# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mmpg130730
_database_code_depnum_ccdc_archive 'CCDC 957679'
_audit_update_record             
;
2013-08-27 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.4761(3)
_cell_length_b                   6.4856(2)
_cell_length_c                   19.7055(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.130(2)
_cell_angle_gamma                90.00
_cell_volume                     1113.71(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5547
_cell_measurement_theta_min      4.88
_cell_measurement_theta_max      66.67

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7604
_exptl_absorpt_correction_T_max  0.9520
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Cu-ImuS microfocus tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9304
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.88
_diffrn_reflns_theta_max         66.71
_reflns_number_total             1953
_reflns_number_gt                1814
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2σ(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)+(0.1155P)²+0.9569P] 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         1953
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1829
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
C1 C -0.0887(2) 0.2836(3) 0.13952(12) 0.0245(5) Uani 1 1 d . . .
C2 C 0.0519(3) 0.2845(3) 0.21098(12) 0.0243(5) Uani 1 1 d . . .
C3 C 0.1844(2) 0.3454(4) 0.19043(12) 0.0275(5) Uani 1 1 d . . .
H3 H 0.2745 0.3976 0.2338 0.033 Uiso 1 1 calc R . .
C4 C 0.2215(2) 0.1430(4) 0.15868(12) 0.0266(5) Uani 1 1 d . . .
H4 H 0.2379 0.0317 0.1961 0.032 Uiso 1 1 calc R . .
C5 C 0.0832(2) 0.0820(4) 0.08864(11) 0.0263(5) Uani 1 1 d . . .
H5A H 0.0753 0.1786 0.0484 0.032 Uiso 1 1 calc R . .
H5B H 0.1004 -0.0579 0.0733 0.032 Uiso 1 1 calc R . .
C6 C -0.0674(2) 0.0839(3) 0.09933(11) 0.0255(5) Uani 1 1 d . . .
H6A H -0.0714 -0.0384 0.1286 0.031 Uiso 1 1 calc R . .
H6B H -0.1536 0.0735 0.0505 0.031 Uiso 1 1 calc R . .
C7 C -0.2414(3) 0.2862(4) 0.14702(14) 0.0338(6) Uani 1 1 d . . .
H7A H -0.2521 0.1605 0.1722 0.051 Uiso 1 1 calc R . .
H7B H -0.3245 0.2929 0.0979 0.051 Uiso 1 1 calc R . .
H7C H -0.2465 0.4070 0.1758 0.051 Uiso 1 1 calc R . .
C8 C -0.0566(3) 0.4634(3) 0.09803(11) 0.0262(5) Uani 1 1 d . . .
C9 C 0.1134(3) 0.5130(4) 0.13166(13) 0.0306(6) Uani 1 1 d . . .
H9A H 0.1314 0.6517 0.1544 0.037 Uiso 1 1 calc R . .
H9B H 0.1576 0.5079 0.0938 0.037 Uiso 1 1 calc R . .
C10 C 0.3673(3) 0.1602(4) 0.14344(14) 0.0337(6) Uani 1 1 d . . .
H10A H 0.3461 0.2439 0.0985 0.040 Uiso 1 1 calc R . .
H10B H 0.4482 0.2306 0.1853 0.040 Uiso 1 1 calc R . .
C11 C 0.4227(3) -0.0498(4) 0.13300(13) 0.0306(6) Uani 1 1 d . . .
C12 C 0.5350(4) -0.2456(4) 0.06685(16) 0.0437(7) Uani 1 1 d . . .
H12A H 0.6275 -0.2720 0.1112 0.066 Uiso 1 1 calc R . .
H12B H 0.5626 -0.2341 0.0240 0.066 Uiso 1 1 calc R . .
H12C H 0.4624 -0.3597 0.0592 0.066 Uiso 1 1 calc R . .
O1 O 0.0586(2) 0.2344(2) 0.27093(8) 0.0305(5) Uani 1 1 d . . .
O2 O -0.1515(2) 0.5509(3) 0.04511(9) 0.0397(5) Uani 1 1 d . . .
O3 O 0.4324(2) -0.1986(3) 0.17193(11) 0.0458(5) Uani 1 1 d . . .
O4 O 0.4650(2) -0.0564(3) 0.07587(10) 0.0378(5) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.510(3) . ?
C1 C2 1.512(3) . ?
C1 C8 1.522(3) . ?
C1 C6 1.572(3) . ?
C2 O1 1.203(3) . ?
C2 C3 1.515(3) . ?
C3 C9 1.537(3) . ?
C3 C4 1.552(3) . ?
C3 H3 1.0000 . ?
C4 C10 1.528(3) . ?
C4 C5 1.536(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.217(3) . ?
C8 C9 1.516(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.502(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.214(3) . ?
C11 O4 1.336(3) . ?
C12 O4 1.439(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C7 C1 C2 115.90(18) . . ?
C7 C1 C8 116.43(19) . . ?
C2 C1 C8 101.99(17) . . ?
C7 C1 C6 112.09(18) . . ?
C2 C1 C6 103.40(17) . . ?
C8 C1 C6 105.55(17) . . ?
O1 C2 C1 126.9(2) . . ?
O1 C2 C3 127.1(2) . . ?
C1 C2 C3 105.81(17) . . ?
C2 C3 C9 102.81(17) . . ?
C2 C3 C4 103.30(18) . . ?
C9 C3 C4 113.30(17) . . ?
C2 C3 H3 112.2 . . ?
C9 C3 H3 112.2 . . ?
C4 C3 H3 112.2 . . ?
C10 C4 C5 111.11(18) . . ?
C10 C4 C3 112.52(19) . . ?
C5 C4 C3 109.37(17) . . ?
C10 C4 H4 107.9 . . ?
C5 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
C6 C5 C4 112.90(17) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C1 112.92(17) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 125.2(2) . . ?
O2 C8 C1 125.5(2) . . ?
C9 C8 C1 109.28(18) . . ?
C8 C9 C3 104.79(18) . . ?
C8 C9 H9A 110.8 . . ?
C3 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C3 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C11 C10 C4 110.6(2) . . ?
C11 C10 H10A 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O3 C11 O4 122.3(2) . . ?
O3 C11 C10 125.3(2) . . ?
O4 C11 C10 112.4(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 O4 C12 115.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 O1 20.8(3) . . . . ?
C8 C1 C2 O1 148.3(2) . . . . ?
C6 C1 C2 O1 -102.3(2) . . . . ?
C7 C1 C2 C3 -163.5(2) . . . . ?
C8 C1 C2 C3 -36.0(2) . . . . ?
C6 C1 C2 C3 73.4(2) . . . . ?
O1 C2 C3 C9 -144.8(2) . . . . ?
C1 C2 C3 C9 39.5(2) . . . . ?
O1 C2 C3 C4 97.1(2) . . . . ?
C1 C2 C3 C4 -78.61(19) . . . . ?
C2 C3 C4 C10 -172.36(18) . . . . ?
C9 C3 C4 C10 77.2(2) . . . . ?
C2 C3 C4 C5 63.6(2) . . . . ?
C9 C3 C4 C5 -46.8(2) . . . . ?
C10 C4 C5 C6 -174.28(19) . . . . ?
C3 C4 C5 C6 -49.5(2) . . . . ?
C4 C5 C6 C1 46.5(2) . . . . ?
C7 C1 C6 C5 177.84(18) . . . . ?
C2 C1 C6 C5 -56.6(2) . . . . ?
C8 C1 C6 C5 50.1(2) . . . . ?
C7 C1 C8 O2 -35.5(3) . . . . ?
C2 C1 C8 O2 -162.7(2) . . . . ?
C6 C1 C8 O2 89.6(2) . . . . ?
C7 C1 C8 C9 146.1(2) . . . . ?
C2 C1 C8 C9 18.9(2) . . . . ?
C6 C1 C8 C9 -88.8(2) . . . . ?
O2 C8 C9 C3 -173.8(2) . . . . ?
C1 C8 C9 C3 4.6(2) . . . . ?
C2 C3 C9 C8 -26.4(2) . . . . ?
C4 C3 C9 C8 84.4(2) . . . . ?
C5 C4 C10 C11 -72.5(2) . . . . ?
C3 C4 C10 C11 164.50(18) . . . . ?
C4 C10 C11 O3 -45.4(3) . . . . ?
C4 C10 C11 O4 136.0(2) . . . . ?
O3 C11 O4 C12 -5.1(3) . . . . ?
C10 C11 O4 C12 173.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        66.71
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_mmpg140923
_database_code_depnum_ccdc_archive 'CCDC 1026312'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Bridge 2 allyl'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 O4'
_chemical_formula_sum            'C21 H26 O4'
_chemical_formula_weight         342.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.5756(9)
_cell_length_b                   6.3249(2)
_cell_length_c                   21.7126(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.223(2)
_cell_angle_gamma                90
_cell_volume                     1814.91(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9182
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12257
_diffrn_reflns_av_unetI/netI     0.1167
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.541
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4137
_reflns_number_gt                2447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1134P)²+0.1555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4137
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.1933
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3287(2) 0.1481(4) 0.46194(14) 0.0232(7) Uani 1 1 d . . . . .
C2 C 0.3918(2) 0.0948(4) 0.41314(14) 0.0231(7) Uani 1 1 d . . . . .
H2 H 0.4233 -0.0483 0.4217 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3071(2) 0.0917(4) 0.35167(14) 0.0232(7) Uani 1 1 d . . . . .
H3 H 0.3364 0.0933 0.3134 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2407(2) -0.1038(4) 0.35205(14) 0.0253(7) Uani 1 1 d . . . . .
H4A H 0.1860 -0.1049 0.3131 0.030 Uiso 1 1 calc R U . . .
H4B H 0.2821 -0.2325 0.3519 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1941(2) -0.1086(5) 0.40964(14) 0.0258(7) Uani 1 1 d . . . . .
H5A H 0.1668 -0.2519 0.4136 0.031 Uiso 1 1 calc R U . . .
H5B H 0.1366 -0.0082 0.4027 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2689(2) -0.0518(5) 0.47214(14) 0.0252(7) Uani 1 1 d . . . . .
H6 H 0.3185 -0.1706 0.4826 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2573(2) 0.3266(4) 0.42988(14) 0.0242(7) Uani 1 1 d . . . . .
H7A H 0.2846 0.4668 0.4453 0.029 Uiso 1 1 calc R U . . .
H7B H 0.1892 0.3102 0.4385 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2528(2) 0.3025(4) 0.35842(14) 0.0246(7) Uani 1 1 d . . . . .
H8 H 0.2951 0.4182 0.3466 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4705(3) 0.2572(5) 0.40724(15) 0.0273(7) Uani 1 1 d . . . . .
C10 C 0.5396(2) 0.2154(5) 0.36372(14) 0.0268(7) Uani 1 1 d . . . . .
C11 C 0.6023(3) 0.3782(5) 0.35249(15) 0.0319(8) Uani 1 1 d . . . . .
H11 H 0.6001 0.5119 0.3721 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6678(3) 0.3467(6) 0.31297(17) 0.0391(9) Uani 1 1 d . . . . .
H12 H 0.7101 0.4585 0.3052 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6712(3) 0.1526(6) 0.28497(18) 0.0437(10) Uani 1 1 d . . . . .
H13 H 0.7165 0.1306 0.2581 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6098(3) -0.0101(6) 0.29543(16) 0.0398(9) Uani 1 1 d . . . . .
H14 H 0.6128 -0.1435 0.2759 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5434(3) 0.0209(5) 0.33454(15) 0.0313(8) Uani 1 1 d . . . . .
H15 H 0.5005 -0.0910 0.3414 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2151(3) -0.0327(5) 0.52642(15) 0.0304(8) Uani 1 1 d . . . . .
H16A H 0.2654 0.0056 0.5655 0.036 Uiso 1 1 calc R U . . .
H16B H 0.1649 0.0831 0.5169 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1622(3) -0.2322(5) 0.53799(16) 0.0361(9) Uani 1 1 d . . . . .
H17 H 0.1997 -0.3600 0.5408 0.043 Uiso 1 1 calc R U . . .
C18 C 0.0692(3) -0.2453(6) 0.54448(19) 0.0547(12) Uani 1 1 d . . . . .
H18A H 0.0289 -0.1215 0.5420 0.066 Uiso 1 1 calc R U . . .
H18B H 0.0418 -0.3788 0.5517 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1494(3) 0.3200(5) 0.31465(15) 0.0288(8) Uani 1 1 d . . . . .
C20 C 0.0659(3) 0.3178(6) 0.20451(16) 0.0395(9) Uani 1 1 d . . . . .
H20A H 0.0424 0.4664 0.2000 0.047 Uiso 1 1 calc R U . . .
H20B H 0.0115 0.2292 0.2145 0.047 Uiso 1 1 calc R U . . .
C21 C 0.0919(3) 0.2443(7) 0.14576(18) 0.0558(12) Uani 1 1 d . . . . .
H21A H 0.1460 0.3330 0.1366 0.084 Uiso 1 1 calc R U . . .
H21B H 0.0321 0.2539 0.1107 0.084 Uiso 1 1 calc R U . . .
H21C H 0.1149 0.0971 0.1509 0.084 Uiso 1 1 calc R U . . .
O1 O 0.38893(18) 0.2041(4) 0.52310(10) 0.0290(6) Uani 1 1 d . . . . .
O2 O 0.47602(18) 0.4256(4) 0.43554(11) 0.0391(7) Uani 1 1 d . . . . .
O3 O 0.0701(2) 0.3479(4) 0.32953(12) 0.0501(7) Uani 1 1 d . . . . .
O4 O 0.15797(17) 0.2999(4) 0.25450(10) 0.0352(6) Uani 1 1 d . . . . .
H1 H 0.422(3) 0.307(6) 0.520(2) 0.061(14) Uiso 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 1.436(4) . ?
C1 C2 1.545(4) . ?
C1 C6 1.545(4) . ?
C1 C7 1.546(4) . ?
C2 C9 1.509(4) . ?
C2 C3 1.549(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.531(4) . ?
C3 C8 1.547(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.526(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.540(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C16 1.526(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.546(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C19 1.508(5) . ?
C8 H8 1.0000 . ?
C9 O2 1.224(3) . ?
C9 C10 1.500(4) . ?
C10 C15 1.390(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.501(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.305(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 O3 1.206(4) . ?
C19 O4 1.343(4) . ?
C20 O4 1.460(4) . ?
C20 C21 1.474(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O1 H1 0.80(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 113.6(2) . . ?
O1 C1 C6 106.0(2) . . ?
C2 C1 C6 108.2(2) . . ?
O1 C1 C7 113.7(2) . . ?
C2 C1 C7 103.8(2) . . ?
C6 C1 C7 111.5(2) . . ?
C9 C2 C1 115.1(2) . . ?
C9 C2 C3 109.6(2) . . ?
C1 C2 C3 100.1(2) . . ?
C9 C2 H2 110.5 . . ?
C1 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C4 C3 C8 113.6(2) . . ?
C4 C3 C2 109.1(2) . . ?
C8 C3 C2 100.6(2) . . ?
C4 C3 H3 111.0 . . ?
C8 C3 H3 111.0 . . ?
C2 C3 H3 111.0 . . ?
C5 C4 C3 112.1(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 113.8(3) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C16 C6 C5 111.3(3) . . ?
C16 C6 C1 113.9(2) . . ?
C5 C6 C1 109.1(2) . . ?
C16 C6 H6 107.4 . . ?
C5 C6 H6 107.4 . . ?
C1 C6 H6 107.4 . . ?
C1 C7 C8 104.9(2) . . ?
C1 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
C1 C7 H7B 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
C19 C8 C7 116.3(3) . . ?
C19 C8 C3 113.5(2) . . ?
C7 C8 C3 105.6(2) . . ?
C19 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C3 C8 H8 107.0 . . ?
O2 C9 C10 119.6(3) . . ?
O2 C9 C2 120.9(3) . . ?
C10 C9 C2 119.4(2) . . ?
C15 C10 C11 119.1(3) . . ?
C15 C10 C9 122.5(3) . . ?
C11 C10 C9 118.4(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C17 C16 C6 113.3(3) . . ?
C17 C16 H16A 108.9 . . ?
C6 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C6 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 125.7(3) . . ?
C18 C17 H17 117.1 . . ?
C16 C17 H17 117.1 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
O3 C19 O4 123.7(3) . . ?
O3 C19 C8 126.9(3) . . ?
O4 C19 C8 109.3(3) . . ?
O4 C20 C21 106.6(3) . . ?
O4 C20 H20A 110.4 . . ?
C21 C20 H20A 110.4 . . ?
O4 C20 H20B 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 O1 H1 110(3) . . ?
C19 O4 C20 117.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C9 -50.8(3) . . . . ?
C6 C1 C2 C9 -168.2(3) . . . . ?
C7 C1 C2 C9 73.2(3) . . . . ?
O1 C1 C2 C3 -168.2(2) . . . . ?
C6 C1 C2 C3 74.4(3) . . . . ?
C7 C1 C2 C3 -44.2(3) . . . . ?
C9 C2 C3 C4 167.7(2) . . . . ?
C1 C2 C3 C4 -70.9(3) . . . . ?
C9 C2 C3 C8 -72.6(3) . . . . ?
C1 C2 C3 C8 48.9(3) . . . . ?
C8 C3 C4 C5 -53.3(3) . . . . ?
C2 C3 C4 C5 58.1(3) . . . . ?
C3 C4 C5 C6 -44.4(3) . . . . ?
C4 C5 C6 C16 173.0(2) . . . . ?
C4 C5 C6 C1 46.4(3) . . . . ?
O1 C1 C6 C16 49.2(3) . . . . ?
C2 C1 C6 C16 171.4(3) . . . . ?
C7 C1 C6 C16 -75.0(3) . . . . ?
O1 C1 C6 C5 174.3(2) . . . . ?
C2 C1 C6 C5 -63.6(3) . . . . ?
C7 C1 C6 C5 50.0(3) . . . . ?
O1 C1 C7 C8 145.9(3) . . . . ?
C2 C1 C7 C8 22.0(3) . . . . ?
C6 C1 C7 C8 -94.3(3) . . . . ?
C1 C7 C8 C19 135.7(3) . . . . ?
C1 C7 C8 C3 8.8(3) . . . . ?
C4 C3 C8 C19 -48.1(3) . . . . ?
C2 C3 C8 C19 -164.5(3) . . . . ?
C4 C3 C8 C7 80.5(3) . . . . ?
C2 C3 C8 C7 -35.9(3) . . . . ?
C1 C2 C9 O2 -6.1(4) . . . . ?
C3 C2 C9 O2 105.7(3) . . . . ?
C1 C2 C9 C10 176.8(3) . . . . ?
C3 C2 C9 C10 -71.4(3) . . . . ?
O2 C9 C10 C15 174.2(3) . . . . ?
C2 C9 C10 C15 -8.6(5) . . . . ?
O2 C9 C10 C11 -5.6(5) . . . . ?
C2 C9 C10 C11 171.5(3) . . . . ?
C15 C10 C11 C12 -0.2(5) . . . . ?
C9 C10 C11 C12 179.6(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C10 -0.7(5) . . . . ?
C11 C10 C15 C14 0.8(5) . . . . ?
C9 C10 C15 C14 -179.1(3) . . . . ?
C5 C6 C16 C17 59.3(4) . . . . ?
C1 C6 C16 C17 -176.8(3) . . . . ?
C6 C16 C17 C18 -131.4(4) . . . . ?
C7 C8 C19 O3 -1.1(4) . . . . ?
C3 C8 C19 O3 121.8(3) . . . . ?
C7 C8 C19 O4 178.8(2) . . . . ?
C3 C8 C19 O4 -58.3(3) . . . . ?
O3 C19 O4 C20 1.4(4) . . . . ?
C8 C19 O4 C20 -178.5(2) . . . . ?
C21 C20 O4 C19 -167.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.80(4) 2.26(4) 2.829(3) 129(4) .
O1 H1 O2 0.80(4) 2.26(4) 2.983(3) 151(4) 3_666

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.124

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mmpg140728
_database_code_depnum_ccdc_archive 'CCDC 1026406'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Bridge 1 CH3 allyl COPh PG RB'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.237(10)
_cell_length_b                   13.706(11)
_cell_length_c                   10.137(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.864(16)
_cell_angle_gamma                90
_cell_volume                     1589(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1849
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      22.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5910
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14992
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         28.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3830
_reflns_number_gt                1893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1033P)²+0.0927P] 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         3830
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2321
_refine_ls_wR_factor_gt          0.1989
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3507(3) 0.0978(2) 0.1826(3) 0.0391(7) Uani 1 1 d . . . . .
C2 C 0.4317(3) 0.0982(2) 0.1005(3) 0.0383(7) Uani 1 1 d . . . . .
C3 C 0.5537(3) 0.0785(2) 0.2059(3) 0.0394(7) Uani 1 1 d . . . . .
H3 H 0.6088 0.0566 0.1590 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5935(3) 0.1752(2) 0.2889(3) 0.0398(7) Uani 1 1 d . . . . .
H4 H 0.5925 0.2279 0.2200 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5065(3) 0.2031(2) 0.3615(4) 0.0518(9) Uani 1 1 d . . . . .
H5A H 0.5191 0.1595 0.4434 0.062 Uiso 1 1 calc R U . . .
H5B H 0.5231 0.2707 0.3977 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3797(3) 0.1966(2) 0.2654(4) 0.0558(10) Uani 1 1 d . . . . .
H6A H 0.3617 0.2513 0.1971 0.067 Uiso 1 1 calc R U . . .
H6B H 0.3292 0.2036 0.3225 0.067 Uiso 1 1 calc R U . . .
C7 C 0.4032(3) 0.0181(2) 0.2896(3) 0.0430(8) Uani 1 1 d . . . . .
C8 C 0.5262(3) -0.0024(2) 0.2923(3) 0.0425(8) Uani 1 1 d . . . . .
H8A H 0.5297 -0.0669 0.2502 0.051 Uiso 1 1 calc R U . . .
H8B H 0.5830 -0.0016 0.3905 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2198(3) 0.0875(2) 0.1011(4) 0.0505(9) Uani 1 1 d . . . . .
H9A H 0.1777 0.0916 0.1682 0.061 Uiso 1 1 calc R U . . .
H9B H 0.1932 0.1426 0.0340 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1888(3) -0.0055(3) 0.0220(4) 0.0505(9) Uani 1 1 d . . . . .
H10 H 0.2155 -0.0150 -0.0543 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1274(3) -0.0753(3) 0.0493(5) 0.0697(11) Uani 1 1 d . . . . .
H11A H 0.0991 -0.0685 0.1248 0.084 Uiso 1 1 calc R U . . .
H11B H 0.1110 -0.1330 -0.0063 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7162(3) 0.1700(2) 0.4000(3) 0.0415(7) Uani 1 1 d . . . . .
H12A H 0.7280 0.2277 0.4622 0.050 Uiso 1 1 calc R U . . .
H12B H 0.7210 0.1114 0.4589 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8149(3) 0.1661(2) 0.3437(3) 0.0399(7) Uani 1 1 d . . . . .
C14 C 0.9356(3) 0.1502(2) 0.4453(3) 0.0385(7) Uani 1 1 d . . . . .
C15 C 0.9630(3) 0.1612(2) 0.5895(3) 0.0517(9) Uani 1 1 d . . . . .
H15 H 0.9047 0.1808 0.6257 0.062 Uiso 1 1 calc R U . . .
C16 C 1.0759(3) 0.1436(3) 0.6801(4) 0.0627(10) Uani 1 1 d . . . . .
H16 H 1.0952 0.1527 0.7787 0.075 Uiso 1 1 calc R U . . .
C17 C 1.1607(3) 0.1130(2) 0.6299(4) 0.0575(10) Uani 1 1 d . . . . .
H17 H 1.2375 0.1001 0.6940 0.069 Uiso 1 1 calc R U . . .
C18 C 1.1352(3) 0.1011(3) 0.4895(5) 0.0616(10) Uani 1 1 d . . . . .
H18 H 1.1941 0.0800 0.4552 0.074 Uiso 1 1 calc R U . . .
C19 C 1.0227(3) 0.1199(2) 0.3957(4) 0.0515(9) Uani 1 1 d . . . . .
H19 H 1.0050 0.1120 0.2971 0.062 Uiso 1 1 calc R U . . .
O1 O 0.4038(2) 0.11300(16) -0.0254(2) 0.0551(7) Uani 1 1 d . . . . .
O2 O 0.3551(2) -0.0214(2) 0.3595(2) 0.0621(7) Uani 1 1 d . . . . .
O3 O 0.7975(2) 0.17476(19) 0.2181(2) 0.0570(7) 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 C2 1.505(4) . ?
C1 C7 1.512(4) . ?
C1 C9 1.525(4) . ?
C1 C6 1.566(4) . ?
C2 O1 1.215(3) . ?
C2 C3 1.518(4) . ?
C3 C8 1.523(4) . ?
C3 C4 1.552(4) . ?
C3 H3 1.0000 . ?
C4 C12 1.524(4) . ?
C4 C5 1.544(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.512(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.200(4) . ?
C7 C8 1.522(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.481(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.306(5) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.220(3) . ?
C13 C14 1.486(4) . ?
C14 C15 1.387(4) . ?
C14 C19 1.394(5) . ?
C15 C16 1.380(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.354(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 101.8(2) . . ?
C2 C1 C9 118.2(3) . . ?
C7 C1 C9 114.7(3) . . ?
C2 C1 C6 103.0(3) . . ?
C7 C1 C6 106.4(2) . . ?
C9 C1 C6 111.4(2) . . ?
O1 C2 C1 125.9(3) . . ?
O1 C2 C3 127.4(3) . . ?
C1 C2 C3 106.7(2) . . ?
C2 C3 C8 99.8(2) . . ?
C2 C3 C4 105.7(2) . . ?
C8 C3 C4 113.6(2) . . ?
C2 C3 H3 112.3 . . ?
C8 C3 H3 112.3 . . ?
C4 C3 H3 112.3 . . ?
C12 C4 C5 109.0(3) . . ?
C12 C4 C3 113.4(2) . . ?
C5 C4 C3 109.4(3) . . ?
C12 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C6 C5 C4 113.7(3) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C1 112.4(3) . . ?
C5 C6 H6A 109.1 . . ?
C1 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O2 C7 C1 125.3(3) . . ?
O2 C7 C8 126.6(3) . . ?
C1 C7 C8 108.1(3) . . ?
C7 C8 C3 105.9(2) . . ?
C7 C8 H8A 110.5 . . ?
C3 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
C3 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C1 113.0(3) . . ?
C10 C9 H9A 109.0 . . ?
C1 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 124.9(4) . . ?
C11 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C13 C12 C4 115.6(3) . . ?
C13 C12 H12A 108.4 . . ?
C4 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C4 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
O3 C13 C14 119.9(3) . . ?
O3 C13 C12 121.7(3) . . ?
C14 C13 C12 118.3(3) . . ?
C15 C14 C19 118.9(3) . . ?
C15 C14 C13 121.5(3) . . ?
C19 C14 C13 119.5(3) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 121.1(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 O1 144.3(3) . . . . ?
C9 C1 C2 O1 17.7(4) . . . . ?
C6 C1 C2 O1 -105.5(3) . . . . ?
C7 C1 C2 C3 -36.8(3) . . . . ?
C9 C1 C2 C3 -163.3(3) . . . . ?
C6 C1 C2 C3 73.4(3) . . . . ?
O1 C2 C3 C8 -138.3(3) . . . . ?
C1 C2 C3 C8 42.7(3) . . . . ?
O1 C2 C3 C4 103.5(3) . . . . ?
C1 C2 C3 C4 -75.4(3) . . . . ?
C2 C3 C4 C12 -179.4(2) . . . . ?
C8 C3 C4 C12 72.2(3) . . . . ?
C2 C3 C4 C5 58.8(3) . . . . ?
C8 C3 C4 C5 -49.7(3) . . . . ?
C12 C4 C5 C6 -171.8(3) . . . . ?
C3 C4 C5 C6 -47.3(4) . . . . ?
C4 C5 C6 C1 48.6(4) . . . . ?
C2 C1 C6 C5 -59.5(4) . . . . ?
C7 C1 C6 C5 47.1(4) . . . . ?
C9 C1 C6 C5 172.8(3) . . . . ?
C2 C1 C7 O2 -164.2(3) . . . . ?
C9 C1 C7 O2 -35.3(4) . . . . ?
C6 C1 C7 O2 88.3(4) . . . . ?
C2 C1 C7 C8 15.8(3) . . . . ?
C9 C1 C7 C8 144.6(3) . . . . ?
C6 C1 C7 C8 -91.8(3) . . . . ?
O2 C7 C8 C3 -169.9(3) . . . . ?
C1 C7 C8 C3 10.1(3) . . . . ?
C2 C3 C8 C7 -31.2(3) . . . . ?
C4 C3 C8 C7 80.8(3) . . . . ?
C2 C1 C9 C10 61.4(4) . . . . ?
C7 C1 C9 C10 -58.7(4) . . . . ?
C6 C1 C9 C10 -179.7(3) . . . . ?
C1 C9 C10 C11 113.6(4) . . . . ?
C5 C4 C12 C13 -166.7(3) . . . . ?
C3 C4 C12 C13 71.1(3) . . . . ?
C4 C12 C13 O3 5.9(4) . . . . ?
C4 C12 C13 C14 -173.5(3) . . . . ?
O3 C13 C14 C15 165.6(3) . . . . ?
C12 C13 C14 C15 -15.0(4) . . . . ?
O3 C13 C14 C19 -16.8(4) . . . . ?
C12 C13 C14 C19 162.6(3) . . . . ?
C19 C14 C15 C16 1.0(5) . . . . ?
C13 C14 C15 C16 178.6(3) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C14 -0.5(5) . . . . ?
C15 C14 C19 C18 0.0(5) . . . . ?
C13 C14 C19 C18 -177.6(3) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

