# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mx5525
_database_code_depnum_ccdc_archive 'CCDC 1541450'
_audit_update_record             
;
2017-05-23 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O5'
_chemical_formula_sum            'C20 H20 N2 O5'
_chemical_formula_weight         368.38
_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'
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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   12.7770(17)
_cell_length_b                   16.254(2)
_cell_length_c                   17.725(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3680.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8855
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4711
_cell_measurement_theta_min      1.5938
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12304
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3754
_reflns_number_total             4166
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.138
_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)+(0.0451P)²+2.2715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.34684(11) 0.41371(8) 0.50488(8) 0.0333(3) Uani 1 1 d . . . . .
O2 O 0.46589(10) 0.57806(9) 0.65648(8) 0.0316(3) Uani 1 1 d . . . . .
O3 O 0.19410(10) 0.63345(9) 0.53649(7) 0.0291(3) Uani 1 1 d . . . . .
O4 O -0.07851(11) 0.58321(9) 0.54273(8) 0.0353(3) Uani 1 1 d . . . . .
O5 O 0.02446(10) 0.62948(8) 0.44811(8) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.01945(13) 0.57419(12) 0.68703(10) 0.0374(4) Uani 1 1 d . . . . .
H1A H -0.0416 0.5660 0.6680 0.045 Uiso 1 1 calc R . . . .
H1B H 0.0295 0.5673 0.7346 0.045 Uiso 1 1 calc R . . . .
N2 N 0.26879(15) 0.48158(12) 0.74968(11) 0.0444(5) Uani 1 1 d . . . . .
C1 C 0.44084(15) 0.39684(12) 0.53944(11) 0.0288(4) Uani 1 1 d . . . . .
C2 C 0.48915(18) 0.32315(13) 0.51986(13) 0.0377(5) Uani 1 1 d . . . . .
H2 H 0.4583 0.2876 0.4853 0.045 Uiso 1 1 calc R . . . .
C3 C 0.58366(19) 0.30416(13) 0.55285(14) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.6167 0.2549 0.5407 0.050 Uiso 1 1 calc R . . . .
C4 C 0.63048(18) 0.35786(14) 0.60424(13) 0.0424(5) Uani 1 1 d . . . . .
H4 H 0.6948 0.3446 0.6256 0.051 Uiso 1 1 calc R . . . .
C5 C 0.58197(16) 0.43005(13) 0.62333(11) 0.0341(5) Uani 1 1 d . . . . .
H5 H 0.6134 0.4655 0.6577 0.041 Uiso 1 1 calc R . . . .
C6 C 0.48506(14) 0.45073(12) 0.59128(10) 0.0264(4) Uani 1 1 d . . . . .
C7 C 0.43075(14) 0.52709(11) 0.61117(10) 0.0241(4) Uani 1 1 d . . . . .
C8 C 0.33140(14) 0.53929(11) 0.57348(10) 0.0248(4) Uani 1 1 d . . . . .
C9 C 0.29634(15) 0.48373(12) 0.52297(11) 0.0286(4) Uani 1 1 d . . . . .
H9 H 0.2330 0.4945 0.4990 0.034 Uiso 1 1 calc R . . . .
C10 C 0.27122(14) 0.61572(11) 0.59306(10) 0.0253(4) Uani 1 1 d . . . . .
H10 H 0.3204 0.6619 0.5954 0.030 Uiso 1 1 calc R . . . .
C11 C 0.21090(14) 0.61047(11) 0.67081(10) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.09937(14) 0.59789(11) 0.64228(11) 0.0253(4) Uani 1 1 d . . . . .
C13 C 0.09738(14) 0.61143(11) 0.56732(10) 0.0257(4) Uani 1 1 d . . . . .
C14 C 0.24404(15) 0.53769(13) 0.71474(11) 0.0302(4) Uani 1 1 d . . . . .
C15 C 0.22730(16) 0.68987(12) 0.71928(11) 0.0312(4) Uani 1 1 d . . . . .
H15 H 0.3029 0.6999 0.7213 0.037 Uiso 1 1 calc R . . . .
C16 C 0.1899(2) 0.68114(15) 0.80042(13) 0.0443(5) Uani 1 1 d . . . . .
H16A H 0.1171 0.6665 0.8008 0.066 Uiso 1 1 calc GR . . . .
H16B H 0.1993 0.7324 0.8264 0.066 Uiso 1 1 calc GR . . . .
H16C H 0.2296 0.6390 0.8253 0.066 Uiso 1 1 calc GR . . . .
C17 C 0.17828(18) 0.76418(13) 0.68043(13) 0.0396(5) Uani 1 1 d . . . . .
H17A H 0.2021 0.7669 0.6291 0.059 Uiso 1 1 calc GR . . . .
H17B H 0.1984 0.8135 0.7065 0.059 Uiso 1 1 calc GR . . . .
H17C H 0.1034 0.7590 0.6812 0.059 Uiso 1 1 calc GR . . . .
C18 C 0.00635(15) 0.60602(11) 0.51930(11) 0.0270(4) Uani 1 1 d . . . . .
C19 C -0.06486(17) 0.62403(13) 0.39716(12) 0.0351(5) Uani 1 1 d . . . . .
H19A H -0.1225 0.6569 0.4162 0.042 Uiso 1 1 calc R . . . .
H19B H -0.0881 0.5674 0.3929 0.042 Uiso 1 1 calc R . . . .
C20 C -0.0303(2) 0.65552(17) 0.32184(14) 0.0517(6) Uani 1 1 d . . . . .
H20A H -0.0863 0.6494 0.2861 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.0294 0.6247 0.3050 0.078 Uiso 1 1 calc GR . . . .
H20C H -0.0119 0.7126 0.3261 0.078 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 1.376(2) . ?
O1 C9 1.347(2) . ?
O2 C7 1.238(2) . ?
O3 C10 1.435(2) . ?
O3 C13 1.398(2) . ?
O4 C18 1.219(2) . ?
O5 C18 1.338(2) . ?
O5 C19 1.458(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C12 1.349(2) . ?
N2 C14 1.147(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(3) . ?
C6 C7 1.465(3) . ?
C7 C8 1.448(2) . ?
C8 C9 1.348(3) . ?
C8 C10 1.502(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C10 C11 1.581(3) . ?
C11 C12 1.526(2) . ?
C11 C14 1.478(3) . ?
C11 C15 1.564(3) . ?
C12 C13 1.347(3) . ?
C13 C18 1.444(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.522(3) . ?
C15 C17 1.525(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.496(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 O1 C1 118.72(15) . . ?
C13 O3 C10 106.41(13) . . ?
C18 O5 C19 115.55(15) . . ?
H1A N1 H1B 120.0 . . ?
C12 N1 H1A 120.0 . . ?
C12 N1 H1B 120.0 . . ?
O1 C1 C2 116.59(18) . . ?
O1 C1 C6 121.59(17) . . ?
C6 C1 C2 121.82(19) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.40(18) . . ?
C1 C6 C7 120.03(17) . . ?
C5 C6 C7 121.57(18) . . ?
O2 C7 C6 123.44(17) . . ?
O2 C7 C8 121.71(17) . . ?
C8 C7 C6 114.85(16) . . ?
C7 C8 C10 117.10(16) . . ?
C9 C8 C7 120.39(17) . . ?
C9 C8 C10 122.51(17) . . ?
O1 C9 C8 124.39(17) . . ?
O1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
O3 C10 C8 110.87(15) . . ?
O3 C10 H10 108.4 . . ?
O3 C10 C11 106.56(14) . . ?
C8 C10 H10 108.4 . . ?
C8 C10 C11 113.98(15) . . ?
C11 C10 H10 108.4 . . ?
C12 C11 C10 100.00(14) . . ?
C12 C11 C15 114.69(15) . . ?
C14 C11 C10 111.26(15) . . ?
C14 C11 C12 109.56(16) . . ?
C14 C11 C15 109.41(16) . . ?
C15 C11 C10 111.65(15) . . ?
N1 C12 C11 123.39(17) . . ?
C13 C12 N1 127.75(18) . . ?
C13 C12 C11 108.82(15) . . ?
O3 C13 C18 119.82(16) . . ?
C12 C13 O3 114.25(16) . . ?
C12 C13 C18 125.92(17) . . ?
N2 C14 C11 179.0(2) . . ?
C11 C15 H15 106.8 . . ?
C16 C15 C11 113.57(17) . . ?
C16 C15 H15 106.8 . . ?
C16 C15 C17 111.80(18) . . ?
C17 C15 C11 110.51(16) . . ?
C17 C15 H15 106.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 124.18(17) . . ?
O4 C18 C13 122.29(17) . . ?
O5 C18 C13 113.52(16) . . ?
O5 C19 H19A 110.2 . . ?
O5 C19 H19B 110.2 . . ?
O5 C19 C20 107.51(18) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 H1A O4 0.86 2.29 2.851(2) 123.3 .
N1 H1B O2 0.86 2.10 2.857(2) 146.2 6_557

_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_mx5721b
_database_code_depnum_ccdc_archive 'CCDC 1541449'
_audit_update_record             
;
2017-05-23 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 Cl N2 O7'
_chemical_formula_sum            'C27 H23 Cl N2 O7'
_chemical_formula_weight         522.92
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   13.668(3)
_cell_length_b                   14.731(3)
_cell_length_c                   13.261(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.59(3)
_cell_angle_gamma                90
_cell_volume                     2482.6(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7334
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.3824
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.84697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.188
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19385
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.116
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   Confocal
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5122
_reflns_number_total             5674
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+1.3336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1264
_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:
 C8(H8), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.12164(4) 0.17017(4) 0.40257(5) 0.04257(16) Uani 1 1 d . . . . .
O1 O 0.46049(11) 0.37660(10) 0.46193(10) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.53239(11) 0.23572(9) 0.74789(10) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.68187(10) 0.43844(9) 0.75836(10) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.69391(12) 0.29049(10) 0.96850(11) 0.0334(3) Uani 1 1 d . . . . .
O5 O 0.76840(12) 0.42565(10) 0.96577(11) 0.0342(4) Uani 1 1 d . . . . .
O6 O 0.45967(11) 0.43389(10) 0.70271(11) 0.0295(3) Uani 1 1 d . . . . .
O7 O 0.50434(11) 0.42395(10) 0.88330(10) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.87977(15) 0.30989(13) 0.69945(16) 0.0387(4) Uani 1 1 d . . . . .
N2 N 0.82724(14) 0.59422(13) 0.68985(15) 0.0340(4) Uani 1 1 d . . . . .
C1 C 0.24470(16) 0.18934(14) 0.50287(16) 0.0290(4) Uani 1 1 d . . . . .
C2 C 0.31443(15) 0.24582(13) 0.48107(15) 0.0254(4) Uani 1 1 d . . . . .
H2 H 0.296267 0.272454 0.413027 0.030 Uiso 1 1 calc R . . . .
C3 C 0.41336(15) 0.26325(13) 0.56198(15) 0.0230(4) Uani 1 1 d . . . . .
C4 C 0.43931(15) 0.22233(13) 0.66307(15) 0.0243(4) Uani 1 1 d . . . . .
C5 C 0.36823(17) 0.16454(14) 0.68404(17) 0.0318(5) Uani 1 1 d . . . . .
H5 H 0.386070 0.137254 0.751690 0.038 Uiso 1 1 calc R . . . .
C6 C 0.27158(17) 0.14803(15) 0.60428(17) 0.0336(5) Uani 1 1 d . . . . .
H6 H 0.224139 0.109320 0.617933 0.040 Uiso 1 1 calc R . . . .
C7 C 0.48585(15) 0.32740(12) 0.54113(14) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.59846(14) 0.32667(12) 0.62213(14) 0.0204(4) Uani 1 1 d . . . . .
H8 H 0.640930 0.289640 0.592275 0.025 Uiso 1 1 calc R . . . .
C9 C 0.61376(14) 0.29027(12) 0.73599(14) 0.0206(4) Uani 1 1 d . . . . .
H9 H 0.679206 0.255109 0.762288 0.025 Uiso 1 1 calc R . . . .
C10 C 0.64563(14) 0.42303(12) 0.64314(14) 0.0205(4) Uani 1 1 d . . . . .
H10 H 0.590802 0.467380 0.605803 0.025 Uiso 1 1 calc R . . . .
C11 C 0.63074(14) 0.37758(12) 0.80583(14) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.52161(15) 0.41577(13) 0.79185(14) 0.0222(4) Uani 1 1 d . . . . .
C13 C 0.39711(16) 0.45403(15) 0.86998(17) 0.0315(5) Uani 1 1 d . . . . .
H13A H 0.384489 0.440972 0.935862 0.038 Uiso 1 1 calc R . . . .
H13B H 0.346102 0.420229 0.811246 0.038 Uiso 1 1 calc R . . . .
C14 C 0.38214(18) 0.55368(15) 0.84592(18) 0.0363(5) Uani 1 1 d . . . . .
H14A H 0.395429 0.566938 0.781240 0.054 Uiso 1 1 calc GR . . . .
H14B H 0.430198 0.587435 0.905542 0.054 Uiso 1 1 calc GR . . . .
H14C H 0.311215 0.570424 0.835593 0.054 Uiso 1 1 calc GR . . . .
C15 C 0.70127(14) 0.35982(13) 0.92378(14) 0.0224(4) Uani 1 1 d . . . . .
C16 C 0.85079(17) 0.40945(17) 1.07308(16) 0.0368(5) Uani 1 1 d . . . . .
H16A H 0.826279 0.365253 1.112652 0.044 Uiso 1 1 calc R . . . .
H16B H 0.866258 0.465488 1.114380 0.044 Uiso 1 1 calc R . . . .
C17 C 0.9482(2) 0.3750(2) 1.0594(2) 0.0594(8) Uani 1 1 d . . . . .
H17A H 0.970628 0.417879 1.017766 0.089 Uiso 1 1 calc GR . . . .
H17B H 0.933606 0.317750 1.022295 0.089 Uiso 1 1 calc GR . . . .
H17C H 1.002883 0.367383 1.129363 0.089 Uiso 1 1 calc GR . . . .
C18 C 0.79054(15) 0.52617(13) 0.65449(15) 0.0238(4) Uani 1 1 d . . . . .
C19 C 0.82134(15) 0.36612(14) 0.65908(15) 0.0245(4) Uani 1 1 d . . . . .
C20 C 0.74164(14) 0.43794(13) 0.60954(14) 0.0213(4) Uani 1 1 d . . . . .
C21 C 0.70392(14) 0.43855(14) 0.48312(14) 0.0231(4) Uani 1 1 d . . . . .
H21A H 0.674207 0.379539 0.456249 0.028 Uiso 1 1 calc R . . . .
H21B H 0.648108 0.483040 0.455102 0.028 Uiso 1 1 calc R . . . .
C22 C 0.78827(15) 0.45962(14) 0.43853(14) 0.0245(4) Uani 1 1 d . . . . .
C23 C 0.80591(17) 0.54888(15) 0.41485(16) 0.0313(5) Uani 1 1 d . . . . .
H23 H 0.767620 0.595832 0.429505 0.038 Uiso 1 1 calc R . . . .
C24 C 0.88028(18) 0.56806(17) 0.36951(17) 0.0382(5) Uani 1 1 d . . . . .
H24 H 0.891578 0.627774 0.353758 0.046 Uiso 1 1 calc R . . . .
C25 C 0.93760(17) 0.49873(19) 0.34773(17) 0.0414(6) Uani 1 1 d . . . . .
H25 H 0.987119 0.511786 0.316957 0.050 Uiso 1 1 calc R . . . .
C26 C 0.92153(17) 0.41030(18) 0.37148(17) 0.0391(5) Uani 1 1 d . . . . .
H26 H 0.960687 0.363774 0.357364 0.047 Uiso 1 1 calc R . . . .
C27 C 0.84684(16) 0.39043(15) 0.41658(16) 0.0308(4) Uani 1 1 d . . . . .
H27 H 0.835989 0.330564 0.432138 0.037 Uiso 1 1 calc R . . . .


_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
Cl1 C1 1.741(2) . ?
O1 C7 1.217(2) . ?
O2 C4 1.367(2) . ?
O2 C9 1.427(2) . ?
O3 C10 1.440(2) . ?
O3 C11 1.419(2) . ?
O4 C15 1.204(2) . ?
O5 C15 1.310(2) . ?
O5 C16 1.473(2) . ?
O6 C12 1.204(2) . ?
O7 C12 1.323(2) . ?
O7 C13 1.478(2) . ?
N1 C19 1.138(3) . ?
N2 C18 1.142(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.406(3) . ?
C3 C4 1.392(3) . ?
C3 C7 1.467(3) . ?
C4 C5 1.394(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.519(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.542(2) . ?
C8 C10 1.541(2) . ?
C9 H9 0.9800 . ?
C9 C11 1.552(2) . ?
C10 H10 0.9800 . ?
C10 C20 1.549(3) . ?
C11 C12 1.540(3) . ?
C11 C15 1.528(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.500(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.497(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C20 1.483(3) . ?
C19 C20 1.487(3) . ?
C20 C21 1.562(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(3) . ?
C22 C23 1.393(3) . ?
C22 C27 1.391(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(3) . ?
C27 H27 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 C9 121.15(14) . . ?
C11 O3 C10 109.75(13) . . ?
C15 O5 C16 117.23(16) . . ?
C12 O7 C13 114.91(15) . . ?
C2 C1 Cl1 119.17(16) . . ?
C2 C1 C6 120.63(18) . . ?
C6 C1 Cl1 120.19(16) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.79(18) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C7 120.01(17) . . ?
C4 C3 C2 119.24(18) . . ?
C4 C3 C7 120.68(17) . . ?
O2 C4 C3 124.06(17) . . ?
O2 C4 C5 115.44(17) . . ?
C3 C4 C5 120.49(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.78(19) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.07(19) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C3 123.27(17) . . ?
O1 C7 C8 120.49(17) . . ?
C3 C7 C8 116.17(15) . . ?
C7 C8 H8 108.4 . . ?
C7 C8 C9 115.60(15) . . ?
C7 C8 C10 111.65(15) . . ?
C9 C8 H8 108.4 . . ?
C10 C8 H8 108.4 . . ?
C10 C8 C9 104.25(14) . . ?
O2 C9 C8 118.26(15) . . ?
O2 C9 H9 108.0 . . ?
O2 C9 C11 110.62(15) . . ?
C8 C9 H9 108.0 . . ?
C8 C9 C11 103.47(14) . . ?
C11 C9 H9 108.0 . . ?
O3 C10 C8 107.13(14) . . ?
O3 C10 H10 109.4 . . ?
O3 C10 C20 106.61(14) . . ?
C8 C10 H10 109.4 . . ?
C8 C10 C20 114.89(15) . . ?
C20 C10 H10 109.4 . . ?
O3 C11 C9 104.41(14) . . ?
O3 C11 C12 109.21(14) . . ?
O3 C11 C15 109.53(15) . . ?
C12 C11 C9 107.78(15) . . ?
C15 C11 C9 111.62(15) . . ?
C15 C11 C12 113.83(15) . . ?
O6 C12 O7 125.56(18) . . ?
O6 C12 C11 119.95(16) . . ?
O7 C12 C11 114.48(15) . . ?
O7 C13 H13A 109.3 . . ?
O7 C13 H13B 109.3 . . ?
O7 C13 C14 111.73(17) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
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 . . ?
O4 C15 O5 126.23(17) . . ?
O4 C15 C11 120.94(17) . . ?
O5 C15 C11 112.81(16) . . ?
O5 C16 H16A 109.7 . . ?
O5 C16 H16B 109.7 . . ?
O5 C16 C17 109.61(19) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C20 179.0(2) . . ?
N1 C19 C20 177.0(2) . . ?
C10 C20 C21 109.24(14) . . ?
C18 C20 C10 108.24(15) . . ?
C18 C20 C19 107.31(15) . . ?
C18 C20 C21 110.39(15) . . ?
C19 C20 C10 109.42(15) . . ?
C19 C20 C21 112.15(16) . . ?
C20 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 C20 115.07(15) . . ?
C22 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C23 C22 C21 120.20(18) . . ?
C27 C22 C21 120.84(18) . . ?
C27 C22 C23 118.91(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.1(2) . . ?
C27 C26 H26 119.9 . . ?
C22 C27 H27 119.8 . . ?
C26 C27 C22 120.4(2) . . ?
C26 C27 H27 119.8 . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1541448'
_audit_update_record             
;
2017-05-23 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_audit_creation_date             2016-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 O7'
_chemical_formula_sum            'C21 H18 O7'
_chemical_formula_weight         382.35
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6133(15)
_cell_length_b                   10.8331(17)
_cell_length_c                   11.794(2)
_cell_angle_alpha                103.557(8)
_cell_angle_beta                 95.557(9)
_cell_angle_gamma                108.701(7)
_cell_volume                     880.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2501
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4762
_cell_measurement_theta_min      1.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.115
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12308
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.808
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 99.4000
_diffrn_measured_fraction_theta_max 27.4762
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9382
	          2theta: -19.8823
scan:
	Number of images: 350
	           Slice: -110.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9382
	          2theta: -19.8823
scan:
	Number of images: 281
	           Slice: -75.5000 - 65.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9382
	          2theta: -19.8823
scan:
	Number of images: 286
	           Slice: -80.0000 - 63.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9382
	          2theta: -19.8823
;
_diffrn_measurement_device       
;
?
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4006
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0545
_diffrn_orient_matrix_UB_12      -0.1092
_diffrn_orient_matrix_UB_13      0.0719
_diffrn_orient_matrix_UB_21      -0.0011
_diffrn_orient_matrix_UB_22      -0.0175
_diffrn_orient_matrix_UB_23      -0.1000
_diffrn_orient_matrix_UB_31      0.0808
_diffrn_orient_matrix_UB_32      -0.0233
_diffrn_orient_matrix_UB_33      0.0285
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3648
_reflns_number_total             4002
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.3304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1149
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.31161(15) 0.64255(10) 0.36930(9) 0.0238(2) Uani 1 1 d . . . . .
O2 O 0.11635(19) 0.23536(11) 0.18247(11) 0.0371(3) Uani 1 1 d . . . . .
O3 O 0.30983(16) 0.60292(11) 0.06355(9) 0.0283(3) Uani 1 1 d . . . . .
O4 O 0.08601(16) 0.72803(12) 0.16069(11) 0.0363(3) Uani 1 1 d . . . . .
O5 O 0.33390(15) 0.88871(11) 0.29217(10) 0.0276(3) Uani 1 1 d . . . . .
O6 O 0.71761(16) 0.80850(13) 0.25664(11) 0.0395(3) Uani 1 1 d . . . . .
O7 O 0.58506(14) 0.85052(11) 0.09865(10) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.2623(2) 0.54252(14) 0.42635(13) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.2713(2) 0.58966(15) 0.55089(13) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.3385(2) 0.72940(16) 0.61231(13) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.3759 0.7937 0.5708 0.031 Uiso 1 1 calc R . . . .
C4 C 0.3489(2) 0.77068(17) 0.73239(14) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.3945 0.8629 0.7722 0.038 Uiso 1 1 calc R . . . .
C5 C 0.2912(3) 0.67457(18) 0.79604(15) 0.0336(4) Uani 1 1 d . . . . .
H5 H 0.2985 0.7035 0.8777 0.040 Uiso 1 1 calc R . . . .
C6 C 0.2245(2) 0.53920(18) 0.73870(14) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.1859 0.4767 0.7818 0.036 Uiso 1 1 calc R . . . .
C7 C 0.2131(2) 0.49199(16) 0.61454(14) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.1493(2) 0.35181(16) 0.55336(15) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.1100 0.2877 0.5948 0.034 Uiso 1 1 calc R . . . .
C9 C 0.1448(2) 0.31026(16) 0.43473(15) 0.0282(3) Uani 1 1 d . . . . .
H9 H 0.1028 0.2178 0.3962 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2031(2) 0.40519(15) 0.36830(13) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.1877(2) 0.35556(15) 0.23827(14) 0.0259(3) Uani 1 1 d . . . . .
C12 C 0.2608(2) 0.46624(15) 0.18523(13) 0.0245(3) Uani 1 1 d . . . . .
C13 C 0.2293(2) 0.47512(16) 0.07506(14) 0.0283(3) Uani 1 1 d . . . . .
H13 H 0.1585 0.4007 0.0112 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3838(2) 0.69500(15) 0.18227(12) 0.0220(3) Uani 1 1 d . . . . .
C15 C 0.3843(2) 0.60285(15) 0.26453(13) 0.0224(3) Uani 1 1 d . . . . .
H15 H 0.5123 0.6038 0.2863 0.027 Uiso 1 1 calc R . . . .
C16 C 0.2478(2) 0.77217(15) 0.20910(13) 0.0231(3) Uani 1 1 d . . . . .
C17 C 0.2187(2) 0.97001(17) 0.33398(15) 0.0304(4) Uani 1 1 d . . . . .
H17A H 0.0867 0.9196 0.2987 0.036 Uiso 1 1 calc R . . . .
H17B H 0.2576 1.0535 0.3108 0.036 Uiso 1 1 calc R . . . .
C18 C 0.2445(2) 1.00174(18) 0.46615(15) 0.0328(4) Uani 1 1 d . . . . .
H18A H 0.2017 0.9187 0.4883 0.049 Uiso 1 1 calc GR . . . .
H18B H 0.1726 1.0569 0.4948 0.049 Uiso 1 1 calc GR . . . .
H18C H 0.3757 1.0500 0.5003 0.049 Uiso 1 1 calc GR . . . .
C19 C 0.5832(2) 0.79084(15) 0.18456(13) 0.0234(3) Uani 1 1 d . . . . .
C20 C 0.7724(2) 0.93985(17) 0.09130(16) 0.0304(4) Uani 1 1 d . . . . .
H20A H 0.8560 0.8887 0.0783 0.037 Uiso 1 1 calc R . . . .
H20B H 0.8267 1.0123 0.1647 0.037 Uiso 1 1 calc R . . . .
C21 C 0.7484(2) 0.99779(18) -0.01042(15) 0.0327(4) Uani 1 1 d . . . . .
H21A H 0.7035 0.9258 -0.0833 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.8677 1.0617 -0.0138 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.6589 1.0429 0.0007 0.049 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 1.3776(17) . ?
O1 C15 1.4332(18) . ?
O2 C11 1.2244(19) . ?
O3 C13 1.3678(19) . ?
O3 C14 1.4509(18) . ?
O4 C16 1.1956(18) . ?
O5 C16 1.3223(19) . ?
O5 C17 1.4710(19) . ?
O6 C19 1.1985(19) . ?
O7 C19 1.3225(18) . ?
O7 C20 1.4682(18) . ?
C1 C2 1.425(2) . ?
C1 C10 1.385(2) . ?
C2 C3 1.413(2) . ?
C2 C7 1.420(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.406(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.418(2) . ?
C7 C8 1.417(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.359(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.422(2) . ?
C10 C11 1.481(2) . ?
C11 C12 1.460(2) . ?
C12 C13 1.330(2) . ?
C12 C15 1.496(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.547(2) . ?
C14 C16 1.539(2) . ?
C14 C19 1.533(2) . ?
C15 H15 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.494(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.500(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C1 O1 C15 112.64(11) . . ?
C13 O3 C14 107.35(11) . . ?
C16 O5 C17 117.34(12) . . ?
C19 O7 C20 114.88(12) . . ?
O1 C1 C2 115.22(12) . . ?
O1 C1 C10 123.40(13) . . ?
C10 C1 C2 121.37(13) . . ?
C3 C2 C1 122.10(13) . . ?
C3 C2 C7 119.55(14) . . ?
C7 C2 C1 118.35(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.39(14) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.41(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.31(15) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.12(15) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.22(14) . . ?
C8 C7 C2 119.56(14) . . ?
C8 C7 C6 122.21(14) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.61(14) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.37(14) . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 118.73(14) . . ?
C1 C10 C11 121.56(13) . . ?
C9 C10 C11 119.59(13) . . ?
O2 C11 C10 123.15(14) . . ?
O2 C11 C12 124.57(15) . . ?
C12 C11 C10 112.25(13) . . ?
C11 C12 C15 118.68(13) . . ?
C13 C12 C11 132.25(14) . . ?
C13 C12 C15 108.89(13) . . ?
O3 C13 H13 122.8 . . ?
C12 C13 O3 114.31(14) . . ?
C12 C13 H13 122.8 . . ?
O3 C14 C15 105.27(11) . . ?
O3 C14 C16 106.88(12) . . ?
O3 C14 C19 108.38(12) . . ?
C16 C14 C15 111.76(12) . . ?
C19 C14 C15 112.11(12) . . ?
C19 C14 C16 112.01(12) . . ?
O1 C15 C12 112.47(12) . . ?
O1 C15 C14 112.06(12) . . ?
O1 C15 H15 110.1 . . ?
C12 C15 C14 101.81(12) . . ?
C12 C15 H15 110.1 . . ?
C14 C15 H15 110.1 . . ?
O4 C16 O5 126.48(15) . . ?
O4 C16 C14 122.73(14) . . ?
O5 C16 C14 110.79(12) . . ?
O5 C17 H17A 110.0 . . ?
O5 C17 H17B 110.0 . . ?
O5 C17 C18 108.62(13) . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O7 125.49(14) . . ?
O6 C19 C14 123.17(14) . . ?
O7 C19 C14 111.34(12) . . ?
O7 C20 H20A 110.2 . . ?
O7 C20 H20B 110.2 . . ?
O7 C20 C21 107.72(13) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
