#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:12:12 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034008.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_4034008
loop_
_publ_author_name
'Lee, Robert'
'Bashrum, Bryan'
'Cagle, Ethan C.'
'Walters, Jillian'
'Massey, Jake'
'Zanghi, Monica'
'Birchfield, Carolyn'
'French, David'
'Joy, Jessica'
'Dos Passos Gomes, Gabriel'
'Wiget, Paul A.'
_publ_section_title
;
 Electronic Donation or Steric Contraction: A Spectroscopic and Structural
 Analysis of Medium-Sized Constrained Rings for Potential Long-Range
 Hyperconjugation.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9897
_journal_page_last               9906
_journal_paper_doi               10.1021/acs.joc.9b00979
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C10 H12 O2'
_chemical_formula_sum            'C10 H12 O2'
_chemical_formula_weight         164.21
_chemical_name_systematic
(1R,2R,5S,6S)-11-oxatricyclo[4.3.1.12,5]undec-3-en-10-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.9440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.04980(10)
_cell_length_b                   6.42590(10)
_cell_length_c                   14.3599(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      58.77
_cell_measurement_theta_min      12.61
_cell_volume                     819.89(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8932
_diffrn_reflns_theta_full        70.0167
_diffrn_reflns_theta_max         70.02
_diffrn_reflns_theta_min         4.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.8844
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.3302
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             353.1488
_exptl_crystal_recrystallization_method 'Recrystallization from hot hexanes'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.2531
_refine_diff_density_min         -0.2348
_refine_diff_density_rms         0.0554
_refine_ls_d_res_high            0.8203
_refine_ls_d_res_low             8.8852
_refine_ls_goodness_of_fit_ref   1.0637
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0637
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0605P)²+0.2471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1438
_reflns_number_total             1553
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00979_si_001.cif
_cod_data_source_block           Wigi_1_0m
_cod_database_code               4034008
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C8(H8a,H8b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O1 O 0.89475(9) 0.21569(14) 0.74613(6) 0.0279(3) Uani 1.000000 .
O2 O 0.47983(10) 0.20112(15) 0.58253(7) 0.0334(3) Uani 1.000000 .
C1 C 0.82611(14) 0.06675(19) 0.55279(9) 0.0264(3) Uani 1.000000 .
H1a H 0.90746(14) -0.03845(19) 0.56444(9) 0.0317(4) Uiso 1.000000 R
H1b H 0.76764(14) 0.04304(19) 0.48807(9) 0.0317(4) Uiso 1.000000 R
C2 C 0.72138(13) 0.03159(18) 0.62464(9) 0.0225(3) Uani 1.000000 .
H2 H 0.66419(13) -0.10120(18) 0.60967(9) 0.0270(3) Uiso 1.000000 R
C3 C 0.80666(13) 0.0288(2) 0.72944(9) 0.0261(3) Uani 1.000000 .
H3 H 0.86954(13) -0.0992(2) 0.74453(9) 0.0313(4) Uiso 1.000000 R
C4 C 0.69679(14) 0.0572(2) 0.79612(9) 0.0320(3) Uani 1.000000 .
H4 H 0.64769(14) -0.0506(2) 0.82386(9) 0.0384(4) Uiso 1.000000 R
C5 C 0.68189(15) 0.2594(2) 0.80853(9) 0.0333(3) Uani 1.000000 .
H5 H 0.61941(15) 0.3236(2) 0.84642(9) 0.0400(4) Uiso 1.000000 R
C6 C 0.78260(14) 0.3704(2) 0.75132(9) 0.0282(3) Uani 1.000000 .
H6 H 0.82705(14) 0.5005(2) 0.78317(9) 0.0339(4) Uiso 1.000000 R
C7 C 0.69490(13) 0.41220(19) 0.64893(9) 0.0244(3) Uani 1.000000 .
H7 H 0.62034(13) 0.52666(19) 0.64989(9) 0.0293(4) Uiso 1.000000 R
C8 C 0.79689(15) 0.46478(19) 0.57723(10) 0.0296(3) Uani 1.000000 .
H8a H 0.73240(15) 0.50893(19) 0.51688(10) 0.0355(4) Uiso 1.000000 R
H8b H 0.86161(15) 0.58433(19) 0.60193(10) 0.0355(4) Uiso 1.000000 R
C9 C 0.89827(15) 0.2848(2) 0.55633(9) 0.0279(3) Uani 1.000000 .
H9a H 0.99096(15) 0.2845(2) 0.60568(9) 0.0334(4) Uiso 1.000000 R
H9b H 0.92839(15) 0.3120(2) 0.49468(9) 0.0334(4) Uiso 1.000000 R
C10 C 0.61345(13) 0.21293(18) 0.61510(8) 0.0220(3) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O1 C3 102.28(9)
H1b C1 H1a 107.5
C2 C1 H1a 108.55(6)
C2 C1 H1b 108.55(6)
C9 C1 H1a 108.55(7)
C9 C1 H1b 108.55(7)
C9 C1 C2 114.87(10)
H2 C2 C1 109.85(6)
C3 C2 C1 113.16(9)
C3 C2 H2 109.85(6)
C10 C2 C1 107.16(9)
C10 C2 H2 109.85(6)
C10 C2 C3 106.87(9)
C2 C3 O1 108.02(9)
H3 C3 O1 112.12(6)
H3 C3 C2 112.12(6)
C4 C3 O1 101.75(10)
C4 C3 C2 110.19(10)
C4 C3 H3 112.12(7)
H4 C4 C3 126.29(7)
C5 C4 C3 107.41(12)
C5 C4 H4 126.29(8)
H5 C5 C4 126.21(8)
C6 C5 C4 107.59(12)
C6 C5 H5 126.21(7)
C5 C6 O1 101.92(10)
H6 C6 O1 112.12(6)
H6 C6 C5 112.12(7)
C7 C6 O1 108.06(10)
C7 C6 C5 110.00(10)
C7 C6 H6 112.12(7)
H7 C7 C6 109.78(6)
C8 C7 C6 113.92(10)
C8 C7 H7 109.78(6)
C10 C7 C6 106.72(10)
C10 C7 H7 109.78(6)
C10 C7 C8 106.72(10)
H8a C8 C7 108.57(7)
H8b C8 C7 108.57(7)
H8b C8 H8a 107.6
C9 C8 C7 114.77(10)
C9 C8 H8a 108.57(7)
C9 C8 H8b 108.57(7)
C8 C9 C1 115.10(10)
H9a C9 C1 108.50(7)
H9a C9 C8 108.50(7)
H9b C9 C1 108.50(7)
H9b C9 C8 108.50(7)
H9b C9 H9a 107.5
C2 C10 O2 124.54(11)
C7 C10 O2 124.51(11)
C7 C10 C2 110.93(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.4364(15)
O1 C6 1.4327(15)
O2 C10 1.2133(15)
C1 H1a 0.9900
C1 H1b 0.9900
C1 C2 1.5443(16)
C1 C9 1.5428(17)
C2 H2 1.0000
C2 C3 1.5556(17)
C2 C10 1.5099(15)
C3 H3 1.0000
C3 C4 1.5166(17)
C4 H4 0.9500
C4 C5 1.322(2)
C5 H5 0.9500
C5 C6 1.5160(18)
C6 H6 1.0000
C6 C7 1.5559(17)
C7 H7 1.0000
C7 C8 1.5451(17)
C7 C10 1.5110(16)
C8 H8a 0.9900
C8 H8b 0.9900
C8 C9 1.5406(17)
C9 H9a 0.9900
C9 H9b 0.9900
