# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_S3o
_database_code_depnum_ccdc_archive 'CCDC 1576709'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
{2-[3-Ethoxy-2-(methoxymethoxy)phenyl]cyclopropane-1,1-diyl}bis(phenylmethanone)
;
_chemical_name_common            ?
_chemical_melting_point_gt       405
_chemical_melting_point_lt       406
_chemical_formula_moiety         'C27 H26 O5'
_chemical_formula_sum            'C27 H26 O5'
_chemical_formula_weight         430.48

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.560(1)
_cell_length_b                   10.760(3)
_cell_length_c                   11.542(3)
_cell_angle_alpha                89.84(3)
_cell_angle_beta                 78.84(2)
_cell_angle_gamma                80.40(2)
_cell_volume                     1148.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      20
_cell_measurement_theta_max      22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8142
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_max         69.937
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4322
_reflns_number_gt                2568
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0400P)²+0.1663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0199(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4322
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O1 O 0.66430(19) 0.1134(2) 0.39583(14) 0.0904(7) Uani 1 1 d . . . . .
O2 O 0.41382(18) 0.1077(2) 0.08800(13) 0.0780(6) Uani 1 1 d . . . . .
O3 O 0.36293(14) 0.42539(15) 0.43054(11) 0.0534(4) Uani 1 1 d . . . . .
O4 O 0.30696(17) 0.37237(18) 0.62825(13) 0.0689(5) Uani 1 1 d . . . . .
O5 O 0.16495(16) 0.61517(15) 0.38484(13) 0.0618(4) Uani 1 1 d . . . . .
C1 C 0.5004(2) 0.1133(2) 0.26634(17) 0.0524(6) Uani 1 1 d . . . . .
C2 C 0.3874(3) 0.0399(2) 0.3274(2) 0.0686(7) Uani 1 1 d . . . . .
H2A H 0.3190 0.0176 0.2822 0.082 Uiso 1 1 calc R U . . .
H2B H 0.4157 -0.0229 0.3828 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3739(2) 0.1748(2) 0.36244(18) 0.0551(6) Uani 1 1 d . . . . .
H3A H 0.4010 0.1879 0.4386 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6465(2) 0.0820(2) 0.29953(18) 0.0591(6) Uani 1 1 d . . . . .
C5 C 0.7655(2) 0.0039(2) 0.21516(18) 0.0546(6) Uani 1 1 d . . . . .
C6 C 0.9074(3) 0.0071(3) 0.2239(2) 0.0658(7) Uani 1 1 d . . . . .
H6A H 0.9270 0.0602 0.2799 0.079 Uiso 1 1 calc R U . . .
C7 C 1.0192(3) -0.0679(3) 0.1501(2) 0.0794(9) Uani 1 1 d . . . . .
H7A H 1.1142 -0.0638 0.1552 0.095 Uiso 1 1 calc R U . . .
C8 C 0.9919(3) -0.1484(3) 0.0692(2) 0.0809(9) Uani 1 1 d . . . . .
H8A H 1.0683 -0.1999 0.0203 0.097 Uiso 1 1 calc R U . . .
C9 C 0.8520(3) -0.1536(3) 0.0600(2) 0.0762(8) Uani 1 1 d . . . . .
H9A H 0.8334 -0.2092 0.0057 0.091 Uiso 1 1 calc R U . . .
C10 C 0.7390(3) -0.0759(2) 0.13165(19) 0.0622(7) Uani 1 1 d . . . . .
H10A H 0.6444 -0.0774 0.1235 0.075 Uiso 1 1 calc R U . . .
C11 C 0.4917(2) 0.1530(2) 0.14247(18) 0.0570(6) Uani 1 1 d . . . . .
C12 C 0.5718(2) 0.2524(2) 0.09161(18) 0.0569(6) Uani 1 1 d . . . . .
C13 C 0.5949(3) 0.2671(3) -0.0302(2) 0.0752(9) Uani 1 1 d . . . . .
H13A H 0.5644 0.2120 -0.0781 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6627(3) 0.3628(4) -0.0794(2) 0.0896(10) Uani 1 1 d . . . . .
H14A H 0.6781 0.3719 -0.1608 0.108 Uiso 1 1 calc R U . . .
C15 C 0.7081(3) 0.4454(3) -0.0099(3) 0.0892(9) Uani 1 1 d . . . . .
H15A H 0.7532 0.5105 -0.0440 0.107 Uiso 1 1 calc R U . . .
C16 C 0.6865(3) 0.4313(3) 0.1105(2) 0.0781(8) Uani 1 1 d . . . . .
H16A H 0.7175 0.4867 0.1578 0.094 Uiso 1 1 calc R U . . .
C17 C 0.6194(3) 0.3358(3) 0.1607(2) 0.0666(7) Uani 1 1 d . . . . .
H17A H 0.6055 0.3267 0.2421 0.080 Uiso 1 1 calc R U . . .
C18 C 0.2601(2) 0.2765(2) 0.33417(17) 0.0527(6) Uani 1 1 d . . . . .
C19 C 0.1559(2) 0.2542(2) 0.27186(19) 0.0632(7) Uani 1 1 d . . . . .
H19A H 0.1567 0.1727 0.2449 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0518(2) 0.3504(3) 0.2493(2) 0.0667(7) Uani 1 1 d . . . . .
H20A H -0.0181 0.3330 0.2087 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0500(2) 0.4724(2) 0.28630(19) 0.0605(6) Uani 1 1 d . . . . .
H21A H -0.0203 0.5373 0.2700 0.073 Uiso 1 1 calc R U . . .
C22 C 0.1528(2) 0.4978(2) 0.34755(17) 0.0508(5) Uani 1 1 d . . . . .
C23 C 0.2571(2) 0.3993(2) 0.37233(16) 0.0477(5) Uani 1 1 d . . . . .
C24 C 0.3135(3) 0.4696(2) 0.55066(17) 0.0581(6) Uani 1 1 d . . . . .
H24A H 0.3783 0.5228 0.5709 0.070 Uiso 1 1 calc R U . . .
H24B H 0.2182 0.5206 0.5588 0.070 Uiso 1 1 calc R U . . .
C25 C 0.4459(3) 0.3145(3) 0.6481(2) 0.0866(9) Uani 1 1 d . . . . .
H25A H 0.4343 0.2516 0.7068 0.130 Uiso 1 1 calc R U . . .
H25B H 0.4935 0.3774 0.6752 0.130 Uiso 1 1 calc R U . . .
H25C H 0.5032 0.2757 0.5757 0.130 Uiso 1 1 calc R U . . .
C26 C 0.0433(3) 0.7131(2) 0.3896(2) 0.0689(7) Uani 1 1 d . . . . .
H26A H -0.0426 0.6879 0.4364 0.083 Uiso 1 1 calc R U . . .
H26B H 0.0261 0.7310 0.3107 0.083 Uiso 1 1 calc R U . . .
C27 C 0.0766(4) 0.8274(3) 0.4450(3) 0.0936(10) Uani 1 1 d . . . . .
H27A H -0.0050 0.8943 0.4524 0.140 Uiso 1 1 calc R U . . .
H27B H 0.1593 0.8536 0.3963 0.140 Uiso 1 1 calc R U . . .
H27C H 0.0971 0.8077 0.5218 0.140 Uiso 1 1 calc R 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
O1 C4 1.214(2) . ?
O2 C11 1.221(3) . ?
O3 C23 1.383(2) . ?
O3 C24 1.431(2) . ?
O4 C24 1.376(3) . ?
O4 C25 1.430(3) . ?
O5 C22 1.366(3) . ?
O5 C26 1.426(3) . ?
C1 C4 1.504(3) . ?
C1 C11 1.505(3) . ?
C1 C2 1.508(3) . ?
C1 C3 1.532(3) . ?
C2 C3 1.486(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C18 1.492(3) . ?
C3 H3A 0.9800 . ?
C4 C5 1.485(3) . ?
C5 C10 1.379(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.371(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.365(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.372(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.473(4) . ?
C12 C17 1.389(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.370(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.369(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.387(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.372(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.378(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.398(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.495(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C23 O3 C24 115.69(16) . . ?
C24 O4 C25 113.1(2) . . ?
C22 O5 C26 117.55(18) . . ?
C4 C1 C11 118.93(18) . . ?
C4 C1 C2 115.8(2) . . ?
C11 C1 C2 117.0(2) . . ?
C4 C1 C3 117.24(17) . . ?
C11 C1 C3 115.25(17) . . ?
C2 C1 C3 58.52(14) . . ?
C3 C2 C1 61.55(16) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C2 C3 C18 123.8(2) . . ?
C2 C3 C1 59.93(15) . . ?
C18 C3 C1 121.12(18) . . ?
C2 C3 H3A 113.9 . . ?
C18 C3 H3A 113.9 . . ?
C1 C3 H3A 113.9 . . ?
O1 C4 C5 120.8(2) . . ?
O1 C4 C1 120.67(19) . . ?
C5 C4 C1 118.36(17) . . ?
C10 C5 C6 118.9(2) . . ?
C10 C5 C4 122.0(2) . . ?
C6 C5 C4 119.0(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C5 C10 C9 120.4(2) . . ?
C5 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
O2 C11 C12 121.0(2) . . ?
O2 C11 C1 120.2(2) . . ?
C12 C11 C1 118.7(2) . . ?
C17 C12 C13 118.6(3) . . ?
C17 C12 C11 122.6(2) . . ?
C13 C12 C11 118.7(2) . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C12 120.8(2) . . ?
C16 C17 H17A 119.6 . . ?
C12 C17 H17A 119.6 . . ?
C23 C18 C19 118.1(2) . . ?
C23 C18 C3 118.82(19) . . ?
C19 C18 C3 123.1(2) . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C22 119.6(2) . . ?
C20 C21 H21A 120.2 . . ?
C22 C21 H21A 120.2 . . ?
O5 C22 C21 124.9(2) . . ?
O5 C22 C23 115.42(19) . . ?
C21 C22 C23 119.7(2) . . ?
O3 C23 C18 119.50(18) . . ?
O3 C23 C22 119.6(2) . . ?
C18 C23 C22 120.83(19) . . ?
O4 C24 O3 112.39(19) . . ?
O4 C24 H24A 109.1 . . ?
O3 C24 H24A 109.1 . . ?
O4 C24 H24B 109.1 . . ?
O3 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 C27 107.5(2) . . ?
O5 C26 H26A 110.2 . . ?
C27 C26 H26A 110.2 . . ?
O5 C26 H26B 110.2 . . ?
C27 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.038



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 2:1'
####################################################################### 
# 
# 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_4d'
_database_code_depnum_ccdc_archive 'CCDC 1576718'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
9-Methyl-8,10-dioxatricyclo[7.2.1.02,7]dodeca-2,4,6-trien-4-amine
;
_chemical_name_common            ?
_chemical_melting_point_gt       423
_chemical_melting_point_lt       424
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.5650(10)
_cell_length_b                   17.417(6)
_cell_length_c                   19.970(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1935.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      20
_cell_measurement_theta_max      22

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.735
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   PSI-SCAN
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2764
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.428
_diffrn_reflns_theta_max         69.869
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             1761
_reflns_number_gt                1234
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0458P)²+0.7802P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0160(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1761
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
N1 N 0.5861(4) 0.27826(11) 0.29223(11) 0.0528(5) Uani 1 1 d . . . . .
H1 H 0.438(6) 0.2779(16) 0.2742(15) 0.083(10) Uiso 1 1 d . . . . .
H2 H 0.630(5) 0.2358(16) 0.3156(13) 0.069(8) Uiso 1 1 d . . . . .
O1 O 0.6406(3) 0.64107(8) 0.36060(8) 0.0543(5) Uani 1 1 d . . . . .
O2 O 0.7562(3) 0.54716(7) 0.43615(7) 0.0458(4) Uani 1 1 d . . . . .
C1 C 0.6573(5) 0.66853(12) 0.47838(13) 0.0596(7) Uani 1 1 d . . . . .
H1A H 0.6263 0.6473 0.5219 0.089 Uiso 1 1 calc R U . . .
H1B H 0.8242 0.6819 0.4749 0.089 Uiso 1 1 calc R U . . .
H1C H 0.5609 0.7137 0.4721 0.089 Uiso 1 1 calc R U . . .
C2 C 0.5956(4) 0.61036(11) 0.42561(11) 0.0428(5) Uani 1 1 d . . . . .
C3 C 0.4658(5) 0.60983(12) 0.31441(11) 0.0525(6) Uani 1 1 d . . . . .
H3A H 0.5437 0.5902 0.2745 0.063 Uiso 1 1 calc R U . . .
H3B H 0.3497 0.6486 0.3014 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3456(4) 0.54575(11) 0.35302(10) 0.0417(5) Uani 1 1 d . . . . .
H4A H 0.1851 0.5332 0.3360 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3403(4) 0.58201(12) 0.42197(11) 0.0458(5) Uani 1 1 d . . . . .
H5A H 0.2254 0.6238 0.4245 0.055 Uiso 1 1 calc R U . . .
H5B H 0.3056 0.5446 0.4567 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5088(4) 0.47679(11) 0.35711(10) 0.0374(5) Uani 1 1 d . . . . .
C7 C 0.4680(4) 0.40844(11) 0.32276(10) 0.0424(5) Uani 1 1 d . . . . .
H7A H 0.3344 0.4043 0.2950 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6227(4) 0.34626(11) 0.32908(10) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.8232(4) 0.35390(11) 0.36985(11) 0.0457(5) Uani 1 1 d . . . . .
H9A H 0.9310 0.3133 0.3736 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8649(4) 0.42096(12) 0.40505(11) 0.0446(5) Uani 1 1 d . . . . .
H10A H 0.9985 0.4251 0.4328 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7072(4) 0.48179(11) 0.39882(10) 0.0380(5) 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
N1 C8 1.409(3) . ?
N1 H1 0.90(3) . ?
N1 H2 0.91(3) . ?
O1 C2 1.426(2) . ?
O1 C3 1.447(3) . ?
O2 C11 1.388(2) . ?
O2 C2 1.433(2) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C5 1.506(3) . ?
C3 C4 1.513(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.508(3) . ?
C4 C5 1.515(3) . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.386(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.389(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.388(3) . ?
C9 C10 1.383(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10A 0.9300 . ?

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
C8 N1 H1 110.4(18) . . ?
C8 N1 H2 112.2(16) . . ?
H1 N1 H2 116(3) . . ?
C2 O1 C3 108.73(16) . . ?
C11 O2 C2 115.38(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 108.19(16) . . ?
O1 C2 C1 110.22(17) . . ?
O2 C2 C1 105.82(18) . . ?
O1 C2 C5 104.17(17) . . ?
O2 C2 C5 110.09(16) . . ?
C1 C2 C5 118.09(19) . . ?
O1 C3 C4 104.47(17) . . ?
O1 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C6 C4 C3 110.43(18) . . ?
C6 C4 C5 107.13(17) . . ?
C3 C4 C5 99.46(17) . . ?
C6 C4 H4A 113.0 . . ?
C3 C4 H4A 113.0 . . ?
C5 C4 H4A 113.0 . . ?
C2 C5 C4 99.33(17) . . ?
C2 C5 H5A 111.9 . . ?
C4 C5 H5A 111.9 . . ?
C2 C5 H5B 111.9 . . ?
C4 C5 H5B 111.9 . . ?
H5A C5 H5B 109.6 . . ?
C11 C6 C7 118.65(19) . . ?
C11 C6 C4 117.54(17) . . ?
C7 C6 C4 123.79(19) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C9 C8 C7 118.47(18) . . ?
C9 C8 N1 120.2(2) . . ?
C7 C8 N1 121.2(2) . . ?
C10 C9 C8 120.95(19) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C6 120.81(18) . . ?
C10 C11 O2 117.12(18) . . ?
C6 C11 O2 122.07(17) . . ?

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
N1 H1 N1 0.90(3) 2.37(3) 3.254(2) 170(3) 6_556
N1 H2 O1 0.91(3) 2.27(3) 3.144(3) 161(2) 8_755

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 1576717'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point_gt       363
_chemical_melting_point_lt       364
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33

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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.139(3)
_cell_length_b                   10.399(6)
_cell_length_c                   14.357(5)
_cell_angle_alpha                80.36(4)
_cell_angle_beta                 69.86(3)
_cell_angle_gamma                89.98(4)
_cell_volume                     1398.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10972
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         25.972
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5486
_reflns_number_gt                2635
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0636P)²+0.4063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5486
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
N1 N 0.7524(2) 0.2746(2) 0.23183(18) 0.0650(7) Uani 1 1 d . . . . .
O1 O 0.1752(2) 0.5537(2) 0.27616(17) 0.0746(6) Uani 1 1 d . . . . .
O2 O 0.34947(18) 0.51952(16) 0.34689(13) 0.0550(5) Uani 1 1 d . . . . .
C1 C 0.1597(4) 0.6420(4) 0.4215(3) 0.0918(11) Uani 1 1 d . . . . .
H1A H 0.1172 0.5616 0.4656 0.138 Uiso 1 1 calc R U . . .
H1B H 0.0875 0.6962 0.4111 0.138 Uiso 1 1 calc R U . . .
H1C H 0.2134 0.6866 0.4513 0.138 Uiso 1 1 calc R U . . .
C2 C 0.2549(3) 0.6133(3) 0.3222(2) 0.0580(7) Uani 1 1 d . . . . .
C3 C 0.2404(3) 0.5897(3) 0.1690(3) 0.0772(9) Uani 1 1 d . . . . .
H3A H 0.1839 0.6490 0.1413 0.093 Uiso 1 1 calc R U . . .
H3B H 0.2529 0.5131 0.1372 0.093 Uiso 1 1 calc R U . . .
C4 C 0.3802(3) 0.6556(3) 0.1532(2) 0.0597(7) Uani 1 1 d . . . . .
H4A H 0.4182 0.7159 0.0886 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3385(3) 0.7253(3) 0.2440(2) 0.0664(8) Uani 1 1 d . . . . .
H5A H 0.4197 0.7543 0.2578 0.080 Uiso 1 1 calc R U . . .
H5B H 0.2816 0.7985 0.2362 0.080 Uiso 1 1 calc R U . . .
C6 C 0.4815(3) 0.5560(2) 0.16843(19) 0.0460(6) Uani 1 1 d . . . . .
C7 C 0.5958(3) 0.5213(3) 0.0931(2) 0.0528(7) Uani 1 1 d . . . . .
H7A H 0.6127 0.5615 0.0268 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6858(3) 0.4297(2) 0.11211(19) 0.0506(6) Uani 1 1 d . . . . .
H8A H 0.7617 0.4097 0.0590 0.061 Uiso 1 1 calc R U . . .
C9 C 0.6642(2) 0.3665(2) 0.21057(19) 0.0458(6) Uani 1 1 d . . . . .
C10 C 0.5479(3) 0.4001(2) 0.28746(19) 0.0467(6) Uani 1 1 d . . . . .
H10A H 0.5298 0.3597 0.3539 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4597(2) 0.4929(2) 0.26553(19) 0.0435(6) Uani 1 1 d . . . . .
C12 C 0.8775(3) 0.2445(3) 0.1545(2) 0.0641(8) Uani 1 1 d . . . . .
H12A H 0.8560 0.2421 0.0940 0.077 Uiso 1 1 calc R U . . .
H12B H 0.9035 0.1581 0.1767 0.077 Uiso 1 1 calc R U . . .
C13 C 1.0015(3) 0.3403(3) 0.1287(3) 0.0855(10) Uani 1 1 d . . . . .
H13A H 1.0807 0.3137 0.0776 0.128 Uiso 1 1 calc R U . . .
H13B H 1.0247 0.3425 0.1879 0.128 Uiso 1 1 calc R U . . .
H13C H 0.9782 0.4257 0.1042 0.128 Uiso 1 1 calc R U . . .
C14 C 0.7460(4) 0.2322(4) 0.3406(3) 0.1115(15) Uani 1 1 d . . . . .
H14A H 0.8394 0.2131 0.3412 0.134 Uiso 1 1 calc R U . . .
H14B H 0.7140 0.3028 0.3777 0.134 Uiso 1 1 calc R U . . .
C15 C 0.6539(6) 0.1208(5) 0.3875(4) 0.149(2) Uani 1 1 d . . . . .
H15A H 0.6561 0.0919 0.4540 0.224 Uiso 1 1 calc R U . . .
H15B H 0.6826 0.0526 0.3485 0.224 Uiso 1 1 calc R U . . .
H15C H 0.5600 0.1419 0.3919 0.224 Uiso 1 1 calc R U . . .
N2 N -0.2478(2) -0.1208(2) 0.76428(17) 0.0636(6) Uani 1 1 d . . . . .
O3 O 0.3248(2) 0.17544(19) 0.73099(15) 0.0665(5) Uani 1 1 d . . . . .
O4 O 0.15899(17) 0.17270(16) 0.65304(12) 0.0515(5) Uani 1 1 d . . . . .
C16 C 0.3550(3) 0.3234(3) 0.5792(2) 0.0780(9) Uani 1 1 d . . . . .
H16A H 0.4051 0.2593 0.5418 0.117 Uiso 1 1 calc R U . . .
H16B H 0.4205 0.3793 0.5912 0.117 Uiso 1 1 calc R U . . .
H16C H 0.3057 0.3747 0.5412 0.117 Uiso 1 1 calc R U . . .
C17 C 0.2520(3) 0.2562(2) 0.6776(2) 0.0511(6) Uani 1 1 d . . . . .
C18 C 0.2549(3) 0.1689(3) 0.8369(2) 0.0720(9) Uani 1 1 d . . . . .
H18A H 0.3094 0.2179 0.8645 0.086 Uiso 1 1 calc R U . . .
H18B H 0.2396 0.0791 0.8721 0.086 Uiso 1 1 calc R U . . .
C19 C 0.1170(3) 0.2290(3) 0.8458(2) 0.0590(7) Uani 1 1 d . . . . .
H19A H 0.0755 0.2630 0.9086 0.071 Uiso 1 1 calc R U . . .
C20 C 0.1651(3) 0.3372(3) 0.7520(2) 0.0634(8) Uani 1 1 d . . . . .
H20A H 0.0866 0.3725 0.7342 0.076 Uiso 1 1 calc R U . . .
H20B H 0.2214 0.4074 0.7596 0.076 Uiso 1 1 calc R U . . .
C21 C 0.0178(2) 0.1351(2) 0.82966(18) 0.0450(6) Uani 1 1 d . . . . .
C22 C -0.0988(3) 0.0671(2) 0.90398(19) 0.0513(6) Uani 1 1 d . . . . .
H22A H -0.1184 0.0785 0.9702 0.062 Uiso 1 1 calc R U . . .
C23 C -0.1872(3) -0.0166(2) 0.88425(19) 0.0493(6) Uani 1 1 d . . . . .
H23A H -0.2647 -0.0597 0.9367 0.059 Uiso 1 1 calc R U . . .
C24 C -0.1611(2) -0.0373(2) 0.78579(19) 0.0442(6) Uani 1 1 d . . . . .
C25 C -0.0415(2) 0.0289(2) 0.71024(18) 0.0444(6) Uani 1 1 d . . . . .
H25A H -0.0197 0.0163 0.6441 0.053 Uiso 1 1 calc R U . . .
C26 C 0.0445(2) 0.1126(2) 0.73269(18) 0.0421(6) Uani 1 1 d . . . . .
C27 C -0.3747(3) -0.1843(3) 0.8409(2) 0.0640(8) Uani 1 1 d . . . . .
H27A H -0.3548 -0.2149 0.9020 0.077 Uiso 1 1 calc R U . . .
H27B H -0.4012 -0.2603 0.8188 0.077 Uiso 1 1 calc R U . . .
C28 C -0.4983(3) -0.0984(3) 0.8654(3) 0.0828(10) Uani 1 1 d . . . . .
H28A H -0.5786 -0.1476 0.9159 0.124 Uiso 1 1 calc R U . . .
H28B H -0.5199 -0.0684 0.8056 0.124 Uiso 1 1 calc R U . . .
H28C H -0.4747 -0.0246 0.8901 0.124 Uiso 1 1 calc R U . . .
C29 C -0.2455(13) -0.0752(12) 0.6007(10) 0.110(4) Uiso 0.37 1 d . . P A 1
H29A H -0.2277 -0.1042 0.5377 0.164 Uiso 0.37 1 calc R U P A 1
H29B H -0.1945 0.0072 0.5892 0.164 Uiso 0.37 1 calc R U P A 1
H29C H -0.3445 -0.0651 0.6312 0.164 Uiso 0.37 1 calc R U P A 1
C30 C -0.1977(13) -0.1759(12) 0.6709(8) 0.081(3) Uiso 0.37 1 d . . P A 1
H30A H -0.2420 -0.2621 0.6801 0.097 Uiso 0.37 1 calc R U P A 1
H30B H -0.0962 -0.1805 0.6464 0.097 Uiso 0.37 1 calc R U P A 1
C31 C -0.2418(5) -0.1122(6) 0.6581(4) 0.0630(13) Uani 0.63 1 d . . P A 2
H31A H -0.3355 -0.1312 0.6583 0.076 Uiso 0.63 1 calc R U P A 2
H31B H -0.2119 -0.0235 0.6223 0.076 Uiso 0.63 1 calc R U P A 2
C32 C -0.1442(6) -0.2036(5) 0.6029(4) 0.0852(17) Uani 0.63 1 d . . P A 2
H32A H -0.1497 -0.1982 0.5370 0.128 Uiso 0.63 1 calc R U P A 2
H32B H -0.1705 -0.2913 0.6395 0.128 Uiso 0.63 1 calc R U P A 2
H32C H -0.0496 -0.1802 0.5969 0.128 Uiso 0.63 1 calc R U P 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
N1 C9 1.378(3) . ?
N1 C12 1.444(3) . ?
N1 C14 1.529(5) . ?
O1 C2 1.406(3) . ?
O1 C3 1.433(4) . ?
O2 C11 1.378(3) . ?
O2 C2 1.454(3) . ?
C1 C2 1.499(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C5 1.499(4) . ?
C3 C4 1.503(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.501(3) . ?
C4 C5 1.530(4) . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.380(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.378(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.398(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.401(3) . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9300 . ?
C12 C13 1.505(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.405(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 C24 1.378(3) . ?
N2 C27 1.444(3) . ?
N2 C30 1.474(12) . ?
N2 C31 1.493(6) . ?
O3 C17 1.418(3) . ?
O3 C18 1.429(3) . ?
O4 C26 1.376(3) . ?
O4 C17 1.449(3) . ?
C16 C17 1.494(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C20 1.509(4) . ?
C18 C19 1.504(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C21 1.501(3) . ?
C19 C20 1.536(4) . ?
C19 H19A 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.384(3) . ?
C21 C26 1.384(3) . ?
C22 C23 1.378(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.399(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.402(3) . ?
C25 C26 1.382(3) . ?
C25 H25A 0.9300 . ?
C27 C28 1.515(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.526(15) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.490(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
C9 N1 C12 121.8(2) . . ?
C9 N1 C14 119.6(2) . . ?
C12 N1 C14 116.1(2) . . ?
C2 O1 C3 108.8(2) . . ?
C11 O2 C2 115.2(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 108.6(2) . . ?
O1 C2 C5 105.3(2) . . ?
O2 C2 C5 109.7(2) . . ?
O1 C2 C1 109.6(2) . . ?
O2 C2 C1 105.3(2) . . ?
C5 C2 C1 118.2(3) . . ?
O1 C3 C4 104.7(2) . . ?
O1 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
O1 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C6 C4 C3 110.4(2) . . ?
C6 C4 C5 107.0(2) . . ?
C3 C4 C5 99.9(2) . . ?
C6 C4 H4A 112.9 . . ?
C3 C4 H4A 112.9 . . ?
C5 C4 H4A 112.9 . . ?
C2 C5 C4 97.9(2) . . ?
C2 C5 H5A 112.2 . . ?
C4 C5 H5A 112.2 . . ?
C2 C5 H5B 112.2 . . ?
C4 C5 H5B 112.2 . . ?
H5A C5 H5B 109.8 . . ?
C11 C6 C7 116.6(2) . . ?
C11 C6 C4 117.9(2) . . ?
C7 C6 C4 125.5(2) . . ?
C8 C7 C6 122.8(2) . . ?
C8 C7 H7A 118.6 . . ?
C6 C7 H7A 118.6 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
N1 C9 C8 121.8(2) . . ?
N1 C9 C10 121.0(2) . . ?
C8 C9 C10 117.2(2) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
O2 C11 C6 121.9(2) . . ?
O2 C11 C10 115.9(2) . . ?
C6 C11 C10 122.2(2) . . ?
N1 C12 C13 114.1(2) . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
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 . . ?
C15 C14 N1 110.5(4) . . ?
C15 C14 H14A 109.6 . . ?
N1 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
N1 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C24 N2 C27 121.6(2) . . ?
C24 N2 C30 120.9(5) . . ?
C27 N2 C30 115.6(5) . . ?
C24 N2 C31 119.5(3) . . ?
C27 N2 C31 115.6(3) . . ?
C17 O3 C18 109.5(2) . . ?
C26 O4 C17 116.01(18) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 108.10(19) . . ?
O3 C17 C16 109.1(2) . . ?
O4 C17 C16 106.0(2) . . ?
O3 C17 C20 104.7(2) . . ?
O4 C17 C20 109.3(2) . . ?
C16 C17 C20 119.2(2) . . ?
O3 C18 C19 104.5(2) . . ?
O3 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
O3 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C21 C19 C18 110.5(2) . . ?
C21 C19 C20 107.0(2) . . ?
C18 C19 C20 100.0(2) . . ?
C21 C19 H19A 112.9 . . ?
C18 C19 H19A 112.9 . . ?
C20 C19 H19A 112.9 . . ?
C17 C20 C19 97.9(2) . . ?
C17 C20 H20A 112.2 . . ?
C19 C20 H20A 112.2 . . ?
C17 C20 H20B 112.2 . . ?
C19 C20 H20B 112.2 . . ?
H20A C20 H20B 109.8 . . ?
C22 C21 C26 116.4(2) . . ?
C22 C21 C19 125.6(2) . . ?
C26 C21 C19 118.0(2) . . ?
C23 C22 C21 122.9(2) . . ?
C23 C22 H22A 118.5 . . ?
C21 C22 H22A 118.5 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
N2 C24 C23 121.5(2) . . ?
N2 C24 C25 121.4(2) . . ?
C23 C24 C25 117.1(2) . . ?
C26 C25 C24 120.9(2) . . ?
C26 C25 H25A 119.5 . . ?
C24 C25 H25A 119.5 . . ?
O4 C26 C25 116.2(2) . . ?
O4 C26 C21 121.6(2) . . ?
C25 C26 C21 122.2(2) . . ?
N2 C27 C28 114.4(2) . . ?
N2 C27 H27A 108.7 . . ?
C28 C27 H27A 108.7 . . ?
N2 C27 H27B 108.7 . . ?
C28 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N2 C30 C29 100.6(9) . . ?
N2 C30 H30A 111.7 . . ?
C29 C30 H30A 111.7 . . ?
N2 C30 H30B 111.7 . . ?
C29 C30 H30B 111.7 . . ?
H30A C30 H30B 109.4 . . ?
C32 C31 N2 113.2(5) . . ?
C32 C31 H31A 108.9 . . ?
N2 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
N2 C31 H31B 108.9 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.045



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 3:1'
####################################################################### 
# 
# 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_4m
_database_code_depnum_ccdc_archive 'CCDC 1580281'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
4-Bromo-6-ethoxy-9-methyl-8,10-dioxatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
;
_chemical_name_common            ?
_chemical_melting_point_gt       382
_chemical_melting_point_lt       383
_chemical_formula_moiety         'C13 H15 Br O3'
_chemical_formula_sum            'C13 H15 Br O3'
_chemical_formula_weight         299.16

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'

_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                   9.9233(7)
_cell_length_b                   15.1382(10)
_cell_length_c                   8.9089(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.8150(10)
_cell_angle_gamma                90
_cell_volume                     1287.64(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5011
_cell_measurement_theta_min      2.522
_cell_measurement_theta_max      30.213

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   0.362
_exptl_transmission_factor_max   0.646
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.186
_shelx_estimated_absorpt_T_min   0.362
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12515
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3417
_reflns_number_gt                2957
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0304P)²+0.4077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3417
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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 0.23727(15) 0.41538(11) 0.34035(19) 0.0194(3) Uani 1 1 d . . . . .
H1A H 0.2190 0.3932 0.2333 0.029 Uiso 1 1 calc R U . . .
H1B H 0.2547 0.4791 0.3415 0.029 Uiso 1 1 calc R U . . .
H1C H 0.1558 0.4037 0.3796 0.029 Uiso 1 1 calc R U . . .
C2 C 0.36391(15) 0.36932(9) 0.44285(17) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.41790(16) 0.23678(10) 0.58100(18) 0.0180(3) Uani 1 1 d . . . . .
H3A H 0.4790 0.1876 0.5667 0.022 Uiso 1 1 calc R U . . .
H3B H 0.3500 0.2141 0.6350 0.022 Uiso 1 1 calc R U . . .
C4 C 0.50456(16) 0.31222(10) 0.67314(17) 0.0160(3) Uani 1 1 d . . . . .
H4A H 0.5283 0.3031 0.7886 0.019 Uiso 1 1 calc R U . . .
C5 C 0.40293(15) 0.38921(10) 0.61682(17) 0.0169(3) Uani 1 1 d . . . . .
H5A H 0.3209 0.3863 0.6597 0.020 Uiso 1 1 calc R U . . .
H5B H 0.4496 0.4473 0.6416 0.020 Uiso 1 1 calc R U . . .
C6 C 0.60971(14) 0.36821(9) 0.46836(17) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.63176(15) 0.33038(10) 0.61550(17) 0.0147(3) Uani 1 1 d . . . . .
C8 C 0.76837(16) 0.31143(10) 0.70433(18) 0.0171(3) Uani 1 1 d . . . . .
H8A H 0.7848 0.2864 0.8055 0.021 Uiso 1 1 calc R U . . .
C9 C 0.87879(15) 0.32965(10) 0.64283(19) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.85898(16) 0.36559(10) 0.49493(19) 0.0181(3) Uani 1 1 d . . . . .
H10A H 0.9367 0.3767 0.4547 0.022 Uiso 1 1 calc R U . . .
C11 C 0.72330(15) 0.38508(9) 0.40645(17) 0.0151(3) Uani 1 1 d . . . . .
C12 C 0.80275(18) 0.43883(12) 0.1926(2) 0.0246(3) Uani 1 1 d . . . . .
H12A H 0.8564 0.3846 0.1854 0.030 Uiso 1 1 calc R U . . .
H12B H 0.8671 0.4823 0.2584 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7387(2) 0.47639(15) 0.0326(2) 0.0377(5) Uani 1 1 d . . . . .
H13A H 0.8128 0.4890 -0.0179 0.057 Uiso 1 1 calc R U . . .
H13B H 0.6887 0.5311 0.0417 0.057 Uiso 1 1 calc R U . . .
H13C H 0.6730 0.4335 -0.0301 0.057 Uiso 1 1 calc R U . . .
O1 O 0.34581(11) 0.27613(7) 0.43171(12) 0.0164(2) Uani 1 1 d . . . . .
O2 O 0.47939(10) 0.39216(7) 0.37810(12) 0.0147(2) Uani 1 1 d . . . . .
O3 O 0.68942(11) 0.41889(7) 0.25889(12) 0.0190(2) Uani 1 1 d . . . . .
Br1 Br 1.06393(2) 0.30125(2) 0.76162(2) 0.02606(6) 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 1.508(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.4222(17) . ?
C2 O2 1.4581(17) . ?
C2 C5 1.522(2) . ?
C3 O1 1.4550(18) . ?
C3 C4 1.527(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C7 1.512(2) . ?
C4 C5 1.533(2) . ?
C4 H4A 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.3724(16) . ?
C6 C7 1.392(2) . ?
C6 C11 1.4067(19) . ?
C7 C8 1.401(2) . ?
C8 C9 1.380(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(2) . ?
C9 Br1 1.9028(15) . ?
C10 C11 1.394(2) . ?
C10 H10A 0.9500 . ?
C11 O3 1.3646(18) . ?
C12 O3 1.4374(18) . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 107.79(11) . . ?
O1 C2 C1 110.36(12) . . ?
O2 C2 C1 105.42(12) . . ?
O1 C2 C5 105.05(11) . . ?
O2 C2 C5 110.29(11) . . ?
C1 C2 C5 117.65(13) . . ?
O1 C3 C4 104.46(12) . . ?
O1 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C7 C4 C3 110.70(12) . . ?
C7 C4 C5 106.63(12) . . ?
C3 C4 C5 99.71(12) . . ?
C7 C4 H4A 113.0 . . ?
C3 C4 H4A 113.0 . . ?
C5 C4 H4A 113.0 . . ?
C2 C5 C4 98.33(11) . . ?
C2 C5 H5A 112.1 . . ?
C4 C5 H5A 112.1 . . ?
C2 C5 H5B 112.1 . . ?
C4 C5 H5B 112.1 . . ?
H5A C5 H5B 109.7 . . ?
O2 C6 C7 122.80(12) . . ?
O2 C6 C11 116.75(12) . . ?
C7 C6 C11 120.45(13) . . ?
C6 C7 C8 119.73(13) . . ?
C6 C7 C4 117.59(13) . . ?
C8 C7 C4 122.69(13) . . ?
C9 C8 C7 119.06(14) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C10 122.17(14) . . ?
C8 C9 Br1 119.00(12) . . ?
C10 C9 Br1 118.79(11) . . ?
C9 C10 C11 118.99(14) . . ?
C9 C10 H10A 120.5 . . ?
C11 C10 H10A 120.5 . . ?
O3 C11 C10 124.80(13) . . ?
O3 C11 C6 115.62(13) . . ?
C10 C11 C6 119.57(13) . . ?
O3 C12 C13 107.02(14) . . ?
O3 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O3 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
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 . . ?
C2 O1 C3 108.73(11) . . ?
C6 O2 C2 114.97(11) . . ?
C11 O3 C12 117.35(12) . . ?

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.059



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 3:1'
####################################################################### 
# 
# 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_4g
_database_code_depnum_ccdc_archive 'CCDC 1576714'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
6-Methoxy-9-methyl-8,10-dioxatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
;
_chemical_name_common            ?
_chemical_melting_point_gt       399
_chemical_melting_point_lt       400
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23

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                   8.638(3)
_cell_length_b                   15.409(7)
_cell_length_c                   8.594(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.43(2)
_cell_angle_gamma                90
_cell_volume                     1064.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12.97
_cell_measurement_theta_max      13.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8160
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.533
_diffrn_reflns_theta_max         25.962
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2085
_reflns_number_gt                1408
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0566P)²+0.1425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2085
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O 0.31641(14) 0.72012(7) 0.50857(14) 0.0529(3) Uani 1 1 d . . . . .
O2 O 0.44289(12) 0.59349(7) 0.64272(12) 0.0417(3) Uani 1 1 d . . . . .
O3 O 0.64052(13) 0.54374(7) 0.93861(12) 0.0491(3) Uani 1 1 d . . . . .
C1 C 0.1688(2) 0.58544(14) 0.4494(2) 0.0653(5) Uani 1 1 d . . . . .
H1A H 0.1329 0.5937 0.5417 0.098 Uiso 1 1 calc R U . . .
H1B H 0.1811 0.5245 0.4335 0.098 Uiso 1 1 calc R U . . .
H1C H 0.0877 0.6095 0.3499 0.098 Uiso 1 1 calc R U . . .
C2 C 0.3323(2) 0.63001(11) 0.48543(18) 0.0462(4) Uani 1 1 d . . . . .
C3 C 0.4290(2) 0.76699(11) 0.4488(2) 0.0555(5) Uani 1 1 d . . . . .
H3A H 0.4934 0.8092 0.5306 0.067 Uiso 1 1 calc R U . . .
H3B H 0.3686 0.7967 0.3447 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5406(2) 0.69675(11) 0.4229(2) 0.0513(4) Uani 1 1 d . . . . .
H4A H 0.5928 0.7139 0.3437 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4140(2) 0.62435(12) 0.3564(2) 0.0546(5) Uani 1 1 d . . . . .
H5A H 0.3361 0.6363 0.2443 0.066 Uiso 1 1 calc R U . . .
H5B H 0.4665 0.5685 0.3586 0.066 Uiso 1 1 calc R U . . .
C6 C 0.60709(18) 0.61795(9) 0.69096(18) 0.0380(3) Uani 1 1 d . . . . .
C7 C 0.6654(2) 0.66802(10) 0.5896(2) 0.0450(4) Uani 1 1 d . . . . .
C8 C 0.8334(2) 0.69043(12) 0.6488(2) 0.0579(5) Uani 1 1 d . . . . .
H8A H 0.8748 0.7236 0.5824 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9382(2) 0.66404(12) 0.8040(3) 0.0618(5) Uani 1 1 d . . . . .
H9A H 1.0499 0.6797 0.8418 0.074 Uiso 1 1 calc R U . . .
C10 C 0.8796(2) 0.61420(11) 0.9051(2) 0.0515(4) Uani 1 1 d . . . . .
H10A H 0.9517 0.5962 1.0098 0.062 Uiso 1 1 calc R U . . .
C11 C 0.71321(19) 0.59130(10) 0.84944(19) 0.0398(4) Uani 1 1 d . . . . .
C12 C 0.7359(2) 0.52590(14) 1.1090(2) 0.0657(5) Uani 1 1 d . . . . .
H12A H 0.6680 0.4959 1.1587 0.099 Uiso 1 1 calc R U . . .
H12B H 0.7746 0.5794 1.1675 0.099 Uiso 1 1 calc R U . . .
H12C H 0.8294 0.4903 1.1161 0.099 Uiso 1 1 calc R 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
O1 C2 1.416(2) . ?
O1 C3 1.448(2) . ?
O2 C6 1.3770(18) . ?
O2 C2 1.4537(18) . ?
O3 C11 1.3675(18) . ?
O3 C12 1.420(2) . ?
C1 C2 1.497(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C5 1.519(2) . ?
C3 C4 1.519(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C7 1.511(2) . ?
C4 C5 1.520(2) . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.389(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.394(2) . ?
C8 C9 1.371(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.384(2) . ?
C10 H10A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 O1 C3 109.10(12) . . ?
C6 O2 C2 115.40(12) . . ?
C11 O3 C12 118.01(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 108.26(12) . . ?
O1 C2 C1 110.28(15) . . ?
O2 C2 C1 105.34(13) . . ?
O1 C2 C5 104.67(13) . . ?
O2 C2 C5 109.49(14) . . ?
C1 C2 C5 118.51(14) . . ?
O1 C3 C4 103.94(13) . . ?
O1 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
O1 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C7 C4 C3 109.97(13) . . ?
C7 C4 C5 107.93(13) . . ?
C3 C4 C5 99.79(15) . . ?
C7 C4 H4A 112.8 . . ?
C3 C4 H4A 112.8 . . ?
C5 C4 H4A 112.8 . . ?
C2 C5 C4 98.39(13) . . ?
C2 C5 H5A 112.1 . . ?
C4 C5 H5A 112.1 . . ?
C2 C5 H5B 112.1 . . ?
C4 C5 H5B 112.1 . . ?
H5A C5 H5B 109.7 . . ?
O2 C6 C7 122.21(14) . . ?
O2 C6 C11 116.74(13) . . ?
C7 C6 C11 121.04(14) . . ?
C6 C7 C8 118.43(15) . . ?
C6 C7 C4 117.44(14) . . ?
C8 C7 C4 124.11(15) . . ?
C9 C8 C7 120.73(16) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C10 120.71(16) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C11 C10 C9 119.71(16) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
O3 C11 C10 125.05(14) . . ?
O3 C11 C6 115.58(13) . . ?
C10 C11 C6 119.37(15) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.116
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 3:1'
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1576712'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1-[4-(2-Hydroxyphenyl)-2-methyl-4,5-dihydrofuran-3-yl]ethanone
;
_chemical_name_common            ?
_chemical_melting_point_gt       362
_chemical_melting_point_lt       363
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24

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'

_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                   9.944(5)
_cell_length_b                   16.675(8)
_cell_length_c                   15.179(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.38(4)
_cell_angle_gamma                90
_cell_volume                     2389(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      19.98
_cell_measurement_theta_max      21.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.700
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7253
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.055
_diffrn_reflns_theta_max         64.973
_diffrn_reflns_theta_full        64.973
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3913
_reflns_number_gt                1763
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0893P)²] 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         3913
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1516
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.005
_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
O1 O 0.9395(3) 0.39185(15) 0.83334(18) 0.0852(8) Uani 1 1 d . . . . .
O2 O 0.8118(3) 0.60651(15) 0.92943(15) 0.0740(7) Uani 1 1 d . . . . .
O3 O 0.9921(3) 0.75929(17) 0.74854(18) 0.0755(8) Uani 1 1 d . . . . .
H1 H 1.001(5) 0.801(2) 0.724(3) 0.093(15) Uiso 1 1 d . . . . .
C1 C 1.0431(5) 0.4700(2) 0.7433(3) 0.1015(15) Uani 1 1 d . . . . .
H1A H 1.0557 0.5262 0.7346 0.152 Uiso 1 1 calc R U . . .
H1B H 0.9927 0.4460 0.6847 0.152 Uiso 1 1 calc R U . . .
H1C H 1.1340 0.4448 0.7682 0.152 Uiso 1 1 calc R U . . .
C2 C 0.9605(4) 0.4592(2) 0.8092(2) 0.0639(10) Uani 1 1 d . . . . .
C3 C 0.9140(4) 0.5313(2) 0.8457(2) 0.0560(9) Uani 1 1 d . . . . .
C4 C 0.8358(4) 0.5325(2) 0.9037(2) 0.0623(10) Uani 1 1 d . . . . .
C5 C 0.7724(4) 0.4675(2) 0.9438(2) 0.0801(12) Uani 1 1 d . . . . .
H5A H 0.8101 0.4695 1.0103 0.120 Uiso 1 1 calc R U . . .
H5B H 0.7945 0.4167 0.9222 0.120 Uiso 1 1 calc R U . . .
H5C H 0.6714 0.4743 0.9251 0.120 Uiso 1 1 calc R U . . .
C6 C 0.8977(4) 0.6623(2) 0.8968(2) 0.0729(11) Uani 1 1 d . . . . .
H6A H 0.9816 0.6776 0.9470 0.088 Uiso 1 1 calc R U . . .
H6B H 0.8441 0.7102 0.8716 0.088 Uiso 1 1 calc R U . . .
C7 C 0.9386(4) 0.61661(19) 0.8207(2) 0.0605(9) Uani 1 1 d . . . . .
H7A H 1.0397 0.6245 0.8296 0.073 Uiso 1 1 calc R U . . .
C8 C 0.8527(4) 0.6431(2) 0.7236(2) 0.0565(9) Uani 1 1 d . . . . .
C9 C 0.7399(4) 0.5996(2) 0.6668(2) 0.0712(11) Uani 1 1 d . . . . .
H9A H 0.7153 0.5512 0.6881 0.085 Uiso 1 1 calc R U . . .
C10 C 0.6640(4) 0.6261(3) 0.5802(2) 0.0848(13) Uani 1 1 d . . . . .
H10A H 0.5908 0.5950 0.5424 0.102 Uiso 1 1 calc R U . . .
C11 C 0.6953(5) 0.6982(3) 0.5490(3) 0.0897(14) Uani 1 1 d . . . . .
H11A H 0.6411 0.7169 0.4910 0.108 Uiso 1 1 calc R U . . .
C12 C 0.8068(4) 0.7436(2) 0.6033(2) 0.0754(11) Uani 1 1 d . . . . .
H12A H 0.8300 0.7920 0.5813 0.090 Uiso 1 1 calc R U . . .
C13 C 0.8834(4) 0.7164(2) 0.6903(2) 0.0601(9) Uani 1 1 d . . . . .
O11 O 0.4158(3) 0.87144(15) 0.80465(19) 0.0895(9) Uani 1 1 d . . . . .
O12 O 0.3293(3) 0.66372(17) 0.93077(16) 0.0807(8) Uani 1 1 d . . . . .
O13 O 0.5038(3) 0.50286(16) 0.75919(18) 0.0780(8) Uani 1 1 d . . . . .
H2 H 0.524(5) 0.456(3) 0.736(3) 0.120(18) Uiso 1 1 d . . . . .
C21 C 0.5081(5) 0.7900(2) 0.7095(3) 0.0912(13) Uani 1 1 d . . . . .
H21A H 0.5107 0.7337 0.6971 0.137 Uiso 1 1 calc R U . . .
H21B H 0.6030 0.8108 0.7304 0.137 Uiso 1 1 calc R U . . .
H21C H 0.4546 0.8174 0.6539 0.137 Uiso 1 1 calc R U . . .
C22 C 0.4387(4) 0.8031(2) 0.7842(2) 0.0636(10) Uani 1 1 d . . . . .
C23 C 0.4063(4) 0.73377(19) 0.8298(2) 0.0539(8) Uani 1 1 d . . . . .
C24 C 0.3388(4) 0.7359(2) 0.8942(2) 0.0621(10) Uani 1 1 d . . . . .
C25 C 0.2747(4) 0.8018(2) 0.9318(3) 0.0889(13) Uani 1 1 d . . . . .
H25A H 0.1781 0.7887 0.9256 0.133 Uiso 1 1 calc R U . . .
H25B H 0.2772 0.8502 0.8981 0.133 Uiso 1 1 calc R U . . .
H25C H 0.3269 0.8095 0.9962 0.133 Uiso 1 1 calc R U . . .
C26 C 0.4181(5) 0.6093(2) 0.8999(2) 0.0761(12) Uani 1 1 d . . . . .
H26A H 0.3728 0.5573 0.8851 0.091 Uiso 1 1 calc R U . . .
H26B H 0.5087 0.6024 0.9478 0.091 Uiso 1 1 calc R U . . .
C27 C 0.4381(4) 0.64732(19) 0.8140(2) 0.0579(9) Uani 1 1 d . . . . .
H27A H 0.5376 0.6425 0.8170 0.069 Uiso 1 1 calc R U . . .
C28 C 0.3454(4) 0.61063(19) 0.7247(2) 0.0533(8) Uani 1 1 d . . . . .
C29 C 0.2206(4) 0.6447(2) 0.6675(2) 0.0613(9) Uani 1 1 d . . . . .
H29A H 0.1910 0.6939 0.6835 0.074 Uiso 1 1 calc R U . . .
C30 C 0.1400(4) 0.6066(3) 0.5873(2) 0.0742(11) Uani 1 1 d . . . . .
H30A H 0.0559 0.6295 0.5503 0.089 Uiso 1 1 calc R U . . .
C31 C 0.1847(5) 0.5350(3) 0.5630(2) 0.0784(12) Uani 1 1 d . . . . .
H31A H 0.1319 0.5102 0.5082 0.094 Uiso 1 1 calc R U . . .
C32 C 0.3059(4) 0.4993(2) 0.6179(2) 0.0735(11) Uani 1 1 d . . . . .
H32A H 0.3353 0.4505 0.6005 0.088 Uiso 1 1 calc R U . . .
C33 C 0.3847(4) 0.5362(2) 0.6997(2) 0.0594(9) 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
O1 C2 1.220(4) . ?
O2 C4 1.339(4) . ?
O2 C6 1.452(4) . ?
O3 C13 1.363(4) . ?
O3 H1 0.81(4) . ?
C1 C2 1.492(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.459(5) . ?
C3 C4 1.345(5) . ?
C3 C7 1.511(4) . ?
C4 C5 1.478(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.541(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.518(4) . ?
C7 H7A 0.9800 . ?
C8 C9 1.385(4) . ?
C8 C13 1.393(5) . ?
C9 C10 1.367(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.363(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.377(5) . ?
C12 H12A 0.9300 . ?
O11 C22 1.222(4) . ?
O12 C24 1.341(4) . ?
O12 C26 1.443(4) . ?
O13 C33 1.361(4) . ?
O13 H2 0.91(5) . ?
C21 C22 1.517(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.436(5) . ?
C23 C24 1.348(5) . ?
C23 C27 1.511(4) . ?
C24 C25 1.473(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.518(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.508(4) . ?
C27 H27A 0.9800 . ?
C28 C33 1.390(4) . ?
C28 C29 1.391(4) . ?
C29 C30 1.383(5) . ?
C29 H29A 0.9300 . ?
C30 C31 1.364(5) . ?
C30 H30A 0.9300 . ?
C31 C32 1.367(5) . ?
C31 H31A 0.9300 . ?
C32 C33 1.386(5) . ?
C32 H32A 0.9300 . ?

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
C4 O2 C6 108.2(3) . . ?
C13 O3 H1 110(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 122.7(3) . . ?
O1 C2 C1 119.6(4) . . ?
C3 C2 C1 117.6(3) . . ?
C4 C3 C2 125.3(3) . . ?
C4 C3 C7 108.9(3) . . ?
C2 C3 C7 125.7(3) . . ?
O2 C4 C3 113.4(3) . . ?
O2 C4 C5 114.6(3) . . ?
C3 C4 C5 132.0(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 C7 105.2(3) . . ?
O2 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
O2 C6 H6B 110.7 . . ?
C7 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C3 C7 C8 115.5(3) . . ?
C3 C7 C6 100.1(3) . . ?
C8 C7 C6 112.6(3) . . ?
C3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C9 C8 C13 117.5(3) . . ?
C9 C8 C7 123.3(3) . . ?
C13 C8 C7 119.1(3) . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
O3 C13 C12 122.4(3) . . ?
O3 C13 C8 116.4(3) . . ?
C12 C13 C8 121.2(4) . . ?
C24 O12 C26 107.4(3) . . ?
C33 O13 H2 111(3) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O11 C22 C23 122.7(3) . . ?
O11 C22 C21 119.3(3) . . ?
C23 C22 C21 118.0(3) . . ?
C24 C23 C22 124.6(3) . . ?
C24 C23 C27 108.5(3) . . ?
C22 C23 C27 127.0(3) . . ?
O12 C24 C23 113.1(3) . . ?
O12 C24 C25 114.4(3) . . ?
C23 C24 C25 132.4(4) . . ?
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 . . ?
O12 C26 C27 106.0(3) . . ?
O12 C26 H26A 110.5 . . ?
C27 C26 H26A 110.5 . . ?
O12 C26 H26B 110.5 . . ?
C27 C26 H26B 110.5 . . ?
H26A C26 H26B 108.7 . . ?
C28 C27 C23 115.5(3) . . ?
C28 C27 C26 113.2(3) . . ?
C23 C27 C26 99.9(3) . . ?
C28 C27 H27A 109.3 . . ?
C23 C27 H27A 109.3 . . ?
C26 C27 H27A 109.3 . . ?
C33 C28 C29 117.8(3) . . ?
C33 C28 C27 117.6(3) . . ?
C29 C28 C27 124.6(3) . . ?
C30 C29 C28 121.1(4) . . ?
C30 C29 H29A 119.4 . . ?
C28 C29 H29A 119.4 . . ?
C31 C30 C29 119.4(4) . . ?
C31 C30 H30A 120.3 . . ?
C29 C30 H30A 120.3 . . ?
C30 C31 C32 121.1(4) . . ?
C30 C31 H31A 119.4 . . ?
C32 C31 H31A 119.4 . . ?
C31 C32 C33 119.5(4) . . ?
C31 C32 H32A 120.2 . . ?
C33 C32 H32A 120.2 . . ?
O13 C33 C32 122.7(3) . . ?
O13 C33 C28 116.4(3) . . ?
C32 C33 C28 120.9(4) . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 3:1'
####################################################################### 
# 
# 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_1p
_database_code_depnum_ccdc_archive 'CCDC 1580258'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
{4-[3-Ethoxy-2-(methoxymethoxy)phenyl]-2-phenyl-4,5-dihydrofuran-3-yl}(phenyl)methanone
;
_chemical_name_common            ?
_chemical_melting_point_gt       363
_chemical_melting_point_lt       364
_chemical_formula_moiety         'C27 H26 O5'
_chemical_formula_sum            'C27 H26 O5'
_chemical_formula_weight         430.48

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.1922(6)
_cell_length_b                   9.9323(8)
_cell_length_c                   16.0391(13)
_cell_angle_alpha                78.0660(10)
_cell_angle_beta                 84.7320(10)
_cell_angle_gamma                86.3020(10)
_cell_volume                     1115.04(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3952
_cell_measurement_theta_min      2.604
_cell_measurement_theta_max      30.429

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   0.962
_exptl_transmission_factor_max   0.978
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12457
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         28.999
_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             5901
_reflns_number_gt                4692
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0496P)²+0.2754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5901
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.029
_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_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
O1 O 0.79313(14) 0.47961(9) 0.33349(6) 0.0285(2) Uani 1 1 d . . . . .
O2 O 0.80121(12) 0.88273(8) 0.14187(5) 0.02107(19) Uani 1 1 d . . . . .
O3 O 0.72072(11) 0.37828(8) 0.12565(5) 0.01687(17) Uani 1 1 d . . . . .
O4 O 0.89709(11) 0.32046(9) 0.01089(6) 0.02181(19) Uani 1 1 d . . . . .
O5 O 0.40933(11) 0.24260(9) 0.13569(6) 0.02186(19) Uani 1 1 d . . . . .
C1 C 0.75094(15) 0.69841(12) 0.25042(7) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.79959(15) 0.83053(12) 0.22800(7) 0.0172(2) Uani 1 1 d . . . . .
C3 C 0.72178(17) 0.78077(12) 0.10363(7) 0.0193(2) Uani 1 1 d . . . . .
H3A H 0.7965 0.7699 0.0503 0.023 Uiso 1 1 calc R U . . .
H3B H 0.5918 0.8094 0.0900 0.023 Uiso 1 1 calc R U . . .
C4 C 0.72603(15) 0.64484(12) 0.17009(7) 0.0168(2) Uani 1 1 d . . . . .
H4A H 0.8376 0.5854 0.1565 0.020 Uiso 1 1 calc R U . . .
C5 C 0.74718(16) 0.60069(12) 0.33344(8) 0.0190(2) Uani 1 1 d . . . . .
C6 C 0.68656(17) 0.64597(13) 0.41514(8) 0.0220(2) Uani 1 1 d . . . . .
C7 C 0.56631(18) 0.76046(15) 0.41944(9) 0.0270(3) Uani 1 1 d . . . . .
H7A H 0.5206 0.8145 0.3688 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5132(2) 0.79560(19) 0.49818(10) 0.0390(4) Uani 1 1 d . . . . .
H8A H 0.4292 0.8725 0.5013 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5826(2) 0.7188(2) 0.57170(10) 0.0481(4) Uani 1 1 d . . . . .
H9A H 0.5487 0.7446 0.6251 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7006(3) 0.6050(2) 0.56788(10) 0.0479(4) Uani 1 1 d . . . . .
H10A H 0.7477 0.5524 0.6187 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7509(2) 0.56713(16) 0.49021(9) 0.0335(3) Uani 1 1 d . . . . .
H11A H 0.8296 0.4871 0.4881 0.040 Uiso 1 1 calc R U . . .
C12 C 0.85997(16) 0.92769(12) 0.27722(7) 0.0186(2) Uani 1 1 d . . . . .
C13 C 0.79026(17) 1.06460(12) 0.26132(8) 0.0220(2) Uani 1 1 d . . . . .
H13A H 0.7066 1.0951 0.2180 0.026 Uiso 1 1 calc R U . . .
C14 C 0.84293(19) 1.15603(14) 0.30868(9) 0.0270(3) Uani 1 1 d . . . . .
H14A H 0.7943 1.2487 0.2981 0.032 Uiso 1 1 calc R U . . .
C15 C 0.9665(2) 1.11215(15) 0.37135(9) 0.0318(3) Uani 1 1 d . . . . .
H15A H 1.0016 1.1746 0.4041 0.038 Uiso 1 1 calc R U . . .
C16 C 1.0390(2) 0.97728(15) 0.38632(9) 0.0313(3) Uani 1 1 d . . . . .
H16A H 1.1250 0.9479 0.4287 0.038 Uiso 1 1 calc R U . . .
C17 C 0.98609(18) 0.88500(13) 0.33950(8) 0.0241(3) Uani 1 1 d . . . . .
H17A H 1.0360 0.7927 0.3500 0.029 Uiso 1 1 calc R U . . .
C18 C 0.54949(15) 0.56697(12) 0.17589(7) 0.0162(2) Uani 1 1 d . . . . .
C19 C 0.55378(15) 0.43976(11) 0.15262(7) 0.0156(2) Uani 1 1 d . . . . .
C20 C 0.38870(16) 0.36748(12) 0.15950(7) 0.0171(2) Uani 1 1 d . . . . .
C21 C 0.22026(16) 0.42446(12) 0.18884(8) 0.0197(2) Uani 1 1 d . . . . .
H21A H 0.1085 0.3766 0.1934 0.024 Uiso 1 1 calc R U . . .
C22 C 0.21695(16) 0.55257(12) 0.21152(7) 0.0196(2) Uani 1 1 d . . . . .
H22A H 0.1019 0.5922 0.2313 0.024 Uiso 1 1 calc R U . . .
C23 C 0.37864(16) 0.62283(12) 0.20558(8) 0.0188(2) Uani 1 1 d . . . . .
H23A H 0.3739 0.7098 0.2218 0.023 Uiso 1 1 calc R U . . .
C24 C 0.76618(17) 0.41611(12) 0.03492(8) 0.0208(2) Uani 1 1 d . . . . .
H24A H 0.6524 0.4181 0.0043 0.025 Uiso 1 1 calc R U . . .
H24B H 0.8173 0.5090 0.0202 0.025 Uiso 1 1 calc R U . . .
C25 C 0.81678(19) 0.19368(13) 0.00823(9) 0.0267(3) Uani 1 1 d . . . . .
H25A H 0.9151 0.1286 -0.0077 0.040 Uiso 1 1 calc R U . . .
H25B H 0.7235 0.2106 -0.0341 0.040 Uiso 1 1 calc R U . . .
H25C H 0.7566 0.1549 0.0647 0.040 Uiso 1 1 calc R U . . .
C26 C 0.24913(17) 0.15879(12) 0.15339(8) 0.0218(2) Uani 1 1 d . . . . .
H26A H 0.1473 0.2022 0.1179 0.026 Uiso 1 1 calc R U . . .
H26B H 0.2027 0.1475 0.2144 0.026 Uiso 1 1 calc R U . . .
C27 C 0.31164(19) 0.02125(13) 0.13231(9) 0.0278(3) Uani 1 1 d . . . . .
H27A H 0.2052 -0.0384 0.1418 0.042 Uiso 1 1 calc R U . . .
H27B H 0.4097 -0.0217 0.1691 0.042 Uiso 1 1 calc R U . . .
H27C H 0.3608 0.0343 0.0723 0.042 Uiso 1 1 calc R 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
O1 C5 1.2263(14) . ?
O2 C2 1.3707(14) . ?
O2 C3 1.4574(14) . ?
O3 C19 1.3860(13) . ?
O3 C24 1.4381(14) . ?
O4 C24 1.3809(14) . ?
O4 C25 1.4289(15) . ?
O5 C20 1.3668(14) . ?
O5 C26 1.4378(14) . ?
C1 C2 1.3471(16) . ?
C1 C5 1.4758(16) . ?
C1 C4 1.5210(16) . ?
C2 C12 1.4749(16) . ?
C3 C4 1.5380(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C18 1.5147(15) . ?
C4 H4A 1.0000 . ?
C5 C6 1.4910(17) . ?
C6 C7 1.3930(18) . ?
C6 C11 1.3939(18) . ?
C7 C8 1.3924(19) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C17 1.3936(17) . ?
C12 C13 1.3992(17) . ?
C13 C14 1.3883(17) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3895(18) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.3873(16) . ?
C18 C23 1.3994(15) . ?
C19 C20 1.4108(15) . ?
C20 C21 1.3880(16) . ?
C21 C22 1.3920(17) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3803(16) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.5055(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C2 O2 C3 107.21(9) . . ?
C19 O3 C24 113.21(8) . . ?
C24 O4 C25 112.44(9) . . ?
C20 O5 C26 116.43(9) . . ?
C2 C1 C5 131.18(11) . . ?
C2 C1 C4 109.09(10) . . ?
C5 C1 C4 119.02(10) . . ?
C1 C2 O2 113.49(10) . . ?
C1 C2 C12 132.66(11) . . ?
O2 C2 C12 113.78(10) . . ?
O2 C3 C4 106.44(9) . . ?
O2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
O2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C18 C4 C1 113.44(9) . . ?
C18 C4 C3 112.54(9) . . ?
C1 C4 C3 100.46(9) . . ?
C18 C4 H4A 110.0 . . ?
C1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
O1 C5 C1 118.00(11) . . ?
O1 C5 C6 120.45(11) . . ?
C1 C5 C6 121.54(10) . . ?
C7 C6 C11 119.33(12) . . ?
C7 C6 C5 122.94(11) . . ?
C11 C6 C5 117.71(12) . . ?
C8 C7 C6 119.86(14) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C9 C8 C7 120.13(15) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C10 C9 C8 120.24(15) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.16(15) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C6 120.25(15) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
C17 C12 C13 119.39(11) . . ?
C17 C12 C2 120.84(11) . . ?
C13 C12 C2 119.77(11) . . ?
C14 C13 C12 120.20(12) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 120.01(13) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.09(12) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C17 120.21(13) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 120.08(12) . . ?
C16 C17 H17A 120.0 . . ?
C12 C17 H17A 120.0 . . ?
C19 C18 C23 118.93(10) . . ?
C19 C18 C4 121.07(10) . . ?
C23 C18 C4 120.00(10) . . ?
O3 C19 C18 120.95(10) . . ?
O3 C19 C20 118.54(10) . . ?
C18 C19 C20 120.46(10) . . ?
O5 C20 C21 124.54(10) . . ?
O5 C20 C19 115.56(10) . . ?
C21 C20 C19 119.90(10) . . ?
C20 C21 C22 119.27(11) . . ?
C20 C21 H21A 120.4 . . ?
C22 C21 H21A 120.4 . . ?
C23 C22 C21 120.89(11) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C18 120.54(11) . . ?
C22 C23 H23A 119.7 . . ?
C18 C23 H23A 119.7 . . ?
O4 C24 O3 108.59(9) . . ?
O4 C24 H24A 110.0 . . ?
O3 C24 H24A 110.0 . . ?
O4 C24 H24B 110.0 . . ?
O3 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 C27 106.81(10) . . ?
O5 C26 H26A 110.4 . . ?
C27 C26 H26A 110.4 . . ?
O5 C26 H26B 110.4 . . ?
C27 C26 H26B 110.4 . . ?
H26A C26 H26B 108.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 2:1'
####################################################################### 
# 
# 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_1q
_database_code_depnum_ccdc_archive 'CCDC 1580257'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Methyl 4-[2-(methoxymethoxy)phenyl]-2-methyl-4,5-dihydrofuran-3-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point_gt       329
_chemical_melting_point_lt       330
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29

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                   9.9599(6)
_cell_length_b                   6.7335(4)
_cell_length_c                   20.4059(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.5220(10)
_cell_angle_gamma                90
_cell_volume                     1365.94(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6537
_cell_measurement_theta_min      2.774
_cell_measurement_theta_max      30.473

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   0.961
_exptl_transmission_factor_max   0.980
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14636
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3636
_reflns_number_gt                3207
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0539P)²+0.4032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3636
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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_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
O1 O -0.06666(7) 0.56689(12) 0.63084(4) 0.02366(17) Uani 1 1 d . . . . .
O2 O 0.09765(7) 0.61110(11) 0.56124(3) 0.01968(16) Uani 1 1 d . . . . .
O3 O 0.16678(7) 0.03972(11) 0.67655(4) 0.02263(17) Uani 1 1 d . . . . .
O4 O 0.50135(7) 0.29046(11) 0.55623(3) 0.02063(16) Uani 1 1 d . . . . .
O5 O 0.72273(7) 0.16892(12) 0.56403(4) 0.02381(17) Uani 1 1 d . . . . .
C1 C 0.11719(9) 0.33761(15) 0.62957(4) 0.01649(19) Uani 1 1 d . . . . .
C2 C 0.07725(10) 0.19148(15) 0.66900(5) 0.0189(2) Uani 1 1 d . . . . .
C3 C 0.27308(10) 0.07445(15) 0.63186(5) 0.0208(2) Uani 1 1 d . . . . .
H3A H 0.2646 -0.0194 0.5945 0.025 Uiso 1 1 calc R U . . .
H3B H 0.3626 0.0562 0.6550 0.025 Uiso 1 1 calc R U . . .
C4 C 0.25603(9) 0.29134(14) 0.60725(5) 0.01562(18) Uani 1 1 d . . . . .
H4A H 0.2545 0.2945 0.5582 0.019 Uiso 1 1 calc R U . . .
C5 C 0.03835(9) 0.51210(15) 0.60958(5) 0.01701(19) Uani 1 1 d . . . . .
C6 C 0.02417(10) 0.78181(16) 0.53614(5) 0.0217(2) Uani 1 1 d . . . . .
H6A H 0.0715 0.8410 0.5003 0.032 Uiso 1 1 calc R U . . .
H6B H 0.0172 0.8796 0.5713 0.032 Uiso 1 1 calc R U . . .
H6C H -0.0662 0.7410 0.5198 0.032 Uiso 1 1 calc R U . . .
C7 C -0.04611(11) 0.16522(18) 0.70555(5) 0.0257(2) Uani 1 1 d . . . . .
H7A H -0.1094 0.2732 0.6943 0.039 Uiso 1 1 calc R U . . .
H7B H -0.0221 0.1675 0.7528 0.039 Uiso 1 1 calc R U . . .
H7C H -0.0882 0.0376 0.6936 0.039 Uiso 1 1 calc R U . . .
C8 C 0.36768(9) 0.42494(14) 0.63599(4) 0.01471(18) Uani 1 1 d . . . . .
C9 C 0.49508(9) 0.41295(14) 0.61035(5) 0.01616(19) Uani 1 1 d . . . . .
C10 C 0.60482(10) 0.51683(15) 0.63878(5) 0.0201(2) Uani 1 1 d . . . . .
H10A H 0.6912 0.5043 0.6219 0.024 Uiso 1 1 calc R U . . .
C11 C 0.58578(10) 0.63937(15) 0.69241(5) 0.0222(2) Uani 1 1 d . . . . .
H11A H 0.6600 0.7106 0.7122 0.027 Uiso 1 1 calc R U . . .
C12 C 0.46026(11) 0.65894(15) 0.71733(5) 0.0215(2) Uani 1 1 d . . . . .
H12A H 0.4479 0.7451 0.7533 0.026 Uiso 1 1 calc R U . . .
C13 C 0.35194(10) 0.55054(14) 0.68901(5) 0.01804(19) Uani 1 1 d . . . . .
H13A H 0.2660 0.5630 0.7063 0.022 Uiso 1 1 calc R U . . .
C14 C 0.62606(10) 0.27487(18) 0.52607(5) 0.0245(2) Uani 1 1 d . . . . .
H14A H 0.6107 0.2084 0.4830 0.029 Uiso 1 1 calc R U . . .
H14B H 0.6607 0.4100 0.5181 0.029 Uiso 1 1 calc R U . . .
C15 C 0.68115(12) -0.02872(17) 0.57772(6) 0.0289(2) Uani 1 1 d . . . . .
H15A H 0.7569 -0.1024 0.5988 0.043 Uiso 1 1 calc R U . . .
H15B H 0.6510 -0.0948 0.5366 0.043 Uiso 1 1 calc R U . . .
H15C H 0.6070 -0.0248 0.6071 0.043 Uiso 1 1 calc R 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
O1 C5 1.2140(12) . ?
O2 C5 1.3557(12) . ?
O2 C6 1.4398(12) . ?
O3 C2 1.3588(12) . ?
O3 C3 1.4581(12) . ?
O4 C9 1.3829(12) . ?
O4 C14 1.4236(11) . ?
O5 C14 1.3944(13) . ?
O5 C15 1.4265(14) . ?
C1 C2 1.3465(14) . ?
C1 C5 1.4575(14) . ?
C1 C4 1.5147(12) . ?
C2 C7 1.4865(14) . ?
C3 C4 1.5503(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.5198(12) . ?
C4 H4A 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.3896(13) . ?
C8 C9 1.4042(13) . ?
C9 C10 1.3937(13) . ?
C10 C11 1.3927(15) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3846(15) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3978(14) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C5 O2 C6 114.63(8) . . ?
C2 O3 C3 107.76(8) . . ?
C9 O4 C14 118.20(8) . . ?
C14 O5 C15 112.78(9) . . ?
C2 C1 C5 125.63(9) . . ?
C2 C1 C4 109.76(8) . . ?
C5 C1 C4 124.59(8) . . ?
C1 C2 O3 113.67(9) . . ?
C1 C2 C7 132.09(10) . . ?
O3 C2 C7 114.24(9) . . ?
O3 C3 C4 106.53(8) . . ?
O3 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
O3 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C1 C4 C8 114.96(8) . . ?
C1 C4 C3 100.38(7) . . ?
C8 C4 C3 111.69(8) . . ?
C1 C4 H4A 109.8 . . ?
C8 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
O1 C5 O2 122.28(9) . . ?
O1 C5 C1 127.31(9) . . ?
O2 C5 C1 110.41(8) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.21(9) . . ?
C13 C8 C4 123.08(8) . . ?
C9 C8 C4 118.60(8) . . ?
O4 C9 C10 123.99(9) . . ?
O4 C9 C8 114.71(8) . . ?
C10 C9 C8 121.30(9) . . ?
C11 C10 C9 118.90(9) . . ?
C11 C10 H10A 120.6 . . ?
C9 C10 H10A 120.6 . . ?
C12 C11 C10 120.97(9) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 119.32(9) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C8 C13 C12 121.24(9) . . ?
C8 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
O5 C14 O4 112.87(8) . . ?
O5 C14 H14A 109.0 . . ?
O4 C14 H14A 109.0 . . ?
O5 C14 H14B 109.0 . . ?
O4 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether : ethyl acetate, 4:1'
