#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:56:06 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/12/7231299.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_7231299
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         'C42 H46 N2 O6'
_chemical_formula_sum            'C42 H46 N2 O6'
_chemical_formula_weight         674.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                97.810(10)
_cell_angle_beta                 93.453(7)
_cell_angle_gamma                93.834(6)
_cell_formula_units_Z            1
_cell_length_a                   4.1680(14)
_cell_length_b                   8.217(3)
_cell_length_c                   24.901(7)
_cell_measurement_reflns_used    7013
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.48
_cell_volume                     840.9(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0762
_diffrn_reflns_av_unetI/netI     0.0643
_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       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25306
_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         27.537
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5942
_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    1.332
_exptl_crystal_description       fragment
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.012(2)
_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   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0536
_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)+(0.0456P)²+0.4048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2622
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00798e7.cif
_cod_data_source_block           scd1706_OctNDI_T100K_orange
_cod_depositor_comments
'Adding full bibliography for 7231291--7231300.cif.'
_cod_original_cell_volume        841.0(5)
_cod_database_code               7231299
_publcif_datablock.id            {2925dfd5-97bb-4a9f-bdcc-729ec34e9730}
_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   0.977
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.3172(3) 0.79069(17) 0.11031(6) 0.0131(3) Uani 1 1 d . .
O1 O -0.0659(3) 0.62524(15) 0.05532(5) 0.0171(3) Uani 1 1 d . .
O2 O 0.6173(3) 0.99164(15) 0.16805(5) 0.0169(3) Uani 1 1 d . .
O3 O 0.1250(3) 0.38285(15) 0.26956(5) 0.0164(3) Uani 1 1 d . .
C1 C 0.1463(4) 0.7358(2) 0.06004(7) 0.0134(4) Uani 1 1 d . .
C2 C 0.5139(4) 0.9376(2) 0.12191(7) 0.0136(4) Uani 1 1 d . .
C3 C 0.5931(4) 1.0235(2) 0.07493(7) 0.0126(4) Uani 1 1 d . .
C4 C 0.8042(4) 1.1622(2) 0.08281(7) 0.0141(4) Uani 1 1 d . .
H4 H 0.8919 1.2053 0.1184 0.017 Uiso 1 1 calc R U
C5 C 0.8905(4) 1.2401(2) 0.03824(7) 0.0138(4) Uani 1 1 d . .
H5 H 1.0390 1.3347 0.0439 0.017 Uiso 1 1 calc R U
C6 C 0.7617(4) 1.1807(2) -0.01327(7) 0.0128(4) Uani 1 1 d . .
C7 C 0.5411(4) 1.0397(2) -0.02233(7) 0.0124(4) Uani 1 1 d . .
C8 C 0.2780(4) 0.6867(2) 0.15280(7) 0.0132(4) Uani 1 1 d . .
C9 C 0.3962(4) 0.5333(2) 0.14582(7) 0.0140(4) Uani 1 1 d . .
H9 H 0.5078 0.4997 0.1145 0.017 Uiso 1 1 calc R U
C10 C 0.3537(4) 0.4271(2) 0.18422(7) 0.0137(4) Uani 1 1 d . .
H10 H 0.4343 0.3210 0.1793 0.016 Uiso 1 1 calc R U
C11 C 0.1913(4) 0.4784(2) 0.23006(7) 0.0132(4) Uani 1 1 d . .
C12 C 0.0822(4) 0.6355(2) 0.23752(7) 0.0151(4) Uani 1 1 d . .
H12 H -0.0218 0.6716 0.2695 0.018 Uiso 1 1 calc R U
C13 C 0.1232(4) 0.7396(2) 0.19900(7) 0.0148(4) Uani 1 1 d . .
H13 H 0.0462 0.8464 0.2041 0.018 Uiso 1 1 calc R U
C14 C 0.2562(4) 0.2248(2) 0.26557(7) 0.0154(4) Uani 1 1 d . .
H14A H 0.4937 0.2379 0.2650 0.019 Uiso 1 1 calc R U
H14B H 0.1684 0.1547 0.2317 0.019 Uiso 1 1 calc R U
C15 C 0.1629(4) 0.1457(2) 0.31469(7) 0.0158(4) Uani 1 1 d . .
H15A H 0.2601 0.0388 0.3136 0.019 Uiso 1 1 calc R U
H15B H -0.0742 0.1235 0.3126 0.019 Uiso 1 1 calc R U
C16 C 0.2705(4) 0.2521(2) 0.36849(7) 0.0162(4) Uani 1 1 d . .
H16A H 0.1656 0.3571 0.3701 0.019 Uiso 1 1 calc R U
H16B H 0.5063 0.2786 0.3697 0.019 Uiso 1 1 calc R U
C17 C 0.1918(4) 0.1714(2) 0.41845(7) 0.0164(4) Uani 1 1 d . .
H17A H -0.0433 0.1426 0.4171 0.020 Uiso 1 1 calc R U
H17B H 0.3019 0.0681 0.4177 0.020 Uiso 1 1 calc R U
C18 C 0.2956(4) 0.2835(2) 0.47132(7) 0.0170(4) Uani 1 1 d . .
H18A H 0.1836 0.3862 0.4717 0.020 Uiso 1 1 calc R U
H18B H 0.5297 0.3139 0.4718 0.020 Uiso 1 1 calc R U
C19 C 0.2294(4) 0.2107(2) 0.52303(7) 0.0162(4) Uani 1 1 d . .
H19A H -0.0052 0.1832 0.5236 0.019 Uiso 1 1 calc R U
H19B H 0.3387 0.1074 0.5230 0.019 Uiso 1 1 calc R U
C20 C 0.3462(5) 0.3291(2) 0.57398(7) 0.0194(4) Uani 1 1 d . .
H20A H 0.5802 0.3572 0.5728 0.023 Uiso 1 1 calc R U
H20B H 0.2361 0.4320 0.5737 0.023 Uiso 1 1 calc R U
C21 C 0.2880(5) 0.2622(3) 0.62691(7) 0.0247(5) Uani 1 1 d . .
H21A H 0.0557 0.2424 0.6299 0.037 Uiso 1 1 calc R U
H21B H 0.3797 0.3425 0.6576 0.037 Uiso 1 1 calc R U
H21C H 0.3912 0.1585 0.6273 0.037 Uiso 1 1 calc R U
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 N1 C1 124.41(14) . .
C2 N1 C8 119.04(14) . .
C1 N1 C8 116.54(14) . .
C11 O3 C14 117.41(13) . .
O1 C1 N1 121.23(15) . .
O1 C1 C6 121.92(16) . 2_675
N1 C1 C6 116.84(15) . 2_675
O2 C2 N1 121.62(16) . .
O2 C2 C3 121.65(16) . .
N1 C2 C3 116.72(15) . .
C4 C3 C7 120.19(16) . 2_675
C4 C3 C2 119.83(16) . .
C7 C3 C2 119.96(16) 2_675 .
C3 C4 C5 120.12(16) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 120.55(16) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 120.40(16) . .
C5 C6 C1 120.13(16) . 2_675
C7 C6 C1 119.47(16) . 2_675
C3 C7 C7 119.8(2) 2_675 2_675
C3 C7 C6 121.28(16) 2_675 .
C7 C7 C6 118.9(2) 2_675 .
C9 C8 C13 120.49(16) . .
C9 C8 N1 118.42(15) . .
C13 C8 N1 121.08(15) . .
C8 C9 C10 120.55(16) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C11 119.05(16) . .
C9 C10 H10 120.5 . .
C11 C10 H10 120.5 . .
O3 C11 C12 115.81(15) . .
O3 C11 C10 124.33(16) . .
C12 C11 C10 119.86(16) . .
C13 C12 C11 120.65(16) . .
C13 C12 H12 119.7 . .
C11 C12 H12 119.7 . .
C12 C13 C8 119.33(16) . .
C12 C13 H13 120.3 . .
C8 C13 H13 120.3 . .
O3 C14 C15 107.73(14) . .
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 113.15(15) . .
C14 C15 H15A 108.9 . .
C16 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
C16 C15 H15B 108.9 . .
H15A C15 H15B 107.8 . .
C15 C16 C17 113.93(15) . .
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 112.24(15) . .
C18 C17 H17A 109.2 . .
C16 C17 H17A 109.2 . .
C18 C17 H17B 109.2 . .
C16 C17 H17B 109.2 . .
H17A C17 H17B 107.9 . .
C17 C18 C19 115.35(15) . .
C17 C18 H18A 108.4 . .
C19 C18 H18A 108.4 . .
C17 C18 H18B 108.4 . .
C19 C18 H18B 108.4 . .
H18A C18 H18B 107.5 . .
C20 C19 C18 112.03(15) . .
C20 C19 H19A 109.2 . .
C18 C19 H19A 109.2 . .
C20 C19 H19B 109.2 . .
C18 C19 H19B 109.2 . .
H19A C19 H19B 107.9 . .
C21 C20 C19 114.29(16) . .
C21 C20 H20A 108.7 . .
C19 C20 H20A 108.7 . .
C21 C20 H20B 108.7 . .
C19 C20 H20B 108.7 . .
H20A C20 H20B 107.6 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.399(2) .
N1 C1 1.405(2) .
N1 C8 1.457(2) .
O1 C1 1.213(2) .
O2 C2 1.216(2) .
O3 C11 1.369(2) .
O3 C14 1.436(2) .
C1 C6 1.487(2) 2_675
C2 C3 1.489(2) .
C3 C4 1.377(2) .
C3 C7 1.409(2) 2_675
C4 C5 1.408(2) .
C4 H4 0.9500 .
C5 C6 1.372(2) .
C5 H5 0.9500 .
C6 C7 1.414(2) .
C6 C1 1.487(2) 2_675
C7 C3 1.409(2) 2_675
C7 C7 1.412(3) 2_675
C8 C9 1.377(2) .
C8 C13 1.386(2) .
C9 C10 1.391(2) .
C9 H9 0.9500 .
C10 C11 1.393(2) .
C10 H10 0.9500 .
C11 C12 1.390(2) .
C12 C13 1.380(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.520(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.522(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.529(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.522(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.524(2) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.523(2) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.522(2) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 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
C2 N1 C1 O1 -165.81(16) . .
C8 N1 C1 O1 13.0(2) . .
C2 N1 C1 C6 14.3(2) . 2_675
C8 N1 C1 C6 -166.91(14) . 2_675
C1 N1 C2 O2 168.73(16) . .
C8 N1 C2 O2 -10.1(2) . .
C1 N1 C2 C3 -11.9(2) . .
C8 N1 C2 C3 169.32(14) . .
O2 C2 C3 C4 4.1(3) . .
N1 C2 C3 C4 -175.27(15) . .
O2 C2 C3 C7 -177.63(16) . 2_675
N1 C2 C3 C7 3.0(2) . 2_675
C7 C3 C4 C5 -0.9(3) 2_675 .
C2 C3 C4 C5 177.38(15) . .
C3 C4 C5 C6 1.0(3) . .
C4 C5 C6 C7 -0.2(3) . .
C4 C5 C6 C1 179.83(15) . 2_675
C5 C6 C7 C3 -179.82(16) . 2_675
C1 C6 C7 C3 0.2(2) 2_675 2_675
C5 C6 C7 C7 -0.8(3) . 2_675
C1 C6 C7 C7 179.20(18) 2_675 2_675
C2 N1 C8 C9 -114.55(18) . .
C1 N1 C8 C9 66.5(2) . .
C2 N1 C8 C13 66.0(2) . .
C1 N1 C8 C13 -112.93(18) . .
C13 C8 C9 C10 2.0(3) . .
N1 C8 C9 C10 -177.52(15) . .
C8 C9 C10 C11 -0.4(3) . .
C14 O3 C11 C12 -175.11(15) . .
C14 O3 C11 C10 5.6(2) . .
C9 C10 C11 O3 177.60(16) . .
C9 C10 C11 C12 -1.7(2) . .
O3 C11 C12 C13 -177.13(16) . .
C10 C11 C12 C13 2.2(3) . .
C11 C12 C13 C8 -0.7(3) . .
C9 C8 C13 C12 -1.4(3) . .
N1 C8 C13 C12 178.02(16) . .
C11 O3 C14 C15 177.64(14) . .
O3 C14 C15 C16 -55.96(19) . .
C14 C15 C16 C17 -177.47(15) . .
C15 C16 C17 C18 -178.53(15) . .
C16 C17 C18 C19 -179.18(15) . .
C17 C18 C19 C20 178.84(16) . .
C18 C19 C20 C21 -179.64(16) . .
