#------------------------------------------------------------------------------
#$Date: 2017-03-09 01:57:57 +0200 (Thu, 09 Mar 2017) $
#$Revision: 194100 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125851.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_4125851
loop_
_publ_author_name
'Lipke, Mark C.'
'Cheng, Tao'
'Wu, Yilei'
'Arslan, Hasan'
'Xiao, Hai'
'Wasielewski, Michael R.'
'Goddard, William A.'
'Stoddart, J. Fraser'
_publ_section_title
;
 Size-Matched Radical Multivalency.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.6b09892
_journal_year                    2017
_chemical_formula_moiety         '2(F6 P), C36 H32 N4'
_chemical_formula_sum            'C36 H32 F12 N4 P2'
_chemical_formula_weight         810.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 126.9238(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.6496(9)
_cell_length_b                   8.7129(3)
_cell_length_c                   20.6646(12)
_cell_measurement_reflns_used    7162
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.056
_cell_measurement_theta_min      3.447
_cell_volume                     3691.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13001
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.447
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.916
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0718 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.8139.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0475
_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)+(0.0772P)²+3.8858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3074
_reflns_number_total             3584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b09892_si_003.cif
_cod_data_source_block           ml3_0ma
_cod_database_code               4125851
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H17A(0.5) H17B(0.5) H24A(0.5) H24B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C17(H17A,H17B), C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C3(H3), C10(H10), C9(H9), C4(H4), C21(H21), C12(H12),
 C19(H19), C16(H16), C22(H22), C11(H11), C15(H15), C23(H23)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
P3 P 0.19010(4) 0.0000 0.41917(4) 0.0313(2) Uani 1 2 d S T P
F3 F 0.22767(9) 0.0000 0.51467(10) 0.0395(4) Uani 1 2 d S T P
F1 F 0.15106(10) 0.0000 0.32270(11) 0.0581(6) Uani 1 2 d S T P
F2 F 0.23675(8) 0.12891(18) 0.42629(9) 0.0555(4) Uani 1 1 d . . .
F4 F 0.14179(8) 0.1291(2) 0.41026(9) 0.0669(5) Uani 1 1 d . . .
P4 P 0.30795(4) 0.5000 0.11031(4) 0.0311(2) Uani 1 2 d S T P
F8 F 0.27333(8) 0.5000 0.15436(10) 0.0347(4) Uani 1 2 d S T P
F7 F 0.35690(8) 0.3708(2) 0.17154(9) 0.0573(4) Uani 1 1 d . . .
F5 F 0.25969(8) 0.37164(18) 0.05031(9) 0.0574(4) Uani 1 1 d . . .
F6 F 0.34431(11) 0.5000 0.06888(12) 0.0535(6) Uani 1 2 d S T P
C8 C 0.46575(9) 0.3222(2) 0.47097(11) 0.0240(4) Uani 1 1 d . . .
N2 N 0.32907(8) 0.30812(18) 0.35336(9) 0.0246(4) Uani 1 1 d . . .
C7 C 0.43453(9) 0.3232(2) 0.38569(11) 0.0251(4) Uani 1 1 d . . .
H7 H 0.4606 0.3293 0.3673 0.030 Uiso 1 1 calc R . .
C6 C 0.36926(9) 0.3159(2) 0.33089(11) 0.0259(4) Uani 1 1 d . . .
H6 H 0.3507 0.3162 0.2749 0.031 Uiso 1 1 calc R . .
C5 C 0.25498(12) 0.0000 0.28496(15) 0.0226(5) Uani 1 2 d S T P
H5 H 0.2685 0.0000 0.3390 0.027 Uiso 1 2 calc RS T P
C3 C 0.22573(9) 0.1376(2) 0.16663(12) 0.0306(5) Uani 1 1 d . . .
H3 H 0.2192 0.2319 0.1396 0.037 Uiso 1 1 calc R . .
C10 C 0.35601(9) 0.3092(2) 0.43405(11) 0.0255(4) Uani 1 1 d . . .
H10 H 0.3283 0.3047 0.4502 0.031 Uiso 1 1 calc R . .
C9 C 0.42136(9) 0.3166(2) 0.49122(11) 0.0245(4) Uani 1 1 d . . .
H9 H 0.4383 0.3181 0.5466 0.029 Uiso 1 1 calc R . .
C4 C 0.21585(15) 0.0000 0.12751(16) 0.0334(7) Uani 1 2 d S T P
H4 H 0.2022 0.0000 0.0734 0.040 Uiso 1 2 calc RS T P
C2 C 0.24520(9) 0.1383(2) 0.24576(11) 0.0243(4) Uani 1 1 d . . .
C1 C 0.25850(9) 0.2867(2) 0.29071(12) 0.0282(4) Uani 1 1 d . . .
H1A H 0.2410 0.3735 0.2521 0.034 Uiso 1 1 calc R . .
H1B H 0.2360 0.2857 0.3163 0.034 Uiso 1 1 calc R . .
C21 C 0.42898(15) 0.0000 0.28578(18) 0.0328(6) Uani 1 2 d S T P
H21 H 0.3880 0.0000 0.2766 0.039 Uiso 1 2 calc RS T P
N4 N 0.61760(11) 0.0000 -0.07480(14) 0.0352(6) Uani 1 2 d S T P
C20 C 0.43178(15) 0.0000 0.22068(18) 0.0344(7) Uani 1 2 d S T P
C12 C 0.59262(10) 0.1377(3) 0.00256(13) 0.0386(5) Uani 1 1 d . . .
H12 H 0.5847 0.2334 0.0173 0.046 Uiso 1 1 calc R . .
C19 C 0.49235(15) 0.0000 0.23628(19) 0.0427(8) Uani 1 2 d S T P
H19 H 0.4947 0.0000 0.1921 0.051 Uiso 1 2 calc RS T P
C16 C 0.60084(10) 0.1352(4) 0.21646(14) 0.0467(6) Uani 1 1 d . . .
H16 H 0.6023 0.2292 0.2409 0.056 Uiso 1 1 calc R . .
N3 N 0.61017(12) 0.0000 0.25598(16) 0.0461(8) Uani 1 2 d S T P
C22 C 0.48608(16) 0.0000 0.36391(19) 0.0347(7) Uani 1 2 d S T P
H22 H 0.4838 0.0000 0.4081 0.042 Uiso 1 2 calc RS T P
C11 C 0.60761(10) 0.1350(3) -0.05043(13) 0.0381(5) Uani 1 1 d . . .
H11 H 0.6112 0.2290 -0.0708 0.046 Uiso 1 1 calc R . .
C15 C 0.58953(10) 0.1382(3) 0.14345(13) 0.0431(6) Uani 1 1 d . . .
H15 H 0.5832 0.2340 0.1177 0.052 Uiso 1 1 calc R . .
C14 C 0.58701(15) 0.0000 0.10447(19) 0.0407(8) Uani 1 2 d S T P
C23 C 0.54648(15) 0.0000 0.37902(18) 0.0332(7) Uani 1 2 d S T P
H23 H 0.5853 0.0000 0.4331 0.040 Uiso 1 2 calc RS T P
C13 C 0.58852(14) 0.0000 0.03631(18) 0.0378(7) Uani 1 2 d S T P
C17 C 0.61612(16) 0.0000 0.33126(19) 0.0514(10) Uani 1 2 d S T P
H17A H 0.6409 0.0919 0.3635 0.062 Uiso 0.5 1 calc R . .
H17B H 0.6409 -0.0919 0.3635 0.062 Uiso 0.5 1 calc R . .
C18 C 0.54982(15) 0.0000 0.31474(18) 0.0374(7) Uani 1 2 d S T P
C24 C 0.63084(15) 0.0000 -0.13480(18) 0.0383(7) Uani 1 2 d S T P
H24A H 0.6569 -0.0919 -0.1267 0.046 Uiso 0.5 1 calc R . .
H24B H 0.6569 0.0919 -0.1267 0.046 Uiso 0.5 1 calc R . .
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
F3 P3 F1 179.01(11) . .
F3 P3 F4 89.59(8) . 6
F3 P3 F4 89.59(8) . .
F2 P3 F3 91.37(8) 6 .
F2 P3 F3 91.37(8) . .
F2 P3 F1 89.32(8) 6 .
F2 P3 F1 89.32(8) . .
F2 P3 F2 90.46(13) 6 .
F2 P3 F4 178.88(11) . 6
F2 P3 F4 90.10(10) 6 6
F2 P3 F4 178.87(11) 6 .
F2 P3 F4 90.10(10) . .
F4 P3 F1 89.71(8) 6 .
F4 P3 F1 89.71(8) . .
F4 P3 F4 89.33(15) 6 .
F7 P4 F8 89.44(7) 6_565 .
F7 P4 F8 89.43(7) . .
F7 P4 F7 89.99(14) . 6_565
F7 P4 F6 89.45(8) 6_565 .
F7 P4 F6 89.45(8) . .
F5 P4 F8 90.32(8) . .
F5 P4 F8 90.32(8) 6_565 .
F5 P4 F7 179.61(9) . 6_565
F5 P4 F7 89.71(9) . .
F5 P4 F7 89.71(9) 6_565 6_565
F5 P4 F7 179.61(9) 6_565 .
F5 P4 F5 90.58(13) . 6_565
F5 P4 F6 90.79(8) . .
F5 P4 F6 90.79(8) 6_565 .
F6 P4 F8 178.42(11) . .
C8 C8 C7 122.4(2) 2_656 .
C8 C8 C9 123.7(2) 2_656 .
C9 C8 C7 113.91(17) . .
C6 N2 C10 118.88(16) . .
C6 N2 C1 119.21(15) . .
C10 N2 C1 121.73(16) . .
C6 C7 C8 121.89(17) . .
C7 C6 N2 121.92(17) . .
C2 C5 C2 120.5(2) 6 .
C4 C3 C2 120.05(19) . .
C9 C10 N2 121.20(17) . .
C10 C9 C8 122.18(17) . .
C3 C4 C3 120.4(2) . 6
C5 C2 C3 119.51(18) . .
C5 C2 C1 119.38(17) . .
C3 C2 C1 121.07(17) . .
N2 C1 C2 110.76(15) . .
C22 C21 C20 119.7(3) . .
C11 N4 C11 119.3(3) 6 .
C11 N4 C24 120.12(13) . .
C11 N4 C24 120.12(13) 6 .
C21 C20 C24 119.9(3) . 5_655
C19 C20 C21 118.6(3) . .
C19 C20 C24 121.6(3) . 5_655
C11 C12 C13 121.3(2) . .
C20 C19 C18 121.8(3) . .
C15 C16 N3 121.6(3) . .
C16 N3 C16 118.6(3) 6 .
C16 N3 C17 120.07(14) 6 .
C16 N3 C17 120.07(14) . .
C21 C22 C23 121.4(3) . .
C12 C11 N4 121.2(2) . .
C16 C15 C14 121.3(3) . .
C15 C14 C15 114.9(3) 6 .
C15 C14 C13 122.41(15) 6 .
C15 C14 C13 122.41(15) . .
C18 C23 C22 119.4(3) . .
C12 C13 C12 114.9(3) . 6
C12 C13 C14 122.39(14) . .
C12 C13 C14 122.39(14) 6 .
N3 C17 C18 111.8(3) . .
C19 C18 C17 121.4(3) . .
C23 C18 C19 119.1(3) . .
C23 C18 C17 119.4(3) . .
N4 C24 C20 111.6(2) . 5_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P3 F3 1.5932(18) .
P3 F1 1.6057(19) .
P3 F2 1.5821(14) 6
P3 F2 1.5822(15) .
P3 F4 1.6001(15) .
P3 F4 1.6000(15) 6
P4 F8 1.6091(17) .
P4 F7 1.5927(15) .
P4 F7 1.5927(15) 6_565
P4 F5 1.5736(15) .
P4 F5 1.5736(15) 6_565
P4 F6 1.6007(19) .
C8 C8 1.412(4) 2_656
C8 C7 1.432(2) .
C8 C9 1.430(3) .
N2 C6 1.363(2) .
N2 C10 1.369(2) .
N2 C1 1.474(2) .
C7 C6 1.346(3) .
C5 C2 1.388(2) 6
C5 C2 1.388(2) .
C3 C4 1.382(3) .
C3 C2 1.393(3) .
C10 C9 1.353(3) .
C4 C3 1.382(3) 6
C2 C1 1.506(3) .
C21 C20 1.390(4) .
C21 C22 1.382(4) .
N4 C11 1.363(3) 6
N4 C11 1.363(3) .
N4 C24 1.469(4) .
C20 C19 1.384(4) .
C20 C24 1.518(4) 5_655
C12 C11 1.361(3) .
C12 C13 1.423(3) .
C19 C18 1.389(4) .
C16 N3 1.370(3) .
C16 C15 1.355(3) .
N3 C16 1.370(3) 6
N3 C17 1.469(4) .
C22 C23 1.384(5) .
C15 C14 1.428(3) .
C14 C15 1.428(3) 6
C14 C13 1.432(4) .
C23 C18 1.381(4) .
C13 C12 1.423(3) 6
C17 C18 1.520(5) .
C24 C20 1.518(4) 5_655
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 0.000 230.2 39.3
2 0.102 0.500 0.575 8.1 0.0
3 0.500 0.500 1.000 230.2 39.3
4 0.398 0.000 0.425 8.1 0.0
5 0.602 0.000 0.575 8.1 0.0
6 0.898 0.500 0.425 8.1 0.0
