#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:24:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178781 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/35/4103556.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_4103556
loop_
_publ_author_name
'Diem H. T. Phan'
'Kevin G. M. Kou'
'Vy M. Dong'
_publ_section_title
;
 Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16354
_journal_page_last               16355
_journal_paper_doi               10.1021/ja107738a
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H18 O2'
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_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
_cell_angle_beta                 110.406(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3628(2)
_cell_length_b                   37.8917(9)
_cell_length_c                   6.4301(2)
_cell_measurement_reflns_used    5918
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.01
_cell_measurement_theta_min      7.35
_cell_volume                     1452.99(7)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            27369
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         7.35
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.8115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), 1724 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.1404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                3946
_reflns_number_total             4517
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja107738a_si_006.cif
_cod_data_source_block           loug15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29 (44 times).

'_geom_angle_publ_flag' value 'Y'
changed to 'y' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (66
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4103556
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
C1A C 0.6730(4) 0.61542(6) 1.0787(3) 0.0398(5) Uani 1 1 d .
C2A C 0.5356(5) 0.63488(7) 1.1858(4) 0.0523(6) Uani 1 1 d .
H2A1 H 0.6015 0.6388 1.3479 0.063 Uiso 1 1 calc R
H2A2 H 0.3719 0.6305 1.1294 0.063 Uiso 1 1 calc R
C3A C 0.6311(4) 0.65559(6) 1.0404(4) 0.0463(5) Uani 1 1 d .
H3A H 0.7602 0.6715 1.1176 0.056 Uiso 1 1 calc R
C4A C 0.4775(4) 0.66739(6) 0.8212(4) 0.0440(5) Uani 1 1 d .
C5A C 0.5592(4) 0.69135(6) 0.6855(4) 0.0396(5) Uani 1 1 d .
C6A C 0.4127(4) 0.70226(6) 0.4740(4) 0.0412(5) Uani 1 1 d .
C7A C 0.4856(4) 0.72438(6) 0.3413(4) 0.0442(5) Uani 1 1 d .
C8A C 0.7054(4) 0.73545(7) 0.4184(4) 0.0526(6) Uani 1 1 d .
H8A H 0.7574 0.7504 0.3278 0.063 Uiso 1 1 calc R
C9A C 0.8533(4) 0.72533(8) 0.6258(4) 0.0547(6) Uani 1 1 d .
H9A H 1.0040 0.7335 0.6764 0.066 Uiso 1 1 calc R
C10A C 0.7799(4) 0.70350(7) 0.7569(4) 0.0475(6) Uani 1 1 d .
H10A H 0.8810 0.6966 0.8984 0.057 Uiso 1 1 calc R
C11A C 0.9089(4) 0.60547(7) 1.2210(4) 0.0527(6) Uani 1 1 d .
H11A H 1.0075 0.6075 1.1336 0.079 Uiso 1 1 calc R
H11B H 0.9109 0.5811 1.2726 0.079 Uiso 1 1 calc R
H11C H 0.9617 0.6213 1.3491 0.079 Uiso 1 1 calc R
C12A C 0.5656(3) 0.59081(6) 0.8898(3) 0.0372(5) Uani 1 1 d .
C13A C 0.6634(4) 0.58542(7) 0.7300(4) 0.0468(5) Uani 1 1 d .
H13A H 0.7958 0.5979 0.7397 0.056 Uiso 1 1 calc R
C14A C 0.5705(5) 0.56216(7) 0.5580(4) 0.0614(7) Uani 1 1 d .
H14A H 0.6396 0.5588 0.4502 0.074 Uiso 1 1 calc R
C15A C 0.3790(5) 0.54377(7) 0.5401(5) 0.0645(8) Uani 1 1 d .
H15A H 0.3149 0.5279 0.4205 0.077 Uiso 1 1 calc R
C16A C 0.2821(4) 0.54874(7) 0.6973(5) 0.0592(7) Uani 1 1 d .
H16A H 0.1506 0.5359 0.6873 0.071 Uiso 1 1 calc R
C17A C 0.3724(4) 0.57205(6) 0.8695(4) 0.0468(5) Uani 1 1 d .
H17A H 0.3015 0.5753 0.9759 0.056 Uiso 1 1 calc R
C18A C 0.3227(5) 0.73494(9) 0.1172(5) 0.0635(7) Uani 1 1 d .
H18A H 0.3963 0.7512 0.0459 0.095 Uiso 1 1 calc R
H18B H 0.1927 0.7466 0.1354 0.095 Uiso 1 1 calc R
H18C H 0.2732 0.7139 0.0246 0.095 Uiso 1 1 calc R
O1A O 0.1974(2) 0.69118(5) 0.3921(3) 0.0514(4) Uani 1 1 d .
H1A H 0.1750 0.6763 0.4787 0.077 Uiso 1 1 calc R
O2A O 0.2817(3) 0.65647(5) 0.7496(3) 0.0544(4) Uani 1 1 d .
C1B C -0.3351(4) 0.92796(6) 0.5817(4) 0.0438(5) Uani 1 1 d .
C2B C -0.4428(5) 0.90844(7) 0.7189(5) 0.0600(7) Uani 1 1 d .
H2B1 H -0.6065 0.9044 0.6541 0.072 Uiso 1 1 calc R
H2B2 H -0.3856 0.9129 0.8807 0.072 Uiso 1 1 calc R
C3B C -0.2954(4) 0.88777(7) 0.6244(5) 0.0528(6) Uani 1 1 d .
H3B H -0.3737 0.8718 0.4968 0.063 Uiso 1 1 calc R
C4B C -0.0727(4) 0.87586(6) 0.7755(4) 0.0497(6) Uani 1 1 d .
C5B C 0.0619(4) 0.85154(6) 0.6956(4) 0.0438(5) Uani 1 1 d .
C6B C 0.2737(4) 0.84038(6) 0.8410(4) 0.0469(6) Uani 1 1 d .
C7B C 0.4078(4) 0.81744(6) 0.7703(4) 0.0494(6) Uani 1 1 d .
C8B C 0.3257(4) 0.80626(8) 0.5546(5) 0.0603(7) Uani 1 1 d .
H8B H 0.4140 0.7905 0.5046 0.072 Uiso 1 1 calc R
C9B C 0.1199(4) 0.81683(9) 0.4056(5) 0.0641(7) Uani 1 1 d .
H9B H 0.0698 0.8087 0.2566 0.077 Uiso 1 1 calc R
C10B C -0.0117(4) 0.83947(7) 0.4768(4) 0.0554(6) Uani 1 1 d .
H10B H -0.1532 0.8469 0.3760 0.067 Uiso 1 1 calc R
C11B C -0.4785(4) 0.93763(7) 0.3477(4) 0.0568(7) Uani 1 1 d .
H11D H -0.5323 0.9619 0.3447 0.085 Uiso 1 1 calc R
H11E H -0.6069 0.9215 0.2954 0.085 Uiso 1 1 calc R
H11F H -0.3894 0.9357 0.2508 0.085 Uiso 1 1 calc R
C12B C -0.1447(4) 0.95276(6) 0.6881(3) 0.0372(5) Uani 1 1 d .
C13B C -0.1248(4) 0.97113(7) 0.8791(4) 0.0498(6) Uani 1 1 d .
H13B H -0.2318 0.9675 0.9494 0.060 Uiso 1 1 calc R
C14B C 0.0487(5) 0.99479(7) 0.9698(5) 0.0627(8) Uani 1 1 d .
H14B H 0.0583 1.0075 1.1003 0.075 Uiso 1 1 calc R
C15B C 0.2063(5) 1.00008(7) 0.8732(6) 0.0668(8) Uani 1 1 d .
H15B H 0.3266 1.0161 0.9369 0.080 Uiso 1 1 calc R
C16B C 0.1885(5) 0.98196(7) 0.6822(6) 0.0630(7) Uani 1 1 d .
H16B H 0.2964 0.9857 0.6131 0.076 Uiso 1 1 calc R
C17B C 0.0150(4) 0.95839(6) 0.5901(4) 0.0482(6) Uani 1 1 d .
H17B H 0.0051 0.9460 0.4587 0.058 Uiso 1 1 calc R
C18B C 0.6341(5) 0.80702(8) 0.9270(5) 0.0631(7) Uani 1 1 d .
H18D H 0.7348 0.8274 0.9565 0.095 Uiso 1 1 calc R
H18E H 0.6947 0.7880 0.8609 0.095 Uiso 1 1 calc R
H18F H 0.6212 0.7988 1.0665 0.095 Uiso 1 1 calc R
O1B O 0.3583(3) 0.85165(5) 1.0530(3) 0.0617(5) Uani 1 1 d .
H1B H 0.2702 0.8664 1.0761 0.093 Uiso 1 1 calc R
O2B O -0.0003(3) 0.88721(5) 0.9691(3) 0.0624(5) 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 0.0181 0.0091 '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 0.0492 0.0322 '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_publ_flag
C2A C1A C12A 120.7(2) y
C2A C1A C11A 117.7(2) y
C12A C1A C11A 114.43(19) y
C2A C1A C3A 59.27(16) y
C12A C1A C3A 118.63(18) y
C11A C1A C3A 114.92(19) y
C1A C2A C3A 62.56(16) y
C1A C2A H2A1 117.5 ?
C3A C2A H2A1 117.5 ?
C1A C2A H2A2 117.5 ?
C3A C2A H2A2 117.5 ?
H2A1 C2A H2A2 114.6 ?
C4A C3A C2A 118.4(2) y
C4A C3A C1A 117.9(2) y
C2A C3A C1A 58.16(15) y
C4A C3A H3A 116.5 ?
C2A C3A H3A 116.5 ?
C1A C3A H3A 116.5 ?
O2A C4A C5A 120.2(2) y
O2A C4A C3A 119.9(2) y
C5A C4A C3A 119.9(2) y
C10A C5A C6A 118.0(2) y
C10A C5A C4A 122.1(2) y
C6A C5A C4A 119.9(2) y
O1A C6A C7A 117.32(19) y
O1A C6A C5A 121.5(2) y
C7A C6A C5A 121.2(2) y
C8A C7A C6A 118.6(2) y
C8A C7A C18A 122.5(2) y
C6A C7A C18A 118.9(2) y
C7A C8A C9A 121.6(2) y
C7A C8A H8A 119.2 ?
C9A C8A H8A 119.2 ?
C10A C9A C8A 119.5(2) y
C10A C9A H9A 120.2 ?
C8A C9A H9A 120.2 ?
C9A C10A C5A 121.0(2) y
C9A C10A H10A 119.5 ?
C5A C10A H10A 119.5 ?
C1A C11A H11A 109.5 ?
C1A C11A H11B 109.5 ?
H11A C11A H11B 109.5 ?
C1A C11A H11C 109.5 ?
H11A C11A H11C 109.5 ?
H11B C11A H11C 109.5 ?
C17A C12A C13A 117.8(2) y
C17A C12A C1A 122.4(2) y
C13A C12A C1A 119.8(2) y
C14A C13A C12A 120.7(2) y
C14A C13A H13A 119.6 ?
C12A C13A H13A 119.6 ?
C15A C14A C13A 120.8(3) y
C15A C14A H14A 119.6 ?
C13A C14A H14A 119.6 ?
C16A C15A C14A 118.9(2) y
C16A C15A H15A 120.5 ?
C14A C15A H15A 120.5 ?
C15A C16A C17A 120.9(3) y
C15A C16A H16A 119.6 ?
C17A C16A H16A 119.6 ?
C16A C17A C12A 120.9(2) y
C16A C17A H17A 119.6 ?
C12A C17A H17A 119.6 ?
C7A C18A H18A 109.5 ?
C7A C18A H18B 109.5 ?
H18A C18A H18B 109.5 ?
C7A C18A H18C 109.5 ?
H18A C18A H18C 109.5 ?
H18B C18A H18C 109.5 ?
C6A O1A H1A 109.5 ?
C2B C1B C12B 120.5(2) y
C2B C1B C11B 118.0(2) y
C12B C1B C11B 114.5(2) y
C2B C1B C3B 59.20(17) y
C12B C1B C3B 118.62(18) y
C11B C1B C3B 114.8(2) y
C1B C2B C3B 62.51(16) y
C1B C2B H2B1 117.5 ?
C3B C2B H2B1 117.5 ?
C1B C2B H2B2 117.5 ?
C3B C2B H2B2 117.5 ?
H2B1 C2B H2B2 114.6 ?
C4B C3B C2B 118.8(2) y
C4B C3B C1B 118.3(2) y
C2B C3B C1B 58.29(17) y
C4B C3B H3B 116.3 ?
C2B C3B H3B 116.3 ?
C1B C3B H3B 116.3 ?
O2B C4B C5B 120.7(2) y
O2B C4B C3B 119.1(2) y
C5B C4B C3B 120.2(2) y
C10B C5B C6B 118.5(2) y
C10B C5B C4B 121.8(2) y
C6B C5B C4B 119.7(2) y
O1B C6B C7B 116.8(2) y
O1B C6B C5B 121.9(2) y
C7B C6B C5B 121.3(2) y
C8B C7B C6B 117.4(2) y
C8B C7B C18B 122.7(3) y
C6B C7B C18B 119.8(2) y
C7B C8B C9B 123.1(3) y
C7B C8B H8B 118.4 ?
C9B C8B H8B 118.4 ?
C10B C9B C8B 119.1(3) y
C10B C9B H9B 120.5 ?
C8B C9B H9B 120.5 ?
C9B C10B C5B 120.5(2) y
C9B C10B H10B 119.7 ?
C5B C10B H10B 119.7 ?
C1B C11B H11D 109.5 ?
C1B C11B H11E 109.5 ?
H11D C11B H11E 109.5 ?
C1B C11B H11F 109.5 ?
H11D C11B H11F 109.5 ?
H11E C11B H11F 109.5 ?
C13B C12B C17B 118.2(2) y
C13B C12B C1B 122.2(2) y
C17B C12B C1B 119.6(2) y
C12B C13B C14B 121.0(2) y
C12B C13B H13B 119.5 ?
C14B C13B H13B 119.5 ?
C15B C14B C13B 120.5(3) y
C15B C14B H14B 119.8 ?
C13B C14B H14B 119.8 ?
C14B C15B C16B 119.2(3) y
C14B C15B H15B 120.4 ?
C16B C15B H15B 120.4 ?
C15B C16B C17B 120.6(3) y
C15B C16B H16B 119.7 ?
C17B C16B H16B 119.7 ?
C16B C17B C12B 120.5(2) y
C16B C17B H17B 119.8 ?
C12B C17B H17B 119.8 ?
C7B C18B H18D 109.5 ?
C7B C18B H18E 109.5 ?
H18D C18B H18E 109.5 ?
C7B C18B H18F 109.5 ?
H18D C18B H18F 109.5 ?
H18E C18B H18F 109.5 ?
C6B O1B H1B 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1a C2a 1.484(3) y
C1a C12a 1.494(3) y
C1a C11a 1.508(3) y
C1a C3a 1.550(3) y
C2a C3a 1.502(4) y
C2a H2a1 0.9900 ?
C2a H2a2 0.9900 ?
C3a C4a 1.477(3) y
C3a H3a 1.0000 ?
C4a O2a 1.239(3) y
C4a C5a 1.474(3) y
C5a C10a 1.394(3) y
C5a C6a 1.416(3) y
C6a O1a 1.352(3) y
C6a C7a 1.387(3) y
C7a C8a 1.376(3) y
C7a C18a 1.506(3) y
C8a C9a 1.392(3) y
C8a H8a 0.9500 ?
C9a C10a 1.374(4) y
C9a H9a 0.9500 ?
C10a H10a 0.9500 ?
C11a H11a 0.9800 ?
C11a H11b 0.9800 ?
C11a H11c 0.9800 ?
C12a C17a 1.386(3) y
C12a C13a 1.389(3) y
C13a C14a 1.376(4) y
C13a H13a 0.9500 ?
C14a C15a 1.373(4) y
C14a H14a 0.9500 ?
C15a C16a 1.368(4) y
C15a H15a 0.9500 ?
C16a C17a 1.376(4) y
C16a H16a 0.9500 ?
C17a H17a 0.9500 ?
C18a H18a 0.9800 ?
C18a H18b 0.9800 ?
C18a H18c 0.9800 ?
O1a H1a 0.8400 ?
C1b C2b 1.489(4) y
C1b C12b 1.497(3) y
C1b C11b 1.508(3) y
C1b C3b 1.552(3) y
C2b C3b 1.503(4) y
C2b H2b1 0.9900 ?
C2b H2b2 0.9900 ?
C3b C4b 1.482(4) y
C3b H3b 1.0000 ?
C4b O2b 1.243(3) y
C4b C5b 1.468(4) y
C5b C10b 1.396(4) y
C5b C6b 1.411(3) y
C6b O1b 1.348(3) y
C6b C7b 1.401(4) y
C7b C8b 1.368(4) y
C7b C18b 1.494(3) y
C8b C9b 1.385(4) y
C8b H8b 0.9500 ?
C9b C10b 1.383(4) y
C9b H9b 0.9500 ?
C10b H10b 0.9500 ?
C11b H11d 0.9800 ?
C11b H11e 0.9800 ?
C11b H11f 0.9800 ?
C12b C13b 1.379(3) y
C12b C17b 1.386(3) y
C13b C14b 1.383(4) y
C13b H13b 0.9500 ?
C14b C15b 1.366(5) y
C14b H14b 0.9500 ?
C15b C16b 1.376(5) y
C15b H15b 0.9500 ?
C16b C17b 1.382(4) y
C16b H16b 0.9500 ?
C17b H17b 0.9500 ?
C18b H18d 0.9800 ?
C18b H18e 0.9800 ?
C18b H18f 0.9800 ?
O1b H1b 0.8400 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1A H1A O2A 0.84 1.8 2.538(2) 146
O1B H1B O2B 0.84 1.8 2.540(3) 146.4
