#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:53:02 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/23/7042320.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_7042320
loop_
_publ_author_name
'Aghabali, Amineh'
'Jun, Sharon'
'Olmstead, Marilyn M.'
'Balch, Alan L.'
_publ_section_title
;
 Piperazine-functionalized C60 and diiodine or iodine monochloride as
 components in forming supramolecular assemblies.
;
_journal_issue                   11
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3710
_journal_page_last               3715
_journal_paper_doi               10.1039/c7dt00026j
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C64 H8 N2, 2.884(C6 H6), 2(I2), 0.116(I2)'
_chemical_formula_sum            'C81.3 H25.3 I4.23 N2'
_chemical_formula_weight         1566.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-01-03 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.748(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0074(12)
_cell_length_b                   16.2272(19)
_cell_length_c                   16.3038(19)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.88
_cell_measurement_theta_min      2.44
_cell_volume                     2571.8(5)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'Apex2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34350
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.797
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.620
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2013)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_description       block
_exptl_crystal_F_000             1503
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.092
_refine_diff_density_max         2.629
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0697P)²+13.1591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5314
_reflns_number_total             6128
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt00026j1.cif
_cod_data_source_block           aa54_a
_cod_depositor_comments
'Adding full bibliography for 7042319--7042321.cif.'
_cod_original_formula_sum        'C81.30 H25.30 I4.23 N2'
_cod_database_code               7042320
_shelx_shelxl_version_number     2016/6
_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   0.402
_shelx_estimated_absorpt_t_max   0.794
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.26215(3) -0.01712(2) 0.52562(2) 0.02827(11) Uani 1 1 d . . . . .
I2 I 0.07362(3) -0.04257(3) 0.37276(2) 0.03763(13) Uani 1 1 d . . . . .
N1 N 0.4247(4) 0.0035(3) 0.6748(2) 0.0231(8) Uani 1 1 d . . . . .
C1 C 0.4526(4) 0.0915(3) 0.7025(3) 0.0189(8) Uani 1 1 d . . . . .
C2 C 0.3159(4) 0.1385(3) 0.6923(3) 0.0214(9) Uani 1 1 d . . . . .
C3 C 0.2652(5) 0.1651(3) 0.7582(3) 0.0220(9) Uani 1 1 d . . . . .
C4 C 0.3523(5) 0.1653(3) 0.8458(3) 0.0224(9) Uani 1 1 d . . . . .
C5 C 0.4858(5) 0.1379(3) 0.8621(3) 0.0224(9) Uani 1 1 d . . . . .
C6 C 0.4085(5) 0.1847(3) 0.5812(3) 0.0239(9) Uani 1 1 d . . . . .
C7 C 0.2870(5) 0.1846(3) 0.6146(3) 0.0252(10) Uani 1 1 d . . . . .
C8 C 0.2024(5) 0.2543(3) 0.6045(3) 0.0280(10) Uani 1 1 d . . . . .
C9 C 0.1455(5) 0.2808(3) 0.6733(4) 0.0297(11) Uani 1 1 d . . . . .
C10 C 0.1781(5) 0.2378(3) 0.7491(3) 0.0268(10) Uani 1 1 d . . . . .
C11 C 0.2092(5) 0.2824(3) 0.8287(3) 0.0278(10) Uani 1 1 d . . . . .
C12 C 0.3159(5) 0.2378(3) 0.8872(3) 0.0266(10) Uani 1 1 d . . . . .
C13 C 0.4167(6) 0.2814(3) 0.9444(3) 0.0288(11) Uani 1 1 d . . . . .
C14 C 0.4422(6) 0.2537(4) 0.5394(3) 0.0299(11) Uani 1 1 d . . . . .
C15 C 0.3561(6) 0.3270(4) 0.5297(3) 0.0318(11) Uani 1 1 d . . . . .
C16 C 0.2379(5) 0.3267(4) 0.5617(3) 0.0324(11) Uani 1 1 d . . . . .
C17 C 0.2017(6) 0.3986(4) 0.6041(4) 0.0347(12) Uani 1 1 d . . . . .
C18 C 0.1452(5) 0.3713(4) 0.6731(4) 0.0328(12) Uani 1 1 d . . . . .
C19 C 0.1756(5) 0.4132(4) 0.7492(4) 0.0347(12) Uani 1 1 d . . . . .
C20 C 0.2069(5) 0.3686(4) 0.8286(4) 0.0324(12) Uani 1 1 d . . . . .
C21 C 0.5853(6) 0.3712(4) 0.5558(3) 0.0335(12) Uani 1 1 d . . . . .
C22 C 0.4432(6) 0.3992(4) 0.5397(3) 0.0340(12) Uani 1 1 d . . . . .
C23 C 0.4105(7) 0.4683(4) 0.5814(4) 0.0373(13) Uani 1 1 d . . . . .
C24 C 0.2860(6) 0.4682(4) 0.6138(4) 0.0368(13) Uani 1 1 d . . . . .
C25 C 0.3171(6) 0.5122(3) 0.6926(4) 0.0361(13) Uani 1 1 d . . . . .
C26 C 0.2620(6) 0.4855(3) 0.7595(4) 0.0354(12) Uani 1 1 d . . . . .
C27 C 0.3460(6) 0.4859(3) 0.8435(4) 0.0367(13) Uani 1 1 d . . . . .
C28 C 0.3120(6) 0.4136(4) 0.8875(4) 0.0338(12) Uani 1 1 d . . . . .
C29 C 0.5159(7) 0.5122(3) 0.6396(4) 0.0364(13) Uani 1 1 d . . . . .
C30 C 0.4596(6) 0.5395(3) 0.7097(4) 0.0373(13) Uani 1 1 d . . . . .
C31 C 0.3524(6) -0.0393(3) 0.7332(3) 0.0284(10) Uani 1 1 d . . . . .
H31A H 0.330605 -0.096593 0.713808 0.034 Uiso 1 1 calc R U . . .
H31B H 0.264926 -0.010564 0.732645 0.034 Uiso 1 1 calc R U . . .
C32 C 0.5555(5) -0.0398(3) 0.6762(3) 0.0281(10) Uani 1 1 d . . . . .
H32A H 0.603795 -0.012073 0.637408 0.034 Uiso 1 1 calc R U . . .
H32B H 0.536210 -0.097338 0.656770 0.034 Uiso 1 1 calc R U . . .
C33 C -0.0848(6) 0.2581(5) 0.4587(4) 0.0498(18) Uani 1 1 d . . . . .
H33 H -0.134753 0.234652 0.495755 0.060 Uiso 1 1 calc R U . . .
C34 C -0.0104(7) 0.2057(5) 0.4162(4) 0.0449(14) Uani 1 1 d . . . . .
H34 H -0.011096 0.147651 0.423493 0.054 Uiso 1 1 calc R U . . .
C35 C 0.0637(6) 0.2414(5) 0.3635(4) 0.0441(15) Uani 1 1 d . . . . .
H35 H 0.113205 0.207208 0.333719 0.053 Uiso 1 1 calc R U . . .
C36 C 0.0665(6) 0.3266(5) 0.3536(4) 0.0452(15) Uani 1 1 d . . . . .
H36 H 0.119572 0.350173 0.318420 0.054 Uiso 1 1 calc R U . . .
C37 C -0.0077(7) 0.3768(5) 0.3950(4) 0.0521(17) Uani 1 1 d . . . . .
H37 H -0.006087 0.434858 0.388190 0.062 Uiso 1 1 calc R U . . .
C38 C -0.0866(7) 0.3412(5) 0.4478(4) 0.0520(18) Uani 1 1 d . . . . .
H38 H -0.139990 0.375152 0.475227 0.062 Uiso 1 1 calc R U . . .
C39 C 0.3565(6) 0.7328(3) 0.7296(3) 0.0268(11) Uani 0.884(2) 1 d G . P A 1
H39 H 0.258771 0.733760 0.715708 0.032 Uiso 0.884(2) 1 calc R U P A 1
C40 C 0.4283(5) 0.7331(3) 0.6664(3) 0.0242(11) Uani 0.884(2) 1 d G . P A 1
H40 H 0.379658 0.734745 0.608779 0.029 Uiso 0.884(2) 1 calc R U P A 1
C41 C 0.5712(5) 0.731(3) 0.6874(7) 0.0446(12) Uani 0.884(2) 1 d G . P A 1
H41 H 0.619570 0.728338 0.643901 0.054 Uiso 0.884(2) 1 calc R U P A 1
I3 I 0.5807(5) 0.7268(13) 0.6915(4) 0.0446(12) Uani 0.116(2) 1 d . . P A 2
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
C32 N1 C31 109.2(4) . .
C32 N1 C1 110.2(4) . .
C31 N1 C1 109.5(4) . .
N1 C1 C5 109.6(4) . 2_656
N1 C1 C2 109.9(4) . .
C5 C1 C2 100.0(4) 2_656 .
N1 C1 C1 108.3(2) . 2_656
C5 C1 C1 114.7(4) 2_656 2_656
C2 C1 C1 114.0(4) . 2_656
C3 C2 C7 119.6(4) . .
C3 C2 C1 124.0(4) . .
C7 C2 C1 109.8(4) . .
C2 C3 C10 120.2(5) . .
C2 C3 C4 121.0(4) . .
C10 C3 C4 107.3(4) . .
C5 C4 C12 121.0(5) . .
C5 C4 C3 120.5(4) . .
C12 C4 C3 107.2(4) . .
C4 C5 C6 119.0(5) . 2_656
C4 C5 C1 123.8(4) . 2_656
C6 C5 C1 110.1(4) 2_656 2_656
C14 C6 C5 120.7(5) . 2_656
C14 C6 C7 120.6(5) . .
C5 C6 C7 108.2(4) 2_656 .
C8 C7 C2 120.8(5) . .
C8 C7 C6 119.7(5) . .
C2 C7 C6 108.7(4) . .
C7 C8 C9 119.4(5) . .
C7 C8 C16 120.0(5) . .
C9 C8 C16 108.7(5) . .
C10 C9 C8 119.4(5) . .
C10 C9 C18 120.2(5) . .
C8 C9 C18 107.3(5) . .
C9 C10 C3 120.4(5) . .
C9 C10 C11 120.0(5) . .
C3 C10 C11 108.5(5) . .
C20 C11 C12 120.7(5) . .
C20 C11 C10 119.9(5) . .
C12 C11 C10 107.9(4) . .
C13 C12 C4 120.2(5) . .
C13 C12 C11 119.4(5) . .
C4 C12 C11 109.1(4) . .
C12 C13 C14 119.0(5) . 2_656
C12 C13 C21 119.9(5) . 2_656
C14 C13 C21 108.9(5) 2_656 2_656
C6 C14 C13 120.0(5) . 2_656
C6 C14 C15 120.2(5) . .
C13 C14 C15 107.0(5) 2_656 .
C16 C15 C22 120.0(5) . .
C16 C15 C14 119.1(5) . .
C22 C15 C14 109.0(5) . .
C15 C16 C17 120.2(5) . .
C15 C16 C8 120.4(5) . .
C17 C16 C8 107.8(5) . .
C24 C17 C18 119.9(6) . .
C24 C17 C16 119.6(5) . .
C18 C17 C16 108.2(5) . .
C19 C18 C17 120.3(5) . .
C19 C18 C9 119.3(5) . .
C17 C18 C9 107.9(5) . .
C18 C19 C26 120.1(5) . .
C18 C19 C20 120.6(5) . .
C26 C19 C20 107.8(5) . .
C11 C20 C28 119.8(5) . .
C11 C20 C19 120.0(5) . .
C28 C20 C19 108.0(5) . .
C28 C21 C22 120.2(5) 2_656 .
C28 C21 C13 120.2(5) 2_656 2_656
C22 C21 C13 107.4(5) . 2_656
C23 C22 C15 120.2(5) . .
C23 C22 C21 119.7(6) . .
C15 C22 C21 107.8(5) . .
C22 C23 C29 120.3(5) . .
C22 C23 C24 119.6(6) . .
C29 C23 C24 108.5(5) . .
C17 C24 C25 120.0(5) . .
C17 C24 C23 120.2(6) . .
C25 C24 C23 107.5(6) . .
C26 C25 C24 120.0(6) . .
C26 C25 C30 119.6(6) . .
C24 C25 C30 108.5(5) . .
C25 C26 C27 119.6(5) . .
C25 C26 C19 119.8(6) . .
C27 C26 C19 108.4(5) . .
C29 C27 C26 121.0(5) 2_656 .
C29 C27 C28 118.7(6) 2_656 .
C26 C27 C28 108.4(5) . .
C21 C28 C20 119.9(5) 2_656 .
C21 C28 C27 120.2(5) 2_656 .
C20 C28 C27 107.4(5) . .
C27 C29 C23 120.8(6) 2_656 .
C27 C29 C30 118.9(6) 2_656 .
C23 C29 C30 108.1(5) . .
C30 C30 C25 120.8(6) 2_656 .
C30 C30 C29 120.1(7) 2_656 .
C25 C30 C29 107.5(6) . .
N1 C31 C32 110.1(4) . 2_656
N1 C31 H31A 109.7 . .
C32 C31 H31A 109.7 2_656 .
N1 C31 H31B 109.7 . .
C32 C31 H31B 109.7 2_656 .
H31A C31 H31B 108.2 . .
N1 C32 C31 109.6(4) . 2_656
N1 C32 H32A 109.7 . .
C31 C32 H32A 109.7 2_656 .
N1 C32 H32B 109.7 . .
C31 C32 H32B 109.7 2_656 .
H32A C32 H32B 108.2 . .
C38 C33 C34 121.6(6) . .
C38 C33 H33 119.2 . .
C34 C33 H33 119.2 . .
C35 C34 C33 118.3(7) . .
C35 C34 H34 120.9 . .
C33 C34 H34 120.9 . .
C34 C35 C36 120.9(6) . .
C34 C35 H35 119.5 . .
C36 C35 H35 119.5 . .
C37 C36 C35 120.0(6) . .
C37 C36 H36 120.0 . .
C35 C36 H36 120.0 . .
C36 C37 C38 119.8(7) . .
C36 C37 H37 120.1 . .
C38 C37 H37 120.1 . .
C33 C38 C37 119.3(6) . .
C33 C38 H38 120.3 . .
C37 C38 H38 120.3 . .
C41 C39 C40 119.1(9) 2_656 .
C41 C39 H39 120.5 2_656 .
C40 C39 H39 120.5 . .
C39 C40 C41 120.0 . .
C39 C40 H40 120.0 . .
C41 C40 H40 120.0 . .
C39 C41 C40 120.8(6) 2_656 .
C39 C41 H41 119.6 2_656 .
C40 C41 H41 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I2 2.7760(5) .
N1 C32 1.482(6) .
N1 C31 1.497(6) .
N1 C1 1.503(6) .
C1 C5 1.537(6) 2_656
C1 C2 1.541(6) .
C1 C1 1.614(8) 2_656
C2 C3 1.364(7) .
C2 C7 1.441(7) .
C3 C10 1.452(7) .
C3 C4 1.485(7) .
C4 C5 1.373(7) .
C4 C12 1.446(7) .
C5 C6 1.444(7) 2_656
C6 C14 1.393(8) .
C6 C7 1.444(7) .
C7 C8 1.399(7) .
C8 C9 1.438(7) .
C8 C16 1.453(8) .
C9 C10 1.389(8) .
C9 C18 1.469(8) .
C10 C11 1.454(7) .
C11 C20 1.398(8) .
C11 C12 1.446(8) .
C12 C13 1.394(7) .
C13 C14 1.445(8) 2_656
C13 C21 1.458(8) 2_656
C14 C15 1.456(7) .
C15 C16 1.402(8) .
C15 C22 1.445(8) .
C16 C17 1.446(8) .
C17 C24 1.396(9) .
C17 C18 1.444(8) .
C18 C19 1.385(9) .
C19 C26 1.443(8) .
C19 C20 1.452(9) .
C20 C28 1.443(8) .
C21 C28 1.390(9) 2_656
C21 C22 1.456(8) .
C22 C23 1.391(9) .
C23 C29 1.431(10) .
C23 C24 1.464(8) .
C24 C25 1.438(9) .
C25 C26 1.402(8) .
C25 C30 1.456(9) .
C26 C27 1.428(10) .
C27 C29 1.410(9) 2_656
C27 C28 1.458(8) .
C29 C30 1.458(8) .
C30 C30 1.368(14) 2_656
C31 C32 1.544(7) 2_656
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C38 1.359(11) .
C33 C34 1.416(10) .
C33 H33 0.9500 .
C34 C35 1.387(9) .
C34 H34 0.9500 .
C35 C36 1.393(11) .
C35 H35 0.9500 .
C36 C37 1.382(10) .
C36 H36 0.9500 .
C37 C38 1.421(11) .
C37 H37 0.9500 .
C38 H38 0.9500 .
C39 C41 1.374(12) 2_656
C39 C40 1.3899 .
C39 H39 0.9500 .
C40 C41 1.3900 .
C40 H40 0.9500 .
C41 H41 0.9500 .
I3 I3 2.777(10) 2_656
