#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:27:34 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225068 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156919.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_7156919
loop_
_publ_author_name
'Sun, Wenxi'
'Peng, Cheng'
'Yao, Zhigang'
'Xu, Fan'
_publ_section_title
;
 Diastereoselective synthesis of α-dicarbonyl cyclopropanes via a
 lanthanide amide-catalysed reaction.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6620
_journal_page_last               6628
_journal_paper_doi               10.1039/c9ob00732f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C29 H24 O3'
_chemical_formula_sum            'C29 H24 O3'
_chemical_formula_weight         420.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-09-11 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.912(4)
_cell_angle_beta                 98.480(4)
_cell_angle_gamma                104.031(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8923(12)
_cell_length_b                   10.3082(14)
_cell_length_c                   14.777(2)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.72
_cell_volume                     1110.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22393
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0670
_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)+(0.0993P)²+0.3602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1852
_reflns_number_gt                3509
_reflns_number_total             4870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00732f2.cif
_cod_data_source_block           b160923a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7156917--7156919.cif.'
_cod_database_code               7156919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -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_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.42144(19) 0.06729(15) 0.26650(11) 0.0311(4) Uani 1 d .
O2 O 0.4163(2) 0.14477(15) 0.07354(10) 0.0320(4) Uani 1 d .
O3 O 0.2147(2) 0.23457(16) 0.13838(11) 0.0330(4) Uani 1 d .
C1 C 0.6340(3) 0.2782(2) 0.27763(14) 0.0227(4) Uani 1 d .
H1 H 0.7628 0.3243 0.2970 0.027 Uiso 1 calc R
C2 C 0.5143(3) 0.3649(2) 0.31144(13) 0.0220(4) Uani 1 d .
H2 H 0.4023 0.3099 0.3217 0.026 Uiso 1 calc R
C3 C 0.5282(3) 0.3344(2) 0.20869(13) 0.0225(4) Uani 1 d .
C4 C 0.5777(3) 0.1273(2) 0.27315(13) 0.0228(4) Uani 1 d .
C5 C 0.7179(3) 0.0542(2) 0.27791(13) 0.0221(4) Uani 1 d .
C6 C 0.8806(3) 0.1014(2) 0.25323(14) 0.0257(5) Uani 1 d .
H6 H 0.9060 0.1838 0.2353 0.031 Uiso 1 calc R
C7 C 1.0044(3) 0.0282(2) 0.25488(15) 0.0301(5) Uani 1 d .
H7 H 1.1117 0.0597 0.2369 0.036 Uiso 1 calc R
C8 C 0.9685(3) -0.0929(2) 0.28354(15) 0.0329(5) Uani 1 d .
H8 H 1.0526 -0.1423 0.2853 0.040 Uiso 1 calc R
C9 C 0.8084(3) -0.1409(2) 0.30954(17) 0.0355(5) Uani 1 d .
H9 H 0.7859 -0.2216 0.3296 0.043 Uiso 1 calc R
C10 C 0.6821(3) -0.0691(2) 0.30573(15) 0.0294(5) Uani 1 d .
H10 H 0.5732 -0.1026 0.3217 0.035 Uiso 1 calc R
C11 C 0.5874(3) 0.5041(2) 0.38123(13) 0.0230(4) Uani 1 d .
C12 C 0.7561(3) 0.5466(2) 0.43673(14) 0.0279(5) Uani 1 d .
H12 H 0.8300 0.4890 0.4282 0.034 Uiso 1 calc R
C13 C 0.8207(3) 0.6753(2) 0.50653(15) 0.0330(5) Uani 1 d .
H13 H 0.9368 0.7023 0.5424 0.040 Uiso 1 calc R
C14 C 0.7140(3) 0.7599(2) 0.52146(15) 0.0320(5) Uani 1 d .
H14 H 0.7576 0.8446 0.5676 0.038 Uiso 1 calc R
C15 C 0.5373(3) 0.7202(2) 0.46753(14) 0.0273(5) Uani 1 d .
C16 C 0.4215(3) 0.8046(2) 0.48407(16) 0.0339(5) Uani 1 d .
H16 H 0.4628 0.8883 0.5312 0.041 Uiso 1 calc R
C17 C 0.2515(3) 0.7657(3) 0.43246(17) 0.0383(6) Uani 1 d .
H17 H 0.1770 0.8219 0.4449 0.046 Uiso 1 calc R
C18 C 0.1881(3) 0.6397(3) 0.35988(17) 0.0355(5) Uani 1 d .
H18 H 0.0722 0.6137 0.3240 0.043 Uiso 1 calc R
C19 C 0.2955(3) 0.5556(2) 0.34198(15) 0.0283(5) Uani 1 d .
H19 H 0.2515 0.4729 0.2939 0.034 Uiso 1 calc R
C20 C 0.4732(3) 0.5918(2) 0.39525(13) 0.0224(4) Uani 1 d .
C21 C 0.6265(3) 0.4421(2) 0.16656(14) 0.0272(5) Uani 1 d .
C22 C 0.5441(4) 0.5385(2) 0.14224(16) 0.0387(6) Uani 1 d .
H22 H 0.4334 0.5400 0.1563 0.046 Uiso 1 calc R
C23 C 0.6277(4) 0.6324(3) 0.09699(19) 0.0531(8) Uani 1 d .
H23 H 0.5715 0.6955 0.0797 0.064 Uiso 1 calc R
C24 C 0.7925(4) 0.6327(3) 0.07756(18) 0.0544(8) Uani 1 d .
H24 H 0.8482 0.6965 0.0478 0.065 Uiso 1 calc R
C25 C 0.8748(4) 0.5392(3) 0.10185(19) 0.0522(8) Uani 1 d .
H25 H 0.9867 0.5399 0.0890 0.063 Uiso 1 calc R
C26 C 0.7917(3) 0.4436(3) 0.14562(16) 0.0375(6) Uani 1 d .
H26 H 0.8479 0.3796 0.1611 0.045 Uiso 1 calc R
C27 C 0.3661(3) 0.2327(2) 0.13839(13) 0.0233(4) Uani 1 d .
C28 C 0.2755(3) 0.0390(3) 0.00046(17) 0.0416(6) Uani 1 d .
H28A H 0.3178 0.0197 -0.0581 0.050 Uiso 1 calc R
H28B H 0.1729 0.0737 -0.0115 0.050 Uiso 1 calc R
C29 C 0.2207(4) -0.0911(3) 0.0295(2) 0.0482(7) Uani 1 d .
H29A H 0.3219 -0.1260 0.0407 0.072 Uiso 1 calc GR
H29B H 0.1287 -0.1589 -0.0201 0.072 Uiso 1 calc GR
H29C H 0.1761 -0.0725 0.0866 0.072 Uiso 1 calc GR
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
C27 O2 C28 117.39(18)
C2 C1 H1 115.9
C2 C1 C3 59.49(13)
C3 C1 H1 115.9
C4 C1 H1 115.9
C4 C1 C2 117.75(17)
C4 C1 C3 119.94(17)
C1 C2 H2 113.3
C3 C2 C1 60.56(13)
C3 C2 H2 113.3
C11 C2 C1 121.90(17)
C11 C2 H2 113.3
C11 C2 C3 124.66(17)
C2 C3 C1 59.95(12)
C2 C3 C27 116.01(17)
C21 C3 C1 119.28(17)
C21 C3 C2 122.87(17)
C21 C3 C27 112.10(16)
C27 C3 C1 117.51(17)
O1 C4 C1 120.55(18)
O1 C4 C5 121.44(18)
C5 C4 C1 118.01(17)
C6 C5 C4 122.52(18)
C6 C5 C10 119.02(19)
C10 C5 C4 118.43(18)
C5 C6 H6 119.5
C7 C6 C5 121.0(2)
C7 C6 H6 119.5
C6 C7 H7 120.2
C6 C7 C8 119.6(2)
C8 C7 H7 120.2
C7 C8 H8 119.8
C9 C8 C7 120.4(2)
C9 C8 H8 119.8
C8 C9 H9 120.0
C10 C9 C8 120.0(2)
C10 C9 H9 120.0
C5 C10 H10 120.0
C9 C10 C5 120.0(2)
C9 C10 H10 120.0
C12 C11 C2 122.06(18)
C12 C11 C20 119.06(18)
C20 C11 C2 118.73(17)
C11 C12 H12 119.1
C11 C12 C13 121.7(2)
C13 C12 H12 119.1
C12 C13 H13 119.9
C14 C13 C12 120.2(2)
C14 C13 H13 119.9
C13 C14 H14 119.7
C13 C14 C15 120.6(2)
C15 C14 H14 119.7
C14 C15 C16 121.6(2)
C14 C15 C20 119.38(19)
C16 C15 C20 119.1(2)
C15 C16 H16 119.3
C17 C16 C15 121.4(2)
C17 C16 H16 119.3
C16 C17 H17 120.1
C16 C17 C18 119.8(2)
C18 C17 H17 120.1
C17 C18 H18 119.7
C19 C18 C17 120.5(2)
C19 C18 H18 119.7
C18 C19 H19 119.4
C18 C19 C20 121.3(2)
C20 C19 H19 119.4
C15 C20 C11 119.05(18)
C19 C20 C11 122.99(18)
C19 C20 C15 117.94(18)
C22 C21 C3 119.1(2)
C26 C21 C3 122.1(2)
C26 C21 C22 118.7(2)
C21 C22 H22 120.1
C23 C22 C21 119.9(3)
C23 C22 H22 120.1
C22 C23 H23 119.8
C24 C23 C22 120.5(3)
C24 C23 H23 119.8
C23 C24 H24 120.0
C25 C24 C23 120.0(2)
C25 C24 H24 120.0
C24 C25 H25 119.9
C24 C25 C26 120.1(3)
C26 C25 H25 119.9
C21 C26 C25 120.9(3)
C21 C26 H26 119.6
C25 C26 H26 119.6
O2 C27 C3 110.32(17)
O3 C27 O2 124.91(19)
O3 C27 C3 124.70(18)
O2 C28 H28A 109.4
O2 C28 H28B 109.4
O2 C28 C29 111.3(2)
H28A C28 H28B 108.0
C29 C28 H28A 109.4
C29 C28 H28B 109.4
C28 C29 H29A 109.5
C28 C29 H29B 109.5
C28 C29 H29C 109.5
H29A C29 H29B 109.5
H29A C29 H29C 109.5
H29B C29 H29C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.217(2)
O2 C27 1.340(2)
O2 C28 1.456(3)
O3 C27 1.199(2)
C1 H1 0.9800
C1 C2 1.513(3)
C1 C3 1.523(3)
C1 C4 1.494(3)
C2 H2 0.9800
C2 C3 1.506(3)
C2 C11 1.490(3)
C3 C21 1.502(3)
C3 C27 1.512(3)
C4 C5 1.485(3)
C5 C6 1.391(3)
C5 C10 1.399(3)
C6 H6 0.9300
C6 C7 1.372(3)
C7 H7 0.9300
C7 C8 1.384(3)
C8 H8 0.9300
C8 C9 1.384(3)
C9 H9 0.9300
C9 C10 1.380(3)
C10 H10 0.9300
C11 C12 1.368(3)
C11 C20 1.428(3)
C12 H12 0.9300
C12 C13 1.411(3)
C13 H13 0.9300
C13 C14 1.357(3)
C14 H14 0.9300
C14 C15 1.413(3)
C15 C16 1.417(3)
C15 C20 1.426(3)
C16 H16 0.9300
C16 C17 1.358(4)
C17 H17 0.9300
C17 C18 1.411(3)
C18 H18 0.9300
C18 C19 1.364(3)
C19 H19 0.9300
C19 C20 1.419(3)
C21 C22 1.394(3)
C21 C26 1.381(3)
C22 H22 0.9300
C22 C23 1.389(3)
C23 H23 0.9300
C23 C24 1.372(4)
C24 H24 0.9300
C24 C25 1.367(4)
C25 H25 0.9300
C25 C26 1.384(3)
C26 H26 0.9300
C28 H28A 0.9700
C28 H28B 0.9700
C28 C29 1.483(4)
C29 H29A 0.9600
C29 H29B 0.9600
C29 H29C 0.9600
