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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/4/50/07/4500722.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_4500722
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
; 
EE-iPrAm 
;
_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                 97.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4631(17)
_cell_length_b                   5.9109(19)
_cell_length_c                   20.402(8)
_cell_measurement_reflns_used    7648
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     773.4(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       8
_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            7417
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0381
_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)+(0.0573P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                1250
_reflns_number_total             1781
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200184c_si_002.cif
_cod_data_source_block           iso-Propylammonium(E,E)-muconate
_cod_database_code               4500722
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_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 0.07801(13) -0.41517(14) 0.82951(4) 0.0296(2) Uani 1 1 d .
O2 O 0.27545(13) -0.13112(14) 0.87357(4) 0.0320(2) Uani 1 1 d .
N1 N -0.02885(15) -0.85996(16) 0.80807(5) 0.0261(3) Uani 1 1 d .
H7A H -0.0430 -0.8643 0.7632 0.039 Uiso 1 1 calc R
H7B H 0.0679 -0.9636 0.8246 0.039 Uiso 1 1 calc R
H7C H 0.0132 -0.7193 0.8222 0.039 Uiso 1 1 calc R
C1 C 0.45295(19) -0.4255(2) 0.97441(6) 0.0272(3) Uani 1 1 d .
H1 H 0.4953 -0.2715 0.9760 0.033 Uiso 1 1 calc R
C2 C 0.31098(18) -0.4895(2) 0.92523(6) 0.0281(3) Uani 1 1 d .
H2 H 0.2676 -0.6432 0.9234 0.034 Uiso 1 1 calc R
C3 C 0.21637(18) -0.3322(2) 0.87282(6) 0.0255(3) Uani 1 1 d .
C4 C -0.23397(19) -0.9136(2) 0.83158(6) 0.0305(3) Uani 1 1 d .
H4 H -0.2766 -1.0698 0.8167 0.037 Uiso 1 1 calc R
C5 C -0.3959(2) -0.7478(2) 0.80045(7) 0.0376(3) Uani 1 1 d .
H5A H -0.5335 -0.7904 0.8120 0.048(4) Uiso 1 1 calc R
H5B H -0.3983 -0.7506 0.7523 0.045(4) Uiso 1 1 calc R
H5C H -0.3608 -0.5951 0.8169 0.042(4) Uiso 1 1 calc R
C6 C -0.2092(2) -0.9076(3) 0.90614(7) 0.0418(4) Uani 1 1 d .
H6A H -0.1002 -1.0144 0.9236 0.046(4) Uiso 1 1 calc R
H6B H -0.3413 -0.9498 0.9218 0.076(6) Uiso 1 1 calc R
H6C H -0.1699 -0.7545 0.9214 0.048(4) 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 0.0353(5) 0.0280(5) 0.0222(5) 0.0015(4) -0.0094(4) -0.0022(3)
O2 0.0362(5) 0.0249(5) 0.0311(5) 0.0043(4) -0.0116(4) -0.0021(4)
N1 0.0309(6) 0.0248(5) 0.0204(5) 0.0001(4) -0.0059(4) 0.0002(4)
C1 0.0334(7) 0.0243(6) 0.0218(6) 0.0015(5) -0.0044(5) 0.0003(5)
C2 0.0341(7) 0.0237(6) 0.0246(6) 0.0022(5) -0.0045(5) -0.0004(5)
C3 0.0279(6) 0.0257(6) 0.0213(6) -0.0001(5) -0.0037(5) 0.0003(5)
C4 0.0303(7) 0.0288(7) 0.0309(7) 0.0015(5) -0.0022(5) -0.0041(5)
C5 0.0320(7) 0.0423(8) 0.0367(8) 0.0014(7) -0.0029(6) 0.0027(6)
C6 0.0433(9) 0.0506(9) 0.0314(8) 0.0074(7) 0.0036(6) 0.0001(7)
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_3
C2 C1 C1 124.29(15) 3_647
C1 C2 C3 123.25(11) .
O2 C3 O1 124.22(11) .
O2 C3 C2 119.20(10) .
O1 C3 C2 116.58(11) .
N1 C4 C6 109.23(11) .
N1 C4 C5 108.76(11) .
C6 C4 C5 112.86(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.2750(14) .
O2 C3 1.2477(15) .
N1 C4 1.4984(16) .
C1 C2 1.3284(17) .
C1 C1 1.442(2) 3_647
C2 C3 1.4901(17) .
C4 C6 1.510(2) .
C4 C5 1.5153(17) .
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 -179.87(15) 3_647
C1 C2 C3 O2 1.82(19) .
C1 C2 C3 O1 -178.27(12) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144506
