#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/12/7231292.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_7231292
loop_
_publ_author_name
'Dharmarwardana, Madushani'
'Arimilli, Bhargav S.'
'Luzuriaga, Michael A.'
'Kwon, Sunah'
'Lee, Hamilton'
'Appuhamillage, Gayan A.'
'McCandless, Gregory T.'
'Smaldone, Ronald A.'
'Gassensmith, Jeremiah J.'
_publ_section_title
;
 The thermo-responsive behavior in molecular crystals of naphthalene
 diimides and their 3D printed thermochromic composites
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6054
_journal_paper_doi               10.1039/C8CE00798E
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C44 H50 N2 O6'
_chemical_formula_sum            'C44 H50 N2 O6'
_chemical_formula_weight         702.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.56(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.362(3)
_cell_length_b                   51.35(4)
_cell_length_c                   8.268(5)
_cell_measurement_reflns_used    5250
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      2.38
_cell_volume                     1848(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1033
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       66
_diffrn_reflns_limit_k_min       -66
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            30722
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       fragment
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0107(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0490P)²+0.7607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2094
_reflns_number_total             4263
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {1d1e1bee-f1e6-4fed-b897-7174805b74de}
_cod_data_source_file            c8ce00798e8.cif
_cod_data_source_block           scd1616_NonNDI_T298K_orange
_cod_depositor_comments
'Adding full bibliography for 7231291--7231300.cif.'
_cod_database_code               7231292
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.0099(6) 0.44230(5) 0.1258(3) 0.0370(6) Uani 1 1 d . .
C2 C 0.3549(6) 0.47183(5) 0.2901(3) 0.0390(7) Uani 1 1 d . .
C3 C 0.2581(6) 0.49372(4) 0.1837(3) 0.0330(6) Uani 1 1 d . .
C4 C 0.0448(6) 0.48945(4) 0.0508(3) 0.0314(6) Uani 1 1 d . .
C5 C 0.3708(6) 0.51827(5) 0.2145(3) 0.0395(7) Uani 1 1 d . .
H5 H 0.5093 0.5210 0.3029 0.047 Uiso 1 1 calc R U
C6 C 0.2797(6) 0.53926(5) 0.1143(3) 0.0395(7) Uani 1 1 d . .
H6 H 0.3570 0.5558 0.1371 0.047 Uiso 1 1 calc R U
C7 C 0.0760(6) 0.53547(4) -0.0178(3) 0.0325(6) Uani 1 1 d . .
C8 C 0.2569(6) 0.42778(5) 0.3863(3) 0.0380(6) Uani 1 1 d . .
C9 C 0.1336(6) 0.43121(5) 0.5341(3) 0.0427(7) Uani 1 1 d . .
H9 H 0.0116 0.4457 0.5517 0.051 Uiso 1 1 calc R U
C10 C 0.1916(6) 0.41303(5) 0.6570(3) 0.0403(7) Uani 1 1 d . .
H10 H 0.1096 0.4154 0.7572 0.048 Uiso 1 1 calc R U
C11 C 0.3707(6) 0.39164(5) 0.6297(3) 0.0380(6) Uani 1 1 d . .
C12 C 0.4859(7) 0.38802(5) 0.4790(3) 0.0478(7) Uani 1 1 d . .
H12 H 0.6006 0.3732 0.4592 0.057 Uiso 1 1 calc R U
C13 C 0.4317(6) 0.40620(5) 0.3582(3) 0.0443(7) Uani 1 1 d . .
H13 H 0.5132 0.4039 0.2579 0.053 Uiso 1 1 calc R U
C14 C 0.3158(7) 0.37429(5) 0.8963(3) 0.0486(8) Uani 1 1 d . .
H14A H 0.0934 0.3742 0.8817 0.058 Uiso 1 1 calc R U
H14B H 0.3793 0.3902 0.9518 0.058 Uiso 1 1 calc R U
C15 C 0.4264(7) 0.35089(5) 0.9938(3) 0.0502(8) Uani 1 1 d . .
H15A H 0.6474 0.3521 1.0137 0.060 Uiso 1 1 calc R U
H15B H 0.3358 0.3513 1.0980 0.060 Uiso 1 1 calc R U
C16 C 0.3498(7) 0.32513(5) 0.9132(3) 0.0515(8) Uani 1 1 d . .
H16A H 0.4470 0.3245 0.8109 0.062 Uiso 1 1 calc R U
H16B H 0.1295 0.3244 0.8890 0.062 Uiso 1 1 calc R U
C17 C 0.4465(7) 0.30118(5) 1.0107(3) 0.0526(8) Uani 1 1 d . .
H17A H 0.6659 0.3021 1.0375 0.063 Uiso 1 1 calc R U
H17B H 0.3442 0.3014 1.1115 0.063 Uiso 1 1 calc R U
C18 C 0.3753(7) 0.27579(5) 0.9251(3) 0.0547(8) Uani 1 1 d . .
H18A H 0.4760 0.2758 0.8238 0.066 Uiso 1 1 calc R U
H18B H 0.1557 0.2750 0.8987 0.066 Uiso 1 1 calc R U
C19 C 0.4696(7) 0.25151(5) 1.0177(3) 0.0550(8) Uani 1 1 d . .
H19A H 0.6890 0.2523 1.0449 0.066 Uiso 1 1 calc R U
H19B H 0.3672 0.2514 1.1185 0.066 Uiso 1 1 calc R U
C20 C 0.3991(8) 0.22636(5) 0.9295(3) 0.0575(8) Uani 1 1 d . .
H20A H 0.1795 0.2255 0.9030 0.069 Uiso 1 1 calc R U
H20B H 0.5002 0.2266 0.8283 0.069 Uiso 1 1 calc R U
C21 C 0.4953(8) 0.20215(5) 1.0214(4) 0.0657(9) Uani 1 1 d . .
H21A H 0.7145 0.2031 1.0486 0.079 Uiso 1 1 calc R U
H21B H 0.3934 0.2020 1.1224 0.079 Uiso 1 1 calc R U
C22 C 0.4287(9) 0.17679(6) 0.9357(5) 0.0878(12) Uani 1 1 d . .
H22A H 0.2116 0.1752 0.9107 0.132 Uiso 1 1 calc R U
H22B H 0.4980 0.1626 1.0044 0.132 Uiso 1 1 calc R U
H22C H 0.5341 0.1763 0.8372 0.132 Uiso 1 1 calc R U
N1 N 0.2031(5) 0.44791(4) 0.2635(2) 0.0365(5) Uani 1 1 d . .
O1 O -0.0808(4) 0.42031(3) 0.0981(2) 0.0508(5) Uani 1 1 d . .
O2 O 0.5587(5) 0.47379(3) 0.3967(2) 0.0529(5) Uani 1 1 d . .
O3 O 0.4489(4) 0.37280(3) 0.7422(2) 0.0496(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
O1 C1 N1 121.1(2) . .
O1 C1 C7 122.4(2) . 3_565
N1 C1 C7 116.6(2) . 3_565
O2 C2 N1 120.1(2) . .
O2 C2 C3 122.6(2) . .
N1 C2 C3 117.3(2) . .
C5 C3 C4 119.9(2) . .
C5 C3 C2 120.3(2) . .
C4 C3 C2 119.8(2) . .
C7 C4 C4 119.8(3) 3_565 3_565
C7 C4 C3 120.9(2) 3_565 .
C4 C4 C3 119.3(3) 3_565 .
C3 C5 C6 120.8(2) . .
C3 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C7 C6 C5 120.3(2) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C4 119.9(2) . 3_565
C6 C7 C1 119.7(2) . 3_565
C4 C7 C1 120.4(2) 3_565 3_565
C13 C8 C9 120.4(2) . .
C13 C8 N1 121.4(2) . .
C9 C8 N1 118.2(2) . .
C8 C9 C10 119.9(2) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C9 119.7(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
O3 C11 C10 125.0(2) . .
O3 C11 C12 115.3(2) . .
C10 C11 C12 119.8(2) . .
C13 C12 C11 120.4(2) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C8 C13 C12 119.8(2) . .
C8 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
O3 C14 C15 107.4(2) . .
O3 C14 H14A 110.2 . .
C15 C14 H14A 110.2 . .
O3 C14 H14B 110.2 . .
C15 C14 H14B 110.2 . .
H14A C14 H14B 108.5 . .
C16 C15 C14 114.0(2) . .
C16 C15 H15A 108.7 . .
C14 C15 H15A 108.7 . .
C16 C15 H15B 108.7 . .
C14 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C15 C16 C17 115.5(2) . .
C15 C16 H16A 108.4 . .
C17 C16 H16A 108.4 . .
C15 C16 H16B 108.4 . .
C17 C16 H16B 108.4 . .
H16A C16 H16B 107.5 . .
C18 C17 C16 114.2(2) . .
C18 C17 H17A 108.7 . .
C16 C17 H17A 108.7 . .
C18 C17 H17B 108.7 . .
C16 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C17 C18 C19 115.8(2) . .
C17 C18 H18A 108.3 . .
C19 C18 H18A 108.3 . .
C17 C18 H18B 108.3 . .
C19 C18 H18B 108.3 . .
H18A C18 H18B 107.4 . .
C20 C19 C18 115.0(2) . .
C20 C19 H19A 108.5 . .
C18 C19 H19A 108.5 . .
C20 C19 H19B 108.5 . .
C18 C19 H19B 108.5 . .
H19A C19 H19B 107.5 . .
C21 C20 C19 115.0(2) . .
C21 C20 H20A 108.5 . .
C19 C20 H20A 108.5 . .
C21 C20 H20B 108.5 . .
C19 C20 H20B 108.5 . .
H20A C20 H20B 107.5 . .
C22 C21 C20 116.0(3) . .
C22 C21 H21A 108.3 . .
C20 C21 H21A 108.3 . .
C22 C21 H21B 108.3 . .
C20 C21 H21B 108.3 . .
H21A C21 H21B 107.4 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C1 N1 C2 123.99(19) . .
C1 N1 C8 118.8(2) . .
C2 N1 C8 117.16(19) . .
C11 O3 C14 117.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.214(3) .
C1 N1 1.404(3) .
C1 C7 1.483(3) 3_565
C2 O2 1.216(3) .
C2 N1 1.406(3) .
C2 C3 1.473(3) .
C3 C5 1.371(3) .
C3 C4 1.412(3) .
C4 C7 1.404(3) 3_565
C4 C4 1.411(4) 3_565
C5 C6 1.402(3) .
C5 H5 0.9300 .
C6 C7 1.378(3) .
C6 H6 0.9300 .
C7 C4 1.405(3) 3_565
C7 C1 1.483(3) 3_565
C8 C13 1.373(3) .
C8 C9 1.376(3) .
C8 N1 1.458(3) .
C9 C10 1.392(3) .
C9 H9 0.9300 .
C10 C11 1.375(3) .
C10 H10 0.9300 .
C11 O3 1.370(3) .
C11 C12 1.385(3) .
C12 C13 1.377(3) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 O3 1.434(3) .
C14 C15 1.509(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.509(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.516(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.506(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.507(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.505(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.503(4) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.502(4) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
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
O2 C2 C3 C5 -8.1(4) . .
N1 C2 C3 C5 172.5(2) . .
O2 C2 C3 C4 172.8(2) . .
N1 C2 C3 C4 -6.6(3) . .
C5 C3 C4 C7 -179.4(2) . 3_565
C2 C3 C4 C7 -0.3(3) . 3_565
C5 C3 C4 C4 1.3(4) . 3_565
C2 C3 C4 C4 -179.7(3) . 3_565
C4 C3 C5 C6 -0.8(4) . .
C2 C3 C5 C6 -179.8(2) . .
C3 C5 C6 C7 -0.4(4) . .
C5 C6 C7 C4 1.0(4) . 3_565
C5 C6 C7 C1 -177.9(2) . 3_565
C13 C8 C9 C10 1.4(4) . .
N1 C8 C9 C10 -177.0(2) . .
C8 C9 C10 C11 -0.4(4) . .
C9 C10 C11 O3 178.5(2) . .
C9 C10 C11 C12 -1.5(4) . .
O3 C11 C12 C13 -177.6(2) . .
C10 C11 C12 C13 2.4(4) . .
C9 C8 C13 C12 -0.5(4) . .
N1 C8 C13 C12 177.9(2) . .
C11 C12 C13 C8 -1.4(4) . .
O3 C14 C15 C16 -57.4(3) . .
C14 C15 C16 C17 -177.7(3) . .
C15 C16 C17 C18 -178.3(3) . .
C16 C17 C18 C19 179.6(3) . .
C17 C18 C19 C20 -179.5(3) . .
C18 C19 C20 C21 179.6(3) . .
C19 C20 C21 C22 -179.7(3) . .
O1 C1 N1 C2 169.6(2) . .
C7 C1 N1 C2 -10.5(3) 3_565 .
O1 C1 N1 C8 -9.2(4) . .
C7 C1 N1 C8 170.7(2) 3_565 .
O2 C2 N1 C1 -167.1(2) . .
C3 C2 N1 C1 12.4(3) . .
O2 C2 N1 C8 11.7(3) . .
C3 C2 N1 C8 -168.8(2) . .
C13 C8 N1 C1 71.1(3) . .
C9 C8 N1 C1 -110.5(3) . .
C13 C8 N1 C2 -107.8(3) . .
C9 C8 N1 C2 70.6(3) . .
C10 C11 O3 C14 5.1(4) . .
C12 C11 O3 C14 -174.9(2) . .
C15 C14 O3 C11 177.5(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204991
