Hierarchical Ordering in Ternary Co-Crystals of C60,N-Benzyl Ammonium Resorcinarene Bromide and Solvent Molecules
Beyeh, N. Kodiah; Pan, Fangfang; Rissanen, Kari; Crystal Growth & Design 14 (2014) 6161–; doi:10.1021/cg5014413

data_4512305
_publ_section_title
;
 Hierarchical Ordering in Ternary Co-Crystals of C60,N-Benzyl Ammonium
 Resorcinarene Bromide and Solvent Molecules
;
_journal_issue                   12
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              6161
_journal_paper_doi               10.1021/cg5014413
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety
'4(Br), C72 H88 N4 O8, C H Cl3, C H0.94 Cl3, C2 H6 O'
_chemical_formula_sum            'C76 H96 Br4 Cl6 N4 O9'
_chemical_formula_weight         1741.91
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                81.3104(19)
_cell_angle_beta                 77.788(2)
_cell_angle_gamma                66.947(2)
_cell_formula_units_Z            2
_cell_length_a                   13.3944(3)
_cell_length_b                   15.7651(4)
_cell_length_c                   20.8205(4)
_cell_measurement_reflns_used    17110
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.2960
_cell_measurement_theta_min      3.5980
_cell_volume                     3942.50(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1053307000
_diffrn_orient_matrix_UB_12      -0.0451323000
_diffrn_orient_matrix_UB_13      -0.0493337000
_diffrn_orient_matrix_UB_21      -0.0600581000
_diffrn_orient_matrix_UB_22      -0.0473392000
_diffrn_orient_matrix_UB_23      -0.0288053000
_diffrn_orient_matrix_UB_31      -0.0370664000
_diffrn_orient_matrix_UB_32      0.0840596000
_diffrn_orient_matrix_UB_33      -0.0500101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28078
_diffrn_reflns_theta_full        66.75
_diffrn_reflns_theta_max         66.75
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.817
_exptl_absorpt_correction_T_max  0.391
_exptl_absorpt_correction_T_min  0.090
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             1788
_exptl_crystal_size_max          0.3786
_exptl_crystal_size_mid          0.1706
_exptl_crystal_size_min          0.1134
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     955
_refine_ls_number_reflns         13954
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+3.5899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                12382
_reflns_number_total             13954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5014413_si_002.cif
_cod_data_source_block           reso-br
_cod_depositor_comments          'Adding full bibliography for 4512305.cif.'
_cod_original_cell_volume        3942.50(16)
_cod_database_code               4512305
_chemical_oxdiff_formula         'C80 H80 N8 I4 N3'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C74-Cl4B
 1.76 with sigma of 0.01
 C74-Cl4A \\sim C74-Cl4B \\sim C74-Cl5 \\sim C74-Cl6
 with sigma of 0.02
 Cl4A-Cl5 \\sim Cl4B-Cl5 \\sim Cl5-Cl6 \\sim Cl4A-Cl6 \\sim Cl4B-Cl6
 with sigma of 0.02
 C34-C35A \\sim C35A-C36A \\sim C34-C35B \\sim C35B-C36B
 with sigma of 0.02
 O9-C75A \\sim O9-C75B
 with sigma of 0.02
 C75A-C76A \\sim C75B-C76B
 with sigma of 0.02
3. Others
 Sof(H34C)=Sof(H34D)=Sof(C35B)=Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36D)=
 Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(H34A)=Sof(H34B)=Sof(C35A)=Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=FVAR(1)
 Sof(Cl4B)=1-FVAR(2)
 Sof(Cl4A)=Sof(H74)=FVAR(2)
 Sof(H9B)=Sof(C75B)=Sof(H75C)=Sof(H75D)=Sof(C76B)=Sof(H76D)=Sof(H76E)=
 Sof(H76F)=1-FVAR(3)
 Sof(H9A)=Sof(C75A)=Sof(H75A)=Sof(H75B)=Sof(C76A)=Sof(H76A)=Sof(H76B)=
 Sof(H76C)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C33(H33), C51(H51), C69(H69), C73(H73), C74(H74)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B),
 C16(H16A,H16B), C17(H17A,H17B), C25(H25A,H25B), C26(H26A,H26B), C34(H34A,H34B),
  C34(H34C,H34D), C35A(H35A,H35B), C35B(H35C,H35D), C43(H43A,H43B), C44(H44A,
 H44B), C52(H52A,H52B), C53(H53A,H53B), C61(H61A,H61B), C62(H62A,H62B),
 C70(H70A,H70B), C71(H71A,H71B), C75A(H75A,H75B), C75B(H75C,H75D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6A), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C42(H42), C46(H46), C47(H47),
 C48(H48), C49(H49), C50(H50), C60(H60), C64(H64), C65(H65), C66(H66), C67(H67),
  C68(H68)
4.d Tetrahedral OH refined with riding coordinates:
 O9(H9A), O9(H9B)
4.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36A(H36A,H36B,H36C), C36B(H36D,H36E,H36F), C54(H54A,
 H54B,H54C), C72(H72A,H72B,H72C), C76A(H76A,H76B,H76C), C76B(H76D,H76E,H76F)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6), O7(H7), O8(H8)
;