#------------------------------------------------------------------------------
#$Date: 2017-03-04 06:37:15 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193047 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/56/4125650.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_4125650
loop_
_publ_author_name
'McAtee, Christopher C.'
'Riehl, Paul S.'
'Schindler, Corinna S.'
_publ_section_title
;
 Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin
 Metathesis.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2960
_journal_page_last               2963
_journal_paper_doi               10.1021/jacs.7b01114
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C24 H18'
_chemical_formula_sum            'C24 H18'
_chemical_formula_weight         306.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.92565(12)
_cell_length_b                   6.76441(5)
_cell_length_c                   16.55751(12)
_cell_measurement_reflns_used    14219
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.8310
_cell_measurement_theta_min      4.1300
_cell_volume                     1559.70(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.132
_diffrn_reflns_theta_min         5.343
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0197(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0399
_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/[σ²(Fo²)+(0.0520P)²+0.4069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1420
_reflns_number_total             1452
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b01114_si_005.cif
_cod_data_source_block           ccm530
_cod_database_code               4125650
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.941
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.34271(8) 0.64491(17) 0.60590(7) 0.0292(3) Uani 1 1 d . .
H1A H 0.2873 0.6391 0.5695 0.044 Uiso 1 1 calc R U
H1B H 0.3771 0.7697 0.5976 0.044 Uiso 1 1 calc R U
H1C H 0.3206 0.6370 0.6620 0.044 Uiso 1 1 calc R U
C2 C 0.40886(8) 0.47464(15) 0.58844(6) 0.0245(3) Uani 1 1 d . .
C3 C 0.49833(7) 0.45362(15) 0.63292(6) 0.0238(3) Uani 1 1 d . .
C4 C 0.52539(8) 0.59227(16) 0.69209(6) 0.0271(3) Uani 1 1 d . .
H4 H 0.4832 0.6984 0.7046 0.032 Uiso 1 1 calc R U
C5 C 0.61170(8) 0.57746(17) 0.73233(6) 0.0290(3) Uani 1 1 d . .
H5 H 0.6280 0.6704 0.7731 0.035 Uiso 1 1 calc R U
C6 C 0.67517(8) 0.42421(17) 0.71263(6) 0.0282(3) Uani 1 1 d . .
H6 H 0.7358 0.4162 0.7387 0.034 Uiso 1 1 calc R U
C7 C 0.65011(8) 0.28509(16) 0.65573(6) 0.0257(3) Uani 1 1 d . .
H7 H 0.6939 0.1820 0.6430 0.031 Uiso 1 1 calc R U
C8 C 0.56067(8) 0.29267(15) 0.61597(6) 0.0235(3) Uani 1 1 d . .
C9 C 0.53157(7) 0.14169(15) 0.55802(6) 0.0229(3) Uani 1 1 d . .
C10 C 0.44425(7) 0.16920(15) 0.51443(6) 0.0231(3) Uani 1 1 d . .
C11 C 0.38644(8) 0.34030(15) 0.53083(6) 0.0245(3) Uani 1 1 d . .
H11 H 0.3299 0.3602 0.4998 0.029 Uiso 1 1 calc R U
C12 C 0.41545(7) 0.02924(15) 0.45751(6) 0.0237(3) Uani 1 1 d . .
H12 H 0.3577 0.0510 0.4283 0.028 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C11 C2 C3 119.26(9) . .
C11 C2 C1 120.57(10) . .
C3 C2 C1 120.17(10) . .
C4 C3 C8 118.99(10) . .
C4 C3 C2 121.11(10) . .
C8 C3 C2 119.90(10) . .
C5 C4 C3 121.44(10) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 119.45(10) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
C7 C6 C5 120.35(10) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C8 121.25(10) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C7 C8 C3 118.40(10) . .
C7 C8 C9 121.81(9) . .
C3 C8 C9 119.79(10) . .
C12 C9 C10 117.75(10) 5_656 .
C12 C9 C8 123.67(10) 5_656 .
C10 C9 C8 118.58(10) . .
C12 C10 C9 119.90(10) . .
C12 C10 C11 120.91(10) . .
C9 C10 C11 119.18(10) . .
C2 C11 C10 123.02(10) . .
C2 C11 H11 118.5 . .
C10 C11 H11 118.5 . .
C10 C12 C9 122.34(10) . 5_656
C10 C12 H12 118.8 . .
C9 C12 H12 118.8 5_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.5030(14) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C11 1.3539(16) .
C2 C3 1.4543(15) .
C3 C4 1.4076(15) .
C3 C8 1.4205(15) .
C4 C5 1.3779(16) .
C4 H4 0.9500 .
C5 C6 1.4007(16) .
C5 H5 0.9500 .
C6 C7 1.3767(15) .
C6 H6 0.9500 .
C7 C8 1.4096(15) .
C7 H7 0.9500 .
C8 C9 1.4587(15) .
C9 C12 1.3955(15) 5_656
C9 C10 1.4262(15) .
C10 C12 1.3948(15) .
C10 C11 1.4357(15) .
C11 H11 0.9500 .
C12 C9 1.3954(15) 5_656
C12 H12 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C11 C2 C3 C4 178.63(9) . .
C1 C2 C3 C4 -0.80(15) . .
C11 C2 C3 C8 -0.39(15) . .
C1 C2 C3 C8 -179.82(9) . .
C8 C3 C4 C5 1.51(15) . .
C2 C3 C4 C5 -177.52(9) . .
C3 C4 C5 C6 1.65(16) . .
C4 C5 C6 C7 -2.43(16) . .
C5 C6 C7 C8 -0.01(16) . .
C6 C7 C8 C3 3.15(15) . .
C6 C7 C8 C9 -177.41(9) . .
C4 C3 C8 C7 -3.85(14) . .
C2 C3 C8 C7 175.20(9) . .
C4 C3 C8 C9 176.70(9) . .
C2 C3 C8 C9 -4.26(14) . .
C7 C8 C9 C12 5.89(15) . 5_656
C3 C8 C9 C12 -174.68(9) . 5_656
C7 C8 C9 C10 -174.01(9) . .
C3 C8 C9 C10 5.43(14) . .
C12 C9 C10 C12 -1.11(16) 5_656 .
C8 C9 C10 C12 178.79(9) . .
C12 C9 C10 C11 178.01(9) 5_656 .
C8 C9 C10 C11 -2.09(14) . .
C3 C2 C11 C10 3.93(15) . .
C1 C2 C11 C10 -176.64(9) . .
C12 C10 C11 C2 176.44(9) . .
C9 C10 C11 C2 -2.67(15) . .
C9 C10 C12 C9 1.16(17) . 5_656
C11 C10 C12 C9 -177.95(9) . 5_656
