# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_ma1molt
_database_code_depnum_ccdc_archive 'CCDC 1444735'
_audit_update_record             
;
2015-12-30 deposited with the CCDC.
2016-03-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_chemical_melting_point          ?

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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   19.5895(10)
_cell_length_b                   7.0388(3)
_cell_length_c                   9.2405(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.626(4)
_cell_angle_gamma                90
_cell_volume                     1273.63(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.8880
_cell_measurement_theta_min      4.1490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0502

_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6903

_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.565
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   87.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   77.0000  -90.0000 130

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   88.40   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   77.0000   30.0000 132

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   90.40   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   77.0000  150.0000 132
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0146217000
_diffrn_orient_matrix_UB_12      -0.0485714000
_diffrn_orient_matrix_UB_13      0.0588004000
_diffrn_orient_matrix_UB_21      0.0291188000
_diffrn_orient_matrix_UB_22      -0.0597761000
_diffrn_orient_matrix_UB_23      0.0054815000
_diffrn_orient_matrix_UB_31      0.0158379000
_diffrn_orient_matrix_UB_32      0.0648797000
_diffrn_orient_matrix_UB_33      0.0491393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1834
_reflns_number_total             2470
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.07580(6) 0.57964(15) 0.39909(11) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.11107(7) 0.28250(15) 0.43463(13) 0.0237(3) Uani 1 1 d . . . . .
O3 O 0.34066(8) 0.35271(19) 0.41616(13) 0.0361(4) Uani 1 1 d . . . . .
C1 C 0.11824(9) 0.4479(2) 0.47113(17) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.16328(9) 0.5254(2) 0.57782(16) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.21214(9) 0.4265(2) 0.68142(17) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.1858 0.3505 0.7523 0.024 Uiso 1 1 calc R . . . .
C4 C 0.26611(10) 0.2998(2) 0.61315(18) 0.0245(4) Uani 1 1 d . . . . .
H4A H 0.2918 0.2312 0.6907 0.029 Uiso 1 1 calc R . . . .
H4B H 0.2431 0.2042 0.5502 0.029 Uiso 1 1 calc R . . . .
C5 C 0.31519(10) 0.4124(2) 0.52513(18) 0.0236(4) Uani 1 1 d . . . . .
C6 C 0.33010(9) 0.6128(2) 0.58015(16) 0.0201(4) Uani 1 1 d . . . . .
H6 H 0.2994 0.7029 0.5257 0.024 Uiso 1 1 calc R . . . .
O7 O 0.31439(6) 0.62400(16) 0.73221(11) 0.0200(3) Uani 1 1 d . . . . .
C8 C 0.24617(9) 0.5984(2) 0.76002(17) 0.0190(4) Uani 1 1 d . . . . .
H8 H 0.2412 0.5822 0.8667 0.023 Uiso 1 1 calc R . . . .
O9 O 0.20743(6) 0.76874(15) 0.71266(11) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.16343(9) 0.7146(2) 0.60489(16) 0.0161(4) Uani 1 1 d . . . . .
C11 C 0.12063(9) 0.8448(2) 0.52842(17) 0.0174(4) Uani 1 1 d . . . . .
H11 H 0.1222 0.9773 0.5476 0.021 Uiso 1 1 calc R . . . .
C12 C 0.07777(9) 0.7711(2) 0.42744(17) 0.0166(4) Uani 1 1 d . . . . .
C13 C 0.40356(10) 0.6781(3) 0.56290(18) 0.0241(4) Uani 1 1 d . . . . .
H13 H 0.4159 0.6532 0.4603 0.029 Uiso 1 1 calc R . . . .
C14 C 0.45341(11) 0.5674(3) 0.6599(2) 0.0355(5) Uani 1 1 d . . . . .
H14A H 0.5002 0.6080 0.6410 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.4488 0.4313 0.6395 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.4434 0.5915 0.7615 0.053 Uiso 1 1 calc GR . . . .
C15 C 0.40887(11) 0.8918(3) 0.5880(2) 0.0320(5) Uani 1 1 d . . . . .
H15A H 0.3943 0.9219 0.6860 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.3795 0.9584 0.5171 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.4563 0.9325 0.5772 0.048 Uiso 1 1 calc GR . . . .
C16 C 0.02647(9) 0.8753(2) 0.33682(17) 0.0202(4) Uani 1 1 d . . . . .
H16A H 0.0330 0.8454 0.2346 0.030 Uiso 1 1 calc GR . . . .
H16B H 0.0320 1.0122 0.3522 0.030 Uiso 1 1 calc GR . . . .
H16C H -0.0195 0.8369 0.3638 0.030 Uiso 1 1 calc GR . . . .


_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 C1 1.4008(19) . ?
O1 C12 1.3729(18) . ?
O2 C1 1.2194(19) . ?
O3 C5 1.2116(19) . ?
C1 C2 1.414(2) . ?
C2 C3 1.505(2) . ?
C2 C10 1.355(2) . ?
C3 C4 1.532(2) . ?
C3 C8 1.552(2) . ?
C4 C5 1.503(2) . ?
C5 C6 1.525(2) . ?
C6 O7 1.4491(18) . ?
C6 C13 1.523(3) . ?
O7 C8 1.380(2) . ?
C8 O9 1.479(2) . ?
O9 C10 1.3533(19) . ?
C10 C11 1.417(2) . ?
C11 C12 1.342(2) . ?
C12 C16 1.484(2) . ?
C13 C14 1.521(3) . ?
C13 C15 1.525(3) . ?

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
C12 O1 C1 123.07(13) . . ?
O1 C1 C2 115.24(13) . . ?
O2 C1 O1 116.00(14) . . ?
O2 C1 C2 128.76(16) . . ?
C1 C2 C3 129.65(14) . . ?
C10 C2 C1 120.39(15) . . ?
C10 C2 C3 109.84(14) . . ?
C2 C3 C4 116.17(13) . . ?
C2 C3 C8 101.18(12) . . ?
C4 C3 C8 110.73(15) . . ?
C5 C4 C3 112.07(14) . . ?
O3 C5 C4 123.50(16) . . ?
O3 C5 C6 121.22(16) . . ?
C4 C5 C6 115.26(14) . . ?
O7 C6 C5 109.25(13) . . ?
O7 C6 C13 108.20(13) . . ?
C13 C6 C5 114.63(14) . . ?
C8 O7 C6 114.02(12) . . ?
O7 C8 C3 114.85(13) . . ?
O7 C8 O9 109.30(12) . . ?
O9 C8 C3 106.48(13) . . ?
C10 O9 C8 107.47(12) . . ?
C2 C10 C11 123.05(15) . . ?
O9 C10 C2 114.25(14) . . ?
O9 C10 C11 122.70(14) . . ?
C12 C11 C10 116.51(14) . . ?
O1 C12 C16 111.25(14) . . ?
C11 C12 O1 121.72(15) . . ?
C11 C12 C16 127.00(15) . . ?
C6 C13 C15 110.01(15) . . ?
C14 C13 C6 112.11(15) . . ?
C14 C13 C15 112.06(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 175.67(15) . . . . ?
O1 C1 C2 C10 0.1(2) . . . . ?
O2 C1 C2 C3 -3.6(3) . . . . ?
O2 C1 C2 C10 -179.15(16) . . . . ?
O3 C5 C6 O7 -159.79(16) . . . . ?
O3 C5 C6 C13 -38.2(2) . . . . ?
C1 O1 C12 C11 -0.7(2) . . . . ?
C1 O1 C12 C16 -179.06(13) . . . . ?
C1 C2 C3 C4 57.8(2) . . . . ?
C1 C2 C3 C8 177.70(16) . . . . ?
C1 C2 C10 O9 178.00(14) . . . . ?
C1 C2 C10 C11 -1.2(2) . . . . ?
C2 C3 C4 C5 65.2(2) . . . . ?
C2 C3 C8 O7 -112.54(15) . . . . ?
C2 C3 C8 O9 8.58(16) . . . . ?
C2 C10 C11 C12 1.4(2) . . . . ?
C3 C2 C10 O9 1.6(2) . . . . ?
C3 C2 C10 C11 -177.59(15) . . . . ?
C3 C4 C5 O3 -146.14(17) . . . . ?
C3 C4 C5 C6 32.4(2) . . . . ?
C3 C8 O9 C10 -8.18(16) . . . . ?
C4 C3 C8 O7 11.20(19) . . . . ?
C4 C3 C8 O9 132.32(13) . . . . ?
C4 C5 C6 O7 21.6(2) . . . . ?
C4 C5 C6 C13 143.25(15) . . . . ?
C5 C6 O7 C8 -64.57(17) . . . . ?
C5 C6 C13 C14 -67.62(19) . . . . ?
C5 C6 C13 C15 166.97(14) . . . . ?
C6 O7 C8 C3 46.84(18) . . . . ?
C6 O7 C8 O9 -72.73(15) . . . . ?
O7 C6 C13 C14 54.56(18) . . . . ?
O7 C6 C13 C15 -70.85(17) . . . . ?
O7 C8 O9 C10 116.42(14) . . . . ?
C8 C3 C4 C5 -49.44(18) . . . . ?
C8 O9 C10 C2 4.30(18) . . . . ?
C8 O9 C10 C11 -176.46(14) . . . . ?
O9 C10 C11 C12 -177.81(15) . . . . ?
C10 C2 C3 C4 -126.33(16) . . . . ?
C10 C2 C3 C8 -6.39(18) . . . . ?
C10 C11 C12 O1 -0.4(2) . . . . ?
C10 C11 C12 C16 177.71(15) . . . . ?
C12 O1 C1 O2 -179.80(14) . . . . ?
C12 O1 C1 C2 0.8(2) . . . . ?
C13 C6 O7 C8 170.02(13) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-16
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ma2molt
_database_code_depnum_ccdc_archive 'CCDC 1444736'
_audit_update_record             
;
2015-12-30 deposited with the CCDC.
2016-03-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.1440(6)
_cell_length_b                   14.5913(10)
_cell_length_c                   11.0130(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.901(7)
_cell_angle_gamma                90
_cell_volume                     1303.91(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    896
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.8810
_cell_measurement_theta_min      3.7520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.1486

_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4691

_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         3.756
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00   35.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   57.0000  150.0000 94
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0689349000
_diffrn_orient_matrix_UB_12      0.0089051000
_diffrn_orient_matrix_UB_13      0.0419491000
_diffrn_orient_matrix_UB_21      -0.0514476000
_diffrn_orient_matrix_UB_22      -0.0016078000
_diffrn_orient_matrix_UB_23      0.0488837000
_diffrn_orient_matrix_UB_31      0.0146265000
_diffrn_orient_matrix_UB_32      -0.0477877000
_diffrn_orient_matrix_UB_33      0.0062126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1334
_reflns_number_total             2494
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
w=exp[0.7600(sinθ/λ)²)]/[σ²(Fo²)+(0.0120P)²] 
where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.7352(2) 0.34115(12) 0.50316(15) 0.0253(5) Uani 1 1 d . . . . .
O2 O 0.6759(2) 0.21011(13) 0.59608(15) 0.0255(5) Uani 1 1 d . . . . .
O3 O 0.2991(2) 0.20698(12) 0.99186(16) 0.0291(5) Uani 1 1 d . . . . .
O7 O 0.3757(2) 0.43277(11) 0.88747(15) 0.0227(5) Uani 1 1 d . . . . .
O9 O 0.5920(2) 0.48697(11) 0.78888(14) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.6781(3) 0.2938(2) 0.6030(2) 0.0227(7) Uani 1 1 d . . . . .
C2 C 0.6321(3) 0.34996(18) 0.6981(2) 0.0195(6) Uani 1 1 d . . . . .
C3 C 0.5758(3) 0.32299(17) 0.8194(2) 0.0205(6) Uani 1 1 d . . . . .
H3 H 0.6674 0.2914 0.8693 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4195(3) 0.26371(18) 0.8138(2) 0.0230(7) Uani 1 1 d . . . . .
H4A H 0.3413 0.2840 0.7453 0.028 Uiso 1 1 calc R . . . .
H4B H 0.4481 0.1988 0.7999 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3408(3) 0.27257(19) 0.9318(2) 0.0216(7) Uani 1 1 d . . . . .
C6 C 0.3177(3) 0.36966(17) 0.9753(2) 0.0212(7) Uani 1 1 d . . . . .
H6 H 0.3842 0.3783 1.0551 0.025 Uiso 1 1 calc R . . . .
C8 C 0.5447(3) 0.41786(17) 0.8744(2) 0.0230(7) Uani 1 1 d . . . . .
H8 H 0.6107 0.4251 0.9546 0.028 Uiso 1 1 calc R . . . .
C10 C 0.6384(3) 0.44158(18) 0.6893(2) 0.0211(6) Uani 1 1 d . . . . .
C11 C 0.6919(3) 0.48800(19) 0.5871(2) 0.0249(7) Uani 1 1 d . . . . .
H11 H 0.6942 0.5530 0.5825 0.030 Uiso 1 1 calc R . . . .
C12 C 0.7390(4) 0.43496(19) 0.4973(2) 0.0245(7) Uani 1 1 d . . . . .
C13 C 0.1374(3) 0.39523(18) 0.9904(2) 0.0227(7) Uani 1 1 d . . . . .
H13 H 0.1336 0.4634 0.9984 0.027 Uiso 1 1 calc R . . . .
C14 C 0.0765(4) 0.35612(19) 1.1051(2) 0.0308(7) Uani 1 1 d . . . . .
H14A H 0.0786 0.2890 1.1012 0.046 Uiso 1 1 calc GR . . . .
H14B H -0.0366 0.3769 1.1127 0.046 Uiso 1 1 calc GR . . . .
H14C H 0.1478 0.3770 1.1758 0.046 Uiso 1 1 calc GR . . . .
C15 C 0.0238(4) 0.37020(19) 0.8768(2) 0.0307(7) Uani 1 1 d . . . . .
H15A H 0.0696 0.3948 0.8041 0.046 Uiso 1 1 calc GR . . . .
H15B H -0.0858 0.3964 0.8837 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.0150 0.3034 0.8701 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.8020(4) 0.4665(2) 0.3811(2) 0.0361(8) Uani 1 1 d . . . . .
H16A H 0.9164 0.4464 0.3782 0.054 Uiso 1 1 calc GR . . . .
H16B H 0.7970 0.5336 0.3769 0.054 Uiso 1 1 calc GR . . . .
H16C H 0.7340 0.4404 0.3120 0.054 Uiso 1 1 calc GR . . . .


_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 C1 1.411(3) . ?
O1 C12 1.371(3) . ?
O2 C1 1.223(3) . ?
O3 C5 1.227(3) . ?
O7 C6 1.444(3) . ?
O7 C8 1.413(3) . ?
O9 C8 1.454(3) . ?
O9 C10 1.362(3) . ?
C1 C2 1.406(4) . ?
C2 C3 1.501(3) . ?
C2 C10 1.342(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.536(4) . ?
C3 C8 1.540(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.503(4) . ?
C5 C6 1.512(3) . ?
C6 H6 1.0000 . ?
C6 C13 1.538(4) . ?
C8 H8 1.0000 . ?
C10 C11 1.414(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.338(3) . ?
C12 C16 1.491(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.508(3) . ?
C13 C15 1.535(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C12 O1 C1 122.4(2) . . ?
C8 O7 C6 110.33(19) . . ?
C10 O9 C8 106.93(18) . . ?
O2 C1 O1 116.4(2) . . ?
O2 C1 C2 128.7(3) . . ?
C2 C1 O1 114.9(2) . . ?
C1 C2 C3 129.1(2) . . ?
C10 C2 C1 120.9(2) . . ?
C10 C2 C3 110.0(2) . . ?
C2 C3 H3 109.8 . . ?
C2 C3 C4 115.2(2) . . ?
C2 C3 C8 100.8(2) . . ?
C4 C3 H3 109.8 . . ?
C4 C3 C8 111.0(2) . . ?
C8 C3 H3 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 109.2(2) . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
O3 C5 C4 123.8(2) . . ?
O3 C5 C6 120.8(2) . . ?
C4 C5 C6 115.3(2) . . ?
O7 C6 C5 109.2(2) . . ?
O7 C6 H6 108.9 . . ?
O7 C6 C13 106.7(2) . . ?
C5 C6 H6 108.9 . . ?
C5 C6 C13 114.0(2) . . ?
C13 C6 H6 108.9 . . ?
O7 C8 O9 105.9(2) . . ?
O7 C8 C3 111.9(2) . . ?
O7 C8 H8 110.3 . . ?
O9 C8 C3 107.9(2) . . ?
O9 C8 H8 110.3 . . ?
C3 C8 H8 110.3 . . ?
O9 C10 C11 122.2(2) . . ?
C2 C10 O9 114.3(2) . . ?
C2 C10 C11 123.4(2) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 C10 116.0(2) . . ?
C12 C11 H11 122.0 . . ?
O1 C12 C16 111.1(2) . . ?
C11 C12 O1 122.2(2) . . ?
C11 C12 C16 126.7(2) . . ?
C6 C13 H13 106.7 . . ?
C14 C13 C6 112.6(2) . . ?
C14 C13 H13 106.7 . . ?
C14 C13 C15 111.9(2) . . ?
C15 C13 C6 111.6(2) . . ?
C15 C13 H13 106.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -176.2(2) . . . . ?
O1 C1 C2 C10 2.2(4) . . . . ?
O2 C1 C2 C3 3.3(5) . . . . ?
O2 C1 C2 C10 -178.3(3) . . . . ?
O3 C5 C6 O7 -179.6(2) . . . . ?
O3 C5 C6 C13 -60.3(3) . . . . ?
O7 C6 C13 C14 -162.19(19) . . . . ?
O7 C6 C13 C15 70.9(3) . . . . ?
O9 C10 C11 C12 177.8(2) . . . . ?
C1 O1 C12 C11 1.4(4) . . . . ?
C1 O1 C12 C16 -179.0(2) . . . . ?
C1 C2 C3 C4 -59.6(4) . . . . ?
C1 C2 C3 C8 -179.1(3) . . . . ?
C1 C2 C10 O9 -179.3(2) . . . . ?
C1 C2 C10 C11 -0.7(4) . . . . ?
C2 C3 C4 C5 -158.0(2) . . . . ?
C2 C3 C8 O7 112.9(2) . . . . ?
C2 C3 C8 O9 -3.2(3) . . . . ?
C2 C10 C11 C12 -0.6(4) . . . . ?
C3 C2 C10 O9 -0.6(3) . . . . ?
C3 C2 C10 C11 178.0(3) . . . . ?
C3 C4 C5 O3 -129.6(3) . . . . ?
C3 C4 C5 C6 49.3(3) . . . . ?
C4 C3 C8 O7 -9.6(3) . . . . ?
C4 C3 C8 O9 -125.7(2) . . . . ?
C4 C5 C6 O7 1.5(3) . . . . ?
C4 C5 C6 C13 120.7(2) . . . . ?
C5 C6 C13 C14 77.2(3) . . . . ?
C5 C6 C13 C15 -49.8(3) . . . . ?
C6 O7 C8 O9 -177.52(17) . . . . ?
C6 O7 C8 C3 65.2(3) . . . . ?
C8 O7 C6 C5 -60.3(3) . . . . ?
C8 O7 C6 C13 176.0(2) . . . . ?
C8 O9 C10 C2 -1.6(3) . . . . ?
C8 O9 C10 C11 179.8(2) . . . . ?
C8 C3 C4 C5 -44.2(3) . . . . ?
C10 O9 C8 O7 -116.9(2) . . . . ?
C10 O9 C8 C3 3.0(3) . . . . ?
C10 C2 C3 C4 121.9(2) . . . . ?
C10 C2 C3 C8 2.3(3) . . . . ?
C10 C11 C12 O1 0.3(4) . . . . ?
C10 C11 C12 C16 -179.2(3) . . . . ?
C12 O1 C1 O2 177.8(2) . . . . ?
C12 O1 C1 C2 -2.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-22
_olex2_submission_special_instructions 'No special instructions were received'
