#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218976.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_7218976
loop_
_publ_author_name
'Yadav, Ashok'
'Ramamoorthy, Boomishankar'
_publ_section_title
;
 Concentration dependent ratiometric turn-on selective fluorescence
 detection of picric acid in aqueous and non-aqueous media
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA15207G
_journal_year                    2014
_chemical_formula_sum            'C27 H27 N6 O4 P'
_chemical_formula_weight         530.51
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-09-18 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   16.08(2)
_cell_length_b                   16.08(2)
_cell_length_c                   6.269(8)
_cell_measurement_reflns_used    2612
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      2.53
_cell_volume                     1404(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker Smart Apex Duo'
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1479
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14052
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_min         4.122
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colurless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             556
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0863
_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)+(0.1859P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2637
_refine_ls_wR_factor_ref         0.2874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1426
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra15207g2.cif
_cod_data_source_block           TRIAL2
_cod_original_cell_volume        1404(4)
_cod_database_code               7218976
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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
P1 P 0.6667 0.3333 0.4591(3) 0.0226(4) Uani 1 3 d S T P
O1 O 0.6667 0.3333 0.6990(7) 0.0258(9) Uani 1 3 d S T P
N1 N 0.6165(2) 0.3930(2) 0.3577(5) 0.0263(7) Uani 1 1 d . . .
H1 H 0.6493 0.4361 0.2593 0.032 Uiso 1 1 calc R U .
C11 C 0.5254(2) 0.3811(2) 0.4145(6) 0.0261(8) Uani 1 1 d . . .
C12 C 0.4814(3) 0.4158(3) 0.2675(6) 0.0285(8) Uani 1 1 d . . .
H12 H 0.5157 0.4465 0.1413 0.034 Uiso 1 1 calc R U .
N13 N 0.3960(2) 0.4077(2) 0.2964(5) 0.0320(8) Uani 1 1 d . . .
C14 C 0.3451(3) 0.3619(3) 0.4784(6) 0.0291(8) Uani 1 1 d . . .
C15 C 0.3837(3) 0.3277(3) 0.6368(6) 0.0281(8) Uani 1 1 d . . .
C16 C 0.4767(3) 0.3390(3) 0.6018(6) 0.0286(8) Uani 1 1 d . . .
H16 H 0.5049 0.3178 0.7062 0.034 Uiso 1 1 calc R U .
C17 C 0.3283(3) 0.2818(3) 0.8231(7) 0.0358(9) Uani 1 1 d . . .
H17 H 0.3538 0.2591 0.9304 0.043 Uiso 1 1 calc R U .
C18 C 0.2379(3) 0.2704(4) 0.8470(8) 0.0451(11) Uani 1 1 d . . .
H18 H 0.2017 0.2406 0.9719 0.054 Uiso 1 1 calc R U .
C19 C 0.1986(3) 0.3031(4) 0.6858(8) 0.0472(12) Uani 1 1 d . . .
H19 H 0.1357 0.2935 0.7024 0.057 Uiso 1 1 calc R U .
C20 C 0.2512(3) 0.3484(3) 0.5059(8) 0.0422(10) Uani 1 1 d . . .
H20 H 0.2247 0.3708 0.4001 0.051 Uiso 1 1 calc R U .
O1S O 0.5113(2) 0.1897(2) 0.9527(5) 0.0350(7) Uani 1 1 d D . .
H1S H 0.479(4) 0.136(4) 0.881(8) 0.052 Uiso 1 1 d D U .
H2S H 0.557(4) 0.226(4) 0.862(8) 0.052 Uiso 1 1 d D 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'
P P 0.1023 0.0942 '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
O1 P1 N1 112.56(12) . 2_655
O1 P1 N1 112.56(12) . 3_665
N1 P1 N1 106.22(14) 2_655 3_665
O1 P1 N1 112.56(12) . .
N1 P1 N1 106.22(14) 2_655 .
N1 P1 N1 106.22(14) 3_665 .
C11 N1 P1 126.2(2) . .
C11 N1 H1 116.9 . .
P1 N1 H1 116.9 . .
C16 C11 N1 124.7(3) . .
C16 C11 C12 117.8(3) . .
N1 C11 C12 117.5(3) . .
N13 C12 C11 124.3(4) . .
N13 C12 H12 117.9 . .
C11 C12 H12 117.9 . .
C12 N13 C14 118.2(3) . .
N13 C14 C15 121.8(3) . .
N13 C14 C20 118.7(4) . .
C15 C14 C20 119.5(4) . .
C14 C15 C17 119.4(3) . .
C14 C15 C16 118.4(3) . .
C17 C15 C16 122.2(3) . .
C11 C16 C15 119.4(3) . .
C11 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C18 C17 C15 120.0(4) . .
C18 C17 H17 120.0 . .
C15 C17 H17 120.0 . .
C17 C18 C19 120.4(4) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C20 C19 C18 120.5(4) . .
C20 C19 H19 119.8 . .
C18 C19 H19 119.8 . .
C19 C20 C14 120.1(4) . .
C19 C20 H20 119.9 . .
C14 C20 H20 119.9 . .
H1S O1S H2S 102(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.504(5) .
P1 N1 1.658(4) 2_655
P1 N1 1.658(4) 3_665
P1 N1 1.658(4) .
N1 C11 1.424(5) .
N1 H1 0.8800 .
C11 C16 1.385(5) .
C11 C12 1.434(5) .
C12 N13 1.326(5) .
C12 H12 0.9500 .
N13 C14 1.383(5) .
C14 C15 1.419(5) .
C14 C20 1.424(6) .
C15 C17 1.430(5) .
C15 C16 1.431(5) .
C16 H16 0.9500 .
C17 C18 1.379(6) .
C17 H17 0.9500 .
C18 C19 1.425(7) .
C18 H18 0.9500 .
C19 C20 1.379(7) .
C19 H19 0.9500 .
C20 H20 0.9500 .
O1S H1S 0.88(4) .
O1S H2S 0.88(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1S 0.88 2.06 2.876(5) 154.5 3_664
O1S H1S N13 0.88(4) 2.06(4) 2.938(5) 177(6) 5_556
O1S H2S O1 0.88(4) 2.02(4) 2.887(5) 167(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199569
