#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/67/4026764.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4026764
loop_
_publ_author_name
'Alexander V. Zabula'
'Cristina Dubceac'
'Alexander S. Filatov'
'Marina A. Petrukhina'
_publ_section_title
;
 Selective Surface Decoration of Corannulene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9572
_journal_page_last               9576
_journal_paper_doi               10.1021/jo201765j
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C22 H14 Cl, Al Cl4'
_chemical_formula_sum            'C22 H14 Al Cl5'
_chemical_formula_weight         482.56
_chemical_name_systematic
; 
 2b-(2-chloroethyl)-2aH, 2bH-corannulene-2a-yl aluminum tetrachloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.706(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.930(4)
_cell_length_b                   14.202(5)
_cell_length_c                   12.708(4)
_cell_measurement_reflns_used    4572
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      2.28
_cell_volume                     2072.7(12)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15523
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0132P)²+10.9622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                2714
_reflns_number_total             4167
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo201765j_si_002.cif
_cod_data_source_block           compound_1
_cod_original_sg_symbol_Hall     '-P 2yn      '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4026764
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6245(5) 0.2497(3) 0.2023(4) 0.0353(12) Uani 1 1 d .
H1A H 0.6304 0.2789 0.1333 0.042 Uiso 1 1 calc R
H1B H 0.5528 0.2733 0.2185 0.042 Uiso 1 1 calc R
C2 C 0.7282(5) 0.2748(4) 0.2931(5) 0.0482(15) Uani 1 1 d .
H2A H 0.7965 0.2393 0.2842 0.058 Uiso 1 1 calc R
H2B H 0.7144 0.2556 0.3634 0.058 Uiso 1 1 calc R
C3 C 0.7567(5) 0.3855(4) 0.2970(5) 0.0430(14) Uani 1 1 d .
C4 C 0.8559(6) 0.3982(4) 0.3978(5) 0.0491(16) Uani 1 1 d .
C5 C 0.9642(5) 0.3879(4) 0.3823(6) 0.0536(18) Uani 1 1 d .
H5 H 1.0287 0.3752 0.4433 0.064 Uiso 1 1 calc R
C6 C 0.9830(5) 0.3962(4) 0.2727(6) 0.0468(16) Uani 1 1 d .
H6 H 1.0588 0.3859 0.2644 0.056 Uiso 1 1 calc R
C7 C 0.8935(6) 0.4186(4) 0.1817(5) 0.0471(15) Uani 1 1 d .
C8 C 0.9036(6) 0.4635(4) 0.0885(6) 0.0550(17) Uani 1 1 d .
H8 H 0.9746 0.4594 0.0685 0.066 Uiso 1 1 calc R
C9 C 0.8070(6) 0.5170(4) 0.0203(5) 0.0527(17) Uani 1 1 d .
H9 H 0.8156 0.5463 -0.0442 0.063 Uiso 1 1 calc R
C10 C 0.7041(6) 0.5262(4) 0.0471(5) 0.0510(16) Uani 1 1 d .
C11 C 0.6194(6) 0.5958(4) 0.0187(5) 0.0496(16) Uani 1 1 d .
H11 H 0.6136 0.6315 -0.0458 0.059 Uiso 1 1 calc R
C12 C 0.5393(6) 0.6159(4) 0.0838(6) 0.0554(18) Uani 1 1 d .
H12 H 0.4837 0.6648 0.0604 0.066 Uiso 1 1 calc R
C13 C 0.5401(5) 0.5671(4) 0.1784(6) 0.0514(16) Uani 1 1 d .
C14 C 0.5004(5) 0.5969(4) 0.2664(6) 0.0489(16) Uani 1 1 d .
H14 H 0.4421 0.6442 0.2562 0.059 Uiso 1 1 calc R
C15 C 0.5479(5) 0.5557(4) 0.3727(7) 0.0578(19) Uani 1 1 d .
H15 H 0.5214 0.5778 0.4323 0.069 Uiso 1 1 calc R
C16 C 0.6322(6) 0.4840(4) 0.3912(6) 0.0520(16) Uani 1 1 d .
C17 C 0.7154(6) 0.4647(4) 0.4898(5) 0.0551(18) Uani 1 1 d .
H17 H 0.6984 0.4797 0.5567 0.066 Uiso 1 1 calc R
C18 C 0.8282(6) 0.4220(4) 0.4927(5) 0.0486(16) Uani 1 1 d .
H18 H 0.8829 0.4107 0.5612 0.058 Uiso 1 1 calc R
C19 C 0.7803(5) 0.4153(4) 0.1953(5) 0.0411(14) Uani 1 1 d .
C20 C 0.6909(5) 0.4670(4) 0.1353(5) 0.0427(14) Uani 1 1 d .
C21 C 0.6147(5) 0.4867(3) 0.1960(5) 0.0406(14) Uani 1 1 d .
C22 C 0.6537(5) 0.4466(4) 0.2974(5) 0.0423(14) Uani 1 1 d .
Al1 Al 0.85787(15) 0.25817(12) 0.86804(15) 0.0404(4) Uani 1 1 d .
Cl1 Cl 0.61856(14) 0.12379(9) 0.18892(13) 0.0480(4) Uani 1 1 d .
Cl2 Cl 1.03039(13) 0.25916(11) 0.97305(14) 0.0526(4) Uani 1 1 d .
Cl3 Cl 0.73705(13) 0.24178(12) 0.96317(14) 0.0532(4) Uani 1 1 d .
Cl4 Cl 0.83760(18) 0.13965(13) 0.76148(17) 0.0726(6) Uani 1 1 d .
Cl5 Cl 0.82501(16) 0.38532(13) 0.77674(15) 0.0647(5) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 Cl1 108.4(4)
C2 C1 H1A 110.0
Cl1 C1 H1A 110.0
C2 C1 H1B 110.0
Cl1 C1 H1B 110.0
H1A C1 H1B 108.4
C1 C2 C3 112.5(4)
C1 C2 H2A 109.1
C3 C2 H2A 109.1
C1 C2 H2B 109.1
C3 C2 H2B 109.1
H2A C2 H2B 107.8
C19 C3 C4 115.2(5)
C19 C3 C22 100.9(5)
C4 C3 C22 112.6(5)
C19 C3 C2 110.3(5)
C4 C3 C2 104.8(4)
C22 C3 C2 113.4(5)
C5 C4 C18 127.8(7)
C5 C4 C3 115.0(6)
C18 C4 C3 117.2(6)
C4 C5 C6 121.3(6)
C4 C5 H5 119.4
C6 C5 H5 119.4
C7 C6 C5 121.9(6)
C7 C6 H6 119.0
C5 C6 H6 119.0
C8 C7 C6 126.7(6)
C8 C7 C19 115.5(6)
C6 C7 C19 116.0(6)
C7 C8 C9 120.9(6)
C7 C8 H8 119.5
C9 C8 H8 119.5
C10 C9 C8 121.4(6)
C10 C9 H9 119.3
C8 C9 H9 119.3
C9 C10 C11 129.9(6)
C9 C10 C20 115.6(6)
C11 C10 C20 113.1(6)
C10 C11 C12 122.4(6)
C10 C11 H11 118.8
C12 C11 H11 118.8
C13 C12 C11 123.0(6)
C13 C12 H12 118.5
C11 C12 H12 118.5
C12 C13 C14 128.4(6)
C12 C13 C21 113.2(6)
C14 C13 C21 116.7(6)
C13 C14 C15 119.7(6)
C13 C14 H14 120.1
C15 C14 H14 120.1
C16 C15 C14 122.3(6)
C16 C15 H15 118.9
C14 C15 H15 118.9
C22 C16 C17 116.3(6)
C22 C16 C15 115.0(6)
C17 C16 C15 126.4(7)
C16 C17 C18 121.8(6)
C16 C17 H17 119.1
C18 C17 H17 119.1
C4 C18 C17 121.1(6)
C4 C18 H18 119.5
C17 C18 H18 119.5
C20 C19 C7 123.4(6)
C20 C19 C3 110.3(5)
C7 C19 C3 122.7(6)
C19 C20 C21 109.6(5)
C19 C20 C10 121.4(6)
C21 C20 C10 123.2(6)
C22 C21 C20 109.7(5)
C22 C21 C13 121.2(6)
C20 C21 C13 123.7(6)
C21 C22 C16 123.6(6)
C21 C22 C3 107.8(5)
C16 C22 C3 124.2(6)
Cl5 Al1 Cl2 109.93(10)
Cl5 Al1 Cl3 110.47(10)
Cl2 Al1 Cl3 109.45(10)
Cl5 Al1 Cl4 110.58(11)
Cl2 Al1 Cl4 109.12(10)
Cl3 Al1 Cl4 107.24(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.488(8)
C1 Cl1 1.796(5)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.607(7)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C19 1.457(8)
C3 C4 1.500(8)
C3 C22 1.506(8)
C4 C5 1.367(8)
C4 C18 1.377(9)
C5 C6 1.474(9)
C5 H5 0.9500
C6 C7 1.382(9)
C6 H6 0.9500
C7 C8 1.378(9)
C7 C19 1.409(8)
C8 C9 1.455(9)
C8 H8 0.9500
C9 C10 1.366(9)
C9 H9 0.9500
C10 C11 1.390(9)
C10 C20 1.443(8)
C11 C12 1.451(9)
C11 H11 0.9500
C12 C13 1.385(9)
C12 H12 0.9500
C13 C14 1.393(9)
C13 C21 1.428(8)
C14 C15 1.441(9)
C14 H14 0.9500
C15 C16 1.406(9)
C15 H15 0.9500
C16 C22 1.391(8)
C16 C17 1.398(9)
C17 C18 1.467(9)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.348(8)
C20 C21 1.372(8)
C21 C22 1.369(8)
Al1 Cl5 2.125(3)
Al1 Cl2 2.128(2)
Al1 Cl3 2.130(2)
Al1 Cl4 2.133(2)
