#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:16:45 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223469 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/29/7232924.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_7232924
loop_
_publ_author_name
'Mandal, Arkalekha'
'Rissanen, Kari'
'Mal, Prasenjit'
_publ_section_title
;
 Unravelling substitution effects on charge transfer characteristics in
 cocrystals of pyrene based donors and 3,5-dinitrobenzoic acid
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              4401
_journal_paper_doi               10.1039/C9CE00561G
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C25 H18 N2 O7'
_chemical_formula_weight         458.41
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-06-19 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                96.283(5)
_cell_angle_beta                 95.365(5)
_cell_angle_gamma                103.343(6)
_cell_formula_units_Z            2
_cell_length_a                   6.6108(5)
_cell_length_b                   9.5147(7)
_cell_length_c                   17.1651(10)
_cell_measurement_reflns_used    3703
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      4.82
_cell_volume                     1036.32(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
'D8 Quest (Photon II detector/ Chi and Kappa scans)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11315
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         4.82
_exptl_absorpt_coefficient_mu    0.109
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                2282
_reflns_number_total             3703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ce00561g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7232924--7232926.cif.'
_cod_original_cell_volume        1036.32(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7232924
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O7 O 0.5890(3) -0.0038(2) 0.42923(13) 0.0428(6) Uani 1 1 d .
O2 O 0.0280(3) 0.0206(2) 0.10600(11) 0.0255(5) Uani 1 1 d .
H2A H -0.004(4) -0.054(4) 0.0570(19) 0.038 Uiso 1 1 d .
O5 O 0.2252(3) 0.4357(2) 0.42526(12) 0.0369(6) Uani 1 1 d .
O6 O 0.1251(3) 0.2034(3) 0.38508(11) 0.0363(6) Uani 1 1 d .
O3 O 0.2595(3) 0.6991(2) 0.11146(12) 0.0319(5) Uani 1 1 d .
O4 O 0.3015(3) 0.7756(2) 0.23709(12) 0.0327(5) Uani 1 1 d .
O1 O 0.0626(3) 0.1786(2) 0.01730(11) 0.0263(5) Uani 1 1 d .
N2 N 0.1746(3) 0.3309(3) 0.37295(14) 0.0271(6) Uani 1 1 d .
N1 N 0.2610(3) 0.6787(3) 0.18124(15) 0.0249(6) Uani 1 1 d .
C1 C 0.8285(4) 0.8124(4) 0.3103(2) 0.0374(8) Uani 1 1 d .
H1 H 0.8646 0.9098 0.3326 0.045 Uiso 1 1 calc R
C2 C 0.8044(4) 0.7772(3) 0.22950(19) 0.0312(7) Uani 1 1 d .
H2 H 0.8248 0.8514 0.1978 0.037 Uiso 1 1 calc R
C3 C 0.7498(4) 0.6320(3) 0.19427(16) 0.0227(6) Uani 1 1 d .
C4 C 0.7213(4) 0.5895(4) 0.11063(17) 0.0285(7) Uani 1 1 d .
H4 H 0.7397 0.6614 0.0776 0.034 Uiso 1 1 calc R
C5 C 0.6687(4) 0.4486(3) 0.07837(16) 0.0266(7) Uani 1 1 d .
H5 H 0.6532 0.4258 0.0237 0.032 Uiso 1 1 calc R
C6 C 0.6363(4) 0.3333(3) 0.12605(15) 0.0214(6) Uani 1 1 d .
C7 C 0.5790(4) 0.1862(3) 0.09486(17) 0.0299(7) Uani 1 1 d .
H7 H 0.5616 0.1601 0.0404 0.036 Uiso 1 1 calc R
C8 C 0.5476(4) 0.0781(3) 0.14337(19) 0.0320(7) Uani 1 1 d .
H8 H 0.5085 -0.0193 0.1212 0.038 Uiso 1 1 calc R
C14 C 0.7995(4) 0.7042(4) 0.35889(18) 0.0332(8) Uani 1 1 d .
H14 H 0.8163 0.7299 0.4134 0.040 Uiso 1 1 calc R
C13 C 0.7452(4) 0.5567(3) 0.32696(16) 0.0238(7) Uani 1 1 d .
C15 C 0.7192(4) 0.5202(3) 0.24360(15) 0.0193(6) Uani 1 1 d .
C16 C 0.6630(4) 0.3708(3) 0.20958(15) 0.0196(6) Uani 1 1 d .
C9 C 0.5737(4) 0.1139(3) 0.22416(18) 0.0296(7) Uani 1 1 d .
H9 H 0.5529 0.0400 0.2560 0.036 Uiso 1 1 calc R
C10 C 0.6309(4) 0.2591(3) 0.25911(16) 0.0232(7) Uani 1 1 d .
C11 C 0.6594(4) 0.3017(4) 0.34335(17) 0.0293(7) Uani 1 1 d .
H11 H 0.6392 0.2298 0.3764 0.035 Uiso 1 1 calc R
C12 C 0.7140(4) 0.4418(4) 0.37541(17) 0.0282(7) Uani 1 1 d .
H12 H 0.7319 0.4651 0.4301 0.034 Uiso 1 1 calc R
C24 C 0.7138(5) 0.0488(4) 0.50183(19) 0.0419(9) Uani 1 1 d .
H24A H 0.8347 0.1237 0.4942 0.050 Uiso 1 1 calc R
H24B H 0.7638 -0.0299 0.5221 0.050 Uiso 1 1 calc R
C25 C 0.5941(6) 0.1101(4) 0.5600(2) 0.0497(10) Uani 1 1 d .
H25B H 0.6822 0.1427 0.6102 0.060 Uiso 1 1 calc R
H25A H 0.5537 0.1938 0.5418 0.060 Uiso 1 1 calc R
C23 C 0.0669(4) 0.1510(3) 0.08610(16) 0.0189(6) Uani 1 1 d .
C17 C 0.1174(4) 0.2716(3) 0.15310(16) 0.0204(6) Uani 1 1 d .
C18 C 0.1627(4) 0.4154(3) 0.13614(15) 0.0197(6) Uani 1 1 d .
H18 H 0.1591 0.4351 0.0842 0.024 Uiso 1 1 calc R
C19 C 0.2128(4) 0.5272(3) 0.19839(16) 0.0200(6) Uani 1 1 d .
C20 C 0.2184(4) 0.5028(3) 0.27628(16) 0.0224(6) Uani 1 1 d .
H20 H 0.2520 0.5797 0.3174 0.027 Uiso 1 1 calc R
C21 C 0.1718(4) 0.3596(3) 0.29054(15) 0.0214(6) Uani 1 1 d .
C22 C 0.1230(4) 0.2433(3) 0.23069(16) 0.0221(6) Uani 1 1 d .
H22 H 0.0946 0.1480 0.2422 0.027 Uiso 1 1 calc R
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
C24 O7 C25 110.1(2) . 2_656
C23 O2 H2A 109.7(17) . .
O6 N2 O5 124.2(2) . .
O6 N2 C21 117.8(2) . .
O5 N2 C21 118.0(3) . .
O4 N1 O3 124.5(2) . .
O4 N1 C19 117.7(2) . .
O3 N1 C19 117.9(2) . .
C2 C1 C14 120.7(3) . .
C2 C1 H1 119.7 . .
C14 C1 H1 119.7 . .
C1 C2 C3 121.1(3) . .
C1 C2 H2 119.5 . .
C3 C2 H2 119.5 . .
C2 C3 C15 118.7(3) . .
C2 C3 C4 123.3(3) . .
C15 C3 C4 118.0(3) . .
C5 C4 C3 122.0(3) . .
C5 C4 H4 119.0 . .
C3 C4 H4 119.0 . .
C4 C5 C6 121.6(3) . .
C4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C7 C6 C16 118.4(2) . .
C7 C6 C5 123.3(3) . .
C16 C6 C5 118.3(3) . .
C8 C7 C6 121.3(3) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C9 C8 C7 120.5(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C1 C14 C13 120.8(3) . .
C1 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C13 C15 118.6(3) . .
C14 C13 C12 122.4(3) . .
C15 C13 C12 119.1(3) . .
C13 C15 C3 120.2(3) . .
C13 C15 C16 119.7(2) . .
C3 C15 C16 120.1(2) . .
C10 C16 C6 120.0(3) . .
C10 C16 C15 120.0(2) . .
C6 C16 C15 120.0(2) . .
C8 C9 C10 121.1(3) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
C9 C10 C16 118.8(3) . .
C9 C10 C11 123.1(3) . .
C16 C10 C11 118.2(3) . .
C12 C11 C10 121.9(3) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C11 C12 C13 121.1(3) . .
C11 C12 H12 119.4 . .
C13 C12 H12 119.4 . .
O7 C24 C25 111.0(3) . .
O7 C24 H24A 109.4 . .
C25 C24 H24A 109.4 . .
O7 C24 H24B 109.4 . .
C25 C24 H24B 109.4 . .
H24A C24 H24B 108.0 . .
O7 C25 C24 111.0(3) 2_656 .
O7 C25 H25B 109.4 2_656 .
C24 C25 H25B 109.4 . .
O7 C25 H25A 109.4 2_656 .
C24 C25 H25A 109.4 . .
H25B C25 H25A 108.0 . .
O1 C23 O2 124.6(2) . .
O1 C23 C17 120.2(2) . .
O2 C23 C17 115.2(2) . .
C22 C17 C18 120.4(2) . .
C22 C17 C23 121.1(2) . .
C18 C17 C23 118.4(2) . .
C19 C18 C17 118.4(2) . .
C19 C18 H18 120.8 . .
C17 C18 H18 120.8 . .
C18 C19 C20 122.7(3) . .
C18 C19 N1 118.8(2) . .
C20 C19 N1 118.5(2) . .
C19 C20 C21 117.2(3) . .
C19 C20 H20 121.4 . .
C21 C20 H20 121.4 . .
C20 C21 C22 122.7(3) . .
C20 C21 N2 118.2(3) . .
C22 C21 N2 119.1(3) . .
C21 C22 C17 118.6(3) . .
C21 C22 H22 120.7 . .
C17 C22 H22 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 C24 1.402(4) .
O7 C25 1.428(4) 2_656
O2 C23 1.298(3) .
O2 H2A 1.01(3) .
O5 N2 1.228(3) .
O6 N2 1.227(3) .
O3 N1 1.234(3) .
O4 N1 1.219(3) .
O1 C23 1.236(3) .
N2 C21 1.469(3) .
N1 C19 1.472(4) .
C1 C2 1.377(4) .
C1 C14 1.384(4) .
C1 H1 0.9300 .
C2 C3 1.397(4) .
C2 H2 0.9300 .
C3 C15 1.421(4) .
C3 C4 1.431(4) .
C4 C5 1.345(4) .
C4 H4 0.9300 .
C5 C6 1.428(4) .
C5 H5 0.9300 .
C6 C7 1.394(4) .
C6 C16 1.423(4) .
C7 C8 1.384(4) .
C7 H7 0.9300 .
C8 C9 1.376(4) .
C8 H8 0.9300 .
C14 C13 1.401(4) .
C14 H14 0.9300 .
C13 C15 1.420(4) .
C13 C12 1.434(4) .
C15 C16 1.426(4) .
C16 C10 1.423(4) .
C9 C10 1.395(4) .
C9 H9 0.9300 .
C10 C11 1.441(4) .
C11 C12 1.338(4) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C24 C25 1.482(5) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 O7 1.428(4) 2_656
C25 H25B 0.9700 .
C25 H25A 0.9700 .
C23 C17 1.488(4) .
C17 C22 1.386(4) .
C17 C18 1.400(4) .
C18 C19 1.380(4) .
C18 H18 0.9300 .
C19 C20 1.380(4) .
C20 C21 1.381(4) .
C20 H20 0.9300 .
C21 C22 1.381(4) .
C22 H22 0.9300 .
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
C14 C1 C2 C3 0.1(4) . .
C1 C2 C3 C15 0.0(4) . .
C1 C2 C3 C4 179.5(2) . .
C2 C3 C4 C5 180.0(2) . .
C15 C3 C4 C5 -0.5(4) . .
C3 C4 C5 C6 0.6(4) . .
C4 C5 C6 C7 179.1(2) . .
C4 C5 C6 C16 -0.6(4) . .
C16 C6 C7 C8 0.3(4) . .
C5 C6 C7 C8 -179.5(2) . .
C6 C7 C8 C9 -0.4(4) . .
C2 C1 C14 C13 0.0(4) . .
C1 C14 C13 C15 -0.4(4) . .
C1 C14 C13 C12 180.0(2) . .
C14 C13 C15 C3 0.5(3) . .
C12 C13 C15 C3 -179.8(2) . .
C14 C13 C15 C16 -179.7(2) . .
C12 C13 C15 C16 -0.1(3) . .
C2 C3 C15 C13 -0.3(3) . .
C4 C3 C15 C13 -179.9(2) . .
C2 C3 C15 C16 179.9(2) . .
C4 C3 C15 C16 0.3(3) . .
C7 C6 C16 C10 -0.1(3) . .
C5 C6 C16 C10 179.7(2) . .
C7 C6 C16 C15 -179.3(2) . .
C5 C6 C16 C15 0.4(3) . .
C13 C15 C16 C10 0.7(3) . .
C3 C15 C16 C10 -179.5(2) . .
C13 C15 C16 C6 179.9(2) . .
C3 C15 C16 C6 -0.3(3) . .
C7 C8 C9 C10 0.4(4) . .
C8 C9 C10 C16 -0.2(4) . .
C8 C9 C10 C11 179.8(2) . .
C6 C16 C10 C9 0.1(3) . .
C15 C16 C10 C9 179.3(2) . .
C6 C16 C10 C11 -179.9(2) . .
C15 C16 C10 C11 -0.7(3) . .
C9 C10 C11 C12 -179.9(3) . .
C16 C10 C11 C12 0.1(4) . .
C10 C11 C12 C13 0.5(4) . .
C14 C13 C12 C11 179.1(2) . .
C15 C13 C12 C11 -0.5(4) . .
C25 O7 C24 C25 -56.7(4) 2_656 .
O7 C24 C25 O7 57.2(4) . 2_656
O1 C23 C17 C22 -180.0(2) . .
O2 C23 C17 C22 0.5(3) . .
O1 C23 C17 C18 -1.0(3) . .
O2 C23 C17 C18 179.5(2) . .
C22 C17 C18 C19 0.0(3) . .
C23 C17 C18 C19 -179.0(2) . .
C17 C18 C19 C20 -0.5(3) . .
C17 C18 C19 N1 179.9(2) . .
O4 N1 C19 C18 178.8(2) . .
O3 N1 C19 C18 -1.8(3) . .
O4 N1 C19 C20 -0.7(3) . .
O3 N1 C19 C20 178.7(2) . .
C18 C19 C20 C21 0.2(4) . .
N1 C19 C20 C21 179.8(2) . .
C19 C20 C21 C22 0.6(4) . .
C19 C20 C21 N2 -179.4(2) . .
O6 N2 C21 C20 177.2(2) . .
O5 N2 C21 C20 -2.4(3) . .
O6 N2 C21 C22 -2.8(3) . .
O5 N2 C21 C22 177.6(2) . .
C20 C21 C22 C17 -1.1(4) . .
N2 C21 C22 C17 178.9(2) . .
C18 C17 C22 C21 0.8(3) . .
C23 C17 C22 C21 179.7(2) . .
