#------------------------------------------------------------------------------
#$Date: 2019-11-24 20:35:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239358 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/60/1556037.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_1556037
loop_
_publ_author_name
'Zhang, Jingfang'
'Tang, Yuhai'
'Wei, Wen'
'Wu, Yong'
'Li, Yang'
'Zhang, Junjie'
'Zheng, Yuansuo'
'Xu, Silong'
_publ_section_title
;
 Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring
 Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3043
_journal_page_last               3046
_journal_paper_doi               10.1021/acs.orglett.7b00805
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration s
_chemical_formula_moiety         'C23 H18 O2'
_chemical_formula_sum            'C23 H18 O2'
_chemical_formula_weight         326.37
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 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                 96.951(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0965(3)
_cell_length_b                   7.8294(3)
_cell_length_c                   17.9271(8)
_cell_measurement_reflns_used    5399
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.84
_cell_volume                     849.41(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9040
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       LUMP
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_extinction_coef       0.167(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0523
_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+0.4883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                3124
_reflns_number_total             3443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00805_si_002.cif
_cod_data_source_block           ljj_20161229_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_refine_ls_hydrogen_treatment' value 'CONSTR' was changed
to 'constr' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1556037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O2 O 0.5374(3) 1.1418(3) 0.28894(10) 0.0325(5) Uani 1 1 d .
C2 C 0.1532(4) 1.1754(4) 0.17504(13) 0.0265(6) Uani 1 1 d .
H2A H 0.2512 1.1502 0.1363 0.032 Uiso 1 1 calc R
H2B H 0.1786 1.2942 0.1930 0.032 Uiso 1 1 calc R
O1 O -0.1248(3) 0.9644(2) 0.16596(9) 0.0243(4) Uani 1 1 d .
C7 C 0.1563(4) 0.9937(3) 0.40775(14) 0.0244(5) Uani 1 1 d .
H7 H 0.0287 1.0448 0.3811 0.029 Uiso 1 1 calc R
C5 C 0.3692(4) 1.0617(3) 0.29922(14) 0.0208(5) Uani 1 1 d .
C8 C 0.1471(4) 0.9274(4) 0.47944(15) 0.0298(6) Uani 1 1 d .
H8 H 0.0155 0.9370 0.5026 0.036 Uiso 1 1 calc R
C3 C 0.0266(4) 0.9275(3) 0.22580(12) 0.0203(5) Uani 1 1 d .
C11 C 0.5374(4) 0.9085(4) 0.41383(14) 0.0251(5) Uani 1 1 d .
H11 H 0.6723 0.9051 0.3923 0.030 Uiso 1 1 calc R
C4 C 0.1859(4) 1.0480(3) 0.23946(13) 0.0210(5) Uani 1 1 d .
C9 C 0.3315(5) 0.8475(4) 0.51653(15) 0.0334(7) Uani 1 1 d .
H9 H 0.3247 0.7997 0.5649 0.040 Uiso 1 1 calc R
C10 C 0.5253(5) 0.8364(4) 0.48407(15) 0.0307(6) Uani 1 1 d .
H10 H 0.6500 0.7797 0.5097 0.037 Uiso 1 1 calc R
C1 C -0.0895(5) 1.1445(3) 0.14567(14) 0.0268(6) Uani 1 1 d .
H1 H -0.1835 1.2191 0.1741 0.032 Uiso 1 1 calc R
C6 C 0.3518(4) 0.9856(3) 0.37492(13) 0.0195(5) Uani 1 1 d .
C23 C 0.1691(4) 0.6602(3) 0.29201(13) 0.0209(5) Uani 1 1 d .
H23 H 0.3150 0.7048 0.2961 0.025 Uiso 1 1 calc R
C18 C -0.0059(4) 0.7571(3) 0.25830(12) 0.0185(5) Uani 1 1 d .
C22 C 0.1330(4) 0.4989(3) 0.31970(15) 0.0269(6) Uani 1 1 d .
H22 H 0.2533 0.4345 0.3438 0.032 Uiso 1 1 calc R
C20 C -0.2536(4) 0.5255(4) 0.27791(16) 0.0299(6) Uani 1 1 d .
H20 H -0.3984 0.4786 0.2723 0.036 Uiso 1 1 calc R
C19 C -0.2185(4) 0.6887(4) 0.25166(15) 0.0258(6) Uani 1 1 d .
H19 H -0.3400 0.7541 0.2290 0.031 Uiso 1 1 calc R
C13 C -0.0432(5) 1.0948(4) 0.00946(16) 0.0330(6) Uani 1 1 d .
H13 H 0.0885 1.0330 0.0251 0.040 Uiso 1 1 calc R
C21 C -0.0786(4) 0.4313(4) 0.31219(15) 0.0287(6) Uani 1 1 d .
H21 H -0.1031 0.3200 0.3307 0.034 Uiso 1 1 calc R
C17 C -0.3557(4) 1.2542(4) 0.03966(17) 0.0334(6) Uani 1 1 d .
H17 H -0.4386 1.3029 0.0759 0.040 Uiso 1 1 calc R
C12 C -0.1615(4) 1.1655(3) 0.06309(14) 0.0245(5) Uani 1 1 d .
C15 C -0.3061(5) 1.1996(5) -0.08868(17) 0.0421(8) Uani 1 1 d .
H15 H -0.3556 1.2105 -0.1408 0.051 Uiso 1 1 calc R
C14 C -0.1131(5) 1.1124(4) -0.06609(17) 0.0396(7) Uani 1 1 d .
H14 H -0.0291 1.0649 -0.1023 0.048 Uiso 1 1 calc R
C16 C -0.4291(5) 1.2718(5) -0.03664(18) 0.0422(8) Uani 1 1 d .
H16 H -0.5614 1.3323 -0.0527 0.051 Uiso 1 1 calc R
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
C4 C2 C1 101.0(2)
C4 C2 H2A 111.6
C1 C2 H2A 111.6
C4 C2 H2B 111.6
C1 C2 H2B 111.6
H2A C2 H2B 109.4
C3 O1 C1 106.96(19)
C6 C7 C8 120.3(2)
C6 C7 H7 119.8
C8 C7 H7 119.8
O2 C5 C4 120.3(2)
O2 C5 C6 119.2(2)
C4 C5 C6 120.4(2)
C9 C8 C7 119.4(2)
C9 C8 H8 120.3
C7 C8 H8 120.3
C4 C3 O1 113.5(2)
C4 C3 C18 133.2(2)
O1 C3 C18 113.1(2)
C10 C11 C6 120.0(2)
C10 C11 H11 120.0
C6 C11 H11 120.0
C3 C4 C5 130.8(2)
C3 C4 C2 107.1(2)
C5 C4 C2 122.0(2)
C10 C9 C8 120.8(2)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 119.9(2)
C9 C10 H10 120.1
C11 C10 H10 120.1
O1 C1 C12 108.2(2)
O1 C1 C2 103.3(2)
C12 C1 C2 118.5(2)
O1 C1 H1 108.8
C12 C1 H1 108.8
C2 C1 H1 108.8
C7 C6 C11 119.5(2)
C7 C6 C5 121.5(2)
C11 C6 C5 118.9(2)
C22 C23 C18 120.5(2)
C22 C23 H23 119.7
C18 C23 H23 119.7
C23 C18 C19 119.0(2)
C23 C18 C3 122.2(2)
C19 C18 C3 118.7(2)
C23 C22 C21 120.0(2)
C23 C22 H22 120.0
C21 C22 H22 120.0
C21 C20 C19 120.1(2)
C21 C20 H20 120.0
C19 C20 H20 120.0
C20 C19 C18 120.3(2)
C20 C19 H19 119.8
C18 C19 H19 119.8
C14 C13 C12 121.2(3)
C14 C13 H13 119.4
C12 C13 H13 119.4
C20 C21 C22 120.0(2)
C20 C21 H21 120.0
C22 C21 H21 120.0
C12 C17 C16 120.4(3)
C12 C17 H17 119.8
C16 C17 H17 119.8
C13 C12 C17 119.0(2)
C13 C12 C1 121.7(2)
C17 C12 C1 119.2(2)
C14 C15 C16 121.1(3)
C14 C15 H15 119.5
C16 C15 H15 119.5
C13 C14 C15 119.4(3)
C13 C14 H14 120.3
C15 C14 H14 120.3
C15 C16 C17 119.0(3)
C15 C16 H16 120.5
C17 C16 H16 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C5 1.235(3)
C2 C4 1.521(3)
C2 C1 1.529(4)
C2 H2A 0.9900
C2 H2B 0.9900
O1 C3 1.359(3)
O1 C1 1.479(3)
C7 C6 1.393(3)
C7 C8 1.394(4)
C7 H7 0.9500
C5 C4 1.455(3)
C5 C6 1.498(3)
C8 C9 1.384(4)
C8 H8 0.9500
C3 C4 1.355(3)
C3 C18 1.478(3)
C11 C10 1.390(4)
C11 C6 1.393(3)
C11 H11 0.9500
C9 C10 1.381(4)
C9 H9 0.9500
C10 H10 0.9500
C1 C12 1.501(3)
C1 H1 1.0000
C23 C22 1.384(4)
C23 C18 1.387(3)
C23 H23 0.9500
C18 C19 1.395(3)
C22 C21 1.386(4)
C22 H22 0.9500
C20 C21 1.379(4)
C20 C19 1.387(4)
C20 H20 0.9500
C19 H19 0.9500
C13 C14 1.377(4)
C13 C12 1.385(4)
C13 H13 0.9500
C21 H21 0.9500
C17 C12 1.393(4)
C17 C16 1.394(4)
C17 H17 0.9500
C15 C14 1.378(5)
C15 C16 1.386(5)
C15 H15 0.9500
C14 H14 0.9500
C16 H16 0.9500
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
C6 C7 C8 C9 -2.5(4)
C1 O1 C3 C4 -12.0(3)
C1 O1 C3 C18 173.07(19)
O1 C3 C4 C5 176.6(2)
C18 C3 C4 C5 -9.7(5)
O1 C3 C4 C2 -7.0(3)
C18 C3 C4 C2 166.7(2)
O2 C5 C4 C3 153.9(3)
C6 C5 C4 C3 -28.9(4)
O2 C5 C4 C2 -22.0(4)
C6 C5 C4 C2 155.2(2)
C1 C2 C4 C3 21.8(3)
C1 C2 C4 C5 -161.4(2)
C7 C8 C9 C10 1.5(4)
C8 C9 C10 C11 1.0(4)
C6 C11 C10 C9 -2.6(4)
C3 O1 C1 C12 151.7(2)
C3 O1 C1 C2 25.2(2)
C4 C2 C1 O1 -27.6(2)
C4 C2 C1 C12 -147.3(2)
C8 C7 C6 C11 0.9(4)
C8 C7 C6 C5 -177.6(2)
C10 C11 C6 C7 1.7(4)
C10 C11 C6 C5 -179.8(3)
O2 C5 C6 C7 138.0(3)
C4 C5 C6 C7 -39.2(3)
O2 C5 C6 C11 -40.5(3)
C4 C5 C6 C11 142.3(3)
C22 C23 C18 C19 -1.0(3)
C22 C23 C18 C3 -177.9(2)
C4 C3 C18 C23 -25.1(4)
O1 C3 C18 C23 148.6(2)
C4 C3 C18 C19 158.0(3)
O1 C3 C18 C19 -28.3(3)
C18 C23 C22 C21 1.6(4)
C21 C20 C19 C18 1.3(4)
C23 C18 C19 C20 -0.5(4)
C3 C18 C19 C20 176.6(2)
C19 C20 C21 C22 -0.7(4)
C23 C22 C21 C20 -0.7(4)
C14 C13 C12 C17 0.7(4)
C14 C13 C12 C1 178.8(3)
C16 C17 C12 C13 -0.2(4)
C16 C17 C12 C1 -178.4(3)
O1 C1 C12 C13 -70.3(3)
C2 C1 C12 C13 46.7(4)
O1 C1 C12 C17 107.8(3)
C2 C1 C12 C17 -135.2(3)
C12 C13 C14 C15 -1.1(5)
C16 C15 C14 C13 0.9(5)
C14 C15 C16 C17 -0.4(5)
C12 C17 C16 C15 0.1(5)
