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_1555606
_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, 3.75(C2 H4 Cl2)'
_chemical_formula_sum            'C61.5 H54 Cl7.5 N15 O3'
_chemical_formula_weight         1317.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.170(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7001(8)
_cell_length_b                   20.2403(14)
_cell_length_c                   29.729(2)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.32
_cell_volume                     6437.2(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0429
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            88463
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         1.217
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1359 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.8436.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             2718
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     896
_refine_ls_number_reflns         14748
_refine_ls_number_restraints     287
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0838
_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^)+(0.1053P)^2^+15.3911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10870
_reflns_number_total             14748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_003.cif
_cod_data_source_block           rn_js_200_co_r_0m
_cod_original_formula_sum        'C61.50 H54 Cl7.50 N15 O3'
_cod_database_code               1555606
_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
2. Restrained distances
 C1_5-C2A_5
 1.54 with sigma of 0.02
 C1_5-Cl1_5 = C2A_5-Cl2A_5 = C2B_5-Cl2B_5
 1.74 with sigma of 0.04
 C2B_2-C1B_2 \\sim C2A_2-C1A_2
 with sigma of 0.04
 C2B_4-C1B_4 \\sim C2A_4-C1A_4
 with sigma of 0.04
 Cl2A_2-C2A_2 \\sim Cl2B_2-C2B_2 \\sim Cl1B_2-C1B_2 \\sim Cl1A_2-C1A_2
 with sigma of 0.02
 C1A_2-Cl2A_2 \\sim C1B_2-Cl2B_2 \\sim C2A_2-Cl1A_2 \\sim C2B_2-Cl1B_2
 with sigma of 0.04
 Cl1A_4-C1A_4 \\sim Cl1B_4-C1B_4 \\sim Cl2A_4-C2A_4 \\sim Cl2B_4-C2B_4
 with sigma of 0.02
 C1A_4-Cl2A_4 \\sim C1B_4-Cl2B_4 \\sim C2A_4-Cl1A_4 \\sim C2B_4-Cl1B_4
 with sigma of 0.04
 Cl1B_3-C1_3 \\sim Cl1A_3-C1_3
 with sigma of 0.02
 C2_3-Cl1A_3 \\sim C2_3-Cl1B_3
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl1B_2 \\sim Cl2B_2 \\sim C2B_2 \\sim C1B_2 \\sim Cl1A_2 \\sim C1A_2 \\sim
C2A_2 \\sim Cl2A_2: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
Cl1B_3 \\sim Cl1A_3 \\sim C1_3 \\sim C2_3 \\sim Cl2_3: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
Cl1_5 \\sim C1_5 \\sim C2A_5 \\sim Cl2A_5 \\sim C2B_5 \\sim Cl2B_5: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 Cl1B_4, C1B_4, C2B_4, Cl2B_4, Cl1A_4, C1A_4, C2A_4, Cl2A_4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1B_2, Cl2B_2, C2B_2, C1B_2, Cl1A_2, C1A_2, C2A_2, Cl2A_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1B_3, Cl1A_3, C1_3, C2_3, Cl2_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1_5, C1_5, C2A_5, Cl2A_5, Cl2B_5, C2B_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 1-FVAR(2)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(2)
 Sof(Cl1B)=Sof(H1BC)=Sof(H1BD)=1-FVAR(3)
 Sof(Cl1A)=Sof(H1AA)=Sof(H1AB)=FVAR(3)
 Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(Cl2B)=1-FVAR(4)
 Sof(Cl2A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=FVAR(4)
 Fixed Sof: Cl1(0.5) C1(0.5) H1A(0.5) H1B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B), C50(H50A,H50B), C51(H51A,
 H51B), C54(H54A,H54B), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB),
 C2B(H2BA,H2BB), C1(H1AA,H1AB), C1(H1BC,H1BD), C2(H2A,H2B), C1A(H1AA,H1AB),
 C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C1(H1A,H1B), C2A(H2AA,H2AB),
 C2B(H2BA,H2BB)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C26(H26), C27(H27), C29(H29), C30(H30),
  C32(H32), C33(H33), C35(H35), C36(H36), C38(H38), C39(H39), C41(H41),
 C42(H42), C44(H44), C48(H48), C52(H52)
;
_shelx_res_checksum              9890
_shelx_hkl_checksum              43325
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'