#------------------------------------------------------------------------------
#$Date: 2021-11-06 21:51:52 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243457.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_7243457
loop_
_publ_author_name
'Sendh, Jagajiban'
'Singh, Munendra Pal'
'Baruah, Jubaraj B.'
_publ_section_title
;
 5-[(Pyren-9-ylmethyl)amino]isophthalic acid with nitrogen containing
 heterocycles: stacking, N--H⋯π interactions and photoluminescence
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6952
_journal_page_last               6966
_journal_paper_doi               10.1039/D1CE01099A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C31 H21 N2 O4'
_chemical_formula_weight         485.50
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-02-01 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                103.891(6)
_cell_angle_beta                 95.539(6)
_cell_angle_gamma                112.603(7)
_cell_formula_units_Z            2
_cell_length_a                   8.8551(7)
_cell_length_b                   9.9074(7)
_cell_length_c                   14.9941(12)
_cell_measurement_reflns_used    2131
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.0550
_cell_measurement_theta_min      3.7550
_cell_volume                     1152.44(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8015
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         2.916
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0582
_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)+(0.0597P)²+0.6308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2823
_reflns_number_total             4082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01099a2.cif
_cod_data_source_block           H2LPHEN
_cod_depositor_comments
'Adding full bibliography for 7243455--7243460.cif.'
_cod_original_cell_volume        1152.43(17)
_cod_database_code               7243457
_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.
;
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
O1 O 0.6250(2) 0.6798(2) 0.08999(16) 0.0594(6) Uani 1 1 d . . . . .
H1A H 0.5771 0.7284 0.0729 0.089 Uiso 1 1 calc R U . . .
N2 N 0.5195(2) 0.8786(2) 0.02645(15) 0.0411(5) Uani 1 1 d . . . . .
O4 O 1.0541(2) 0.4886(3) 0.1163(2) 0.0802(8) Uani 1 1 d . . . . .
H4 H 1.1451 0.4867 0.1129 0.120 Uiso 1 1 calc R U . . .
O2 O 0.3829(2) 0.5619(3) 0.12633(19) 0.0760(7) Uani 1 1 d . . . . .
O3 O 1.0135(3) 0.2880(3) 0.16600(19) 0.0815(8) Uani 1 1 d . . . . .
N1 N 0.4806(3) 0.2075(3) 0.29290(19) 0.0625(7) Uani 1 1 d . . . . .
H1 H 0.4054 0.2305 0.3161 0.075 Uiso 1 1 calc R U . . .
C2 C 0.5969(3) 0.4805(3) 0.15573(18) 0.0387(6) Uani 1 1 d . . . . .
C6 C 0.8055(3) 0.3836(3) 0.16694(18) 0.0395(6) Uani 1 1 d . . . . .
C28 C 0.6254(3) 0.9590(3) -0.01988(18) 0.0396(6) Uani 1 1 d . . . . .
C7 C 0.7459(3) 0.4786(3) 0.13565(18) 0.0398(6) Uani 1 1 d . . . . .
H7 H 0.8053 0.5402 0.1016 0.048 Uiso 1 1 calc R U . . .
C29 C 0.3937(3) 0.9176(3) 0.04607(18) 0.0406(6) Uani 1 1 d . . . . .
C4 C 0.5691(3) 0.2945(3) 0.24049(19) 0.0454(7) Uani 1 1 d . . . . .
C10 C 0.6369(3) 0.1214(3) 0.39804(18) 0.0435(6) Uani 1 1 d . . . . .
C8 C 0.9663(3) 0.3797(3) 0.1502(2) 0.0490(7) Uani 1 1 d . . . . .
C3 C 0.5095(3) 0.3897(3) 0.20763(18) 0.0440(6) Uani 1 1 d . . . . .
H3 H 0.4099 0.3921 0.2208 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7176(3) 0.2922(3) 0.21867(18) 0.0440(6) Uani 1 1 d . . . . .
H5 H 0.7587 0.2288 0.2389 0.053 Uiso 1 1 calc R U . . .
C15 C 0.6573(3) 0.0060(3) 0.42905(19) 0.0451(7) Uani 1 1 d . . . . .
C1 C 0.5233(3) 0.5768(3) 0.12309(19) 0.0449(7) Uani 1 1 d . . . . .
C23 C 0.8013(3) -0.0694(3) 0.54483(19) 0.0463(7) Uani 1 1 d . . . . .
C27 C 0.7569(3) 0.9195(3) -0.0453(2) 0.0485(7) Uani 1 1 d . . . . .
H27 H 0.7703 0.8391 -0.0293 0.058 Uiso 1 1 calc R U . . .
C30 C 0.2771(3) 0.8349(3) 0.0930(2) 0.0515(7) Uani 1 1 d . . . . .
H30 H 0.2858 0.7525 0.1087 0.062 Uiso 1 1 calc R U . . .
C13 C 0.8834(3) 0.2030(3) 0.55912(19) 0.0500(7) Uani 1 1 d . . . . .
C14 C 0.7786(3) 0.0441(3) 0.51000(19) 0.0455(7) Uani 1 1 d . . . . .
C26 C 0.8627(3) 0.9989(4) -0.0927(2) 0.0557(8) Uani 1 1 d . . . . .
H26 H 0.9465 0.9706 -0.1107 0.067 Uiso 1 1 calc R U . . .
C31 C 0.1527(4) 0.8758(4) 0.1151(2) 0.0595(8) Uani 1 1 d . . . . .
H31 H 0.0762 0.8204 0.1456 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5056(3) 0.0798(4) 0.3117(2) 0.0550(8) Uani 1 1 d . . . . .
H9A H 0.5365 0.0288 0.2576 0.066 Uiso 1 1 calc R U . . .
H9B H 0.3999 0.0069 0.3184 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5554(4) -0.1561(3) 0.3813(2) 0.0538(7) Uani 1 1 d . . . . .
H16 H 0.4744 -0.1854 0.3275 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7402(4) 0.2737(3) 0.4467(2) 0.0574(8) Uani 1 1 d . . . . .
H11 H 0.7280 0.3510 0.4260 0.069 Uiso 1 1 calc R U . . .
C12 C 0.8616(4) 0.3123(4) 0.5260(2) 0.0589(8) Uani 1 1 d . . . . .
H12 H 0.9295 0.4152 0.5572 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6964(4) -0.2290(4) 0.4957(2) 0.0584(8) Uani 1 1 d . . . . .
C24 C 1.0261(4) 0.1268(4) 0.6716(2) 0.0672(9) Uani 1 1 d . . . . .
H24 H 1.1087 0.1547 0.7243 0.081 Uiso 1 1 calc R U . . .
C22 C 0.9225(4) -0.0305(4) 0.6260(2) 0.0601(8) Uani 1 1 d . . . . .
C17 C 0.5768(4) -0.2649(4) 0.4140(2) 0.0603(8) Uani 1 1 d . . . . .
H17 H 0.5100 -0.3675 0.3815 0.072 Uiso 1 1 calc R U . . .
C21 C 0.9377(5) -0.1471(5) 0.6588(3) 0.0711(10) Uani 1 1 d . . . . .
H21 H 1.0172 -0.1217 0.7125 0.085 Uiso 1 1 calc R U . . .
C25 C 1.0070(4) 0.2376(4) 0.6396(2) 0.0639(9) Uani 1 1 d . . . . .
H25 H 1.0772 0.3398 0.6714 0.077 Uiso 1 1 calc R U . . .
C19 C 0.7185(5) -0.3396(4) 0.5305(3) 0.0709(10) Uani 1 1 d . . . . .
H19 H 0.6540 -0.4430 0.4989 0.085 Uiso 1 1 calc R U . . .
C20 C 0.8369(6) -0.2968(6) 0.6126(3) 0.0854(12) Uani 1 1 d . . . . .
H20 H 0.8470 -0.3724 0.6361 0.102 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
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C28 N2 C29 117.3(2) . . ?
C8 O4 H4 109.5 . . ?
C4 N1 C9 124.5(2) . . ?
C4 N1 H1 117.7 . . ?
C9 N1 H1 117.7 . . ?
C7 C2 C3 120.2(2) . . ?
C7 C2 C1 122.5(2) . . ?
C3 C2 C1 117.3(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 C8 121.9(2) . . ?
C5 C6 C8 117.6(2) . . ?
N2 C28 C27 119.7(2) . . ?
N2 C28 C29 121.3(2) . 2_675 ?
C27 C28 C29 119.0(2) . 2_675 ?
C2 C7 C6 119.3(2) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N2 C29 C30 119.6(2) . . ?
N2 C29 C28 121.4(2) . 2_675 ?
C30 C29 C28 119.0(2) . 2_675 ?
N1 C4 C5 122.3(2) . . ?
N1 C4 C3 119.6(2) . . ?
C5 C4 C3 118.0(2) . . ?
C11 C10 C15 119.1(3) . . ?
C11 C10 C9 120.8(3) . . ?
C15 C10 C9 120.1(2) . . ?
O3 C8 O4 122.7(3) . . ?
O3 C8 C6 124.2(3) . . ?
O4 C8 C6 113.1(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C10 C15 C14 120.3(3) . . ?
C10 C15 C16 122.4(3) . . ?
C14 C15 C16 117.2(3) . . ?
O2 C1 O1 122.6(2) . . ?
O2 C1 C2 123.3(2) . . ?
O1 C1 C2 114.2(2) . . ?
C22 C23 C14 121.8(3) . . ?
C22 C23 C18 119.3(3) . . ?
C14 C23 C18 118.8(3) . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C31 C30 C29 120.0(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C12 C13 C25 123.4(3) . . ?
C12 C13 C14 118.8(3) . . ?
C25 C13 C14 117.8(3) . . ?
C15 C14 C23 122.1(3) . . ?
C15 C14 C13 119.2(3) . . ?
C23 C14 C13 118.7(2) . . ?
C27 C26 C31 120.8(3) . 2_675 ?
C27 C26 H26 119.6 . . ?
C31 C26 H26 119.6 2_675 . ?
C30 C31 C26 121.2(3) . 2_675 ?
C30 C31 H31 119.4 . . ?
C26 C31 H31 119.4 2_675 . ?
N1 C9 C10 115.3(3) . . ?
N1 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
N1 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C19 C18 C17 123.2(3) . . ?
C19 C18 C23 118.6(3) . . ?
C17 C18 C23 118.2(3) . . ?
C25 C24 C22 121.2(3) . . ?
C25 C24 H24 119.4 . . ?
C22 C24 H24 119.4 . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 C24 122.3(3) . . ?
C23 C22 C24 118.1(3) . . ?
C16 C17 C18 122.7(3) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C24 C25 C13 122.3(3) . . ?
C24 C25 H25 118.8 . . ?
C13 C25 H25 118.8 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
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
O1 C1 1.312(3) . ?
O1 H1A 0.8200 . ?
N2 C28 1.347(3) . ?
N2 C29 1.348(3) . ?
O4 C8 1.311(3) . ?
O4 H4 0.8200 . ?
O2 C1 1.201(3) . ?
O3 C8 1.196(3) . ?
N1 C4 1.378(3) . ?
N1 C9 1.450(4) . ?
N1 H1 0.8600 . ?
C2 C7 1.388(3) . ?
C2 C3 1.390(3) . ?
C2 C1 1.489(3) . ?
C6 C7 1.389(3) . ?
C6 C5 1.393(3) . ?
C6 C8 1.483(4) . ?
C28 C27 1.420(4) . ?
C28 C29 1.433(3) 2_675 ?
C7 H7 0.9300 . ?
C29 C30 1.414(4) . ?
C29 C28 1.433(3) 2_675 ?
C4 C5 1.393(4) . ?
C4 C3 1.402(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.398(4) . ?
C10 C9 1.511(4) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C15 C14 1.409(4) . ?
C15 C16 1.455(4) . ?
C23 C22 1.410(4) . ?
C23 C14 1.419(4) . ?
C23 C18 1.444(4) . ?
C27 C26 1.354(4) . ?
C27 H27 0.9300 . ?
C30 C31 1.355(4) . ?
C30 H30 0.9300 . ?
C13 C12 1.362(4) . ?
C13 C25 1.425(4) . ?
C13 C14 1.439(4) . ?
C26 C31 1.412(4) 2_675 ?
C26 H26 0.9300 . ?
C31 C26 1.412(4) 2_675 ?
C31 H31 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C16 C17 1.354(4) . ?
C16 H16 0.9300 . ?
C11 C12 1.391(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C18 C19 1.389(4) . ?
C18 C17 1.414(4) . ?
C24 C25 1.358(5) . ?
C24 C22 1.416(5) . ?
C24 H24 0.9300 . ?
C22 C21 1.404(4) . ?
C17 H17 0.9300 . ?
C21 C20 1.358(5) . ?
C21 H21 0.9300 . ?
C25 H25 0.9300 . ?
C19 C20 1.397(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
