#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/05/7120583.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_7120583
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 99.997(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.026(2)
_cell_length_b                   33.756(5)
_cell_length_c                   7.9533(14)
_cell_measurement_reflns_used    7185
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.41
_cell_volume                     1328.9(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       blade
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.840
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0502
_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)+(0.0783P)²+0.4261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3266
_reflns_number_total             4061
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {4a4983a4-0a80-4720-bfd2-e5377475b215}
_cod_data_source_file            c7cc04346e2.cif
_cod_data_source_block           scd0381_05112016_Monoclinic_100K
_cod_original_cell_volume        1328.8(6)
_cod_database_code               7120583
_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   0.923
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.67779(19) 0.60970(3) 0.79878(11) 0.0147(2) Uani 1 1 d . .
O2 O -0.06737(18) 0.53784(3) 0.58139(11) 0.0146(2) Uani 1 1 d . .
O3 O 0.10927(19) 0.67389(3) 0.11841(11) 0.0143(2) Uani 1 1 d . .
N1 N 0.3241(2) 0.57126(3) 0.67603(12) 0.0112(2) Uani 1 1 d . .
C1 C 0.5495(2) 0.57933(3) 0.80167(15) 0.0111(2) Uani 1 1 d . .
C2 C 0.1436(2) 0.53964(3) 0.68085(14) 0.0108(2) Uani 1 1 d . .
C3 C 0.2281(2) 0.50886(3) 0.81278(14) 0.0102(2) Uani 1 1 d . .
C4 C 0.4620(2) 0.51462(3) 0.93653(14) 0.0098(2) Uani 1 1 d . .
C5 C 0.0766(2) 0.47482(4) 0.81341(14) 0.0115(2) Uani 1 1 d . .
H5 H -0.0799 0.4710 0.7290 0.014 Uiso 1 1 calc R U
C6 C 0.1535(2) 0.44565(3) 0.93893(15) 0.0119(2) Uani 1 1 d . .
H6 H 0.0492 0.4222 0.9383 0.014 Uiso 1 1 calc R U
C7 C 0.3789(2) 0.45097(3) 1.06267(14) 0.0101(2) Uani 1 1 d . .
C8 C 0.2705(2) 0.59806(3) 0.53116(15) 0.0111(2) Uani 1 1 d . .
C9 C 0.4228(2) 0.59426(4) 0.40310(15) 0.0127(2) Uani 1 1 d . .
H9 H 0.5592 0.5745 0.4112 0.015 Uiso 1 1 calc R U
C10 C 0.3760(3) 0.61941(4) 0.26201(15) 0.0124(2) Uani 1 1 d . .
H10 H 0.4811 0.6170 0.1741 0.015 Uiso 1 1 calc R U
C11 C 0.1740(2) 0.64807(3) 0.25072(15) 0.0111(2) Uani 1 1 d . .
C12 C 0.0216(3) 0.65157(3) 0.38130(15) 0.0129(2) Uani 1 1 d . .
H12 H -0.1157 0.6712 0.3737 0.015 Uiso 1 1 calc R U
C13 C 0.0696(3) 0.62665(3) 0.52167(15) 0.0127(2) Uani 1 1 d . .
H13 H -0.0337 0.6291 0.6105 0.015 Uiso 1 1 calc R U
C14 C 0.2537(3) 0.67025(4) -0.02198(15) 0.0161(3) Uani 1 1 d . .
H14A H 0.2266 0.6435 -0.0733 0.019 Uiso 1 1 calc R U
H14B H 0.4495 0.6743 0.0180 0.019 Uiso 1 1 calc R U
C15 C 0.1438(3) 0.70155(4) -0.15208(15) 0.0168(3) Uani 1 1 d . .
H15A H -0.0530 0.6973 -0.1871 0.020 Uiso 1 1 calc R U
H15B H 0.2286 0.6980 -0.2545 0.020 Uiso 1 1 calc R U
C16 C 0.1918(3) 0.74411(4) -0.08836(16) 0.0168(3) Uani 1 1 d . .
H16A H 0.0864 0.7622 -0.1725 0.020 Uiso 1 1 calc R U
H16B H 0.1230 0.7470 0.0203 0.020 Uiso 1 1 calc R U
C17 C 0.4865(3) 0.75662(5) -0.0599(2) 0.0258(3) Uani 1 1 d . .
H17A H 0.5930 0.7387 0.0227 0.039 Uiso 1 1 calc R U
H17B H 0.5031 0.7838 -0.0156 0.039 Uiso 1 1 calc R U
H17C H 0.5537 0.7554 -0.1683 0.039 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 117.39(9) . .
C1 N1 C2 125.01(10) . .
C1 N1 C8 117.42(10) . .
C2 N1 C8 117.56(10) . .
O1 C1 N1 121.14(11) . .
O1 C1 C7 122.22(11) . 3_667
N1 C1 C7 116.64(10) . 3_667
O2 C2 N1 121.13(10) . .
O2 C2 C3 122.52(11) . .
N1 C2 C3 116.35(10) . .
C5 C3 C4 120.42(10) . .
C5 C3 C2 119.69(11) . .
C4 C3 C2 119.89(10) . .
C7 C4 C3 121.35(10) 3_667 .
C7 C4 C4 119.26(13) 3_667 3_667
C3 C4 C4 119.39(13) . 3_667
C3 C5 C6 120.12(11) . .
C3 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C7 C6 C5 120.39(11) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C4 120.40(11) . 3_667
C6 C7 C1 119.66(10) . 3_667
C4 C7 C1 119.92(11) 3_667 3_667
C9 C8 C13 120.96(11) . .
C9 C8 N1 118.46(10) . .
C13 C8 N1 120.58(10) . .
C8 C9 C10 119.95(11) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C9 119.58(11) . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
O3 C11 C10 124.60(11) . .
O3 C11 C12 115.57(10) . .
C10 C11 C12 119.83(11) . .
C13 C12 C11 120.41(11) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C8 119.27(11) . .
C12 C13 H13 120.4 . .
C8 C13 H13 120.4 . .
O3 C14 C15 107.31(10) . .
O3 C14 H14A 110.3 . .
C15 C14 H14A 110.3 . .
O3 C14 H14B 110.3 . .
C15 C14 H14B 110.3 . .
H14A C14 H14B 108.5 . .
C14 C15 C16 114.29(11) . .
C14 C15 H15A 108.7 . .
C16 C15 H15A 108.7 . .
C14 C15 H15B 108.7 . .
C16 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C17 C16 C15 113.84(12) . .
C17 C16 H16A 108.8 . .
C15 C16 H16A 108.8 . .
C17 C16 H16B 108.8 . .
C15 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 1.2135(15) .
O2 C2 1.2095(15) .
O3 C11 1.3616(13) .
O3 C14 1.4387(15) .
N1 C1 1.4010(16) .
N1 C2 1.4055(15) .
N1 C8 1.4527(14) .
C1 C7 1.4848(16) 3_667
C2 C3 1.4852(15) .
C3 C5 1.3790(17) .
C3 C4 1.4096(17) .
C4 C7 1.4095(16) 3_667
C4 C4 1.416(2) 3_667
C5 C6 1.4076(16) .
C5 H5 0.9500 .
C6 C7 1.3775(17) .
C6 H6 0.9500 .
C7 C4 1.4095(16) 3_667
C7 C1 1.4848(16) 3_667
C8 C9 1.3821(16) .
C8 C13 1.3892(17) .
C9 C10 1.3940(16) .
C9 H9 0.9500 .
C10 C11 1.3939(17) .
C10 H10 0.9500 .
C11 C12 1.3984(17) .
C12 C13 1.3852(16) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.5142(17) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.5286(18) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.519(2) .
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_4
C2 N1 C1 O1 -171.30(11) .
C8 N1 C1 O1 7.58(17) .
C2 N1 C1 C7 8.49(17) 3_667
C8 N1 C1 C7 -172.63(10) 3_667
C1 N1 C2 O2 169.00(11) .
C8 N1 C2 O2 -9.89(16) .
C1 N1 C2 C3 -11.50(16) .
C8 N1 C2 C3 169.62(10) .
O2 C2 C3 C5 6.65(18) .
N1 C2 C3 C5 -172.85(10) .
O2 C2 C3 C4 -173.29(11) .
N1 C2 C3 C4 7.21(16) .
C5 C3 C4 C7 179.45(11) 3_667
C2 C3 C4 C7 -0.61(17) 3_667
C5 C3 C4 C4 -1.0(2) 3_667
C2 C3 C4 C4 178.90(12) 3_667
C4 C3 C5 C6 0.57(18) .
C2 C3 C5 C6 -179.37(10) .
C3 C5 C6 C7 0.48(18) .
C5 C6 C7 C4 -1.04(18) 3_667
C5 C6 C7 C1 177.45(10) 3_667
C1 N1 C8 C9 78.29(14) .
C2 N1 C8 C9 -102.73(13) .
C1 N1 C8 C13 -102.04(14) .
C2 N1 C8 C13 76.93(15) .
C13 C8 C9 C10 0.13(19) .
N1 C8 C9 C10 179.79(11) .
C8 C9 C10 C11 -0.45(18) .
C14 O3 C11 C10 2.29(17) .
C14 O3 C11 C12 -177.52(11) .
C9 C10 C11 O3 -179.35(11) .
C9 C10 C11 C12 0.46(18) .
O3 C11 C12 C13 179.67(11) .
C10 C11 C12 C13 -0.15(18) .
C11 C12 C13 C8 -0.17(18) .
C9 C8 C13 C12 0.18(18) .
N1 C8 C13 C12 -179.48(11) .
C11 O3 C14 C15 179.31(10) .
O3 C14 C15 C16 63.50(15) .
C14 C15 C16 C17 68.56(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122373772
