# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7a
_database_code_depnum_ccdc_archive 'CCDC 1440383'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA12-7a
#==============================================================================
_audit_creation_date             'October 29 2013'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
'Ethyl 2-((3R*,4S*)-3-(1-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-oxochroman-4-yl)acetate'
_chemical_name_common            ?
_chemical_melting_point          90.0
_chemical_formula_moiety         'C25 H38 O5 Si'
_chemical_formula_sum            'C25 H38 O5 Si'
_chemical_formula_weight         446.64
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5246(7)
_cell_length_b                   7.1824(5)
_cell_length_c                   33.424(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7154(10)
_cell_angle_gamma                90.00
_cell_volume                     2518.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5017
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.52
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11783
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4464
_reflns_number_gt                3789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0447P)²+1.2637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4464
_refine_ls_number_parameters     355
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Si1 Si 0.48175(7) 0.39846(10) 0.18811(2) 0.0273(3) Uani 0.6635(18) 1 d P A 1
C16 C 0.3616(5) 0.2176(7) 0.17285(14) 0.0669(17) Uani 0.6635(18) 1 d P A 1
H16A H 0.3083 0.2605 0.1492 0.100 Uiso 0.6635(18) 1 calc PR A 1
H16B H 0.3079 0.1946 0.1949 0.100 Uiso 0.6635(18) 1 calc PR A 1
H16C H 0.4051 0.1022 0.1663 0.100 Uiso 0.6635(18) 1 calc PR A 1
C17 C 0.5925(5) 0.3365(9) 0.24035(17) 0.0336(12) Uani 0.6635(18) 1 d P A 1
H17A H 0.6134 0.2035 0.2408 0.050 Uiso 0.6635(18) 1 calc PR A 1
H17B H 0.5453 0.3671 0.2636 0.050 Uiso 0.6635(18) 1 calc PR A 1
H17C H 0.6714 0.4095 0.2414 0.050 Uiso 0.6635(18) 1 calc PR A 1
C18 C 0.4064(2) 0.6346(5) 0.19223(8) 0.0342(7) Uani 0.6635(18) 1 d PU A 1
C19 C 0.3365(11) 0.6939(12) 0.1514(3) 0.049(2) Uani 0.6635(18) 1 d PU A 1
H19A H 0.2690 0.6039 0.1436 0.073 Uiso 0.6635(18) 1 calc PR A 1
H19B H 0.3975 0.6976 0.1308 0.073 Uiso 0.6635(18) 1 calc PR A 1
H19C H 0.2989 0.8177 0.1541 0.073 Uiso 0.6635(18) 1 calc PR A 1
C20 C 0.3099(8) 0.6332(10) 0.2239(2) 0.059(2) Uani 0.6635(18) 1 d PU A 1
H20A H 0.3532 0.6011 0.2500 0.088 Uiso 0.6635(18) 1 calc PR A 1
H20B H 0.2435 0.5409 0.2165 0.088 Uiso 0.6635(18) 1 calc PR A 1
H20C H 0.2711 0.7568 0.2253 0.088 Uiso 0.6635(18) 1 calc PR A 1
C21 C 0.5102(3) 0.7792(4) 0.20426(10) 0.0464(8) Uani 0.6635(18) 1 d PU A 1
H21A H 0.4711 0.9022 0.2063 0.070 Uiso 0.6635(18) 1 calc PR A 1
H21B H 0.5720 0.7826 0.1839 0.070 Uiso 0.6635(18) 1 calc PR A 1
H21C H 0.5538 0.7450 0.2303 0.070 Uiso 0.6635(18) 1 calc PR A 1
O5 O 0.86611(9) 0.28193(14) -0.01716(3) 0.0195(2) Uani 1 1 d . . .
O4 O 0.92211(10) 0.20348(17) 0.04680(3) 0.0269(3) Uani 1 1 d . . .
O1 O 0.68693(10) 0.71974(14) 0.09017(3) 0.0234(3) Uani 1 1 d . . .
O2 O 0.51824(9) 0.55569(14) 0.06940(3) 0.0183(2) Uani 1 1 d . . .
C9 C 0.45356(13) 0.3850(2) 0.06745(4) 0.0163(3) Uani 1 1 d . . .
C23 C 0.84151(13) 0.24589(19) 0.02065(4) 0.0163(3) Uani 1 1 d . . .
O3 O 0.58616(11) 0.41641(15) 0.15277(3) 0.0258(3) Uani 1 1 d . . .
C4 C 0.52018(13) 0.2188(2) 0.06764(4) 0.0153(3) Uani 1 1 d . . .
C1 C 0.64161(13) 0.5665(2) 0.08605(4) 0.0166(3) Uani 1 1 d . A .
C8 C 0.32173(14) 0.3922(2) 0.06440(4) 0.0199(3) Uani 1 1 d . . .
H8 H 0.2784 0.5084 0.0636 0.024 Uiso 1 1 calc R . .
C3 C 0.66316(13) 0.22911(19) 0.06825(4) 0.0148(3) Uani 1 1 d . A .
H3 H 0.7006 0.1083 0.0783 0.018 Uiso 1 1 calc R . .
C6 C 0.31839(14) 0.0574(2) 0.06414(4) 0.0226(3) Uani 1 1 d . . .
H6 H 0.2718 -0.0560 0.0637 0.027 Uiso 1 1 calc R . .
C5 C 0.45128(14) 0.0536(2) 0.06631(4) 0.0190(3) Uani 1 1 d . . .
H5 H 0.4948 -0.0624 0.0669 0.023 Uiso 1 1 calc R . .
C24 C 0.99784(13) 0.2604(2) -0.02730(5) 0.0204(3) Uani 1 1 d . . .
H24A H 1.0313 0.1368 -0.0186 0.025 Uiso 1 1 calc R . .
H24B H 1.0526 0.3577 -0.0138 0.025 Uiso 1 1 calc R . .
C22 C 0.70036(13) 0.2626(2) 0.02527(4) 0.0179(3) Uani 1 1 d . . .
H22A H 0.6543 0.1719 0.0071 0.022 Uiso 1 1 calc R . .
H22B H 0.6718 0.3888 0.0166 0.022 Uiso 1 1 calc R . .
C7 C 0.25403(14) 0.2260(2) 0.06261(4) 0.0229(3) Uani 1 1 d . . .
H7 H 0.1635 0.2278 0.0603 0.027 Uiso 1 1 calc R . .
C2 C 0.71268(13) 0.38701(19) 0.09660(4) 0.0155(3) Uani 1 1 d . . .
H2 H 0.8039 0.4085 0.0916 0.019 Uiso 1 1 calc R A .
C14 C 0.86004(16) 0.0746(2) 0.14836(5) 0.0305(4) Uani 1 1 d U A .
H14A H 0.8756 0.0814 0.1196 0.037 Uiso 1 1 calc R . .
H14B H 0.8669 -0.0574 0.1568 0.037 Uiso 1 1 calc R . .
C10 C 0.70855(15) 0.3521(2) 0.14294(4) 0.0211(3) Uani 1 1 d U A .
C15 C 0.72637(15) 0.1462(2) 0.15409(4) 0.0229(3) Uani 1 1 d U . .
H15A H 0.7088 0.1289 0.1825 0.027 Uiso 1 1 calc R A .
H15B H 0.6636 0.0711 0.1373 0.027 Uiso 1 1 calc R . .
C11 C 0.81297(18) 0.4676(2) 0.16614(5) 0.0351(4) Uani 1 1 d U . .
H11A H 0.8072 0.5979 0.1565 0.042 Uiso 1 1 calc R A .
H11B H 0.7973 0.4680 0.1949 0.042 Uiso 1 1 calc R . .
C13 C 0.96019(19) 0.1896(3) 0.17292(6) 0.0450(5) Uani 1 1 d U . .
H13A H 1.0464 0.1449 0.1678 0.054 Uiso 1 1 calc R A .
H13B H 0.9494 0.1738 0.2019 0.054 Uiso 1 1 calc R . .
C25 C 0.99650(16) 0.2789(3) -0.07171(5) 0.0402(5) Uani 1 1 d . . .
H25A H 0.9430 0.1808 -0.0846 0.060 Uiso 1 1 calc R . .
H25B H 1.0836 0.2671 -0.0798 0.060 Uiso 1 1 calc R . .
H25C H 0.9620 0.4010 -0.0800 0.060 Uiso 1 1 calc R . .
C12 C 0.94758(18) 0.3953(3) 0.16178(6) 0.0452(5) Uani 1 1 d U A .
H12A H 0.9687 0.4125 0.1337 0.054 Uiso 1 1 calc R . .
H12B H 1.0092 0.4686 0.1793 0.054 Uiso 1 1 calc R . .
Si1B Si 0.55555(12) 0.49062(18) 0.19691(3) 0.0184(5) Uani 0.3365(18) 1 d P A 2
C16B C 0.6173(5) 0.7319(6) 0.20608(15) 0.0285(12) Uani 0.3365(18) 1 d P A 2
H16D H 0.7077 0.7266 0.2156 0.043 Uiso 0.3365(18) 1 calc PR A 2
H16E H 0.5693 0.7924 0.2264 0.043 Uiso 0.3365(18) 1 calc PR A 2
H16F H 0.6072 0.8032 0.1810 0.043 Uiso 0.3365(18) 1 calc PR A 2
C17B C 0.5471(8) 0.327(2) 0.2356(4) 0.034(2) Uani 0.3365(18) 1 d P A 2
H17D H 0.5517 0.2011 0.2245 0.051 Uiso 0.3365(18) 1 calc PR A 2
H17E H 0.4665 0.3423 0.2479 0.051 Uiso 0.3365(18) 1 calc PR A 2
H17F H 0.6185 0.3464 0.2559 0.051 Uiso 0.3365(18) 1 calc PR A 2
C18B C 0.3775(5) 0.4977(8) 0.18918(14) 0.0258(11) Uani 0.3365(18) 1 d PU A 2
C19B C 0.3261(6) 0.2989(10) 0.1762(2) 0.0264(15) Uani 0.3365(18) 1 d PU A 2
H19D H 0.2344 0.3060 0.1685 0.040 Uiso 0.3365(18) 1 calc PR A 2
H19E H 0.3417 0.2121 0.1987 0.040 Uiso 0.3365(18) 1 calc PR A 2
H19F H 0.3704 0.2548 0.1533 0.040 Uiso 0.3365(18) 1 calc PR A 2
C20B C 0.3351(17) 0.644(2) 0.1569(6) 0.025(2) Uani 0.3365(18) 1 d PU A 2
H20D H 0.2425 0.6366 0.1508 0.037 Uiso 0.3365(18) 1 calc PR A 2
H20E H 0.3778 0.6194 0.1325 0.037 Uiso 0.3365(18) 1 calc PR A 2
H20F H 0.3580 0.7687 0.1670 0.037 Uiso 0.3365(18) 1 calc PR A 2
C21B C 0.3175(16) 0.5570(15) 0.2286(5) 0.038(2) Uani 0.3365(18) 1 d PU A 2
H21D H 0.3526 0.6776 0.2377 0.057 Uiso 0.3365(18) 1 calc PR A 2
H21E H 0.3375 0.4632 0.2494 0.057 Uiso 0.3365(18) 1 calc PR A 2
H21F H 0.2248 0.5674 0.2233 0.057 Uiso 0.3365(18) 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Si1 O3 1.6831(12) . ?
Si1 C16 1.854(4) . ?
Si1 C18 1.882(3) . ?
Si1 C17 2.067(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.525(9) . ?
C18 C21 1.537(4) . ?
C18 C19 1.555(11) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O5 C23 1.3360(17) . ?
O5 C24 1.4623(17) . ?
O4 C23 1.2060(17) . ?
O1 C1 1.2029(17) . ?
O2 C1 1.3722(17) . ?
O2 C9 1.4014(17) . ?
C9 C8 1.384(2) . ?
C9 C4 1.384(2) . ?
C23 C22 1.5109(19) . ?
O3 C10 1.4318(19) . ?
O3 Si1B 1.6258(15) . ?
C4 C5 1.389(2) . ?
C4 C3 1.5051(19) . ?
C1 C2 1.5174(19) . ?
C8 C7 1.389(2) . ?
C8 H8 0.9500 . ?
C3 C22 1.5389(19) . ?
C3 C2 1.5409(19) . ?
C3 H3 1.0000 . ?
C6 C7 1.386(2) . ?
C6 C5 1.395(2) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C24 C25 1.489(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C7 H7 0.9500 . ?
C2 C10 1.5729(19) . ?
C2 H2 1.0000 . ?
C14 C15 1.525(2) . ?
C14 C13 1.525(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C10 C15 1.533(2) . ?
C10 C11 1.535(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 C12 1.527(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C12 1.527(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
Si1B C17B 1.754(14) . ?
Si1B C16B 1.867(5) . ?
Si1B C18B 1.871(5) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B C20B 1.544(16) . ?
C18B C21B 1.565(16) . ?
C18B C19B 1.575(9) . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?

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
O3 Si1 C16 109.29(14) . . ?
O3 Si1 C18 106.61(11) . . ?
C16 Si1 C18 111.7(2) . . ?
O3 Si1 C17 104.71(18) . . ?
C16 Si1 C17 114.0(2) . . ?
C18 Si1 C17 110.1(2) . . ?
C20 C18 C21 108.8(4) . . ?
C20 C18 C19 108.4(5) . . ?
C21 C18 C19 108.6(5) . . ?
C20 C18 Si1 110.7(3) . . ?
C21 C18 Si1 109.44(19) . . ?
C19 C18 Si1 110.8(4) . . ?
C23 O5 C24 117.38(11) . . ?
C1 O2 C9 120.55(11) . . ?
C8 C9 C4 122.50(13) . . ?
C8 C9 O2 116.78(13) . . ?
C4 C9 O2 120.70(12) . . ?
O4 C23 O5 123.72(13) . . ?
O4 C23 C22 125.80(13) . . ?
O5 C23 C22 110.47(11) . . ?
C10 O3 Si1B 124.27(10) . . ?
C10 O3 Si1 142.00(10) . . ?
Si1B O3 Si1 36.74(5) . . ?
C9 C4 C5 118.26(13) . . ?
C9 C4 C3 117.57(12) . . ?
C5 C4 C3 124.15(13) . . ?
O1 C1 O2 116.83(13) . . ?
O1 C1 C2 124.57(13) . . ?
O2 C1 C2 118.56(12) . . ?
C9 C8 C7 118.57(14) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C4 C3 C22 109.01(11) . . ?
C4 C3 C2 109.39(11) . . ?
C22 C3 C2 111.09(11) . . ?
C4 C3 H3 109.1 . . ?
C22 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C7 C6 C5 120.26(14) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C4 C5 C6 120.23(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O5 C24 C25 106.87(12) . . ?
O5 C24 H24A 110.3 . . ?
C25 C24 H24A 110.3 . . ?
O5 C24 H24B 110.3 . . ?
C25 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
C23 C22 C3 114.24(11) . . ?
C23 C22 H22A 108.7 . . ?
C3 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C3 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C6 C7 C8 120.12(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C1 C2 C3 110.31(11) . . ?
C1 C2 C10 108.13(11) . . ?
C3 C2 C10 116.93(11) . . ?
C1 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C10 C2 H2 107.0 . . ?
C15 C14 C13 110.73(15) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O3 C10 C15 110.47(12) . . ?
O3 C10 C11 109.27(13) . . ?
C15 C10 C11 109.29(13) . . ?
O3 C10 C2 105.83(11) . . ?
C15 C10 C2 112.34(12) . . ?
C11 C10 C2 109.56(12) . . ?
C14 C15 C10 112.98(13) . . ?
C14 C15 H15A 109.0 . . ?
C10 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C10 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C12 C11 C10 113.51(15) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C14 C13 C12 110.51(14) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 C12 C11 111.64(16) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O3 Si1B C17B 118.4(5) . . ?
O3 Si1B C16B 111.16(18) . . ?
C17B Si1B C16B 122.6(4) . . ?
O3 Si1B C18B 98.88(16) . . ?
C17B Si1B C18B 90.5(3) . . ?
C16B Si1B C18B 109.2(3) . . ?
Si1B C16B H16D 109.5 . . ?
Si1B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
Si1B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
Si1B C17B H17D 109.5 . . ?
Si1B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
Si1B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C20B C18B C21B 106.8(8) . . ?
C20B C18B C19B 110.6(8) . . ?
C21B C18B C19B 109.0(7) . . ?
C20B C18B Si1B 110.1(7) . . ?
C21B C18B Si1B 111.1(7) . . ?
C19B C18B Si1B 109.3(3) . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C20B H20D 109.5 . . ?
C18B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C18B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C18B C21B H21D 109.5 . . ?
C18B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C18B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anti-16b
_database_code_depnum_ccdc_archive 'CCDC 1440384'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA12-anti-16b
#==============================================================================
_audit_creation_date             'MAY 12 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((3S*,4S*)-6-bromo-2-oxo-3-((S*)-3-oxocycloheptyl)chroman-4-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          127
_chemical_formula_moiety         'C20 H23 Br O5'
_chemical_formula_sum            'C20 H23 Br O5'
_chemical_formula_weight         423.29
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1552(8)
_cell_length_b                   17.356(2)
_cell_length_c                   14.5825(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.177(2)
_cell_angle_gamma                90.00
_cell_volume                     1803.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3254
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.35
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.7535
_exptl_absorpt_correction_T_max  0.7854
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8683
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3188
_reflns_number_gt                2741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.4382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     236
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.72091(3) 0.906945(13) 0.495953(16) 0.01955(10) Uani 1 1 d . . .
C1 C 0.0011(3) 0.64356(13) 0.48884(14) 0.0143(5) Uani 1 1 d U . .
C2 C 0.1852(3) 0.60109(12) 0.48723(14) 0.0133(5) Uani 1 1 d U . .
H2 H 0.1720 0.5492 0.5157 0.016 Uiso 1 1 calc R . .
C3 C 0.3354(3) 0.64699(12) 0.54705(14) 0.0130(5) Uani 1 1 d U . .
H3 H 0.4605 0.6220 0.5433 0.016 Uiso 1 1 calc R . .
C4 C 0.3417(3) 0.72743(12) 0.50961(14) 0.0121(5) Uani 1 1 d U . .
C5 C 0.5062(3) 0.77092(13) 0.51309(14) 0.0134(5) Uani 1 1 d U . .
H5 H 0.6225 0.7492 0.5369 0.016 Uiso 1 1 calc R . .
C6 C 0.4978(3) 0.84610(13) 0.48134(15) 0.0140(5) Uani 1 1 d U . .
C7 C 0.3336(3) 0.87838(13) 0.44095(15) 0.0155(5) Uani 1 1 d U . .
H7 H 0.3325 0.9294 0.4172 0.019 Uiso 1 1 calc R . .
C8 C 0.1715(3) 0.83485(13) 0.43603(14) 0.0152(5) Uani 1 1 d U . .
H8 H 0.0571 0.8554 0.4081 0.018 Uiso 1 1 calc R . .
C9 C 0.1771(3) 0.76109(13) 0.47202(14) 0.0133(5) Uani 1 1 d U . .
C10 C 0.2295(3) 0.58978(12) 0.38551(15) 0.0126(5) Uani 1 1 d U . .
H10 H 0.2459 0.6416 0.3573 0.015 Uiso 1 1 calc R . .
C11 C 0.0609(3) 0.54942(14) 0.33289(15) 0.0201(5) Uani 1 1 d U . .
H11A H 0.0376 0.5009 0.3657 0.024 Uiso 1 1 calc R . .
H11B H -0.0506 0.5826 0.3369 0.024 Uiso 1 1 calc R . .
C12 C 0.0734(3) 0.53016(14) 0.23305(16) 0.0200(5) Uani 1 1 d U . .
C13 C 0.2148(4) 0.57040(15) 0.17960(16) 0.0233(6) Uani 1 1 d U . .
H13A H 0.2163 0.6260 0.1947 0.028 Uiso 1 1 calc R . .
H13B H 0.1779 0.5649 0.1128 0.028 Uiso 1 1 calc R . .
C14 C 0.4119(4) 0.53664(15) 0.20227(16) 0.0243(6) Uani 1 1 d U . .
H14A H 0.4022 0.4797 0.2012 0.029 Uiso 1 1 calc R . .
H14B H 0.4910 0.5519 0.1530 0.029 Uiso 1 1 calc R . .
C15 C 0.5098(3) 0.56064(14) 0.29345(16) 0.0218(5) Uani 1 1 d U . .
H15A H 0.5320 0.6169 0.2914 0.026 Uiso 1 1 calc R . .
H15B H 0.6342 0.5353 0.3004 0.026 Uiso 1 1 calc R . .
C16 C 0.4103(3) 0.54311(14) 0.37934(16) 0.0191(5) Uani 1 1 d U . .
H16A H 0.4973 0.5540 0.4345 0.023 Uiso 1 1 calc R . .
H16B H 0.3793 0.4875 0.3799 0.023 Uiso 1 1 calc R . .
C17 C 0.2890(3) 0.64781(13) 0.64859(15) 0.0174(5) Uani 1 1 d U . .
H17A H 0.1636 0.6712 0.6520 0.021 Uiso 1 1 calc R . .
H17B H 0.2835 0.5941 0.6710 0.021 Uiso 1 1 calc R . .
C18 C 0.4311(4) 0.69209(13) 0.71063(15) 0.0189(5) Uani 1 1 d U . .
C19 C 0.7568(4) 0.69792(15) 0.76502(17) 0.0293(6) Uani 1 1 d U . .
H19A H 0.8540 0.6585 0.7816 0.035 Uiso 1 1 calc R . .
H19B H 0.7094 0.7167 0.8227 0.035 Uiso 1 1 calc R . .
C20 C 0.8427(4) 0.76299(16) 0.71823(17) 0.0280(6) Uani 1 1 d U . .
H20A H 0.8810 0.7456 0.6588 0.042 Uiso 1 1 calc R . .
H20B H 0.9529 0.7816 0.7567 0.042 Uiso 1 1 calc R . .
H20C H 0.7511 0.8048 0.7083 0.042 Uiso 1 1 calc R . .
O1 O -0.1469(2) 0.61561(9) 0.50190(11) 0.0206(4) Uani 1 1 d U . .
O2 O 0.0048(2) 0.72156(9) 0.47107(10) 0.0149(3) Uani 1 1 d U . .
O3 O -0.0290(3) 0.48051(11) 0.19788(12) 0.0342(5) Uani 1 1 d U . .
O4 O 0.3954(3) 0.74699(10) 0.75697(11) 0.0273(4) Uani 1 1 d U . .
O5 O 0.6025(2) 0.66257(9) 0.70741(11) 0.0234(4) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Br1 C6 1.910(2) . ?
C1 O1 1.195(3) . ?
C1 O2 1.379(3) . ?
C1 C2 1.512(3) . ?
C2 C3 1.543(3) . ?
C2 C10 1.557(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.501(3) . ?
C3 C17 1.546(3) . ?
C3 H3 1.0000 . ?
C4 C9 1.383(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.410(3) . ?
C10 C11 1.539(3) . ?
C10 C16 1.536(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.504(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.214(3) . ?
C12 C13 1.504(4) . ?
C13 C14 1.535(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.509(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O4 1.209(3) . ?
C18 O5 1.334(3) . ?
C19 O5 1.460(3) . ?
C19 C20 1.481(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O1 C1 O2 117.4(2) . . ?
O1 C1 C2 126.2(2) . . ?
O2 C1 C2 116.36(19) . . ?
C1 C2 C3 107.63(18) . . ?
C1 C2 C10 109.20(18) . . ?
C3 C2 C10 114.35(18) . . ?
C1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C10 C2 H2 108.5 . . ?
C4 C3 C2 108.47(17) . . ?
C4 C3 C17 110.84(18) . . ?
C2 C3 C17 110.32(18) . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C17 C3 H3 109.1 . . ?
C9 C4 C5 118.1(2) . . ?
C9 C4 C3 119.0(2) . . ?
C5 C4 C3 122.9(2) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 Br1 118.25(17) . . ?
C7 C6 Br1 119.50(17) . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 122.4(2) . . ?
C8 C9 O2 116.8(2) . . ?
C4 C9 O2 120.7(2) . . ?
C11 C10 C16 110.93(18) . . ?
C11 C10 C2 108.33(18) . . ?
C16 C10 C2 111.55(18) . . ?
C11 C10 H10 108.7 . . ?
C16 C10 H10 108.7 . . ?
C2 C10 H10 108.7 . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11A 107.8 . . ?
C10 C11 H11A 107.8 . . ?
C12 C11 H11B 107.8 . . ?
C10 C11 H11B 107.8 . . ?
H11A C11 H11B 107.1 . . ?
O3 C12 C11 118.7(2) . . ?
O3 C12 C13 121.3(2) . . ?
C11 C12 C13 120.0(2) . . ?
C12 C13 C14 111.0(2) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 115.5(2) . . ?
C15 C14 H14A 108.4 . . ?
C13 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 117.1(2) . . ?
C14 C15 H15A 108.0 . . ?
C16 C15 H15A 108.0 . . ?
C14 C15 H15B 108.0 . . ?
C16 C15 H15B 108.0 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 C10 113.62(19) . . ?
C15 C16 H16A 108.8 . . ?
C10 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C10 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C3 112.80(19) . . ?
C18 C17 H17A 109.0 . . ?
C3 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C3 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O4 C18 O5 124.3(2) . . ?
O4 C18 C17 124.9(2) . . ?
O5 C18 C17 110.8(2) . . ?
O5 C19 C20 112.3(2) . . ?
O5 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
O5 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O2 C9 120.51(18) . . ?
C18 O5 C19 117.9(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.065

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anti-17a
_database_code_depnum_ccdc_archive 'CCDC 1440385'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA12-anti-17a
#==============================================================================
_audit_creation_date             'January 29 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((2S*,3'R*,4'S*)-2',4-dioxo-[2,3'-bichroman]-4'-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          86.0
_chemical_formula_moiety         'C22 H20 O6'
_chemical_formula_sum            'C22 H20 O6'
_chemical_formula_weight         380.38
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21    '
_symmetry_space_group_name_Hall  'P 2c -2ac '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   34.732(4)
_cell_length_b                   13.1317(14)
_cell_length_c                   8.2791(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3776.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5244
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.21
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            17978
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6383
_reflns_number_gt                5777
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.5188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_number_reflns         6383
_refine_ls_number_parameters     507
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.69170(5) 0.44787(14) 0.4077(3) 0.0185(4) Uani 1 1 d . . .
C2 C 0.70592(5) 0.47805(14) 0.5741(2) 0.0152(4) Uani 1 1 d . . .
H2 H 0.7343 0.4899 0.5677 0.018 Uiso 1 1 calc R . .
C3 C 0.69855(5) 0.39148(14) 0.6947(2) 0.0154(4) Uani 1 1 d . . .
H3 H 0.7055 0.4150 0.8058 0.019 Uiso 1 1 calc R . .
C4 C 0.65618(5) 0.36536(14) 0.6897(2) 0.0144(4) Uani 1 1 d . . .
C5 C 0.63475(6) 0.33597(14) 0.8243(3) 0.0192(4) Uani 1 1 d . . .
H5 H 0.6468 0.3322 0.9272 0.023 Uiso 1 1 calc R . .
C6 C 0.59600(6) 0.31215(15) 0.8090(3) 0.0220(5) Uani 1 1 d . . .
H6 H 0.5816 0.2918 0.9010 0.026 Uiso 1 1 calc R . .
C7 C 0.57837(6) 0.31813(15) 0.6592(3) 0.0253(5) Uani 1 1 d . . .
H7 H 0.5518 0.3022 0.6492 0.030 Uiso 1 1 calc R . .
C8 C 0.59903(6) 0.34697(15) 0.5244(3) 0.0223(5) Uani 1 1 d . . .
H8 H 0.5870 0.3506 0.4214 0.027 Uiso 1 1 calc R . .
C9 C 0.63748(6) 0.37035(14) 0.5426(2) 0.0177(4) Uani 1 1 d . . .
C10 C 0.68663(5) 0.57754(14) 0.6263(2) 0.0147(4) Uani 1 1 d . . .
H10 H 0.6585 0.5648 0.6413 0.018 Uiso 1 1 calc R . .
C11 C 0.69171(6) 0.66531(15) 0.5094(2) 0.0166(4) Uani 1 1 d . . .
H11A H 0.7195 0.6779 0.4914 0.020 Uiso 1 1 calc R . .
H11B H 0.6799 0.6478 0.4042 0.020 Uiso 1 1 calc R . .
C12 C 0.67303(5) 0.76010(15) 0.5763(2) 0.0165(4) Uani 1 1 d . . .
C13 C 0.67201(5) 0.76680(14) 0.7543(2) 0.0147(4) Uani 1 1 d . . .
C14 C 0.65668(5) 0.85291(14) 0.8305(3) 0.0178(4) Uani 1 1 d . . .
H14 H 0.6449 0.9050 0.7679 0.021 Uiso 1 1 calc R . .
C15 C 0.65858(5) 0.86237(15) 0.9964(3) 0.0196(5) Uani 1 1 d . . .
H15 H 0.6481 0.9207 1.0480 0.023 Uiso 1 1 calc R . .
C16 C 0.67599(6) 0.78591(15) 1.0880(3) 0.0210(5) Uani 1 1 d . . .
H16 H 0.6775 0.7929 1.2020 0.025 Uiso 1 1 calc R . .
C17 C 0.69107(6) 0.70019(15) 1.0148(2) 0.0188(4) Uani 1 1 d . . .
H17 H 0.7030 0.6487 1.0779 0.023 Uiso 1 1 calc R . .
C18 C 0.68861(5) 0.69000(14) 0.8481(2) 0.0155(4) Uani 1 1 d . . .
C19 C 0.72309(5) 0.29865(14) 0.6507(2) 0.0158(4) Uani 1 1 d . . .
H19A H 0.7141 0.2708 0.5461 0.019 Uiso 1 1 calc R . .
H19B H 0.7502 0.3203 0.6373 0.019 Uiso 1 1 calc R . .
C20 C 0.72116(5) 0.21655(14) 0.7763(2) 0.0145(4) Uani 1 1 d . . .
C21 C 0.73234(6) 0.04229(14) 0.8326(3) 0.0197(4) Uani 1 1 d . . .
H21A H 0.7063 0.0274 0.8750 0.024 Uiso 1 1 calc R . .
H21B H 0.7492 0.0614 0.9242 0.024 Uiso 1 1 calc R . .
C22 C 0.74833(6) -0.04955(14) 0.7472(3) 0.0244(5) Uani 1 1 d . . .
H22A H 0.7316 -0.0673 0.6562 0.037 Uiso 1 1 calc R . .
H22B H 0.7496 -0.1069 0.8227 0.037 Uiso 1 1 calc R . .
H22C H 0.7743 -0.0342 0.7072 0.037 Uiso 1 1 calc R . .
C1B C 0.56796(6) 0.98721(14) 0.5921(3) 0.0195(5) Uani 1 1 d . . .
C2B C 0.54955(5) 0.95297(14) 0.4345(2) 0.0153(4) Uani 1 1 d . . .
H2B H 0.5222 0.9335 0.4562 0.018 Uiso 1 1 calc R . .
C3B C 0.54999(5) 1.04096(14) 0.3126(2) 0.0148(4) Uani 1 1 d . . .
H3B H 0.5400 1.0165 0.2062 0.018 Uiso 1 1 calc R . .
C4B C 0.59107(5) 1.07513(14) 0.2940(3) 0.0180(4) Uani 1 1 d . . .
C5B C 0.60691(6) 1.10684(16) 0.1474(3) 0.0263(5) Uani 1 1 d . . .
H5B H 0.5915 1.1071 0.0528 0.032 Uiso 1 1 calc R . .
C6B C 0.64483(7) 1.13790(17) 0.1388(3) 0.0364(7) Uani 1 1 d . . .
H6B H 0.6553 1.1599 0.0387 0.044 Uiso 1 1 calc R . .
C7B C 0.66747(6) 1.13695(17) 0.2757(4) 0.0402(7) Uani 1 1 d . . .
H7B H 0.6935 1.1589 0.2693 0.048 Uiso 1 1 calc R . .
C8B C 0.65278(6) 1.10437(16) 0.4222(3) 0.0320(6) Uani 1 1 d . . .
H8B H 0.6684 1.1029 0.5162 0.038 Uiso 1 1 calc R . .
C9B C 0.61473(5) 1.07401(14) 0.4280(3) 0.0204(5) Uani 1 1 d . . .
C10B C 0.57138(5) 0.85876(15) 0.3752(2) 0.0149(4) Uani 1 1 d . . .
H10B H 0.5993 0.8762 0.3637 0.018 Uiso 1 1 calc R . .
C11B C 0.56744(6) 0.76903(15) 0.4896(2) 0.0179(4) Uani 1 1 d . . .
H11C H 0.5794 0.7864 0.5946 0.022 Uiso 1 1 calc R . .
H11D H 0.5398 0.7549 0.5087 0.022 Uiso 1 1 calc R . .
C12B C 0.58634(5) 0.67578(14) 0.4223(3) 0.0166(4) Uani 1 1 d . . .
C13B C 0.58707(5) 0.66869(14) 0.2454(2) 0.0144(4) Uani 1 1 d . . .
C14B C 0.60204(5) 0.58244(15) 0.1681(2) 0.0183(4) Uani 1 1 d . . .
H14B H 0.6128 0.5290 0.2309 0.022 Uiso 1 1 calc R . .
C15B C 0.60131(5) 0.57402(16) 0.0027(3) 0.0200(4) Uani 1 1 d . . .
H15B H 0.6114 0.5151 -0.0488 0.024 Uiso 1 1 calc R . .
C16B C 0.58555(5) 0.65336(15) -0.0891(3) 0.0197(4) Uani 1 1 d . . .
H16B H 0.5850 0.6479 -0.2035 0.024 Uiso 1 1 calc R . .
C17B C 0.57084(5) 0.73938(16) -0.0157(2) 0.0171(4) Uani 1 1 d . . .
H17B H 0.5604 0.7930 -0.0790 0.020 Uiso 1 1 calc R . .
C18B C 0.57154(5) 0.74667(14) 0.1518(2) 0.0146(4) Uani 1 1 d . . .
C19B C 0.52437(5) 1.12832(14) 0.3752(2) 0.0169(4) Uani 1 1 d . . .
H19C H 0.4982 1.1018 0.3964 0.020 Uiso 1 1 calc R . .
H19D H 0.5350 1.1538 0.4787 0.020 Uiso 1 1 calc R . .
C20B C 0.52181(5) 1.21507(15) 0.2573(3) 0.0170(4) Uani 1 1 d . . .
C21B C 0.51243(6) 1.39387(14) 0.2337(3) 0.0239(5) Uani 1 1 d . . .
H21C H 0.4895 1.3871 0.1635 0.029 Uiso 1 1 calc R . .
H21D H 0.5354 1.4026 0.1643 0.029 Uiso 1 1 calc R . .
C22B C 0.50796(6) 1.48400(16) 0.3450(3) 0.0283(5) Uani 1 1 d . . .
H22D H 0.4850 1.4746 0.4124 0.042 Uiso 1 1 calc R . .
H22E H 0.5052 1.5462 0.2807 0.042 Uiso 1 1 calc R . .
H22F H 0.5308 1.4897 0.4141 0.042 Uiso 1 1 calc R . .
O1 O 0.70782(4) 0.46573(11) 0.28281(16) 0.0245(3) Uani 1 1 d . . .
O2 O 0.65726(4) 0.39780(10) 0.40045(16) 0.0197(3) Uani 1 1 d . . .
O3 O 0.66046(4) 0.82695(10) 0.48843(16) 0.0213(3) Uani 1 1 d . . .
O4 O 0.70334(4) 0.60323(10) 0.78130(16) 0.0177(3) Uani 1 1 d . . .
O5 O 0.71321(4) 0.23017(10) 0.91690(16) 0.0189(3) Uani 1 1 d . . .
O6 O 0.73060(4) 0.12508(9) 0.71513(16) 0.0168(3) Uani 1 1 d . . .
O1B O 0.55626(4) 0.96727(11) 0.72483(18) 0.0295(4) Uani 1 1 d . . .
O2B O 0.60063(4) 1.04413(10) 0.58005(18) 0.0230(3) Uani 1 1 d . . .
O3B O 0.59919(4) 0.60862(10) 0.51072(16) 0.0208(3) Uani 1 1 d . . .
O4B O 0.55608(4) 0.83331(10) 0.21840(15) 0.0163(3) Uani 1 1 d . . .
O5B O 0.52358(4) 1.20758(10) 0.11231(17) 0.0234(3) Uani 1 1 d . . .
O6B O 0.51667(4) 1.30409(9) 0.33468(17) 0.0201(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 O1 1.199(2) . ?
C1 O2 1.366(2) . ?
C1 C2 1.517(3) . ?
C2 C10 1.531(3) . ?
C2 C3 1.534(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(2) . ?
C3 C19 1.531(2) . ?
C3 H3 1.0000 . ?
C4 C9 1.381(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.410(2) . ?
C10 O4 1.449(2) . ?
C10 C11 1.515(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.221(2) . ?
C12 C13 1.477(3) . ?
C13 C18 1.397(3) . ?
C13 C14 1.400(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 O4 1.366(2) . ?
C19 C20 1.499(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O5 1.209(2) . ?
C20 O6 1.344(2) . ?
C21 O6 1.460(2) . ?
C21 C22 1.504(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1B O1B 1.201(3) . ?
C1B O2B 1.363(2) . ?
C1B C2B 1.521(3) . ?
C2B C10B 1.532(3) . ?
C2B C3B 1.534(3) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.504(3) . ?
C3B C19B 1.541(3) . ?
C3B H3B 1.0000 . ?
C4B C9B 1.380(3) . ?
C4B C5B 1.396(3) . ?
C5B C6B 1.381(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.380(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.383(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.381(3) . ?
C8B H8B 0.9500 . ?
C9B O2B 1.407(2) . ?
C10B O4B 1.442(2) . ?
C10B C11B 1.518(3) . ?
C10B H10B 1.0000 . ?
C11B C12B 1.497(3) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B O3B 1.230(2) . ?
C12B C13B 1.468(3) . ?
C13B C18B 1.393(3) . ?
C13B C14B 1.401(3) . ?
C14B C15B 1.374(3) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.401(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.381(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.390(3) . ?
C17B H17B 0.9500 . ?
C18B O4B 1.374(2) . ?
C19B C20B 1.503(3) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B O5B 1.206(2) . ?
C20B O6B 1.345(2) . ?
C21B O6B 1.453(2) . ?
C21B C22B 1.508(3) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?

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
O1 C1 O2 117.74(19) . . ?
O1 C1 C2 125.47(17) . . ?
O2 C1 C2 116.78(17) . . ?
C1 C2 C10 109.68(15) . . ?
C1 C2 C3 110.08(16) . . ?
C10 C2 C3 112.06(15) . . ?
C1 C2 H2 108.3 . . ?
C10 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C4 C3 C19 110.77(15) . . ?
C4 C3 C2 108.22(15) . . ?
C19 C3 C2 110.01(15) . . ?
C4 C3 H3 109.3 . . ?
C19 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C9 C4 C5 117.81(17) . . ?
C9 C4 C3 118.12(17) . . ?
C5 C4 C3 124.08(18) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 120.67(18) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C4 122.80(19) . . ?
C8 C9 O2 115.93(18) . . ?
C4 C9 O2 121.25(16) . . ?
O4 C10 C11 110.01(15) . . ?
O4 C10 C2 105.87(15) . . ?
C11 C10 C2 114.71(16) . . ?
O4 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C2 C10 H10 108.7 . . ?
C12 C11 C10 110.04(16) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O3 C12 C13 122.91(18) . . ?
O3 C12 C11 121.86(19) . . ?
C13 C12 C11 115.21(17) . . ?
C18 C13 C14 119.30(18) . . ?
C18 C13 C12 120.11(18) . . ?
C14 C13 C12 120.46(18) . . ?
C15 C14 C13 120.19(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.77(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.41(19) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
O4 C18 C17 117.36(17) . . ?
O4 C18 C13 122.11(18) . . ?
C17 C18 C13 120.52(18) . . ?
C20 C19 C3 112.50(15) . . ?
C20 C19 H19A 109.1 . . ?
C3 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C3 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
O5 C20 O6 123.40(18) . . ?
O5 C20 C19 124.84(18) . . ?
O6 C20 C19 111.72(16) . . ?
O6 C21 C22 107.44(17) . . ?
O6 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O6 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1B C1B O2B 117.92(19) . . ?
O1B C1B C2B 125.36(19) . . ?
O2B C1B C2B 116.71(17) . . ?
C1B C2B C10B 107.79(15) . . ?
C1B C2B C3B 109.72(15) . . ?
C10B C2B C3B 113.15(16) . . ?
C1B C2B H2B 108.7 . . ?
C10B C2B H2B 108.7 . . ?
C3B C2B H2B 108.7 . . ?
C4B C3B C2B 107.55(15) . . ?
C4B C3B C19B 111.10(15) . . ?
C2B C3B C19B 109.50(15) . . ?
C4B C3B H3B 109.6 . . ?
C2B C3B H3B 109.6 . . ?
C19B C3B H3B 109.6 . . ?
C9B C4B C5B 117.84(18) . . ?
C9B C4B C3B 118.64(18) . . ?
C5B C4B C3B 123.51(19) . . ?
C6B C5B C4B 120.6(2) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C7B C6B C5B 119.9(2) . . ?
C7B C6B H6B 120.1 . . ?
C5B C6B H6B 120.1 . . ?
C8B C7B C6B 120.8(2) . . ?
C8B C7B H7B 119.6 . . ?
C6B C7B H7B 119.6 . . ?
C7B C8B C9B 118.2(2) . . ?
C7B C8B H8B 120.9 . . ?
C9B C8B H8B 120.9 . . ?
C4B C9B C8B 122.6(2) . . ?
C4B C9B O2B 120.99(16) . . ?
C8B C9B O2B 116.4(2) . . ?
O4B C10B C11B 110.40(16) . . ?
O4B C10B C2B 107.05(15) . . ?
C11B C10B C2B 112.50(16) . . ?
O4B C10B H10B 108.9 . . ?
C11B C10B H10B 108.9 . . ?
C2B C10B H10B 108.9 . . ?
C12B C11B C10B 111.29(16) . . ?
C12B C11B H11C 109.4 . . ?
C10B C11B H11C 109.4 . . ?
C12B C11B H11D 109.4 . . ?
C10B C11B H11D 109.4 . . ?
H11C C11B H11D 108.0 . . ?
O3B C12B C13B 122.84(18) . . ?
O3B C12B C11B 121.59(19) . . ?
C13B C12B C11B 115.53(17) . . ?
C18B C13B C14B 118.95(18) . . ?
C18B C13B C12B 120.13(18) . . ?
C14B C13B C12B 120.89(17) . . ?
C15B C14B C13B 120.89(19) . . ?
C15B C14B H14B 119.6 . . ?
C13B C14B H14B 119.6 . . ?
C14B C15B C16B 119.20(19) . . ?
C14B C15B H15B 120.4 . . ?
C16B C15B H15B 120.4 . . ?
C17B C16B C15B 120.9(2) . . ?
C17B C16B H16B 119.5 . . ?
C15B C16B H16B 119.5 . . ?
C16B C17B C18B 119.3(2) . . ?
C16B C17B H17B 120.4 . . ?
C18B C17B H17B 120.4 . . ?
O4B C18B C17B 116.79(17) . . ?
O4B C18B C13B 122.47(17) . . ?
C17B C18B C13B 120.74(19) . . ?
C20B C19B C3B 112.33(16) . . ?
C20B C19B H19C 109.1 . . ?
C3B C19B H19C 109.1 . . ?
C20B C19B H19D 109.1 . . ?
C3B C19B H19D 109.1 . . ?
H19C C19B H19D 107.9 . . ?
O5B C20B O6B 123.48(18) . . ?
O5B C20B C19B 125.57(18) . . ?
O6B C20B C19B 110.94(17) . . ?
O6B C21B C22B 107.21(18) . . ?
O6B C21B H21C 110.3 . . ?
C22B C21B H21C 110.3 . . ?
O6B C21B H21D 110.3 . . ?
C22B C21B H21D 110.3 . . ?
H21C C21B H21D 108.5 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C1 O2 C9 120.88(15) . . ?
C18 O4 C10 113.77(14) . . ?
C20 O6 C21 115.12(14) . . ?
C1B O2B C9B 120.55(15) . . ?
C18B O4B C10B 114.16(14) . . ?
C20B O6B C21B 116.41(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anti-18a
_database_code_depnum_ccdc_archive 'CCDC 1440386'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA-anti-18a
#==============================================================================
_audit_creation_date             'July 16 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((2R*,3R*,3'R*,4'S*)-3-bromo-3-methyl-2',4-dioxo-[2,3'-bichroman]-4'-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          149
_chemical_formula_moiety         'C23 H21 Br O6'
_chemical_formula_sum            'C23 H21 Br O6'
_chemical_formula_weight         473.31
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6704(12)
_cell_length_b                   9.7676(9)
_cell_length_c                   16.2166(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0590(10)
_cell_angle_gamma                90.00
_cell_volume                     1991.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2685
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.50
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    2.103
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.8016
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3501
_reflns_number_gt                2887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0271P)²+0.6580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3501
_refine_ls_number_parameters     273
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.115716(18) 0.31604(3) 0.350347(14) 0.01770(8) Uani 1 1 d . . .
C1 C 0.49305(18) 0.2762(2) 0.51721(14) 0.0107(5) Uani 1 1 d U . .
C2 C 0.39083(17) 0.3499(2) 0.53167(13) 0.0094(5) Uani 1 1 d U . .
H2 H 0.4024 0.4492 0.5207 0.011 Uiso 1 1 calc R . .
C3 C 0.36218(17) 0.3400(2) 0.62147(13) 0.0109(5) Uani 1 1 d U . .
H3 H 0.2829 0.3459 0.6173 0.013 Uiso 1 1 calc R . .
C4 C 0.39244(17) 0.2018(2) 0.65913(14) 0.0120(5) Uani 1 1 d U . .
C5 C 0.34364(19) 0.1486(2) 0.72493(14) 0.0161(6) Uani 1 1 d U . .
H5 H 0.2910 0.2014 0.7474 0.019 Uiso 1 1 calc R . .
C6 C 0.37006(19) 0.0213(3) 0.75796(15) 0.0194(6) Uani 1 1 d U . .
H6 H 0.3364 -0.0122 0.8031 0.023 Uiso 1 1 calc R . .
C7 C 0.44587(19) -0.0582(3) 0.72525(15) 0.0192(6) Uani 1 1 d U . .
H7 H 0.4638 -0.1462 0.7478 0.023 Uiso 1 1 calc R . .
C8 C 0.49532(18) -0.0086(2) 0.65942(14) 0.0157(6) Uani 1 1 d U . .
H8 H 0.5471 -0.0621 0.6364 0.019 Uiso 1 1 calc R . .
C9 C 0.46784(17) 0.1202(2) 0.62802(14) 0.0120(5) Uani 1 1 d U . .
C10 C 0.40583(17) 0.4604(2) 0.67634(14) 0.0117(5) Uani 1 1 d U . .
H10A H 0.3780 0.5468 0.6501 0.014 Uiso 1 1 calc R . .
H10B H 0.3786 0.4529 0.7308 0.014 Uiso 1 1 calc R . .
C11 C 0.52571(18) 0.4688(2) 0.69083(14) 0.0120(5) Uani 1 1 d U . .
C12 C 0.67242(18) 0.5630(3) 0.78064(15) 0.0174(6) Uani 1 1 d U . .
H12A H 0.7112 0.5462 0.7322 0.021 Uiso 1 1 calc R . .
H12B H 0.6975 0.4964 0.8248 0.021 Uiso 1 1 calc R . .
C13 C 0.6919(2) 0.7065(3) 0.81182(17) 0.0242(6) Uani 1 1 d U . .
H13A H 0.6705 0.7713 0.7667 0.036 Uiso 1 1 calc R . .
H13B H 0.7677 0.7184 0.8312 0.036 Uiso 1 1 calc R . .
H13C H 0.6503 0.7235 0.8579 0.036 Uiso 1 1 calc R . .
C14 C 0.30604(17) 0.2985(2) 0.46098(14) 0.0113(5) Uani 1 1 d U . .
H14 H 0.3322 0.3276 0.4079 0.014 Uiso 1 1 calc R . .
C15 C 0.19597(18) 0.3643(2) 0.46025(14) 0.0116(5) Uani 1 1 d U . .
C16 C 0.12882(17) 0.2951(2) 0.52106(14) 0.0122(5) Uani 1 1 d U . .
C17 C 0.14903(17) 0.1487(2) 0.53616(14) 0.0111(5) Uani 1 1 d U . .
C18 C 0.08413(18) 0.0715(3) 0.58242(14) 0.0143(5) Uani 1 1 d U . .
H18 H 0.0266 0.1145 0.6047 0.017 Uiso 1 1 calc R . .
C19 C 0.10264(19) -0.0656(3) 0.59597(14) 0.0171(6) Uani 1 1 d U . .
H19 H 0.0577 -0.1175 0.6269 0.020 Uiso 1 1 calc R . .
C20 C 0.1881(2) -0.1283(3) 0.56390(15) 0.0181(6) Uani 1 1 d U . .
H20 H 0.2012 -0.2231 0.5735 0.022 Uiso 1 1 calc R . .
C21 C 0.25383(18) -0.0544(2) 0.51848(14) 0.0145(5) Uani 1 1 d U . .
H21 H 0.3115 -0.0978 0.4967 0.017 Uiso 1 1 calc R . .
C22 C 0.23452(17) 0.0840(2) 0.50501(13) 0.0106(5) Uani 1 1 d U . .
C23 C 0.19903(19) 0.5184(2) 0.46763(16) 0.0183(6) Uani 1 1 d U . .
H23A H 0.1263 0.5545 0.4598 0.027 Uiso 1 1 calc R . .
H23B H 0.2392 0.5566 0.4251 0.027 Uiso 1 1 calc R . .
H23C H 0.2335 0.5443 0.5228 0.027 Uiso 1 1 calc R . .
O1 O 0.54560(12) 0.30906(16) 0.46349(9) 0.0141(4) Uani 1 1 d U . .
O2 O 0.52229(12) 0.16236(15) 0.56224(9) 0.0134(4) Uani 1 1 d U . .
O3 O 0.58451(12) 0.41367(17) 0.64807(10) 0.0179(4) Uani 1 1 d U . .
O4 O 0.55746(12) 0.54764(17) 0.75656(9) 0.0175(4) Uani 1 1 d U . .
O5 O 0.06390(13) 0.36149(17) 0.55459(10) 0.0177(4) Uani 1 1 d U . .
O6 O 0.30236(12) 0.15132(15) 0.45831(9) 0.0115(4) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Br1 C15 1.997(2) . ?
C1 O1 1.203(3) . ?
C1 O2 1.357(3) . ?
C1 C2 1.525(3) . ?
C2 C3 1.547(3) . ?
C2 C14 1.555(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.511(3) . ?
C3 C10 1.536(3) . ?
C3 H3 1.0000 . ?
C4 C9 1.386(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.402(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.205(3) . ?
C11 O4 1.336(3) . ?
C12 O4 1.469(3) . ?
C12 C13 1.500(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O6 1.439(3) . ?
C14 C15 1.534(3) . ?
C14 H14 1.0000 . ?
C15 C23 1.511(3) . ?
C15 C16 1.536(3) . ?
C16 O5 1.226(3) . ?
C16 C17 1.469(3) . ?
C17 C18 1.399(3) . ?
C17 C22 1.401(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 O6 1.380(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
O1 C1 O2 118.0(2) . . ?
O1 C1 C2 122.8(2) . . ?
O2 C1 C2 119.0(2) . . ?
C1 C2 C3 114.67(18) . . ?
C1 C2 C14 104.92(17) . . ?
C3 C2 C14 116.95(18) . . ?
C1 C2 H2 106.5 . . ?
C3 C2 H2 106.5 . . ?
C14 C2 H2 106.5 . . ?
C4 C3 C10 113.24(18) . . ?
C4 C3 C2 111.04(18) . . ?
C10 C3 C2 112.83(19) . . ?
C4 C3 H3 106.4 . . ?
C10 C3 H3 106.4 . . ?
C2 C3 H3 106.4 . . ?
C9 C4 C5 117.0(2) . . ?
C9 C4 C3 121.2(2) . . ?
C5 C4 C3 121.8(2) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C4 122.8(2) . . ?
C8 C9 O2 114.9(2) . . ?
C4 C9 O2 122.3(2) . . ?
C11 C10 C3 114.53(19) . . ?
C11 C10 H10A 108.6 . . ?
C3 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C3 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O3 C11 O4 124.7(2) . . ?
O3 C11 C10 124.5(2) . . ?
O4 C11 C10 110.72(19) . . ?
O4 C12 C13 107.58(19) . . ?
O4 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O4 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 C15 113.08(18) . . ?
O6 C14 C2 111.19(17) . . ?
C15 C14 C2 114.57(18) . . ?
O6 C14 H14 105.7 . . ?
C15 C14 H14 105.7 . . ?
C2 C14 H14 105.7 . . ?
C23 C15 C14 113.72(19) . . ?
C23 C15 C16 113.5(2) . . ?
C14 C15 C16 112.69(19) . . ?
C23 C15 Br1 108.13(15) . . ?
C14 C15 Br1 105.72(15) . . ?
C16 C15 Br1 101.99(14) . . ?
O5 C16 C17 123.6(2) . . ?
O5 C16 C15 120.5(2) . . ?
C17 C16 C15 115.9(2) . . ?
C18 C17 C22 118.8(2) . . ?
C18 C17 C16 120.8(2) . . ?
C22 C17 C16 120.4(2) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
O6 C22 C21 116.2(2) . . ?
O6 C22 C17 123.0(2) . . ?
C21 C22 C17 120.8(2) . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 O2 C9 121.54(18) . . ?
C11 O4 C12 117.55(18) . . ?
C22 O6 C14 118.64(17) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.065

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-14a
_database_code_depnum_ccdc_archive 'CCDC 1440387'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA-syn-14a
#==============================================================================
_audit_creation_date             'April 21 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((3S*,4S*)-2-oxo-3-((R*)-3-oxocyclopentyl)chroman-4-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          89.0
_chemical_formula_moiety         'C18 H20 O5'
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21    '
_symmetry_space_group_name_Hall  'P 2c -2ac '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   25.583(3)
_cell_length_b                   6.8787(8)
_cell_length_c                   17.4038(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3062.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5810
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.47
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14062
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4775
_reflns_number_gt                4424
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.7653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(7)
_refine_ls_number_reflns         4775
_refine_ls_number_parameters     417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.73598(7) 0.7824(3) 0.31943(12) 0.0144(4) Uani 1 1 d . . .
C2 C 0.66491(8) 0.6192(3) 0.38420(12) 0.0133(4) Uani 1 1 d . . .
C3 C 0.62876(8) 0.6398(3) 0.44243(12) 0.0175(5) Uani 1 1 d . . .
H3 H 0.6214 0.7640 0.4637 0.021 Uiso 1 1 calc R . .
C4 C 0.60342(8) 0.4750(3) 0.46918(12) 0.0195(5) Uani 1 1 d . . .
H4 H 0.5785 0.4857 0.5095 0.023 Uiso 1 1 calc R . .
C5 C 0.61421(8) 0.2943(3) 0.43739(13) 0.0175(5) Uani 1 1 d . . .
H5 H 0.5968 0.1818 0.4560 0.021 Uiso 1 1 calc R . .
C6 C 0.65046(8) 0.2779(3) 0.37839(12) 0.0147(4) Uani 1 1 d . . .
H6 H 0.6577 0.1539 0.3568 0.018 Uiso 1 1 calc R . .
C7 C 0.67627(7) 0.4419(3) 0.35049(11) 0.0123(4) Uani 1 1 d . . .
C8 C 0.71590(8) 0.4388(3) 0.28614(12) 0.0132(4) Uani 1 1 d . . .
H8 H 0.7311 0.3053 0.2815 0.016 Uiso 1 1 calc R . .
C9 C 0.75935(8) 0.5832(3) 0.30727(12) 0.0129(4) Uani 1 1 d . . .
H9 H 0.7846 0.5904 0.2635 0.015 Uiso 1 1 calc R . .
C10 C 0.78934(8) 0.5244(3) 0.38009(12) 0.0139(4) Uani 1 1 d . . .
H10 H 0.7647 0.5288 0.4246 0.017 Uiso 1 1 calc R . .
C11 C 0.83729(8) 0.6521(3) 0.39923(12) 0.0163(4) Uani 1 1 d . . .
H11A H 0.8592 0.6743 0.3531 0.020 Uiso 1 1 calc R . .
H11B H 0.8265 0.7791 0.4208 0.020 Uiso 1 1 calc R . .
C12 C 0.86634(8) 0.5300(3) 0.45910(13) 0.0192(5) Uani 1 1 d . . .
H12A H 0.9042 0.5592 0.4584 0.023 Uiso 1 1 calc R . .
H12B H 0.8526 0.5552 0.5113 0.023 Uiso 1 1 calc R . .
C13 C 0.85622(8) 0.3219(3) 0.43526(12) 0.0177(5) Uani 1 1 d . . .
C14 C 0.81305(8) 0.3208(3) 0.37576(12) 0.0163(4) Uani 1 1 d . . .
H14A H 0.7866 0.2206 0.3880 0.020 Uiso 1 1 calc R . .
H14B H 0.8273 0.2950 0.3239 0.020 Uiso 1 1 calc R . .
C15 C 0.69095(8) 0.4978(3) 0.20900(12) 0.0145(4) Uani 1 1 d . . .
H15A H 0.6738 0.6257 0.2156 0.017 Uiso 1 1 calc R . .
H15B H 0.7192 0.5142 0.1706 0.017 Uiso 1 1 calc R . .
C16 C 0.65114(8) 0.3563(3) 0.17705(12) 0.0149(4) Uani 1 1 d . . .
C17 C 0.63465(8) 0.0215(3) 0.15130(13) 0.0186(5) Uani 1 1 d . . .
H17A H 0.6560 -0.0908 0.1346 0.022 Uiso 1 1 calc R . .
H17B H 0.6160 0.0730 0.1058 0.022 Uiso 1 1 calc R . .
C017 C 0.71233(8) -0.1219(3) 0.58926(12) 0.0171(4) Uani 1 1 d . . .
H01A H 0.7339 -0.1579 0.6343 0.021 Uiso 1 1 calc R . .
H01B H 0.6994 -0.2417 0.5641 0.021 Uiso 1 1 calc R . .
C18 C 0.59549(9) -0.0444(3) 0.21011(14) 0.0220(5) Uani 1 1 d . . .
H18A H 0.6136 -0.0773 0.2580 0.033 Uiso 1 1 calc R . .
H18B H 0.5769 -0.1591 0.1909 0.033 Uiso 1 1 calc R . .
H18C H 0.5704 0.0603 0.2198 0.033 Uiso 1 1 calc R . .
C1B C 0.61109(8) -0.2485(3) 0.66856(12) 0.0145(4) Uani 1 1 d . . .
C2B C 0.54096(8) -0.0699(3) 0.60857(12) 0.0144(4) Uani 1 1 d . . .
C3B C 0.50396(8) -0.0763(3) 0.55084(12) 0.0177(5) Uani 1 1 d . . .
H3B H 0.4964 -0.1947 0.5250 0.021 Uiso 1 1 calc R . .
C4B C 0.47801(9) 0.0936(3) 0.53125(12) 0.0193(5) Uani 1 1 d . . .
H4B H 0.4522 0.0917 0.4921 0.023 Uiso 1 1 calc R . .
C5B C 0.48967(8) 0.2662(3) 0.56873(13) 0.0177(5) Uani 1 1 d . . .
H5B H 0.4720 0.3825 0.5548 0.021 Uiso 1 1 calc R . .
C6B C 0.52712(8) 0.2694(3) 0.62659(12) 0.0136(4) Uani 1 1 d . . .
H6B H 0.5350 0.3881 0.6519 0.016 Uiso 1 1 calc R . .
C7B C 0.55318(7) 0.1004(3) 0.64764(12) 0.0132(4) Uani 1 1 d . . .
C8B C 0.59424(8) 0.0916(3) 0.70970(12) 0.0121(4) Uani 1 1 d . . .
H8B H 0.6105 0.2230 0.7154 0.014 Uiso 1 1 calc R . .
C9B C 0.63642(8) -0.0543(3) 0.68442(12) 0.0138(4) Uani 1 1 d . . .
H9B H 0.6618 -0.0708 0.7276 0.017 Uiso 1 1 calc R . .
C10B C 0.66670(8) 0.0118(3) 0.61276(12) 0.0130(4) Uani 1 1 d . . .
H10B H 0.6417 0.0208 0.5687 0.016 Uiso 1 1 calc R . .
C11B C 0.74328(9) 0.0041(3) 0.53290(12) 0.0185(5) Uani 1 1 d . . .
H11C H 0.7806 -0.0336 0.5324 0.022 Uiso 1 1 calc R . .
H11D H 0.7291 -0.0079 0.4802 0.022 Uiso 1 1 calc R . .
C12B C 0.73660(8) 0.2084(3) 0.56292(12) 0.0179(5) Uani 1 1 d . . .
C13B C 0.69375(8) 0.2090(3) 0.62234(13) 0.0178(5) Uani 1 1 d . . .
H13A H 0.6689 0.3169 0.6130 0.021 Uiso 1 1 calc R . .
H13B H 0.7084 0.2227 0.6747 0.021 Uiso 1 1 calc R . .
C14B C 0.57088(8) 0.0294(3) 0.78756(12) 0.0156(4) Uani 1 1 d . . .
H14C H 0.5536 -0.0982 0.7809 0.019 Uiso 1 1 calc R . .
H14D H 0.5999 0.0114 0.8246 0.019 Uiso 1 1 calc R . .
C15B C 0.53187(8) 0.1694(3) 0.82198(12) 0.0158(4) Uani 1 1 d . . .
C16B C 0.51434(8) 0.5044(3) 0.84725(13) 0.0215(5) Uani 1 1 d . . .
H16A H 0.5354 0.6187 0.8626 0.026 Uiso 1 1 calc R . .
H16B H 0.4964 0.4542 0.8936 0.026 Uiso 1 1 calc R . .
C17B C 0.47434(9) 0.5656(3) 0.78913(14) 0.0272(5) Uani 1 1 d . . .
H17C H 0.4920 0.6099 0.7423 0.041 Uiso 1 1 calc R . .
H17D H 0.4532 0.6718 0.8102 0.041 Uiso 1 1 calc R . .
H17E H 0.4517 0.4550 0.7769 0.041 Uiso 1 1 calc R . .
O1 O 0.75445(6) 0.93405(19) 0.29871(9) 0.0190(3) Uani 1 1 d . . .
O2 O 0.68998(5) 0.79093(18) 0.35973(8) 0.0151(3) Uani 1 1 d . . .
O3 O 0.87920(6) 0.1792(2) 0.45847(9) 0.0252(4) Uani 1 1 d . . .
O4 O 0.61048(6) 0.4029(2) 0.14828(9) 0.0219(3) Uani 1 1 d . . .
O5 O 0.66879(5) 0.17187(18) 0.18248(9) 0.0164(3) Uani 1 1 d . . .
O1B O 0.62849(6) -0.4044(2) 0.68683(9) 0.0203(3) Uani 1 1 d . . .
O2B O 0.56544(5) -0.24680(19) 0.62748(9) 0.0165(3) Uani 1 1 d . . .
O3B O 0.76139(6) 0.3503(2) 0.54315(9) 0.0221(4) Uani 1 1 d . . .
O4B O 0.49171(6) 0.1219(2) 0.85217(9) 0.0244(4) Uani 1 1 d . . .
O5B O 0.54876(5) 0.3542(2) 0.81639(9) 0.0171(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 O1 1.200(2) . ?
C1 O2 1.371(2) . ?
C1 C9 1.510(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.384(3) . ?
C2 O2 1.410(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.511(3) . ?
C8 C9 1.535(3) . ?
C8 C15 1.541(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.536(3) . ?
C9 H9 1.0000 . ?
C10 C14 1.528(3) . ?
C10 C11 1.545(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.531(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.213(3) . ?
C13 C14 1.514(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O4 1.198(2) . ?
C16 O5 1.350(2) . ?
C17 O5 1.458(2) . ?
C17 C18 1.502(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C017 C11B 1.530(3) . ?
C017 C10B 1.541(3) . ?
C017 H01A 0.9900 . ?
C017 H01B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C1B O1B 1.204(2) . ?
C1B O2B 1.369(3) . ?
C1B C9B 1.510(3) . ?
C2B C3B 1.381(3) . ?
C2B C7B 1.390(3) . ?
C2B O2B 1.407(2) . ?
C3B C4B 1.386(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.387(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.390(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.389(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.508(3) . ?
C8B C9B 1.538(3) . ?
C8B C14B 1.542(3) . ?
C8B H8B 1.0000 . ?
C9B C10B 1.537(3) . ?
C9B H9B 1.0000 . ?
C10B C13B 1.532(3) . ?
C10B H10B 1.0000 . ?
C11B C12B 1.509(3) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B O3B 1.214(3) . ?
C12B C13B 1.507(3) . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C14B C15B 1.511(3) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B O4B 1.199(3) . ?
C15B O5B 1.346(2) . ?
C16B O5B 1.460(2) . ?
C16B C17B 1.499(3) . ?
C16B H16A 0.9900 . ?
C16B H16B 0.9900 . ?
C17B H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?

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
O1 C1 O2 117.04(18) . . ?
O1 C1 C9 126.17(18) . . ?
O2 C1 C9 116.76(17) . . ?
C3 C2 C7 122.88(19) . . ?
C3 C2 O2 116.14(17) . . ?
C7 C2 O2 120.97(18) . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.53(19) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.76(18) . . ?
C2 C7 C8 117.86(17) . . ?
C6 C7 C8 124.37(17) . . ?
C7 C8 C9 107.42(16) . . ?
C7 C8 C15 111.36(16) . . ?
C9 C8 C15 109.77(16) . . ?
C7 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C15 C8 H8 109.4 . . ?
C1 C9 C8 109.50(16) . . ?
C1 C9 C10 108.74(16) . . ?
C8 C9 C10 112.88(16) . . ?
C1 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C14 C10 C9 113.53(16) . . ?
C14 C10 C11 102.50(16) . . ?
C9 C10 C11 115.13(16) . . ?
C14 C10 H10 108.5 . . ?
C9 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C12 C11 C10 102.74(16) . . ?
C12 C11 H11A 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C11 104.43(17) . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O3 C13 C12 126.2(2) . . ?
O3 C13 C14 125.3(2) . . ?
C12 C13 C14 108.48(17) . . ?
C13 C14 C10 104.57(16) . . ?
C13 C14 H14A 110.8 . . ?
C10 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
C10 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C16 C15 C8 115.41(16) . . ?
C16 C15 H15A 108.4 . . ?
C8 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C8 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
O4 C16 O5 124.86(19) . . ?
O4 C16 C15 124.39(18) . . ?
O5 C16 C15 110.69(17) . . ?
O5 C17 C18 111.10(18) . . ?
O5 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
O5 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C11B C017 C10B 102.96(17) . . ?
C11B C017 H01A 111.2 . . ?
C10B C017 H01A 111.2 . . ?
C11B C017 H01B 111.2 . . ?
C10B C017 H01B 111.2 . . ?
H01A C017 H01B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1B C1B O2B 117.44(18) . . ?
O1B C1B C9B 125.52(19) . . ?
O2B C1B C9B 116.99(17) . . ?
C3B C2B C7B 122.45(19) . . ?
C3B C2B O2B 116.60(18) . . ?
C7B C2B O2B 120.94(18) . . ?
C2B C3B C4B 118.72(19) . . ?
C2B C3B H3B 120.6 . . ?
C4B C3B H3B 120.6 . . ?
C3B C4B C5B 120.2(2) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B C6B 120.15(19) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C7B C6B C5B 120.59(19) . . ?
C7B C6B H6B 119.7 . . ?
C5B C6B H6B 119.7 . . ?
C6B C7B C2B 117.91(18) . . ?
C6B C7B C8B 123.84(18) . . ?
C2B C7B C8B 118.24(17) . . ?
C7B C8B C9B 108.06(16) . . ?
C7B C8B C14B 111.76(16) . . ?
C9B C8B C14B 110.01(16) . . ?
C7B C8B H8B 109.0 . . ?
C9B C8B H8B 109.0 . . ?
C14B C8B H8B 109.0 . . ?
C1B C9B C10B 109.25(17) . . ?
C1B C9B C8B 109.18(16) . . ?
C10B C9B C8B 113.12(15) . . ?
C1B C9B H9B 108.4 . . ?
C10B C9B H9B 108.4 . . ?
C8B C9B H9B 108.4 . . ?
C13B C10B C9B 113.67(16) . . ?
C13B C10B C017 102.41(16) . . ?
C9B C10B C017 114.87(16) . . ?
C13B C10B H10B 108.5 . . ?
C9B C10B H10B 108.5 . . ?
C017 C10B H10B 108.5 . . ?
C12B C11B C017 104.30(17) . . ?
C12B C11B H11C 110.9 . . ?
C017 C11B H11C 110.9 . . ?
C12B C11B H11D 110.9 . . ?
C017 C11B H11D 110.9 . . ?
H11C C11B H11D 108.9 . . ?
O3B C12B C13B 124.9(2) . . ?
O3B C12B C11B 126.3(2) . . ?
C13B C12B C11B 108.83(18) . . ?
C12B C13B C10B 104.56(17) . . ?
C12B C13B H13A 110.8 . . ?
C10B C13B H13A 110.8 . . ?
C12B C13B H13B 110.8 . . ?
C10B C13B H13B 110.8 . . ?
H13A C13B H13B 108.9 . . ?
C15B C14B C8B 115.31(16) . . ?
C15B C14B H14C 108.4 . . ?
C8B C14B H14C 108.4 . . ?
C15B C14B H14D 108.4 . . ?
C8B C14B H14D 108.4 . . ?
H14C C14B H14D 107.5 . . ?
O4B C15B O5B 124.32(19) . . ?
O4B C15B C14B 124.47(19) . . ?
O5B C15B C14B 111.18(17) . . ?
O5B C16B C17B 111.22(18) . . ?
O5B C16B H16A 109.4 . . ?
C17B C16B H16A 109.4 . . ?
O5B C16B H16B 109.4 . . ?
C17B C16B H16B 109.4 . . ?
H16A C16B H16B 108.0 . . ?
C16B C17B H17C 109.5 . . ?
C16B C17B H17D 109.5 . . ?
H17C C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
H17C C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C1 O2 C2 120.61(15) . . ?
C16 O5 C17 116.10(15) . . ?
C1B O2B C2B 120.59(15) . . ?
C15B O5B C16B 116.63(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-14b
_database_code_depnum_ccdc_archive 'CCDC 1440388'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA12-syn-14b
#==============================================================================
_audit_creation_date             'April 22 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((3S*,4S*)-6-bromo-2-oxo-3-((R*)-3-oxocyclopentyl)chroman-4-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          94.0
_chemical_formula_moiety         'C18 H19 Br O5'
_chemical_formula_sum            'C18 H19 Br O5'
_chemical_formula_weight         395.24
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration ad

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c     '
_symmetry_space_group_name_Hall  'P -2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.3068(19)
_cell_length_b                   9.6829(16)
_cell_length_c                   24.116(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.091(2)
_cell_angle_gamma                90.00
_cell_volume                     2571.7(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3963
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.08
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1212
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_T_max  0.8683
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            12184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6361
_reflns_number_gt                5637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_number_reflns         6361
_refine_ls_number_parameters     652
_refine_ls_number_restraints     452
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0589
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.20567(3) 0.00390(4) 0.862738(18) 0.02461(11) Uani 1 1 d . . .
Br1B Br 0.84268(3) 0.98574(4) 0.698334(16) 0.02049(11) Uani 1 1 d . . .
Br1C Br 0.52285(3) 0.01117(4) 0.50573(2) 0.02513(11) Uani 1 1 d . . .
C1 C 0.2499(3) 0.4294(4) 0.64064(15) 0.0129(8) Uani 1 1 d U . .
C2 C 0.1293(3) 0.3561(3) 0.62183(15) 0.0127(8) Uani 1 1 d U . .
H2 H 0.0695 0.4214 0.5985 0.015 Uiso 1 1 calc R . .
C3 C 0.0779(3) 0.3049(3) 0.67255(16) 0.0148(8) Uani 1 1 d U . .
H3 H 0.0226 0.2262 0.6576 0.018 Uiso 1 1 calc R . .
C4 C 0.1784(3) 0.2445(3) 0.71826(16) 0.0130(8) Uani 1 1 d U . .
C5 C 0.1529(3) 0.1617(3) 0.76144(15) 0.0127(8) Uani 1 1 d U . .
H5 H 0.0710 0.1430 0.7626 0.015 Uiso 1 1 calc R . .
C6 C 0.2464(3) 0.1068(3) 0.80238(16) 0.0168(8) Uani 1 1 d U . .
C7 C 0.3676(3) 0.1254(3) 0.80141(16) 0.0159(8) Uani 1 1 d U . .
H7 H 0.4304 0.0826 0.8289 0.019 Uiso 1 1 calc R . .
C8 C 0.3939(3) 0.2087(3) 0.75889(16) 0.0155(8) Uani 1 1 d U . .
H8 H 0.4758 0.2240 0.7568 0.019 Uiso 1 1 calc R . .
C9 C 0.2996(3) 0.2697(3) 0.71933(15) 0.0121(8) Uani 1 1 d U . .
C10 C 0.1487(3) 0.2333(3) 0.58381(15) 0.0128(8) Uani 1 1 d U . .
H10 H 0.1980 0.1608 0.6081 0.015 Uiso 1 1 calc R . .
C11 C 0.2126(3) 0.2751(3) 0.53639(16) 0.0154(8) Uani 1 1 d U . .
H11A H 0.1816 0.3647 0.5193 0.019 Uiso 1 1 calc R . .
H11B H 0.3015 0.2822 0.5513 0.019 Uiso 1 1 calc R . .
C12 C 0.1815(3) 0.1585(4) 0.49295(17) 0.0199(9) Uani 1 1 d U . .
H12A H 0.1815 0.1922 0.4542 0.024 Uiso 1 1 calc R . .
H12B H 0.2406 0.0819 0.5026 0.024 Uiso 1 1 calc R . .
C13 C 0.0565(3) 0.1118(3) 0.49653(16) 0.0147(8) Uani 1 1 d U . .
C14 C 0.0288(3) 0.1688(3) 0.55067(16) 0.0148(8) Uani 1 1 d U . .
H14A H 0.0022 0.0942 0.5731 0.018 Uiso 1 1 calc R . .
H14B H -0.0360 0.2395 0.5418 0.018 Uiso 1 1 calc R . .
C15 C -0.0007(3) 0.4114(3) 0.69493(15) 0.0152(8) Uani 1 1 d U . .
H15A H -0.0575 0.4533 0.6619 0.018 Uiso 1 1 calc R . .
H15B H -0.0501 0.3620 0.7176 0.018 Uiso 1 1 calc R . .
C16 C 0.0667(3) 0.5259(3) 0.73085(15) 0.0137(8) Uani 1 1 d U . .
C17 C 0.0437(3) 0.7043(4) 0.79592(15) 0.0174(9) Uani 1 1 d U . .
H17A H 0.0569 0.7860 0.7734 0.021 Uiso 1 1 calc R . .
H17B H 0.1224 0.6772 0.8209 0.021 Uiso 1 1 calc R . .
C18 C -0.0482(3) 0.7362(4) 0.83087(18) 0.0242(10) Uani 1 1 d U . .
H18A H -0.1261 0.7601 0.8054 0.036 Uiso 1 1 calc R . .
H18B H -0.0195 0.8141 0.8563 0.036 Uiso 1 1 calc R . .
H18C H -0.0588 0.6550 0.8535 0.036 Uiso 1 1 calc R . .
C1B C 0.9224(3) 0.5607(4) 0.48124(16) 0.0152(8) Uani 1 1 d U . .
C2B C 0.8033(3) 0.6343(3) 0.45841(15) 0.0127(8) Uani 1 1 d U . .
H2B H 0.7461 0.5673 0.4346 0.015 Uiso 1 1 calc R . .
C3B C 0.7428(3) 0.6892(3) 0.50554(15) 0.0136(8) Uani 1 1 d U . .
H3B H 0.6933 0.7708 0.4887 0.016 Uiso 1 1 calc R . .
C4B C 0.8365(3) 0.7442(3) 0.55511(16) 0.0133(8) Uani 1 1 d U . .
C5B C 0.8049(3) 0.8298(3) 0.59613(15) 0.0130(8) Uani 1 1 d U . .
H5B H 0.7223 0.8540 0.5931 0.016 Uiso 1 1 calc R . .
C6B C 0.8934(3) 0.8799(3) 0.64139(15) 0.0152(8) Uani 1 1 d U . .
C7B C 1.0150(3) 0.8490(3) 0.64691(16) 0.0169(8) Uani 1 1 d U . .
H7B H 1.0748 0.8855 0.6776 0.020 Uiso 1 1 calc R . .
C8B C 1.0473(3) 0.7647(3) 0.60734(15) 0.0157(8) Uani 1 1 d U . .
H8B H 1.1304 0.7424 0.6104 0.019 Uiso 1 1 calc R . .
C9B C 0.9598(3) 0.7115(3) 0.56270(15) 0.0137(8) Uani 1 1 d U . .
C10B C 0.8267(3) 0.7528(3) 0.41932(15) 0.0153(8) Uani 1 1 d U . .
H10B H 0.8728 0.8279 0.4434 0.018 Uiso 1 1 calc R . .
C11B C 0.8975(3) 0.7085(4) 0.37420(16) 0.0185(9) Uani 1 1 d U . .
H11C H 0.9859 0.7045 0.3910 0.022 Uiso 1 1 calc R . .
H11D H 0.8699 0.6170 0.3580 0.022 Uiso 1 1 calc R . .
C12B C 0.8682(3) 0.8211(4) 0.32871(17) 0.0238(9) Uani 1 1 d U . .
H12C H 0.9269 0.8982 0.3377 0.029 Uiso 1 1 calc R . .
H12D H 0.8706 0.7836 0.2908 0.029 Uiso 1 1 calc R . .
C13B C 0.7408(3) 0.8696(4) 0.32982(16) 0.0184(9) Uani 1 1 d U . .
C14B C 0.7085(3) 0.8141(3) 0.38248(15) 0.0152(8) Uani 1 1 d U . .
H14C H 0.6453 0.7417 0.3726 0.018 Uiso 1 1 calc R . .
H14D H 0.6773 0.8889 0.4033 0.018 Uiso 1 1 calc R . .
C15B C 0.6531(3) 0.5879(3) 0.52334(16) 0.0161(8) Uani 1 1 d U . .
H15C H 0.6061 0.6381 0.5469 0.019 Uiso 1 1 calc R . .
H15D H 0.5951 0.5553 0.4887 0.019 Uiso 1 1 calc R . .
C16B C 0.7122(3) 0.4640(4) 0.55621(15) 0.0157(8) Uani 1 1 d U . .
C17B C 0.6773(3) 0.2808(4) 0.61617(17) 0.0213(9) Uani 1 1 d U . .
H17C H 0.7523 0.3055 0.6445 0.026 Uiso 1 1 calc R . .
H17D H 0.6958 0.2034 0.5927 0.026 Uiso 1 1 calc R . .
C18B C 0.5787(4) 0.2400(4) 0.64574(19) 0.0267(11) Uani 1 1 d U . .
H18D H 0.5589 0.3187 0.6675 0.040 Uiso 1 1 calc R . .
H18E H 0.6068 0.1628 0.6716 0.040 Uiso 1 1 calc R . .
H18F H 0.5062 0.2120 0.6173 0.040 Uiso 1 1 calc R . .
C1C C 0.6072(3) 0.4651(3) 0.29913(16) 0.0143(8) Uani 1 1 d U . .
C2C C 0.4849(3) 0.3968(3) 0.28021(15) 0.0127(8) Uani 1 1 d U . .
H2C H 0.4305 0.4618 0.2539 0.015 Uiso 1 1 calc R . .
C3C C 0.4307(3) 0.3746(3) 0.33234(16) 0.0150(8) Uani 1 1 d U . .
H3C H 0.3554 0.3177 0.3205 0.018 Uiso 1 1 calc R . .
C4C C 0.5199(3) 0.2962(3) 0.37668(16) 0.0140(8) Uani 1 1 d U . .
C5C C 0.4862(3) 0.2032(3) 0.41486(16) 0.0155(8) Uani 1 1 d U . .
H5C H 0.4027 0.1868 0.4136 0.019 Uiso 1 1 calc R . .
C6C C 0.5752(3) 0.1350(3) 0.45461(16) 0.0176(8) Uani 1 1 d U . .
C7C C 0.6970(3) 0.1532(3) 0.45733(15) 0.0160(8) Uani 1 1 d U . .
H7C H 0.7560 0.1035 0.4843 0.019 Uiso 1 1 calc R . .
C8C C 0.7322(3) 0.2449(3) 0.42022(15) 0.0156(8) Uani 1 1 d U . .
H8C H 0.8159 0.2598 0.4216 0.019 Uiso 1 1 calc R . .
C9C C 0.6434(3) 0.3152(3) 0.38072(15) 0.0141(8) Uani 1 1 d U . .
C10C C 0.4965(3) 0.2639(3) 0.24677(16) 0.0153(8) Uani 1 1 d U . .
H10C H 0.5471 0.1952 0.2728 0.018 Uiso 1 1 calc R . .
C11C C 0.5532(3) 0.2898(4) 0.19520(17) 0.0213(9) Uani 1 1 d U . .
H11E H 0.5225 0.3769 0.1756 0.026 Uiso 1 1 calc R . .
H11F H 0.6428 0.2944 0.2071 0.026 Uiso 1 1 calc R . .
C12C C 0.5125(3) 0.1649(4) 0.15674(18) 0.0263(10) Uani 1 1 d U . .
H12E H 0.5059 0.1892 0.1163 0.032 Uiso 1 1 calc R . .
H12F H 0.5706 0.0876 0.1670 0.032 Uiso 1 1 calc R . .
C13C C 0.3894(3) 0.1264(3) 0.16715(17) 0.0196(9) Uani 1 1 d U . .
C14C C 0.3727(3) 0.1994(4) 0.21982(16) 0.0170(9) Uani 1 1 d U . .
H14E H 0.3480 0.1333 0.2464 0.020 Uiso 1 1 calc R . .
H14F H 0.3096 0.2719 0.2099 0.020 Uiso 1 1 calc R . .
C15C C 0.3964(3) 0.5138(3) 0.35542(16) 0.0154(8) Uani 1 1 d U . .
H15E H 0.4715 0.5673 0.3703 0.018 Uiso 1 1 calc R . .
H15F H 0.3462 0.5670 0.3236 0.018 Uiso 1 1 calc R . .
C16C C 0.3277(3) 0.4998(4) 0.40186(16) 0.0162(8) Uani 1 1 d U . .
C17C C 0.2732(3) 0.6133(4) 0.47982(17) 0.0223(9) Uani 1 1 d U . .
H17E H 0.3131 0.5510 0.5111 0.027 Uiso 1 1 calc R . .
H17F H 0.1891 0.5805 0.4648 0.027 Uiso 1 1 calc R . .
C18C C 0.2722(5) 0.7572(4) 0.5012(2) 0.0428(13) Uani 1 1 d U . .
H18G H 0.3558 0.7902 0.5142 0.064 Uiso 1 1 calc R . .
H18H H 0.2314 0.7594 0.5330 0.064 Uiso 1 1 calc R . .
H18I H 0.2286 0.8169 0.4705 0.064 Uiso 1 1 calc R . .
O1 O 0.2802(2) 0.5328(2) 0.62015(11) 0.0173(6) Uani 1 1 d U . .
O2 O 0.3352(2) 0.3645(2) 0.68279(11) 0.0151(6) Uani 1 1 d U . .
O3 O -0.0126(2) 0.0415(2) 0.46189(12) 0.0250(6) Uani 1 1 d U . .
O4 O 0.1719(2) 0.5552(2) 0.73500(11) 0.0179(6) Uani 1 1 d U . .
O5 O -0.0074(2) 0.5900(2) 0.75831(11) 0.0189(6) Uani 1 1 d U . .
O1B O 0.9579(2) 0.4620(2) 0.45982(11) 0.0188(6) Uani 1 1 d U . .
O2B O 1.0009(2) 0.6194(2) 0.52707(11) 0.0160(6) Uani 1 1 d U . .
O3B O 0.6759(2) 0.9399(3) 0.29381(12) 0.0277(7) Uani 1 1 d U . .
O4B O 0.8157(2) 0.4296(2) 0.56086(11) 0.0180(6) Uani 1 1 d U . .
O5B O 0.6321(2) 0.4001(2) 0.58012(11) 0.0210(6) Uani 1 1 d U . .
O1C O 0.6443(2) 0.5610(2) 0.27583(11) 0.0199(6) Uani 1 1 d U . .
O2C O 0.6849(2) 0.4111(2) 0.34666(11) 0.0158(5) Uani 1 1 d U . .
O3C O 0.3156(2) 0.0518(3) 0.13686(12) 0.0292(7) Uani 1 1 d U . .
O4C O 0.2672(2) 0.4009(2) 0.40843(12) 0.0206(6) Uani 1 1 d U . .
O5C O 0.3405(2) 0.6136(2) 0.43443(12) 0.0193(6) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Br1 C6 1.904(4) . ?
Br1B C6B 1.903(3) . ?
Br1C C6C 1.907(4) . ?
C1 O1 1.200(4) . ?
C1 O2 1.384(4) . ?
C1 C2 1.513(5) . ?
C2 C10 1.547(5) . ?
C2 C3 1.549(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.510(5) . ?
C3 C15 1.537(5) . ?
C3 H3 1.0000 . ?
C4 C9 1.386(5) . ?
C4 C5 1.395(5) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(5) . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(5) . ?
C8 H8 0.9500 . ?
C9 O2 1.394(4) . ?
C10 C11 1.539(5) . ?
C10 C14 1.541(5) . ?
C10 H10 1.0000 . ?
C11 C12 1.526(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.504(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.215(4) . ?
C13 C14 1.514(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.504(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O4 1.205(4) . ?
C16 O5 1.333(4) . ?
C17 O5 1.464(4) . ?
C17 C18 1.511(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C1B O1B 1.197(4) . ?
C1B O2B 1.374(4) . ?
C1B C2B 1.513(5) . ?
C2B C10B 1.545(5) . ?
C2B C3B 1.547(5) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.503(5) . ?
C3B C15B 1.541(4) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.398(5) . ?
C4B C9B 1.401(5) . ?
C5B C6B 1.390(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.384(5) . ?
C7B C8B 1.366(5) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.386(5) . ?
C8B H8B 0.9500 . ?
C9B O2B 1.389(4) . ?
C10B C14B 1.546(5) . ?
C10B C11B 1.551(5) . ?
C10B H10B 1.0000 . ?
C11B C12B 1.529(5) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.521(5) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B O3B 1.211(4) . ?
C13B C14B 1.499(5) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.508(5) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B O4B 1.197(4) . ?
C16B O5B 1.332(4) . ?
C17B O5B 1.466(4) . ?
C17B C18B 1.506(5) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C1C O1C 1.209(4) . ?
C1C O2C 1.379(4) . ?
C1C C2C 1.507(5) . ?
C2C C3C 1.533(5) . ?
C2C C10C 1.541(5) . ?
C2C H2C 1.0000 . ?
C3C C4C 1.499(5) . ?
C3C C15C 1.542(4) . ?
C3C H3C 1.0000 . ?
C4C C9C 1.391(5) . ?
C4C C5C 1.401(5) . ?
C5C C6C 1.390(5) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.375(5) . ?
C7C C8C 1.382(5) . ?
C7C H7C 0.9500 . ?
C8C C9C 1.395(5) . ?
C8C H8C 0.9500 . ?
C9C O2C 1.390(4) . ?
C10C C14C 1.536(5) . ?
C10C C11C 1.543(5) . ?
C10C H10C 1.0000 . ?
C11C C12C 1.530(5) . ?
C11C H11E 0.9900 . ?
C11C H11F 0.9900 . ?
C12C C13C 1.516(5) . ?
C12C H12E 0.9900 . ?
C12C H12F 0.9900 . ?
C13C O3C 1.215(4) . ?
C13C C14C 1.503(5) . ?
C14C H14E 0.9900 . ?
C14C H14F 0.9900 . ?
C15C C16C 1.507(5) . ?
C15C H15E 0.9900 . ?
C15C H15F 0.9900 . ?
C16C O4C 1.208(4) . ?
C16C O5C 1.343(4) . ?
C17C O5C 1.468(4) . ?
C17C C18C 1.487(5) . ?
C17C H17E 0.9900 . ?
C17C H17F 0.9900 . ?
C18C H18G 0.9800 . ?
C18C H18H 0.9800 . ?
C18C H18I 0.9800 . ?

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
O1 C1 O2 117.7(3) . . ?
O1 C1 C2 126.2(3) . . ?
O2 C1 C2 116.0(3) . . ?
C1 C2 C10 107.4(3) . . ?
C1 C2 C3 112.8(3) . . ?
C10 C2 C3 110.5(3) . . ?
C1 C2 H2 108.7 . . ?
C10 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C4 C3 C15 113.8(3) . . ?
C4 C3 C2 110.2(3) . . ?
C15 C3 C2 114.3(3) . . ?
C4 C3 H3 105.9 . . ?
C15 C3 H3 105.9 . . ?
C2 C3 H3 105.9 . . ?
C9 C4 C5 117.2(3) . . ?
C9 C4 C3 121.5(3) . . ?
C5 C4 C3 121.2(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 122.5(3) . . ?
C5 C6 Br1 118.1(3) . . ?
C7 C6 Br1 119.4(3) . . ?
C6 C7 C8 117.7(3) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C4 C9 C8 122.6(3) . . ?
C4 C9 O2 122.0(3) . . ?
C8 C9 O2 115.2(3) . . ?
C11 C10 C14 103.1(3) . . ?
C11 C10 C2 113.1(3) . . ?
C14 C10 C2 113.1(3) . . ?
C11 C10 H10 109.1 . . ?
C14 C10 H10 109.1 . . ?
C2 C10 H10 109.1 . . ?
C12 C11 C10 104.0(3) . . ?
C12 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C11 104.9(3) . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
O3 C13 C12 126.5(3) . . ?
O3 C13 C14 124.8(3) . . ?
C12 C13 C14 108.7(3) . . ?
C13 C14 C10 105.4(3) . . ?
C13 C14 H14A 110.7 . . ?
C10 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C10 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C16 C15 C3 116.0(3) . . ?
C16 C15 H15A 108.3 . . ?
C3 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C3 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
O4 C16 O5 124.7(3) . . ?
O4 C16 C15 125.7(3) . . ?
O5 C16 C15 109.6(3) . . ?
O5 C17 C18 106.0(3) . . ?
O5 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
O5 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1B C1B O2B 117.3(3) . . ?
O1B C1B C2B 125.2(3) . . ?
O2B C1B C2B 117.2(3) . . ?
C1B C2B C10B 108.1(3) . . ?
C1B C2B C3B 113.5(3) . . ?
C10B C2B C3B 111.0(3) . . ?
C1B C2B H2B 108.0 . . ?
C10B C2B H2B 108.0 . . ?
C3B C2B H2B 108.0 . . ?
C4B C3B C15B 113.2(3) . . ?
C4B C3B C2B 110.9(3) . . ?
C15B C3B C2B 114.5(3) . . ?
C4B C3B H3B 105.8 . . ?
C15B C3B H3B 105.8 . . ?
C2B C3B H3B 105.8 . . ?
C5B C4B C9B 116.6(3) . . ?
C5B C4B C3B 121.8(3) . . ?
C9B C4B C3B 121.7(3) . . ?
C6B C5B C4B 120.6(3) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C7B C6B C5B 121.5(3) . . ?
C7B C6B Br1B 120.2(3) . . ?
C5B C6B Br1B 118.3(3) . . ?
C8B C7B C6B 118.6(3) . . ?
C8B C7B H7B 120.7 . . ?
C6B C7B H7B 120.7 . . ?
C7B C8B C9B 120.5(3) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B H8B 119.7 . . ?
C8B C9B O2B 116.0(3) . . ?
C8B C9B C4B 122.2(3) . . ?
O2B C9B C4B 121.8(3) . . ?
C2B C10B C14B 113.0(3) . . ?
C2B C10B C11B 114.2(3) . . ?
C14B C10B C11B 102.7(3) . . ?
C2B C10B H10B 108.9 . . ?
C14B C10B H10B 108.9 . . ?
C11B C10B H10B 108.9 . . ?
C12B C11B C10B 104.1(3) . . ?
C12B C11B H11C 110.9 . . ?
C10B C11B H11C 110.9 . . ?
C12B C11B H11D 110.9 . . ?
C10B C11B H11D 110.9 . . ?
H11C C11B H11D 109.0 . . ?
C13B C12B C11B 105.1(3) . . ?
C13B C12B H12C 110.7 . . ?
C11B C12B H12C 110.7 . . ?
C13B C12B H12D 110.7 . . ?
C11B C12B H12D 110.7 . . ?
H12C C12B H12D 108.8 . . ?
O3B C13B C14B 125.8(4) . . ?
O3B C13B C12B 125.7(3) . . ?
C14B C13B C12B 108.5(3) . . ?
C13B C14B C10B 106.2(3) . . ?
C13B C14B H14C 110.5 . . ?
C10B C14B H14C 110.5 . . ?
C13B C14B H14D 110.5 . . ?
C10B C14B H14D 110.5 . . ?
H14C C14B H14D 108.7 . . ?
C16B C15B C3B 114.3(3) . . ?
C16B C15B H15C 108.7 . . ?
C3B C15B H15C 108.7 . . ?
C16B C15B H15D 108.7 . . ?
C3B C15B H15D 108.7 . . ?
H15C C15B H15D 107.6 . . ?
O4B C16B O5B 125.2(3) . . ?
O4B C16B C15B 125.3(3) . . ?
O5B C16B C15B 109.5(3) . . ?
O5B C17B C18B 106.9(3) . . ?
O5B C17B H17C 110.3 . . ?
C18B C17B H17C 110.3 . . ?
O5B C17B H17D 110.3 . . ?
C18B C17B H17D 110.3 . . ?
H17C C17B H17D 108.6 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
O1C C1C O2C 117.0(3) . . ?
O1C C1C C2C 126.0(3) . . ?
O2C C1C C2C 117.0(3) . . ?
C1C C2C C3C 108.8(3) . . ?
C1C C2C C10C 110.1(3) . . ?
C3C C2C C10C 114.1(3) . . ?
C1C C2C H2C 107.9 . . ?
C3C C2C H2C 107.9 . . ?
C10C C2C H2C 107.9 . . ?
C4C C3C C2C 109.1(3) . . ?
C4C C3C C15C 111.7(3) . . ?
C2C C3C C15C 110.7(3) . . ?
C4C C3C H3C 108.4 . . ?
C2C C3C H3C 108.4 . . ?
C15C C3C H3C 108.4 . . ?
C9C C4C C5C 117.2(3) . . ?
C9C C4C C3C 119.1(3) . . ?
C5C C4C C3C 123.7(3) . . ?
C6C C5C C4C 119.8(3) . . ?
C6C C5C H5C 120.1 . . ?
C4C C5C H5C 120.1 . . ?
C7C C6C C5C 122.2(3) . . ?
C7C C6C Br1C 120.2(3) . . ?
C5C C6C Br1C 117.5(3) . . ?
C6C C7C C8C 118.9(3) . . ?
C6C C7C H7C 120.5 . . ?
C8C C7C H7C 120.5 . . ?
C7C C8C C9C 119.2(3) . . ?
C7C C8C H8C 120.4 . . ?
C9C C8C H8C 120.4 . . ?
O2C C9C C4C 121.0(3) . . ?
O2C C9C C8C 116.3(3) . . ?
C4C C9C C8C 122.7(3) . . ?
C14C C10C C2C 112.5(3) . . ?
C14C C10C C11C 103.3(3) . . ?
C2C C10C C11C 112.7(3) . . ?
C14C C10C H10C 109.4 . . ?
C2C C10C H10C 109.4 . . ?
C11C C10C H10C 109.4 . . ?
C12C C11C C10C 103.7(3) . . ?
C12C C11C H11E 111.0 . . ?
C10C C11C H11E 111.0 . . ?
C12C C11C H11F 111.0 . . ?
C10C C11C H11F 111.0 . . ?
H11E C11C H11F 109.0 . . ?
C13C C12C C11C 104.8(3) . . ?
C13C C12C H12E 110.8 . . ?
C11C C12C H12E 110.8 . . ?
C13C C12C H12F 110.8 . . ?
C11C C12C H12F 110.8 . . ?
H12E C12C H12F 108.9 . . ?
O3C C13C C14C 125.9(4) . . ?
O3C C13C C12C 125.3(4) . . ?
C14C C13C C12C 108.7(3) . . ?
C13C C14C C10C 105.7(3) . . ?
C13C C14C H14E 110.6 . . ?
C10C C14C H14E 110.6 . . ?
C13C C14C H14F 110.6 . . ?
C10C C14C H14F 110.6 . . ?
H14E C14C H14F 108.7 . . ?
C16C C15C C3C 113.8(3) . . ?
C16C C15C H15E 108.8 . . ?
C3C C15C H15E 108.8 . . ?
C16C C15C H15F 108.8 . . ?
C3C C15C H15F 108.8 . . ?
H15E C15C H15F 107.7 . . ?
O4C C16C O5C 124.3(3) . . ?
O4C C16C C15C 124.9(3) . . ?
O5C C16C C15C 110.8(3) . . ?
O5C C17C C18C 107.6(3) . . ?
O5C C17C H17E 110.2 . . ?
C18C C17C H17E 110.2 . . ?
O5C C17C H17F 110.2 . . ?
C18C C17C H17F 110.2 . . ?
H17E C17C H17F 108.5 . . ?
C17C C18C H18G 109.5 . . ?
C17C C18C H18H 109.5 . . ?
H18G C18C H18H 109.5 . . ?
C17C C18C H18I 109.5 . . ?
H18G C18C H18I 109.5 . . ?
H18H C18C H18I 109.5 . . ?
C1 O2 C9 120.7(3) . . ?
C16 O5 C17 117.1(3) . . ?
C1B O2B C9B 121.2(3) . . ?
C16B O5B C17B 116.3(3) . . ?
C1C O2C C9C 120.5(3) . . ?
C16C O5C C17C 115.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.061

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-15a
_database_code_depnum_ccdc_archive 'CCDC 1440389'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA-syn-15a
#==============================================================================
_audit_creation_date             'July 16 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((3S*,4S*)-2-oxo-3-((R*)-3-oxocyclohexyl)chroman-4-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          97.5
_chemical_formula_moiety         'C19 H22 O5'
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.37
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1059(12)
_cell_length_b                   7.0831(6)
_cell_length_c                   16.4912(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.0800(10)
_cell_angle_gamma                90.00
_cell_volume                     1610.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3451
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.59
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            7482
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2841
_reflns_number_gt                2505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0426P)²+0.6685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     218
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.68170(9) -0.01027(18) 0.65943(9) 0.0157(3) Uani 1 1 d U . .
C2 C 0.63205(9) 0.17179(18) 0.61674(8) 0.0143(3) Uani 1 1 d U . .
H2 H 0.5985 0.1495 0.5513 0.017 Uiso 1 1 calc R . .
C3 C 0.71029(9) 0.32389(18) 0.63200(8) 0.0133(3) Uani 1 1 d U . .
H3 H 0.6783 0.4472 0.6076 0.016 Uiso 1 1 calc R . .
C4 C 0.76849(9) 0.34233(18) 0.73105(8) 0.0133(3) Uani 1 1 d U . .
C5 C 0.80423(9) 0.51322(18) 0.77366(8) 0.0146(3) Uani 1 1 d U . .
H5 H 0.7913 0.6267 0.7401 0.018 Uiso 1 1 calc R . .
C6 C 0.85859(9) 0.51883(19) 0.86480(9) 0.0168(3) Uani 1 1 d U . .
H6 H 0.8832 0.6358 0.8932 0.020 Uiso 1 1 calc R . .
C7 C 0.87703(9) 0.3542(2) 0.91453(9) 0.0179(3) Uani 1 1 d U . .
H7 H 0.9143 0.3588 0.9769 0.021 Uiso 1 1 calc R . .
C8 C 0.84107(9) 0.1822(2) 0.87338(9) 0.0172(3) Uani 1 1 d U . .
H8 H 0.8532 0.0689 0.9070 0.021 Uiso 1 1 calc R . .
C9 C 0.78730(9) 0.17993(18) 0.78238(8) 0.0145(3) Uani 1 1 d U . .
C10 C 0.55351(9) 0.22414(18) 0.65107(8) 0.0132(3) Uani 1 1 d U . .
H10 H 0.5864 0.2598 0.7152 0.016 Uiso 1 1 calc R . .
C11 C 0.48529(9) 0.05751(18) 0.64209(9) 0.0161(3) Uani 1 1 d U . .
H11A H 0.4568 0.0140 0.5796 0.019 Uiso 1 1 calc R . .
H11B H 0.5230 -0.0483 0.6795 0.019 Uiso 1 1 calc R . .
C12 C 0.40382(9) 0.11050(19) 0.66996(9) 0.0178(3) Uani 1 1 d U . .
H12A H 0.4319 0.1457 0.7336 0.021 Uiso 1 1 calc R . .
H12B H 0.3611 -0.0001 0.6624 0.021 Uiso 1 1 calc R . .
C13 C 0.34378(9) 0.2757(2) 0.61469(9) 0.0205(3) Uani 1 1 d U . .
H13A H 0.3071 0.2334 0.5527 0.025 Uiso 1 1 calc R . .
H13B H 0.2964 0.3156 0.6387 0.025 Uiso 1 1 calc R . .
C14 C 0.40642(9) 0.44125(19) 0.61540(8) 0.0166(3) Uani 1 1 d U . .
C15 C 0.49528(9) 0.39524(18) 0.59826(8) 0.0160(3) Uani 1 1 d U . .
H15A H 0.5384 0.5070 0.6135 0.019 Uiso 1 1 calc R . .
H15B H 0.4746 0.3701 0.5341 0.019 Uiso 1 1 calc R . .
C16 C 0.77520(9) 0.26501(19) 0.58408(9) 0.0159(3) Uani 1 1 d U . .
H16A H 0.8050 0.1413 0.6078 0.019 Uiso 1 1 calc R . .
H16B H 0.7336 0.2478 0.5202 0.019 Uiso 1 1 calc R . .
C17 C 0.85487(9) 0.40285(19) 0.59294(8) 0.0152(3) Uani 1 1 d U . .
C18 C 0.89209(10) 0.7278(2) 0.58576(9) 0.0202(3) Uani 1 1 d U . .
H18A H 0.8579 0.8369 0.5487 0.024 Uiso 1 1 calc R . .
H18B H 0.9383 0.6784 0.5623 0.024 Uiso 1 1 calc R . .
C19 C 0.94700(10) 0.7918(2) 0.68003(9) 0.0233(3) Uani 1 1 d U . .
H19A H 0.9011 0.8347 0.7044 0.035 Uiso 1 1 calc R . .
H19B H 0.9903 0.8960 0.6815 0.035 Uiso 1 1 calc R . .
H19C H 0.9854 0.6865 0.7157 0.035 Uiso 1 1 calc R . .
O1 O 0.66209(7) -0.16442(13) 0.62620(6) 0.0217(2) Uani 1 1 d U . .
O2 O 0.75423(6) 0.00214(12) 0.74335(6) 0.0168(2) Uani 1 1 d U . .
O3 O 0.38658(7) 0.60353(14) 0.62604(6) 0.0221(2) Uani 1 1 d U . .
O4 O 0.93708(7) 0.35853(14) 0.60717(6) 0.0225(2) Uani 1 1 d U . .
O5 O 0.82181(6) 0.58118(13) 0.57964(6) 0.0174(2) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 O1 1.2033(16) . ?
C1 O2 1.3733(16) . ?
C1 C2 1.5134(18) . ?
C2 C3 1.5421(18) . ?
C2 C10 1.5536(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5120(17) . ?
C3 C16 1.5467(17) . ?
C3 H3 1.0000 . ?
C4 C9 1.3872(18) . ?
C4 C5 1.3931(18) . ?
C5 C6 1.3884(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3871(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3922(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3848(18) . ?
C8 H8 0.9500 . ?
C9 O2 1.4097(15) . ?
C10 C11 1.5337(17) . ?
C10 C15 1.5414(17) . ?
C10 H10 1.0000 . ?
C11 C12 1.5259(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5320(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5040(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.2185(16) . ?
C14 C15 1.5158(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5098(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O4 1.2074(16) . ?
C17 O5 1.3430(16) . ?
C18 O5 1.4588(16) . ?
C18 C19 1.5027(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
O1 C1 O2 117.65(12) . . ?
O1 C1 C2 125.32(12) . . ?
O2 C1 C2 117.03(11) . . ?
C1 C2 C3 108.54(10) . . ?
C1 C2 C10 109.94(10) . . ?
C3 C2 C10 114.98(10) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C10 C2 H2 107.7 . . ?
C4 C3 C2 107.80(10) . . ?
C4 C3 C16 111.40(10) . . ?
C2 C3 C16 109.37(10) . . ?
C4 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C16 C3 H3 109.4 . . ?
C9 C4 C5 118.16(12) . . ?
C9 C4 C3 118.14(11) . . ?
C5 C4 C3 123.70(11) . . ?
C6 C5 C4 120.48(12) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.22(12) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.20(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 118.57(12) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C4 122.35(12) . . ?
C8 C9 O2 116.56(11) . . ?
C4 C9 O2 121.06(11) . . ?
C11 C10 C15 110.15(10) . . ?
C11 C10 C2 111.35(10) . . ?
C15 C10 C2 109.04(10) . . ?
C11 C10 H10 108.8 . . ?
C15 C10 H10 108.8 . . ?
C2 C10 H10 108.8 . . ?
C12 C11 C10 111.98(11) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 111.29(11) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 111.90(11) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O3 C14 C13 123.08(12) . . ?
O3 C14 C15 121.22(12) . . ?
C13 C14 C15 115.66(11) . . ?
C14 C15 C10 114.10(10) . . ?
C14 C15 H15A 108.7 . . ?
C10 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C10 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C3 115.00(11) . . ?
C17 C16 H16A 108.5 . . ?
C3 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C3 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
O4 C17 O5 124.11(12) . . ?
O4 C17 C16 124.52(12) . . ?
O5 C17 C16 111.33(10) . . ?
O5 C18 C19 111.42(11) . . ?
O5 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
O5 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 O2 C9 120.38(10) . . ?
C17 O5 C18 116.53(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-15b
_database_code_depnum_ccdc_archive 'CCDC 1440390'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA12-syn-15b
#==============================================================================
_audit_creation_date             'January 16 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((3S*,4S*)-6-bromo-2-oxo-3-((R*)-3-oxocyclohexyl)chroman-4-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          97.0
_chemical_formula_moiety         'C19 H21 Br O5'
_chemical_formula_sum            'C19 H21 Br O5'
_chemical_formula_weight         409.27
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1  '
_symmetry_space_group_name_Hall  '-P 1 '



loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.854(3)
_cell_length_b                   14.268(4)
_cell_length_c                   14.396(4)
_cell_angle_alpha                94.289(4)
_cell_angle_beta                 102.730(4)
_cell_angle_gamma                95.207(4)
_cell_volume                     1758.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4477
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.43
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_T_max  0.8909
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            17095
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6156
_reflns_number_gt                4996
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0009P)²+30.7076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6156
_refine_ls_number_parameters     453
_refine_ls_number_restraints     312
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1991
_refine_ls_wR_factor_gt          0.1936
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.61939(9) 1.15163(6) 0.95372(6) 0.0199(2) Uani 1 1 d . . .
Br1B Br 0.59022(10) 0.62859(6) 0.93164(7) 0.0275(3) Uani 1 1 d . . .
C1 C 0.2268(9) 0.7652(6) 0.6555(6) 0.0185(16) Uani 1 1 d U . .
C2 C 0.1746(9) 0.8552(5) 0.6120(6) 0.0161(15) Uani 1 1 d U . .
H2 H 0.0656 0.8399 0.5729 0.019 Uiso 1 1 calc R . .
C3 C 0.1733(9) 0.9309(5) 0.6931(6) 0.0149(15) Uani 1 1 d U . .
H3 H 0.1525 0.9919 0.6654 0.018 Uiso 1 1 calc R . .
C4 C 0.3315(9) 0.9438(5) 0.7612(6) 0.0141(15) Uani 1 1 d U . .
C5 C 0.3949(9) 1.0304(5) 0.8134(6) 0.0151(15) Uani 1 1 d U . .
H5 H 0.3406 1.0847 0.8057 0.018 Uiso 1 1 calc R . .
C6 C 0.5400(9) 1.0352(6) 0.8771(6) 0.0183(16) Uani 1 1 d U . .
C7 C 0.6258(9) 0.9592(6) 0.8862(6) 0.0183(16) Uani 1 1 d U . .
H7 H 0.7259 0.9649 0.9283 0.022 Uiso 1 1 calc R . .
C8 C 0.5638(9) 0.8752(6) 0.8335(6) 0.0189(16) Uani 1 1 d U . .
H8 H 0.6223 0.8225 0.8375 0.023 Uiso 1 1 calc R . .
C9 C 0.4174(9) 0.8671(6) 0.7748(6) 0.0179(15) Uani 1 1 d U . .
C10 C 0.2810(9) 0.8841(6) 0.5437(6) 0.0176(16) Uani 1 1 d U . .
H10 H 0.3876 0.9069 0.5832 0.021 Uiso 1 1 calc R . .
C11 C 0.2936(10) 0.8001(6) 0.4747(6) 0.0209(17) Uani 1 1 d U . .
H11A H 0.1881 0.7740 0.4380 0.025 Uiso 1 1 calc R . .
H11B H 0.3402 0.7498 0.5116 0.025 Uiso 1 1 calc R . .
C12 C 0.3935(10) 0.8289(6) 0.4052(6) 0.0224(17) Uani 1 1 d U . .
H12A H 0.5006 0.8518 0.4417 0.027 Uiso 1 1 calc R . .
H12B H 0.3993 0.7731 0.3615 0.027 Uiso 1 1 calc R . .
C13 C 0.3262(10) 0.9064(6) 0.3469(6) 0.0246(18) Uani 1 1 d U . .
H13A H 0.4005 0.9294 0.3093 0.030 Uiso 1 1 calc R . .
H13B H 0.2283 0.8795 0.3014 0.030 Uiso 1 1 calc R . .
C14 C 0.2932(9) 0.9888(6) 0.4090(6) 0.0195(16) Uani 1 1 d U . .
C15 C 0.2169(10) 0.9651(6) 0.4888(6) 0.0194(17) Uani 1 1 d U . .
H15A H 0.1040 0.9482 0.4619 0.023 Uiso 1 1 calc R . .
H15B H 0.2295 1.0223 0.5345 0.023 Uiso 1 1 calc R . .
C16 C 0.0433(9) 0.9004(6) 0.7428(6) 0.0194(16) Uani 1 1 d U . .
H16A H -0.0577 0.8942 0.6955 0.023 Uiso 1 1 calc R . .
H16B H 0.0594 0.8372 0.7650 0.023 Uiso 1 1 calc R . .
C17 C 0.0341(9) 0.9676(6) 0.8274(6) 0.0199(16) Uani 1 1 d U . .
C18 C 0.0052(10) 1.1265(6) 0.8786(6) 0.0218(17) Uani 1 1 d U . .
H18A H -0.0295 1.0946 0.9302 0.026 Uiso 1 1 calc R . .
H18B H -0.0748 1.1674 0.8517 0.026 Uiso 1 1 calc R . .
C19 C 0.1559(9) 1.1859(6) 0.9191(6) 0.0207(18) Uani 1 1 d U . .
H19A H 0.2319 1.1468 0.9525 0.031 Uiso 1 1 calc R . .
H19B H 0.1401 1.2370 0.9643 0.031 Uiso 1 1 calc R . .
H19C H 0.1950 1.2131 0.8673 0.031 Uiso 1 1 calc R . .
C1B C 0.1958(9) 0.2476(6) 0.6293(6) 0.0176(16) Uani 1 1 d U . .
C2B C 0.1451(9) 0.3387(6) 0.5901(6) 0.0171(16) Uani 1 1 d U . .
H2B H 0.0377 0.3243 0.5485 0.020 Uiso 1 1 calc R . .
C3B C 0.1368(9) 0.4074(6) 0.6757(6) 0.0166(15) Uani 1 1 d U . .
H3B H 0.1105 0.4695 0.6522 0.020 Uiso 1 1 calc R . .
C4B C 0.2968(9) 0.4219(6) 0.7437(6) 0.0164(15) Uani 1 1 d U . .
C5B C 0.3592(9) 0.5066(6) 0.7956(6) 0.0171(16) Uani 1 1 d U . .
H5B H 0.3032 0.5604 0.7898 0.021 Uiso 1 1 calc R . .
C6B C 0.5063(10) 0.5122(6) 0.8571(6) 0.0193(16) Uani 1 1 d U . .
C7B C 0.5911(10) 0.4349(6) 0.8655(6) 0.0218(17) Uani 1 1 d U . .
H7B H 0.6912 0.4398 0.9076 0.026 Uiso 1 1 calc R . .
C8B C 0.5276(9) 0.3510(6) 0.8119(6) 0.0198(16) Uani 1 1 d U . .
H8B H 0.5847 0.2976 0.8160 0.024 Uiso 1 1 calc R . .
C9B C 0.3811(9) 0.3443(6) 0.7523(6) 0.0173(15) Uani 1 1 d U . .
C10B C 0.2558(9) 0.3738(6) 0.5270(6) 0.0172(16) Uani 1 1 d U . .
H10B H 0.3632 0.3886 0.5685 0.021 Uiso 1 1 calc R . .
C11B C 0.2606(10) 0.2978(6) 0.4472(6) 0.0210(17) Uani 1 1 d U . .
H11C H 0.2959 0.2403 0.4759 0.025 Uiso 1 1 calc R . .
H11D H 0.1543 0.2808 0.4068 0.025 Uiso 1 1 calc R . .
C12B C 0.3690(10) 0.3312(6) 0.3854(6) 0.0224(17) Uani 1 1 d U . .
H12C H 0.3683 0.2804 0.3345 0.027 Uiso 1 1 calc R . .
H12D H 0.4765 0.3444 0.4251 0.027 Uiso 1 1 calc R . .
C13B C 0.3204(11) 0.4202(6) 0.3399(6) 0.0255(18) Uani 1 1 d U . .
H13C H 0.4016 0.4449 0.3078 0.031 Uiso 1 1 calc R . .
H13D H 0.2224 0.4036 0.2904 0.031 Uiso 1 1 calc R . .
C14B C 0.2963(9) 0.4961(6) 0.4115(6) 0.0210(17) Uani 1 1 d U . .
C15B C 0.2056(10) 0.4639(6) 0.4841(6) 0.0195(17) Uani 1 1 d U . .
H15C H 0.0934 0.4530 0.4526 0.023 Uiso 1 1 calc R . .
H15D H 0.2194 0.5152 0.5365 0.023 Uiso 1 1 calc R . .
C16B C 0.0103(9) 0.3686(6) 0.7235(6) 0.0172(16) Uani 1 1 d U . .
H16C H -0.0910 0.3646 0.6767 0.021 Uiso 1 1 calc R . .
H16D H 0.0292 0.3033 0.7378 0.021 Uiso 1 1 calc R . .
C17B C -0.0047(9) 0.4224(5) 0.8136(6) 0.0168(16) Uani 1 1 d U . .
C18B C 0.0201(11) 0.5759(6) 0.8954(6) 0.0227(18) Uani 1 1 d U . .
H18C H 0.0984 0.5577 0.9496 0.027 Uiso 1 1 calc R . .
H18D H -0.0833 0.5678 0.9112 0.027 Uiso 1 1 calc R . .
C19B C 0.0594(12) 0.6767(6) 0.8798(7) 0.034(2) Uani 1 1 d U . .
H19D H 0.1579 0.6833 0.8593 0.051 Uiso 1 1 calc R . .
H19E H 0.0697 0.7169 0.9396 0.051 Uiso 1 1 calc R . .
H19F H -0.0237 0.6961 0.8303 0.051 Uiso 1 1 calc R . .
O1 O 0.1651(7) 0.6866(4) 0.6306(4) 0.0249(14) Uani 1 1 d U . .
O2 O 0.3550(7) 0.7771(4) 0.7292(4) 0.0201(12) Uani 1 1 d U . .
O3 O 0.3225(7) 1.0701(4) 0.3926(4) 0.0273(14) Uani 1 1 d U . .
O4 O 0.0357(9) 0.9444(5) 0.9054(5) 0.0396(18) Uani 1 1 d U . .
O5 O 0.0203(7) 1.0555(4) 0.8037(4) 0.0192(12) Uani 1 1 d U . .
O1B O 0.1356(7) 0.1690(4) 0.5986(4) 0.0240(13) Uani 1 1 d U . .
O2B O 0.3194(6) 0.2557(4) 0.7054(4) 0.0185(12) Uani 1 1 d U . .
O3B O 0.3424(7) 0.5776(4) 0.4120(5) 0.0288(14) Uani 1 1 d U . .
O4B O -0.0311(7) 0.3874(4) 0.8823(4) 0.0255(14) Uani 1 1 d U . .
O5B O 0.0185(6) 0.5172(4) 0.8100(4) 0.0177(12) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Br1 C6 1.909(8) . ?
Br1B C6B 1.902(8) . ?
C1 O1 1.195(10) . ?
C1 O2 1.360(10) . ?
C1 C2 1.534(11) . ?
C2 C3 1.532(11) . ?
C2 C10 1.557(11) . ?
C2 H2 1.0000 . ?
C3 C4 1.510(11) . ?
C3 C16 1.532(11) . ?
C3 H3 1.0000 . ?
C4 C9 1.390(11) . ?
C4 C5 1.398(11) . ?
C5 C6 1.397(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(11) . ?
C7 C8 1.369(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(11) . ?
C8 H8 0.9500 . ?
C9 O2 1.404(10) . ?
C10 C11 1.527(11) . ?
C10 C15 1.530(11) . ?
C10 H10 1.0000 . ?
C11 C12 1.529(12) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.513(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.217(10) . ?
C14 C15 1.500(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O4 1.192(10) . ?
C17 O5 1.333(10) . ?
C18 O5 1.459(10) . ?
C18 C19 1.489(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1B O1B 1.204(10) . ?
C1B O2B 1.357(10) . ?
C1B C2B 1.522(11) . ?
C2B C3B 1.535(11) . ?
C2B C10B 1.551(11) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.521(11) . ?
C3B C16B 1.524(11) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.373(11) . ?
C4B C9B 1.389(11) . ?
C5B C6B 1.396(11) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.388(12) . ?
C7B C8B 1.376(12) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.379(11) . ?
C8B H8B 0.9500 . ?
C9B O2B 1.392(10) . ?
C10B C15B 1.528(11) . ?
C10B C11B 1.530(11) . ?
C10B H10B 1.0000 . ?
C11B C12B 1.516(12) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.526(12) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.501(12) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B O3B 1.197(10) . ?
C14B C15B 1.524(12) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B C17B 1.495(11) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B O4B 1.198(10) . ?
C17B O5B 1.356(9) . ?
C18B O5B 1.432(10) . ?
C18B C19B 1.494(12) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?

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
O1 C1 O2 117.7(7) . . ?
O1 C1 C2 126.0(8) . . ?
O2 C1 C2 116.3(7) . . ?
C3 C2 C1 108.9(6) . . ?
C3 C2 C10 114.9(7) . . ?
C1 C2 C10 108.6(6) . . ?
C3 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C10 C2 H2 108.1 . . ?
C4 C3 C2 108.6(6) . . ?
C4 C3 C16 112.0(7) . . ?
C2 C3 C16 109.1(6) . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C16 C3 H3 109.0 . . ?
C9 C4 C5 118.0(7) . . ?
C9 C4 C3 119.5(7) . . ?
C5 C4 C3 122.4(7) . . ?
C6 C5 C4 118.5(7) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C7 C6 C5 122.3(7) . . ?
C7 C6 Br1 119.6(6) . . ?
C5 C6 Br1 118.1(6) . . ?
C8 C7 C6 118.7(7) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 120.1(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 122.2(8) . . ?
C8 C9 O2 117.4(7) . . ?
C4 C9 O2 120.5(7) . . ?
C11 C10 C15 110.7(7) . . ?
C11 C10 C2 111.2(7) . . ?
C15 C10 C2 109.4(6) . . ?
C11 C10 H10 108.5 . . ?
C15 C10 H10 108.5 . . ?
C2 C10 H10 108.5 . . ?
C10 C11 C12 111.3(7) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 111.2(7) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 112.5(7) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O3 C14 C15 122.0(8) . . ?
O3 C14 C13 121.3(8) . . ?
C15 C14 C13 116.6(7) . . ?
C14 C15 C10 114.6(7) . . ?
C14 C15 H15A 108.6 . . ?
C10 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C10 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C3 114.3(7) . . ?
C17 C16 H16A 108.7 . . ?
C3 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C3 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O4 C17 O5 124.0(8) . . ?
O4 C17 C16 124.0(8) . . ?
O5 C17 C16 112.0(7) . . ?
O5 C18 C19 111.2(7) . . ?
O5 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
O5 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1B C1B O2B 117.3(7) . . ?
O1B C1B C2B 125.6(7) . . ?
O2B C1B C2B 117.1(7) . . ?
C1B C2B C3B 107.3(7) . . ?
C1B C2B C10B 109.0(6) . . ?
C3B C2B C10B 116.0(7) . . ?
C1B C2B H2B 108.1 . . ?
C3B C2B H2B 108.1 . . ?
C10B C2B H2B 108.1 . . ?
C4B C3B C16B 112.3(7) . . ?
C4B C3B C2B 108.0(6) . . ?
C16B C3B C2B 110.0(6) . . ?
C4B C3B H3B 108.9 . . ?
C16B C3B H3B 108.9 . . ?
C2B C3B H3B 108.9 . . ?
C5B C4B C9B 119.8(7) . . ?
C5B C4B C3B 123.3(7) . . ?
C9B C4B C3B 116.9(7) . . ?
C4B C5B C6B 118.8(7) . . ?
C4B C5B H5B 120.6 . . ?
C6B C5B H5B 120.6 . . ?
C7B C6B C5B 121.5(8) . . ?
C7B C6B Br1B 119.7(6) . . ?
C5B C6B Br1B 118.8(6) . . ?
C8B C7B C6B 118.8(8) . . ?
C8B C7B H7B 120.6 . . ?
C6B C7B H7B 120.6 . . ?
C9B C8B C7B 120.1(8) . . ?
C9B C8B H8B 119.9 . . ?
C7B C8B H8B 119.9 . . ?
C8B C9B C4B 121.0(8) . . ?
C8B C9B O2B 117.0(7) . . ?
C4B C9B O2B 121.9(7) . . ?
C15B C10B C11B 110.0(7) . . ?
C15B C10B C2B 110.5(6) . . ?
C11B C10B C2B 111.3(7) . . ?
C15B C10B H10B 108.3 . . ?
C11B C10B H10B 108.3 . . ?
C2B C10B H10B 108.3 . . ?
C12B C11B C10B 111.7(7) . . ?
C12B C11B H11C 109.3 . . ?
C10B C11B H11C 109.3 . . ?
C12B C11B H11D 109.3 . . ?
C10B C11B H11D 109.3 . . ?
H11C C11B H11D 107.9 . . ?
C11B C12B C13B 111.5(7) . . ?
C11B C12B H12C 109.3 . . ?
C13B C12B H12C 109.3 . . ?
C11B C12B H12D 109.3 . . ?
C13B C12B H12D 109.3 . . ?
H12C C12B H12D 108.0 . . ?
C14B C13B C12B 112.6(7) . . ?
C14B C13B H13C 109.1 . . ?
C12B C13B H13C 109.1 . . ?
C14B C13B H13D 109.1 . . ?
C12B C13B H13D 109.1 . . ?
H13C C13B H13D 107.8 . . ?
O3B C14B C13B 123.1(8) . . ?
O3B C14B C15B 120.9(8) . . ?
C13B C14B C15B 116.0(7) . . ?
C14B C15B C10B 113.6(7) . . ?
C14B C15B H15C 108.8 . . ?
C10B C15B H15C 108.8 . . ?
C14B C15B H15D 108.8 . . ?
C10B C15B H15D 108.8 . . ?
H15C C15B H15D 107.7 . . ?
C17B C16B C3B 117.2(7) . . ?
C17B C16B H16C 108.0 . . ?
C3B C16B H16C 108.0 . . ?
C17B C16B H16D 108.0 . . ?
C3B C16B H16D 108.0 . . ?
H16C C16B H16D 107.2 . . ?
O4B C17B O5B 123.0(7) . . ?
O4B C17B C16B 125.0(7) . . ?
O5B C17B C16B 112.0(7) . . ?
O5B C18B C19B 108.9(7) . . ?
O5B C18B H18C 109.9 . . ?
C19B C18B H18C 109.9 . . ?
O5B C18B H18D 109.9 . . ?
C19B C18B H18D 109.9 . . ?
H18C C18B H18D 108.3 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C1 O2 C9 121.5(6) . . ?
C17 O5 C18 117.2(6) . . ?
C1B O2B C9B 120.1(6) . . ?
C17B O5B C18B 116.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.064
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.149

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-16b
_database_code_depnum_ccdc_archive 'CCDC 1440391'

_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
#============================================================================== 
# CBA-syn-16b
#==============================================================================
_audit_creation_date             'May 07 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 2-((3S*,4S*)-6-bromo-2-oxo-3-((R*)-3-oxocycloheptyl)chroman-4-yl)acetate
;
_chemical_name_common            ?
_chemical_melting_point          84.0
_chemical_formula_moiety         'C20 H23 Br O5'
_chemical_formula_sum            'C20 H23 Br O5'
_chemical_formula_weight         423.29
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0177(12)
_cell_length_b                   6.6196(6)
_cell_length_c                   23.898(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3020(10)
_cell_angle_gamma                90.00
_cell_volume                     1898.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5070
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.59
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.193
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_T_max  0.8797
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8856
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3352
_reflns_number_gt                3025
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0261P)²+1.0095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     236
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.290767(14) 0.80014(3) 0.517570(7) 0.01479(7) Uani 1 1 d . . .
C1 C 0.67272(14) 0.2126(3) 0.66868(7) 0.0118(4) Uani 1 1 d U . .
C2 C 0.70814(14) 0.4309(3) 0.67340(7) 0.0117(4) Uani 1 1 d U . .
H2 H 0.7528 0.4475 0.7097 0.014 Uiso 1 1 calc R . .
C3 C 0.60213(13) 0.5615(3) 0.67615(7) 0.0114(4) Uani 1 1 d U . .
H3 H 0.6232 0.7077 0.6763 0.014 Uiso 1 1 calc R . .
C4 C 0.52671(14) 0.5170(3) 0.62473(7) 0.0115(4) Uani 1 1 d U . .
C5 C 0.45607(14) 0.6598(3) 0.59856(7) 0.0121(4) Uani 1 1 d U . .
H5 H 0.4559 0.7954 0.6116 0.015 Uiso 1 1 calc R . .
C6 C 0.38584(13) 0.6017(3) 0.55311(7) 0.0125(4) Uani 1 1 d U . .
C7 C 0.38495(14) 0.4062(3) 0.53234(7) 0.0138(4) Uani 1 1 d U . .
H7 H 0.3359 0.3696 0.5014 0.017 Uiso 1 1 calc R . .
C8 C 0.45673(14) 0.2652(3) 0.55745(7) 0.0135(4) Uani 1 1 d U . .
H8 H 0.4588 0.1311 0.5434 0.016 Uiso 1 1 calc R . .
C9 C 0.52536(14) 0.3222(3) 0.60321(7) 0.0116(4) Uani 1 1 d U . .
C10 C 0.78449(14) 0.4872(3) 0.62529(7) 0.0114(4) Uani 1 1 d U . .
H10 H 0.7381 0.4874 0.5892 0.014 Uiso 1 1 calc R . .
C11 C 0.87727(15) 0.3303(3) 0.62094(8) 0.0178(4) Uani 1 1 d U . .
H11A H 0.8424 0.1998 0.6098 0.021 Uiso 1 1 calc R . .
H11B H 0.9142 0.3119 0.6587 0.021 Uiso 1 1 calc R . .
C12 C 0.96759(16) 0.3781(3) 0.57986(9) 0.0239(5) Uani 1 1 d U . .
H12A H 0.9306 0.4167 0.5433 0.029 Uiso 1 1 calc R . .
H12B H 1.0111 0.2538 0.5739 0.029 Uiso 1 1 calc R . .
C13 C 1.04865(16) 0.5478(3) 0.59905(9) 0.0280(5) Uani 1 1 d U . .
H13A H 1.0602 0.5424 0.6404 0.034 Uiso 1 1 calc R . .
H13B H 1.1216 0.5226 0.5831 0.034 Uiso 1 1 calc R . .
C14 C 1.00880(16) 0.7611(3) 0.58197(9) 0.0227(4) Uani 1 1 d U . .
H14A H 1.0451 0.8615 0.6077 0.027 Uiso 1 1 calc R . .
H14B H 1.0311 0.7908 0.5436 0.027 Uiso 1 1 calc R . .
C15 C 0.88450(16) 0.7795(3) 0.58370(8) 0.0178(4) Uani 1 1 d U . .
C16 C 0.83122(16) 0.7008(3) 0.63539(8) 0.0195(4) Uani 1 1 d U . .
H16A H 0.7702 0.7927 0.6451 0.023 Uiso 1 1 calc R . .
H16B H 0.8874 0.6984 0.6674 0.023 Uiso 1 1 calc R . .
C17 C 0.54386(14) 0.5115(3) 0.73008(7) 0.0139(4) Uani 1 1 d U . .
H17A H 0.5116 0.3741 0.7268 0.017 Uiso 1 1 calc R . .
H17B H 0.5999 0.5112 0.7621 0.017 Uiso 1 1 calc R . .
C18 C 0.45264(15) 0.6594(3) 0.74196(7) 0.0159(4) Uani 1 1 d U . .
C19 C 0.28760(17) 0.7030(4) 0.79112(9) 0.0303(5) Uani 1 1 d U . .
H19A H 0.2278 0.6983 0.7609 0.036 Uiso 1 1 calc R . .
H19B H 0.3120 0.8450 0.7962 0.036 Uiso 1 1 calc R . .
C20 C 0.24558(18) 0.6222(4) 0.84463(9) 0.0362(6) Uani 1 1 d U . .
H20A H 0.2271 0.4788 0.8400 0.054 Uiso 1 1 calc R . .
H20B H 0.1788 0.6972 0.8540 0.054 Uiso 1 1 calc R . .
H20C H 0.3034 0.6379 0.8749 0.054 Uiso 1 1 calc R . .
O1 O 0.71181(10) 0.07496(19) 0.69613(5) 0.0156(3) Uani 1 1 d U . .
O2 O 0.58960(10) 0.16693(17) 0.62918(5) 0.0132(3) Uani 1 1 d U . .
O3 O 0.82758(12) 0.8481(2) 0.54481(6) 0.0297(4) Uani 1 1 d U . .
O4 O 0.44555(12) 0.8288(2) 0.72461(6) 0.0286(3) Uani 1 1 d U . .
O5 O 0.38121(11) 0.5770(2) 0.77658(6) 0.0255(3) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Br1 C6 1.9079(17) . ?
C1 O1 1.202(2) . ?
C1 O2 1.368(2) . ?
C1 C2 1.509(2) . ?
C2 C3 1.544(2) . ?
C2 C10 1.557(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.513(2) . ?
C3 C17 1.538(2) . ?
C3 H3 1.0000 . ?
C4 C9 1.388(3) . ?
C4 C5 1.394(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 O2 1.408(2) . ?
C10 C11 1.532(2) . ?
C10 C16 1.536(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.538(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.539(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.502(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.210(2) . ?
C15 C16 1.516(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.509(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O4 1.197(2) . ?
C18 O5 1.342(2) . ?
C19 O5 1.458(2) . ?
C19 C20 1.500(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O1 C1 O2 117.14(16) . . ?
O1 C1 C2 125.82(16) . . ?
O2 C1 C2 117.04(14) . . ?
C1 C2 C3 108.04(14) . . ?
C1 C2 C10 110.46(13) . . ?
C3 C2 C10 114.85(14) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C10 C2 H2 107.7 . . ?
C4 C3 C17 111.00(13) . . ?
C4 C3 C2 108.26(14) . . ?
C17 C3 C2 109.37(14) . . ?
C4 C3 H3 109.4 . . ?
C17 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C9 C4 C5 118.03(15) . . ?
C9 C4 C3 118.39(15) . . ?
C5 C4 C3 123.56(16) . . ?
C6 C5 C4 119.29(16) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 121.99(16) . . ?
C7 C6 Br1 119.42(13) . . ?
C5 C6 Br1 118.58(13) . . ?
C8 C7 C6 118.86(16) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 C7 119.16(17) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 122.66(16) . . ?
C8 C9 O2 115.87(15) . . ?
C4 C9 O2 121.36(15) . . ?
C11 C10 C16 111.97(14) . . ?
C11 C10 C2 110.50(14) . . ?
C16 C10 C2 109.26(14) . . ?
C11 C10 H10 108.3 . . ?
C16 C10 H10 108.3 . . ?
C2 C10 H10 108.3 . . ?
C10 C11 C12 116.55(15) . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C11 C12 C13 114.70(17) . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 114.11(17) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 111.24(16) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O3 C15 C14 121.91(18) . . ?
O3 C15 C16 120.53(17) . . ?
C14 C15 C16 117.52(17) . . ?
C15 C16 C10 110.86(15) . . ?
C15 C16 H16A 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C3 112.88(15) . . ?
C18 C17 H17A 109.0 . . ?
C3 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C3 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O4 C18 O5 123.99(17) . . ?
O4 C18 C17 125.49(17) . . ?
O5 C18 C17 110.49(16) . . ?
O5 C19 C20 107.54(18) . . ?
O5 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O5 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O2 C9 120.20(13) . . ?
C18 O5 C19 116.36(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052

