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_1555607
_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(C16 H10), 3(C H Cl3)'
_chemical_formula_sum            'C73 H52 Cl9.01 N15 O3'
_chemical_formula_weight         1506.73
_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             2016-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.117(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.133(5)
_cell_length_b                   13.761(4)
_cell_length_c                   32.115(9)
_cell_measurement_reflns_used    9127
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.31
_cell_measurement_theta_min      2.25
_cell_volume                     7125(4)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1152
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            127040
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.096
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_min         1.269
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7270
_exptl_absorpt_correction_T_min  0.6310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1436 before and 0.1101 after correction.
The Ratio of minimum to maximum transmission is 0.8680.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             3089
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.0017(6)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1187
_refine_ls_number_reflns         12583
_refine_ls_number_restraints     1438
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1792
_refine_ls_R_factor_gt           0.1047
_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^)+(0.1933P)^2^+12.9093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2882
_refine_ls_wR_factor_ref         0.3751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6547
_reflns_number_total             12583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_007.cif
_cod_data_source_block           rn_js242py_0m_a
_cod_database_code               1555607
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl3_6-C1_6 = Cl1_6-C1_6 = Cl2_6-C1_6
 1.7 with sigma of 0.04
 Cl1_6-Cl2_6 = Cl1_6-Cl3_6 = Cl2_6-Cl3_6
 2.8 with sigma of 0.04
 C9A_2-C10A_2 \\sim C9A_2-C8A_2 \\sim C8A_2-C7A_2 \\sim C7A_2-C12A_2 \\sim
C12A_2-C11A_2 ~
 C11A_2-C10A_2 \\sim C8A_2-C16A_2 \\sim C16A_2-C15A_2 \\sim C3A_2-C15A_2 \\sim
C4A_2-C3A_2 ~
 C7A_2-C4A_2 \\sim C5A_2-C4A_2 \\sim C5A_2-C14A_2 \\sim C14A_2-C13A_2 \\sim
C13A_2-C12A_2 ~
 C3A_2-C2A_2 \\sim C2A_2-C1A_2 \\sim C6A_2-C1A_2 \\sim C6A_2-C5A_2
 with sigma of 0.02
 Cl4A_4-C1A_4 \\sim Cl2B_4-C1B_4 \\sim Cl3A_4-C1A_4 \\sim Cl3B_4-C1B_4 \\sim
Cl2A_4-C1A_4
 with sigma of 0.02
 Cl2A_4-Cl3A_4 \\sim Cl2A_4-Cl4A_4 \\sim Cl3A_4-Cl4A_4 \\sim Cl2B_4-Cl3B_4
\\sim Cl2B_4-Cl4B_4
 \\sim Cl3B_4-Cl4B_4
 with sigma of 0.04
 C49B_1-C48_1 \\sim C49A_1-C48_1
 with sigma of 0.02
 N12_1-C49B_1 \\sim N12_1-C49A_1
 with sigma of 0.02
 N10_1-C48_1 \\sim N10A_1-C48_1
 with sigma of 0.02
 N12_1-N11_1 \\sim N12_1-N11A_1
 with sigma of 0.02
 N11_1-N10_1 \\sim N11A_1-N10A_1
 with sigma of 0.02
 C48_1-N11_1 \\sim C48_1-N11A_1
 with sigma of 0.04
 N12_1-N10_1 \\sim N10_1-N12_1
 with sigma of 0.04
 C49B_1-N10A_1 \\sim C49A_1-N10_1
 with sigma of 0.02
 C49B_1-N11A_1 \\sim C49A_1-N11_1
 with sigma of 0.04
3. Rigid bond restraints
 C1A_2, C2A_2, C3A_2, C4A_2, C5A_2, C6A_2, C7A_2, C8A_2, C9A_2, C10A_2, C11A_2,
  C12A_2, C13A_2, C14A_2, C15A_2, C16A_2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1B_2, C2B_2, C3B_2, C4B_2, C5B_2, C6B_2, C7B_2, C8B_2, C9B_2, C10B_2, C11B_2,
  C12B_2, C13B_2, C14B_2, C15B_2, C16B_2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1A_2 \\sim C2A_2 \\sim C3A_2 \\sim C4A_2 \\sim C5A_2 \\sim C6A_2 \\sim C7A_2
\\sim C8A_2 \\sim C9A_2 \\sim C10A_2 \\sim C11A_2 \\sim C12A_2 \\sim C13A_2
\\sim C14A_2 \\sim C15A_2 \\sim C16A_2: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
C1B_2 \\sim C2B_2 \\sim C3B_2 \\sim C4B_2 \\sim C5B_2 \\sim C6B_2 \\sim C7B_2
\\sim C8B_2 \\sim C9B_2 \\sim C10B_2 \\sim C11B_2 \\sim C12B_2 \\sim C13B_2
\\sim C14B_2 \\sim C15B_2 \\sim C16B_2: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Cl3_3 \\sim Cl2_3 \\sim Cl4_3 \\sim C1_1: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C1_6 \\sim Cl1_6 \\sim Cl2_6 \\sim Cl3_6: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C1A_7 \\sim Cl2A_7 \\sim Cl3A_7 \\sim Cl4A_7: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C1B_4 \\sim Cl2B_4 \\sim Cl3B_4 \\sim Cl4B_4 \\sim C1A_4 \\sim Cl2A_4 \\sim
Cl3A_4 \\sim Cl4A_4: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C49B_1 \\sim C49A_1 \\sim C48_1 \\sim N10_1 \\sim N10A_1 \\sim N11_1 \\sim
N11A_1 \\sim N12_1: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
5. Rigid body (RIGU) restrains
 Cl3_3, Cl2_3, Cl4_3, C1_3
 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
 C1A_7, Cl2A_7, Cl3A_7, Cl4A_7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B_4, Cl2B_4, Cl3B_4, Cl4B_4, C1A_4, Cl2A_4, Cl3A_4, Cl4A_4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C49B_1, C48_1, N10A_1, N11A_1, N12_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C49A_1, N10_1, N11_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C1A_2, C2A_2, C3A_2, C4A_2, C5A_2, C6A_2, C7A_2, C8A_2, C9A_2, C10A_2, C11A_2,
C12A_2, C13A_2, C14A_2, C15A_2, C16A_2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1B_2, C2B_2, C3B_2, C4B_2, C5B_2, C6B_2, C7B_2, C8B_2, C9B_2, C10B_2, C11B_2,
C12B_2, C13B_2, C14B_2, C15B_2, C16B_2}
{Cl2_3, Cl3_3, Cl4_3, C1_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl2A_7, Cl3A_7, Cl4A_7, C1A_7}
7. Others
 1*[Sof(Cl2)+Sof(Cl3)+Sof(Cl4)+Sof(C1)+Sof(H1)]+1*[Sof(C1)+Sof(H1)+Sof(Cl1)+
 Sof(Cl2)+Sof(Cl3)]+1*[Sof(Cl2A)+Sof(Cl3A)+Sof(Cl4A)+Sof(C1A)+Sof(H1A)]=1 with
 esd of 0.001
 Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=
 Sof(H6B)=Sof(C7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=
 Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=
 Sof(H15B)=Sof(C16B)=Sof(H16B)=1-FVAR(1)
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=
 Sof(H6A)=Sof(C7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=FVAR(1)
 Sof(C1B)=Sof(H1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(Cl4B)=1-FVAR(2)
 Sof(C1A)=Sof(H1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(Cl4A)=FVAR(2)
 Sof(Cl2)=Sof(Cl3)=Sof(Cl4)=Sof(C1)=Sof(H1)=FVAR(3)
 Sof(C1)=Sof(H1)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(4)
 Sof(Cl2A)=Sof(Cl3A)=Sof(Cl4A)=Sof(C1A)=Sof(H1A)=FVAR(5)
 Sof(N10A)=Sof(N11A)=Sof(C49B)=Sof(H49B)=1-FVAR(6)
 Sof(N10)=Sof(N11)=Sof(C49A)=Sof(H49A)=FVAR(6)
8.a Ternary CH refined with riding coordinates:
 C1(H1), C1A(H1A), C1B(H1B), C1(H1), C1(H1), C1A(H1A)
8.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)
8.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), C49A(H49A), C49B(H49B), C53(H53), C1A(H1A), C2A(H2A),
 C6A(H6A), C9A(H9A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C15A(H15A),
  C16A(H16A), C1B(H1B), C2B(H2B), C6B(H6B), C9B(H9B), C10B(H10B), C11B(H11B),
 C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B)
;
_shelx_res_checksum              59249
_shelx_hkl_checksum              35930
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'