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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/12/7231296.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_7231296
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                 93.622(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.2348(19)
_cell_length_b                   51.591(19)
_cell_length_c                   8.261(3)
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.37
_cell_volume                     1801.2(12)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;
_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  0.1141
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25071
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_min         2.502
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5789
_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    1.296
_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         0.331
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0050(13)
_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   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0837
_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)+(0.0473P)²+1.4208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             4162
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {7317a522-28c8-42c2-a7c7-c7814ef44e0d}
_cod_data_source_file            c8ce00798e8.cif
_cod_data_source_block           scd1625_NonNDI_T200K_orange
_cod_depositor_comments
'Adding full bibliography for 7231291--7231300.cif.'
_cod_original_cell_volume        1801.1(13)
_cod_database_code               7231296
_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 0.0276(7) 0.44202(5) 0.1181(3) 0.0232(7) Uani 1 1 d . .
C2 C 0.3672(7) 0.47169(5) 0.2897(3) 0.0239(7) Uani 1 1 d . .
C3 C 0.2622(7) 0.49379(5) 0.1851(3) 0.0209(6) Uani 1 1 d . .
C4 C 0.0482(7) 0.48942(5) 0.0502(3) 0.0204(6) Uani 1 1 d . .
C5 C 0.3706(7) 0.51834(5) 0.2205(3) 0.0253(7) Uani 1 1 d . .
H5 H 0.5136 0.5211 0.3121 0.030 Uiso 1 1 calc R U
C6 C 0.2713(7) 0.53936(5) 0.1221(3) 0.0246(7) Uani 1 1 d . .
H6 H 0.3458 0.5563 0.1484 0.029 Uiso 1 1 calc R U
C7 C 0.0666(7) 0.53563(5) -0.0124(3) 0.0202(6) Uani 1 1 d . .
C8 C 0.2746(7) 0.42751(5) 0.3808(3) 0.0238(7) Uani 1 1 d . .
C9 C 0.1503(7) 0.43095(5) 0.5294(3) 0.0258(7) Uani 1 1 d . .
H9 H 0.0237 0.4457 0.5484 0.031 Uiso 1 1 calc R U
C10 C 0.2110(7) 0.41269(5) 0.6521(3) 0.0238(7) Uani 1 1 d . .
H10 H 0.1289 0.4151 0.7554 0.029 Uiso 1 1 calc R U
C11 C 0.3910(7) 0.39116(5) 0.6220(3) 0.0236(7) Uani 1 1 d . .
C12 C 0.5054(7) 0.38749(5) 0.4695(3) 0.0276(7) Uani 1 1 d . .
H12 H 0.6232 0.3723 0.4481 0.033 Uiso 1 1 calc R U
C13 C 0.4490(7) 0.40569(5) 0.3494(3) 0.0264(7) Uani 1 1 d . .
H13 H 0.5294 0.4033 0.2457 0.032 Uiso 1 1 calc R U
C14 C 0.3386(8) 0.37397(5) 0.8889(3) 0.0279(7) Uani 1 1 d . .
H14A H 0.1047 0.3742 0.8750 0.033 Uiso 1 1 calc R U
H14B H 0.4096 0.3901 0.9450 0.033 Uiso 1 1 calc R U
C15 C 0.4491(8) 0.35055(5) 0.9875(3) 0.0293(7) Uani 1 1 d . .
H15A H 0.3513 0.3510 1.0932 0.035 Uiso 1 1 calc R U
H15B H 0.6813 0.3516 1.0093 0.035 Uiso 1 1 calc R U
C16 C 0.3680(8) 0.32489(5) 0.9044(3) 0.0294(7) Uani 1 1 d . .
H16A H 0.4720 0.3242 0.8005 0.035 Uiso 1 1 calc R U
H16B H 0.1366 0.3242 0.8789 0.035 Uiso 1 1 calc R U
C17 C 0.4671(8) 0.30107(5) 1.0044(3) 0.0284(7) Uani 1 1 d . .
H17A H 0.6974 0.3020 1.0331 0.034 Uiso 1 1 calc R U
H17B H 0.3570 0.3013 1.1066 0.034 Uiso 1 1 calc R U
C18 C 0.3933(8) 0.27569(5) 0.9160(3) 0.0293(7) Uani 1 1 d . .
H18A H 0.1630 0.2749 0.8872 0.035 Uiso 1 1 calc R U
H18B H 0.5028 0.2756 0.8137 0.035 Uiso 1 1 calc R U
C19 C 0.4894(8) 0.25151(5) 1.0123(3) 0.0305(7) Uani 1 1 d . .
H19A H 0.7195 0.2522 1.0416 0.037 Uiso 1 1 calc R U
H19B H 0.3787 0.2514 1.1144 0.037 Uiso 1 1 calc R U
C20 C 0.4151(8) 0.22644(5) 0.9216(3) 0.0304(7) Uani 1 1 d . .
H20A H 0.5230 0.2266 0.8187 0.037 Uiso 1 1 calc R U
H20B H 0.1844 0.2255 0.8939 0.037 Uiso 1 1 calc R U
C21 C 0.5165(8) 0.20235(5) 1.0175(4) 0.0340(8) Uani 1 1 d . .
H21A H 0.7472 0.2033 1.0448 0.041 Uiso 1 1 calc R U
H21B H 0.4095 0.2023 1.1207 0.041 Uiso 1 1 calc R U
C22 C 0.4429(9) 0.17706(6) 0.9292(4) 0.0479(10) Uani 1 1 d . .
H22A H 0.2136 0.1754 0.9078 0.072 Uiso 1 1 calc R U
H22B H 0.5218 0.1625 0.9965 0.072 Uiso 1 1 calc R U
H22C H 0.5459 0.1769 0.8262 0.072 Uiso 1 1 calc R U
N1 N 0.2182(6) 0.44773(4) 0.2586(3) 0.0225(6) Uani 1 1 d . .
O1 O -0.0591(5) 0.42015(3) 0.0865(2) 0.0305(5) Uani 1 1 d . .
O2 O 0.5741(5) 0.47388(4) 0.3971(2) 0.0328(5) Uani 1 1 d . .
O3 O 0.4720(5) 0.37228(3) 0.7339(2) 0.0297(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 121.7(2) . .
O1 C1 C7 122.0(3) . 3_565
N1 C1 C7 116.3(2) . 3_565
O2 C2 N1 120.8(2) . .
O2 C2 C3 122.1(3) . .
N1 C2 C3 117.1(2) . .
C5 C3 C4 120.4(2) . .
C5 C3 C2 120.1(3) . .
C4 C3 C2 119.5(2) . .
C7 C4 C3 121.2(2) 3_565 .
C7 C4 C4 119.7(3) 3_565 3_565
C3 C4 C4 119.1(3) . 3_565
C3 C5 C6 120.4(3) . .
C3 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C7 C6 C5 120.6(3) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C6 C7 C4 119.8(2) . 3_565
C6 C7 C1 119.8(2) . 3_565
C4 C7 C1 120.4(2) 3_565 3_565
C9 C8 C13 120.8(3) . .
C9 C8 N1 118.0(2) . .
C13 C8 N1 121.2(2) . .
C8 C9 C10 119.8(3) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C11 C10 C9 119.5(3) . .
C11 C10 H10 120.3 . .
C9 C10 H10 120.3 . .
O3 C11 C10 124.7(2) . .
O3 C11 C12 115.3(2) . .
C10 C11 C12 120.1(2) . .
C13 C12 C11 120.4(3) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C8 119.5(3) . .
C12 C13 H13 120.3 . .
C8 C13 H13 120.3 . .
O3 C14 C15 107.8(2) . .
O3 C14 H14A 110.1 . .
C15 C14 H14A 110.1 . .
O3 C14 H14B 110.1 . .
C15 C14 H14B 110.1 . .
H14A C14 H14B 108.5 . .
C14 C15 C16 113.5(2) . .
C14 C15 H15A 108.9 . .
C16 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
C16 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C15 C16 C17 114.2(2) . .
C15 C16 H16A 108.7 . .
C17 C16 H16A 108.7 . .
C15 C16 H16B 108.7 . .
C17 C16 H16B 108.7 . .
H16A C16 H16B 107.6 . .
C18 C17 C16 113.1(2) . .
C18 C17 H17A 109.0 . .
C16 C17 H17A 109.0 . .
C18 C17 H17B 109.0 . .
C16 C17 H17B 109.0 . .
H17A C17 H17B 107.8 . .
C19 C18 C17 114.5(2) . .
C19 C18 H18A 108.6 . .
C17 C18 H18A 108.6 . .
C19 C18 H18B 108.6 . .
C17 C18 H18B 108.6 . .
H18A C18 H18B 107.6 . .
C20 C19 C18 113.6(2) . .
C20 C19 H19A 108.8 . .
C18 C19 H19A 108.8 . .
C20 C19 H19B 108.8 . .
C18 C19 H19B 108.8 . .
H19A C19 H19B 107.7 . .
C19 C20 C21 113.3(2) . .
C19 C20 H20A 108.9 . .
C21 C20 H20A 108.9 . .
C19 C20 H20B 108.9 . .
C21 C20 H20B 108.9 . .
H20A C20 H20B 107.7 . .
C22 C21 C20 114.2(3) . .
C22 C21 H21A 108.7 . .
C20 C21 H21A 108.7 . .
C22 C21 H21B 108.7 . .
C20 C21 H21B 108.7 . .
H21A C21 H21B 107.6 . .
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 124.4(2) . .
C1 N1 C8 118.8(2) . .
C2 N1 C8 116.8(2) . .
C11 O3 C14 117.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.210(3) .
C1 N1 1.402(4) .
C1 C7 1.485(4) 3_565
C2 O2 1.212(3) .
C2 N1 1.404(3) .
C2 C3 1.482(4) .
C3 C5 1.372(4) .
C3 C4 1.409(4) .
C4 C7 1.409(4) 3_565
C4 C4 1.416(5) 3_565
C5 C6 1.404(4) .
C5 H5 0.9500 .
C6 C7 1.379(4) .
C6 H6 0.9500 .
C7 C4 1.409(4) 3_565
C7 C1 1.485(4) 3_565
C8 C9 1.377(4) .
C8 C13 1.380(4) .
C8 N1 1.461(3) .
C9 C10 1.396(4) .
C9 H9 0.9500 .
C10 C11 1.378(4) .
C10 H10 0.9500 .
C11 O3 1.371(3) .
C11 C12 1.391(4) .
C12 C13 1.376(4) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 O3 1.435(3) .
C14 C15 1.515(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.520(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.525(4) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.522(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.521(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.518(4) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.521(4) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.517(4) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 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
_geom_torsion_site_symmetry_4
O2 C2 C3 C5 -8.1(4) . .
N1 C2 C3 C5 172.4(3) . .
O2 C2 C3 C4 172.5(3) . .
N1 C2 C3 C4 -7.0(4) . .
C5 C3 C4 C7 -179.7(3) . 3_565
C2 C3 C4 C7 -0.4(4) . 3_565
C5 C3 C4 C4 1.3(5) . 3_565
C2 C3 C4 C4 -179.3(3) . 3_565
C4 C3 C5 C6 -0.5(4) . .
C2 C3 C5 C6 -179.8(3) . .
C3 C5 C6 C7 -0.7(4) . .
C5 C6 C7 C4 1.0(4) . 3_565
C5 C6 C7 C1 -178.0(3) . 3_565
C13 C8 C9 C10 2.5(4) . .
N1 C8 C9 C10 -177.0(3) . .
C8 C9 C10 C11 -1.0(4) . .
C9 C10 C11 O3 178.4(3) . .
C9 C10 C11 C12 -1.3(4) . .
O3 C11 C12 C13 -177.6(3) . .
C10 C11 C12 C13 2.2(4) . .
C11 C12 C13 C8 -0.7(4) . .
C9 C8 C13 C12 -1.6(4) . .
N1 C8 C13 C12 177.9(3) . .
O3 C14 C15 C16 -56.1(3) . .
C14 C15 C16 C17 -178.0(3) . .
C15 C16 C17 C18 -178.0(3) . .
C16 C17 C18 C19 180.0(3) . .
C17 C18 C19 C20 -179.7(3) . .
C18 C19 C20 C21 179.1(3) . .
C19 C20 C21 C22 179.7(3) . .
O1 C1 N1 C2 169.5(3) . .
C7 C1 N1 C2 -11.7(4) 3_565 .
O1 C1 N1 C8 -9.0(4) . .
C7 C1 N1 C8 169.8(2) 3_565 .
O2 C2 N1 C1 -166.0(3) . .
C3 C2 N1 C1 13.5(4) . .
O2 C2 N1 C8 12.6(4) . .
C3 C2 N1 C8 -167.9(2) . .
C9 C8 N1 C1 -113.3(3) . .
C13 C8 N1 C1 67.2(4) . .
C9 C8 N1 C2 68.0(3) . .
C13 C8 N1 C2 -111.5(3) . .
C10 C11 O3 C14 5.3(4) . .
C12 C11 O3 C14 -174.9(3) . .
C15 C14 O3 C11 177.4(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204991
