#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:06:56 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200588 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/70/1547072.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_1547072
loop_
_publ_author_name
'Sicignano, Marina'
'Dentoni Litta, Antonella'
'Schettini, Rosaria'
'De Riccardis, Francesco'
'Pierri, Giovanni'
'Tedesco, Consiglia'
'Izzo, Irene'
'Della Sala, Giorgio'
_publ_section_title
;
 Highly Diastereoselective Crown Ether Catalyzed Arylogous Michael
 Reaction of 3-Aryl Phthalides.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4383
_journal_page_last               4386
_journal_paper_doi               10.1021/acs.orglett.7b02113
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C29 H22 O3'
_chemical_formula_sum            'C29 H22 O3'
_chemical_formula_weight         418.46
_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
_audit_creation_date             2017-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                116.064(7)
_cell_angle_beta                 93.344(8)
_cell_angle_gamma                103.846(15)
_cell_formula_units_Z            2
_cell_length_a                   9.229(7)
_cell_length_b                   11.780(9)
_cell_length_c                   11.881(8)
_cell_measurement_reflns_used    4153
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2484
_cell_measurement_theta_min      1.9425
_cell_volume                     1106.6(14)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
'SIR2014 (Burla et al., 2015)'
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.1434
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9115
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.634
_diffrn_reflns_theta_min         1.943
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0721P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2768
_reflns_number_total             4974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02113_si_002.cif
_cod_data_source_block           compound3aa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1547072
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C25(H25), C28(H28), C10(H10), C18(H18), C29(H29), C17(H17),
 C3(H3), C27(H27), C14(H14), C5(H5), C4(H4), C19(H19), C20(H20), C26(H26),
 C13(H13), C12(H12), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O2 O 0.96860(14) 0.80934(13) 0.42882(12) 0.0265(3) Uani 1 1 d .
O3 O 1.00973(17) 0.68770(15) -0.02570(13) 0.0392(4) Uani 1 1 d .
O1 O 1.08632(17) 0.94019(15) 0.63169(14) 0.0411(4) Uani 1 1 d .
C7 C 0.9577(2) 0.67875(19) 0.32509(18) 0.0245(4) Uani 1 1 d .
C9 C 0.7920(2) 0.5942(2) 0.28648(19) 0.0267(5) Uani 1 1 d .
C15 C 1.0158(2) 0.6992(2) 0.21308(19) 0.0258(5) Uani 1 1 d .
H15 H 1.0046 0.6098 0.1409 0.031 Uiso 1 1 calc R
C6 C 1.05989(19) 0.62886(19) 0.38525(18) 0.0236(4) Uani 1 1 d .
C23 C 0.9365(2) 0.75665(19) 0.04073(18) 0.0267(5) Uani 1 1 d .
C16 C 1.1829(2) 0.7780(2) 0.24700(18) 0.0258(5) Uani 1 1 d .
C2 C 1.2196(2) 0.7077(2) 0.5895(2) 0.0323(5) Uani 1 1 d .
H2 H 1.2622 0.7755 0.6743 0.039 Uiso 1 1 calc R
C1 C 1.1212(2) 0.72422(19) 0.50859(18) 0.0263(5) Uani 1 1 d .
C21 C 1.2883(2) 0.7151(2) 0.1902(2) 0.0323(5) Uani 1 1 d .
H21 H 1.2548 0.6236 0.1305 0.039 Uiso 1 1 calc R
C22 C 0.9148(2) 0.7623(2) 0.16709(18) 0.0257(5) Uani 1 1 d .
H22A H 0.8071 0.7167 0.1605 0.031 Uiso 1 1 calc R
H22B H 0.9363 0.8559 0.2318 0.031 Uiso 1 1 calc R
C25 C 0.7643(2) 0.8990(2) 0.06208(19) 0.0289(5) Uani 1 1 d .
H25 H 0.7438 0.8974 0.1389 0.035 Uiso 1 1 calc R
C28 C 0.8239(2) 0.9065(2) -0.1600(2) 0.0334(5) Uani 1 1 d .
H28 H 0.8445 0.9091 -0.2364 0.040 Uiso 1 1 calc R
C10 C 0.6827(2) 0.6431(2) 0.3515(2) 0.0323(5) Uani 1 1 d .
H10 H 0.7108 0.7295 0.4218 0.039 Uiso 1 1 calc R
C18 C 1.3889(2) 0.9814(2) 0.3632(2) 0.0361(5) Uani 1 1 d .
H18 H 1.4232 1.0727 0.4233 0.043 Uiso 1 1 calc R
C29 C 0.8921(2) 0.8380(2) -0.11611(19) 0.0296(5) Uani 1 1 d .
H29 H 0.9600 0.7943 -0.1621 0.036 Uiso 1 1 calc R
C17 C 1.2352(2) 0.9126(2) 0.33315(19) 0.0296(5) Uani 1 1 d .
H17 H 1.1649 0.9579 0.3719 0.035 Uiso 1 1 calc R
C3 C 1.2530(2) 0.5889(2) 0.5418(2) 0.0333(5) Uani 1 1 d .
H3 H 1.3195 0.5738 0.5944 0.040 Uiso 1 1 calc R
C27 C 0.7254(2) 0.9717(2) -0.0939(2) 0.0366(5) Uani 1 1 d .
H27 H 0.6784 1.0187 -0.1248 0.044 Uiso 1 1 calc R
C14 C 0.7484(2) 0.4672(2) 0.1845(2) 0.0341(5) Uani 1 1 d .
H14 H 0.8223 0.4329 0.1392 0.041 Uiso 1 1 calc R
C5 C 1.0935(2) 0.5086(2) 0.33673(19) 0.0285(5) Uani 1 1 d .
H5 H 1.0519 0.4412 0.2517 0.034 Uiso 1 1 calc R
C8 C 1.0640(2) 0.8375(2) 0.53573(19) 0.0294(5) Uani 1 1 d .
C4 C 1.1903(2) 0.4915(2) 0.4179(2) 0.0323(5) Uani 1 1 d .
H4 H 1.2144 0.4103 0.3874 0.039 Uiso 1 1 calc R
C19 C 1.4919(2) 0.9171(2) 0.3057(2) 0.0391(6) Uani 1 1 d .
H19 H 1.5968 0.9642 0.3254 0.047 Uiso 1 1 calc R
C20 C 1.4414(2) 0.7837(2) 0.2192(2) 0.0385(6) Uani 1 1 d .
H20 H 1.5119 0.7391 0.1797 0.046 Uiso 1 1 calc R
C26 C 0.6960(2) 0.9680(2) 0.0172(2) 0.0344(5) Uani 1 1 d .
H26 H 0.6289 1.0128 0.0632 0.041 Uiso 1 1 calc R
C13 C 0.5976(2) 0.3902(2) 0.1481(2) 0.0418(6) Uani 1 1 d .
H13 H 0.5690 0.3035 0.0783 0.050 Uiso 1 1 calc R
C12 C 0.4894(2) 0.4391(3) 0.2128(2) 0.0421(6) Uani 1 1 d .
H12 H 0.3863 0.3863 0.1884 0.051 Uiso 1 1 calc R
C11 C 0.5322(2) 0.5657(2) 0.3135(2) 0.0394(6) Uani 1 1 d .
H11 H 0.4576 0.6002 0.3575 0.047 Uiso 1 1 calc R
C24 C 0.86254(19) 0.83192(19) -0.00435(18) 0.0250(4) 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
C8 O2 C7 111.26(15)
O2 C7 C9 108.33(14)
O2 C7 C15 107.38(16)
O2 C7 C6 102.97(15)
C9 C7 C15 111.55(16)
C6 C7 C9 112.66(16)
C6 C7 C15 113.34(14)
C10 C9 C7 120.73(18)
C10 C9 C14 119.03(18)
C14 C9 C7 120.23(16)
C16 C15 C7 112.70(16)
C16 C15 C22 111.99(16)
C22 C15 C7 109.66(14)
C1 C6 C7 108.74(17)
C1 C6 C5 120.17(18)
C5 C6 C7 131.07(18)
O3 C23 C22 120.50(18)
O3 C23 C24 120.71(18)
C24 C23 C22 118.75(16)
C21 C16 C15 119.48(19)
C21 C16 C17 118.19(18)
C17 C16 C15 122.32(16)
C3 C2 C1 117.3(2)
C6 C1 C2 122.62(19)
C6 C1 C8 108.88(17)
C2 C1 C8 128.49(19)
C20 C21 C16 121.0(2)
C23 C22 C15 113.93(15)
C26 C25 C24 120.78(19)
C29 C28 C27 120.6(2)
C11 C10 C9 119.9(2)
C19 C18 C17 120.1(2)
C28 C29 C24 120.69(18)
C18 C17 C16 120.86(18)
C2 C3 C4 120.45(19)
C26 C27 C28 119.49(19)
C13 C14 C9 120.55(19)
C4 C5 C6 117.23(19)
O2 C8 C1 108.14(17)
O1 C8 O2 121.01(19)
O1 C8 C1 130.8(2)
C3 C4 C5 122.21(19)
C18 C19 C20 119.7(2)
C19 C20 C21 120.18(18)
C27 C26 C25 120.23(19)
C12 C13 C14 120.2(2)
C13 C12 C11 119.3(2)
C12 C11 C10 120.9(2)
C25 C24 C23 122.05(17)
C25 C24 C29 118.17(18)
C29 C24 C23 119.77(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C7 1.463(2)
O2 C8 1.363(2)
O3 C23 1.225(2)
O1 C8 1.203(2)
C7 C9 1.526(3)
C7 C15 1.556(3)
C7 C6 1.517(3)
C9 C10 1.387(3)
C9 C14 1.389(3)
C15 C16 1.522(3)
C15 C22 1.532(3)
C6 C1 1.372(3)
C6 C5 1.397(3)
C23 C22 1.501(3)
C23 C24 1.484(3)
C16 C21 1.391(3)
C16 C17 1.394(3)
C2 C1 1.391(3)
C2 C3 1.381(3)
C1 C8 1.464(3)
C21 C20 1.386(3)
C25 C26 1.389(3)
C25 C24 1.396(3)
C28 C29 1.377(3)
C28 C27 1.387(3)
C10 C11 1.387(3)
C18 C17 1.391(3)
C18 C19 1.381(3)
C29 C24 1.399(3)
C3 C4 1.385(3)
C27 C26 1.380(3)
C14 C13 1.388(3)
C5 C4 1.387(3)
C19 C20 1.385(3)
C13 C12 1.377(3)
C12 C11 1.380(3)
