A Nonalternant Aromatic Belt: Methylene-Bridged [6]Cycloparaphenylene Synthesized from Pillar[6]arene.
Li, Yuanming; Segawa, Yasutomo; Yagi, Akiko; Itami, Kenichiro; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c06007

data_4135107
_publ_section_title
;
 A Nonalternant Aromatic Belt: Methylene-Bridged [6]Cycloparaphenylene
 Synthesized from Pillar[6]arene.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c06007
_journal_year                    2020
_chemical_formula_moiety         '2(C21 H12), 0.5(C H2 Cl2), 0.5(C6 H14)'
_chemical_formula_sum            'C45.5 H32 Cl'
_chemical_formula_weight         614.16
_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             2020-04-09
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                107.588(2)
_cell_angle_beta                 92.5269(19)
_cell_angle_gamma                101.5278(19)
_cell_formula_units_Z            2
_cell_length_a                   11.4850(3)
_cell_length_b                   11.7900(3)
_cell_length_c                   12.1794(3)
_cell_measurement_reflns_used    7469
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.2240
_cell_measurement_theta_min      1.7810
_cell_volume                     1530.72(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -45.00  73.00   0.50   55.00    --  -10.74  41.00 -99.00  236
  2  \w    -23.00  86.00   0.50   55.00    --   11.29  41.00 -99.00  218
  3  \w     -7.00  40.00   0.50   55.00    --  -10.74 -99.00  90.00   94
  4  \w    -14.00  61.00   0.50   55.00    --   11.29 -99.00 120.00  150
  5  \w     -5.00  22.00   0.50   55.00    --  -10.74 -99.00 -30.00   54
  6  \w    -68.00  30.00   0.50   55.00    --   11.29 -41.00 107.00  196
  7  \w    -92.00 -61.00   0.50   55.00    --  -10.74-179.00-120.00   62
  8  \w     38.00  68.00   0.50   55.00    --   11.29 179.00 120.00   60
  9  \w     46.00  95.00   0.50   55.00    --   11.29 179.00  90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0346419000
_diffrn_orient_matrix_UB_12      -0.0330119000
_diffrn_orient_matrix_UB_13      0.0318416000
_diffrn_orient_matrix_UB_21      0.0455254000
_diffrn_orient_matrix_UB_22      -0.0322573000
_diffrn_orient_matrix_UB_23      0.0021896000
_diffrn_orient_matrix_UB_31      0.0273963000
_diffrn_orient_matrix_UB_32      0.0454183000
_diffrn_orient_matrix_UB_33      0.0525457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18175
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.884
_diffrn_reflns_theta_min         1.765
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+0.8066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1702
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4249
_reflns_number_total             6100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c06007_si_002.cif
_cod_data_source_block           4
_cod_original_cell_volume        1530.71(6)
_cod_original_formula_sum        'C45.50 H32 Cl'
_cod_database_code               4135107
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Cl'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_diffrn_oxdiff_digest_frames
;
0102a7f271436d8e6e57f9a9dcda62749700025acb9
;
_diffrn_oxdiff_digest_hkl
;
01b8e569f4b8789eeb9bab7794fbd716c9774d
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C49-C47
 2.54 with sigma of 0.02
 C48-C50
 2.54 with sigma of 0.02
 C46-C47 = C47-C48 = C48-C49 = C49-C50 = C50-C51
 1.54 with sigma of 0.01
 C51-C49
 2.54 with sigma of 0.02
 C46-C48
 2.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Rigid body (RIGU) restrains
 C46, C47, C48, C49, C50, C51
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C43(0.5) H0AA(0.5) H0AB(0.5) Cl44(0.5) Cl45(0.5) C51(0.5)
 H1AA(0.5) H1AB(0.5) H1AC(0.5) C50(0.5) H1BA(0.5) H1BB(0.5) C49(0.5) H1CA(0.5)
 H1CB(0.5) C48(0.5) H1DA(0.5) H1DB(0.5) C47(0.5) H1EA(0.5) H1EB(0.5) C46(0.5)
 H1FA(0.5) H1FB(0.5) H1FC(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C29(H9A,H9B), C36(H14A,H14B), C1(H25A,H25B), C15(H35A,H35B), C22(H17A,H17B),
 C8(H42A,H42B), C43(H0AA,H0AB), C50(H1BA,H1BB), C49(H1CA,H1CB), C48(H1DA,H1DB),
 C47(H1EA,H1EB)
6.b Me refined with riding coordinates:
 C51(H1AA,H1AB,H1AC), C46(H1FA,H1FB,H1FC)
6.c Aromatic/amide H refined with riding coordinates:
 C32(H21), C41(H3), C35(H11), C3(H41), C24(H18), C21(H29), C6(H40), C38(H16),
 C14(H33), C18(H23), C11(H37), C27(H7)
;
_shelx_res_checksum              27044
_shelx_hkl_checksum              68160
_olex2_exptl_crystal_mounting_method Loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.821
_oxdiff_exptl_absorpt_empirical_full_min 0.494