#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:17:11 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200620 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/71/1547101.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_1547101
loop_
_publ_author_name
'Huang, Wei-Lun'
'Raja, Arun'
'Hong, Bor-Cherng'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Acetalization-Reduction-Nef
 Reaction for a One-Pot Entry to the Functionalized Aflatoxin System.
 Total Synthesis of (-)- Dihydroaflatoxin D2 and (-)- and
 (+)-Microminutinin.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3494
_journal_page_last               3497
_journal_paper_doi               10.1021/acs.orglett.7b01473
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H11 Cl O3'
_chemical_formula_weight         226.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1106(4)
_cell_length_b                   9.3146(6)
_cell_length_c                   18.4160(11)
_cell_measurement_reflns_used    5129
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.21
_cell_measurement_theta_min      4.80
_cell_volume                     1048.20(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4088
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.964
_diffrn_reflns_theta_min         4.802
_exptl_absorpt_coefficient_mu    3.109
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.094(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.301
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0400
_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)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                1866
_reflns_number_total             1934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b01473_si_002.cif
_cod_data_source_block           ic17661
_cod_database_code               1547101
_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. 
;
_shelx_estimated_absorpt_t_min   0.305
_shelx_estimated_absorpt_t_max   0.860
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.14145(12) 0.29239(10) 0.06457(4) 0.0424(3) Uani 1 1 d . .
O1 O 0.7664(4) 0.2907(3) 0.41340(13) 0.0487(6) Uani 1 1 d . .
O2 O 0.8513(5) 0.1751(3) 0.31224(17) 0.0563(7) Uani 1 1 d . .
O3 O 0.8634(3) 0.4869(2) 0.24985(10) 0.0333(5) Uani 1 1 d . .
H3 H 0.9529 0.5372 0.2264 0.050 Uiso 1 1 calc R U
C1 C 0.7320(5) 0.2562(4) 0.34374(18) 0.0370(7) Uani 1 1 d . .
C2 C 0.5273(4) 0.3300(3) 0.31626(15) 0.0259(6) Uani 1 1 d . .
H2 H 0.4019 0.2632 0.3252 0.031 Uiso 1 1 calc R U
C3 C 0.5035(4) 0.4556(3) 0.36971(13) 0.0259(6) Uani 1 1 d . .
H3A H 0.6019 0.5354 0.3538 0.031 Uiso 1 1 calc R U
C4 C 0.5967(5) 0.3889(4) 0.43797(17) 0.0413(7) Uani 1 1 d . .
H4A H 0.6593 0.4637 0.4700 0.050 Uiso 1 1 calc R U
H4B H 0.4817 0.3365 0.4650 0.050 Uiso 1 1 calc R U
C5 C 0.5268(4) 0.3660(3) 0.23629(14) 0.0244(5) Uani 1 1 d . .
C6 C 0.3552(4) 0.3215(3) 0.19244(14) 0.0260(5) Uani 1 1 d . .
H6 H 0.2384 0.2674 0.2127 0.031 Uiso 1 1 calc R U
C7 C 0.3537(5) 0.3557(3) 0.11909(16) 0.0293(6) Uani 1 1 d . .
C8 C 0.5179(5) 0.4376(3) 0.08907(15) 0.0314(6) Uani 1 1 d . .
H8 H 0.5127 0.4632 0.0392 0.038 Uiso 1 1 calc R U
C9 C 0.6904(5) 0.4824(3) 0.13205(15) 0.0309(6) Uani 1 1 d . .
H9 H 0.8051 0.5381 0.1115 0.037 Uiso 1 1 calc R U
C10 C 0.6962(4) 0.4461(3) 0.20528(15) 0.0262(6) Uani 1 1 d . .
C11 C 0.2743(5) 0.5134(5) 0.37766(18) 0.0462(9) Uani 1 1 d . .
H11A H 0.1775 0.4370 0.3953 0.069 Uiso 1 1 calc R U
H11B H 0.2219 0.5476 0.3304 0.069 Uiso 1 1 calc R U
H11C H 0.2743 0.5930 0.4124 0.069 Uiso 1 1 calc R U
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'
Cl Cl 0.3639 0.7018 '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
C1 O1 C4 109.7(2)
C10 O3 H3 109.5
O2 C1 O1 121.2(3)
O2 C1 C2 128.8(3)
O1 C1 C2 110.0(3)
C5 C2 C1 115.4(2)
C5 C2 C3 117.1(2)
C1 C2 C3 102.1(2)
C5 C2 H2 107.2
C1 C2 H2 107.2
C3 C2 H2 107.2
C11 C3 C4 114.6(2)
C11 C3 C2 115.0(2)
C4 C3 C2 100.6(2)
C11 C3 H3A 108.8
C4 C3 H3A 108.8
C2 C3 H3A 108.8
O1 C4 C3 105.5(2)
O1 C4 H4A 110.6
C3 C4 H4A 110.6
O1 C4 H4B 110.6
C3 C4 H4B 110.6
H4A C4 H4B 108.8
C6 C5 C10 118.8(2)
C6 C5 C2 120.2(2)
C10 C5 C2 121.0(2)
C5 C6 C7 120.2(3)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 120.9(3)
C8 C7 Cl1 119.9(2)
C6 C7 Cl1 119.2(2)
C7 C8 C9 119.5(3)
C7 C8 H8 120.2
C9 C8 H8 120.2
C8 C9 C10 120.1(3)
C8 C9 H9 120.0
C10 C9 H9 120.0
O3 C10 C9 122.3(2)
O3 C10 C5 117.2(2)
C9 C10 C5 120.5(2)
C3 C11 H11A 109.5
C3 C11 H11B 109.5
H11A C11 H11B 109.5
C3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.743(3)
O1 C1 1.339(4)
O1 C4 1.455(4)
O2 C1 1.200(4)
O3 C10 1.364(3)
O3 H3 0.8400
C1 C2 1.514(4)
C2 C5 1.511(4)
C2 C3 1.536(4)
C2 H2 1.0000
C3 C11 1.508(4)
C3 C4 1.513(4)
C3 H3A 1.0000
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.387(4)
C5 C10 1.398(4)
C6 C7 1.388(4)
C6 H6 0.9500
C7 C8 1.376(4)
C8 C9 1.383(4)
C8 H8 0.9500
C9 C10 1.391(4)
C9 H9 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
_geom_hbond_site_symmetry_A
O3 H3 O2 0.84 1.89 2.724(3) 169.4 3_755
C3 H3A O3 1.00 2.53 3.130(3) 117.9 .
