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_1555604
_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, 1(C22 H12), 3(C2 H4 Cl2)'
_chemical_formula_sum            'C82 H63 Cl6 N15 O3'
_chemical_formula_weight         1519.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.721(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1030(17)
_cell_length_b                   13.8295(15)
_cell_length_c                   31.954(4)
_cell_measurement_reflns_used    8439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.42
_cell_volume                     7108.0(14)
_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      293.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_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  0.0843
_diffrn_reflns_av_unetI/netI     0.1193
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            92449
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         1.276
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.7985.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             3144
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1271
_refine_ls_number_reflns         14393
_refine_ls_number_restraints     1824
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.0757
_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^)+(0.1272P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2486
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6965
_reflns_number_total             14393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_013.cif
_cod_data_source_block           rn_js_200_bzpe_0m_a
_cod_original_cell_volume        7108.1(13)
_cod_database_code               1555604
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2B_4-C1B_4 = C2A_4-C1A_4
 1.54 with sigma of 0.02
 Cl1B_4-C1B_4 = Cl2A_4-C2A_4 = Cl1A_4-C1A_4 = Cl2B_4-C2B_4
 1.8 with sigma of 0.02
 C2A_2-C1A_2 \\sim C3A_2-C2A_2 \\sim C4A_2-C3A_2 \\sim C5A_2-C4A_2 \\sim
C6A_2-C5A_2 \\sim C6A_2-
 C1A_2 \\sim C5A_2-C22A_2 \\sim C22A_2-C21A_2 \\sim C21A_2-C20A_2 \\sim
C7A_2-C20A_2 \\sim C7A_2-
 C6A_2 \\sim C8A_2-C7A_2 \\sim C9A_2-C8A_2 \\sim C9A_2-C10A_2 \\sim
C11A_2-C10A_2 \\sim C12A_2-
 C11A_2 \\sim C13A_2-C12A_2 \\sim C14A_2-C13A_2 \\sim C9A_2-C14A_2 \\sim
C15A_2-C14A_2 \\sim C16A_2-
 C15A_2 \\sim C17A_2-C16A_2 \\sim C8A_2-C17A_2 \\sim C18A_2-C17A_2 \\sim
C19A_2-C18A_2 \\sim C20A_2-
 C19A_2 \\sim C1A_2-C10A_2
 with sigma of 0.02
 C2B_2-C1B_2 \\sim C3B_2-C2B_2 \\sim C4B_2-C3B_2 \\sim C5B_2-C4B_2 \\sim
C6B_2-C5B_2 \\sim C6B_2-
 C1B_2 \\sim C1B_2-C10B_2 \\sim C11B_2-C10B_2 \\sim C12B_2-C11B_2 \\sim
C13B_2-C12B_2 \\sim C14B_2-
 C13B_2 \\sim C9B_2-C14B_2 \\sim C9B_2-C10B_2 \\sim C15B_2-C14B_2 \\sim
C16B_2-C15B_2 \\sim C17B_2-
 C16B_2 \\sim C8B_2-C17B_2 \\sim C9B_2-C8B_2 \\sim C18B_2-C17B_2 \\sim
C19B_2-C18B_2 \\sim C20B_2-
 C19B_2 \\sim C7B_2-C20B_2 \\sim C21B_2-C20B_2 \\sim C22B_2-C21B_2 \\sim
C5B_2-C22B_2
 with sigma of 0.02
 C2A_3-C1A_3 \\sim C2B_3-C1B_3
 with sigma of 0.02
 Cl1B_3-C1B_3 \\sim Cl1A_3-C1A_3 \\sim Cl2B_3-C2B_3 \\sim Cl2A_3-C2A_3
 with sigma of 0.02
 C2B_3-Cl1B_3 \\sim C1B_3-Cl2B_3 \\sim C1A_3-Cl2A_3 \\sim C2A_3-Cl1A_3
 with sigma of 0.04
 C52_1-N14A_1 \\sim C52_1-N14B_1
 with sigma of 0.04
 N13_1-N15A_1 \\sim N13_1-N15B_1
 with sigma of 0.04
 N14B_1-C53B_1 \\sim N14A_1-C53A_1
 with sigma of 0.04
 N15B_1-C53B_1 \\sim N15A_1-C53A_1
 with sigma of 0.04
 N15B_1-C52_1 \\sim N15A_1-C52_1
 with sigma of 0.02
 N15B_1-N14B_1 \\sim N15A_1-N14A_1
 with sigma of 0.02
 N14B_1-N13_1 \\sim N14A_1-N13_1
 with sigma of 0.02
 Cl1B_4-C2B_4 \\sim C1B_4-Cl2B_4 \\sim C1A_4-Cl2A_4 \\sim C2A_4-Cl1A_4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1A_3 \\sim C1B_3 \\sim C2A_3 \\sim C2B_3: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl1A_3 \\sim Cl1B_3 \\sim Cl2A_3 \\sim Cl2B_3: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
N15B_1 \\sim C53B_1 \\sim N14B_1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
N15A_1 \\sim C53A_1 \\sim N14A_1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C1A_2 \\sim C2A_2 \\sim C6A_2 \\sim C10A_2 \\sim C3A_2 \\sim C5A_2 \\sim C7A_2
\\sim C9A_2 \\sim C11A_2 \\sim C4A_2 \\sim C22A_2 \\sim C8A_2 \\sim C20A_2
\\sim C14A_2 \\sim C12A_2 \\sim C21A_2 \\sim C17A_2 \\sim C19A_2 \\sim C13A_2
\\sim C15A_2 \\sim C16A_2 \\sim C18A_2: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C1B_2 \\sim C2B_2 \\sim C6B_2 \\sim C10B_2 \\sim C3B_2 \\sim C5B_2 \\sim C7B_2
\\sim C9B_2 \\sim C11B_2 \\sim C4B_2 \\sim C22B_2 \\sim C8B_2 \\sim C20B_2
\\sim C14B_2 \\sim C12B_2 \\sim C21B_2 \\sim C17B_2 \\sim C19B_2 \\sim C13B_2
\\sim C15B_2 \\sim C16B_2 \\sim C18B_2: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C2A_4 \\sim C1B_4 \\sim C2B_4 \\sim C1A_4: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl1B_4 \\sim Cl2A_4 \\sim Cl1A_4 \\sim Cl2B_4: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl1C_5 \\sim C1C_5 \\sim C2C_5 \\sim Cl2C_5 \\sim Cl1B_5 \\sim C1B_5 \\sim
C2B_5 \\sim Cl2B_5 \\sim Cl1A_5 \\sim C1A_5 \\sim C2A_5 \\sim Cl2A_5: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C1A_2, C2A_2, C6A_2, C10A_2, C3A_2, C5A_2, C7A_2, C9A_2, C11A_2, C4A_2,
 C22A_2, C8A_2, C20A_2, C14A_2, C12A_2, C21A_2, C17A_2, C19A_2, C13A_2, C15A_2,
 C16A_2, C18A_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2A_3, Cl1A_3, C1A_3, C2A_3, Cl2B_3, Cl1B_3, C1B_3, C2B_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_2, C2B_2, C6B_2, C10B_2, C3B_2, C5B_2, C7B_2, C9B_2, C11B_2, C4B_2,
 C22B_2, C8B_2, C20B_2, C14B_2, C12B_2, C21B_2, C17B_2, C19B_2, C13B_2, C15B_2,
 C16B_2, C18B_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2B_4, Cl1B_4, C1B_4, C2B_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
 Cl1C_5, C1C_5, C2C_5, Cl2C_5, Cl1A_5, C1A_5, C2A_5, Cl2A_5, Cl1B_5, C1B_5,
 C2B_5, Cl2B_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{Cl1A_3, Cl2A_3, C1A_3, C2A_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1A_5, Cl2A_5, C1A_5, C2A_5}
{Cl1A_3, Cl2A_3, C1A_3, C2A_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B_5, Cl2B_5, C1B_5, C2B_5}
{Cl1A_3, Cl2A_3, C1A_3, C2A_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1C_5, Cl2C_5, C1C_5, C2C_5}
6. Others
 1*[Sof(Cl1A)+Sof(Cl2A)+Sof(C1A)+Sof(H1AA)+Sof(H1AB)+Sof(C2A)+Sof(H2AA)+
 Sof(H2AB)]+1*[Sof(Cl1B)+Sof(Cl2B)+Sof(C1B)+Sof(H1BA)+Sof(H1BB)+Sof(C2B)+
 Sof(H2BA)+Sof(H2BB)]+1*[Sof(Cl1C)+Sof(Cl2C)+Sof(C1C)+Sof(H1CA)+Sof(H1CB)+
 Sof(C2C)+Sof(H2CA)+Sof(H2CB)]=1 with esd of 0.001
 Sof(N14B)=Sof(N15B)=Sof(C53B)=Sof(H53B)=1-FVAR(1)
 Sof(N14A)=Sof(N15A)=Sof(C53A)=Sof(H53A)=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(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=
 Sof(C6B)=Sof(C7B)=Sof(C8B)=Sof(C9B)=Sof(C10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=
 Sof(H16B)=Sof(C17B)=Sof(C19B)=Sof(H19B)=Sof(C18B)=Sof(H18B)=Sof(C20B)=
 Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=1-FVAR(3)
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=FVAR(3)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 1-FVAR(4)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(4)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(5)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 FVAR(6)
 Sof(Cl1C)=Sof(Cl2C)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(C2C)=Sof(H2CA)=Sof(H2CB)=
 FVAR(7)
7.a Free rotating group:
 C1B(C2B,C3B,C4B,C5B,C6B,C7B,C8B,C9B,C10B,C11B,C12B,C13B,C14B,C15B,C16B,C17B,
 C19B,C18B,C20B,C21B,C22B)
7.b 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), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB),
  C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C1C(H1CA,
 H1CB), C2C(H2CA,H2CB)
7.c 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), C45(H45), C49(H49), C53A(H53A), C53B(H53B), C2A(H2A), C3A(H3A),
 C4A(H4A), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A), C2B(H2B), C3B(H3B), C4B(H4B),
 C11B(H11B), C12B(H12B), C13B(H13B), C15B(H15B), C16B(H16B), C19B(H19B),
 C18B(H18B), C21B(H21B), C22B(H22B)
;
_shelx_res_checksum              63917
_shelx_hkl_checksum              55070
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'