#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:23:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/01/7210134.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_7210134
loop_
_publ_author_name
'Kodama, Satoshi'
'Johmoto, Kohei'
'Sekine, Akiko'
'Fujii, Kotaro'
'Uekusa, Hidehiro'
_publ_section_title
;
 Structural understanding of solid-state photodimerization reactions of
 cinnamic amide derivatives in terms of reaction cavities -- color
 developer for thermosensitive paper
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              4667
_journal_paper_doi               10.1039/c3ce40130h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         '2(C16 H15 N O2)'
_chemical_formula_sum            'C32 H30 N2 O4'
_chemical_formula_weight         506.58
_chemical_name_systematic
;
?
;
_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                 93.012(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8016(6)
_cell_length_b                   12.5421(10)
_cell_length_c                   16.2644(14)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.99
_cell_volume                     1385.5(2)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13035
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.4775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0477
_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)+(0.0614P)²+0.1719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                1505
_reflns_number_total             3147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40130h.txt
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7210134
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
C1 C 0.2954(7) 0.0106(2) -0.0911(3) 0.189(2) Uani 1 1 d .
H1A H 0.2908 0.0024 -0.1499 0.283 Uiso 1 1 calc R
H1B H 0.1976 -0.0343 -0.0684 0.283 Uiso 1 1 calc R
H1C H 0.4235 -0.0094 -0.0686 0.283 Uiso 1 1 calc R
C2 C 0.2547(6) 0.1267(2) -0.06964(18) 0.1061(11) Uani 1 1 d .
C3 C 0.3994(5) 0.1937(2) -0.03876(17) 0.0993(9) Uani 1 1 d .
H3 H 0.5269 0.1678 -0.0302 0.119 Uiso 1 1 calc R
C4 C 0.3612(4) 0.29857(19) -0.02006(15) 0.0760(7) Uani 1 1 d .
H4 H 0.4630 0.3418 0.0008 0.091 Uiso 1 1 calc R
C5 C 0.1737(3) 0.34062(16) -0.03188(13) 0.0627(6) Uani 1 1 d .
C6 C 0.0259(4) 0.27338(17) -0.06280(16) 0.0810(7) Uani 1 1 d .
H6 H -0.1018 0.2991 -0.0712 0.097 Uiso 1 1 calc R
C7 C 0.0671(5) 0.1680(2) -0.08126(18) 0.1008(9) Uani 1 1 d .
H7 H -0.0341 0.1241 -0.1019 0.121 Uiso 1 1 calc R
C8 C 0.1370(3) 0.45531(15) -0.01142(13) 0.0596(5) Uani 1 1 d .
H8 H 0.2623 0.4940 -0.0074 0.072 Uiso 1 1 calc R
C9 C 0.0468(3) 0.03784(17) 0.27730(13) 0.0662(6) Uani 1 1 d .
C10 C -0.1084(3) 0.10720(17) 0.27930(13) 0.0668(6) Uani 1 1 d .
H10 H -0.2187 0.0887 0.3076 0.080 Uiso 1 1 calc R
C11 C -0.1025(3) 0.20494(17) 0.23939(14) 0.0678(6) Uani 1 1 d .
H11 H -0.2083 0.2517 0.2414 0.081 Uiso 1 1 calc R
C12 C 0.0591(3) 0.23277(16) 0.19691(12) 0.0580(5) Uani 1 1 d .
C13 C 0.2145(3) 0.16240(19) 0.19458(15) 0.0775(7) Uani 1 1 d .
H13 H 0.3244 0.1804 0.1658 0.093 Uiso 1 1 calc R
C14 C 0.2082(3) 0.0656(2) 0.23453(16) 0.0840(8) Uani 1 1 d .
H14 H 0.3138 0.0187 0.2325 0.101 Uiso 1 1 calc R
C15 C -0.0619(3) 0.38843(15) 0.11312(13) 0.0578(5) Uani 1 1 d .
C16 C 0.0153(3) 0.48118(15) 0.06613(13) 0.0585(5) Uani 1 1 d .
H16 H 0.0898 0.5295 0.1035 0.070 Uiso 1 1 calc R
N1 N 0.0775(2) 0.33209(13) 0.15545(11) 0.0644(5) Uani 1 1 d .
H1 H 0.1934 0.3596 0.1579 0.077 Uiso 1 1 calc R
O1 O 0.0493(2) -0.05963(14) 0.31631(12) 0.0939(6) Uani 1 1 d .
H1O H -0.0541 -0.0680 0.3393 0.141 Uiso 1 1 calc R
O2 O -0.2380(2) 0.36447(11) 0.11181(10) 0.0716(5) Uani 1 1 d .
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
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 C7 117.4(2) . .
C3 C2 C1 122.3(3) . .
C7 C2 C1 120.3(3) . .
C2 C3 C4 121.8(3) . .
C2 C3 H3 119.1 . .
C4 C3 H3 119.1 . .
C3 C4 C5 121.1(2) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C4 C5 C6 117.6(2) . .
C4 C5 C8 119.8(2) . .
C6 C5 C8 122.53(19) . .
C5 C6 C7 120.5(2) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C2 C7 C6 121.6(3) . .
C2 C7 H7 119.2 . .
C6 C7 H7 119.2 . .
C5 C8 C16 118.64(18) . 3_565
C5 C8 C16 118.34(17) . .
C16 C8 C16 89.45(15) 3_565 .
C5 C8 H8 109.6 . .
C16 C8 H8 109.6 3_565 .
C16 C8 H8 109.6 . .
C10 C9 C14 119.2(2) . .
C10 C9 O1 122.93(19) . .
C14 C9 O1 117.84(19) . .
C9 C10 C11 120.5(2) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C12 C11 C10 120.20(19) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C11 C12 C13 119.07(19) . .
C11 C12 N1 123.55(19) . .
C13 C12 N1 117.37(18) . .
C14 C13 C12 120.5(2) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C9 C14 C13 120.4(2) . .
C9 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
O2 C15 N1 122.63(19) . .
O2 C15 C16 123.01(19) . .
N1 C15 C16 114.34(18) . .
C15 C16 C8 116.70(17) . 3_565
C15 C16 C8 117.35(15) . .
C8 C16 C8 90.55(15) 3_565 .
C15 C16 H16 110.3 . .
C8 C16 H16 110.3 3_565 .
C8 C16 H16 110.3 . .
C15 N1 C12 128.69(17) . .
C15 N1 H1 115.7 . .
C12 N1 H1 115.7 . .
C9 O1 H1O 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.526(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.370(4) .
C2 C7 1.381(4) .
C3 C4 1.378(3) .
C3 H3 0.9300 .
C4 C5 1.384(3) .
C4 H4 0.9300 .
C5 C6 1.386(3) .
C5 C8 1.500(3) .
C6 C7 1.387(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C16 1.550(3) 3_565
C8 C16 1.578(3) .
C8 H8 0.9800 .
C9 C10 1.370(3) .
C9 C14 1.375(3) .
C9 O1 1.377(2) .
C10 C11 1.389(3) .
C10 H10 0.9300 .
C11 C12 1.374(3) .
C11 H11 0.9300 .
C12 C13 1.379(3) .
C12 N1 1.425(2) .
C13 C14 1.379(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 O2 1.234(2) .
C15 N1 1.343(2) .
C15 C16 1.502(3) .
C16 C8 1.550(3) 3_565
C16 H16 0.9800 .
N1 H1 0.8600 .
O1 H1O 0.8200 .
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_4
C7 C2 C3 C4 -0.2(5) . .
C1 C2 C3 C4 179.6(3) . .
C2 C3 C4 C5 -0.1(4) . .
C3 C4 C5 C6 0.3(3) . .
C3 C4 C5 C8 -179.6(2) . .
C4 C5 C6 C7 -0.3(4) . .
C8 C5 C6 C7 179.6(2) . .
C3 C2 C7 C6 0.2(5) . .
C1 C2 C7 C6 -179.6(3) . .
C5 C6 C7 C2 0.0(4) . .
C4 C5 C8 C16 144.6(2) . 3_565
C6 C5 C8 C16 -35.4(3) . 3_565
C4 C5 C8 C16 -109.1(2) . .
C6 C5 C8 C16 71.0(3) . .
C14 C9 C10 C11 -0.7(4) . .
O1 C9 C10 C11 179.5(2) . .
C9 C10 C11 C12 0.4(3) . .
C10 C11 C12 C13 0.0(3) . .
C10 C11 C12 N1 -179.0(2) . .
C11 C12 C13 C14 -0.2(4) . .
N1 C12 C13 C14 178.9(2) . .
C10 C9 C14 C13 0.5(4) . .
O1 C9 C14 C13 -179.7(2) . .
C12 C13 C14 C9 0.0(4) . .
O2 C15 C16 C8 -2.6(3) . 3_565
N1 C15 C16 C8 176.03(16) . 3_565
O2 C15 C16 C8 -108.4(2) . .
N1 C15 C16 C8 70.2(2) . .
C5 C8 C16 C15 -1.9(3) . .
C16 C8 C16 C15 120.7(2) 3_565 .
C5 C8 C16 C8 -122.6(2) . 3_565
C16 C8 C16 C8 0.0 3_565 3_565
O2 C15 N1 C12 7.8(3) . .
C16 C15 N1 C12 -170.83(18) . .
C11 C12 N1 C15 -37.5(3) . .
C13 C12 N1 C15 143.4(2) . .
