[15]Paracyclophane and [16]paracyclophane: facile syntheses, crystal structures and selective complexation with cesium cations in the gas phase
Liu, Peiren; Li, Qi; Zeng, Hong; Shi, Bingbing; Liu, Jiyong; Huang, Feihe; Organic Chemistry Frontiers 6 (2019) 309–; doi:10.1039/C8QO01218K

data_1554541
_publ_section_title
;
 [15]Paracyclophane and [16]paracyclophane: facile syntheses, crystal
 structures and selective complexation with cesium cations in the gas
 phase
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              309
_journal_paper_doi               10.1039/C8QO01218K
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C42 H36'
_chemical_formula_sum            'C42 H36'
_chemical_formula_weight         540.71
_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
_audit_creation_date             2018-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-16 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                105.144(4)
_cell_angle_beta                 93.375(3)
_cell_angle_gamma                90.360(3)
_cell_formula_units_Z            4
_cell_length_a                   11.3720(4)
_cell_length_b                   13.1796(6)
_cell_length_c                   24.5090(10)
_cell_measurement_reflns_used    7210
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2505
_cell_measurement_theta_min      1.7907
_cell_volume                     3538.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -75.00   19.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000  -30.0000 126

  2 omega  -36.00   59.25   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000   90.0000 127

  3 omega  -15.00   73.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  -90.0000 118
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0147544000
_diffrn_orient_matrix_UB_12      0.0234880000
_diffrn_orient_matrix_UB_13      0.0281744000
_diffrn_orient_matrix_UB_21      0.0605283000
_diffrn_orient_matrix_UB_22      0.0110844000
_diffrn_orient_matrix_UB_23      0.0082880000
_diffrn_orient_matrix_UB_31      -0.0049826000
_diffrn_orient_matrix_UB_32      0.0493605000
_diffrn_orient_matrix_UB_33      -0.0063634000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23487
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.794
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.015
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     757
_refine_ls_number_reflns         12867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0708P)^2^+0.2775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7143
_reflns_number_total             12867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01218k2.cif
_cod_data_source_block           180625_lq_p6_2_sq
_cod_database_code               1554541
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C15(H15A,H15B), C22(H22A,H22B), C29(H29A,H29B),
 C36(H36A,H36B), C43(H43A,H43B), C50(H50A,H50B), C57(H57A,H57B), C64(H64A,H64B),
  C71(H71A,H71B), C78(H78A,H78B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25), C27(H27), C28(H28),
  C31(H31), C32(H32), C34(H34), C35(H35), C38(H38), C39(H39), C41(H41),
 C42(H42), C45(H45), C46(H46), C48(H48), C49(H49), C52(H52), C53(H53), C55(H55),
  C56(H56), C59(H59), C60(H60), C62(H62), C63(H63), C66(H66), C67(H67),
 C69(H69), C70(H70), C73(H73), C74(H74), C76(H76), C77(H77), C80(H80), C81(H81),
  C83(H83), C84(H84)
;
_shelx_res_checksum              5919
_shelx_hkl_checksum              30364
_shelx_fab_checksum              52286
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'