#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:00:04 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/39/1553904.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_1553904
loop_
_publ_author_name
'Shi, Xinzhe'
'Roisnel, Thierry'
'Soulé, Jean-François'
'Doucet, Henri'
_publ_section_title
;
 Synthesis of mono- and di-arylated acenaphthylenes and programmed access
 to dibenzo[j,l]fluoranthenes via palladium-catalysed C--H bond
 functionalisation
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              398
_journal_paper_doi               10.1039/C7QO00799J
_journal_volume                  5
_journal_year                    2018
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H14 Cl2'
_chemical_formula_sum            'C24 H14 Cl2'
_chemical_formula_weight         373.25
_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'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2017-06-02 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.382(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8237(12)
_cell_length_b                   11.3330(7)
_cell_length_c                   10.2994(8)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.65
_cell_measurement_wavelength     0.71073
_cell_volume                     1788.6(2)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4736
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.479
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_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     119
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0422P)²+1.4346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1756
_reflns_number_total             2048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00799j2.cif
_cod_data_source_block           SX25_SP2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1553904
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.32828(8) 0.16558(11) 0.44358(15) 0.0203(3) Uani 1 1 d . . .
C2 C 0.34445(9) 0.26123(12) 0.37459(15) 0.0215(3) Uani 1 1 d . . .
H2 H 0.326399 0.260500 0.274177 0.026 Uiso 1 1 calc R U .
C3 C 0.38762(9) 0.35836(12) 0.45508(14) 0.0201(3) Uani 1 1 d . . .
H3 H 0.398624 0.424790 0.408671 0.024 Uiso 1 1 calc R U .
C4 C 0.41517(8) 0.36029(11) 0.60289(14) 0.0181(3) Uani 1 1 d . . .
C5 C 0.39573(8) 0.26281(12) 0.66821(14) 0.0201(3) Uani 1 1 d . . .
H5 H 0.412517 0.263489 0.768315 0.024 Uiso 1 1 calc R U .
C6 C 0.35247(9) 0.16547(12) 0.58942(15) 0.0211(3) Uani 1 1 d . . .
H6 H 0.339618 0.099715 0.634671 0.025 Uiso 1 1 calc R U .
C7 C 0.46354(9) 0.46293(11) 0.68616(14) 0.0182(3) Uani 1 1 d . . .
C8 C 0.43886(9) 0.58702(12) 0.64277(14) 0.0194(3) Uani 1 1 d . . .
C9 C 0.37326(9) 0.64179(13) 0.53047(15) 0.0240(3) Uani 1 1 d . . .
H9 H 0.329807 0.596977 0.457607 0.029 Uiso 1 1 calc R U .
C10 C 0.500000 0.65790(17) 0.750000 0.0195(4) Uani 1 2 d S T P
C11 C 0.500000 0.78079(17) 0.750000 0.0229(4) Uani 1 2 d S T P
C12 C 0.56703(10) 0.83550(13) 0.86939(17) 0.0274(3) Uani 1 1 d . . .
H12 H 0.569725 0.919084 0.876953 0.033 Uiso 1 1 calc R U .
C13 C 0.62801(10) 0.76743(13) 0.97401(16) 0.0281(3) Uani 1 1 d . . .
H13 H 0.672676 0.805752 1.052227 0.034 Uiso 1 1 calc R U .
Cl1 Cl 0.27588(2) 0.04204(3) 0.34336(4) 0.02943(13) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 121.73(12) . .
C2 C1 Cl1 118.87(11) . .
C6 C1 Cl1 119.40(10) . .
C1 C2 C3 118.66(13) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C2 C3 C4 121.29(13) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C4 C5 118.23(12) . .
C3 C4 C7 120.09(12) . .
C5 C4 C7 121.67(12) . .
C6 C5 C4 121.16(13) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C1 C6 C5 118.88(12) . .
C1 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
C7 C7 C4 127.92(7) 2_656 .
C7 C7 C8 108.40(7) 2_656 .
C4 C7 C8 123.67(11) . .
C9 C8 C10 118.37(13) . .
C9 C8 C7 135.25(13) . .
C10 C8 C7 106.36(12) . .
C8 C9 C13 118.36(14) . 2_656
C8 C9 H9 120.8 . .
C13 C9 H9 120.8 2_656 .
C11 C10 C8 124.76(8) . 2_656
C11 C10 C8 124.76(8) . .
C8 C10 C8 110.48(17) 2_656 .
C10 C11 C12 115.84(9) . .
C10 C11 C12 115.84(9) . 2_656
C12 C11 C12 128.32(18) . 2_656
C13 C12 C11 120.06(14) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C9 122.57(14) . 2_656
C12 C13 H13 118.7 . .
C9 C13 H13 118.7 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.383(2) .
C1 C6 1.385(2) .
C1 Cl1 1.7468(14) .
C2 C3 1.3890(19) .
C2 H2 0.9500 .
C3 C4 1.3966(19) .
C3 H3 0.9500 .
C4 C5 1.4005(19) .
C4 C7 1.4747(18) .
C5 C6 1.3848(19) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C7 1.379(3) 2_656
C7 C8 1.4822(18) .
C8 C9 1.3737(19) .
C8 C10 1.4089(17) .
C9 C13 1.425(2) 2_656
C9 H9 0.9500 .
C10 C11 1.393(3) .
C11 C12 1.4224(17) .
C11 C12 1.4224(17) 2_656
C12 C13 1.377(2) .
C12 H12 0.9500 .
C13 H13 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
C6 C1 C2 C3 1.2(2) . .
Cl1 C1 C2 C3 -178.78(10) . .
C1 C2 C3 C4 0.5(2) . .
C2 C3 C4 C5 -2.0(2) . .
C2 C3 C4 C7 177.88(12) . .
C3 C4 C5 C6 1.7(2) . .
C7 C4 C5 C6 -178.11(12) . .
C2 C1 C6 C5 -1.5(2) . .
Cl1 C1 C6 C5 178.55(10) . .
C4 C5 C6 C1 -0.1(2) . .
C3 C4 C7 C7 -136.55(18) . 2_656
C5 C4 C7 C7 43.3(2) . 2_656
C3 C4 C7 C8 44.05(19) . .
C5 C4 C7 C8 -136.10(14) . .
C7 C7 C8 C9 -178.68(16) 2_656 .
C4 C7 C8 C9 0.8(2) . .
C7 C7 C8 C10 -0.10(17) 2_656 .
C4 C7 C8 C10 179.40(11) . .
C10 C8 C9 C13 1.91(19) . 2_656
C7 C8 C9 C13 -179.65(15) . 2_656
C9 C8 C10 C11 -1.10(14) . .
C7 C8 C10 C11 -179.96(6) . .
C9 C8 C10 C8 178.90(14) . 2_656
C7 C8 C10 C8 0.04(6) . 2_656
C8 C10 C11 C12 -0.68(10) 2_656 .
C8 C10 C11 C12 179.32(10) . .
C8 C10 C11 C12 179.32(10) 2_656 2_656
C8 C10 C11 C12 -0.68(10) . 2_656
C10 C11 C12 C13 1.59(16) . .
C12 C11 C12 C13 -178.41(16) 2_656 .
C11 C12 C13 C9 -0.8(2) . 2_656
