#------------------------------------------------------------------------------
#$Date: 2019-11-26 13:39:50 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/75/4037598.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_4037598
loop_
_publ_author_name
'Tummatorn, Jumreang'
'Batsomboon, Paratchata'
'Clark, Ronald J.'
'Alabugin, Igor V.'
'Dudley, Gregory B.'
_publ_section_title
;
 Strain-promoted azide-alkyne cycloadditions of benzocyclononynes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2093
_journal_page_last               2097
_journal_paper_doi               10.1021/jo300188y
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.6350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1194(18)
_cell_length_b                   7.8260(11)
_cell_length_c                   14.852(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1386.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14081
_diffrn_reflns_theta_full        27.19
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9869
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0002(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0425
_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)+(0.0620P)²+0.5388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2654
_reflns_number_total             3074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300188y_si_003.cif
_cod_data_source_block           greg15
_cod_database_code               4037598
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.51500(10) 0.83349(17) 0.30147(9) 0.0217(3) Uani 1 1 d .
H1 H 0.4846 0.9422 0.2646 0.026 Uiso 1 1 calc R
C2 C 0.45526(11) 0.80228(17) 0.37166(9) 0.0245(3) Uani 1 1 d .
H2A H 0.4046 0.7029 0.3464 0.029 Uiso 1 1 calc R
H2B H 0.5129 0.7713 0.4380 0.029 Uiso 1 1 calc R
C3 C 0.38673(12) 0.95283(19) 0.38365(10) 0.0304(3) Uani 1 1 d .
H3A H 0.4250 1.0609 0.3818 0.037 Uiso 1 1 calc R
H3B H 0.3846 0.9448 0.4494 0.037 Uiso 1 1 calc R
C4 C 0.26570(13) 0.9587(2) 0.30318(11) 0.0368(4) Uani 1 1 d .
H4A H 0.2225 0.8607 0.3111 0.044 Uiso 1 1 calc R
H4B H 0.2286 1.0655 0.3093 0.044 Uiso 1 1 calc R
C5 C 0.26893(12) 0.95143(19) 0.20552(11) 0.0314(3) Uani 1 1 d .
C6 C 0.29734(11) 0.93189(18) 0.13976(10) 0.0274(3) Uani 1 1 d .
C7 C 0.36234(11) 0.88296(17) 0.08365(9) 0.0249(3) Uani 1 1 d .
H7A H 0.4187 0.9721 0.0907 0.030 Uiso 1 1 calc R
H7B H 0.3119 0.8714 0.0125 0.030 Uiso 1 1 calc R
C8 C 0.42076(10) 0.71306(16) 0.12386(9) 0.0206(3) Uani 1 1 d .
C9 C 0.49117(10) 0.69125(16) 0.22488(9) 0.0199(3) Uani 1 1 d .
C10 C 0.53730(10) 0.52867(16) 0.25569(9) 0.0209(3) Uani 1 1 d .
C11 C 0.51556(11) 0.39159(16) 0.19032(9) 0.0219(3) Uani 1 1 d .
C12 C 0.44135(11) 0.41513(16) 0.09073(9) 0.0221(3) Uani 1 1 d .
C13 C 0.39604(11) 0.57550(17) 0.05842(9) 0.0222(3) Uani 1 1 d .
H13 H 0.3474 0.5920 -0.0094 0.027 Uiso 1 1 calc R
C14 C 0.33796(12) 0.29088(19) -0.06825(10) 0.0298(3) Uani 1 1 d .
H14A H 0.2689 0.3414 -0.0698 0.045 Uiso 1 1 calc R
H14B H 0.3214 0.1784 -0.1001 0.045 Uiso 1 1 calc R
H14C H 0.3689 0.3654 -0.1037 0.045 Uiso 1 1 calc R
C15 C 0.64264(12) 0.17516(19) 0.19228(11) 0.0317(3) Uani 1 1 d .
H15A H 0.6066 0.1567 0.1205 0.047 Uiso 1 1 calc R
H15B H 0.6755 0.0676 0.2256 0.047 Uiso 1 1 calc R
H15C H 0.7018 0.2613 0.2078 0.047 Uiso 1 1 calc R
C16 C 0.57071(12) 0.39045(19) 0.40918(10) 0.0296(3) Uani 1 1 d .
H16A H 0.4934 0.4191 0.3971 0.044 Uiso 1 1 calc R
H16B H 0.6188 0.3997 0.4802 0.044 Uiso 1 1 calc R
H16C H 0.5735 0.2733 0.3870 0.044 Uiso 1 1 calc R
O1 O 0.63379(8) 0.85658(13) 0.35817(7) 0.0306(2) Uani 1 1 d .
H1A H 0.6624 0.7644 0.3863 0.046 Uiso 1 1 calc R
O2 O 0.41808(8) 0.27262(12) 0.03253(7) 0.0280(2) Uani 1 1 d .
O3 O 0.56071(8) 0.23349(12) 0.22585(7) 0.0267(2) Uani 1 1 d .
O4 O 0.60974(8) 0.50731(12) 0.35500(6) 0.0249(2) 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'
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
O1 C1 C9 111.24(10)
O1 C1 C2 110.53(10)
C9 C1 C2 112.27(10)
O1 C1 H1 107.5
C9 C1 H1 107.5
C2 C1 H1 107.5
C3 C2 C1 115.97(11)
C3 C2 H2A 108.3
C1 C2 H2A 108.3
C3 C2 H2B 108.3
C1 C2 H2B 108.3
H2A C2 H2B 107.4
C2 C3 C4 113.38(12)
C2 C3 H3A 108.9
C4 C3 H3A 108.9
C2 C3 H3B 108.9
C4 C3 H3B 108.9
H3A C3 H3B 107.7
C5 C4 C3 108.68(12)
C5 C4 H4A 110.0
C3 C4 H4A 110.0
C5 C4 H4B 110.0
C3 C4 H4B 110.0
H4A C4 H4B 108.3
C6 C5 C4 164.05(15)
C5 C6 C7 162.13(14)
C6 C7 C8 108.68(10)
C6 C7 H7A 110.0
C8 C7 H7A 110.0
C6 C7 H7B 110.0
C8 C7 H7B 110.0
H7A C7 H7B 108.3
C13 C8 C9 120.54(11)
C13 C8 C7 117.81(11)
C9 C8 C7 121.50(11)
C10 C9 C8 117.43(11)
C10 C9 C1 119.47(11)
C8 C9 C1 123.05(11)
C11 C10 C9 122.42(11)
C11 C10 O4 119.77(11)
C9 C10 O4 117.79(11)
O3 C11 C10 119.58(11)
O3 C11 C12 121.33(11)
C10 C11 C12 118.92(11)
O2 C12 C13 124.75(11)
O2 C12 C11 115.72(11)
C13 C12 C11 119.52(11)
C12 C13 C8 121.06(12)
C12 C13 H13 119.5
C8 C13 H13 119.5
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O4 C16 H16A 109.5
O4 C16 H16B 109.5
H16A C16 H16B 109.5
O4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C1 O1 H1A 109.5
C12 O2 C14 116.93(10)
C11 O3 C15 114.66(10)
C10 O4 C16 114.96(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4410(15)
C1 C9 1.5279(17)
C1 C2 1.5627(17)
C1 H1 1.0000
C2 C3 1.5367(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.539(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.470(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.192(2)
C6 C7 1.4700(18)
C7 C8 1.5266(17)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C13 1.3950(18)
C8 C9 1.4064(17)
C9 C10 1.4013(18)
C10 C11 1.3943(18)
C10 O4 1.3922(15)
C11 O3 1.3782(15)
C11 C12 1.4033(18)
C12 O2 1.3653(15)
C12 C13 1.3860(18)
C13 H13 0.9500
C14 O2 1.4333(16)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 O3 1.4349(16)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 O4 1.4455(16)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
O1 H1A 0.8400
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
O1 C1 C2 C3 105.50(13)
C9 C1 C2 C3 -129.65(12)
C1 C2 C3 C4 86.21(15)
C2 C3 C4 C5 -52.43(17)
C3 C4 C5 C6 16.8(7)
C4 C5 C6 C7 8.9(10)
C5 C6 C7 C8 35.6(5)
C6 C7 C8 C13 120.49(12)
C6 C7 C8 C9 -55.08(15)
C13 C8 C9 C10 1.85(17)
C7 C8 C9 C10 177.31(11)
C13 C8 C9 C1 -175.67(11)
C7 C8 C9 C1 -0.21(17)
O1 C1 C9 C10 54.62(14)
C2 C1 C9 C10 -69.84(14)
O1 C1 C9 C8 -127.91(12)
C2 C1 C9 C8 107.63(13)
C8 C9 C10 C11 -0.06(18)
C1 C9 C10 C11 177.56(11)
C8 C9 C10 O4 178.12(10)
C1 C9 C10 O4 -4.26(16)
C9 C10 C11 O3 -177.97(10)
O4 C10 C11 O3 3.89(17)
C9 C10 C11 C12 -2.55(18)
O4 C10 C11 C12 179.31(10)
O3 C11 C12 O2 -0.34(17)
C10 C11 C12 O2 -175.68(11)
O3 C11 C12 C13 178.70(11)
C10 C11 C12 C13 3.36(18)
O2 C12 C13 C8 177.31(11)
C11 C12 C13 C8 -1.64(18)
C9 C8 C13 C12 -1.02(18)
C7 C8 C13 C12 -176.64(11)
C13 C12 O2 C14 -2.20(18)
C11 C12 O2 C14 176.79(11)
C10 C11 O3 C15 -113.51(13)
C12 C11 O3 C15 71.18(15)
C11 C10 O4 C16 -65.54(15)
C9 C10 O4 C16 116.23(12)
