#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:27:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178479 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/00/4030015.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_4030015
loop_
_publ_author_name
'Xue, Jing Yang'
'Ikemoto, Koki'
'Takahashi, Norihisa'
'Izumi, Tomoo'
'Taka, Hideo'
'Kita, Hiroshi'
'Sato, Sota'
'Isobe, Hiroyuki'
_publ_section_title
;
 Cyclo-meta-phenylene Revisited: Nickel-Mediated Synthesis, Molecular
 Structures, and Device Applications.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9735
_journal_page_last               9739
_journal_paper_doi               10.1021/jo501903n
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C36 H24'
_chemical_formula_sum            'C36 H24'
_chemical_formula_weight         456.55
_chemical_name_common            '[6]cyclo-m-phenylene'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-27
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.289(3)
_cell_length_b                   15.382(3)
_cell_length_c                   6.0239(12)
_cell_measurement_reflns_used    3342
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      66.82
_cell_measurement_theta_min      3.65
_cell_volume                     1123.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8005
_diffrn_reflns_theta_full        67.33
_diffrn_reflns_theta_max         67.33
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0362
_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)+(0.0621P)²+0.2064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1723
_reflns_number_total             1960
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo501903n_si_003.cif
_cod_data_source_block           6CMP
_cod_depositor_comments
'Adding full bibliography for 4030014--4030018.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4030015
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.68339(10) 0.43314(7) -0.17470(19) 0.0178(3) Uani 1 1 d .
H1 H 0.6267 0.4698 -0.2490 0.021 Uiso 1 1 calc R
C2 C 0.78858(10) 0.44114(8) -0.2266(2) 0.0187(3) Uani 1 1 d .
C3 C 0.87110(10) 0.38728(8) -0.1153(2) 0.0214(3) Uani 1 1 d .
H2 H 0.9441 0.3916 -0.1470 0.026 Uiso 1 1 calc R
C4 C 0.84695(10) 0.32773(8) 0.0408(2) 0.0220(3) Uani 1 1 d .
H3 H 0.9039 0.2914 0.1159 0.026 Uiso 1 1 calc R
C5 C 0.74193(10) 0.32004(8) 0.0895(2) 0.0207(3) Uani 1 1 d .
H4 H 0.7266 0.2783 0.1965 0.025 Uiso 1 1 calc R
C6 C 0.65772(10) 0.37347(7) -0.0179(2) 0.0182(3) Uani 1 1 d .
C7 C 0.45534(10) 0.38908(7) -0.1324(2) 0.0177(3) Uani 1 1 d .
H5 H 0.4693 0.4106 -0.2729 0.021 Uiso 1 1 calc R
C8 C 0.54434(10) 0.36716(7) 0.0309(2) 0.0178(3) Uani 1 1 d .
C9 C 0.52228(10) 0.33683(7) 0.2369(2) 0.0199(3) Uani 1 1 d .
H6 H 0.5815 0.3225 0.3532 0.024 Uiso 1 1 calc R
C10 C 0.41511(11) 0.32746(7) 0.2727(2) 0.0210(3) Uani 1 1 d .
H7 H 0.4010 0.3063 0.4135 0.025 Uiso 1 1 calc R
C11 C 0.32795(10) 0.34842(7) 0.1070(2) 0.0199(3) Uani 1 1 d .
H8 H 0.2544 0.3408 0.1333 0.024 Uiso 1 1 calc R
C12 C 0.34731(10) 0.38074(7) -0.0986(2) 0.0180(3) Uani 1 1 d .
C13 C 0.26919(10) 0.47133(7) -0.4273(2) 0.0181(3) Uani 1 1 d .
H9 H 0.3351 0.5047 -0.4012 0.022 Uiso 1 1 calc R
C14 C 0.25637(10) 0.40374(8) -0.2816(2) 0.0188(3) Uani 1 1 d .
C15 C 0.15808(10) 0.35706(8) -0.3175(2) 0.0217(3) Uani 1 1 d .
H10 H 0.1471 0.3105 -0.2200 0.026 Uiso 1 1 calc R
C16 C 0.07659(11) 0.37854(8) -0.4948(2) 0.0240(3) Uani 1 1 d .
H11 H 0.0092 0.3471 -0.5167 0.029 Uiso 1 1 calc R
C17 C 0.09158(10) 0.44511(8) -0.6411(2) 0.0218(3) Uani 1 1 d .
H12 H 0.0349 0.4587 -0.7631 0.026 Uiso 1 1 calc R
C18 C 0.18917(10) 0.49208(8) -0.6100(2) 0.0189(3) 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 0.0181 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_3
C2 C1 C6 122.41(11) .
C2 C1 H1 118.8 .
C6 C1 H1 118.8 .
C1 C2 C3 118.14(12) .
C1 C2 C18 119.52(11) 3_664
C3 C2 C18 122.31(12) 3_664
C4 C3 C2 120.16(12) .
C4 C3 H2 119.9 .
C2 C3 H2 119.9 .
C5 C4 C3 121.08(11) .
C5 C4 H3 119.5 .
C3 C4 H3 119.5 .
C4 C5 C6 120.12(12) .
C4 C5 H4 119.9 .
C6 C5 H4 119.9 .
C1 C6 C5 118.09(12) .
C1 C6 C8 120.38(11) .
C5 C6 C8 121.53(11) .
C12 C7 C8 122.53(11) .
C12 C7 H5 118.7 .
C8 C7 H5 118.7 .
C7 C8 C9 117.89(12) .
C7 C8 C6 120.27(11) .
C9 C8 C6 121.82(11) .
C10 C9 C8 120.30(12) .
C10 C9 H6 119.9 .
C8 C9 H6 119.9 .
C11 C10 C9 120.83(12) .
C11 C10 H7 119.6 .
C9 C10 H7 119.6 .
C10 C11 C12 120.23(12) .
C10 C11 H8 119.9 .
C12 C11 H8 119.9 .
C7 C12 C11 118.20(11) .
C7 C12 C14 119.68(11) .
C11 C12 C14 122.10(11) .
C14 C13 C18 122.37(11) .
C14 C13 H9 118.8 .
C18 C13 H9 118.8 .
C13 C14 C15 118.29(12) .
C13 C14 C12 120.09(11) .
C15 C14 C12 121.58(11) .
C16 C15 C14 119.93(12) .
C16 C15 H10 120.0 .
C14 C15 H10 120.0 .
C15 C16 C17 121.02(12) .
C15 C16 H11 119.5 .
C17 C16 H11 119.5 .
C16 C17 C18 120.13(12) .
C16 C17 H12 119.9 .
C18 C17 H12 119.9 .
C13 C18 C17 118.21(12) .
C13 C18 C2 120.23(11) 3_664
C17 C18 C2 121.45(11) 3_664
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3839(18) .
C1 C6 1.3899(17) .
C1 H1 0.9500 .
C2 C3 1.3940(17) .
C2 C18 1.4786(17) 3_664
C3 C4 1.3790(19) .
C3 H2 0.9500 .
C4 C5 1.3744(19) .
C4 H3 0.9500 .
C5 C6 1.3954(17) .
C5 H4 0.9500 .
C6 C8 1.4731(18) .
C7 C12 1.3814(18) .
C7 C8 1.3889(17) .
C7 H5 0.9500 .
C8 C9 1.3929(18) .
C9 C10 1.3763(19) .
C9 H6 0.9500 .
C10 C11 1.3787(18) .
C10 H7 0.9500 .
C11 C12 1.3901(18) .
C11 H8 0.9500 .
C12 C14 1.4797(18) .
C13 C14 1.3859(17) .
C13 C18 1.3888(17) .
C13 H9 0.9500 .
C14 C15 1.3915(18) .
C15 C16 1.3803(19) .
C15 H10 0.9500 .
C16 C17 1.3825(18) .
C16 H11 0.9500 .
C17 C18 1.3865(18) .
C17 H12 0.9500 .
C18 C2 1.4786(17) 3_664
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 -0.37(17) . .
C6 C1 C2 C18 -178.09(10) . 3_664
C1 C2 C3 C4 0.36(17) . .
C18 C2 C3 C4 178.01(10) 3_664 .
C2 C3 C4 C5 0.12(18) . .
C3 C4 C5 C6 -0.60(18) . .
C2 C1 C6 C5 -0.09(17) . .
C2 C1 C6 C8 -179.73(10) . .
C4 C5 C6 C1 0.58(17) . .
C4 C5 C6 C8 -179.78(11) . .
C12 C7 C8 C9 -0.90(17) . .
C12 C7 C8 C6 177.13(10) . .
C1 C6 C8 C7 28.08(16) . .
C5 C6 C8 C7 -151.54(11) . .
C1 C6 C8 C9 -153.97(11) . .
C5 C6 C8 C9 26.40(17) . .
C7 C8 C9 C10 1.41(16) . .
C6 C8 C9 C10 -176.59(10) . .
C8 C9 C10 C11 -0.50(17) . .
C9 C10 C11 C12 -0.98(17) . .
C8 C7 C12 C11 -0.53(17) . .
C8 C7 C12 C14 -178.83(10) . .
C10 C11 C12 C7 1.47(17) . .
C10 C11 C12 C14 179.73(10) . .
C18 C13 C14 C15 -1.95(18) . .
C18 C13 C14 C12 175.93(11) . .
C7 C12 C14 C13 -34.11(16) . .
C11 C12 C14 C13 147.66(11) . .
C7 C12 C14 C15 143.69(12) . .
C11 C12 C14 C15 -34.54(17) . .
C13 C14 C15 C16 0.10(18) . .
C12 C14 C15 C16 -177.74(11) . .
C14 C15 C16 C17 1.14(19) . .
C15 C16 C17 C18 -0.58(19) . .
C14 C13 C18 C17 2.49(18) . .
C14 C13 C18 C2 -173.79(11) . 3_664
C16 C17 C18 C13 -1.19(18) . .
C16 C17 C18 C2 175.05(11) . 3_664
