#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/07/7150718.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_7150718
loop_
_publ_author_name
'Zhang, Xiaoxiang'
'Rao, Weidong'
'Chan, Sally'
'Chan, Philip Wai Hong'
_publ_section_title
;
 Iron(III) chloride-catalysed direct nucleophilic α-substitution of
 Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl
 compounds, and thiols
;
_journal_issue                   20
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4186
_journal_paper_doi               10.1039/b908447a
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H21 Cl O3'
_chemical_formula_sum            'C27 H21 Cl O3'
_chemical_formula_weight         428.89
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0930(5)
_cell_length_b                   13.4335(5)
_cell_length_c                   14.4720(6)
_cell_measurement_reflns_used    6322
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.09
_cell_measurement_theta_min      2.38
_cell_volume                     2156.59(15)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35079
_diffrn_reflns_theta_full        31.31
_diffrn_reflns_theta_max         31.31
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_correction_T_min  0.9414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6767
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_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+0.1012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                6067
_reflns_number_total             6767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b908447a.txt
_cod_data_source_block           chan29
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7150718
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73912(11) 0.20776(10) 0.05399(10) 0.0254(3) Uani 1 1 d . . .
H1 H 0.6774 0.2247 0.0967 0.031 Uiso 1 1 calc R . .
C2 C 0.71412(13) 0.20802(11) -0.03995(11) 0.0300(3) Uani 1 1 d . . .
H2 H 0.6359 0.2251 -0.0614 0.036 Uiso 1 1 calc R . .
C3 C 0.80414(14) 0.18311(10) -0.10212(11) 0.0303(3) Uani 1 1 d . . .
C4 C 0.91693(14) 0.15493(11) -0.07201(11) 0.0322(3) Uani 1 1 d . . .
H4 H 0.9770 0.1352 -0.1150 0.039 Uiso 1 1 calc R . .
C5 C 0.94161(12) 0.15572(11) 0.02235(10) 0.0270(3) Uani 1 1 d . . .
H5 H 1.0197 0.1374 0.0433 0.032 Uiso 1 1 calc R . .
C6 C 0.85391(10) 0.18288(8) 0.08670(9) 0.0200(2) Uani 1 1 d . . .
C7 C 0.88262(10) 0.18165(9) 0.18958(9) 0.0187(2) Uani 1 1 d . . .
H7 H 0.9722 0.1774 0.1958 0.022 Uiso 1 1 calc R . .
C8 C 0.84267(10) 0.27533(8) 0.23873(9) 0.0187(2) Uani 1 1 d . . .
C9 C 0.73615(11) 0.29953(9) 0.27735(11) 0.0237(2) Uani 1 1 d . . .
H9 H 0.6690 0.2557 0.2786 0.028 Uiso 1 1 calc R . .
C10 C 0.73339(11) 0.40201(10) 0.31822(10) 0.0248(3) Uani 1 1 d . . .
H10A H 0.7104 0.3998 0.3843 0.030 Uiso 1 1 calc R . .
H10B H 0.6758 0.4452 0.2847 0.030 Uiso 1 1 calc R . .
C11 C 0.86274(11) 0.43938(10) 0.30654(11) 0.0258(3) Uani 1 1 d . . .
H11A H 0.8640 0.5036 0.2730 0.031 Uiso 1 1 calc R . .
H11B H 0.9018 0.4486 0.3674 0.031 Uiso 1 1 calc R . .
C12 C 0.92628(10) 0.35963(9) 0.25160(9) 0.0196(2) Uani 1 1 d . . .
C13 C 0.82921(10) 0.08750(8) 0.23469(9) 0.0182(2) Uani 1 1 d . . .
H13 H 0.7394 0.0877 0.2284 0.022 Uiso 1 1 calc R . .
C14 C 0.88244(11) -0.00496(9) 0.18645(9) 0.0210(2) Uani 1 1 d . . .
C15 C 0.80400(11) -0.07424(9) 0.13292(9) 0.0215(2) Uani 1 1 d . . .
C16 C 0.68295(12) -0.05516(10) 0.11367(10) 0.0265(3) Uani 1 1 d . . .
H16 H 0.6464 0.0043 0.1356 0.032 Uiso 1 1 calc R . .
C17 C 0.61570(13) -0.12301(11) 0.06246(11) 0.0324(3) Uani 1 1 d . . .
H17 H 0.5336 -0.1093 0.0488 0.039 Uiso 1 1 calc R . .
C18 C 0.66803(15) -0.21041(12) 0.03139(11) 0.0344(3) Uani 1 1 d . . .
H18 H 0.6215 -0.2571 -0.0027 0.041 Uiso 1 1 calc R . .
C19 C 0.78838(15) -0.22977(12) 0.05005(13) 0.0364(3) Uani 1 1 d . . .
H19 H 0.8243 -0.2895 0.0282 0.044 Uiso 1 1 calc R . .
C20 C 0.85643(12) -0.16253(10) 0.10040(11) 0.0286(3) Uani 1 1 d . . .
H20 H 0.9388 -0.1762 0.1129 0.034 Uiso 1 1 calc R . .
C21 C 0.86433(10) 0.08218(9) 0.33692(9) 0.0217(2) Uani 1 1 d . . .
C22 C 0.78488(11) 0.02585(9) 0.40137(10) 0.0238(2) Uani 1 1 d . . .
C23 C 0.67891(13) -0.02104(11) 0.37194(11) 0.0318(3) Uani 1 1 d . . .
H23 H 0.6580 -0.0214 0.3083 0.038 Uiso 1 1 calc R . .
C24 C 0.60432(14) -0.06705(12) 0.43624(13) 0.0398(4) Uani 1 1 d . . .
H24 H 0.5325 -0.0991 0.4164 0.048 Uiso 1 1 calc R . .
C25 C 0.63398(18) -0.06645(13) 0.52840(13) 0.0457(5) Uani 1 1 d . . .
H25 H 0.5815 -0.0966 0.5721 0.055 Uiso 1 1 calc R . .
C26 C 0.73957(19) -0.02236(14) 0.55806(12) 0.0454(4) Uani 1 1 d . . .
H26 H 0.7601 -0.0233 0.6218 0.055 Uiso 1 1 calc R . .
C27 C 0.81577(16) 0.02336(11) 0.49492(11) 0.0335(3) Uani 1 1 d . . .
H27 H 0.8889 0.0529 0.5153 0.040 Uiso 1 1 calc R . .
Cl1 Cl 0.77506(4) 0.19108(3) -0.21995(3) 0.04467(11) Uani 1 1 d . . .
O1 O 1.02929(8) 0.36352(7) 0.22208(7) 0.0264(2) Uani 1 1 d . . .
O2 O 0.99006(9) -0.01922(8) 0.19204(9) 0.0336(2) Uani 1 1 d . . .
O3 O 0.95432(9) 0.12431(8) 0.36443(7) 0.0321(2) 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.94(13) . . ?
C3 C2 C1 119.46(13) . . ?
C4 C3 C2 121.03(14) . . ?
C4 C3 Cl1 119.70(12) . . ?
C2 C3 Cl1 119.24(12) . . ?
C3 C4 C5 119.11(14) . . ?
C4 C5 C6 121.29(13) . . ?
C5 C6 C1 118.11(13) . . ?
C5 C6 C7 120.26(11) . . ?
C1 C6 C7 121.59(11) . . ?
C8 C7 C6 112.93(10) . . ?
C8 C7 C13 111.78(10) . . ?
C6 C7 C13 110.03(10) . . ?
C9 C8 C12 108.29(11) . . ?
C9 C8 C7 130.78(11) . . ?
C12 C8 C7 120.92(10) . . ?
C8 C9 C10 113.79(10) . . ?
C9 C10 C11 103.81(10) . . ?
C12 C11 C10 105.27(10) . . ?
O1 C12 C8 125.24(11) . . ?
O1 C12 C11 126.23(11) . . ?
C8 C12 C11 108.53(10) . . ?
C21 C13 C7 110.46(10) . . ?
C21 C13 C14 107.60(10) . . ?
C7 C13 C14 108.78(9) . . ?
O2 C14 C15 120.72(11) . . ?
O2 C14 C13 118.31(11) . . ?
C15 C14 C13 120.96(10) . . ?
C16 C15 C20 119.18(12) . . ?
C16 C15 C14 123.42(11) . . ?
C20 C15 C14 117.40(11) . . ?
C17 C16 C15 120.13(12) . . ?
C18 C17 C16 120.24(13) . . ?
C17 C18 C19 119.96(13) . . ?
C20 C19 C18 120.34(14) . . ?
C19 C20 C15 120.15(13) . . ?
O3 C21 C22 121.18(13) . . ?
O3 C21 C13 120.26(12) . . ?
C22 C21 C13 118.55(11) . . ?
C27 C22 C23 119.34(13) . . ?
C27 C22 C21 118.28(13) . . ?
C23 C22 C21 122.33(13) . . ?
C24 C23 C22 119.75(15) . . ?
C25 C24 C23 120.32(17) . . ?
C24 C25 C26 120.49(15) . . ?
C25 C26 C27 120.12(17) . . ?
C26 C27 C22 119.95(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(2) . ?
C1 C6 1.3990(17) . ?
C2 C3 1.385(2) . ?
C3 C4 1.378(2) . ?
C3 Cl1 1.7388(16) . ?
C4 C5 1.393(2) . ?
C5 C6 1.3953(18) . ?
C6 C7 1.5227(18) . ?
C7 C8 1.5119(17) . ?
C7 C13 1.5417(16) . ?
C8 C9 1.3469(17) . ?
C8 C12 1.4756(16) . ?
C9 C10 1.4988(18) . ?
C10 C11 1.5296(17) . ?
C11 C12 1.5090(18) . ?
C12 O1 1.2211(14) . ?
C13 C21 1.5316(18) . ?
C13 C14 1.5423(16) . ?
C14 O2 1.2117(15) . ?
C14 C15 1.4912(17) . ?
C15 C16 1.3952(17) . ?
C15 C20 1.4023(18) . ?
C16 C17 1.3915(19) . ?
C17 C18 1.385(2) . ?
C18 C19 1.387(2) . ?
C19 C20 1.384(2) . ?
C21 O3 1.2146(16) . ?
C21 C22 1.4897(18) . ?
C22 C27 1.397(2) . ?
C22 C23 1.400(2) . ?
C23 C24 1.390(2) . ?
C24 C25 1.374(3) . ?
C25 C26 1.381(3) . ?
C26 C27 1.388(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25944040
