#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:54:42 +0300 (Fri, 05 May 2023) $
#$Revision: 283389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062387.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_7062387
loop_
_publ_author_name
'Zheng, Zihang'
'Ju, Zhengkun'
'Ma, Shuang'
'Liu, Zhiqi'
'Xiang, Wenxin'
'Chen, Jinqiu'
'Yang, Bo'
'Mu, Zifeng'
'Zhang, Jing'
'Li, Pan'
'Sheng, Peng'
_publ_section_title
;
 Napthalene diimide derivative based organic cocrystal frameworks as
 cathode electrodes for stable lithium batteries
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7476
_journal_page_last               7480
_journal_paper_doi               10.1039/D3NJ00698K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C16 H10 N2 O4, C24 H12, 2(C), [+ solvents]'
_chemical_formula_sum            'C42 H26 Cl2 N2 O4'
_chemical_formula_weight         693.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-19
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                94.520(9)
_cell_angle_beta                 94.515(8)
_cell_angle_gamma                103.410(8)
_cell_formula_units_Z            1
_cell_length_a                   7.2003(9)
_cell_length_b                   10.1086(13)
_cell_length_c                   11.0066(14)
_cell_measurement_reflns_used    3785
_cell_measurement_temperature    197.00
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      4.05
_cell_volume                     772.95(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      197.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_min         4.049
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.307
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1282 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.6708.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.059
_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     227
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0613
_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)+(0.0853P)²+0.4151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2277
_reflns_number_total             2832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00698k2.cif
_cod_data_source_block           cu_20211217_ny_cn1_0m
_cod_depositor_comments
'Adding full bibliography for 7062387--7062388.cif.'
_cod_database_code               7062387
_shelx_shelxl_version_number     2018/3
_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_max   0.802
_shelx_estimated_absorpt_t_min   0.754
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23553(13) 0.51982(9) 0.06615(9) 0.0862(4) Uani 1 1 d . . . . .
C21 C 0.4993(7) 0.5322(4) 0.0591(3) 0.0931(12) Uani 1 1 d . . . . .
H21A H 0.573612 0.628590 0.067411 0.112 Uiso 1 1 calc R U . . .
H21B H 0.550815 0.483258 0.123183 0.112 Uiso 1 1 calc R U . . .
O1 O -0.3830(3) -0.10338(19) 0.14225(14) 0.0508(5) Uani 1 1 d . . . . .
O2 O -0.3479(3) 0.33293(18) 0.29335(16) 0.0519(5) Uani 1 1 d . . . . .
N1 N -0.3592(3) 0.1150(2) 0.21991(16) 0.0416(5) Uani 1 1 d . . . . .
C1 C -0.2987(4) 0.1637(3) 0.1036(2) 0.0552(7) Uani 1 1 d . . . . .
H1A H -0.219166 0.106731 0.068560 0.083 Uiso 1 1 calc R U . . .
H1B H -0.224350 0.258799 0.118278 0.083 Uiso 1 1 calc R U . . .
H1C H -0.412225 0.157972 0.046286 0.083 Uiso 1 1 calc R U . . .
C2 C -0.3988(3) -0.0253(2) 0.22888(19) 0.0396(5) Uani 1 1 d . . . . .
C3 C -0.3767(3) 0.2132(2) 0.3118(2) 0.0403(5) Uani 1 1 d . . . . .
C4 C -0.4587(3) -0.0732(2) 0.34639(19) 0.0368(5) Uani 1 1 d . . . . .
C5 C -0.4720(3) 0.0231(2) 0.44395(19) 0.0341(5) Uani 1 1 d . . . . .
C6 C -0.5011(3) -0.2104(2) 0.3615(2) 0.0411(5) Uani 1 1 d . . . . .
H6 H -0.493838 -0.274825 0.295443 0.049 Uiso 1 1 calc R U . . .
C7 C -0.5549(3) -0.2561(2) 0.4735(2) 0.0414(5) Uani 1 1 d . . . . .
H7 H -0.581985 -0.351008 0.483104 0.050 Uiso 1 1 calc R U . . .
C8 C -0.5688(3) -0.1642(2) 0.56987(19) 0.0362(5) Uani 1 1 d . . . . .
C9 C 0.0720(4) -0.1402(3) 0.1878(2) 0.0510(6) Uani 1 1 d . . . . .
H9 H 0.077029 -0.203176 0.120064 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1229(3) -0.0013(3) 0.1763(2) 0.0488(6) Uani 1 1 d . . . . .
H10 H 0.163400 0.029633 0.101196 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1152(3) 0.0949(3) 0.2748(2) 0.0436(6) Uani 1 1 d . . . . .
C12 C 0.1631(3) 0.2362(3) 0.2648(2) 0.0495(6) Uani 1 1 d . . . . .
H12 H 0.201178 0.268507 0.189640 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1558(3) 0.3291(3) 0.3625(2) 0.0480(6) Uani 1 1 d . . . . .
H13 H 0.188502 0.424141 0.353411 0.058 Uiso 1 1 calc R U . . .
C14 C 0.1000(3) 0.2843(2) 0.4759(2) 0.0442(6) Uani 1 1 d . . . . .
C15 C 0.0490(3) 0.1423(2) 0.4881(2) 0.0383(5) Uani 1 1 d . . . . .
C16 C 0.0575(3) 0.0480(2) 0.3872(2) 0.0391(5) Uani 1 1 d . . . . .
C17 C -0.0073(3) 0.0951(2) 0.6008(2) 0.0388(5) Uani 1 1 d . . . . .
C18 C -0.0129(3) 0.1899(3) 0.7016(2) 0.0453(6) Uani 1 1 d . . . . .
C19 C 0.0423(4) 0.3307(3) 0.6878(2) 0.0500(6) Uani 1 1 d . . . . .
H19 H 0.041811 0.395301 0.755314 0.060 Uiso 1 1 calc R U . . .
C20 C 0.0970(4) 0.3765(3) 0.5782(3) 0.0515(6) Uani 1 1 d . . . . .
H20 H 0.133376 0.471982 0.571516 0.062 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
Cl1 C21 H21A 111.5 . . ?
Cl1 C21 H21B 111.5 . . ?
C21 C21 Cl1 101.5(4) 2_665 . ?
C21 C21 H21A 111.5 2_665 . ?
C21 C21 H21B 111.5 2_665 . ?
H21A C21 H21B 109.3 . . ?
C2 N1 C1 117.7(2) . . ?
C2 N1 C3 125.14(19) . . ?
C3 N1 C1 117.1(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 120.2(2) . . ?
O1 C2 C4 122.4(2) . . ?
N1 C2 C4 117.3(2) . . ?
O2 C3 N1 120.4(2) . . ?
O2 C3 C8 122.7(2) . 2_456 ?
N1 C3 C8 116.9(2) . 2_456 ?
C5 C4 C2 119.6(2) . . ?
C6 C4 C2 120.5(2) . . ?
C6 C4 C5 120.0(2) . . ?
C5 C5 C4 119.3(3) 2_456 . ?
C5 C5 C8 119.7(3) 2_456 2_456 ?
C8 C5 C4 121.0(2) 2_456 . ?
C4 C6 H6 119.7 . . ?
C4 C6 C7 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C5 C8 C3 120.0(2) 2_456 2_456 ?
C7 C8 C3 120.1(2) . 2_456 ?
C7 C8 C5 119.9(2) . 2_456 ?
C10 C9 H9 119.4 . . ?
C10 C9 C18 121.2(2) . 2_556 ?
C18 C9 H9 119.4 2_556 . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C16 119.3(2) . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 C16 118.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.2(2) . . ?
C20 C14 C13 122.2(2) . . ?
C20 C14 C15 118.6(2) . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 C17 120.2(2) . . ?
C17 C15 C16 120.5(2) . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 C17 119.8(2) . 2_556 ?
C15 C16 C17 119.6(2) . 2_556 ?
C15 C17 C16 119.9(2) . 2_556 ?
C18 C17 C15 120.1(2) . . ?
C18 C17 C16 119.9(2) . 2_556 ?
C9 C18 C17 119.0(2) 2_556 . ?
C19 C18 C9 122.4(2) . 2_556 ?
C19 C18 C17 118.6(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C14 C20 H20 119.4 . . ?
C19 C20 C14 121.2(2) . . ?
C19 C20 H20 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.882(5) . ?
C21 C21 1.410(8) 2_665 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
O1 C2 1.219(3) . ?
O2 C3 1.216(3) . ?
N1 C1 1.469(3) . ?
N1 C2 1.393(3) . ?
N1 C3 1.395(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.478(3) . ?
C3 C8 1.479(3) 2_456 ?
C4 C5 1.416(3) . ?
C4 C6 1.376(3) . ?
C5 C5 1.409(4) 2_456 ?
C5 C8 1.410(3) 2_456 ?
C6 H6 0.9500 . ?
C6 C7 1.401(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(4) . ?
C9 C18 1.412(4) 2_556 ?
C10 H10 0.9500 . ?
C10 C11 1.412(4) . ?
C11 C12 1.405(4) . ?
C11 C16 1.417(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.418(4) . ?
C14 C15 1.417(3) . ?
C14 C20 1.408(4) . ?
C15 C16 1.420(3) . ?
C15 C17 1.418(3) . ?
C16 C17 1.428(4) 2_556 ?
C17 C18 1.417(3) . ?
C18 C19 1.411(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C4 C5 179.21(19) . . . . ?
O1 C2 C4 C6 -0.6(3) . . . . ?
N1 C2 C4 C5 -0.5(3) . . . . ?
N1 C2 C4 C6 179.67(18) . . . . ?
C1 N1 C2 O1 0.0(3) . . . . ?
C1 N1 C2 C4 179.74(19) . . . . ?
C1 N1 C3 O2 2.1(3) . . . . ?
C1 N1 C3 C8 -178.01(19) . . . 2_456 ?
C2 N1 C3 O2 -176.32(19) . . . . ?
C2 N1 C3 C8 3.6(3) . . . 2_456 ?
C2 C4 C5 C5 -179.6(2) . . . 2_456 ?
C2 C4 C5 C8 0.8(3) . . . 2_456 ?
C2 C4 C6 C7 178.94(19) . . . . ?
C3 N1 C2 O1 178.43(19) . . . . ?
C3 N1 C2 C4 -1.9(3) . . . . ?
C4 C6 C7 C8 0.9(3) . . . . ?
C5 C4 C6 C7 -0.9(3) . . . . ?
C6 C4 C5 C5 0.2(4) . . . 2_456 ?
C6 C4 C5 C8 -179.30(18) . . . 2_456 ?
C6 C7 C8 C3 -179.26(19) . . . 2_456 ?
C6 C7 C8 C5 -0.2(3) . . . 2_456 ?
C9 C10 C11 C12 -179.0(2) . . . . ?
C9 C10 C11 C16 1.0(3) . . . . ?
C9 C18 C19 C20 -179.1(2) 2_556 . . . ?
C10 C11 C12 C13 -179.7(2) . . . . ?
C10 C11 C16 C15 179.78(19) . . . . ?
C10 C11 C16 C17 -0.2(3) . . . 2_556 ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C12 C11 C16 C17 179.69(18) . . . 2_556 ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 C20 177.9(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C13 C14 C15 C17 180.00(19) . . . . ?
C13 C14 C20 C19 -180.0(2) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C14 C15 C16 C17 179.63(18) . . . 2_556 ?
C14 C15 C17 C16 -179.63(18) . . . 2_556 ?
C14 C15 C17 C18 0.1(3) . . . . ?
C15 C14 C20 C19 -1.2(4) . . . . ?
C15 C17 C18 C9 179.1(2) . . . 2_556 ?
C15 C17 C18 C19 -1.4(3) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C16 C15 C17 C16 -0.6(3) . . . 2_556 ?
C16 C15 C17 C18 179.16(18) . . . . ?
C16 C17 C18 C9 -1.2(3) 2_556 . . 2_556 ?
C16 C17 C18 C19 178.36(19) 2_556 . . . ?
C17 C15 C16 C11 -179.44(18) . . . . ?
C17 C15 C16 C17 0.6(3) . . . 2_556 ?
C17 C18 C19 C20 1.4(4) . . . . ?
C18 C9 C10 C11 -0.6(4) 2_556 . . . ?
C18 C19 C20 C14 -0.1(4) . . . . ?
C20 C14 C15 C16 -177.88(19) . . . . ?
C20 C14 C15 C17 1.2(3) . . . . ?
