#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/07/4500721.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_4500721
loop_
_publ_author_name
'Nishizawa, Natsuko'
'Nakamura, Junya'
'Matsumoto, Akikazu'
_publ_section_title
;
 Single-Crystal-to-Single-Crystal Transformation of Di(isopropylammonium)
 (Z,Z)-Muconate into the (E,E)-Muconate during One-Way Photoisomerization
 in the Solid State
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3442
_journal_paper_doi               10.1021/cg200184c
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C12 H24 N2 O4 '
_chemical_formula_sum            'C12 H24 N2 O4'
_chemical_formula_weight         260.33
_chemical_name_systematic
; 
(Z,Z)-muconic isoprorylammonium 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.904(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5119(14)
_cell_length_b                   5.8624(8)
_cell_length_c                   20.426(5)
_cell_measurement_reflns_used    5715
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.4
_cell_volume                     778.0(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_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  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6434
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0531
_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)+(0.0964P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1641
_reflns_number_gt                1259
_reflns_number_total             1767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200184c_si_001.cif
_cod_data_source_block           ZZ-iPr_salt
_cod_database_code               4500721
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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 0.45278(19) 1.19047(18) 0.12821(5) 0.0371(4) Uani 1 1 d .
O2 O 0.28944(18) 0.90043(19) 0.17170(5) 0.0363(4) Uani 1 1 d .
N1 N 0.1809(2) 0.4587(2) 0.19178(7) 0.0319(4) Uani 1 1 d .
H7A H 0.280(3) 0.359(4) 0.1745(10) 0.046(5) Uiso 1 1 d .
H7B H 0.220(3) 0.622(4) 0.1797(9) 0.044(5) Uiso 1 1 d .
H7C H 0.197(3) 0.454(3) 0.2374(11) 0.043(5) Uiso 1 1 d .
C1 C 0.4967(3) 0.8868(3) 0.01332(8) 0.0332(4) Uani 1 1 d .
H1 H 0.5285 0.7652 -0.0150 0.043(5) Uiso 1 1 calc R
C2 C 0.4502(3) 0.8293(3) 0.07420(7) 0.0346(4) Uani 1 1 d .
H2 H 0.4515 0.6711 0.0843 0.042 Uiso 1 1 calc R
C3 C 0.3966(3) 0.9881(3) 0.12800(7) 0.0312(4) Uani 1 1 d .
C4 C -0.0358(3) 0.4076(3) 0.16702(8) 0.0377(4) Uani 1 1 d .
H4 H -0.0710 0.2497 0.1811 0.045 Uiso 1 1 calc R
C5 C -0.1780(3) 0.5733(3) 0.19774(9) 0.0440(5) Uani 1 1 d .
H5A H -0.1533 0.5685 0.2456 0.066 Uiso 1 1 calc R
H5B H -0.3212 0.5312 0.1856 0.066 Uiso 1 1 calc R
H5C H -0.1518 0.7278 0.1820 0.066 Uiso 1 1 calc R
C6 C -0.0517(3) 0.4162(4) 0.09285(9) 0.0540(6) Uani 1 1 d .
H6A H -0.0200 0.5708 0.0783 0.081 Uiso 1 1 calc R
H6B H -0.1917 0.3752 0.0764 0.081 Uiso 1 1 calc R
H6C H 0.0464 0.3083 0.0758 0.081 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0513(8) 0.0329(7) 0.0288(6) -0.0041(4) 0.0156(5) -0.0064(5)
O2 0.0487(8) 0.0376(7) 0.0243(6) 0.0001(4) 0.0146(5) -0.0051(5)
N1 0.0392(8) 0.0348(8) 0.0227(7) -0.0013(5) 0.0090(6) -0.0010(6)
C1 0.0406(9) 0.0346(9) 0.0253(8) -0.0034(6) 0.0094(6) 0.0018(7)
C2 0.0476(10) 0.0303(8) 0.0274(8) 0.0001(6) 0.0127(7) 0.0013(7)
C3 0.0371(9) 0.0341(8) 0.0229(8) 0.0010(6) 0.0063(6) 0.0019(7)
C4 0.0403(10) 0.0393(9) 0.0346(9) -0.0027(6) 0.0103(7) -0.0044(8)
C5 0.0409(10) 0.0529(11) 0.0388(10) -0.0022(8) 0.0080(8) 0.0011(8)
C6 0.0465(12) 0.0816(15) 0.0342(10) -0.0127(9) 0.0038(8) -0.0027(11)
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
C4 N1 H7A 113.5(11) . .
C4 N1 H7B 110.4(10) . .
H7A N1 H7B 107.2(16) . .
C4 N1 H7C 111.9(12) . .
H7A N1 H7C 108.6(17) . .
H7B N1 H7C 104.7(15) . .
C2 C1 C1 126.67(18) . 3_675
C2 C1 H1 116.7 . .
C1 C1 H1 116.7 3_675 .
C1 C2 C3 126.97(15) . .
C1 C2 H2 116.5 . .
C3 C2 H2 116.5 . .
O1 C3 O2 123.84(14) . .
O1 C3 C2 120.84(14) . .
O2 C3 C2 115.32(14) . .
N1 C4 C5 108.77(14) . .
N1 C4 C6 109.28(14) . .
C5 C4 C6 113.16(15) . .
N1 C4 H4 108.5 . .
C5 C4 H4 108.5 . .
C6 C4 H4 108.5 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.2412(19) .
O2 C3 1.2779(19) .
N1 C4 1.497(2) .
N1 H7A 0.96(2) .
N1 H7B 1.03(2) .
N1 H7C 0.93(2) .
C1 C2 1.343(2) .
C1 C1 1.437(3) 3_675
C1 H1 0.9500 .
C2 C3 1.500(2) .
C2 H2 0.9500 .
C4 C5 1.508(2) .
C4 C6 1.512(3) .
C4 H4 1.0000 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 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
C1 C1 C2 C3 -0.5(4) 3_675
C1 C2 C3 O1 -23.4(3) .
C1 C2 C3 O2 155.86(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144505
