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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/05/7120584.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_7120584
loop_
_publ_author_name
'Dharmarwardana, Madushani'
'Welch, Raymond Patrick'
'Kwon, Sunah'
'Nguyen, Victoria K.'
'McCandless, Gregory T.'
'Omary, Mohammad A.'
'Gassensmith, Jeremiah J.'
_publ_section_title
;
 Thermo-Mechanically Responsive Crystalline Organic Cantilever
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04346E
_journal_year                    2017
_chemical_formula_moiety         'C34 H30 N2 O6'
_chemical_formula_sum            'C34 H30 N2 O6'
_chemical_formula_weight         562.60
_chemical_melting_point          635
_chemical_name_common            BNDI
_chemical_name_systematic
'butoxyphenyl N-substituted naphthalene diimide '
_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
;
2016-08-03 deposited with the CCDC.
2017-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                100.182(11)
_cell_angle_beta                 93.124(14)
_cell_angle_gamma                94.102(14)
_cell_formula_units_Z            1
_cell_length_a                   4.1636(8)
_cell_length_b                   8.1371(18)
_cell_length_c                   20.104(5)
_cell_measurement_reflns_used    6075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.57
_cell_volume                     667.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.993
_diffrn_measured_fraction_theta_max 0.912
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14793
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.537
_diffrn_reflns_theta_min         2.552
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       fragment
_exptl_crystal_F_000             296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0449
_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)+(0.0555P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2854
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {dc48d5fa-6034-47e2-beca-65b2ac4106b6}
_cod_data_source_file            c7cc04346e2.cif
_cod_data_source_block           scd0497_Triclinic_100K
_cod_database_code               7120584
_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   0.994
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
O1 O 0.6252(2) 1.01365(11) 0.70924(4) 0.0149(2) Uani 1 1 d . .
O2 O -0.0723(2) 0.63226(11) 0.57043(4) 0.0154(2) Uani 1 1 d . .
O3 O 0.1453(2) 0.41476(11) 0.83759(4) 0.0147(2) Uani 1 1 d . .
N1 N 0.3144(3) 0.80567(12) 0.63843(5) 0.0115(2) Uani 1 1 d . .
C1 C 0.5169(3) 0.95419(14) 0.65216(6) 0.0110(2) Uani 1 1 d . .
C2 C 0.1415(3) 0.74407(14) 0.57577(6) 0.0114(2) Uani 1 1 d . .
C3 C 0.2342(3) 0.82118(14) 0.51740(6) 0.0107(2) Uani 1 1 d . .
C4 C 0.1014(3) 0.75410(15) 0.45315(6) 0.0123(2) Uani 1 1 d . .
H4 H -0.0499 0.6586 0.4465 0.015 Uiso 1 1 calc R U
C5 C 0.1888(3) 0.82643(15) 0.39758(6) 0.0120(2) Uani 1 1 d . .
H5 H 0.0990 0.7784 0.3534 0.014 Uiso 1 1 calc R U
C6 C 0.4038(3) 0.96659(14) 0.40676(6) 0.0106(2) Uani 1 1 d . .
C7 C 0.5420(3) 1.03681(14) 0.47210(6) 0.0100(2) Uani 1 1 d . .
C8 C 0.2784(3) 0.70653(15) 0.69140(6) 0.0114(2) Uani 1 1 d . .
C9 C 0.1262(3) 0.76481(15) 0.74961(6) 0.0135(2) Uani 1 1 d . .
H9 H 0.0472 0.8728 0.7562 0.016 Uiso 1 1 calc R U
C10 C 0.0904(3) 0.66481(15) 0.79792(6) 0.0141(3) Uani 1 1 d . .
H10 H -0.0115 0.7047 0.8381 0.017 Uiso 1 1 calc R U
C11 C 0.2029(3) 0.50563(15) 0.78809(6) 0.0120(2) Uani 1 1 d . .
C12 C 0.3613(3) 0.44887(15) 0.73016(6) 0.0121(2) Uani 1 1 d . .
H12 H 0.4429 0.3415 0.7236 0.015 Uiso 1 1 calc R U
C13 C 0.3987(3) 0.55103(15) 0.68201(6) 0.0125(2) Uani 1 1 d . .
H13 H 0.5075 0.5136 0.6425 0.015 Uiso 1 1 calc R U
C14 C 0.2785(3) 0.25521(15) 0.83178(6) 0.0142(3) Uani 1 1 d . .
H14A H 0.5149 0.2689 0.8284 0.017 Uiso 1 1 calc R U
H14B H 0.1820 0.1785 0.7906 0.017 Uiso 1 1 calc R U
C15 C 0.2025(3) 0.18434(16) 0.89444(6) 0.0156(3) Uani 1 1 d . .
H15A H 0.2988 0.0759 0.8924 0.019 Uiso 1 1 calc R U
H15B H -0.0343 0.1627 0.8950 0.019 Uiso 1 1 calc R U
C16 C 0.3296(3) 0.30131(17) 0.95968(6) 0.0184(3) Uani 1 1 d . .
H16A H 0.2278 0.4083 0.9622 0.022 Uiso 1 1 calc R U
H16B H 0.5651 0.3260 0.9582 0.022 Uiso 1 1 calc R U
C17 C 0.2660(4) 0.2306(2) 1.02350(7) 0.0277(3) Uani 1 1 d . .
H17A H 0.0327 0.2120 1.0269 0.042 Uiso 1 1 calc R U
H17B H 0.3601 0.3102 1.0633 0.042 Uiso 1 1 calc R U
H17C H 0.3643 0.1240 1.0213 0.042 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
C11 O3 C14 117.36(9) . .
C1 N1 C2 124.13(10) . .
C1 N1 C8 118.84(10) . .
C2 N1 C8 117.03(10) . .
O1 C1 N1 121.44(10) . .
O1 C1 C6 121.87(11) . 2_676
N1 C1 C6 116.68(10) . 2_676
O2 C2 N1 120.85(10) . .
O2 C2 C3 122.11(11) . .
N1 C2 C3 117.04(10) . .
C4 C3 C7 120.30(10) . 2_676
C4 C3 C2 120.00(11) . .
C7 C3 C2 119.70(10) 2_676 .
C3 C4 C5 120.27(11) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 120.44(11) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 120.04(10) . .
C5 C6 C1 119.75(10) . 2_676
C7 C6 C1 120.19(10) . 2_676
C3 C7 C6 121.06(10) 2_676 .
C3 C7 C7 119.27(13) 2_676 2_676
C6 C7 C7 119.67(13) . 2_676
C13 C8 C9 120.58(11) . .
C13 C8 N1 117.98(10) . .
C9 C8 N1 121.44(11) . .
C10 C9 C8 119.52(11) . .
C10 C9 H9 120.2 . .
C8 C9 H9 120.2 . .
C9 C10 C11 120.40(11) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
O3 C11 C12 124.34(11) . .
O3 C11 C10 115.77(10) . .
C12 C11 C10 119.89(11) . .
C13 C12 C11 119.31(11) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
C8 C13 C12 120.27(11) . .
C8 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
O3 C14 C15 107.57(10) . .
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 112.64(11) . .
C14 C15 H15A 109.1 . .
C16 C15 H15A 109.1 . .
C14 C15 H15B 109.1 . .
C16 C15 H15B 109.1 . .
H15A C15 H15B 107.8 . .
C15 C16 C17 113.74(12) . .
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 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2127(15) .
O2 C2 1.2128(15) .
O3 C11 1.3620(14) .
O3 C14 1.4364(15) .
N1 C1 1.3995(16) .
N1 C2 1.4081(16) .
N1 C8 1.4529(15) .
C1 C6 1.4864(16) 2_676
C2 C3 1.4815(16) .
C3 C4 1.3789(17) .
C3 C7 1.4094(16) 2_676
C4 C5 1.4047(16) .
C4 H4 0.9500 .
C5 C6 1.3777(17) .
C5 H5 0.9500 .
C6 C7 1.4100(16) .
C6 C1 1.4864(16) 2_676
C7 C3 1.4094(16) 2_676
C7 C7 1.411(2) 2_676
C8 C13 1.3799(17) .
C8 C9 1.3869(17) .
C9 C10 1.3803(17) .
C9 H9 0.9500 .
C10 C11 1.3938(18) .
C10 H10 0.9500 .
C11 C12 1.3935(17) .
C12 C13 1.3910(17) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.5146(17) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.5221(18) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.5247(18) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 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 169.74(11) . .
C8 N1 C1 O1 -10.59(17) . .
C2 N1 C1 C6 -11.22(17) . 2_676
C8 N1 C1 C6 168.44(10) . 2_676
C1 N1 C2 O2 -166.71(11) . .
C8 N1 C2 O2 13.62(17) . .
C1 N1 C2 C3 13.62(17) . .
C8 N1 C2 C3 -166.05(10) . .
O2 C2 C3 C4 -7.22(18) . .
N1 C2 C3 C4 172.45(11) . .
O2 C2 C3 C7 172.72(11) . 2_676
N1 C2 C3 C7 -7.62(16) . 2_676
C7 C3 C4 C5 0.20(18) 2_676 .
C2 C3 C4 C5 -179.87(11) . .
C3 C4 C5 C6 -1.06(18) . .
C4 C5 C6 C7 1.07(18) . .
C4 C5 C6 C1 -177.42(11) . 2_676
C5 C6 C7 C3 179.15(11) . 2_676
C1 C6 C7 C3 -2.37(17) 2_676 2_676
C5 C6 C7 C7 -0.2(2) . 2_676
C1 C6 C7 C7 178.24(13) 2_676 2_676
C1 N1 C8 C13 -113.09(13) . .
C2 N1 C8 C13 66.60(15) . .
C1 N1 C8 C9 67.34(15) . .
C2 N1 C8 C9 -112.97(13) . .
C13 C8 C9 C10 -1.10(18) . .
N1 C8 C9 C10 178.46(11) . .
C8 C9 C10 C11 -0.71(19) . .
C14 O3 C11 C12 4.89(17) . .
C14 O3 C11 C10 -175.48(11) . .
C9 C10 C11 O3 -177.69(11) . .
C9 C10 C11 C12 1.96(19) . .
O3 C11 C12 C13 178.21(11) . .
C10 C11 C12 C13 -1.41(18) . .
C9 C8 C13 C12 1.65(19) . .
N1 C8 C13 C12 -177.93(11) . .
C11 C12 C13 C8 -0.38(18) . .
C11 O3 C14 C15 176.17(10) . .
O3 C14 C15 C16 -56.78(14) . .
C14 C15 C16 C17 -178.12(11) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122373772
