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_1550686
_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         '2(C54 H45)'
_chemical_formula_sum            'C108 H90'
_chemical_formula_weight         1387.79
_chemical_name_common            9
_chemical_name_systematic        M4A-008
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-01 deposited with the CCDC.    2019-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.002(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.3411(8)
_cell_length_b                   28.1487(6)
_cell_length_c                   24.3410(7)
_cell_measurement_reflns_used    10042
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      56.4130
_cell_measurement_theta_min      3.6620
_cell_volume                     20535.4(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_type            HyPix
_diffrn_measured_fraction_theta_full 0.875
_diffrn_measured_fraction_theta_max 0.995
_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    -86.00 -39.00   1.00   25.00    --  -88.04 109.00  23.00   47
  2  \w    -90.00 -18.00   1.00   25.00    --  -88.04 125.00  60.00   72
  3  \w      3.00  28.00   1.00    5.00    --    0.00  57.00 120.00   25
  4  \w     48.00  73.00   1.00    5.00    --    0.00  57.00 120.00   25
  5  \w    102.00 142.00   1.00   25.00    --   88.04 109.00  23.00   40
  6  \w     96.00 151.00   1.00   25.00    --   88.04 125.00-150.00   55
  7  \w     33.00  76.00   1.00   25.00    --   88.04 -57.00 -60.00   43
  8  \w     56.00  97.00   1.00   25.00    --   88.04-109.00 -72.00   41
  9  \w     30.00 112.00   1.00   25.00    --   88.04 -77.00 -90.00   82
 10  \w    -23.00  26.00   1.00    5.00    --    0.00  77.00-180.00   49
 11  \w    -74.00  15.00   1.00    5.00    --    0.00 -19.00 -30.00   89
 12  \w   -134.00 -84.00   1.00   25.00    --  -88.04-109.00 -72.00   50
 13  \w   -161.00 -74.00   1.00   25.00    --  -88.04 -37.00 -60.00   87
 14  \w   -162.00 -79.00   1.00   25.00    --  -88.04 -37.00 -30.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0158347000
_diffrn_orient_matrix_UB_12      -0.0486983000
_diffrn_orient_matrix_UB_13      0.0272386000
_diffrn_orient_matrix_UB_21      0.0452398000
_diffrn_orient_matrix_UB_22      0.0218844000
_diffrn_orient_matrix_UB_23      0.0332732000
_diffrn_orient_matrix_UB_31      -0.0186202000
_diffrn_orient_matrix_UB_32      0.0119340000
_diffrn_orient_matrix_UB_33      0.0503436000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.875
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51204
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.500
_diffrn_reflns_theta_min         3.670
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull dark red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.898
_exptl_crystal_description       needle
_exptl_crystal_F_000             5904
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.855
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     843
_refine_ls_number_reflns         16287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.1683
_refine_ls_R_factor_gt           0.1246
_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^)+(0.1090P)^2^+103.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2951
_refine_ls_wR_factor_ref         0.3349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8826
_reflns_number_total             16287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05416a2.cif
_cod_data_source_block           exp_545
_cod_database_code               1550686
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.952
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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. Uiso/Uaniso restraints and constraints
Uanis(C01R) = Uanis(C02I)
Uanis(C3) = Uanis(C01Z)
Uanis(C02A) = Uanis(C02L)
Uanis(C02K) = Uanis(C1AA)
Uanis(C032) = Uanis(C02K) = Uanis(C031) = Uanis(C02W)
Uanis(C02Q) = Uanis(C02N) = Uanis(C01Z) = Uanis(C02Y)
Uanis(C01V) = Uanis(C01W) = Uanis(C026) = Uanis(C028) = Uanis(C02H) =
Uanis(C027)
Uanis(C02E) = Uanis(C024) = Uanis(C020) = Uanis(C022) = Uanis(C01O) =
Uanis(C01E) = Uanis(C01U) = Uanis(C02V) = Uanis(C02G)
Uanis(C1AA) = Uanis(C4) = Uanis(C0AA)
Uanis(C02Z) = Uanis(C02X) = Uanis(C02O) = Uanis(C02B) = Uanis(C02P) =
Uanis(C02U)
Uanis(C02S) = Uanis(C02T) = Uanis(C030)
Uanis(C3) = Uanis(C1) = Uanis(C6)
3. Others
 Fixed Sof: C02N(0.5) H02G(0.5) H02H(0.5) H02I(0.5) C02Q(0.5) H02J(0.5)
 H02K(0.5) H02L(0.5) C02W(0.5) H4AA(0.5) HI(0.5) HJ(0.5) C02Y(0.5) H02S(0.5)
 H02T(0.5) H02V(0.5) C031(0.5) H03D(0.5) H03E(0.5) H03F(0.5) C032(0.5)
 H03G(0.5) H03H(0.5) H03I(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C3(0.5)
 H3A(0.5) H3B(0.5) H3C(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C0AA(0.5)
 H0AB(0.5) H0AC(0.5) H0AD(0.5) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5) C1AA(0.5)
 H1AB(0.5) H1AC(0.5) H1AD(0.5)
4.a Ternary CH refined with riding coordinates:
 C00B(H00B), C01K(H01K), C01Q(H01Q), C01R(H01R)
4.b Me refined with riding coordinates:
 C02C(H02W,H02Y,H), C02S(H02M,H02N,H02O), C02V(H3AA,HG,HH), C1(H1A,H1B,H1C)
4.c Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C013(H013), C014(H014), C015(H015), C017(H017), C018(H018),
 C019(H019), C01A(H01A), C01B(H01H), C01D(H01D), C01F(H01F), C01G(H01G),
 C01H(H01I), C01P(H01P), C01S(H01S), C01X(H01X), C01Y(H01Y), C020(H020),
 C022(H022), C026(H026), C027(H027), C029(H029), C02H(H02), C02L(H1AA),
 C02U(H02U), C02X(H02X)
4.d Idealised Me refined as rotating group:
 C01M(H01B,H01C,H01E), C01U(H01J,H01L,H01M), C021(H02A,H02B,H02C), C02D(H02D,
 H02E,H02F), C02G(H02Z,HA,HB), C02J(H0AA,HC,HD), C02M(H2AA,HE,HF), C02N(H02G,
 H02H,H02I), C02Q(H02J,H02K,H02L), C02T(H02P,H02Q,H02R), C02W(H4AA,HI,HJ),
 C02Y(H02S,H02T,H02V), C030(H03A,H03B,H03C), C031(H03D,H03E,H03F), C032(H03G,
 H03H,H03I), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C0AA(H0AB,H0AC,H0AD), C4(H4A,H4B,
 H4C), C1AA(H1AB,H1AC,H1AD)
;
_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 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.556