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_1555614
_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, C18 H12, 3(C1 H1 Cl3)'
_chemical_formula_sum            'C75 H54 Cl9 N15 O3'
_chemical_formula_weight         1532.38
_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
_audit_creation_date             2016-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.878(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.056(2)
_cell_length_b                   13.8514(17)
_cell_length_c                   32.082(4)
_cell_measurement_reflns_used    7092
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.37
_cell_measurement_theta_min      2.25
_cell_volume                     7131.1(15)
_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 1.000
_diffrn_measured_fraction_theta_max 0.973
_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  0.1207
_diffrn_reflns_av_unetI/netI     0.1334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            71481
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.282
_diffrn_reflns_theta_min         1.400
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1314 before and 0.1001 after correction.
The Ratio of minimum to maximum transmission is 0.8137.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             3144
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.652
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1058
_refine_ls_number_reflns         15592
_refine_ls_number_restraints     1099
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1930
_refine_ls_R_factor_gt           0.0980
_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^)+(0.1797P)^2^+0.4374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2734
_refine_ls_wR_factor_ref         0.3441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7076
_reflns_number_total             15592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_008.cif
_cod_data_source_block           rn_js_200tp_0m_a
_cod_original_cell_volume        7131.1(16)
_cod_database_code               1555614
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H30B_1-H11_2
 -2 with sigma of 0.02
 Cl1B_3-C1B_3 \\sim Cl2B_3-C1B_3 \\sim Cl1_3-C1B_3 \\sim Cl3A_3-C1A_3 \\sim
Cl2A_3-C1A_3 ~
 Cl1A_3-C1A_3
 with sigma of 0.02
 Cl1B_3-Cl2B_3 \\sim Cl3A_3-Cl2A_3 \\sim Cl1B_3-Cl1_3 \\sim Cl3A_3-Cl1A_3 \\sim
Cl1_3-Cl2B_3 ~
 Cl1A_3-Cl2A_3
 with sigma of 0.04
 Cl2B_5-C1B_5 \\sim Cl3B_5-C1B_5 \\sim Cl1B_5-C1B_5 \\sim Cl2A_5-C1A_5 \\sim
Cl1_5-C1A_5 ~
 Cl1A_5-C1A_5
 with sigma of 0.02
 Cl2B_5-Cl3B_5 \\sim Cl2A_5-Cl1_5 \\sim Cl3B_5-Cl1B_5 \\sim Cl1A_5-Cl2A_5 \\sim
Cl2A_5-Cl1_5 ~
 Cl1B_5-Cl2B_5
 with sigma of 0.04
 Cl2B_4-C1B_4 \\sim Cl3B_4-C1B_4 \\sim Cl1B_4-C1B_4 \\sim Cl1A_4-C1A_4 \\sim
Cl2A_4-C1A_4 ~
 Cl3A_4-C1A_4
 with sigma of 0.02
 Cl2B_4-Cl3B_4 \\sim Cl1A_4-Cl2A_4 \\sim Cl1B_4-Cl2A_4 \\sim Cl2A_4-Cl3A_4
\\sim Cl1B_4-Cl2B_4
 \\sim Cl3A_4-Cl1A_4
 with sigma of 0.04
 N9_1-C30A_1 \\sim N9_1-C30B_1
 with sigma of 0.02
 C30A_1-C29_1 \\sim C30B_1-C29_1
 with sigma of 0.02
 N7B_1-C29_1 \\sim N7A_1-C29_1
 with sigma of 0.02
 N8B_1-N7B_1 \\sim N8A_1-N7A_1
 with sigma of 0.02
 N9_1-N8B_1 \\sim N9_1-N8A_1
 with sigma of 0.02
 N9_1-N7A_1 \\sim N7A_1-N7B_1
 with sigma of 0.04
 C29_1-N8A_1 \\sim C29_1-N8B_1
 with sigma of 0.04
 C30A_1-N8A_1 \\sim C30B_1-N8B_1
 with sigma of 0.04
 C30A_1-N7A_1 \\sim C30B_1-N7B_1
 with sigma of 0.04
 C9_2-C10_2 \\sim C9_2-C8_2 \\sim C8_2-C7_2 \\sim C7_2-C12_2 \\sim C12_2-C11_2
\\sim C11_2-C10_2 ~
 C14_2-C13_2 \\sim C15_2-C14_2 \\sim C16_2-C15_2 \\sim C17_2-C16_2 \\sim
C18_2-C17_2 \\sim C18_2-
 C13_2 \\sim C4_2-C3_2 \\sim C3_2-C2_2 \\sim C2_2-C1_2 \\sim C6_2-C1_2 \\sim
C6_2-C5_2 \\sim C7_2-C5_2
 \\sim C13_2-C12_2 \\sim C4_2-C18_2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C16_2 \\sim C5_1 \\sim C6_2 \\sim C4_2 \\sim C7_2 \\sim H6_2 \\sim C1_2 \\sim
C3_2 \\sim C18_2 \\sim C12_2 \\sim C8_2 \\sim H1_2 \\sim C2_2 \\sim H3_2 \\sim
C17_2 \\sim C13_2 \\sim C11_2 \\sim H8_2 \\sim C9_2 \\sim H2_2 \\sim H17_2
\\sim C14_2 \\sim C10_2 \\sim H11_2 \\sim H9_2 \\sim H16_2 \\sim C15_2 \\sim
H14_2 \\sim H10_2 \\sim H15_2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C1B_3 \\sim Cl1B_3 \\sim Cl2B_3 \\sim Cl1_3 \\sim C1A_3 \\sim Cl1A_3 \\sim
Cl2A_3 \\sim Cl3A_3: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C1B_5 \\sim Cl1B_5 \\sim Cl2B_5 \\sim Cl3B_5 \\sim C1A_5 \\sim Cl1A_5 \\sim
Cl2A_5 \\sim Cl1_5: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C1B_4 \\sim Cl1B_4 \\sim Cl3B_4 \\sim Cl2B_4 \\sim C1A_4 \\sim Cl1A_4 \\sim
Cl2A_4 \\sim Cl3A_4: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
N9_1 \\sim N8B_1 \\sim N8A_1 \\sim N7B_1 \\sim N7A_1 \\sim C29_1 \\sim C30A_1
\\sim C30B_1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C16_2, C5_1, C6_2, C4_2, C7_2, H6_2, C1_2, C3_2, C18_2, C12_2, C8_2, H1_2,
 C2_2, H3_2, C17_2, C13_2, C11_2, H8_2, C9_2, H2_2, H17_2, C14_2, C10_2, H11_2,
 H9_2, H16_2, C15_2, H14_2, H10_2, H15_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_3, Cl1B_3, Cl2B_3, Cl1_3, C1A_3, Cl1A_3, Cl2A_3, Cl3A_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_5, Cl1B_5, Cl2B_5, Cl3B_5, C1A_5, Cl1A_5, Cl2A_5, Cl1_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_4, Cl1B_4, Cl3B_4, Cl2B_4, C1A_4, Cl1A_4, Cl2A_4, Cl3A_4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30B_1, N9_1, N8B_1, N7B_1, C29_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30A_1, N8A_1, N7A_1
 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(Cl3B)=Sof(C1B)=Sof(H1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl1)=Sof(C1A)=Sof(H1A)=FVAR(1)
 Sof(N7B)=Sof(N8B)=Sof(C30B)=Sof(H30B)=1-FVAR(2)
 Sof(N7A)=Sof(N8A)=Sof(C30A)=Sof(H30A)=FVAR(2)
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl1)=Sof(C1B)=Sof(H1B)=1-FVAR(3)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C1A)=Sof(H1A)=FVAR(3)
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(C1B)=Sof(H1B)=1-FVAR(4)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C1A)=Sof(H1A)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1A(H1A), C1B(H1B), C1A(H1A), C1B(H1B)
6.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C25(H25A,H25B), C28(H28A,H28B), C40(H40A,H40B), C47(H47A,
 H47B), C54(H54A,H54B)
6.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), C24(H24), C27(H27), C30A(H30A),
 C30B(H30B), C35(H35), C36(H36), C38(H38), C39(H39), C42(H42), C43(H43),
 C45(H45), C46(H46), C49(H49), C50(H50), C52(H52), C53(H53), C1(H1), C2(H2),
 C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              36769
_shelx_hkl_checksum              50833
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'