#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:26:35 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554511.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_1554511
loop_
_publ_author_name
'Ng, Chee Koon'
'Tam, Teck Lip Dexter'
'Wei, Fengxia'
'Lu, Xuefeng'
'Wu, Jishan'
_publ_section_title
;
 Anion--π and anion--π-radical interactions in
 bis(triphenylphosphonium)-naphthalene diimide salts
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              110
_journal_paper_doi               10.1039/C8QO01122B
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C66 H66 N2 O4 P2, Br1'
_chemical_formula_sum            'C66 H66 Br N2 O4 P2'
_chemical_formula_weight         1095.72
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   24.7543(7)
_cell_length_b                   24.7543(7)
_cell_length_c                   30.0212(9)
_cell_measurement_reflns_used    89076
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.506
_cell_measurement_theta_min      3.595
_cell_volume                     15931.6(8)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APPEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            89076
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.506
_diffrn_reflns_theta_min         3.595
_exptl_absorpt_coefficient_mu    1.553
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5168
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.147
_exptl_transmission_factor_max   0.804
_exptl_transmission_factor_min   0.705
_refine_diff_density_max         1.929
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         6700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.005
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.1345
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3998
_refine_ls_wR_factor_ref         0.4175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5690
_reflns_number_total             6700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01122b2.cif
_cod_data_source_block           cu_i180_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        15931.6(10)
_cod_original_sg_symbol_H-M      'R -3'
_cod_original_formula_sum        'C66 H66 Br1 N2 O4 P2'
_cod_database_code               1554511
_shelx_shelxl_version_number     2018/3
_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_max   0.804
_shelx_estimated_absorpt_t_min   0.705
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br2(0.11333) Br1(0.242) Br0A(0.14)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C4(H4A,H4B), C5(H5A,H5B), C3AA(H3AA,H3AB), C5AA(H5AA,H5AB)
3.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30),
  C32(H32)
3.d Idealised Me refined as rotating group:
 C4AA(H4AA,H4AB,H4AC), C6AA(H6AA,H6AB,H6AC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.42705(5) 0.00344(4) 0.13037(3) 0.0585(4) Uani 1 1 d . . .
O4 O 0.34718(16) -0.04694(19) -0.08421(9) 0.0774(8) Uani 1 1 d . . .
N5 N 0.34268(16) -0.04132(16) -0.00863(10) 0.0615(7) Uani 1 1 d . . .
C1 C 0.36861(18) -0.03345(17) 0.03393(10) 0.0580(8) Uani 1 1 d . . .
C2 C 0.3742(2) -0.0378(2) -0.04833(11) 0.0644(9) Uani 1 1 d . . .
C0AA C 0.43920(19) -0.02102(18) -0.04383(11) 0.0604(8) Uani 1 1 d . . .
C2AA C 0.43410(18) -0.01350(17) 0.03732(11) 0.0577(8) Uani 1 1 d . . .
C1AA C 0.47301(19) -0.01832(19) -0.08169(10) 0.0614(8) Uani 1 1 d . . .
H1AA H 0.452590 -0.028557 -0.109775 0.074 Uiso 1 1 calc R . .
C6 C 0.46813(18) -0.00880(17) -0.00118(10) 0.0570(8) Uani 1 1 d . . .
C7 C 0.46446(19) 0.00115(18) 0.07966(10) 0.0586(8) Uani 1 1 d . . .
C8 C 0.4892(2) 0.0383(2) 0.17108(11) 0.0633(9) Uani 1 1 d . . .
C10 C 0.2779(2) -0.0550(2) -0.01254(13) 0.0675(9) Uani 1 1 d . . .
H10A H 0.256301 -0.070246 0.016375 0.081 Uiso 1 1 calc R . .
H10B H 0.255641 -0.088103 -0.035056 0.081 Uiso 1 1 calc R . .
C11 C 0.3958(2) 0.0546(2) 0.12523(12) 0.0698(10) Uani 1 1 d . . .
C12 C 0.3738(2) -0.0719(2) 0.15326(13) 0.0668(9) Uani 1 1 d . . .
C13 C 0.5930(3) 0.0922(3) 0.22627(16) 0.0883(14) Uani 1 1 d . . .
H13 H 0.628833 0.110673 0.244856 0.106 Uiso 1 1 calc R . .
C14 C 0.5104(2) 0.0016(2) 0.19112(11) 0.0719(10) Uani 1 1 d . . .
H14 H 0.489220 -0.042135 0.185954 0.086 Uiso 1 1 calc R . .
C15 C 0.5623(3) 0.0286(3) 0.21847(13) 0.0838(13) Uani 1 1 d . . .
H15 H 0.576824 0.003531 0.231928 0.101 Uiso 1 1 calc R . .
C16 C 0.5197(2) 0.1017(2) 0.17920(15) 0.0760(10) Uani 1 1 d . . .
H16 H 0.505615 0.127252 0.165913 0.091 Uiso 1 1 calc R . .
C17 C 0.3421(3) 0.0428(3) 0.14873(17) 0.0842(13) Uani 1 1 d . . .
H17 H 0.321194 0.007252 0.167425 0.101 Uiso 1 1 calc R . .
C18 C 0.3583(2) -0.1264(2) 0.13039(17) 0.0778(11) Uani 1 1 d . . .
H18 H 0.369603 -0.125146 0.100016 0.093 Uiso 1 1 calc R . .
C19 C 0.3554(3) -0.0744(3) 0.19769(15) 0.0819(12) Uani 1 1 d . . .
H19 H 0.366156 -0.037090 0.213460 0.098 Uiso 1 1 calc R . .
C20 C 0.3213(3) -0.1318(4) 0.2184(2) 0.1004(19) Uani 1 1 d . . .
H20 H 0.307218 -0.133844 0.248107 0.120 Uiso 1 1 calc R . .
C21 C 0.4270(3) 0.1065(3) 0.09776(17) 0.0892(14) Uani 1 1 d . . .
H21 H 0.463058 0.113206 0.081839 0.107 Uiso 1 1 calc R . .
C22 C 0.5725(3) 0.1279(3) 0.20777(19) 0.0935(14) Uani 1 1 d . . .
H22 H 0.593526 0.171370 0.213860 0.112 Uiso 1 1 calc R . .
C23 C 0.3256(3) -0.1832(3) 0.1528(3) 0.0964(15) Uani 1 1 d . . .
H23 H 0.315466 -0.220949 0.137888 0.116 Uiso 1 1 calc R . .
C24 C 0.3079(3) -0.1847(3) 0.1967(2) 0.102(2) Uani 1 1 d . . .
H24 H 0.285999 -0.223564 0.211717 0.123 Uiso 1 1 calc R . .
C27 C 0.3204(4) 0.0835(4) 0.1442(2) 0.109(2) Uani 1 1 d . . .
H27 H 0.283472 0.075626 0.159402 0.131 Uiso 1 1 calc R . .
C30 C 0.4055(5) 0.1484(4) 0.0936(2) 0.118(3) Uani 1 1 d . . .
H30 H 0.426188 0.184273 0.075208 0.142 Uiso 1 1 calc R . .
C32 C 0.3508(5) 0.1352(5) 0.1183(3) 0.129(3) Uani 1 1 d . . .
H32 H 0.335319 0.163320 0.116566 0.155 Uiso 1 1 calc R . .
Br2 Br 0.333333 0.666667 0.11756(13) 0.0936(8) Uani 0.34 3 d S T P
O1 O 0.33612(14) -0.04271(14) 0.06726(8) 0.0643(7) Uani 1 1 d . . .
C3 C 0.2769(3) 0.0064(3) -0.0269(2) 0.0941(15) Uani 1 1 d . . .
H3 H 0.297994 0.020660 -0.056445 0.113 Uiso 1 1 calc R . .
C4 C 0.2083(4) -0.0114(5) -0.0320(4) 0.130(3) Uani 1 1 d . . .
H4A H 0.186306 -0.032419 -0.004222 0.156 Uiso 1 1 calc R . .
H4B H 0.206676 0.027639 -0.034460 0.156 Uiso 1 1 calc R . .
C5 C 0.3089(5) 0.0583(4) 0.0057(2) 0.111(2) Uani 1 1 d . . .
H5A H 0.350767 0.064556 0.012543 0.133 Uiso 1 1 calc R . .
H5B H 0.284633 0.047381 0.033758 0.133 Uiso 1 1 calc R . .
C3AA C 0.1744(4) -0.0504(4) -0.0684(4) 0.133(3) Uani 1 1 d . . .
H3AA H 0.172084 -0.091233 -0.064633 0.160 Uiso 1 1 calc R . .
H3AB H 0.197727 -0.031438 -0.096187 0.160 Uiso 1 1 calc R . .
C4AA C 0.3151(7) 0.1179(5) -0.0131(3) 0.151(4) Uani 1 1 d . . .
H4AA H 0.326083 0.121228 -0.044777 0.226 Uiso 1 1 calc GR . .
H4AB H 0.347905 0.153761 0.002982 0.226 Uiso 1 1 calc GR . .
H4AC H 0.275434 0.117263 -0.009801 0.226 Uiso 1 1 calc GR . .
C5AA C 0.1082(6) -0.0615(7) -0.0736(8) 0.241(11) Uani 1 1 d . . .
H5AA H 0.081906 -0.089732 -0.049470 0.290 Uiso 1 1 calc R . .
H5AB H 0.109268 -0.021277 -0.069747 0.290 Uiso 1 1 calc R . .
Br1 Br 0.2628(2) -0.2243(3) 0.32592(13) 0.1488(18) Uani 0.242 1 d . . .
Br0A Br 0.4709(5) 0.2587(6) -0.0189(6) 0.1892(6) Uani 0.14 1 d . . .
C6AA C 0.0800(11) -0.0877(11) -0.1150(10) 0.326(18) Uani 1 1 d . . .
H6AA H 0.096325 -0.055026 -0.137915 0.489 Uiso 1 1 calc GR . .
H6AB H 0.034692 -0.105597 -0.112632 0.489 Uiso 1 1 calc GR . .
H6AC H 0.089314 -0.120408 -0.123305 0.489 Uiso 1 1 calc GR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C7 P1 C8 104.99(17) . .
C7 P1 C12 114.38(18) . .
C11 P1 C7 111.15(17) . .
C11 P1 C8 106.56(19) . .
C11 P1 C12 114.6(2) . .
C12 P1 C8 104.14(19) . .
C1 N5 C2 124.4(3) . .
C1 N5 C10 118.5(3) . .
C2 N5 C10 117.1(3) . .
N5 C1 C2AA 118.1(3) . .
O1 C1 N5 120.3(4) . .
O1 C1 C2AA 121.6(3) . .
O4 C2 N5 120.0(4) . .
O4 C2 C0AA 123.8(3) . .
N5 C2 C0AA 116.1(3) . .
C1AA C0AA C2 119.4(3) . .
C1AA C0AA C6 119.8(4) . .
C6 C0AA C2 120.8(3) . .
C6 C2AA C1 119.8(3) . .
C6 C2AA C7 119.7(3) . .
C7 C2AA C1 120.5(3) . .
C7 C1AA C0AA 122.0(3) 10_655 .
C2AA C6 C0AA 120.5(3) . .
C2AA C6 C6 121.1(4) . 10_655
C6 C6 C0AA 118.4(4) 10_655 .
C2AA C7 P1 123.2(3) . .
C1AA C7 P1 117.8(3) 10_655 .
C1AA C7 C2AA 118.8(3) 10_655 .
C14 C8 P1 119.2(3) . .
C16 C8 P1 120.9(3) . .
C16 C8 C14 119.6(4) . .
N5 C10 C3 109.7(4) . .
C17 C11 P1 120.6(4) . .
C21 C11 P1 117.8(4) . .
C21 C11 C17 121.6(4) . .
C18 C12 P1 121.6(3) . .
C18 C12 C19 120.2(4) . .
C19 C12 P1 117.6(4) . .
C22 C13 C15 120.4(5) . .
C15 C14 C8 120.1(5) . .
C14 C15 C13 120.0(5) . .
C8 C16 C22 118.8(5) . .
C27 C17 C11 118.6(6) . .
C12 C18 C23 118.7(5) . .
C20 C19 C12 119.4(6) . .
C24 C20 C19 120.5(5) . .
C30 C21 C11 119.9(6) . .
C13 C22 C16 120.9(6) . .
C24 C23 C18 120.2(6) . .
C20 C24 C23 120.9(5) . .
C32 C27 C17 121.0(7) . .
C21 C30 C32 117.1(7) . .
C27 C32 C30 121.9(6) . .
C4 C3 C10 107.2(5) . .
C5 C3 C10 112.9(5) . .
C5 C3 C4 110.4(6) . .
C3AA C4 C3 117.8(8) . .
C3 C5 C4AA 110.2(7) . .
C4 C3AA C5AA 114.7(13) . .
C6AA C5AA C3AA 114(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C7 1.798(3) .
P1 C8 1.810(4) .
P1 C11 1.792(4) .
P1 C12 1.797(4) .
O4 C2 1.227(5) .
N5 C1 1.399(5) .
N5 C2 1.403(4) .
N5 C10 1.468(5) .
C1 C2AA 1.443(5) .
C1 O1 1.231(4) .
C2 C0AA 1.454(6) .
C0AA C1AA 1.393(5) .
C0AA C6 1.424(5) .
C2AA C6 1.400(5) .
C2AA C7 1.428(5) .
C1AA C7 1.386(6) 10_655
C6 C6 1.413(8) 10_655
C8 C14 1.395(6) .
C8 C16 1.379(6) .
C10 C3 1.593(7) .
C11 C17 1.401(7) .
C11 C21 1.390(8) .
C12 C18 1.386(7) .
C12 C19 1.401(6) .
C13 C15 1.383(9) .
C13 C22 1.340(9) .
C14 C15 1.382(7) .
C16 C22 1.420(8) .
C17 C27 1.365(8) .
C18 C23 1.395(8) .
C19 C20 1.384(8) .
C20 C24 1.348(11) .
C21 C30 1.389(8) .
C23 C24 1.382(11) .
C27 C32 1.357(14) .
C30 C32 1.431(14) .
C3 C4 1.533(10) .
C3 C5 1.488(11) .
C4 C3AA 1.421(14) .
C5 C4AA 1.515(9) .
C3AA C5AA 1.527(16) .
C5AA C6AA 1.42(3) .
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 0.000 0.000 938.8 69.8
2 0.333 0.667 0.667 938.8 69.8
3 0.667 0.333 0.333 938.8 69.8
