#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/13/7231300.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_7231300
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
;
2018-04-27 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.663(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.154(2)
_cell_length_b                   51.72(2)
_cell_length_c                   8.253(3)
_cell_measurement_reflns_used    8467
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.36
_cell_volume                     1769.5(13)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0947
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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            36862
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         2.595
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6533
_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    1.319
_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         0.327
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+1.0464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2862
_reflns_number_total             4080
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {bd220014-04c7-4a39-95fb-63a99dfcf3f8}
_cod_data_source_file            c8ce00798e7.cif
_cod_data_source_block           scd1613_NonNDI_T100K_orange
_cod_depositor_comments
'Adding full bibliography for 7231291--7231300.cif.'
_cod_original_cell_volume        1769.6(14)
_cod_database_code               7231300
_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   0.974
_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 0.0369(5) 0.44197(3) 0.1146(2) 0.0132(4) Uani 1 1 d . .
C2 C 0.3758(4) 0.47162(3) 0.2892(2) 0.0137(4) Uani 1 1 d . .
C3 C 0.2655(4) 0.49376(3) 0.1857(2) 0.0118(4) Uani 1 1 d . .
C4 C 0.0507(4) 0.48934(3) 0.0497(2) 0.0117(4) Uani 1 1 d . .
C5 C 0.3718(4) 0.51835(3) 0.2239(2) 0.0133(4) Uani 1 1 d . .
H5 H 0.5158 0.5211 0.3164 0.016 Uiso 1 1 calc R U
C6 C 0.2676(4) 0.53946(4) 0.1264(2) 0.0136(4) Uani 1 1 d . .
H6 H 0.3400 0.5564 0.1541 0.016 Uiso 1 1 calc R U
C7 C 0.0605(4) 0.53567(3) -0.0093(2) 0.0123(4) Uani 1 1 d . .
C8 C 0.2845(4) 0.42735(3) 0.3774(2) 0.0127(4) Uani 1 1 d . .
C9 C 0.1621(5) 0.43085(4) 0.5279(2) 0.0141(4) Uani 1 1 d . .
H9 H 0.0368 0.4457 0.5480 0.017 Uiso 1 1 calc R U
C10 C 0.2224(4) 0.41253(3) 0.6501(2) 0.0134(4) Uani 1 1 d . .
H10 H 0.1403 0.4150 0.7539 0.016 Uiso 1 1 calc R U
C11 C 0.4033(4) 0.39075(3) 0.6190(2) 0.0133(4) Uani 1 1 d . .
C12 C 0.5174(5) 0.38705(4) 0.4649(2) 0.0152(4) Uani 1 1 d . .
H12 H 0.6357 0.3719 0.4428 0.018 Uiso 1 1 calc R U
C13 C 0.4591(5) 0.40532(3) 0.3451(2) 0.0148(4) Uani 1 1 d . .
H13 H 0.5382 0.4028 0.2408 0.018 Uiso 1 1 calc R U
C14 C 0.3518(5) 0.37389(3) 0.8867(2) 0.0149(4) Uani 1 1 d . .
H14A H 0.1133 0.3743 0.8735 0.018 Uiso 1 1 calc R U
H14B H 0.4266 0.3900 0.9422 0.018 Uiso 1 1 calc R U
C15 C 0.4638(5) 0.35046(3) 0.9859(2) 0.0153(4) Uani 1 1 d . .
H15A H 0.3637 0.3509 1.0915 0.018 Uiso 1 1 calc R U
H15B H 0.7005 0.3515 1.0080 0.018 Uiso 1 1 calc R U
C16 C 0.3806(5) 0.32484(3) 0.9024(2) 0.0157(4) Uani 1 1 d . .
H16A H 0.4884 0.3241 0.7989 0.019 Uiso 1 1 calc R U
H16B H 0.1450 0.3242 0.8759 0.019 Uiso 1 1 calc R U
C17 C 0.4794(5) 0.30109(3) 1.0039(2) 0.0163(4) Uani 1 1 d . .
H17A H 0.7137 0.3020 1.0341 0.020 Uiso 1 1 calc R U
H17B H 0.3646 0.3013 1.1053 0.020 Uiso 1 1 calc R U
C18 C 0.4055(5) 0.27573(3) 0.9149(2) 0.0162(4) Uani 1 1 d . .
H18A H 0.1711 0.2749 0.8851 0.019 Uiso 1 1 calc R U
H18B H 0.5189 0.2757 0.8130 0.019 Uiso 1 1 calc R U
C19 C 0.5028(5) 0.25161(3) 1.0122(2) 0.0155(4) Uani 1 1 d . .
H19A H 0.7369 0.2524 1.0426 0.019 Uiso 1 1 calc R U
H19B H 0.3879 0.2515 1.1137 0.019 Uiso 1 1 calc R U
C20 C 0.4290(5) 0.22652(3) 0.9205(2) 0.0163(4) Uani 1 1 d . .
H20A H 0.1945 0.2256 0.8911 0.020 Uiso 1 1 calc R U
H20B H 0.5421 0.2267 0.8185 0.020 Uiso 1 1 calc R U
C21 C 0.5300(5) 0.20252(3) 1.0180(2) 0.0182(4) Uani 1 1 d . .
H21A H 0.7648 0.2034 1.0467 0.022 Uiso 1 1 calc R U
H21B H 0.4183 0.2025 1.1204 0.022 Uiso 1 1 calc R U
C22 C 0.4558(5) 0.17726(4) 0.9286(3) 0.0248(5) Uani 1 1 d . .
H22A H 0.2225 0.1758 0.9046 0.037 Uiso 1 1 calc R U
H22B H 0.5318 0.1627 0.9968 0.037 Uiso 1 1 calc R U
H22C H 0.5654 0.1771 0.8270 0.037 Uiso 1 1 calc R U
N1 N 0.2278(4) 0.44757(3) 0.25619(17) 0.0125(3) Uani 1 1 d . .
O1 O -0.0458(3) 0.42002(2) 0.08059(15) 0.0166(3) Uani 1 1 d . .
O2 O 0.5858(3) 0.47391(2) 0.39785(15) 0.0174(3) Uani 1 1 d . .
O3 O 0.4861(3) 0.37193(2) 0.73043(15) 0.0159(3) 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 121.56(16) . .
O1 C1 C7 121.99(17) . 3_565
N1 C1 C7 116.45(16) . 3_565
O2 C2 N1 120.88(16) . .
O2 C2 C3 122.00(17) . .
N1 C2 C3 117.12(16) . .
C5 C3 C4 120.72(16) . .
C5 C3 C2 119.89(17) . .
C4 C3 C2 119.38(16) . .
C7 C4 C3 121.37(16) 3_565 .
C7 C4 C4 119.7(2) 3_565 3_565
C3 C4 C4 118.9(2) . 3_565
C3 C5 C6 120.20(17) . .
C3 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C7 C6 C5 120.39(17) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C4 120.06(16) . 3_565
C6 C7 C1 119.67(17) . 3_565
C4 C7 C1 120.25(17) 3_565 3_565
C9 C8 C13 120.48(16) . .
C9 C8 N1 118.05(16) . .
C13 C8 N1 121.47(16) . .
C8 C9 C10 120.05(17) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C9 119.48(17) . .
C11 C10 H10 120.3 . .
C9 C10 H10 120.3 . .
O3 C11 C10 124.69(16) . .
O3 C11 C12 115.41(16) . .
C10 C11 C12 119.90(16) . .
C13 C12 C11 120.30(17) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C8 119.74(17) . .
C12 C13 H13 120.1 . .
C8 C13 H13 120.1 . .
O3 C14 C15 107.68(15) . .
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 . .
C14 C15 C16 113.41(16) . .
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 113.96(16) . .
C15 C16 H16A 108.8 . .
C17 C16 H16A 108.8 . .
C15 C16 H16B 108.8 . .
C17 C16 H16B 108.8 . .
H16A C16 H16B 107.7 . .
C18 C17 C16 112.88(16) . .
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 114.34(16) . .
C19 C18 H18A 108.7 . .
C17 C18 H18A 108.7 . .
C19 C18 H18B 108.7 . .
C17 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
C20 C19 C18 113.42(16) . .
C20 C19 H19A 108.9 . .
C18 C19 H19A 108.9 . .
C20 C19 H19B 108.9 . .
C18 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C21 C20 C19 113.07(16) . .
C21 C20 H20A 109.0 . .
C19 C20 H20A 109.0 . .
C21 C20 H20B 109.0 . .
C19 C20 H20B 109.0 . .
H20A C20 H20B 107.8 . .
C22 C21 C20 113.78(17) . .
C22 C21 H21A 108.8 . .
C20 C21 H21A 108.8 . .
C22 C21 H21B 108.8 . .
C20 C21 H21B 108.8 . .
H21A C21 H21B 107.7 . .
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 124.20(15) . .
C1 N1 C8 118.90(15) . .
C2 N1 C8 116.89(15) . .
C11 O3 C14 117.18(14) . .
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(2) .
C1 N1 1.400(2) .
C1 C7 1.487(3) 3_565
C2 O2 1.216(2) .
C2 N1 1.406(2) .
C2 C3 1.484(3) .
C3 C5 1.376(3) .
C3 C4 1.407(3) .
C4 C7 1.406(3) 3_565
C4 C4 1.422(4) 3_565
C5 C6 1.408(3) .
C5 H5 0.9500 .
C6 C7 1.382(3) .
C6 H6 0.9500 .
C7 C4 1.406(3) 3_565
C7 C1 1.487(3) 3_565
C8 C9 1.384(3) .
C8 C13 1.386(3) .
C8 N1 1.456(2) .
C9 C10 1.395(3) .
C9 H9 0.9500 .
C10 C11 1.388(3) .
C10 H10 0.9500 .
C11 O3 1.368(2) .
C11 C12 1.398(3) .
C12 C13 1.378(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 O3 1.441(2) .
C14 C15 1.519(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.523(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.528(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.525(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.524(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.523(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.523(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.522(3) .
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 -8.2(3) . .
N1 C2 C3 C5 172.11(16) . .
O2 C2 C3 C4 172.29(17) . .
N1 C2 C3 C4 -7.4(2) . .
C5 C3 C4 C7 -179.83(17) . 3_565
C2 C3 C4 C7 -0.3(3) . 3_565
C5 C3 C4 C4 1.1(3) . 3_565
C2 C3 C4 C4 -179.36(19) . 3_565
C4 C3 C5 C6 -0.4(3) . .
C2 C3 C5 C6 -179.85(16) . .
C3 C5 C6 C7 -0.6(3) . .
C5 C6 C7 C4 0.8(3) . 3_565
C5 C6 C7 C1 -177.60(16) . 3_565
C13 C8 C9 C10 2.0(3) . .
N1 C8 C9 C10 -177.21(17) . .
C8 C9 C10 C11 -0.6(3) . .
C9 C10 C11 O3 177.89(17) . .
C9 C10 C11 C12 -1.4(3) . .
O3 C11 C12 C13 -177.45(17) . .
C10 C11 C12 C13 1.9(3) . .
C11 C12 C13 C8 -0.4(3) . .
C9 C8 C13 C12 -1.5(3) . .
N1 C8 C13 C12 177.69(17) . .
O3 C14 C15 C16 -55.4(2) . .
C14 C15 C16 C17 -177.57(16) . .
C15 C16 C17 C18 -177.72(16) . .
C16 C17 C18 C19 179.66(16) . .
C17 C18 C19 C20 -179.56(16) . .
C18 C19 C20 C21 179.42(16) . .
C19 C20 C21 C22 179.57(17) . .
O1 C1 N1 C2 168.89(17) . .
C7 C1 N1 C2 -11.5(2) 3_565 .
O1 C1 N1 C8 -10.0(3) . .
C7 C1 N1 C8 169.57(15) 3_565 .
O2 C2 N1 C1 -165.90(17) . .
C3 C2 N1 C1 13.8(2) . .
O2 C2 N1 C8 13.0(2) . .
C3 C2 N1 C8 -167.31(15) . .
C9 C8 N1 C1 -115.10(19) . .
C13 C8 N1 C1 65.7(2) . .
C9 C8 N1 C2 65.9(2) . .
C13 C8 N1 C2 -113.3(2) . .
C10 C11 O3 C14 5.6(3) . .
C12 C11 O3 C14 -175.09(16) . .
C15 C14 O3 C11 177.38(15) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204991
