#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/19/4001993.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_4001993
loop_
_publ_author_name
'Srivastava, Anant Kumar'
'Praveenkumar, B.'
'Mahawar, Indra Kumar'
'Divya, Pillutla'
'Shalini, S.'
'Boomishankar, Ramamoorthy'
_publ_section_title
;
 Anion Driven [CuIIL2]nFrameworks: Crystal Structures,
 Guest-Encapsulation, Dielectric, and Possible Ferroelectric Properties
;
_journal_issue                   12
_journal_name_full               'Chemistry of Materials'
_journal_page_first              3811
_journal_paper_doi               10.1021/cm5014575
_journal_volume                  26
_journal_year                    2014
_chemical_formula_moiety         'C16 H15 N4 O P'
_chemical_formula_sum            'C16 H15 N4 O P'
_chemical_formula_weight         310.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.104(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.300(6)
_cell_length_b                   6.107(4)
_cell_length_c                   22.774(13)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.41
_cell_measurement_theta_min      3.42
_cell_volume                     1430.4(15)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.1042
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17954
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         4.229
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0697
_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)+(0.0785P)²+3.5110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1781
_reflns_number_total             2516
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            compound_L.cif
_cod_data_source_block           compound_L
_cod_depositor_comments
'Adding full bibliography for 4001992--4001997.cif.'
_cod_original_cell_volume        1430.6(15)
_cod_database_code               4001993
#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'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
P1 P 0.08988(11) 0.03038(18) 0.19317(5) 0.0179(3) Uani 1 1 d . .
O1 O 0.1283(3) -0.1996(5) 0.20699(12) 0.0205(7) Uani 1 1 d . .
N1 N 0.2087(3) 0.2070(6) 0.18821(15) 0.0174(8) Uani 1 1 d . .
H1A H 0.2235 0.3010 0.2171 0.021 Uiso 1 1 calc R U
N2 N 0.0097(3) 0.0349(6) 0.12840(15) 0.0167(8) Uani 1 1 d . .
H2 H 0.0002 -0.0932 0.1110 0.020 Uiso 1 1 calc R U
N3 N -0.0706(3) 0.6004(5) 0.08001(15) 0.0172(8) Uani 1 1 d . .
N4 N 0.3810(4) 0.0360(7) 0.05716(17) 0.0256(9) Uani 1 1 d . .
C1 C 0.4472(5) 0.2195(8) 0.0475(2) 0.0273(11) Uani 1 1 d . .
H1B H 0.5035 0.2215 0.0158 0.033 Uiso 1 1 calc R U
C2 C 0.4377(5) 0.4067(8) 0.0813(2) 0.0274(11) Uani 1 1 d . .
H2A H 0.4867 0.5336 0.0728 0.033 Uiso 1 1 calc R U
C3 C 0.3554(4) 0.4067(7) 0.12774(19) 0.0220(10) Uani 1 1 d . .
H3 H 0.3450 0.5343 0.1509 0.026 Uiso 1 1 calc R U
C4 C 0.2890(4) 0.2152(7) 0.13929(18) 0.0166(9) Uani 1 1 d . .
C5 C -0.0456(4) 0.2131(7) 0.09692(17) 0.0138(9) Uani 1 1 d . .
C6 C -0.0180(4) 0.4329(7) 0.11095(18) 0.0154(9) Uani 1 1 d . .
H6 H 0.0401 0.4640 0.1437 0.019 Uiso 1 1 calc R U
C7 C -0.1517(5) 0.5557(7) 0.03395(19) 0.0205(10) Uani 1 1 d . .
H7 H -0.1883 0.6741 0.0116 0.025 Uiso 1 1 calc R U
C8 C 0.3060(4) 0.0352(7) 0.10247(19) 0.0214(10) Uani 1 1 d . .
H8 H 0.2606 -0.0959 0.1105 0.026 Uiso 1 1 calc R U
C9 C -0.1312(4) 0.1716(7) 0.04917(19) 0.0204(10) Uani 1 1 d . .
H9 H -0.1530 0.0253 0.0384 0.025 Uiso 1 1 calc R U
C10 C -0.1846(5) 0.3454(7) 0.0173(2) 0.0243(11) Uani 1 1 d . .
H10 H -0.2433 0.3199 -0.0156 0.029 Uiso 1 1 calc R U
C11 C -0.0093(4) 0.1454(7) 0.24816(19) 0.0196(10) Uani 1 1 d . .
C12 C 0.0009(4) 0.3560(7) 0.27083(19) 0.0198(10) Uani 1 1 d . .
H12 H 0.0628 0.4551 0.2565 0.024 Uiso 1 1 calc R U
C13 C -0.0798(5) 0.4218(8) 0.3145(2) 0.0242(11) Uani 1 1 d . .
H13 H -0.0724 0.5655 0.3303 0.029 Uiso 1 1 calc R U
C14 C -0.1704(5) 0.2784(8) 0.3350(2) 0.0258(11) Uani 1 1 d . .
H14 H -0.2247 0.3235 0.3652 0.031 Uiso 1 1 calc R U
C15 C -0.1829(4) 0.0686(8) 0.3118(2) 0.0270(11) Uani 1 1 d . .
H15 H -0.2463 -0.0290 0.3256 0.032 Uiso 1 1 calc R U
C16 C -0.1030(4) 0.0038(7) 0.26893(19) 0.0216(10) Uani 1 1 d . .
H16 H -0.1115 -0.1396 0.2530 0.026 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'
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
O1 P1 N1 116.40(19)
O1 P1 N2 108.61(17)
N1 P1 N2 105.45(18)
O1 P1 C11 112.0(2)
N1 P1 C11 104.2(2)
N2 P1 C11 109.9(2)
C4 N1 P1 123.0(3)
C4 N1 H1A 118.5
P1 N1 H1A 118.5
C5 N2 P1 129.6(3)
C5 N2 H2 115.2
P1 N2 H2 115.2
C7 N3 C6 118.4(4)
C8 N4 C1 117.2(4)
N4 C1 C2 123.3(4)
N4 C1 H1B 118.4
C2 C1 H1B 118.4
C1 C2 C3 119.1(4)
C1 C2 H2A 120.4
C3 C2 H2A 120.4
C4 C3 C2 118.1(4)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C8 118.0(4)
C3 C4 N1 119.4(4)
C8 C4 N1 122.5(4)
C9 C5 C6 117.7(4)
C9 C5 N2 118.8(4)
C6 C5 N2 123.5(4)
N3 C6 C5 122.6(4)
N3 C6 H6 118.7
C5 C6 H6 118.7
N3 C7 C10 122.8(4)
N3 C7 H7 118.6
C10 C7 H7 118.6
N4 C8 C4 124.2(4)
N4 C8 H8 117.9
C4 C8 H8 117.9
C10 C9 C5 119.3(4)
C10 C9 H9 120.4
C5 C9 H9 120.4
C7 C10 C9 119.2(4)
C7 C10 H10 120.4
C9 C10 H10 120.4
C12 C11 C16 119.1(4)
C12 C11 P1 125.9(4)
C16 C11 P1 115.0(3)
C11 C12 C13 119.9(4)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 120.0(4)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 120.5(4)
C13 C14 H14 119.8
C15 C14 H14 119.8
C16 C15 C14 119.4(4)
C16 C15 H15 120.3
C14 C15 H15 120.3
C15 C16 C11 121.0(4)
C15 C16 H16 119.5
C11 C16 H16 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.488(3)
P1 N1 1.640(4)
P1 N2 1.651(4)
P1 C11 1.801(5)
N1 C4 1.424(5)
N1 H1A 0.8800
N2 C5 1.407(5)
N2 H2 0.8800
N3 C7 1.333(6)
N3 C6 1.340(5)
N4 C8 1.322(6)
N4 C1 1.336(6)
C1 C2 1.385(7)
C1 H1B 0.9500
C2 C3 1.392(7)
C2 H2A 0.9500
C3 C4 1.387(6)
C3 H3 0.9500
C4 C8 1.399(6)
C5 C9 1.386(6)
C5 C6 1.405(6)
C6 H6 0.9500
C7 C10 1.376(6)
C7 H7 0.9500
C8 H8 0.9500
C9 C10 1.382(6)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.388(6)
C11 C16 1.398(6)
C12 C13 1.390(6)
C12 H12 0.9500
C13 C14 1.380(7)
C13 H13 0.9500
C14 C15 1.389(7)
C14 H14 0.9500
C15 C16 1.369(7)
C15 H15 0.9500
C16 H16 0.9500
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 H1A O1 0.88 2.24 2.899(5) 131.1 2
N2 H2 N3 0.88 2.12 2.973(5) 164.7 1_545
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139089336
