Wavy-shaped Polycyclic Hydrocarbons with Controlled Aromaticity
Ma, Ji; Zhang, Ke; Schellhammer, Karl Sebastian; Fu, Yubin; Komber, Hartmut; Xu, Chi; Popov, Alexey A.; Hennersdorf, Felix; Weigand, Jan J.; Zhou, Shengqiang; Pisula, Wojciech; Ortmann, Frank; Berger, Reinhard Franz Josef; Liu, Junzhi; Feng, Xinliang; Chemical Science  (2019) –; doi:10.1039/C8SC05416A

data_1550685
_publ_section_title
;
 Wavy-shaped Polycyclic Hydrocarbons with Controlled Aromaticity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05416A
_journal_year                    2019
_chemical_formula_moiety         'C108 H86'
_chemical_formula_sum            'C108 H86'
_chemical_formula_weight         1383.76
_chemical_name_systematic        M4-008
_chemical_properties_physical
Moisture-sensitive,Oxygen-sensitive,Light-sensitive
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-03-13 deposited with the CCDC.    2019-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.134(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.1458(6)
_cell_length_b                   13.4627(4)
_cell_length_c                   22.3724(6)
_cell_measurement_reflns_used    6121
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.7990
_cell_measurement_theta_min      3.8740
_cell_volume                     4071.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_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    -73.00 -35.00   0.50   12.50    --  -24.50-178.00 -90.00   76
  2  \w    -51.00  -6.00   0.50   12.50    --  -24.50  57.00 150.00   90
  3  \w    -47.00  47.00   0.50   12.50    --  -24.50  38.00  60.00  188
  4  \w      1.00  43.00   0.50   12.50    --  -24.50  57.00 150.00   84
  5  \w      2.00  46.00   0.50   12.50    --   24.50  38.00 -30.00   88
  6  \w      8.00  55.00   0.50   12.50    --   24.50 -99.00-150.00   94
  7  \w     57.00  82.00   0.50   12.50    --   24.50 178.00 -90.00   50
  8  \w     51.00  97.00   0.50   12.50    --   24.50  38.00 -30.00   92
  9  \w     23.00  48.00   0.50   12.50    --   24.50 -99.00-120.00   50
 10  \w     72.00 119.00   0.50   50.00    --  111.00-125.00 -30.00   94
 11  \w    110.00 177.00   0.50   50.00    --  111.00 125.00  30.00  134
 12  \w     89.00 178.00   0.50   50.00    --  111.00  30.00  90.00  178
 13  \w     41.00  69.00   0.50   50.00    --  111.00-125.00 -30.00   56
 14  \w    114.00 139.00   0.50   50.00    --  111.00 -61.00-150.00   50
 15  \w     37.00 133.00   0.50   50.00    --  111.00 -77.00 -60.00  192
 16  \w     53.00  80.00   0.50   50.00    --  111.00 -61.00-150.00   54
 17  \w    129.00 154.00   0.50   50.00    --  111.00  30.00  60.00   50
 18  \w     93.00 175.00   0.50   50.00    --  111.00  45.00 150.00  164
 19  \w     88.00 125.00   0.50   50.00    --  111.00  30.00  60.00   74
 20  \w     83.00 175.00   0.50   50.00    --  111.00  61.00-120.00  184
 21  \w    102.00 129.00   0.50   50.00    --  111.00  34.00 141.00   54
 22  \w    114.00 145.50   0.50   50.00    --  111.00  45.00-180.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0566986000
_diffrn_orient_matrix_UB_12      -0.0236294000
_diffrn_orient_matrix_UB_13      0.0685886000
_diffrn_orient_matrix_UB_21      0.0849218000
_diffrn_orient_matrix_UB_22      -0.0452043000
_diffrn_orient_matrix_UB_23      -0.0211581000
_diffrn_orient_matrix_UB_31      0.0505979000
_diffrn_orient_matrix_UB_32      0.1024246000
_diffrn_orient_matrix_UB_33      0.0065180000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.567
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       block
_exptl_crystal_F_000             1468
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane/ ether acetate'
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         8423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1070P)^2^+0.4956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.1881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6041
_reflns_number_total             8423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05416a2.cif
_cod_data_source_block           feng048_sq
_cod_original_cell_volume        4071.5(2)
_cod_database_code               1550685
_chemical_oxdiff_formula         'C226 H194 '
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C18(H18), C19(H19), C21(H21),
 C25(H25), C30(H30), C31(H31), C32(H32), C39(H39), C41(H41), C48(H48), C50(H50)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C52(H52A,H52B,H52C), C53(H53A,
 H53B,H53C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              72531
_shelx_fab_checksum              10210
_shelx_shelxl_version_number     2014/7
_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 3.717
_oxdiff_exptl_absorpt_empirical_full_min 0.642