[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_1554540
_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_absolute_configuration unk
_chemical_formula_moiety         'C35 H30'
_chemical_formula_sum            'C35 H30'
_chemical_formula_weight         450.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-16 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   44.902(3)
_cell_length_b                   11.1591(10)
_cell_length_c                   10.6337(7)
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1961
_cell_measurement_theta_min      2.9696
_cell_volume                     5328.2(7)
_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
;
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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -85.00    1.25   0.7500   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000   90.0000 115

  2 omega  -22.00   34.25   0.7500   27.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000 -120.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0018220000
_diffrn_orient_matrix_UB_12      -0.0322086000
_diffrn_orient_matrix_UB_13      -0.0569794000
_diffrn_orient_matrix_UB_21      -0.0114454000
_diffrn_orient_matrix_UB_22      -0.0346816000
_diffrn_orient_matrix_UB_23      0.0281571000
_diffrn_orient_matrix_UB_31      -0.0107471000
_diffrn_orient_matrix_UB_32      0.0423782000
_diffrn_orient_matrix_UB_33      -0.0203140000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16649
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.976
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79585
_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    1.123
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -10.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         8228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0587P)^2^+0.2831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1705
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    0.649
_reflns_Friedel_fraction_max     0.645
_reflns_number_gt                5003
_reflns_number_total             8228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01218k2.cif
_cod_data_source_block           180424_liupr02_170
_cod_original_cell_volume        5328.1(7)
_cod_database_code               1554540
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.48
_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), C54(H54A,H54B), C61(H61A,H61B),
  C68(H68A,H68B)
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), C56(H56),
  C57(H57), C59(H59), C60(H60), C63(H63), C64(H64), C66(H66), C67(H67),
 C70(H70), C71(H71)
;
_shelx_res_checksum              79541
_shelx_hkl_checksum              48479
_olex2_submission_special_instructions 'No special instructions were received'