#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/18/1511883.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_1511883
loop_
_publ_author_name
'Yamamoto, Kosuke'
'Okazumi, Mieko'
'Suemune, Hiroshi'
'Usui, Kazuteru'
_publ_section_title
;
 Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior
 Side of the Helix by Metal-catalyzed Cycloisomerization.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1806
_journal_page_last               1809
_journal_paper_doi               10.1021/ol400332j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         309.37
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.11-0'
_cell_angle_alpha                90
_cell_angle_beta                 102.872(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.060(3)
_cell_length_b                   8.342(2)
_cell_length_c                   15.779(4)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.4238
_cell_measurement_theta_min      2.4033
_cell_volume                     1547.5(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14196
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.203
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.7928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                2617
_reflns_number_total             2718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400332j_si_004.cif
_cod_data_source_block           I
_cod_database_code               1511883
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.79678(6) 0.95974(9) 0.24060(5) 0.0206(2) Uani d . 1
C C1 0.71336(10) 1.02934(14) 0.17169(8) 0.0282(2) Uani d . 1
H H1A 0.6387 1.0002 0.1782 0.042 Uiso calc R 1
H H1B 0.7244 0.9906 0.1169 0.042 Uiso calc R 1
H H1C 0.721 1.1439 0.1737 0.042 Uiso calc R 1
C C2 0.79817(9) 0.99048(12) 0.32496(6) 0.0192(2) Uani d . 1
C C3 0.89039(9) 0.91956(12) 0.38127(6) 0.0187(2) Uani d . 1
C C4 0.98284(9) 0.83613(12) 0.35730(6) 0.0186(2) Uani d . 1
C C5 1.03392(9) 0.84316(12) 0.28350(6) 0.0191(2) Uani d . 1
C C6 1.02864(9) 0.97902(12) 0.22540(6) 0.0195(2) Uani d . 1
C C7 0.99225(9) 1.13285(12) 0.24578(6) 0.0206(2) Uani d . 1
H H7 0.9692 1.1476 0.2977 0.025 Uiso calc R 1
C C8 0.99027(10) 1.26060(13) 0.19077(8) 0.0249(2) Uani d . 1
H H8 0.9666 1.3606 0.2059 0.03 Uiso calc R 1
C C9 1.02374(10) 1.24109(14) 0.11179(8) 0.0275(2) Uani d . 1
H H9 1.0182 1.3263 0.0731 0.033 Uiso calc R 1
C C10 1.02724(9) 0.72689(12) 0.42649(6) 0.0214(2) Uani d . 1
C C11 0.97380(10) 0.75470(13) 0.49569(6) 0.0236(2) Uani d . 1
H H11 0.9912 0.7026 0.5491 0.028 Uiso calc R 1
C C12 0.89127(9) 0.87181(12) 0.47198(6) 0.0215(2) Uani d . 1
C C13 0.82261(10) 0.93140(13) 0.52618(6) 0.0255(2) Uani d . 1
H H13 0.837 0.8888 0.582 0.031 Uiso calc R 1
C C14 0.73769(10) 1.04328(14) 0.50813(8) 0.0282(2) Uani d . 1
H H14 0.7079 1.0762 0.5548 0.034 Uiso calc R 1
C C15 0.69010(10) 1.11450(13) 0.42753(8) 0.0272(2) Uani d . 1
H H15 0.6351 1.192 0.4289 0.033 Uiso calc R 1
C C16 0.71221(9) 1.08752(12) 0.34700(8) 0.0231(2) Uani d . 1
H H16 0.6645 1.1398 0.3008 0.028 Uiso calc R 1
C C17 1.10631(10) 0.60689(13) 0.41539(8) 0.0249(2) Uani d . 1
H H17 1.1372 0.5379 0.4608 0.03 Uiso calc R 1
C C18 1.13610(9) 0.59418(13) 0.33785(8) 0.0253(2) Uani d . 1
H H18 1.1791 0.5066 0.3277 0.03 Uiso calc R 1
C C19 1.10320(9) 0.71182(13) 0.27124(6) 0.0224(2) Uani d . 1
C C20 1.14373(10) 0.70023(13) 0.19314(8) 0.0263(2) Uani d . 1
H H20 1.1847 0.61 0.1838 0.032 Uiso calc R 1
C C21 1.12405(10) 0.81737(14) 0.13223(8) 0.0263(2) Uani d . 1
H H21 1.1453 0.8027 0.0796 0.032 Uiso calc R 1
C C22 1.07069(9) 0.96340(13) 0.14871(6) 0.0229(2) Uani d . 1
C C23 1.06454(10) 1.09637(16) 0.09198(6) 0.0273(2) Uani d . 1
H H23 1.0887 1.0849 0.0403 0.033 Uiso calc R 1
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'
O O 0.0106 0.0060 '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
C2 O1 C1 121.61(9)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C3 112.39(9)
O1 C2 C16 120.01(10)
C3 C2 C16 127.59(10)
C2 C3 C4 126.54(10)
C2 C3 C12 124.28(10)
C4 C3 C12 106.57(9)
C10 C4 C3 106.76(10)
C10 C4 C5 119.33(10)
C3 C4 C5 133.91(10)
C19 C5 C4 116.88(10)
C19 C5 C6 117.52(10)
C4 C5 C6 125.36(10)
C7 C6 C22 117.69(10)
C7 C6 C5 122.46(10)
C22 C6 C5 119.60(10)
C8 C7 C6 121.53(10)
C8 C7 H7 119.2
C6 C7 H7 119.2
C7 C8 C9 120.29(11)
C7 C8 H8 119.9
C9 C8 H8 119.9
C23 C9 C8 119.71(11)
C23 C9 H9 120.1
C8 C9 H9 120.1
C11 C10 C17 130.46(11)
C11 C10 C4 109.22(10)
C17 C10 C4 120.14(11)
C12 C11 C10 109.44(10)
C12 C11 H11 125.3
C10 C11 H11 125.3
C11 C12 C13 124.73(11)
C11 C12 C3 107.46(10)
C13 C12 C3 127.80(11)
C14 C13 C12 128.99(11)
C14 C13 H13 115.5
C12 C13 H13 115.5
C13 C14 C15 127.80(11)
C13 C14 H14 116.1
C15 C14 H14 116.1
C16 C15 C14 130.05(11)
C16 C15 H15 115.0
C14 C15 H15 115.0
C15 C16 C2 128.57(11)
C15 C16 H16 115.7
C2 C16 H16 115.7
C18 C17 C10 119.16(10)
C18 C17 H17 120.4
C10 C17 H17 120.4
C17 C18 C19 121.68(11)
C17 C18 H18 119.2
C19 C18 H18 119.2
C5 C19 C20 119.75(10)
C5 C19 C18 120.42(11)
C20 C19 C18 119.78(10)
C21 C20 C19 121.64(11)
C21 C20 H20 119.2
C19 C20 H20 119.2
C20 C21 C22 120.07(11)
C20 C21 H21 120.0
C22 C21 H21 120.0
C23 C22 C6 119.26(11)
C23 C22 C21 120.99(11)
C6 C22 C21 119.66(11)
C9 C23 C22 121.21(11)
C9 C23 H23 119.4
C22 C23 H23 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3521(14)
O1 C1 1.4297(14)
C1 H1A 0.96
C1 H1B 0.96
C1 H1C 0.96
C2 C3 1.3914(16)
C2 C16 1.4182(16)
C3 C4 1.4347(16)
C3 C12 1.4835(15)
C4 C10 1.4313(15)
C4 C5 1.4347(15)
C5 C19 1.4170(16)
C5 C6 1.4502(16)
C6 C7 1.4162(16)
C6 C22 1.4183(16)
C7 C8 1.3713(16)
C7 H7 0.93
C8 C9 1.4024(17)
C8 H8 0.93
C9 C23 1.3658(18)
C9 H9 0.93
C10 C11 1.4053(17)
C10 C17 1.4199(17)
C11 C12 1.3853(17)
C11 H11 0.93
C12 C13 1.4070(17)
C13 C14 1.3678(18)
C13 H13 0.93
C14 C15 1.405(2)
C14 H14 0.93
C15 C16 1.3739(17)
C15 H15 0.93
C16 H16 0.93
C17 C18 1.3541(18)
C17 H17 0.93
C18 C19 1.4280(17)
C18 H18 0.93
C19 C20 1.4267(17)
C20 C21 1.3540(18)
C20 H20 0.93
C21 C22 1.4284(17)
C21 H21 0.93
C22 C23 1.4169(17)
C23 H23 0.93
