#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:01:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180284 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/70/7117055.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_7117055
loop_
_publ_author_name
'Takashi Otani'
'Kanako Ueki'
'Kinryo Cho'
'Kan Kanai'
'Kotaro Tateno'
'Takao Saito'
_publ_section_title
;
 Construction of dibenzo-fused seven- to nine-membered carbocycles via
 Bronsted acid-promoted intramolecular Friedel-Crafts-type alkenylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              7895
_journal_paper_doi               10.1039/C5cc01257K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C21 H24'
_chemical_formula_weight         276.40
_chemical_name_systematic
(E)-5-(2,2-Dimethylpropylidene)-10,11-dihydro-3-methyl-5H-dibenzo[a,d]cycloheptene
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.555(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.881(5)
_cell_length_b                   16.344(13)
_cell_length_c                   17.969(14)
_cell_measurement_temperature    293(2)
_cell_volume                     1719(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.919
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9235
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_min         2.278
_exptl_absorpt_coefficient_mu    0.060
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_description       cube
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.133
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0949P)²+0.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1912
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             3933
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc01257k2.cif
_cod_data_source_block           ydkr-1
_cod_database_code               7117055
#BEGIN Tags that were not found in dictionaries:
_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.
;
#END Tags that were not found in dictionaries
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9814(3) 0.11990(10) 0.15865(10) 0.0496(5) Uani 1 1 d . . . . .
H1 H 1.0516 0.0865 0.1960 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8043(3) 0.17160(10) 0.17676(10) 0.0472(5) Uani 1 1 d . . . . .
C3 C 0.7398(3) 0.17015(10) 0.25629(10) 0.0443(4) Uani 1 1 d . . . . .
C4 C 0.6967(4) 0.22301(11) 0.12070(11) 0.0546(5) Uani 1 1 d . . . . .
C5 C 0.9110(3) 0.27762(11) 0.34626(10) 0.0506(5) Uani 1 1 d . . . . .
H2 H 1.0281 0.2414 0.3618 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6984(3) 0.09790(11) 0.28773(10) 0.0496(5) Uani 1 1 d . . . . .
H3 H 0.7176 0.0534 0.2567 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7378(3) 0.25297(10) 0.29251(10) 0.0444(4) Uani 1 1 d . . . . .
C8 C 0.5636(3) 0.30850(11) 0.26764(11) 0.0491(5) Uani 1 1 d . . . . .
C9 C 0.6263(3) 0.07403(11) 0.36402(11) 0.0528(5) Uani 1 1 d . . . . .
C10 C 1.0574(4) 0.11605(12) 0.08765(11) 0.0573(5) Uani 1 1 d . . . . .
C11 C 0.5650(4) 0.38604(11) 0.30011(12) 0.0579(5) Uani 1 1 d . . . . .
H4 H 0.4481 0.4226 0.2852 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3916(3) 0.28298(13) 0.20424(13) 0.0622(6) Uani 1 1 d . . . . .
H23 H 0.2642 0.3209 0.2007 0.075 Uiso 1 1 calc R U . . .
H24 H 0.3333 0.2291 0.2146 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7360(4) 0.40979(12) 0.35391(12) 0.0613(6) Uani 1 1 d . . . . .
H6 H 0.7339 0.4619 0.3746 0.074 Uiso 1 1 calc R U . . .
C14 C 0.9107(4) 0.35592(12) 0.37692(11) 0.0588(5) Uani 1 1 d . . . . .
H7 H 1.0272 0.3719 0.4127 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7782(4) 0.21850(14) 0.04960(12) 0.0686(6) Uani 1 1 d . . . . .
H8 H 0.7116 0.2522 0.0119 0.082 Uiso 1 1 calc R U . . .
C16 C 0.4968(4) 0.28110(13) 0.12942(12) 0.0665(6) Uani 1 1 d . . . . .
H25 H 0.3759 0.2676 0.0908 0.080 Uiso 1 1 calc R U . . .
H26 H 0.5475 0.3361 0.1193 0.080 Uiso 1 1 calc R U . . .
C17 C 0.9506(4) 0.16700(14) 0.03313(12) 0.0692(6) Uani 1 1 d . . . . .
H10 H 0.9963 0.1662 -0.0150 0.083 Uiso 1 1 calc R U . . .
C18 C 1.2507(4) 0.05873(15) 0.07254(14) 0.0771(7) Uani 1 1 d . . . . .
H11 H 1.3227 0.0383 0.1191 0.116 Uiso 1 1 calc R U . . .
H12 H 1.3610 0.0878 0.0467 0.116 Uiso 1 1 calc R U . . .
H13 H 1.1908 0.0138 0.0423 0.116 Uiso 1 1 calc R U . . .
C19 C 0.4725(6) -0.00206(19) 0.35214(17) 0.1100(11) Uani 1 1 d . . . . .
H14 H 0.3384 0.0116 0.3198 0.165 Uiso 1 1 calc R U . . .
H15 H 0.4286 -0.0204 0.3995 0.165 Uiso 1 1 calc R U . . .
H16 H 0.5547 -0.0448 0.3298 0.165 Uiso 1 1 calc R U . . .
C20 C 0.8342(5) 0.0482(3) 0.41460(17) 0.1225(13) Uani 1 1 d . . . . .
H17 H 0.9178 0.0077 0.3897 0.184 Uiso 1 1 calc R U . . .
H18 H 0.7868 0.0256 0.4599 0.184 Uiso 1 1 calc R U . . .
H19 H 0.9301 0.0949 0.4263 0.184 Uiso 1 1 calc R U . . .
C21 C 0.4929(6) 0.13901(18) 0.40106(19) 0.1208(14) Uani 1 1 d . . . . .
H20 H 0.5901 0.1851 0.4137 0.181 Uiso 1 1 calc R U . . .
H21 H 0.4386 0.1171 0.4456 0.181 Uiso 1 1 calc R U . . .
H22 H 0.3652 0.1561 0.3673 0.181 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 0.0033 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'
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
C10 C1 C2 123.40(18) . .
C1 C2 C4 118.92(18) . .
C1 C2 C3 117.95(16) . .
C4 C2 C3 123.13(18) . .
C6 C3 C7 126.96(17) . .
C6 C3 C2 118.93(16) . .
C7 C3 C2 114.08(14) . .
C15 C4 C2 116.6(2) . .
C15 C4 C16 117.21(18) . .
C2 C4 C16 126.22(19) . .
C7 C5 C14 120.72(17) . .
C3 C6 C9 132.97(17) . .
C5 C7 C8 119.59(17) . .
C5 C7 C3 121.66(16) . .
C8 C7 C3 118.62(17) . .
C11 C8 C7 118.55(18) . .
C11 C8 C12 122.96(17) . .
C7 C8 C12 118.40(17) . .
C20 C9 C21 110.8(3) . .
C20 C9 C6 109.46(17) . .
C21 C9 C6 114.67(18) . .
C20 C9 C19 106.7(2) . .
C21 C9 C19 107.8(2) . .
C6 C9 C19 107.02(18) . .
C17 C10 C1 117.1(2) . .
C17 C10 C18 122.7(2) . .
C1 C10 C18 120.27(19) . .
C13 C11 C8 121.49(18) . .
C8 C12 C16 111.74(18) . .
C11 C13 C14 119.93(19) . .
C13 C14 C5 119.66(19) . .
C17 C15 C4 123.4(2) . .
C4 C16 C12 118.75(17) . .
C15 C17 C10 120.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.393(3) .
C1 C2 1.404(3) .
C2 C4 1.413(3) .
C2 C3 1.514(3) .
C3 C6 1.341(3) .
C3 C7 1.503(3) .
C4 C15 1.409(3) .
C4 C16 1.531(3) .
C5 C7 1.394(3) .
C5 C14 1.393(3) .
C6 C9 1.524(3) .
C7 C8 1.409(3) .
C8 C11 1.395(3) .
C8 C12 1.507(3) .
C9 C20 1.511(3) .
C9 C21 1.513(3) .
C9 C19 1.540(3) .
C10 C17 1.389(3) .
C10 C18 1.518(3) .
C11 C13 1.382(3) .
C12 C16 1.533(3) .
C13 C14 1.385(3) .
C15 C17 1.372(3) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C10 C1 C2 C4 -0.3(3) . . . .
C10 C1 C2 C3 -179.55(16) . . . .
C1 C2 C3 C6 -50.7(2) . . . .
C4 C2 C3 C6 130.1(2) . . . .
C1 C2 C3 C7 127.30(17) . . . .
C4 C2 C3 C7 -51.9(2) . . . .
C1 C2 C4 C15 -0.3(3) . . . .
C3 C2 C4 C15 178.91(17) . . . .
C1 C2 C4 C16 177.95(17) . . . .
C3 C2 C4 C16 -2.8(3) . . . .
C7 C3 C6 C9 3.8(3) . . . .
C2 C3 C6 C9 -178.50(19) . . . .
C14 C5 C7 C8 1.5(3) . . . .
C14 C5 C7 C3 177.36(18) . . . .
C6 C3 C7 C5 72.7(3) . . . .
C2 C3 C7 C5 -105.1(2) . . . .
C6 C3 C7 C8 -111.5(2) . . . .
C2 C3 C7 C8 70.8(2) . . . .
C5 C7 C8 C11 -2.6(3) . . . .
C3 C7 C8 C11 -178.52(17) . . . .
C5 C7 C8 C12 174.13(17) . . . .
C3 C7 C8 C12 -1.8(3) . . . .
C3 C6 C9 C20 -98.6(3) . . . .
C3 C6 C9 C21 26.7(3) . . . .
C3 C6 C9 C19 146.1(2) . . . .
C2 C1 C10 C17 0.4(3) . . . .
C2 C1 C10 C18 179.76(18) . . . .
C7 C8 C11 C13 2.0(3) . . . .
C12 C8 C11 C13 -174.57(19) . . . .
C11 C8 C12 C16 104.6(2) . . . .
C7 C8 C12 C16 -71.9(2) . . . .
C8 C11 C13 C14 -0.3(3) . . . .
C11 C13 C14 C5 -0.8(3) . . . .
C7 C5 C14 C13 0.2(3) . . . .
C2 C4 C15 C17 0.8(3) . . . .
C16 C4 C15 C17 -177.6(2) . . . .
C15 C4 C16 C12 175.50(18) . . . .
C2 C4 C16 C12 -2.8(3) . . . .
C8 C12 C16 C4 61.0(2) . . . .
C4 C15 C17 C10 -0.7(3) . . . .
C1 C10 C17 C15 0.1(3) . . . .
C18 C10 C17 C15 -179.3(2) . . . .
