#------------------------------------------------------------------------------
#$Date: 2019-11-25 21:45:21 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241892 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/17/4131723.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_4131723
loop_
_publ_author_name
'Jin, Zexin'
'Teo, Yew Chin'
'Teat, Simon J.'
'Xia, Yan'
_publ_section_title
;
 Regioselective Synthesis of [3]Naphthylenes and Tuning of Their
 Antiaromaticity.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15933
_journal_page_last               15939
_journal_paper_doi               10.1021/jacs.7b09222
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C34 H24'
_chemical_formula_weight         432.53
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.358(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8079(5)
_cell_length_b                   5.2899(3)
_cell_length_c                   26.0814(17)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9724
_cell_measurement_theta_min      2.8749
_cell_volume                     1065.80(11)
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_collection       'Bruker APEX 3'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/5'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_number            25376
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        27.706
_diffrn_reflns_theta_max         28.972
_diffrn_reflns_theta_min         2.879
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 2012/1 Bruker AXS Madison WI USA'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0461
_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)+(0.0419P)²+0.9236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1880
_reflns_number_total             2184
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b09222_si_004.cif
_cod_data_source_block           twin4_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4131723
_shelx_shelxl_version_number     2014/7
_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   0.982
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.4740(2) -0.0315(3) 0.26392(6) 0.0216(4) Uani 1 1 d . .
H1A H 0.4725 -0.1474 0.2360 0.026 Uiso 1 1 calc R U
C2 C 0.6093(2) 0.1411(3) 0.27467(7) 0.0209(4) Uani 1 1 d . .
H2A H 0.7007 0.1422 0.2543 0.025 Uiso 1 1 calc R U
C3 C 0.6103(2) 0.3106(3) 0.31501(6) 0.0192(4) Uani 1 1 d . .
H3A H 0.7028 0.4280 0.3218 0.023 Uiso 1 1 calc R U
C4 C 0.4778(2) 0.3138(3) 0.34628(6) 0.0174(4) Uani 1 1 d . .
C5 C 0.4827(2) 0.4973(3) 0.38842(6) 0.0171(4) Uani 1 1 d . .
C6 C 0.3516(2) 0.4756(3) 0.41638(6) 0.0181(4) Uani 1 1 d . .
C7 C 0.2686(2) 0.5826(3) 0.45971(6) 0.0182(4) Uani 1 1 d . .
C8 C 0.2748(2) 0.7730(3) 0.49704(6) 0.0195(4) Uani 1 1 d . .
H8A H 0.3662 0.8931 0.5020 0.023 Uiso 1 1 calc R U
C9 C 0.1410(2) 0.7774(3) 0.52632(6) 0.0190(4) Uani 1 1 d . .
H9A H 0.1408 0.9048 0.5520 0.023 Uiso 1 1 calc R U
C10 C -0.0037(2) 0.4009(3) 0.48044(6) 0.0171(4) Uani 1 1 d . .
C11 C 0.1346(2) 0.4052(3) 0.45133(6) 0.0170(3) Uani 1 1 d . .
C12 C 0.2131(2) 0.2921(3) 0.40679(6) 0.0174(4) Uani 1 1 d . .
C13 C 0.1983(2) 0.1241(3) 0.36753(6) 0.0176(4) Uani 1 1 d . .
C14 C 0.3387(2) 0.1347(3) 0.33573(6) 0.0176(4) Uani 1 1 d . .
C15 C 0.3416(2) -0.0336(3) 0.29399(6) 0.0196(4) Uani 1 1 d . .
H15A H 0.2501 -0.1520 0.2862 0.024 Uiso 1 1 calc R U
C16 C 0.6226(2) 0.6923(3) 0.39864(7) 0.0209(4) Uani 1 1 d . .
H16A H 0.5987 0.8036 0.4268 0.031 Uiso 1 1 calc R U
H16B H 0.6263 0.7926 0.3672 0.031 Uiso 1 1 calc R U
H16C H 0.7344 0.6083 0.4086 0.031 Uiso 1 1 calc R U
C17 C 0.0531(2) -0.0627(3) 0.35540(7) 0.0210(4) Uani 1 1 d . .
H17A H -0.0282 -0.0434 0.3804 0.032 Uiso 1 1 calc R U
H17B H 0.1002 -0.2347 0.3575 0.032 Uiso 1 1 calc R U
H17C H -0.0074 -0.0317 0.3203 0.032 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 0.0040 0.0020
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
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
C15 C1 C2 119.83(16) . .
C15 C1 H1A 120.1 . .
C2 C1 H1A 120.1 . .
C3 C2 C1 119.90(16) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C2 C3 C4 121.74(16) . .
C2 C3 H3A 119.1 . .
C4 C3 H3A 119.1 . .
C3 C4 C14 118.65(15) . .
C3 C4 C5 120.17(15) . .
C14 C4 C5 121.18(14) . .
C6 C5 C4 114.33(15) . .
C6 C5 C16 123.72(15) . .
C4 C5 C16 121.95(14) . .
C5 C6 C12 124.88(15) . .
C5 C6 C7 145.66(16) . .
C12 C6 C7 89.41(13) . .
C8 C7 C11 122.81(15) . .
C8 C7 C6 145.70(16) . .
C11 C7 C6 91.39(13) . .
C9 C8 C7 116.44(15) . .
C9 C8 H8A 121.8 . .
C7 C8 H8A 121.8 . .
C8 C9 C10 122.57(15) . 3_566
C8 C9 H9A 118.7 . .
C10 C9 H9A 118.7 3_566 .
C11 C10 C9 124.63(15) . 3_566
C11 C10 C10 114.23(18) . 3_566
C9 C10 C10 121.14(18) 3_566 3_566
C7 C11 C10 122.80(15) . .
C7 C11 C12 90.44(13) . .
C10 C11 C12 146.70(15) . .
C13 C12 C6 123.55(15) . .
C13 C12 C11 147.58(16) . .
C6 C12 C11 88.75(13) . .
C12 C13 C14 114.52(15) . .
C12 C13 C17 124.90(15) . .
C14 C13 C17 120.58(14) . .
C15 C14 C4 117.90(15) . .
C15 C14 C13 120.61(15) . .
C4 C14 C13 121.49(15) . .
C1 C15 C14 121.97(16) . .
C1 C15 H15A 119.0 . .
C14 C15 H15A 119.0 . .
C5 C16 H16A 109.5 . .
C5 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C5 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C13 C17 H17A 109.5 . .
C13 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C13 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C15 1.385(2) .
C1 C2 1.394(2) .
C1 H1A 0.9500 .
C2 C3 1.381(2) .
C2 H2A 0.9500 .
C3 C4 1.407(2) .
C3 H3A 0.9500 .
C4 C14 1.437(2) .
C4 C5 1.463(2) .
C5 C6 1.345(2) .
C5 C16 1.498(2) .
C6 C12 1.447(2) .
C6 C7 1.493(2) .
C7 C8 1.397(2) .
C7 C11 1.399(2) .
C8 C9 1.381(2) .
C8 H8A 0.9500 .
C9 C10 1.420(2) 3_566
C9 H9A 0.9500 .
C10 C11 1.407(2) .
C10 C9 1.420(2) 3_566
C10 C10 1.458(3) 3_566
C11 C12 1.513(2) .
C12 C13 1.348(2) .
C13 C14 1.469(2) .
C13 C17 1.502(2) .
C14 C15 1.409(2) .
C15 H15A 0.9500 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
