#------------------------------------------------------------------------------
#$Date: 2019-05-22 03:36:04 +0300 (Wed, 22 May 2019) $
#$Revision: 215364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/10/1551078.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_1551078
loop_
_publ_author_name
'Mukhopadhyay, Pritam'
'Kumar, sharvan'
'Shukla, Jyoti'
'Mandal, Kalyanshis'
'Kumar, Yogendra'
'Prakash, Ravi'
'Ram, Panch'
_publ_section_title
;
 Doubly-Zwitterionic, Di-reduced, Highly Electron-Rich, Air-Stable
 Naphthalenediimides: Redox-Switchable Islands of Aromatic-Antiaromatic
 States
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00962K
_journal_year                    2019
_chemical_formula_moiety         'C40 H46 N2 O4 P2, 2(B F4)'
_chemical_formula_sum            'C40 H46 B2 F8 N2 O4 P2'
_chemical_formula_weight         854.35
_chemical_melting_point          548.15
_chemical_name_common            'Triethyldiphosphonium NDI dication'
_chemical_name_systematic
"'N,N-dibenzyl-2,6-triethyldiphosphonium-naphthalene-l,4,5,8-tetracarboxylic acid bisimide-bis-tetrafluoroborate' ?"
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-07-05 deposited with the CCDC.    2019-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                94.362(3)
_cell_angle_beta                 91.419(2)
_cell_angle_gamma                116.416(3)
_cell_formula_units_Z            1
_cell_length_a                   9.2333(6)
_cell_length_b                   10.3160(7)
_cell_length_c                   11.4148(8)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.21
_cell_volume                     968.83(12)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1450
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.215
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.988
_exptl_transmission_factor_min   0.969
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0467
_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)+(0.1000P)²+0.0974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4437
_reflns_number_total             4823
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc00962k2.cif
_cod_data_source_block           PMSK39_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '275 \%C' was changed to '548.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1551078
_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_min   0.969
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
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
P1 P 0.09730(4) 0.82314(3) 0.72645(3) 0.00751(12) Uani 1 1 d . .
F2 F 0.30851(11) 0.80547(10) 0.22786(8) 0.0241(2) Uani 1 1 d . .
F3 F 0.13590(11) 0.84354(10) 0.34838(8) 0.0240(2) Uani 1 1 d . .
F1 F 0.33832(11) 1.03474(10) 0.27389(9) 0.0241(2) Uani 1 1 d . .
F4 F 0.12263(11) 0.87302(11) 0.15379(8) 0.0253(2) Uani 1 1 d . .
O2 O 0.35735(11) 0.55217(10) 0.45376(8) 0.0121(2) Uani 1 1 d . .
O1 O 0.72462(11) 0.87302(10) 0.23271(8) 0.0142(2) Uani 1 1 d . .
N1 N 0.55230(12) 0.71358(11) 0.35018(9) 0.0087(2) Uani 1 1 d . .
C1 C 0.37100(14) 1.02423(13) 0.61525(10) 0.0076(2) Uani 1 1 d . .
C5 C 0.51097(14) 0.94389(12) 0.46860(10) 0.0073(2) Uani 1 1 d . .
C3 C 0.29285(14) 0.76904(13) 0.56969(11) 0.0086(2) Uani 1 1 d . .
H3 H 0.2263 0.6726 0.5814 0.010 Uiso 1 1 calc R U
C6 C 0.63929(14) 0.85242(13) 0.31551(11) 0.0088(2) Uani 1 1 d . .
C9 C 0.46073(15) 0.49635(13) 0.20027(11) 0.0095(2) Uani 1 1 d . .
C4 C 0.41180(14) 0.79917(13) 0.49133(10) 0.0076(2) Uani 1 1 d . .
C2 C 0.26886(14) 0.88023(13) 0.63298(10) 0.0078(2) Uani 1 1 d . .
C19 C -0.04289(15) 0.89075(14) 0.68121(11) 0.0109(3) Uani 1 1 d . .
H19A H -0.1236 0.8707 0.7390 0.013 Uiso 1 1 calc R U
H19B H 0.0157 0.9955 0.6808 0.013 Uiso 1 1 calc R U
C10 C 0.38675(16) 0.54946(14) 0.12185(11) 0.0124(3) Uani 1 1 d . .
H10 H 0.4090 0.6470 0.1304 0.015 Uiso 1 1 calc R U
C14 C 0.42658(16) 0.35028(14) 0.18579(11) 0.0122(3) Uani 1 1 d . .
H14 H 0.4743 0.3140 0.2385 0.015 Uiso 1 1 calc R U
C17 C 0.15673(16) 0.86559(15) 0.88196(11) 0.0143(3) Uani 1 1 d . .
H17A H 0.1568 0.9574 0.9080 0.017 Uiso 1 1 calc R U
H17B H 0.0771 0.7910 0.9246 0.017 Uiso 1 1 calc R U
C7 C 0.43494(14) 0.67769(13) 0.43189(11) 0.0086(2) Uani 1 1 d . .
C8 C 0.58502(15) 0.59538(13) 0.29640(11) 0.0102(3) Uani 1 1 d . .
H8A H 0.5902 0.5371 0.3577 0.012 Uiso 1 1 calc R U
H8B H 0.6904 0.6381 0.2638 0.012 Uiso 1 1 calc R U
C11 C 0.27950(16) 0.45604(15) 0.03065(12) 0.0155(3) Uani 1 1 d . .
H11 H 0.2286 0.4913 -0.0206 0.019 Uiso 1 1 calc R U
C12 C 0.24774(16) 0.31049(15) 0.01544(12) 0.0162(3) Uani 1 1 d . .
H12 H 0.1774 0.2491 -0.0464 0.019 Uiso 1 1 calc R U
C13 C 0.32145(16) 0.25762(14) 0.09300(12) 0.0155(3) Uani 1 1 d . .
H13 H 0.3009 0.1605 0.0833 0.019 Uiso 1 1 calc R U
C15 C -0.01627(16) 0.62665(14) 0.70160(12) 0.0127(3) Uani 1 1 d . .
H15A H -0.1255 0.5996 0.7250 0.015 Uiso 1 1 calc R U
H15B H -0.0240 0.5994 0.6176 0.015 Uiso 1 1 calc R U
C20 C -0.12955(17) 0.82577(15) 0.56018(12) 0.0170(3) Uani 1 1 d . .
H20A H -0.0509 0.8382 0.5031 0.025 Uiso 1 1 calc R U
H20B H -0.1928 0.8742 0.5388 0.025 Uiso 1 1 calc R U
H20C H -0.1995 0.7240 0.5624 0.025 Uiso 1 1 calc R U
C16 C 0.04955(18) 0.53594(15) 0.76442(14) 0.0202(3) Uani 1 1 d . .
H16A H 0.1568 0.5590 0.7410 0.030 Uiso 1 1 calc R U
H16B H -0.0200 0.4344 0.7436 0.030 Uiso 1 1 calc R U
H16C H 0.0531 0.5575 0.8481 0.030 Uiso 1 1 calc R U
B1 B 0.22599(18) 0.88848(16) 0.25017(13) 0.0129(3) Uani 1 1 d . .
C18 C 0.32429(18) 0.8762(2) 0.91255(13) 0.0271(4) Uani 1 1 d . .
H18A H 0.3285 0.7893 0.8805 0.041 Uiso 1 1 calc R U
H18B H 0.3438 0.8873 0.9966 0.041 Uiso 1 1 calc R U
H18C H 0.4056 0.9587 0.8798 0.041 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
C19 P1 C17 112.61(6) . .
C19 P1 C15 104.85(6) . .
C17 P1 C15 106.55(6) . .
C19 P1 C2 110.88(6) . .
C17 P1 C2 113.52(6) . .
C15 P1 C2 107.85(6) . .
C7 N1 C6 124.37(10) . .
C7 N1 C8 117.34(10) . .
C6 N1 C8 118.30(10) . .
C2 C1 C5 120.28(11) . 2_676
C2 C1 C6 121.41(11) . 2_676
C5 C1 C6 118.31(10) 2_676 2_676
C5 C5 C4 118.36(14) 2_676 .
C5 C5 C1 120.71(13) 2_676 2_676
C4 C5 C1 120.93(11) . 2_676
C4 C3 C2 121.91(11) . .
C4 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
O1 C6 N1 120.96(11) . .
O1 C6 C1 120.87(11) . 2_676
N1 C6 C1 118.14(10) . 2_676
C14 C9 C10 119.28(12) . .
C14 C9 C8 118.94(11) . .
C10 C9 C8 121.67(11) . .
C3 C4 C5 120.38(11) . .
C3 C4 C7 119.06(11) . .
C5 C4 C7 120.56(11) . .
C1 C2 C3 118.24(11) . .
C1 C2 P1 124.73(9) . .
C3 C2 P1 116.94(9) . .
C20 C19 P1 114.40(9) . .
C20 C19 H19A 108.7 . .
P1 C19 H19A 108.7 . .
C20 C19 H19B 108.7 . .
P1 C19 H19B 108.7 . .
H19A C19 H19B 107.6 . .
C11 C10 C9 119.85(12) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C9 C14 C13 120.71(12) . .
C9 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C18 C17 P1 113.20(9) . .
C18 C17 H17A 108.9 . .
P1 C17 H17A 108.9 . .
C18 C17 H17B 108.9 . .
P1 C17 H17B 108.9 . .
H17A C17 H17B 107.8 . .
O2 C7 N1 120.89(11) . .
O2 C7 C4 122.43(11) . .
N1 C7 C4 116.67(10) . .
N1 C8 C9 114.58(10) . .
N1 C8 H8A 108.6 . .
C9 C8 H8A 108.6 . .
N1 C8 H8B 108.6 . .
C9 C8 H8B 108.6 . .
H8A C8 H8B 107.6 . .
C12 C11 C10 120.62(13) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C13 C12 C11 119.61(13) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 119.91(12) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C16 C15 P1 117.43(10) . .
C16 C15 H15A 107.9 . .
P1 C15 H15A 107.9 . .
C16 C15 H15B 107.9 . .
P1 C15 H15B 107.9 . .
H15A C15 H15B 107.2 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
F4 B1 F2 110.58(11) . .
F4 B1 F3 109.36(11) . .
F2 B1 F3 109.39(11) . .
F4 B1 F1 109.53(11) . .
F2 B1 F1 109.15(11) . .
F3 B1 F1 108.80(11) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C19 1.8038(13) .
P1 C17 1.8066(13) .
P1 C15 1.8153(13) .
P1 C2 1.8286(12) .
F2 B1 1.3913(16) .
F3 B1 1.3948(17) .
F1 B1 1.3989(17) .
F4 B1 1.3901(17) .
O2 C7 1.2186(15) .
O1 C6 1.2155(15) .
N1 C7 1.3881(15) .
N1 C6 1.3898(15) .
N1 C8 1.4758(15) .
C1 C2 1.3949(16) .
C1 C5 1.4116(17) 2_676
C1 C6 1.4870(16) 2_676
C5 C5 1.409(2) 2_676
C5 C4 1.4103(16) .
C5 C1 1.4116(17) 2_676
C3 C4 1.3749(17) .
C3 C2 1.4123(16) .
C3 H3 0.9300 .
C6 C1 1.4870(16) 2_676
C9 C14 1.3907(17) .
C9 C10 1.3947(18) .
C9 C8 1.5128(17) .
C4 C7 1.4807(16) .
C19 C20 1.5250(18) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C10 C11 1.3930(18) .
C10 H10 0.9300 .
C14 C13 1.3955(18) .
C14 H14 0.9300 .
C17 C18 1.531(2) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C11 C12 1.392(2) .
C11 H11 0.9300 .
C12 C13 1.385(2) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C15 C16 1.5316(18) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
