
C5 C4 H4 116.0
C3 C4 H4 116.0
C4 C5 C7 116.69(19)
C4 C5 C6 123.9(2)
C7 C5 C6 119.4(2)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O1 C7 N1 122.3(2)
O1 C7 C5 121.7(2)
N1 C7 C5 116.01(18)
C13 C8 C9 119.8(2)
C13 C8 N1 118.9(2)
C9 C8 N1 121.2(2)
C10 C9 C8 119.7(2)
C10 C9 H9 120.1
C8 C9 H9 120.1
C11 C10 C9 120.4(3)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 119.9(2)
C10 C11 H11 120.0
C12 C11 H11 120.0
C11 C12 C13 120.3(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
C8 C13 C12 119.7(2)
C8 C13 H13 120.1
C12 C13 H13 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.228(2)
N1 C7 1.354(3)
N1 C8 1.420(3)
N1 H1 0.8600
C1 C2 1.469(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.319(4)
C2 H2 0.9300
C3 C4 1.441(3)
C3 H3 0.9300
C4 C5 1.334(3)
C4 H4 0.9300
C5 C7 1.492(3)
C5 C6 1.502(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C8 C13 1.379(3)
C8 C9 1.383(3)
C9 C10 1.380(3)
C9 H9 0.9300
C10 C11 1.369(4)
C10 H10 0.9300
C11 C12 1.372(4)
C11 H11 0.9300
C12 C13 1.382(3)
C12 H12 0.9300
C13 H13 0.9300
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
C1 C2 C3 C4 176.5(3)
C2 C3 C4 C5 -171.0(3)
C3 C4 C5 C7 177.1(2)
C3 C4 C5 C6 -2.6(4)
C8 N1 C7 O1 3.7(3)
C8 N1 C7 C5 -177.06(19)
C4 C5 C7 O1 17.3(3)
C6 C5 C7 O1 -163.1(3)
C4 C5 C7 N1 -162.0(2)
C6 C5 C7 N1 17.7(3)
C7 N1 C8 C13 -137.8(2)
C7 N1 C8 C9 43.8(3)
C13 C8 C9 C10 0.4(3)
N1 C8 C9 C10 178.8(2)
C8 C9 C10 C11 0.5(4)
C9 C10 C11 C12 -0.8(4)
C10 C11 C12 C13 0.3(4)
C9 C8 C13 C12 -0.9(3)
N1 C8 C13 C12 -179.4(2)
C11 C12 C13 C8 0.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661453
2 PubChem 139145499
