# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_2MePyNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450582'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFMX01_2MePyNO_1           
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: Due to unresolved disorder
;
_vrf_PLAT097_2MePyNO_1           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.02 eA-3  
RESPONSE: Due to unresolved disorder
;
# end Validation Reply Form
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '4(C6 H7 N O), C32 H32 O8'
_chemical_formula_sum            'C56 H60 N4 O12'
_chemical_formula_weight         981.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.1876(12)
_cell_length_b                   20.8706(7)
_cell_length_c                   17.9257(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.239(5)
_cell_angle_gamma                90
_cell_volume                     10124.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3718
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.3900
_cell_measurement_theta_min      3.3460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78414
_exptl_absorpt_correction_type   gaussian
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             4160
_exptl_crystal_size_max          0.5439
_exptl_crystal_size_mid          0.0742
_exptl_crystal_size_min          0.0543
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16567
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.745
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   52.00   89.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00  138.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4926 -125.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00   88.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   77.00  170.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
  6 omega   79.00  162.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega  -80.00   -8.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4926  125.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega -115.00  -20.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4926  -37.0000  -60.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0167890000
_diffrn_orient_matrix_UB_12      -0.0692889000
_diffrn_orient_matrix_UB_13      -0.0227266000
_diffrn_orient_matrix_UB_21      0.0512374000
_diffrn_orient_matrix_UB_22      -0.0155181000
_diffrn_orient_matrix_UB_23      -0.0104537000
_diffrn_orient_matrix_UB_31      0.0184221000
_diffrn_orient_matrix_UB_32      -0.0201756000
_diffrn_orient_matrix_UB_33      0.0858801000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6212
_reflns_number_total             8895
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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         1.018
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     814
_refine_ls_number_reflns         8895
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.025
_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)+(0.0898P)²+5.6263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1891
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4D) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C2B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: O1A(0.75) O1B(0.25) O1C(0.4) O1D(0.6) N1A(0.75) N1B(0.25) N1C(0.4)
 N1D(0.6) C1A(0.75) H1A(0.75) C1B(0.25) H1B(0.25) C1C(0.4) H1C(0.4) C1D(0.6)
 H1D(0.6) C2A(0.75) H2A(0.75) C2B(0.25) H2B(0.25) C2C(0.4) H2C(0.4) C2D(0.6)
 H2D(0.6) C3A(0.75) H3A(0.75) C3B(0.25) H3B(0.25) C3C(0.4) H3C(0.4) C3D(0.6)
 H3D(0.6) C4A(0.75) H4A(0.75) C4B(0.25) H4B(0.25) C4C(0.4) H4C(0.4) C4D(0.6)
 H4D(0.6) C5A(0.75) C5B(0.25) C5C(0.4) C5D(0.6) C6A(0.75) H6AA(0.75) H6AB(0.75)
 H6AC(0.75) C6B(0.25) H6BA(0.25) H6BB(0.25) H6BC(0.25) C6C(0.4) H6CA(0.4)
 H6CB(0.4) H6CC(0.4) C6D(0.6) H6DA(0.6) H6DB(0.6) H6DC(0.6)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
4.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F), C2(H2), C2A(H2A),
 C2B(H2B), C2C(H2C), C2D(H2D), C2E(H2E), C2F(H2F), C3A(H3A), C3B(H3B), C3C(H3C),
  C3D(H3D), C3E(H3E), C3F(H3F), C4A(H4A), C4B(H4B), C4C(H4C), C4D(H4D),
 C4E(H4E), C4F(H4F), C5(H5), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23),
 C26(H26)
4.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC), C6C(H6CA,H6CB,H6CC), C6D(H6DA,H6DB,
 H6DC), C6E(H6EA,H6EB,H6EC), C6F(H6FA,H6FB,H6FC), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
4.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O11(H11), O13(H13), O18(H18), O20(H20), O25(H25), O27(H27)
;
_atom_sites_solution_hydrogens   mixed
_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
O1A O 0.13957(12) 0.39612(17) -0.00825(19) 0.0481(8) Uani 0.75 1 d . . P A 2
O1B O 0.1561(3) 0.3617(4) -0.0370(5) 0.0301(16) Uani 0.25 1 d . . P B -1
O1C O 0.2478(4) 0.2226(7) 0.4112(7) 0.035(2) Uani 0.4 1 d . . P C 2
O1D O 0.2585(3) 0.2160(4) 0.3914(5) 0.0393(15) Uani 0.6 1 d . . P D 1
O1E O 0.12984(9) 0.33421(11) 0.32762(14) 0.0475(6) Uani 1 1 d . . . . .
O1F O -0.02335(11) 0.40807(11) -0.11010(13) 0.0521(7) Uani 1 1 d . . . . .
O4 O 0.01096(11) 0.29556(11) -0.12206(13) 0.0525(7) Uani 1 1 d . . . . .
H4 H -0.0008 0.3311 -0.1194 0.079 Uiso 1 1 calc GR . . . .
O6 O 0.01342(9) 0.29603(10) 0.14333(13) 0.0421(5) Uani 1 1 d . . . . .
H6 H 0.0251(15) 0.279(2) 0.188(3) 0.048(11) Uiso 1 1 d . . . . .
O11 O 0.21826(9) 0.12403(15) -0.13643(16) 0.0582(7) Uani 1 1 d . . . . .
H11 H 0.2345 0.1040 -0.0985 0.087 Uiso 1 1 calc GR . . . .
O13 O 0.07533(11) 0.25056(12) -0.19797(15) 0.0558(7) Uani 1 1 d . . . . .
H13 H 0.0540 0.2612 -0.1774 0.084 Uiso 1 1 calc GR . . . .
O18 O 0.28235(9) 0.05123(18) 0.25176(15) 0.0652(8) Uani 1 1 d . . . . .
H18 H 0.2650 0.0641 0.2784 0.098 Uiso 1 1 calc GR . . . .
O20 O 0.27473(8) 0.05736(11) -0.01731(13) 0.0396(5) Uani 1 1 d . . . . .
H20 H 0.3012 0.0757 0.0004 0.059 Uiso 1 1 calc GR . . . .
O25 O 0.07326(7) 0.23907(9) 0.27070(12) 0.0338(5) Uani 1 1 d . . . . .
H25 H 0.0926 0.2650 0.2972 0.051 Uiso 1 1 calc GR . . . .
O27 O 0.22159(8) 0.11189(11) 0.32692(13) 0.0401(5) Uani 1 1 d . . . . .
H27 H 0.2330 0.1446 0.3506 0.060 Uiso 1 1 calc GR . . . .
N1A N 0.14554(14) 0.34221(19) 0.0338(2) 0.0417(9) Uani 0.75 1 d . . P A 2
N1B N 0.1675(4) 0.3075(6) 0.0044(6) 0.027(2) Uani 0.25 1 d . . P B -1
N1C N 0.2957(7) 0.2470(10) 0.4268(9) 0.033(3) Uani 0.4 1 d . . P C 2
N1D N 0.3031(4) 0.2395(6) 0.4073(6) 0.032(2) Uani 0.6 1 d . . P D 1
N1E N 0.13655(10) 0.35964(12) 0.39748(17) 0.0418(7) Uani 1 1 d . . . . .
N1F N -0.04349(10) 0.43476(12) -0.17900(14) 0.0354(6) Uani 1 1 d . . . . .
C1 C 0.02010(10) 0.19316(13) 0.08174(16) 0.0297(6) Uani 1 1 d . . . . .
C1A C 0.1442(3) 0.2864(3) -0.0037(3) 0.0566(15) Uani 0.75 1 d . . P A 2
H1A H 0.1405 0.2861 -0.0570 0.068 Uiso 0.75 1 calc R . P A 2
C1B C 0.1393(5) 0.2914(8) 0.0524(9) 0.047(3) Uani 0.25 1 d . . P B -1
H1B H 0.1147 0.3201 0.0554 0.056 Uiso 0.25 1 calc R . P B -1
C1C C 0.3203(10) 0.2667(10) 0.4852(19) 0.064(13) Uani 0.4 1 d . . P C 2
H1C H 0.3063 0.2649 0.5263 0.076 Uiso 0.4 1 calc R . P C 2
C1D C 0.3201(4) 0.2655(6) 0.4878(9) 0.035(5) Uani 0.6 1 d . . P D 1
H1D H 0.3008 0.2647 0.5222 0.042 Uiso 0.6 1 calc R . P D 1
C1E C 0.09919(13) 0.36065(15) 0.4314(2) 0.0436(8) Uani 1 1 d . . . . .
H1E H 0.0688 0.3427 0.4056 0.052 Uiso 1 1 calc R . . . .
C1F C -0.06088(12) 0.39710(15) -0.24190(18) 0.0385(7) Uani 1 1 d . . . . .
H1F H -0.0592 0.3528 -0.2363 0.046 Uiso 1 1 calc R . . . .
C2 C 0.02208(10) 0.16330(13) 0.01322(16) 0.0297(6) Uani 1 1 d . . . . .
H2 H 0.0262 0.1191 0.0140 0.036 Uiso 1 1 calc R . . . .
C2A C 0.1484(3) 0.2290(3) 0.0367(3) 0.0688(18) Uani 0.75 1 d . . P A 2
H2A H 0.1449 0.1902 0.0101 0.083 Uiso 0.75 1 calc R . P A 2
C2B C 0.1440(9) 0.2356(16) 0.0975(16) 0.044(7) Uani 0.25 1 d . U P B -1
H2B H 0.1241 0.2251 0.1291 0.053 Uiso 0.25 1 calc R . P B -1
C2C C 0.3672(7) 0.2923(12) 0.5033(15) 0.061(12) Uani 0.4 1 d . . P C 2
H2C H 0.3836 0.3055 0.5534 0.073 Uiso 0.4 1 calc R . P C 2
C2D C 0.3674(6) 0.2910(7) 0.5068(6) 0.035(5) Uani 0.6 1 d . . P D 1
H2D H 0.3798 0.3092 0.5558 0.042 Uiso 0.6 1 calc R . P D 1
C2E C 0.10540(16) 0.38764(16) 0.5030(2) 0.0545(10) Uani 1 1 d . . . . .
H2E H 0.0796 0.3883 0.5259 0.065 Uiso 1 1 calc R . . . .
C2F C -0.08091(12) 0.42325(16) -0.31380(19) 0.0412(7) Uani 1 1 d . . . . .
H2F H -0.0922 0.3971 -0.3571 0.049 Uiso 1 1 calc R . . . .
C3 C 0.01826(11) 0.19529(13) -0.05630(17) 0.0333(6) Uani 1 1 d . . . . .
C3A C 0.1577(4) 0.2298(6) 0.1142(6) 0.061(3) Uani 0.75 1 d . . P A 2
H3A H 0.1639 0.1917 0.1422 0.073 Uiso 0.75 1 calc R . P A 2
C3B C 0.1859(6) 0.1953(7) 0.0875(8) 0.050(3) Uani 0.25 1 d . . P B -1
H3B H 0.1939 0.1578 0.1164 0.060 Uiso 0.25 1 calc R . P B -1
C3C C 0.3882(13) 0.2971(17) 0.443(2) 0.051(8) Uani 0.4 1 d . . P C 2
H3C H 0.4212 0.3080 0.4504 0.061 Uiso 0.4 1 calc R . P C 2
C3D C 0.3965(9) 0.2909(10) 0.4580(14) 0.042(4) Uani 0.6 1 d . . P D 1
H3D H 0.4272 0.3109 0.4731 0.050 Uiso 0.6 1 calc R . P D 1
C3E C 0.15140(17) 0.41422(17) 0.5412(2) 0.0592(11) Uani 1 1 d . . . . .
H3E H 0.1566 0.4328 0.5899 0.071 Uiso 1 1 calc R . . . .
C3F C -0.08411(13) 0.48906(17) -0.3211(2) 0.0449(8) Uani 1 1 d . . . . .
H3F H -0.0976 0.5078 -0.3695 0.054 Uiso 1 1 calc R . . . .
C4 C 0.01364(13) 0.26232(14) -0.05529(18) 0.0394(7) Uani 1 1 d . . . . .
C4A C 0.15804(19) 0.2879(3) 0.1527(3) 0.0516(12) Uani 0.75 1 d . . P A 2
H4A H 0.1617 0.2882 0.2059 0.062 Uiso 0.75 1 calc R . P A 2
C4B C 0.2135(5) 0.2119(6) 0.0362(8) 0.042(3) Uani 0.25 1 d . . P B -1
H4B H 0.2387 0.1853 0.0306 0.050 Uiso 0.25 1 calc R . P B -1
C4C C 0.3588(4) 0.2855(7) 0.3756(6) 0.052(3) Uani 0.4 1 d . . P C 2
H4C H 0.3702 0.2944 0.3328 0.062 Uiso 0.4 1 calc R . P C 2
C4D C 0.3802(3) 0.2596(3) 0.3816(4) 0.0394(15) Uani 0.6 1 d . U P D 1
H4D H 0.4006 0.2577 0.3489 0.047 Uiso 0.6 1 calc R . P D 1
C4E C 0.18901(15) 0.41243(17) 0.5053(2) 0.0553(10) Uani 1 1 d . . . . .
H4E H 0.2196 0.4300 0.5307 0.066 Uiso 1 1 calc R . . . .
C4F C -0.06692(13) 0.52666(16) -0.2557(2) 0.0439(8) Uani 1 1 d . . . . .
H4F H -0.0698 0.5710 -0.2602 0.053 Uiso 1 1 calc R . . . .
C5 C 0.01311(13) 0.29371(14) 0.01244(18) 0.0405(7) Uani 1 1 d . . . . .
H5 H 0.0110 0.3382 0.0125 0.049 Uiso 1 1 calc R . . . .
C5A C 0.15293(16) 0.3453(2) 0.1119(3) 0.0428(10) Uani 0.75 1 d . . P A 2
C5B C 0.2031(4) 0.2667(5) -0.0048(7) 0.032(2) Uani 0.25 1 d . . P B -1
C5C C 0.3115(4) 0.2609(6) 0.3613(5) 0.039(2) Uani 0.4 1 d . . P C 2
C5D C 0.3327(2) 0.2327(3) 0.3598(3) 0.0342(12) Uani 0.6 1 d . . P D 1
C5E C 0.18221(13) 0.38548(15) 0.4336(2) 0.0491(9) Uani 1 1 d . . . . .
C5F C -0.04562(12) 0.49997(14) -0.18389(19) 0.0375(7) Uani 1 1 d . . . . .
C6 C 0.01571(12) 0.26039(14) 0.07981(17) 0.0353(6) Uani 1 1 d . . . . .
C6A C 0.1557(2) 0.4095(2) 0.1501(3) 0.0509(11) Uani 0.75 1 d . . P A 2
H6AA H 0.1882 0.4269 0.1582 0.076 Uiso 0.75 1 calc GR . P A 2
H6AB H 0.1486 0.4049 0.1992 0.076 Uiso 0.75 1 calc GR . P A 2
H6AC H 0.1319 0.4378 0.1174 0.076 Uiso 0.75 1 calc GR . P A 2
C6B C 0.2308(5) 0.2889(6) -0.0607(9) 0.045(3) Uani 0.25 1 d . . P B -1
H6BA H 0.2565 0.3181 -0.0348 0.067 Uiso 0.25 1 calc GR . P B -1
H6BB H 0.2085 0.3102 -0.1040 0.067 Uiso 0.25 1 calc GR . P B -1
H6BC H 0.2452 0.2526 -0.0791 0.067 Uiso 0.25 1 calc GR . P B -1
C6C C 0.2770(4) 0.2483(7) 0.2820(5) 0.066(3) Uani 0.4 1 d . . P C 2
H6CA H 0.2822 0.2799 0.2461 0.099 Uiso 0.4 1 calc GR . P C 2
H6CB H 0.2434 0.2507 0.2845 0.099 Uiso 0.4 1 calc GR . P C 2
H6CC H 0.2832 0.2064 0.2649 0.099 Uiso 0.4 1 calc GR . P C 2
C6D C 0.3109(2) 0.1996(3) 0.2857(3) 0.0432(12) Uani 0.6 1 d . . P D 1
H6DA H 0.3043 0.1557 0.2956 0.065 Uiso 0.6 1 calc GR . P D 1
H6DB H 0.3336 0.2010 0.2545 0.065 Uiso 0.6 1 calc GR . P D 1
H6DC H 0.2807 0.2204 0.2585 0.065 Uiso 0.6 1 calc GR . P D 1
C6E C 0.22082(14) 0.38106(19) 0.3909(3) 0.0613(11) Uani 1 1 d . . . . .
H6EA H 0.2252 0.3370 0.3788 0.092 Uiso 1 1 calc GR . . . .
H6EB H 0.2515 0.3979 0.4228 0.092 Uiso 1 1 calc GR . . . .
H6EC H 0.2105 0.4054 0.3436 0.092 Uiso 1 1 calc GR . . . .
C6F C -0.02487(16) 0.53647(16) -0.1112(2) 0.0542(9) Uani 1 1 d . . . . .
H6FA H -0.0430 0.5264 -0.0746 0.081 Uiso 1 1 calc GR . . . .
H6FB H -0.0274 0.5815 -0.1223 0.081 Uiso 1 1 calc GR . . . .
H6FC H 0.0092 0.5252 -0.0895 0.081 Uiso 1 1 calc GR . . . .
C7 C 0.01867(12) 0.16036(14) -0.13057(16) 0.0346(6) Uani 1 1 d . . . . .
H7 H 0.0035 0.1893 -0.1737 0.042 Uiso 1 1 calc R . . . .
C8 C 0.07134(12) 0.14869(14) -0.13358(16) 0.0342(6) Uani 1 1 d . . . . .
C9 C 0.09781(11) 0.09418(14) -0.10198(16) 0.0327(6) Uani 1 1 d . . . . .
H9 H 0.0817 0.0634 -0.0805 0.039 Uiso 1 1 calc R . . . .
C10 C 0.14696(11) 0.08252(14) -0.10038(16) 0.0332(6) Uani 1 1 d . . . . .
C11 C 0.17025(13) 0.12980(17) -0.13285(18) 0.0432(8) Uani 1 1 d . . . . .
C12 C 0.14542(14) 0.18414(19) -0.16507(19) 0.0517(9) Uani 1 1 d . . . . .
H12 H 0.1615 0.2147 -0.1869 0.062 Uiso 1 1 calc R . . . .
C13 C 0.09669(13) 0.19432(15) -0.16568(17) 0.0425(8) Uani 1 1 d . . . . .
C14 C 0.17385(12) 0.02187(14) -0.06570(17) 0.0349(6) Uani 1 1 d . . . . .
H14 H 0.1984 0.0131 -0.0938 0.042 Uiso 1 1 calc R . . . .
C15 C 0.20226(11) 0.03114(13) 0.01949(17) 0.0319(6) Uani 1 1 d . . . . .
C16 C 0.17997(11) 0.02271(13) 0.07848(17) 0.0313(6) Uani 1 1 d . . . . .
H16 H 0.1465 0.0126 0.0647 0.038 Uiso 1 1 calc R . . . .
C17 C 0.20449(11) 0.02845(14) 0.15699(17) 0.0346(6) Uani 1 1 d . . . . .
C18 C 0.25433(12) 0.04543(18) 0.17600(19) 0.0431(8) Uani 1 1 d . . . . .
C19 C 0.27795(12) 0.05532(16) 0.11874(19) 0.0405(7) Uani 1 1 d . . . . .
H19 H 0.3111 0.0668 0.1326 0.049 Uiso 1 1 calc R . . . .
C20 C 0.25243(11) 0.04817(14) 0.04067(18) 0.0344(6) Uani 1 1 d . . . . .
C21 C 0.17728(12) 0.01651(15) 0.21861(17) 0.0362(7) Uani 1 1 d . . . . .
H21 H 0.2026 0.0075 0.2674 0.043 Uiso 1 1 calc R . . . .
C22 C 0.14965(11) 0.07595(14) 0.23240(16) 0.0301(6) Uani 1 1 d . . . . .
C23 C 0.10006(10) 0.08748(13) 0.19193(15) 0.0290(6) Uani 1 1 d . . . . .
H23 H 0.0838 0.0573 0.1556 0.035 Uiso 1 1 calc R . . . .
C24 C 0.07384(10) 0.14112(13) 0.20290(15) 0.0264(5) Uani 1 1 d . . . . .
C25 C 0.09883(10) 0.18599(13) 0.25812(15) 0.0282(6) Uani 1 1 d . . . . .
C26 C 0.14821(11) 0.17693(13) 0.29873(16) 0.0317(6) Uani 1 1 d . . . . .
H26 H 0.1647 0.2074 0.3345 0.038 Uiso 1 1 calc R . . . .
C27 C 0.17295(10) 0.12228(14) 0.28579(16) 0.0317(6) Uani 1 1 d . . . . .
C28 C 0.02089(10) 0.15463(13) 0.15462(15) 0.0292(6) Uani 1 1 d . . . . .
H28 H 0.0058 0.1816 0.1865 0.035 Uiso 1 1 calc R . . . .
C29 C -0.01098(11) 0.09364(14) 0.13453(17) 0.0342(6) Uani 1 1 d . . . . .
H29A H 0.0024 0.0661 0.1025 0.051 Uiso 1 1 calc GR . . . .
H29B H -0.0442 0.1052 0.1070 0.051 Uiso 1 1 calc GR . . . .
H29C H -0.0109 0.0716 0.1815 0.051 Uiso 1 1 calc GR . . . .
C30 C -0.01337(12) 0.09976(15) -0.14262(18) 0.0385(7) Uani 1 1 d . . . . .
H30A H 0.0000 0.0702 -0.1010 0.058 Uiso 1 1 calc GR . . . .
H30B H -0.0136 0.0802 -0.1912 0.058 Uiso 1 1 calc GR . . . .
H30C H -0.0465 0.1110 -0.1432 0.058 Uiso 1 1 calc GR . . . .
C31 C 0.13963(12) -0.03684(15) -0.07713(19) 0.0389(7) Uani 1 1 d . . . . .
H31A H 0.1590 -0.0747 -0.0601 0.058 Uiso 1 1 calc GR . . . .
H31B H 0.1221 -0.0410 -0.1311 0.058 Uiso 1 1 calc GR . . . .
H31C H 0.1164 -0.0315 -0.0473 0.058 Uiso 1 1 calc GR . . . .
C32 C 0.14396(14) -0.04299(15) 0.1997(2) 0.0444(8) Uani 1 1 d . . . . .
H32A H 0.1267 -0.0482 0.2385 0.067 Uiso 1 1 calc GR . . . .
H32B H 0.1639 -0.0802 0.1990 0.067 Uiso 1 1 calc GR . . . .
H32C H 0.1205 -0.0377 0.1497 0.067 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
O1A N1A 1.339(5) . ?
O1B N1B 1.341(13) . ?
O1C N1C 1.40(3) . ?
O1D N1D 1.303(15) . ?
O1E N1E 1.324(4) . ?
O1F N1F 1.329(3) . ?
O4 H4 0.8200 . ?
O4 C4 1.367(4) . ?
O6 H6 0.86(4) . ?
O6 C6 1.377(4) . ?
O11 H11 0.8200 . ?
O11 C11 1.378(5) . ?
O13 H13 0.8200 . ?
O13 C13 1.371(4) . ?
O18 H18 0.8200 . ?
O18 C18 1.372(4) . ?
O20 H20 0.8200 . ?
O20 C20 1.370(4) . ?
O25 H25 0.8200 . ?
O25 C25 1.374(4) . ?
O27 H27 0.8200 . ?
O27 C27 1.380(4) . ?
N1A C1A 1.341(7) . ?
N1A C5A 1.357(6) . ?
N1B C1B 1.365(18) . ?
N1B C5B 1.361(16) . ?
N1C C1C 1.16(4) . ?
N1C C5C 1.398(13) . ?
N1D C1D 1.490(19) . ?
N1D C5D 1.355(11) . ?
N1E C1E 1.356(5) . ?
N1E C5E 1.379(4) . ?
N1F C1F 1.349(4) . ?
N1F C5F 1.364(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.408(4) . ?
C1 C28 1.529(4) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.387(8) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.40(3) . ?
C1C H1C 0.9300 . ?
C1C C2C 1.38(4) . ?
C1D H1D 0.9300 . ?
C1D C2D 1.38(2) . ?
C1E H1E 0.9300 . ?
C1E C2E 1.367(5) . ?
C1F H1F 0.9300 . ?
C1F C2F 1.368(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.341(12) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.50(3) . ?
C2C H2C 0.9300 . ?
C2C C3C 1.38(5) . ?
C2D H2D 0.9300 . ?
C2D C3D 1.36(3) . ?
C2E H2E 0.9300 . ?
C2E C3E 1.400(6) . ?
C2F H2F 0.9300 . ?
C2F C3F 1.380(5) . ?
C3 C4 1.405(4) . ?
C3 C7 1.521(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.394(13) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.40(2) . ?
C3C H3C 0.9300 . ?
C3C C4C 1.28(4) . ?
C3D H3D 0.9300 . ?
C3D C4D 1.47(3) . ?
C3E H3E 0.9300 . ?
C3E C4E 1.385(7) . ?
C3F H3F 0.9300 . ?
C3F C4F 1.382(5) . ?
C4 C5 1.383(5) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.391(7) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.348(17) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.386(14) . ?
C4D H4D 0.9300 . ?
C4D C5D 1.403(9) . ?
C4E H4E 0.9300 . ?
C4E C5E 1.366(6) . ?
C4F H4F 0.9300 . ?
C4F C5F 1.376(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C5A C6A 1.497(7) . ?
C5B C6B 1.507(18) . ?
C5C C6C 1.504(12) . ?
C5D C6D 1.472(8) . ?
C5E C6E 1.499(6) . ?
C5F C6F 1.482(4) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C6C H6CA 0.9600 . ?
C6C H6CB 0.9600 . ?
C6C H6CC 0.9600 . ?
C6D H6DA 0.9600 . ?
C6D H6DB 0.9600 . ?
C6D H6DC 0.9600 . ?
C6E H6EA 0.9600 . ?
C6E H6EB 0.9600 . ?
C6E H6EC 0.9600 . ?
C6F H6FA 0.9600 . ?
C6F H6FB 0.9600 . ?
C6F H6FC 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.520(5) . ?
C7 C30 1.534(4) . ?
C8 C9 1.391(4) . ?
C8 C13 1.407(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.399(5) . ?
C10 C11 1.399(4) . ?
C10 C14 1.516(4) . ?
C11 C12 1.372(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.525(4) . ?
C14 C31 1.537(4) . ?
C15 C16 1.384(4) . ?
C15 C20 1.404(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 C18 1.395(5) . ?
C17 C21 1.531(4) . ?
C18 C19 1.386(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(4) . ?
C21 H21 0.9800 . ?
C21 C22 1.521(4) . ?
C21 C32 1.536(5) . ?
C22 C23 1.404(4) . ?
C22 C27 1.390(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(4) . ?
C24 C25 1.401(4) . ?
C24 C28 1.528(4) . ?
C25 C26 1.392(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.390(4) . ?
C28 H28 0.9800 . ?
C28 C29 1.541(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
C4 O4 H4 109.5 . . ?
C6 O6 H6 117(3) . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 109.5 . . ?
C18 O18 H18 109.5 . . ?
C20 O20 H20 109.5 . . ?
C25 O25 H25 109.5 . . ?
C27 O27 H27 109.5 . . ?
O1A N1A C1A 117.8(4) . . ?
O1A N1A C5A 120.0(4) . . ?
C1A N1A C5A 122.2(4) . . ?
O1B N1B C1B 117.8(11) . . ?
O1B N1B C5B 122.0(10) . . ?
C5B N1B C1B 120.0(12) . . ?
O1C N1C C5C 115.1(14) . . ?
C1C N1C O1C 127.8(17) . . ?
C1C N1C C5C 116(2) . . ?
O1D N1D C1D 112.2(8) . . ?
O1D N1D C5D 123.3(9) . . ?
C5D N1D C1D 123.9(9) . . ?
O1E N1E C1E 120.5(3) . . ?
O1E N1E C5E 118.0(3) . . ?
C1E N1E C5E 121.5(3) . . ?
O1F N1F C1F 119.6(3) . . ?
O1F N1F C5F 118.5(3) . . ?
C1F N1F C5F 121.9(3) . . ?
C2 C1 C6 116.7(3) . . ?
C2 C1 C28 121.6(2) . . ?
C6 C1 C28 121.7(3) . . ?
N1A C1A H1A 119.9 . . ?
N1A C1A C2A 120.1(5) . . ?
C2A C1A H1A 119.9 . . ?
N1B C1B H1B 116.9 . . ?
N1B C1B C2B 126.1(17) . . ?
C2B C1B H1B 116.9 . . ?
N1C C1C H1C 114.9 . . ?
N1C C1C C2C 130(3) . . ?
C2C C1C H1C 114.9 . . ?
N1D C1D H1D 123.0 . . ?
C2D C1D N1D 113.9(10) . . ?
C2D C1D H1D 123.0 . . ?
N1E C1E H1E 119.5 . . ?
N1E C1E C2E 121.1(3) . . ?
C2E C1E H1E 119.5 . . ?
N1F C1F H1F 119.6 . . ?
N1F C1F C2F 120.9(3) . . ?
C2F C1F H1F 119.6 . . ?
C1 C2 H2 117.9 . . ?
C3 C2 C1 124.3(3) . . ?
C3 C2 H2 117.9 . . ?
C1A C2A H2A 120.2 . . ?
C3A C2A C1A 119.6(7) . . ?
C3A C2A H2A 120.2 . . ?
C1B C2B H2B 124.8 . . ?
C1B C2B C3B 110.3(19) . . ?
C3B C2B H2B 124.8 . . ?
C1C C2C H2C 122.0 . . ?
C3C C2C C1C 116(3) . . ?
C3C C2C H2C 122.0 . . ?
C1D C2D H2D 118.2 . . ?
C3D C2D C1D 123.6(14) . . ?
C3D C2D H2D 118.2 . . ?
C1E C2E H2E 120.7 . . ?
C1E C2E C3E 118.7(4) . . ?
C3E C2E H2E 120.7 . . ?
C1F C2F H2F 120.5 . . ?
C1F C2F C3F 119.0(3) . . ?
C3F C2F H2F 120.5 . . ?
C2 C3 C4 116.8(3) . . ?
C2 C3 C7 122.4(2) . . ?
C4 C3 C7 120.8(3) . . ?
C2A C3A H3A 120.1 . . ?
C2A C3A C4A 119.8(9) . . ?
C4A C3A H3A 120.1 . . ?
C2B C3B H3B 118.7 . . ?
C4B C3B C2B 122.6(16) . . ?
C4B C3B H3B 118.7 . . ?
C2C C3C H3C 122.6 . . ?
C4C C3C C2C 115(3) . . ?
C4C C3C H3C 122.6 . . ?
C2D C3D H3D 119.5 . . ?
C2D C3D C4D 120.9(18) . . ?
C4D C3D H3D 119.5 . . ?
C2E C3E H3E 120.4 . . ?
C4E C3E C2E 119.2(4) . . ?
C4E C3E H3E 120.4 . . ?
C2F C3F H3F 120.5 . . ?
C2F C3F C4F 119.1(3) . . ?
C4F C3F H3F 120.5 . . ?
O4 C4 C3 118.5(3) . . ?
O4 C4 C5 121.1(3) . . ?
C5 C4 C3 120.4(3) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A C3A 120.2(6) . . ?
C5A C4A H4A 119.9 . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B C3B 119.4(14) . . ?
C5B C4B H4B 120.3 . . ?
C3C C4C H4C 117.3 . . ?
C3C C4C C5C 125.5(18) . . ?
C5C C4C H4C 117.3 . . ?
C3D C4D H4D 121.2 . . ?
C5D C4D C3D 117.5(12) . . ?
C5D C4D H4D 121.2 . . ?
C3E C4E H4E 119.2 . . ?
C5E C4E C3E 121.5(3) . . ?
C5E C4E H4E 119.2 . . ?
C3F C4F H4F 119.3 . . ?
C5F C4F C3F 121.5(3) . . ?
C5F C4F H4F 119.3 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
N1A C5A C4A 117.7(4) . . ?
N1A C5A C6A 119.2(4) . . ?
C4A C5A C6A 123.1(4) . . ?
N1B C5B C6B 115.2(11) . . ?
C4B C5B N1B 121.4(12) . . ?
C4B C5B C6B 123.3(13) . . ?
N1C C5C C6C 118.9(11) . . ?
C4C C5C N1C 116.0(12) . . ?
C4C C5C C6C 125.1(9) . . ?
N1D C5D C4D 119.4(7) . . ?
N1D C5D C6D 116.2(7) . . ?
C4D C5D C6D 124.3(6) . . ?
N1E C5E C6E 116.8(3) . . ?
C4E C5E N1E 118.0(4) . . ?
C4E C5E C6E 125.1(3) . . ?
N1F C5F C4F 117.6(3) . . ?
N1F C5F C6F 117.2(3) . . ?
C4F C5F C6F 125.2(3) . . ?
O6 C6 C1 122.8(3) . . ?
O6 C6 C5 116.7(3) . . ?
C5 C6 C1 120.5(3) . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C5C C6C H6CA 109.5 . . ?
C5C C6C H6CB 109.5 . . ?
C5C C6C H6CC 109.5 . . ?
H6CA C6C H6CB 109.5 . . ?
H6CA C6C H6CC 109.5 . . ?
H6CB C6C H6CC 109.5 . . ?
C5D C6D H6DA 109.5 . . ?
C5D C6D H6DB 109.5 . . ?
C5D C6D H6DC 109.5 . . ?
H6DA C6D H6DB 109.5 . . ?
H6DA C6D H6DC 109.5 . . ?
H6DB C6D H6DC 109.5 . . ?
C5E C6E H6EA 109.5 . . ?
C5E C6E H6EB 109.5 . . ?
C5E C6E H6EC 109.5 . . ?
H6EA C6E H6EB 109.5 . . ?
H6EA C6E H6EC 109.5 . . ?
H6EB C6E H6EC 109.5 . . ?
C5F C6F H6FA 109.5 . . ?
C5F C6F H6FB 109.5 . . ?
C5F C6F H6FC 109.5 . . ?
H6FA C6F H6FB 109.5 . . ?
H6FA C6F H6FC 109.5 . . ?
H6FB C6F H6FC 109.5 . . ?
C3 C7 H7 106.7 . . ?
C3 C7 C30 111.7(3) . . ?
C8 C7 C3 110.8(2) . . ?
C8 C7 H7 106.7 . . ?
C8 C7 C30 113.9(3) . . ?
C30 C7 H7 106.7 . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 C13 116.4(3) . . ?
C13 C8 C7 121.3(3) . . ?
C8 C9 H9 117.8 . . ?
C8 C9 C10 124.5(3) . . ?
C10 C9 H9 117.8 . . ?
C9 C10 C14 122.2(3) . . ?
C11 C10 C9 116.5(3) . . ?
C11 C10 C14 121.4(3) . . ?
O11 C11 C10 122.6(3) . . ?
C12 C11 O11 116.4(3) . . ?
C12 C11 C10 121.0(3) . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
O13 C13 C8 122.6(3) . . ?
O13 C13 C12 116.8(3) . . ?
C12 C13 C8 120.6(3) . . ?
C10 C14 H14 106.8 . . ?
C10 C14 C15 111.5(2) . . ?
C10 C14 C31 112.8(3) . . ?
C15 C14 H14 106.8 . . ?
C15 C14 C31 111.6(2) . . ?
C31 C14 H14 106.8 . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 C20 117.6(3) . . ?
C20 C15 C14 120.7(3) . . ?
C15 C16 H16 118.0 . . ?
C15 C16 C17 124.0(3) . . ?
C17 C16 H16 118.0 . . ?
C16 C17 C18 116.8(3) . . ?
C16 C17 C21 120.6(3) . . ?
C18 C17 C21 122.6(3) . . ?
O18 C18 C17 121.7(3) . . ?
O18 C18 C19 117.2(3) . . ?
C19 C18 C17 121.1(3) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
O20 C20 C15 118.1(3) . . ?
O20 C20 C19 122.0(3) . . ?
C19 C20 C15 119.8(3) . . ?
C17 C21 H21 106.8 . . ?
C17 C21 C32 111.8(3) . . ?
C22 C21 C17 111.5(2) . . ?
C22 C21 H21 106.8 . . ?
C22 C21 C32 112.7(3) . . ?
C32 C21 H21 106.8 . . ?
C23 C22 C21 122.5(3) . . ?
C27 C22 C21 121.0(3) . . ?
C27 C22 C23 116.6(3) . . ?
C22 C23 H23 118.0 . . ?
C24 C23 C22 124.0(3) . . ?
C24 C23 H23 118.0 . . ?
C23 C24 C25 117.2(2) . . ?
C23 C24 C28 123.0(2) . . ?
C25 C24 C28 119.7(2) . . ?
O25 C25 C24 118.1(2) . . ?
O25 C25 C26 121.2(2) . . ?
C26 C25 C24 120.7(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26 120.0 . . ?
O27 C27 C22 117.8(3) . . ?
O27 C27 C26 120.6(3) . . ?
C22 C27 C26 121.6(3) . . ?
C1 C28 H28 106.9 . . ?
C1 C28 C29 111.5(2) . . ?
C24 C28 C1 111.1(2) . . ?
C24 C28 H28 106.9 . . ?
C24 C28 C29 113.2(2) . . ?
C29 C28 H28 106.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C14 C31 H31A 109.5 . . ?
C14 C31 H31B 109.5 . . ?
C14 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C32 H32A 109.5 . . ?
C21 C32 H32B 109.5 . . ?
C21 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 0 12 0.2195 -5.0006 0.0001 12.0002 -0.1888 -0.3817 0.9385
6 0 -12 0.3152 6.0005 -0.0001 -12.0001 0.1720 0.4329 -0.9200
-14 9 1 0.0332 -13.9992 8.9999 0.9996 -0.4113 -0.8674 -0.3536
14 -9 -1 0.0384 13.9992 -8.9999 -0.9996 0.4113 0.8674 0.3536
13 9 0 0.0197 12.9977 9.0003 0.0007 -0.8419 0.5263 0.0579
-13 -9 0 0.0346 -12.9977 -9.0003 -0.0007 0.8419 -0.5263 -0.0579
-1 14 0 0.0135 -1.0010 14.0001 0.0001 -0.9533 -0.2685 -0.3009
1 -14 -1 0.0354 1.0011 -14.0002 -1.0002 0.9760 0.2790 0.2150

_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_3MePyNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450583'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_3MePyNO_1           
;
PROBLEM: Missing # of FCF Reflection(s) Below Th(Min) ...         12 Report
RESPONSE: These reflections are affected by beamstop
;
# end Validation Reply Form
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C6 H7 N O), C32 H32 O8'
_chemical_formula_sum            'C44 H46 N2 O10'
_chemical_formula_weight         762.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9'
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      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                   9.9521(7)
_cell_length_b                   13.7594(10)
_cell_length_c                   15.1539(12)
_cell_angle_alpha                113.562(7)
_cell_angle_beta                 94.266(6)
_cell_angle_gamma                90.364(6)
_cell_volume                     1895.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.2270
_cell_measurement_theta_min      3.5260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91323
_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_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12446
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.943
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   46.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   48.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   28.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -26.00   48.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   35.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305   77.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00   34.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2305   77.0000 -120.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0493178000
_diffrn_orient_matrix_UB_12      0.0371119000
_diffrn_orient_matrix_UB_13      0.0217761000
_diffrn_orient_matrix_UB_21      -0.0274494000
_diffrn_orient_matrix_UB_22      -0.0052708000
_diffrn_orient_matrix_UB_23      -0.0463198000
_diffrn_orient_matrix_UB_31      -0.0439331000
_diffrn_orient_matrix_UB_32      -0.0419845000
_diffrn_orient_matrix_UB_33      -0.0025063000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4730
_reflns_number_total             6848
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.246
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.050
_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)+(0.0549P)²+0.1289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C2(H2), C2A(H2A), C2B(H2B), C3A(H3A), C3B(H3B), C5(H5),
 C5A(H5A), C5B(H5B), C9(H9), C12(H12), C16(H16), C23(H23), C26(H26)
2.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O11(H11), O20(H20)
;
_atom_sites_solution_hydrogens   mixed
_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
O1A O -0.21358(18) 0.76943(13) -0.04000(12) 0.0331(4) Uani 1 1 d . . . . .
O1B O -0.03793(16) 0.33302(12) 0.29004(12) 0.0284(4) Uani 1 1 d . . . . .
O4 O 0.07591(18) 1.19786(14) 0.35107(13) 0.0309(4) Uani 1 1 d . . . . .
H4 H 0.037(3) 1.242(3) 0.320(2) 0.077(11) Uiso 1 1 d . . . . .
O6 O 0.34190(19) 1.08270(14) 0.07552(12) 0.0306(4) Uani 1 1 d . . . . .
H6 H 0.292(3) 1.133(3) 0.060(2) 0.072(11) Uiso 1 1 d . . . . .
O11 O -0.05812(16) 0.68816(13) 0.37582(13) 0.0301(4) Uani 1 1 d . . . . .
H11 H -0.0095 0.6475 0.3896 0.045 Uiso 1 1 calc GR . . . .
O13 O -0.05827(17) 1.01281(15) 0.34465(13) 0.0307(4) Uani 1 1 d . . . . .
H13 H -0.016(3) 1.073(2) 0.3525(19) 0.032(8) Uiso 1 1 d . . . . .
O18 O 0.37485(17) 0.39940(13) 0.10913(12) 0.0243(4) Uani 1 1 d . . . . .
H18 H 0.319(3) 0.340(3) 0.085(2) 0.073(11) Uiso 1 1 d . . . . .
O20 O 0.10341(16) 0.51031(13) 0.37953(12) 0.0282(4) Uani 1 1 d . . . . .
H20 H 0.0680 0.4514 0.3478 0.042 Uiso 1 1 calc GR . . . .
O25 O 0.30833(18) 0.85237(14) -0.01961(12) 0.0295(4) Uani 1 1 d . . . . .
H25 H 0.332(3) 0.921(2) 0.007(2) 0.063(11) Uiso 1 1 d . . . . .
O27 O 0.31570(17) 0.52492(13) 0.00825(12) 0.0252(4) Uani 1 1 d . . . . .
H27 H 0.360(4) 0.489(3) 0.043(3) 0.082(12) Uiso 1 1 d . . . . .
N1A N -0.1145(2) 0.77451(15) 0.02638(14) 0.0245(5) Uani 1 1 d . . . . .
N1B N -0.16621(19) 0.35980(15) 0.30520(15) 0.0239(5) Uani 1 1 d . . . . .
C1 C 0.3913(2) 1.02561(18) 0.20202(17) 0.0214(5) Uani 1 1 d . . . . .
C1A C -0.0344(3) 0.86313(19) 0.06797(18) 0.0296(6) Uani 1 1 d . . . . .
H1A H -0.0490 0.9207 0.0515 0.036 Uiso 1 1 calc R . . . .
C1B C -0.2652(3) 0.3016(2) 0.24045(19) 0.0323(6) Uani 1 1 d . . . . .
H1B H -0.2456 0.2416 0.1872 0.039 Uiso 1 1 calc R . . . .
C2 C 0.3569(2) 1.02469(17) 0.28908(16) 0.0192(5) Uani 1 1 d . . . . .
H2 H 0.4056 0.9826 0.3141 0.023 Uiso 1 1 calc R . . . .
C2A C 0.0692(3) 0.8675(2) 0.13503(18) 0.0330(7) Uani 1 1 d . . . . .
H2A H 0.1245 0.9285 0.1645 0.040 Uiso 1 1 calc R . . . .
C2B C -0.3963(3) 0.3316(3) 0.2536(2) 0.0433(8) Uani 1 1 d . . . . .
H2B H -0.4661 0.2912 0.2097 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2540(2) 1.08300(17) 0.34072(17) 0.0203(5) Uani 1 1 d . . . . .
C3A C 0.0912(3) 0.7822(2) 0.15863(18) 0.0323(6) Uani 1 1 d . . . . .
H3A H 0.1621 0.7854 0.2034 0.039 Uiso 1 1 calc R . . . .
C3B C -0.4241(3) 0.4223(3) 0.3326(2) 0.0445(8) Uani 1 1 d . . . . .
H3B H -0.5126 0.4433 0.3408 0.053 Uiso 1 1 calc R . . . .
C4 C 0.1815(2) 1.14435(18) 0.30156(17) 0.0234(6) Uani 1 1 d . . . . .
C4A C 0.0082(2) 0.6912(2) 0.11596(17) 0.0265(6) Uani 1 1 d . . . . .
C4B C -0.3217(3) 0.4810(2) 0.3984(2) 0.0341(7) Uani 1 1 d . . . . .
C5 C 0.2105(2) 1.14684(18) 0.21419(17) 0.0250(6) Uani 1 1 d . . . . .
H5 H 0.1607 1.1879 0.1887 0.030 Uiso 1 1 calc R . . . .
C5A C -0.0947(2) 0.69018(19) 0.04984(17) 0.0242(6) Uani 1 1 d . . . . .
H5A H -0.1520 0.6303 0.0206 0.029 Uiso 1 1 calc R . . . .
C5B C -0.1929(2) 0.44617(18) 0.38362(18) 0.0257(6) Uani 1 1 d . . . . .
H5B H -0.1224 0.4831 0.4288 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3147(2) 1.08720(18) 0.16523(17) 0.0228(6) Uani 1 1 d . . . . .
C6A C 0.0260(3) 0.5959(2) 0.13966(19) 0.0363(7) Uani 1 1 d . . . . .
H6AA H 0.0049 0.6132 0.2049 0.054 Uiso 1 1 calc GR . . . .
H6AB H 0.1177 0.5747 0.1330 0.054 Uiso 1 1 calc GR . . . .
H6AC H -0.0333 0.5387 0.0963 0.054 Uiso 1 1 calc GR . . . .
C6B C -0.3437(3) 0.5821(2) 0.4842(2) 0.0525(9) Uani 1 1 d . . . . .
H6BA H -0.3190 0.5729 0.5427 0.079 Uiso 1 1 calc GR . . . .
H6BB H -0.4370 0.5991 0.4822 0.079 Uiso 1 1 calc GR . . . .
H6BC H -0.2890 0.6388 0.4821 0.079 Uiso 1 1 calc GR . . . .
C7 C 0.2191(2) 1.07672(18) 0.43473(16) 0.0210(5) Uani 1 1 d . . . . .
H7 H 0.1543 1.1318 0.4628 0.025 Uiso 1 1 calc R . . . .
C8 C 0.1487(2) 0.97088(18) 0.41677(16) 0.0195(5) Uani 1 1 d . . . . .
C9 C 0.2107(2) 0.89528(17) 0.44328(16) 0.0196(5) Uani 1 1 d . . . . .
H9 H 0.2992 0.9096 0.4705 0.024 Uiso 1 1 calc R . . . .
C10 C 0.1483(2) 0.79912(18) 0.43163(16) 0.0199(5) Uani 1 1 d . . . . .
C11 C 0.0159(2) 0.77936(18) 0.38996(17) 0.0239(6) Uani 1 1 d . . . . .
C12 C -0.0484(2) 0.85157(19) 0.36127(17) 0.0258(6) Uani 1 1 d . . . . .
H12 H -0.1361 0.8361 0.3323 0.031 Uiso 1 1 calc R . . . .
C13 C 0.0153(2) 0.94658(19) 0.37480(17) 0.0236(6) Uani 1 1 d . . . . .
C14 C 0.2214(2) 0.71777(18) 0.45928(16) 0.0215(5) Uani 1 1 d . . . . .
H14 H 0.1548 0.6851 0.4846 0.026 Uiso 1 1 calc R . . . .
C15 C 0.2674(2) 0.62992(18) 0.36918(16) 0.0193(5) Uani 1 1 d . . . . .
C16 C 0.3662(2) 0.64910(18) 0.31660(16) 0.0197(5) Uani 1 1 d . . . . .
H16 H 0.4082 0.7163 0.3407 0.024 Uiso 1 1 calc R . . . .
C17 C 0.4050(2) 0.57399(17) 0.23082(16) 0.0180(5) Uani 1 1 d . . . . .
C18 C 0.3387(2) 0.47378(17) 0.19517(16) 0.0199(5) Uani 1 1 d . . . . .
C19 C 0.2395(2) 0.45105(19) 0.24489(17) 0.0210(5) Uani 1 1 d . . . . .
H19 H 0.198(2) 0.3807(18) 0.2203(16) 0.017(6) Uiso 1 1 d . . . . .
C20 C 0.2048(2) 0.52894(18) 0.33060(16) 0.0205(5) Uani 1 1 d . . . . .
C21 C 0.5135(2) 0.59857(18) 0.17591(17) 0.0206(5) Uani 1 1 d . . . . .
H21 H 0.5334 0.5306 0.1247 0.025 Uiso 1 1 calc R . . . .
C22 C 0.4616(2) 0.66844(17) 0.12514(16) 0.0184(5) Uani 1 1 d . . . . .
C23 C 0.5045(2) 0.77438(18) 0.15467(16) 0.0209(5) Uani 1 1 d . . . . .
H23 H 0.5681 0.8028 0.2074 0.025 Uiso 1 1 calc R . . . .
C24 C 0.4581(2) 0.84004(18) 0.11027(16) 0.0204(5) Uani 1 1 d . . . . .
C25 C 0.3632(2) 0.79552(18) 0.03041(17) 0.0228(6) Uani 1 1 d . . . . .
C26 C 0.3196(2) 0.69065(18) -0.00178(17) 0.0225(5) Uani 1 1 d . . . . .
H26 H 0.2574 0.6618 -0.0554 0.027 Uiso 1 1 calc R . . . .
C27 C 0.3674(2) 0.62828(17) 0.04486(17) 0.0202(5) Uani 1 1 d . . . . .
C28 C 0.5027(2) 0.95698(17) 0.14715(17) 0.0220(5) Uani 1 1 d . . . . .
H28 H 0.5124 0.9728 0.0903 0.026 Uiso 1 1 calc R . . . .
C29 C 0.6389(2) 0.98435(18) 0.20706(18) 0.0273(6) Uani 1 1 d . . . . .
H29A H 0.6662 1.0563 0.2206 0.041 Uiso 1 1 calc GR . . . .
H29B H 0.7050 0.9374 0.1715 0.041 Uiso 1 1 calc GR . . . .
H29C H 0.6308 0.9766 0.2667 0.041 Uiso 1 1 calc GR . . . .
C30 C 0.3426(2) 1.10385(18) 0.50734(17) 0.0241(6) Uani 1 1 d . . . . .
H30A H 0.4123 1.0557 0.4800 0.036 Uiso 1 1 calc GR . . . .
H30B H 0.3187 1.0978 0.5652 0.036 Uiso 1 1 calc GR . . . .
H30C H 0.3745 1.1752 0.5225 0.036 Uiso 1 1 calc GR . . . .
C31 C 0.3353(2) 0.76552(19) 0.53923(17) 0.0257(6) Uani 1 1 d . . . . .
H31A H 0.4057 0.7945 0.5159 0.039 Uiso 1 1 calc GR . . . .
H31B H 0.3706 0.7113 0.5581 0.039 Uiso 1 1 calc GR . . . .
H31C H 0.3012 0.8208 0.5939 0.039 Uiso 1 1 calc GR . . . .
C32 C 0.6452(2) 0.64056(19) 0.23902(18) 0.0251(6) Uani 1 1 d . . . . .
H32A H 0.7106 0.6550 0.2019 0.038 Uiso 1 1 calc GR . . . .
H32B H 0.6785 0.5884 0.2614 0.038 Uiso 1 1 calc GR . . . .
H32C H 0.6294 0.7047 0.2934 0.038 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
O1A N1A 1.336(2) . ?
O1B N1B 1.342(2) . ?
O4 H4 0.97(3) . ?
O4 C4 1.377(3) . ?
O6 H6 0.95(3) . ?
O6 C6 1.383(3) . ?
O11 H11 0.8200 . ?
O11 C11 1.383(3) . ?
O13 H13 0.88(3) . ?
O13 C13 1.366(3) . ?
O18 H18 0.91(3) . ?
O18 C18 1.373(3) . ?
O20 H20 0.8200 . ?
O20 C20 1.376(3) . ?
O25 H25 0.89(3) . ?
O25 C25 1.379(3) . ?
O27 H27 0.95(4) . ?
O27 C27 1.383(3) . ?
N1A C1A 1.348(3) . ?
N1A C5A 1.354(3) . ?
N1B C1B 1.339(3) . ?
N1B C5B 1.348(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.390(3) . ?
C1 C28 1.528(3) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.376(4) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.371(4) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.387(4) . ?
C3 C4 1.389(3) . ?
C3 C7 1.526(3) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.389(3) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.372(4) . ?
C4 C5 1.389(3) . ?
C4A C5A 1.375(3) . ?
C4A C6A 1.500(3) . ?
C4B C5B 1.374(3) . ?
C4B C6B 1.508(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C5A H5A 0.9300 . ?
C5B H5B 0.9300 . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.526(3) . ?
C7 C30 1.525(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.406(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C10 C11 1.395(3) . ?
C10 C14 1.516(3) . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.522(3) . ?
C14 C31 1.528(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 C18 1.403(3) . ?
C17 C21 1.525(3) . ?
C18 C19 1.391(3) . ?
C19 H19 0.96(2) . ?
C19 C20 1.383(3) . ?
C21 H21 0.9800 . ?
C21 C22 1.523(3) . ?
C21 C32 1.526(3) . ?
C22 C23 1.396(3) . ?
C22 C27 1.397(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(3) . ?
C24 C25 1.401(3) . ?
C24 C28 1.528(3) . ?
C25 C26 1.381(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.379(3) . ?
C28 H28 0.9800 . ?
C28 C29 1.530(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
C4 O4 H4 109.5(19) . . ?
C6 O6 H6 111(2) . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 115.7(17) . . ?
C18 O18 H18 113(2) . . ?
C20 O20 H20 109.5 . . ?
C25 O25 H25 114(2) . . ?
C27 O27 H27 109(2) . . ?
O1A N1A C1A 119.4(2) . . ?
O1A N1A C5A 119.61(19) . . ?
C1A N1A C5A 121.0(2) . . ?
O1B N1B C5B 119.59(19) . . ?
C1B N1B O1B 119.1(2) . . ?
C1B N1B C5B 121.2(2) . . ?
C2 C1 C28 121.2(2) . . ?
C6 C1 C2 116.8(2) . . ?
C6 C1 C28 121.9(2) . . ?
N1A C1A H1A 120.3 . . ?
N1A C1A C2A 119.3(2) . . ?
C2A C1A H1A 120.3 . . ?
N1B C1B H1B 120.4 . . ?
N1B C1B C2B 119.3(3) . . ?
C2B C1B H1B 120.4 . . ?
C1 C2 H2 118.1 . . ?
C3 C2 C1 123.8(2) . . ?
C3 C2 H2 118.1 . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A C1A 120.3(2) . . ?
C3A C2A H2A 119.9 . . ?
C1B C2B H2B 120.1 . . ?
C1B C2B C3B 119.8(3) . . ?
C3B C2B H2B 120.1 . . ?
C2 C3 C7 121.3(2) . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 C7 121.5(2) . . ?
C2A C3A H3A 119.8 . . ?
C2A C3A C4A 120.3(2) . . ?
C4A C3A H3A 119.8 . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B C2B 120.3(3) . . ?
C4B C3B H3B 119.9 . . ?
O4 C4 C3 116.7(2) . . ?
O4 C4 C5 122.0(2) . . ?
C3 C4 C5 121.3(2) . . ?
C3A C4A C6A 122.9(2) . . ?
C5A C4A C3A 117.7(2) . . ?
C5A C4A C6A 119.4(2) . . ?
C3B C4B C5B 117.7(3) . . ?
C3B C4B C6B 123.2(3) . . ?
C5B C4B C6B 119.0(3) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
N1A C5A C4A 121.4(2) . . ?
N1A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
N1B C5B C4B 121.6(2) . . ?
N1B C5B H5B 119.2 . . ?
C4B C5B H5B 119.2 . . ?
O6 C6 C1 117.2(2) . . ?
O6 C6 C5 121.2(2) . . ?
C1 C6 C5 121.5(2) . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C4B C6B H6BA 109.5 . . ?
C4B C6B H6BB 109.5 . . ?
C4B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C3 C7 H7 106.7 . . ?
C8 C7 C3 111.81(18) . . ?
C8 C7 H7 106.7 . . ?
C30 C7 C3 111.00(19) . . ?
C30 C7 H7 106.7 . . ?
C30 C7 C8 113.52(19) . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 C13 116.7(2) . . ?
C13 C8 C7 121.2(2) . . ?
C8 C9 H9 117.9 . . ?
C8 C9 C10 124.1(2) . . ?
C10 C9 H9 117.9 . . ?
C9 C10 C14 122.2(2) . . ?
C11 C10 C9 116.8(2) . . ?
C11 C10 C14 121.0(2) . . ?
O11 C11 C10 122.6(2) . . ?
C12 C11 O11 116.5(2) . . ?
C12 C11 C10 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
O13 C13 C8 123.3(2) . . ?
O13 C13 C12 116.2(2) . . ?
C12 C13 C8 120.5(2) . . ?
C10 C14 H14 106.7 . . ?
C10 C14 C15 109.61(19) . . ?
C10 C14 C31 113.75(19) . . ?
C15 C14 H14 106.7 . . ?
C15 C14 C31 112.87(19) . . ?
C31 C14 H14 106.7 . . ?
C16 C15 C14 121.5(2) . . ?
C20 C15 C14 121.46(19) . . ?
C20 C15 C16 116.8(2) . . ?
C15 C16 H16 118.1 . . ?
C17 C16 C15 123.8(2) . . ?
C17 C16 H16 118.1 . . ?
C16 C17 C18 117.1(2) . . ?
C16 C17 C21 122.0(2) . . ?
C18 C17 C21 120.98(19) . . ?
O18 C18 C17 117.4(2) . . ?
O18 C18 C19 121.4(2) . . ?
C19 C18 C17 121.2(2) . . ?
C18 C19 H19 119.6(13) . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.9(13) . . ?
O20 C20 C15 117.40(19) . . ?
O20 C20 C19 120.80(19) . . ?
C19 C20 C15 121.8(2) . . ?
C17 C21 H21 106.2 . . ?
C17 C21 C32 112.08(19) . . ?
C22 C21 C17 111.64(18) . . ?
C22 C21 H21 106.2 . . ?
C22 C21 C32 113.88(19) . . ?
C32 C21 H21 106.2 . . ?
C23 C22 C21 123.0(2) . . ?
C23 C22 C27 116.2(2) . . ?
C27 C22 C21 120.8(2) . . ?
C22 C23 H23 117.9 . . ?
C24 C23 C22 124.2(2) . . ?
C24 C23 H23 117.9 . . ?
C23 C24 C25 117.0(2) . . ?
C23 C24 C28 122.8(2) . . ?
C25 C24 C28 120.2(2) . . ?
O25 C25 C24 122.8(2) . . ?
O25 C25 C26 116.6(2) . . ?
C26 C25 C24 120.6(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(2) . . ?
C27 C26 H26 119.7 . . ?
O27 C27 C22 122.3(2) . . ?
C26 C27 O27 116.2(2) . . ?
C26 C27 C22 121.4(2) . . ?
C1 C28 H28 107.1 . . ?
C1 C28 C29 111.96(19) . . ?
C24 C28 C1 109.36(18) . . ?
C24 C28 H28 107.1 . . ?
C24 C28 C29 113.87(19) . . ?
C29 C28 H28 107.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C14 C31 H31A 109.5 . . ?
C14 C31 H31B 109.5 . . ?
C14 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C32 H32A 109.5 . . ?
C21 C32 H32B 109.5 . . ?
C21 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_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_4MePyNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450584'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C6 H7 N O), C H4 O, C32 H32 O8'
_chemical_formula_sum            'C45 H50 N2 O11'
_chemical_formula_weight         794.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N1 O9'
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'

_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                   11.6839(4)
_cell_length_b                   13.6838(6)
_cell_length_c                   14.7557(6)
_cell_angle_alpha                67.409(4)
_cell_angle_beta                 89.351(3)
_cell_angle_gamma                67.249(4)
_cell_volume                     1982.39(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6920
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.9940
_cell_measurement_theta_min      3.8300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95115
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             844
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 6 6 0.0338
3 -6 -5 0.0339
3 7 -2 0.0686
-4 -7 3 0.0964
-7 -4 -4 0.0632
-1 0 9 0.0574
7 4 4 0.0481
6 4 -4 0.0609
0 0 -9 0.1021

_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.078
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0000 6.0000 6.0000 0.8362 -0.4243 0.4077
3.0000 -6.0000 -5.0000 -0.8730 0.3535 -0.3255
3.0000 7.0000 -2.0000 0.5858 -0.2587 -0.7198
-4.0000 -7.0000 3.0000 -0.5116 0.2495 0.8721
-7.0000 -4.0000 -4.0000 0.4406 0.8371 0.3580
-1.0000 0.0000 9.0000 -0.2201 -0.5750 0.8106
7.0000 4.0000 4.0000 -0.4406 -0.8371 -0.3580
6.0000 4.0000 -4.0000 -0.0355 -0.2096 -0.9464
0.0000 -0.0000 -9.0000 0.3310 0.6366 -0.7406

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11197
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.739
_diffrn_reflns_theta_min         3.287
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  30.00   1.00    2.00    --  -41.90  37.00 -60.00   96
  2  ω    -96.00  -5.00   1.00    2.00    --  -41.90 125.00   0.00   91
  3  ω   -108.00 -18.00   1.00    2.00    --  -41.90 -37.00 120.00   90
  4  ω     33.00  61.00   1.00    4.00    --  106.66-125.00 -30.00   28
  5  ω     72.00 120.00   1.00    4.00    --  106.66-125.00 -30.00   48
  6  ω     34.00 128.00   1.00    4.00    --  106.66 -61.00-180.00   94
  7  ω     96.00 159.00   1.00    4.00    --  106.66  61.00-120.00   63
  8  ω    114.00 175.00   1.00    4.00    --  106.66 125.00-150.00   61
  9  ω     35.00 119.00   1.00    4.00    --  106.66 -45.00 -90.00   84
 10  ω     35.00 114.00   1.00    4.00    --  106.66-125.00  90.00   79
 11  ω     32.00 108.00   1.00    4.00    --  106.66 -94.00 150.00   76
 12  ω     26.00 156.00   1.00    4.00    --  106.66 -15.00  60.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1108992000
_diffrn_orient_matrix_UB_12      0.1206994000
_diffrn_orient_matrix_UB_13      -0.0367766000
_diffrn_orient_matrix_UB_21      -0.0615820000
_diffrn_orient_matrix_UB_22      -0.0307691000
_diffrn_orient_matrix_UB_23      -0.0707349000
_diffrn_orient_matrix_UB_31      -0.0699800000
_diffrn_orient_matrix_UB_32      -0.0493262000
_diffrn_orient_matrix_UB_33      0.0822943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6037
_reflns_number_total             6933
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.228
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         6933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.023
_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)+(0.0555P)²+0.5275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C2(H2), C2A(H2A), C2B(H2B), C4A(H4A), C4B(H4B), C5(H5),
 C5A(H5A), C5B(H5B), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26)
2.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O11(H11), O13(H13), O18(H18), O25(H25), O27(H27)
;
_atom_sites_solution_hydrogens   mixed
_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
O1A O 0.83309(9) 0.03500(9) 0.63752(7) 0.0247(2) Uani 1 1 d . . . . .
O1B O 0.99297(10) 0.25430(9) 0.64067(7) 0.0271(2) Uani 1 1 d . . . . .
O1S O 1.15311(11) 0.24655(10) 1.12603(8) 0.0298(2) Uani 1 1 d . . . . .
H1S H 1.096(2) 0.224(2) 1.1189(18) 0.061(7) Uiso 1 1 d . . . . .
O4 O 0.27712(9) 0.45527(9) 0.52971(7) 0.0211(2) Uani 1 1 d . . . . .
H4 H 0.2656 0.4903 0.4690 0.032 Uiso 1 1 calc GR . . . .
O6 O 0.46644(9) 0.71635(8) 0.51211(7) 0.0212(2) Uani 1 1 d . . . . .
H6 H 0.4433 0.7399 0.4524 0.032 Uiso 1 1 calc GR . . . .
O11 O 0.80029(9) -0.06752(9) 1.02905(7) 0.0249(2) Uani 1 1 d . . . . .
H11 H 0.7871 -0.0722 1.0849 0.037 Uiso 1 1 calc GR . . . .
O13 O 0.62946(9) 0.16670(9) 0.68724(7) 0.0233(2) Uani 1 1 d . . . . .
H13 H 0.6991 0.1227 0.6835 0.035 Uiso 1 1 calc GR . . . .
O18 O 0.97173(9) 0.16006(9) 1.24133(7) 0.0231(2) Uani 1 1 d . . . . .
H18 H 1.0289 0.0984 1.2781 0.035 Uiso 1 1 calc GR . . . .
O20 O 0.80089(10) -0.10583(9) 1.23551(7) 0.0230(2) Uani 1 1 d . . . . .
H20 H 0.869(2) -0.1552(19) 1.2776(16) 0.042(6) Uiso 1 1 d . . . . .
O25 O 0.80047(9) 0.40776(9) 0.67191(7) 0.0217(2) Uani 1 1 d . . . . .
H25 H 0.8618 0.3538 0.6692 0.032 Uiso 1 1 calc GR . . . .
O27 O 0.98648(9) 0.20348(9) 1.01709(7) 0.0226(2) Uani 1 1 d . . . . .
H27 H 1.0414 0.1651 0.9942 0.034 Uiso 1 1 calc GR . . . .
N1A N 0.77924(11) -0.00245(10) 0.58585(9) 0.0201(2) Uani 1 1 d . . . . .
N1B N 1.00134(11) 0.29221(10) 0.54333(9) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.51303(12) 0.54639(12) 0.66027(10) 0.0166(3) Uani 1 1 d . . . . .
C1A C 0.75769(14) 0.05008(13) 0.48576(11) 0.0233(3) Uani 1 1 d . . . . .
H1A H 0.7795 0.1121 0.4535 0.028 Uiso 1 1 calc R . . . .
C1B C 1.06540(14) 0.35801(13) 0.50577(11) 0.0244(3) Uani 1 1 d . . . . .
H1B H 1.1067 0.3747 0.5476 0.029 Uiso 1 1 calc R . . . .
C1S C 1.14559(16) 0.33895(16) 1.03602(13) 0.0368(4) Uani 1 1 d . . . . .
H1SA H 1.1814 0.3085 0.9886 0.055 Uiso 1 1 calc GR . . . .
H1SB H 1.1912 0.3792 1.0480 0.055 Uiso 1 1 calc GR . . . .
H1SC H 1.0591 0.3919 1.0103 0.055 Uiso 1 1 calc GR . . . .
C2 C 0.49516(12) 0.44524(12) 0.71098(9) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.5374 0.3971 0.7757 0.020 Uiso 1 1 calc R . . . .
C2A C 0.70366(14) 0.01286(13) 0.43073(11) 0.0236(3) Uani 1 1 d . . . . .
H2A H 0.6898 0.0497 0.3617 0.028 Uiso 1 1 calc R . . . .
C2B C 1.06988(14) 0.40062(13) 0.40559(11) 0.0257(3) Uani 1 1 d . . . . .
H2B H 1.1142 0.4463 0.3801 0.031 Uiso 1 1 calc R . . . .
C3 C 0.41717(12) 0.41269(12) 0.66945(10) 0.0170(3) Uani 1 1 d . . . . .
C3A C 0.66969(13) -0.07908(13) 0.47729(11) 0.0234(3) Uani 1 1 d . . . . .
C3B C 1.00919(14) 0.37656(13) 0.34163(11) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.35397(12) 0.48653(12) 0.57246(10) 0.0178(3) Uani 1 1 d . . . . .
C4A C 0.69276(15) -0.13045(14) 0.58080(12) 0.0276(3) Uani 1 1 d . . . . .
H4A H 0.6712 -0.1922 0.6146 0.033 Uiso 1 1 calc R . . . .
C4B C 0.94663(15) 0.30612(14) 0.38413(11) 0.0275(3) Uani 1 1 d . . . . .
H4B H 0.9064 0.2867 0.3441 0.033 Uiso 1 1 calc R . . . .
C5 C 0.36858(12) 0.58857(12) 0.51949(10) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.3254 0.6372 0.4551 0.022 Uiso 1 1 calc R . . . .
C5A C 0.74692(14) -0.09162(13) 0.63412(11) 0.0255(3) Uani 1 1 d . . . . .
H5A H 0.7612 -0.1268 0.7033 0.031 Uiso 1 1 calc R . . . .
C5B C 0.94333(14) 0.26460(14) 0.48471(11) 0.0253(3) Uani 1 1 d . . . . .
H5B H 0.9010 0.2175 0.5122 0.030 Uiso 1 1 calc R . . . .
C6 C 0.44789(12) 0.61753(12) 0.56313(10) 0.0174(3) Uani 1 1 d . . . . .
C6A C 0.61094(16) -0.12073(16) 0.41807(13) 0.0327(4) Uani 1 1 d . . . . .
H6AA H 0.5212 -0.0785 0.4060 0.049 Uiso 1 1 calc GR . . . .
H6AB H 0.6326 -0.2022 0.4546 0.049 Uiso 1 1 calc GR . . . .
H6AC H 0.6415 -0.1080 0.3557 0.049 Uiso 1 1 calc GR . . . .
C6B C 1.01262(17) 0.42385(16) 0.23211(12) 0.0352(4) Uani 1 1 d . . . . .
H6BA H 1.0484 0.4797 0.2156 0.053 Uiso 1 1 calc GR . . . .
H6BB H 0.9287 0.4607 0.1961 0.053 Uiso 1 1 calc GR . . . .
H6BC H 1.0629 0.3614 0.2145 0.053 Uiso 1 1 calc GR . . . .
C7 C 0.39762(12) 0.30233(12) 0.72587(10) 0.0178(3) Uani 1 1 d . . . . .
H7 H 0.3920 0.2705 0.6777 0.021 Uiso 1 1 calc R . . . .
C8 C 0.50580(13) 0.20835(12) 0.80811(10) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.49898(12) 0.18328(12) 0.90842(10) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.4260 0.2281 0.9247 0.020 Uiso 1 1 calc R . . . .
C10 C 0.59513(13) 0.09488(12) 0.98576(10) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.70221(13) 0.02727(12) 0.95924(10) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.71483(13) 0.05139(12) 0.86020(10) 0.0201(3) Uani 1 1 d . . . . .
H12 H 0.7881 0.0070 0.8439 0.024 Uiso 1 1 calc R . . . .
C13 C 0.61786(13) 0.14189(12) 0.78560(10) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.58891(13) 0.07232(12) 1.09481(10) 0.0172(3) Uani 1 1 d . . . . .
H14 H 0.6087 -0.0106 1.1313 0.021 Uiso 1 1 calc R . . . .
C15 C 0.69054(12) 0.09567(12) 1.13565(9) 0.0168(3) Uani 1 1 d . . . . .
C16 C 0.69045(12) 0.20625(12) 1.09810(9) 0.0165(3) Uani 1 1 d . . . . .
H16 H 0.6245 0.2670 1.0490 0.020 Uiso 1 1 calc R . . . .
C17 C 0.78390(12) 0.23022(12) 1.13038(9) 0.0164(3) Uani 1 1 d . . . . .
C18 C 0.88002(13) 0.13818(12) 1.20675(10) 0.0181(3) Uani 1 1 d . . . . .
C19 C 0.88553(13) 0.02649(12) 1.24400(10) 0.0196(3) Uani 1 1 d . . . . .
H19 H 0.9509 -0.0342 1.2937 0.024 Uiso 1 1 calc R . . . .
C20 C 0.79272(13) 0.00564(12) 1.20656(10) 0.0183(3) Uani 1 1 d . . . . .
C21 C 0.78997(12) 0.34741(12) 1.07602(10) 0.0170(3) Uani 1 1 d . . . . .
H21 H 0.8701 0.3406 1.1034 0.020 Uiso 1 1 calc R . . . .
C22 C 0.79342(12) 0.37035(12) 0.96625(9) 0.0163(3) Uani 1 1 d . . . . .
C23 C 0.70085(12) 0.46232(12) 0.88867(10) 0.0163(3) Uani 1 1 d . . . . .
H23 H 0.6352 0.5161 0.9037 0.020 Uiso 1 1 calc R . . . .
C24 C 0.70109(12) 0.47842(12) 0.78900(10) 0.0165(3) Uani 1 1 d . . . . .
C25 C 0.79942(13) 0.39533(12) 0.76896(10) 0.0178(3) Uani 1 1 d . . . . .
C26 C 0.89547(13) 0.30331(12) 0.84397(10) 0.0194(3) Uani 1 1 d . . . . .
H26 H 0.9612 0.2497 0.8288 0.023 Uiso 1 1 calc R . . . .
C27 C 0.89291(12) 0.29168(12) 0.94152(10) 0.0182(3) Uani 1 1 d . . . . .
C28 C 0.60126(12) 0.58047(12) 0.70439(10) 0.0172(3) Uani 1 1 d . . . . .
H28 H 0.6462 0.6093 0.6512 0.021 Uiso 1 1 calc R . . . .
C29 C 0.52645(14) 0.68256(12) 0.73151(10) 0.0218(3) Uani 1 1 d . . . . .
H29A H 0.4737 0.7482 0.6729 0.033 Uiso 1 1 calc GR . . . .
H29B H 0.5836 0.7029 0.7588 0.033 Uiso 1 1 calc GR . . . .
H29C H 0.4753 0.6605 0.7798 0.033 Uiso 1 1 calc GR . . . .
C30 C 0.26980(13) 0.33462(13) 0.76232(10) 0.0223(3) Uani 1 1 d . . . . .
H30A H 0.2693 0.3712 0.8064 0.033 Uiso 1 1 calc GR . . . .
H30B H 0.2564 0.2655 0.7970 0.033 Uiso 1 1 calc GR . . . .
H30C H 0.2040 0.3873 0.7063 0.033 Uiso 1 1 calc GR . . . .
C31 C 0.45989(13) 0.14014(13) 1.11455(10) 0.0217(3) Uani 1 1 d . . . . .
H31A H 0.4615 0.1170 1.1849 0.032 Uiso 1 1 calc GR . . . .
H31B H 0.3976 0.1241 1.0884 0.032 Uiso 1 1 calc GR . . . .
H31C H 0.4395 0.2219 1.0828 0.032 Uiso 1 1 calc GR . . . .
C32 C 0.68502(13) 0.44509(12) 1.09363(10) 0.0204(3) Uani 1 1 d . . . . .
H32A H 0.6930 0.5170 1.0588 0.031 Uiso 1 1 calc GR . . . .
H32B H 0.6916 0.4270 1.1635 0.031 Uiso 1 1 calc GR . . . .
H32C H 0.6048 0.4525 1.0696 0.031 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
O1A N1A 1.3417(15) . ?
O1B N1B 1.3437(15) . ?
O1S H1S 0.86(3) . ?
O1S C1S 1.413(2) . ?
O4 H4 0.8200 . ?
O4 C4 1.3800(16) . ?
O6 H6 0.8200 . ?
O6 C6 1.3722(16) . ?
O11 H11 0.8200 . ?
O11 C11 1.3811(16) . ?
O13 H13 0.8200 . ?
O13 C13 1.3758(16) . ?
O18 H18 0.8200 . ?
O18 C18 1.3697(16) . ?
O20 H20 0.86(2) . ?
O20 C20 1.3806(17) . ?
O25 H25 0.8200 . ?
O25 C25 1.3762(16) . ?
O27 H27 0.8200 . ?
O27 C27 1.3668(16) . ?
N1A C1A 1.3469(19) . ?
N1A C5A 1.350(2) . ?
N1B C1B 1.344(2) . ?
N1B C5B 1.3464(19) . ?
C1 C2 1.3941(19) . ?
C1 C6 1.4004(19) . ?
C1 C28 1.5245(18) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.377(2) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.374(2) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.3930(19) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.389(2) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.391(2) . ?
C3 C4 1.3966(19) . ?
C3 C7 1.5240(18) . ?
C3A C4A 1.392(2) . ?
C3A C6A 1.503(2) . ?
C3B C4B 1.388(2) . ?
C3B C6B 1.499(2) . ?
C4 C5 1.3901(19) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.376(2) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.377(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3872(19) . ?
C5A H5A 0.9300 . ?
C5B H5B 0.9300 . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.5174(18) . ?
C7 C30 1.5391(19) . ?
C8 C9 1.3940(19) . ?
C8 C13 1.398(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.3946(19) . ?
C10 C11 1.3951(19) . ?
C10 C14 1.5240(17) . ?
C11 C12 1.3887(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3874(19) . ?
C14 H14 0.9800 . ?
C14 C15 1.5274(18) . ?
C14 C31 1.5278(19) . ?
C15 C16 1.3968(19) . ?
C15 C20 1.3922(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.3912(19) . ?
C17 C18 1.4006(19) . ?
C17 C21 1.5227(18) . ?
C18 C19 1.386(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(2) . ?
C21 H21 0.9800 . ?
C21 C22 1.5301(17) . ?
C21 C32 1.5329(19) . ?
C22 C23 1.3901(19) . ?
C22 C27 1.403(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.4010(18) . ?
C24 C25 1.393(2) . ?
C24 C28 1.5176(18) . ?
C25 C26 1.391(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.3874(19) . ?
C28 H28 0.9800 . ?
C28 C29 1.5340(19) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
C1S O1S H1S 108.9(16) . . ?
C4 O4 H4 109.5 . . ?
C6 O6 H6 109.5 . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 109.5 . . ?
C18 O18 H18 109.5 . . ?
C20 O20 H20 110.1(14) . . ?
C25 O25 H25 109.5 . . ?
C27 O27 H27 109.5 . . ?
O1A N1A C1A 119.28(12) . . ?
O1A N1A C5A 120.06(11) . . ?
C1A N1A C5A 120.66(12) . . ?
O1B N1B C1B 119.91(12) . . ?
O1B N1B C5B 118.96(12) . . ?
C1B N1B C5B 121.12(12) . . ?
C2 C1 C6 117.24(12) . . ?
C2 C1 C28 123.33(12) . . ?
C6 C1 C28 119.41(12) . . ?
N1A C1A H1A 119.7 . . ?
N1A C1A C2A 120.59(13) . . ?
C2A C1A H1A 119.7 . . ?
N1B C1B H1B 120.0 . . ?
N1B C1B C2B 119.96(13) . . ?
C2B C1B H1B 120.0 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1 C2 H2 118.4 . . ?
C3 C2 C1 123.20(12) . . ?
C3 C2 H2 118.4 . . ?
C1A C2A H2A 119.7 . . ?
C1A C2A C3A 120.68(13) . . ?
C3A C2A H2A 119.7 . . ?
C1B C2B H2B 119.5 . . ?
C1B C2B C3B 121.06(14) . . ?
C3B C2B H2B 119.5 . . ?
C2 C3 C4 117.49(12) . . ?
C2 C3 C7 122.74(12) . . ?
C4 C3 C7 119.77(12) . . ?
C2A C3A C4A 116.92(14) . . ?
C2A C3A C6A 121.20(14) . . ?
C4A C3A C6A 121.88(14) . . ?
C2B C3B C6B 121.29(14) . . ?
C4B C3B C2B 116.91(14) . . ?
C4B C3B C6B 121.79(14) . . ?
O4 C4 C3 118.35(12) . . ?
O4 C4 C5 120.50(12) . . ?
C5 C4 C3 121.15(12) . . ?
C3A C4A H4A 119.4 . . ?
C5A C4A C3A 121.28(14) . . ?
C5A C4A H4A 119.4 . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B C3B 120.94(14) . . ?
C5B C4B H4B 119.5 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.66(12) . . ?
C6 C5 H5 120.2 . . ?
N1A C5A C4A 119.86(13) . . ?
N1A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
N1B C5B C4B 119.97(14) . . ?
N1B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
O6 C6 C1 117.63(12) . . ?
O6 C6 C5 121.10(12) . . ?
C5 C6 C1 121.27(12) . . ?
C3A C6A H6AA 109.5 . . ?
C3A C6A H6AB 109.5 . . ?
C3A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C3B C6B H6BA 109.5 . . ?
C3B C6B H6BB 109.5 . . ?
C3B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C3 C7 H7 106.8 . . ?
C3 C7 C30 109.13(11) . . ?
C8 C7 C3 113.78(11) . . ?
C8 C7 H7 106.8 . . ?
C8 C7 C30 113.12(11) . . ?
C30 C7 H7 106.8 . . ?
C9 C8 C7 122.53(12) . . ?
C9 C8 C13 116.88(12) . . ?
C13 C8 C7 120.58(12) . . ?
C8 C9 H9 118.1 . . ?
C8 C9 C10 123.84(13) . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 116.83(12) . . ?
C9 C10 C14 123.22(12) . . ?
C11 C10 C14 119.93(12) . . ?
O11 C11 C10 122.36(12) . . ?
O11 C11 C12 116.33(12) . . ?
C12 C11 C10 121.30(12) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.84(13) . . ?
C13 C12 H12 120.1 . . ?
O13 C13 C8 118.48(12) . . ?
O13 C13 C12 120.32(12) . . ?
C12 C13 C8 121.18(12) . . ?
C10 C14 H14 107.2 . . ?
C10 C14 C15 109.62(10) . . ?
C10 C14 C31 114.27(11) . . ?
C15 C14 H14 107.2 . . ?
C15 C14 C31 110.93(11) . . ?
C31 C14 H14 107.2 . . ?
C16 C15 C14 121.59(12) . . ?
C20 C15 C14 121.21(12) . . ?
C20 C15 C16 117.01(12) . . ?
C15 C16 H16 118.3 . . ?
C17 C16 C15 123.41(12) . . ?
C17 C16 H16 118.3 . . ?
C16 C17 C18 117.25(12) . . ?
C16 C17 C21 120.98(12) . . ?
C18 C17 C21 121.33(12) . . ?
O18 C18 C17 118.40(12) . . ?
O18 C18 C19 120.49(12) . . ?
C19 C18 C17 121.06(12) . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.62(13) . . ?
C20 C19 H19 120.2 . . ?
O20 C20 C15 117.32(12) . . ?
O20 C20 C19 121.22(12) . . ?
C19 C20 C15 121.41(13) . . ?
C17 C21 H21 107.2 . . ?
C17 C21 C22 108.60(10) . . ?
C17 C21 C32 112.25(11) . . ?
C22 C21 H21 107.2 . . ?
C22 C21 C32 114.07(11) . . ?
C32 C21 H21 107.2 . . ?
C23 C22 C21 124.09(12) . . ?
C23 C22 C27 117.22(12) . . ?
C27 C22 C21 118.64(12) . . ?
C22 C23 H23 118.2 . . ?
C22 C23 C24 123.58(12) . . ?
C24 C23 H23 118.2 . . ?
C23 C24 C28 123.30(12) . . ?
C25 C24 C23 116.89(12) . . ?
C25 C24 C28 119.81(11) . . ?
O25 C25 C24 118.07(12) . . ?
O25 C25 C26 120.47(12) . . ?
C26 C25 C24 121.45(12) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.82(13) . . ?
C27 C26 H26 120.1 . . ?
O27 C27 C22 117.45(12) . . ?
O27 C27 C26 121.57(12) . . ?
C26 C27 C22 120.98(12) . . ?
C1 C28 H28 106.3 . . ?
C1 C28 C29 110.78(11) . . ?
C24 C28 C1 113.31(11) . . ?
C24 C28 H28 106.3 . . ?
C24 C28 C29 113.28(11) . . ?
C29 C28 H28 106.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C14 C31 H31A 109.5 . . ?
C14 C31 H31B 109.5 . . ?
C14 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C32 H32A 109.5 . . ?
C21 C32 H32B 109.5 . . ?
C21 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.909
####################################################################### 
# 
# 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_4MeOPyNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450585'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C6 H7 N O2), C32 H32 O8'
_chemical_formula_sum            'C44 H46 N2 O12'
_chemical_formula_weight         794.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N4 O9'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.6065(3)
_cell_length_b                   14.6623(3)
_cell_length_c                   14.2271(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.6411(18)
_cell_angle_gamma                90
_cell_volume                     3787.28(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9711
_cell_measurement_temperature    123.0
_cell_measurement_theta_max      73.1520
_cell_measurement_theta_min      3.8470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91492
_exptl_absorpt_correction_type   gaussian
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.1322
_exptl_crystal_size_mid          0.0824
_exptl_crystal_size_min          0.064
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.744
_diffrn_reflns_theta_min         3.875
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega -117.00   -4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -19.0000 -120.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676  -99.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega   45.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676 -125.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00  109.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  122.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega   95.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega   79.00  172.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  9 omega   30.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
 10 omega   79.00  176.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00   91.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 12 omega   29.00  138.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000   30.0000 109

#__ type_ start__ end____ width___ exp.time_
 13 omega -115.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
 14 omega -118.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 15 omega    1.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676  -99.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
 16 omega   73.00  115.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   77.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   77.0000 -150.0000 105

#__ type_ start__ end____ width___ exp.time_
 18 omega   77.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  -30.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0724644000
_diffrn_orient_matrix_UB_12      0.0532513000
_diffrn_orient_matrix_UB_13      0.0079207000
_diffrn_orient_matrix_UB_21      0.0277059000
_diffrn_orient_matrix_UB_22      -0.0361026000
_diffrn_orient_matrix_UB_23      0.1032738000
_diffrn_orient_matrix_UB_31      0.0345185000
_diffrn_orient_matrix_UB_32      -0.0828924000
_diffrn_orient_matrix_UB_33      -0.0399762000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3081
_reflns_number_total             3356
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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         0.194
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.050
_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)+(0.0432P)²+2.5663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0839
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2(H2), C2A(H2A), C4A(H4A), C5(H5), C5A(H5A), C9(H9), C12(H12)
2.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O11(H11), O13(H13)
;
_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
O1A O 0.40201(5) 0.00077(6) 0.15499(7) 0.0236(2) Uani 1 1 d . . . . .
O2A O 0.33203(6) -0.35424(6) 0.07220(7) 0.0267(2) Uani 1 1 d . . . . .
O4 O 0.66658(5) 0.12625(6) 0.26389(6) 0.0201(2) Uani 1 1 d . . . . .
H4 H 0.6485 0.0797 0.2843 0.030 Uiso 1 1 calc GR . . . .
O6 O 0.43956(5) 0.11403(6) 0.02904(6) 0.0202(2) Uani 1 1 d . . . . .
H6 H 0.4306 0.0712 0.0640 0.030 Uiso 1 1 calc GR . . . .
O11 O 0.69078(4) 0.35154(6) 0.63582(6) 0.0183(2) Uani 1 1 d . . . . .
H11 H 0.7347 0.3540 0.6668 0.028 Uiso 1 1 calc GR . . . .
O13 O 0.81423(4) 0.37005(6) 0.37437(6) 0.0193(2) Uani 1 1 d . . . . .
H13 H 0.8507 0.3707 0.4212 0.029 Uiso 1 1 calc GR . . . .
N1A N 0.38411(5) -0.08700(7) 0.13673(7) 0.0184(2) Uani 1 1 d . . . . .
C1 C 0.50463(6) 0.25554(8) 0.05713(8) 0.0150(2) Uani 1 1 d . . . . .
C1A C 0.39682(7) -0.14795(9) 0.20882(9) 0.0226(3) Uani 1 1 d . . . . .
H1A H 0.4179 -0.1279 0.2724 0.027 Uiso 1 1 calc R . . . .
C2 C 0.56526(6) 0.30278(8) 0.10967(8) 0.0149(2) Uani 1 1 d . . . . .
H2 H 0.5693 0.3659 0.0966 0.018 Uiso 1 1 calc R . . . .
C2A C 0.37992(8) -0.23894(9) 0.19275(9) 0.0239(3) Uani 1 1 d . . . . .
H2A H 0.3887 -0.2812 0.2446 0.029 Uiso 1 1 calc R . . . .
C3 C 0.62060(6) 0.26322(8) 0.18040(8) 0.0148(2) Uani 1 1 d . . . . .
C3A C 0.34980(7) -0.26782(9) 0.09927(9) 0.0208(3) Uani 1 1 d . . . . .
C4 C 0.61294(6) 0.17016(8) 0.19741(8) 0.0161(2) Uani 1 1 d . . . . .
C4A C 0.33582(7) -0.20274(9) 0.02590(9) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.3142 -0.2207 -0.0382 0.026 Uiso 1 1 calc R . . . .
C5 C 0.55308(6) 0.12050(8) 0.14701(8) 0.0170(3) Uani 1 1 d . . . . .
H5 H 0.5491 0.0573 0.1597 0.020 Uiso 1 1 calc R . . . .
C5A C 0.35314(7) -0.11338(9) 0.04602(9) 0.0209(3) Uani 1 1 d . . . . .
H5A H 0.3433 -0.0694 -0.0042 0.025 Uiso 1 1 calc R . . . .
C6 C 0.49915(6) 0.16324(8) 0.07812(8) 0.0159(2) Uani 1 1 d . . . . .
C6A C 0.34257(9) -0.42365(10) 0.14485(11) 0.0329(3) Uani 1 1 d . . . . .
H6AA H 0.3108 -0.4113 0.1899 0.049 Uiso 1 1 calc GR . . . .
H6AB H 0.3942 -0.4239 0.1798 0.049 Uiso 1 1 calc GR . . . .
H6AC H 0.3300 -0.4832 0.1145 0.049 Uiso 1 1 calc GR . . . .
C7 C 0.68692(6) 0.31706(8) 0.23523(8) 0.0157(2) Uani 1 1 d . . . . .
H7 H 0.7315 0.2798 0.2330 0.019 Uiso 1 1 calc R . . . .
C8 C 0.68650(6) 0.33025(8) 0.34165(8) 0.0154(2) Uani 1 1 d . . . . .
C9 C 0.62398(6) 0.31607(8) 0.37884(8) 0.0156(2) Uani 1 1 d . . . . .
H9 H 0.5793 0.3005 0.3351 0.019 Uiso 1 1 calc R . . . .
C10 C 0.62308(6) 0.32342(8) 0.47620(8) 0.0157(2) Uani 1 1 d . . . . .
C11 C 0.68920(7) 0.34805(8) 0.53918(8) 0.0156(2) Uani 1 1 d . . . . .
C12 C 0.75186(6) 0.36606(8) 0.50466(8) 0.0162(2) Uani 1 1 d . . . . .
H12 H 0.7956 0.3856 0.5478 0.019 Uiso 1 1 calc R . . . .
C13 C 0.75106(6) 0.35572(8) 0.40737(9) 0.0155(2) Uani 1 1 d . . . . .
C14 C 0.55570(6) 0.30142(8) 0.51691(8) 0.0158(2) Uani 1 1 d . . . . .
H14 H 0.5720 0.2564 0.5701 0.019 Uiso 1 1 calc R . . . .
C15 C 0.52823(7) 0.38570(9) 0.56216(10) 0.0237(3) Uani 1 1 d . . . . .
H15A H 0.5138 0.4329 0.5129 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.5676 0.4090 0.6139 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.4856 0.3691 0.5886 0.036 Uiso 1 1 calc GR . . . .
C16 C 0.69689(7) 0.40899(9) 0.18760(9) 0.0194(3) Uani 1 1 d . . . . .
H16A H 0.6991 0.3989 0.1202 0.029 Uiso 1 1 calc GR . . . .
H16B H 0.7427 0.4377 0.2219 0.029 Uiso 1 1 calc GR . . . .
H16C H 0.6552 0.4490 0.1904 0.029 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
O1A N1A 1.3405(13) . ?
O2A C3A 1.3445(16) . ?
O2A C6A 1.4331(17) . ?
O4 H4 0.8400 . ?
O4 C4 1.3754(14) . ?
O6 H6 0.8400 . ?
O6 C6 1.3780(14) . ?
O11 H11 0.8400 . ?
O11 C11 1.3697(14) . ?
O13 H13 0.8400 . ?
O13 C13 1.3740(14) . ?
N1A C1A 1.3418(17) . ?
N1A C5A 1.3497(17) . ?
C1 C2 1.3936(16) . ?
C1 C6 1.3943(17) . ?
C1 C14 1.5181(16) 2_655 ?
C1A H1A 0.9500 . ?
C1A C2A 1.3783(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3984(16) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3914(18) . ?
C3 C4 1.3985(17) . ?
C3 C7 1.5274(16) . ?
C3A C4A 1.3960(18) . ?
C4 C5 1.3913(17) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3645(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3891(17) . ?
C5A H5A 0.9500 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7 H7 1.0000 . ?
C7 C8 1.5280(16) . ?
C7 C16 1.5380(17) . ?
C8 C9 1.3949(17) . ?
C8 C13 1.4017(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3932(17) . ?
C10 C11 1.4016(16) . ?
C10 C14 1.5261(16) . ?
C11 C12 1.3859(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3892(17) . ?
C14 C1 1.5182(16) 2_655 ?
C14 H14 1.0000 . ?
C14 C15 1.5320(17) . ?
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
C3A O2A C6A 118.45(11) . . ?
C4 O4 H4 109.5 . . ?
C6 O6 H6 109.5 . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 109.5 . . ?
O1A N1A C1A 119.77(10) . . ?
O1A N1A C5A 119.76(10) . . ?
C1A N1A C5A 120.46(11) . . ?
C2 C1 C6 117.13(11) . . ?
C2 C1 C14 122.74(11) . 2_655 ?
C6 C1 C14 120.07(10) . 2_655 ?
N1A C1A H1A 119.3 . . ?
N1A C1A C2A 121.48(12) . . ?
C2A C1A H1A 119.3 . . ?
C1 C2 H2 117.9 . . ?
C1 C2 C3 124.19(11) . . ?
C3 C2 H2 117.9 . . ?
C1A C2A H2A 120.6 . . ?
C1A C2A C3A 118.86(12) . . ?
C3A C2A H2A 120.6 . . ?
C2 C3 C7 122.58(11) . . ?
C4 C3 C2 116.25(10) . . ?
C4 C3 C7 121.16(10) . . ?
O2A C3A C2A 125.66(12) . . ?
O2A C3A C4A 115.86(11) . . ?
C2A C3A C4A 118.48(12) . . ?
O4 C4 C3 119.32(10) . . ?
O4 C4 C5 119.21(11) . . ?
C5 C4 C3 121.46(11) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A C3A 120.18(12) . . ?
C5A C4A H4A 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.04(11) . . ?
C6 C5 H5 120.0 . . ?
N1A C5A C4A 120.50(12) . . ?
N1A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
O6 C6 C1 119.22(10) . . ?
O6 C6 C5 119.87(11) . . ?
C5 C6 C1 120.91(11) . . ?
O2A C6A H6AA 109.5 . . ?
O2A C6A H6AB 109.5 . . ?
O2A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C3 C7 H7 106.5 . . ?
C3 C7 C8 113.13(10) . . ?
C3 C7 C16 112.94(10) . . ?
C8 C7 H7 106.5 . . ?
C8 C7 C16 110.67(10) . . ?
C16 C7 H7 106.5 . . ?
C9 C8 C7 122.84(10) . . ?
C9 C8 C13 116.79(11) . . ?
C13 C8 C7 120.35(10) . . ?
C8 C9 H9 118.0 . . ?
C10 C9 C8 123.92(11) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C11 117.10(11) . . ?
C9 C10 C14 123.41(10) . . ?
C11 C10 C14 119.41(10) . . ?
O11 C11 C10 118.31(11) . . ?
O11 C11 C12 120.91(10) . . ?
C12 C11 C10 120.76(11) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.38(10) . . ?
C13 C12 H12 119.8 . . ?
O13 C13 C8 119.02(10) . . ?
O13 C13 C12 120.01(10) . . ?
C12 C13 C8 120.97(11) . . ?
C1 C14 C10 111.99(9) 2_655 . ?
C1 C14 H14 106.8 2_655 . ?
C1 C14 C15 112.64(10) 2_655 . ?
C10 C14 H14 106.8 . . ?
C10 C14 C15 111.49(10) . . ?
C15 C14 H14 106.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O11 H11 O4 0.84 1.91 2.7439(11) 173.7 7_656
O13 H13 O6 0.84 2.01 2.8440(12) 173.9 8_556
C15 H15B O11 0.98 2.40 3.0182(15) 120.8 .

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 7 6 0.0306 -5.0000 7.0001 6.0000 0.0580 0.2284 -0.9927
5 -7 -6 0.0334 5.0000 -7.0001 -6.0000 -0.0580 -0.2284 0.9927
6 -4 6 0.0601 6.0001 -3.9999 6.0000 0.2693 0.9303 0.2988
-7 4 -5 0.0618 -7.0001 4.0000 -5.0000 -0.3339 -0.8547 -0.3733
9 5 -4 0.0525 9.0000 4.9998 -4.0000 0.8867 -0.3443 0.0561
-10 -5 4 0.0263 -10.0001 -4.9998 4.0001 -0.9592 0.3165 -0.0906
6 -7 -4 0.0328 6.0001 -7.0000 -4.0000 0.0303 0.0059 0.9473
-5 8 4 0.0362 -5.0001 8.0000 4.0000 0.0954 -0.0143 -0.9956
3 9 0 0.0441 3.0000 8.9999 -0.0000 0.6966 -0.2418 -0.6425
-2 -6 -7 0.0359 -2.0000 -6.0000 -7.0000 -0.5199 -0.5617 0.7081

_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_2MeNPyNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450586'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_2MeNPyNO_1          
;
PROBLEM: D-H Without Acceptor      *O2W    -- *H2WB   ...     Please Check 
RESPONSE: Due to fractional disorder
;
# end Validation Reply Form

_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
'2(C6 H6 N2 O3), 4(C H4 O), 2(H2 O), C32 H32 O8'
_chemical_formula_sum            'C48 H64 N4 O20'
_chemical_formula_weight         1017.03
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O9'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.8492(6)
_cell_length_b                   20.9713(8)
_cell_length_c                   11.4872(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.111(6)
_cell_angle_gamma                90
_cell_volume                     2497.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5901
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.6600
_cell_measurement_theta_min      3.4500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.1869
_exptl_crystal_size_mid          0.1451
_exptl_crystal_size_min          0.0828
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16891
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         2.988
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   51.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega   16.00   51.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   57.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -87.00   -2.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -57.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -85.00   10.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   12.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00    8.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3868   90.0000  -77.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -32.00   54.00   1.0000   57.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3868  -90.0000  167.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0519229000
_diffrn_orient_matrix_UB_12      0.0220113000
_diffrn_orient_matrix_UB_13      -0.0159005000
_diffrn_orient_matrix_UB_21      0.0364569000
_diffrn_orient_matrix_UB_22      0.0216614000
_diffrn_orient_matrix_UB_23      0.0443044000
_diffrn_orient_matrix_UB_31      0.0256394000
_diffrn_orient_matrix_UB_32      0.0137687000
_diffrn_orient_matrix_UB_33      -0.0442788000
_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'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                7249
_reflns_number_total             8754
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    ?
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 2879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         8754
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.063
_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)+(0.1093P)²+1.7773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.1896
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3B) \\sim Ueq, Uanis(N2B) \\sim Ueq, Uanis(O2B) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: O1W(0.5) H1WA(0.5) H1WB(0.5) O2W(0.5) H2WA(0.5) H2WB(0.5)
 Fixed U33: O3A(0.12544)
4.a Riding coordinates:
 O1W(H1WA,H1WB), O2S(H2S), O2W(H2WA,H2WB), O3W(H3WA,H3WB)
4.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
4.c Aromatic/amide H refined with riding coordinates:
 C4B(H4B), C2B(H2B), C1B(H1B), C1A(H1A), C2(H2), C2A(H2A), C4A(H4A), C5(H5),
 C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26)
4.d Fitted hexagon refined as free rotating group:
 N1B(C5B,C4B,C3B,C2B,C1B)
4.e Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,
 H4SC), C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O3S(H3S), O4(H4), O4S(H4S), O6(H6), O11(H11), O13(H13), O18(H18),
 O20(H20), O25(H25), O27(H27)
;
_atom_sites_solution_hydrogens   mixed
_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
O1A O 1.1010(4) 0.7396(2) 0.0796(5) 0.0425(11) Uani 1 1 d . . . . .
O1B O 0.0350(7) 0.6347(5) -0.5853(6) 0.107(2) Uani 1 1 d . . . . .
O1S O 0.6216(5) 0.3806(3) 0.4506(4) 0.0521(13) Uani 1 1 d . . . . .
H1S H 0.5523 0.3895 0.4616 0.078 Uiso 1 1 calc GR . . . .
O1W O -0.0678(12) 0.6446(7) -0.3599(13) 0.084(5) Uani 0.5 1 d . . P A 1
H1WA H -0.1481 0.6497 -0.3820 0.126 Uiso 0.5 1 d R . P A 1
H1WB H -0.0364 0.6468 -0.4199 0.126 Uiso 0.5 1 d R . P A 1
O2A O 1.0104(8) 0.8884(5) -0.3977(8) 0.116(3) Uani 1 1 d . . . . .
O2B O 0.6023(11) 0.5572(8) -0.4819(8) 0.135(4) Uani 1 1 d . U . . .
O2S O 0.5796(7) 0.8948(3) 0.4666(5) 0.0737(19) Uani 1 1 d . . . . .
H2S H 0.5807 0.8884 0.3948 0.111 Uiso 1 1 d R . . . .
O2W O 0.0156(13) 0.6247(6) -0.3665(11) 0.067(3) Uani 0.5 1 d . . P B 2
H2WA H 0.0091 0.6249 -0.4384 0.100 Uiso 0.5 1 d R . P B 2
H2WB H -0.0476 0.6449 -0.3619 0.100 Uiso 0.5 1 d R . P B 2
O3A O 0.9557(7) 0.9592(4) -0.2873(8) 0.102(2) Uani 1 1 d . . . . .
O3B O 0.6212(10) 0.6644(7) -0.4732(7) 0.154(4) Uani 1 1 d . U . . .
O3S O 0.9741(4) 0.6259(2) 0.0264(4) 0.0449(10) Uani 1 1 d . . . . .
H3S H 1.0023 0.6624 0.0311 0.067 Uiso 1 1 calc GR . . . .
O3W O 0.1154(4) 0.5232(2) -0.0041(5) 0.0434(11) Uani 1 1 d . . . . .
H3WA H 0.0875 0.5550 0.0280 0.065 Uiso 1 1 d R . . . .
H3WB H 0.1122 0.5318 -0.0789 0.065 Uiso 1 1 d R . . . .
O4 O 0.6541(4) 0.88637(17) 0.2507(3) 0.0221(8) Uani 1 1 d . . . . .
H4 H 0.6534 0.9249 0.2385 0.033 Uiso 1 1 calc GR . . . .
O4S O 0.0987(5) 0.5207(3) -0.2630(5) 0.0573(14) Uani 1 1 d . . . . .
H4S H 0.0516 0.5521 -0.2765 0.086 Uiso 1 1 calc GR . . . .
O6 O 0.6436(4) 0.88701(18) -0.1714(4) 0.0247(9) Uani 1 1 d . . . . .
H6 H 0.6408 0.9256 -0.1609 0.037 Uiso 1 1 calc GR . . . .
O11 O 0.3541(4) 0.51721(18) 0.1493(4) 0.0264(9) Uani 1 1 d . . . . .
H11 H 0.2778 0.5245 0.1148 0.040 Uiso 1 1 calc GR . . . .
O13 O 0.3553(4) 0.74518(18) 0.1678(4) 0.0268(9) Uani 1 1 d . . . . .
H13 H 0.2777 0.7384 0.1405 0.040 Uiso 1 1 calc GR . . . .
O18 O 0.6500(4) 0.37759(18) -0.1786(3) 0.0235(9) Uani 1 1 d . . . . .
H18 H 0.6388 0.3392 -0.1723 0.035 Uiso 1 1 calc GR . . . .
O20 O 0.6592(4) 0.36850(17) 0.2357(3) 0.0225(9) Uani 1 1 d . . . . .
H20 H 0.6259 0.3864 0.2824 0.034 Uiso 1 1 calc GR . . . .
O25 O 0.3290(4) 0.73939(19) -0.2347(4) 0.0298(10) Uani 1 1 d . . . . .
H25 H 0.3688 0.7718 -0.2410 0.045 Uiso 1 1 calc GR . . . .
O27 O 0.3524(4) 0.51544(18) -0.2376(4) 0.0291(9) Uani 1 1 d . . . . .
H27 H 0.2744 0.5215 -0.2556 0.044 Uiso 1 1 calc GR . . . .
N1A N 1.0725(5) 0.7811(2) -0.0123(5) 0.0365(12) Uani 1 1 d . . . . .
N1B N 0.1583(5) 0.6329(3) -0.5654(4) 0.072(2) Uani 1 1 d . . . . .
C5B C 0.2324(8) 0.6882(3) -0.5475(5) 0.086(4) Uani 1 1 d G . . . .
C4B C 0.3654(7) 0.6841(4) -0.5235(5) 0.095(5) Uani 1 1 d G . . . .
H4B H 0.4150 0.7211 -0.5114 0.114 Uiso 1 1 calc R . . . .
C3B C 0.4244(4) 0.6249(5) -0.5174(4) 0.073(3) Uani 1 1 d G . . . .
C2B C 0.3503(6) 0.5697(3) -0.5354(5) 0.068(3) Uani 1 1 d G . . . .
H2B H 0.3898 0.5300 -0.5313 0.081 Uiso 1 1 calc R . . . .
C1B C 0.2173(6) 0.5737(3) -0.5594(5) 0.069(3) Uani 1 1 d G . . . .
H1B H 0.1678 0.5367 -0.5714 0.083 Uiso 1 1 calc R . . . .
N2A N 0.9939(8) 0.9079(6) -0.3009(11) 0.094(4) Uani 1 1 d . . . . .
N2B N 0.5655(11) 0.6151(7) -0.4893(7) 0.101(4) Uani 1 1 d . U . . .
C1 C 0.6202(5) 0.7897(2) -0.0753(5) 0.0193(12) Uani 1 1 d . . . . .
C1A C 1.0996(7) 0.7647(4) -0.1141(8) 0.0523(19) Uani 1 1 d . . . . .
H1A H 1.1370 0.7253 -0.1187 0.063 Uiso 1 1 calc R . . . .
C1S C 0.7208(9) 0.4043(4) 0.5456(8) 0.063(2) Uani 1 1 d . . . . .
H1SA H 0.8019 0.3903 0.5370 0.095 Uiso 1 1 calc GR . . . .
H1SB H 0.7117 0.3891 0.6215 0.095 Uiso 1 1 calc GR . . . .
H1SC H 0.7177 0.4501 0.5444 0.095 Uiso 1 1 calc GR . . . .
C2 C 0.6151(5) 0.7582(3) 0.0296(5) 0.0189(12) Uani 1 1 d . . . . .
H2 H 0.6028 0.7142 0.0258 0.023 Uiso 1 1 calc R . . . .
C2A C 1.0736(8) 0.8044(5) -0.2110(8) 0.063(2) Uani 1 1 d . . . . .
H2A H 1.0901 0.7929 -0.2831 0.075 Uiso 1 1 calc R . . . .
C2S C 0.6947(10) 0.8764(7) 0.5389(8) 0.093(4) Uani 1 1 d . . . . .
H2SA H 0.7616 0.8953 0.5111 0.139 Uiso 1 1 calc GR . . . .
H2SB H 0.7011 0.8308 0.5366 0.139 Uiso 1 1 calc GR . . . .
H2SC H 0.7040 0.8899 0.6209 0.139 Uiso 1 1 calc GR . . . .
C3 C 0.6273(5) 0.7888(3) 0.1402(5) 0.0195(12) Uani 1 1 d . . . . .
C3A C 1.0207(7) 0.8637(5) -0.1973(8) 0.064(3) Uani 1 1 d . . . . .
C3S C 0.8924(7) 0.6198(4) 0.1015(6) 0.0500(19) Uani 1 1 d . . . . .
H3SA H 0.8304 0.6538 0.0842 0.075 Uiso 1 1 calc GR . . . .
H3SB H 0.9430 0.6219 0.1855 0.075 Uiso 1 1 calc GR . . . .
H3SC H 0.8483 0.5796 0.0859 0.075 Uiso 1 1 calc GR . . . .
C4 C 0.6453(5) 0.8543(3) 0.1435(5) 0.0188(12) Uani 1 1 d . . . . .
C4A C 0.9940(6) 0.8811(4) -0.0914(8) 0.0504(19) Uani 1 1 d . . . . .
H4A H 0.9590 0.9209 -0.0843 0.060 Uiso 1 1 calc R . . . .
C4S C 0.0402(8) 0.4704(4) -0.3463(8) 0.063(2) Uani 1 1 d . . . . .
H4SA H 0.0305 0.4841 -0.4283 0.094 Uiso 1 1 calc GR . . . .
H4SB H -0.0430 0.4605 -0.3375 0.094 Uiso 1 1 calc GR . . . .
H4SC H 0.0940 0.4332 -0.3288 0.094 Uiso 1 1 calc GR . . . .
C5 C 0.6537(5) 0.8882(3) 0.0407(5) 0.0189(12) Uani 1 1 d . . . . .
H5 H 0.6678 0.9320 0.0448 0.023 Uiso 1 1 calc R . . . .
C5A C 1.0203(5) 0.8380(3) 0.0043(6) 0.0337(14) Uani 1 1 d . . . . .
C6 C 0.6405(5) 0.8554(3) -0.0664(5) 0.0188(11) Uani 1 1 d . . . . .
C6A C 0.9959(7) 0.8489(4) 0.1217(7) 0.0491(18) Uani 1 1 d . . . . .
H6AA H 0.9365 0.8174 0.1336 0.074 Uiso 1 1 calc GR . . . .
H6AB H 0.9598 0.8906 0.1224 0.074 Uiso 1 1 calc GR . . . .
H6AC H 1.0755 0.8458 0.1861 0.074 Uiso 1 1 calc GR . . . .
C6B C 0.154(2) 0.7475(7) -0.5503(14) 0.184(10) Uani 1 1 d . . . . .
H6BA H 0.0952 0.7531 -0.6304 0.276 Uiso 1 1 calc GR . . . .
H6BB H 0.2105 0.7837 -0.5300 0.276 Uiso 1 1 calc GR . . . .
H6BC H 0.1063 0.7437 -0.4923 0.276 Uiso 1 1 calc GR . . . .
C7 C 0.6273(5) 0.7529(2) 0.2554(5) 0.0181(11) Uani 1 1 d . . . . .
H7 H 0.5807 0.7795 0.2986 0.022 Uiso 1 1 calc R . . . .
C8 C 0.5547(5) 0.6895(2) 0.2272(4) 0.0158(11) Uani 1 1 d . . . . .
C9 C 0.6179(4) 0.6306(3) 0.2466(4) 0.0183(9) Uani 1 1 d . . . . .
H9 H 0.7074 0.6303 0.2770 0.022 Uiso 1 1 calc R . . . .
C10 C 0.5533(5) 0.5719(2) 0.2227(4) 0.0187(11) Uani 1 1 d . . . . .
C11 C 0.4205(5) 0.5736(2) 0.1743(5) 0.0181(11) Uani 1 1 d . . . . .
C12 C 0.3535(4) 0.6313(3) 0.1558(4) 0.0211(9) Uani 1 1 d . . . . .
H12 H 0.2640 0.6316 0.1253 0.025 Uiso 1 1 calc R . . . .
C13 C 0.4210(5) 0.6882(3) 0.1833(5) 0.0204(12) Uani 1 1 d . . . . .
C14 C 0.6242(5) 0.5085(2) 0.2490(5) 0.0190(12) Uani 1 1 d . . . . .
H14 H 0.5777 0.4817 0.2918 0.023 Uiso 1 1 calc R . . . .
C15 C 0.6273(5) 0.4728(2) 0.1352(5) 0.0166(11) Uani 1 1 d . . . . .
C16 C 0.6177(5) 0.5047(3) 0.0262(5) 0.0192(12) Uani 1 1 d . . . . .
H16 H 0.6046 0.5485 0.0239 0.023 Uiso 1 1 calc R . . . .
C17 C 0.6265(5) 0.4746(3) -0.0793(5) 0.0194(12) Uani 1 1 d . . . . .
C18 C 0.6438(5) 0.4081(2) -0.0744(5) 0.0179(11) Uani 1 1 d . . . . .
C19 C 0.6546(5) 0.3756(3) 0.0312(5) 0.0194(12) Uani 1 1 d . . . . .
H19 H 0.6671 0.3317 0.0332 0.023 Uiso 1 1 calc R . . . .
C20 C 0.6473(5) 0.4065(2) 0.1350(5) 0.0186(12) Uani 1 1 d . . . . .
C21 C 0.6212(6) 0.5109(2) -0.1952(5) 0.0209(12) Uani 1 1 d . . . . .
H21 H 0.5749 0.4840 -0.2640 0.025 Uiso 1 1 calc R . . . .
C22 C 0.5471(5) 0.5733(2) -0.2058(4) 0.0189(11) Uani 1 1 d . . . . .
C23 C 0.6073(5) 0.6330(3) -0.1944(4) 0.0198(9) Uani 1 1 d . . . . .
H23 H 0.6962 0.6340 -0.1799 0.024 Uiso 1 1 calc R . . . .
C24 C 0.5423(5) 0.6910(3) -0.2033(5) 0.0189(11) Uani 1 1 d . . . . .
C25 C 0.4087(6) 0.6875(2) -0.2231(5) 0.0224(12) Uani 1 1 d . . . . .
C26 C 0.3464(5) 0.6289(3) -0.2332(4) 0.0239(10) Uani 1 1 d . . . . .
H26 H 0.2578 0.6274 -0.2456 0.029 Uiso 1 1 calc R . . . .
C27 C 0.4151(6) 0.5731(3) -0.2249(5) 0.0217(12) Uani 1 1 d . . . . .
C28 C 0.6103(6) 0.7554(3) -0.1942(5) 0.0218(12) Uani 1 1 d . . . . .
H28 H 0.5579 0.7822 -0.2602 0.026 Uiso 1 1 calc R . . . .
C29 C 0.7441(6) 0.7501(3) -0.2120(6) 0.0309(14) Uani 1 1 d . . . . .
H29A H 0.7773 0.7920 -0.2178 0.046 Uiso 1 1 calc GR . . . .
H29B H 0.7381 0.7269 -0.2855 0.046 Uiso 1 1 calc GR . . . .
H29C H 0.8009 0.7281 -0.1440 0.046 Uiso 1 1 calc GR . . . .
C30 C 0.7658(6) 0.7460(3) 0.3392(6) 0.0306(14) Uani 1 1 d . . . . .
H30A H 0.8149 0.7203 0.2996 0.046 Uiso 1 1 calc GR . . . .
H30B H 0.7645 0.7259 0.4139 0.046 Uiso 1 1 calc GR . . . .
H30C H 0.8046 0.7874 0.3564 0.046 Uiso 1 1 calc GR . . . .
C31 C 0.7634(5) 0.5153(3) 0.3326(5) 0.0227(12) Uani 1 1 d . . . . .
H31A H 0.7996 0.4737 0.3553 0.034 Uiso 1 1 calc GR . . . .
H31B H 0.7632 0.5386 0.4044 0.034 Uiso 1 1 calc GR . . . .
H31C H 0.8143 0.5377 0.2902 0.034 Uiso 1 1 calc GR . . . .
C32 C 0.7597(6) 0.5186(3) -0.2018(6) 0.0295(13) Uani 1 1 d . . . . .
H32A H 0.7583 0.5394 -0.2766 0.044 Uiso 1 1 calc GR . . . .
H32B H 0.7989 0.4773 -0.1987 0.044 Uiso 1 1 calc GR . . . .
H32C H 0.8085 0.5438 -0.1341 0.044 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
O1A N1A 1.333(7) . ?
O1B N1B 1.290(8) . ?
O1S H1S 0.8200 . ?
O1S C1S 1.381(10) . ?
O1W H1WA 0.8394 . ?
O1W H1WB 0.8546 . ?
O2A N2A 1.247(15) . ?
O2B N2B 1.274(15) . ?
O2S H2S 0.8395 . ?
O2S C2S 1.337(11) . ?
O2W H2WA 0.8082 . ?
O2W H2WB 0.8204 . ?
O3A N2A 1.178(14) . ?
O3B N2B 1.184(14) . ?
O3S H3S 0.8200 . ?
O3S C3S 1.414(8) . ?
O3W H3WA 0.8594 . ?
O3W H3WB 0.8680 . ?
O4 H4 0.8200 . ?
O4 C4 1.381(6) . ?
O4S H4S 0.8200 . ?
O4S C4S 1.440(9) . ?
O6 H6 0.8200 . ?
O6 C6 1.386(7) . ?
O11 H11 0.8200 . ?
O11 C11 1.371(6) . ?
O13 H13 0.8200 . ?
O13 C13 1.376(7) . ?
O18 H18 0.8200 . ?
O18 C18 1.376(6) . ?
O20 H20 0.8200 . ?
O20 C20 1.380(6) . ?
O25 H25 0.8200 . ?
O25 C25 1.371(7) . ?
O27 H27 0.8200 . ?
O27 C27 1.374(7) . ?
N1A C1A 1.332(10) . ?
N1A C5A 1.359(8) . ?
N1B C5B 1.3900 . ?
N1B C1B 1.3900 . ?
C5B C4B 1.3900 . ?
C5B C6B 1.502(17) . ?
C4B H4B 0.9300 . ?
C4B C3B 1.3900 . ?
C3B C2B 1.3900 . ?
C3B N2B 1.483(13) . ?
C2B H2B 0.9300 . ?
C2B C1B 1.3900 . ?
C1B H1B 0.9300 . ?
N2A C3A 1.470(11) . ?
C1 C2 1.390(8) . ?
C1 C6 1.394(7) . ?
C1 C28 1.519(8) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.351(12) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.394(8) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.397(13) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?
C3 C4 1.386(7) . ?
C3 C7 1.523(7) . ?
C3A C4A 1.380(13) . ?
C3S H3SA 0.9600 . ?
C3S H3SB 0.9600 . ?
C3S H3SC 0.9600 . ?
C4 C5 1.405(7) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.386(10) . ?
C4S H4SA 0.9600 . ?
C4S H4SB 0.9600 . ?
C4S H4SC 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.381(8) . ?
C5A C6A 1.467(10) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.531(7) . ?
C7 C30 1.534(8) . ?
C8 C9 1.397(8) . ?
C8 C13 1.389(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.404(8) . ?
C10 C11 1.384(8) . ?
C10 C14 1.521(7) . ?
C11 C12 1.394(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(8) . ?
C14 H14 0.9800 . ?
C14 C15 1.515(7) . ?
C14 C31 1.539(8) . ?
C15 C16 1.396(7) . ?
C15 C20 1.407(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(8) . ?
C17 C18 1.407(7) . ?
C17 C21 1.520(7) . ?
C18 C19 1.365(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(7) . ?
C21 H21 0.9800 . ?
C21 C22 1.523(8) . ?
C21 C32 1.535(8) . ?
C22 C23 1.400(8) . ?
C22 C27 1.383(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.395(8) . ?
C24 C25 1.401(8) . ?
C24 C28 1.528(7) . ?
C25 C26 1.392(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.375(8) . ?
C28 H28 0.9800 . ?
C28 C29 1.528(8) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
C1S O1S H1S 109.5 . . ?
H1WA O1W H1WB 111.9 . . ?
C2S O2S H2S 106.5 . . ?
H2WA O2W H2WB 103.8 . . ?
C3S O3S H3S 109.5 . . ?
H3WA O3W H3WB 110.4 . . ?
C4 O4 H4 109.5 . . ?
C4S O4S H4S 109.5 . . ?
C6 O6 H6 109.5 . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 109.5 . . ?
C18 O18 H18 109.5 . . ?
C20 O20 H20 109.5 . . ?
C25 O25 H25 109.5 . . ?
C27 O27 H27 109.5 . . ?
O1A N1A C5A 118.1(5) . . ?
C1A N1A O1A 117.9(6) . . ?
C1A N1A C5A 124.0(6) . . ?
O1B N1B C5B 121.7(7) . . ?
O1B N1B C1B 118.3(7) . . ?
C5B N1B C1B 120.0 . . ?
N1B C5B C6B 112.9(10) . . ?
C4B C5B N1B 120.0 . . ?
C4B C5B C6B 127.0(10) . . ?
C5B C4B H4B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C3B N2B 124.4(8) . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B N2B 115.6(8) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B C3B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
N1B C1B H1B 120.0 . . ?
C2B C1B N1B 120.0 . . ?
C2B C1B H1B 120.0 . . ?
O2A N2A C3A 117.9(12) . . ?
O3A N2A O2A 124.5(10) . . ?
O3A N2A C3A 117.5(12) . . ?
O2B N2B C3B 115.4(11) . . ?
O3B N2B O2B 133.3(14) . . ?
O3B N2B C3B 111.1(13) . . ?
C2 C1 C6 116.9(5) . . ?
C2 C1 C28 122.9(5) . . ?
C6 C1 C28 120.1(5) . . ?
N1A C1A H1A 119.4 . . ?
N1A C1A C2A 121.2(8) . . ?
C2A C1A H1A 119.4 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1 C2 H2 118.2 . . ?
C1 C2 C3 123.6(5) . . ?
C3 C2 H2 118.2 . . ?
C1A C2A H2A 121.7 . . ?
C1A C2A C3A 116.6(8) . . ?
C3A C2A H2A 121.7 . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C2 C3 C7 122.7(5) . . ?
C4 C3 C2 117.2(5) . . ?
C4 C3 C7 120.1(5) . . ?
C2A C3A N2A 117.4(10) . . ?
C4A C3A N2A 120.2(10) . . ?
C4A C3A C2A 122.3(7) . . ?
O3S C3S H3SA 109.5 . . ?
O3S C3S H3SB 109.5 . . ?
O3S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
O4 C4 C3 118.7(5) . . ?
O4 C4 C5 119.8(5) . . ?
C3 C4 C5 121.5(5) . . ?
C3A C4A H4A 120.7 . . ?
C3A C4A C5A 118.6(7) . . ?
C5A C4A H4A 120.7 . . ?
O4S C4S H4SA 109.5 . . ?
O4S C4S H4SB 109.5 . . ?
O4S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.7(5) . . ?
C6 C5 H5 120.6 . . ?
N1A C5A C4A 117.3(7) . . ?
N1A C5A C6A 117.5(6) . . ?
C4A C5A C6A 125.2(6) . . ?
O6 C6 C1 116.9(5) . . ?
C5 C6 O6 121.0(5) . . ?
C5 C6 C1 122.1(5) . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C3 C7 H7 107.0 . . ?
C3 C7 C8 112.2(4) . . ?
C3 C7 C30 110.0(5) . . ?
C8 C7 H7 107.0 . . ?
C8 C7 C30 113.5(4) . . ?
C30 C7 H7 107.0 . . ?
C9 C8 C7 122.4(4) . . ?
C13 C8 C7 120.7(5) . . ?
C13 C8 C9 116.9(5) . . ?
C8 C9 H9 118.3 . . ?
C8 C9 C10 123.3(4) . . ?
C10 C9 H9 118.3 . . ?
C9 C10 C14 122.2(5) . . ?
C11 C10 C9 117.2(5) . . ?
C11 C10 C14 120.6(5) . . ?
O11 C11 C10 118.8(5) . . ?
O11 C11 C12 119.9(5) . . ?
C10 C11 C12 121.3(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
O13 C13 C8 118.4(5) . . ?
O13 C13 C12 119.9(5) . . ?
C12 C13 C8 121.6(5) . . ?
C10 C14 H14 107.2 . . ?
C10 C14 C31 112.9(4) . . ?
C15 C14 C10 113.5(4) . . ?
C15 C14 H14 107.2 . . ?
C15 C14 C31 108.5(4) . . ?
C31 C14 H14 107.2 . . ?
C16 C15 C14 121.5(4) . . ?
C16 C15 C20 116.3(5) . . ?
C20 C15 C14 122.2(5) . . ?
C15 C16 H16 118.1 . . ?
C17 C16 C15 123.9(5) . . ?
C17 C16 H16 118.1 . . ?
C16 C17 C18 117.1(5) . . ?
C16 C17 C21 122.8(5) . . ?
C18 C17 C21 120.1(5) . . ?
O18 C18 C17 117.8(5) . . ?
C19 C18 O18 121.9(5) . . ?
C19 C18 C17 120.4(5) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.5(5) . . ?
C20 C19 H19 119.2 . . ?
O20 C20 C15 123.1(5) . . ?
C19 C20 O20 116.0(4) . . ?
C19 C20 C15 120.9(5) . . ?
C17 C21 H21 107.3 . . ?
C17 C21 C22 112.5(4) . . ?
C17 C21 C32 108.1(5) . . ?
C22 C21 H21 107.3 . . ?
C22 C21 C32 114.1(5) . . ?
C32 C21 H21 107.3 . . ?
C23 C22 C21 122.7(5) . . ?
C27 C22 C21 120.5(5) . . ?
C27 C22 C23 116.8(5) . . ?
C22 C23 H23 117.9 . . ?
C24 C23 C22 124.1(4) . . ?
C24 C23 H23 117.9 . . ?
C23 C24 C25 116.3(5) . . ?
C23 C24 C28 122.8(5) . . ?
C25 C24 C28 120.9(5) . . ?
O25 C25 C24 124.6(5) . . ?
O25 C25 C26 114.6(5) . . ?
C26 C25 C24 120.9(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
O27 C27 C22 118.5(5) . . ?
O27 C27 C26 120.0(5) . . ?
C26 C27 C22 121.5(5) . . ?
C1 C28 C24 112.7(4) . . ?
C1 C28 H28 107.2 . . ?
C1 C28 C29 109.7(5) . . ?
C24 C28 H28 107.2 . . ?
C24 C28 C29 112.7(5) . . ?
C29 C28 H28 107.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C14 C31 H31A 109.5 . . ?
C14 C31 H31B 109.5 . . ?
C14 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C32 H32A 109.5 . . ?
C21 C32 H32B 109.5 . . ?
C21 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8 0 -16 0.0586 8.0022 0.0022 -16.0008 -0.1610 -0.4171 0.9137
2 28 4 0.0747 1.9963 28.0021 3.9984 0.4491 0.8565 0.2597
-14 6 -1 0.0318 -13.9991 5.9937 -1.0006 0.8747 -0.4249 -0.2321
15 -4 -1 0.0426 14.9992 -3.9934 -0.9996 -0.8508 0.4160 0.3738
-14 -10 8 0.0655 -13.9992 -10.0059 8.0010 0.3794 -0.3726 -0.8510
-1 -1 16 0.0720 -1.0028 -0.9991 16.0010 -0.2243 0.6507 -0.7480
11 16 4 0.0586 10.9966 16.0058 3.9993 -0.2823 0.9248 0.3252
-13 2 -4 0.0346 -12.9982 1.9938 -4.0005 0.7824 -0.6079 -0.1287
-14 11 1 0.0322 -14.0000 10.9941 0.9992 0.9530 -0.2280 -0.2518
12 -14 2 0.0557 11.9999 -13.9948 2.0012 -0.9629 0.2230 0.0264
-9 -15 13 0.0726 -9.0001 -15.0033 13.0016 -0.0697 -0.0771 -1.0130
-4 -29 3 0.0783 -3.9973 -29.0024 3.0020 -0.4786 -0.6410 -0.6347

_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_4PhPyNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450587'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C11 H9 N O), C32 H32 O8'
_chemical_formula_sum            'C54 H50 N2 O10'
_chemical_formula_weight         886.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9'
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'

_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                   13.3203(4)
_cell_length_b                   16.1527(4)
_cell_length_c                   20.8931(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.307(2)
_cell_angle_gamma                90
_cell_volume                     4422.80(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      74.2060
_cell_measurement_theta_min      4.3200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 -3 0 0.0263
8 3 0 0.0197
-2 3 13 0.1129
3 -3 -13 0.1099
-2 10 -2 0.0197
-1 -10 1 0.0073

_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.039
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8.0000 -2.9999 -0.0000 0.0529 0.0901 0.9785
8.0000 2.9999 0.0000 -0.0529 -0.0901 -0.9785
-2.0000 3.0000 13.0000 0.4707 0.8753 -0.1316
3.0000 -3.0000 -13.0000 -0.4526 -0.9097 0.0206
-1.9995 10.0000 -2.0000 -0.8026 0.5927 -0.0391
-1.0005 -10.0000 1.0000 0.6943 -0.5370 0.3924

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12192
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.748
_diffrn_reflns_theta_min         3.372
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -25.00   1.00   20.00    --  -41.78 -37.00-180.00   90
  2  ω    -96.00  -7.00   1.00   20.00    --  -41.78 125.00 -30.00   89
  3  ω     18.00  46.00   1.00   20.00    --   41.78 -37.00-120.00   28
  4  ω     74.00 174.00   1.00   80.00    --  106.66  77.00-180.00  100
  5  ω    105.00 178.00   1.00   80.00    --  106.66 125.00  60.00   73
  6  ω     32.00 135.00   1.00   80.00    --  106.66 -77.00  90.00  103
  7  ω     42.00 119.00   1.00   80.00    --  106.66 -45.00 -90.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0180660000
_diffrn_orient_matrix_UB_12      -0.0658168000
_diffrn_orient_matrix_UB_13      0.0541739000
_diffrn_orient_matrix_UB_21      -0.0344795000
_diffrn_orient_matrix_UB_22      0.0619215000
_diffrn_orient_matrix_UB_23      0.0477330000
_diffrn_orient_matrix_UB_31      -0.1109995000
_diffrn_orient_matrix_UB_32      -0.0301548000
_diffrn_orient_matrix_UB_33      -0.0202376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7976
_reflns_number_total             12192
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.241
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         12192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      0.871
_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)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7434(6) 0.2566(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
3.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C2(H2), C2A(H2A), C2B(H2B), C4A(H4A), C4B(H4B), C5(H5),
 C5A(H5A), C5B(H5B), C7A(H7A), C7B(H7B), C8A(H8A), C8B(H8B), C9(H9), C9A(H9A),
 C9B(H9B), C10A(H10A), C10B(H10B), C11A(H11A), C11B(H11B), C12(H12), C16(H16),
 C19(H19), C23(H23), C26(H26)
3.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O11(H11), O13(H13), O18(H18), O20(H20), O25(H25), O27(H27)
;
_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
O1A O 0.74385(11) 0.52748(9) 0.56447(7) 0.0249(3) Uani 1 1 d . . . . .
O1B O 0.73799(12) 0.53017(10) 0.37126(7) 0.0280(3) Uani 1 1 d . . . . .
O4 O 0.56079(10) 0.84575(10) 0.19023(6) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.5721 0.8432 0.1530 0.030 Uiso 1 1 calc GR . . . .
O6 O 0.92700(10) 0.84510(10) 0.23662(6) 0.0192(3) Uani 1 1 d . . . . .
H6 H 0.9174 0.8473 0.1968 0.029 Uiso 1 1 calc GR . . . .
O11 O 0.59377(11) 0.64203(9) 0.56264(6) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.6285 0.6007 0.5601 0.031 Uiso 1 1 calc GR . . . .
O13 O 0.58766(11) 0.64194(10) 0.33334(6) 0.0213(3) Uani 1 1 d . . . . .
H13 H 0.6226 0.6005 0.3431 0.032 Uiso 1 1 calc GR . . . .
O18 O 0.91708(10) 0.85262(10) 0.74419(6) 0.0212(3) Uani 1 1 d . . . . .
H18 H 0.9054 0.8494 0.7813 0.032 Uiso 1 1 calc GR . . . .
O20 O 0.55083(10) 0.85216(10) 0.69654(6) 0.0212(3) Uani 1 1 d . . . . .
H20 H 0.5590 0.8496 0.7363 0.032 Uiso 1 1 calc GR . . . .
O25 O 0.88499(11) 0.64308(9) 0.37159(7) 0.0217(3) Uani 1 1 d . . . . .
H25 H 0.8441 0.6052 0.3721 0.033 Uiso 1 1 calc GR . . . .
O27 O 0.89228(11) 0.63688(9) 0.60106(6) 0.0200(3) Uani 1 1 d . . . . .
H27 H 0.8552 0.5968 0.5907 0.030 Uiso 1 1 calc GR . . . .
N1A N 0.74674(13) 0.44582(11) 0.55615(8) 0.0210(4) Uani 1 1 d . . . . .
N1B N 0.74449(13) 0.45537(11) 0.34559(8) 0.0245(4) Uani 1 1 d . . . . .
C1 C 0.83438(14) 0.82210(13) 0.32278(9) 0.0156(4) Uani 1 1 d . . . . .
C1A C 0.82141(16) 0.41128(14) 0.52871(10) 0.0250(5) Uani 1 1 d . . . . .
H1A H 0.8701 0.4451 0.5152 0.030 Uiso 1 1 calc R . . . .
C1B C 0.8242(2) 0.43594(17) 0.31653(15) 0.0446(7) Uani 1 1 d . . . . .
H1B H 0.8735 0.4757 0.3134 0.053 Uiso 1 1 calc R . . . .
C2 C 0.73949(14) 0.81616(12) 0.34185(9) 0.0159(4) Uani 1 1 d . . . . .
H2 H 0.7380 0.8071 0.3856 0.019 Uiso 1 1 calc R . . . .
C2A C 0.82646(17) 0.32723(14) 0.52042(10) 0.0250(5) Uani 1 1 d . . . . .
H2A H 0.8780 0.3049 0.5010 0.030 Uiso 1 1 calc R . . . .
C2B C 0.8332(2) 0.35865(17) 0.29173(15) 0.0448(7) Uani 1 1 d . . . . .
H2B H 0.8891 0.3466 0.2724 0.054 Uiso 1 1 calc R . . . .
C3 C 0.64679(15) 0.82303(13) 0.29897(9) 0.0159(4) Uani 1 1 d . . . . .
C3A C 0.75473(16) 0.27459(14) 0.54091(10) 0.0213(4) Uani 1 1 d . . . . .
C3B C 0.76061(16) 0.29745(15) 0.29479(11) 0.0259(5) Uani 1 1 d . . . . .
C4 C 0.65148(14) 0.83905(12) 0.23366(9) 0.0158(4) Uani 1 1 d . . . . .
C4A C 0.67881(15) 0.31275(14) 0.56911(10) 0.0225(4) Uani 1 1 d . . . . .
H4A H 0.6295 0.2803 0.5834 0.027 Uiso 1 1 calc R . . . .
C4B C 0.67871(17) 0.32045(15) 0.32417(11) 0.0272(5) Uani 1 1 d . . . . .
H4B H 0.6275 0.2822 0.3270 0.033 Uiso 1 1 calc R . . . .
C5 C 0.74379(15) 0.84610(12) 0.21311(9) 0.0167(4) Uani 1 1 d . . . . .
H5 H 0.7454 0.8565 0.1695 0.020 Uiso 1 1 calc R . . . .
C5A C 0.67579(15) 0.39723(14) 0.57611(10) 0.0229(4) Uani 1 1 d . . . . .
H5A H 0.6244 0.4212 0.5948 0.027 Uiso 1 1 calc R . . . .
C5B C 0.67245(17) 0.39849(15) 0.34898(11) 0.0285(5) Uani 1 1 d . . . . .
H5B H 0.6172 0.4122 0.3685 0.034 Uiso 1 1 calc R . . . .
C6 C 0.83436(14) 0.83773(12) 0.25722(9) 0.0156(4) Uani 1 1 d . . . . .
C6A C 0.75774(15) 0.18391(13) 0.53301(10) 0.0215(4) Uani 1 1 d . . . . .
C6B C 0.77012(17) 0.21319(14) 0.26885(11) 0.0259(5) Uani 1 1 d . . . . .
C7 C 0.54368(15) 0.81510(13) 0.32055(9) 0.0172(4) Uani 1 1 d . . . . .
H7 H 0.4996 0.7819 0.2876 0.021 Uiso 1 1 calc R . . . .
C7A C 0.78013(16) 0.14920(14) 0.47586(11) 0.0244(4) Uani 1 1 d . . . . .
H7A H 0.7947 0.1835 0.4430 0.029 Uiso 1 1 calc R . . . .
C7B C 0.84402(17) 0.19614(15) 0.23098(11) 0.0290(5) Uani 1 1 d . . . . .
H7B H 0.8859 0.2385 0.2210 0.035 Uiso 1 1 calc R . . . .
C8 C 0.55315(14) 0.76882(13) 0.38474(9) 0.0160(4) Uani 1 1 d . . . . .
C8A C 0.78075(16) 0.06382(14) 0.46796(11) 0.0270(5) Uani 1 1 d . . . . .
H8A H 0.7948 0.0413 0.4296 0.032 Uiso 1 1 calc R . . . .
C8B C 0.85585(17) 0.11686(16) 0.20807(11) 0.0326(5) Uani 1 1 d . . . . .
H8B H 0.9054 0.1066 0.1828 0.039 Uiso 1 1 calc R . . . .
C9 C 0.54328(13) 0.80824(13) 0.44280(9) 0.0158(4) Uani 1 1 d . . . . .
H9 H 0.5275 0.8644 0.4411 0.019 Uiso 1 1 calc R . . . .
C9A C 0.76037(16) 0.01193(14) 0.51726(11) 0.0276(5) Uani 1 1 d . . . . .
H9A H 0.7606 -0.0452 0.5119 0.033 Uiso 1 1 calc R . . . .
C9B C 0.7949(2) 0.05325(16) 0.22238(12) 0.0383(6) Uani 1 1 d . . . . .
H9B H 0.8030 0.0002 0.2068 0.046 Uiso 1 1 calc R . . . .
C10 C 0.55562(14) 0.76877(13) 0.50327(9) 0.0153(4) Uani 1 1 d . . . . .
C10A C 0.73959(16) 0.04620(14) 0.57480(11) 0.0272(5) Uani 1 1 d . . . . .
H10A H 0.7270 0.0118 0.6082 0.033 Uiso 1 1 calc R . . . .
C10B C 0.7222(2) 0.06860(17) 0.25983(13) 0.0493(7) Uani 1 1 d . . . . .
H10B H 0.6814 0.0255 0.2700 0.059 Uiso 1 1 calc R . . . .
C11 C 0.58058(14) 0.68481(14) 0.50430(9) 0.0169(4) Uani 1 1 d . . . . .
C11A C 0.73773(15) 0.13079(14) 0.58215(10) 0.0245(5) Uani 1 1 d . . . . .
H11A H 0.7229 0.1531 0.6204 0.029 Uiso 1 1 calc R . . . .
C11B C 0.7089(2) 0.14767(17) 0.28254(13) 0.0432(7) Uani 1 1 d . . . . .
H11B H 0.6585 0.1573 0.3072 0.052 Uiso 1 1 calc R . . . .
C12 C 0.59121(15) 0.64294(13) 0.44783(9) 0.0182(4) Uani 1 1 d . . . . .
H12 H 0.6077 0.5869 0.4496 0.022 Uiso 1 1 calc R . . . .
C13 C 0.57739(14) 0.68428(14) 0.38900(9) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.54401(14) 0.81478(13) 0.56507(9) 0.0157(4) Uani 1 1 d . . . . .
H14 H 0.4985 0.7818 0.5870 0.019 Uiso 1 1 calc R . . . .
C15 C 0.64479(15) 0.82399(13) 0.61216(9) 0.0165(4) Uani 1 1 d . . . . .
C16 C 0.73973(14) 0.81395(12) 0.59369(8) 0.0153(4) Uani 1 1 d . . . . .
H16 H 0.7413 0.8005 0.5506 0.018 Uiso 1 1 calc R . . . .
C17 C 0.83249(15) 0.82302(13) 0.63637(9) 0.0159(4) Uani 1 1 d . . . . .
C18 C 0.82728(15) 0.84495(13) 0.70049(9) 0.0163(4) Uani 1 1 d . . . . .
C19 C 0.73457(15) 0.85732(12) 0.72028(9) 0.0178(4) Uani 1 1 d . . . . .
H19 H 0.7331 0.8740 0.7627 0.021 Uiso 1 1 calc R . . . .
C20 C 0.64374(14) 0.84489(13) 0.67703(9) 0.0167(4) Uani 1 1 d . . . . .
C21 C 0.93627(14) 0.80954(13) 0.61631(9) 0.0159(4) Uani 1 1 d . . . . .
H21 H 0.9759 0.7735 0.6492 0.019 Uiso 1 1 calc R . . . .
C22 C 0.92728(14) 0.76504(13) 0.55132(8) 0.0155(4) Uani 1 1 d . . . . .
C23 C 0.93763(14) 0.80606(12) 0.49376(9) 0.0147(4) Uani 1 1 d . . . . .
H23 H 0.9543 0.8620 0.4964 0.018 Uiso 1 1 calc R . . . .
C24 C 0.92441(14) 0.76823(13) 0.43247(9) 0.0152(4) Uani 1 1 d . . . . .
C25 C 0.89918(14) 0.68421(13) 0.43026(8) 0.0160(4) Uani 1 1 d . . . . .
C26 C 0.88932(14) 0.64105(13) 0.48607(9) 0.0181(4) Uani 1 1 d . . . . .
H26 H 0.8735 0.5849 0.4835 0.022 Uiso 1 1 calc R . . . .
C27 C 0.90289(14) 0.68087(13) 0.54590(9) 0.0158(4) Uani 1 1 d . . . . .
C28 C 0.93489(14) 0.81459(13) 0.37073(9) 0.0154(4) Uani 1 1 d . . . . .
H28 H 0.9815 0.7824 0.3491 0.019 Uiso 1 1 calc R . . . .
C29 C 0.98167(15) 0.90069(13) 0.38372(10) 0.0202(4) Uani 1 1 d . . . . .
H29A H 0.9351 0.9357 0.4014 0.030 Uiso 1 1 calc GR . . . .
H29B H 0.9947 0.9240 0.3437 0.030 Uiso 1 1 calc GR . . . .
H29C H 1.0446 0.8965 0.4142 0.030 Uiso 1 1 calc GR . . . .
C30 C 0.49439(15) 0.90067(14) 0.32113(10) 0.0241(5) Uani 1 1 d . . . . .
H30A H 0.5366 0.9354 0.3522 0.036 Uiso 1 1 calc GR . . . .
H30B H 0.4283 0.8952 0.3330 0.036 Uiso 1 1 calc GR . . . .
H30C H 0.4873 0.9250 0.2786 0.036 Uiso 1 1 calc GR . . . .
C31 C 0.49543(15) 0.90055(13) 0.55198(10) 0.0205(4) Uani 1 1 d . . . . .
H31A H 0.5410 0.9360 0.5339 0.031 Uiso 1 1 calc GR . . . .
H31B H 0.4826 0.9238 0.5920 0.031 Uiso 1 1 calc GR . . . .
H31C H 0.4323 0.8955 0.5218 0.031 Uiso 1 1 calc GR . . . .
C32 C 0.99377(15) 0.89138(13) 0.61831(10) 0.0204(4) Uani 1 1 d . . . . .
H32A H 1.0594 0.8821 0.6067 0.031 Uiso 1 1 calc GR . . . .
H32B H 1.0025 0.9141 0.6614 0.031 Uiso 1 1 calc GR . . . .
H32C H 0.9556 0.9295 0.5881 0.031 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
O1A N1A 1.332(2) . ?
O1B N1B 1.331(2) . ?
O4 H4 0.8200 . ?
O4 C4 1.379(2) . ?
O6 H6 0.8200 . ?
O6 C6 1.383(2) . ?
O11 H11 0.8200 . ?
O11 C11 1.385(2) . ?
O13 H13 0.8200 . ?
O13 C13 1.377(2) . ?
O18 H18 0.8200 . ?
O18 C18 1.374(2) . ?
O20 H20 0.8200 . ?
O20 C20 1.375(2) . ?
O25 H25 0.8200 . ?
O25 C25 1.377(2) . ?
O27 H27 0.8200 . ?
O27 C27 1.382(2) . ?
N1A C1A 1.354(3) . ?
N1A C5A 1.351(3) . ?
N1B C1B 1.351(3) . ?
N1B C5B 1.340(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.393(3) . ?
C1 C28 1.527(3) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.372(3) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.365(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.402(3) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.392(3) . ?
C3 C4 1.401(3) . ?
C3 C7 1.526(3) . ?
C3A C4A 1.401(3) . ?
C3A C6A 1.475(3) . ?
C3B C4B 1.395(3) . ?
C3B C6B 1.479(3) . ?
C4 C5 1.378(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.374(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.371(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C5A H5A 0.9300 . ?
C5B H5B 0.9300 . ?
C6A C7A 1.399(3) . ?
C6A C11A 1.400(3) . ?
C6B C7B 1.396(3) . ?
C6B C11B 1.397(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(3) . ?
C7 C30 1.531(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.389(3) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.386(3) . ?
C8 C9 1.397(3) . ?
C8 C13 1.402(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.392(3) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.375(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.396(3) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.373(4) . ?
C10 C11 1.396(3) . ?
C10 C14 1.521(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.376(3) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.385(4) . ?
C11 C12 1.389(3) . ?
C11A H11A 0.9300 . ?
C11B H11B 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.523(3) . ?
C14 C31 1.533(3) . ?
C15 C16 1.396(3) . ?
C15 C20 1.399(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(3) . ?
C17 C18 1.399(3) . ?
C17 C21 1.530(3) . ?
C18 C19 1.385(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C21 H21 0.9800 . ?
C21 C22 1.522(3) . ?
C21 C32 1.525(3) . ?
C22 C23 1.401(3) . ?
C22 C27 1.398(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.401(3) . ?
C24 C25 1.397(3) . ?
C24 C28 1.519(3) . ?
C25 C26 1.385(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(3) . ?
C28 H28 0.9800 . ?
C28 C29 1.528(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
C4 O4 H4 109.5 . . ?
C6 O6 H6 109.5 . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 109.5 . . ?
C18 O18 H18 109.5 . . ?
C20 O20 H20 109.5 . . ?
C25 O25 H25 109.5 . . ?
C27 O27 H27 109.5 . . ?
O1A N1A C1A 120.26(18) . . ?
O1A N1A C5A 119.80(17) . . ?
C5A N1A C1A 119.93(19) . . ?
O1B N1B C1B 120.34(19) . . ?
O1B N1B C5B 120.16(18) . . ?
C5B N1B C1B 119.5(2) . . ?
C2 C1 C28 122.69(16) . . ?
C6 C1 C2 116.92(17) . . ?
C6 C1 C28 120.38(17) . . ?
N1A C1A H1A 119.4 . . ?
N1A C1A C2A 121.2(2) . . ?
C2A C1A H1A 119.4 . . ?
N1B C1B H1B 119.6 . . ?
N1B C1B C2B 120.8(2) . . ?
C2B C1B H1B 119.6 . . ?
C1 C2 H2 118.2 . . ?
C3 C2 C1 123.67(17) . . ?
C3 C2 H2 118.2 . . ?
C1A C2A H2A 119.7 . . ?
C1A C2A C3A 120.7(2) . . ?
C3A C2A H2A 119.7 . . ?
C1B C2B H2B 119.2 . . ?
C1B C2B C3B 121.5(2) . . ?
C3B C2B H2B 119.2 . . ?
C2 C3 C4 116.87(17) . . ?
C2 C3 C7 122.95(16) . . ?
C4 C3 C7 120.17(17) . . ?
C2A C3A C6A 122.30(19) . . ?
C4A C3A C2A 116.4(2) . . ?
C4A C3A C6A 121.3(2) . . ?
C2B C3B C4B 115.8(2) . . ?
C2B C3B C6B 122.1(2) . . ?
C4B C3B C6B 122.1(2) . . ?
O4 C4 C3 117.96(17) . . ?
C5 C4 O4 120.92(17) . . ?
C5 C4 C3 121.10(18) . . ?
C3A C4A H4A 119.4 . . ?
C5A C4A C3A 121.3(2) . . ?
C5A C4A H4A 119.4 . . ?
C3B C4B H4B 119.4 . . ?
C5B C4B C3B 121.1(2) . . ?
C5B C4B H4B 119.4 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.21(17) . . ?
C6 C5 H5 119.9 . . ?
N1A C5A C4A 120.6(2) . . ?
N1A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
N1B C5B C4B 121.2(2) . . ?
N1B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
O6 C6 C1 118.59(17) . . ?
O6 C6 C5 120.20(16) . . ?
C5 C6 C1 121.20(17) . . ?
C7A C6A C3A 120.51(19) . . ?
C7A C6A C11A 118.6(2) . . ?
C11A C6A C3A 120.93(19) . . ?
C7B C6B C3B 120.3(2) . . ?
C7B C6B C11B 117.6(2) . . ?
C11B C6B C3B 122.1(2) . . ?
C3 C7 H7 107.2 . . ?
C3 C7 C30 109.66(17) . . ?
C8 C7 C3 111.40(16) . . ?
C8 C7 H7 107.2 . . ?
C8 C7 C30 113.87(16) . . ?
C30 C7 H7 107.2 . . ?
C6A C7A H7A 119.8 . . ?
C8A C7A C6A 120.4(2) . . ?
C8A C7A H7A 119.8 . . ?
C6B C7B H7B 119.6 . . ?
C8B C7B C6B 120.9(2) . . ?
C8B C7B H7B 119.6 . . ?
C9 C8 C7 122.41(19) . . ?
C9 C8 C13 116.43(18) . . ?
C13 C8 C7 121.09(17) . . ?
C7A C8A H8A 119.9 . . ?
C7A C8A C9A 120.3(2) . . ?
C9A C8A H8A 119.9 . . ?
C7B C8B H8B 119.8 . . ?
C9B C8B C7B 120.5(2) . . ?
C9B C8B H8B 119.8 . . ?
C8 C9 H9 117.9 . . ?
C8 C9 C10 124.24(19) . . ?
C10 C9 H9 117.9 . . ?
C8A C9A H9A 120.2 . . ?
C8A C9A C10A 119.6(2) . . ?
C10A C9A H9A 120.2 . . ?
C8B C9B H9B 120.2 . . ?
C10B C9B C8B 119.6(2) . . ?
C10B C9B H9B 120.2 . . ?
C9 C10 C14 122.06(18) . . ?
C11 C10 C9 116.49(17) . . ?
C11 C10 C14 121.45(17) . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A C9A 120.0(2) . . ?
C11A C10A H10A 120.0 . . ?
C9B C10B H10B 119.7 . . ?
C9B C10B C11B 120.6(3) . . ?
C11B C10B H10B 119.7 . . ?
O11 C11 C10 119.40(17) . . ?
O11 C11 C12 119.24(19) . . ?
C12 C11 C10 121.35(18) . . ?
C6A C11A H11A 119.4 . . ?
C10A C11A C6A 121.2(2) . . ?
C10A C11A H11A 119.4 . . ?
C6B C11B H11B 119.5 . . ?
C10B C11B C6B 120.9(2) . . ?
C10B C11B H11B 119.5 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.17(19) . . ?
C13 C12 H12 119.9 . . ?
O13 C13 C8 119.12(17) . . ?
O13 C13 C12 119.58(19) . . ?
C12 C13 C8 121.30(18) . . ?
C10 C14 H14 107.3 . . ?
C10 C14 C15 112.60(15) . . ?
C10 C14 C31 113.19(16) . . ?
C15 C14 H14 107.3 . . ?
C15 C14 C31 108.79(17) . . ?
C31 C14 H14 107.3 . . ?
C16 C15 C14 123.18(16) . . ?
C16 C15 C20 117.54(18) . . ?
C20 C15 C14 119.27(17) . . ?
C15 C16 H16 118.2 . . ?
C15 C16 C17 123.59(17) . . ?
C17 C16 H16 118.2 . . ?
C16 C17 C18 116.62(17) . . ?
C16 C17 C21 123.36(16) . . ?
C18 C17 C21 120.01(17) . . ?
O18 C18 C17 118.19(17) . . ?
O18 C18 C19 120.34(17) . . ?
C19 C18 C17 121.46(18) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.27(17) . . ?
C20 C19 H19 119.9 . . ?
O20 C20 C15 118.24(17) . . ?
O20 C20 C19 121.33(16) . . ?
C19 C20 C15 120.43(17) . . ?
C17 C21 H21 107.0 . . ?
C22 C21 C17 112.39(16) . . ?
C22 C21 H21 107.0 . . ?
C22 C21 C32 113.13(16) . . ?
C32 C21 C17 110.07(16) . . ?
C32 C21 H21 107.0 . . ?
C23 C22 C21 122.57(18) . . ?
C27 C22 C21 120.77(17) . . ?
C27 C22 C23 116.58(17) . . ?
C22 C23 H23 117.9 . . ?
C24 C23 C22 124.23(18) . . ?
C24 C23 H23 117.9 . . ?
C23 C24 C28 123.04(18) . . ?
C25 C24 C23 116.37(17) . . ?
C25 C24 C28 120.58(17) . . ?
O25 C25 C24 119.48(17) . . ?
O25 C25 C26 119.21(18) . . ?
C26 C25 C24 121.31(17) . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.54(18) . . ?
C27 C26 H26 119.7 . . ?
O27 C27 C22 119.30(17) . . ?
O27 C27 C26 119.74(18) . . ?
C26 C27 C22 120.96(17) . . ?
C1 C28 H28 107.0 . . ?
C1 C28 C29 109.03(16) . . ?
C24 C28 C1 113.16(15) . . ?
C24 C28 H28 107.0 . . ?
C24 C28 C29 113.22(16) . . ?
C29 C28 H28 107.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C14 C31 H31A 109.5 . . ?
C14 C31 H31B 109.5 . . ?
C14 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C32 H32A 109.5 . . ?
C21 C32 H32B 109.5 . . ?
C21 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O1A N1A C1A C2A 179.20(19) . . . . ?
O1A N1A C5A C4A -178.67(18) . . . . ?
O1B N1B C1B C2B 178.0(3) . . . . ?
O1B N1B C5B C4B -178.5(2) . . . . ?
O4 C4 C5 C6 -178.84(19) . . . . ?
O11 C11 C12 C13 179.37(18) . . . . ?
O18 C18 C19 C20 -176.28(19) . . . . ?
O25 C25 C26 C27 -179.81(18) . . . . ?
N1A C1A C2A C3A -0.7(4) . . . . ?
N1B C1B C2B C3B 0.7(5) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C1 C2 C3 C7 179.07(19) . . . . ?
C1A N1A C5A C4A 0.3(3) . . . . ?
C1A C2A C3A C4A 0.6(3) . . . . ?
C1A C2A C3A C6A -179.8(2) . . . . ?
C1B N1B C5B C4B 0.8(4) . . . . ?
C1B C2B C3B C4B 0.4(4) . . . . ?
C1B C2B C3B C6B -179.2(3) . . . . ?
C2 C1 C6 O6 179.18(18) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C28 C24 22.6(3) . . . . ?
C2 C1 C28 C29 -104.4(2) . . . . ?
C2 C3 C4 O4 179.71(18) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C7 C8 -21.2(3) . . . . ?
C2 C3 C7 C30 105.8(2) . . . . ?
C2A C3A C4A C5A -0.1(3) . . . . ?
C2A C3A C6A C7A -41.0(3) . . . . ?
C2A C3A C6A C11A 139.4(2) . . . . ?
C2B C3B C4B C5B -0.9(4) . . . . ?
C2B C3B C6B C7B -10.4(3) . . . . ?
C2B C3B C6B C11B 167.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C7 C8 C9 108.7(2) . . . . ?
C3 C7 C8 C13 -68.1(2) . . . . ?
C3A C4A C5A N1A -0.4(3) . . . . ?
C3A C6A C7A C8A -178.6(2) . . . . ?
C3A C6A C11A C10A 179.4(2) . . . . ?
C3B C4B C5B N1B 0.3(4) . . . . ?
C3B C6B C7B C8B 178.0(2) . . . . ?
C3B C6B C11B C10B -177.3(2) . . . . ?
C4 C3 C7 C8 159.74(19) . . . . ?
C4 C3 C7 C30 -73.3(2) . . . . ?
C4 C5 C6 O6 -179.76(18) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4A C3A C6A C7A 138.5(2) . . . . ?
C4A C3A C6A C11A -41.1(3) . . . . ?
C4B C3B C6B C7B 170.0(2) . . . . ?
C4B C3B C6B C11B -12.0(4) . . . . ?
C5A N1A C1A C2A 0.3(3) . . . . ?
C5B N1B C1B C2B -1.3(4) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
C6 C1 C28 C24 -159.20(19) . . . . ?
C6 C1 C28 C29 73.8(2) . . . . ?
C6A C3A C4A C5A -179.6(2) . . . . ?
C6A C7A C8A C9A -0.8(3) . . . . ?
C6B C3B C4B C5B 178.8(2) . . . . ?
C6B C7B C8B C9B -0.1(4) . . . . ?
C7 C3 C4 O4 -1.1(3) . . . . ?
C7 C3 C4 C5 -179.72(19) . . . . ?
C7 C8 C9 C10 -177.23(18) . . . . ?
C7 C8 C13 O13 -3.3(3) . . . . ?
C7 C8 C13 C12 176.65(18) . . . . ?
C7A C6A C11A C10A -0.2(3) . . . . ?
C7A C8A C9A C10A -0.2(3) . . . . ?
C7B C6B C11B C10B 0.7(4) . . . . ?
C7B C8B C9B C10B -0.2(4) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C8 C9 C10 C14 179.98(18) . . . . ?
C8A C9A C10A C11A 1.0(3) . . . . ?
C8B C9B C10B C11B 0.8(4) . . . . ?
C9 C8 C13 O13 179.71(16) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 O11 -179.93(16) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C14 C15 -111.2(2) . . . . ?
C9 C10 C14 C31 12.7(2) . . . . ?
C9A C10A C11A C6A -0.8(3) . . . . ?
C9B C10B C11B C6B -1.1(5) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C10 C14 C15 C16 17.6(3) . . . . ?
C10 C14 C15 C20 -163.49(18) . . . . ?
C11 C10 C14 C15 68.0(2) . . . . ?
C11 C10 C14 C31 -168.13(18) . . . . ?
C11 C12 C13 O13 -179.69(18) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C11A C6A C7A C8A 1.0(3) . . . . ?
C11B C6B C7B C8B -0.1(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C14 C10 C11 O11 0.9(3) . . . . ?
C14 C10 C11 C12 -179.96(18) . . . . ?
C14 C15 C16 C17 179.4(2) . . . . ?
C14 C15 C20 O20 3.3(3) . . . . ?
C14 C15 C20 C19 -177.10(19) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C15 C16 C17 C21 178.20(19) . . . . ?
C16 C15 C20 O20 -177.77(18) . . . . ?
C16 C15 C20 C19 1.8(3) . . . . ?
C16 C17 C18 O18 178.58(18) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C16 C17 C21 C22 -14.4(3) . . . . ?
C16 C17 C21 C32 112.7(2) . . . . ?
C17 C18 C19 C20 2.6(3) . . . . ?
C17 C21 C22 C23 104.5(2) . . . . ?
C17 C21 C22 C27 -72.2(2) . . . . ?
C18 C17 C21 C22 165.08(18) . . . . ?
C18 C17 C21 C32 -67.9(2) . . . . ?
C18 C19 C20 O20 176.23(19) . . . . ?
C18 C19 C20 C15 -3.3(3) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
C21 C17 C18 O18 -0.9(3) . . . . ?
C21 C17 C18 C19 -179.76(19) . . . . ?
C21 C22 C23 C24 -176.38(18) . . . . ?
C21 C22 C27 O27 -3.5(3) . . . . ?
C21 C22 C27 C26 176.57(17) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C22 C23 C24 C28 179.24(18) . . . . ?
C23 C22 C27 O27 179.60(16) . . . . ?
C23 C22 C27 C26 -0.3(3) . . . . ?
C23 C24 C25 O25 179.96(17) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C23 C24 C28 C1 -113.1(2) . . . . ?
C23 C24 C28 C29 11.6(3) . . . . ?
C24 C25 C26 C27 1.0(3) . . . . ?
C25 C24 C28 C1 66.0(2) . . . . ?
C25 C24 C28 C29 -169.31(17) . . . . ?
C25 C26 C27 O27 179.70(18) . . . . ?
C25 C26 C27 C22 -0.4(3) . . . . ?
C27 C22 C23 C24 0.5(3) . . . . ?
C28 C1 C2 C3 179.8(2) . . . . ?
C28 C1 C6 O6 0.9(3) . . . . ?
C28 C1 C6 C5 -178.94(18) . . . . ?
C28 C24 C25 O25 0.8(3) . . . . ?
C28 C24 C25 C26 -179.99(18) . . . . ?
C30 C7 C8 C9 -15.9(3) . . . . ?
C30 C7 C8 C13 167.22(17) . . . . ?
C31 C14 C15 C16 -108.7(2) . . . . ?
C31 C14 C15 C20 70.2(2) . . . . ?
C32 C21 C22 C23 -20.9(3) . . . . ?
C32 C21 C22 C27 162.36(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.750
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7434(6)
2 0.2566(6)

####################################################################### 
# 
# 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_IsQNO_1
_database_code_depnum_ccdc_archive 'CCDC 1450588'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C9 H7 N O), 3(C H4 O), 3(O), C32 H32 O8'
_chemical_formula_sum            'C53 H58 N2 O16'
_chemical_formula_weight         979.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9'
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'

_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   16.5611(4)
_cell_length_b                   20.8203(8)
_cell_length_c                   14.9973(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5171.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4649
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.2550
_cell_measurement_theta_min      3.9500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.2448
_exptl_crystal_size_mid          0.0959
_exptl_crystal_size_min          0.092
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13761
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.728
_diffrn_reflns_theta_min         3.632
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176  -57.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176   77.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega   43.00   79.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega   77.00  171.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   31.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega  109.00  139.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  -60.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0313120000
_diffrn_orient_matrix_UB_12      -0.0012783000
_diffrn_orient_matrix_UB_13      -0.0966243000
_diffrn_orient_matrix_UB_21      -0.0875098000
_diffrn_orient_matrix_UB_22      0.0042134000
_diffrn_orient_matrix_UB_23      0.0345018000
_diffrn_orient_matrix_UB_31      0.0043288000
_diffrn_orient_matrix_UB_32      0.0738830000
_diffrn_orient_matrix_UB_33      -0.0037629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3758
_reflns_number_total             4622
_reflns_odcompleteness_completeness 97.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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         0.633
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.059
_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)+(0.0771P)²+3.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1590
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1S-O1S
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5W) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O1W(0.25) H2S(0.5) O2W(0.5) O3W(0.125) O4W(0.125) O5W(0.25)
 O6W(0.25) H2SA(0.5) H2SB(0.5) H2SC(0.5)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
5.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2(H2), C4A(H4A), C5(H5), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A),
 C9(H9), C9A(H9A), C12(H12), C15(H15), C18(H18)
5.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
5.d Idealised tetrahedral OH refined as rotating group:
 O2S(H2S), O3(H3), O11(H11), O13(H13), O17(H17)
;
_atom_sites_solution_hydrogens   mixed
_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
O1A O 0.48365(11) 0.37043(11) -0.29364(11) 0.0553(6) Uani 1 1 d . . . . .
O1S O 0.63882(12) 0.35564(17) -0.25816(12) 0.0821(9) Uani 1 1 d D . . . .
H1S H 0.5939(18) 0.369(2) -0.279(3) 0.123 Uiso 1 1 d DR . . . .
O1W O 0.8534(3) 0.2500 -0.0945(4) 0.0598(15) Uani 0.5 2 d S T P A 2
O2S O 0.4507(3) 0.2500 0.3826(3) 0.1008(13) Uani 1 2 d S T P . .
H2S H 0.4112 0.2561 0.4145 0.151 Uiso 0.5 1 calc GR . . . .
O2W O 0.8383(3) 0.2771(3) -0.0121(4) 0.0898(18) Uani 0.5 1 d . . . B -1
O3 O 0.40320(9) 0.36522(8) -0.14229(10) 0.0334(4) Uani 1 1 d . . . . .
H3 H 0.4248 0.3587 -0.1907 0.050 Uiso 1 1 calc GR . . . .
O3W O 0.6327(9) 0.2500 0.4506(15) 0.064(4) Uani 0.25 2 d S T P C 2
O4W O 0.6220(9) 0.2500 0.5082(11) 0.051(3) Uani 0.25 2 d S T P D 3
O5W O 0.5700(7) 0.2711(7) 0.4883(10) 0.088(5) Uani 0.25 1 d . U . E 1
O6W O 0.5989(9) 0.2925(7) 0.4492(9) 0.074(3) Uani 0.25 1 d . . . F -4
O11 O 0.62867(9) 0.50529(8) 0.13578(10) 0.0324(4) Uani 1 1 d . . . . .
H11 H 0.6204 0.5441 0.1339 0.049 Uiso 1 1 calc GR . . . .
O13 O 0.34439(9) 0.50377(8) 0.07381(10) 0.0332(4) Uani 1 1 d . . . . .
H13 H 0.3524 0.5426 0.0718 0.050 Uiso 1 1 calc GR . . . .
O17 O 0.64760(10) 0.36486(8) -0.08499(10) 0.0376(4) Uani 1 1 d . . . . .
H17 H 0.6485 0.3578 -0.1388 0.056 Uiso 1 1 calc GR . . . .
N1A N 0.45121(12) 0.39942(12) -0.36430(13) 0.0406(5) Uani 1 1 d . . . . .
C1 C 0.35876(11) 0.30899(11) -0.01344(14) 0.0284(5) Uani 1 1 d . . . . .
C1A C 0.48544(14) 0.39450(14) -0.44357(15) 0.0401(6) Uani 1 1 d . . . . .
H1A H 0.5338 0.3722 -0.4491 0.048 Uiso 1 1 calc R . . . .
C1S C 0.6959(2) 0.3469(2) -0.3181(2) 0.0866(13) Uani 1 1 d . . . . .
H1SA H 0.6951 0.3031 -0.3379 0.130 Uiso 1 1 calc GR . . . .
H1SB H 0.7475 0.3563 -0.2921 0.130 Uiso 1 1 calc GR . . . .
H1SC H 0.6867 0.3749 -0.3679 0.130 Uiso 1 1 calc GR . . . .
C2 C 0.34491(16) 0.2500 0.02685(19) 0.0288(7) Uani 1 2 d S T P . .
H2 H 0.3250 0.2500 0.0848 0.035 Uiso 1 2 calc RS T P . .
C2A C 0.45044(14) 0.42213(13) -0.51965(15) 0.0375(6) Uani 1 1 d . . . . .
C2S C 0.4265(6) 0.2500 0.2920(5) 0.133(3) Uani 1 2 d S T P . .
H2SA H 0.3797 0.2232 0.2850 0.199 Uiso 0.5 1 calc GR . . G -1
H2SB H 0.4697 0.2337 0.2557 0.199 Uiso 0.5 1 calc GR . . G -1
H2SC H 0.4138 0.2931 0.2739 0.199 Uiso 0.5 1 calc GR . . G -1
C3A C 0.37645(14) 0.45495(13) -0.51084(16) 0.0365(5) Uani 1 1 d . . . . .
C4A C 0.34347(14) 0.46024(14) -0.42420(17) 0.0438(6) Uani 1 1 d . . . . .
H4A H 0.2954 0.4825 -0.4159 0.053 Uiso 1 1 calc R . . . .
C5 C 0.40560(17) 0.2500 -0.14294(19) 0.0294(7) Uani 1 2 d S T P . .
H5 H 0.4267 0.2500 -0.2004 0.035 Uiso 1 2 calc RS T P . .
C5A C 0.38087(15) 0.43334(15) -0.35338(16) 0.0470(7) Uani 1 1 d . . . . .
H5A H 0.3587 0.4379 -0.2967 0.056 Uiso 1 1 calc R . . . .
C6 C 0.38983(12) 0.30773(11) -0.10009(14) 0.0291(5) Uani 1 1 d . . . . .
C6A C 0.48676(18) 0.41623(16) -0.60433(17) 0.0517(7) Uani 1 1 d . . . . .
H6A H 0.5362 0.3955 -0.6102 0.062 Uiso 1 1 calc R . . . .
C7 C 0.34242(12) 0.37241(12) 0.03338(14) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.3155 0.4004 -0.0100 0.036 Uiso 1 1 calc R . . . .
C7A C 0.44928(19) 0.44099(17) -0.67753(18) 0.0601(8) Uani 1 1 d . . . . .
H7A H 0.4730 0.4366 -0.7334 0.072 Uiso 1 1 calc R . . . .
C8 C 0.41930(12) 0.40692(12) 0.06255(13) 0.0284(5) Uani 1 1 d . . . . .
C8A C 0.37518(18) 0.47316(16) -0.66923(19) 0.0566(8) Uani 1 1 d . . . . .
H8A H 0.3503 0.4898 -0.7198 0.068 Uiso 1 1 calc R . . . .
C9 C 0.49343(13) 0.37589(12) 0.07082(13) 0.0289(5) Uani 1 1 d . . . . .
H9 H 0.4957 0.3320 0.0595 0.035 Uiso 1 1 calc R . . . .
C9A C 0.33909(16) 0.48039(14) -0.58807(18) 0.0465(6) Uani 1 1 d . . . . .
H9A H 0.2901 0.5020 -0.5835 0.056 Uiso 1 1 calc R . . . .
C10 C 0.56446(13) 0.40735(12) 0.09529(13) 0.0290(5) Uani 1 1 d . . . . .
C11 C 0.55918(12) 0.47296(11) 0.11334(13) 0.0288(5) Uani 1 1 d . . . . .
C12 C 0.48589(13) 0.50519(12) 0.10820(13) 0.0294(5) Uani 1 1 d . . . . .
H12 H 0.4830 0.5486 0.1224 0.035 Uiso 1 1 calc R . . . .
C13 C 0.41686(12) 0.47227(12) 0.08177(13) 0.0286(5) Uani 1 1 d . . . . .
C14 C 0.64556(13) 0.37291(12) 0.10242(15) 0.0319(5) Uani 1 1 d . . . . .
H14 H 0.6856 0.4005 0.0733 0.038 Uiso 1 1 calc R . . . .
C15 C 0.64624(17) 0.2500 0.0966(2) 0.0301(7) Uani 1 2 d S T P . .
H15 H 0.6460 0.2500 0.1586 0.036 Uiso 1 2 calc RS T P . .
C16 C 0.64640(11) 0.30919(11) 0.05330(14) 0.0292(5) Uani 1 1 d . . . . .
C17 C 0.64616(12) 0.30765(11) -0.03960(15) 0.0306(5) Uani 1 1 d . . . . .
C18 C 0.64567(18) 0.2500 -0.0859(2) 0.0316(7) Uani 1 2 d S T P . .
H18 H 0.6450 0.2500 -0.1479 0.038 Uiso 1 2 calc RS T P . .
C19 C 0.67055(16) 0.36723(13) 0.20051(16) 0.0432(6) Uani 1 1 d . . . . .
H19A H 0.6304 0.3433 0.2326 0.065 Uiso 1 1 calc GR . . . .
H19B H 0.6754 0.4094 0.2259 0.065 Uiso 1 1 calc GR . . . .
H19C H 0.7215 0.3454 0.2045 0.065 Uiso 1 1 calc GR . . . .
C20 C 0.28524(15) 0.36596(13) 0.11368(16) 0.0391(6) Uani 1 1 d . . . . .
H20A H 0.2364 0.3449 0.0953 0.059 Uiso 1 1 calc GR . . . .
H20B H 0.2726 0.4079 0.1364 0.059 Uiso 1 1 calc GR . . . .
H20C H 0.3110 0.3411 0.1594 0.059 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
O1A N1A 1.333(3) . ?
O1S H1S 0.852(19) . ?
O1S C1S 1.317(4) . ?
O2S H2S 0.8200 . ?
O2S C2S 1.417(7) . ?
O3 H3 0.8200 . ?
O3 C6 1.372(3) . ?
O5W O5W 0.88(3) 8_565 ?
O11 H11 0.8200 . ?
O11 C11 1.375(3) . ?
O13 H13 0.8200 . ?
O13 C13 1.373(3) . ?
O17 H17 0.8200 . ?
O17 C17 1.372(3) . ?
N1A C1A 1.321(3) . ?
N1A C5A 1.372(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.398(3) . ?
C1 C7 1.520(3) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.403(3) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C2 C1 1.388(3) 8_565 ?
C2 H2 0.9300 . ?
C2A C3A 1.409(3) . ?
C2A C6A 1.410(3) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?
C3A C4A 1.414(3) . ?
C3A C9A 1.416(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.351(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) 8_565 ?
C5 C6 1.388(3) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.363(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.526(3) . ?
C7 C20 1.538(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.404(4) . ?
C8 C9 1.393(3) . ?
C8 C13 1.391(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.364(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(3) . ?
C9A H9A 0.9300 . ?
C10 C11 1.395(3) . ?
C10 C14 1.526(3) . ?
C11 C12 1.389(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(3) . ?
C14 H14 0.9800 . ?
C14 C16 1.518(3) . ?
C14 C19 1.533(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(3) 8_565 ?
C15 C16 1.393(3) . ?
C16 C17 1.394(3) . ?
C17 C18 1.387(3) . ?
C18 C17 1.387(3) 8_565 ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
C1S O1S H1S 115(3) . . ?
C2S O2S H2S 109.5 . . ?
C6 O3 H3 109.5 . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 109.5 . . ?
C17 O17 H17 109.5 . . ?
O1A N1A C5A 118.71(19) . . ?
C1A N1A O1A 120.5(2) . . ?
C1A N1A C5A 120.8(2) . . ?
C2 C1 C6 116.7(2) . . ?
C2 C1 C7 122.56(19) . . ?
C6 C1 C7 120.7(2) . . ?
N1A C1A H1A 119.2 . . ?
N1A C1A C2A 121.5(2) . . ?
C2A C1A H1A 119.2 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1 C2 C1 124.5(3) . 8_565 ?
C1 C2 H2 117.8 . . ?
C1 C2 H2 117.8 8_565 . ?
C1A C2A C3A 118.8(2) . . ?
C1A C2A C6A 121.4(2) . . ?
C3A C2A C6A 119.8(2) . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C2A C3A C4A 117.4(2) . . ?
C2A C3A C9A 119.0(2) . . ?
C4A C3A C9A 123.6(2) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A C3A 120.9(2) . . ?
C5A C4A H4A 119.6 . . ?
C6 C5 H5 120.0 8_565 . ?
C6 C5 H5 120.0 . . ?
C6 C5 C6 120.0(3) . 8_565 ?
N1A C5A H5A 119.7 . . ?
C4A C5A N1A 120.6(2) . . ?
C4A C5A H5A 119.7 . . ?
O3 C6 C1 118.2(2) . . ?
O3 C6 C5 120.78(19) . . ?
C5 C6 C1 121.1(2) . . ?
C2A C6A H6A 120.1 . . ?
C7A C6A C2A 119.9(3) . . ?
C7A C6A H6A 120.1 . . ?
C1 C7 H7 106.9 . . ?
C1 C7 C8 113.14(17) . . ?
C1 C7 C20 113.30(19) . . ?
C8 C7 H7 106.9 . . ?
C8 C7 C20 109.29(18) . . ?
C20 C7 H7 106.9 . . ?
C6A C7A H7A 119.8 . . ?
C6A C7A C8A 120.5(3) . . ?
C8A C7A H7A 119.8 . . ?
C9 C8 C7 122.9(2) . . ?
C13 C8 C7 119.71(19) . . ?
C13 C8 C9 117.4(2) . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A C7A 121.0(3) . . ?
C9A C8A H8A 119.5 . . ?
C8 C9 H9 118.4 . . ?
C8 C9 C10 123.3(2) . . ?
C10 C9 H9 118.4 . . ?
C3A C9A H9A 120.1 . . ?
C8A C9A C3A 119.8(3) . . ?
C8A C9A H9A 120.1 . . ?
C9 C10 C14 122.7(2) . . ?
C11 C10 C9 117.2(2) . . ?
C11 C10 C14 120.1(2) . . ?
O11 C11 C10 118.31(19) . . ?
O11 C11 C12 120.6(2) . . ?
C12 C11 C10 121.1(2) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
O13 C13 C8 118.33(19) . . ?
O13 C13 C12 120.5(2) . . ?
C12 C13 C8 121.1(2) . . ?
C10 C14 H14 106.8 . . ?
C10 C14 C19 109.95(18) . . ?
C16 C14 C10 112.63(17) . . ?
C16 C14 H14 106.8 . . ?
C16 C14 C19 113.3(2) . . ?
C19 C14 H14 106.8 . . ?
C16 C15 H15 117.8 . . ?
C16 C15 H15 117.8 8_565 . ?
C16 C15 C16 124.4(3) 8_565 . ?
C15 C16 C14 123.2(2) . . ?
C15 C16 C17 116.5(2) . . ?
C17 C16 C14 120.3(2) . . ?
O17 C17 C16 118.4(2) . . ?
O17 C17 C18 120.2(2) . . ?
C18 C17 C16 121.4(2) . . ?
C17 C18 C17 119.9(3) 8_565 . ?
C17 C18 H18 120.0 8_565 . ?
C17 C18 H18 120.0 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
C7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1A N1A C1A C2A 177.1(2) . . . . ?
O1A N1A C5A C4A -176.1(3) . . . . ?
O11 C11 C12 C13 177.31(17) . . . . ?
O17 C17 C18 C17 178.46(16) . . . 8_565 ?
N1A C1A C2A C3A -1.0(4) . . . . ?
N1A C1A C2A C6A -179.4(3) . . . . ?
C1 C7 C8 C9 -18.6(3) . . . . ?
C1 C7 C8 C13 161.13(18) . . . . ?
C1A N1A C5A C4A 2.7(4) . . . . ?
C1A C2A C3A C4A 2.5(4) . . . . ?
C1A C2A C3A C9A -177.2(3) . . . . ?
C1A C2A C6A C7A 176.9(3) . . . . ?
C2 C1 C6 O3 179.1(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C7 C8 106.4(2) . . . . ?
C2 C1 C7 C20 -18.8(3) . . . . ?
C2A C3A C4A C5A -1.6(4) . . . . ?
C2A C3A C9A C8A -0.4(4) . . . . ?
C2A C6A C7A C8A 0.9(5) . . . . ?
C3A C2A C6A C7A -1.5(5) . . . . ?
C3A C4A C5A N1A -1.0(4) . . . . ?
C4A C3A C9A C8A 179.9(3) . . . . ?
C5A N1A C1A C2A -1.7(4) . . . . ?
C6 C1 C2 C1 -0.9(4) . . . 8_565 ?
C6 C1 C7 C8 -72.9(2) . . . . ?
C6 C1 C7 C20 162.01(19) . . . . ?
C6 C5 C6 O3 -178.39(15) 8_565 . . . ?
C6 C5 C6 C1 0.6(4) 8_565 . . . ?
C6A C2A C3A C4A -179.0(3) . . . . ?
C6A C2A C3A C9A 1.2(4) . . . . ?
C6A C7A C8A C9A 0.0(5) . . . . ?
C7 C1 C2 C1 179.83(17) . . . 8_565 ?
C7 C1 C6 O3 -1.6(3) . . . . ?
C7 C1 C6 C5 179.4(2) . . . . ?
C7 C8 C9 C10 178.35(18) . . . . ?
C7 C8 C13 O13 0.1(3) . . . . ?
C7 C8 C13 C12 -179.75(18) . . . . ?
C7A C8A C9A C3A -0.3(5) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C8 C9 C10 C14 -178.85(18) . . . . ?
C9 C8 C13 O13 179.84(17) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C9 C10 C11 O11 -178.66(17) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C9 C10 C14 C16 18.3(3) . . . . ?
C9 C10 C14 C19 -109.2(2) . . . . ?
C9A C3A C4A C5A 178.1(3) . . . . ?
C10 C11 C12 C13 -2.2(3) . . . . ?
C10 C14 C16 C15 -107.8(2) . . . . ?
C10 C14 C16 C17 71.2(2) . . . . ?
C11 C10 C14 C16 -161.58(19) . . . . ?
C11 C10 C14 C19 71.0(3) . . . . ?
C11 C12 C13 O13 -178.09(17) . . . . ?
C11 C12 C13 C8 1.7(3) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
C14 C10 C11 O11 1.2(3) . . . . ?
C14 C10 C11 C12 -179.32(18) . . . . ?
C14 C16 C17 O17 1.9(3) . . . . ?
C14 C16 C17 C18 -179.0(2) . . . . ?
C15 C16 C17 O17 -179.0(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C15 C16 C14 179.51(17) 8_565 . . . ?
C16 C15 C16 C17 0.5(4) 8_565 . . . ?
C16 C17 C18 C17 -0.6(4) . . . 8_565 ?
C19 C14 C16 C15 17.8(3) . . . . ?
C19 C14 C16 C17 -163.2(2) . . . . ?
C20 C7 C8 C9 108.6(2) . . . . ?
C20 C7 C8 C13 -71.6(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7 0 -7 0.0590 -6.9999 0.0003 -6.9999 0.8955 0.3710 -0.0039
1 13 0 0.1377 0.9999 13.0003 0.0003 -0.0480 -0.0327 0.9648
7 -1 7 0.0263 6.9999 -1.0003 6.9999 -0.8943 -0.3753 -0.0699
0 -13 0 0.1000 0.0001 -13.0003 -0.0003 0.0166 -0.0548 -0.9605
8 0 -7 0.0558 8.0001 0.0000 -7.0001 0.4259 -0.9416 0.0610
-8 0 7 0.0362 -8.0001 -0.0000 7.0001 -0.4259 0.9416 -0.0610

_olex2_submission_special_instructions 'No special instructions were received'
