Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic Hydrocarbons.
Samanta, Jayanta; Natarajan, Ramalingam; Organic letters 18 (2016) 3394–3397; doi:10.1021/acs.orglett.6b01554

data_1555613
_publ_section_title
;
 Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic
 Hydrocarbons.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3394
_journal_page_last               3397
_journal_paper_doi               10.1021/acs.orglett.6b01554
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C54 H39 N15 O3, 2.75(C H Cl3)'
_chemical_formula_sum            'C56.75 H41.75 Cl8.25 N15 O3'
_chemical_formula_weight         1274.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                99.418(11)
_cell_angle_beta                 94.933(10)
_cell_angle_gamma                90.930(10)
_cell_formula_units_Z            4
_cell_length_a                   10.110(2)
_cell_length_b                   21.965(5)
_cell_length_c                   27.902(6)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.26
_cell_volume                     6087(2)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            97099
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         0.743
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1180 before and 0.0851 after correction.
The Ratio of minimum to maximum transmission is 0.8577.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             2606
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.34
_refine_diff_density_max         1.770
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.0028(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.388
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1552
_refine_ls_number_reflns         21026
_refine_ls_number_restraints     253
_refine_ls_restrained_S_all      1.406
_refine_ls_R_factor_all          0.1818
_refine_ls_R_factor_gt           0.1239
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3630
_refine_ls_wR_factor_ref         0.4048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12006
_reflns_number_total             21026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_002.cif
_cod_data_source_block           rn_js_250215_0m_a
_cod_database_code               1555613
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl1_5-Cl3_6
 -2.8 with sigma of 0.02
3. Rigid bond restraints
 C1_6, Cl1_6, Cl2_6, Cl3_6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1B_6, Cl1B_6, Cl2B_6, Cl3B_6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Cl1_5 \\sim Cl2_5 \\sim Cl3_5: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C1_8 \\sim Cl1_8 \\sim Cl2_8 \\sim Cl3_8: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C1B_8 \\sim Cl1B_8 \\sim Cl2B_8 \\sim Cl3B_8: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(Cl1B_6) = Uanis(Cl2B_6) = Uanis(Cl3B_6) = Uanis(Cl1_6) = Uanis(Cl2_6) =
Uanis(Cl3_6)
Uanis(C1_6) = Uanis(C1B_6)
5. Rigid body (RIGU) restrains
 C1_8, Cl1_8, Cl2_8, Cl3_8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_8, Cl1B_8, Cl2B_8, Cl3B_8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1_6, Cl1_6, Cl2_6, Cl3_6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_6, Cl1B_6, Cl2B_6, Cl3B_6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1_4, Cl2_4, Cl3_4, C1_4}
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1_5, Cl2_5, Cl3_5, C1_5}
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1_6, Cl2_6, Cl3_6, C1_6}
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B_6, Cl2B_6, Cl3B_6, C1B_6}
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1_7, Cl2_7, Cl3_7, C1_7}
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1_8, Cl2_8, Cl3_8, C1_8}
{Cl1_3, Cl2_3, Cl3_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B_8, Cl2B_8, Cl3B_8, C1B_8}
7. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(C1B)=Sof(H1B)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C1)=Sof(H1)=FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(C1B)=Sof(H1B)=0.5*(1-FVAR(3))
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C1)=Sof(H1)=0.5*FVAR(3)
8.a Ternary CH refined with riding coordinates:
 C1(H1), C1(H1), C1(H1), C1(H1), C1B(H1B), C1(H1), C1(H1), C1B(H1B)
8.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C29(H29A,H29B), C32(H32A,H32B), C45(H45A,
 H45B), C48(H48A,H48B), C13(H13A,H13B), C16(H16A,H16B), C29(H29A,H29B),
 C32(H32A,H32B), C45(H45A,H45B), C48(H48A,H48B)
8.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C18(H18), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C31(H31), C34(H34), C35(H35),
  C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44), C47(H47),
 C50(H50), C51(H51), C53(H53), C54(H54), C8(H8), C9(H9), C11(H11), C12(H12),
 C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27),
  C28(H28), C31(H31), C34(H34), C35(H35), C37(H37), C38(H38), C40(H40),
 C41(H41), C43(H43), C44(H44), C47(H47), C50(H50), C51(H51), C53(H53), C54(H54)
;
_shelx_res_checksum              85703
_shelx_hkl_checksum              20946
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'